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
  • C07D263/56—Benzoxazoles; Hydrogenated benzoxazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
  • C07D263/57—Aryl or substituted aryl radicals
• • 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
  • C07D263/60—Naphthoxazoles; Hydrogenated naphthoxazoles
• • D—TEXTILES; PAPER
  • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
  • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
  • D06M16/00—Biochemical treatment of fibres, threads, yarns, fabrics, or fibrous goods made from such materials, e.g. enzymatic

Definitions

• the present invention provides a method for combating harmful microorganisms, which comprises applying to a desired site an effective amount of a 2-(2'-hydroxyphenyl)- oxazole of the formula N i R CX or an alkali metal salt thereof, where R is an aromatic ring system containing at most 2 six-membered rings, which is fused on as indicated by the valency lines, and X represents a benzene residue substituted by a hydroxyl group in ortho-position relatively to the bond with the oxazole ring.
• 2-(2'-hydroxypheny1)-oxazoles of the formula in which R has the above meaning, Me is a hydrogen or alkali metal atom, and at least one of the symbols X and X represents a halogen atom, an amino group or an alkyl group containing up to 4 carbon atoms and the other is a hydrogen or halogen atom or an alkyl group with up to 4 carbon atoms.
• the present invention is specially concerned with a method for combating harmful microin which Me has the above meaning; at least one of the symbols X and X stands for a halogen atom or an alkyl group with up to 4 carbon atoms and the other for a hydrogen or halogen atom or for an alkyl group with up to 4 carbon atoms, and one to four of the symbols R to R represent hydrogen or halogen atoms and two of these symbols, not standing for hydrogen or halogen atoms, represent phenyl, alkyl, alkoxy, phenylalkyl, cyclohexyl, nitro, primary amino, alkylamino, acylamino, trihalomethyl, aminosulphonyl, methylaminosulphony groups or sulphonic acid groups (possibly in the form of their alkali metal salts); or two vicinal symbols R to R together form the complement to a fused-on carbocycle, which is preferably unsubstituted, and any alkyl
• R to R may be chosen independently of one another, that is to say for instance that one and the same molecule may contain 1 to 4 halogen atoms side by side with 0 to 3 hydrogen atoms and 0 to 2, preferably 0 to 1, of the other substituents of the kinds indicated above.
• Preferred compounds are the 2-(2-hydroxyphenyl)- benzoxazoles of the formula in which one or both of the symbols R and R are hydrogen, chlorine or bromine atoms, methyl, methoxy or nitro groups and, when one of these symbols does not satisfy this definition, it stands for a phenyl, cyclohexyl group or a phenylalkyl group containing up to 9 carbon atoms; R represents a hydrogen or halogen atom; X a hydrogen, chlorine or bromine atom or a methyl group and X a chlorine or bromine atom.
• R is a hydrogen, chlorine or bromine atom, a methyl, phenyl or cyclohexyl group
• R R X and X have the above meaningsare preferred because of their good antimicrobial activity.
• Extremely satisfactory results in combating microorganisms have been obtained with 2-(2'-hydroxyphenyl)benzoxazoles of the formula N HO Xa 53' where R and R each is a hydrogen, chlorine or bror mine atom or a methyl group, and R X and X have the above meanings.
• the following compounds may be mentioned, for example:
• the 2-(2-hydroxyphenyl)-oxazoles of the Formula 1 can be prepared by known methods by cyclizing an orthohydroxyamino compound of the formula where R has the above meaningwith a functional derivative of a 2-hydroxybenzene-l-carboxylic acid (HOOC-X) and, if desired, introducing further substituents, for example halogen atoms or sulphonic acid groups, into the resulting oxazole compound and/or converting it into an alkali metal salt thereof.
• HOOC-X 2-hydroxybenzene-l-carboxylic acid
• the present invention includes also the use of the 2-(2'- hydroxyphenyl)-oxazoles in pest control quite generally.
• the antimicrobial compounds may be used on a very broad basis, especially for protecting organic substrates from infestation by destructive and pathogenic (including phytopathogenic) microorganisms. Accordingly, the aforementioned compounds may be used as preservatives or disinfectants for textile materials and other industrial products of many kinds, in plant protection, agriculture, veterinary medicine and cosmetics.
• the oxazoles may be used for producing preserving and disinfecting finishes on fibres and textile materials, including both natural and synthetic fibres on which they produce a durable protection against harmful (including pathogenic) microorganisms, for example fungi and bacteria.
• the compounds may be added before, during or after a treatment of such textile materials with other substances, for example dyeing or printing pastes, dressing agents etc.
• Textile materials treated in this manner are also protected against body odour (perspiration) caused by microorganisms.
• the oxazoles may also be used as preservatives in the cellulose and paper industry, inter alia for preventing the known slime formation in paper-making machines due to microorganisms.
• the oxazoles when the oxazoles are combined with surface-active, especially detergent, substances, there are ob tained detergents and cleansing agents having a excellent antibacterial or antimycotic effect.
• the compounds of the Formulae 1 to 11 can be incorporated, for example, with soaps, or combined with soap-free detergents or surfaceactive substances or they may be combined with mixtures of soaps and soap-free detergents, and their antimicrobial activity is fully maintained in such combinations.
• Cleansing preparations containing compounds of the formulae shown above may also be used in industry and the home, in the food industry, for example in dairies, breweries or abattoirs. They may also be used as ingred- 'ients of preparations used for cleansing or disinfecting hospitals or surgeries.
• the effect of the oxazoles can also be utilized in pro vinding plastic materials with a preserving and disinfecting finish.
• plasticizers When plasticizers are used it is advantageous to dissolve or disperse the antimicrobial compound in the plasticizer and then to incorporate it with the plastic material. It is advantageous to ensure that the additive is as evenly as possible distributed in the plastic material.
• Plastic materials having antimicrobial properties can be used for making utilitarian articles of all kinds in which an activity against a wide variety of germs, for example bacteria and fungi, is desirable, for example in doormats, bathroom curtains, seats, treads in swimming baths, wall coverings or the like. By incorporation with waxes and polishing compositions, floor and furniture polishes are obtained that have a disinfecting activity.
• the antimicrobially active substances can be applied to the textile materials to be protected in a variety of ways, for example by impregnating or spraying with solutions or suspensions containing the above-mentioned compounds as active ingredients. Depending on the individual use, the content of active substance may vary from 1 to 30 g. per litre of treatment liquor.
• the form in which the active substances of this invention are applied may be similar to the conventional formulations of pesticidal preparations; for example, prepara tions containing the said active substances may, if desired, further contain additives such as vehicles, solvents, diluents, dispersants, wetting agents, adhesives or the like and also other pesticides.
• a mixture of 4.05 parts of the dimethylamine salt and 20 parts by volume of 2 N sodium hydroxide solution is heated for 15 minutes on a water bath, during which dimethylamine is given off.
• the solution is cooled to 25 C. and acidified with 2 N hydrochloric acid.
• the precipitate is filtered off and once recrystallized from aqueous alcohol, to yield about 2.6 parts of the compound D of the formula melting above 400 C.
• EXAMPLE 1 Determining the minimal inhibitory concentration (MIC) against bacteria in the dilution test
• the MIC minimal inhibitory concentration
• the MIC is determined by a method adapted from the standard procedure, which furnishes an approximation to absolute minimal inhibitory values of an active substance.
• a solution of 1% and 0.3% strength each of the above substances in dimethylsulphoxide are poured into small tubes containing glucose broth and with these solutions dilution series are prepared in which each member is a tenfold dilution of the preceding one.
• the following continuous dilution series is obtained: 1000, 300, 100, 30, 10, 3 parts per million and so
• the solutions are inoculated with Staphylococcus aureus and then incubated for 48 hours at 37 C. (bacteriostatic test).
• MIC Minimum inhibitory concentration
• Antibacterial soaps in cake form are manufactured by adding 1.2 g. of a compound of the Formula 1 to the following mixture:
• the solutions are inoculated with the bacteria Staphylococcus aureus, Escherichia coli, and incubated for 24 hours at 37 C. After this time, 0.05 ml. is withdrawn with a pipette from each solution and poured out over brain heart infusion slant-agar. 'Ihe agar tubes are then incubated for another 24 hours at 37 C., and then the minimal lethal concentration in parts per million is determined.
• the valuation extends, on one hand, to the inhibitory zones (IZ in mm.) found around the blanks and, on the other hand, to the growth (6%) detected underneath them by microscopic examination:
• Staphylococcus aureus Compound IZ (mm.) percent What is claimed is:
• a method for combatting bacteria which comprises applying to said bacteria an anti-bacterially effective amount of a 2-(2-hydroxyphenyl)-benzoaxole of the formula in which R represents a member selected from the group consisting of hydrogen, chlorine, bromine, alkyl with up to 4 carbon atoms, phenyl, cyclohexyl and methoxy, R represents a member selected from the group consisting of hydrogen, chlorine, bormine and methyl and R is hydrogen, cholrine or bromine and X and X represent chlorine or bromine each.
• R represents a member selected from the group consisting of hydrogen, chlorine, bromine, methyl, phenyl and cyclohexyl.

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Life Sciences & Earth Sciences (AREA)
• Biochemistry (AREA)
• Chemical Kinetics & Catalysis (AREA)
• General Chemical & Material Sciences (AREA)
• Microbiology (AREA)
• Engineering & Computer Science (AREA)
• Textile Engineering (AREA)
• Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
• Agricultural Chemicals And Associated Chemicals (AREA)

Applications Claiming Priority (1)

Publications (1)

Family

ID=4423163

Family Applications (1)

Country Status (9)

Cited By (18)

Families Citing this family (1)

• 1966
  • 1966-11-30 CH CH1715466A patent/CH465959A/de unknown
• 1967
  • 1967-11-21 DE DE19671617994 patent/DE1617994A1/de active Pending
  • 1967-11-21 FR FR1573858D patent/FR1573858A/fr not_active Expired
  • 1967-11-29 SE SE16377/67A patent/SE339357B/xx unknown
  • 1967-11-29 BE BE707275D patent/BE707275A/xx unknown
  • 1967-11-29 NL NL6716245A patent/NL6716245A/xx unknown
  • 1967-11-29 GB GB54406/67A patent/GB1185238A/en not_active Expired
  • 1967-11-29 AT AT1077167A patent/AT277472B/de not_active IP Right Cessation
• 1970
  • 1970-07-14 US US54850A patent/US3706834A/en not_active Expired - Lifetime

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