Cyazofamid Summary of Analytical Chemistry and Residue Data Barcode D396051

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UNITED STATES ENVIRONMENTAL PROTECTION AGENCY

WASHINGTON, D.C. 20460

OFFICE OF CHEMICAL SAFETY AND

 POLLUTION PREVENTION

MEMORANDUM

Date: 25-APR-2012 

Subject: Cyazofamid. Petition for the Establishment of Permanent Tolerances and 

Registration for Use on Basil, Succulent Beans, the Fruiting Vegetable Group 8-10, 

the Leafy Greens Subgroup 4A, and the Tuberous and Corm Vegetable Subgroup 1C. 

Summary of Analytical Chemistry and Residue Data.

PC Code: 085651 DP Barcode: D396051

MRID Nos.: See Below Registration No.: 71512-3

Petition No.: 1E7929 Regulatory Action: Section 3 Registration

Assessment Type: Single Chemical/Aggregate Case No.: NA

TXR No.: None CAS No.: 120116-88-3

Decision No.: 456373 40 CFR 180.601

From: Nancy Dodd, Chemist

Risk Assessment Branch III (RAB3)

Health Effects Division (HED) (7509P)

Through: Leung Cheng, Senior Chemist

RAB3/HED (7509P)

To: Barbara Madden/Laura Nollen, RM #5

Risk Integration, Minor Use and Emergency Response Branch (RIMUERB)

Registration Division (7505P)

MRID Summary Table

MRID No. Study Type Comments

48629401 860.1500 New DER; 48629401.der.doc

48629402 860.1500 New DER; 48629402.der.doc

48629403 860.1500 New DER; 48629403.der.doc

48629404 860.1500 New DER; 48629404.der.doc

48629405 860.1500 New DER; 48629401.der.doc

46537730 860.1520 No DER
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Table of Contents

Background..................................................................................................................................... 3

Executive Summary........................................................................................................................ 3

Pre-Registration Data Needs....................................................................................................... 5

Condition-of-Registration Data Needs ....................................................................................... 5

Tolerance Considerations................................................................................................................ 5

Analytical Method ...................................................................................................................... 5

Recommended Tolerances.......................................................................................................... 5

International Harmonization ....................................................................................................... 6

Revisions to Petitioned-For Tolerances...................................................................................... 6

Residue Profile................................................................................................................................ 7

Residue Chemistry Guidelines........................................................................................................ 9

Directions for Use (860.1200) .................................................................................................... 9

Nature of the Residue (860.1300/1850).................................................................................... 12

Residue Analytical Methods (860.1340) .................................................................................. 14

Multiresidue Methods (860.1360) ............................................................................................ 15

Storage Stability (860.1380)..................................................................................................... 16

Water, Fish, and Irrigated Crops (860.1400)............................................................................ 17

Food Handling (860.1460)........................................................................................................ 17

Meat, Milk, Poultry, and Eggs (860.1480) ............................................................................... 17

Crop Field Trials (860.1500) .................................................................................................... 19

Processed Food and Feed (860.1520)....................................................................................... 28

Rotational Crops (Field; 860.1900) .......................................................................................... 29

Tolerance Derivation .................................................................................................................... 29

Appendix A. Field Trial Geographic Distribution....................................................................... 42

Appendix B: International Residue Limits................................................................................... 44

Appendix C: Chemical Names and Structures of Cyazofamid and Identified Metabolites ......... 45
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Background

The Interregional Research Project No. 4 (IR-4) has proposed establishment of permanent 

tolerances for residues of the fungicide cyazofamid [4-chloro-2-cyano-N, N-dimethyl-5-(4-

methylphenyl)-1H-imidazole-1-sulfonamide] and its metabolite CCIM [4-chloro-5-(4-

methylphenyl)-1H-imidazole-2-carbonitrile] on basil (fresh and dried), succulent beans, 

succulent shelled beans, the fruiting vegetable group 8-10, the leafy greens subgroup 4A, and the 

tuberous and corm vegetable subgroup 1C. These proposed new uses are to be added to the 

Ranman 400SC label (EPA Reg. No. 71512-3). Ranman 400SC is a soluble concentrate 

formulation which contains 3.33 lb active ingredient (ai) per gallon (400 grams ai/liter; 34.5% 

ai).

Cyazofamid is a fungicide which belongs to a novel chemical class based on the cyanoimidazole 

moiety. Cyazofamid is a broad spectrum fungicide active against oomycete fungi (such as

Phytophthora, Plasmopara, Pseudoperonospora, and Pythium) and Plasmodiophoromycetes 

(Plasmodiospora brassicae). It specifically interferes with the cytochrome bc1 complex 

(ubiquinol cytochrome c oxidoreductase) in the mitochondrial respiratory chain of oomycetes 

fungi. 

Permanent tolerances are established in 40 CFR §180.601 on various raw agricultural 

commodities (RACs) at levels ranging from 0.02 ppm on potato to 12.0 ppm on turnip greens 

and the Brassica leafy greens subgroup 5B. A tolerance with regional registration is established 

on grape at 1.5 ppm. Time-limited tolerances under a Section 18 have been established on dried 

basil at 144 ppm and fresh basil at 12 ppm; these tolerances will expire on 12/31/14. No 

tolerances have been established on livestock commodities. 

Ranman® 400SC can be applied using ground, aerial, or sprinkler irrigation equipment. 

Multiple foliar applications can be made to all proposed crops. Tomatoes grown for transplant 

and basil can be grown in the greenhouse. A soil drench can be applied to fruiting vegetables at 

transplant or to tomatoes in the greenhouse. A band or soil drench application can be made to 

the leafy greens subgroup 4A at transplant or seeding. The tuberous and corm vegetable 

subgroup can be treated at-planting, in-furrow at planting, or lay-by/hilling. Maximum 

application rates per crop growing season are 0.43 lb ai/A for beans (succulent podded and 

succulent shelled), fruiting vegetables, and the leafy greens subgroup 4A; 0.7 lb ai/A for basil, 

and 0.71 lb ai/A for the tuberous and corm vegetable subgroup 4A. The preharvest intervals are 

0 days for basil, beans (succulent podded and succulent shelled), fruiting vegetables, and the 

leafy greens subgroup 4A, and 7 days for the tuberous and corm vegetable subgroup 1C. The 

plantback interval is 0 days for crops on the label and 30 days for other crops. The label 

indicates that Ranman 400SC should be tank mixed with an organosilicone surfactant, non-ionic 

surfactant, or a blend of an organosilicone and a non-ionic surfactant. 

Executive Summary

The Interregional Research Project No. 4 (IR-4) has proposed establishment of permanent 

tolerances for residues of the fungicide cyazofamid and its metabolite CCIM on basil (fresh and 

dried), succulent beans, succulent shelled beans, the fruiting vegetable group 8-10, the leafy
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greens subgroup 4A, and the tuberous and corm vegetable subgroup 1C. 

Ranman 400 SC is a suspension concentrate formulation. Cyazofamid has limited systemic 

activity. It can be applied using ground, aerial or sprinkler irrigation equipment. It can be 

applied to the soil and as multiple foliar applications. It can be applied to basil grown in the 

greenhouse and to tomato transplants in the greenhouse. Maximum application rates per crop 

growing season are 0.43 lb ai/A for beans (succulent podded and succulent shelled), fruiting 

vegetables, and the leafy greens subgroup 4A; 0.7 lb ai/A for basil, and 0.71 lb ai/A for the 

tuberous and corm vegetable subgroup 4A. The preharvest intervals are 0 days for basil, beans 

(succulent podded and succulent shelled), fruiting vegetables, and the leafy greens subgroup 4A, 

and 7 days for the tuberous and corm vegetable subgroup 1C. 

The residues of concern for the tolerance expression and risk assessment are parent and the 

metabolite CCIM in treated plants and parent only in rotational crops. No residues are expected 

to occur in livestock commodities.

Adequate enforcement methods are available, including a multiresidue method (Protocol D) and 

a high performance liquid chromatography/ultraviolet detection (HPLC/UV) method with a 

confirmatory method (liquid chromatography/tandem mass spectrometric detection; 

LC/MS/MS). The methods determine cyazofamid and the metabolite CCIM. The limit of 

quantitation (LOQ) of the HPLC/UV and LC/MS/MS methods is 0.01 ppm for each analyte. 

Adequate storage stability data are available to support the storage intervals of the field trials and 

processing studies.

Provided the requested revisions are made to the Ranman 400 SC label, the field trials are 

adequate to establish tolerances on all the proposed commodities at levels recommended in Table 

1 below. Detectable residues may occur in food. Field trial decline studies show that residues in 

agricultural commodities decline with increasing preharvest intervals.

 

Adequate processing studies are available. The potato and tomato processing studies are 

adequate to indicate that combined residues of cyazofamid and CCIM are not likely to 

concentrate in processed commodities.

The proposed and registered uses fall under 40 CFR §180.6(a)(3) with respect to livestock 

commodities, i.e., there is no reasonable expectation that finite residues will occur in livestock 

commodities.

Based on a study on confined accumulation in rotational crops, cyazofamid (parent) is expected 

to be present at a level of less than 0.01 ppm at a plantback interval of 30 days. The rotational 

crop plantback interval of 0 days for crops which are on the label and 30 days for other crops is 

appropriate.

Regulatory Recommendations

Provided the revisions to the Section B/label are made as requested below (in the Pre-
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Registration Data Needs section), the available residue chemistry data are adequate to support 

registration of the crop/crop group commodities requested by the petitioner at the tolerance

levels recommended in Table 1 below (in the Recommended Tolerances section).

Pre-Registration Data Needs

Directions for Use (860.1200)

The Ranman 400 SC label should be amended to prohibit applications to cowpea grown for 

livestock feeds because no residue data are available for cowpea forage and hay. The statement 

“Do not apply to cowpea used for livestock feed” should be added to the label. Cowpea is a 

succulent shelled bean.

The label indicates that Ranman 400 SC should be tank mixed with an organosilicone surfactant, 

non-ionic surfactant, or a blend of an organosilicone and non-ionic surfactant. The label should 

be revised to specify that an organosilicone surfactant can be used on basil, snap beans, lima 

beans, pepper, potato, spinach and tomato, and either a nonionic surfactant or an organosilicone 

surfactant can be used on head and leaf lettuce. 

Meat, Milk, Poultry, and Eggs (860.1480)

Tolerances for residues of cyazofamid in poultry and swine commodities are not required 

provided that application to cowpea used for livestock feed is prohibited on the label. 

Condition-of-Registration Data Needs

None

Tolerance Considerations

Analytical Method

Adequate enforcement methods are available to determine residues of cyazofamid and its 

metabolite CCIM in lettuce, basil, snap bean, lima bean, pepper, potato, spinach, and tomato. An 

enforcement method for non-fatty commodities is FDA’s Multiresidue Protocol D (without 

cleanup), which completely recovers (>80% recovery) cyazofamid and metabolite CCIM. In 

addition, the HPLC/UV method (MRID 45409020; revised in MRID 46550401) is acceptable for 

use as a single analyte enforcement method provided a confirmatory method such as the 

LC/MS/MS method is used. 

Recommended Tolerances

Tolerances are established in 40 CFR §180.601 with the following tolerance expression, as per 

the Steve Knizner memo dated 5/27/09:

Tolerances are established for residues of the fungicide cyazofamid, including its metabolites 
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and degradates, in or on the commodities in the following table. Compliance with the 

tolerance levels specified in the following table is to be determined by measuring only the 

sum of 4-chloro-2-cyano-N, N-dimethyl-5-(4-methylphenyl)-1H-imidazole-1-sulfonamide 

and its metabolite, 4-chloro-5-(4-methylphenyl)-1H-imidazole-2-carbonitrile, calculated as 

the stoichiometric equivalent of cyazofamid, in or on the following commodities.

HED recommends for establishment of the tolerances on the commodities in Table 1 below using 

the same tolerance expression as above:

Table 1. Tolerance Summary for Cyazofamid.

Commodity Established/Proposed 

Tolerance 

(ppm)

Recommended 

Tolerance1

(ppm)

Comments (correct commodity 

definition)

Bean, succulent 0.4 0.5

Bean, succulent, shelled 0.07 0.08

Leafy greens subgroup 4A 9.0 10

Basil, fresh leaves 30 30

Basil, dried leaves 80 90

Vegetable, tuberous and corm, 

subgroup 1C

0.02 0.02

Vegetable, fruiting, group 8-10 0.40 0.9

1 See “Revisions to Petitioned-For Tolerance” section.

When the above tolerances are established, the existing tolerances on spinach, potato, the fruiting 

vegetable group 8 and okra can be removed as requested by the petitioner.

International Harmonization

There are no Codex or Mexican maximum residue limits (MRLs) on the proposed crops. Canada 

has a tolerance at 0.02 ppm on potatoes, which is the same level as the US tolerance on the crop 

group (vegetable, tuberous and corm, subgroup 1C). Canada also has a tolerance of 0.2 ppm on 

tomatoes, which is less than the recommended US tolerance of 0.9 ppm on the crop group 

(vegetable, fruiting, group 8-10). 

The tolerance definition for the US and Canada are the same. Both the US and Canada include 

parent and the metabolite, 4- chloro-5-(4-methylphenyl)-1H-imidazole-2-carbonitrile, in the 

tolerance expression.

Revisions to Petitioned-For Tolerances

Bean,succulent: HED recommends increasing the proposed tolerance from 0.4 ppm to 0.5 ppm 

for succulent bean. The Organization for Economic Cooperation and Development (OECD) 

tolerance calculator gave a value of 0.5 for snap bean when average field trial values were 

entered (n = 8). 

Bean, succulent, shelled: HED recommends increasing the proposed tolerance for succulent 

shelled bean from 0.07 ppm to 0.08 ppm since the OECD tolerance calculator gave a value of 

0.08 ppm for lima bean when average field trial values were entered (n = 6).
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Leafy greens subgroup 4A: HED recommends increasing the proposed tolerance for the leafy

greens subgroup 4A from 9 ppm to 10 ppm. The established tolerance on spinach is 9.0 ppm. 

The representative commodities for the leafy greens subgroup 4A are head lettuce, leaf lettuce, 

and spinach. The OECD calculator gave values of 4 ppm for head lettuce, 8 ppm for leaf lettuce, 

and 10 ppm for spinach. The highest value of the representative commodities is 10 ppm.

Basil, dried leaves: HED recommends increasing the proposed tolerance for dried basil leaves 

from 80 ppm to 90 ppm. The OECD calculator value for dried basil leaves is 90 ppm when 

average field trial values were entered (n = 4).

Vegetable, fruiting, group 8-10: HED recommends increasing the proposed tolerance for the 

fruiting vegetable group 8-10 from 0.40 to 0.9 ppm. A tolerance of 0.40 ppm is established for 

the fruiting vegetable group 8. The representative commodities for Crop Group 8-10 are tomato, 

standard size, and one cultivar of small tomato; bell pepper and one cultivar of small nonbell 

pepper. The residue data on the fruiting vegetable group 8 support the fruiting vegetable group 

8-10. The OECD calculator using average field trial values gives values of 0.2 ppm for tomato

(n = 16), 0.4 ppm for bell pepper (n = 6) and 0.9 ppm for nonbell pepper (n = 3). The highest 

value of the representative commodities is 0.9 ppm.

Residue Profile

Table 2. Test Compound Nomenclature.

Compound Chemical Structure

Common name Cyazofamid

Company experimental name N/A

IUPAC name 4-chloro-2-cyano-N, N-dimethyl-5-p-tolylimidazole-1-sulfonamide

CAS name 4-chloro-2-cyano-N,N-dimethyl-5-(4-methylphenyl)-1H-imidazole-1-sulfonamide

CAS registry number 120116-88-3

End-use product (EP) Ranman® 400SC Agricultural Fungicide (EPA Reg. No. 71512-3)

Compound Chemical Structure of metabolite

Common name CCIM

IUPAC name 4-chloro-5-p-tolylimidazole-2-carbonitrile

CAS name 4-chloro-5-(4-methylphenyl)-1H-imidazole-2-carbonitrile

N

N

H3C

Cl

CN

SO2N(CH3)

2

N

H

N

H3C

Cl

CN
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Table 3. Physicochemical Properties of the Technical Grade Cyazofamid.

Parameter Value Reference

Melting point (°C) 152.7 PMRA Regulatory Note REG2006-

05 on Cyazofamid, 12/6/06

pH 4.9 e-Pesticide Manual, 13th Edition

Density at 20 °C (g/mL) 1.446

Water solubility (at 20 °C) pH Solubility (mg/L) REG2006-05

5

7

9

0.121

0.107

0.109

Solvent solubility (at 21.2°C) Solvent Solubility (g/L)

Acetone

Ethyl acetate

Methanol

Dichloromethane

Toluene

Hexane

n-Octanol

Acetonitrile

2-Propanol

43.1

16.19

1.74

94.82

6.0

0.03

0.04

29.446

0.43

Vapor pressure at 25°C <1.33 x 10-5Pa

Dissociation constant (pKa) Does not dissociate in water. No pKain 

the pH range of 2-12.

Octanol/water partition 

coefficient 

Log KOW = 3.2

KOW = 1.585 x 103

UV/visible absorption spectrum pH Λmax (nm)

2

7

10

285

279

287

Cyazofamid technical is a solid at room temperature with low vapor pressure. The formulation is 

a suspension concentrate. Detectable residues may occur in food. Field trial decline studies 

show that residues in agricultural commodities decline with increasing preharvest intervals. 

According to EPA’s Pesticide Fact Sheet (September 2004), cyazofamid has limited systemic 

activity so it is used as a protectant fungicide applied by ground or aerial spray. Exposure to 

surface water is possible through water runoff, soil erosion, or spray drift. 
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Residue Chemistry Guidelines

Directions for Use (860.1200)

Table 4. Summary of Proposed Directions for Use of Cyazofamid.

Applic. 

Timing, Type, 

and Equip.

Formulati

on

[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*

Basil

Postemergence.

Foliar 

broadcast 

sprays using 

ground, aerial,

or sprinkler 

irrigation 

equipment. 

Can be grown 

in a 

greenhouse.

Ranman 

400SC

[71512-3]

0.072-

0.078

9 0.7 0

Normal water volume is 

50-75 gals water per 

acre.

For downy mildew on 

basil, make applications 

on a 7 to 10 day 

schedule.

Beans, Succulent Podded and Succulent Shelled

Cicer arietinum (chickpea, garbanzo bean); Lupinus spp. (including sweet lupine, white sweet lupine, white 

lupine, and grain lupine). Phaseolus spp. (including kidney bean, lima bean, mung bean, navy bean, pinto bean, 

snap bean, and waxbean); Vicia faba (broad bean, fava bean); Vigna spp. (including asparagus bean, blackeyed 

pea and cowpea)

Postemergence.

Foliar 

broadcast 

sprays using 

ground, aerial,

or sprinkler 

irrigation 

equipment.

Ranman 

400SC

[71512-3]

0.072 6 0.43 0 Normal water volumes 

are 20-60 gals water per 

acre.

For downy mildew on 

lima beans: Make 

applications on a 7 to 10 

day schedule.

For cottony leak control: 

Make the initial 

application at full bloom 

(1st pods) and repeat on 

a 7-14-day schedule.

For Phytophthora blight 

control: Make the 1st

application at 100% 

bloom-pin pod 

development and a 2nd

application at late pinsmall pod development 

and repeat every seven 

days.

Fruiting Vegetables (Crop Group 8-10)

African eggplant; bush tomato; bell pepper; cocona; currant tomato; eggplant; garden huckleberry; goji berry; 

groundcherry; martynia; naranjilla; okra; pea eggplant; pepino; nonbell pepper; roselle; scarlet eggplant; 
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sunberry; tomatillo; tomato; tree tomato; cultivars, varieties, and/or hybrids of these

Postemergence. 

Broadcast 

foliar or soil 

drench to the 

base of the 

plants at 

transplanting

or in 

transplant 

water. 

Ground, 

aerial, or 

sprinkler 

irrigation 

equipment. 

Tomatoes for 

transplant can 

be grown in 

the 

greenhouse. 

A soil drench 

can be applied 

to tomatoes in 

the 

greenhouse.

Ranman 

400SC

[71512-3]

0.054-

0.072

Soil 

drench: 

0.078 lb 

ai/100 gals 

water

6 0.43 0

Normal water volumes 

are 30-60 gals water per 

acre.

For late blight control, 

make applications on a 7

to 10 day schedule.

For Phytophthora blight 

control, apply to the 

base of the plants at the 

time of transplanting. 

Alternatively, apply in 

transplant water at the 

time of transplanting. 

Apply 0.072 lb ai/A in 

transplant water in a 

water volume of at least 

50 gals/A for the initial 

application. Apply on a 

7 to 10 day schedule.

Tomato Greenhouse 

Transplant Production: 

For control of Pythium 

spp., make a single 

fungicide application to 

the seeding tray at the 

time of planting or at 

any time thereafter up 

until 1 week before 

transplanting. Apply the 

fungicide solution as a 

drench to thoroughly 

wet the growing medium 

(1 pt of solution per 

square foot if the 

growing medium is 4 

inches deep). Do not 

use a surfactant with this 

drench application.

Leafy Greens, Crop Subgroup 4A

Amaranth (leafy amaranth, Chinese spinach, tampala); arugula (Roquette); chervil; edible-leaved 

chrysanthemum; garland chrysanthemum; corn salad; garden cress; upland cress (yellow rocket, winter cress); 

dandelion; dock (sorrel); endive (escarole); lettuce (head and leaf); orach; parsley; garden purslane; winter 

purslane; radicchio (red chicory); spinach; New Zealand spinach; vine spinach (Malabar spinach, Indian spinach).

Posttransplant; 

Post-seeding;

Postemergence.

Foliar 

broadcast or 

soil drench 

Ranman 

400SC

[71512-3]

0.072** 6 0.43 0 Downy mildew: Apply 

at 7-14-day intervals.

Pythium: Make first 

application as a band to 

the soil as a directed, 

post- transplant or postseeding application; 
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band spray 

using ground, 

aerial, or 

sprinkler 

irrigation 

equipment.

alternatively, apply in 

transplant water at the 

time of transplant as a 

soil drench in at least 50 

gals water per acre. 

Apply at 7 to 10 day 

intervals.

Normal water volumes 

are 20-60 gals water per 

acre.

Tuberous and Corm Vegetables, Crop Subgroup 1C

Arracacha; arrowroot; Chinese artichoke; Jerusalem artichoke; edible canna; bitter cassava; sweet cassava; 

chayote (root); chufa; dasheen (taro); ginger; leren; potato; sweet potato; tanier; turmeric; yam bean; true yam

Postemergence 

foliar sprays 

using ground, 

aerial, or 

sprinkler 

irrigation 

equipment.

Can also be atplanting, infurrow at 

planting, or 

lay-by/ hilling

Ranman 

400SC

[71512-3]

Foliar: 

0.036-

0.072**

At 

planting: 

0.42 fl oz 

per 1000 

linear feet

(0.16 lb 

ai/A based 

on a 36” 

row

spacing)

Lay-by/ 

Hilling: 

0.072

10 0.72** 7 Normal water volumes 

are 20-50 gals water per 

acre.

For foliar blight, make 

applications on a 7 to10

day schedule.

For tuber and corm rot 

control, make the last 2 

to 3 applications prior to 

harvest at the rate of 

0.072 lb ai/A applied 

weekly.

For pink rot, Phythium 

root and crown rot 

control at planting, 

apply 0.42 fl oz product 

per 1000 linear foot of 

row in-furrow at 

planting using a 

minimum of 5 gals 

water per acre. Apply in 

a 6-8 inch band directly 

over the seed pieces 

prior to furrow closure. 

Mefenoxam can be 

added as a tank mix.

For additional control of 

Pythium root and crown 

rot, in combination with 

an at-planting, in-furrow

application, apply as a 

broadcast spray at 0.072

lb ai/A in a minimum of 

20 gals of finished spray 

solution per acre at 

hilling.

* Use directions and limitations:
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The plantback interval is 0 days for crops on the label and 30 days for other crops. 

Spray volumes will usually range from 20-100 gals per acre for dilute sprays and 5-10 gals/A for concentrate sprays 

and aerial sprays. Aerial sprays should be made in a minimum of 5 gals of water per acre.

Alternate sprays of Ranman 400SC with a fungicide with a different mode of action; do not make more than three 

consecutive applications of Ranman 400SC followed by at least three applications of fungicides having different 

modes of action before applying additional RANMAN 400SC. 

Ranman 400SC should be tank mixed with an organosilicone surfactant, non-ionic surfactant, or a blend of an 

organosilicone and a non-ionic surfactant. 

** 2.75 fl oz product /A = 0.0715 lb ai/A and 27.5 fl oz product /A= 0.715 lb ai/A. HED rounds up to 0.072 and 

0.72, respectively, as per EPA’s Hot Sheet # 10.

Conclusions. 

Provided the revisions given below are made, the Ranman 400SC label is adequate to allow 

evaluation of the residue data relative to the proposed use.

The Ranman 400 SC label should be amended to prohibit applications to legumes grown for 

livestock feeds because no residue data are available for cowpea forage and hay. The statement 

“Do not apply to cowpea used for livestock feed” should be added to the label. Cowpea is a 

succulent shelled bean.

An organosilicone surfactant (OSS) was used in all field trials on basil, snap beans, lima beans, 

pepper, potato, and spinach and on several field trials on tomato. Either a nonionic surfactant 

(NIS) or OSS was used in all field trials on head lettuce and leaf lettuce. The label indicates that 

Ranman 400 SC should be tank mixed with an organosilicone surfactant, non-ionic surfactant, or 

a blend of an organosilicone and non-ionic surfactant. The label should be revised to specify that 

an organosilicone surfactant can be used on basil, snap beans, lima beans, pepper, potato, 

spinach and tomato, and either a nonionic surfactant or an organosilicone surfactant can be used 

on head and leaf lettuce. 

Nature of the Residue (860.1300/1850)

Amelia Acierto, 2/18/04, DP# D298915, Cyazofamid – Meeting Report of the Metabolism Assessment Review 

Committee (MARC).

Amelia Acierto, 2/20/04, DP# D285680, PP#1F06305, Cyazofamid. Petition for the Establishment of Permanent 

Tolerances for Use on Cucurbits, Potatoes, Tomatoes, and Imported Wine Grapes. Summary of Analytical 

Chemistry and Residue Data; Plants: 45409015.der, 45409016.der, 45409017.der; Goat: 45409018.der; Hen: 

45409019.der; Rotational Crops: 45409036.der.

Breann Hanson, 8/3/10, DP# D376500, Cyazofamid. Human Health Risk Assessment for Proposed Section 18 Use 

on Basil.
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CHEMICAL: CYAZOFAMID

Date: 18-February-2004

Table 5. Residues of Concern in Plants, Livestock, Rotational Crops, and Water

Matrix For Risk Assessment For Tolerance Expression

Plants Parent and CCIM Parent and CCIM

Livestock No decision (For future cattle feeding 

studies, the MARC recommended that the 

petitioner analyze parent, CCIM, CCBA, 

and CCBA-cysteine conjugate.)

No decision

Rotational crops Parent only Parent only

Water Parent, CCIM, CCIM-AM, and CTCA N/A

Nature of the Residue - Plants

The nature of the residue in basil, lettuce, snap bean, lima bean, pepper, potato spinach, and 

tomato is adequately understood based on previously submitted metabolism studies conducted on 

grape, potato, and tomato. The results of the metabolism studies in plants indicated that the 

parent and CCIM are the major residues (>10% TRR). There are no specific toxicity concerns 

for all other minor metabolites. For the risk assessment and tolerance expression, the parent

cyazofamid and the metabolite CCIM are the residues of concern in primary (treated) plants. 

Nature of the Residue – Livestock

Provided that application to cowpea used for livestock feed is prohibited on the label, the 

registered and proposed uses of cyazofamid fall under 40 CFR §180.6(a)(3) with respect to 

livestock commodities, i.e., there is no reasonable expectation that finite residues will occur in 

livestock commodities. 

Goat and hen metabolism studies have been reviewed; however, residues of concern in livestock 

commodities have not been identified (A. Acierto, 2/18/04, DP# D298915). Based on the 

available goat metabolism study, the MARC determined that the following metabolites should be 

analyzed for future cattle feeding studies: cyazofamid, CCIM, CCBA (4-(4-chloro-2-

cyanoimidazol-5-yl)benzoic acid, and the CCBA-cysteine conjugate. Provided that application 

to cowpea used for livestock feed is prohibited on the label, there are no poultry or swine 

feedstuffs associated with registered or proposed uses (Table 1 Feedstuffs, June 2008).

Confined Accumulation in Rotational Crops

A confined accumulation in rotational crop study was previously submitted in conjunction with 

an earlier petition (PP#1F06305; DP# D285680, A. Acierto, 2/20/04; 45409036.der). The results 

of these data showed that cyazofamid and structurally related metabolites are each expected to be 

present at a level less than 0.01 ppm at a plantback interval of 30 days. For the risk assessment 

and tolerance expression, parent is the only residue of concern in rotational crops. Therefore, the

rotational crop plantback interval (PBI) of 0 days for crops which are on the label and 30 days 

for other crops is appropriate. 
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Residue Analytical Methods (860.1340)

Amelia Acierto, 2/20/04, DP# D285680, PP#1F06305, Cyazofamid. Petition for the Establishment of Permanent 

Tolerances for Use on Cucurbits, Potatoes, Tomatoes, and Imported Wine Grapes. Summary of Analytical 

Chemistry and Residue Data; Plants: 45409022.der, 45409020.der.

Breann Hanson, 8/3/10, DP# D376500, Cyazofamid. Human Health Risk Assessment for Proposed Section 18 Use 

on Basil.

Elizabeth Kolbe, 10/22/03, DP# D286108, PP# 3F6595. Cyazofamid on Potatoes, Tomatoes, Cucurbit and Grapes. 

Tolerance Method Review and Multi-Residue Method Review. PC Code 085651 (MRID#: 454090-33, 456385-08, 

454090-34, 454090-32, 454090-20, 454090-22); ACB # B02-(58-61).

Elizabeth Kolbe, 2/27/06, DP# D326164, PP# 3F6595. Review of Resubmitted Analytical Method for Cyazofamid 

and its Metabolite CCIM in Crops. PC Code 085651 (MRID#: 46550401); ACB Project # B06-13.

Enforcement Methods – Plants

Adequate enforcement methodology is available to enforce the proposed tolerances. Cyazofamid 

and metabolite CCIM are completely recovered (>80% recovery) in non-fatty commodities using 

FDA’s Multiresidue Protocol D (without cleanup) (MRID 45409022). Tomatoes were fortified 

with cyazofamid at 0.05 ppm and with CCIM at 0.1 ppm; recoveries were adequate. The 

multiresidue method can be used as an enforcement method.

In addition, an HPLC/UV method (MRID 45409020; revised in MRID 46550401) is acceptable 

for use as a single analyte enforcement method provided a confirmatory method such as the 

LC/MS/MS method discussed below is used. An independent laboratory validation of the 

HPLC/UV method (MRID 45409020) was conducted on tomatoes; adequate recoveries were 

obtained on tomatoes for cyazofamid and CCIM at an LOQ of 0.01 ppm for each analyte. 

Successful radiovalidation of the HPLC/UV method was conducted on samples from the grape 

and potato metabolism studies (MRIDs 45409016 and 45409017).

Data Collection Method – Plants

48629401.der (includes MRID 48629405): Lettuce (head and leaf)

48629402.der: Basil

48629403.der: Snap bean (a succulent bean)

48629404.der : Lima bean (a succulent shelled bean)

Samples of lettuce, basil, snap bean and lima bean were analyzed for residues of cyazofamid and 

its metabolite CCIM using the LC/MS/MS method; the method is a modified version of the 

method in MRID 45409020. The limits of quantitation (LOQs; determined as the lowest level of 

method validation, LLMV) were 0.01 ppm for each analyte in head lettuce, leaf lettuce, snap 

bean, lima bean, and fresh basil and 0.1 ppm for each analyte in dried basil. The method was 

adequate for data collection based on acceptable method validation and concurrent recovery data. 

The fortification levels used in concurrent method recovery and method validation were adequate 

to bracket expected residue levels. Concurrent recoveries and residues in the treated samples

were not corrected for residues in controls. The analytical method does not specify conversion 

of metabolite residues to parent equivalents; therefore, quantifiable residues of CCIM were 

converted to parent equivalents by the study reviewer using a molecular weight conversion factor 
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of 1.49 (MW of cyazofamid 324.79 ÷ MW of CCIM 217.65).

Field trials on pepper, spinach, tomato and potato were previously reviewed. The data collection 

method for pepper and spinach was the LC/MS/MS method. The data collection method for 

tomato and potato was the HPLC/UV method. All LOQs were 0.01 ppm for each analyte in each 

crop.

Conclusions. 

The data collection and enforcement methods are adequate to determine residues of cyazofamid 

and its metabolite CCIM in lettuce, basil, snap bean, lima bean, pepper, potato, spinach, and 

tomato. An enforcement method for non-fatty commodities is FDA’s Multiresidue Protocol D 

(without cleanup), which completely recovers (>80% recovery) cyazofamid and metabolite 

CCIM. In addition, an HPLC/UV method (MRID 45409020; revised in MRID 46550401) is 

acceptable for use as a single analyte enforcement method provided a confirmatory method such 

as the LC/MS/MS method is used. 

The data collection method (LC/MS/MS), a modified version of the method in MRID 45409020, 

is adequate for determination of cyazofamid and CCIM in residue samples, based on adequate 

recoveries and limits of quantitation, which were 0.01 ppm for each analyte in head lettuce, leaf 

lettuce, snap bean, lima bean, fresh basil, pepper, and spinach and 0.1 ppm for each analyte in 

dried basil. The HPLC/UV method is adequate for determination of residues of cyazofamid and 

CCIM in potato and tomato at the LOQ of 0.01 ppm for each analyte.

Multiresidue Methods (860.1360)

Amelia Acierto, 2/20/04, DP# D285680, PP#1F06305, Cyazofamid. Petition for the Establishment of Permanent 

Tolerances for Use on Cucurbits, Potatoes, Tomatoes, and Imported Wine Grapes. Summary of Analytical 

Chemistry and Residue Data; 45409022.der

Elizabeth Kolbe, 10/22/03, DP# D286108, PP# 3F6595. Cyazofamid on Potatoes, Tomatoes, Cucurbit and Grapes. 

Tolerance Method Review and Multi-Residue Method Review.

Cyazofamid and its metabolite CCIM were analyzed according to the FDA Multiresidue Method 

(MRM) Test guidelines in PAM, Volume I, Appendix II (1/94). Testing using Protocols A and 

B is not required because cyazofamid and CCIM do not have an N-methylcarbamate structure 

and are not acid or phenol compounds. Using Protocol C, injections of cyazofamid and CCIM 

yielded adequate responses to several of the Section 302 GLC systems. Cyazofamid and CCIM 

were completely recovered (>80% recovery) using Protocol D (without cleanup). Cyazofamid 

was partially recovered (50-80% recovery) using Protocols E and F. CCIM was not further 

tested with Protocols E and F because <30% of CCIM was recovered from the Florisil column 

cleanup tests. 

Conclusions. 

Adequate multiresidue methods data (MRID 45409022) have been submitted. The FDA 

Multiresidue Method Protocol D (without cleanup) meets the requirement of OCSPP 860.1360 

for non-fatty commodities. Residues of cyazofamid and CCIM are completely recovered (>80% 
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recovery) from non-fatty commodities through the FDA Multiresidue Method Protocol D 

(without cleanup). In MRID 45409022, tomatoes were fortified with cyazofamid at 0.05 ppm 

and with CCIM at 0.1 ppm; recoveries using Protocol D were adequate. The multiresidue 

method can be used as an enforcement method. The multiresidue methods data have been 

forwarded by the Analytical Chemistry Branch of the Biological and Economic Analysis Branch 

(ACB/BEAD) to FDA (D286108, E. Kolbe, 10/22/03).

Storage Stability (860.1380)

48629401.der (includes MRID 48629405): Lettuce (head and leaf)

48629402.der: Basil

48629403.der: Snap bean

48629404.der: Lima bean

Storage stability data generated concurrently with the field trial studies are reported below.

Table 6. Summary of Storage Conditions and Durations of Samples from Crop Field Trial Studies. 

Matrix Storage 

Temperature 

(°C)

Actual Storage 

Duration1

Interval of Demonstrated Storage Stability (days)2,3

Basil, fresh

-20 8-284 days

(0.3-9.3 months)

Residues of cyazofamid were stable in/on fresh basil 

stored frozen for up to 284 days (9.3 months).

Residues of CCIM in/on fresh basil declined by 46% 

after 284 days (9.3 months) of freezer storage.

Basil, dried

-20 155-299 days

(5.1-9.8 months)

Residues of cyazofamid and CCIM were reasonably stable 

in/on dried basil stored frozen for up to 297 days (9.8 

months).

Beans, lima

-20 63-147 days

(2.1-4.8 months)

Residues of cyazofamid and CCIM were stable in/on lima 

beans stored frozen for up to 140 days (4.6 months).

Beans, snap3

-20 861-946 days

(28.3-31.1 months)

Residues of cyazofamid and CCIM were stable in/on snap 

beans stored frozen for up to 887 days (29.2 months).

Lettuce, head

-20 to -8.9 208-634 days

(6.8-20.8 months)

Residues of cyazofamid and CCIM were stable in/on leaf 

lettuce stored frozen for up to 634 days (20.8 months).

Lettuce, leaf

-20 to -8.9 251-624 days

(8.3-20.5 months)

1 Storage duration is from collection to analysis. Samples were analyzed within 0-1 day of extraction.

2 Storage stability data were generated concurrently with the field trial study.

3 No 0-day data were provided.

4 Pods with seeds

Conclusions. 

The available storage stability data are adequate to support the storage durations and conditions 

of the field trial samples. Except for residues of the metabolite CCIM in fresh basil, the data are 

adequate to conclude that residues of cyazofamid and CCIM in the field trial samples were stable 

during frozen storage. Residues of CCIM in fresh basil declined by 46% after 284 days (9.3 

months) of freezer storage; therefore, residues in fresh basil in the field trials were corrected for 

loss of CCIM in storage.
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Water, Fish, and Irrigated Crops (860.1400)

There are no proposed uses that are relevant to this guideline topic.

Food Handling (860.1460)

DER Reference List

There are no proposed uses that are relevant to this guideline topic.

Meat, Milk, Poultry, and Eggs (860.1480)

Amelia Acierto, 2/20/04, DP# D285680, PP#1F06305, Cyazofamid. Petition for the Establishment of Permanent 

Tolerances for Use on Cucurbits, Potatoes, Tomatoes, and Imported Wine Grapes. Summary of Analytical 

Chemistry and Residue Data; 45409018.der.

Livestock feed items are associated with the registered uses on carrots and potatoes and with the 

proposed uses on potato (as part of the tuberous and corm vegetable subgroup 1C) and cowpea. 

Livestock feed items are carrot culls, potato culls, processed potato waste, and cowpea seed, 

forage, and hay. There are no other proposed crops that are associated with significant livestock 

feed items (Table 1 Feedstuffs, June 2008).

The established tolerance on potato of 0.02 ppm is being converted into a tolerance on the 

tuberous and corm vegetable subgroup 1C at the same level.

There is an established tolerance on turnip greens. Turnip greens are grown for human 

consumption and are not likely to be used as a livestock feed.

Since no residue data have been submitted for cowpea forage and hay, the Ranman 400SC label 

(EPA Reg. No. 71512-3) should be amended to prohibit application to cowpea grown for 

livestock feed. The statement “Do not apply to cowpea used for livestock feed” should be added 

to the label.

With the restriction against use on cowpea used for livestock feed, there are no poultry or swine 

feed items associated with the registered or proposed uses.
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Table 7. Calculation of Dietary Burdens of Cyazofamid Residues to Livestock.

Feedstuff Type1 % Dry 

Matter2 % Diet2

Established

Tolerance or 

HAFT (ppm)

3

Dietary Contribution 

(ppm)

4

Beef Cattle

Untreated R -- 15 0 0

Potato, culls CC 20 30 0.02 0.03

Potato, processed waste CC 15 30 0.02 0.04

Untreated CC -- 20 0 0

Untreated PC -- 5 0 0

TOTAL BURDEN -- -- 100 -- 0.07

Dairy Cattle

Untreated R -- 45 0 0

Carrots, culls5 CC 12 10 0.09 0.075

Untreated CC -- 35 0 0

Untreated PC -- 10 0 0

TOTAL BURDEN -- -- 100 -- 0.075

1

 R: Roughage; CC: Carbohydrate concentrate; PC: Protein concentrate.

2

 Table 1 Feedstuffs (July 2008). 

3 The established tolerance is used for the registered use (carrot); the highest average field trial (HAFT) value is 

used for the proposed use (potato). 

4

 Contribution for beef and dairy cattle = tolerance ÷ % DM x % diet.

5

Potato culls and potato processed waste can also be fed to dairy cattle; however, both carrot and potato feed items 

are not expected to be fed.

No ruminant feeding study has been submitted. Based on the goat metabolism study (MRID 

45409018; PP#1F06305), residues in milk and ruminant tissues reflecting a dosing level of 10

ppm are reported in Table 8 below. In the metabolism study, two lactating goats per treatment 

group were orally dosed with the radiolabelled cyazofamid test substances for five consecutive 

days at a nominal rate of 10 ppm based on the food consumption during the acclimation period. 

The dosing level of 10 ppm is equivalent to 143x and 133x the maximum dietary burden of 

cyazofamid in beef and dairy cattle, respectively

Table 8. Total Radioactive Residues, Expressed as Cyazofamid Equivalents, in Goat Matrices from a 

Metabolism Study after Dosing with Radiolabelled Cyazofamid at 10 ppm.

Goat Matrix [Benzene14C]Cyazofamid (ppm) [Imidazole14C]Cyazofamid (ppm)

Milk 0.004-0.006 0.002-0.010

Liver 0.126 0.125

Kidney 0.07 0.106

Loin muscle 0.004 0.006

Rear leg muscle nondetectable (<0.01) nondetectable (<0.01)

Omental fat 0.006 0.01

Perirenal fat 0.01 0.01
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Table 9. Summary of Ruminant Metabolism Studies with Cyazofamid.

Commodity Feeding Level

(ppm)

Max. Residue in 

Tissue (ppm)

Tissue-to-Feed 

Ratio

Dietary Burden 

(ppm)

Expected 

Residue (ppm)

Milk 10 0.01 0.001 0.075 0.000075

Muscle (cattle) 0.01 0.001 0.07 0.00007

Fat (cattle) 0.01 0.001 0.07 0.00007

Liver (cattle) 0.126 0.0126 0.07 0.00088

Kidney (cattle) 0.106 0.0106 0.07 0.00088

Conclusions. 

The results of the goat metabolism study indicate that tolerances for residues of cyazofamid in 

ruminant commodities are not required for the purpose of this petition since there is no 

reasonable expectation that finite residues will occur in ruminant commodities [40 CFR 

§180.6(a)(3)]. 

Tolerances for residues of cyazofamid in poultry and swine commodities are not required 

provided that application to cowpea used for livestock feed is prohibited on the label. With that 

label prohibition, there are no poultry or swine feed items associated with the proposed or 

registered uses, and the proposed and registered uses fall under 40 CFR §180.6(a)(3) for poultry

commodities.

Crop Field Trials (860.1500)

48629401.der (includes MRID 48629405) (Lettuce, Head and Leaf)

48629402.der (Basil)

48629403.der (Snap Bean)

48629404.der (Lima Bean)

Table 10. Summary of Residues from Field Trials with Cyazofamid1,2

Crop Matrix Analyte

Applic. 

Rate

(lb ai/acre)

PHI 

(days) n

Residues (ppm)

Min. Max. LAFT HAFT Median Mean SD

BASIL Proposed Use = 0.7 lb ai/acre total application rate, 0-day PHI

Basil, fresh

(leaves and 

stems)3

Cyazofamid 

+ CCIM

0.693-

0.721 0 6 2.4 15 2.6 14 8.5 8.4 5.1

Basil, dried

(leaves and 

stems)3

Cyazofamid 

+ CCIM

0.693-

0.721 0 4 11 46 11 43 30 28 13

BEAN, LIMA Proposed Use = 0.43 lb ai/acre total application rate, 0-day PHI

Bean, lima

(succulent 

seeds)

Cyazofamid 

+ CCIM

0.427-

0.523 0-1 6 <0.02 <0.057 <0.02 <0.050 0.020 0.025 0.012

BEAN, SNAP Proposed Use = 0.43 lb ai/acre total application rate, 0-day PHI

Bean, snap

(pods with 

seeds)

Cyazofamid 

+ CCIM

0.426-

0.507 0 8 <0.022 <0.23 <0.029 <0.21 0.12 0.12 0.072

LETTUCE, HEAD Proposed Use = 0.43 lb ai/acre total application rate, 0-day PHI
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Lettuce, head

(head with 

wrapper 

leaves)

Cyazofamid 

+ CCIM

0.419-

0.506 0 11 <0.06 2.0 <0.080 1.8 0.65 0.83 0.61

LETTUCE, LEAF Proposed Use = 0.43 lb ai/acre total application rate, 0-day PHI

Lettuce, leaf

(leaves)

Cyazofamid 

+ CCIM

0.427-

0.587 0 11 <0.49 4.6 <0.54 4.5 1.8 2.1 1.3

1 Except for sample min/max, values reflect per trial averages; n = no. of field trials.

2 LAFT = Lowest Average Field Trial; HAFT = Highest Average Field Trial; SD = Standard Deviation. For 

computation of the LAFT, HAFT, median, mean, and standard deviation, values < LOQ are assumed to be at the 

LOQ.

3 Data for fresh basil include field trials and greenhouse trials. Data for dried basil reflect field trials.

The following data were previously reviewed and are included here for use in crop group 

establishment:

47528401.der (Pepper)

45409033.der (Potato)

47870704.der (Spinach)

45409031.de1 (includes MRIDs 45638507 and 45638508)(Tomato)

Table 11. Summary of Residues from Field Trials on Pepper, Spinach, and Tomato with Cyazofamid) 1, 2

Crop Matrix Analyte

Applic. 

Rate

(lb ai/acre)

PHI 

(days) n

Residues (ppm)

Min. Max. LAFT HAFT Median Mean SD

PEPPER Proposed Use = 0.43 lb ai/acre total application rate, 0-day PHI

Pepper , Bell Cyazofamid 

+ CCIM

0.418-

0.429

0 6 <0.047 0.297 <0.048 <0.236 0.075 0.101 0.069

Pepper, 

Nonbell

Cyazofamid 

+ CCIM

0.419-

0.426

0 3 <0.221 0.331 <0.258 0.321 0.259 0.279 0.036

POTATO Proposed Use = 0.71 lb ai/A total application rate, 7-day PHI

Potato Cyazofamid 

+ CCIM

0.698-

0.743 7 18 <0.02 <0.02 <0.02 <0.02 <0.02 <0.02 <0.02

SPINACH Proposed Use = 0.43 lb ai/acre total application rate, 0-day PHI

Spinach Cyazofamid 

+ CCIM

0.347-

0.366

0 10 1.5 6.6 1.6 6.5 3.1 3.3 1.5

TOMATO Proposed Use = 0.43 lb ai/acre total application rate, 0-day PHI

Tomato Cyazofamid 

+ CCIM

0.413-

0.434

0 16 <0.02 <0.17 <0.02 <0.16 0.055 0.063 0.035

1 Except for sample min/max, values reflect per trial averages; n = no. of field trials.

2 LAFT = Lowest Average Field Trial; HAFT = Highest Average Field Trial; SD = Standard Deviation. For 

computation of the LAFT, HAFT, median, mean, and standard deviation, values < LOQ are assumed to be at the 

LOQ of 0.01 ppm for each analyte. 

Basil

The Interregional Research Project Number 4 (IR-4) has submitted field trial data for cyazofamid 

on basil. Four field trials were conducted in the United States during the 2009-2010 growing 

seasons in the North American Free Trade Agreement (NAFTA) Growing Zones 2 (MD and NC; 

2 trials) and 10 (CA and AZ; 2 trials). In addition, two greenhouse trials were conducted in 

Zones 3 (FL) and 10 (CA).
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Each trial consisted of one untreated plot and one treated plot. At each trial location, the treated 

plot received nine foliar broadcast or directed applications of a 3.33 lb ai/gal suspension 

concentrate (SC) formulation of cyazofamid (Ranman® 400SC) at 0.074-0.083 lb 

ai/A/application, for a total seasonal rate of 0.693-0.721 lb ai/A. Applications were made at 6- to 

8-day retreatment intervals (RTIs) using ground equipment in spray volumes of 21.07-46.28 

gal/A. An organosilicone surfactant (OSS), Silwet L-77, was added to the spray mixture for each 

of the applications. The use rates of adjuvant:formulated product were mostly 2:3 or 3:4, v/v. 

Samples of fresh basil leaves and stems were harvested from all trials at a 0-day preharvest 

interval (PHI); additional samples were collected at PHIs of 4, 7, 10, and 14 days from one trial 

(MD04) to assess residue decline. Additional leaves and stems were collected from four trials 

and dried for 1-3 days under ambient conditions or in an oven or forced air dryer to produce 

dried basil.

Samples were analyzed for residues of cyazofamid and its metabolite CCIM using an 

LC/MS/MS method adapted from a Pyxant Labs, Inc. analytical method. The limits of 

quantitation (LOQs; determined as the lowest level of method validation, LLMV) in fresh and 

dried basil were 0.01 and 0.1 ppm, respectively, for each analyte. The method was adequate for 

data collection based on acceptable method validation and concurrent recovery data. The 

fortification levels used in concurrent method recovery were adequate to bracket expected 

residue levels. Concurrent recoveries and residues in the treated samples were not corrected for 

residues in controls. The analytical method does not specify conversion of metabolite residues to 

parent equivalents; therefore, quantifiable residues of CCIM were converted to parent 

equivalents by the study reviewer using a molecular weight conversion factor of 1.49 (MW of 

cyazofamid 324.79 ÷ MW of CCIM 217.65).

Samples were stored frozen (-20 °C) from collection to analysis for 8-284 days (0.3-9.3 months) 

for fresh basil and 155-299 days (5.1-9.8 months) for dried basil. Samples were analyzed within 

0-1 days of extraction. To support the sample storage intervals, a concurrent storage stability

study was conducted with the field trial study. The data demonstrate that residues of cyazofamid 

and CCIM were reasonably stable in/on dried basil stored frozen for up to 297 days and residues 

of cyazofamid were stable in/on fresh basil stored frozen for up to 284 days, but residues of 

CCIM in/on fresh basil declined by 46% after 284 days of freezer storage. No 0-day data were 

provided. Samples of fresh basil were stored up to 284 days prior to analysis; therefore, the 

CCIM residue values for fresh basil were adjusted for residue decline on storage. No corrections 

for potential decline during storage are needed for residues of cyazofamid and CCIM in/on dried 

basil or for residues of cyazofamid in/on fresh basil from the submitted field trials; however, 

storage stability studies should always include a 0-day sampling interval to establish the residue 

levels present at the time samples are placed into storage [see OCSPP 860.1380(d)(6)(i)].

Following nine foliar broadcast or directed applications of the 3.33 lb ai/gal SC formulation of 

cyazofamid at 0.693-0.721 lb ai/A, residues (and per trial averages) of cyazofamid, CCIM, and 

combined residues, respectively, in/on fresh basil leaves and stems (from greenhouse and field 

trials) harvested at a 0-day PHI were 2.3-15 (2.5-14), 0.037-0.28 (0.040-0.28), and 2.4-15 (2.6-

14) ppm; corresponding residues (and per trial averages) in/on dried basil leaves and stems (field 

trials only) were 9.3-43 (9.6-40), 1.5-16 (1.6-16), and 11-46 (11-43) ppm. 
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Residues were generally higher in samples from the greenhouse trials than in samples from the 

field trials. In the field trials, residues (and per trial averages) of cyazofamid, CCIM, and 

combined residues, respectively, in/on fresh basil leaves and stems harvested at a 0-day PHI 

were 2.3-10 (2.5-9.4), 0.037-0.28 (0.040-0.28), and 2.4-10 (2.6-9.6) ppm; corresponding residues 

(and per trial averages) in/on fresh basil leaves and stems in the greenhouse trials were 12-15 

(14-14), 0.092-0.15 (0.096-0.13), and 12-15 (14-14) ppm. Dried basil leaves and stems were not 

collected in the greenhouse trials.

In the residue decline trial with fresh basil leaves and stems, average residues of cyazofamid and 

CCIM declined from 2.6 ppm at the 0-day PHI to <0.34 ppm at the 14-day PHI.

Bean, lima

IR-4 has submitted field trial data for cyazofamid on lima beans. Eight field trials were 

conducted in the United States during the 2009 growing season in the NAFTA Growing Zones 2 

(MD and NC; 4 trials), 5 (WI; 1 trial), 10 (CA; 2 trials), and 11 (ID; 1 trial). Two trial pairs 

(MD15/MD24 and NC30/NC31) were each conducted at the same location. Careful examination 

of the field trial records in accordance with ChemSAC guidance (Field Trial Differentiation, 

2012 Protocol) indicates that the only differences between each pair of trials were: use of 

different varieties of lima beans (all trials), use of different tank mixes for all applications (all 

trials); and a 6-day off-set in application dates (NC30/NC31 trials only). HED has concluded 

that the differences between the trials are insufficient to classify them as separate trials; 

therefore, each pair of trials constitutes a single trial with replicate samples for purposes of 

OCSPP 860.1500 data requirements. The adjustment in trial numbers results in a total of six 

field trials, with two trials conducted in NAFTA Zone 2.

Each trial consisted of one untreated plot and one treated plot. At each trial location, the treated 

plot received at least six foliar broadcast or directed applications of a 3.33 lb ai/gal SC

formulation of cyazofamid (Ranman® 400SC) at 0.069-0.076 lb ai/A/application, for a total 

seasonal rate of 0.427-0.523 lb ai/A. One additional application was required at three trial sites 

to allow the crop to mature (CA134) or due to unexpected rainfall occurring after the sixth 

application, thereby potentially impacting the residues if the samples were harvested following 

the rainfall (NC30 and NC31). Applications were made at 6- to 8-day RTIs using ground 

equipment in spray volumes of 32.51-46.08 gal/A. An OSS, Silwet L-77, was added to the spray

mixture for each of the applications. The use rate of adjuvant:formulated product was 3:4, v/v. 

Samples of lima beans were harvested from all trials at a 0-day PHI, except for Trial NC31, 

where samples were harvested at a 1-day PHI to allow plants to dry following rainfall that 

occurred 3 hours after the last application.

Samples were analyzed for residues of cyazofamid and its metabolite CCIM using an 

LC/MS/MS method adapted from a Pyxant Labs, Inc. analytical method. The LOQ, determined 

as the LLMV, was 0.01 ppm for each analyte. The method was adequate for data collection 

based on acceptable method validation and concurrent recovery data. The fortification levels 

used in method validation and concurrent method recovery were adequate to bracket expected 

residue levels. Concurrent recoveries and residues in the treated samples were not corrected for 

residues in controls. The analytical method does not specify conversion of metabolite residues to 
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parent equivalents. Residues of CCIM were not converted to parent equivalents in this study

because residues of the metabolite were below the LOQ in/on all samples.

Samples were stored frozen (-20 °C) from collection to analysis for 63-147 days (2.1-4.8 

months). Samples were analyzed within 0-1 days of extraction. Storage stability data generated 

concurrently with the field trial study demonstrate that residues of cyazofamid and CCIM were 

stable in/on samples of lima beans stored frozen for up to 140 days; no 0-day data were provided. 

These data are acceptable to support the storage conditions and durations of samples from the 

submitted field trials; however, storage stability studies should always include a 0-day sampling 

interval to establish the residue levels present at the time samples are placed into storage [see 

OCSPP 860.1380(d)(6)(i)].

Following six to seven foliar broadcast or directed applications of the 3.33 lb ai/gal SC 

formulation of cyazofamid at 0.427-0.523 lb ai/A, residues (and per trial averages) of 

cyazofamid, CCIM, and combined residues, respectively, in/on lima bean succulent seeds 

harvested at a 0- to 1-day PHI were <0.01-0.047 (<0.01-0.040), <0.01 (<0.01), and <0.02-<0.057 

(<0.02-<0.050) ppm. Cyazofamid residues were only detected in the ID20 trial. No residue 

decline data were submitted.

Bean, snap

IR-4 has submitted field trial data for cyazofamid on snap beans. Eight field trials were 

conducted in the United States during the 2007 growing season in the NAFTA Growing Zones 2 

(NJ, MD, and GA; 3 trials), 5 (MI and WI; 2 trials), 10 (CA; 2 trials), and 11 (WA; 1 trial). 

Each trial consisted of one untreated plot and one treated plot. At each trial location, the treated 

plot received at least six foliar broadcast or directed applications of a 3.33 lb ai/gal SC

formulation of cyazofamid (Ranman® 400SC) at 0.069-0.079 lb ai/A/application, for a total 

seasonal rate of 0.426-0.507 lb ai/A. One additional application was required at the CA10 trial 

to allow the crop to mature. Applications were made at 6- to 9-day RTIs using ground 

equipment in spray volumes of 31.90-60.08 gal/A. An OSS, Silwet L-77, was added to the spray

mixture for each of the applications. The use rate of adjuvant:formulated product was 3:4, v/v. 

Samples of snap bean pods with seed and snap bean plants with pods were harvested from all 

trials at a 0-day PHI; additional samples of snap bean pods with seed were collected at PHIs of 2, 

7, and 12 days from one trial (GA*11) to assess residue decline.

Samples were analyzed for residues of cyazofamid and its metabolite CCIM using an

LC/MS/MS method adapted from a Pyxant Labs, Inc. analytical method. The LOQ, determined 

as the LLMV, was 0.01 ppm for each analyte. The method was adequate for data collection 

based on acceptable method validation and concurrent recovery data. The fortification levels 

used in method validation and concurrent method recovery were adequate to bracket expected 

residue levels. Concurrent recoveries and residues in the treated samples were not corrected for 

residues in controls. The analytical method does not specify conversion of metabolite residues to 

parent equivalents; therefore, quantifiable residues of CCIM were converted to parent 

equivalents by the study reviewer using a molecular weight conversion factor of 1.49 (MW of 

cyazofamid 324.79 ÷ MW of CCIM 217.65).
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Samples were stored frozen (-20 °C) from collection to analysis for 861-946 days (28.3-31.1 

months) for pods with seeds and 847-944 days (27.9-31.0 months) for plants with pods. Samples 

were analyzed within 0-1 days of extraction. Storage stability data generated concurrently with 

the field trial study demonstrate that residues of cyazofamid and CCIM were stable in/on 

samples of snap bean stored frozen for up to 887-889 days; no 0-day data were provided. These 

data are acceptable to support the storage conditions and durations of samples from the submitted 

field trials; however, storage stability studies should always include a 0-day sampling interval to 

establish the residue levels present at the time samples are placed into storage [see OCSPP

860.1380(d)(6)(i)].

Following six to seven foliar broadcast or directed applications of the 3.33 lb ai/gal SC 

formulation of cyazofamid at 0.426-0.507 lb ai/A, residues (and per trial averages) of 

cyazofamid, CCIM, and combined residues, respectively, in/on snap bean pods with seeds 

harvested at a 0-day PHI were 0.012-0.22 (0.019-0.20), <0.01 (<0.01), and <0.022-<0.23 

(<0.029-<0.21) ppm; corresponding residues (and per trial averages) in/on snap bean plants with 

pods were 1.0-3.6 (1.4-3.3), 0.017-0.099 (0.029-0.088), and 1.1-3.6 (1.4-3.3) ppm. 

In the residue decline trial with snap bean pods with seeds, average residues of cyazofamid 

declined from 0.20 ppm at the 0-day PHI to 0.13 ppm at the 12-day PHI; residues of CCIM were 

<0.01 ppm in/on all samples.

Lettuce, head and leaf

IR-4 has submitted field trial data for cyazofamid on head and leaf lettuce. Twenty-six field 

trials were conducted in the United States and Canada during the 2008-2009 growing seasons in 

the NAFTA Growing Zones. Thirteen head lettuce trials were conducted in Zones 1 (NY; 1 

trial), 3 (FL; 1 trial), 5 (ON; 2 trials), 5A (QC; 1 trial), 5B (QC; 1 trial), 10 (NM and CA; 6 

trials), and 12 (BC; 1 trial), and thirteen leaf lettuce trials were conducted in Zones 2 (MD; 1 

trial), 3 (FL; 1 trial), 5 (ON; 2 trials), 5A (QC; 1 trial), 5B (QC; 1 trial), 10 (NM and CA; 6 

trials), and 12 (BC; 1 trial). 

Four trial pairs [08-CA*04/08-CA*05 (Salinas, CA, head lettuce); 08-CA03/08-CA19 (Holtville, 

CA; head lettuce); 08-NM14/08-NM12 (Las Cruces, NM; leaf lettuce); and 08-CA*22/08-

CA*21 (Salinas, CA; leaf lettuce)] were each conducted at the same location. Careful 

examination of the field trial records in accordance with ChemSAC guidance (Field Trial 

Differentiation, 2012 Protocol) indicates that the only differences between each pair of trials 

were: use of different varieties of lettuce (all trials), use of different tank mixes for all 

applications (all trials); an 8-day off-set in application dates (CA*22/CA*21 trials only); and a 

difference in soil type (loam vs. sandy loam; CA*22/CA*21 trials only). HED has concluded 

that the differences between the trials are insufficient to classify them as separate trials; 

therefore, each pair of trials constitutes a single trial with replicate samples for purposes of 

OCSPP 860.1500 data requirements. The adjustment in trial numbers results in a total of 22 field 

trials (11 head lettuce trials and 11 leaf lettuce trials), with four trials each for head lettuce and 

leaf lettuce conducted in NAFTA Zone 10.
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Each trial consisted of one untreated plot and one treated plot. At each trial location, the treated 

plot received at least six applications of a 3.33 lb ai/gal SC formulation of cyazofamid 

(Ranman® 400SC) at 0.065-0.079 lb ai/A/application (0.073-0.088 kg ai/ha/application), for a 

total seasonal rate of 0.419-0.587 lb ai/A (0.471-0.658 kg ai/ha). The first application was made 

to soil as a post-plant application after seeding or a post-transplant application. These 

applications were made on the day of or 1 day following planting or transplanting. Subsequent 

applications were made as foliar broadcast or directed applications with RTIs of 6-78 days 

between applications 1 and 2 and 5-15 days (mostly 6-8 days) between applications 2 through 8; 

applications were timed so that mature lettuce could be collected immediately following the final 

application (after the test substance had dried). One to two additional applications were required 

in five trials (CA*05, CA*04, NM11, NM14, and ON Trial 690) to allow the crop to mature. All 

applications were made using ground equipment in spray volumes of 30-49 gal/A (283-460 

L/ha). A non-ionic surfactant (NIS; Sylgard 309) or OSS (Silwet L-77) was added to the spray

mixture for each of the applications except for the first post-plant applications (all trials) and 

some post-transplant applications. The use rate of adjuvant:formulated product was 3:4, v/v. 

Samples of head lettuce with wrapper leaves and leaf lettuce were harvested from all trials at a 0-

day PHI; additional samples were collected at PHIs of 4, 7, 15, and 21 days from one leaf lettuce 

trial (CA*22) to assess residue decline. In addition, samples of head lettuce without wrapper 

leaves were also collected at the three 2009 Canadian head lettuce trials.

Samples were analyzed for residues of cyazofamid and metabolite CCIM using an LC/MS/MS

method adapted from a Pyxant Labs, Inc. analytical method. The LOQ, determined as the 

LLMV, was 0.01 ppm for each analyte. The method was adequate for data collection based on 

acceptable method validation and concurrent recovery data. The fortification levels used in 

concurrent method recovery were adequate to bracket expected residue levels. Concurrent 

recoveries and residues in the treated samples were not corrected for residues in controls. Since 

the analytical method does not specify conversion of metabolite residues to parent equivalents, 

quantifiable residues of CCIM were converted to parent equivalents by the study reviewer using 

a molecular weight (MW) conversion factor of 1.49 (MW of cyazofamid of 324.79 ÷ MW of 

CCIM of 217.65).

Samples were stored frozen (-20 to -8.9 °C) from collection to analysis for 208-634 days (6.8-

20.8 months) for head lettuce and 251-624 days (8.3-20.5 months) for leaf lettuce. Samples were 

analyzed within 0-1 days of extraction. Storage stability data generated concurrently with the 

field trial study demonstrate that residues of cyazofamid and CCIM were stable in/on samples of 

leaf lettuce stored frozen for up to 634 days; no 0-day data were provided. These data are 

acceptable to support the storage conditions and durations of samples from the submitted field 

trials. Any storage stability studies which may be submitted in the future should always include 

a 0-day sampling interval to establish the residue levels present at the time samples are placed 

into storage [see OCSPP 860.1380(d)(6)(i)].

Following one soil banded application made post-planting or post-transplant and five to seven 

foliar broadcast or directed applications (six to eight total applications) of the 3.33 lb ai/gal SC 

formulation of cyazofamid at 0.419-0.587 lb ai/A (0.471-0.658 kg ai/ha), residues (and per trial 

averages) of cyazofamid, CCIM, and combined residues, respectively, in/on head lettuce with 

wrapper leaves harvested at a 0-day PHI were 0.05-2.0 (0.070-1.8), <0.01-0.044 (<0.01-0.038), 
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and <0.06-2.0 (<0.080-1.8) ppm; corresponding residues (and per trial averages) in/on head 

lettuce without wrapper leaves were <0.01-0.57 (<0.01-0.55), <0.01-0.019 (<0.01-0.018), and 

<0.02-0.59 (<0.02-0.58) ppm. Residues (and per trial averages) of cyazofamid, CCIM, and 

combined residues, respectively, in/on leaf lettuce harvested at a 0-day PHI were 0.48-4.5 (0.53-

4.5), <0.01-0.074 (<0.013-0.064), and <0.49-4.6 (<0.54-4.5) ppm.

In the residue decline trial with leaf lettuce, average combined residues of cyazofamid and CCIM 

declined from 2.8 ppm at the 0-day PHI to <0.12 ppm at the 21-day PHI.

Crop Groups

Fruiting Vegetable Group 8-10

A tolerance of 0.40 ppm is established for the fruiting vegetable group 8. The representative 

commodities for Crop Group 8-10 are tomato, standard size, and one cultivar of small tomato; 

bell pepper and one cultivar of small nonbell pepper. 

Tomato

Residue data have previously been reviewed for tomatoes (DP# D285680, A. Acierto, 2/20/04 

and 10/1/04; 45409031.der). The residue data included data on the standard size tomato and on 

Roma tomato, which is a small tomato. Sixteen field trials were conducted on tomato with a PHI

of 0 days. Six broadcast foliar applications were made at the rate of approximately 0.071 lb 

ai/A/application for a total of 0.413-0.434 lb ai/A/season with retreatment intervals of mostly 6-8 

days and a 0-day PHI. An OSS was used in several field trials on tomato. The use rate of 

adjuvant:formulated product was 3:4, v/v.

Pepper

Residue data have previously been reviewed for bell and nonbell pepper (DP# D357042, A. 

Acierto, 3/18/09; 47528401.der). Six field trials were conducted on bell pepper and three field 

trials were conducted on nonbell pepper. Six broadcast foliar applications were made at the rate 

of 0.067-0.075 lb ai/A/application for a total of 0.418-0.429 lb ai/A/season with retreatment 

intervals of 6-8 days and a 0-day PHI. An OSS was used in all field trials on pepper. The use 

rate of adjuvant:formulated product was 3:4, v/v. 

Conclusion re. fruiting vegetable group 8-10.

The currently registered label for fruiting vegetables (letter dated 8/13/10) and the proposed label 

for the fruiting vegetable group 8-10 are the same regarding the methods of application, number 

of applications, application rates, interval between foliar applications, and PHI.

The residue data supporting the established fruiting vegetable group 8 tolerance support the 

fruiting vegetable group 8-10 tolerance; however, the OECD calculator using average field trial 

residues gives tolerance levels of 0.2 ppm for tomato, 0.4 ppm for bell pepper, and 0.9 ppm for

nonbell pepper; therefore, the tolerance for the fruiting vegetable crop group should be 0.9 ppm 
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instead of the proposed 0.40 ppm.

Leafy greens subgroup 4A

The representative commodities for the leafy greens subgroup 4A are head lettuce, leaf lettuce, 

and spinach. The head and leaf lettuce field trials adequately reflect the proposed use. The 

spinach trials reflect five applications instead of the proposed six.

Head Lettuce: Six to seven applications were made to head lettuce, at 0.07-0.08 lb 

ai/A/application. The first application was a post-plant or post-transplant directed band applied 

0-1 day after seeding or transplanting. Five or six foliar applications were made, mostly six to 

eight days apart. The PHI was 0 days. The total applied was 0.419-0.506 lb ai/A/crop. An NIS

or OSS surfactant was used with all foliar applications.

Leaf Lettuce: Six to eight applications were made to head lettuce, at 0.07 -0.08 lb 

ai/A/application. The first application was a post-plant or post-transplant directed band applied 

0-1 day after seeding or transplanting. Five to seven foliar applications were made, six to eight 

days apart. The PHI was 0 days. The total applied was 0.427-0.587 lb ai/A/crop. An NIS or 

OSS was used with all foliar applications.

Spinach: Field trials on spinach were previously reviewed (MRID 47870704; D371162, A. 

Acierto, 2/24/10). At each test location, five foliar applications of Ranman 400SC were made at 

the target rate of 0.072 lb ai/A/application for a total of 0.347-0.366 lb ai/A/season, with 7 (± 1)

day intervals and a 0-day PHI. An OSS, Silwet L-77, was used in all field trials. Foliar 

broadcast applications were made at all field sites except TX*12, where foliar directed 

applications were made. 

Five applications totaling 0.347-0.366 lb ai/A were made in the field trials, whereas the proposed 

use would allow six applications totaling 0.43 lb ai/A. The current Ranman 400SC label (letter 

dated 8/13/10) restricts the number of applications on spinach to five. The OECD calculator 

using average field trial residues gives a value of 10 ppm for spinach. 

Conclusion re. leafy greens subgroup 4A.

The highest residue value for spinach was 6.6 ppm, reflecting five foliar applications. A 10 ppm 

tolerance can be reasonably expected to be adequate to cover an additional sixth application.

Vegetable, tuberous and corm, subgroup 1C

A tolerance is established on potato at 0.02 ppm. The only representative commodity for the 

tuberous and corm vegetable subgroup 1C is potato. 

Field trial data on potato were previously reviewed (D285680, A. Acierto, 2/20/04; 

45409033.der). Residue data reflected seven to ten broadcast foliar applications for total 

application rates of 0.698-0.743 lb ai/A with retreatment intervals of 5-8 days and a 7-day PHI. 

An OSS, Silwet L-77, was used in all field trials. The LOQ of the HPLC/UV method (MRID 
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45409020) was 0.01 ppm for each analyte. Combined residues of cyazofamid and CCIM were 

all <0.02 ppm. The residue data on potato can be used to support a subgroup 1C tolerance. 

The current Ranman 400SC label (letter dated 8/13/10) for potato is consistent with the proposed 

use directions for potato with respect to methods of application, number of applications, 

application rates, interval between foliar applications, and PHI.

Conclusion re. tuberous and corm vegetable subgroup 1C. The previously submitted residue 

data on potato supports the proposed use and the proposed 0.02 ppm tolerance on the tuberous 

and corm vegetable subgroup 1C.

Processed Food and Feed (860.1520)

Amelia Acierto, 2/20/04, DP# D285680, PP#1F06305, Cyazofamid. Petition for the Establishment of Permanent 

Tolerances for Use on Cucurbits, Potatoes, Tomatoes, and Imported Wine Grapes. Summary of Analytical 

Chemistry and Residue Data; 45409033.de2 (potato) and 45409031.de2 (tomato)

Amelia Acierto, 3/18/09, DP# D357042, Cyazofamid. Amend Section 3 to Add Uses on Fruiting Vegetables, Okra, 

Grape (East of the Rocky Mountains), and Greenhouse Vegetable Transplants. Summary of Analytical Chemistry 

and Residue Data.

No additional processing studies have been submitted. Processing studies have previously been 

reviewed on potato and tomato. The analytical method used in the potato and tomato processing 

studies was the HPLC/UV enforcement method (MRID 45409020).

Potato: No detectable residues of cyazofamid or CCIM were found in the potato tubers used for 

processing or the processed commodities (chips, flakes, and wet peel). The reviewer requested 

that a study be conducted at 5x because the RAC samples that were used for processing bore 

nondetectable (<0.01 ppm) residues after treatments at an exaggerated rate of ~1.9x, which is 

less than the maximum theoretical concentration factor of 5.0x for potatoes. The petitioner 

submitted the following response in MRID 46537730:

“The maximum label application for cyazofamid to potatoes is 0.071 lb ai/A applied 10 

times at 7-day intervals. For the processing study, applications 1 through 6 were made at 

0.070-0.073 lb ai/A and at 7-day intervals. Applications 7 through 10 were made at 5-

day intervals. The final application was at a l0x rate (0.713 lb ai/A). Cyazofamid has 

been shown to have a half-life of about 1 day on crops such as cucumber, cantaloupe, 

summer squash and tomato. With this short half-life there is essentially no carryover 

from one application to the next even with the shorter 5-day interval. Consequently the 

final application is the only application that will potentially result in residues on the RAC 

and it was applied at 10 X the label rate. In addition, the label PHI is 7 days but in the 

potatoes grown for processing the samples were collected at a PHI of 3 days. The 

potatoes were delivered to the processor within a couple of hours of sampling since the 

processor was only 20 miles from the field site. The samples were stored for 19 days at 7 

°C ± 3 °C prior to processing.

The use of exaggerated rates of application is to assure that residues are present to 
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determine the concentration or lack thereof after processing. Two representative samples 

were taken for analysis in the field. One sample had 0.02 ppm cyazofamid and 0.01 ppm 

CCIM. The other sample had <0.01 ppm for both compounds. Therefore, the desired 

residues were present in the field. Samples taken 19 days later at the time of processing 

had residues <0.01 ppm for both compounds. Storage for periods longer than 19 days is 

typical for potatoes being processed into chips or granules. The processing loss is clearly

in the storage phase of the processing, not in the production of the potatoes. Considering

that the last application rate used was 10X the proposed rate and the PHI was decreased 

to 3 days, it is unlikely that repeating the study with multiple applications at 5X at 7-day

intervals would achieve residues any higher than those found in this study. 

Consequently, it is ISK Biosciences Corporation’s opinion that this study is scientifically

valid and that a replacement is not needed.”

The potato processing study is adequate to conclude that the combined residues in the processed 

commodities are not likely to exceed the 0.02 ppm tolerance level on the potato tuber.

Tomato: The tomato processing data indicated that residues of cyazofamid do not concentrate in 

tomato paste and puree (processing factors of <0.3x) and residues of CCIM do not concentrate 

significantly in puree but concentrated by a factor of 4x in tomato paste. Although concentration 

of CCIM in tomato paste was observed, combined residues of cyazofamid and CCIM are not 

likely to concentrate in tomato processed commodities to exceed the tolerance on the RAC.

Conclusions. No additional processing studies have been submitted and none are required. The 

previously submitted tomato and potato processing studies are adequate to show that residues in 

tomato and potato processed commodities will not concentrate above the tolerance levels for the 

raw agricultural commodities; therefore, separate tolerances on the processed commodities of 

tomato and potato are not required.

Rotational Crops (Field; 860.1900)

Breann Hanson, 8/3/10, DP# D376500, Cyazofamid. Human Health Risk Assessment for Proposed Section 18 Use 

on Basil.

Since the results of the confined rotational crop study showed that cyazofamid and structurally

related metabolites are each expected to be present at a level less than 0.01 ppm at a plantback 

interval of 30 days, no field rotational crop studies are required. 

Tolerance Derivation

The Organization for Economic Cooperation and Development (OECD) tolerance calculation 

procedures were used to determine tolerance estimates for the raw agricultural commodities. 

Average values of replicate samples for each field trial constituted the database.

For consideration of crop group or subgroup tolerances, the representative commodities were 

evaluated individually to determine a tolerance estimate for each representative crop; the highest 

tolerance estimate was used for the crop group or subgroup tolerance.
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All trials were conducted within ±25% of the good agricultural practices (GAP) application rate 

and PHI. Therefore, proportionality was not considered for any of the trials.

An organosilicone surfactant (OSS) was used in all field trials on basil, snap beans, lima beans, 

pepper, potato, and spinach and on several field trials on tomato. A nonionic surfactant (NIS) or 

OSS was used in all field trials on head lettuce and leaf lettuce. The adjuvant: Ranman 400SC 

use rate was 3:4 (v/v) for all crops except basil; for basil, the adjuvant use rate was mostly 2:3 or 

3:4 (v/v). 

The data collection methods were an HPLC/UV method or an LC/MS/MS method which is a 

modified version of the HPLC/UV method. Both methods determine parent and CCIM with an 

LOQ of 0.01 for each analyte in basil, snap bean, lima bean, lettuce, pepper, potato, spinach, and 

tomato RACs, and an LOQ of 0.1 ppm for each analyte in dried basil.

An OECD tolerance calculation was not conducted for potato since all residues in the potato 

field trial were less than the LOQ.

Some censored data (combined residues <0.02 ppm) were included in the data set for lima bean. 

The tomato data set contained one censored residue level. 

The residue values used as inputs and the recommended tolerances are summarized below.
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Basil, fresh (MRID 48629402)

A tolerance of 30 ppm is appropriate for fresh basil based on six trials (four field trials and two 

greenhouse trials) at a total seasonal application rate of 0.693-0.721 lb ai/A with a 0-day PHI.

0.693-0.721 lb ai/A; 0-day PHI

Residues (mg/kg) n

2.6 1

2.9 1

7.4 1

9.6 1

14 2

Cyazofamid

Basil -fresh

USA

0.693-0.721 lb ai/A; 0-day PHI

Total number of data (n) 6

Percentage of censored data 0%

Number of non-censored data 6

Lowest residue 2.600

Highest residue 14.000

Median residue 8.500

Mean 8.417

Standard deviation (SD) 5.080

Correction factor for censoring (CF) 1.000

Proposed MRL estimate

- Highest residue 14.000

- Mean + 4 SD 28.738

- CF x 3 Mean 25.250

Unrounded MRL 28.738

Rounded MRL 30

High uncertainty of MRL estimate.

[Small dataset]
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Basil, dried (MRID 48629402)

A tolerance of 90 ppm is appropriate for dried basil.

0.693-0.721 lb ai/A; 0-day PHI

Residues (mg/kg) n

11 1

29 1

30 1

43 1

Cyazofamid

Basil-dried

USA

0.693-0.721 lb ai/A; 0-day PHI

Total number of data (n) 4

Percentage of censored data 0%

Number of non-censored data 4

Lowest residue 11.000

Highest residue 43.000

Median residue 29.500

Mean 28.250

Standard deviation (SD) 13.150

Correction factor for censoring (CF) 1.000

Proposed MRL estimate

- Highest residue 43.000

- Mean + 4 SD 80.849

- CF x 3 Mean 84.750

Unrounded MRL 84.750

Rounded MRL 90

High uncertainty of MRL estimate.

[Small dataset]
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Bean, lima (MRID 48629404)

A tolerance of 0.08 ppm is appropriate for bean, succulent, shelled based on the residue data for 

lima bean.

0.427-0.523 lb ai/A; 0-1 day PHI

Residues (mg/kg) n

< 0.02 5

0.05 1

Cyazofamid

Crop

Lima Bean

0.427-0.523 lb ai/A; 0-day PHI

Total number of data (n) 6

Percentage of censored data 83%

Number of non-censored data 1

Lowest residue 0.020

Highest residue 0.050

Median residue 0.020

Mean 0.025

Standard deviation (SD) 0.012

Correction factor for censoring (CF) 0.444

Proposed MRL estimate

- Highest residue 0.050

- Mean + 4 SD 0.074

- CF x 3 Mean 0.033

Unrounded MRL 0.074

Rounded MRL 0.08

High uncertainty of MRL estimate.

[Small dataset and high level of censoring]
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Bean, snap (MRID 48629403)

A tolerance of 0.5 ppm is appropriate for bean, succulent based on the residue data for snap 

bean.

0.426-0.507 lb ai/A; 0-day PHI

Residues (mg/kg) n

0.029 1

0.056 1

0.068 1

0.11 1

0.12 1

0.2 2

0.21 1

Cyazofamid

Snap bean

USA

0.426-0.507 lb ai/A; 0-day PHI

Total number of data (n) 8

Percentage of censored data 0%

Number of non-censored data 8

Lowest residue 0.029

Highest residue 0.210

Median residue 0.115

Mean 0.124

Standard deviation (SD) 0.072

Correction factor for censoring (CF) 1.000

Proposed MRL estimate

- Highest residue 0.210

- Mean + 4 SD 0.411

- CF x 3 Mean 0.372

Unrounded MRL 0.411

Rounded MRL 0.5
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Lettuce, head (MRIDs 48629401 and 48629405)

The appropriate tolerance for the leafy greens subgroup 4A is 10 ppm, which is the highest level 

for the representative crops of the subgroup: head lettuce (4 ppm), leaf lettuce (8 ppm), and 

spinach (10 ppm).

0.419-0.506 lb ai/A; 0-day PHI

Residues (mg/kg) n

0.08 1

0.2 1

0.27 1

0.47 1

0.51 1

0.65 1

0.74 1

1.3 1

1.5 1

1.6 1

1.8 1

Cyazofamid

Head lettuce

USA and Canada

0.419-0.506 lb ai/A; 0-day PHI

Total number of data (n) 11

Percentage of censored data 0%

Number of non-censored data 11

Lowest residue 0.080

Highest residue 1.800

Median residue 0.650

Mean 0.829

Standard deviation (SD) 0.612

Correction factor for censoring (CF) 1.000

Proposed MRL estimate

- Highest residue 1.800

- Mean + 4 SD 3.278

- CF x 3 Mean 2.487

Unrounded MRL 3.278

Rounded MRL 4
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Lettuce, leaf (MRIDs 48629401 and 48629405)

The appropriate tolerance for the leafy greens subgroup 4A is 10 ppm, which is the highest level 

for the representative crops of the subgroup: head lettuce (4 ppm), leaf lettuce (8 ppm), and 

spinach (10 ppm).

0.427-0.587 lb ai/A; 0-day PHI

Residues (mg/kg) n

0.54 1

0.8 1

0.91 1

0.93 1

1.4 1

1.8 1

2.8 2

2.9 1

3.6 1

4.5 1

cyazofamid

Leaf lettuce

USA and Canada

0.427-0.587 lb ai/A; 0-day PHI

Total number of data (n) 11

Percentage of censored data 0%

Number of non-censored data 11

Lowest residue 0.540

Highest residue 4.500

Median residue 1.800

Mean 2.089

Standard deviation (SD) 1.308

Correction factor for censoring (CF) 1.000

Proposed MRL estimate

- Highest residue 4.500

- Mean + 4 SD 7.322

- CF x 3 Mean 6.267

Unrounded MRL 7.322

Rounded MRL 8
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Pepper, bell (MRID 47528401)

The appropriate tolerance for the fruiting vegetable group 8-10 is 0.9 ppm, which is the highest 

level for the representative crops of the subgroup: bell pepper (0.4 ppm), nonbell pepper (0.9 

ppm), and tomato (0.2 ppm).

0.418-0.429 lb ai/A; 0-day PHI

Residues (mg/kg) n

0.048 1

0.065 1

0.068 1

0.082 1

0.108 1

0.236 1

Cyazofamid

Bell Pepper

USA

0.418-0.429 lb ai/A; 0-day PHI

Total number of data (n) 6

Percentage of censored data 0%

Number of non-censored data 6

Lowest residue 0.048

Highest residue 0.236

Median residue 0.075

Mean 0.101

Standard deviation (SD) 0.069

Correction factor for censoring (CF) 1.000

Proposed MRL estimate

- Highest residue 0.236

- Mean + 4 SD 0.377

- CF x 3 Mean 0.304

Unrounded MRL 0.377

Rounded MRL 0.4

High uncertainty of MRL estimate.

[Small dataset]
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Pepper, nonbell (MRID 47528401)

The appropriate tolerance for the fruiting vegetable group 8-10 is 0.9 ppm, 

which is the highest level for the representative crops of the subgroup: bell 

pepper (0.4 ppm), nonbell pepper (0.9 ppm), and tomato (0.2 ppm).

 0.419-0.426 lb ai/A; 0-day PHI

Residues (mg/kg) n

0.258 1

0.259 1

0.321 1

Cyazofamid

Nonbell Pepper

USA

0.419-0.426 lb ai/A; 0-day

Total number of data (n) 3

Percentage of censored data 0%

Number of non-censored data 3

Lowest residue 0.258

Highest residue 0.321

Median residue 0.259

Mean 0.279

Standard deviation (SD) 0.036

Correction factor for censoring (CF) 1.000

Proposed MRL estimate

- Highest residue 0.321

- Mean + 4 SD 0.424

- CF x 3 Mean 0.838

Unrounded MRL 0.838

Rounded MRL 0.9

High uncertainty of MRL estimate.

[Small dataset]
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Spinach (MRID 47870704)

The appropriate tolerance for the leafy greens subgroup 4A is 10 ppm, which is the highest level 

for the representative crops of the subgroup: head lettuce (4 ppm), leaf lettuce (8 ppm), and 

spinach (10 ppm).

0.347-0.366 lb ai/A; 0-day PHI

Residues (mg/kg) n

1.61 1

2.03 1

2.1 1

2.18 1

2.94 1

3.34 1

3.49 1

3.64 1

4.74 1

6.52 1

Cyazofamid

Spinach

USA

0.347-0.366 lb ai/A; 0-Day PHI

Total number of data (n) 10

Percentage of censored data 0%

Number of non-censored data 10

Lowest residue 1.610

Highest residue 6.520

Median residue 3.140

Mean 3.259

Standard deviation (SD) 1.486

Correction factor for censoring (CF) 1.000

Proposed MRL estimate

- Highest residue 6.520

- Mean + 4 SD 9.203

- CF x 3 Mean 9.777

Unrounded MRL 9.777

Rounded MRL 10
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Tomato (MRID #s 45409031, 45638507, 45638508)

The appropriate tolerance for the fruiting vegetable group 8-10 is 0.9 ppm, which is the highest 

level for the representative crops of the subgroup: bell pepper (0.4 ppm), nonbell pepper (0.9 

ppm), and tomato (0.2 ppm).

0.413-0.434 lb ai/A; 0-day PHI

Residues (mg/kg) n

< 0.02 1

0.035 1

0.04 2

0.045 2

0.05 2

0.06 3

0.065 1

0.075 1

0.085 1

0.12 1

0.16 1

Cyazofamid

Tomato

USA

0.413-0.434 lb ai/A; 0-day PHI

Total number of data (n) 16

Percentage of censored data 6%

Number of non-censored data 15

Lowest residue 0.020

Highest residue 0.160

Median residue 0.055

Mean 0.063

Standard deviation (SD) 0.035

Correction factor for censoring (CF) 0.958

Proposed MRL estimate

- Highest residue 0.160

- Mean + 4 SD 0.202

- CF x 3 Mean 0.181

Unrounded MRL 0.202

Rounded MRL 0.2
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References

Acierto, A., 2/18/04, DP# D298915, Cyazofamid – Meeting Report of the Metabolism 

Assessment Review

Acierto, A., 2/20/04, DP# D285680, PP#1F06305, Cyazofamid. Petition for the Establishment of 

Permanent Tolerances for Use on Cucurbits, Potatoes, Tomatoes, and Imported Wine Grapes. 

Summary of Analytical Chemistry and Residue Data.

Acierto, A., 3/18/09, DP# D357042, Cyazofamid. Amend Section 3 to Add Uses on Fruiting 

Vegetables, Okra, Grape (East of the Rocky Mountains), and Greenhouse Vegetable 

Transplants. Summary of Analytical Chemistry and Residue Data.

Acierto, A., 2/24/10, DP# D371162, Cyazofamid. Tolerance Petition for Uses on Brassica 

(Cole) Leafy Vegetables Crop Group 5, Turnip Greens, Spinach, and Hops. Summary of 

Analytical Chemistry and Residue Data.

Hanson, B., 8/3/10, DP# D376500, Cyazofamid. Human Health Risk Assessment for Proposed 

Section 18 Use on Basil.

Kolbe, E., 10/22/03, DP# D286108, PP# 3F6595. Cyazofamid on Potatoes, Tomatoes, Cucurbit 

and Grapes. Tolerance Method Review and Multi-Residue Method Review. PC Code 085651 

(MRID#: 454090-33, 456385-08, 454090-34, 454090-32, 454090-20, 454090-22); ACB # B02-

(58-61).

Kolbe, E., 2/27/06, DP# D326164, PP# 3F6595. Review of Resubmitted Analytical Method for 

Cyzofamid and its Metabolite CCIM in Crops. PC Code 085651 (MRID#: 46550401); ACB 

Project # B06-13. 

OPPTS/US EPA, September 2004, Pesticide Fact Sheet: Cyazofamid
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Appendix A. Field Trial Geographic Distribution.

TABLE A.1. Trial Numbers and Geographical Locations.

NAFTA 

Growing 

Zones

Head Lettuce Leaf Lettuce

Submitted Requested1Submitted Requested1

Canada US Canada US

1 1 -- 1

2

/12-- -- 1

2

/12

1A -- -- -- -- -- --

2 -- -- 1

2

/121 -- 1

2

/12

3 1 -- 1/1 1 -- 1/1

4 -- -- -- -- -- --

5 2 1 -- 2 1 --

5A 1 -- -- 1 -- --

5B 1 3 -- 1 3 --

6 -- -- -- -- -- --

7 -- -- -- -- -- --

7A -- -- -- -- -- --

8 -- -- -- -- -- --

9 -- -- -- -- -- --

10 4

3

-- 6/4 4

3

-- 6/4

11 -- -- -- -- -- --

12 1 1 -- 1 1 --

Total 1135 8/6 1135 8/6

1

For the US, as per OCSPP 860.1500, Table 5 for head and leaf lettuce. The second number reflects a 25% reduction in the 

number of trials allowed for the crop as a representative commodity in support of a crop group/subgroup tolerance or when 

application results in no quantifiable residues. For Canada, as per Regulatory Directive - Dir98-02, Section 9 - Crop Field Trials. 

Appendix III, Table 2 for lettuce.

2 Trial can be conducted in either Zone 1 or Zone 2.

3 HED has concluded that trial pairs 08-CA*04/08-CA*05 and 08-CA03/08-CA19 for head lettuce, and trial pairs 08-NM14/08-

NM12, and 08-CA*22/08-CA*21 for leaf lettuce each constitute a single trial with replicate samples for purposes of OCSPP 

860.1500 data requirements.

TABLE A.2. Trial Numbers and Geographical Locations.

NAFTA Growing Regions Basil

Submitted Requested1

Canada U.S.

1 -- -- --

1A -- -- --

2 2 (field trials) -- --

3 1 (greenhouse trial) -- --

4 -- -- --

5 -- -- --

5A -- -- --

5B -- -- --

6 -- -- --

7 -- -- --

7A -- -- --

8 -- -- --
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TABLE A.2. Trial Numbers and Geographical Locations.

NAFTA Growing Regions Basil

Submitted Requested1

Canada U.S.

9 -- -- --

10 2 (field trials)

1 (greenhouse trial)

-- --

11 -- -- --

12 -- -- --

Total 4 (field trials)

2 (greenhouse trials)

-- 3

1 As per OCSPP 860.1500, Tables 2 and 3 for basil as a representative commodity of the herb crop group/subgroup; Tables 1 and 

5 do not include basil. Three field trials are required in major basil producing regions.

TABLE A.3. Trial Numbers and Geographical Locations.

NAFTA 

Growing 

Zones

Snap Bean Lima Bean

Submitted Requested1Submitted Requested1

Canada US Canada US

1 -- -- 1/1 -- -- --

1A -- -- -- -- -- --

2 3 -- 1/1 2

2

-- 4/3

3 -- -- 1/1 -- -- --

4 -- -- -- -- -- --

5 2 -- 3/2 1 -- 1/1

5A -- -- -- -- -- --

5B -- -- -- -- -- --

6 -- -- -- -- -- --

7 -- -- -- -- -- --

7A -- -- -- -- -- --

8 -- -- -- -- -- --

9 -- -- -- -- -- --

10 2 -- 1/0 2 -- 2/1

11 1 -- 1/1 1 -- 1/1

12 -- -- -- -- -- --

Total 8 8/6 6

2

8/6

1 As per OCSPP 860.1500, Table 5 for snap bean or lima bean. The second number reflects a 25% reduction in the number of 

trials allowed for the crop as a representative commodity in support of a crop group/subgroup tolerance or when application 

results in no quantifiable residues. 

2

 HED has concluded that lima bean trial pairs MD15/MD24 and NC30/NC31 each constitute a single trial with replicate 

samples for purposes of OCSPP 860.1500 data requirements.
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Appendix B: International Residue Limits 

Cyazofamid (085651; 02/01/2012)

Table B. Summary of US and International Tolerances and Maximum Residue Limits 

Residue Definition:

US Canada Mexico2 Codex3

40 CFR 180.601:

sum of 4-chloro-2-cyano-N,Ndimethyl-5-(4-methylphenyl)-1Himidazole-1-sulfonamide and its 

metabolite, 4- chloro-5-(4-

methylphenyl)-1H-imidazole-2-

carbonitrile, calculated as the 

stoichiometric equivalent of 

cyazofamid

4-chloro-2-cyano-N,Ndimethyl-5-(4-methylphenyl)-

1H-imidazole-1-sulfonamide, 

including the metabolite

4-chloro-5-(4-methylphenyl)-

1H-imidazole-2-

carbonitrile

None

Commodity1 Tolerance (ppm) /Maximum Residue Limit (mg/kg)

US Canada Mexico2 Codex3

Bean, succulent 0.5

Bean, succulent, shelled 0.08

Leafy greens subgroup 4A 10

Basil, fresh leaves 30

Basil, dried leaves 90

Vegetable, tuberous and corm,

subgroup 1C 0.02 0.02 potatoes

Vegetable, fruiting, group 8-

10 0.9

0.2 tomatoes

Completed: M. Negussie; 02/02/2012

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.
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Appendix C: Chemical Names and Structures of Cyazofamid and Identified Metabolites

Table C. Identification of Compounds from the Cyazofamid Metabolism Studies.

Common name/ 

code/matrix

Chemical name Chemical structure

Cyazofamid/

IKF-916

4-chloro-2-cyano-N,N-dimethyl-5-(4-

methylphenyl)-1H-imidazole-1-sulfonamide

N

N

H3C

Cl

CN

SO2N(CH3)

2

CCIM 4-chloro-5-p-tolylimidazole-2-carbonitrile

N

H

N

H3C

Cl

CN

CCBA 4-(4-chloro-2-cyanoimidazol-5-yl)benzoic 

acid

N

H

N

Cl

CN

HO

O

CCIM-AM 4-chloro-5-p-tolylimidazole-2-carboxamide

N

H

N

H C3

Cl

O

NH2

CTCA 4-chloro-5-p-tolylimidazole-2-carboxylic acid