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Trifloxystrobin

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CAS:141517-21-7
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Trifloxystrobin Basic information
Description References
Product Name:Trifloxystrobin
Synonyms:STRATEGO;TEGA;Benzeneacetic acid, .alpha.-(methoxyimino)-2-(E)-1-3-(trifluoromethyl)phenylethylideneaminooxymethyl-, methyl ester, (.alpha.E)-;methyl (e)-α-methoxyimino-2-[(e)-1-(3-trifluoromethylphenyl)ethylidenaminooxymethyl]phenylacetate;trifloxystrobin (bsi, pa iso);TRIFLOXYSTROBIN;Methyl (2Z)-2-methoxyimino-2-[2-[[1-[3-(trifluoromethyl)phenyl]ethylideneamino]oxymethyl]phenyl]acetate;alpha-(Methoxyimino)-2-[[[(E)-[1-[3-(trifluoromethyl)phenyl]ethylidene]amino]oxy]methylbenzene acetic acid, (E,E)-Methyl ester
CAS:141517-21-7
MF:C20H19F3N2O4
MW:408.37
EINECS:480-070-0
Product Categories:Agro-Products;Aromatics;Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals;OLED
Mol File:141517-21-7.mol
Trifloxystrobin Structure
Trifloxystrobin Chemical Properties
Melting point 72.9°
Boiling point bp~312°
density 1.21±0.1 g/cm3(Predicted)
Fp >70 °C
storage temp. Sealed in dry,2-8°C
solubility Chloroform: Slightly Soluble; Methanol: Slightly Soluble
form Solid
color White to off-white
Stability:Hygroscopic, Moisture Sensitive
Major Applicationagriculture
environmental
InChIInChI=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-
InChIKeyMGNJFZURPQVGJE-BWAHOGKJSA-N
SMILESC1(=CC=CC=C1CONC(=C)C1C=CC=C(C(F)(F)F)C=1)/C(=N/OC)/C(=O)OC
LogP5.112 (est)
EPA Substance Registry SystemTrifloxystrobin (141517-21-7)
Safety Information
Hazard Codes Xi,N
Risk Statements 43-50/53
Safety Statements 24-37-46-60-61
RIDADR UN3077 9/PG 3
WGK Germany 2
Storage Class11 - Combustible Solids
Hazard ClassificationsAquatic Acute 1
Aquatic Chronic 1
Lact.
Skin Sens. 1
Hazardous Substances Data141517-21-7(Hazardous Substances Data)
ToxicityLD50 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)
MSDS Information
Trifloxystrobin Usage And Synthesis
DescriptionTrifloxystrobin is a synthetic derivative of the naturally occurring strobilurins found in several genera of wood-decaying fungi such as Strobilurus tenacellus. It is a strobilurin foliar fungicide. Trifloxystrobin inhibits mitochondrial respiration by blocking electron transfer within the respirator chain. Therefore, trifloxystrobin is a potent inhibitor of 2 fungal spore germination and mycelial growth. It has a high level of activity against many fungal pathogens within the Ascomycete, Deuteromycete, Basidiomycete, and Oomycete classes.
Pests controlled by trifloxystrobin include grape and cucurbit powdery mildew, apple scab and powdery mildew, peanut leafspot, and brown patch of turfgrass. It could be applied to cereals, ornamental, vegetables (carrots, asparagus, cucurbits, fruiting vegetables, root vegetables (except radish)), fruits (apples, pears, grapes, strawberries) and tropical crops.
References[1] http://sitem.herts.ac.uk/aeru/iupac/Reports/664.htm
[2] EPA Pesticide Fact Sheet
Chemical PropertiesOff-White to Pale Beige Solid
UsesAgricultural fungicide.
UsesTrifloxystrobin is a broad-spectrum foliar fungicide used in plant pritection. Trifloxystrobin functions by inhibiting fungal spore germination.
DefinitionChEBI: 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 an oxime O-ether, an organofluorine compound, a methyl ester and a methoxyiminoacetate strobilurin antifungal agent.
Synthesis
3'-(TRIFLUOROMETHYL)ACETOPHENONE OXIME

99705-50-7

(E)-Methyl-2-(2-broMoMethylphenyl)-2-MethoxyiMinoacetate

133409-72-0

Triadimefon

43121-43-3

The general procedure for the synthesis of 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)butan-2-one from 3'-(trifluoromethyl)acetophenone oxime and (E)-2-(2-bromomethylphenyl)-2-methoxyiminoacetic acid methyl ester is as follows: Example 13: Synthesis of trioxamate 1. dissolve methyl (E)-2-(2-bromomethylphenyl)-2-methoxyiminoacetate (315 g, 1.10 mol) in 1500 ml of methyl isobutyl ketone. 2. To the above solution was added Intermediate-II (203.16 g, 1.0 mol) followed by potassium carbonate (145 g, 1.05 mol) at room temperature. 3. The reaction mixture was heated to 115°C and maintained for 12 hours. 4. After completion of the reaction, the mixture was cooled to room temperature and filtered to remove the potassium bromide by-products and excess potassium carbonate. 5. The solid from filtration is washed with methyl isobutyl ketone and can be recycled in the next batch for the preparation of trioxamate. 6. The filtrate was washed with water, dried over anhydrous sodium sulfate and subsequently concentrated under vacuum to give the crude product. 7. The crude product was recrystallized in methanol to give a white trioxamethyltriazine product weighing 348 g in 85% yield and >98% purity.

MetabolismTrifloxystrobin is described as “mesostemic” due to its ability to redistribute to untreated plant parts through vapor action, limited but effective cuticular penetration, and translaminarmovement by diffusion (30). It is rainfast by virtue of its high affinity for the waxy cuticular layer.
Toxicity evaluationTrifloxystrobin has an acute oral LD50 > 5,000 and an acute dermal LD50 > 2,000 mg/kg in rats. It is not a skin or eye irritant, is nonmutagenic and nonteratogenic. It shows rapid absorption and elimination in the rat. It has no toxicity to birds in acute studies (LD50 > 2,000 mg/kg) but has an LC50 of 0.015 mg/L in rainbow trout. The bee LD50 = 200 μg/bee. Environmental fate studies show it to be hydrolytically stable at pH 5, with a DT50 of 11.4 weeks at pH 7. It has a photolytic DT50 of 31.5 h at pH 7 (25 C) in water, a soil adsorption coefficient (Koc) of 1,642-3,745 ml/g, and a soil DT50 of 5.4 days under field conditions.
References[1] Patent: WO2017/85747, 2017, A2. Location in patent: Page/Page column 21
[2] Patent: WO2013/144924, 2013, A1. Location in patent: Page/Page column 33; 34
Trifloxystrobin Preparation Products And Raw materials
Raw materials3'-(TRIFLUOROMETHYL)ACETOPHENONE OXIME-->(E)-Methyl-2-(2-broMoMethylphenyl)-2-MethoxyiMinoacetate
Tag:Trifloxystrobin(141517-21-7) Related Product Information
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