141517-21-7

Basic information

• Product Name: Trifloxystrobin
• Synonyms: FLINT;TRIFLOXYSTROBIN;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);Methyl (2Z)-2-methoxyimino-2-[2-[[1-[3-(trifluoromethyl)phenyl]ethylideneamino]oxymethyl]phenyl]acetate
• CAS NO: 141517-21-7
• Molecular Formula: C₂₀H₁₉F₃N₂O₄
• Molecular Weight: 408.37
• Product Categories: Agro-Products;Aromatics;Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 141517-21-7.mol

Chemical Properties

• Melting Point: 72.9°
• Boiling Point: bp~312°
• Flash Point: >70 °C
• Appearance: /
• Density: 1.219 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.511
• Storage Temp.: 0-6°C
• CAS DataBase Reference: Trifloxystrobin(CAS DataBase Reference)
• NIST Chemistry Reference: Trifloxystrobin(141517-21-7)
• EPA Substance Registry System: Trifloxystrobin(141517-21-7)

Safety Data

• Hazard Codes: Xi,N
• Statements: 43-50/53
• Safety Statements: 24-37-46-60-61
• RIDADR: UN3077 9/PG 3
• WGK Germany: 2
• Hazardous Substances Data: 141517-21-7(Hazardous Substances Data)

Usage

References

[1] http://sitem.herts.ac.uk/aeru/iupac/Reports/664.htm [2] EPA Pesticide Fact Sheet

Chemical Properties

Off-White to Pale Beige Solid

Uses

Different sources of media describe the Uses of 141517-21-7 differently. You can refer to the following data:
1. Agricultural fungicide.
2. Trifloxystrobin is a broad-spectrum foliar fungicide used in plant pritection. Trifloxystrobin functions by inhibiting fungal spore germination.

Metabolism

Trifloxystrobin 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 evaluation

Trifloxystrobin 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.

InChI:InChI=1/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/h4-11H,12H2,1-3H3/b24-13+,25-18+

Upstream product

• 133409-72-0 methyl (E)-2-[2-(bromomethyl)phenyl]-2-(methoxyimino)acetate 
• 1462379-43-6 (E)-2-methoxyimino-2-(o-tolyl)acetic acid 
• 120974-97-2 methyl-(E)-2-(2-tolyl)-2-methoxyiminoacetate 
• 99705-50-7 1-[3-(trifluoromethyl)phenyl]ethanone oxime 
• 189813-45-4 (E)-methyl 2-(2-(chloromethyl)phenyl)-2-(methoxyimino)acetate 
• 4385-35-7 isochroman-3-one 
• 95-53-4 o-toluidine 
• 85589-34-0 2-hydroxy-2-(2-methylphenyl)acetonitrile 
• 529-20-4 2-methylphenyl aldehyde 

Relevant articles and documents

Synthesis of 8-substituted 5H,9H-6-oxa-7-azabenzocyclononene- 10,11- dione- 11-O-methyloximes, a new [1,2]-oxazonine ring system

Reaction of (2-bromomethyl-phenyl)-methoxyimino-acetic acid methyl ester 4 with oximes 1 in the presence of NaH/DMF yields 8-substituted 5H,9H-6-oxa- 7-aza-benzocyclononene-10,11-dione-11-O-methyloximes 3 together with the expected open chain compounds 2. Some spectroscopic data as well as synthetic and mechanistic aspects of the formation of the novel compounds 3 are discussed. (C) 2000 Elsevier Science Ltd.

Method for preparing trifloxystrobin by adopting microchannel reactor

The invention belongs to the technical field of organic synthesis, and particularly relates to a method for preparing trifloxystrobin by adopting a microchannel reactor. The method comprises the following steps: dissolving a raw material methyl (E)-2-(2-chloromethylphenyl)-2-methoxyiminoacetate or methyl (E)-2-(2-bromomethylphenyl)-2-methoxyiminoacetate and m-trifluoromethyl acetophenone oxime into a solvent; dissolving sodium methoxide in a solvent; and finally, pumping the two solutions into a micro-channel reactor for complete reaction to obtain a trifloxystrobin feed liquid, and carrying out elutriation and recrystallization to obtain the trifloxystrobin product,wherein the content of trifloxystrobin is 99% or above, and the yield of the step can reach 94% or above. The preparation method provided by the invention has the advantages of simple process operation, high product quality, high yield, less three wastes, small environmental pollution, continuous production, safety and the like, and is suitable for industrial production.

Preparation method of trifloxystrobin

The invention discloses a preparation method of trifloxystrobin. The method comprises the following steps: step 1, carrying out ultrasonic reaction on 3-trifluoromethylacetophenone oxime and (E)-2-(2'-bromomethyl phenyl)-2- carbonylacetic acid methyl ester -O-methylketone oxime in the presence of an acid-binding agent and an organic solvent; step 2, after finishing of the reaction, performing filtering to remove solids, performing washing with water, and carrying out reduced pressure distillation to remove a solvent to obtain a trifloxystrobin crude product; and step 3, recrystallizing a trifloxystrobin crude product with a low-polarity organic solvent, prforming filtering and drying to obtain a trifloxystrobin finished product. Compared with the traditional preparation method, the preparation method disclosed by the invention has the beneficial effects that firstly, an ultrasonic reaction instrument is adopted for reaction, and a low-boiling-point solvent is used for replacing a high-boiling-point reaction solvent, so that the production safety of the product is improved; secondly, the preparation method provided by the invention uses an ultrasonic reaction instrument for reaction, so that the reaction time is greatly shortened, the raw material conversion rate is high, the impurity content is obviously reduced; meanwhile, the production efficiency and the purity of the trifloxystrobin product are improved.

AN IMPROVED PROCESS FOR THE PREPARATION OF TRIFLOXYSTROBIN

The present invention relates to an improved process for the preparation of trifloxystrobin of formula (I), which is simple, economical, efficient, user and environment friendly, moreover commercially viable with higher yield and chemical purity.

Trifloxystrobin and preparation method of intermittent thereof

The invention relates to a preparation method of trifloxystrobin. Preparation reaction of the trifloxystrobin is as shown in the description, wherein R is selected from C2-C5 linear alkyl or C3-C5 branched alkyl; in bromination reaction, a brominating agent is selected from NBS or 1,3-dibromo-5,5-dimethylhydantoin.

A NOVEL PROCESS FOR THE PREPARATION OF TRIFLOXYSTROBIN

The present invention relates to a novel process for preparation of methyl (αE)-(α- (methoxyimino)-2-[[[(E)-[1-[3- (trifluoromethyl) phenyl] ethylidene] amino] oxy] methyl] benzeneaceate (Trifloxystrobin) compound of formula (I) in free form or in agro chemically acceptable salt form useful as a pest control agent.The present invention also relates to a novel process for preparation of methyl (2E)-[2-(bromomethyl) phenyl] (methoxyimino) ethanoate of formula (X) intermediate of Trifloxystrobin. [Formula should be inserted here].

Trifloxystrobin synthesizing method

The invention discloses a trifloxystrobin synthesizing method, and relates to the preparation of trifloxystrobin in organic chemicals. The trifloxystrobin synthesizing method comprises the following steps of using hydroxy methyl phenylacetic acid lactone as raw material to react with TBN (tributyrin), absolute methanol and sodium methoxide to obtain (E)-3-keto-4-(isonitroso)isochroman; using the (E)-3-keto-4-(isonitroso)isochroman to react with acetone and potassium carbonate, and dropwise adding the acetone solution of dimethyl sulfate after a large amount of bright yellow solids occurs, so as to obtain (E)-3-keto-4-(methoxyimino)isochroman; dissolving the obtained (E)-3-ketone-4-(methoxyimino)isochroman by methanol, and dropwise adding thionyl chloride under the low-temperature condition to prepare (E)-2-chlororated methyl-alpha-methoxyimino methyl phenylacetate; after the catalysis of 3-(trifluoromethyl)acetophenone and hydroxylamine hydrochloride, using absolute ethyl alcohol and as solvent to obtain light earthy yellow solid (E)-3-(trifluoromethyl)acetophenone oxime; enabling the (E)-2-bromomethyl-alpha-methoxyimino methyl phenylacetate and the (E)- 3-(trifluoromethyl)acetophenone oxime to react in a DMF (dimethyl formamide) solution of the potassium hydroxide, so as to obtain the white solid of trifloxystrobin.

AN IMPROVED PROCESS FOR THE SYNTHESIS OF STROBILURIN FUNGICIDES VIZ TRIFLOXYSTROBIN AND KRESOXIM-METHYL

The present invention relates to an improved process for the synthesis of E-isomer of compound of formula (5). It further relates to the conversion of formula (5), wherein R is H, to Intermediate (I) and subsequently to substantially pure Trifloxystrobin, compound of formula (I) in good yield.

Synergistic Active Compound Combinations Comprising Phenyltriazoles

The present invention relates to novel active compound combinations comprising, firstly, at least one known compound of the formula (I) in which R1 and R2 have the meanings given in the description. and at least one further known active compound from groups (2) to (27) listed in the description, which combinations are highly suitable for controlling animal pests such as insects and unwanted acarids and also phytopathogenic fungi.