Bifenazate Summary of Analytical Chemistry and Residue Data DP#: D388800

Page 1 of 22 **UNITED STA TES ENVIRONMENTA**  **L PROTECTION A GENCY** 

**WA SHINGTON, D.C. 20460**  OFFICE OF CHEMICAL SAFETY AND POLLUTION PREVENTION **MEMORANDUM Date:**  15 - May- 20 1 4 **SUBJECT:** Bifenazate. Section 3 Registration Request to Add New Uses on Timothy Forage and Hay ; Herb, Subgroup 19A; and to Expand Existing Uses on Pome Fruit, Group 11, and Fruiting Vegetables, Group 8. **Summary of Analytical Chemistry and**  **Residue Data. PC Code:**  000586 **DP Barcode:** D388800 **Decision No.:** 446177 **Registration Nos. :**  400 - 503, 400 - 514 **Petition No.**  **:** 1E7847 **Regulatory Actions:** Section 3 Registration **Risk Assessment Type:** NA **Case No.:** 7609 **T XR No.:**  NA **CAS No.:** 149877 - 41 - 8 **MRID Nos.:** 48560601, 47327701 **40 CFR:** §180.572 **From:** Will iam D. Wassell, Chemist

Risk Assessment Branch 1 (RAB1) Health Effects Division (HED, 7509P) **Through** : George F. Kramer, Ph.D., Senior Chemist

RAB1/HED (7509P) **To:** William D. Wassell, Risk Assessor

RAB1/HED (7509P) and Barbara Madden , RM 05 Registration Division (RD; 7505P) **Executive Summary** Bifenazate (1 - methylethyl 2 - (4 - methoxy [1,1’ - biphenyl] - 3 - yl )h ydrazinecarboxylate) is a selective miticide/insecticide which controls the motile stage of mites either b y direct contact or through contact with foliar residues. There is conflicting evidence in the literature for bifenazate being a mitochondrial inhibitor or a GABA (gamma - aminobuty ric acid) channel modulator. The Interregional Research Project No. 4 (IR - 4) has submitted a petition proposing the establishment of permanent tolerances for residues of the acaricide bifenazate and its metabolite D3598 [diazinecarbox yl ic acid, 2 - (4 - methoxy- [1,1’biphenyl] - 3 - yl , 1 - methylethyl ester], (expressed as bifenazate) in/on the following raw agricultural commodities (RACs):Bifenazate Summary of Analytical Chemistry and Residue Data DP#: D388800

Page 2 of 22 **Commodity Proposed Tolerance**  Herb Subgroup 19A, fresh leaves 30 ppm Herb Subgroup 19A, dried leaves, except chervil, dried , and chive, dried 140 ppm Fruit, Pome, Group 11 - 10 0.75 ppm Vegetable, Fruiting, Group 8 - 10 2.0 ppm Note: Bifenazate tolerances are established for residues in/on pome fruit (Group 11) and fruiting vegetables (Group 8) at the requested levels. IR - 4 has proposed expanding the existing tolerances to cover additional commodities that are included in the revised crop Groups 11 - 10 and 8 - 10. The petitioner further states that the established tolerances for residues in/on pome fruit, group 11; and fruiting vegetables, group 8 may be deleted upon establishment of the uses and tolerances for residues in/on pom e fruit, group 11 - 10; and fruiting vegetables, group 8 - 10. Additionally , IR - 4 proposes the establishment of tolerances with regional registrations for residues of bifenazate and its metabolite D3598 in/on the following RACs:

**Commodity Proposed Toleran**  **ce** Timothy, forage 140 ppm Timothy, hay 120 ppm The end - use products (EPs) relevant to this registration request are Acramite ® 50WS (EPA Reg. No. 400 - 503 ) , a 50% by

weight wettable - powder (WP) in water - soluble bags (WSP), and Acramite ® 4SC (EPA Reg. No. 400 - 514), a 4 lb/gal s uspension - concentrate (SC) formulation [equivalent to a flowable - concentrate (FlC) formulation]. IR - 4 has proposed one foliar spray application to herbs and timothy by ground or aerial (timothy only) equipment at a rate of 0.38 to 0.50 lb ai/A to herbs and 0.43 to 0. 7 5 lb ai/A for timothy . The proposed pre - harvest intervals (PHIs) are 0 day s for timothy forage, 7 day s for timothy hay , and 3 day s for herbs. The established use pattern for pome fruit and fruiting vegetables is one application using ground equipment at a maximum rate of 0.38 to 0.50 lb ai/A with PHI s of 3 and 7 day s for fruiting vegetables and pome fruit, respectivel y. Application by aerial equipment is permitted for fruiting vegetables . Tolerances are established (40 CFR §180.572(a)(1) ) for residues of bifenazate and its metabolite D3598 (expressed as bifenazate) in/on various crops and livestock commodities (fat only). Additionally , tolerances are established (40 CFR §180.572(a)(2)) for residues of bifenazate and the metabolites D3598 (expressed as bifenazate), A1530 (1,1 ′ - biphenyl , 4 - ol) and A1530 - sulfate (1,1 ′ - biphenyl, 4 - oxy sulfonic acid) (expressed as 1,1 ′ - biphenyl , 4 - ol) (expressed as ,1 ′ - biphenyl , 4 - ol) i n milk and livestock tissues (excluding fat). Time - limited tolerances are established (40 CFR §180.572(b)) for residues of bifenazate and D3598 in/on timothy forage at 50 ppm and timothy hay at 150 ppm. These tolerances will expire on 12/31/201 6 . Additi onal plant metabolism data have not been submitted. The qualitative nature of the residue in plants is adequatel y understood based on acceptable studies with apple, orange, cotton, and radish. A briefing document, summarizing the studies (except the radi sh study) was presented to the Metabolism Assessment Review Committee (MARC). The MARC concluded that forBifenazate Summary of Analytical Chemistry and Residue Data DP#: D388800

Page 3 of 22 tolerance expression and risk assessment purposes, the residues of concern in crops are bifenazate and its metabolite D3598 (calculated as the stoich iometric equivalent of bifenazate). Additional livestock metabolism data have not been submitted. The nature of the residue in livestock is adequatel y understood based on studies with lactating goats and laying hens; however, livestock feedstuffs are not derived from the proposed crops of the subject petition with the exception of timothy . The proposed use on timothy is for a regional use in two counties of Nevada (Eureka and Humboldt Counties). Applications can onl y be made to timothy that is intended for use as horse feed. The use on timothy was discussed and approved by the ChemSAC (meeting of 1/12/2011). Thus, secondary residues of bifenazate in livestock tissues are not of concern for this petition. The existing poultry

metabolism study

is adequate to allow HED to conclude that tolerances for poultry tissues and eggs are not needed for the purpose of this petition (Category 3 of 40 CFR §180.6). There is no reasonable expectation of finite residues in poultry matrices. This decision will be revisited in the future if additional crops with poultry feed stuffs are proposed for registration. The qualitative nature of the residue in rotational crops is adequatel y understood based on an acceptable confine d rotational metabolism study . The MARC reviewed the confined rotational crop study

and concluded that the residues of concern in/on rotational crops could not be determined from the available data. The MARC concluded that a 30 - day rotational crop restri ction is appropriate based on the available data. Appropriate rotational crop restrictions appear on the product labels for Acramite ® 4SC and Acramite ® 50WS. There are adequate residue anal ytical methods for tolerance enforcement. For plants, high perfo rmance liquid chromatography with oxidative coulometric electrochemical detector (HPL C/ELCD) Method UCC - D2341 is available as a primary enforcement method for the combined residues of bifenazate and its metabolite D3598. The method has been forwarded to the Food and Drug Administration (FDA) for inclusion in the Pesticides Analy tical Manual, Volume II (PAM II). The limit of quantification (LOQ) and limit of detection (LOD) of Method UCC - D2341 are 0.01 and 0.005 ppm, respectively . In addition, a liquid chromatographic s ys tem with tandem mass spectrometers (LC - MS/MS) method (NCL ME 245) was recentl y submitted as a confirmatory

method and has been forwarded to FDA. The data - collection methods used for the anal ys is of samples taken from supporting magnitude of the residue studies are LC - MS/MS (basil) and HPL C/EL CD (timothy forage and hay). The LOQ for basil samples was 0.047 ppm for bifenazate and 0.048 ppm for D3598. The calculated LOD for bifenazate and D3598 in/on fresh basil samples were reported to b e 0.0095 ppm and 0.0082 ppm, respectivel y, and in/on dried basil as 0.012 ppm and 0.019 ppm, respectivel y. The lowest level method validation (LLMV) for residues in/on timothy was 0.01 ppm for bifenazate and D3598. Based on recoveries from timothy forage and hay

samples fortified with bifenazate or D3598 at the LLMV, the estimated LODs were 0.004 ppm and 0.0042 ppm for bifenazate and D3598, respectively . The LOQ was 0.01 ppm for both compounds. The requirements for Multireresidue Methods (MRMs) testin g data are fulfilled. Bifenazate and the metabolites D3598, A1530, and A1530 - sulfate are not quantitatively recovered through the FDA MRMs.Bifenazate Summary of Analytical Chemistry and Residue Data DP#: D388800

Page 4 of 22 Storage stability

data are not required for the subject petition as all samples were extracted and anal yz ed within 30 day s of harvest. The longest storage intervals were 14 day s for basil samples and 22 day s for timothy

samples. IR - 4 has submitted adequate field trial data for bifenazate on basil. Four field trials were conducted in the 2008 growing season. At each trial, basil was treated with a single foliar application of Acramite ® 50 WS, at the approximate rate of 0.75 lb ai/A (1.5x the proposed application rate). The fresh basil samples were collected at a PHI of 3 day s. At one of the trials, additional s amples were collected for drying. The maximum combined residues of bifenazate and D3598 in fresh basil were 15 ppm. The maximum combined residues of bifenazate and D3598 in dried basil was 91 ppm . For the trial that included dried basil, the maximum combined residues of bifenazate and D3598 were 9.5 ppm in fresh basil and 91 ppm in dried basil which represents a concentration factor of 9.6x for residues in dried basil. The residue data for basil from the submitted crop field trials were anal yz ed using the Organization for Economic Co operation and Development (OECD) tolerance calculation procedures (see Appendix II). Based on the data set, the recommended tolerance for residues of bifenazate and D3598 (calculated as the stoichiometric equivalent of bifenazate) is 30 ppm in/on fresh herbs and 300 ppm in/on dried herbs. IR - 4 has submitted adequate field trial data for bifenazate on grasses. These data are intended to satisfy requirements for residue data for timothy forage and hay . Thirteen field trials were conducted in the United States during the 2004 growing season. At each trial , grasses received one foliar application of Acramite ® 4SC at a rate of approximately 0.75 lb ai/A. Grass forage samples were collected 4 hours after application and grass hay samples at 6 to 7 day s after application. The maximum combined residues of bifenazate and D3598 in/on grass forage were 83.5 ppm. The maximum combined residues of bifenazate and D3598 in/on grass hay in the submitted studies were 76.3 ppm. The resid ue data for grass forage and hay from the submitted crop field trials were analyzed using the OECD tolerance calculation procedures (see Appendix II). Based on the data set, the recommended tolerances for residues of bifenazate and D3598 (calculated as th e stoichiometric equivalent of bifenazate) are 200 ppm in/on grass forage and 150 ppm in grass hay . Analy tical reference standards for bifenazate and its metabolites D23 - 06 (D3598) , D23 - 15, D23 - 16 (A1530) and D23 - 19 (A1530) are currentl y available at the EPA National Pesticide Standards Repository

(personal communication with Theresa Cole , Anal ytical Chemistry Branch (ACB), 01/25/2012). However, the standard for metabolites D23 - 15 and D23 - 16 expire on 6/30/2012 and 05/31/2012, respectively . Additionall y, the Repository does not have standards for bifenazate metabolite D23 - 22. The registrant must either recertify the lots in the repository

and send in an updated certificate of anal ys is (COA), or submit new standards (different lot #) if the previous lots will not be recertified. **Regulatory Recommendations and Residue Chemistry Deficiencies** HED has examined the residue chemistry database for bifenazate. Provided a revised Section F (see below) is submitted and the petitioner resolve s the deficiency pertaining to the availability of anal ytical - grade standards at the EPA National Pesticide Standards Repository (see below), there are no residue chemistry or toxicological data deficiencies that would preclude the establishment of permanent tolerances for residues of bifenazate and its metabolites as outlined in Table 2.2.2. A human - health risk assessment will be prepared as a separate document.Bifenazate Summary of Analytical Chemistry and Residue Data DP#: D388800

Page 5 of 22 The following residue chemistry data deficiencies must be fulfilled prior to granting the u ses/tolerances. 860.1550 Proposed Tolerances In the subject petition, the proposed tolerance expression is in terms of the combined residues of bifenazate (1 - methylethyl 2 - (4 - methoxy [1,1’ - biphenyl ] - 3 - yl )h ydrazinecarbox yl ate) and diazinecarbox yl ic acid, 2 - (4 - methoxy- [1,1’ - biphenyl] - 3 - yl , 1 - methylethyl ester (expressed as bifenazate). The established tolerance expression for livestock commodities is in terms of the combined residues of bifenazate and diazinecarbox yl ic acid, 2 - (4 - methoxy- [1,1’biphenyl] - 3 - yl, 1 - methylethyl ester (D3598, expressed as bifenazate), A1530 (1,1’ - biphenyl , 4 - ol) and A1530 - sulfate (expressed as A1530; 1,1’biphenyl , 4 - oxysulfonic acid). The proposed tolerance expressions need to be modified to comply

with the interim guidance on t olerance expressions (Memo, 5/27/2008, S. Knizner). The current tolerance expressions for bifenazate tolerances in 40 CFR § 180.572(a)(1) and 40 CFR § 180.572(b) are as follows: Tolerances are established for residues of bifenazate (1 - methylethyl 2 - (4 - methoxy[1,1' - biphenyl] - 3 -

yl)hydrazinecarboxylate) including its metabolites and degradates, in or on the commodities listed in the following table. Compliance with the tolerance levels specified are to be determined by measuring only the sum of bifenazate and its metabolite, diazinecarboxylic acid, 2 - (4 - methoxy- [1,1' - biphenyl] - 3 -

yl), 1 - methylethyl ester , **(expressed as bifenazate)** in or on the following food commodities: The tolerance expression should be changed to conform to current HED policy . Specifically , the tolerance expression for 40 CFR §180.572(a)(1) should be as follows: Tolerances are established for residues **of the insecticide** bifenazate (1 - methylethyl 2 - (4 - methoxy[1,1'

- biphenyl] - 3 -

yl)hydrazinecarboxylate) including its metabolites and degrada tes, in or on the commodities listed in the following table. Compliance with the tolerance levels specified are to be determined by measuring only the sum of bifenazate and its metabolite, diazinecarboxylic acid, 2 - (4 - methoxy- [1,1' - biphenyl] - 3 -

yl), 1 - meth ylethyl ester

, **(calculated as the stoichiometric equivalent of bifenazate)** in or on the following food commodities: The current tolerance expressions for bifenazate tolerances in 40 CFR § 180.572(a)(2) is as follows: Tolerances are established for resid ues of bifenazate (1 - methylethyl 2 - (4 - methoxy[1,1 ′ - biphenyl] - 3 -

yl) hydrazinecarboxylate) including its metabolites and degradates, in or on the commodities listed in the following table. Compliance with the tolerance levels specified are to be determined b y measuring only the sum of bifenazate and its metabolites diazinecarboxylic acid, 2 - (4 - methoxy- [1,1 ′ - biphenyl] - 3 -

yl), 1 - methylethyl ester **(expressed as bifenazate)** ; 1,1 ′ - biphenyl, 4 - ol; and 1,1 ′

- biphenyl, 4 - oxysulfonic acid **(expressed as 1,1 ′** 

**- biphenyl, 4** **- ol)**  in or on the following food commodities:Bifenazate Summary of Analytical Chemistry and Residue Data DP#: D388800

Page 6 of 22 The tolerance expression for 40 CFR §180.572(a)(2) should be modified as follows: Tolerances are established for residues of **the insecticide** bifenazate (1 - methylethyl 2 - (4 - methoxy[1,1 ′

- biphenyl] - 3 -

yl) hydrazin ecarboxylate) including its metabolites and degradates, in or on the commodities listed in the following table. Compliance with the tolerance levels specified are to be determined by measuring only the sum of bifenazate and its metabolites diazinecarboxylic acid, 2 - (4 - methoxy- [1,1 ′ - biphenyl] - 3 -

yl), 1 - methylethyl ester; 1,1 ′

- biphenyl, 4 - ol; and 1,1 ′

- biphenyl, 4 - oxysulfonic acid **(calculated as the stoichiometric equivalent of bifenazate)**  in or on the following food commodities: 860.165 0 Submittal of Analy tical Reference Standards Analy tical reference standards for bifenazate and its metabolites D23 - 06 (D3598), D23 - 15, D23 - 16 (A1530) and D23 - 19 (A1530) are currently available at the EPA National Pesticide Standards Repository (personal communication with Theresa Cole, Anal ytical Chemistry

Branch (ACB), 01/25/2012). However, the standard for metabolites D23 - 15 and D23 - 16 expire d on 6/30/2012 and 05/31/2012, respectivel y. Additionally , the Repository

does not have standards for bifenazat e metabolite D23 - 22. The registrant must either recertify

the lots in the repository

and send in an updated certificate of anal ys is (COA), or submit new standards (different lot #) if the previous lots will not be recertified. If new standards are being submitted, they should be sent to the Anal ytical Chemistry Lab, which is located at Fort Meade, to the attention of either Theresa Cole at the following address: USEPA National Pesticide Standards Repository /Anal ytical Chemistry

Branch/OPP 701 Mapes Ro ad Fort George G. Meade, MD 20755 - 5350 (Note that the mail will be returned if the extended zip code is not used.) **Background** The chemical structure and nomenclature of bifenazate and its metabolites are presented in Table 1, and the phys icochemical properties of the technical grade of bifenazate are presented in Table 2.Bifenazate Summary of Analytical Chemistry and Residue Data DP#: D388800

Page 7 of 22 **Table 1. Test Compound Nomenclature.** Com pound

Common name Bifenazate Com pany experimental name D2341 IUPAC name isopropyl 3 - (4 - methoxybiphenyl - 3 - yl)carbazate or isopropyl 2 - (4 - methoxybiphenyl - 3 - yl)hydrazinoformate CAS name 1 - methylethyl 2 - (4 - methoxy[1,1 ′ -biphenyl] - 3 - yl)hydrazinecarboxylate CAS registry number 149877 - 41 - 8 End - use products (EPs) Acramite ® 50WS (EPA Reg. No. 400 - 503) Acramite ® 4SC ( EPA Reg. No. 400 - 514) Com pound

Common name None Com pany experimental name D3598 IUPAC name isopropyl - (4 - methoxy - [1,1’ - biphenyl] - 3 - yl)diazenecarboxylate CAS name diazenecarboxylic acid, 2 - (4 - methoxy - [1,1’ - biphenyl] - 3 - yl), 1 - methylethyl ester CAS registry number 149878 - 40 - 8 Com pound O H Common name None Com pany experimental name A1530 IUPAC name 1,1’ -biphenyl, 4 - ol CAS name p - hydroxybiphenyl CAS registry number 92 - 69 - 3 Com pound O S O 3 H Common name None Com pany experimental name A1530 sulfate, biphenyl - 4 - ol - sulfate IUPAC name Unknown CAS name Unknown CAS registry number Unknown O N H N H O C H 3 O C H 3 C H 3

O N N O C H 3 O C H 3 C H 3Bifenazate Summary of Analytical Chemistry and Residue Data DP#: D388800

Page 8 of 22 **Table 2. Physicochemical Properties of the Technical Grade of Bifenazate.** Melting range 124 - 125oC

MRID 46064101 pH 6.78 Density 1.19 g/cm3 Water solubility 2.1 mg/L (20°C) Solvent solubility 102 mg/mL ethyl acetate (20°C) Vapor pressure <1 x 10 - 8 atm M 3 /mole (25°C) Dissociation constant, pKa 12.94 at 23 C Octanol/water partition coefficient, Log(KOW) 3.4 UV/visible absorption spectrum Max 264 nm in water **860.1200 Directions for Use** The proposed use directions are presented in Table 3 below. The information presented in Table 3 was obtained from undated draft labels for Acramite ® 50WS (EPA Reg. No. 400 - 503) and Acramite ® 4SC (EPA Reg. No. 400 - 514). **Table 3. Summary of Proposed and Registered Directions for Use of Bifenazate.** Applic. Timing, Ty pe, and Equip. Form

ulation [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 **Herb, Subgroup 19A (Except Dried Chervil and Dried Chive, Proposed Use)** Ground Application Acramite ®

50WS [400 - 503] 0.38 to

0.50 1 0.50 (implied) 3 Application is to be made in a minimum of 50 gal/A using ground equipment. For maximum control, applications must be made as soon as mites appear. **Pom e Fruit, Group 8**  **- 10 (Registered Use)**  Ground Application Acramite ® 4SC

[400 - 514] Acramite ® 50WS [400 - 503] 0.38 to

0.50 1 0.50 (implied) 7 Application is to be made in a minimum of 50 gal/A using ground equipment. For maximum control, applications must be made as soon as mites appear. **Fruiting Vegetables, Group 8 -**  **10 (Registered Use)** Ground Application Acramite ® 4SC

[400 - 514] Acramite ® 50WS [400 - 503] 0.38 to

0.50 1 0.50 (implied) 3 Application is to be made in a minimum of 50 gal/A using ground equipment or 10 gal/A using aerial equipment. For maximum control, applications must be made as so on as mites appear. **Timothy (Proposed Use)**Bifenazate Summary of Analytical Chemistry and Residue Data DP#: D388800

Page 9 of 22 **Table 3. Summary of Proposed and Registered Directions for Use of Bifenazate.** Applic. Timing, Ty pe, and Equip. Form

ulation [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 Ground or Aerial Application Acramite ® 4SC

[400 - 514] 0.43 to

0. 7 5 1 0. 7 5 (implied) 0 (forage) 7 (hay) Application is to be

made in a minimum of 20 gal/A using ground equipment or 10 gal/A by air. For maximum control, applications must be made as soon as mites appear. The following rotational crop restriction is specified: “This product has a plantback restriction of 30 day s. Do not plant another crop within 30 day s after last Acramite ® application due to chances of bifenazate residues showing up in rotational crops.” Conclusions: The proposed use directions are adequate to allow evaluation of the residue data relative to the proposed use. **860.1300 Nature of the Residue -**  **Plants** Residue Chemistry Memo; DP# 324430, 7/19/06, T. Bloem (Discussion of Radish Metabolism Study). Residu e Chemistry Memo; DP# 276801, 8/16/01, T. Bloem (HED MARC Memo of Residues of Concern). Residue Chemistry Memo; DP# 276623, 7/31/01, T. Bloem (MARC Briefing Document). Residue Chemistry Memo; DP# 349556, 3/9/09, W.D. Wassell. Additional plant metabolism data have not been submitted. The qualitative nature of the residue in plants is adequatel y understood based on acceptable studies with apple, orange, cotton, and radish. A briefing document, summarizing the salient features o f these studies (except the radish study), was presented to the HED MARC. The MARC concluded that for tolerance expression and risk assessment purposes, the residues of concern in crops are bifenazate and its metabolite D3598 (calculated as the stoichiome tric equivalent of bifenazate). The metabolic routes in all crops were similar with major residues being comprised of bifenazate and lesser amounts of D3598. The metabolic route in tested plants proceeded via oxidation of the hydrazine moiety

of bifenazate to form D3598 which is further degraded and bound b y reaction with natural products. The HED MARC discussed the possible formation of hydrazine in plants and concluded that formation of hydrazines is unlikely due to the oxidation of the parent to the conjugated diazene. The MARC suggested that if the petitioner submits additional metabolism studies, the presence of biphenylhydrazine should be monitored as a confirmatory measure. Subsequent to the MARC decision, radish and corn metabolism studies were submitted. Radish plants were treated with single spray application of bifenazate at 0.375 or 0.75 lb ai/A, and mature root and top samples were harvested 7 day s after application. No further anal ytical work was performed in/on the radish root samples since the total radioactive residues (TRRs) were <0.01 ppm. Anal ys is of the radish tops indicated that bifenazate and D3598 were the major residues. Hydrox yl ated D3598 and D2303 were also identified; biphenyl hydrazine was included as a reference standard but was not identified as a residue in the study . The cornBifenazate Summary of Analytical Chemistry and Residue Data DP#: D388800

Page 10 of 22 metabolism study

was deemed unacceptable. The OPPTS Guidelines (860.1300) specify that if metabolism studies on three dissimilar crops show that the route of metabolism is similar then additio nal plant metabolism studies are not required. The bifenazate route of metabolism has been demonstrated to be similar in/on apple, orange, cotton, and radish. Additional plant metabolism data are not required for this petition. **860.1300 Nature of the Re sidue**  **- Livestock**  Residue Chemistry Memo; DP# 276801, 8/16/01, T. Bloem (HED MARC Memo of Residues of Concern). ChemSAC Minutes of 01/12/11(Memo dated 01/27/11). Additional livestock metabolism data have not been submitted. The nature of the residue in livestock is adequatel y understood based on studies with lactating goats and laying hens; however, livestock feedstuffs are not derived from the proposed crops of the subject petition with the exception of timothy . The proposed use on timothy is for a reg ional use in 2 counties of Nevada (Eureka and Humboldt Counties). Applications can onl y be made to timothy that is intended for use as horse feed. The use on timothy was discussed and approved by the ChemSAC (meeting of 1/12/11). Thus, secondary residue s of bifenazate in livestock tissues are not of concern for this petition. **860.1340 Residue Analytical Methods** Plant Commodities DER Reference: 47467702.der.doc (Includes MRID 47467704). Residue Chemistry Memo; DP# 313261, 7/19/06, T. Bloem (Confirmatory enforcement method). Residue Chemistry Memo; DP# 328814, 5/17/06, T. Bloem (Letter to FDA for inclusion of confirmatory enforcement method in PAM Volume II). Residue Chemistry Memo; DP# 281973, 8/29/02, T. Bloem (Letter to FDA for inclusion of primary enforcement method in PAM Volume II). Residue Chemistry Memo; DP# 277089, 8/16/01, T. Bloem (Primary enforcement method). Enforcement methods : There are adequate residue anal ytical methods for tolerance enforcement. For plants, the HPLC/ELCD Method UCC - D2341 is available as a primary enforcement method for the combined residues of bifenazate and its metabolite D3598. The method has been forwarded to the FDA for inclusion in the PAM II. The LOQ and LOD of Method UCC - D2341 are 0.01 and 0.005 ppm, respectivel y. In addition, a L C - MS/MS method (NCLME 245) was recentl y submitted as a confirmatory method and has been forwarded to FDA. Data - collection methods : The data - collection methods used for the anal ys is of samples taken from supporting magnitude of the residue studies are the LC/MS/MS method (NCLME 245) (basil) and HPLC/EL CD Method UCC - D2341 (grass). Basil samples (fresh and dried) were extracted with acetonitrile containing 0.1% of glacial acetic acid. Residues in the samples were reacted with 3 mLof 0.25% ascorbic acid in 5:95 acetonitrile: water and 45 μLof 10% acetic acid in water to convert D3598 into bifenazate. Total residues were determined by L C/MS/MS. The LOQ for residues in/on basil samples based upon the LLMV was 0.047 ppm for b ifenazate and 0.048 ppm for D3598. The calculated LOD for bifenazate and D3598 in/on fresh basilBifenazate Summary of Analytical Chemistry and Residue Data DP#: D388800

Page 11 of 22 samples were reported to be 0.0095 ppm and 0.0082 ppm, respectivel y, and in/on dried basil as 0.012 ppm and 0.019 ppm, respectivel y. Bifenazate and D3598 r esidues were extracted from homogenized timothy forage and hay

by blending twice with acetonitrile and acetic acid (0.1%) solution. The extracts were combined and filtered into a graduated cylinder and brought to a known final volume with acetonitrile. An aliquot of the sample extract was then partitioned with methylene chloride and 2% aqueous sodium sulfate. The methylene chloride phase from the partition was evaporated to near dry ness and the extract was diluted with HPL C mobile phase. After an incubation period of at least 2 hours in order to convert residues of D3598 to bifenazate, the samples were anal yz ed for residues by reverse phase HPL C/OCLD. The LLMV for this study was 0.01 ppm for bifenazate and D3598. Based on recoveries from timothy forage and hay

samples fortified with bifenazate or D3598 at the LLMV, the estimated LODs were 0.004 ppm and 0.0042 ppm for bifenazate and D3598, respectively . The LOQ was 0.01 ppm for both compounds. Conclusions: There are adequate residue anal ytical metho ds for tolerance enforcement and data collection for plant commodities. **860.1360 Multiresidue Methods** Residue Chemistry Memo; PP#5E6992; DP# 324430, 7/19/06, T. Bloem. HED previousl y reviewed MRM data for bifenazate, D3598, A1530, and A1530 - sulfate which were submitted to the FDA. These data indicate that bifenazate, D3598, A1530, and A1530 - sulfate are not quantitatively recovered through the FDA MRMs. **860.1380 Storage Stability** The storage durations and conditions of samples from the magnitude of the residue studies submitted to support this petition are presented in Table 4. **Table 4. Summary of Storage Conditions and Durations of Sam ples from Crop Filed Trials.**  Matrix Storage Temperature Actual Storage Duration Interval of Demonstrated Storage Stability Basil Frozen at the field sites within 40 minutes

of collection and stored at approximately < - 20°C until sample preparation at the analytical laboratory. 14 days Not applicable. Timothy At the field sites, samples were transferred

to frozen storage within 3.5 hours of collection. Some samples were placed on dry ice immediately. Stored at approximately - 19 to - 28°C until sample preparation at the analytical laboratory. 22 days Not applicable.

Conclusions: Storage stability data are not required as all samples were extracted and anal yz ed within 30 day s of harvest (longest interval: 22 day s).Bifenazate Summary of Analytical Chemistry and Residue Data DP#: D388800

Page 12 of 22 **860.1480 Meat, Milk, Poultry, and Eggs** Livestock feedstuffs are not derived from the proposed crops of the subject petition with the exception of timothy . The proposed use on timothy is for a regional use in 2 counties of Nevada (Eureka and Humboldt Counties). Applications can only be made to timothy

that is intended for use as horse feed. The use on timothy was discussed and approved b y the ChemSAC (meeting of 1/12/11). Thus, secondary residues of bifenazate in livestock tissues are not of concern for this petition. **860.1500 Crop Field Trials** Basil: DER Reference: 48260601.der.doc. The IR - 4 has submitted field trial data for bifenazate on basil. Four field trials were conducted in the 2008 growing season, one in California (North American Free Trade Agreement (NAFTA Region 10), one in South Carolina (NAFTA Region 2), and two in Georgi a (NAFTA Region 2). At each trial, basil was treated with a single foliar application of Acramite ® 50 WS, which contains 50% as the ai, at the approximate rate of 0.75 lb ai/A (1.5x). A commercially available adjuvant (non - ionic surfactant) was added to the spray mixture. The fresh basil samples were collected at a PHI of 3 days. At the 08 - CA *85 trial, additional samples were collected for drying. The anal ytical results show that after a total seasonal application rate of 0.75 lb ai/A at a 3 - day P HI , the maximum combined residues of bifenazate and D3598 in/on fresh basil were 15 ppm (08 - GA *06). The maximum combined residues of bifenazate and D3598 in/on dried basil was 91 ppm (08 - CA *85) which represents a concentration factor of 9.89X for residu es in dried basil. A summary

of residue data for bifenazate in/on basil is presented in Table 5.Bifenazate Summary of Analytical Chemistry and Residue Data DP#: D388800

Page 13 of 22 **TABLE 5. Summary of Residue Data from Crop Field Trials with**  **Bifenazate. Comm**  **odity Total Applic.**  **Rate 2**  **(lb ai/A) PHI** 

**(days) Residue Levels (ppm)**  **1 n**  **Min. Max.**  **HAFT 3**  **Median Me**  **an Std.**  **Dev.** Basil (fresh) 0.745

– 0.784 3 8 3.4 15 14.5 9.1 8.9 4.2 Basil (dried) 0.745 3 1 91 91 NA4 NA NA NA 1 These values represent the combined residues of bifenazate and D3598 reported as bifenazate equivalents. 2 One foliar application of Acramite ® 50WS at approximately 0.75 lb ai/A was made. 3 HAFT = highest average field trial. 4 NA = not applicable. Conclusions : The submitted residue data are adequate to fulfill data requirements for basil, the representative crop for the herb subgroup 19A (fresh and dried) . The number and locations of the crop field trials are adequate for a foliar use on herbs. The available data do support the proposed use pattern. The residue data for basil from the submitted crop field trials were anal yz ed using the OECD tolerance calculation procedures (see Appendix II). Based on the data set, the recommended tolerance for residues of bifenazate and D3598 (calculated as the sto ichiometric equivalent of bifenazate) is 30 ppm for residues in/on fresh basil. For dried basil, the recommended tolerance for residues of bifenazate and D3598 (calculated as the stoichiometric equivalent of bifenazate) is 300 ppm (30 x 9. 6 = 2 88 , rounded up to 300) for residues in/on fresh basil. Grass: DER Reference: 47327701.der.doc. IR - 4 has submitted field trial data for bifenazate on grasses. These data are intended to satisfy requirements for residue data for timothy forage and hay . Thirteen fi eld trials were conducted in the United States encompassing NAFTA Zone 2: MD (2 trials), NC (1 trial), NJ (1 trial), and TN (1 trial); Zone 3: FL (2 trials); Zone 6: TX (1 trial); Zone 8: CO (1 trial); Zone 10: CA (1 trial); Zone 11: ID (1 trial) and WA (1 trial); and Zone 12: OR (1 trial) during the 2004 growing season. At each trial location, grasses received one foliar application of Acramite ® 4SC at a rate of approximately

0.75 lb ai/A. An adjuvant was added to the spray mixture for all applications. Grass forage samples were collected 4 hours after application and grass hay samples at 6 to 7 day s after application. Maximum residues of bifenazate and D3598 in/on grass forage following a total application of approximately

0.75 lb ai/A and a PHI of 0 d ay s was 83.5 ppm. The maximum residues of bifenazate and D3598 in/on grass hay following a total application of approximately 0.75 lb ai/A and a PHI of 7 day s was 81.5 ppm. A summary of residue data for bifenazate in/on grass is presented in Table 6.Bifenazate Summary of Analytical Chemistry and Residue Data DP#: D388800

Page 14 of 22 **TABLE6. Summary of Residue Data from Crop Field Trials with Bifenazate.**  Commodity Total Applic.

Rate (lb ai/A) PHI

(days) Residue Levels 1 (ppm)

n Min. Max. HAFT 2 Median Mean Std. Dev. Grass Forage 0.72 to 0.77 0 12 27.0 83.5 83.5 5 3 . 5 53.5 19.4 Grass Hay 0.072 to 0.77 6 - 7 1 0 14.1 76.3 76.3 31.9 39.3 20.0 1 Residues are reported as bifenazate equivalents. 2 HAFT = highest average field trial. Conclusions : The submitted residue data are adequate to fulfill data requirements for a regional use for bifenazate on Timothy that is used for horse feed only . The number and locations of the crop field trials are adequate for a regional use on timothy . The available data do support the proposed use pattern. The residue data for grass forage and hay f rom the submitted crop field trials were anal yz ed using the OECD tolerance calculation procedures (see Appendix II). Based on the data set, the recommended tolerances for residues of bifenazate and D3598 are 200 ppm for residues in grass forage and 150 pp m for residues in grass hay . Pome Fruit, Group 11 - 10: No additional crop field trial data were submitted for bifenazate in/on pome fruits. A tolerance for residues of bifenazate and its metabolite in/on pome fruit, group 11 - 10 has been established at 0.75 ppm [40 CFR §180.572]. IR - 4 has proposed to expand the use/tolerance to additional commodities included in the revised Group 11 - 10. The tolerance level should be established at the same level as that of Group 11. As the proposed use on the pome fruit, Group 11 - 10 is identical to the existing use on pome fruit, Group 11 on the product labels for Acramite ® 50WS (EPA Reg. No. 400 - 503) and Acramite ® 4SC (EPA Reg. No. 400 - 514), the existing toleranc e for residues in/on Group 11 can be translated to Group 11 - 10. Fruiting Vegetables, Group 8 - 10; No additional fruiting vegetables fi eld trial data were submitted. A tolerance for residues of bifenazate and D3698 in/on fruiting vegetables, Group 8 has b een established at 2.0 ppm [40 CFR §180.572]. IR - 4 has proposed to expand the use/tolerance to additional commodities included in the revised Group 8 - 10. The tolerance level should be established at the same level as that of Group 8. As the proposed u se on the fruiting vegetables, Group 8 - 10 is identical to the existing use on Group 8 on the product labels for Acramite ® 50WS (EPA Reg. No. 400 - 503) and Acramite ® 4SC (EPA Reg. No. 400 - 514), the existing tolerance for residues in/on Group 8 can be translated to Group 8 - 10. **860.1650 Submittal of Analytical Reference Standards** Analy tical reference standards for bifenazate and its metabolites D23 - 06, D23 - 15, D23 - 16 and D23 - 19 are currentl y available at the EPA National Pesticide Standards Repository (personalBifenazate Summary of Analytical Chemistry and Residue Data DP#: D388800

Page 15 of 22 communication with Theresa Cole, Analy tical Chemistry

Branch (ACB), 01/25/2012). However, the standard for metabolites D23 - 15 and D23 - 16 expire in 6/30/2012 and 05/31/2012, respectivel y. Additionally, the Repository does not have standards for bifenazate metabolite D23 - 22. The registrant must either recertify the lots in the repository

and send in an updated COA, or submit new standards (different lot #) if the previous lots will not be recertified. If new standards are being submitted, they should be sent to the Anal ytical Chemistry L ab, which is located at Fort Meade, to the attention of either Theresa Cole at the following address: USEPA National Pesticide Standards Repository /Anal ytical Chemistry

Branch/OPP 701 Mapes Road Fort George G. Meade, MD 20755 - 5350 (Note that the mail will be returned if the extended zip code is not used.) **860.1850 Confined Accumulation in Rotational Crops** Residue Chemistry Memo; DP# 324430, 7/19/06, T. Bloem. Residue Chemistry Memo DP# 277089, 8/16/01, T. Bloem. The qualitative nature of the residue in rotational crops is adequatel y understood based on an acceptable confined rotational metabolism study . The MARC reviewed the confined rotational crop study

and concluded that the residues of concern in/on rotational crops could not be determined from the available data. The MARC concluded that a 30 - day rotational crop restriction is appropriate based on the available data. The submitted labels have appropriate rotational crop restrictions of 30 - day s for all crops. **860.1900 Field Accumulation in Rotational Crops** No field rotational crop data have been submitted. The following rotational crop restriction is specified for the Acramite ® 4SC product: “Do not plant another crop within 30 day s after last Acramite ® 4SC application due to chances of bifenazate residues showing up in rotational crops.” **860.1550 Proposed Tolerances** In the subject petition, the proposed tolerance expression is in terms of the combined residues of bifenazate (1 - methyl ethyl 2 - (4 - methoxy [1,1’ - biphenyl] - 3 - yl )h ydrazinecarboxylate) and diazinecarbox yl ic acid, 2 - (4 - methoxy- [1,1’ - biphenyl] - 3 - yl , 1 - methylethyl ester (expressed as bifenazate). The established tolerance expression for livestock commodities is in terms of the combined residues of bifenazate and diazinecarbox yl ic acid, 2 - (4 - methoxy- [1,1’biphenyl] - 3 - yl , 1 - methylethyl ester (D3598, expressed as bifenazate), A1530 (1,1’ - biphenyl, 4 - ol) and A1530 - sulfate (expressed as A1530; 1,1’biphenyl, 4 - oxysulfonic acid). The proposed tolerance expressions need to be modified to comply with the interim guidance on tolerance expressions (Memo, 5/27/20089, S. Knizner). The current tolerance expressions for bifenazate tolerances in 40 CFR § 180.572(a)(1) and 40 CFR § 180.572(b) are as follows:Bifenazate Summary of Analytical Chemistry and Residue Data DP#: D388800

Page 16 of 22 Tolerances are established for residues of bifenazate (1 - methylethyl 2 - (4 - methoxy[1,1' - biphenyl] - 3 -

yl)hydrazinecarboxylate) including its metabolites and degradates, in or on the commodities listed in the following table. Compliance with the tolerance leve ls specified are to be determined by measuring only the sum of bifenazate and its metabolite, diazinecarboxylic acid, 2 - (4 - methoxy - [1,1'

- biphenyl] - 3 -

yl), 1 - methylethyl ester, **(expressed as bifenazate)** in or on the following food commodities: The tolerance expression should be changed to conform to current HED policy . Specificall y, the tolerance expression for 40 CFR §180.572(a)(1) should be as follows: Tolerances are established for residues **of the insecticide** bifenazate (1 - methylethyl 2 - (4 - methoxy[1,1'

- biphenyl] - 3 -

yl)hydrazinecarboxylate) including its metabolites and degradates, in or on the commodities listed in the following table. Compliance with the tolerance levels specified are to be determined by measuring only the sum of bifenazate and its meta bolite, diazinecarboxylic acid, 2 - (4 - methoxy- [1,1' - biphenyl] - 3 -

yl), 1 - methylethyl ester, **(calculated as the stoichiometric equivalent of bifenazate)**  in or on the following food commodities: The current tolerance expressions for bifenazate tolerances in 40 CFR § 180.572(a)(2) is as follows: Tolerances are established for residues of bifenazate (1 - methylethyl 2 - (4 - methoxy[1,1 ′ - biphenyl] - 3 -

yl) hydrazinecarboxylate) including its metabolites and degradates, in or on the commodities listed in the following ta ble. Compliance with the tolerance levels specified are to be determined by measuring only the sum of bifenazate and its metabolites diazinecarboxylic acid, 2 - (4 - methoxy - [1,1 ′

- biphenyl] - 3 -

yl), 1 - methylethyl ester **(expressed as bifenazate)** ; 1,1 ′ - biphenyl, 4 - ol; and 1,1 ′

- biphenyl, 4 - oxysulfonic acid **(expressed as 1,1 ′**  **- biphenyl, 4** **- ol)**  in or on the following food commodities: The tolerance expression for 40 CFR §180.572(a)(2) should be modified as follows: Tolerances are established for residues of **the insecticide**  bifenazate (1 - methylethyl 2 - (4 - methoxy[1,1 ′

- biphenyl] - 3 -

yl) hydrazinecarboxylate) including its metabolites and degradates, in or on the commodities listed in the following table. Compliance with the tolerance levels specified are to be determ ined by measuring only the sum of bifenazate and its metabolites diazinecarboxylic acid, 2 - (4 - methoxy- [1,1 ′ - biphenyl] - 3 -

yl), 1 - methylethyl ester; 1,1 ′ - biphenyl, 4 - ol; and 1,1 ′

- biphenyl, 4 - oxysulfonic acid **(calculated as the stoichiometric equivalent of bif**  **enazate)** in or on the following food commodities:Bifenazate Summary of Analytical Chemistry and Residue Data DP#: D388800

Page 17 of 22 **Tolerance Summary for Bifenazate**  **. Comm**  **odity Proposed**  **Tolerance (ppm)**  **Recommended**

**Tolerance (ppm)**  **Correct Commodity**

**Definition/Comments To be established under 40 CFR**  **§180. 572**  **(a) General.**  **(1)** Herb, subgroup 19A, fresh leaves 30 30 Herb, subgroup 19A, fresh leaves, except chervil and chive Herb, subgroup 19A, dried leaves, except chervil, dried and chive, dried 140 300 Timothy, forage 140 200 Tolerance with regional registrations Timothy, hay 120 150 Tolerance with regional registrations Fruit, pome, group 11 - 10 0. 75 0. 75 Vegetable, fruiting, group 8 - 10 2.0 4.0 Tolerance level for harmonization with PMRA An International Residue Limit (IRL) Status Form is appended to this document. There are currentl y no established Codex, Canadian, or Mexican maximum residue limits (MRL s) for bifenazate in/on herbs, and timothy forage and hay . The tolerance expression for plant commodities are harmonized between the U. S. and Canada, but not with Codex. Can adian MRL s are established for residues in/on apples, bell peppers and tomatoes, but not for other crops in the pome fruit and fruiting vegetables crop groups. The Canadian MRL s for residues in apples, bell peppers and tomatoes are not harmonized with the U. S. tolerance levels for residues in pome fruits and fruiting vegetables. Codex MRLs are established for pome fruits, peppers and tomato, but not for the other members of the fruiting vegetables crop group. Additionally the Codex MRL s for residues in pome fruits, peppers, and tomato are not harmonized with the U.S. tolerance levels. Attachments: 1. Chemical Structures 2. Tolerance - Assessment Calculations. 3. International Residue Limit Status S heet RDI: RAB1 ( 09 / 19 /2012) W. Wassell : S - 10958: Potomac Yard 1 (PY1): (703)305 - 6135): 7509P: RAB1Bifenazate Summary of Analytical Chemistry and Residue Data DP#: D388800

Page 18 of 22 **A ttachment 1:**  Chemical Structures

**C hemical**  **N am**  **e C**  **hemical S**  **tructure** bifenazate (D2341) hydrazinecarboxylic acid, 2 - (4 - methoxy- [1,1’ -biphenyl] - 3 - yl), 1 - methylethyl ester D3598 diazinecarboxylic acid, 2 - (4 - methoxy- [1,1’ - biphenyl] - 3 - yl), 1 - methylethyl ester D4642 diazinecarboxylic acid, 2 - (4 - methoxy- [1,1’ - biphenyl] - 3 - yl), 1 - methylethyl ester 2 - oxide O C H 3 N N O C H 3

O C H 3 O H D9963 4 - methoxy- [1,1’ -biphenyl] - 3 - ol O C H 3 O H D1989 1,1’ -biphenyl, 4 - methoxy O C H 3 D9569 [1,1’ -biphenyl] - 4,4’ - diol O H H O A1530 1,1’ -biphenyl, 4 - ol O H A1530 - sulfate O S O 3 H

D9472 O H O H D23 - 14; biphenyl hydrazine; (4 - methoxy- [1,1’ -biphenyl] - 3 - yl)hydrazine O C H 3 N H N H 2 O N H N H O C H 3 O C H 3 C H 3

O N N O C H 3 O C H 3 C H 3Bifenazate Summary of Analytical Chemistry and Residue Data DP#: D388800

Page 19 of 22 **Attachment 2. Tolerance -** **Assessment Calculations. Bifenazate**  **Basil USA**  **0.75 lb ai/A Total number of data (n)**  4 **Percentage of censored data** 0% **Number of non -**  **censored data** 4 **Lowest residue** 3.450 **Highest residue** 14.500 **Median residue** 8.875 **Mean** 8.925 **Standard deviation (SD)** 4.540 **Correction factor for censoring (CF)**  1.000 **Proposed MRL estimate**

**- Highest residue**  14.500

**- Mean + 4 SD**  27.086

**- CF x 3 Mean**  26.775 **Unrounded MRL** 27.086 **Rounded MRL 30**  High uncertainty of MRL estimate. [Small dataset] **Residues (mg/kg) n**  3.45 1 8.25 1 9.5 1 14.5 1Bifenazate Summary of Analytical Chemistry and Residue Data DP#: D388800

Page 20 of 22 **Bifenazate grass forage**  **USA 0.75 lb ai/A**  **Total number of data (n)** 12 **Percentage of censored data** 0% **Number of non -**  **censored data** 12 **Lowest residue** 27.000 **Highest residue** 83.500 **Median residue** 53.450 **Mean** 53.533 **Standard deviation (SD)** 19.423 **Correction factor for censoring (CF)** 1.000 **Proposed MRL estimate**

**- Highest residue**  83.500

**- Mean + 4 SD**  131.224

**- CF x 3 Mean**  160.600 **Unrounded MRL** 160.600 **Rounded MRL 200**  **Residues (mg/kg) n** 

27 1 28.6 1 34.1 1 35.7 1 48.2 1 52.6 1 54.3 1 58.9 1 70.5 1 73 1 76 1 83.5 1Bifenazate Summary of Analytical Chemistry and Residue Data DP#: D388800

Page 21 of 22 **Bifenazate grass hay**  **USA 0.75 lb ai/A**  **Total number of data (n)** 10 **Percentage of censored data** 0% **Number of non -**  **censored data** 10 **Lowest residue** 14.100 **Highest residue** 76.300 **Median residue** 31.900 **Mean** 39.324 **Standard deviation (SD)** 19.980 **Correction factor for censoring (CF)** 1.000 **Proposed MRL estimate**

**- Highest residue**  76.300

**- Mean + 4 SD**  119.245

**- CF x 3 Mean**  117.972 **Unrounded MRL** 119.245 **Rounded MRL 150**  **Residues (mg/kg) n**  14.1 1 19.6 1 25.9 1 28.24 1 31.2 1 32.6 1 51.6 1 53.6 1 60.1 1 76.3 1Bifenazate Summary of Analytical Chemistry and Residue Data DP#: D388800

Page 22 of 22 **A ttachment 3:**  International Residue Limit Status Sheets Bifenazate ( 000586 ; 09/05/2012) Summary of US and International Tolerances and Maximum Residue Limits Residue Definition : US Canada Mexico 2 Codex 3 40 CFR 180.572: Plant/Livestock fat: Sum of Bifenazate (1 - methylethyl 2 - (4 - methoxy[1,1' -biphenyl] - 3 - yl)hydrazinecarboxylate) and its metabolite diazinecarboxylic acid, 2 - (4 - methoxy - [1,1' - biphenyl] - 3 - yl), 1 - methylethyl ester ( D3598) (expressed as bifenazate) Livestock (except fat): sum of bifenazate and its metabolites D3598 (expressed as bifenazate); 1,1 ′ -biphenyl, 4 - ol; and 1, 1 ′ - biphenyl, 4 - oxysulfonic acid (expressed as 1,1 ′ -biphenyl, 4 - ol) Plant/Livestock fat: 1 - methylethyl 2 - (4 - me thoxy[1,1' -biphenyl] - 3 - yl) hydrazinecarboxylate, including the metabolite diazenecarboxylic acid, 2 - (4 - methoxy - [1,1' -biphenyl] - 3 - yl),1 - methylethyl ester Livestock except fat: 1 - methylethyl 2 - (4 - me thoxy[1,1' -biphenyl] - 3 - yl)hydrazinecarboxylate, including the metabolites diazenecarboxylic acid, 2 - (4 - methoxy - [1,1' - biphenyl] - 3 - yl), 1 - methylethyl ester and [1,1' - biphenyl] - 4 - ol and [1,1' -biphenyl] - 4 - ol sulfate Sum of Bifenazate and bifenazatediazene, diazinecarboxylic acid, 2 - (4 - methoxy - [1,1' - biphenyl] - 3 - yl), 1 - methylethyl ester (expressed as bifenazate) Bifenazate is a fat soluble compound. Commodity 1 Tolerance (ppm) /Maximum Residue Limit (mg/kg) US Canada Mexico 2 Codex 3 Fruit, pome, group 11 0.75 0.6 apples 0.7 pome fruits Vegetable, fruiting, group 8 2.0 1.1 bell peppers 0.35 tomatoes 3 peppers chili Peppers, sweet including (pimento or pimiento) 0.5 tomato Herb subgroup 19A, fresh leaves 30 40 mints Herb subgroup 19A, dried leaves except chervil, dried and chive, dried. 140 Timothy, forage 140 Timothy, Hay 120 Com pleted: M. Negussie; 09/10/2012 1 Includes only commodities of interest for this action. Tolerance values should be the HED recommendations and not those proposed by the applicant. 2 Mexico adopts US tolerances and/or Codex MRLs for its export purposes. 3 * = absent at the limit of quantitation; Po = postharvest treatment, such as treatment of stored grains. PoP = processed postharvest treated commodity, such as processing of treated stored wheat. (fat) = to be measured on the fat portion of the sample. MRLs indicated as proposed have not been finalized by the CCPR and the CAC.