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트리프록시스토로빈

Trifloxystrobin

HCID 11664966
노트반응
기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
부분 구조 검색유사 구조 찾기

기본 정보

CAS
141517-21-7
표준 SMILES
CO/N=C(/C(=O)OC)c1ccccc1CO/N=C(\C)c1cccc(C(F)(F)F)c1
InChIKey
ONCZDRURRATYFI-TVJDWZFNSA-N
분자식
C20H19F3N2O4
평균 분자량
408.4 g/mol
단동위원소 질량
408.12969158

개요

Trifloxystrobin is the methyl ester of (2E)-(methoxyimino)[2-({[(E)-{1-[3-(trifluoromethyl)phenyl]ethylidene}amino]oxy}methyl)phenyl]acetic acid. A foliar applied fungicide for cereals which is particularly active against Ascomycetes, Deuteromycetes and Oomycetes. It has a role as a mitochondrial cytochrome-bc1 complex inhibitor and an antifungal agrochemical. It is a methyl ester, an oxime O-ether, an organofluorine compound and a methoxyiminoacetate strobilurin antifungal agent.

이름 및 식별자

우선 이름
Trifloxystrobin
IUPAC
methyl (2E)-2-methoxyimino-2-[2-[[(E)-1-[3-(trifluoromethyl)phenyl]ethylideneamino]oxymethyl]phenyl]acetate
현지명
트리프록시스토로빈
영어명
Trifloxystrobin
분자식
C20H19F3N2O4
분자량
408.37

이름 및 동의어

Trifloxystrobin141517-21-7TrifloxystrobineCGA 279202ConsistZatotrifloxy-strobinTWISTFlint (fungicide)methyl (2E)-2-methoxyimino-2-[2-[[(E)-1-[3-(trifluoromethyl)phenyl]ethylideneamino]oxymethyl]phenyl]acetateCHEBI:81833DTXSID4032580
이름 더 보기
트리프록시스토로빈TEGArifloxystrobinAprixSwiftDexterSTRATEGOoxystrobinTrifioxystrobin
Benzeneacetic acid, alpha-(methoxyimino)-2-[[[(E)-[1-[3-(trifluoromethyl)phenyl]ethylidene]amino]oxy]methyl]-, methyl ester, (alphaE)-methyl (2E)-2-(methoxyimino)-2-[2-({[(E)-{1-[3-(trifluoromethyl)phenyl]ethylidene}amino]oxy}methyl)phenyl]acetateCGA-279202(E,E)-methoxyimino-(2-(1-(3-trifluoromethylphenyl)ethylideneaminooxymethyl)phenyl)acetic acid methyl estermethyl (2E)-2-(methoxyimino)-2-(2-((((E)-(1-(3-(trifluoromethyl)phenyl)ethylidene)amino)oxy)methyl)phenyl)acetatemethyl (2E)-2-methoxyimino-2-(2-(((E)-1-(3-(trifluoromethyl)phenyl)ethylideneamino)oxymethyl)phenyl)acetateRefChem:905418DTXCID501509092

데이터베이스 식별자

CAS

물성

구조 계산 물성

XLogP
4.9
극성 표면적
69.5 Ų
수소 결합 공여자 수
0
수소 결합 수용자 수
9
회전 가능 결합 수
8
무거운 원자 수
29
형식 전하
0
복잡도
607

실험 및 물리화학적 성질

pHpH = 7.7 at 25 °C
Pesticides · 6건

Pesticides

Agrochemicals -> Pesticide active substances

Active substance -> EU Pesticides database: Approved

Pesticides -> Fungicides

Pesticide

Pesticide (Trifloxystrobin) -> USDA PDB

LogPlog Kow = 4.5 at 25 °C
OdorOdorless
Density1.36 g/mL at 21 °C
Color/FormWhite powder
Solubility · 2건

In water, 0.610 mg/L at 25 °C

In acetone, dichloromethane and ethyl acetate >500, hexane 11, methanol 76, octanol 18, toluene 500 (all in g/L, 25 °C)

Flash Point>70.00 °C (>158.00 °F)
Endocrine DisruptorsPotential endocrine disrupting compound
Boiling Pointapproximately 312 °C
Decomposition · 2건

안전 및 규제

안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.

GHS 분류

GHS Classification · 6건

Warning

H317: May cause an allergic skin reaction [Warning Sensitization, Skin]

P203, P260, P261, P263, P264, P270, P272, P273, P280, P302+P352, P318, P321, P333+P317, P362+P364, P391, and P501 (click each P-code to see the statement)

Warning

H317 (99.4%): May cause an allergic skin reaction [Warning Sensitization, Skin]

P203, P260, P261, P263, P264, P270, P272, P273, P280, P302+P352, P318, P321, P333+P317, P362+P364, P391, and P501 (click each P-code to see the statement)

유해성 정보

Regulatory Information · 4건

Regulation (EC) No 396/2005 (amended)

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

03/68/EC, Reg. (EU) 2016/950, Reg. (EU) 2017/841, Reg. (EU) 2018/1060, Reg. (EU) 2023/543, Reg. (EU) No 540/2011, Reg. (EU) No 823/2012

Trifloxystrobin: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

Hazards Summary · 1건

Not likely human carcinogen; Target organs after high-dose chronic feeding are liver and kidneys; Strong sensitizer in guinea pig testing; [Reference #1] May cause skin sensitization; [eChemPortal: ESIS] An irritant; May cause skin sensitization; [MSDSonline]

Special Reports · 2건

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).

FIFRA Requirements · 3건

화학 및 산업

약리 정보

Mechanism of Action · 2건

... 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/

Biological Half-LifeThe tissue half-lives /in rats/ ranged from 13 to 42 hours.
Metabolism/Metabolites · 3건

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.

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화합물 노트

불러오는 중…

이 페이지에서기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
141517-21-7
PubChem CID
11664966
DTXSID
DTXSID4032580
ChEBI
CHEBI:81833
EC Number
604-237-6
Nikkaji
J1.067.674F、J1.647.660I

Hazardous decomposition products formed under fire conditions - Carbon oxides, nitrogen oxides (NOx), hydrogen fluoride.

Decompn starting at 285 °C.

Melting Point72.9 °C

물리화학적 성질

녹는점
72.9 ° · 72.9°
끓는 점
312 ° · bp~312°
밀도
1.21 · 1.21±0.1 g/cm3(Predicted)
인화점
70 °C · >70 °C
저장 조건
2 · Sealed in dry,2-8°C
용해도
Chloroform: Slightly Soluble; Methanol: Slightly Soluble
물리적 상태
Solid
색상
White to off-white
Henry's Law Constant
4.3 · 4.3×102 mol/(m3Pa) at 25℃, MacBean (2012)
안정성
흡습성, 수분 민감성
주요 응용
농업환경
InChI
InChI=1S/C20H19F3N2O4/c1-13(14-8-6-9-16(11-14)20(21,22)23)24-29-12-15-7-4-5-10-17(15)18(25-28-3)19(26)27-2/h4-11,24H,1,12H2,2-3H3/b25-18-
InChIKey
MGNJFZURPQVGJE-BWAHOGKJSA-N
SMILES
C1(=CC=CC=C1CONC(=C)C1C=CC=C(C(F)(F)F)C=1)/C(=N/OC)/C(=O)OC
LogP
5.112 · 5.112 (est)
EPA
Trifloxystrobin (141517-21-7)

화학적 성질

Off-White to Pale Beige Solid

Tolerances are established for residues of trifloxystrobin, including its metabolites and degradates, in or on the commodities in the table below. Compliance with the tolerance levels specified below is to be determined by measuring only the sum of trifloxystrobin, benzeneacetic acid, (E,E)-a-(methoxyimino)-2-[[[[1-[3-(trifluoromethyl) phenyl]ethylidene] amino]oxy]methyl]-, methyl ester, and the free form of its acid metabolite CGA-321113, (E,E)-methoxyimino-[2-[1-(3-trifluoromethyl-phenyl)-ethylideneaminooxymethyl]-phenyl]acetic acid, calculated as the stoichiometric equivalent of trifloxystrobin, in or on the commodity.[Table#6884]

Timeline: Registration review decision and begin post-decision follow-up. Estimated Date: 2018.

Pesticide Fact Sheet: Name of Chemical: Trifloxystrobin; Reason for Issuance: New Chemical Registration, Date Issued: September 20, 1999.

Hazard Classes and Categories · 5건

Skin Sens. 1 (99.4%)

Reproductive toxicity - effects on or via lactation

Serious eye damage/eye irritation - Category 2A

Skin sensitization - Category 1B

Lact.

Skin, Eye, and Respiratory IrritationsCauses moderate eye irritation.
Hazardous Reactivities and Incompatibilities · 2건

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/

안전 및 보호

Fire Fighting Procedures · 2건

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.

Storage Conditions · 3건

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

Store in a cool, dry place and in such a manner as to prevent cross contamination with other pesticides, fertilizers, food, and feed. Store in original container and out of the reach of children, preferably in a locked storage area.

Store in a well-ventilated, secure area out of reach of children and domestic animals. Do not eat, drink, smoke, or apply cosmetics; wash thoroughly after handling.

Cleanup Methods · 2건

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.

Disposal Methods · 3건

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.

Preventive Measures · 5건

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.

Allowable Tolerances · 1건

Tolerances are established for residues of trifloxystrobin, including its metabolites and degradates, in or on the commodities in the table below. Compliance with the tolerance levels specified below is to be determined by measuring only the sum of trifloxystrobin, benzeneacetic acid, (E,E)-a-(methoxyimino)-2-[[[[1-[3-(trifluoromethyl) phenyl]ethylidene] amino]oxy]methyl]-, methyl ester, and the free form of its acid metabolite CGA-321113, (E,E)-methoxyimino-[2-[1-(3-trifluoromethyl-phenyl)-ethylideneaminooxymethyl]-phenyl]acetic acid, calculated as the stoichiometric equivalent of trifloxystrobin, in or on the commodity.[Table#6883]

Personal Protective Equipment (PPE) · 5건

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.

독성 정보

Health EffectsExposure to Trifloxystrobin might cause hepatocellular hypertrophy.
Ecotoxicity Values · 5건

LD50; Species: Colinus virginianus (Bobwhite quail) oral >2000 mg/kg

LD50; Species: Anas platyrhynchos (Mallard duck) oral >2250 mg/kg

LD50; Species: Apis mellifera (Honey Bee) adult; topical, general >200 ug/bee[USEPA, Office of Pesticide Programs; Pesticide Ecotoxicity Database (2000) on alpha-(Methoxyimino)-2-[[[(E)-[1-

LC50; Species: Lepomis macrochirus (Bluegill sunfish) weight 0.51 g; Conditions: freshwater, flow through; Concentration: 54 ppb for 96 hr (95% confidence interval: 48-61 ppb) /96.4% purity/[USEPA, Office of Pesticide Programs; Pesticide Ecotoxicity Database (2000) on alpha-(Methoxyimino)-2-[[[(E)-[1-

For more Ecotoxicity Values (Complete) data for Trifloxystrobin (18 total), please visit the HSDB record page.

Environmental Fate · 3건

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).

Food Survey Values · 2건

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).

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 RoutesOccupational exposure to trifloxystrobin may occur through inhalation and dermal contact with this compound at workplaces where trifloxystrobin is produced or used.
Toxicity Summary · 1건

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.

Ecotoxicity Excerpts · 5건

/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.

Animal ConcentrationsTrifloxystrobin has been detected in hen, goat, and rat(1).
Ongoing Test Status · 1건

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/]

Effluent ConcentrationsTrifloxystrobin 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).
Soil Adsorption/Mobility · 1건

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.

규제 정보

FIFRA Requirements · 3건

Tolerances are established for residues of trifloxystrobin, including its metabolites and degradates, in or on the commodities in the table below. Compliance with the tolerance levels specified below is to be determined by measuring only the sum of trifloxystrobin, benzeneacetic acid, (E,E)-a-(methoxyimino)-2-[[[[1-[3-(trifluoromethyl) phenyl]ethylidene] amino]oxy]methyl]-, methyl ester, and the free form of its acid metabolite CGA-321113, (E,E)-methoxyimino-[2-[1-(3-trifluoromethyl-phenyl)-ethylideneaminooxymethyl]-phenyl]acetic acid, calculated as the stoichiometric equivalent of trifloxystrobin, in or on the commodity.[Table#6884]

Timeline: Registration review decision and begin post-decision follow-up. Estimated Date: 2018.

Pesticide Fact Sheet: Name of Chemical: Trifloxystrobin; Reason for Issuance: New Chemical Registration, Date Issued: September 20, 1999.

안전 데이터

wgk
2
ridadr
UN3077 9/PG 3
독성
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)
risk_code
43-50/53
hazard_code
Xi,N
safety_code
24-37-46-60-61
Hazard Classifications
Aquatic Acute 1Aquatic Chronic 1Lact.Skin Sens. 1
스토리지 클래스
11 - Combustible Solids
유해 물질 데이터
141517-21-7(Hazardous Substances Data)

Major metabolic pathways of trifloxystrobin included 1) hydrolysis of the methyl ester to he 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. Metabolites are excreted in the feces.

MeSH Pharmacological ClassificationChemicals that kill or inhibit the growth of fungi in agricultural applications, on wood, plastics, or other materials, in swimming pools, etc.
Absorption, Distribution and Excretion · 2건

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.

용도 및 제조

Uses · 5건

Used as broad-spectrum fungicide for cereals, fruits, vegetables, and ornamentals; [HSDB]

Farming (Pesticides) [Category: Industry]

For trifloxystrobin (USEPA/OPP Pesticide Code: 129112) ACTIVE products with label matches. /SRP: Registered for use in the U.S. but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./

Fungicide, seed treatment/protectant

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

Methods of ManufacturingPreparation: J.M. Clough et al., European Patent Office patent 472300; eidem, United States of America patent 5238956 (1992, 1993 both to ICI).
Formulations/Preparations · 5건

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.

General Manufacturing InformationThe 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.

응용 분야

용도Trifloxystrobin is a broad-spectrum foliar fungicide used in plant pritection. Trifloxystrobin functions by inhibiting fungal spore germination.

상·하류 제품 정보

상류 원료

3'-(트리플루오로메틸)아세토페논옥심(E)-Methyl-2-(2-broMoMethylphenyl)-2-MethoxyiMinoacetate

공급사100 곳

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/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.