UNITED STATES EN V IRONMENTAL PROTECTION AGENCY WASHINGTON , D

. C

. 20460 

### MAY 0 6 2015 MEMORANDUM OFFICE OF CHE M ICAL SAFETY A N D POLLUTIO N PREV ENT IO N

SUBJECT: BEAD Chem ical Profile (SCP) for Registration Review: Tetraconazole (120603) 

### FROM: Leon ard Yourman, Plant Patholo g ist 

# A Biol ogical Ana lys i s Branc h 

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THRU :

TO: R afae l A. Prieto , Environmental P rotection

# Spec**al ,A**  . / /_
.

# ~ Sc ience ln fo(lllation and Analysis Bra nch 

## I

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# f 1'-0 

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M ichelle Ranville , Economist Economic Ana lysis Bran c h Biolo g ical and Econ omi c Anal Arnet Jones, Chief Biolo g ical Ana lysis Branc Di ann Sims , Chief Science Information and Ana lysi s Branch .._ Timothy Kiely. Ch ief

# ~**~ (~** **,** Economic Analysis Branch J

### ~ Biological and Eco nomic Analy · Div i sion (75 3P Veronica Dutc h , C hemical Review Manager Ri sk Management and Impl eme nt at ion Bran ch 5 P est ic ide Re -evaluation Di vision (7508P)
Peer Review Pane l date: Ma rc h 1 8, 20 1 5

### SUM MA R Y Tetraconazole i s a de methylati o n inhibitin g ( DMI) fun gic id e first u sed in 1999 under a Section 18 Emergency Exe mpti on for managing Ce rcospo ra leaf spot on s ugar beet. It is registered for use on soy beans, sugar beets, co rn , peanuts , pecans , and some berri es. In terms of percent crop treated , tetraconazole was u sed on 30 percent of the sugar beet crop. Th e predominant u ses in te rm s of pound s a . i. app lied
.are o n sugar beets w ith 4 0 , 000 lbs and soybean s with 30 , 000 lb s applied annuall y (average use 2004-2012). Fo r the years 2008

- 2012, overall tetraconazole annual ag ricultural u sage averaged 77 , 000 lbs of a.i. treating an average of 1
. 1 million acres with an overall average application rate of 0.07 p ounds a.i. per ac re.


### INTR OD UCT IO N The Biologica l and Economic A nal ysis Div i sion ( BEAD ) Chemical Profil e ( BCP ) provides an overview of the pest management r o l es and quantitative usage information fo r tetraconazole. The BCP in c l udes summaries of previous B EAD products and avai lable pub li c and/ or private u se and usa ge data for tetrac o nazo le t o d es crib e th e ro le of th is chemical in pest man ageme nt. Additional informat io n o n use is avail able in the Tetraconazole Label Data Report. In fom1ation provided in this BEAD Chemical Profil e ( B C P ) may be used by s takehold e rs (e.g., users an d regis trant s), OPP risk assesso r s and OPP risk m an age rs, and the ge neral public during th e Registration Review process of this pest icide. Tetraconazole i s a d e mcthylati o n inhibi tin g (DM I) fun gicide li sted by th e F un g icide R es i s tanc e Action Comm ittee as a Group 3 f un g ic id e ( FRA C, 2014). Tetraconazole was g i ven a Section 3 registration in 2005. H owever, in 1 999, it was the first DM I fungicide avai lable (with a Section 18 lab e l) for u se o n s uga r bee t to man age Ce rco spo ra le af spo t initially in Minn esota and No rth Dakota ( F e d eral R egis ter. 1 999). The predominant use of tetraco n azole in terms of percent cro p treated is on sugar beet s with 30 percent of the crop treat ed. The predominant u ses in te rm s of pounds a. i. applied are o n sugar beets with 40 ,000 lbs and soy b ean s with 30,0 00 lb s applied annually , o n average, from 2004-2012 (Sc reenin g -Level Usag e Ana l ysis. Nove mber 20 14 ).


### USE S IT ES Agricultural u ses T etraconazo le is registered for use o n corn (fie ld , pop )
. peanuts. pecans. soybean s, and s u gar beets. It is also registered for so me crops of the IR-4 crop su b groups including l 3-07F (sma ll fmit v in e climbing subgroup , except fu zzy kiwifruit) and 13

- 070 (low grow in g berry s ub group, excluding cranberry). Non-agricultural use s There are no non-agricultural reg istered uses fo r tetraconazole.

2

### FORMULATIONS AND APPLICATION METHO DS Tetraconazo le i s formulated a s an emul s ifiable concentrate . Depending on the crop , it m ay be applied broadcast by grou nd or ai r , by chemigat io n o r sp rinkl er irrigat io n , or wit h a hi g h volume or low vo lume sprayer.


### HI ST ORY O F TETRACONAZOLE AN D BEAD PRODUCTS B EA D reviewed Sec ti on l 8 · Emergency Exemption requests for suga r beets grown in M o nt ana, No rth Da ko ta , Minnesota , and Co lorado p ri or to the Sec tion 3 re g is tration. T he Sect io n 18 requests we re to control Cerco spo ra leaf spot disease (c aused by 

### Cercospora beticola) and were ba se d on disease re s is tance to o ther fung i cides
. BEAD has no t conducte d a ny oth e r assessments fo r tetraconazole. In 2 005 , tetraconazole rece i ved a Section 18 l abe l fo r man ag in g As ian soybean rust. Asian soybean rust has had limited impact on soybean production , but tetraconazole is use d to manage Ce rcospora blight. frogeye l eaf s pot , po w dery mildew , brown s pot , and an thracnose.


### USAGE Usage Tre nd s Fi gure 1 present s tetraconazole usage in pounds a. i
. applied and Fi gure 2 shows tot a l area treated in acres over the 

### 1999

- 20 12 timeframe ( Propri e tary Data, 

### 1999-201 2). Figures 

### 1 and 

### 2 s how that over this t ime period th e re was a decrease until 2006 , a s pik e in 2008 , and then a decrease in u se in t e rms of both pounds applied and acres treated. The increa se d us e may be due to the concern of As ian soybean rust 

### (Phakopsora spp.) ha vi ng been identified in the U.S. fo r the first time aro und thi s period. Preve ntati ve fungicide sprays of variou s fungicides (primaril y Group 3 o r Group 

### 11 fung icides) we re applied. Th e decline in tetraconazo le u se may be at least partially explained by additional r eg istra t ion s of DMI fungicides for managing Cercospora leaf spot in sugar beet (e
. g. , Carlson et a l. , 20 1 3)

3ct 

### "' "O c :J 0 a. 120,000**~°>** R><:) R>"" R>"' R>,,, R>t>. R>" R><o**~** R>'b R>°>**~<:) ~""** **~"' ~**  

### '\..(:) '\..(:) -f5 '\..(:) '\..(:) '\..(:) '\..(:) '\..(:) '\..\:) '\..(:) '\..<:) '\..<:) '\..<:) Year Figure 1. 

### Tota l Po unds of Tetraconazole A p p li ed ( 1999-2012). So u rec : Proprietary Dat a, 1999

-20 12

Vi' QI 

## ... u <t**~** "O QI 

# - ni QI 

## ...tni QI 

## ... <t 1,600,000

Year Figure 

### 2. Total Area Treated (TAT) of Tetraconazole in Acres ( 1999-2012). Source: Proprietary Data, 1999-2012


### For the years 2000 -20 04 , tetraconazole annua l agricultu ral usage averaged 88,000 lbs of active ingredient (a. i. ) treatin g an average of 900,000 acres, with a n overa ll avera ge app li ca ti on rate of 0.10 pounds a.i. per acre. (Proprietary data , 2000

- 2004). F o r th e years 2008-20 12, tetraco nazole ann u a l ag ri c ultural usage averaged 77 , 000 lbs of a. i
. treating an average of 1.1 million acres , w ith an overall average app licati on rate of 0.07 pounds a.i
. per acre . (Prop riet ary data. 2008-2012).

4

### For the 2000

- 2004 time period , essentially all tetraconazole use was on sugar beet (Table I ). For the 2000

- 2004 time period , the states with the hi g hes t use of te traconazo le were Minnesota and No rth Dak o ta. For th e 2008-2012 tim e period , the cro ps receiving the mo st te tra conazo l e were soy bean and sugar beets (Tables I and 2). For the 2008

- 2012 time period , the states with th e highest use oftetraconazo le were Mi nn esota and Illinoi s (Tab l e 3). The percent of total use of te tracona zo le on s ugar beets ma y hav e decreased re lative to soy bean due to reg istration s of other DMI fungicides fo r managing Cerco spo ra leaf spot o n s ugar beet and an increased use of O M I fungicides in response to the concern fo r Asian soybean rust th at fi rst was obser ved in the U.S
. in 2004 (Rupe and Sconyers, 2008). Soybeans is the top crop during the 2008-20 12 tim e span , replac in g suga r beets , wh ich was th e main c rop in terms of tetraconazole use durin g the 2003

- 2007 time span (figure 3). Use of tetraco nazo le on other crops s uch as grapes, is negl igible for th e 2010-2012 time s pan and ze ro fo r the earli e r years.

80,000

VI a. 0 

## u a. 0 

### .._

..... 0 

## .... ct VI -0 c :::l 0 0..**~ ~** **~ ~** **~ ~** **~ ~**  

### Y N 'I-" '\.G '\.cs "'cs "'cs '\.G "'" 

### "'<:) "'<:) '\." Year F ig ure 

### 3. P ounds of T etraconazole for Top Crops, 2003

- 20 12. -+- Sugar Beets

-+- Soybeans

- • Grape s (Wine & Rais in)



### Tab le 1. 

### Comparison of Crops with Hi ghes t Use ofTetraconazole in Terms of Pounds App li ed for Years 2000-2004 a nd 2008-2012. 2000-20 0 4 2008-20 12 C r oo % L bs Crop % Lb s Sugar bee t s > 99 Soybeans 63

Aooles < I Sugar bee t s 35 Other• 2 • O th er include s: Win e grapes. raisin grapes . peanuts. com. drv beans/ peas. and table "grap es. So u rce : Proprietary Dat a. 2000-2004 , 200 8- 20 12.

5

### T bl 2 T I U 

### T C d 

### A IR 2008 2012 a e 

## . etraco na zo e se o n op rops an Average 

### . . ate, 

## - C rop Tot a l Pound s A p p li e d Total A r ca T re ated * A l Rate ( l b s Al/acres) ** Soybeans 250.000 4,000.000 0.062 Sugar beets 140 , 000 1 ,400.000 0.093 So ur ce: Propri eta r y Data , 2008-201 2 * T otal A rea Treated s ums all acres treated for a crop , in cluding tho se ac res that receive multiple tr e atment s . 

### ** Average Al rates fo r fruit s and ve ge tabl es are lo wer than tho se r e ported for soybeans a nd s uga r bee ts. For exa mpl e. the a verage A l rate fo r grapes is 0.033 lb s Al/acre. Geograph i c D i stribution of Tetracon az ole Use A ccording to the following map , North Caroli na i s the stat e with th e hi g he s t u sage (0.8 lb s) i n term s of pounds per 1 , 000 crop ac re s grow n.

Pou nd s Act ive I ngredient p er 1 , 000**C~op** Acre s Grown i=J NoOet e <O 05 005

- 0 4

. 0
. 5·08

- >08 

### Figure 4. Annu a l averagc ·a g ricultural u se inte n s ity of tetraco n azo le (2 009-2013 ). T he map i ncluded he rein is primar il y fo r the use of the ri sk ass ess o rs in the Environmental Fate and Effects Division. The map provides a ve ry bro ad geographical view of th e a ve rage annual amount ( in pound s) of the active in gredie nt ap pli ed per 1 ,000 ac res of cro p acres grown. T he se data are included in the maps because ri s k assessors are intere s t e d in th e amount of a pe st ic ide used across agricultural land
. The calculated va lu es pre se nted in the map are not e quival e nt to an app l ica ti on rate ( lb 

### ai l A). 

### 6The data u se d to make these maps hav e several limitations. Any interpretation of the maps should consider the underlying data and the associated limit at ion s carefully. The nwne rator (annual average pound s applied) is based on private market surveys of pesticide u se in agriculture averaged over the last five years (Proprietary Data , 2008-2012). These surveys cover about 60 crops and are targeted in states that produce the maj o rity of the crop. Although the sur veys capture mo s t of the use of a particular active in g red ient in agriculture, th ere are several limitation s to these surveys.

• States with minor production of a surveyed crop are not sampled • No t all types of pesticide s are su r veye d in every crop in every yea r • Many specialty crops with very small ac rea ges are not included in the survey The result of the se limitations is that states that show no usage may actually have a sma ll amount of the active ingredient being u se d. In so me cases the displayed us e intensity may be di s torted because the surveyed crops and the reported pesticide usage may not accurately represent the actual pe s ticide u s age on the crops produced in the state. The denominator ( 1,000 crop acres grown) was also obtained from the same private market survey database. The "C rop Acres Grown" variab l e represents the total acres grown in a g iven state of al I of the su rveyed crops. Thi s va lue is indep e ndent of pesticide u sage and pesticide re g istration. It is important to note that the s urveyed crops (about 60) are sampl ed from states that are major producer s of each crop. Therefore , there are cases where the actual crop acreage in a s tate i s higher than that reported by crop acres grown in the survey becau se e ither that state and / or crop was not included in the survey. The reader should pay particular attent ion to the figure legends and re alize that a map prepared for a particular chemical is not directly comparable to a map prepared for a different chemical as th e legend bins will likely be different.


### Tab le 3
. Co mparison of States with Highest Use of Tetraconazole in Term s of Pounds Al for Y ea rs 2000-2004 and 2008-2012 2000-2004 2008-2012 S t ate % L bs State % Lb s Minnesota 61 Minne so ta 2 1 North Dako ta 30 lllin ois 15

Michigan 7 North Carolina 10

Other• 2 Other• 54 

### * Othe r includes: Co lo rado. Montan a, Nebra ska , and • Other include s: North Dakota , I owa, Mi ss iss ippi. North Carolina. Tennes s ee, Michi gan. Arkansas, So uth Dakota. Ohio. C alifornia. Ind iana. Mont ana. Alabama. Sou th Carolina, Kentucky, Loui s iana , Kan s as, Co lo rado. Nebraska , Virgini a, Wi sco ns in , Mi sso uri , Florid a, Georgia , and I daho. Sou rce : Proprietary Data. 2000

-2004. 2 008- 20 12.

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### CHEMICAL AND USE CHARACTERISTICS FOR TETRACONAZOLE Tetraconazole is a demethylation inhibiting ( DMI ) fungicide l isted by the Fun gicide Resistance Action Committee as a Group 3 fungicide (FRAC , 2014). Other Group 3 fungicides include tebu conazo l e , myclobutanil , metco naz o le, difenoconazole , and several others. DMI fungicides provide protectant and some curative activity due to systemic xylem mobility. As is the case with a ll disease mana ge ment strategies , pre-infection protec tive applications allow for the most effective di sease management. Group 3 fungicides are conside red c ros s-res i stant for purposes of resi stance management although the spec ific mode of action may vary among individual active ingred ient s within the Gro up 3 fu ngicid es . Th erefo re , while an individual Group 3 active ingredient may be more effect iv e against a particular pathogen/host system than another Group 3 fungicide Group 3 , fungicides should not be used as alternating partners in a fungicide spray pro gram (FRAC, 2014). Typically , an individual fungicide wou ld not be relied on exclusively to manage a disease and tetraconazol e would be one among other fungicides included in a s pray program. A fungicide used in a tank-mix or alternated with other fungicides wou ld include those of different modes of action (i .e. , different fung icide Groups). Resistance to at least two important fungicide groups, Group 3 and Group 11 (Qol-quinone outside inhi bitors s uch as pyraclostrobin) , has been observed for powdery mildew pathogens on grape in the mid-Atlantic region where dual resistance is known (e.g. , DeMarsay , 2012)
. For grapes in eastern Washington, resistance by powd e ry mild ew pathogens to Group 3 and Group 11 fungicides had not become a probl e m (as of 20 I 1 ) , but " this could change rapidly given the nature of powdery mildew and the resistance history (in grapes) of Group 11 and Group 3 fungicides,. (Grove and Nelson , 2011 ).


### ROLE OF TETRACONAZOLE IN PEST MANAGEMENT Tetraconazole is used for managing severa l diseases on labeled crop (some applications manage more than one disease). Tetraconazole was first used in 

### 1999, as an emergency treatment for Cercospora le af spot on sugar beets. Under high disease pressure , there was up to 30% lo ss of recoverable sugar with revenue losses reported up to 43 % (Khan and Smith , 2005). In 

### 1998, the fungicides used to treat Cercospora leaf spot were fentin hydroxide , mancozeb, and thiophanatemethyl. These provided incon s iste nt contro l , espec i ally thiophanate-methyl due to high populations of thiophanate

- methyl-resistant pathogens. Tetraconazole has provided effective control of Cercospora leaf spot since 

### 1999. According to Carlson et al. (2013), from an historical perspec tive , te tracona zo le and pyrac lostrobin have had a large impact on controlling Cercospora leaf spot. ln 

### 1998 , their survey indi cated th at 36% of respondents found Cercospora leaf spot to be their worst production problem. Afte r the introduction oftetraconazole and pyraclostrobin , by 2000 , 3% of respond e nts felt that Cercospora leaf spot was a problem. Th is percent has remained below I % s ince that time. Additional registrations has like ly caused the use of tetraconazole to decline (Tab le 1 ). Since that time several other DMI fungicides have been reg istered includin g prothioconazole (Proline) , propiconazo le (Ti lt). Cenbuconazole (Enable) , difenoconazole 

### + propiconazo le (Inspire XT) , and flutriafol (Topguard) (Khan and Hakk, 2013). In addition , Group 11 fungicides (pyrac lo s trobin , azoxystrob in , and trifloxystrobin) are registered and used with other regi stered fungicides as rotating partners for



### 8resistance managment. Ho wever , when tested (Secor et al. , 2013) C. 

### b e 1icola resistance to tetraconazole and difenoconazole 

### + propiconazol e ( Inspire) ha s increa se d significant ly s inc e 20 11. Tetraconazole and o th er DMI a nd Qol fungicides we re among those that were considered effe ctive in managin g Asian soybean ru s t if the di sease became a probl e m after be ing first introduc ed into the U.S. in 2004. In 2005, tetrac o na zo le rec e i ved a Section 18 lab e l for managing Asian soybean rust. Asian soybean ru s t has had limited impact o n soybean production, but tetraconazole is u se d to manage Cercospora bl ig ht , frogeye leaf spo t , powde r y mildew , 

### brovm spot , and anthrac nose. These disea ses may occur in hi g h de nsity plantings where humidity initiate s pathogen activity. The ex t ent of th e r ece nt increased use of tetraconazole on soybean is likel y a result of several factors including price in centives fo r higher quality beans and perc e iv e d valu e o f additiona l input for crop production . Exte nsion s pec ialist s de bate th e value o f fun g icide applications o n soybean. but man y growe r s attribute an incre ase in yi e ld to fungicides (e.g
. , Roberson , 20 I 0). Lesser u ses of tetraconazole in c lud e g rapes and s mall berrie s where te traconazo le (as well as several o th er fungicides) is very effective ag ain st powdery mildew (e
. g .. UC , 2013)
. On peanuts , tetraconazole is used to manage earl y leaf s pot 

### (Cercospo ra arachidicola) and late l eaf spot 

### (Cercospo ridium persona/um) as well as web blotch 

### (Phoma arachidicola) and peanut ru s t 

### (Puccinia a ra chidis). Several pecan di seases may be mana ged with tetraconazo le , including powdery mildew , scab , br own leaf spot , downy mild ew , and leaf blotch. Co m di s eases managed with tetraconazole include gray leaf spot , rusts , anthracnose, eye spot , northern c o rn leaf blight , no11hern corn leaf spot , and southern corn leaf bli g ht
. 

### DATA NEE DS Obtai nin g add iti ona l usage in format i o n o n s mall v in e fruits and pecans ( including lbs applied , total area treated , states , application rate s , target pests) may improve future B EAD assess me nt s of the importance of t etracona zo le and may be required as part of the reg i s trati on rev iew of thi s pesticide.


### REFERENCES Car lson , A. 

### L. , Khan , M. F. R. , and Boetel , M.A. 20 1 3
. Survey of fungicide u se in sugarbeet in Minnesota and eastern North Dakota in 20 1 3
. North Dakota S tate U ni vers ity Exte n sio n . http ://www . sbreb
. org/research / plant/plant 13 / CarlsonSurveyOIFungicidc
. pdf. Accessed February 2015. D eMarsay , A. 2012. Guide lin es for Dev e lo ping an Effe ctiv e Fung ic id e Spray Pro g ram for Win e Grapes in Maryland. 20 1 2. http ://marylandgrapcs
. org/ growinu/ FungicideSprayProgramGuidc2012
. pdf. Accessed February 

### 20 15.

9Federal R egister. 1 999. Tetraconazole

- Pesticid c tolerances for emergency exemptions 11 / 99
. Federal R egister: Dec. 6. 1999 (Vol 64. Number 233). http: //pmcp.cce.cornell.edu / prolile s/funQnema t/tcmtb- z iram / tetraconazole/ tetracon exm 1199.html. Accessed February 2015
. FRAC. 2014. f ungic idc Resistance Action Committee Code List: Fungicides Sorted by Mode of Act ion. http ://\\ '' w. frac. info / pub! icati o n / anhang/ 2014% 20FRAC% 20Codc% 20 Li s t. pdf. Accessed February 2015. Grove, G. G. and Ne lson, M. E. 20 1 1. New Fun gicides for Grapevine Po wdery Mildew Mana ge ment , 20 11. Washington State Un iversity Extens io n. http ://wvnv.wmvgu.orn/ files /document s/ 2011 Jul\' 26 Powderv Mildcw.pdf. Accessed February 2015. Khan. M. F. R. a nd H akk, P. 20 1 3
. Efficacy of fungicides for controlling Cercospora leaf spot on sugarbeet. North Dakota State University Extension. http: //wv..rvv . sbrcb.oru/ rcscarch/plant/plant 13 / KhanEfficacyOtFungicidcsCLS.pdf. Accessed February 2015. Khan , M. F. R. and Smi th , L. J. 2005
. Evalu ating fungicides for contro llin g Cercospora l eaf s pot on suga r beet. Crop Protection 24:79-86. http :/ / wwv.-.scicncedircct.com/ s cicnce / a11icle/ pii/ S0261219.f0-WO 167X
. Accessed February 2015. Propri etary Data. 1999-2012; 2000

- 2004; 2008-2012. Rob erson, R. 20 10. Do soybean fungicides pay? Farm Industry News. J uly 16. 20 I 0. http: // farm i ndu s trvnew s .com / fungicide s/do

- soybcan

- fungicidcs-pav
. Accessed February 20 15. Rupe. 

### J. and Sconyers. L. 2008. Soybean Rust. The Plant Health Instructor. American Phytopathology Society. http: // 'vvww.apsnct
. org/ cdcenter / intropp/ lessons / l'unui/ Basicliomvcctes/ Pagcs/ SovbcanRust.aspx
. Accessed February 20 15. Secor, G
. , Riv e ra , V., Bo lton, M., and Khan, M

. 2013
. Sensitiv ity of 

### Cercospora beticola to foliar fungicides in 2013. North Dakota State University Extension. http: //www.sbrcb.org/rcscarch/ plant / plant 13 / SecorSensitivityOfCcrcosporaBeticola.pdf. Accessed February 2015. UC. 20 13. 20 1 3 Fungicide Efficacy and T reatm e nt Timin g for Grapevines. UC Pest Management G ui delines , Unive rs ity of Californ ia Extens ion. http: //wv.w.ipm
. ucdavis.edu/PMG/ r3029021 l l .html. Accessed Feb ruary 2015.

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