CS262794B1 - 4- [2- (aryloxyacetyl) benzoyl] morpholines and processes for their preparation - Google Patents

4- [2- (aryloxyacetyl) benzoyl] morpholines and processes for their preparation Download PDF

Info

Publication number
CS262794B1
CS262794B1 CS877786A CS778687A CS262794B1 CS 262794 B1 CS262794 B1 CS 262794B1 CS 877786 A CS877786 A CS 877786A CS 778687 A CS778687 A CS 778687A CS 262794 B1 CS262794 B1 CS 262794B1
Authority
CS
Czechoslovakia
Prior art keywords
benzoyl
morpholine
aryloxyacetyl
morpholines
preparation
Prior art date
Application number
CS877786A
Other languages
Czech (cs)
Slovak (sk)
Other versions
CS778687A1 (en
Inventor
Margita Doc Rndr Csc Lacova
Stefan Rndr Csc Varkonda
Maria Rndr Csc Henselova
Ester Rndr Ticha
Vaclav Rndr Csc Konecny
Original Assignee
Lacova Margita
Varkonda Stefan
Henselova Maria
Ticha Ester
Konecny Vaclav
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Lacova Margita, Varkonda Stefan, Henselova Maria, Ticha Ester, Konecny Vaclav filed Critical Lacova Margita
Priority to CS877786A priority Critical patent/CS262794B1/en
Publication of CS778687A1 publication Critical patent/CS778687A1/en
Publication of CS262794B1 publication Critical patent/CS262794B1/en

Links

Landscapes

  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

Abstract

Riešenie sa zakladá na 4-[2-(aryloxyacetyl)benzoyl]morfo!línoch, v ktorých aryl je R-substituovaný fenyl, pričom R znamená vodík, metylovú skupinu, jeden alebo tri atómy chlóru a na spósobe ich přípravy pozostávajúcom z reakcie aryloxymetylénftalidov s morfolínom pri teplote 45 až 60 °C. Uvedené zlúčeniny sa vyznačujú auxinoidnou a fungicídnou účinnosťou.The solution is based on 4-[2-(aryloxyacetyl)benzoyl]morpholines, in which the aryl is R-substituted phenyl, where R means hydrogen, a methyl group, one or three chlorine atoms, and on a method of their preparation consisting of the reaction of aryloxymethylene phthalides with morpholine at a temperature of 45 to 60 °C. The mentioned compounds are characterized by auxinoid and fungicidal activity.

Description

Z derivátov 2-aryloxyacetylbenzoových kyselin sa herbicidnými a stimulačnými účinkami vyznačujú ich sodné soli (Lácová M., Koleková A., Hlásniková A.: Acta Fac. Rer. Nat. Univ. Gomenianae, v tlačij, estery (Lácová M., Varkonda S., Hýblová O., Konečný V.: čs. aut. osv. č. 236 406) a amidy (Lácová M., Synák J.: čs. aut. osv. č. 151 633.Among the 2-aryloxyacetylbenzoic acid derivatives, their sodium salts are characterized by herbicidal and stimulating effects (Lácová M., Koleková A., Hlásniková A .: Acta Fac. Rer. Nat. Univ. Gomenianae, in press, esters (Lácová M., Varkonda S ., Hýblová O., Konecný V .: Czechoslovak auto-enlightenment No. 236 406) and amides (Lácová M., Synák J .: Czechoslovak auto-enlightenment No. 151 633).

Teraz sa zistili 4-[ 2-(aryloxyacetyl Jbenzoyl]morfolíny všeobecného vzorca I4- [2- (Aryloxyacetyl) benzoyl] morpholines of the formula I have now been found

v ktorom R znamená vodík, metylovú skupinu, jeden alebo tri atomy chlóru.wherein R is hydrogen, methyl, one or three chlorine atoms.

Súčasne bol zistený spůsob přípravy zlúčenín všeobecného vzorca I reakciou aryloxymetylénftalidu s morfolinom, čo možnoAt the same time, a process for the preparation of compounds of the formula I by reacting aryloxymethylenephthalide with morpholine,

v ktorej substituent R má už uvedený význam.wherein R is as defined above.

U zláčenín pódia všeobecného vzorca boPREDMETFor podium compounds of the general formula boPREDMET

1. 4- [ 2- (aryloxyacetyl) benzoyl ] morf olíny všeobecného vzorca I li súčasne zistené auxinoidné účinky, napr. aktivita 4-(2-(3 metyl-4-chlórf enoxyacetyl)benzoyl J morf olinu dosahovala úroveň 87 až 93 % standardu (kys. 3-indolyloctovej). Fungicídna účinnost' bola pozitivna na Tilletia foetida a na Phytophtora infestans.1. 4- [2- (aryloxyacetyl) benzoyl] morpholines of the general formula (I) if the auxinoid effects observed simultaneously, e.g. the activity of 4- (2- (3-methyl-4-chlorophenoxyacetyl) benzoyl) morpholine reached a level of 87-93% of the standard (3-indolylacetic acid) The fungicidal activity was positive for Tilletia foetida and Phytophtora infestans.

Nasledujúce příklady ilustrujú ale neobmedzujú predmet vynálezu.The following examples illustrate but do not limit the invention.

Claims (2)

Spůsob přípravy 4-[2-(aryloxyacetyl)benzoyl Jmorfolínov Aryloxyrnetylénftalid (10 mmólov) a morfolín (25 cm3) sa mieša pri teplote cca 45 až 60' °C 1 h., potom sa nechá doreagovať pri teplote miestnosti 1 h. Morfolín sa oddestiluje a destilačný zvyšok sa prekryštalizuje z etanolu, acetonu alebo z octanu etylového. Podlá příkladu 1 holi připravené nasledujúce zlúčeniny:Preparation of 4- [2- (aryloxyacetyl) benzoyl] morpholines Aryloxymethylene phthalide (10 mmol) and morpholine (25 cm 3) are stirred at a temperature of about 45 to 60 ° C for 1 hour, then allowed to react at room temperature for 1 hour. The morpholine is distilled off and the residue is recrystallized from ethanol, acetone or ethyl acetate. The following compounds were prepared according to Example 1: 1. 4-(2-( 3-metyl-4-chlórfenoxyacetyl jbenzoyl] morfolín teplota topenia 154 až 156 °C. Analýza pre1. 4- (2- (3-methyl-4-chlorophenoxyacetyl) benzoyl] morpholine, m.p. 154-156 ° C. CieH2oClN04, M — 361,8; vypočítané 63,07 pere. C, 5,57 % H, 9,79 % Cl, 3,86 % N; zistené 63,24 %C, 5,80% H, 10,04% Cl, 3,59 % N;C 16 H 20 ClNO 4, M-361.8; calculated 63.07 pere. C, 5.57; H, 9.79; N, 3.86; found 63.24% C, 5.80% H, 10.04% Cl, 3.59% N; 2. 4-(2-( 2-metyl-4-chlórfenoxyacetyl) benzoyl] morfolín teplota topenia 149 až 153 °C. Analýza pre2. 4- (2- (2-methyl-4-chlorophenoxyacetyl) benzoyl] morpholine, m.p. 149-153 ° C. C19H20CINO4, M = 361,8: vypočítané 63,07 pere. C, 5,57 % H, 9,79 % Cl, 3,87 % N; zistené 63,11 % C, 5,42 % H, 9,96 % Cl, 4,07 0/0 N;C19H20ClNO4, M = 361.8: calculated 63.07 pen. C, 5.57; H, 9.79; N, 3.87; found 63.11% C, 5.42% H, 9.96% Cl, 4.07% N; 3. 4-[2-(2,4,5-trichlórf enoxyacetyl)benzoyl ] morfolín teplota topenia 175 až 178 °C. Analýza pře3. 4- [2- (2,4,5-Trichlorophenoxyacetyl) benzoyl] morpholine, m.p. 175-178 ° C. Analýza př C18H18CI3NO4, M = 418,7: vypočítané 51,63 pere. C, 4,33 % N, 25,40 % Cl, 3,34 % N; zistené 51,77 % C, 4,26 % H, 25,89 % Cl, 3,22 % N.C18H18Cl3NO4, M = 418.7: calculated 51.63 pen. C, 4.33; N, 25.40; N, 3.34; found: C 51.77, H 4.26, Cl 25.89, N 3.22. ynAlezu podlá bodu 1, vyznačujúci sa tým, že sa uvádza do reakcie slučenina vzorca II ωynAlez according to claim 1, characterized in that the compound of formula II ω is reacted v ktorom R znamená vodík, metylovú skupinu, jeden alebo tri atómy chlóru.wherein R is hydrogen, methyl, one or three chlorine atoms. 2. Spůsob přípravy 4-[2-(aryloxyacetyljbenzoyl jmorfolínov všeobecného vzorca I v ktorom R má zhora uvedený význam, s morfolinom, s výhodou pri teplote 45 až 60 stupňov Celzia.2. A process for the preparation of 4- [2- (aryloxyacetyl) benzoyl] morpholines of the general formula I in which R is as defined above, with morpholine, preferably at a temperature of 45 to 60 degrees Celsius.
CS877786A 1987-10-30 1987-10-30 4- [2- (aryloxyacetyl) benzoyl] morpholines and processes for their preparation CS262794B1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CS877786A CS262794B1 (en) 1987-10-30 1987-10-30 4- [2- (aryloxyacetyl) benzoyl] morpholines and processes for their preparation

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CS877786A CS262794B1 (en) 1987-10-30 1987-10-30 4- [2- (aryloxyacetyl) benzoyl] morpholines and processes for their preparation

Publications (2)

Publication Number Publication Date
CS778687A1 CS778687A1 (en) 1988-08-16
CS262794B1 true CS262794B1 (en) 1989-04-14

Family

ID=5427605

Family Applications (1)

Application Number Title Priority Date Filing Date
CS877786A CS262794B1 (en) 1987-10-30 1987-10-30 4- [2- (aryloxyacetyl) benzoyl] morpholines and processes for their preparation

Country Status (1)

Country Link
CS (1) CS262794B1 (en)

Also Published As

Publication number Publication date
CS778687A1 (en) 1988-08-16

Similar Documents

Publication Publication Date Title
SU888821A3 (en) Method of preparing 5-(substituted phehyl)-oxazolidinones or their sulphur-containing analogs
SU507234A3 (en) The method of obtaining 1,4-dihydropyridines or their salts
SU514569A3 (en) The method of producing pyridazine derivatives
EP0097821B1 (en) Dihydropyridines with an antagonistic activity to calcium, process for their preparation, and pharmaceutical compositions containing them
HU186539B (en) Process for producing 1-bracket-1-cyclohexenyl-methyl-bracket closed-2-bracket-2-chloroethyl-bracket closed-pyrrolidine
ES485073A1 (en) Pyridyl-substituted thiazolidine and 1,3-thiazine derivatives, processes for their preparation, agricultural compositions containing said derivatives and methods for regulating plant growth and protecting plants from fungi.
SU882409A3 (en) Method of preparing halogen-substituted mercaptoacylamino acids
CS262794B1 (en) 4- [2- (aryloxyacetyl) benzoyl] morpholines and processes for their preparation
US3006916A (en) W-dialkylaminoalkyl
NO166712B (en) PROCEDURE FOR THE PREPARATION OF PYRROLIDO DERIVATIVES.
KR920010926B1 (en) Process for preparing ranitidine and the salt thereof
SI8510847A8 (en) Process for preparation of 2-(n-benzyl-n-methylamino)-ethyl methyl 2,6-dimethyl-4-(m-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate and its hydrochloride salts
CA1164876A (en) Process for the preparation of cimetidine
KR890009879A (en) Method for preparing 5-amino-1-phenyl-4-nitropyrazole
US4119637A (en) 4-Hydroxymethyl-2-pyrrolidinones
US3060192A (en) Production of enantiomers of alphamethyl-phenethyl hydrazine and intermediate
US4483983A (en) Substituted derivatives of thiamorpholinone
US4958030A (en) Process for the preparation of 3-phenylpyrrole derivatives
GB2036723A (en) Mercaptoacylpiperazine carboxylic acid compounds
KR920000375B1 (en) Process for preparing substituted guanylthioureas
US5106846A (en) 2,3-thiomorpholinedione-2-oxime derivatives and pharmaceutical compositions containing them
US4952702A (en) Process for the preparation of (1,4-diaryl-pyrazol-3-yl)-acetic acids
EP0536512A1 (en) A method and intermediates for the preparation of 6-fluorobenzisothiazoles
ES8403124A1 (en) Process for the preparation of vincaminic acid esters
US2831863A (en) Di-(n-alkyl-3-piperidyloxy) alkanes and salts thereof