### Page 1 of 58 UNITED STATES ENVIRONMENTA L PROTECTION AGENCY

WASHINGTON, D.C. 20460 OFFICE OF CHEMICAL SAFETY AND POLLUTION PREVENTION 

### MEMORANDUM Date : 2/15 /11 SUBJECT: Bromox ynil . P etition for Tolerances in Support of New Use s on Grass and Grain

S orghum . Summary

of Analy tical Chemistry

and Residue Data. PC Code s : 035301, 035302 DP Barcode: D378614 Decision No.: 425581 Registration No. : 264 - 1023 Petition No.: 9F7678 Regulatory Action s : Section 3 Registration Risk A ssessment Type: NA Case No.: 2070 T XR No.: NA CAS No.: 1689 - 84 - 5 MRID No.: NA 40 CFR: 180. 324 FROM: Nancy

Dodd, Chemist Risk Assessment Branch III Health Effects Division (7509P) THROUGH: L eung Cheng, Senior Chemist

Risk Assessment Branch III Health Effects Division (7509P) TO: Joanne Miller/Bethany Benbow, RM#23

Registration Division (7505P) The MRIDs associated with this action (MRIDs 47815001 and 47815002) have been reviewed under D P Number 380770 (Toiya Goodlow, 8/17/10). The residue chemistry summary document is presented here.Bromoxynil Summary of Analytical Chemistry and Residue Data DP#: 378614



### Page 2 of 58 Executive Summary Bromox ynil (3, 5 - dibromo - 4 - hydrox ybenzonitrile) i s a contact herbicide which is registered for application as the octanoic and/ or heptanoic acid esters for control of broadleaf weeds in v arious crops. The octanoic and heptanoic esters are rapidly converted to the phenol (bromoxy nil). Bromox ynil inhibits photosynthetic electron trans port and oxidative phosphorylation in mitochondria . Baye r CropScience has proposed Section 3 registration for annual and perennial grasses grown for seed , conservation reserve program acres (CRP) , and grain sorghum on the HUSKIETM Herbicide label . HUSKIETM Herbicide (EPA Registration No. 264 - 1023) is an emulsifiable concentrate which contains 13.4% bromoxy nil octanoate, 12.9% bromoxy nil heptanoate, 3.3% py rasulfotole, and 70.4% inerts. The formulation contains 1.75 lbs bromoxy nil active ingredient per gall on. In support of the proposed uses on grass and grain sorghum , Bayer CropScience has proposed t olerances under PP#9F7678 for residues of the herbicide bromox ynil (3,5 - dibromo - 4 - hydrox yb enzonitrile) resulting from the a pplication of its oc tanoic and/or h eptanoic acid ester in or on the following raw agricultural commodities: Grass, forage ................................ ................................ .................. 18 ppm Grass, hay ................................ ................................ ........................ 5.0 ppm Sorghum, grain ................................ ................................ ................. 0.2 ppm HED not es that the proposed tolerances are higher than the established tolerances on these commodities. The establ ished tolerances for grass and sorghum commodities are 3.0 ppm for grass, forage ; 3.0 ppm for grass, hay ; 0.5 ppm for sorghum, grain, forage ; 0.05 ppm for sorghum, grain, grain ; and 0.2 ppm for sorghum, grain, stover . The grain of grain sorghum contribute s to aspirated grain fractions; the established tolerance for grain, aspirated fractions is 0.3 ppm. Tolerances are established under 40 CFR §180.324 (a) (1) for residues of the herbicide bromox yn il (3.5 - dibromo - 4 - hydrox ybenzonitrile) resulting from appli cation of its octanoic and/or heptanoic acid ester in or on alfalfa, barley, field and pop corn, flax, garlic, aspirated grain fractions, grass, oat, onion, peppermint, rye, sorghum, spearmint, and wheat commodities at levels ranging from 0.05 ppm to 9.0 ppm. Tolerances are established under 40 CFR §180.324( a) (2) for residues of the herbicide bromoxy nil (3.5 - dibromo - 4 - hydrox yb enzonitrile) and its metabolite 3,5 - dibromo - 4 - hydrox ybenzoic acid (DBHA) resulting from application of its octanoic and/or heptanoi c acid ester in or on cotton commodities at levels ranging from 1.5 to 7.0 ppm and in egg, milk, and the meat, fat, and meat by products of cattle, goat, hog, horse, poultry , and sheep at levels ranging from 0.05 to 3.5 ppm. The nature of the residue in grass and grain sorghum i s adequatel y understood based on acceptable metabolism studies on alfalfa, sweet corn, and transgenic (BXN) cotton using bromox yn il octanoate. The residue of concern in plants other than cotton is bromoxy nil. The residues of concern in cotton are bromox ynil and the metabolite 3,5 - dibromo - 4 - hydrox ybenzoic acid (DBHA).Bromoxynil Summary of Analytical Chemistry and Residue Data DP#: 378614



### Page 3 of 58 The nature of the residue in livestock is adequ ately understood for bromoxy

nil, based on acceptable ruminant and poultry metabolism studies using bromox ynil octanoate . As determined by an AD HOC meeting of the Residues of Concern Knowledgebase Subcommittee (ROCKS) on 2/10/11, b romox yn il is the residue of concern in livestock commodities for the tolerance expression while bromoxynil and DBHA are the residues of concern in livestock commodities for the risk assessment. Adequate anal ytical methodology is available for tolerance enforcement for bromoxy nil per se in grass and grain sorghum commodities. Method Iin PAM , Vol. II, is a gas liquid chromatography/microcoulom etric detection ( GLC/MCD ) method that has undergone a successful EPA method validation on wheat grain. Method Ia is the same method except that it uses gas chromatography/electron capture detection ( GC/ECD ) for determination of methylated bromox yn il. Ade quate anal ytical methodology is available for tolerance enforcement for bromoxy nil per se in livestock commodities. M ethod A is a GC/MCD or GC/ECD method for the anal ys is of bromox yn il per se residues in livestock tissues and is essentially the same as Me thod I. Method B is a GC/ECD method that is also similar to Method I , with modifications to the cleanup procedures . Multiresidue methods data for bromox ynil butyr ate and bromox ynil octanoate have been submitted. Recovery

of bromoxy

nil octanoate and bro moxy nil buty rate using FDA Multiresidue Method 303: Method II for Nonfattty Foods (Mills, Onley, Gaither Method) is variable. B romox ynil was not detected through Florisil elution. The data have been forwarded to FDA and included in the PESTDATA database. Adequate storage stability data are available to support the storage durations and conditions of samples from the submitted crop field trial studies on grain sorghum and grass. Storage stability data are available that demonstrate that bromox yn il resi dues are stable in the f orage, grain , and stover of grain sorghum and in the forage, hay , and seed of grass stored frozen at - 10°C for 12 months . Based on the cattle and poultry feeding studies and the calculated livestock dietary burdens, the established livestock tolerances are adequate except for milk . The established livestock tolerances are 1 ppm on the fat of cattle, goat, hog, horse, and sheep; 3.5 ppm on meat by products of cattle, goat, hog, horse, and sheep; 0.5 ppm on meat of cattle, goat, hog, horse, and sheep; 0.05 ppm on poultry fat; 0.3 ppm on poultry

meat by products; 0.05 ppm on poultry meat; 0.05 ppm on egg; and 0.1 ppm on milk. A higher tolerance of 0.4 ppm must be proposed for milk. The submitted residue data for grass are adequate to f ulfill data requirements. The number and locations of the crop field trials are in accordance with OPPTS Guideline 860.1500, and the field trials reflect the proposed use pattern. The residue data for grass were entered into the Agency ’s tolerance spread sheet as specified by the Guidance for Setting Pesticide Tolerances Based on Field Trial Data SOP to determine an appropriate tolerance level; see Appendix I . Using the tolerance calculator, the residue data support the proposed tolerance s of 18 ppm on gr ass forage and 5.0 ppm on grass hay .Bromoxynil Summary of Analytical Chemistry and Residue Data DP#: 378614



### Page 4 of 58 The submitted residue data for grain sorghum are adequate to fulfill data requirements. The number and locations of crop field trials are in accordance with OPPTS Guideline 860.1500, and the field trials reflect the proposed use pattern. The residue data for grain sorghum were entered into the Agency ’s tolerance spreadsheet as specified by the Guidance for Setting Pesticide Tolerances Based on Field Trial Data SOP to determine an appropriate tolerance level; see App endix I . Using the tolerance calculator, the residue data support the proposed tolerance of 0.2 ppm on the grain of grain sorghum and also support the established tolerance of 0.2 ppm on the stover of grain sorghum. Based on the tolerance calculator, HED is recommending that the proposed tolerance of 0.5 ppm on the forage of grain sorghum be increased to 0.8 ppm. Adequate processing studies on corn, sorghum, and wheat are available to support a tolerance on aspirated grain fractions (grain dust). The st udies all indicate that residues concentrate in aspirated grain fractions. Because the tolerance on the grain of grain sorghum is being increased from 0.05 ppm to 0.2 ppm, higher residues may occur in aspirated grain fractions; therefore, the petitioner must submit a revised Section F to propose a higher tolerance of 1.2 ppm for grain, aspirated grain fractions . There are no processed commodities associated with use on grass. The processed commodity associated with use on grain sorghum is flour; however, residue data are not needed on sorghum flour at this time since it is used exclusively in the United States as a component for dry

wall, and not as either a human food or feedstuff. Analy tical reference standards are available for bromoxy nil, bromoxy

nil heptanoate, and bromox yn il octanoate. No anal ytical reference standard for the cotton metabolite 3,5 - dibromo 4 - hydroxy

benzoic acid (DBHA) is available . In the confined rotational crop study in which s oil was treated with 14 

### C - bromox yn il octanoate at a rate of 0.41 lb ai, low level residues were found in the rotational crops spinach, beets, and wheat. The residues consisted of multiple, polar components. The field rotational crop studies, together with the confined rotational crop data, are adequate to demonstrate that detectable bromoxy nil residues would not be expected in crops rotated at 30 day s (or more) following application of bromoxy nil octanoate to primary

crops on the Huskie TM 

### Herbicide label . Based on the available bromox yn il rotational crop d ata, a 30 - day plantback interval (PBI) is adequate for bromox ynil for all rotational crops planted after application of Huskie TM 

### Herbicide . The petitioner must submit a revised Section F to propose tolerances which reflect the recommended tolerance levels and correct commodity definitions as specified in Table 17. Because the tolerance on the grain of grain sorghum is being increased from 0.05 ppm to 0.2 ppm, higher residues may occur in aspirated grain fractions. HED has determined that a higher tolerance of 1.2 ppm is needed for grain, aspirated grain fractions . Based on input of the residue data into the tolerance spreadsheet ( Guidance for Setting Pesticide Tolerances Based on Field Trial Data ), HED is recommending a tolerance of 0.8 ppm for sorghum, grain, forage in lieu of the established tolerance of 0.5 ppm .Bromoxynil Summary of Analytical Chemistry and Residue Data DP#: 378614



### Page 5 of 58 Based on calculated residues in dairy cattle for the tolerance assessment, the established tolerance on milk must be increased from 0.1 ppm to 0.4 ppm. Other livestock tolerances remain unch anged. Regulatory Recommendations and Residue Chemistry Deficiencies HED has examined the residue chemistry database for bromox ynil. Pending submission of a revised Section B (see requirements under Directions for Use) and a revise d Section F (see requirements under Proposed Tolerances) , there are no residue chemistry issues that would preclude granting permanent tolerances on grass and grain sorghum commodities and registration for the requested use s on annual and perennial grasses grown for seed, conservation reserve program acres (CRP), and grain sorghum. Tolerance levels for residues of bromox ynil are recommended as follow: Grass, forage ................................ ................................ .................. 18 ppm Grass, hay ................................ ................................ ........................ 5.0 ppm Grain, aspirated grain fractions ................................ ........................ 1.2 ppm Milk ................................ ................................ ................................ . 0.4 ppm Sorghum , grain, grain ................................ ................................ ...... 0.2 ppm Sorghum, grain, forage ................................ ................................ .... 0.8 ppm Note: The established tolerance o f 0.2 ppm on sorghum, grain, stover is to remain unchanged. A human health risk assessment is forthcoming. Note s to PM: T he tolerance expression for bromoxynil in 40 CFR § 180.324(a) (1) should be revised according to HED’s Interim Guidance on Tolerance Expressions (5/27/09, S. Knizner) to state:
“ Tolerances are established for residues of bromoxynil, including its metabolites and degradates, in or on the commoditie s in the table below. Compliance with the tolerance levels specified below is to be determined by measuring only bromoxynil (3,5 - dibromo - 4 - hydroxybenzonitrile) resulting from application of its octanoic and/or heptanoic acid ester. T he tolerance expressi on for bromoxynil in 40 CFR § 180.324(a)(2) should be revised according to HED’s Interim Guidance on Tolerance Expressions (5/27/09, S. Knizner) to state:
“ Tolerances are established for residues of bromoxynil, including its metabolites and degradates, in or on the commodities in the table below. Compliance with the tolerance levels specified below is to be determined by measuring only bromoxynil (3, 5 - dibromo - 4 - hydroxybenzonitrile) and its metabolite 3,5 - dibromo - 4 - hydroxybenzoic acid (DBHA) resulting from application of its octanoic and/or heptanoic acid ester.Bromoxynil Summary of Analytical Chemistry and Residue Data DP#: 378614



### Page 6 of 58 All livestock commodities should be moved from 40 CFR § 180.324(a)(2) to 40 CFR § 180.324(a)(1), leaving only cotton, gin byproducts ; cotton, hulls ; and cotton, undelinted seed in 40 CFR § 180.324(a)(2 ). Although not required to support the current registration action, an analytical reference standard for the cotton metabolite 3,5 - dibromo - 4 - hydroxybenzoic acid (DBHA) must be submitted to the repository (OPPTS 860.1650). OPPTS 860.1200 Directions fo r Use A revised Section B/label must be submitted with the following revisions: a) The grass section of the HUSKIE TM 

### Herbicide label should have an “APPLI CATION METHODS” section which states the type(s) of application (eg. foliar spray, broadcast spray , etc.), the method(s) of application (i.e., ground, air, or both), and the minimum gallons spray per acre for each method. b) The sorghum section should either state that aerial applications are not to be made or state the minimum spray

volume for aerial applications. c) The label contains rotational crop plantback intervals for some crops but not all crops. A 30 - day rotational crop restriction is adequate for bromox yn il. The petitioner must consider rotational crop plantback requirements for all active ingredients on the label and then i ndicate a plantback interval for all crops which are not primary (treated) crops on the label or are not already listed in the Crop Rotation Guidelines section of the label. 860.15 50 Proposed Tolerances Because the tolerance on the grain of grain sorghum is being increased from 0.05 ppm to 0.2 ppm, higher residues may occur in aspirated grain fractions. HED has determined that a higher tolerance of 1.2 ppm is needed for grain, aspirated grain fractions . Based on i nput of the residue data into the tolerance spreadsheet ( Guidance for Setting Pesticide Tolerances Based on Field Trial Data ), HED is recommending a tolerance of 0.8 ppm for sorghum, grain, forage in lieu of the established tolerance of 0.5 ppm . Based on calculated residues in dairy cattle for the tolerance assessment, the established tolerance on milk must be increased from 0.1 ppm to 0.4 ppm. Other livestock tolerance levels remain unchanged. The petitioner must submit a revised Section F to propose to lerances which reflect the recommended tolerance levels and correct commodity definitions as specified in Table 17 . Background The chemical structure and nomenclature of bromoxy nil is presented in Table 1. The phy sicochemical properties of the technical grade of bromox yn il are presented in Table 2. In addition, the chemical names and structures of the two esters and the DBHA metabolite referenced herein are presented in Appendix I I .Bromoxynil Summary of Analytical Chemistry and Residue Data DP#: 378614



### Page 7 of 58 Table 1. Test Compound Nomenclature. Chemical Structure

Em piri cal Formula C 7 H 3 Br2NO Common N ame bromoxynil or bromoxynil phenol Com pany Experimental Name AE F025943 IUPAC Name 3,5 - dibromo - 4 - hydroxybenzonitrile CAS Name 3,5 - dibromo - 4 - hydroxybenzonitrile CAS Registry Number 1689 - 84 - 5 (phenol) 1689 - 99 - 2 (octanoate ) 56634 - 95 - 8 (heptanoate) End - use Product/EP Huskie TM Herbicide Chemical C lass Benzonitrile H erbicide Known impurities of concern None

T able 2. Physicochemical Properties of Brom oxynil (Brom oxynil Phenol) Parameter Value Reference (MRID) Molecul ar Weight 276.9 4781500 1 Melting point/range 190 .5 °C 4781500 1 pH @ ambient 3.68 47815001 Density 2.31 g/cm3 at 2 0 ° C 47815001 Water solubility 0.090 g/L at 25oC 4781500 1 Solvent solubility (20oC) Hept ane Xylene Methanol Octanol Acetone Ethyl acetate Acetonitrile 0.15 g/L 8.8 g/L 80.5 g/L 46.7 g/L 186 g/L 97.7 g/L 51.1 g/L 47815001

Vapor pressure 1.4 Pa at 20  C 47815001 Dissociation constant, pKa 3.86 47815001 Octanol/water partition coefficient, Log(KOW) 2.90 (K ow = 794) 4781500 1 UV/visible ab sorption spectrum Primary λmax = 221.2 Primary λmax = 286.8 47815001 

### 860.1200 Directions for Use Baye r CropScience has proposed Section 3 registration for annual and perennial grasses grown for seed , conservation reserve program acres (CRP) , and grain s orghum on the HUSKIETM Herbicide label . HUSKIETM Herbicide (EPA Registration No. 264 - 1023) controls broadleafBromoxynil Summary of Analytical Chemistry and Residue Data DP#: 378614



### Page 8 of 58 weeds and mannagrass in grasses and broadleaf weeds in grain sorghum. HUSKIETM Herbicide is an emulsifiable concentrate which contains 13.4% bromox yn il octanoate, 12.9% bromoxy nil heptanoate, 3.3% p yr asulfotole, and 70.4% inerts. The formulation contains 1.75 lbs bromoxy nil per gallon. Table 3. Summary of Direction s for Use of Brom oxynil . Applic. Timing, Ty pe, and Equipment Form

ulation [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 1,2,3 Grass (Grasses Grown for Seed and Conservation Reserve ProgramAcres) ( Perennial Ryegrass, Annual Ryegrass, Tall F escue, Fine Fescue, Kentucky B luegrass , O rchardgrass , and Timothy)Bromoxynil Summary of Analytical Chemistry and Residue Data DP#: 378614



### Page 9 of 58 Table 3. Summary of Direction s for Use of Brom oxynil . Applic. Timing, Ty pe, and Equipment Form

ulation [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 1,2,3 Pre - emergence and/or post emergence HUSKIETM

Herbicide (EPA Reg. No. 264 - 1023) 13.5 - 15

oz/A (0.18 - 0.205 lb ai/A) 2 30 oz (0.41 lb ai/A) Forage: 7

Hay : 30 Use in annual and

perennial grasses grown for seed and conservation reserve program acres (CRP) . Apply from pre emergence to established perennial ryegrass, annual ryegrass, tall fescue, fine fescue, Kentucky bluegrass and orchardgrass. Apply to established timothy. Observe an interval of at least 30 days between appl i cations. HUSKIETM Herbicide may be tank mixed with herbicides, insecticides, fungicides, and spray additives.* The restricted entry interval is 12 hours. Sorghum , GrainBromoxynil Summary of Analytical Chemistry and Residue Data DP#: 378614



### Page 10 of 58 Table 3. Summary of Direction s for Use of Brom oxynil . Applic. Timing, Ty pe, and Equipment Form

ulation [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 1,2,3 Postemergence, Foliar spray, Ground equipment HUSKIETM

Herbicide (EPA Reg. No. 264 - 102 3) 12.8 - 16

oz/A ( 0.18 - 0.22 lb ai/A) 2 32 oz (0.44 lb ai/A) Forage: 7

Grain: 60 Stover: 60 Apply to sorghum

between the 3 leaf stage of growth up to 12 inches. Apply in minimum of 10 - 15 gallons of water per acre, as needed to obtain thorough spray coverage . Do not apply through any type of irrigation system. Observe an interval of at least 11 days between applications. HUSKIETM Herbicide may be tank mixed with herbicides and insecticides.** Do not apply HUSKIETM Herbicide in a tank mix with Lorsban as an unacceptable crop response may occur. One pound of ammonium sulfate per acre may be added to optimize herbicidal activity. The restricted entry interval is 12 hours. 1 Crop Rotation Plantback Intervals: 1 month: wheat, barley, oats, rye, and triticale 4 months: alfalfa, millet, grain sorghum, and soybeans 9 months: canola, canaryseed, chickpeas, corn, dry beans, flax, field peas, green beans, green peas, lentils (except in MN, MT, ND, and SD), mustards, potatoes, safflower, sunflowers, and sugarbeets 18 months: lentils in MN, MT, ND and SD 2 Grass: For weed control, HUSKIETM Herbicide may be tank mixed with Puma®, Nortron, Rely, 2.4 - D ester/amine, AimTM, Bronate AdvancedTM, Buctril®, Curtail M/Curtail®, Dicamba, Goal, Glean, MCPA ester/MCPA amine, Sencor®, Starane®/Starane NXT/Starane Ultra, or WideMatchTM.Bromoxynil Summary of Analytical Chemistry and Residue Data DP#: 378614



### Page 11 of 58 For insect co ntrol, HUSKIETM Herbicide may be tank mixed with Baythroid®XL, Capture, Lorsban®, Mustang MaxTM, or Warrior® Insecticides. For disease control, HUSKIETM Herbicide may be tank mixed with fungicides such as Absolute, Tilt®, Quadris®, QuiltTM, or Bravo. Some tank mix options require the use of a non - ionic surfactant (NIS). Use the amount of the NIS recommended on the tank mix partner label or at a concentration of 0.25 - 0.5% v/v (1 - 2 qt per 100 gallons of spray solution) . At least 80% of the surfactant product must be active non - ionic surfactant. 3 Grain Sorghum: For grass control, HUSKIETM Herbicide may be tank mixed with 0.25 - 1.0 lb atrazine per acre. For weed control, HUSKIETM Herbicide plus atrazine may be tank mixed with phenoxy broadleaf herbic i des such as 2,4 - D or dicamba. For insect control, HUSKIETM Herbicide may be tank mix ed with Baythroid®XL An unacceptable crop response may occur if HuskieTM Herbicide is applied to acreage that has been previously treated with mesotrione. Sensitivity of sweet sorghum (sorgo), sudangrass, sorghum - sudangrass hybrids, or dual -purpose sorghum varieties to HUSKIETM Herbicide is not known and the use of HUSKIETM Herbicide on these sorghum ty pes is not recommended. 

### Conclusions A revised Section B/label must be submitted with the following revisions: a) The grass section of the HUSKIE TM 

### Her bicide label should have an “APPLI CATION METHODS” section which states the type(s) of application (eg. foliar spray, broadcast spray, etc.), the method(s) of application (i.e., ground, air, or both), and the minimum gallons spray per acre for each method. b) The sorghum section should either state that aerial applications are not to be made or state the minimum spray

volume for aerial applications. c) The label contains rotational crop plantback intervals for some crops but not all crops. A 30 - day rotational crop restriction is adequate for bromoxy nil. The petitioner must consider rotational crop plantback requirements for all active ingredients on the label and then indicate a plantback interval for all crops which are not primary (treated) crops on the label or are not already listed in the Crop Rotation Guidelines section of the label.Bromoxynil Summary of Analytical Chemistry and Residue Data DP#: 378614



### Page 12 of 58 860.1300 Nature of the Residue - Plants Madden, B., 6/24/98, DP Number 246944, Bromoxynil (Case #2070: PC Codes 035301 and 035302): Revised Human Health Risk Assess ment for Bromoxynil Irene, S., 4/25/97, DP Number 000000, 035301.001, PP#3F04233. New Tolerances for Bromoxynil on Cotton Commodities. Changes from HED’s April 8, 1997 Risk Assessment. Griffin, R., Boyle, K., Fort, F., Hansen, L., Kramer, G., and Robbi ns, S., 4/8/97, D P Number 231906 , PP#3F04233. Extension of Conditional Registration for the Use of Bromoxynil on Transgenic Cotton. Kramer, G.F., 9 /1 7 /93 , DP Number 189368 , PP# 3G04197 

### . Bromoxynil octanoate and heptanoate in or on transgenic Bromotol co tton. Evaluation of residue and analytical data for an EUP and temporary tolerances . 

### No new plant metabolism studies were submitted with this petition. A cceptable metabolism studies are available on alfalfa, sweet corn, and transgenic (BXN) cotton using bromox ynil octanoate. The nature of the residue in alfalfa , sweet corn, and cotton following application of 14 

### C - bromox yn il octanoate is adequatel y understood. The metabolic pathway involves hydrol ys is of the ester, oxidation of the nitrile group to the acid via the amide, and conjugation; debromination occurs in a parallel pathway . Based on these studies, the residue of concern in plants other than cotton is the major metabolite, bromox yn il. Because transgenic cotton metabolizes bromoxy

nil primarily to 3,5 - dibromo - 4 - hydrox ybenzoic acid [78.6% of the total radioactive residues (TRR)] , the residues of concern in cotton are bromoxy nil and its metabolite 3,5 - dibromo - 4 - hydrox yb enzoic acid (DBHA). The residues of concern in cotton were reassessed in an AD HO C meeting of the Residues of Concern Knowledgebase Subcommittee (ROCKS) on 2/10/11 . The Committee confirmed that DBHA should be included in the tolerance expression for cotton since it is a major residue in cotton ( 78.6% of the TRR) and is an indicator of misuse. Based on a study in cotton, the translocation of bromox yn il octanoate is extremely minimal. Bromox ynil octanoate ( 14 

### C - labelled) was applied to a single leaf or boll and harvest ed after 7 day s ( from leaves) or 47 day s ( from bolls). A very smal l amount ( 0.15% or less of the total radioactive residue [ TRR]) was translocated to adjacent leaves. No residues were found in cottonseed. Conclusions The nature of the residue in grass and grain sorghum i s adequatel y understood based on acceptable me tabolism studies on alfalfa, sweet corn, and transgenic (BXN) cotton using bromox yn il octanoate. The residue of concern in plants other than cotton is bromoxy nil. The residues of concern in cotton are bromox ynil and its metabolite 3,5 - dibromo - 4 - hydrox ybenzoic acid (DBHA).Bromoxynil Summary of Analytical Chemistry and Residue Data DP#: 378614



### Page 13 of 58 860.1300 Nature of the Residue
– Livestock Madden, B., 6/24/98, DP Number 246944, Bromoxynil (Case #2070: PC Codes 035301 and 035302): Revised Human Health Risk Assessment for Bromoxynil Swartz, C., 3/19/98, DP Number 244250, Bromoxyn il Octanoate. List B Reregistration Case No. 2070/Chemical ID No. 035302. Issues Discussed by HED’s ChemSAC on 2/25/98. Irene, S., 4/25/97, DP Number 000000, 035301.001, PP#3F04233. New Tolerances for Bromoxynil on Cotton Commodities. Changes from HED ’s April 8, 1997 Risk Assessment. Griffin, R., Boyle, K., Fort, F., Hansen, L., Kramer, G., and Robbins, S., 4/8/97, DP Number 231906 , PP#3F04233. Extension of Conditional Registration for the Use of Bromoxynil on Transgenic Cotton. Funk, S., 9/2/92, DP Number 179470, Registration of Bromoxynil Octanoate . GLN 171 - 4(b): Nature of the Residue in Ruminants and Poultry. 

### No new livestock metabolism studies were submitted with this petition. Ruminant and poultry metabolism studies are available. The nature of the residue in livestock is adequ atel y understood for bromox ynil, based on acceptable ruminant and poultry metabolism studies using bromox ynil octanoate . When 14 

### C - bromox yn il octanoate was administered to lactating goats, 90% of the TRR was recovered as bromox ynil per se . The parent compound was found onl y in milk (1.7% of the TRR). DBHA was found only in liver (4% of the TRR) ; it was found after base hydrol ys is of the non - extracted liver residue . When 14 

### C - bromox yn il octanoate was administered to layi ng hens, 73 - 100% of the TRR was recovered as bromox ynil per se . The parent compound was found onl y in eggs (4 - 6% of the TRR). Polar unknowns accounted for 3% of the TRR in liver. Residues of concern in livestock were reassessed in an AD HOC meeting of the Residues of Concern Knowledgebase Subcommittee (ROCKS) on 2/10/11 . The Committee determined that the residues of concern in livestock are bromox yn il for the tolerance expression and bromoxy nil and DBHA for the risk assessment. The Committee determ ined that DBHA does not need to be included in the tolerance expression for livestock commodities for the reasons listed below. These conclusions apply

to existing and proposed uses only . 1) When livestock are fed bromoxy nil octanoate, DBHA is a minor metabo lite in livestock, present o nl y in liver (4% of the TRR). 2) Cotton is the only

registered/proposed transgenic crop and cotton commodities are not driving the dietary

burden. 3) DBHA is less toxic than bromox yn il as indicated in the following tests: a Salmonell a ty phimurium Reverse Mutation Assay (Ames Test) , a developmental toxicology study (rat), and a subchronic toxicity study (rat). There is no toxicity concern (cancer/noncancer) at anticipated exposure levels. The DEREK indicated a poly halogenated cancer alert but since DBHA is an acid, the concern is eliminated. 4) The effect that conversion of the nitrile group to a carbox ylgroup has on developmental toxicity and liver toxicity is likely to carry over to carcinogenicity

as well. The carboxyl group will be ionized at phy siological pH and this will result in rapid excretion of DBHA and retard cellular uptake and migration of DBHA through intracellular membranes to interact with receptors associated with carcinogenicity . There is therefore little concernBromoxynil Summary of Analytical Chemistry and Residue Data DP#: 378614



### Page 14 of 58 for carcinogenicity for DBHA. C onclusions The nature of the residue in livestock is adequ ately understood, based on acceptable ruminant and poultry

metabolism studies using bromox ynil octanoate . B romox ynil is the residue of concern in livestock commodities for the tolerance expression while bromox yn il and DBHA are the residues of concern in livestock commodities for the risk assessment. 860.1340 Residue Analytical Methods Madden, B., 6/24/98, DP Number 246944, Bromoxynil (Case #2070: PC Codes 035301 and 035302): Revised Human Health Risk Assessment for Bromoxynil Swartz, C., 3/2/98, DP Number 243651 , Bromoxynil Octanoate. List B Reregistration Case No. 2070/Chemical ID No. 03530, Rhône
-Poulenc Submission of Additional Field Trials Conducted at Reduced R ates on Transgenic BXN Cotton. Kramer, G.F., 3/11/97, DP Number 232957, ID# 000264 - 00540. PP# 3F04233. Bromoxynil Octanoate and Heptanoate in or on Transgenic BXN Cotton. Amendment of 12/18/96. Submission of Residue Data. 

### Enforcement Methods Plants : Adequate anal ytical methodology is available for tolerance enforcement for bromoxy nil per se in plants. Method Iin PAM , Vol. II, is a gas liquid chromatography/microcoulometric d etection ( GL C/MCD ) method that has undergone a successful EPA method valid ation on wheat grain. This method involves alkaline hydroly sis in methanolic potassium hydroxide to convert residues to bromoxy

nil, cleanup by

liquid - liquid partitioning, methylation using diazomethane, further cleanup on a Florisil column, and determination by GLC/MCD. Method Ia is the same method except that it uses gas chromatography/ electron capture detection ( GC/ECD ) for determination of methylated bromoxy

nil. Livestock : Adequate anal ytical methodology is available for tolerance enforcement for bro moxy nil per se in livestock commodities. M ethod A is a GC/MCD or GC/ECD method for the anal ys is of bromox yn il per se residues in livestock tissues and is essentially the same as Method I. Method B is a GC/ECD method that is also similar to Method I , with modifications to the cleanup procedures . Data Collection Methods Goodlow , T., 8/17/10, DP Number 380770, Bromoxynil: Review of HUSKIE HERBICIDE

– Magnitude of the Residue in/on Sorghum and Grass 

### Samples of sorghum forage, grain, and stover and of grass forage and hay were anal yz ed for residues of bromox ynil using Bayer Method No. BR - 001 - P05 - 01. The method hydrol ys es the esters bromox ynil heptanoate and bromox ynil octanoate to bromox yn il phenol. Bromoxy nilBromoxynil Summary of Analytical Chemistry and Residue Data DP#: 378614



### Page 15 of 58 standards were corrected for purity and prepare d in parent compound molar equivalents during initial standard solution preparation, so all residues are reported in parent compound equivalents. This high performance liquid chromatography/tandem mass spectroscop y ( HPL C - MS/MS ) anal ytical method quantifie s residues of bromox yn il from a single sample using isotope labeled internal standards with a multi - level calibration curve. Briefl y, a 2.0 - or 0.5 - g aliquot of sorghum matrices was weighed into a 60 - mLvial and a methanol solution of potassium hydroxide ( 5% w/v) was added. The sample was heated to 60°C for at least 60 minutes. The samples were cooled and an isotopic internal standard was added to the sample extract. A 5 - mLaliquot was acidified and purified b y C18 solid phase extraction (C - 18 SPE). The solvent was removed from the sample and the residue was reconstituted for analysis b y HP LC - MS/MS. HPL C separation was performed with an Xterra MSC18 HPL C column, 3.56 um, 50 x 2.1 mm column using 9:1 water/acetonitrile (ACN) with 0.1% acetic acid (HOAc) and A CN with 0.1% formic acid as the mobile phase on a Thermo Finnigan Surveyor HPLC. The HPL C was interfaced to a ThermoFinnigan Quantum Ultra tandem mass spectrometer for analy te detection. The lowe st level of method validation was 0.01 ppm in sorghum forage , grain, and stover and in grass forage and hay . T he limits of detection ( LOD s ) were 0 .00246 ppm, 0.00379 ppm, and 0.00315 ppm for bromoxy nil in sorghum forage, grain, and stover, respectively . The LOD s were 0. 00531 ppm and 0.00287 ppm for bromox yni l in grass forage and grass hay , respectivel y. Conclusions Plants: Adequate anal ytical methodology is available for tolerance enforcement for bromoxy nil per se in grass and grain sorghum commodities. Method Iin PAM , Vol. II, is a gas liquid chromatography

/microcoulometric d etection ( GLC/MCD ) method that has undergone a successful EPA method validation on wheat grain. Method Ia is the same method except that it uses gas chromatography/electron capture detection ( GC/ECD ) for determination of methylated brom oxy nil. The data collection method ( Baye r Method No. BR - 001 - P05 - 01 ) is acceptable for data collection based on concurrent recoveries . Bromoxy nil residues in sorghum forage, grain, and stover and in grass forage and hay were quantitated b y high performanc e l iquid chromatography /tandem mass spectroscop y ( HP LC - MS/MS ) using stable isotopically labeled bromoxy

nil as an internal standard. The lowest level of method validation ( LLMV ) for bromoxy nil was 0.01 ppm in all matrices. Livestock: Adequate anal ytical methodology is available for tolerance enforcement for bromoxy nil per se in livestock commodities. M ethod A is a GC/MCD or GC/ECD method for the anal ys is of bromox yn il per se residues in livestock tissues and is essentially the same as Method I. Method B is a GC/ECD method that is also similar to Method I , with modifications to the cleanup procedures .Bromoxynil Summary of Analytical Chemistry and Residue Data DP#: 378614



### Page 16 of 58 860.1360 Multiresidue Methods Griffith, F.D., 11/4/92 , DP Number 179705, PP#0F3848 - B ROMOXYNIL (B UCTRIL ®) ON RICE G RAIN AND STRAW

. REVIEW OF THE M

AY 26 AND A UGUST 7, 1992 A MEND MENTS. Madden, B., 6/24/98, DP Number 246944, Bromoxynil (Case #2070: PC Codes 035301 and 035302): Revised Human Health Risk Assessment for Bromoxynil 

### The FDA PESTDATA database ( P esticide Anal yt ical Manual , Vol. I, Appendix I , 3 rd 

### edition, 1994, revised October 1999 ) indicates that recovery of bromoxy

nil octanoate and bromoxy nil buty rate using FDA Multiresidue Method 303: Method II for Nonfatty Foods (Mills, Onley, Gaither Method) is variable. B romox ynil was not detected throu gh F lorisil elution. No data were reported for the methyl ether of bromoxy nil. Conclusions Multiresidue methods data for bromox ynil butyr ate and bromox ynil octanoate have been submitted. Recovery

of bromoxy

nil octanoate and bromoxy nil buty rate using F DA Multiresidue Method 303: Method II for Nonfatty Foods (Mills, Onley, Gaither Method) is variable. B romox ynil was not detected through Florisil elution. The data have been forwarded to FDA and included in the PESTDATA database. 860.1380 Storage Stab ility Goodlow , T., 8/17/10, DP Number 380770, Bromoxynil: Review of HUSKIE HERBICIDE

– Magnitude of the Residue in/on Sorghum and Grass 

### Grain sorghum: The maximum frozen storage interval from sampling to extraction of bromox yn il was 351 days for forage, 275 day s for grain, and 273 day s for stover. All samples were anal yz ed within 3 day s of extraction. Storage stability data are available that demonstrate bromox yn il residues are stable in sorghum forage, grain and stover stored frozen at - 10°C for 12 mo nths ( D P Numbers 204403 and 199274, S. Knizner , 7/14/94 ; MRID 43108801). Grass: The maximum frozen storage interval from sampling to extraction prior to anal ys is of bromox yn il was 350 days for grass forage and 313 day s for grass hay . All samples were anal yz ed within 2 day s of extraction. Storage stability data are available that demonstrate bromox yn il residues are stable in grass forage, hay, and seed stored frozen at - 10°C for 12 months ( D P Numbers 204403 and 199274, S. Knizner, 7/14/94 ; MRID 43108801 ). These data adequatel y support the storage durations and conditions of samples from the submitted crop field trial study . The storage conditi ons and durations of samples fro m the crop field trials are summarized in Table 4.Bromoxynil Summary of Analytical Chemistry and Residue Data DP#: 378614



### Page 17 of 58 T able 4 . Summary of Sto rage Conditions and Durations of Samples from Crop Field Trial Studies on Brom oxynil Matrix Maximum Storage

Tem perature 1 (°C) Actual Storage

Duration2 Interval of Demonstrated Storage Stability 3

Grass Grass forage <0 187

– 350 days (6.0 to 11.3 months) Residues are stable in/on grass forage and hay and variety of other crops (i.e. wheat, barley, sorghum, and corn) stored frozen at - 10°C for up to 12 months. Grass hay <0 143 to 313 days (4.6 to 10.1 months) Sorghum , Grain Sorghum Forage <0 179 to 351 days (5.8 to 11.3 months) Residues are stable in/on sorghum forage, grain and stover and a variety of other crops (i.e. w heat, barley, grass, and corn) stored frozen at - 10°C for up to 12 months (MRID 43108801). Sorghum Grain <0 166 to 275 days (5.4 to 8.9 months) Sorghum Stover <0 166 to 273 days (5.4 to 8.8 months) 1 Sam ples were stored at the field site and analytical laboratory at <0°C. The storage temperature at BRP between 5/16/2008 and 2/5/2009 was not recorded, however, the freezers were w orking properly and all samples remained frozen. 2 Storage duration is from date of sampling to date of extraction. Grass forage and hay samples were analyzed within 0 to 2 days of extraction. Sorghum forage, grain and stover s am ples were analyzed within 1 to 3 days of extraction. 3 Refer to DP Numbers 199274/204403, S. Knizner, 7/14/94; M RID 43108801 . 

### Conclusions Adequate storage stability data are available to support the storage durations and conditions of samples from the submitted crop field trial studies on grain sorghum and grass. Storage stability data are available that demonstrate that bromox yn il residues are stable in the f orage, grain , and stover of grain sorghum and in the forage, hay , and seed of grass stored frozen at - 10°C for 12 months . 860.1400 Water, Fish, and Irrigated Crops This guideline topic is not relevant to the proposed use s . 860.1460 Food Handling This guideline topic is not relevant to the proposed use s .Bromoxynil Summary of Analytical Chemistry and Residue Data DP#: 378614



### Page 18 of 58 860.1480 Meat, Milk, Poultry, and Eggs Kramer, G.F., 3/11/97, DP Numb er 232957, Bromoxynil Octanoate and Heptanoate in or on Transgenic BXN Cotton. Amendment of 12/18/96. Submission of Residue Data. Swartz, C., 1/20/98, DP Number 239914, Bromoxynil Octanoate. List B Reregistration Case No. 2070/Chemical ID No. 035302 . Revised Anticipated Residues Assessment Based on Revised Labeling Submitted in Conjunction with PP#3F4233 (9/24/97). 

### Livestock feed items associated with grass are forage, hay , and silage ; l ivestock feed items associated with grain so rghum are grain, forage/silage, stover , and aspirated grain fractions ( Table 1 Feedstuffs , June 2008). Cattle and poultry

feeding studies were previously reviewed (DP Number 232957, G. F. Kramer, 3/11/97). Results of the feeding studies with both feeding levels and resi dues reported as bromox yn il per se (DP Number 239914, C. Swartz, 1/20/98 ) are reported below:

Table 5 . Average Brom oxynil Octanoate Residues in Cattle Tissues Feeding Level (ppm) Average Brom oxynil Residues (ppm) Milk Liver Kidney Fat Muscle 4.2 0.05 1.97 2.26 0.68 0.37 12.6 0.14 4.04 5.89 2.11 0.86 42.0 0.48 10.65 16.26 4.75 2.59

Table 6 . Average Brom oxynil Octanoate Residues in Poultry Tissues Feeding Level (ppm) Average Brom oxynil Residues (ppm) Liver Muscle Skin & Fat 0.07 0.063 Not anal yzed Not analyzed 0.21 0.083 <0.05 <0.05 0.70 0.21 0.05 0.0 8 1 Residues in eggs were not detectable ( <0.05 p pm) at the highest feeding level ( 0.70 ppm). 

### Residues in milk from the low dose group were nondetectable (<0.05 ppm) prior to day 18 and were 0.0 5 ppm thereafter. Residues in milk from the medium dose group plateaued on day 14 at an average of 0.14 ppm. Residues in milk from the high dose group plateaued after 21 day s at an average of 0.48 ppm The maximum reasonably balanced diet ary burdens (MRB DB) f or bromoxy

nil residues in livestock commodities can be calculated as follows . Table 7a applies to the tolerance assessment; Table 7b applies to the risk assessment. Table 7a. MaximumReasonably Balanced Dietary Burdens for Brom oxynil in Livestock D iets a % Diet b Dietary Contributions (ppm) 

### Feedstuff Type Tolerance, ppm % Dry

Matter Beef Dairy Poultry Swine Beef D ai ry Poultry Swine Grass forage R 18 25 Nuc 45 Nu Nu -- 32.4 -- -- Barley hay R 9 .0 88 10 -- Nu Nu 1.02 -- -- -- Cotton gin by

products R 7.0 90 5 -- -- -- 0.39 -- -- -- Grain sorghum, grain CC 0.2 86 40 45 75 80 0.093 0.105 0.15 0.16Bromoxynil Summary of Analytical Chemistry and Residue Data DP#: 378614



### Page 19 of 58 Barley grain CC 0.05 88 40 -- -- 5 0.023 -- -- 0.0025 Cotton, undelinted seed PC 1.5 88 Nu 10 Nu Nu -- 0.17 -- -- Cotton meal PC 1.5 89 5 -- 20 15 0.084 -- 0.30 0.225 Alfalfa meal PC 0.5 89 Nu -- 5 -- -- -- 0.025 -- Totals 100 100 100 100 1.6 32.7 0.48 0.39

a All data are based on Table 1 Feedstuffs (June 2008). Residue levels for beef and dairy are corrected for moisture content and are determined by formula: tolerance /%DM x % in diet. Residue levels for poultry and swine are considered “as - is” and are determined by formula: tolerance x % in diet. b Ty pical compositions of daily rations for the animals of choice for Table 1 Fe edstuffs (June 2008) data follow : Feedlot beef have a daily ration of 15% roughage (R), 80% carbohydrate concentrate (CC), and 5% protein concentrate (PC) as the slaughter time (last 4 - 6 months) gets closer. High -production lactating dairy cows have a d aily ration of 45% R, 45% CC, and 10% PC. A laying hen that will give a steady egg production is fed 75% CC and 25% PC. (The laying hen diet should be used to calculate poultry burdens.). A market hog diet that will give steady growth consists of 85% CC and 15% PC.

c Nu: Not used Table 7 b . Maximum Reasonably Balanced Dietary Burdens for Brom oxynil in Livestock Diets (js/bs revision 10 / 05 / 10) a

% Diet b Dietary Contributions (ppm) Feedstuff Type Tolerance, ppm % Dry

Matter Beef Dairy Poultry Swine Beef D ai ry Poultry Swine Barley, hay R 9.0 88 10 45 -- -- 1.02 4.6 -- -- Cotton gin by

products R 7.0 90 5 -- -- -- 0.39 -- -- -- Grain sorghum, grain CC 0.2 86 40 45 75 80 0.093 0.105 0.15 0.16 Barley grain CC 0.05 88 40 -- -- 5 0.023 -- -- 0.0 025 Cotton, undelinted seed PC 1.5 88 Nuc 10 Nu Nu -- 0.17 -- -- Cotton meal PC 1.5 89 5 -- 20 15 0.084 -- 0.30 0.225 Alfalfa meal PC 0.5 89 Nu -- 5 -- -- -- 0.025 -- Totals 100 100 100 100 1.6 4.9 0.48 0.39

a All data are based on Table 1 Fe edstuffs (June 2008). Residue levels for beef and dairy are corrected for moisture content and are determined by formula: tolerance /%DM x % in diet. Residue levels for poultry and swine are considered “as - is” and are determined by formula: tolerance x % in diet. b Ty pical compositions of daily rations for the animals of choice for Table 1 Feedstuffs (June 2008) data follow : Feedlot beef have a daily ration of 15% roughage (R), 80% carbohydrate concentrate (CC), and 5% protein concentrate (PC) as the slaughter time (last 4 - 6 months) gets closer. High -production lactating dairy cows have a daily ration of 45% R, 45% CC, and 10% PC. A laying hen that will give a steady egg production is fed 75% CC and 25% PC. (The laying hen diet should be used to ca lculate poultry burdens.). A market hog diet that will give steady growth consists of 85% CC and 15% PC.

c Nu: Not usedBromoxynil Summary of Analytical Chemistry and Residue Data DP#: 378614



### Page 20 of 58 Comments: 1) The proposed label allows use on Conservation Reserve Program (CPR) acres. Under this program farmlands are considered retired from active crop planting for a period of time to control topsoil erosion usually by a vegetative ground cover. It is also used to increase wildlife population across the US. Haying and grazing are authorized under certain conditions to impro ve the quality and performance of the CPR cover or provide emergency relief to livestock producers affected by a severe drought or natural disaster. In these cases, haying and grazing are onl y allowed no more that one out of every three ye ars. These acti vities would be used for growing cattle, and generall y not used for feedlot beef or high production dairy as defined b y Table 1 Feedstuffs (June 2008) . Forage commodities from these areas are not considered significant. 2) The proposed label allows use on grass grown for seed. With grass crops the purpose is to produce grass seed. Therefore , in grass seed growing areas, grazing would not occur, and hay would not be produced. The only feedstuff produced is grass straw. In the Pacific NW (to include ID , OR and WA), much of the grass straw is sold and shipped to the Orient for livestock feeding (>500,000 tons/y r). Only small amounts are fed to US cattle. In addition, other amounts are directed into energy producing processes. Th e amount that is fed i s use d for growing cattle, and not used for feedlot beef or high production dairy as defined by Table 1 Feedstuffs (June 2008) . Grass straw from other grass seed producing states allow controlled field burning to remove straw. Best estimates using a valu e of 2.2 tons/A for all varieties of U . S . grass seed, approximately 2,000,000 tons of straw would be generated across the U . S. Grass straw will not be considered significant. 3) The proposed label allows use on grain sorghum only (grain and forage). Uses on other ty pes of sorghum are not allowed. Grain from grain sorghum is included in the proposed dail y cattle diets. 4) Tolerances are established on cotton, undelinted seed, cotton gin b yproducts and cotton hulls. The Agency does not consider cotton hulls to be a significant feed item . Undelinted cotton seed and cotton gin by products are included in the proposed diet. Table 8 . Transfer Coefficients and Calculated Residues of Brom oxynil in Dairy Cattle Commodities Matrix Feeding Level

(ppm) Maximum Residues

at Feeding Level (ppm) Transfer

Coefficient 1 Calculated Dietary

Burden (ppm) Calculated

Residues (ppm) 2 Milk 4.2 0.05 0.012 32.7 (for tolerance assessment) 0.39 4.9 (for risk assessment) 0.058 1 Obtained by dividing the maximum residues at the feeding level by the feeding level. 2 Obtained by multiplying the transfer coefficient by the calculated dietary burden.Bromoxynil Summary of Analytical Chemistry and Residue Data DP#: 378614



### Page 21 of 58 Table 9 . Transfer Coefficients and Calculated Residues of Brom oxynil in Beef Cattle Comm odities Matrix Feeding Level

(ppm) Maximum Residues

at Feeding Level (ppm) Transfer

Coefficient 1 Calculated Dietary

Burden (ppm) Calculated

Residues (ppm) 2 Fat 4.2 0.68 0.16 1.6 3 0.26 Kidney 2.26 0.54 0.86 Liver 1.97 0.47 0.75 Muscle 0.37 0.088 0.14 1 Obtained by dividing the maximum residues at the feeding level by the feeding level. 2 Obtained by multiplying the transfer coefficient by the calculated dietary burden. 3 This value is used for both the tolerance assessment and the risk assessment. Table 1 0 . Transfer Co efficients and C alculated Residues of Brom oxynil in Poultry Comm odities Matrix Feeding Level

(ppm) Maximum Residues at

Feeding Level (ppm) Transfer Coefficient 1 Calculated Dietary

Burden (ppm) Calculated

Residues (ppm) 3 Eggs 0.70 <0.05 2 0.071 0.48 4 0. 034 Skin/Fat 0.70 0.08 0.11 0.055 Liver 0.21 0.08 3 0.39 0.19 Muscle 0.70 0.05 0.071 0.034 1 Obtained by dividing the maximum residues at the feeding level by the feeding level. 2 Residues in eggs were <0.05 ppm at the highest feeding level ( 0.7 0 ppm). 3 Obtained by multiplying the transfer coefficient by the calculated dietary burden. 4 This value is used for both the tolerance assessment and the risk assessment. Table 1 1 . Transfer Coefficients and C alculated Residues of Brom oxynil in Swin e Comm odities Matrix Feeding Level

(ppm) Maximum Residues

at Feeding Level (ppm) Transfer

Coefficient 1 Calculated Dietary

Burden (ppm) Calculated

Residues (ppm) 2 Fat 4.2 0.68 0.16 0.39 3 0.063 Kidney 2.26 0.54 0.21 Liver 1.97 0.47 0.18 Muscle 0. 37 0.088 0.034 1 Obtained by dividing the maximum residues at the feeding level by the feeding level. 2 Obtained by multiplying the transfer coefficient by the calculated dietary burden. 3 This value is used for both the tolerance assessment and the risk assessment. 

### Conclusions Based on the cattle and poultry feeding studies and the calculated livestock dietary burdens, the established livestock tolerances are adequate except for milk . The established livestock tolerances are 1 ppm on the fat of cattle, goat, hog, horse, and sheep; 3.5 ppm on meat by products of cattle, goat, hog, horse, and sheep; 0.5 ppm on meat of cattle, goat, hog, horse, and sheep; 0.05 ppm on poultry fat; 0.3 ppm on poultry

meat by products; 0.05 ppm on poultry meat; 0.05 ppm on egg; and 0.1 ppm on milk. A higher tolerance of 0.4 ppm must be proposed for milk. Note: Anticipated residue calculations are attached (Appendix IV) for dietary exposure assessment.Bromoxynil Summary of Analytical Chemistry and Residue Data DP#: 378614



### Page 22 of 58 860.1500 Crop Field Trials Goodlow , T., 8/17/10, DP Number 380770, Bromoxynil: Review of HUSKIE HERBICIDE

– Magnitude of the Residue in/on Sorghum and Grass 

### Grass The raw agricultural commodities associated with grass are forage and hay . Baye r CropScience has submitted field trial data for the product HUSKIE herbicide on grass (Bermuda, bluegrass, and fescue). HUSKIE herbicide is an emulsifiable concentrate mixture containing three active ingredients: py rasulfotole (37.5 g ai/L), bromoxy nil (210 g ai/L), and mefenp yr - diethyl safener (9.38 g ai/L). Twel ve trials were c onducted in the United States and Canada during the 2008 growing season. The trials encompassed Zones 1 (1 trial in Atlantic Provinces, Canada) , 2 (1 trial in GA), 3 (1 trial in FL), 4 (1 trial in AR), 5 (1 trial in WI ; 1 trial in NE), 9 (1 trial in ID ) , 10 (1 trial in CA), 11 (1 trial in ID; 1 trial in WA), and 12 (1 trial in British Columbia, Canada; 1 trial in OR). Each site consisted of one control plot and two treatment plots, with one treatment plot for sampling forage and one for sampling hay . The treatment plots each received two applications of the formulated product at a target rate of 16.1 fl oz HUSKIE/A/application, which corresponds to 0.22 lb bromoxy nil/A/application (0.25 kg bromox yn il/ha/application). Actual total application rates ranged from 31 to 37 fl oz HUSKIE/A/season with a 27 - to 30 - day re - treatment interval (RTI) . Spray volumes ranged from 10 to 24 gal/A (89 to 225 L/ha). An adjuvant was not used in the spray applications. Grass forage samples were collected at target pre - harvest interval (PHI) of 0 day s and 7 day s. Grass hay samples were collected at a target PHI of 30 day s. A residue decline trial was also conducted at one site, in which forage samples were collected at PHI s of 0, 1, 3, 7, 10, and 14 day s and hay samples were collected at PHI s of 20, 25, 30, 36, and 40 day s. Bromox ynil residue was quantitated by LC - MS/MS using stable isotopically labeled bromox ynil as an internal standard. The LLM V for bromoxy nil was 0.01 ppm in grass forage and grass hay . The method is accep table based on concurrent recoveries. The maximum frozen storage interval from sampling to extraction prior to analy sis of bromox yn il was 350 days for grass forage and 313 day s for grass hay . All samples were anal yz ed within 2 day s of extraction. Storag e stability data are available that demonstrate bromox yn il residues are stable in grass forage, hay, and seed stored frozen at - 10°C for 12 months ( MRID 43108801, D204403 and D199274, S. Knizner). These data adequatel y support the storage durations and con ditions of samples from the submitted crop field trial study . After two applications of Huskie Herbicide to grass at a total rate of 0.43 to 0.51 lb ai/A for bromox yn il, residues of bromoxy nil in the grass forage samples ranged from 3.37 ppm to 37.8 ppm at a PHI of 0 day s and from 0.0921 ppm to 14.2 ppm at a PHI of 7 to 11 day s. Bromoxy nil in grass hay

samples, collected at a PHI of 28 to 31 day s from plots treated with Huskie Herbicide a total rate of 0.43 to 0.45 lb ai/A, ranged from below the LLMV (0 .01 ppm) to 2.26 ppm. Residue decline data showed that residues of bromoxy nil decreased with time in gras s forage and hay . A slight increase in bromoxy nil residues was observed in grass hay between the 30 and 35 day PHIinterval .Bromoxynil Summary of Analytical Chemistry and Residue Data DP#: 378614



### Page 23 of 58 TABLE 1 2 . Summ ary of Residue Data fromCrop Field Trials with Brom oxynil Matrix Total

Applic. Rate lb a.i./A (kg a.i./ha) PHI

(days) Residue Levels 1 (ppm)

n Min. Max. HAFT 2 Median (STMdR) Mean

(STMR) Std. Dev. Grass Grass Forage 0.43 - 0.51

(0.48 - 0.57) 0 24 3.37 37.8 3 7.1 18.2 18.9 11.6

7 - 11 24 0.0921 14.2 13.7 0.520 2.81 5.03 Grass Hay 0.43 - 0.45

(0.48 - 0.50) 28 - 31 24 <0.01 2.26 2.05 0.089 0.333 0.58 1 LLMV = 0.01 ppm for grass forage and grass hay. LOD = 0.00531 ppm for forage and 0.00287 ppm for hay. 2 HAFT = Highest Average Field Trial. 

### C onclusions : The submitted residue data for grass are adequate to fulfill data requirements. The number and locations of the crop field trials are in accordance with OPPTS Guideline 860.1500, and the field trials reflect the proposed use pattern. The residue data for grass were entered into the Agency ’s tolerance spreadsheet as specified b y the Guidance for Setting Pesticide Tolerances Based on Field Trial Data SOP to determine an appropriate tolerance level; see Appendix I. Using the tolerance calculator, the residue data support the proposed tolerance s of 18 ppm on grass forage and 5.0 ppm on grass hay . Grain Sorghum The raw agricultural commodities associated with grain sorghum are grain, forage/silage , stover, and as pirated grain fractions. Baye r CropScience has submitted field trial data for the product HUSKIE herbicide on grain sorghum. HUSKIE herbicide is an emulsifiable concentrate mixture containing three active ingredients: py

rasulfotole (37.5 g ai/L), bromox ynil (210 g ai/L), and mefenpy r - diethyl safener (9.38 g ai/L). Twelve trials were conducted in the United States during the 2008 growing season. The trials encompassed Zones 2 (1 trial in GA) , 4 (1 trial in MS), 5 (1 trial each in IN, IA , OH, MN), 6 (1 trial each in OK, TX), 7 (1 trial in ND), and 8 (l trial each in CO, OK, TX). Each site consisted of one control plot and two treatment plots, with one treatment plot for sampling forage and one for sampling grain and stover. The treatment plots each received two applications of the formulated product at a target rate of 16.1 fl oz HUSKIE/A/application, which corresponds to 0.22 lb bromoxy nil/A/application (0.25 kg bromoxy nil/ha/application). Actual total application rates ranged from 32 to 33 fl oz HUSKIE/A/season. The re - treatment interval (RTI) ranged from 11 to 16 day s and the spray volumes ranged from 12 to 20 gal/A (112 to 188 L/ha). An adjuvant was not used in the spray applications. Sorghum forage samples were collected at target pre - harvest interv als (PHI) of 0 day s and 7 day s and also at earliest commercial harvest (ECH) (BBCH 81, beginning of ripening, to BBCH 87, hard dough), which corresponded to PHIs of 32 to 82 day s. Sorghum grain and stover samples were collected at a target PHI of 60 days. A residue decline trial was also conducted at one site, in which forage samples were collected at PHI s of 0, 1, 3, 7, 10, and 14 day s with additional samples collected at five intervals before, at, and after earliest commercial harvest (ECH - 14, ECH - 7, E CH, ECH+7, and ECH+14 day s; actual PHI s were 18, 25, 32, 39, and 46 day s). Grain and stover samples were collected at five intervals corresponding to target PHI s of 47, 53, 60, 67, and 74 day s.Bromoxynil Summary of Analytical Chemistry and Residue Data DP#: 378614



### Page 24 of 58 Bromox ynil residues were quantitated b y LC - MS/MS using stable isotopically labeled bromox yn il as an internal standard. The LLMV for bromoxy nil was 0.01 ppm in all matrices. The method is acceptable based on concurrent recoveries. The residues are reported in terms of bromox yn il phenol. The maximum frozen storage interval from sampling to extraction of bromoxy nil was 351 days for forage, 275 day s for grain, and 273 day s for stover. All samples were analyzed within 3 day s of extraction. Storage stability data are available that demonstrate bromoxy nil residues are st able in sorghum forage, grain and stover stored frozen at - 10°C for 12 months ( MRID 43108801, D204403 and D199274, S. Knizner). These data adequatel y support the storage durations and conditions of samples from the submitted crop field trial study . After two applications of Huskie Herbicide to sorghum at a total rate of 0.43 to 0.44 lb ai/A for bromox yn il, residues of bromoxy nil in the forage samples ranged from 4.16 ppm to 27.2 ppm at a PHI of 0 day s, from 0.072 ppm to 0.61 ppm at a PHIof 5 to 8 day s, and from <LLMV (0.01 ppm) to 0.30 ppm at ECH (PHI of 32 to 82 day s). Residues in grain and stover samples collected at a PHI of 56 to 60 day s from plots treated at a total rate of 0.43 to 0.44 lb ai/A ranged from below the LLMV (0.01 ppm) to 0.11 ppm and from 0.011 ppm to 0.11 ppm, respectivel y. Residue decline data showed that residues of bromoxy nil decreased with time in/on sorghum earl y forage. The residues also generally decreased with time in/on sorghum forage collected around earliest commercial harve st (ECH - 14 day to ECH +14 day); however, a spike in residues was observed at the ECH - 7 day interval. In/on sorghum stover, the residues increased with time. The decline of bromoxy nil residue with time in/on sorghum grain could not be assessed due to residue levels below the LLMV.

TABLE 1 3 . Summ ary of Residue Data fromCrop Field Trials with Brom oxynil Matrix Total

Applic. Rate lb a.i./A (kg a.i./ha) PHI 1 (days) Residue Levels 2, 3 (ppm) n Min. Max. HAFT 4 Median (STMdR) Mean

(STMR) Std.

Dev. Grain Sorghum Sorghum Forage 0.431 -

0.442 (0.482 - 0.498) 0 24 4.16 27.2 25.2 11.1 12.0 5.21

5 to 8 24 0.072 0.61 0.58 0.28 0.30 0.16 ECH ( 32 to 82) 24 <0.01 0.30 0.30 <0.01 0.037 0.081 Sorghum Grain 56 to 60 24 <0.01 0.11 0.103 0.011 0.028 0.030 Sorghum Stover 56 to 60 24 0.011 0.11 0.097 0.060 0.061 0.032 1 ECH = Earliest commercial harvest 2 LLMV = 0.01 ppm for forage, grain, and stover. LOD = 0.00246 ppm for forage, 0.00379 ppm for grain, or 0.00315 for stover. LLMV (0.01 ppm) was used whe n values were <LLMV. 3 Residues reported as bromoxynil phenol. 4 HAFT = Highest Average Field Trial. 

### Conclusions : The submitted residue data for grain sorghum are adequate to fulfill data requirements. The number and locations of crop field trials are in accordance with OPPTS Guideline 860.1500, and the field trials reflect the proposed use pattern. The residue data for grain sorghum were entered into the Agency ’s tolerance spreadsheet as specified b y the Guidance for Setting Pesticide Tolerances Based on Field Trial Data SOP to determine an appropriate tolerance level; see Appendix I . Using the tolerance calculator, theBromoxynil Summary of Analytical Chemistry and Residue Data DP#: 378614



### Page 25 of 58 residue data support the proposed tolerance of 0.2 ppm on the grain of grain sorghum and also support the established tolerance of 0 .2 ppm on the stover of grain sorghum. Based on the tolerance calculator , HED is recommending that the proposed tolerance of 0.5 ppm on the forage of grain sorghum be increased to 0.8 ppm. Grain, Aspirated Grain Fractions Funk, S., 6/28/94, DP Number 18 4641, Bromoxynil Octanoate (Chemical 035302; List B; Case 2070). Additional Data for Magnitude of the Residue in/on Barley (Grain, Forage, Straw, Grain Dust), Garlic, Corn (Grain Dust), and Sorghum (Grain Dust). Processing Studies for Barley, Sorghum, and Corn . Swartz, C., 3/6/96, DP Number 195998, Bromoxynil Octanoate. List B Reregistration Case No. 2070/Chemical ID No. 035302. Magnitude of the residue: Alfalfa; Grasses (Grown for Seed); Wheat Process ing/Aspirated Grain Fractions. 

### Residues in aspirated grain fractions must be determined for uses on corn, sorghum, so ybeans, and wheat. Studies on residues in aspirated grain fractions of barley , corn, sorghum , and wheat have been previousl y reviewed . As shown in Table 14 (from DP Number 184641) and Ta ble 15 (from DP Number 195998), these studies indicated that residues concentrate in aspirated grain fractions. Table 14. Brom oxynil Residues (D etected as B rom oxynil M ethyl E ther) in or on Barley, Corn, and

Sorghum Grain and Processed F ractions followin g 10x T reatm ent (5 lb ai/A) w ith the 2 lb/gal EC Formulation Crop (MRID) Milling

Process Processed Fraction Residues Found a (ppm) Concurrent

Method Recovery (%) b Concentration

Factor Barley (42460502) Dry Grain RAC Hulls Pearl barley Bran Flo ur Grain dust 0.18 - 0.22

0.40 - 0.56 0.02 - 0.04 0.06 - 0.1 0.02 - 0.06 0.8 - 2.0 96

90 86 116 98 114 2.2 - 2.5x

n/c c n/c n/c 4 - 9.1x Field corn (42571401) Dry Grain RAC Meal Grits Flour Aspirated (2540) e Aspirated (2030) f Aspirated (other) g Crude oil Refined oil <0.02

<0.02 <0.02 <0.02 0.04 - 0.07 0.05 - 0.06 0.07 - 0.11 <0.02 <0.02 83

82 82 85 80 77 74 71 84 n/c c

n/c n/c 4 - 7x d 5 - 6x d 7 - 11x d n/c n/c Wet Grain RAC Starch

Aspirated (2540) e Aspirated (2030) f Aspirated (other) g Crude oil Refined oil <0.02

<0.02 0.03 - 0.07 0.04 - 0.06 0.08 - 0.11 <0.02 <0.02 83

78 72 79 90 78 99 n/c

3 - 7x d 4 - 6x d 8 - 11x d n/c n/c Sorghum (42465401) Dry Grain RAC Flour Grain dust <0.02 - 0.03 h

<0.02 0.19 - 0.36 h 75 70 93 n/c

12xhBromoxynil Summary of Analytical Chemistry and Residue Data DP#: 378614



### Page 26 of 58 Wet Grain RAC Starch

Grain dust <0.02

<0.02 0.12 - 0.29 76 84 81 n/c

--

aThree treated samples analyzed per fraction. Residue values for treated samples were not corrected for concurrent recoveries. bAll concurrent method recovery samples fortified at 0.1 ppm with bromo xynil octanoate; method recoveries corrected for residues in or on control samples [all <0.02 ppm (nondetectable)]. cn/c = no concentration. dAssumes bromoxynil concentration on the rac at 50% of the LOQ , or 0.01 ppm. e Aspirated grain particles > screen size 2540. f

Aspirated grain particles > screen size 2030. g Composite sample of aspirated grain particles < screen size 2030. hResidues were <0.02 ppm (nondetectable) in or on two treated grain samples, and were 0.03 ppm in or on a third; the concentration factor is calculated for the dust sample (0.36 ppm) obtained from the grain sample bearing detectable residues.

Table 15. Brom oxynil Residues in Wheat Processing F ractions 

### . Commodity Residues (ppm) a Residue/10 (ppm) b Grain <0.02, 0.02, 0.03 NA Bran 0.07, 0.06, 0.08 0.007; 0.006; 0.008 Middlings <0.02 (3) NA Shorts <0.02 (3) NA Flour <0.02 (3) NA Aspirated grain fractions 2.16, 1.55, 1.53 0.216; 0.155; 0.153

a Each residue value represents one sample unless otherwise indic ated in parentheses. Residue values were not corrected for concurrent method recoveries or residues in untreated samples. Residues represent application at a 10x rate. b The tolerance for w

heat aspirated grain fractions is based on the residue divided b y the degree of exaggeration (10x) since no quantifiable residues were found in the grain at 1x, residues were found in the grain at the exaggerated rate, and those resi dues divided by the exaggerated rate (10x) are greater than or equal to twice the LOQ o f the method ( OPPTS 860. 1520). 

### A tolerance for aspirated grain fractions of 0.3 ppm was established based on wheat since wheat was determined to yi eld the highest residues in aspirated grain fractions . Since the sorghum grain tolerance will increase fr om 0.05 ppm to 0.2 ppm, residues on sorghum aspirated grain fractions will increase . Using the HAFT for sorghum grain of 0.103 from MRID 47815002 and the concentration factor of 12x from Table 14 , the aspirated grain fractions tolerance should now be 1.2 ppm . Conclusions. Adequate processing studies on corn, sorghum, and wheat are available to support a tolerance on aspirated grain fractions (grain dust). The studies all indicate that residues concentrate in aspirated grain fractions. Because the tol erance on the grain of grain sorghum is being increased from 0.05 ppm to 0.2 ppm, higher residues may occur in aspirated grain fractions; therefore, the petitioner must submit a revised Section F to propose a higher tolerance of 1.2 ppm for grain, aspirated grain fractions .Bromoxynil Summary of Analytical Chemistry and Residue Data DP#: 378614



### Page 27 of 58 860.1520 Processed Food and Feed There are no processed commodities associated with use on grass. The processed commodity associated with use on grain sorghum is flour; however, residue data are not needed on sorghum flour at this time since it is used exclusively in the United States as a component for dry

wall, and not as either a human food or feedstuff. Aspirated grain fractions are discussed under 860.1500. 860.1650 Submittal of Analytical Reference Standa rds Analy tical reference standards for bromoxy nil (expiration date 5/7/2011), bromoxy nil heptanoate (expiration date 9/15/2018), and bromox ynil octanoate (expiration date 2/13/2017) are currently available in the National Pesticide Standards Repository . No anal ytical reference standard for the cotton metabolite 3,5 - dibromo - 4 - hydrox yb enzoic acid (DBHA) is available (e - mail from Charles Stafford to Nancy Dodd on 10/20/10). Conclusions Analy tical reference standards are available for bromoxy nil, bromoxy

n il heptanoate, and bromox yn il octanoate. No anal ytical reference standard for the cotton metabolite 3,5 - dibromo 4 - hydroxy

benzoic acid (DBHA) is available . 860.1850 Confined Accumulation in Rotational Crops Madden, B., 6/24/98, DP Number 246944, Bromox ynil (Case #2070: PC Codes 035301 and 035302): Revised Human Health Risk Assessment for Bromoxynil Kramer, G.F., 3/11/97, DP Number 232957, ID# 000264 - 00540. PP# 3F04233. Bromoxynil Octanoate and Heptanoate in or on Transgenic BXN Cotton. Amendment of 12/18/96. Submission of Residue Data. Swartz, C., 2/15/96, DP Number 204985, Bromoxynil Octanoate. List B Reregistration Case No. 2070/Chemical ID No. 035302. Guideline Ref. No. 165
- 2: Rotational Crops, Limited Field Studies. 

### In a confined rotational crop study conducted by Rhone - Poulenc (M RID No. 00115657 , Environmental Fate and Effects Division (E FED ) Phase 4 Review dated 1/17/91 ) , soil was treated with 14 

### C - bromoxynil octanoate in an EC formulation at 0.51 lb ai/A. Ten months after treatment, spinac h, radishes and oats were planted; 12 months after treatment, soy beans and turnips were also planted. Total radioactive residues in spinach soy bean trash and oat straw were 0.02 ppm, while the TRR in all other samples was <0.01 ppm. Since radioactive res idues were so low, there was no attempt to identify bromoxynil metabolites in rotational crops. In a c onfined rotational crop study submitted by Union Carbide ( MRID No. 00149623 , 1 984 ) , s oil was treated with 14 

### C - bromox yn il octanoate in the UC ME - 4 formulation at a rate of 0.41 lb ai/A. Rotational crops spinach, beets and wheat were planted at intervals of 35, 120 and 360 day s after soil treatment. Average total radioactive residues [ 14 

### C - bromox ynil octanoate equivalents] in rotational crops samples are pr esented in Table 16 .Bromoxynil Summary of Analytical Chemistry and Residue Data DP#: 378614



### Page 28 of 58 Table 16 . Total Radioactive Residues in Rotational Crops (MRID No. 00149623) Crop 35 - Day Samples (ppm) 120 - Day Samples (ppm) 360 - Day Samples (ppm) Spinach (leaf) 0.086 0.039 0.087 Beets, tops 0.026 0.012 0.02 Beets , roots 0.04 0.012 0.013 Wheat straw 0.051 0.035 0.06 Wheat hulls 0.054 0.02 0.068 Wheat grain 0.02 <0.01 <0.01 

### The registrant attempted to characterize/identify the radioactivity

found in the 35 - day

samples. Following methanolic base hydroly sis of rotational crops samples, extracts were acidified and partitioned into ethyl acetate. Extractable radioactivity ranged from 16 - 40 %TRR. Analy sis of the radioactivity using thin layer chromatography (TL C) demonstrated that the radioactivity was polar, and consisted of multiple, low - level components. In the Union Carbide study report, soil metabolism data were also discussed. The petitioner indicated that bromox ynil octanoate breaks down rapidly in soils, and is associated with organic matter ; ultimately , residues are incorporated into natural products. Conclusions In the confined rotational crop study in which s oil was treated with 14 

### C - bromox yn il octanoate at a rate of 0.41 lb ai, low level residues were found in the rotational crops spin ach, beets, and wheat. The residues consisted of multiple, polar components. 860.1900 Field Accumulation in Rotational Crops Madden, B., 6/24/98, DP Number 246944, Bromoxynil (Case #2070: PC Codes 035301 and 035302): Revised Human Health Risk Assessment for Bromoxynil Swartz, C., 2/20 /96, DP Number 204985, Bromoxynil Octanoate. List B Reregistration Case No. 2070/Chemical ID No. 035302. Guideline Ref. No. 165
- 2: Rotational Crops, Limited Field Studies. 

### L imited rotational crop field trials were condu cted in CA and TX (MRID 43279401) . S oil was treated with Buctril ® 2E at 0.5 lb ai/A. Winter wheat, collard greens and radishes were rotated into the plots 30 and 120 day s after treatment. Samples from the 30 - day plots were harvested at maturity . Resid

ues were less than the limit of quantitation ( <0.02 ppm) in winter wheat forage, radish tops and roots, and in collard greens harvested from the 30 - day plantback plots; residues were less than the limit of detection (<0.01) in wheat grain and straw harvest ed from the 30 - day interval. Since residues were so low in the 30 - day samples, the 120 - day

samples were not anal yz ed, and 365 - day

plots were not planted. Conclusions The field rotational crop studies, together with the confined rotational crop data, ar e adequate to demonstrate that detectable bromoxy nil residues would not be expected in crops rotated at 30 day s (or more) following application of bromoxy nil octanoate to primary

crops on the Huskie TMBromoxynil Summary of Analytical Chemistry and Residue Data DP#: 378614



### Page 29 of 58 Herbicide label . Based on the available bromox yn il rot ational crop data, a 30 - day plantback interval (PBI) is adequate for bromox ynil for all rotational crops planted after application of Huskie TM 

### Herbicide . (Note: Transgenic cotton is not on the Huskie TM 

### Herbicide label. To support the use on transgenic c otton ( DP Number 23957 (G. Kramer, 3/11/97) , a new limited field rotational crop study is required. The magnitude of bromoxy nil and DBHA should be determined in rotational crops planted following treatment of geneticall y- modified cotton with bromoxy nil at the maximum use rate of 1.5 lb ai/A . ) 860.1550 Proposed Tolerances Tolerances are established under 40 CFR §180.324(a) for residues of the herbicide bromoxynil (3.5 - dibromo - 4 - hydrox ybenzonitrile) resulting from application of its octanoic and/or heptano ic acid ester in or on alfalfa, barley , field and pop corn, flax, garlic, aspirated grain fractions, grass, oat, onion, peppermint, rye, sorghum, spearmint, and wheat commodities at levels ranging from 0.05 ppm to 9.0 ppm. Tolerances are established under 40 CFR §180.324(b) for residues of the herbicide bromox ynil (3.5 - dibromo - 4 - hydrox yb enzonitrile) and its metabolite 3,5 - dibromo - 4 - hydrox yb enzoic acid (DBHA) resulting from application of its octanoic and/or heptanoic acid ester in or on cotton commodities at levels ranging from 1.5 to 7.0 ppm and in egg, milk, and the meat, fat, and meat b yproducts of cattle, goat, hog, horse, poultry, and sheep at levels ranging from 0.05 to 3.5 ppm. No maximum residue limits or tolerances are esta blished for bromox ynil by Codex or Mexico. T olerance s have been established by Canada for grain of sorghum grain at 0.1 ppm and for milk at 0.1 ppm . The Canadian tolerance expression is “ 3,5 - dibromo - 4 - hydroxybenzonitrile, including the metabolite 3,5 - dibromo - 4 - hydrox yb enzoic a cid” ; however, c ompliance with the tolerance levels in the U.S. will be determined by measuring only

bromoxy nil (3,5 - dibromo - 4 - hydrox yb enzonitrile). The petitioner must submit a revised Section F to propose tolerances which reflect the recommended tole rance levels and correct commodity definitions as specified in Table 17 . Because the tolerance on the grain of grain sorghum is being increased from 0.05 ppm to 0.2 ppm, higher residues may occur in aspirated grain fractions . HED has determined that a h igher tolerance of 1.2 ppm is needed for grain, aspirated grain fractions . Based on input of the residue data into the tolerance spreadsheet ( Guidance for Setting Pesticide Tolerances Based on Field Trial Data ), HED is recommending a tolerance of 0.8 ppm for sorghum, grain, forage in lieu of the established tolerance of 0.5 ppm . Based on calculated residues in dairy cattle for the tolerance assessment, the established tolerance on milk must be increased from 0.1 ppm to 0.4 ppm. Other livestock tolerance levels remain unchanged. As determined b y an AD HOC meeting of the Residues of Concern Knowledgebase Subcommittee (ROCKS) on 2/10/11, b romox yn il is the residue of concern in milk and other livestock commodities for the tolerance expression while bromoxy n il and DBHA are the residues of concern in livestock commodities for the risk assessment.Bromoxynil Summary of Analytical Chemistry and Residue Data DP#: 378614



### Page 30 of 58 Table 17 . Tolerance Summary for Brom oxynil . Commodity Tolerance (ppm) Comments; Correct Commodity Definition Established Proposed Recommended Grass, forage 3.0 18 18 Grass, hay 3.0 5.0 5.0 Grain, aspirated fractions 0.3 -- 1.2 Grain, aspirated grain fractions Milk 0.1 -- 0.4 Sorghum, grain 0.05 0.2 0.2 Sorghum, grain, grain Sorghum, grain, forage 0.5 -- 0.8 Sorghum, grain, stover 0.2 -- 0.2 

### Re ferences DP#: D380770 Subject: Bromox ynil: Review of HUSKIE HERBI CIDE

– Magnitude of the Residue in/on

Sorghum and Grass . From: Toiya Goodlow To: Cassi Walls Date: 8/17/10 MRIDs: 47815001, 47815002 DP#: D246944 Subject: Bromox ynil (Case #2070: PC Codes 035301 and 035302): Revised Human Health

Risk Assessment for Bromoxy nil . From: Barbara Madden To: Linda Werrell Date: 6/24/98 MRIDs: NA DP#: D244250 Subject: Bromoxynil Octanoate. List B Reregistration Case No. 2070/Chemical ID No.

035302. Issues Discussed by HED’s ChemSAC on 2/25/98. From: Christina Swartz To: Barbara Madden, Linda Werrell/Kathy Monk, and Tobi Colvin - Snyder Date: 3/19/98 MRID: NoneBromoxynil Summary of Analytical Chemistry and Residue Data DP#: 378614



### Page 31 of 58 DP#: D 243651 Subject: Bromox ynil Octanoate. List B Reregistration Case No. 2070/Chemical ID No.

03530 . Rhône - Poulenc Submission of Additional Field Trials Conducted at Reduced Rates on Transgenic BXN Cotton. From: Christina Swartz To: Jane Smith Date: 3/2/98 MRIDs: 44458900, 44458902 DP#: D239914 Subject: Bromox ynil Octanoate. List B Reregistration Cas e No. 2070/Chemical ID No.

035302. Revised Anticipated Residues Assessment Based on Revised Labeling Submitted in Conjunction with PP#3F4233 (9/24/97). From: Christina Swartz To: Jane Smith, Linda Werrell/Kathy Monk/Tobi Colvin - Snyder Date: 1/20/98 MRID : None DP#: D232957 Subject: ID # 000264 - 00540. PP# 3F04233. Bromoxy nil Octanoate and Heptanoate in or on Transgenic BXN Cotton. Amendment of 12/18/96. Submission of Residue Data. MRID# 441833 - 01. Barcode D232957. Chemicals 035302 & 128920. Case 04 9993. From: G. F. Kramer , Ph.D. To: R. Griffin/K. Bo yl e Date: 3/11/97 MRIDs: 44183301 DP#: D231906 Subject: PP#3F04233. Extension of Conditional Registration for the Use of Bromoxyn il

on Transgenic Cotton. From: R. Griffin, K. Bo yl e, F. Fort, L . Hansen, G. Kramer, and S. Robbins To: D. Stubbs Date: 4/8/97 MRID: None DP#: D204985 Subject: Bromox ynil Octanoate. List B Reregistration Case No. 2070/Chemical ID No.

035302. Guideline Ref. No. 165 - 2: Rotational Crops, Limited Field Studies. From: Christina B. Swartz To: Kathry

n Davis Date: 2/15/96 MRID: 43279401Bromoxynil Summary of Analytical Chemistry and Residue Data DP#: 378614



### Page 32 of 58 DP#: D195998 Subject: Bromox ynil Octanoate. List B Reregistration Case No. 2070/Chemical ID No.

035302. Magnitude of the residue: Alfalfa; Grasses (Grown for Seed); Wheat Processing/Aspirated Gr ain Fractions From: Christina B. Swartz To: Kathry

n Davis Date: 3/6/96 MRIDs: 42950101, 42950102, and 42950103 DP#: D189368 Subject: PP# 3G04197. Bromox ynil octanoate and heptanoate in or on transgenic

Bromotol cotton. Evaluation of residue and anal yt ical data for an EUP and temporary

tolerances. From: G.F. Kramer, Ph.D. To: Robert Taylor/Karen Hicks Date: 9 /17/ 93 MRIDs: 42677701, 42677702 and 42677703 DP#: D184641, D185636, and D182875 Subject: Bromox ynil Octanoate (Chemical 035302; List B; Case 2070 ). Additional Data

for Magnitude of the Residue in/on Barley (Grain, Forage, Straw, Grain Dust), Garlic, Corn (Grain Dust), and Sorghum (Grai n Dust). Processing Studies for Barley , Sorghum, and Corn. From: Stephen Funk, Ph.D. To: Kathry

n Davis Date: 6/28/94 MRIDs: 42540601, 42540602, 42571401, 42465401, and 42460502 DP#: D179705 Subject: PP#0F3848 - B ROMOXYNIL 

### (B UCTRIL 

### ®) ON 

### RICE 

### G RAIN AND 

### S TRAW 

### . REVIEW OF

THE 

### M AY 

### 26 AND 

### AUGUST 

### 7, 1992 AMEND MENTS 

### . From: Francis D. Griffith, Jr. Date: 11/4/92 MRID s: 42344901, 42344902, and 42433401 DP#: D000000, 035301.001 Subject: PP#3F04233. New Tolerances for Bromox ynil on Cotton Commodities. Changes

f rom HED’s April 8, 1997 Risk Assessment. From: Stephanie Irene Date: 4/25/97 MRID: None Attachments: Appendix I - International Residue Limit Status sheet Appendix I I - Chemical Name and Structure Table Appendix II I - Tolerance Assessment Calculations Appendix IV

– Anticipated Residues Calculations for Dietary Exposure Assessment Templat e Version April 2008Bromoxynil Summary of Analytical Chemistry and Residue Data DP#: 378614



### Page 33 of 58 Appendix 1 

## International Residue Limits Bromox ynil (035301; 09/15/2010) Summary of US and International Tolerances and Maximum Residue Limits Residue Definition : US Canada Mexico 2 

### Codex 3 40 CFR 180.324: Plant: bromoxynil ( 3,5 - dib romo - 4 - hydroxybenzonitrile ) Livestock: bromoxynil (3,5 - dibromo - 4 - hydroxybenzonitrile) and its metabolite 3,5 - dibromo - 4 - hydroxybenzoic acid (DBHA) 3,5 - dibromo - 4 - hydroxybenzonitrile, including the metabolite 3,5 - dibromo - 4 - hydroxybenzoic acid None

Commodity 1 Tolerance (ppm) /Maximum Residue Limit (mg/kg) US Canada Mexico 2 Codex Grain, aspirated grain fractions 1.2 Grass, forage 18 Grass, hay 5.0 Milk 0.4 0.1 Sorghum, grain, forage 0.8 Sorghum, grain , grain 0.2 0.1 Com pleted: M. Negu ssie;09/16/2010 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 not been finalized by the CCPR and the CAC.Bromoxynil Summary of Analytical Chemistry and Residue Data DP#: 378614



### Page 34 of 58 Appendix II APPENDIX I I . Chemical Names and Structures of Brom oxynil , its Esters and Metabolite. Common name; Com pany code Chemical name Chemical structure bromoxynil 3,5 - dibromo - 4 - hydroxybenzonitrile

bromoxynil octanoate 2.6 - dibromo - 4 - cyanophenyl octanoate

bromoxynil heptanoate 2.6 - dibromo - 4 - cyanophenyl heptanoate

DBHA 3,5 - dibromo - 4 - hydroxybenzoic acid OH Br Br

O HOBromoxynil Summary of Analytical Chemistry and Residue Data DP#: 378614



### Page 35 of 58 Appendix III Tolerance Assessment C alculations For each of the crops listed below, the Guidance for Setting Pesticide Tolerances Based on Field Trial Data ( SOP ) , along with the tolerance spreadsheet ( February 2008 version) , was used for calculating recommended tolerances. (For n>15, resul ts are the same as for the September 2009 version.) Grass Forage The dataset used to establish a tolerance for bromoxy nil on grass forage consisted of field trial data representing total application rates of 0.42 - 0.51 lb ai/A (2 applications at ~0.22 lb ai/A/application) with PHI s of 7 - 11 day s. As specified by the Guidance for Setting Pesticide Tolerances Based on Field Trial Data (SOP), the field trial application rates are within 25% of the maximum label application rate for grass forage; however, th e PHIs of 7 - 11 day s for grass forage were not within 25% of the proposed 7 - day PHI . The residue values that were entered into the tolerance spreadsheet are provided below. All 24 field trial sample results for grass forage were above the LOQ (>0.01 ppm) . M aximum likelihood estimation (MLE) procedures were not needed to impute censored values. Visual inspection of the lognormal probability plot and the results from the approximate Shapiro Francia Normality

test indicate that the dataset for grass forage is not lognormal. The “Mean + 3SD ” m ethod was used to calculate the tolerance for the data set. The tolerance value calculated using the “Mean + 3SD” method represents an upper bound estimate of the 89 th 

### percentile for any distribution. Using the tolerance spreadsheet, the recommended tolerance for grass forage is 18 ppm.Bromoxynil Summary of Analytical Chemistry and Residue Data DP#: 378614



### Page 36 of 58 Regulator: EPA Chemical: bromoxynil Crop: Grass forage PHI: 7 - 11 days App. Rate: 0.43 - 0.51 lb ai/A Submitter: Bayer CropScience

Residues LN(Residues) Z scores 0 .107 - 2.23 - 0.73 0.106 - 2.24 - 0.88 0.800 - 0.22 0.26 0.620 - 0.48 0.16 13.100 2.57 1.04 14.200 2.65 1.95 2.890 1.06 0.88 2.840 1.04 0.73 0.095 - 2.35 - 1.24 0.098 - 2.33 - 1.04 0.842 - 0.17 0.48 0.500 - 0.69 - 0.16 0.925 - 0.08 0.60 0.837 - 0.18 0.37 0.180 - 1.71 - 0.26 0.171 - 1.77 - 0.37 13.800 2.62 1.50 13.600 2.61 1.24 0.095 - 2.35 - 1.50 0.092 - 2.38 - 1.95 0.505 - 0.68 - 0.05 0.536 - 0.62 0.05 0.162 - 1.82 - 0.48 0.147 - 1.92 - 0.60Bromoxynil Summary of Analytical Chemistry and Residue Data DP#: 378614



### Page 37 of 58 Regulator: EPA Chemical: bromoxynil Crop: Grass forage PHI: 7-11 days App. Rate: 0.43-0.51 days Submitter: Bayer CropScience

n: 24 min: 0.09 max: 14.20 median: 0.52 average: 2.80 95th Percentile 99th Percentile 99.9th Percentile

12 15 19 (15) (19) (--) 12 40 140 (40) (170) (--) 5.0 18 3.0 0.8826 0.05 >= p-value > 0.01 : Reject lognormality assumption Approximate Shapiro-Francia Normality Test EU Method I Normal

UCLMedian95th 95/99 Rule EU Method II Distribution-Free Mean+3SD

Lognormal Probability Plot

99.9 99 98 95 90 80 70 50 30 20 10 5 2 1 0.1 15.0000 7.5000 3.7500 1.8750 0.9375 0.4688 0.2344 0.1172 0.0586 y = 1.7031x - 0.4864 R 2 = 0.8826

PercentilesConcentrations EPA bromoxynil Grass forage 7-11 days 0.43-0.51 days Bayer CropScienceBromoxynil Summary of Analytical Chemistry and Residue Data DP#: 378614



### Page 38 of 58 Grass Hay The dataset used to estab lish a tolerance for bromoxy nil on grass hay

consisted of field trial data representing total application rates of 0.4 3 - 0. 45 lb ai/A (2 applications at ~0.22 lb ai/A/application) with PHI s of 28 - 31 day s. As specified by the Guidance for Setting Pesticide Tolerances Based on Field Trial Data (SOP), the field trial application rates and PHI s are within 25% of the maximum label application rate and minimum label PHI , respectively . The residue values that were entered into the tolerance spreadsheet are provided below. Three of the 24 field trial sample results for grass hay were between the LOD (0.00287) and the LOQ (0.01 ppm); the reported values were used. Maximum likelihood estimation (MLE) procedures were not used. Visual inspection of the lognormal pro bability plot and the results from the approximate Shapiro Francia Normality

test indicate that the dataset for grass hay i s lognormal. S ince the dataset was large (greater than 15 samples) and reasonabl y lognormal , the minimum of the 95% upper confidence limit (UCL) on the 95 th 

### percentile and the point estimate of the 99 th 

### percentile was selected as the tolerance value . Using the tolerance spreadsheet, the recommended to lerance f or grass hay is 5.0 ppm.Bromoxynil Summary of Analytical Chemistry and Residue Data DP#: 378614



### Page 39 of 58 Regulator: EPA Chemical: Bromoxynil Crop: Grass hay PHI: 28 - 31 days App. Rate: 0.43 - 0.45 lb ai/A Submitter: Bayer CropScience

Residues LN(Residues) Z scores 0.004 - 5.42 - 1.95 0.006 - 5.04 - 1.50 0.008 - 4.79 - 1.24 0.063 - 2.76 - 0.60 0.084 - 2.47 - 0.05 0.034 - 3.38 - 0.73 0.028 - 3.59 - 0.88 0.848 - 0.16 1.24 0.772 - 0.26 1.04 0.075 - 2.59 - 0.26 0.071 - 2.64 - 0.37 0.093 - 2.37 0.05 0.099 - 2.31 0.16 0.012 - 4.45 - 1.04 0.189 - 1.67 0.48 0.374 - 0.98 0.88 1.850 0.62 1.50 2.260 0.82 1.95 0.346 - 1.06 0.73 0.258 - 1.35 0. 60 0.183 - 1.70 0.37 0.175 - 1.74 0.26 0.064 - 2.76 - 0.48 0.083 - 2.49 - 0.16Bromoxynil Summary of Analytical Chemistry and Residue Data DP#: 378614



### Page 40 of 58 Regulator: EPA Chemical: Bromoxynil Crop: Grass hay PHI: 28-31 days App. Rate: 0.43-0.45 lb ai/A Submitter: Bayer CropScience

n: 24 min: 0.00 max: 2.26 median: 0.09 average: 0.33 95th Percentile 99th Percentile 99.9th Percentile 1.3 1.7 2.5 (1.7) (2.5) (--) 1.6 5.0 18 (5.0) (25) (--) 0.70 2.5 0.50 0.9776 p-value > 0.05 : Do not reject lognormality assumption Approximate Shapiro-Francia Normality Test EU Method I Normal

UCLMedian95th 95/99 Rule EU Method II Distribution-Free Mean+3SD

99.9 99 98 95 90 80 70 50 30 20 10 5 2 1 0.1 3.0000 1.5000 0.7500 0.3750 0.1875 0.0938 0.0469 0.0234 0.0117 0.0059 0.0029 y = 1.7005x - 2.2739 R2 = 0.9776Concentrations

Percentiles Log nor ma l Pro

bab il ity

Plot EPA Bro moxynil Grass hay 28 - 31 d ays ...Bromoxynil Summary of Analytical Chemistry and Residue Data DP#: 378614



### Page 41 of 58 Sorghum Grain The dataset used to establish a tolerance for bromoxy nil on sorghum grain consisted of field trial data representing a total application rate of 0. 44 lb ai/A (2 applications at 0.22 lb ai/A/application) with PHI s of 56 - 60 day s. As specified by the Guidance for Setting Pesticide Tolerances Based on Field Trial Data (SOP), the field trial application rates and PHI s are within 25% of the maximum label application rate and minimum label PHI , respectively . The residue values that were entered into the tolerance spreadsheet are provided below. Eleven of the 24 field trial sample results for sorghum grain were below the LOQ (<0.01 ppm). M aximum likeliho od estimation (MLE) procedures were needed to impute censored values. Visual inspection of the lognormal probability plot and the results from the approximate Shapiro Francia Normality

test indicate that the dataset for sorghum grain is lognormal. Since the dataset was large (greater than 15 samples) and reasonably lognormal , the minimum of the 95% upper confidence limit (UCL) on the 95 th 

### percentile and the point estimate of the 99 th 

### percentile was selected as the tolerance value . Using the tolerance spreadsheet, the recommended tolerance for sorghum grain is 0.2 0 ppm.Bromoxynil Summary of Analytical Chemistry and Residue Data DP#: 378614



### Page 42 of 58 Regulator: EPA Chemical: Bromoxynil Crop: Sorghum grain PHI: 56 - 60 days App. Rate: 0.44 lb ai/A Submitter: Bayer CropScience

Residues LN(Residues) Z scores 0.003 - 5.72 - 1.95 0.004 - 5.47 - 1.50 0.005 - 5.31 - 1.24 0.006 - 5.18 - 1.04 0.006 - 5.08 - 0.88 0.007 - 4.99 - 0.73 0.007 - 4.91 - 0.60 0.008 - 4.84 - 0.48 0.008 - 4.78 - 0.37 0.009 - 4.72 - 0.26 0.009 - 4.66 - 0.16 0.013 - 4.38 0.16 0.011 - 4.48 0.05 0.035 - 3. 37 0.60 0.040 - 3.21 0.88 0.082 - 2.50 1.24 0.067 - 2.71 1.04 0.018 - 4.02 0.26 0.019 - 3.99 0.37 0.010 - 4.59 - 0.05 0.105 - 2.25 1.95 0.101 - 2.29 1.50 0.035 - 3.34 0.73 0.030 - 3.52 0.48Bromoxynil Summary of Analytical Chemistry and Residue Data DP#: 378614



### Page 43 of 58 Regulator: EPA Chemical: Bromoxynil Crop: Sorghum grain PHI: 56-60 days App. Rate: 0.44 lb ai/A Submitter: Bayer CropScience

n: 24 min: 0.00 max: 0.11 median: 0.01 average: 0.03 95th Percentile 99th Percentile 99.9th Percentile 0.08 0.10 0.15 (0.10) (0.15) (--) 0.09 0.20 0.40 (0.20) (0.45) (--) 0.08 0.15 0.06 0.9390 p-value > 0.05 : Do not reject lognormality assumption Approximate Shapiro-Francia Normality Test EU Method I Normal

UCLMedian95th 95/99 Rule EU Method II Distribution-Free Mean+3SD

99.9 99 98 95 90 80 70 50 30 20 10 5 2 1 0.1 1.0000 0.5000 0.2500 0.1250 0.0625 0.0313 0.0156 0.0078 0.0039 0.0020 y = 1.0433x - 4.1798 R2 = 0.939Concentrations

Percentiles Log nor ma l P robab il ity

P lot EPA Bro moxynil Sorghum

grain 56 - 60 da

ys ...Bromoxynil Summary of Analytical Chemistry and Residue Data DP#: 378614



### Page 44 of 58 Sorghum Forage The dataset used to estab lish a tolerance for bromoxy nil on sorghum forage consisted of field trial data representing a total application rate of 0.43 - 0.44 lb ai/A (2 applications at ~ 0.22 lb ai/A/application) with PHI s of 5 - 8 days . As specified by the Guidance for Setting Pestic ide Tolerances Based on Field Trial Data (SOP), the field trial application rates and PHI s are within 25% of the maximum label application rate and minimum label PHI , respectively . The residue values that were entered into the tolerance spreadsheet are provided below. All 24 field trial sample results for sorghum forage were above the LOQ (>0.01 ppm). M aximum likelihood estimation (MLE) procedures were not needed to impute censored values. Visual inspection of the lognormal probability plot and the res ults from the approximate Shapiro Francia Normality

test indicate that the dataset for sorghum forage is not lognormal. The “Mean + 3SD ” m ethod was used to calculate the tolerance for the data set. The tolerance value calculated using the “Mean + 3 SD” m ethod represents an upper bound estimate of the 89 th 

### percentile for any distribution. Using the tolerance spreadsheet, th e recommended tolerance f or sorghum forage is 0.8 0 ppm.Bromoxynil Summary of Analytical Chemistry and Residue Data DP#: 378614



### Page 45 of 58 Regulator: EPA Chemical: bromoxynil Crop: Sorghum

forage PHI: 5 - 8 days App. Rate: 0.43 - 0.44 lb ai/A Submitter: Bayer CropScience

Residues LN(Residues) Z scores 0.072 - 2.64 - 1.95 0.072 - 2.63 - 1.50 0.107 - 2.23 - 0.73 0.103 - 2.27 - 0.88 0.469 - 0.76 0.88 0.411 - 0.89 0.37 0.203 - 1.59 - 0.48 0.169 - 1.78 - 0 .60 0.465 - 0.77 0.73 0.471 - 0.75 1.04 0.284 - 1.26 - 0.05 0.325 - 1.12 0.26 0.083 - 2.49 - 1.24 0.098 - 2.32 - 1.04 0.282 - 1.27 - 0.16 0.418 - 0.87 0.60 0.542 - 0.61 1.50 0.609 - 0.50 1.95 0.515 - 0.66 1.24 0.417 - 0.87 0.48 0.284 - 1.26 0.05 0.268 - 1.32 - 0.37 0.279 - 1.28 - 0.26 0.297 - 1.21 0.16Bromoxynil Summary of Analytical Chemistry and Residue Data DP#: 378614



### Page 46 of 58 Regulator: EPA Chemical: bromoxynil Crop: Sorghum forage PHI: 5-8 days App. Rate: 0.43-0.44 lb ai/A Submitter: Bayer CropScience

n: 24 min: 0.07 max: 0.61 median: 0.28 average: 0.30 95th Percentile 99th Percentile 99.9th Percentile 0.60 0.70 0.90 (0.70) (0.90) (--) 0.80 1.3 2.5 (1.3) (2.5) (--) 1.0 0.80 1.5 0.9020 0.05 >= p-value > 0.01 : Reject lognormality assumption Approximate Shapiro-Francia Normality Test EU Method I Normal

UCLMedian95th 95/99 Rule EU Method II Distribution-Free Mean+3SD

Lognormal Probability Plot

99.9 99 98 95 90 80 70 50 30 20 10 5 2 1 0.1 1.0000

0.5000

0.2500

0.1250

0.0625 y = 0.6767x - 1.3899 R 2 = 0.902

PercentilesConcentrations EPA bromoxynil Sorghum forage 5-8 days 0.43-0.44 lb ai/A Bayer CropScienceBromoxynil Summary of Analytical Chemistry and Residue Data DP#: 378614



### Page 47 of 58 Sorghum Stover The dataset used to establish a tolerance for bromoxy nil on sorghum stover consisted of field trial data representing a total application rate of 0.44 lb ai/A (2 application s at 0.22 lb ai/A/application) with PHI s of 56 - 60 day s. As specified by the Guidance for Setting Pesticide Tolerances Based on Field Trial Data (SOP), the field trial application rates and PHI s are within 25% of the maximum label application rate and mini mum label PHI , respectively . The residue values that were entered into the tolerance spreadsheet are provided below. All 24 field trial sample results for sorghum forage were above the LOQ (>0.01 ppm). M aximum likelihood estimation (MLE) procedures were not needed to impute censored values. Visual inspection of the lognormal probability plot and the results from the approximate Shapiro Francia Normality

test indicate that the dataset for sorghum stover is not lognormal. The “Mean + 3SD ” m ethod was use d to calculate the tolerance for the data set. The tolerance value calculated using the “Mean + 3SD” method represents an upper bound estimate of the 89 th 

### percentile for any distribution. Using the tolerance spreadsheet, the recommended tolerance for sorghum stover is 0.20 ppm.Bromoxynil Summary of Analytical Chemistry and Residue Data DP#: 378614



### Page 48 of 58 Regulator: EPA Chemical: bromoxynil Crop: Sorghum

stover PHI: 56 - 60 days App. Rate: 0.44 lb ai/A Submitter: Bayer CropScience

Residues LN(Residues) Z scores 0.011 - 4.52 - 1.50 0.015 - 4.19 - 1.04 0.018 - 4.02 - 0.88 0.023 - 3.79 - 0.73 0.075 - 2.60 0.37 0.074 - 2.61 0.26 0.103 - 2.27 1.24 0.061 - 2.79 0.05 0.059 - 2.83 - 0.05 0.088 - 2.44 0.88 0.108 - 2.23 1.50 0.085 - 2.47 0.60 0.053 - 2.95 - 0.48 0.059 - 2.83 - 0.16 0.013 - 4.35 - 1.24 0.011 - 4.55 - 1 .95 0.082 - 2.50 0.48 0.110 - 2.21 1.95 0.058 - 2.85 - 0.37 0.087 - 2.45 0.73 0.049 - 3.02 - 0.60 0.059 - 2.83 - 0.26 0.101 - 2.29 1.04 0.062 - 2.79 0.16Bromoxynil Summary of Analytical Chemistry and Residue Data DP#: 378614



### Page 49 of 58 Regulator: EPA Chemical: bromoxynil Crop: Sorghum stover PHI: 56-60 days App. Rate: 0.44 lb ai/A Submitter: Bayer CropScience

n: 24 min: 0.01 max: 0.11 median: 0.06 average: 0.06 95th Percentile 99th Percentile 99.9th Percentile 0.15 0.15 0.20 (0.15) (0.20) (--) 0.20 0.30 0.60 (0.30) (0.60) (--) 0.20 0.20 0.35 0.8357 p-value <= 0.01: Reject lognormality assumption Approximate Shapiro-Francia Normality Test EU Method I Normal

UCLMedian95th 95/99 Rule EU Method II Distribution-Free Mean+3SD

Lognormal Probability Plot

99.9 99 98 95 90 80 70 50 30 20 10 5 2 1 0.1 1.0000 0.5000 0.2500 0.1250 0.0625 0.0313 0.0156 0.0078 y = 0.7241x - 3.0143 R 2 = 0.8357

PercentilesConcentrations EPA bromoxynil Sorghum stover 56-60 days 0.44 lb ai/A Bayer CropScienceBromoxynil Summary of Analytical Chemistry and Residue Data DP#: 378614



### Page 50 of 58 Appendix IV Livestock Anticipated Residue Calculations for Dietary Exposure Assessm ent Livestock Anticipated Residues - Chronic and Cancer

Table 1. Livestock Anticipated Residues for Chronic and Cancer Assessments Comm odity Recommended/ Established Tolerance (ppm) Average Field

Trial Residue (ppm) % Crop

Treated (average) Anticipate d Residue in

DEEM Run (ppm) Plant Commodities Alfalfa, hay Alfalfa, m eal 0.5

-- 0.13

- -- 5 <1

-- --

0.0013 Barley, grain 0.05 0.01 1 20 0.002 Barley, hay 9.0 0.43 8 20 0.086 Corn, field, grain 0.05 0.01 7 <2.5 0.00025 Corn, pop, grain 0.05 0.01 7 <2.5 0.0 0025 Cotton, gin byproducts 7.0 3.2 6 <2.5 0.08 Cotton, m eal -- 0.10 6 <2.5 0.0025 Cotton, undelinted seed 1.5 0.30 6 <2.5 0.0075 Flax, seed 0.1 <0.01 9 100 0.01 Garlic 0.1 0.01 2 50 0.005 Oat, grain 0.05 0.01 1 5 0.0005 Onion, bulb 0.1 0.01 2 55 0.0055 Peppermint, hay Peppermint, oil 0.1

-- --

0.03 3 100

-- --

0.03 Rye, grain 0.05 0.01 1 100 0.01 Sorghum, grain, grain 0.2 0.028 4 <2.5 0.0007 Spearmint, hay Spearmint, oil 0.1

-- --

0.03 3 100

-- --

0.03 Wheat, grain 0.05 0.01 1 15 0.0015 Livestock Commodities Cattle, fat 1 --- 0.0024 Cattle, meat byproducts 3.5 Kidney 0.0081 Liver 0.0070 Cattle, meat 0.5 0.0013 Egg 0.05 0.000078 Goat, fat 1 0.0024 Goat, meat byproducts 3.5 Kidney 0.0081 Liver 0.0070 Goat, meat 0.5 0.0013 Hog, fat 1 0.00015 Hog, meat byproducts 3.5 Kidney 0.00051 Liver 0.00044 Hog, meat 0.5 0.000083 Horse, fat 1 0.0024 Horse, meat byproducts 3.5 Kidney 0.0081 Liver 0.0070 Horse, meat 0.5 0.0013 Milk 0.4 0.00054 Poultry, fat 0.0 5 0.00013 Poultry, meat byproducts 0.3 Liver 0.00099Bromoxynil Summary of Analytical Chemistry and Residue Data DP#: 378614



### Page 51 of 58 Poultry, meat 0.05 0.000078 Sheep, fat 1 0.0024 Sheep, meat byproducts 3.5 Kidney 0.0081 Liver 0.0070 Sheep, meat 0.5 0.0013 1 DP Number 235876, C. Swartz, 5/14/97, DP Number 234836, C. Swartz, 4/3/97, DP Number 233336, C. Swartz, 3/20/97, and DP Number 228201, C. Swartz, 7/29/96. Residue data for wheat and barley grains were translated to oats and rye. All residues in wheat and barley grains were <0.02 ppm (<LOQ), except for one residue of 0.03 ppm in barley grain which was considered to be anomalous. Therefore, the anticipated residue for grain of barley, oat, rye and wheat is 0.01 ppm, or 1⁄2 LOQ (LOQ = 0.02 ppm). Since residues do not concentrate in processed commodities of cereal grains, the anticipated residue of 0.01 ppm should be used for the processed commodities of cereal grains in DEEM. 2 DP Number 235876, C. Swartz, 5/14/97, DP Number 234836, C. Swartz, 4/3/97, DP Number 233336, C. Swartz, 3/20/97, and DP Number 228201, C. Swartz, 7/29/96. Residue data on onions were translated to garlic. Residues on onions were <0.02 ppm (<LOQ). Therefore, the anticipated residue for onions and garlic is 0.01 ppm, or 1⁄2 LOQ (LOQ = 0.02 ppm). 3 DP Number 235876, C. Swartz, 5/14/97, DP Numbe r 234836, C. Swartz, 4/3/97, and DP Number 233336, C. Swartz, 3/20/97. A processing reduction factor of 3x applies to mint oil. 4 DP Number 380770, T. Goodlow , 8/17/10, MRID 47815002 (grain sorghum) and MRID 47815001 (grass). The average residue was use d for the chronic assessment. 5 DP Number 195998, C. Swartz, 3/6/96, MRIDs 00150382, 42950101; MRID 44386601. In the calculation of the average residues for alfalfa hay, 0.02 ppm was used for residues reported as <0.02 ppm. For alfalfa meal, the alfalfa hay residues and percent crop treated values are used (OPPTS 860.1000). 6 DP Number 44458900, C. Swartz, 3/2/98. A 0.3x reduction factor is applicable to cottonseed meal based on a processing study. Residues reflect the maximum seasonal rate of 1.5 lb ai/A and a 75 - day PHI. 7 DP Number 191340, C. Swartz, 10/24/94, MRID 42757601 and D183667, S. Knizner, 11/13/92, MRID 42501601; MRID 44386601. All residues in corn grain were <0.02 ppm (<LOQ). Therefore, the anticipated residue for corn grain is 0.01 ppm , or 1⁄2 LOQ (LOQ = 0.02 ppm). 8 MRID 44386601. The residue data on barley hay which are used reflect the recommended 45 - day PHI. 9 DP Number 178167, S. Knizner, 10/29/92, MRID 42283201). All residues in flax seed were <0.02 ppm. Therefore, the anticipated residue for flax seed is 0.01 ppm, or 1⁄2 LOQ (LOQ = 0.02 ppm). Since residues do not concentrate in processed commodities of flax seed, the anticipated residue of 0.01 ppm should be used for the processed commodities of flax seed.Bromoxynil Summary of Analytical Chemistry and Residue Data DP#: 378614



### Page 52 of 58 Livestock Anticipated Residues - Acute

Table 2. Livestock Anticipated Residues for Acute Assessments Comm odity Established/ Recommended Tolerance

(ppm) Residue to be Used in Acute DEEM Run Alfalfa, hay Alfalfa, m eal (partially blended) 0.5

- - - 5 HAFT 0.25 5 MAX 0 .38 5 AV 0.13 5 Barley, grain (blended) 0.05 0.01 1 Barley, hay (partially blended) 9.0 HAFT 3.7 8 MAX 4.29 8 AV 0.43 8 Corn, field, grain 0.05 0.01 7 Corn, pop, grain 0.05 0.01 7 Cotton, gin byproducts (partially blended) 7.0 HAFT 6.4 6 MAX 6.5 6 AV 3.2 6 Cotton, m eal 10 (blended) -- HAFT 0.31 6 MAX 0.33 6 AV 0.10 6 Cotton, undelinted seed (blended) 1.5 HAFT 1.03 6 MAX 1.11 6 AV 0.30 6 Flax, seed 0.1 0.01 9 Garlic 0.1 0.1 2 Oat, grain 0.05 0.01 1 Onion, bulb 0.1 0.1 2 Peppermint, hay Peppermint, oil 0.1

-- 3 -- 0.03 3 Rye, grain 0.05 0.01 1 Sorghum, grain, grain (blended) 0.2 HAFT 0.103 4 MAX 0.11 4 AV 0.028 4 Spearmint, hay Spearmint, oil 0.1

-- 3 -- 0.03 3 Wheat, grain 0.05 0.01 1 Livestock Commodities Cattle, fat 1 0.13 Cattle, meat byproducts 3. 5 Kidney 0.43 Liver 0.38 Cattle, meat 0.5 0.070 Egg 0.05 0.0038 Goat, fat 1 0.13 Goat, meat byproducts 3.5 Kidney 0.43 Liver 0.38 Goat, meat 0.5 0.070 Hog, fat 1 0.0062 Hog, meat byproducts 3.5 Kidney 0.020 Liver 0.018 Hog, meat 0.5 0.0033 Horse, fat 1 0.13 Horse, meat byproducts 3.5 Kidney 0.43 Liver 0.38 Horse, meat 0.5 0.070Bromoxynil Summary of Analytical Chemistry and Residue Data DP#: 378614



### Page 53 of 58 Milk 0. 4 0.0032 Poultry, fat 0.05 0.0061 Poultry, meat byproducts 0.3 Liver 0.048 Poultry, meat 0.05 0.0038 Sheep, fat 1 0.13 Sheep, meat byproducts 3.5 Kidney 0.43 Liver 0.38 Sheep, meat 0.5 0.070 1 DP Number 235876, C. Swartz, 5/14/97, DP Number 234836, C. Swartz, 4/3/97, DP Number 233336, C. Swartz, 3/20/97, and DP Number 228201, C. Swartz, 7/29/96. Residue data from wheat and barley we re translated to oats and rye and also used for corn grain. All residues were <0.02 ppm (<LOQ), except for one residue of 0.03 ppm in barley grain which was considered to be anomalous. Since barley, oats, and wheat grain are considered to be blended, the anticipated residue for the grain of barley, oats, rye and wheat for the acute assessment is 0.01 ppm, or 1⁄2 LOQ (LOQ = 0.02 ppm). Since residues do not concentrate in processed commodities of cereal grains, the anticipated residue of 0.01 ppm should be u sed for the processed commodities of cereal grains in DEEM. 2 DP Number 235876, C. Swartz, 5/14/97, DP Number 234836, C. Swartz, 4/3/97, and DP Number 233336, C. Swartz, 3/20/97. Since garlic and onions are not considered to be blended, the tolerance l evel of 0.1 ppm should be used for the acute assessment. 3 DP Number 235876, C. Swartz, 5/14/97, DP Number 234836, C. Swartz, 4/3/97, DP Number 233336, C. Swartz, 3/20/97. A separate tolerance is not established for mint oil since residues decrease on pr ocessing. A processing reduction factor of 3x applies to mint oil (0.1 ppm x 1/3 = 0.03 ppm). 4 DP Number 380770, T. Goodlow , 8/17/10, MRID 47815002 (grain sorghum). 5 DP Number 195998, C. Swartz, 3/6/96, MRIDs 00150382, 42950101 (alfalfa); MRID 443866 01. In the calculation of the average residues for alfalfa hay, 0.02 ppm was used for residues reported as <0.02 ppm. For alfalfa meal, the alfalfa hay residues are used (OPPTS 860.1000). 6 DP Number 44458900, C. Swartz, 3/2/98. A 0.3x reduction factor is applicable to cottonseed meal based on a processing study. Residues reflect the maximum seasonal rate of 1.5 lb ai/A and a 75 - day PHI. 7 DP Number 191340, C. Swartz, 10/24/94, MRID 42757601 and DP Number 183667, S. Knizner, 11/13/92, MRID 42501601 (c orn). All residues in corn grain were <0.02 ppm (<LOQ). Therefore, the anticipated residue for corn grain is 0.01 ppm, or 1⁄2 LOQ (LOQ = 0.02 ppm). 8 Barley. MRID 44386601. The residue data on barley hay which are used reflect the recommended 45 - day PH I. 9 DP Number 178167, S. Knizner, 10/29/92, MRID 42283201. All residues in flax seed were <0.02 ppm. Since flax is considered to be blended, the anticipated residue for flax seed for the acute assessment is 0.01 ppm, or 1⁄2 LOQ (LOQ = 0.02 ppm). Since residues do not concentrate in processed commodities of flax seed, the anticipated residue of 0.01 ppm should be used for the processed commodities of flax seed.Bromoxynil Summary of Analytical Chemistry and Residue Data DP#: 378614



### Page 54 of 58 Dairy Cattle and Poultry Feeding Studies Cattle and poultry

feeding studies were previous ly reviewed (DP Number 232957, G. F. Kramer, 3/11/97). Results of the feeding studies with both feeding levels and residues reported as bromox yn il per se (DP Number 239914, C. Swartz, 1/20/98) are reported below: Table 3. Average Brom oxynil Residues in Cattle Tissues Feeding Level (ppm) Average Brom oxynil Residues (ppm) Milk Liver Kidney Fat Muscle 4.2 0.05 1.97 2.26 0.68 0.37 12.6 0.14 4.04 5.89 2.11 0.86 42.0 0.48 10.65 16.26 4.75 2.59

Table 4 . Average Brom oxynil Residues in Poultry Tissues Feeding Level (ppm) Average Brom oxynil Residues (ppm) Liver Muscle Skin & Fat 0.07 0.063 Not analyzed Not analyzed 0.21 0.083 <0.05 <0.05 0.70 0.21 0.05 0.08 1 Residues in eggs were not detectable ( <0.05 p pm) at the highest feeding level ( 0.70 ppm). 

### Calculation of Anticipated Residues for Livestock Commodities - Chronic and Cancer Assessments Table 5 . Livestock Feed Items for Chronic Assessment Comm odity Recommended/ Established Tolerance (ppm) Average Field

Trial Residue (ppm) % Crop

Treated (av erage) Anticipated

Residue (ppm) Alfalfa, meal -- 1 0.13 <1 0.0013 Barley, grain 0.05 0.01 20 0.002 Barley, hay 9.0 0.43 20 0.086 Cotton, gin byproducts 7.0 3.2 <2.5 0.08 Cotton, meal -- 2 0.10 <2.5 0.0025 Cotton, undelinted seed 1.5 0.30 <2.5 0.0075 Sorghum, grain, grain 0.2 0.028 <2.5 0.0007 1 Residues in alfalfa hay are used for alfalfa meal. In this table, the alfalfa hay tolerance is used for alfalfa meal. 2 No separate tolerance is established for cotton meal. A 0.3x reduction factor is app lied to undelinted cotton seed residues to obtain average residues in cotton meal.Bromoxynil Summary of Analytical Chemistry and Residue Data DP#: 378614



### Page 55 of 58 Table 6 . Brom oxynil Dietary Contributions for Chronic Assessment u sing Average Residues fromField Trials as Anticipated Residues (AR)

% Diet Dietary Contributions (ppm) 

### Feedstuff Type AR, ppm 1 % Dry Matter Beef Dairy Poultry Swine Beef Diary Poultry 2 Swine 2 Barley, hay R 0.086 88 10 45 -- -- 0.0098 0.044 -- -- Cotton byproducts R 0.08 90 5 -- -- -- 0.0044 -- -- -- Grain sorghum, grain CC 0.0007 86 40 45 75 80 0.00032 0.00036 0.00052 0.00056 Barley grain CC 0.002 88 40 -- -- 5 -- -- Cotton, undelinted seed PC 0.0075 88 Nu 10 Nu Nu -- 0.00085 -- -- Cotton meal PC 0.0025 89 5 -- 20 15 0.00014 -- 0.00050 0.00038 Alfalfa meal PC 0.0013 89 Nu -- 5 -- -- - - 0.000065 -- Totals 100 100 100 100 0.015 0.045 0.0011 0.00094

1 The anticipated residues for livestock feed items are the average residues from field trials. 2 Poultry and swine calculations do not include division by percent dry matter. 

### Calculati on of Anticipated Residues for Livestock Commodities
– Acute Assessment Table 7 . Livestock Feed Items for Acute Analysis for Beef Cattle, Poultry, and Swine Comm odity Recommended/

Established Tolerance (ppm) Anticipated Residue (ppm) 1 Alfalfa, meal 2

- - 4 0.25 Barley, grain 3 0.05 0.01 Barley, hay2 9.0 3.7 Cotton, gin byproducts 2 7.0 6.4 Cotton, meal 3

-- 5 0.10 Cotton, undelinted seed 3 1.5 0.30 Sorghum, grain, grain 3 0.2 0.028 1 In an acute analysis for beef cattle, poultry, and swine, average fiel d trial residues can be used for blended commodities and the highest average field trial (HAFT) values can be used for partially blended and nonblended commodities (Dietary Exposure Science Advisory Council, September 2009, Dietary Exposure Analysis ). 2 Partially blended (Stasikowski, M., 8/20/99, Classification of Food Forms with Respect to Level of Blending. HED Standard Operating Procedure 99.6 ) 3 Blended (SOP 99.6) 4/Alfalfa meal is included in the livestock diet using the alfalfa hay tolerance (OPPTS 860.1000). The alfalfa hay tolerance is 0.5 ppm. 5 The cotton, undelinted seed tolerance is 1.5 ppm and is adequate to cover residues in cotton meal.Bromoxynil Summary of Analytical Chemistry and Residue Data DP#: 378614



### Page 56 of 58 Table 8 . Brom oxynil Dietary Contributions for Acute Assessment for Beef Cattle, Poultry, and Swine Usi ng Average Field Trial Residues for Blended Commodities and the Highest Average Field Trial (HAFT) Values for Partially Blended and Nonblended Commodities % Diet b Dietary Contributions (ppm) 

### Feedstuff Type AR, ppm 1 % Dry Matter Beef Poultry Swine Beef Poultry Swine Barley, hay R 3.7 88 10 -- -- 0.42 -- -- Cotton, gin byproducts R 6.4 90 5

-- -- -- 0.36 -- -- Grain sorghum, grain CC 0.028 86 40 75 80 0.013 0.021 0.022 Barley grain CC 0.01 88 40 -- 5 0.0045 -- 0.0005 Cotton, undelinted see d PC 0.30 88 Nu Nu Nu -- -- -- Cotton meal PC 0.10 89 5 20 15 0.0056 0.02 0.015 Alfalfa meal PC 0.25 89 Nu 5 -- -- 0.012 -- Totals 100 100 100 0.80 0.053 0.038

Table 9. Livestock Feed Items for Acute Assessment for Dairy Cattle Comm odity Recom mended/ Established Tolerance (ppm) Anticipated Residue (ppm) 1 Alfalfa, meal -- 2 0.13 Barley, grain 0.05 0.01 Barley, hay 9.0 0.43 Cotton, gin byproducts 7.0 3.2 Cotton, meal -- 3 0.10 Cotton, undelinted seed 1.5 0.30 Sorghum, grain, grain 0.2 0.02 8 1 In an acute analysis for dairy cattle, tolerance level residues may be replaced with average field trial residues for blended, nonblended, and partially blended feed items commodities (Dietary Exposure Science Advisory Council, September 2009, Dietary Exposure Analysis ). 2/Alfalfa meal is included in the livestock diet using the alfalfa hay tolerance (OPPTS 860.1000). The alfalfa hay tolerance is 0.5 ppm. 3 The cotton, undelinted seed tolerance is 1.5 ppm and is adequate to cover residues in cotton me al.Bromoxynil Summary of Analytical Chemistry and Residue Data DP#: 378614



### Page 57 of 58 Table 10 . Brom oxynil Dietary Contributions for Acute Assessment for Dairy Cattle using Average Field Trial Residues for Blended, Nonblended, and Partially Blended Commodities % Diet b Dietary Contributions (ppm) 

### Feedstuff Type AR, ppm 1 % Dry Matter Dairy Diary Barley, hay R 0.43 88 45 0.22 Cotton, gin byproducts R 3.2 90 -- -- Grain sorghum, grain CC 0.028 86 45 0.015 Barley grain CC 0.01 88 -- -- Cotton, undelinted seed PC 0.30 88 10 0.034 Cotton meal PC 0.10 89 -- -- Alfalfa meal PC 0.13 89 -- -- Totals 100 0.269 

### Anticipated Residues in Meat and Milk for Use in DEEM Chronic Anticipated Residues Table 11 . Transfer Coefficients and Chronic Anticipated Residues of Brom oxynil in Dairy Cattle Comm odities Matrix Feeding L evel

(ppm) Maximum Residu es

at Feeding Level (ppm) Transfer

Coefficient 1 Calculated Dietary

Burden (ppm) Calculated

Anticipated Residues (ppm) 2 Milk 4.2 0.05 0.012 0.045 0.00054 1 Obtained by dividing the maximum residues at the feeding level by the feeding level. 2 Obtained by multiplying the transfer coefficient by the calculated dietary burden. Table 12 . Transfer Coefficients and Chronic Anticipated Residues of Brom oxynil in Beef Cattle Comm odities Matrix Feeding Level

(ppm) Maximum Residu es

at Feeding Level (ppm) Transfer

Coefficient 1 Calculated Dietary

Burden (ppm) Calculated

Anticipated Residues (ppm) 2 Fat 4.2 0.68 0.16 0.015 0.0024 Kidney 2.26 0.54 0.0081 Liver 1.97 0.47 0.0070 Muscle 0.37 0.088 0.0013 1 Obtained by dividin g the maximum residues at the feeding level by the feeding level. 2 Obtained by multiplying the transfer coefficient by the calculated dietary burden. Table 13 . Transfer Coefficients and Chronic Anticipated Residues of Brom oxynil in Poultry Commodities Matrix Feeding Level

(ppm) Maximum Residu es

at Feeding Level (ppm) Transfer

Coefficient 1 Calculated Dietary

Burden (ppm) Calculated

Anticipated Residues (ppm) 3 Eggs 0.70 <0.05 2 0.071 0.0011 0.000078 Skin/Fat 0.70 0.08 0.11 0.00013 Liver 0.07 0.063 0.90 0.00099 Muscle 0.70 0.05 0.071 0.000078 1 Obtained by dividing the maximum residues at the feeding level by the feeding level. 2 Residues in eggs were <0.05 ppm at the highest feeding level (1.0 ppm). 3 Obtained by multiplying the transfer coefficient by the calculated dietary burden.Bromoxynil Summary of Analytical Chemistry and Residue Data DP#: 378614



### Page 58 of 58 Table 14. Transfer Coefficients and Chronic Anticipated Residues of Brom oxynil in Swine Comm odities Matrix Feeding Level

(ppm) Maximum Residu es

at Feeding Level (ppm) Transfer

Coefficient 1 Calcu lated Dietary

Burden (ppm) Calculated

Anticipated Residues (ppm) 2 Fat 4.2 0.68 0.16 0.00094 0.00015 Kidney 2.26 0.54 0.00051 Liver 1.97 0.47 0.00044 Muscle 0.37 0.088 0.000083 1 Obtained by dividing the maximum residues at the feeding level by the feeding level. 2 Obtained by multiplying the transfer coefficient by the calculated dietary burden. 

### Acute Anticipated Residues Table 15 . Transfer Coefficients and Acute Anticipated Residues of Brom oxynil in Dairy Cattle (Milk) Matrix Feeding Level

(ppm) Maximum Residu es

at Feeding Level (ppm) Transfer

Coefficient 1 Calculated Dietary

Burden (ppm) Calculated

Anticipated Residues (ppm) 2 Milk 4.2 0.05 0.012 0.269 0.0032 1 Obtained by dividing the maximum residues at the feeding level by the feeding level. 2 Obtained by multiplying the transfer coefficient by the calculated dietary burden. Table 16 . Transfer Coefficients and Acute Anticipated Residues of Brom oxynil in Beef Cattle Commodities Matrix Feeding Level

(ppm) Maximum Residu es

at Feeding Level (ppm) Transfer

Coefficient 1 Calculated Dietary

Burden (ppm) Calculated

Anticipated Residues (ppm) 2 Fat 4.2 0.68 0.16 0.80 0.13 Kidney 2.26 0.54 0.43 Liver 1.97 0.47 0.38 Muscle 0.37 0.088 0.070 1 Obtained by dividing the max imum residues at the feeding level by the feeding level. 2 Obtained by multiplying the transfer coefficient by the calculated dietary burden. Table 17 . Transfer Coefficients and Acute Anticipated Residues of Brom oxynil in Poultry Commodities Matrix Feeding Level

(ppm) Maximum Residu es

at Feeding Level (ppm) Transfer

Coefficient 1 Calculated Dietary

Burden (ppm) Calculated

Anticipated Residues (ppm) 3 Eggs 0.70 <0.05 2 0.071 0.053 0.0038 Skin/Fat 0.70 0.08 0.11 0.0061 Liver 0.07 0.063 0.90 0.048 Muscle 0.70 0.05 0.071 0.0038 1 Obtained by dividing the maximum residues at the feeding level by the feeding level. 2 Residues in eggs were <0.05 ppm at the highest feeding level (1.0 ppm). 3 Obtained by multiplying the transfer coefficient by the calculated dietary burden. Table 18 . Transfer Coefficients and Acute Anticipated Residues of Brom oxynil in Swine Comm odities Matrix Feeding Level

(ppm) Maximum Residu es

at Feeding Level (ppm) Transfer

Coefficient 1 Calculated Dietary

Burden (ppm) Ca lculated

Anticipated Residues (ppm) 2 Fat 4.2 0.68 0.16 0.038 0.0062 Kidney 2.26 0.54 0.020 Liver 1.97 0.47 0.018 Muscle 0.37 0.088 0.0033 1 Obtained by dividing the maximum residues at the feeding level by the feeding level. 2 Obtained by multiplying the transfer coefficient by the calculated dietary burden.