EP0000924B1 - Phényléthers hétérocycliques et leur procédé de préparation - Google Patents

Phényléthers hétérocycliques et leur procédé de préparation Download PDF

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Publication number
EP0000924B1
EP0000924B1 EP78100686A EP78100686A EP0000924B1 EP 0000924 B1 EP0000924 B1 EP 0000924B1 EP 78100686 A EP78100686 A EP 78100686A EP 78100686 A EP78100686 A EP 78100686A EP 0000924 B1 EP0000924 B1 EP 0000924B1
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EP
European Patent Office
Prior art keywords
methyl
compounds
formula
benzoxazol
benzimidazol
Prior art date
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Expired
Application number
EP78100686A
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German (de)
English (en)
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EP0000924A1 (fr
Inventor
Reinhard Dr. Handte
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Hoechst AG
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Hoechst AG
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Publication date
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
    • C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
    • C07D263/58—Benzoxazoles; Hydrogenated benzoxazoles 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles 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
    • C07D235/26—Oxygen atoms
    • 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

Definitions

  • n 0-2
  • R radicals from the group halogen, CF 3 , N0 2 , methyl, fluorine, chlorine being the haiogen and / or bromine is preferred.
  • A N-alkyl, N-methyl is preferred.
  • the compounds of formula II can be z. B. from the corresponding 2-mercapto or 2-oxo compounds by halogenation or else from the 2-amino compounds by diazotization and subsequent Sandmeyer reaction (see BCA 59, 396 j; Am. Chem. J. 21 [1899], 111
  • the compounds of formula IV can be prepared by the method (a) by using 2 moles or more of the compound 11 to 1 mole of the compound III.
  • reaction temperatures are between 80 ° and 250 ° C, preferably 90 ° to 150 ° C, optionally at the boiling point of the solvent used.
  • compound IV is increasingly formed as an undesirable by-product per se. However, this converts back to I above 80 ° with further III (see variant b)).
  • the reaction can also be carried out at temperatures above the boiling point in a closed vessel under autogenous pressure; this is necessary if the solvent used boils below 80 °.
  • Polar aprotic solvents e.g. B.
  • acid amides such as dimethylformamide, dimethylacetamide, diethylacetamide, N-methylpyrrolidone and hexamethylphosphoric triamide, also dimethyl sulfoxide; Nitriles such as acetonitrile or propionitrile, ketones such as acetone, methyl ethyl ketone or methyl isobutyl ketone. But aliphatic alcohols and aromatic hydrocarbons such as toluene or xylene can also be used.
  • the basic organic and inorganic bases such as, for. B. tertiary amines such as pyridine, triethylamine, alcoholates such as Na, K-methylate, ethylate, butylate, but especially inorganic bases such as potassium or sodium hydroxide or the corresponding carbonates. They are used at least in stoichiometric, but preferably at least equimolar amounts or an excess of 10-20% above. Larger excesses are possible, but offer no advantage and lead to an increased salt load.
  • tertiary amines such as pyridine, triethylamine, alcoholates such as Na, K-methylate, ethylate, butylate, but especially inorganic bases such as potassium or sodium hydroxide or the corresponding carbonates. They are used at least in stoichiometric, but preferably at least equimolar amounts or an excess of 10-20% above. Larger excesses are possible, but offer no advantage and lead to an increased salt load.
  • the molar ratio of the reactants II: III and IV: 111 can be varied within wide limits.
  • compound III can be used in a double molar amount or more, based on li.
  • Working with approximately equimolar amounts has the additional advantage that that the reaction products can be processed without further purification.
  • the preparation process (a) is generally carried out by first heating the compound of the formula III with the basic compound in a suitable solvent to the reaction temperature, at least partially forming the salt of the compound III. Then the compound of formula II, optionally dissolved in the same solvent, is added and the mixture is stirred at elevated temperature until the reaction has ended.
  • the salt (mono salt) of compound III can also be completely prepared first and reacted with II. It is also possible to add the reactants in a different order.
  • the required reaction time depends on the reaction temperature, the solvent and the ratio II: III and decreases with increasing temperature and increasing excess of 111. The reaction is usually complete after 30 minutes to 50 hours.
  • the production process (b) is carried out analogously to (a) by using a compound of the formula IV instead of a compound II, which in turn can be obtained from II and III.
  • the bases used here are used to prepare the salts of the compounds III, which in turn react with the bisethers of the formula IV to give the compounds (salts) of the formula 1.
  • the reaction mixture is acidified, the salt formed is filtered off and, if appropriate after washing with water, the solvent is distilled off.
  • excess III its removal is taken up in a water-immiscible solvent - for example in hot xylene - and washed several times with a little hot water, the organic phase is dried and the solvent is distilled off.
  • Other processing methods are described in the examples.
  • the compounds of formula I are precursors for effective biocides, e.g. B. for herbicides, in particular for those as proposed in the German patent application P 26 40 730.7.
  • valuable selective herbicides are obtained from the compounds of formula 1 by reaction with 2-halogenopropionic acid derivatives such as esters and amides in a manner known per se.
  • 2-halogenopropionic acid derivatives such as esters and amides
  • 2-halogenopropionic acid derivatives such as esters and amides
  • 2-halogenopropionic acid derivatives such as esters and amides
  • 2-halogenopropionic acid derivatives such as esters and amides
  • 2-halogenopropionic acid derivatives such as esters and amides
  • the salt content is filtered off and the filtrate is stirred into about 21 ice water.
  • the pH is adjusted to 2 with 10% sulfuric acid and the light precipitate is filtered off with suction, washed neutral with water and dried. After drying, it is taken up in hot xylene and washed several times with hot water to remove excess hydroquinone. Cooling the xylene phase and suctioning off the precipitate provides 106.8 g (81.7% of theory) of 4- (5'-chlorobenzoxazolyl-2'-oxy) phenol with an mp of 179.5 ° -181 ° C.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Thiazole And Isothizaole Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Claims (2)

1. Ethers phényliques hétérocycliques répondant à la formule I:
Figure imgb0019
dans laquelle:
les R représentent des radicaux identiques ou différents pris dans l'ensemble constitué par les halogènes, CF3, N02, CN, les alkyles en C1-C4 les alcoxy en C1-C4 et les alkylthio en C1-C4;
A représente O, S ou N-(C1-C4)alkyle et
n . est un nombre de 0 à 3,

avec la restriction que n ne peut pas être égal à lorsque A représente S.
2. Procédé de préparation de composés de formule I selon la revendication 1, procédé caractérisé en ce qu'on fait réagir:
a) des composés répondant à la formule II:
Figure imgb0020
dans laquelle Hal désigne un halogène, de préférence CI ou Br, ou
b) des composés de formule IV:
Figure imgb0021
avec des composés de formule III:
Figure imgb0022
en présence de composés basiques.
EP78100686A 1977-08-30 1978-08-17 Phényléthers hétérocycliques et leur procédé de préparation Expired EP0000924B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE2738963 1977-08-30
DE19772738963 DE2738963A1 (de) 1977-08-30 1977-08-30 Heterocyclische phenylaether und verfahren zu ihrer herstellung

Publications (2)

Publication Number Publication Date
EP0000924A1 EP0000924A1 (fr) 1979-03-07
EP0000924B1 true EP0000924B1 (fr) 1981-04-29

Family

ID=6017626

Family Applications (1)

Application Number Title Priority Date Filing Date
EP78100686A Expired EP0000924B1 (fr) 1977-08-30 1978-08-17 Phényléthers hétérocycliques et leur procédé de préparation

Country Status (6)

Country Link
US (1) US4263440A (fr)
EP (1) EP0000924B1 (fr)
JP (1) JPS5446783A (fr)
CA (1) CA1119604A (fr)
DE (2) DE2738963A1 (fr)
IT (1) IT1098396B (fr)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2738963A1 (de) * 1977-08-30 1979-03-15 Hoechst Ag Heterocyclische phenylaether und verfahren zu ihrer herstellung
US4221784A (en) * 1979-04-05 1980-09-09 Massachusetts Institute Of Technology Process and composition for treating disorders by administering lecithin
DE2914300A1 (de) * 1979-04-09 1980-11-13 Hoechst Ag Heterocyclische phenylether und diese enthaltende herbizide mittel
DE3311285A1 (de) * 1983-03-28 1984-10-11 Cassella Ag, 6000 Frankfurt Verfahren zur herstellung heterocyclischer phenylether
US4790868A (en) * 1986-03-17 1988-12-13 Ppg Industries, Inc. Herbicidally active substituted phenoxy or phenylthio benzoxazolone (or benzthiazolone) compounds
US4746351A (en) * 1986-05-12 1988-05-24 Ppg Industries, Inc. Herbicidally active substituted phenoxy benzoxazole (or benzothiazole)
US9629370B1 (en) * 2015-12-01 2017-04-25 Rotam Agrochem International Company Limited Synergistic herbicidal composition and use thereof
US9617247B1 (en) * 2015-12-01 2017-04-11 Rotam Agrochem International Company Limited Form of halosulfuron-methyl, a process for its preparation and use of the same

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2541003A (en) * 1948-08-17 1951-02-06 American Cyanamid Co Process for reacting salts of phenols with halo-alkanoic acid compounds
US3004034A (en) * 1959-12-30 1961-10-10 Monsanto Chemicals 2-(2-cyclohexenoxy)benzothiazole
US3658835A (en) * 1966-08-22 1972-04-25 Eastman Kodak Co 1-phenyl-5-aryloxytetrazoles
GB1372521A (en) * 1970-10-13 1974-10-30 Coalite Chemical Products Ltd Ethers
DE2640730C2 (de) * 1976-09-10 1983-08-25 Hoechst Ag, 6230 Frankfurt Benzoxazolyloxy- und Benzothiazolyloxy-phenoxy-Verbindungen und diese enthaltende herbizide Mittel
DE2738963A1 (de) * 1977-08-30 1979-03-15 Hoechst Ag Heterocyclische phenylaether und verfahren zu ihrer herstellung

Also Published As

Publication number Publication date
CA1119604A (fr) 1982-03-09
EP0000924A1 (fr) 1979-03-07
US4263440A (en) 1981-04-21
IT1098396B (it) 1985-09-07
DE2860652D1 (en) 1981-08-06
DE2738963A1 (de) 1979-03-15
JPS5446783A (en) 1979-04-12
IT7827077A0 (it) 1978-08-28

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