Triflumizole
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Triflumizole
structure -
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CAS No:
68694-11-1
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Formula:
C15H15ClF3N3O
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Chemical Name:
Triflumizole
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Synonyms:
Benzenamine,4-chloro-N-[1-(1H-imidazol-1-yl)-2-propoxyethylidene]-2-(trifluoromethyl)-,[N(E)]-;1H-Imidazole,1-[1-[[4-chloro-2-(trifluoromethyl)phenyl]imino]-2-propoxyethyl]-,(E)-;1H-Imidazole,1-[(1E)-1-[[4-chloro-2-(trifluoromethyl)phenyl]imino]-2-propoxyethyl]-;[N(E)]-4-Chloro-N-[1-(1H-imidazol-1-yl)-2-propoxyethylidene]-2-(trifluoromethyl)benzenamine;Triflumizol;Triflumizole;Trifmine;NF 114;SSP 11;Procure;Condor;Trifumine;Trifumin;Terraguard;Procure (fungicide);99387-89-0;99403-07-3;121280-28-2;124282-24-2;128395-88-0;136169-57-8;1135441-23-4
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CAS No:
Description
COLOURLESS CRYSTALS.
COLOURLESS CRYSTALS.
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.
Triflumizole Basic Attributes
345.75
345.75
614-708-8
7J6Y4H9MV5
1252
3077
DTXSID2032500
Colorless crystals
2933290015
Characteristics
39.4
4.8 (calculated)
COLOURLESS CRYSTALS.
1.4 g/cm3
63 °C
No boiling point at normal pressure; decomposes at 150°C
208.6±31.5 °C
1.533
Solubility in water, mg/l at 20°C: 10.2 (practically insoluble )
0-6°C
Vapour pressure at 25°C: negligible
Oral-Rat LD50: 715 mg/kg; Oral-Mouse LD50: 510 mg/kg
Combustion produces toxic nitrogen oxides, chlorides and fluoride gases
Risk of fire and explosion if formulations contain flammable/explosive solvents.
Henry's Law constant = 6.2X10-8 atm-cu m/mol at 25 °C (est)
pKa = 3.70 at 25 °C
177.09 Ų [M+H]+
Hydroxyl radical reaction rate constant = 5.4X10-11 cu cm/mole-sec at 25 °C (est)
Safety Information
III
9
UN 3077 9 / PGIII
3
22-51/53
61
NI4490000
Xn,N
The warehouse is ventilated, low temperature and dry; stored and transported separately from food materials
Stable under recommended storage conditions.
P273
H302-H411
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.
Incompatible materials: Strong acids and strong bases.
Liquid formulations containing organic solvents may be flammable. Gives off irritating or toxic fumes (or gases) in a fire.
|Danger|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P201, P202, P260, P261, P264, P270, P272, P273, P280, P281, P301+P312, P302+P352, P308+P313, P314, P321, P330, P333+P313, P363, P391, P405, and P501|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|Aggregated GHS information provided by 135 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|Warning|P264, P270, P273, P301+P312, P330, P391, and P501
Eye/face protection: Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).|Skin protection: Handle with gloves.|Body Protection: Complete suit protecting against chemicals. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.|Respiratory protection: For nuisance exposures use type P95 (US) or type P1 (EU EN 143) particle respirator. For higher level protection use type OV/AG/P99 (US) or type ABEK-P2 (EU EN 143) respirator cartridges. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).|Chemical-resistant gloves. Long-sleeved shirt and long pants. Protective eyewear. Shoes plus socks.
Liquid formulations containing organic solvents may be flammable.
Risk of fire and explosion if formulations contain flammable/explosive solvents.
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.
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.
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.
Causes moderate eye irritation.
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.
Provision to contain effluent from fire extinguishing. Separated from food and feedstuffs. Well closed. Store in an area without drain or sewer access.
Evaporation at 20 °C is negligible; a harmful concentration of airborne particles can, however, be reached quickly on spraying or when dispersed, especially if powdered.
The substance is mildly irritating to the eyes.
Repeated or prolonged contact may cause skin sensitization. The substance may have effects on the liver. This may result in impaired functions. Animal tests show that this substance possibly causes toxicity to human reproduction or development.
STRICT HYGIENE!
Use ventilation.
Protective gloves.
Wear safety spectacles.
Toxicity
moderately toxic
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.
LD50 Rat oral 2230 mg/kg (Terraguard 50W)|LD50 Rat (male) oral 1057 mg/kg bw|LD50 Rat (female) oral 1780 mg/kg bw|LC50 Rat inhalation >3.6 mg/L/4 hr|For more Non-Human Toxicity Values (Complete) data for Triflumizole (6 total), please visit the HSDB record page.
/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. ...
Triflumizole's production may result in its release to the environment through various waste streams; its use as a fungicide(1) will result in its direct release to the environment(SRC).
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).
The rate constant for the vapor-phase reaction of triflumizole with photochemically-produced hydroxyl radicals has been estimated as 5.1X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 7 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Triflumizole is not expected to undergo rapid hydrolysis in the environment; experiments indicate that hydrolysis is pH dependent and triflumizole is most stable at neutral pH with a reported half-life of 101 days at pH 7(3). Abiotic degradation of radio-labeled triflumizole in water-sediments systems, using filtered pond water, sand, and clay loam, resulted in half-lives ranging from 48.7 to 123 days(3). Triflumizole contains chromophores that absorb at wavelengths >290 nm(4) and, therefore, may be 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).
BCF values of 699 and 1417 were measured in fish for triflumizole(SRC), using carp (Cyprinus carpio) which were exposed over 60 days in the OECD 305 test(1). A whole body BCF of 390 was reported for triflumizole in bluegill fish (Lepomic macrochirus) exposed for 28 days in the 165-4/OPPTS 950.1730 EPA bioconcetration test guideline(2). According to a classification scheme(3), these BCF values suggests that bioconcentration in aquatic organisms is high to very high(SRC).
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.
The Henry's Law constant for triflumizole is estimated as 6.2X10-8 atm-cu m/mole(SRC) derived from its vapor pressure, 2.55X10-8 mm Hg(1), and water solubility, 10.2 mg/L(1). This Henry's Law constant indicates that triflumizole is expected to be essentially nonvolatile from water surfaces(2). Triflumizole's estimated Henry's Law constant indicates that volatilization from moist soil surfaces in not expected(SRC). Triflumizole is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).
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).
Occupational exposure to triflumizole may occur through inhalation and dermal contact with this compound at workplaces where triflumizole is produced or used. Use data indicates that the general population may be exposed to triflumizole via ingestion of food with residues of this chemical, dermal contact with agriculture crops having residues of this chemical, and dermal contact with consumer products containing triflumizole. (SRC)
Drug Information
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/
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.
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).
/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/|/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/|/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W TKO /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/|Get medical aid. Eyes: Flush immediately with plenty of water. Skin: Wash thoroughly with soap and water. Remove contaminated clothing and shoes. Inhalation: Remove to fresh air.|For more Antidote and Emergency Treatment (Complete) data for Triflumizole (7 total), please visit the HSDB record page.
/SIGNS AND SYMPTOMS/ Harmful if swallowed. Harmful if absorbed through skin. Causes moderate eye irritation. ... Prolonged or frequently repeated skin contact may cause allergic reactions in some individuals.|/SURVEILLANCE/ A report on the results of its yearly health examination of the personnel involved in the production of triflumizole at the Takaoka plant (Japan) in the period May 1996 to May 2002 was prepared as a consequence of the Japanese "Occupational Safety and Health Law" and has been submitted to the regulatory authority. Commercial production of triflumizole started in 1985 at this plant. The health examination consisted of physical examination, hematology, urine analysis and blood chemistry. 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.|/OTHER TOXICITY INFORMATION/ 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.
1-(1-((4-chloro-2-(trifluoromethyl)phenyl)imino)-2-propoxyethyl)-1H-imidazole
The substance can be absorbed into the body by inhalation of dust and by ingestion.
Redness.
Triflumizole Use and Manufacturing
In the presence of PCl5, 4-chloro-α, α, α-trifluorotoluidine reacts with N-n-propoxyacetic acid to produce N-(n-propoxymethylformyl)-4-chloro-α, α , Α-Trifluorotoluidine, the resulting amide compound interacts with phosgene in the presence of triethylamine, and finally condenses with imidazole to synthesize fluconazole.
Triflumizole is an conazole fungicide is an imidazole fungicide used on many food and ornamental crops.
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.
The WHO Recommended Classification of Pesticides by Hazard identifies Bensulide (technical grade) as Class II: moderately hazardous; Main Use: fungicide, other than for seed treatment.
A procedure for high-performance liquid chromatographic (HPLC) determination of triflumizole and its metabolite (Met) in crops was examined. Triflumizole and Met in sample crops were extracted with methanol and re-extracted into methylene chloride. After clean-up of the extract on a Florisil column, triflumizole and Met were determined by HPLC with UV detection at 238 nm. The HPLC column was packed with Nucleosil 5 C18 (ODS, 5 micron) and the eluent was acetonitrile-3 mM carbonate buffer (7:3, v/v, pH 9.0). The detection limit was 0.01-0.02 ppm and the recoveries from spiked crops (0.5 ppm) were 73-99% for triflumizole and 74-94% for Met. Triflumizole and Met were determined simultaneously and the method was shown to be applicable to residue analysis of these compounds in crops sprayed with Trifmine in fields.|Triflumizole (TRI) and its metabolite [4-chloro-alpha,alpha,alpha-trifluoro-N-(1-amino-2-propoxythylidene)- O-toluidine] (MET) were extracted with methanol and reverse-extracted with dichloromethane. After evaporation to dryness, the residue in dichloromethane layer was dissolved in mobile phase for high performance liquid chromatographic determination with external standard method. ...|An alternative method has been developed to determine more than 50 pesticides in alcoholic beverages using hollow fibre liquid phase microextraction (HF-LPME) followed by ultra-high pressure liquid chromatography coupled to tandem mass spectrometry (UHPLC-MS/MS), without any further clean-up step. Pesticides were extracted from the sample to the organic solvent immobilized in the fibre and they were desorbed in methanol prior to chromatographic analysis. Experimental parameters related to microextraction such as type of organic solvent, extraction time and agitation rate have been optimized. The extraction method has been validated for several types of alcoholic beverages such as wine and beer, and no matrix effect was observed. The technique requires minimal sample handling and solvent consumption. Using optimum conditions, low detection limits (0.01-5.61 ug/L) and good linearity (R(2)>0.95) were obtained. Repeatability and interday precision ranged from 3.0 to 16.8% and from 5.9 to 21.2%, respectively. Finally the optimized method was applied to real samples and carbaryl, triadimenol, spyroxamine, epoxiconazole, triflumizol and fenazaquin were detected in some of the analyzed samples. The obtained results indicated that the new method can be successfully applied for extraction and determination of pesticides in alcoholic beverages, increasing sample throughput.
The purpose of this study was to confirm the presence of the metabolite FM-6-1 in rat feces and urine recovered during the main metabolism studies. Portions of the methanol fraction of 0- to 2-day urine and methanol extract of 0- to 2-day feces (~74 kBq) in each experimental group or sex of the high and low single-dose studies were combined and purified using silica gel column chromatography, fractioned according to the radioactive chromatograms and analyzed by TLC. The fraction corresponding to FM-6-1 was subjected to preparative TLC, and the radioactive band was extracted with acetone and then analyzed using gas chromatography-mass spectrometry (GC-MS) and compared with the FM-6-1 standard. The GC-MS results confirmed the presence of FM-6-1 in the urine and fecal sample.
Agrochemicals -> Fungicides|Fungicides|Environmental transformation -> Pesticides (parent, predecessor)
Triflumizole has known environmental transformation products that include FA1-1, FD1-1, FM5-1, and FM6-1.
Computed Properties
Molecular Weight:345.75
XLogP3:4
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:6
Exact Mass:345.0855743
Monoisotopic Mass:345.0855743
Topological Polar Surface Area:39.4
Heavy Atom Count:23
Complexity:406
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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