Page **1** of **21 UNITED STA** **TES ENVIRONMENTA L PROTECTION A** **GENCY**

WA SHINGTON, D.C. 20460 OFFICE OF CHEMICAL SAFETY AND POLLUTION PREVENTION **Date:** D ecember 6 , 2011 **MEMORANDUM SUBJECT:**  **S -**  **Metolachlor** . Petition for the Use on Coriander ( Cilantro ) and Garden Beet

L eaves. Summary

of Analy tical Chemistry

and Residue Data. **PC Code:** 108800 **DP Barcode:** D 392447 **Decision No.:** 451816 **Registration No. :**  100 - 81 6 **Petition No.:** 1E7898 **Regulatory Action:** Section 3 **Risk Assessment Type:** Single Chemical **Case No.:** 0001 **T XR**  **No.:** NA **CAS No.:** 87392 - 12 - 9 **MRID No.:** 48536501 **40 CFR:** 180.368 FROM: W. Cutchin, Chemist

Alternative Risk Integration Assessment Team (ARIA) In ert Ingredients Assessment Branch (IIAB ) Registration Division (RD; 7505P) THROUGH: S. Hummel, Senior S cientist

Registration Action Branch 4 (RAB4) Health Effects Division (HED; 7509P) TO: D. Rate, Ph.D., Team Co - Leader

Section 18 Team Minor Use and Emergency Response Branch RD (7505P) **Executive Summary** Under PP#1E7898, the petitioner, Interregio nal Research Project No.4 ( IR - 4 ) , on behalf of the Agricultural Experiment Station of the IR - 4 Project and the Agricultural Experiment Stations of New York, North Carolina and South Carolina ( coriander (cilantro) ); and California, Oklahoma, Texas and Tenne ssee (b eet, garden, leaves ), request the establishment of tolerance s for residues of S - metolachlor, including its metabolites and degradates, in or on the commodities in the table below. **Comm odity**  **Proposed T**  **olerance ppm**  Cilantro, leaves, fresh 8.0Page **2** of **21** Cil antro, leaves, dried 8.0 Coriander, seed 0.13 Beet, garden, leaves 1.8 S - Metolachlor (an isomer enriched form of metolachlor) is a selective, chloroacetanilide herbicide that is applied to a variety of crops as a preplant, preplant incorporated, preemergence, or postemergence application, primarily for the control of grass weeds. S - Metolachlor is registered for use on a wide variety of crops including: corn, cotton, grasses grown for seed, legume vegetables, peanuts, potatoes, safflower, sorghum, sunfl ower, and tomato es ( 40 CFR: 180.368 ) . Compliance with the tolerance levels specified below is to be determined by measuring only

the sum of free and bound S - metolachlor, S - 2 - chloro -N - (2 - ethyl - 6 - methylphenyl ) -N - (2 - methoxy- 1 - methylethyl)acetamide, its R- en antiomer, and its metabolites, determined as the derivatives 2 - (2 - ethyl - 6 - methylphenyl)amino - 1 - propanol (SYN506357 (S enantiomer of CGA 37913)) and 4 - (2 - ethyl - 6 - methylphenyl) - 2 - hydrox y- 5 - methyl - 3 - morpholinone (SYN 508500 (S - enantiomer of CGA - 49751)), calculated as the stoichiometric equivalent of S - metolachlor, in or on the commodities . S - metolachlor is to be applied to coriander (cilantro) as a broadcast, foliar application at 0.64 - 0.96 lbs ai/A 30 day s before the leaf harvest and 70 day s before seed. Us e the lower end of S metolachlor rate range for soils that are relatively coarse textured and the higher rates on fine textured soils. S - metolachlor is to be applied to beets grown for leaves as a broadcast, pre emergence soil surface treatment at 0.63 - 1 .26 lbs ai/A after the crop has been planted but before the crop and weeds emerge. A second a ppl ication of S - metolachlor may be made to beets as one post emergence, broadcast treatment at 0.63 - 1.26 lbs ai/A when plants are at 1 to 2 true leaf stage. Use the lower end of S - metolachlor rate range for soils that are relatively coarse textured and the higher rates on fine textured soils. The qualitative nature of metolachlor residues in plants is adequatel y understood based upon the adequate corn, potato, and soy bean metabolism studies. The metabolism of metolachlor involves conjugation with glutathione, breakage of this bond to form the mercaptan, conjugation of the mercaptan with glucuronic acid, O - demethylation of the methyl ether, and conjugation of the resultant alcohol with a neutral sugar. Residues of concern in plants include metolachlor and its metabolites, determined as the derivatives CGA - 37913 and CGA - 49751. The Agency previously

concluded that the residues of concern for S - metolachlor are the same as for metolachl or. Adequate studies are available depicting the metabolism of metolachlor in ruminants and poultry . As in plants, metolachlor residues of concern in livestock commodities include metolachlor and its metabolites, determined as the derivatives CGA - 37913 and CGA - 49751. The residues of concern for S - metolachlor in livestock are the same as those for metolachlor. Adequate methodology

is available for enforcing the established and recommended tolerances. PAM Vol. II, lists a gas chromatography with nitrogen phosphorous detector ( GC/NPD ) method (Method I) for determining residues in/on crop commodities and a gas chromatography with mass spectroscop y detector ( GC/MSD ) method (Method II) for determining residues in livestock commodities. These methods determine residues of metolachlor and its metabolites as either CGA - 37913 or CGA - 49751 following acid hydroly sis. IR - 4 and S yn genta have proposed a highPage **3** of **21**

pressure liquid chromatography with mass spectroscopy

/mass spectroscop y ( HP LC /MS/MS ) enantiomer- specific method for the enforcement of the propose d tolerances, Method 1848 - 01. The method uses a chiral HPL C column to separate out the S - enantiomers (SYN506357 and SYN508500) of the hydrolysis products CGA - 37913 and CGA - 49751. This method has be en determined to be adequate for enforcement purposes . Adequate data are available on the recovery of metolachlor through Multiresidue Method Testing Protocols. The FDA PESTDATA database indicates that metolachlor is completely recovered through Method 3 02, PAM Vol. I . Coriander (cilantro) fresh, dried and seed samples were anal yz ed using the “Working Method for PR 09595: Analysis of s - Metolachlor in Cilantro as Metabolites s - CGA - 37913 (SYN - 506357) and s - CGA - 49751 (SYN - 508500), A. Le, Document I .D. Working Method for 09595.06 - BER06.doc, Effective Date: 04 - 18 - 08,” a modification of Sy ngenta Method No. 1848 - 01. Samples of the raw agricultural commodities, leaves and stems, and seed were refluxed in acid and partitioned into dichloromethane (DCM). An aliqu ot was purified with column chromatography and concentrated into aqueous acetonitrile. The lower limit of method validation ( LLM V) for residues of SYN 506357 and SYN 508500 was 0.05 ppm in all matrices. Based on the LLMV, the calculated limits of detecti on (L OD) ranged from 0.01 32 - 0.0175 ppm for SYN 506357 and SYN 508500 in coriander (cilantro) fresh, dried and seed samples. The calculated limits of quantitation (LOQ) ranged from 0.0359 - 0.0526 ppm for SYN 506357 and SYN 508500 in coriander (cilantro) fre sh, dried and seed samples, respectively . The method is adequate for data collection. Previously

submitted storage stability data indicates that the residues of metolachlor are stable on a variety of commodities for up to 2 yrs. Coriander (cilantro) fre sh leaves and stems, dried leaves and stems and seed samples were stored frozen for a maximum of 708 days, 702 day s, and 416 day s, respectively . The results of the storage stability study with coriander (cilantro) samples and previousl y s ubmitted storage stability data are adequate to show that residues of S metolachlor were stable for the duration of this study . There are no proposed uses in w ater, fish, irrigated crops and f ood handling establishments ; therefore, discussions of S - metolachlor residues on the s e topic s are not are germane to this petition. There are no coriander (cilantro) or garden beet leaf livestock feed items of regulatory interest ; therefore , a discussion of S - metolachlor residues on livestock food items is not germane to this petitio n . The submitted study

is adequate in number and geographic location of residue field trials. Five field trials were conducted in EPA Region s 2 (2) , 6, 9, and 10. At all sites, two plots received a single broadcast application of S - metolachlor at the approximate rate of 0.64 lb ai/A or 0.96 lb ai/A. Coriander (cilantro) fresh leaf and stem samples were harvested approximately 30 (27 - 34) day s pre - harvest interval (PHI), after the application and placed into frozen storage shortl y after harvest. At one s ite , additional treated plots received a single broadcast application of S metolachlor at the approximate rate of 0.64 lb ai/A or 0.96 lb ai/A, where coriander (cilantro)Page **4** of **21**

seed were collected. At another site , additional treated plots received a single bro adcast application of S - metolachlor at the approximate rate of 0.64 lb ai/A or 0.96 lb ai/A, and coriander (cilantro) leaves and stems were collected at 27 day s and dried in an oven. N o spray adjuvant was used at the trials. No residue decline studies were submitted. The anal ytical results show that after a single foliar broadcast application of S - metolachlor at the approximate rate of 0.64 lb ai/A and 0.96 lb ai/A with a 27 to 34 - day s PHI, the maximum total S metolachlor residues as parent equivalents w ere approximately 3.7 ppm and 4.1 ppm in coriander (cilantro) fresh leaves and stems, respectivel y. The maximum total S - metolachlor residues as parent equivalents were increased from approximately <0.131 ppm (fresh samples) to 0.834 ppm (dried samples) in the 0.64 lb ai/A treated plot. The maximum total S - metolachlor residues as parent equivalents were increased from approximately 0.170 ppm (fresh samples) to 2.031 ppm (dried samples) in the 0.96 lb ai/A treated plot. The maximum total S - metolachlor resi dues as parent equivalents were <0.131 ppm in coriander (cilantro) seed at both application rates. Based on the results of these trials, the appropriate tolerance for residues of S - metolachlor in/on coriander (cilantro) leaves is 8.0 ppm. However, the Ag ency uses the preferred name coriander not cilantro for this raw agricultural commodity and, in addition, does not differentiate between dry and fresh leaves for coriander (cilantro). Therefore, a revised Section F should be submitted to indicate a reques t for coriander, leaves at 8.0 ppm and the cilantro dried and fresh leaves should be removed. The study data indicates that the requested tolerance on coriander , seed at 0.13 ppm is adequate. No new data have been submitted in support of the requested tolerance on beet, garden, leaves. The request is based on the currently established tolerance for residues of S - metolachlor on Brassica leafy

vegetables (Sub - group 5B), of 1.8 ppm . The Chemistry Science Advisory C ouncil (ChemSAC) has considered the issu e and determined that since the use pattern for beet greens is the same as that for leafy Brassica (sub group 5B), and beet greens are similar to the commodities in the leafy Brassica subgroup 5B, it is appropriate to translate this tolerance of 1.8 ppm to beet greens. Based on the CHEMSAC d etermination and that the proposed use pattern for beet, garden, leaves is the same as l eafy Brassica greens, subgroup 5B , IIAB recommends for the proposed tolerance of 1.8 ppm on beet, garden, leaves . There is no crop associated with this petition which requires residue data for processed fractions. Analy tical standards for the following compounds related to metolachlor are currently available in the EPA National Pesticide Standards Repository . The rotational crop restrictions listed on the label are appropriate for these proposed uses. **Regulatory Recommendations and Residue Chemistry Deficiencies** IIAB has examined the residue chemistry database for S - metolachlor. Pending receipt of an update d Section F for coriander , leaves at 8.0 ppm with the cilantro, dried and fresh l eaves removed , IIAB has no objection to the establishment of the tolerances described in Table 9, below.Page **5** of **21**

A human health risk assessment is forthcoming. 860.1500 Crop Field Trials The Agency

use s the preferred name coriander not cilantro for this raw agricultural commodity and, in addition, does not differentiate between dry and fresh leaves for coriander (cilantro). Therefore, a revised Section F should be submitted to indicate a request for co riander, leaves at 8.0 ppm and the cilantro dried and fresh leaves should be removed. **Background** The chemical structure and nomenclature of S - metolachlor and its regulated hydrol ytic derivatives are presented in Table 1, and the phys icochemical propertie s of S - metolachlor are presented in Table 2. **Table 1. Nom enclature of**  **S -**  **Me tolachlor**  **and its Regulated Derivatives** Com pound

C H 3 N C 2 H 5 C C H 2 O C l C C H 3 C H 2 O C H 3 H

Common name S - Metolachlor Com pany experimental name N/A IUPAC name (S) - 2 - chloro -N - (2 - ethyl - 6 - methyl -ph enyl) -N - (2 - methoxy - 1 - methyl - ethyl) - acetamide CAS name 2 - chloro -N - (2 - ethyl - 6 - methylphenyl) -N - [(1 S ) - 2 - methoxy - 1 - methylethyl] - acetamide CAS registry number 87392 - 12 - 9 End - use product (EP) Dual II Magnum (EPA Reg. No: 100 - 816 )

O H N H Com pany experimental name SYN506357 (S - enantiomer of CGA 37913) IUPAC name (S) - 2 - [(2 - ethyl - 6 - methylphenyl) amino] -propan - 1 - ol CAS name (S) - 2 - [(2 - ethyl - 6 - methylphenyl) amino] - 1 -propanol CAS # 82508 - 08 - 5

N O

O O H Com pany experimental name SYN 50 8500 (S - enantiomer of CGA - 49751) IUPAC name (S) - 4 - (2 - ethyl - 6 - methylphenyl) - 2 - hydroxy - 5 - methylmorpholin - 3 - onePage **6** of **21**

**Table 1. Nom enclature of**  **S -**  **Me tolachlor**  **and its Regulated Derivatives** CAS name 4 - (2 - ethyl - 6 - methylphenyl) - 2 - hydroxy - 5 - methyl - 3 - mo rpholone CAS # 61520 - 54 - 5 **Table 2. Physicochemical Properties of the Technical Gr ade S**  **- Me** **tolachlor Param**  **eter Value**  **References (MRID)** Melting point/range Not applicable, liquid at room tem perature 46829503 pH 7.8 at 25°C (1% aqueous dispersion) Density 1.117 g/cm3 at 20°C Water solubility (25°C) 0.48 g/L Solvent solubility mg/L at 25°C Com pletely miscible with methanol, acetone, toluene, n - octanol, n - hexane, ethyl acetate, dichloromethane Vapor pressure at 25°C 2.8 x 10 - 5 mm Hg Dissociation constant (pKa) No dissociation constant in pH range 2 - 12 Octanol/water partition co efficient Log (Kow) 3.05 at 25°C UV/visible absorption spectrum Neutral: 534 l/mol.cm @ 266.4 nm 443 l/mol.cm @ 274.4 nm Acidic: 534 l/mol.cm @ 266.4 nm 444 l/mol.cm @ 274.4 nm Basic: 534 l/mol.cm @ 266.4 nm 411 l/mol.cm

@ 274.4 nm **860.1200 Directions for Use** The petitioner provided a text listing of proposed uses in Section B of the petition . Apply S metolachlor to coriander (cilantro) formulated as Dual MAGNUM ( EPA Reg. No.: 100 - 816 ) as a broadcast, foliar app lication (0.64 - 0.96 lbs ai/A) at 30 day s before the leaf harvest and 70 day s before seed. Use the lower end of S - metolachlor rate range for soils that are relativel y coarse textured and the higher rates on fine textured soils. Apply S - metolachlor to beet s grown for leaves as a broadcast, pre - emergence soil surface treatment at 0.63 - 1.26 lbs ai/A after the crop has been planted but before the crop and weeds emerge. A second a ppl ication of S - metolachlor to beets may

be made as one post emergence, broadcas t treatment at 0.63 - 1.26 lbs ai/A when plants are at 1 to 2 true leaf stage. Use the lower end of S - metolachlor rate range for soils that are relativel y coarse textured and the higher rates on fine textured soils. The proposed uses are presented below in Table 3. **Table 3. Summary of Proposed Directions for Use of S**  **- Metolachlor.**  Applic. Timing; Ty pe; and Equip. (minimum volume) 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 Coriander (cilantro)Page **7** of **21**

**Table 3. Summary of Proposed Directions for Use of S**  **- Metolachlor.**  Applic. Timing; Ty pe; and Equip. (minimum volume) 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 Broadcast Foliar (20 GPA) 7.62 lb/gal EC [100 - 816] 0.64 - 0.96 1 0.96 30 - leaves 70 - seeds REI: 24hrs Beet, garden, leaves (for varieties grown for tops only) Postemergence to Soil & Broadcast Foliar (1 0 - 40 GPA) 7.62 lb/gal EC [100 - 816] 0.6 3 - 1.26 2 2.52 30 First appl. broadcast, pre - emergence soil surface treatment Second appl. when plants are at 1 to 2 true leaf stage. REI: 24hrs Conclusions : The proposed use directions are adequate. **860.1300 Nature of the Residue**  **- Plants**  The qualitative nature of metolachlor residues in plants is adequatel y understood based upon the adequate corn, potato, and soy bean metabolism studies. The metabolism of metolachlor involves conjugation with glutathione, breakage of this bond to form the mercaptan, conjugation of the mercaptan with glucuronic acid, O - demethylation of the methyl ether, and conjugation of the resultant alcohol with a neutral sugar. A minor pathway may involve sugar conjugation of metolachlor directly

to the corresponding oxo - compounds. Residues of concern in plants include metolachlor and its metabolites, determined as the derivatives CGA - 37913 and CGA - 49751. The Agency

previousl y concluded that the residues of concern for S - metolachlor are the same as for metolachlor (DP# 226780, L. Kutney , 11/15/96). The Agency

has also reviewed plant metabolism data on S - metolachlor from field tests on soy beans and corn, in vitro tests on corn seedlings, and greenhouse tests on seedlings of corn, sorghum, so ybe ans and peanuts (DP#s 278742 and 279110 , S. Kinard , 8/15/03). These data support Sy

ngenta’s assertion that the metabolism of S - metolachlor in plants is similar to that for the racemic mixture. The data did not address whether there is any conversion of the S - isomers of metolachlor or its metabolites to the R- isomer forms; however, HED previously concluded that such conversion of isomers in plants is not likely to be significant. **860.1300 Nature of the Residue -**  **Livestock** Adequate studies are available depicting the metabolism of metolachlor in ruminants and poultry . Metolachlor is rapidly metabolized and almost totally eliminated in the urine and feces of ruminants (goats), non - ruminants (rats), and poultry . Metolachlor per se was not detected in any o f the excreta or tissues. As in plants, metolachlor residues of concern in livestock commodities include metolachlor and its metabolites, determined as the derivatives CGA - 37913 and CGA - 49751. The residues of concern for S - metolachlor in livestock are th e same as thosePage **8** of **21**

for metolachlor. The Agency

has also reviewed livestock metabolism data on S - metolachlor (DP#s 278742 , S. Kinard , 8/15/03). Data from a goat metabolism study indicated that S - metolachlor was readil y absorbed and extensively metabolized by goats via glutathione conjugation and/or oxidation reactions. Oxidized metabolites were also conjugated with glucuronic acid. Data from a poultry metabolism study

indicated that S - metolachlor was also extensively metabolized via O demethylation and subs equent glucuronic acid conjugation or oxidation to dihydrox y or carbox yl ic acid metabolites that may also be conjugated with glucuronic acid. **860.1340 Residue Analytical Methods** Enforcement methods: Adequate methodology is available for enforcing the es tablished and recommended tolerances. PAM Vol. II, Pesticide Regulation Section 180.368, lists a GC/NPD method (Method I) for determining residues in/on crop commodities and a GC/MSD method (Method II) for determining residues in livestock commodities. These methods determine residues of metolachlor and its metabolites as either CGA - 37913 or CGA - 49751 following acid hydrol ys is. IR - 4 and Sy

ngenta have proposed an HP LC/MS/MS enantiomer- specific method for the enforcement of the proposed tolerances, Metho d 1848 - 01. This method has been previousl y reviewed b y HED (DP# 296904 , R. L oranger , 4/17/06). The method uses a chiral HPLC column to separate out the S - enantiomers (SYN506357 and SYN508500) of the hydroly sis products CGA - 37913 and CGA - 49751. Data -ga thering methods: Coriander (cilantro) fresh, dried and seed samples were anal yz ed for residues of S - metolachor using the “Working Method for PR 09595: Analysis of s - Metolachlor in Cilantro as Metabolites s - CGA - 37913 (SYN - 506357) and s - CGA - 49751 (SYN - 50850 0), A. Le, Document I.D. Working Method for 09595.06 - BER06.doc, Effective Date: 04 - 18 - 08,” a modification of Sy

ngenta Method No. 1848 - 01, dated June 26, 2003 entitled “Anal ytical Method for the Enantioselective Determination of Residues of s - Metolachlor as Metabolites SYN 506357 and SYN - 508500 in Agricultural Commodities by Chiral High Performance Liquid Chromatograph with Mass Spectrometric Detection.” Samples of the raw agricultural commodities , leaves and stems, and seed were refluxed in 6N HCL . The cooled extract was filtered and residues were partitioned from a pH adjusted aliquot into DCM and dried with sodium sulfate. An aliquot was purified with alumina column chromatography and concentrated into 30% acetonitrile (aqueous). The residues were qu antified by reversed phase HPL C with positive ion atmosphere pressure chemical ionization tandem mass spectrometric detection (MS/MS). The residue anal ytical method for S - metolachlor residues in/on coriander (cilantro) samples was validated both prior to and concurrently with field samples. For method validation, control samples of coriander (cilantro) fresh, dried and seed were fortified with SYN 506357 and SYN 508500 at 0.05, 0.5, 2, and 5.0 ppm. Concurrent recoveries were conducted at 0.05, 0.5, and 1 ppm. The LLMV for residues of SYN 506357 and SYN 508500 was 0.05 ppm in all matrices.Page **9** of **21**

Several validation recoveries for SNY - 508500 (s - CGA 49751) on seed were lower than the acceptable range of 70 - 120%. Method validation recoveries on seed ranged from 59 - 72% (avg. 66 ± 5%) and concurrent recoveries ranged from 50 - 84% (avg. 67 ± 14%). **Table 4. Summary of Recoveries of S**  **- Metolachlor from**  **Coriander (cilantro) Matrix**  **Analyte Spike**  **level (m**  **g/kg) Sample** 

**size (n) Recoveries (%)**  **Me an ± std dev**  **Me thod Va**  **lidation** Fresh leaves and stems SYN - 506357

(s - CGA 37913) 0.05

0.5 6 94, 92, 78, 80, 81 83 **±** 8 85.2 **±** 7 0.5 6 92, 87, 86, 82, 81, 83 85 **±** 4 5.0 6 72, 93, 92, 92, 81, 93 87 **±** 9 Fresh leaves and stems SYN - 508 500

(s - CGA 49751) 0.05 6 74, 76, 78, 76, 76, 74 76 **±** 2 77.6 **±** 3

0.5 6 79, 78, 79, 72, 81, 82 79 ± 4 0.5 6 79, 78, 76, 79, 85, 74 78 ± 4 Dried leaves and stems SYN - 506357

(s - CGA 37913) 0.05 3 89, 100, 96 95 ± 6 89.3 **±** 16

0.5 3 77, 77, 74 76 ± 2 2 6 71, 83, 85, 120, 81, 118 93 ± 21 Dried leaves and stems SYN - 508500

(s - CGA 49751) 0.05 3 72, 84, 74 77 ± 6 83.0 **±** 18

0.5 3 62, 62, 62 62 ± 0 2 6 87, 105, 113, 110, 77, 88 97 ± 15 Seed SYN - 506357

(s - CGA 37913) 0.05 3 7 8, 84, 85 82 ± 4 81 **±** 3

0.5 3 82, 82, 76 80 ± 3 Seed SYN - 508500

(s - CGA 49751) 0.05 5 66, 64, 64 65 ± 1 66 **±** 5

0.5 3 72, 70, 59 67 ± 7 **Concurrent Validation** Fresh leaves and stems SYN - 506357

(s - CGA 37913) 0.05 7 96, 84, 108, 100, 92, 86 91 ± 12 86 **±** 11

0.5 5 84, 90, 86, 74, 74 82 ± 7 Fresh leaves and stems SYN - 508500

(s - CGA 49751) 0.05 7 70, 84, 72, 80, 92, 100, 98 83 ± 12 82 **±** 11 0.5 4 80, 78, 76, 70 76 ± 4 Dried leaves and stems SYN - 506357

(s - CGA 37913) 0.05 3 84, 108, 86 93 ± 13 82 **±** 11

0.5 3 71, 79, 73 74 ± 4 1.0 3 80, 82, 77 79 ± 2 Dried leaves and stems SYN - 508500

(s - CGA 49751) 0.05 3 76, 85, 101 87 ± 12 88 **±** 16

0.5 3 72, 72, 74 73 ± 1 1.0 3 109, 108, 96 104 ± 7 Seed SYN - 506357

(s - CGA 37913) 0.05 5 80, 76, 94, 106 , 84 88 ± 4 81 **±** 13

0.5 3 67, 71, 71 70 ± 2 Seed SYN - 508500 0.05 5 65, 76, 78, 78, 84 76 ± 7 67 **±** 14Page **10** of **21**

**Table 4. Summary of Recoveries of S**  **- Metolachlor from**  **Coriander (cilantro) Matrix**  **Analyte Spike**  **level (m**  **g/kg) Sample** 

**size (n) Recoveries (%)**  **Me an ± std dev**  (s - CGA 49751) 0.5 3 50, 50, 52 51 ± 1 Based on recoveries at the LLMV, the LOD ( std. dev. x one - tailed t - statistic) were calculated . The LOQ ( 3 x L OD) were also calculated . The LLMV, LOD and LOQ for SYN - 506357 and SYN - 508500 in/on the three matrices are listed below: **Table 5. Summary of S -**  **Me tolachlor Analytical Method Limits**  **Comm odity**  **Analyte Calculated LOD**  **(ppm) Calculated LOQ** 

**(ppm) LLM**  **V**

**(p pm)**  Coriander (cilantro) Fresh Sam ples SYN - 506357

SYN - 508500 0.0145 0.0132 0.0436

0.0396 0.05

0.05 Coriander (cilantro) Dried Sam ples SYN - 506357

SYN - 508500 0.0160 0.0175 0.0480

0.0526 0.05

0.05 Coriander (cilantro) Seed Sam ples SYN - 506357

SYN - 508500 0.0 154 0.0120 0.0463

0.0359 0.05

0.05 Conclusions : There are adequate enforcement methods available. The data collection method was adequate for the determination of S - metolachlor residues in coriander (cilantro) commodities. **860.1360 Multiresidue Method s**  Adequate data are available on the recovery of metolachlor through Multiresidue Method Testing Protocols. The FDA PESTDATA database indicates that metolachlor is completely recovered through Method 302, PAM Vol. I(3 rd ed., revised 10/97). **860.1380 St orage Stability**  Adequate storage stability data are available for crop commodities . Previously submitted data (DP# 292881 , S. Kinard , 8/15/03) indicate that: CGA - 37913 is stable at ≤ - 10°C for at least 2 ye ars in corn (grain and forage), peanut, potato (tubers, wet peel and flakes), soy bean (hulls and meal) and tomatoes, for at least 29 months in cottonseed oil, and for at least 37 months in cottonseed and corn oil; and CGA - 49751 is stable at ≤ - 10°C for at least 2 years in corn (grain, forage, and oil), peanuts, potatoes (tubers, wet peel and flakes), so yb eans (hulls and meal) and tomatoes, and for at least 37 months in cotton seed and cottonseed oil. In additio n, storage stability studies conducted concurrently with previously

submitted asparagus, carrot, and green onion field trials indicate that both analy tes are stable at - 20oC for at least 14.1 months in asparagus, 24.3 months in carrots, and 21.7 months in green onions. Coriander (cilantro) fresh leaves and stems, dried leaves and stems and seed samples were stored frozen for a maximum of 708 day s, 702 day s, and 416 day s, respectively . Recoveries of SYN -Page **11** of **21**

506357 and SYN - 508500 from stored coriander (cilantro) samples were corrected for concurrent recoveries. The maximum frozen storage intervals for field treated coriander (cilantro) fresh leaves and stems, dried leaves and stems, and seed samples in this study were 708 day s, 702 day s, and 416 day s respectiv ely . The results of the storage stability study showed that recoveries of S metolachlor residues in/on coriander (cilantro) fresh leaves and stems were 52% (corrected 70%) and 72% (corrected 87%) for SYN - 506357 and SYN - 508500, respectivel y. The recoverie s of S metolachlor residues in/on coriander (cilantro) dried leaves were 84% (corrected 88%) and 62% (corrected 82%) for SYN - 506357 and SYN - 508500, respectivel y. The recoveries of S metolachlor residues in/on coriander (cilantro) seed were 92% (corrected 110%) and 63% (corrected 80%) for SYN - 506357 and SYN - 508500, respectivel y. **Table 6. Stability of S -**  **Me tolachlor in**  **Coriander (cilantro) Sam** **ples Following Storage at -**  **20 o**  **C Matrix**  **(RAC or Extract)**  **Analyte Stored Sample**  **Recovery (%) Concurrent** 

**Recovery (%)**  **Stored Sample**

**Average Corrected**  **Recovery (%) 1**  **Actual**

**Storage Duration**  **(days) Interval of** 

**Dem onstrated**  **Storage Stability (days)**  Coriander (cilantro) fresh leaves and stems SYN 506357 53, 52, 52 75 70 708 720 SYN 508500 71, 70, 74 82 87 Coriander (cilantro) dried leaves and stems SYN 506357 67/83

70/106 72/104 81/111 88 624 - 702 678 - 686 SYN 508500 58/76

52/66 55/66 71/80 82 Coriander (cilantro) seed SYN 506357 72/112

99/70 83/114 85/81 110 366 - 416 399 - 413 SYN 508500 50/7 9

73/54 50/69 80/77 80 1 Average Corrected Recovery (%) = 100 x [Average Stored Sample Recovery (%) ÷ Average Concurrent Recovery (%)] Conclusions: The previously submitted storage stability data indicates that the residues of metolachlor are stable o n a variety of commodities for up to 2 yrs. The results of the storage stability study with coriander (cilantro) samples and previously submitted data are adequate to show that residues of S - metolachlor were stable for the duration of this study . **860.14 00 Water, Fish, and Irrigated Crops**  There are no proposed uses that are germane to this guideline topic. **860.1460 Food Handling** There are no proposed uses that are germane to this guideline topic .Page **12** of **21**

**860.1480 Meat, Milk, Poultry, and Eggs** There are no co riander (cilantro) or garden beet leaf feed items of regulatory interest, therefore a discussion of S - metolachlor residues on livestock food items is not germane to this guideline topic . **860.1500 Crop Field Trials** Coriander (cilantro) DER References: 485 36501.der.doc The IR - 4 has submitted field trial data for S - metolachlor on coriander (cilantro) . Five field trials were conducted in the 2006 - growing season, one in South Carolina (EPA Region 2), one in Georgia (EPA Region 2), one in Texas (EPA Region 6) , one in New Mexico (EPA Region 9), and one in California (EPA Region 10). At each trial, there were at least two treated plots. At all sites, two of the plots received a single broadcast application of S - metolachlor at the approximate rate of 0.64 lb ai/A or 0.96 lb ai/A. Coriander (cilantro) fresh leaf and stem samples were harvested approximately 30 (27 - 34) days after the application and placed into frozen storage shortly after harvest. At the New Mexico trial, additional treated plots received a s ingle broadcast application of S - metolachlor at the approximate rate of 0.64 lb ai/A or 0.96 lb ai/A, where coriander (cilantro) seed were collected. At the California trial, additional treated plots received a single broadcast application of S metolachlo r at the approximate rate of 0.64 lb ai/A or 0.96 lb ai/A, timed to be approximately 30 day s before harvest, when coriander (cilantro) fresh leaves and stems were dried. All applications were made within 17 - 36 gallons per acre spray solution and no spray adjuvant was used at the trials. Coriander (cilantro) fresh leaves and stems samples were collected between 27 - 34 day s after the final application at all sites. Coriander (cilantro) seed samples were collected at 70 day s after the application. Coriand er (cilantro) leaves and stems were collected at 27 day s and dried in an oven at 155° F before sampling. The anal ytical results show that after a single foliar broadcast application of S - metolachlor at the approximate rate of 0.64 lb ai/A and 0.96 lb ai/A with a 27 to 34 - day s pre - harvest interval (PHI), the maximum total S - metolachlor residues as parent equivalents were approximately 3.7 ppm and 4.1 ppm in coriander (cilantro) fresh leaves and stems, respectivel y. The maximum total S metolachlor residues as parent equivalents were increased from approximately <0.131 ppm (fresh samples) to 0.834 ppm (dried samples) in the 0.64 lb ai/A treated plot. The maximum total S - metolachlor residues as parent equivalents were increased from approximately 0.170 ppm (f resh samples) to 2.031 ppm (dried samples) in the 0.96 lb ai/A treated plot. The concentration factor from fresh samples to dried samples was 6 - 12X. The maximum total S - metolachlor residues as parent equivalents were <0.131 ppm in coriander (cilantro) se ed at both application rates. No residue decline studies were submitted.Page **13** of **21 T**  **able 7 . Residue Data from**  **Coriander (cilantro) Crop Field Trials with**  **S -**  **Metolachlor Trial ID**  **(City,State/Year) Region**  **Crop/ Variety**  **Comm odity**  **Total Rate (lbs ai/A)**  **PHI**

**(days) Residue**  **SYN**   ** 506357** **(ppm) Residue** 

**SYN**   ** 508500** **(ppm) SYN**  **- 506357** 

**as parent equivalents**  **1 (ppm)**  **SYN -**  **508500**

**as parent equivalents**  **2 (ppm)**  **S -**  **metolachlor**

**total residues as parent**  **equivalents (ppm)**  06 - SC*09 (Charleston, SC, 2006) 2 Coriander

(cilantro) / Santo Fre sh leaves 0.63 34 0.090 0.096 0.103

0.092 0.132

0.141 0.117

0.105 0.249

0.246 0.88 0.124

0.118 0.153

0.122 0.182

0.173 0.174

0.139 0.356

0.312 06 - GA*11 (Tifton, GA, 2006) 2 Coriander (cilantro) / Santo Monogerm Fresh leaves 0.64 27 1.682 2.008 0.821

0.924 2.473

2.952 0.936

1.053 3.409

4.005 0.97 1.992

1.873 1.163

1.112 2.928

2.753 1.326

1.268 4.254

4.021 06 - TX* 37 (Weslaco, TX, 2006) 6 Coriander

(cilantro) / leisure Fresh leaves 0.64 32 <0.05 <0.05 <0.05

<0.05 <0.074

<0.074 <0.057

<0.057 <0.131

<0.131 0.96 0.068

0.056 0.059

0.055 0.100

0.082 0.067

0.063 0.167

0.145 06 - CA*109 (Salinas, CA, 2006) 10 Coriander

(cilantro) / Santo Fresh leaves 0.65 27 <0.05 <0.05 <0.05

<0.05 <0.074

<0.074 <0.057

<0.057 <0.131

<0.131 0.97 <0.05

<0.05 0.079

0.089 <0.074

<0.074 0.090

0.101 0.164

0.175 Dried Leaves 0.66 28 0.174* 0.507* 0.256 0.578 0.834

0.98 0.594* 1.016* 0.873 1.158 2.031 06 -NM14 (Las Cruces, NM, 2006) 9 Coriander

(cilantro) / Santo Fresh leaves 0.64 28 <0 .05 <0.05 <0.05

0.05 <0.074

<0.074 <0.057

0.057 <0.131

<0.131 0.97 0.090

0.057 0.112

0.066 0.132

0.084 0.128

0.075 0.260

0.159 Seed 0.64 70 <0.05 <0.05 <0.05* <0.05* <0.074

<0.074 <0.057

<0.057 <0.131

<0.131 0.96 <0.05

<0.05 <0.05* <0.05 * <0.074

<0.074 <0.057

<0.057 <0.131

<0.131 * Result is the average of the duplicate analyses of a single sample. 1 SYN - 506357 values were multiplied by 1.47 to obtain parent equivalents. Values of 0.074 ppm represent the method’s LOQ as parent equivalents . 2 SYN - 508500 values were multiplied by 1.14 to obtain parent equivalents. Values of 0.057 ppm represent the method’s LOQ as parent equivalents. **T able 8**  **. Summary of Residue Data from Crop Field Trials with S**  **- Metolachlor**  **Comm odity**  **Total**

**Applic. Rate (l** **b ai/A) PHI**  **1**

**(days) Analyte**  **Residue Levels (ppm) 2** 

**n Min.**  **Max. HAFT**  **3 Median**  **Me an**  **Std. Dev.**  Coriander (cilantro) fresh leaves/stems 0.63

– 0.65 27

– 34 Total S metolachlor as parent equivalents 10 <0.13 4.0 3.7 <0.13 0.87 1.53 Coriander (cilantro) fre sh leaves/stems 0.88

– 0.97 27

– 34 10 0.14 4.2 4.1 0.22 1.0 1.6 Coriander (cilantro) dried leaves/stems 0.66 27 1 0.83 0.83 - 0.83 0.83 -Page **14** of **21**

**T able 8**  **. Summary of Residue Data from Crop Field Trials with S**  **- Metolachlor**  **Comm odity**  **Total**

**Applic. Rate (l** **b ai/A) PHI**  **1**

**(days) Analyte**  **Residue Levels (ppm) 2** 

**n Min.**  **Max. HAFT**  **3 Median**  **Me an**  **Std. Dev.**  Coriander (cilantro) dried leaves/stems 0.98 27 1 1.6 1.6 - 1.6 1.6 - Coriander (cilantro) seed 0 .64 70 2 <0.13 0.13 - <0.13 <0.13 - Coriander (cilantro) seed 0.96 70 2 <0.13 <0.13 - <0.13 <0.13 - 1 PHI = Post harvest interval 2 Sum of SYN - 506357 and SYN - 508500 residues as parent equivalents 3 HAFT = Highest Average Field Trial Conclusions : The submitted study is adequate in number and geographic location of residue field trials . The study data indicates that the highest residues for coriander (cilantro) w ere found in fresh leaves at the higher application rate. Th is data w as entere d into the OECD MRL Calculator. Based on the results of these trials, the Calculator indicates that the appropriate tolerance for residues of S - metolachlor in/on coriander (cilantro) leaves is 8.0 ppm. However, the Agency uses the preferred name coriande r not cilantro for this raw agricultural commodity and, in addition, does not differentiate between dry and fresh leaves for coriander (cilantro) . Therefore, **a revised Section F should**  **be submitted to indicate a request for**  **coriander ,**  **leaves at 8.0 ppm an d**  **the cilantro**  **dried and fresh leaves should**  **be removed.** The study data indicates that the requested tolerance on coriander , seed at 0.13 ppm is adequate. IIAB recommends for the requested tolerance. Beet, Garden, Leaves No new data have been submitted in support of the requested tolerance on beet, garden, leaves. The IR - 4 Project Headquarters received a request from California, Texas, Tennessee, and Oklahoma for the use of S - metolachlor as herbicide to control weeds in beet, garden, leaves production. The request is based on the currentl y established tolerance for residues of S metolachlor on Brassica leafy vegetables (Sub - group 5B), of 1.8 ppm . The ChemSAC ( 4/ 6/2011 ) has considered the issue: “... Tolerances for S - metolachlor are published in 40 CFR § 180.368 (a) (2). Both the Brassica leafy

vegetables and the turnip greens tolerances were established 17 - Sep - 2010, in connection with PP#9E7607, based on data on the representative commodity mustard greens. These data were translated to turnip green s. Tolerances have already been established for residues of S - metolachlor on vegetable, root, exc sugarbeet, subgroup 1B at 0.3 ppm (Established 17 - Sep - 2008, in connectionPage **15** of **21**

with PP#3E6787), and beet, sugar, root at 0.5 ppm and beet, sugar, tops, at 15 ppm (also established 17 - Sep - 2008, but in connection with PP#6E4638). A tolerance for residues of S - metolachlor on leaves of root and tuber vegetables (Crop Group 2) would not be appropriate because there are not tolerances on the corresponding roots (all of Crop Group 1). A tolerance for residues of S - metolachlor on Carrot of 0.20 ppm was proposed in connection with PP#7E4916, and was increased to 0.40 ppm in connection with PP#9E7607. The maximum seasonal application rate on sugarbeets is 3.81 lb ai/A, with no more than 2.53 lb ai/A applied postemergence. The single application rate on sugarbeets is 2.53 lb ai/A. On carrots, a maximum of one application of 1.9 lb ai/A is allowed with a 64 day PHI . On leafy Brassica (sub - group 5B), a maximum of one application of 1.27 lb ai/A is allowed with a 30 day

PHI . The use pattern for sugar beets allows much more S - metolachlor to be applied than to leafy Brassica (sub - group 5B); therefore, it would be inappropriate to translate the sugarbeet data to beet greens. However, since the use pattern for beet greens is the same as that for leafy Brassica (sub group 5B), and beet greens are similar to the commodities in the leafy Brassica subgroup 5B, it is appropriate to translate this tolerance of 1.8 ppm to beet greens.” Conclusions: Based on the CHEMSAC d etermination and that the proposed use pattern for beet, garden, leaves is the same as l eafy Brassica greens, subgroup 5B , IIAB recommends for the proposed tolerance of 1.8 ppm on beet, garden, leav es . **860.1520 Processed Food and Feed** There is no crop associated with this petition which requires residue data for processed fractions. **860.1650 Submittal of Analytical Reference Standards** Analy tical standards for the following compounds related to metolachlor are currently available in the EPA National Pesticide Standards Repository ( D P#s 369005 & 375955, S. Hummel, 6/15/10 ; expiration data in parentheses ): metolachlor (11/10/2010); S - metolachlor (8/1/2012); metolachlor derivative CGA - 37913 (4/30/2010); metolachlor derivative CGA - 49751 (4/30/2011); metolachlor, ethane sulfonic acid sodium salt (CGA - 354743, 4/1/2011); and metolachlor, oxanilic acid (CGA - 51202, 4/1/2011). **860.1850/860.1900 Confined/Field Accumulation in Rotation al Crops**  D369005 and D375955 , S. Hummel , 6/15/10 Confined and field rotational data requirements were recently examined (DP# 369005 and 375955, S. Hummel , 6/15/10 ) . An adequate confined rotational crop study is available, although additional information pertaining to the study remains outstanding. The residues of concern in rotated crops are the same as in the primary crops, S - metolachlor, its R- enantiomer, and its metabolites determined as CGA - 37913 and CGA - 49751. HED has determined that adequatePage **16** of **21**

fiel d rotational crop data have been submitted which support the existing rotational crop restrictions on the label for EPA Reg. Nos. 100 - 816 pending additional label amendments ( i.e. , Rotational crop directions for crops with a 60 - day plantback interval must be amended to prohibit a second application of S - metolachlor to any of these crops replanted within 60 day s of the original application.). Conclusions: Although additional data for the confined rotational crop study remains outstanding , it is not a defi ciency for this petition. Rotational crop directions for crops with a 60 - day plantback interval have be en amended to prohibit a second application of S - metolachlor to any of these crops replanted within 60 day s of the original application. This is no longer a deficiency

for S - metolachlor peti ti ons. **860.1550 Proposed Tolerances** Tolerances are currentl y established under 40 CFR §180. 368 for residues of S - metolachlor, including its metabolites and degradates, in or on the commodity(s), as defined. Complian ce with the tolerance levels specified in the following table below is to be determined by measuring onl y the sum of free and bound S - metolachlor, S - 2 - chloro -N - (2 - ethyl - 6 - methylphenyl) -N - (2 - methoxy- 1 - methylethyl)acetamide, its R- enantiomer, and its metabol ites, determined as the derivatives, 2 - (2 - ethyl - 6 - methylphenyl )amino - 1 - propanol and 4 - (2 - ethyl - 6 - methylphenyl ) - 2 - hydrox y- 5 - methyl - 3 - morpholinone, calculated as the stoichiometric equivalent of S - metolachlor, in or on the commodity . The submitted coriander (cilantro) study is adequate in number and geographic location of residue field trials and supports the proposed tolerance. The Agency uses the preferred name coriander not cilantro for this raw agricultural commodity and, in addition, does not differentiate between dry

and fresh leaves for coriander (cilantro). Therefore, a revised Section F should be submitted to indicate a request for coriander, leaves at 8.0 ppm and the cilantro dried and fresh leaves should be removed. The study data indicates th at the requested tolerance on coriander , seed at 0.13 ppm is adequate. Based on the CHEMSAC d etermination and that the proposed use pattern for beet, garden, leaves is the same as l eafy Brassica greens, subgroup 5B , IIAB recommends for the proposed tolerance of 1.8 ppm on beet, garden, leaves . No maximum residue limits (MRL s) for S - metolachlor on coriander have been established or proposed b y Codex , Canada , or Mexico . No MRLs for S - metolachlor on beet, garden, leaves have been established or proposed b y Codex or Mexico . An MRL for S - metolachlor on beet, garden, leaves ha s been established in Canada . However, beet, garden, leaves are not a significant import/export commodity and are not expected to be a trade irritant with Canada. **Table 9**  **. Toleranc e Summary for**  **S -**  **me tolachlor**  **.** Commodity Proposed Tolerance (ppm) RD - Recommended

Tolerance (ppm) Correct Commodity Definition Cilantro, leaves, fresh 8.0 NA Cilantro, leaves, dried 8.0 NA Coriander, seed 0.13 0.13Page **17** of **21**

**Table 9**  **. Toleranc e Summary for**  **S -**  **me tolachlor**  **.** Commodity Proposed Tolerance (ppm) RD - Recommended

Tolerance (ppm) Correct Commodity Definition Beet, garden, leaves 1.8 1.8 Coriander , leaves NA 8.0 **References** DP Number: D369005, D375955 Subject: S - Metolachlor. Petition for the Establishment of Permanent Tolerances for New

Uses on Bushberry

Subgroup 13 - 07B; Caneberry Subgroup 13 - 07A; Carrot; Cucumber; Lea fy

Brassica Greens Subgroup 5B; Melon Subgroup 9A; Okra; Bulb Onion Subgroup 3 - 07A; Green Onion Subgroup 3 - 07B; Sesame Seed; Sorghum; and Turnip Greens. Summary of Analytical Chemistry

and Residue Data. From: S. Hummel To: B. Daiss Dated: 6/15/10 MRIDs: 47829401 - 08, 4802 0601 DP#: D 226780 Subject: Replacement of Metolachlor Technical (Racemic Metolachlor) with Alpha Metolachlor (formerl y called Chiral Metolachlor) Technical; Review of Bridging Data. From: L. Kutney To: R. Griffin Dated: 11/15/96 MRIDs: 43928901 - 03, 43928 939 - 42 DP Number: D274328 Subject: Metolachlor and S - Metolachlor Residue Chemistry Chapter for the Tolerance Reassessment Eligibility

Decision (TRED) From: S. Kinard To: C . Jarvis Dated: 2/28/02 MRIDs: NA DP Number: D278742, D279110 Subject: S - Meto lachlor**.** Information Supporting the Assertion That the Metabolism of Smetolachlor Is Essentially the Same as for the Racemic Mixture. From: S. Kinard To: S. Kinard Dated: 8/15/03 MRIDs: 45499603, 45499604, 45499605, 45533103Page **18** of **21**

DP#: D 296904 Subject: PP# 3E6787. S - Metolachlor. Petition for Tolerances on Various Crops, Crop

Groups, and Livestock Commodities. Summary of Anal ytical Chemistry

and Residue Data. From: R. L oranger To: B. Madden/S. Jackson Dated: 4/17/06 MRIDs: 45499609, 45499610, 46046501 - 0 6 DP#: D 292881 Subject: PP#s: 7F04897, 9E06055, 7E04916, 2E06374, 4E04420, 8E05029, and 8E05030.

Revised Metolachlor and S - metolachlor Residue Chemistry Chapter for the Tolerance Reassessment Eligibility Decision (TRED) and Registration for Use on Asparagus, Carrots, Cotton, Horseradish, Green Onions, Peppers, Rhubarb, Sugar Beet, Sunflower, and Swiss Chard. From: S. Kinard To: H. Jamerson Dated: 8/15/03 MRIDs: 44378401, 44908701, 45544701 DP#s: D 332846, D 332847, D 332848, D 332849, D 350604, D 350942, D 351 174,

D 351226 Subject: S - Metolachlor. Amended Use Directions for Sorghum and So ybeans; Revisions

to Rotational Crop Restrictions; Registrant’s Responses to Deficiencies Noted in the Revised S - Metolachlor TRED. Summary of Analy tical Chemistry

and Residue D ata. From: D. McNeill y To: E. Wilson/J. Miller and R. L ouie/N. Anderson Dated: 10/21/08 MRIDs: 46829501 - 04, 47121701 - 02, 47304701 - 02 Attachments: Inte rnational Residue Limit Status S heet Tolerance/MRLSpreadsheetPage **19** of **21**

**ATTACHMENT I International Residue L**  **imits** S - metolachlor (108800; 11/28/2011) Summary of US and International Tolerances and Maximum Residue Limits Residue Definition : US Canada Mexico 2 Codex 3 40 CFR: 180.368 sum of free and bound S metolachlor, S - 2 - chloro - N - (2 - ethyl - 6 - methylphenyl ) -N - (2 - methoxy- 1 - methylethyl)acetamide, its Renantiomer, and its metabolites, determined as the derivatives, 2 - (2 - ethyl - 6 - methylphenyl )amino - 1 - propanol and 4 - (2 - ethyl - 6 - methylphenyl ) - 2 - hydroxy- 5 - methyl - 3 - morpholinone calculated as the stoichiometric equivalent of S - metolachlor 2 - chloro -N - (2 - ethyl - 6 - methylphenyl ) -N - [(1 S ) - 2 - methoxy- 1 - methylethyl)acetamide and 2 - chloro - N - (2 - ethyl - 6 - methylphenyl ) -N - [(1 R) - 2 - methoxy- 1 - methylethyl)acetamide, including the metabolites 2 - [(2 - ethyl - 6 - methylphenyl )amino] - 1 - propanol an d 4 - (2 - ethyl - 6 - methylphenyl) - 2 - hydrox y- 5 - methyl - 3 - morpholinone None

Commodity 1 Tolerance (ppm) /Maximum Residue Limit (mg/kg) US Canada Mexico 2 Codex 3 Coriander, seed 0.13 Beet, garden, tops 1.8 0.8 garden beet tops Coriander, leaves 8.0

Completed: M. Negussie; 11/29/2011 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 U S 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.Page **20** of **21**

**A TTACHMENT I**  **I Tolerance**  **- Assessment Calculations**  The submitted U.S. residue data for coriander ( cilantro ) , fresh leaves ( 10 data points) were entered into the OECD MRLCalculator in order to determine appropriate tolerance levels. **Residues (mg/kg) n**  0.145 1 0.159 1 0.164 1 0.167 1 0.175 1 0.26 1 0.312 1 0.356 1 4.021 1 4.254 1

**S -**  **metolachlor Cilantro Fresh**  **USA** 0.88

– 0.97 lb ai/A **Total number of data (n)** 10 **Percentage of censored data** 0% **Number of non -**  **censored data** 10 **Lowest residue** 0.145 **Highest residue** 4.254 **Median residue** 0.218 **Mean** 1.001 **Standard deviation (SD)** 1.655 **Correction factor for censoring (CF)** 1.000 **P roposed MRL estimate** 

**- Highest residue**  4.254

**- Mean + 4 SD**  7.623

**- CF x 3 Mean**  3.004 **Unrounded MRL** 7.623 **Rounded MRL 8** Page **21** of **21**