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Triflumizole

HCID 91699
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
149465-52-1
Standard SMILES
CCCOCC(=Nc1ccc(Cl)cc1C(F)(F)F)n1ccnc1
InChIKey
HSMVPDGQOIQYSR-UHFFFAOYSA-N
Molecular formula
C15H15ClF3N3O
Average molar mass
345.75 g/mol
Monoisotopic mass
345.0855743

Overview

Triflumizole is a carboxamidine resulting from the formal condensation of the amino group of 4-chloro-2-(trifluoromethyl)aniline with the oxygen of the acetyl group of N-(propoxyacetyl)imidazole. A sterol demethylation inhibitor, it is used as a fungicide for the control of powdery mildew, scab and other diseases on a variety of crops. It has a role as an EC 1.14.13.70 (sterol 14alpha-demethylase) inhibitor and an antifungal agrochemical. It is a member of imidazoles, an ether, a carboxamidine, a member of monochlorobenzenes, a member of (trifluoromethyl)benzenes, a conazole fungicide and an imidazole fungicide.

Names & identifiers

Preferred name
Triflumizole
IUPAC
N-[4-chloro-2-(trifluoromethyl)phenyl]-1-imidazol-1-yl-2-propoxyethanimine
English name
TRIFLUMIZOLE
Molecular formula
C15H15ClF3N3O
Molecular weight
345.75

Names & synonyms

Triflumizole68694-11-1TriflumizolTerraguardTrifmineProcureTrifumineCondortrifuminNF-114DTXSID20325007J6Y4H9MV5
Show more names
DuotopSS-P-11riflumizole
SSP-11(E)-4-Chloro-alpha,alpha,alpha-trifluoro-N-(1-imidazol-1-yl-2-propoxyethylidene)-o-toluidine1-(1-((4-Chloro-2-(trifluoromethyl)phenyl)imino)-2-propoxyethyl)-1H-imidazolePROCURE (FUNGICIDE)DTXCID0012500CHEBI:817844-Chloro-alpha,alpha,alpha-trifluoro-N-(1-imidazol-1-yl-2-propoxyethylidene)-o-toluidine(1E)-N-[4-chloro-2-(trifluoromethyl)phenyl]-1-(1H-imidazol-1-yl)-2-propoxyethan-1-imine

Database identifiers

CAS
149465-52-1、68694-11-1、99387-89-0
PubChem CID
91699
DTXSID
DTXSID20860885
ChEMBL
CHEMBL463781
ChEBI
CHEBI:81784
UNII
7J6Y4H9MV5
EC Number
614-708-8、619-427-4
Nikkaji
J26.588H、J43.105B

Properties

Computed structural properties

XLogP
4
Topological polar surface area
39.4 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
6
Rotatable bonds
6
Heavy atoms
23
Formal charge
0
Complexity
406

Experimental & physicochemical properties

Pesticides · 6 items

Fungicides

Active substance -> EU Pesticides database: Not approved

Pesticides -> Fungicides

Environmental transformation -> Pesticides (parent, predecessor)

Fungicides

Pesticide (Triflumizole) -> USDA PDB

LogP · 3 items

log Kow = 5.06 at pH 6.5; log Kow = 5.10 at pH 6.9; log Kow = 5.12 at pH 7.9

4.8 (calculated)

4.5

Density1.4 g/cm³
Color/FormColorless crystals
Solubility · 3 items

In water, 10.2 mg/L at 20 °C and pH 7

In chloroform = 2.22 mg/L at 20 °C; hexane = 0.0176 mg/L at 20 °C; xylene = 0.639 mg/L at 20 °C; acetone = 1.44 mg/L at 20 °C; methanol = 0.496 mg/L at 20 °C

Solubility in water, mg/l at 20 °C: 10.2 (practically insoluble)

Boiling PointNo boiling point at normal pressure; decomposes at 150 °C
DecompositionDecomposes on burning. This produces toxic and corrosive fumes including nitrogen oxides, hydrogen fluoride, and hydrogen chloride.

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 6 items

Danger

H302: Harmful if swallowed [Warning Acute toxicity, oral]

P203, P260, P261, P264, P270, P272, P273, P280, P301+P317, P302+P352, P318, P319, P321, P330, P333+P317, P362+P364, P391, P405, and P501 (click each P-code to see the statement)

Danger

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P203, P260, P261, P264, P270, P272, P273, P280, P301+P317, P302+P352, P318, P319, P321, P330, P333+P317, P362+P364, P391, P405, and P501 (click each P-code to see the statement)

Hazard information

Regulatory Information · 5 items

Chemical: 1H-Imidazole, 1-[1-[[4-chloro-2-(trifluoromethyl)phenyl]imino]-2-propoxyethyl]-

Hazard Traits - Reproductive Toxicity

Commission Regulation (EC) No 1490/2002

Triflumizole is listed in the dataset of EPA Human Health Benchmarks for Pesticides under the Safe Drinking Water Act (40 eCFR 141)

2010/27/EU, Reg. (EU) 2022/801, Reg. (EU) No 540/2011

Other Safety Information · 2 items

IMAP assessments - 1H-Imidazole, 1-[1-[[4-chloro-2-(trifluoromethyl)phenyl]imino]-2-propoxyethyl]-, (E)-: Environment tier I assessment

Evaluation - Chemicals not considered for in depth evaluation - Not commercially active in Australia

Fire HazardsLiquid formulations containing organic solvents may be flammable. Gives off irritating or toxic fumes (or gases) in a fire.
Fire PotentialLiquid formulations containing organic solvents may be flammable.
Hazards SummaryTLV Basis is liver changes. The NOAEL in animal studies is 3.5 mg/kg in male rats fed trifumizole for 2 years. [ACGIH]

Chemistry & industry

Pharmacology

Metabolism/Metabolites · 1 item

The metabolism of triflumizole was investigated by analyzing fecal and urine samples retained from ... previous studies: single oral administration of 10 or 300 mg/kg bw and 14 consecutive oral doses of 10 mg/kg bw per day. ... Triflumizole is extensively metabolized: less than 2% of the radiolabel recovered from urine or feces was identified as parent compound. A few differences in metabolite pattern were observed between males and females after repeated low and single high doses, but not after a single low dose. The major urinary metabolites are the sulfate conjugates of FM-8-1 and FA-1-5, each representing approximately 20% of the radiolabel recovered after the single low dose from that matrix and, respectively, approximately 11% and 20% after the high dose. In feces, FD-2-1 is a major metabolite in all dose regimens (~6-10% of the recovered radiolabel). Considerable differences between dose regimens exist with respect to other major metabolites. FM-2-1 is the major metabolite after a single oral low dose (~9% of radiolabel recovered in feces), but represents less than 2% for the other dose regimens. FA-1-1 is a major metabolite after single and repeated low dosing (~5-10%), but not after single oral high dosing (<3%), whereas FD-1-1 is the major metabolite after a single oral high dose (~16%) and a minor metabolite after single and repeated low doses (<2%). The metabolite FM-6-1 was tentatively identified by TLC co-chromatography, and the radioactive band corresponding to the authentic FM-6-1 was obscure, because of its low radioactivity.

Absorption, Distribution and Excretion · 2 items

Following oral treatment of rats with /a single oral dose of 10 mg/kg/ [phenyl- U-(14)C]-NF-114, no sex-related differences were observed in absorption, metabolism, distribution or excretion. Maximum concentrations of radioactivity in plasma were attained within 1 hour of dosing in both sexes. Low levels of radioactivity were detectable in all tissue, organ, and blood samples. Radioactivity in urine accounted for 69.5-74.4% of the dose and feces accounted for 21.7-21.9% of the dose. /From table/

M&F: 10 or 300 mg/kg as single oral dose: Following oral treatment of rats with [phenyl- U-(14)C]-NF-114, approximately 93.8-100.6% of the administered dose was recovered. Urine was the major route of excretion. Low levels of radioactivity were detectable in all tissue, organ, and blood samples collected 2 days (10 mg/kg group) or 4 days (300 mg/kg group) post-dose with tissue concentrations generally higher in males than females. The metabolite profile in the excreta was quantitatively and qualitatively similar between the sexes and dose groups. /From table/

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Melting Point · 2 items

63.5 °C

63 °C

Vapor Pressure · 3 items

0.0000014 [mmHg]

1.4X10-6 mm Hg at 25 °C

Vapor pressure at 25 °C: negligible

Physical DescriptionCOLOURLESS CRYSTALS.
Stability/Shelf LifeStable under recommended storage conditions.
Dissociation ConstantspKa = 3.70 at 25 °C

Physicochemical properties

Melting point
63.5 °C · 63.5°C
Boiling point
421.2 · 421.2±55.0 °C(Predicted)
Density
1.3288 · 1.3288 (estimate)
storage temp.
0 · 0-6°C
solubility
Chloroform (Slightly), Methanol (Slightly)
form
Solid
pka
3.21 · 3.21±0.10(Predicted)
color
White to off-white
Henry's Law Constant
1.9 · 1.9×105 mol/(m3Pa) at 25℃, Duchowicz et al. (2020)
Major Application
agricultureenvironmental
InChI
1S/C15H15ClF3N3O/c1-2-7-23-9-14(22-6-5-20-10-22)21-13-4-3-11(16)8-12(13)15(17,18)19/h3-6,8,10H,2,7,9H2,1H3/b21-14+
InChIKey
HSMVPDGQOIQYSR-KGENOOAVSA-N
SMILES
CCCOC\C(=N/c1ccc(Cl)cc1C(F)(F)F)n2ccnc2
FDA UNII
7 J6Y4H9MV5 · 7J6Y4H9MV5
EPA Substance Registry System
Triflumizole (68694-11-1)
UNSPSC Code
41116107 · 41116107
NACRES
24 · NA.24
Symbol(GHS)
7 · GHS07,GHS09
Signal word
Warning
Hazard statements
302 · H302-H411
Precautionary statements
273 · P273-P301+P312+P330
target organs
Liver
PPE
95 · dust mask type N95 (US), Eyeshields, Gloves
Hazard Codes
Xn,N
Risk Statements
22 · 22-51/53
Safety Statements
61 · 61
RIDADR
3077 · UN 3077 9 / PGIII
WGK Germany
3 · 3
RTECS
4490000 · NI4490000
HS Code
29332900 · 29332900
Storage Class
6.1 C · 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
Hazard Classifications
4 OralAquatic · Acute Tox. 4 OralAquatic Acute 1Aquatic Chronic 1Repr. 1BSkin Sens. 1STOT RE 2
Hazardous Substances Data
68694 · 68694-11-1(Hazardous Substances Data)
UN ClassificationUN Hazard Class: 9; UN Pack Group: III
FIFRA Requirements · 3 items

Tolerances are established for residues of the fungicide triflumizole, including its metabolites and degradates, in or on the commodities listed in the table below. Compliance with the tolerance levels specified below is to be determined by measuring only the parent compound triflumizole, 1-(1-((4-chloro-2-(trifluoromethyl)phenyl)imino)-2-propoxyethyl)-1H-imidazole, and its metabolites containing the 4-chloro-2-trifluoromethylaniline moiety, calculated as stoichiometric equivalent of the parent compound.[Table#8401]

Tolerances are established for residues of the fungicide triflumizole, including its metabolites and degradates, in or on the commodities of animal origin listed in the table below. Compliance with the tolerance levels specified below is to be determined by measuring only the parent compound triflumizole, 1-(1-((4-chloro-2-(trifluoromethyl)phenyl)imino)-2-propoxyethyl)-1H-imidazole, the metabolite 4-chloro-2-hydroxy-6-trifluoromethylaniline sulfate, and other metabolites containing the 4-chloro-2-trifluoromethylaniline moiety, calculated as the parent compound.[Table#8402]

New Active Ingredients ... includes chemicals not previously registered as pesticides, as well as pesticide active ingredients initially registered after November 1, 1984 and that currently have active product registrations. By law, these pesticides must meet new safety standards, such as those described in the Food Quality Protection Act of 1996 and, if new safety standards are met, will be reviewed again on a 15-year cycle. Triflumizole is designated by EPA as a New Pesticide Active Ingredient. Active Ingredient Number: 128879; Type of Pesticide: conventional - fungicide; Use Site: food use, ornamentals; Year: 1991.

Chemical Dangers · 1 item

Decomposes on heating and on burning. This produces toxic and corrosive fumes including nitrogen oxides, hydrogen fluoride, hydrogen chloride and carbon monoxide. Reacts with strong acids and strong bases. This generates toxic, fire and explosion hazard.

Packaging and LabellingDo not transport with food and feedstuffs.
Toxic Combustion Products · 2 items

Special hazards arising from the substance or mixture: Carbon oxides, nitrogen oxides (NOx), hydrogen chloride gas, hydrogen fluoride.

Gives off irritating or toxic fumes (or gases) in a fire.

Hazard Classes and Categories · 4 items

Acute Tox. 4 (100%)

Reproductive toxicity - category 1B

Acute toxicity (Oral) - Category 4

Repr. 1B

Explosive Limits and PotentialRisk of fire and explosion if formulations contain flammable/explosive solvents.

Safety & protection

Fire FightingIn case of fire in the surroundings, use appropriate extinguishing media.
First Aid Measures · 4 items

Fresh air, rest.

Remove contaminated clothes. Rinse and then wash skin with water and soap.

Rinse with plenty of water for several minutes (remove contact lenses if easily possible).

Rinse mouth. Refer for medical attention .

Safe StorageProvision to contain effluent from fire extinguishing. Separated from food and feedstuffs. Well closed. Store in an area without drain or sewer access.
Fire Fighting Procedures · 2 items

Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.

Advice for firefighters: Wear self contained breathing apparatus for fire fighting if necessary.

Storage Conditions · 3 items

Keep container tightly closed in a dry and well-ventilated place.

Store in a cool, dry, well-ventilated place, away from feed, food, children, and animals.

Store in a cool, dry, secure location. Do not store above 45 °C (113 °F).

Cleanup Methods · 2 items

ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Avoid breathing dust. Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Methods and materials for containment and cleaning up: Pick up and arrange disposal without creating dust. Sweep up and shovel. Keep in suitable, closed containers for disposal.

Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations. Do NOT wash away into sewer.

Disposal Methods · 4 items

SRP: Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in air, soil or water; effects on animal, aquatic and plant life; and conformance with environmental and public health regulations. If it is possible or reasonable use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination.

Product: Offer surplus and non-recyclable solutions to a licensed disposal company; Contaminated packaging: Dispose of as unused product.

Do not contaminate water when disposing of equipment washwaters or rinsate. This product is toxic to fish. Do not discharge effluent containing this product into lakes, streams, ponds, estuaries, oceans, or public waters unless in accordance with the requirements of a National Pollutant Discharge Elimination System (NPDES) permit and the permitting authority has been notified in writing prior to discharge. Do not discharge effluent containing this product to sewer systems without previously notifying the local sewage treatment plant authority. For guidance, contact your State Water Board ot Regional Office of the Environmental Protection Agency.

Wastes resulting from the use of this product may be disposed of at an approved waste disposal facility.

Spillage Disposal · 1 item

Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Do NOT let this chemical enter the environment. Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations.

Preventive Measures · 5 items

ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Avoid breathing dust. Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided.

Precautions for safe handling: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Provide appropriate exhaust ventilation at places where dust is formed. Normal measures for preventive fire protection.

Appropriate engineering controls: Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday.

Gloves must be inspected prior to use. Use proper glove removal technique (without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands.

For more Preventive Measures (Complete) data for Triflumizole (7 total), please visit the HSDB record page.

Eye PreventionWear safety spectacles.
Inhalation RiskEvaporation at 20 °C is negligible; a harmful concentration of airborne particles can, however, be reached quickly on spraying or when dispersed, especially if powdered.
Skin PreventionProtective gloves.

Toxicology

Health Effects · 1 item

In human, a neuromuscular impairment and decreased locomotor activity were observed following a single exposure of 100 mg/kg/day. The liver is the primary target organ of triflumizole in the rat, mouse, and dog. It increased liver weight, hepatocyte fatty vacuolization, hypertrophy, inflammation, fatty degeneration, and caused necrosis. Chronic effects of triflumizole included hepatocyte fatty vacuolization, hepatocyte hypertrophy, focal inflammation, and necrosi,; fatty degeneration, eosinophilic foci of hepatocyte alteration, hepatic nodules, bile duct hyperplasia, and hyaline degeneration/fibrosis of the bile duct. Liver effects were seen in rat and mouse subchronic and chronic/carcinogenicity studies. The fetal effects were also seen in rats. Triflumizole has a reproductive toxicity as well, the gestation length was increased in rats receiving high dose of triflumizole.

Ecotoxicity Values · 5 items

LC50; Species: Colinus virginianus (Northern Bobwhite Quail) age 14 days; dietary >5620 ppm for 8 days[USEPA, Office of Pesticide Programs; Pesticide Ecotoxicity Database (2000) on 1-[(1E)-1-[

LD50; Species: Colinus virginianus (Northern Bobwhite Quail) age 34 wk; oral via capsule >2510 mg/kg[USEPA, Office of Pesticide Programs; Pesticide Ecotoxicity Database (2000) on 1-[(1E)-1-[

LC50; Species: Anas platyrhynchos (Mallard Duck) age 9 days; dietary >5620 ppm for 8 days[USEPA, Office of Pesticide Programs; Pesticide Ecotoxicity Database (2000) on 1-[(1E)-1-[

LD50; Species: Apis mellifera (Honey Bee) adult; topical, general >160 ug/bee[USEPA, Office of Pesticide Programs; Pesticide Ecotoxicity Database (2000) on 1-[(1E)-1-[

For more Ecotoxicity Values (Complete) data for Triflumizole (17 total), please visit the HSDB record page.

Environmental Fate · 3 items

TERRESTRIAL FATE: Based on a classification scheme(1), a Koc value of 1400(2) indicates that triflumizole is expected to have low mobility in soil(SRC). The pKa of triflumizole is 3.7(3), indicating that this compound, a weak base, will exist in the neutral form in the environment(SRC). Volatilization of triflumizole from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 6.2X10-8 atm-cu m/mole(4) derived from its vapor pressure, 1.4X10-6 mm Hg(3), and water solubility, 10.2 mg/L(3). Triflumizole is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure. Triflumizole was scarcely detected (less than 1 ppb) in leaching water from golf courses 3 to 37 days after application of pesticide indicating minimal to no potential for leaching into groundwater(5). Triflumizole has been reported to be slightly degraded under soil aerobic conditions(6), suggesting that biodegradation is not an important environmental fate process in soil(SRC).

AQUATIC FATE: Based on a classification scheme(1), a Koc value of 1400(2) indicates that triflumizole is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 6.2X10-8 atm-cu m/mole(4) derived from its vapor pressure, 1.4X10-6 mm Hg(5), and water solubility, 10.2 mg/L(5). According to a classification scheme(6), a BCF of 390(7) indicates bioconcentration in aquatic organisms is high(SRC). Triflumizole has been reported to be degraded under aquatic anaerobic conditions(8), suggesting that biodegradation is not an important environmental fate process in water(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), triflumizole, which has a vapor pressure of 1.4X10-6 mm Hg at 25 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase triflumizole is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 7 hours(SRC), calculated from its rate constant of 5.4X10-11 cu cm/molecule-sec at 25 °C(SRC), that was derived using a structure estimation method(3). Particulate-phase triflumizole may be removed from the air by wet and dry deposition. Triflumizole contains chromophores that absorb at wavelengths >290 nm(4) and, therefore, is susceptible to direct photolysis by sunlight(SRC). Triflumizole has a photolysis half-life of 1.2 days based on a reported photolysis rate constant in sunlight-water equal to 0.574/day(5).

Food Survey Values · 1 item

Results from an agricultural product monitoring effort in Japan during April 1995 through March 2000 reported triflumizole detections in 7 out of 86 samples of strawberries and grapes at concentrations between 0.5 and less than 0.01 ug/g(1). Triflumizole residues on strawberries examined in 1992 and 1993 were between 0.01 and 2.0 ug/g(2). Triflumizole was detected in 3 out of 173 agricultural product samples from a local market in Japan at concentrations of 1.9 to 494 ng/g(3).

Adverse EffectsOccupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.
Exposure RoutesThe substance can be absorbed into the body by inhalation of dust and by ingestion.
Toxicity Summary · 1 item

IDENTIFICATION AND USE: Triflumizole is a fungicide used for the control of powdery mildew, such as Sphaerotheca fuliginea, Sphaerotheca pannosa, Erysiphe cichoracearum, and others. HUMAN EXPOSURE AND TOXICITY: A report on the results of its yearly health examination of the personnel involved in the production of triflumizole at the Takaoka plant (Japan) during the period May 1996 to May 2002 was published. No adverse health effects attributable to chemical exposure were observed. In addition, it was reported that in the period covered, no events of acute poisoning by exposure or skin and/or eye irritation were observed. Repeated or prolonged contact may cause skin sensitization. The substance may have effects on the liver and blood. This may result in liver impairment and a decrease in hemoglobin. ANIMAL STUDIES: Triflumizole is sensitizing to the skin of guinea pigs. It is mildly irritating to the eye of rabbits. An acute inhalation toxicity test for triflumizole was conducted in rats. Symptoms of toxicity included hunched posture, lethargy and chromodacryorrhoea (head and/or snout) among the majority of the animals. Signs of oral toxicity from triflumizole observed in rats included ataxia, hypotonia, ventral position, lacrimation, urinary incontinence, decreased body temperature, decreased heart rate and respiration rate, and ptosis. Triflumizole did not produce tumors in rats after 104 weeks of treatment. In developmental studies in rats no statistically significant treatment-related external, visceral, or skeletal malformations or variations were noted. In a mouse study, prenatal triflumizole exposure increases adipose depot weight and diverts mesenchymal stromal stem cells fate toward the adipocyte lineage. Triflumizole was not mutagenic in the Ames test with or without metabolic activation. ECOTOXICITY STUDIES: Using rare minnow (Gobiocypris rarus) at early-life stages, the developmental toxicity of five widely used triazole fungicides including triflumizole was rated as highly toxic.

Ecotoxicity Excerpts · 1 item

/AQUATIC SPECIES/ Using rare minnow (Gobiocypris rarus) at early-life stages as experimental models, the developmental toxicity of five widely used triazole fungicides (myclobutanil, fluconazole, flusilazole, triflumizole, and epoxiconazole) were investigated following exposure to 1-15 mg/L for 72 hr. Meanwhile, morphological parameters (body length, body weight, and heart rate), enzyme activities (superoxide dismutase (SOD), glutathione S-transferase (GST), adenosine triphosphatase (ATPase), and acetyl cholinesterase (AChE)), and mRNA levels (hsp70, mstn, mt, apaf1, vezf1, and cyp1a) were also recorded following exposure to 0.2, 1.0, and 5.0 mg/L for 72 hr. Results indicated that increased malformation and mortality, decreased body length, body weight, and heart rate provide a concentration-dependent pattern; values of 72 hr LC50 (median lethal concentration) and EC50 (median effective concentration) ranged from 3 to 12 mg/L. Most importantly, the results of the present study suggest that even at the lowest concentration, 0.2 mg/L, five triazole fungicides also caused notable changes in enzyme activities and mRNA levels. Overall, the present study points out that those five triazole fungicides are highly toxic to the early development of G. rarus embryos. ...

Signs and SymptomsRedness.
Ongoing Test Status · 1 item

EPA has released the Interactive Chemical Safety for Sustainability (iCSS) Dashboard. The iCSS Dashboard provides an interactive tool to explore rapid, automated (or in vitro high-throughput) chemical screening data generated by the Toxicity Forecaster (ToxCast) project and the federal Toxicity Testing in the 21st century (Tox21) collaboration. /The title compound was tested by ToxCast and/or Tox21 assays/[USEPA; ICSS Dashboard Application; Available from, as of December 8, 2016: http://actor.epa.gov/dashboard/]

ICSC Environmental DataThe substance is very toxic to aquatic organisms. The substance may cause long-term effects in the aquatic environment. Avoid release to the environment in circumstances different to normal use.
Soil Adsorption/Mobility · 1 item

The mobility of triflumizole was examined using soil thin layer chromatography with a silt loam containing 2% organic matter; results indicated that this chemical will be slightly mobile in soil(1). Triflumizole has a reported soil adsorption coefficient equal to 1400(2). According to a classification scheme(3), this Koc value suggests that triflumizole is expected to have low mobility in soil.

Regulatory information

FIFRA Requirements · 3 items

Tolerances are established for residues of the fungicide triflumizole, including its metabolites and degradates, in or on the commodities listed in the table below. Compliance with the tolerance levels specified below is to be determined by measuring only the parent compound triflumizole, 1-(1-((4-chloro-2-(trifluoromethyl)phenyl)imino)-2-propoxyethyl)-1H-imidazole, and its metabolites containing the 4-chloro-2-trifluoromethylaniline moiety, calculated as stoichiometric equivalent of the parent compound.[Table#8401]

Tolerances are established for residues of the fungicide triflumizole, including its metabolites and degradates, in or on the commodities of animal origin listed in the table below. Compliance with the tolerance levels specified below is to be determined by measuring only the parent compound triflumizole, 1-(1-((4-chloro-2-(trifluoromethyl)phenyl)imino)-2-propoxyethyl)-1H-imidazole, the metabolite 4-chloro-2-hydroxy-6-trifluoromethylaniline sulfate, and other metabolites containing the 4-chloro-2-trifluoromethylaniline moiety, calculated as the parent compound.[Table#8402]

New Active Ingredients ... includes chemicals not previously registered as pesticides, as well as pesticide active ingredients initially registered after November 1, 1984 and that currently have active product registrations. By law, these pesticides must meet new safety standards, such as those described in the Food Quality Protection Act of 1996 and, if new safety standards are met, will be reviewed again on a 15-year cycle. Triflumizole is designated by EPA as a New Pesticide Active Ingredient. Active Ingredient Number: 128879; Type of Pesticide: conventional - fungicide; Use Site: food use, ornamentals; Year: 1991.

Safety data

PPE
dust mask type N95 (US), Eyeshields, Gloves
wgk
3
rtecs
NI4490000
ridadr
UN 3077 9 / PGIII
hs_code
29332900
risk_code
22-51/53
Signal word
Warning
Symbol(GHS)
GHS07,GHS09
hazard_code
Xn,N
safety_code
61
Storage Class
6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
target organs
Liver
Hazard statements
H302-H411
Hazard Classifications
Acute Tox. 4 OralAquatic Acute 1Aquatic Chronic 1Repr. 1BSkin Sens. 1STOT RE 2
Precautionary statements
P273-P301+P312+P330
Hazardous Substances Data
68694-11-1(Hazardous Substances Data)

Uses & manufacturing

Uses · 5 items

Used as a fungicide for powdery mildew; [ACGIH]

For triflumizole (USEPA/OPP Pesticide Code: 128879) ACTIVE products with label matches. /SRP: Registered for use in the USA but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./

Triflumizole is a fungicide used for the control of powdery mildew, such as Sphaerotheca fuliginea, Sphaerotheca pannosa, Erysiphe cichoracearum and others.

Fungicide.

This is a man-made compound that is used as a pesticide.

Methods of ManufacturingTriflumizole is produced by reaction of 2-trifluoromethyl-4-chloropropoxyacetanilide with imidazole in the presence of phosphorous pentachloride.
Formulations/Preparations · 5 items

Procure 50WS (Macdermid Agricultural Solutions, Inc): Active ingredient: Triflumizole 50.0%.

Terraguard 50W (Macdermid Agricultural Solutions, Inc): Active ingredient: Triflumizole 50.0%.

A815 Technical (Macdermid Agricultural Solutions, Inc): Active ingredient: Triflumizole 97.0%.

Procure 50 WDG (Macdermid Agricultural Solutions, Inc): Active ingredient: Triflumizole 50.0%.

For more Formulations/Preparations (Complete) data for Triflumizole (14 total), please visit the HSDB record page.

Use Classification · 2 items

Environmental transformation -> Pesticides (parent, predecessor)

Fungicides

General Manufacturing InformationThe WHO Recommended Classification of Pesticides by Hazard identifies Bensulide (technical grade) as Class II: moderately hazardous; Main Use: fungicide, other than for seed treatment.

Applications

UsesTriflumizole is an conazole fungicide is an imidazole fungicide used on many food and ornamental crops.

Upstream & downstream products

Upstream raw materials

Amine compoundPropoxyacetic acidTriethylamineImidazolePhosgeneTriflumizole

Suppliers60 total

阿诺西(上海)生物技术有限公司400-1107768 15058188853 · [email protected]
湖北永阔科技有限公司027-59223108 15972152991 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
湖北万得化工有限公司15377098680 15377098680 · [email protected]
Qingdao Trust Agri Chemical Co.,Ltd+86-008615963231493 +86-008613573296305 · [email protected]
河北创海生物科技有限公司+86-86-13131129325 · [email protected]
Dayang Chem (Hangzhou) Co.,Ltd.+86-0571-88938639 17705817739 · [email protected]
深圳市思美泉生物科技有限公司17683743113;18038040196 · [email protected]
湖北魏氏化学试剂股份有限公司027-59102966 18717199209 · [email protected]
湖北广奥生物科技有限公司027-02702759223056 18162699093 · [email protected]
湖北成海化工有限公司027-59220433 18327245847 · [email protected]
四川库利南科技有限公司400-1166-196 18981987031 · [email protected]
ZHEJIANG JIUZHOU CHEM CO., LTD+86-0576225566889 +86-13454675544 · [email protected];[email protected];[email protected]
艾科试剂4008-755-333 18080918076 · [email protected]
武汉普洛夫生物科技有限公司17612776928 · [email protected]
南京生利德生物科技有限公司025-57798810 18652991625 · [email protected]
深圳菲斯生物科技有限公司0755-83725350 13380397412 · [email protected]
上海拓目化工有限公司13391076197 · [email protected]
湖北巨胜科技有限公司027-59599241 18871490274 · [email protected]
厦门志信化学有限公司+86-5922680277 +86-13806087780 · [email protected]
泰安嘉岳生物化工有限公司15318151873 · [email protected]
湖北世腾化工科技有限公司18971850150 19086915685 · [email protected]
湖北美钡新材料有限公司18271819653 · [email protected]
上海源叶生物科技有限公司18916372613 · [email protected]
湖北齐飞医药化工有限公司027-59322506 18071128681 · [email protected]
南京罗迈美生物科技有限公司[email protected]
湖北世腾化工科技有限公司19086915685 18971850150 · [email protected]
深圳市森迪生物科技有限公司18124570582 TEL:0755-23574479 2355327139 · [email protected]
武汉曙欧科技有限公司17792809151;18872220797 · [email protected]
武汉华玖医药科技有限公司027-59225746 18062681621 · [email protected]
武汉研哲科技有限公司15527250409 · [email protected]
上海臻励生物科技有限公司021-16621358918; 18516310516;16621358918;13045646768 · [email protected]
ATK CHEMICAL COMPANY LIMITED+undefined-21-51877795 · [email protected]
北京坛墨质检科技有限公司010-52889049 · [email protected]
深圳聚合生化科技有限公司+86-400-002-6226 13028896684 · [email protected]
Aladdin Scientific[email protected]
湖北摆渡化学有限公司027-59106051 13627137652 · [email protected]
湖北斯维图新材料科技有限公司13277095679 · [email protected]
湖北信康医药化工有限公司027-027-59308705 18871579363 · [email protected]
常州翔龙医药科技有限公司18661161657 · [email protected]
湖北拓邦化工有限公司027-59106185 13986192185 · [email protected]
济南光尘医药科技有限公司18563726319 · [email protected]
湖北麦凯斯精化科技有限责任公司13026126800 13026126800;13027176014 · [email protected]
如东众意化工有限公司13306234115 · [email protected]
北京勤诚亦信科技开发有限公司010-67787816; 13811243025 · [email protected]
SUZHOU SENFEIDA CHEMICAL CO.,LTD+86-0512-83500002 +86-15195660023 · [email protected]
南京枫景晴生物科技有限公司15062262630 · [email protected]
重庆卡兰医药有限公司[email protected]
黄石荆晟生物科技有限公司17771199833; 17771199833 · [email protected]
河北贞田食品添加剂有限公司0551-77777777-5 13333333333
Additional notes · 1 item

DefinitionChEBI: Triflumizole is a carboxamidine resulting from the formal condensation of the amino group of 4-chloro-2-(trifluoromethyl)aniline with the oxygen of the acetyl group of N-(propoxyacetyl)imidazole. A sterol demethylation inhibitor, it is used as a fungicide for the control of powdery mildew, scab and other diseases on a variety of crops. It has a role as an EC 1.14.13.70 (sterol 14alpha-demethylase) inhibitor and an antifungal agrochemical. It is a member of monochlorobenzenes, a member of imidazoles, a member of (trifluoromethyl)benzenes, a carboxamidine, an ether, a conazole fungicide and an imidazole fungicide.