CS207766B2 - Method of making the methylester 3-/2,6-dichlor-4-trifluormethylphenoxy/-alpha-phenoxypropion acid - Google Patents

Method of making the methylester 3-/2,6-dichlor-4-trifluormethylphenoxy/-alpha-phenoxypropion acid Download PDF

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Publication number
CS207766B2
CS207766B2 CS794395A CS439579A CS207766B2 CS 207766 B2 CS207766 B2 CS 207766B2 CS 794395 A CS794395 A CS 794395A CS 439579 A CS439579 A CS 439579A CS 207766 B2 CS207766 B2 CS 207766B2
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CS
Czechoslovakia
Prior art keywords
alkoxy
alpha
optionally substituted
phenoxypropion
trifluormethylphenoxy
Prior art date
Application number
CS794395A
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Czech (cs)
Inventor
Heinz Foerster
Ludwig Eue
Robert R Schmidt
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Bayer Ag
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Publication date
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Publication of CS207766B2 publication Critical patent/CS207766B2/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
    • C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
    • C07D295/182—Radicals derived from carboxylic acids
    • C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N39/00—Biocides, pest repellants or attractants, or plant growth regulators containing aryloxy- or arylthio-aliphatic or cycloaliphatic compounds, containing the group or, e.g. phenoxyethylamine, phenylthio-acetonitrile, phenoxyacetone
    • A01N39/02—Aryloxy-carboxylic acids; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/257—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings
    • C07C43/295—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings containing hydroxy or O-metal groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40—Unsaturated compounds
    • C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
    • C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
    • C07C59/66—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings
    • C07C59/68—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings the oxygen atom of the ether group being bound to a non-condensed six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
    • C07D277/62—Benzothiazoles
    • C07D277/68—Benzothiazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
    • C07D277/82—Nitrogen atoms

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Dentistry (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Agronomy & Crop Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Thiazole And Isothizaole Compounds (AREA)

Abstract

1. Phenoxypropionic acid derivatives of the formula see diagramm : EP0003584,P20,F1 in which R represents hydroxyl, alkoxy which is optionally substituted by alkoxy, alkylthio, carbalkoxy, phenylmethylaminocarbonyl and/or halogen ; amino, hydrazino, alkylamino which is optionally substituted by alkoxy or dialkylamino, dialkylamino, alkenylamino, arylamino or N-aryl-N-alkylamino, it being possible for the aryl radical in each case to be substituted by alkyl, alkoxy, carbalkoxy, halogen and/or nitro, and furthermore represents a saturated heterocyclic ring with 5 or 6 ring members which is optionally substituted by alkyl and is bonded via nitrogen, or represents the radical of the formula see diagramm : EP0003584,P21,F2

Description

Způsob podle vynálezu ilustruje, avšak nikterak neomezuje následující příklad:The process of the present invention illustrates but does not limit the following example:

PříkladExample

Do roztoku 97 g (0,3 mol) 2,6-dichlor-4-trifluormethyl-3‘-hydroxydifenyletheru a 17,8 g methoxidu sodného ve 400 ml methanolu se při teplotě 45 až 50 °C přikape během 2 hodin 55,1 g methylesteru a-brompropionové kyseliny. Směs se ponechá dále míchat 3 hodiny při teplotě 45 až 50 °C a potom se zpracuje - tím, že se - reakční směs zahustí, zbytek se - vyjme 1 litrem methylenchloridu, roztok se- zfiltruje, potom se postupně - promyje vodným roztokem hydroxidu sodného a vodou a po vysušení se zahustí. Tímto způsobem se získá 59,0 g (64,4 % teorie) methylesteru 3- (2,6-dichloг-4-trifluormethyifenoxy)-a-fenoxypropionové kyseliny ve formě nahnědlého oleje (.nD2O=l,5206).To a solution of 97 g (0.3 mol) of 2,6-dichloro-4-trifluoromethyl-3'-hydroxydiphenyl ether and 17.8 g of sodium methoxide in 400 ml of methanol at 45-50 ° C is added dropwise 55.1 over 2 hours g of .alpha.-bromopropionic acid methyl ester. The mixture was allowed to stir for 3 hours at 45-50 ° C and then worked up by concentrating the reaction mixture, removing the residue with 1 liter of methylene chloride, filtering the solution, and then washing it successively with aqueous sodium hydroxide solution. and water, and, after drying, are concentrated. This gives 59.0 g (64.4% of theory) of 3- (2,6-4-dichloг trifluormethyifenoxy) -a-phenoxy-propionic acid as a brownish oil (.nD H2O = l, 5206).

Analýza pro C17H13CI2F3O4 vypočteno:Analysis for C17H13Cl2F3O4 calculated:

C 49,9 %, H 3,2 %, Cl 17,4 - %; nalezeno:C 49.9%, H 3.2%, Cl 17.4 -%; found:

C 49,6 °/o, H 3,6 O/o, Cl 16,8 %.C 49.6%, H 3.6%, Cl 16.8%.

2,6-Dichlor-4--г^fluoгmethyL·3‘-hydroxydifenylether nutný- jako- výchozí látka a·- odpo vídající vzorci2,6-Dichloro-4-γ-fluoromethyl · 3‘-hydroxydiphenyl ether required as starting material and · corresponding to the formula

ClCl

207786 se vyrobí následujícím způsobem:207786 is produced as follows:

Do směsi 330 g (3 mol) resorcinu a 111 g (1,5 mol) hydroxidu vápenatého ve 2 litrech dimethylsulfoxidu se při teplotě 120 až 130 stupňů Celsia přikape během 7 hodin 358 g (1,5 mol) 3,4,5-trichlorbenzotrichloridu. Potom se reakční směs dále míchá ještě 8 hodin při 130 °C. Po ochlazení na teplotu místnosti se reakční směs vylije do 7 litrů vody, přičemž se reakční produkt vyloučí ve formě oleje. Tento olej se extrahuje 3 litry toluenu, organická fáze se oddělí a po vysušení se zahustí. Získaný zbytek se destiluje.To a mixture of 330 g (3 mol) of resorcin and 111 g (1.5 mol) of calcium hydroxide in 2 liters of dimethylsulphoxide, 358 g (1.5 mol) of 3,4,5- trichlorobenzotrichloridu. The reaction mixture was then stirred at 130 ° C for a further 8 hours. After cooling to room temperature, the reaction mixture was poured into 7 L of water, whereupon the reaction product precipitated as an oil. This oil is extracted with 3 liters of toluene, the organic phase is separated off and, after drying, concentrated. The residue is distilled.

Tímto způsobem se získá 350 g (73 % teorie ) 2,6-dichlor-4-trifluomethyl-3‘-hydroxydifenyletheru ve formě pevné látky o teplotě tání 64 až 65 °C.350 g (73% of theory) of 2,6-dichloro-4-trifluoromethyl-3'-hydroxydiphenyl ether are obtained in the form of a solid, m.p. 64-65 ° C.

Teplota varu 123 až 130 °C/20 PaBoiling point 123-130 ° C / 20 Pa

Analýza pro C13H7CI2F3O2 vypočteno:Analysis for C 13 H 7 Cl 2 F 3 O 2 calculated:

C 48,3 %, H 2,2 %, Cl 22,0 %; nalezeno:C 48.3%, H 2.2%, Cl 22.0%; found:

C 48,3 °/o, H 2,3 θ/ο, Cl 21,8 %.C 48.3%, H 2.3%, Cl 21.8%.

Claims (1)

Způsob výroby methylesteru 3-(2,6-dichlor-4-trif luormethylf enoxy) -a-fenoxypropionové kyseliny vzorce I,A process for the preparation of 3- (2,6-dichloro-4-trifluoromethyl-phenoxy) -α-phenoxy-propionic acid methyl ester of the formula I, O-CH-COOCl·^O-CH-COOCl 4 PŘEDMĚT uvádí v reakci s methylesterem a-brompropionové kyseliny vzorce IIIThe object discloses in reaction with α-bromopropionic acid methyl ester of formula III Br—CH—COOCH3 (III) vyznačující se tím, že se difenylether vzorce IIBr - CH - COOCH 3 (III) characterized in that the diphenyl ether of formula II is used СНз v přítomnosti činidla, které váže kyselinu, a v přítomnosti ředidla.In the presence of an acid binding agent, and in the presence of a diluent.
CS794395A 1978-02-13 1979-02-13 Method of making the methylester 3-/2,6-dichlor-4-trifluormethylphenoxy/-alpha-phenoxypropion acid CS207766B2 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE19782805981 DE2805981A1 (en) 1978-02-13 1978-02-13 PHENOXYPROPIONIC ACID DERIVATIVES, PROCESS FOR THEIR PRODUCTION AND USE AS HERBICIDES

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CS207766B2 true CS207766B2 (en) 1981-08-31

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CS794395A CS207766B2 (en) 1978-02-13 1979-02-13 Method of making the methylester 3-/2,6-dichlor-4-trifluormethylphenoxy/-alpha-phenoxypropion acid
CS79965A CS207765B2 (en) 1978-02-13 1979-02-13 Herbicide means and method of making the activa component

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CS79965A CS207765B2 (en) 1978-02-13 1979-02-13 Herbicide means and method of making the activa component

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EP (1) EP0003584B1 (en)
JP (1) JPS54122239A (en)
AT (1) AT363713B (en)
BR (1) BR7900838A (en)
CS (2) CS207766B2 (en)
DD (1) DD141988A5 (en)
DE (2) DE2805981A1 (en)
DK (1) DK58379A (en)
HU (1) HU182927B (en)
IL (1) IL56634A (en)
PL (1) PL116325B1 (en)
TR (1) TR20653A (en)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2950401A1 (en) * 1979-12-14 1981-07-02 Bayer Ag, 5090 Leverkusen PHENOXYBENZOESIC DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS HERBICIDES AND PLANT GROWTH REGULATORS
US4599442A (en) * 1981-06-16 1986-07-08 Rhone-Poulenc, Inc. (Bisalkoxycarbonyl)alkyl 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoates
DE3319290A1 (en) * 1983-05-27 1984-11-29 Bayer Ag, 5090 Leverkusen OPTICALLY ACTIVE PHENOXYPROPIONIC ACID DERIVATIVES
EP0179015B1 (en) * 1984-09-17 1988-04-13 Schering Aktiengesellschaft 7-(aryloxy)-2-naphthoxyalkanecarboxylic acid derivatives, processes for the preparation of these compounds, as well as agents having herbicidal activity containing these compounds
DE3434447A1 (en) * 1984-09-17 1986-03-27 Schering AG, 1000 Berlin und 4709 Bergkamen 7-Aryloxy-2-naphthyloxyalkane carboxcylic acid derivatives, process for the preparation of these compounds and compositions having herbicidal action containing them
JPS62267275A (en) * 1986-05-16 1987-11-19 Aguro Kanesho Kk Propionic acid thiol ester derivative
FR2632618A1 (en) * 1988-06-08 1989-12-15 Commissariat Energie Atomique AIR CUSHION TRANSPORT DEVICE WITH MAGNETIC GUIDE
AR057455A1 (en) 2005-07-22 2007-12-05 Merck & Co Inc INHIBITORS OF HIV REVERSE TRANSCRIPTASE AND PHARMACEUTICAL COMPOSITION
CN114957166B (en) * 2022-05-26 2023-07-25 湖南省农业生物技术研究所 Phenylacetamide compound and preparation method and application thereof

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GB1563195A (en) * 1975-08-20 1980-03-19 Sori Soc Rech Ind Derivating of phenoxy-alkylcarboxylic acids
US4070178A (en) * 1975-09-03 1978-01-24 Rohm And Haas Company Herbicidal diphenyl ethers
NZ181994A (en) * 1975-09-27 1978-09-20 Ishihara Sangyo Kaisha (2-chloro-4-trifluorom-ethylphenoxy)-phenoxy acids,esters,ethers,amides and nitriles and herbicidal compositions
JPS5828262B2 (en) * 1976-03-17 1983-06-15 石原産業株式会社 Phenoxyphenoxyalkane carboxylic acid derivatives and herbicides containing them
GB1565972A (en) * 1976-04-15 1980-04-23 Sori Soc Rech Ind M-substituted phenoxypropionic acid dervatives
AU2716177A (en) * 1976-07-21 1979-01-25 Ciba Geigy Ag Herbicides
CH626318A5 (en) * 1977-03-08 1981-11-13 Ciba Geigy Ag

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DE2805981A1 (en) 1979-08-16
EP0003584B1 (en) 1981-01-21
EP0003584A1 (en) 1979-08-22
ATA102179A (en) 1981-01-15
CS207765B2 (en) 1981-08-31
DK58379A (en) 1979-08-14
BR7900838A (en) 1979-09-04
IL56634A (en) 1982-09-30
DE2960083D1 (en) 1981-03-12
HU182927B (en) 1984-03-28
PL213377A1 (en) 1980-03-24
AT363713B (en) 1981-08-25
TR20653A (en) 1982-03-25
IL56634A0 (en) 1979-05-31
DD141988A5 (en) 1980-06-04
JPS54122239A (en) 1979-09-21
PL116325B1 (en) 1981-06-30

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