UNITED STATES ENVIRONMENTAL PROTECTION AGENCY

WASHINGTON, D.C.  20460

	OFFICE OF PREVENTION, PESTICIDE

	AND TOXIC SUBSTANCES

  SEQ CHAPTER \h \r 1 MEMORANDUM

Date:  		February  24, 2010

SUBJECT:	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.

PC Code:  085651	DP Barcode:  D371162

Decision No.:  420982	Registration No.:  EPA Reg. Nos. 71512-2 & 

71512-3                                                                 
        

Petition No.:  9E7615	Regulatory Action:  Section 3 Registration 

Risk Assessment Type:  NA	Case No.:  NA

TXR No.:  NA	CAS No.:  120116-88-3

MRID No.:  See MRID Summary Table	40 CFR:  180.601

	Ver.Apr.08

FROM:	Amelia M. Acierto, Chemist

		Risk Assessment Branch III

		Health Effects Division (7509P)	  SEQ CHAPTER \h \r 1 

		

THROUGH:	Stephen Funk, Senior Science Advisor

		Risk Assessment Branch III

		Health Effects Division (7509P)

		

TO:		Barbara Madden RM, 05

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

       	Registration Division (7505P)

	  SEQ CHAPTER \h \r 1   SEQ CHAPTER \h \r 1 

MRID Summary Table

MRID No.	Study Type	Comments

47870701	860.1500 Broccoli	New DER; 47870701.der.doc

47870702	860.1500 Cabbage	New DER; 47870702.der.doc

47870703	860.1500 mustard greens	New DER; 47870703.der.doc

47870704	860.1500 spinach	New DER; 47870704.der.doc

47870705	860.1500 hops	New DER; 47870705.der.doc



Executive Summary 

The Interregional Research Project No. 4 (IR-4), State Agricultural
Experiment Station, Rutgers, The State University of New Jersey, New
Brunswick, New Jersey 08902, on behalf of the IR-4 Project and the
Agricultural Experiment Stations of Florida, Oklahoma, New York,
California, Georgia, North Carolina, Oregon, Virginia, Tennessee, Ohio,
and Washington, has submitted a petition proposing the establishment of
permanent tolerances for the combined residues of the fungicide
cyazofamid
[4-chloro-2-cyano-N,N-dimethyl-5-(4-methylphenyl)-1H-imidazole-1-sulfona
mide] and its metabolite CCIM
[4-chloro-5-(4-methylphenyl)-1H-imidazole-2-carbonitrile] in/on the
following raw agricultural commodities (RACs):

	Brassica, Head and Stem, subgroup 5A 
.......................................  1.2 ppm 

	Brassica, Leafy Greens, subgroup 5B 
...........................................12.0

	Turnip greens 
........................................................................
........12.0 

	Spinach 
........................................................................
.................  9.0

	Hops   ................................................................
........................... 10.0

This petition is associated with a FIFRA Section 3 request to amend the
registration to add to the labels the minor uses in/on the listed crops
for Cyazofamid Technical (EPA Reg. No. 71512-2) and for the end-use
product, Ranman® 400 SC (EPA Reg. No. 71512-3), a suspension
concentrate (SC) formulation containing 3.33 lb ai/gal.  

Ranman® 400SC is the product proposed for minor uses on Brassica crop
subgroup 5A and 5B as a single post transplant soil drench applied to
the base of the plants at the rate of 0.118 lb ai/A followed by multiple
(5) foliar applications at a target rate of 0.072 lb ai/A/application
with a maximum seasonal foliar application rate of 0.360 lb ai/A or a
total applied rate of 0.478 lb ai/A/season (1 soil drench + 5 foliar
applications).  Soil drench application was not proposed for spinach or
hops.  The formulated product is proposed for use on spinach as five
foliar sprays at the target rate of 0.072 lb ai/A/application with a
maximum seasonal rate of 0.36 lb ai/A and six foliar applications on
hops at the target rate of 0.072 lb ai/A/application with a maximum
seasonal rate of 0.426 lb ai/A.  Re-treatment intervals (RTIs) of 7 to
10 days are proposed for all the crops, starting when disease is first
detected or when weather or disease pressure is expected to initiate a
disease epidemic.  Preharvest intervals (PHIs) are proposed at 0 day for
the Brassica vegetables and spinach and 3 days for hops.  Except for
hops, Silwet L-77, a non-ionic organosilicone surfactant, is recommended
to be tank mixed at a 4:3 ratio for all foliar sprays. 

Tolerances have been established in 40 CFR §180.601(a) for the combined
residues of cyazofamid and CCIM expressed as cyazofamid in/on carrot,
roots at 0.09 ppm, okra at 0.40 ppm, potato at 0.02 ppm, vegetable,
cucurbit, group 9 at 0.10 ppm, and vegetable, fruiting, group 8 at 0.40
ppm.  In addition, tolerances with regional registrations are
established in 40 CFR §180.601(c) in/on grape at 1.5 ppm.

The  nature of the residues in crops is adequately understood for the
purposes of this petition based on the available grape, potato, tomato,
goat and hen metabolism studies.  The metabolism studies indicate that
several of the metabolites resulting from the cyazofamid metabolism are
common to both plants and livestock.  HED concluded that, for risk
assessment and tolerance expression, cyazofamid and CCIM are the
residues of concern in both plants and livestock.   However,  based on
available ruminant metabolism studies in goats, HED required that for
future cattle feeding studies, cyazofamid, CCIM, CCBA
[4-(4-chloro-2-cyanoimidazole-5-yl)benzoic acid] and CCBA-cysteine
conjugates should be analyzed (PP# 1F6305, D285680, Amelia M. Acierto,
2/20/2004).

An acceptable analytical method is available for enforcement purposes. 
The Agency finds that the FDA Multi-Residue Method, Protocol D (without
cleanup) meets the requirement of the Residue Chemistry Test Guideline
860.1360 to enforce tolerances for non-fatty commodities and recommends
its use as the enforcement method.  In addition, an acceptable high
performance liquid chromatography/ultraviolet detector (HPLC/UV) method
is available for use as a single analyte confirmatory method. 

An adequate data collection method derived from “Independent
Laboratory Validation of the Residue Method for IKF-916 and CCIM in
Tomatoes”, Document Number 013033-0, Pyxant Labs Inc, is available. 
Quantification of the residues of cyazofamid and CCIM is achieved by
liquid chromatography with tandem mass spectrometric detection
(LC/MS/MS).  The calculated LOQ and LOD were 0.03 ppm and 0.01 ppm,
respectively, for cyazofamid and 0.02 ppm and 0.006 ppm, respectively,
for CCIM.  The lowest level of method validation (LLMV) was 0.05 ppm for
both cyazofamid and CCIM. 

The crop field trial data submitted are adequate to support the proposed
new minor uses of cyazofamid in/on Brassica vegetables, spinach and
hops.  The combined residues of cyazofamid and CCIM following one post
transplant soil drench plus foliar applications (total rate of 0.479-
0.552 lb ai/A/season), ranged from 0.185-0.915 ppm for brocolli,
0.125-0.895 ppm for cabbage and 6.86 ppm for mustard greens.  In
spinach, residues following a total application of 0.347-0.366 lb
ai/A/season ranged from 1.45-6.62 ppm.  In hop cones, residues following
application of 0.425-0.443 lb ai/A/season ranged from 2.92-7.03 ppm. 
Residue decline data show that cyazofamid and CCIM residues in mustard
greens and spinach decreased with increasing pre-harvest intervals.

Adequate storage stability data are available to support the storage
durations and conditions of samples of cabbage, mustard greens, spinach
and hops.  Although the concurrent recoveries were acceptable for
broccoli, the storage stability data were erratic, which, according to
the petitioner may have been due to the spiking solution that appeared
to have degraded (separated) during frozen storage.  The petitioner
proposed to use the available storage stability data on tomatoes,
potatoes and grapes and the current data on cabbage to support the
storage stability of the residues of cyazofamid and CCIM for broccoli. 

The tolerance spreadsheet calculations indicate that the proposed
tolerances for the combined residues of cyazofamid and CCIM are
appropriate.

Canada has established maximum residue limits (MRL) for residues of
cyazofamid in/on several commodities, but has not established maximum
residue limits for the commodities of this petition.   No maximum
residue limits (MRLs) for residues of cyazofamid have been establishedby
the Codex Alimentarius Commission. 

  SEQ CHAPTER \h \r 1 Regulatory Recommendations and Residue Chemistry
Deficiencies

HED has examined the residue chemistry database for cyazofamid and
concludes that provided the forthcoming Human Health Risk Assessment
does not identify any risks of concern, there are no residue chemistry
issues that would preclude granting the requested Section 3 registration
for the proposed minor uses and the establishment of tolerances for the
combined residues of cyazofamid and its metabolite CCIM in/on the
commodities listed below. 

 (a) General. Tolerances are established for residues of the fungicide
cyazofamid, including its metabolites and degradates, in or on the
commodities in the table below.  Compliance with the tolerance levels
specified below is to be determined by measuring only the sum of
4-chloro-2-cyano-N,N-dimethyl-5-(4-methylphenyl)-1H-imidazole-1-sulfonam
ide and its metabolite,
4-chloro-5-(4-methylphenyl)-1H-imidazole-2-carbonitrile, calculated as
the stoichiometric equivalent of cyazofamid, in or on the commodity.

 

	Brassica, Head and Stem, subgroup 5A 
.......................................  1.2 ppm 

	Brassica, Leafy Greens, subgroup 5B 
...........................................12.0

	Turnip greens 
........................................................................
........12.0 

	Spinach 
........................................................................
.................  9.0

	Hops   ................................................................
........................... 10.0

Note to PM:  HED recommends modification of the tolerance expressions
for cyazofamid according to the new compliance/measurement policy
(Interim Guidance on Tolerance Expressions, Steve Knizner, May 27,
2009).  The tolerance definition entry in 40 CFR 180.601 should be
revised as shown above.		

A human health risk assessment is forthcoming.

Background

Cyazofamid is a broad-spectrum fungicide active against oomycete fungi
(such as Phytophthora, Plasmopara, Pseudoperonospora, and Pythium) and
Plasmodiophoromycetes (Plasmodiospora brassicae).  It inhibits all
stages of fungal development in the life cycle of Phytophthora infestans
which causes late blight disease in potatoes and tomatoes, and inhibits
the germination and formation of zoosporangia, germination of
cytospores, zoospore mobility, and mycelial growth.  It controls downy
mildew in cucurbit vegetables and grapes.  

Cyazofamid is the active ingredient in the end-use product (EUP) Ranman
400 SC, a suspension concentrate containing 3.33 lb ai/gal.  Ranman 400
SC is proposed for minor use in the control of club root (Pasmodiophora
brassiceae) and downy mildew (Peronospora parasitica) in Brassica
vegetables, white rust (Albugo occidentalis) disease in spinach; and
downy mildew (Pseudoperonospora humuli) in hops.  

The chemical structure, nomenclature and physicochemical properties of
the technical grade of cyazofamid and its metabolite CCIM, are shown in
Tables 1 and 2.

Table 1.	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-sulfonam
ide

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



Table 2.	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 10-5 Pa

	Dissociation constant (pKa)	Does not dissociate in water. No pKa in the
pH range of 2-12.

	Octanol/water partition coefficient 	LogKOW = 3.2

Λmax (nm)



2

7

10	285

279

287

	

860.1200 Directions for Use

IR-4 has submitted a proposed supplemental label for the product to be
used on crops: (Ranman® 400SC, EPA Reg. No. 71512-3) a suspension
concentrate formulation containing 3.33 lb ai/gal.  The proposed use
directions for Ranman® 400SC is summarized in Table 3.  

Table 3.	Summary of Directions for Use of Ranman® 400SC (EPA Reg. No.
71512-3)

Applic. Timing, Type, and Equip.	Applic. Rate 

fl oz

(lb ai/A)	Max. No. Applic. per Season	Max. Seasonal Applic. Rate

fl oz (lb ai/A)	TRI

(days)	PHI

(days)	Use Directions and Limitations

Crop Group 5, Brassica (Cole) Leafy vegetables: Broccoli; Chinese
broccoli (gai lon); broccoli raab (rapini); Brussels sprouts; cabbage;
Chinese cabbage (bok choy); Chinese cabbage (napa); Chinese mustard (gai
choy); cauliflower; cavalo broccolo; collards; kale; kohlrabi; mizuna;
mustard greens; mustard spinach; rape greens; turnip greens 1,2,3,4

Transplant Soil Drench  (for control of Club root disease) 2	12.9 to
25.75

(0.333-0.665/

100 gal)	 1 

	25.75

(0.665 lb ai/100 gal)	

	

	Soil drench immediately after transplant: make a single application
within the rate range listed and apply 1.7 fl. oz per plant as
transplant water.  

Foliar (For the control of Downy mildew disease) 3	2.75

(0.072)	5	13.75

(0.36)	7 to 10	0	Begin spray when disease is first seen or weather and
downy mildew disease pressure are expected to initiate a disease
epidemic.  

Use longer interval for preventive or low disease pressure.

Do not apply more than six (1 soil + 5 foliar) applications of RANMAN
400SC per season.

Spinach

Foliar (For control of white rust disease) 5

	2.1 to 2.75 (0.054 to 0.071)	5	13.75

(0.36)	7 to 10	0	Begin spray when disease is first seen or weather and
white rust disease pressure are expected to initiate a disease epidemic.
 

Use longer interval for preventive or low disease pressure.

Hops

Foliar (for control of Downy mildew ease) 6	2.1 to 2.75 (0.054 to 0.0

(0.071)	6	16.5

(0.426)	7 to 10	3	Begin spray when disease is first seen or weather and
downy mildew disease pressure are expected to initiate a disease
epidemic.  

Use longer interval for preventive or low disease pressure.

Use water spray of at least 100 gal/A.

 Resistance management: Do not apply more than six (1 soil + 5 foliar)
applications of RANMAN 400SC per crop.  Alternate foliar 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.

2  Soil Incorporation:  Alternatively, if desired and for soil with low
infiltration rates, apply 20 fl oz per acre in a minimum bandwidth of 9
inches along the planting row and incorporate to a soil depth of 6 to 8
inches with a precision incorporator in the same operation.  Apply in a
water volume of at least 50 gal per acre.  Transplant the seedlings into
the treated band.  If planting into a bed, a broadcast application can
be made prior to forming the bed.

3 Use of an organosilicone and a nonionic surfactant is recommended when
disease infection is severe at water volumes up to 60 gal/A. 

4 Restrictions: Do not apply more than 39.5 fl oz per acre per crop
growing season [1 soil application at 25.75 fl oz/A and 5 foliar
applications at 2.75 fl oz/A/application (13.75 fl oz/A)].

5 Resistance management: Do not apply more than five applications of
RANMAN® 400SC per crop.  Alternate foliar 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.

6 Resistance management: Do not apply more than six applications of
RANMAN® 400SC per crop.  Alternate foliar 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. 

 

Conclusions.  The submitted use directions are sufficient to allow
evaluation of the submitted residue data relative to the proposed uses. 
The use direction is according to the proposed supplemental label.   HED
notes that soil incorporation of Ranman® 400 SC at the rate of 20 fl oz
per acre before transplant is included in the supplemental label as an
alternative to the post transplant soil drench application.   No data
have been submitted to support the soil incorporation method.  However,
HED notes that incorporation of Ranman 400SC into the soil (before
transplant) is already on the current label and has been used on crop
field studies from earlier petitions (PP#8E7427). No further data are
required. 

860.1300 Nature of the Residue  Plants 

Residue Chemistry Memo DP# 323339, 2/8/07, A. Acierto (PP#1F06305)

Residue Chemistry Memo DP# 285680, 2/20/04, A. Acierto (PP#1F06305)

No plant metabolism studies were submitted with this petition.  The
qualitative nature of the residues in plants is adequately understood
for the purposes of this petition based on metabolism studies conducted
on grape, potato, and tomato, as well as a confined rotational crop in
which the cyazofamid test substances were radiolabeled in either the
phenyl ring ([benzene-14C]cyazofamid) or in the fourth position of the
imidazole ring ([imidazole-14C]cyazofamid).  The plant and livestock
metabolism studies indicate that several of the metabolites resulting
from the cyazofamid metabolism are common to both plants and livestock. 
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.  The
confined rotational crop study conducted at the 0.64X rate indicated
that levels for all metabolites of concern are very low (<0.010 ppm)
after a 30-day plant-back interval.   HED previously concluded that for
risk assessment and tolerance expression, cyazofamid and its CCIM
metabolite are the residues of concern in plants.  

860.1300 Nature of the Residue – Livestock

Residue Chemistry Memo DP# 323339, 2/8/07, A. Acierto (PP#1F06305)

No livestock metabolism studies were submitted with this petition.  The
qualitative nature of the residues in livestock is adequately understood
for the purposes of this petition based on metabolism studies conducted
in goat and hen in which the cyazofamid test substances were
radiolabeled in either the phenyl ring ([benzene-14C]cyazofamid) or in
the fourth position of the imidazole ring ([imidazole-14C]cyazofamid). 
These studies have been reviewed and deemed acceptable pending
submission of additional information pertaining to sample storage
intervals.  The livestock metabolism studies indicate that several of
the metabolites resulting from the cyazofamid metabolism are common to
both plants and livestock.  HED concluded that for risk assessment and
tolerance expression, the parent, cyazofamid and CCIM metabolite are the
residues of concern in livestock.   

860.1340 Residue Analytical Methods

Enforcement Method:  Adequate enforcement methodology is available to
enforce the proposed tolerances.  Cyazofamid and metabolite CCIM are
completely recovered (>80% recovery) using FDA’s Multiresidue Protocol
D (without cleanup).  In addition, an acceptable HPLC/UV method is
available for use as a single analyte confirmatory method.

Quantification of the residues of cyazofamid and CCIM in the current
crop field trials was achieved by liquid chromatography with tandem mass
spectrometric detection (LC/MS/MS)   

as described in “Independent Laboratory Validation of the Residue
Method for IKF-916 and CCIM in Tomatoes”, Document Number 013033-0,
Pyxant Labs Inc.  The calculated LOQ and LOD were 0.03 ppm and 0.01 ppm,
respectively, for cyazofamid and 0.02 ppm and 0.006 ppm, respectively,
for CCIM.  The lowest level of method validation (LLMV) was 0.05 ppm for
both cyazofamid and CCIM.  The method was validated at 0.01, 0.1 and 10
ppm for cyazofamid and CCIM prior to and concurrently with study
samples. 

The extraction method used for broccoli, cabbage, mustard greens and
spinach is described briefly as follows:  Five gram   SEQ CHAPTER \h \r
1 samples are extracted twice with 50 ml of acetonitrile (ACN) using an
Ultra-Turrax homogenizer.  The combined extracts are filtered through
Whatman filter paper.  About 50 ml of ACN and 5 ml water are added to
the filter cake, homogenized and again filtered.  The sample extract is
rinsed with 5 ml ACN.  Rinsate is added to the filter cake and
partitioned with 100 ml hexane.  The acetonitrile phase is collected and
concentrated to 1-2 ml (except for cabbage which is concentrated to 10
ml) using a rotary evaporator in a water bath at about 45oC.  The
residues are dissolved in 20% ACN:water, passed through a Nexus solid
phase extraction column (SPE) and eluted with 60% ACN:water.  Cyazofamid
and CCIM residues are quantified by LC/MS/MS.  

For hop cones, 1.0 g sample is extracted twice with 50 ml ACN and the
combined extracts are partitioned with hexane.  The ACN extract is
collected, diluted to a fixed volume with ACN, divided into two
fractions and cleaned up separately for the residues of cyazofamid and
CCIM.  For cyazofamid, the fraction is concentrated to dryness,
dissolved in 5 ml of 50:50 ethyl acetate:hexane, sonicated for 15 -30
seconds and passed through a NH2 Solid Phase Extraction (SPE) column. 
Cyazofamid residues are eluted from the column which is then rinsed
twice with 5 ml of 50:50 ethyl acetate:hexane.  The cleaned up extract
is evaporated to dryness, diluted to12.5 ml with 50:50 ACN:water and
analysed by LC/MS/MS.  For CCIM, the fraction is evaporated to 2 ml.  A
10 ml volume of 30% ACN:water is added, sonicated for 15-30 seconds and
passed through a Stratea-X Polymer SPE column for clean-up.  The column
is rinsed with 30% ACN:water.  All eluant were discarded.  CCIM was
eluted with 60% ACN:water into a centrifuge tube and diluted to 12.5 ml
with 50:50 ACN:water for analysis by LC/MS/MS.  

The calculations for LOQs and LODs for each crop were provided.

860.1360 Multiresidue Methods

Residue Chemistry Memo DP# 285680, 2/20/04, A. Acierto (PP#1F06305)

Adequate multiresidue method data for cyazofamid and its metabolites
were submitted previously in conjunction with PP#1F06305.  

The Agency previously concluded that the FDA Multiresidue Method,
Protocol D (without cleanup) meets the requirement of the Residue
Chemistry Test Guideline 860.1360 to enforce tolerances for non-fatty
commodities and recommended its use as the enforcement method for
residues of cyazofamid and CCIM in grape, tomato, the cucurbit vegetable
group, and potato (Memo dated 10/22/03, E. Kolbe, ACB, BEAD).  

860.1380 Storage Stability

Storage stability data submitted previously demonstrated that cyazofamid
and its metabolite CCIM were reasonably stable for up to ~36 months in
tomatoes and up to ~21 months in leaf lettuce (DP# 285680, 2/20/04, A.
Acierto).

A current freezer storage stability study was conducted using two sets
of untreated control crop field samples which were fortified separately
with cyazofamid and CCIM and stored at <-20oC.   Broccoli, cabbage,
mustard greens and spinach samples were fortified at 1.0 ppm and stored
for 788 and 802 days.  The hop cone samples were fortified with 0.10 ppm
cyazofamid and CCIM and stored for 509 days.  

Residues of cyazofamid and CCIM were quantified after the storage
duration using the LC/MS/MS method.  HED notes that 0-day data were not
provided with this study.   

The storage conditions and durations of samples from the crop field
studies are presented in Table 4.

TABLE  4.	Summary of Storage Conditions and Durations of Samples from
the Crop Field Trials.



Matrix (RAC)	

Analytes	Storage Temp. (oC)	Actual Storage Duration

(Days)	Interval of Demonstrated Storage Stability

(Days)	Storage Stability Recoveries

(%)

Broccoli	Cyazofamid	<-20 

	773

	788	146, 34, 73





802	172, 66, 91

	CCIM

	788	140, 55, 86





802	158, 80, 106



Cabbage 	Cyazofamid	<-20 	860	860	108, 114, 115

	CCIM



99, 100, 100

Mustard Green (Leaves)	Cyazofamid,	

<-20

<−20	927	949	103, 100, 104

	CCIM



113, 118, 123

Hop Cones	Cyazofamid,	

<-20

	

531-552 

	509	85, 79, 92

	CCIM



76, 79, 79



Conclusion.  The submitted storage stability data indicate that residues
of cyzofamid are stable in cabbage, mustard greens, spinach and hop
cones.  Although the broccoli data were erratic, there are sufficient
data from the representative crop group 5 to support the stability data
for broccoli.  No additional storage stability study is required. 
However, the petitioner is reminded that zero- day data should be
submitted in future petitions as required in Guideline 860.1300. 

  

860.1400 Water, Fish, and Irrigated Crops

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

860.1460 Food Handling

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

860.1480 Meat, Milk, Poultry, and Eggs

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

860.1500 Crop Field Trials	

Broccoli

DER References:	47870701.der.doc

Six field trials were conducted in the United States encompassing Region
6: TX (1 trial), Region 10: CA (4 trials), and Region 12: OR (1 trial)
during the 2006 growing season.  At each test location, experimental
plants were treated with one post transplant drench application of
Ranman 400SC at the rate of 0.118 lb ai/1000 plants to the base of the
plants, followed by five foliar applications except CA40 and OR27, which
received six foliar applications.  All foliar applications targeted the
rate of 0.072 lb ai/A, at 7(±1) day intervals and 0-day pre-harvest
interval (PHI).  A non-ionic organosilicone surfactant (Silwet L-77) was
used in a 4:3 ratio.  Foliar broadcast applications were made at all
field sites except site TX*13, where foliar directed applications were
made.  A minimum of about 2 pounds of broccoli flower heads including
florets, stem (stalk) and jacket leaves were collected from a minimum of
12 plants from the treated and untreated control plots.  Treated samples
were frozen within 25 minutes of sampling and kept frozen until prepared
for analysis.

Cabbage

DER References:	47870702.der.doc 

Nine trials were conducted in the United States encompassing Region 1:
NY (1 trial), Region 2: NJ (3 trials), Region 3: FL (1 trial), Region 5:
WI (1 trial), Region 6: TX (1 trial), Region 8: CO (1 trial), and Region
10: CA (1 trial) during the 2006 growing season.  At each test location,
experimental plants were treated with one post transplant drench
application of Ranman 400SC at the rate of 0.118 lb a.i./1000 plants to
the base of the plants, followed by five foliar applications except
NY07, which received six foliar applications.  All foliar applications
targeted the rate of 0.072 lb ai/A, at 7 (±1) day intervals and 0-day
pre-harvest interval (PHI) using a non-ionic organosilicone surfactant
(Silwet L-77) in a 4:3 ratio.  Foliar broadcast applications were made
at all field sites except sites MD21, FL17, and TX*14, where foliar
directed applications were made.  Twelve heads were collected from each
plot, cut into halves or quarters and frozen within 40 min of sampling.
Wrapper leaves were also retained.  All samples were kept frozen until
prepared for analysis.

Mustard Greens

DER References:	47870703.der.doc

Nine trials were conducted in the United States encompassing Region 2:
MD (1 trial), NJ (1 trial), GA (1 trial); Region 3: FL (1 trial); Region
4: TN (1 trial); Region 5: WI (1 trial); Region 6: TX (1 trial); and
Region 10: CA (2 trials) during the 2006 growing season.  One decline
trial (TX*15) was conducted with sampling at 0, 1, 3, 6, and 7 days
after the last application.  

	

At each test location, experimental plants were treated with one post
transplant drench application of Ranman 400SC at the rate of 0.118 lb
ai/1000 plants to the base of the plants, followed by five foliar
applications at a target rate of 0.072 lb ai/A, at 7(±1) day intervals
and 0-day pre-harvest interval (PHI) except for the decline studies
which were harvested after 0, 1, 3, 6 and 7 days.  A non-ionic
organosilicone surfactant (Silwet L-77) was used in a 4:3 ratio.  Foliar
broadcast applications were made at all field sites except sites MD06,
TX*15, and CA44, where foliar directed applications were made.  Two
treated and two untreated control samples were collected from each field
trial.  Four pounds of above ground leaves were collected per sample. 
The treated samples were frozen within 35 minutes, shipped frozen and
kept frozen until prepared for extraction and analysis.

Spinach  

DER References:	47870704.der.doc

Ten field trials were conducted in the United States encompassing Region
1: NY (1 trial); Region 2: NJ (1 trial), SC (1 trial), TN (1 trial);
Region 4: TN (1 trial); Region 6: TX (2 trials); Region 9: CO (1 trial)
and Region 10: CA (2 trials) during the 2006 growing season.  The number
and geographic distribution of the supervised crop field trials on
spinach are adequate.  At each test location, experimental plants were
treated with five foliar applications of Ranman 400SC at the target rate
of 0.072 lb a.i./A, at 7 (± 1) day intervals and 0-day pre-harvest
interval (PHI).  An organosilicone surfactant “Silwet L-77” was used
in a 4:3 ratio.  Foliar broadcast applications were made at all field
sites except TX*12, where foliar directed applications were made.  One
decline trial was conducted with sampling at 0, 1, 3, 6, and 7 days
after the last application.  Two samples each of treated and untreated
samples were collected from each trial.  A minimum of 2 pounds of above
ground leaves were collected from a minimum of 12 plants per treatment
and frozen within 25 minutes.  Samples were kept frozen from sampling
until prepared for extraction and analysis. 

Hops

DER References:	47870705.der.doc

Three field trials were conducted in the United States encompassing
Region 11: ID (1 trial), WA (1 trial); and Region 12: OR (1 trial)
during the 2006 growing season.  The number and geographic distribution
of the supervised crop field trials on hops are adequate.  At each test
location, experimental plants were treated with six foliar directed
applications of Ranman 400SC at a target rate of 0.071 lb ai/A, at 7 (±
1) day intervals and 2-4 days pre-harvest interval (PHI).  No adjuvants
were used in any of the hop field trials.  Hop cones were harvested 2-4
days after the last application using techniques simulating commercial
practices.  The cones were dried before sampling, then kept frozen until
extracted for analysis.

All raw agricultural commodities were analyzed for residues of
cyazofamid and CCIM using the LC/MS/MS method which was validated prior
to and concurrently with field samples. The results of the crop field
trials show that after one post transplant drench application and five
to six foliar applications totaling 0.467–0.552 lb ai/A at 7 (± 1)
day intervals and 0-day PHI, the maximum total residue (cyazofamid +
CCIM) detected was 0.915 ppm in broccoli flower heads,  0.895 ppm in
cabbage heads with wrapper leaves, and 7.0 ppm in mustard greens.  In
spinach, after five foliar applications totaling 0.347- 0.366 lb ai/A
applied at 7 (± 1) day intervals and  0-day PHI, the maximum total
residues (cyazofamid and CCIM) detected in the leaves were 6.62 ppm.  In
hop cones, following six foliar applications totaling 0.425-0.443 lb
ai/A at 7 (± 1) days intervals and 2-4 days PHI, the maximum combined
residues of cyazofamid and CCIM were 7.35 ppm.  Residues detected in all
the control samples were <0.01 ppm for both cyazofamid and CCIM.

	

Residue decline data show that cyazofamid and CCIM residues in spinach
and mustard greens decreased with increasing pre-harvest intervals. 
Results of the crop field trials are summarized in Table 5 and Table 6.

There are sufficient data from the representative crop group 5 to
support the storage stability data for broccoli.  No additional storage
stability study is required.  However, the petitioner is reminded that
zero-day data should be submitted in future petitions as required in
Guideline 860.1300. 

TABLE 5.	  SEQ CHAPTER \h \r 1 Residue Data from Crop Field Trials with
Cyazofamid (Ranman 400 SC)

Trial ID/(City, State)/Year	EPA Growing Region	Crop/ Variety	Commodity
or Matrix	Total Rate,

(lbs a.i./A)	PHI (days)	Cyazo-famid

(ppm)	CCIM

(ppm)	Combined Residues1

Broccoli1

CA*38/Salinas, CA/2006	10	Broccoli/ Everest	Flower Head	0.485	0	0.91,
0.76	<0.01, <0.01	0.915, 0.765

CA*39 Salinas, CA/2006	10	Broccoli/ Marathon	Flower Head	0.482	0	0.41,
0.33	<0.01, <0.01	0.415, 0.335

CA40/Hotville, CA/2006	10	Broccoli/ Heritage	Flower Head	0.552	0	0.26,
0.19	<0.01, <0.01	0.265, 0.195

CA41/Hotville, CA/2006	10	Broccoli/ Triathalon	Flower Head	0.479	0	0.28,
0.39	<0.01, <0.01	0.285, 0.395

OR27/Aurora, OR/2006	12	Broccoli/ General	Flower Head	0.552	0	0.47, 0.45
<0.01, <0.01	0.475, 0.455

TX*13/Weslaco, TX/2006	6	Broccoli/ Gypsy	Flower Head	0.486	0	0.18, 0.27
<0.01, <0.01	0.185, 0.275

Cabbage2

CA*42/ Salinas, CA/ 2006	10	Cabbage/ Charmant	Head with Wrapper Leaves
0.482	0	0.25, 0.25	<0.01, <0.01	0.255, 0.255

CO05/Brighton, CO/ 2006	8	Cabbage/ Rocket	Head with Wrapper Leaves	0.483
0	0.30, 0.29 	<0.01, <0.01	0.305, 0.295

FL17/ Citra, FL/2006	3	Cabbage/ Bravo	Head with Wrapper Leaves	0.496	0	

0.61, 0.50	0.016, 0.012	0.626, 0.512

MD21/Salisbury, MD/ 2006	2	Cabbage/ Primax	Head with Wrapper Leaves
0.478	0	

0.87, 0.63	0.025, 0.020	0.895, 0.650

NJ08/Bridgeton, NJ/ 2006	2	Cabbage/ Wisconsin Golden Acre	Head with
Wrapper Leaves	0.467	0	0.40, 0.16	0.013, <0.01	0.413, 0.165

NY07/Freeville, NY/ 2006	1	Cabbage/ Bobcat (Hybrid Cabbage)	Head with
Wrapper Leaves	0.531	0	0.22, 0.17	<0.01, <0.01	0.225, 0.175

SC*05/Charlston, SC/ 2006	2	Cabbage/ Copenhagen	Head with Wrapper Leaves
0.478	0	0.16, 0.14	<0.01, <0.01	0.165, 0.145

TX*14/Weslaco, TX/ 2006 	6	Cabbage/ Blue Vantage	Head with Wrapper
Leaves	0.482	0	0.33, 0.31	<0.01, <0.01	0.335, 0.315

WI10/Arlington, WI/2006	5	Cabbage/ Blue Vantage	Head with Wrapper Leaves
0.476	0	0.12, 0.13	<0.01, <0.01	0.125, 0.135

Mustard Greens3

CA*43/ Salinas, CA/2006	10	Greens (Mustard)/ Green Wave	Mustard Greens

(leaves)	0.482	0	2.9, 3.9	0.030, 0.040	2.93, 3.94

CA44/ Riverside, CA/ 2006	10	Greens (Mustard)/ Florida Broadleaf	Mustard
Greens

(leaves)	0.483	0	3.0, 3.6	0.032, 0.032	3.03, 3.63

FL18/Citra, FL /2006	3	Greens (Mustard)/ Florida Broadleaf	Mustard
Greens

(leaves)	0.503	0	6.0, 5.9	0.094, 0.090	6.09, 5.99

GA*06/Tifton, GA/2006	2	Greens (Mustard)/ Green Wave	Mustard Greens

(leaves)	0.491	0	6.8, 5.8	0.056, 0.050	6.86, 5.85

MD06/ Salisbury, MD/ 2006	2	Greens (Mustard)/ Green Wave	Mustard Greens

(leaves)	0.483	0	5.5, 5.5	0.050, 0.050	5.55, 5.55

NJ09/ Bridgeton, NJ/ 2006	2	Greens (Mustard)/ Southern Curled	Mustard
Greens

(leaves)	0.472	0	3.0, 4.0	0.13, 0.17	3.13, 4.17

TN06/Jackson, TN/2006	4	Grenns (Mustard)/ Florida Broadleaf	Mustard
Greens

(leaves)	0.494	0	1.5, 1.3	0.11, 0.10	1.61, 1.40

TX*15/ Weslaco, TX / 2006 	6	Greens (Mustard)/ Florida Broadleaf	Mustard
Greens

(leaves)	0.477	0	2.1, 1.7	0.038, 0.032	2.138, 1.732





	1	1.2, 1.4	0.019, 0.019	1.219, 1.419





	3	0.33, 0.38	<0.01, <0.01	0.335, 0.385





	6	0.061, 0.066	<0.01, <0.01	0.066, 0.071





	7	0.022, 0.024	<0.01, <0.01	0.027, 0.029

WI11 / Arlington, WI	5	Mustard Greens / Florida Broadleaf	Mustard Greens

(leaves)	0.474	0	3.8, 3.6	0.19, 0.17	3.990, 3.77

Spinach/ 4

CA* 36/ Salinas, CA/ 2006	10	Spinach/ Whale F106	Greens

(leaves)	0.364	0	3.9, 3.3	0.044, 0.045	3.944, 3.345

CA*37/Salinas, CA/2006	10	Spinach/ Space F1	Greens

(leaves)	0.360	0	3.0, 3.6	0.036, 0.043	3.036, 3.643

CO04/Fort Collins, CO/ 2006	9	Spinach/ Bloomsdale Savoy	Greens

(leaves)	0.365	0	2.4, 1.9	0.036, 0.032	2.436, 1.932





	1	2.5, 1.6	0.031, 0.023	2.531, 1.623





	3	1.2, 1.2	0.015, 0.012	1.215, 1.212





	4	0.9, 1.0	0.013, 0.016	0.913, 1.016





	6	0.69, 0.82	<0.01, 0.011	0.695, 0.831

NJ07/ Bridgeton, NJ/ 2006	2	Spinach/ Melody	Greens

(leaves)	0.347	0	6.3, 6.5	0.12, 0.12	6.42, 6.62

NY06/ Freeville, NY/ 2006	1	Spinach/ Tyee F1	Greens

(leaves)	0.361	0	2.1, 1.9	0.031, 0.027	2.131, 1.927

SC*04/ Charleston, SC /2006	2	Spinach/ Skookum Hybrid	Greens

(leaves)	0.361	0	2.6, 3.1	0.081, 0.094	2.681, 3.194

TN07/ Crossville, TN/ 2006	2	Spinach/ Bloomsdale	Greens

(leaves)	0.366	0	3.6, 3.2	0.10, 0.086	3.70, 3.286

TN08/Jackson, TN / 2006	4	Spinach/ Bloomsdale	Greens

(leaves)	0.365	0

	1.8, 2.2	0.088, 0.11	1.888, 2.31

TX*11/ Weslaco, TX/ 2006 	6	Spinach/ Samish	Greens

(leaves)	0.359	0	1.7, 1.4	0.064, 0.054	1.764, 1.454

TX*12/ Weslaco, TX/ 2006 	6	Spinach/ Spargo F1	Greens

(leaves)	0.359	0	4.1, 5.1	0.13, 0.15	4.23, 5.25

Hops

09823.07-ID01 /Parma, ID/ 2007 	11	Hops/ Nagget	Mature hop cones	0.425	4
5.7, 6.9	0.13, 0.13	5.83, 7.03

09823.07-OR04 /Aurora, OR/ 2007	12	Hops/ Nagget	Mature hop cones	0.440	2
2.8, 3.6	0.21, 0.28	3.01, 3.88

09823.07-WA02/B-49 Field/2007	11	Hops/ Nagget	Mature hop cones	0.443	3
2.5, 2.5	0.42, 0.45	2.92, 2.95











1For Residue values <LOQ (0.01 ppm), ½ LOQ (0.005 ppm) was used to
calculate combined residues

3For residue values <LOQ (0.01 ppm), ½ LOQ (0.005 ppm) was used for
CCIM residues

40.005 ppm was used for CCIM residues (< 0.01 ppm) to calculate combined
residues

 

TABLE 6.	Summary of Residue Data from Crop Field Trials with Cyazofamid

Commodity	Analyte 	Total Application Rate

 (lbs a.i./A)	PHI (days)	Residue Levels (ppm)





n	Min.	Max.	HAFT1	Median2

(STMdR)	Mean2

(STMR)	Standard Deviation2

Broccoli

Broccoli Flower Head	Cyazofamid	0.479–0.552	0	12	0.18	0.91	0.84	0.36
0.41	0.22

	CCIM	NA3	0	12	< 0.01	< 0.01	0.005	0.005	0.005	0

Cabbage

Cabbage Head with Wrapper Leaves	Cyazofamid	0.467–0.531	0	18	0.12	0.87
0.75	0.27	0.32	0.21

	CCIM	NA3	0	18	< 0.01	0.025	0.02	0.01	0.01	0.01

Mustard Greens

Mustard Greens

(leaves)	Cyazofamid	0.472 – 0.503	0	18	1.3	6.8	6.3	3.7	3.9	1.7

Mustard Greens

(leaves)	Cyazofamid	0.477	1	2	1.2	1.4	1.3	1.3	1.3	0.14

Mustard Greens

(leaves)	Cyazofamid	0.477	3	2	0.33	0.38	0.36	0.36	0.36	0.035

Mustard Greens

(leaves)	Cyazofamid	0.477	6	2	0.061	0.066	0.064	0.064	0.064	0.0035

Mustard Greens

(leaves)	Cyazofamid	0.477	7	2	0.022	0.024	0.023	0.023	0.023	0.0014

Mustard Greens

(leaves)	CCIM	NA4	0	18	0.030	0.19	0.18	0.053	0.081	0.053

Mustard Greens	CCIM	NA	1	2	0.019	0.019	0.019	0.019	0.019	0

(leaves)	CCIM	NA	3	2	<0.01	0.012	0.009	0.009	0.009	0.005

Mustard Greens	CCIM	NA	6	2	<0.01	<0.01	0.005	0.005	0.005	0

(leaves)	CCIM	NA	7	2	<0.01	<0.01	0.005	0.005	0.005	0

Spinach Leaves

Spinach Leaves	Cyazofamid	0.347 - 0.366   	0	20	1.4	6.5	6.4	3.1	3.2	1.4

Spinach Leaves	Cyazofamid	0.365	1	2	1.6	2.5	2.1	2.1	2.1	0.64

Spinach Leaves	Cyazofamid	0.365	3	2	1.2	1.2	1.2	1.2	1.2	0

Spinach Leaves	Cyazofamid	0.365	4	2	0.90	1.0	0.95	0.95	0.95	0.071

Spinach Leaves	Cyazofamid	0.365	6	2	0.69	0.82	0.76	0.76	0.76	0.092

Spinach Leaves	CCIM	NA3	0	20	0.027	0.15	0.14	0.073	0.075	0.038

Spinach Leaves	CCIM	NA	1	2	0.023	0.031	0.027	0.027	0.027	0.01

Spinach Leaves	CCIM	NA	3	2	0.012	0.015	0.0135	0.0135	0.0135	0.0021

Spinach Leaves	CCIM	NA	4	2	0.013	0.016	0.0145	0.0145	0.0145	0.0021

Hops

Hop Cones

	Cyazofamid	0.425-0.443	2-4	6	2.5	6.9	6.3	3.2	4.0	1.9

	CCIM	NA2	2 - 4	6	0.13	0.45	0.435	0.245	0.27	0.14

1Highest Average Field Trial

2For residue values <LOQ, half of the LOQ (0.005 ppm) was used to
calculate the median, mean, HAFT, and standard deviation

3Not Applicable 

Conclusion. The submitted crop field studies are adequate to support the
proposed minor uses.  The studies were   SEQ CHAPTER \h \r 1 conducted
consistent with standard agricultural practices as per proposed use
pattern.  The number and geographic distribution of the supervised crop
field trials are adequate.  Weather conditions at the field sites were
generally considered normal;   SEQ CHAPTER \h \r 1 anomalous weather
conditions were reported at some field sites, which did not have any
adverse impact on the studies.  

Residue decline data show that cyazofamid and CCIM residues in mustard
greens and spinach decreased with increasing pre-harvest intervals.

Adequate storage stability data are available.

860.1550 Proposed Tolerances

HED has concluded previously that the parent and the metabolite CCIM are
the residues of concern for risk assessment and tolerance expression in
plants.  Tolerances are currently established in 40 CFR §180.601(a) for
the combined residues of cyazofamid and CCIM expressed as cyazofamid
in/on carrot, roots at 0.09 ppm, okra at 0.40 ppm, potato at 0.02 ppm,
vegetable, cucurbit, group 9 at 0.10 ppm, and vegetable, fruiting, group
8 at 0.40 ppm.  In addition, tolerances with regional registrations are
established in 40 CFR §180.601(c) in/on grape at 1.5 ppm.  HED
recommends modification of the tolerance expressions for cyazofamid
according to the new compliance/measurement policy (Interim Guidance on
Tolerance Expressions, Steve Knizner, May 27, 2009) to read as follows:	


“HED recommends that the tolerance definition entry in 40 CFR 180.601
be revised as follows:  (a) General. Tolerances are established for
residues of the fungicide cyazofamid, including its metabolites and
dehgradates, in or on the commodities in the table below.  Compliance
with the tolerance levels specified below is to be determined by
measuring only the sum of
4-chloro-2-cyano-N,N-dimethyl-5-(4-methylphenyl)-1H-imidazole-1-sulfonam
ide and its metabolite,
4-chloro-5-(4-methylphenyl)-1H-imidazole-2-carbonitrile, calculated as
the stoichiometric equivalent of cyazofamid, in or on the commodity.”

The Agency’s SOP “Guidelines for Setting Pesticide Tolerances Based
on Field Trial Data” was utilized for determining the appropriate
tolerance level for each commodity (Appendix II).  

As the minimum and maximum recommended tolerances differ by less than
5x, a crop group tolerance is appropriate for the Brassica Head and
Stem, Crop Subgroup 5A.  Although cabbage belongs to both crop subgroup
5A and 5B, the tolerance of 12.0 ppm is appropriate for Brassica, Leafy
Greens, Crop Subgroup 5B based on mustard greens, the representative
crop.  

HED has concluded that turnip greens will be moved from the leaves of
root and tuber vegetables crop group (group 2) to the Brassica leafy
vegetables crop group 5, subgroup 5B: (memorandum,  B. Schneider,
6/14/2002).  However, until the regulations have been finalized in the
Federal Register, a separate tolerance is needed for turnip greens at
the same level as the Brassica, Leafy Greens, Crop Subgroup 5B at 12.0
ppm.

The recommended tolerances for spinach and hops are 9 and 10.0 ppm,
respectively.  The recommended tolerances are listed in Table 7.

Canada has established maximum residue limits (MRL) for residues of
cyazofamid in/on several commodities, but has not established maximum
residue limits for the commodities of this petition.   No maximum
residue limits (MRLs) for residues of cyazofamid have been establishedby
the Codex Alimentarius Commission. 

Table 7. 	Tolerance Summary for Cyazofamid.

Commodity	Proposed  Tolerance (ppm	Existing Tolerance (ppm)	Recommended
Tolerance (ppm)	Comments; Correct Commodity Definition

40 CFR 180.601 (a)

Brassica, head & stem, crop subgroup 5A 	1.2

1.2

	Brassica, leafy greens, crop subgroup 5B	12.0

12.0

	Hops	10.0

10.0

	Spinach	9.0

9.0

	Turnip greens	12.0

12.0	Until the regulations have been finalized in the Federal Register
to move turnip greens from the leaves of root and tuber vegetables crop
group (group 2) to the Brassica leafy greens subgroup 5B, a separate
tolerance is needed at the same level as the Brassica, Leafy Greens,
Subgroup 5B.1



1Memorandum, B. Schneider, 6/14/2002.

E.	REFERENCES

DP Barcode:	D285680

Subject:	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 

From:		Amelia Acierto

To:		Janet Whitehurst/Cynthia Giles-Parker, PM Team #22

Date:		2/20/2004

MRID:		45638502, 45638503, 45638504, 45638505, 45638506-45638510,
45409014-			45409019, 45409020, 45409022, 45409023-45409025,
45409026-45409035, 			45409036 

DP Barcode:	357042

Subject:	Amend Section 3 Registration to Add Uses on Fruiting
Vegetables, Okra, Grape (East of the Rocky Mountains), and Greenhouse
Vegetable Transplants.  Summary of Analytical Chemistry and Residue
Data.

From:		Amelia Acierto

To:		Barbara Madden, RM #5

Date:		3/18/2009

MRID:		47528401, 47528402, 47532601

  SEQ CHAPTER \h \r 1 Attachments:  

Appendix I -   International Residue Limit Status sheet

Appendix II - Tolerance Assessment Calculations

Template Version April 2008

APPENDIX  I

INTERNATIONAL RESIDUE LIMIT STATUS

Chemical Name: 
4-Chloro-2-cyano-N,N-dimethyl-5-(4-methylphenyl)-1H-imidazole-1-sulfonam
ide 	Common Name:

Cyazofamid	□ Proposed tolerance

□ Reevaluated tolerance

X Other  Recommended	Date: 12/2/08

Codex Status (Maximum Residue Limits)	U. S. Tolerances

√ No Codex proposal step 6 or above

□ No Codex proposal step 6 or above for the crops requested	Petition
Number:  PP#9E7615

DP#:  371163

□ No Limits

√ No Limits for the crops requested	√ No Limits

□ No Limits for the crops requested

Residue definition: 
4-chloro-2-cyano-N,N-dimethyl-5-(4-methylphenyl)-1H-imidazole-1-sulfonam
ide, including the metabolite
4-chloro-5-(4-methylphenyl)-1H-imidazole-2-carbonitrile 	Residue
definition:  N/A

Mexico adopts Codex MRLs or US tolerances for its export purposes.

Crop(s)	MRL (mg/kg)	Crop(s)	MRL (mg/kg)

























	Notes/Special Instructions:

S. Funk,  3/6/2010



Appendix II.  Tolerance Assessment Calculations.

 that were small (≤15 samples) and reasonably lognormal, the upper
bound estimate of the 95th percentile based on the median residue value
was compared to the minimum of the 95% UCL on the 95th percentile and
the point estimate of the 99th percentile, and the minimum value was
selected as the tolerance value.  For datasets that were not lognormal,
the upper bound on the 89th percentile was selected as the tolerance
value (distribution-free method).  The rounding procedures specified in
the SOP were also used.

Brassica, Crop Subgroup 5A

The dataset used to establish tolerances for residues of Cyazofamid on
Brassica Crop Subgroup 5A consisted of field trial data for the
representative crops: broccoli and cabbage and represented application
rates of 0.485-0.506 lb ai/A (1 soil drench +5-6 foliar applications)
with a  PHI of 0 day.  As specified by the SOP, the field trial
application rates and PHIs are within 25% of the maximum label
application rate and minimum label PHI, respectively.  The residue
values used to calculate the tolerance are provided in Table I.  

All field trial sample results for broccoli and cabbage were above the
LOQ (0.01 ppm).  The dataset for was 12 samples for broccoli, and 18
samples for cabbage. The dataset for each crop was entered into the
tolerance spreadsheet.  Visual inspection of the lognormal probability
plots for each crop (Figures I-1and I-3) indicates that the datasets for
both crops are reasonably lognormal.  The results from the approximate
Shapiro-Francia test statistic (Figures I-2 and I-4) confirmed that the
assumption of lognormality should not be rejected.  

Using the tolerance spreadsheet, the recommended tolerances are 1.2 ppm
for broccoli, and 1.1 ppm for cabbage.  Because the minimum and maximum
recommended tolerances differ by less than 5x, a crop group tolerance is
appropriate Brassica, Crop Subgroup 5A.  The recommended value is 1.2
ppm, the maximum of the recommended individual tolerances.

Brassica, Crop Subgroup 5B

The dataset used to assess a tolerance for Cyazofamid residues in/on
Brassica Crop Subgroup 5B consisted of field trial data for the
representative crop mustard greens and represented application rates of
0.484 lb ai/A (1 soil drench + 5-6 foliar applications) with a  PHI of 0
day.  As specified by the SOP, the field trial application rates and
PHIs are within 25% of the maximum label application rate and minimum
label PHI, respectively.  The residue values used to calculate the
tolerance are included in Table I.  

All field trial sample results for broccoli and cabbage were above the
LOQ (0.01 ppm).  The dataset for mustard greens was 18 samples. The
dataset for the crop was entered into the tolerance spreadsheet.  Visual
inspection of the lognormal probability plots for each crop (Figure I-5)
indicates that the dataset for mustard greens is reasonably lognormal. 
The results from the approximate Shapiro-Francia test statistic (Figure
I-6) confirmed that the assumption of lognormality should not be
rejected.  

Using the tolerance spreadsheet, the recommended tolerance for mustard
greens is 12 ppm.  Because mustard greens is the representative
commodity for Brassica Crop Subgroup 5B, a crop group tolerance is
appropriate.  The recommended value is 12 ppm is recommended for
individual tolerances.

Spinach 

The dataset used to assess a tolerance for Cyazofamid residues in/on
spinach consisted of field trial data and represented application rate
of 0.361lb ai/A (5 foliar applications) with a  PHI of 0 day.  As
specified by the SOP, the field trial application rates and PHIs are
within 25% of the maximum label application rate and minimum label PHI,
respectively.  The residue values used to calculate the tolerance are
provided in Table II-1.  

All field trial sample results for spinach were above the LOQ (0.01
ppm).  The dataset for spinach was 20 samples. The dataset for the crop
was entered into the tolerance spreadsheet.  Visual inspection of the
lognormal probability plots for each crop (Figure II-1) indicates that
the dataset for mustard greens is reasonably lognormal.  The results
from the approximate Shapiro-Francia test statistic (Figure II-2)
confirmed that the assumption of lognormality should not be rejected.  

Using the tolerance spreadsheet, the recommended tolerance for spinach
is 9 ppm.  

Hops

The dataset used to assess a tolerance for Cyazofamid residues in/on
hops consisted of field trial data and represented application rates of
0.436 lb ai/A (6 foliar applications) with a  PHI of 0 day.  As
specified by the SOP, the field trial application rates and PHIs are
within 25% of the maximum label application rate and minimum label PHI,
respectively.  The residue values used to calculate the tolerance are
provided in Table II-1.  

The field trial sample results for hops were above the LOQ (0.01 ppm). 
The dataset for hop was 6 samples. The dataset for the crop was entered
into the tolerance spreadsheet.  Visual inspection of the lognormal
probability plots for each crop (Figure II-3) indicates that the dataset
for hops is reasonably lognormal.  The results from the approximate
Shapiro-Francia test statistic (Figure II-4) confirmed that the
assumption of lognormality should not be rejected.  

Using the tolerance spreadsheet, the recommended tolerance for hops is
10 ppm.  

Table I.  Residue data used to calculate tolerance for cyazofamid
residues on broccoli, cabbage and mustard greens.

	Brassica  Crop Subgroup 5A	Brassica  Crop Subgroup 5B

Regulator:	EPA	EPA	EPA

Chemical:	Cyazofamid	Cyazofamid	Cyazofamid

Crop:	

Broccoli	Cabbage	Mustard Greens

PHI:	0 day	0 day	0 day

App. Rate: (1 Soil Drench + 5 Foliar)	0.506 lb ai/A	0.485 lb ai/A	0.484
lb ai/A

Submitter:	IR-4	IR-4	IR-4

MRID Citation:	MRID 47528401	MRID 47528402	MRID 47528403

	Residues	Residues	Residues

	0.915	0.255	2.93, 

	0.415	0.255	3.03, 

	0.265	0.626	6.09, 

	0.285 	0.895	6.86, 

	0.475 	0.413	5.55

	0.185	0.225	3.13

	 0.765	0.165	1.61

	0.335	0.335	2.14 

	0.195	0.125	3.99

	0.395	0.305	3.94

	0.455	0.295	3.63

	0.275	0.512	5.99



0.650	5.85



0.165	5.55



0.175	4.17



0.145	1.40



0.315	1.73



,0.135	3.77



Figure I-1. Lognormal Probability Plot of Cyazofamid Residues in/on
Broccoli Following One Post Transplant Drench and Five to Six Foliar
Applications of RanMan 400 SC at a Total Rate of 0.506 lb ai/A.

Figure I-2. Tolerance spreadsheet summary of cyazofamid field trial data
for broccoli.

 

Figure I-3. Lognormal Probability Plot of Cyazofamid Residues in/on
Cabbage Following One Post Transplant Drench and Five to Six Foliar
Applications of RanMan 400 SC at a Total Rate of 0.485 lb ai/A.

 

Figure I-4. Tolerance spreadsheet summary of cyazofamid field trial data
for cabbage.

 

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ty Plot of Cyazofamid Residues in/on Mustard Greens Following One Post
Transplant Drench and Five Foliar Applications of RanMan 400 SC at a
Total Rate of 0.484 lb ai/A.

 

Figure I-6. Tolerance spreadsheet summary of cyazofamid field trial data
for mustard greens.

 

Table II-  Residue data used to calculate tolerance for cyazofamid
residues on spinach and hops.

Regulator:	EPA	EPA

Chemical:	Cyazofamid	Cyazofamid

Crop:	Spinach	Hops

PHI:	0 day	0 day

App. Rate: (Foliar)	0.36 lb ai/A	0.436 lb ai/A

Submitter:	IR-4	IR-4

MRID Citation:	MRID 47528404	MRID 47528405

	Residues	Residues

	3.944 	5.83

	3.036 	3.01

	2.436 	2.92

	6.42 	7.03

	2.131 	3.88

	2.681 	2.95

	3.70 



1.888 



1.764 



4.23 



3.345



3.643



1.932



6.62



1.927



3.194



3.286



2.31



1.454



5.25

	

Figure II-1.  Lognormal Probability Plot of Cyazofamid Residues in/on
Spinach Following Five Foliar Applications of RanMan 400 SC at a Total
Rate of 0.361 lb ai/A.

 

Figure II-2. Tolerance spreadsheet summary of cyazofamid field trial
data for spinach.

 

Figure II-3.  Lognormal Probability Plot of Cyazofamid Residues in/on
Hops Following Six Foliar Applications of RanMan 400 SC at a Total Rate
of 0.436 lb ai/A.

 

Figure I-4. Tolerance spreadsheet summary of cyazofamid field trial data
for hops.

 

Cyazofamid	Summary of Analytical Chemistry and Residue Data	DP#:  371162

Page   PAGE  3  of   NUMPAGES  29 

