United State* Office of Pesticides and Toxic Sufattaneat
Environmental Protection Office of Pesticide Programs (TS-766C)
Agency Washington. DC 20460
vvEPA Pesticide
Fact Sheet
Name of Chemical: CAPTAPOL
Reason for Issuance:
Date Issued: October i, 1934
Fact Sheet Number:
35
1. Description of Chemical
Generic Name: cis-N-[(1,1,2,2-tetracnloroethyl)
tEIo] -4-cyclohexene-l, 2-dicarboocimide
Cannon Name: Captafol
Trade Names: Difolatan, Polcid, Haipen, Merpafol, Ortho 5865,
Sanspor and Sulfemmide
EPA Shaughnessy Code: 081701
Chemical Abstract Service (CAS) Number: 2425-06-1
Year of Initial Registration: May 21, 1962
Pesticide Type: Fungicide
Chemical Family: Phthalunide
U.S. Producer: Chevron Chemical Ccnpany
2. Use Patterns and Formulations
Application Sites: Apples (Midwestern and Eastern states only),
apricots, blueberries, cherries (unspecified-use in California and Oregon
only), cherries (sour), cranberries, grapefruit, lemons, limes (Florida
only), macadamia nuts (Hawaii), nectarines, oranges (Florida only),
peaches, pineapples, plums, prunes, tangerines, corn (sweet, Florida
only), cucumbers, melons, onions, potatoes, taro (wetland) (Hawaii only),
tomatoes (mechanically harvested only), watermelons, peanuts, seed
treatment uses (corn (field), cotton, peanuts, rice and sorghum (grain and
forage)] and wood.
Types of Formulations: Dusts, emulsifiable concentrates, flowable
suspensions, wettable powders, and water dispersible granules.
Types and Methods of Application: Dusting, spraying, misting, and dipping
under pressure for wood treatment.
Application Rates: See use patterns in USDA Compilations of Registered
Uses of Fungicides and Nematicides, Part I, Pages C-09-95.01 through
C-09-95.11.
Usual Carriers: Clay, talc, silica, water.
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3. Scientific Fiz ]in
th nical tharacteristi :
Physical State: Crystalline solid
Color: ite
Odor: Slight characteristic pungent odor
Melting Point: Range 156—161°C (162°C, pure compound)
Stability: Stable under ordinary environmental conditions.
I composes slowly at melting point. Very slight
hydrolytic decomposition at acid or neutral pH at
ambient temperature. Strong aodium and potassiuu
hydroxide solutions may cause spontaneous ignition
of concentate forms. In neutral or weakly basic
solution, captafol slowly decomposes at a rate
depending upon pH and temperature, being very slow
below 7.0 and rapid above 9.0.
Toxicity Characteristics :
Acute oral LD 50 — Rat — males 6780 mg/kg, Category III
females 6330 mg/kg, Category III
Acute inhalation LC 50 — Data gap
Dermal Irritation — Rabbit — iixderate dermal irritation at 72 hours,
Category III. Severe dermal sensitization.
Eye Irritation — Rabbit — corneal opacity, iris and conj*mctive irritation
present through day 21, Category I.
Teratology — Rat — no teratogenic effects seen. Highest dose tested:
100 mg/kg/day.
Rabbit — recently submitted tests currently under review.
H*mater — no effect level (NOEL) for fetotoxicity and
possible teratogenic effects — 300 mg/kg. New study at be
submitted by the registrant.
Oncogenicity —Mouse — Oncogenic lesions were observed at 1000 and
- 3000 parts per million (ppm) but not at 300 ppm.
Information concerning the control groups is
being requested from the registrant in order
for a final risk assessment to be performed.
— Rat — Oncogenic lesions were seen at all dose levels.
Additional histopathology examinations of liver
and mammary tissues at low (56 ppm) and mid
(241 ppm) dose levels have been requested from
the registrant. This information is necessary
f or a complete risk assessment to be performed.
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Physiological and Bioth nical Bthavioral tharacteristics :
Foliar Absorption: Captafol and/or its metabolites and dearadrates
is (are) absorbed by roots and shoots of plants.
Translocation Ca tafol and/or its metabol ites and dearadrates is (are)
translocated in plant tissue. Captafol and/or its metabolites and
deciradates is (are) absorbed and trarislocated within p1 ants as a
result of sped treatment, soil treatn nt and foliar application.
Methani n of Pest icidal Action: tfl b n
Metaboli n and Persistence in Plants and Animals: The metabo1i and
acc’.imilation of captafol in plants are not uri]erstocxL The metabol i n
of captafol is wx3erstood for rizninants but riot for avian species.
The foll ing metakolites have been identified in animal tissues:
delta 4 -tetrahvdLc hthal imide
r*ithal imide
4, 5-epoxyhexahvci Lcdlthal imicie
4, 5-dih drc cyhexahydL Jhthal imide
3-vdrc cy-de1 ta 4 -tetrahvdrc*ithal imide
racy-de1 ta 3 —tetrah dLc*jhtha1 thiide
delta 4 -tetrahy&u hthal nic acid
del ta 4 - tetrahydrochtharic acid
The above metabolites, with the exception of delta 4 -tetrahyck x hthalic acid,
re found in milk. Pb Parent captafol per se i s detected in nm inant
tissues or in milk.
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Envi Lct u. nta.l tharacteristic :
Absorption and Leathing in Basic Soil Types:
Captafol se does not leadi fran basic soils. The lead abi1ity
and persistence of its metabolites and degr ates are not understood.
Microbial Breaiuici.in: Ina)eguate data. Limited data indicate that captafol
se has a half—life of <3, 5, and 8 days in nonsterile organic,
sandy and clay loam soils, respectively. The soil degredates and
netabolites have not been identified.
Tri fran Pbotodeccuçz siticm and/or Volatilization: Inedequate data.
Bioacainulation: t data.
Resultant Average Persistence: In equate data on netabolites and
degredates.
Ecvlngical characteristics :
Hazards to fish and wildlife
Rainb trait: 96—hr LC j = 0.027 — 0.190 ppi
Bluegill sunfish: 96—hr IC 50 0.045 — 0.230 ppe
characterized as very highly t cic’ to both oold water arid warm
water fish. Ina3equate data for fish acctinulation.
Avian Tacicity: I D 50 = >2510 pp
LCc = >5620 ppn
Da mia ma a : 96-hr IC 50 = 3.34
Moderately to very highly tc cic to freshwater invertebrates.
Avian Reproducticm: Strong tential for reproductive effect in
birds (based on ai l entary information).
Potential probl related to endangered species:
Mditional data on exposure persistence, avian reproduction
sti.thes, and acc .mnilation are required to c r lete the endangered
species assesa nt for captafol.
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Efficacy Review Results:
Captafol product registrations with EPA have been supported with efficacy
data. To lerant strains of target plant patixDgens have not been reportea.
Tolerance Asses nents:
1. List of Crops and Tolerances:
The fo1lc ing table lists the present status for tolerances in parts per
million (p n) for residues of captafol:
Parts Per Million in Captaf ol
Residues
Raw Agricultural Caiiicdity U.S.
Canada
Mexico
Codex
Apples 0.25 0.1(N) 5.0
Apricots 30.0 0.5 15.0
Blueberries 35.0 — —
Cherries, sour 50.0 10.0 10.0
Cherries, sweet 2.0 2.0 2.0
Citrus fruit 0.5 — —
Corn, Fresh (sweet K+CWHR) 0.1 (N) — —
Cranberries 8.0 — 8.0
Cuci.utbers 2.0 2.0 2.0
Macadamia nuts 0.1(N) — 0.1 (N)
Melons 5.0 2.0 2.0
Nectarines 2.0 — —
Peanuts, hulls 2.0 — —a
Peanuts, meats (hulls re uved) 0.05 — 0.05
Chions 0.1(N) 0.1 (N) 0.5
Peaches 30.0 15.0 15.0
Pineapples 0.1(N) — 10.0
Plti (fresh prunes) 2.0 0.2 10.0
Potatoes 0.5 0.1(N) 0.5
Taro (corme) 0.02 — —
I natoes 15.0 5.0 5.0
Carrots 0.5
( c) MRL for whole peanuts is 0.5 ppn.
2. Seed Applications:
No tolerances have been established for captafol in or on any crop for
which captafol is registered solely for seed treatment or plant propagule
uses, because heretofore seed treatment and plant propagule uses have been
considered to be nonf cod uses. These crops include: corn (field), cotton,
rice, sorgh n (grain and age, strawberries (propagating bed use), and
sugarcane (seed piece use).
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Results of ‘r lerance Asses nent
Sufficient data are available to determine that the currently established
tolerances for residue of captafol in or on the follcMina CClmTCdities are
adequate: apricots, blueberries, cranberries, macadamia nuts, nectarines,
pead es, peanut hulls, and taro corms (40 CFR 180.267). However, additional
data concernina residues of metabolite PI must be sutinitted for all
cm dities since the residues of concern in or on plants have recently been
mdjfjed to include THPI. In addition to WpI data, other residue data are
required to support the tolerance for captafol in or on the following ccnin:x3ities:
apples, citrus fruits, corn (sweet), cuctmbers, melons, onions, peanuts,
pineapoles, plums (prunes), potatoes, arid tanatoes. I data and tolerance
c’hanaes must be sutinitted for sweet and sour cherries. Residue data and
tolerance proposals irust be submitted for the following cc1im ities: crops
receiving only seed treabiients (cotton, field corn, rice arid sorghum), pears
(state label use only), strawberries Fpropaciatina bed use: Section 24(c)l,
sugarcane (seed piece use), and taro foliage. lerances for the following
ccmidities are penciina: carrots, coffee beans, pecans, soybeans, and soybean
forage arid hay. Plant metaboli n of captafol is not adeauatelv understood,
therefore tolerance for residues other than caotafol and ‘E PI may need to
be souaht if those residues are de ned to be of concern. A poultry
metabolj n study will be needed. Also, feedina studies are reauired for
ruminants and Doultrv. diticnal storaae stability data are necessatv to
val idate the residue data. b crop aroup tolerance may be estabi ished
based on the available data.
The Theoretical Maximum Residue Contribution (‘1!1RC) is I .d 7Q nc/day based
pn a 1.c—kq diet. The thanae in the residue definition (by including the
metabolite ‘! 1PI), the reauested tolerance proposals arid the pendina tolerances
noted above will affect a change in the ‘I C level.
The maximum permissible intake (MPI) for a 60 kg person is 1.68 rw /day
based on an acceptable daily intake (ADI) of 0.028 mg/kg. The present RC
represents R6.8% of the MPI. The inclusion of the ma,or metabolite (‘t PI) in
the tolerance expression may result in an increase in the RC arid a greater
percentage of the MPI utilized.
The DI for captafol is based on a chronic toxicity study in rats. A
PEEL was established at 56 ppm for non-onooaenic effects. In that study
the next hiahest dose level caused cholanaiectasis in liver, increase
in hyperplasia of tubule epithelium, megalocytic cells arid
transitional cell hyoerplasia in kidney, increased erosion/ulceration,
hypericertosis/acanthosis, around substance in alandular mucosa, and dilated
pits in stcznath. The reported dosage level was corrected fran 7 ppm to 5(
ppm based on the instability of caotafol in the diet. In the rat, F pm is
aporo ciinately equivalent to 2.R mq/ka. rising a safety factor o 100 and a
PiZL of 2.8 mg/kg/day, the ADI uld be fl.02R ma/kg for h nans. The only
reaistrant of technical captafol, theuron th nical Ozmany, has been requested
to canpiete the histooatholoav examination of the low arid mid-dose liver and
m inary aland tissues: therefore, the MJ L for cholanqiectasis in the liver
may thanae. The CFL of 45 pan is for syst uic effects excluding
ie issue of oncogenicity for which a risk asses nent will be performed.
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Probl that are Kn n to Rave Occurred with Use of th th nical
1. Captafol is a skin sensitizer. Incidents of faam rkers being
disabled fran its effect have been re rted. Restrictinq the use of
captafol to nethanically harvested tanatoes, arid labeling requiri
use of gl es arid protective clothing by citrus harvesters have reduced
this pr.tl n.
4. &tmnary of Regulatory Positions arid Rationale
Based on the cmcoaenic arid fish tc cicity potential risks of hazard,
captafol is bsina placed under ecial Review by the ivirorinental Protection
Agency. The pres .utptian of risk of hazards out ighirig the derived benefits
n ist be rebutted by the manufacturers of pesticide pzvducts that have captafol
as an active ingredient. Based on the oncogenic potential and the fish
toxicity potential, captafol is classified as a “Restricted Use” pesticide.
All captafol products nust be relabeled as “Restricted t e ” pesticides.
The foll i labeling restrictions will be recuired for continued
registration of captafol products:
All tethnical orade, manufacturino-use (MtIP’s) arid end—use products
( YP’s) nust bear ppotopriate labeling as specified belc and in 4fl C ’R
1F2.lfl.
1. Precautionary statenents to be used on labeling of all end-use captafol
products:
a. All end-use product labels must reflect the follc* ,iriq stat nents:
i rR.tCrED (BE P rIC1DE. For retail sale to, and use only by
Certified applicators or persons under the direct supervision of
a Certified A licator, and only for those uses co’rered by the
Certified A licator’s certification.
“This product is classified as a “Restricted Use Pesticide”
because it contains captafol whith has been determined to
cause ti.znors in laboratory animals.”
cposure to captafol durina mixing, loadina, and apolication
may be hazardous to your health.
This product contains captafol whith has been determined to
cause tuiors in laboratory animals .
b. All end-use products imist have the labelina precaution under
‘Direction for t e ”: 1 ar ij pervicuS qlcwes and full body
clothing during handling arid a çlication”.
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C. Al] end-use products intended for crc use, except seed, seed
piece, and plant prcx aaule treatzrents must bear the foll ina
use restrictions:
i. i x , not rotate treated crc with cr s other than those
with registered captafol uses.
ii. t not al1c persons to enter treated areas within 24 hours
follcNina application unless full body clothing is i rn.
Ccnspicuously post reentry information at sites of app] icat ion.
iii. I X , not use captafol—treated rice seed in fields subeequently
to be used for agricultural crqs other than those with
req istered captafol uses
iiii. Water fran cranberry boqs, wetland taro fields (foliarly
treated with captafol) and rice fields planted with captafol-
treated rice seed must not be used for irriaation of crcos
other than those with registered captafol uses.
2. For oroducts that bear label claims for use in areenhouses:
a. ly the acolicator is oermitted in the areenhouse durino applicatior.
of captafol to soil. ( en vents to areenhouse during apol icatior
and for at least 1 hour after application.
b. rkers plantina in caotafol treated soil in greenhouses must
wear irpervious qlc es and full body clothing.
3. All products, manufacturina—use and end-use, must bear the labeling
precautionary statanents.
Causes irreversible eye d naqe. Harmful if s llcx ed or inhaled.
May cause allergic skin reactions. IX, not et in eyes. Wear goqales
or face shield when handling. Avoid contact with skin and clothing.
R T 7e and separately launder clothing before reuse.
This product contains captafol whi& has been determined
to cause tumors in laboratory animals
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In a3ditión, the following specific envirorgnental hazard labeling
r uir ents apply to either tedinical, manufacturing—use or end—use product
as irxhcated.
a. All tedinical arid IbVP’ s must bear the following precautionary
state rents:
This pesticide is extr nely toxic to fish. Do not disdiarge
into lakes, streams, ponds, or public waters unless in accordance
with an NPV permit. For guidance contact your Regional
Office of the EnviroruTEntal Protection Agency. Do not
disd arge effluent containing captafol into sewage syst ns
without obtaining permission fran the sewage treatnent authority.
b. All JP’s that allow for foliar applications except foliar application
to cranberries, must bear the hazard precaution:
This pesticide is extr ly toxic to fish. Do riot apply directly
to water. Drift arid runoff fran treated areas may be hazardous
to aguatic organi ns in neighboring areas. Do not contaminate
water by cleaning of equip nt or disposal of wastes.
c. All EXJP’s that allow foliar application to cranberries must bear the
tol lc iing environn ntal hazard precautions:
This pesticide is extr nely toxic to fish. Fish may be killed
at recaiirerided application rates. Drift arid runoff fran treated
areas may be hazardous to uat1c organi in neighboring areas.
Do not contaminate water by cleaning of equip!ent or disposal of
wastes.
d. All alP’s that allow seed trea nt must bear the following enviLcAw ntal
hazard precaution:
This pesticide is extreit ly toxic to fish. Do not contaminate
water by cleaning of equiplent or diposal of wastes.
4. Both MUP’s arid alP’s may need special labeling to protect endangered
species. This will be determined after required envirorm ntal
theiu.stry data are reviewed, arid in conjunction with EPA’S evaluation
of the potential risk of hazards to endangered species.
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Rased on historical use exrierience (himian health effects reprts)
and the benefits frcm the nest icide uses, the Aqencv will
allc the reaistration of cantafol products to continue for existinci
use—patterns until the risk of hazards is better defined tJ)r the
data suh utted in resconse to the Caotafol Reaistration Standard and
the caip ) etion of a Specia’ Review by the Aqencv and provided
that the reauirerl labelina under the Standard is suhiiitterl within the
time specified.
c. &minarv of Malor Data ( acs
Product thet istrv Data a
Description of beainnina materials and manufacturina orocess
Discussion of Formation of hypurities
Preliminary Analysis o Product Samnles
Density, Bulk Density, or Specific Gravity
Va r Pressure
Dissociation Constant
Oc’tanolmater Partition Coefficient
Solubility
Toxicoloqv
Inhalation LC 50 — Rat ( )
nfl-day feedino — dent, Non—rodent (18)
fl-day Ir* al.ation — Rat (18)
thronic ‘T’oxicitv - 2 snecies: xient and Non-rodent (16)
C iccxjenicitv stuiy - 2 species: Rat and Mouse preferred (6)
‘Peratoqenicity 2 species - needs hamsters stix)y usina t test aroups,
one dosed on day 7, and the other dose on day 8 of aestation (17)
flene I&itation (17)
flennal Absorption (6)
Residue O, i istrv (24)
Analytical Method
P1 ant Metabol is
Animal eta 1i (poultry)
Storaae Stability
Maqnitu e of Residues on all food—use crcos
Envirormanta] Fate
Soil Metabo1i - Aerobic soil (24)
— Anaerobic aauatic (24)
— Aerobic aauatic (24)
Degradation — Hydrolysis (6)
— Photodegrac3ation in water, soil and air (6)
Dissipation — Soil (24)
— Aquatic (sediment) (24)
Reentry (24)
a! Data to be subnitted in ntrber of months after receipt of the
Oiidance for the Rereqistration of Pesticide Products Containing
Captafol, EPA Case Mimber 116.
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I’ bilitv St ies ( 6 )a
Lead ing and AbsorotlonA)esorpt ion
Acc m ulation Sttx ies (24)
J tationai Crc s
Wildlife and uatic Oraani s
Acute 50 Estuarine and
Marine Orqani ns (6)
. O ntact Person
Fuqene M. Wilson
Office of Pesticide Proarams
Reqistraticri Division (‘PS—767C)
Crystal Mall 12
1921 Jefferson Davis Hwy.
Arlington, VA
Telej*ione (703) 557—1900
DISaAIMER: The information in this i nical Information Fact Sheet is for
informational pur ses only and may not be used to fulfill data requir nents
for pesticide registration or rereqistraticn.
a. Data to be sutviitted in number of months after receipt of the
( iidance for the Rereaistration of Pesticide Products Containing
Captafol, EPA Case t .unber 116.
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