Trifloxystrobin

408.37

408.37

604-237-6

DTXSID4032580

White powder

69.15000

5.11

1.21±0.1 g/cm3(Predicted)

72.9°

bp~312°

>70 °C

1.511

In water, 0.610 mg/L at 25 °C

0-6°C

2.55X10-8 mm Hg at 25 °C

LD50 in rats (mg/kg): >5000 orally; >2000 dermally; LC50 by inhalation in rats (mg/m3): >4646; LC50 in bobwhite quail (mg/kg): >2000; LC50 in rainbow trout (mg/l): 0.015 (Margot)

Odorless

pH = 7.7 at 25 °C

Henry's Law constant = 2.27X10-8 atm-cu m/mol at 25 °C (est)

Trifloxystrobin does not show any dissociation in the pH ranges 2 to 12.

Decomposition starting at 285 °C|Hydroxyl radical reaction rate constant = 7.04X10-12 cu cm/molecule sec at 25 °C (est)

UN30779/PG3

2

43-50/53

24-37-46-60-61

Xi,N

Stable under recommended storage conditions.

P273-P280-P501

H317-H410

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. Contact a licensed professional waste disposal service to dispose of this material; Contaminated packaging: Dispose of as unused product.|Wastes resulting from the use of this product may be disposed of on site or at an approved facility.

Incompatible materials: Strong oxidizing agents.|Does not contain any oxidizing or reducing substances. /Flint 50 WG and Compass 50 WG Stratego 250 EC/ /from table/

California Environmental Protection Agency/Department of Pesticide Regulation; Summary of Toxicology Data, Trifloxystrobin, Chemical Code No.5321 p.8 (May 17, 2000, last revised June 26, 2001)[Available from, as of December 20, 2016: http://www.cdpr.ca.gov/docs/risk/toxsums/toxsumlist.htm]|Health Canada, Pest Management Regulatory Agency; Regulatory Note- Trifloxystrobin REG2004-03 (January 30, 2004).

|Warning|H317: May cause an allergic skin reaction [Warning Sensitization, Skin]|P261, P272, P273, P280, P302+P352, P321, P333+P313, P363, P391, and P501|H317 (100%): May cause an allergic skin reaction [Warning Sensitization, Skin]|Aggregated GHS information provided by 134 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|P261, P271, P272, P273, P280, P302+P352, P304+P312, P304+P340, P312, P321, P333+P313, P363, P391, and P501|P260, P261, P264, P272, P280, P302+P352, P305+P351+P338, P314, P321, P333+P313, P337+P313, P363, and P501

Eye/face protection: Face shield and safety glasses. 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).|Protective clothing: Long-sleeved shirt and long pants. Shoes plus socks. Waterproof gloves.

Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.|Advice for firefighters: Wear self-contained breathing apparatus for firefighting 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.|If the container is leaking or material spilled for any reason or cause, carefully sweep material into a pile. ... Do not walk through spilled material. ... In spill or leak incidents, keep unauthorized people away.

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.|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 Trifloxystrobin (6 total), please visit the HSDB record page.

Causes moderate eye irritation.

Trifloxystrobin was present in effluents from 2 winery wastewater treatment plants in Bordeaux, France at concentrations of less than 0.02 ug/L and less than 0.004 ug/L(1).

SEDIMENT: Seasonal monitoring studies were conducted at 18 sites in southeastern Australia streams, sampling took place between September 2008 and March 2009(1,2). Trifloxystrobin was detected in sediment samples with an average detection frequency of 3%, a mean concentration of 3.2 ug/kg and a maximum of 8.0 ug/kg(1,2).|SOIL: Trifloxystrobin has been reported to occur in soil(1).

IDENTIFICATION AND USE: Trifloxystrobin is a white powder. It is used as agricultural fungicide. HUMAN EXPOSURE AND TOXICITY: Trifloxystrobin is harmful if absorbed through skin. Prolonged or frequently repeated skin contact may cause allergic reactions in some individuals. ANIMAL STUDIES: Trifloxystrobin was considered to be of low acute toxicity by the oral route in mice and rats, by the dermal route in rabbits, and by the inhalation route in rats. Trifloxystrobin was not selectively neurotoxic following acute gavage or subchronic dietary administration in rats. There were no treatment-related effects upon the mating, fertility, or litter size in rats. It was not mutagenic in S. typhimurium strains TA98, TA100, TA102, TA1535, or TA1357, or in E. coli strain WP2 uvrA with and without metabolic activation. ECOTOXICITY STUDIES: Trifloxystrobin is toxic to nontarget aquatic organisms. Trifloxystrobin could affect the activities of antioxidant enzymes, disrupt photosynthesis in Chlorella vulgaris, and damage cellular structure. Trifloxystrobin is highly toxic to fish embryos. It is very toxic to Daphnia magna and can cause harm to D. magna at environmentally relevant concentrations. Trifloxystrobin was very highly toxic to sheepshead minnows.

LD50 Rabbit dermal >2000 mg/kg|LD50 Rat oral >4000 mg/kg|LD50 Rat oral >5000 mg/kg|LD50 Rat dermal >2000 mg/kg

/AQUATIC SPECIES/ Contamination of aquatic systems is a major environmental stress that can interfere with predator-prey interactions, altering prey or predator behavior differentially. We determined toxicity parameters of the fungicide trifloxystrobin (TFS) and examined its effects on predation rate, using a fish predator (Synbranchus marmoratus) and four anuran tadpole species as prey (Rhinella arenarum, Physalaemus santafecinus, Leptodactylus latrans, and Elachistocleis bicolor). TFS was not equally toxic to the four tadpole species, E. bicolor being the most sensitive species, followed by P. santafecinus, R. arenarum, and L. latrans. Predation rates were evaluated using different treatments that combined predator and prey exposed or not to this fungicide. TFS would alter the outcome of eel-tadpole interaction by reducing prey movements; thus, prey detection would decrease and therefore tadpole survival would increase. In addition, eels preyed selectively upon non-exposed tadpoles avoiding the exposed ones almost all throughout the period evaluated. Predation rate differed among prey species; such differences were not due to TFS exposure, but to interspecific differences in behavior. The mechanism that would explain TFS-induced reduction in predation rates remains unclear; however, what is clear is that sublethal TFS concentrations have the potential to alter prey behavior, thereby indirectly altering predator-prey interactions. In addition, we consider that predator-prey relationships are measurable responses of toxicant exposure and provide ecological insight into how contaminants modify predator-prey interactions.|/AQUATIC SPECIES/ ... To investigate fungicide toxicity, Hyalella azteca amphipods were exposed to 2 fungicide formulations, Headline and Stratego, and their active strobilurin ingredients, pyraclostrobin and trifloxystrobin. Water-only exposures resulted in similar median lethal concentration (LC50; 20-25 ug/L) values for formulations and strobilurin ingredients, suggesting that toxicity is due to strobilurin ingredients. These values were below concentrations that could occur following spray drift over embedded cropland wetlands. When fungicides were added to overlying water of sediment-water microcosms, toxicity was reduced by 500% for Headline and 160% for Stratego, compared with water-only exposures, based on the total amount of fungicide added to the systems. In addition, when fungicides were added to sediment prior to the addition of water, the reduction in toxicity was even greater, with no toxicity occurring at environmentally relevant levels. Differences in toxicity among exposure groups were explained by dissipation from water as toxicity values based on measured water concentrations were within 20% between all systems. The present study reinforces previous studies that Headline and Stratego are toxic to nontarget aquatic organisms. However, the presence of sediment is likely to ameliorate some toxicity of fungicide formulations, especially if spraying occurs prior to wetland inundation.|/AQUATIC SPECIES/ ... In this study, the early life stage of grass carp (Ctenopharyngodon idella), which is one of the most important aquaculture species in China, was chosen to measure the acute toxicity of three common strobilurin-derived fungicides (trifloxystrobin (TFS), azoxystrobin (AZ) and kresoxim-methyl (KM)). As endpoints, normal developmental parameters (lethal concentration (LC50) and average heart rate), expression of relative genes, and three antioxidant enzyme activities in the developing juveniles were recorded during a 48 hr exposure. The results revealed that values of LC50 were TFS 0.051 (0.046-0.058) mg/L, AZ 0.549 (0.419-0.771) mg/L and KM 0.338 (0.284-0.407) mg/L for juveniles. For the potential toxicity mechanisms, these three fungicides increased catalase (CAT) and peroxidase (POD) activity and decreased superoxide dismutase (SOD) activity, significantly inhibited expressions of three growth-related genes (IGF-1, IGF-2 and GHR) and two energy-related-genes (CCK and PYY), and caused pronounced up-regulation a stress-gene (HSP70). The present study demonstrated potential toxic effects of TFS, AZ and KM on the early development of C. idella. Overall, three strobilurins (TFS, AZ and KM) might cause serious damages to the aquatic species; therefore, their pollution supervision in water ecological environment should be strengthened.|/AQUATIC SPECIES/ Trifloxystrobin is a systemic broad-spectrum foliar strobilurin fungicides that enters the aquatic environment during agricultural application. It is highly toxic and poses a potential risk to aquatic organisms ... . In this study, hatchability, time to hatching, and larval mortality were measured. Additionally, the expression of biomarker genes, including those involved in sex hormone pathways (er, vtg, cyp17, and cyp19a), thyroid hormone pathways (tr(alpha) and dio2), and aryl hydrocarbon receptor pathways (ahr and cyp1a), was determined after embryos of medaka (Oryzias latipes) were exposed to different levels of trifloxystrobin (0, 0.1, 1, 10, and 100 ug/L) for 28 days. The results showed that there were significant differences between controls and the 100 ug/L treatment group in both hatchability and time to hatching of fertilized eggs (p<0.05). Larval mortality was significantly increased in the 0.1, 1, and 10 ug/L treatment groups (p<0.05). These results indicate that embryonic and larval development may be affected by trifloxystrobin exposure. Moreover, the mRNA levels of the er gene were significantly up-regulated at levels of trifloxystrobin above 1 ug/L treatment groups. Up-regulation of vtg, cyp17, and cyp19a mRNA levels was observed in the larvae at the lower concentration treatment groups. The mRNA levels of cyp1a genes were significantly up-regulated at all of the treatment groups. These results suggest that trifloxystrobin is a potential endocrine disruptor through effects on the sex hormone pathway and xenobiotic metabolism. The changes in cyp1a expression can be used as a highly sensitive biomarker to assess trifloxystrobin contamination in the early life stages of fish.|For more Ecotoxicity Excerpts (Complete) data for Trifloxystrobin (13 total), please visit the HSDB record page.

Trifloxystrobin's production may result in its release to the environment through various waste streams; its use as an agricultural fungicide(1) will result in its direct release to the environment(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), Koc values of 351.5 to 6300(2,3), indicate that trifloxystrobin is expected to have moderate to no mobility in soil(SRC). Volatilization of trifloxystrobin from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.2X10-8 atm-cu m/mole(SRC), derived from its vapor pressure, 2.55X10-8 mm Hg(4), and water solubility, 6.1X10-1 mg/L(4). Trifloxystrobin is degraded in soil under certain environmental conditions via abiotic and biotic processes; reported environmental half-lives range from 1.8 to 5 days(3,5).|AQUATIC FATE: Based on a classification scheme(1), Koc values of 351.5 to 6300(2,3), indicate that trifloxystrobin may adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(4) based upon an estimated Henry's Law constant of 2.2X10-8 atm-cu m/mole(SRC), derived from its vapor pressure, 2.55X10-8 mm Hg(5), and water solubility, 6.1X10-1 mg/L(5). According to a classification scheme(6), a BCF of 540(7), suggests bioconcentration in aquatic organisms is high(SRC). Under certain environmental conditions trifloxystrobin is degraded in water via abiotic and biotic processes, reported environmental half-lives range from 1.8 to 5 days(3,8).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), trifloxystrobin, which has a vapor pressure of 2.55X10-8 mm Hg at 25 °C(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase trifloxystrobin may be removed from the air by wet and dry deposition(SRC). Trifloxystrobin contains chromophores that absorb at wavelengths >290 nm(3) and, therefore, may be susceptible to direct photolysis by sunlight(SRC).

The rate constant for the vapor-phase reaction of trifloxystrobin with photochemically-produced hydroxyl radicals has been estimated as 7.0X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 55 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). The bioactive isomer of trifloxystrobin (EE) can be converted into biologically inactive isomers in the environment by photolysis, in addition alkaline hydrolysis of trifloxystrobin results in the production of trifloxystrobin-acid which is also biologically inactive(2,3). The hydrolysis half-life at pH 7 and 20 °C, determined from guideline study OECD 111, is 80.1 days, the major product reported was the acid(2). Trifloxystrobin is susceptible to direct photolysis in water; photolysis half-lives determined from a guideline study at 25 °C, pH 5 and 7, are 20.4 and 31.5 hours (0.7 to 1.3 days), respectively(2,3).

A whole body BCF of 540 was reported for trifloxystrobin in bluegill fish (Lepomic macrochirus) exposed for 28 days, in the EPA bioconcentration guideline 165-4/OPPTS 950.1730 test(1). According to a classification scheme(2), this BCF suggests that bioconcentration in aquatic organisms is high(SRC).

Trifloxystrobin has reported values for log Koc = 3.8 (Koc = 6300) and log Koc = 3.5 (Koc = 2709)(1,2). Using US EPA guideline studies and soils from India and Germany (silty clay, clay, and sandy loam), desorption of trifloxystrobin ranged from 8.0 to 13.1%; Koc values ranged from 351.5 to 811.8(3). According to a classification scheme(4), these Koc values suggests that trifloxystrobin is expected to have moderate to no mobility in soil.

The Henry's Law constant for trifloxystrobin is estimated as 2.2X10-8 atm-cu m/mole(SRC) derived from its vapor pressure, 2.55X10-8 mm Hg(1), and water solubility, 6.1X10-1 mg/L(1). This Henry's Law constant indicates that trifloxystrobin is expected to be essentially nonvolatile from water surfaces(2). Trifloxystrobin's estimated Henry's Law constant indicates that volatilization from moist soil surfaces in not expected(SRC). Trifloxystrobin is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).

DRINKING WATER: Specific concentrations were not reported however, in a study published in 2006, the free form of the acid metabolite of zoxamide, CG-321113, was listed as a priority transformation product in Great British drinking water supplies as a result of zoxamide pesticide application(1).|SURFACE WATER: Trifloxystrobin has been reported to occur in water(1). Seasonal monitoring studies were conducted at 18 sites in southeastern Australia streams, sampling took place between September 2008 and March 2009(2). Trifloxystrobin was detected in water samples with an average detection frequency of 25%, a mean concentration of 0.08 ug/L and a maximum of 0.73 ug/L; the greatest detection frequency occurred in December (50%) while the lowest detection frequency occurred in February, March, and September (13%)(2,3).

Trifloxystrobin was detected in 1 out of 173 agricultural product samples from a local market in Japan at a concentration of 15.2 ng/g(1). Trifloxystrobin has been reported to occur in wheat, apple, cucumber, sugar beet, and other rotational crops up to 1 ug/kg, with an average between 81 to 115% remaining after 18 months of storage(2). In the United States in 1998, oranges treated with trifloxystrobin had residues of 0.04 to 0.20 mg/kg in the fruit samples 26 to 30 days after application; grapefruit had residues of 0.03 to 0.09 mg/kg in the fruit samples 30 to 36 days after application; lemons had residues of less than 0.02 to 0.15 mg/kg in the fruit samples 28 to 37 days after application; pome fruits (apples and pears) had residues of 0.03 to 0.37 mg/kg in the fruit samples 13 to 21 days after application; cherries had residues of 0.27 to 0.63 mg/kg in the fruit samples 1 to 2 days after application(2).|Residues of trifloxystrobin were detected at concentrations less than 0.10 ppm in commercial hop samples taken from Idaho, Oregon, and Washington in 2006 and 2007(1). In an FDA total diet study analyzing foods in 4 market basket studies from the fiscal year 2012, trifloxystrobin was detected in 9 of 159 food items considered to be infant and toddler foods at a range of 0.0001 to 0.0009 ppm and in 24 of 912 food items other than infant and toddler foods at a range of 0.0001 to 0.016 ppm(2). In an FDA total diet study analyzing foods in 4 market basket studies from the fiscal year 2013, trifloxystrobin was detected in 44 of 1,070 food items at a range of 0.0001 to 0.013 ppm(3).

Occupational exposure to trifloxystrobin may occur through inhalation and dermal contact with this compound at workplaces where trifloxystrobin is produced or used. Limited agriculture and turfgrass and ornamental applications of trifloxystribin may result in exposure of farm workers and landscapers, respectively(1). Limited monitoring data indicate that the general population may be exposed to trifloxystrobin via ingestion of food with residues of this chemical. (SRC)

Chemicals that kill or inhibit the growth of fungi in agricultural applications, on wood, plastics, or other materials, in swimming pools, etc. (See all compounds classified as Fungicides, Industrial.)

Male and female rats were dosed by gavage with either [Glyoxyl-Phenyl-(U)-(14)C] (spec. act. range: 54.3 to 63.5 uCi/mg, radiochemical purity range: >97 to >99%) or [Trifluormethyl-Phenyl-(U)-14C] /trifloxystrobin/ (CGA- 279202) (spec. act.: 59.2 uCi/mg, radiochemical purity: >99%). For all of the groups except D2, the animals were dosed with [Glyoxyl-Phenyl-(U)-(14)C]-/trifloxystrobin/ (CGA 279202). In Groups B1 and D1, urine and feces samples were collected up to 7 days from 5 animals/sex dosed with 0.5 or 100 mg/kg of the test material, respectively. For Group C1, 5 animals/sex were pretreated for 14 days with 0.5 mg/kg of unlabelled /trifloxystrobin/ (CGA 279202) (purity: 99.7%), followed by 0.5 mg/kg of the labelled test material. Urine and feces samples were likewise collected from these animals for up to 7 days. In Group D2, 5 animals/sex were dosed with 100 mg/kg of [Trifluormethyl-Phenyl-(U)-(14)C] /trifloxystrobin/ (CGA-279202) and urine and feces samples were collected up to 7 days. Twelve animals/sex were dosed with either 0.5 or 100 mg/kg of the test material in Groups F1 and 5 and Groups F2 and 6, respectively. Tissue residues were determined at 4 time points based upon pharmacokinetic determinations derived from the previous groups. The bile ducts of animals in Group G were cannulated. In Groups G1 and 3, 6 males and 5 females were treated with 0.5 mg/kg of the test material. Six males and 4 females were dosed with 100 mg/kg of the test material in Groups G2 and 4, respectively. At the low dose level, 56 to 65% of the dose was absorbed with 41 to 47% of the dose recovered from the bile. In the high dose group, 25 to 45% of the dose was absorbed with 19 to 35% of the dose recovered from the bile. In the low dose treatment, 18 to 19% and 79% of the dose was excreted in the urine and feces, respectively, of the males. For the females, 35 to 42% was excreted in the urine and 56 to 63% in the feces. Pretreatment with unlabelled test material did not alter the pattern of excretion. In the high dose groups, the males excreted 10 to 12% and 82 to 84% in the urine and feces, respectively. The females excreted 27% in the urine and 64 to 66% in the feces. Very minimal levels of radiolabel were recovered from the expired air of the animals in Group D2. The half lives for the depletion of radiolabel from the tissues ranged from 13 to 42 hours except for the spleen and blood of the high dose females (68 and 82 hours, respectively). The times to maximal concentration of the test material in the blood were either 12 to 24 hours after dosing. The times to maximal concentration ranged from 23 to 67 hours after dosing. Residual retention of the radiolabel in the carcass after 7 days was very minimal with 0.3 to 0.5% of the dose administered recovered.|Trifloxystrobin was moderately absorbed from the gastrointestinal tract and rapidly distributed. In the low-dose group, approximately 56% and 65% administered dose (AD) was absorbed in males and females respectively (based on the total recovery from urine, feces, bile and tissues), with 41 and 47% being in bile of males and females, respectively. In the high-dose, group, the degree of absorption was 41 and 27%, while the bile content was 35% and 19%, respectively for males and females. The blood kinetics revealed a moderate absorption rate in both sexes with two peaks (after 0.5 and 12 hours at the low dose and 12 and 24 hours at the high dose). The highest residues were found in blood, kidneys, spleen and liver and were comparable between sexes. Excretion of the radioactivity was rapid. Approximately 85-96% of the dose was excreted within 48 hours. The route of elimination was influenced by the sex of the animals, females eliminated twice the amount with the urine than males, accounting for 27-42% and 12-19% of the dose, respectively. The amounts excreted via feces were 79-82% and 56-64% of the dose in males and females, respectively. In both sexes biliary excretion was the major route of elimination. The involvement of an enterohepatic shunt mechanism in the elimination process is indicated.

In rats, the absorbed compound was rapidly cleared with extensive metabolism, particularly through hydrolysis of the ester group. Other significant metabolic routes were O-demethylation of the methoxyimino group and oxidation of the methyl side chain to the corresponding alcohol and carboxylic acid.|Male and female rats were dosed by gavage with either [Glyoxyl-Phenyl-(U)-14C] (radiochemical purity range: >97 to >99%) or [Trifluormethyl-Phenyl-(U)-14C]-/trifloxystrobin/ (CGA- 279202) (radiochemical purity: >99%). For all of the groups except D2, the animals were dosed with [Glyoxyl-Phenyl-(U)-14C]-/trifloxystrobin/ (CGA 279202). ...Thirty five metabolites were isolated and identified from the urine, feces and bile samples. Major metabolic pathways included 1) hydrolysis of the methyl ester to the corresponding acid, 2) O-demethylation of the methoxyimino group, and 3) oxidation of the methyl side chain to a primary alcohol, followed by further oxidation to the carboxylic acid. This last reaction was a more prominent metabolic pathway in the female rats with the resultant isolation of major sex-specific urinary metabolites. Cleavage of the glyoxyl-phenyl and trifluoromethyl-phenyl moieties accounted for 10% of the dose. For the trifluoromethyl phenyl fragment, oxidation of the hydroxyimino group led to the formation of a nitro compound and oxidation of the methyl group resulted in the formation of the carboxylic acid. In addition, hydrolysis of the imino group formed an intermediate ketone with succeeding reactions ultimately leading to trifluoromethyl benzoic acid. For the glyoxyl-phenyl moiety, oxidation resulted in the formation of a benzoic acid. O-demethylation of the methoxyimino group resulted in the hydroxyimino compound. Hydrolysis of the imino group yielded the a-keto acid followed by decarboxylation to the phthalic acid. Conjugates with glucuronide or sulfate were isolated from the bile. Four to 7% and 31 to 47% of the low and high doses, respectively, were eliminated in feces as the unmetabolized test material. The absorbed dose was predominantly isolated in the bile. Further processing returned the test material and/or metabolites to the intestinal tract and elimination in the feces or reuptake via the enterohepatic pathway.

The tissue half-lives /in rats/ ranged from 13 to 42 hours.

... The present study was performed in order to identify the skin toxicity mechanism of trifloxystrobin using HaCaT (keratinocyte of human skin) cells. Following 24 or 48 hr treatment, cell viability, and subsequent Annexin V-FITC/propidium iodide assay, TUNEL assay and Western blotting were performed to investigate the cell death mechanism of trifloxystrobin. Exposure to trifloxystrobin resulted in diminished viability of HaCaT cells in both a time- and concentration-dependent manner. The cell death was derived through apoptotic pathways in the HaCaT cells. Furthermore, we explored the effect of trifloxystrobin on TRAIL-mediated extrinsic apoptosis using siRNA transfection. Knockdown of death receptor 5 suppressed trifloxystrobin-provoked apoptosis. These results indicate that trifloxystrobin induces TRAIL-mediated apoptosis and has an inhibitory effect in keratinocytes that can interfere with the barrier function and integrity of the skin ...|Strobilurin fungicidal activity inhibits mitochondrial respiration by disrupting the cytochrome complex, thus blocking electron transfer. /Strobilurin fungicides/

Get medical aid. Eyes: Immediately rinse with plenty of running water. Skin: Flush with plenty of soap and water; remove contaminated clothing. Inhalation: Remove victim to fresh air. Apply artificial respiration if necessary.|Remove the patient from source of exposure. Provide supportive treatment directed to symptoms. Significant acute toxicity is not generally expected; therefore, exposure can be asymptomatic and symptoms usually do not warrant medical attention. Consider skin decontamination ... . Flush eyes with water or normal saline. If eye irritation, redness or swelling persists for more than 15 minutes, recommend consultation with an ophthalmologist. /Strobilurin fungicides/|/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/

/SIGNS AND SYMPTOMS/ Harmful if absorbed through skin. Prolonged or frequently repeated skin contact may cause allergic reactions in some individuals.|/SIGNS AND SYMPTOMS/ Significant acute toxicity is not generally expected; therefore, exposure can be asymptomatic and symptoms usually do not warrant medical attention. /Strobilurin fungicides/|/ALTERNATIVE and IN VITRO TESTS/ ... The present study was performed in order to identify the skin toxicity mechanism of trifloxystrobin using HaCaT (keratinocyte of human skin) cells. Following 24 or 48 hr treatment, cell viability, and subsequent Annexin V-FITC/propidium iodide assay, TUNEL assay and Western blotting were performed to investigate the cell death mechanism of trifloxystrobin. Exposure to trifloxystrobin resulted in diminished viability of HaCaT cells in both a time- and concentration-dependent manner. The cell death was derived through apoptotic pathways in the HaCaT cells. Furthermore, we explored the effect of trifloxystrobin on TRAIL-mediated extrinsic apoptosis using siRNA transfection. Knockdown of death receptor 5 suppressed trifloxystrobin-provoked apoptosis. These results indicate that trifloxystrobin induces TRAIL-mediated apoptosis and has an inhibitory effect in keratinocytes that can interfere with the barrier function and integrity of the skin ...|/ALTERNATIVE and IN VITRO TESTS/ ... In the present study, we investigated the impact of trifloxystrobin on exposed skin at the cellular organelle level using HaCaT, the human skin keratinocyte cell line. Cells were treated with trifloxystrobin for 48 hr and trifloxystrobin showed detrimental effects on mitochondria evidenced by altered mitochondrial membrane potential and morphology. To identify autophagic degradation of the damaged mitochondria, confocal imaging and Western blotting were performed. Trifloxystrobin induced autophagy-related proteins in HaCaT cells. The mitochondrial reactive oxygen species scavenger mitoTEMPO was applied to further explore the mechanism of trifloxystrobin-mediated mitophagy in human skin cells. PINK1 and Parkin were overexpressed by trifloxystrobin, and mitoTEMPO alleviated the effects on mitophagy induction. Taken together, our findings indicated that mitochondrial damage and mitophagy may play a role in trifloxystrobin-induced toxicity in human keratinocytes and this could be suggested as a mechanism of cutaneous diseases developed by exposure.

(E,E)-methoxyimino-(2-(1-(3-trifluoromethylphenyl)ethylideneaminooxymethyl)phenyl)acetic acid methyl ester

Trifloxystrobin Technical (Bayer Cropscience LP): Active ingredient: Trifloxystrobin 98.89%.|Flint Fungicide (Bayer Cropscience LP): Active ingredient: Trifloxystrobin 50.0%.|Stratego Fungicide (Bayer Cropscience LP): Active ingredient: Trifloxystrobin 11.4%; Propiconazole 11.4%.|Gem (Bayer Cropscience LP): Active ingredient: Trifloxystrobin 25.0%.|For more Formulations/Preparations (Complete) data for Trifloxystrobin (37 total), please visit the HSDB record page.

The WHO Recommended Classification of Pesticides by Hazard identifies Trifloxystrobin as unlikely to present an acute hazard in normal use; Main Use: fungicide, other than for seed treatment.

The Quinone outside Inhibitors (QoI) are one of the most important and recent fungicide groups used in viticulture and also allowed by Integrated Pest Management. Azoxystrobin, kresoxim-methyl and trifloxystrobin are the main active ingredients for treating downy and powdery mildews that can be present in grapes and wines. In this paper, a method is reported for the analysis of these three QoI-fungicides in grapes and wine. After liquid-liquid extraction and a clean-up on commercial silica cartridges, analysis was by isocratic HPLC with diode array detection (DAD) with a run time of 13 min. Confirmation was by solid-phase micro-extraction (SPME), followed by GC/MS determination. The main validation parameters for the three compounds in grapes and wine were a limit of detection up to 0.073 mg/kg, a precision not exceeding 10.0% and an average recovery of 93% +/- 38.|Analytical methods for the determination of trifloxystrobin and four of its metabolites were developed in a leaching study conducted in Hawaii. To duplicate plots at each of five locations representing various agricultural areas in Hawaii, trifloxystrobin was applied at label rates and allowed to leach under normal rain and irrigation conditions. Soil samples were collected at weekly to monthly intervals and the residual concentrations of trifloxystrobin and metabolites measured. A quantitative analytical method for their determination in various soil samples was developed using accelerated solvent extraction (ASE), coupled with liquid chromatography-tandem mass spectrometry. Extraction solvent with various ratios of methanol to water, addition of EDTANa2 to the extract solvent, and ASE cell temperature were adjusted to improve recovery. Deuterated (E, E)-trifloxystrobin was chosen as the internal standard of the analytical method. The limit of quantitation was 2.5 ppb in the soil for trifloxystrobin and its metabolites. Laboratory aerobic degradation studies with the soils from the five sites were also conducted to measure the same compounds.|An analytical method was developed for the determination of eleven agrochemicals [abamectin (as B1a), bifenazate, bifenthrin, carfentrazone-ethyl, cymoxanil, hexythiazox, imidacloprid, mefenoxam, pymetrozine, quinoxyfen, and trifloxystrobin] in dried hops. The method utilized polymeric and NH2 solid phase extraction (SPE) column cleanups and liquid chromatography with mass spectrometry (LC-MS/MS). Method validation and concurrent recoveries from untreated dried hops ranged from 71 to 126% for all compounds over three levels of fortification (0.10, 1.0, and 10.0 ppm). Commercially grown hop samples collected from several field sites had detectable residues of bifenazate, bifenthrin, hexythiazox, and quinoxyfen. The control sample used was free of contamination below the 0.050 ppm level for all agrochemicals of interest. The limit of quantitation and limit of detection for all compounds were 0.10 and 0.050 ppm, respectively.|The present study describes a new solvent-free method for the sensitive determination of seven strobilurin fungicides (azoxystrobin, metominostrobin, kresoxim-methyl, trifloxystrobin, picoxystrobin, dimoxystrobin and pyraclostrobin) in baby food samples. Direct immersion solid-phase microextraction (DI-SPME) coupled to gas chromatography with mass spectrometry in the selected ion monitoring mode, GC-MS (SIM), is used. All analyses were performed with 2 g of sample mass, 14 mL of sample extract volume and sample extract buffered at pH 5. Optimal extraction conditions were 60 degrees C for 40 min under continuous stirring using a Polydimethylsiloxane/Divinylbenzene (PDMS-DVB) fiber. Desorption was carried out at 240 degrees C for 4 min. The standard additions method is recommended and quantitation limits ranged from 0.01 to 0.4 ng/g at a signal to noise ratio of 10, depending on the compound. Recoveries obtained for spiked samples were satisfactory for all the compounds. The method was validated according to the Commission Decision 2002/657/EC. Different baby foods were analyzed by the proposed method and none of the samples contained residues above the detection limits.|For more Analytic Laboratory Methods (Complete) data for Trifloxystrobin (20 total), please visit the HSDB record page.

Agrochemicals -> Fungicides