triflumizole (Terraguard, Procure) EPA Pesticide Fact Sheet 10/91
EPA PESTICIDE FACT SHEET
Name Of Chemical: [[4-chloro-2(trifluoromethyl)phenyl]imino]-
2-Propoxy-ethyl-1H-imidazole
Reason for Issuance: Registration of New Active Ingredient
Date Issued: 10-24-9l
Fact Sheet Number: 228
DESCRIPTION OF CHEMICAL
_______________________
Generic Name: 1-[1-[[4-chloro-2-(trifluoromethyl)phenyl]imino]-
2-propoxyethyl]-1H-imidazole
Common Name: Triflumizole
Trade Name: Terraguard
EPA Shaughnessy Code: 128879
Chemical Abstracts Service (CAS) Number: 68694
Year of Initial Registration: 1991
Pesticide Type: Fungicide
U.S. and Foreign Producers: Uniroyal Chemical Company, Inc.
74 Amity Road
Bethany, CT 06525
USE PATTERNS AND FORMULATIONS
_____________________________
APPLICATION SITES: The manufacturing use product (MP) is for use only in the
formulation of fungicides. The end-use product is for use in control of
Cylindrocladium root and petiole rot on Spathiphyllum.
TYPES OF FORMULATION: The technical grade is a white crystalline formulation
containing 97% active ingredient. The end-use product is a wettable powder
containing 50% active ingredient.
TYPES AND METHODS OF APPLICATION: The end-use product is a protectant
fungicide to be used as a soil drench, foliar spray or through chemigation for
control of diseases on ornamentals grown in enclosed commercial structures
such as greenhouses, shade houses and interior scapes.
APPLICATION RATES: For all methods of treatment for Terraguard (soil drench,
foliar spray and/or chemigation), the pesticide is applied at the rate of 4 to
8 oz. per 100 gallons of water. This treatment is repeated every 2 to 4 weeks
or as needed. For best results use sufficient volume to ensure adequate soil
penetration.
SCIENCE FINDINGS
________________
Summary Science Statement
Available acute toxicity studies indicate that triflumizole is in
Toxicity Category I (Danger) based on the primary eye irritation study with
rabbits.
Chronic feeding/oncogenicity studies were conducted in both the rat and
mouse. The chronic feeding study in the rat suggests that the liver is the
main target organ with the ovary and kidney as secondary target organs.
Although there was an accompanying increase in organ weights, no carcinogenic
effects were seen.
In the chronic feeding study in mice, the results of blood chemistry,
organ weights and gross and histological examinations also indicate the liver
as the target organ.
Triflumizole did not induce either genotoxic effects or chromosomal
aberrations in a series of mutagenicity studies.
The teratology studies were conducted in the rabbit and rat. In the rat
studies, incidences of dilatation of the renal pelvis and increased 14th
rudimentary ribs were seen. In the rabbit, an increase in postimplantation
losses was noted.
Environmental fate data indicate that triflumizole has low potential for
leaching. Aerobic soil metabolism data indicates that triflumizole is
degraded rapidly by soil microbes to several products of which one is CO2.
Hydrolysis data show that the parent compound is quite stable at near neutral
pHs and undergoes slow hydrolysis at either mild acidic or basic conditions.
Studies also show that triflumizole has a half-life of 18 days in sandy loam
soil under laboratory conditions.
Ecological studies indicate triflumizole is practically non-toxic to
honeybees and birds. Triflumizole is categorized as being moderately toxic to
highly toxic to fish. Since this is a minor use registration and since
greenhouse applications have been traditionally treated as indoor uses, the
hazards to nontarget species and endangered species are considered to be
minimal.
TOXICOLOGICAL CHARACTERISTICS
_____________________________
Acute Toxicity
Acute oral toxicity in rats: LD50 2.43 g/kg males
LD50 2.05 g/kg females
Toxicity Category III
Acute dermal toxicity in rats: LD50 is greater than 2000 mg/kg
Toxicity Category III
Acute inhalation toxicity in rats: LC50 is greater than 3.2 mg/L
Toxicity Category III
Primary eye irritation in rabbit: Ocular opacity; Toxicity Category I
Primary dermal-irritation in rabbit: Negative: No irritation observed;
Toxicity Category IV
Dermal sensitization in guinea pigs: Positive for contact sensitization
CHRONIC STUDIES
_______________
Rodent Feeding/Oncogenicity
___________________________
A 2-year feeding/oncogenicity study with Sprague-Dawley rats was
conducted. Rats were fed 0, 5, 20 or 80 mg/kg/day doses of triflumizole
equivalent to 0, 100, 400 and 1600 ppm triflumizole for 104 weeks with an
interim sacrifice at 52 weeks. Numerous organ weights, clinical chemistry and
hematology parameters and microscopic changes indicate the main target organ
is the liver, with fatty vacuolization and periacinar hepatic hypertrophy seen
at all dose levels tested. Ovarian organ weights as well as well-developed
follicles indicate the ovary as a target. Kidney weights were affected as
well with increased cortical cysts seen in the kidneys of mid and high dose
animals. The NOEL is greater than 100 ppm, based on fatty vacuolization and
periacinar hepatic hypertrophy seen at all dose levels tested. An increase in
tumor incidence was not noted in any treatment groups.
A 2-year feeding/oncogenicity study with male and female mice using
dietary concentrations of 0, 100, 400 and 1600 ppm equivalent to 0, 15, 60 and
240 mg/kg/day was conducted. There were interim sacrifices at 26, 54, 78 and
104 weeks. Major effects were seen in the liver at all doses tested.
Clinical chemistry changes reflecting liver toxicity included changes in
alkaline phosphatase, BUN, SGOT, SGPT and cholesterol. Absolute and relative
liver weights were increased at all time periods in the high dose males and
females and in some animals of the mid dose groups. At sacrifice, liver
changes in all dose groups included hepatic nodules and cytoplasmic
alterations. The systemic NOEL was less than 100 ppm. Although there was a
slight increase the incidence of lymphoma in both treated males and females,
it was judged not be compound-related.
A 3-month feeding study in rats was conducted using dietary
concentrations of o, 20, 200 and 2000 ppm equivalent to 0, 2, 20 and 200
mg/kg/day. The NOEL was 200 ppm. The LEL was 2000 ppm (HDT) based on slight
decrease in food consumption and body weight and changes in blood chemistry.
A 3-month feeding study with mice was conducted using dietary
concentrations of 0, 20, 200 and 2000 ppm equivalent to 0, 3, 30, 300
mg/kg/day. The NOEL was 200 ppm and the LEL was 2000 ppm based on liver
effects.
A 30-day feeding study with rats was conducted using dietary
concentrations of 20, 200 and 2000 ppm equivalent to 0, 2, 20 and 200
mg/kg/day. The NOEL was 200 ppm and the LEL was 2000 ppm based on liver
changes, necrosis and fatty metamorphosis.
A 30-day feeding study with mice was conducted using dietary
concentrations of 20, 200 and 2000 ppm equivalent to 0, 3, 30 and 300
mg/kg/day. The NOEL was 200 ppm and the LEL was 2000 ppm based on enlarged
livers.
Non-Rodent Feeding Studies
__________________________
A 1-year feeding study with beagle dogs using dietary concentrations of
0, 100, 300 and 1000 ppm equivalent to 0, 2.5, 7.5 and 25 mg/kg/day was
conducted. The NOEL was 300 ppm and the LEL was 1000 ppm based on liver and
blood chemistry changes.
TERATOLOGY
__________
A teratology study using Sprague-Dawley rats was conducted by
administering levels of 0, 10, 35 and 120 mg/kg/day by gavage. The
teratogenic NOEL was greater than 12 0 mg/kg/day (HDT). The maternal NOEL in
this test was 10 mg/kg/day and maternal LEL was 35 mg/kg/day based on
decreased body weight and decreased water and food consumption. The fetotoxic
NOEL was greater than 10 mg/kg/day (LDT) based on dilation of renal pelvis.
A complementary study was conducted using dose levels of O and 3 mg/kg:
the NOEL was 3 mg/kg. Another teratology study using rats was conducted using
dose levels of 0, 3, 7, and 35 mg/kg by gavage. The maternal NOEL was 7
mg/kg. The maternal LEL was 35 mg/kg based on reduced body weight gain and
decreased food consumption. The developmental NOEL was 7 mg/kg. The
developmental LEL was 35 mg/kg based on death and increase in incidence of
14th rudimentary ribs and cervical ribs. The A/D ratio was determined to be
7/7 = 1.
A teratology study was conducted in rabbits by administering dosage rates
of 0, 50, 100 and 200 mg/kg by gavage. The maternal NOEL was 50 mg/kg. The
maternal LEL was 100 mg/kg based on decreased food consumption, body weights
and organ weights. The developmental NOEL was greater than 50 mg/kg (LDT)
based on decreases in fetal and placental body weights and 24-hour survivals.
The A/D ratio was determined to be 50/greater than 50 = greater than 1. A
range finding study was conducted in rabbits using dose rates of 0, 10, 50,
100, 200 and 300 mg/kg by gavage. The maternal NOEL was 100 mg/kg. The
maternal LEL was 200 mg/kg based on decreased body weight and food
consumption. The developmental NOEL was 100 mg/kg. The developmental LEL was
200 mg/kg based on increased postimplantation losses.
Another teratology study was conducted in rabbits using lower doses (O,
5, 25 and 50 mg/kg by gavage). There was no evidence of clear maternal
toxicity. The offspring showed no adverse effects. The maternal NOEL was
greater than 50 mg/kg and the developmental NOEL was greater than 50
mg/kg/day.
REPRODUCTION
____________
In a 2-generation rat reproduction study, dose levels of 0, 30, 70 and
170 ppm in feed were used. No parental toxicity was observed. The parental
NOEL was greater than 170 ppm (HDT). The reproductive NOEL was 70 ppm. The
reproductive LEL was 170 ppm based on increased gestation lengths. The
developmental NOEL was 70 ppm. The developmental LEL was 170 ppm based on
reduced Fla litter size and increased fetal incidences of hydroureter and
space between body walls and organs.
In a 3-generation rat reproduction study, dose levels of 0, 70, 170 and
420 ppm in feed resulted in a NOEL greater than 70 ppm (LDT) based on
increased gestation length. At 170 ppm there was pup mortality. At 420 ppm,
there was reduced body weight gain, increased length of estrous cycles,
reduced vaginal cornification, extended gestation length and high pup
mortality.
Another 3-generation rat reproduction study as conducted using lower dose
levels (0, 30, 70 and 170 ppm). The reproduction NOEL was greater than 30 ppm
based on increased gestation lengths at all doses tested. The developmental
NOEL was 70 ppm. The developmental LEL was 170 ppm based on increased
incidence of hydroureter and space between the body wall and organs, increased
pup mortality and reduced pup weight. The parental NOEL was greater than 170
ppm (HDT).
MUTAGENICITY
____________
Triflumizole was negative for mutagenicity in the mitotic gene conversion
test, rec assay test, in vitro mouse micronucleus test, reverse mutation in
Salmonella and E. coli test and unscheduled DNA synthesis test.
ENVIRONMENTAL FATE
__________________
Environmental fate studies for leaching/adsorption/desorption show that
unaged Carbon 14 triflumizole was slightly mobile in a column (30.4 cm length)
of sandy soil treated with 214 micrograms (1 lb ai/A) of phenyl ring-labeled
Carbon 14 triflumizole (radiopurity 93.4%) and leached with 63.7 column CM of
distilled water. Seventy-eight percent of the recovered radioactivity was
found in the top six inches of soil. The majority (greater than 81%) of the
radioactivity in each soil segment was triflumizole. This, together with the
leachate data, indicates low potential for leaching and indicates that
triflumizole should not pose a problem in field runoff or in contamination of
ground water.
Data from an aerobic soil metabolism study of Carbon 14 triflumizole in
sandy loam soil indicate that triflumizole underwent soil degradation with a
half-life of 18 days. The parent compound degraded via three degradation
intermediates to 4-chloro-2-trifluoromethylaniline, which volatilized from the
soil and/or underwent further degradation to C02 by microorganisms.
Hydrolysis studies show that phenyl-labeled Carbon 14 triflumizole
(radiochemical purity greater than 99%), at 5 ppm, degraded in sterile aqueous
0.01 M buffered solutions with half-lives of 7 to 15 days at pH 5, greater
than 30 days at pH 7 and 3 to 17 days at pH 9 when incubated in the dark at 25
plus or minus 1 C. The registrant-calculated half-lives were 8 to 9 days (pH
5), 64.6 days (pH 7) and 3.9 days (pH 9). At 30 days posttreatment, Carbon 14
triflumizole accounted for 73.5% of the applied radioactivity in the pH 7
solution. 4-Chloro-alpha-alpha-alpha-trifluoro-N-2-propoxyacetyl-0-toluidine
was identified as the major degradate at all three pHs, with maximum
concentrations of 83.1% of the applied at pH 5, 20.8% at pH 7 and 84.0% at pH
9. Material balances ranged from 96 to 1O3% during the test period.
ECOLOGICAL CHARACTERISTICS
__________________________
Studies submitted show that triflumizole is practically nontoxic to
honeybees (LD50 greater than 160 ug per bee) and birds (LC50 greater than
5,620 ppm and LD50 greater than 2,510 ppm). Since it is unlikely that
triflumizole will come into contact with these species, it is not expected to
pose a threat to honeybees and birds (nontarget and endangered species).
Triflumizole is categorized as being moderately toxic to highly toxic to fish.
The expected levels of triflumizole in a farm pond are not predicted to exceed
1/10 of the warmwater fish LC50 (1.2 ppm) which is the nontarget species
cutoff point. There are only two endangered fish species in Florida. The
shortnosed sturgeon (Acipenser brevinostrum) is in Duval and Putnam Counties.
The Okaloosa darter (Etheostoma okaloosae) is in Walton and Okaloosa
Counties. None of these four counties is in southern Florida where the
pesticide will be used. The expected levels of triflumizole in a farm pond
are not predicted to exceed 1/20 of the warmwater fish LC50 (1.2 ppm) which is
the endangered species cutoff point. Triflumizole is not expected to be a
threat to endangered fish. Since this is a minor use registration and
greenhouse applications have been traditionally treated as indoor uses, the
hazards to non-target species and endangered species is considered to be
minimal. All available ecological data indicate that the use of triflumizole
on Spathiphyllum will not cause undue environmental damage.
BENEFITS
________
This chemical has low mammalian toxicity. Its use as a fungicide on
ornamentals does not pose any unreasonable effect to man or the environment.
Triflumizole is effective at low rates in controlling Cylindrocladium.
CONTACT PERSON AT EPA
_____________________
Susan T. Lewis
Product Manager (PM) 21
Registration Division (H7505C)
Environmental Protection Agency
401 M Street SW.
Washington, DC 20460
Office Location and Telephone Number:
Rm 227, CM#2
1921 Jefferson Davis Highway
Arlington, VA 22202 (703) 557 -1900
DISCLAIMER: This information presented in this Pesticide Fact Sheet is for
informational purposes only and may not be used to fulfill data requirements
for pesticide registration and/or reregistration.
Disclaimer: Please read
the pesticide label prior to use. The information contained at this web
site is not a substitute for a pesticide label. Trade names used herein
are for convenience only; no endorsement of products is intended, nor is
criticism of unnamed products implied. Most of this information is historical
in nature and may no longer be applicable.
To Top
For more information relative to pesticides and their use in New York State, please contact the PMEP staff at:
| |
5123 Comstock Hall
Cornell University
Ithaca, NY 14853-0901
(607) 255-1866
|
|
 |
This site is supported, in part, by funding from the
 |
Questions regarding the development of this web site should be directed to the
PMEP Webmaster
