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WO2011048011A2 - Dérivés de benzotropolone à titre d'agents antimicrobiens - Google Patents

Dérivés de benzotropolone à titre d'agents antimicrobiens Download PDF

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Publication number
WO2011048011A2
WO2011048011A2 PCT/EP2010/065464 EP2010065464W WO2011048011A2 WO 2011048011 A2 WO2011048011 A2 WO 2011048011A2 EP 2010065464 W EP2010065464 W EP 2010065464W WO 2011048011 A2 WO2011048011 A2 WO 2011048011A2
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Prior art keywords
biocide
preservative
alkyl
substituted
hydrogen
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PCT/EP2010/065464
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WO2011048011A3 (fr
WO2011048011A4 (fr
Inventor
Barbara Wagner
Dietmar Ochs
Karin Bieler
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BASF SE
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BASF SE
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Publication of WO2011048011A4 publication Critical patent/WO2011048011A4/fr
Anticipated expiration legal-status Critical
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Classifications

    • 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
    • A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
    • A01N35/06—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical containing keto or thioketo groups as part of a ring, e.g. cyclohexanone, quinone; Derivatives thereof, e.g. ketals
    • 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
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/42—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing within the same carbon skeleton a carboxylic group or a thio analogue, or a derivative thereof, and a carbon atom having only two bonds to hetero atoms with at the most one bond to halogen, e.g. keto-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
    • A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
    • A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
    • 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
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/14—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings
    • A01N43/16—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings with oxygen as the ring hetero atom
    • 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
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/24—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms
    • A01N43/26—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings
    • A01N43/28—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings with two hetero atoms in positions 1,3
    • A01N43/30—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings with two hetero atoms in positions 1,3 with two oxygen atoms in positions 1,3, condensed with a carbocyclic ring

Definitions

  • the present invention relates to the use of specific benzotropolone derivatives for the antimicrobial treatment of surfaces, as antimicrobial active substances against gram-positive and gram-negative bacteria, yeasts and fungi and also for the preservation of cosmetics, household products, textiles and plastics and for use as disinfectants.
  • the present invention relates to the use of benzotropolone derivatives of formula
  • R 2 , R3, R 4 , R5 and R 6 independently of one another are hydrogen; OH; d-C 3 oalkyl, C 2 -C 30 al- kenyl, CrC 3 oalkoxy, C 3 -Ci 2 cycloalkyl or CrC 30 hydroxyalkyl, which may be substituted by one or more E and/or interrupted by one or more D; C 6 -C 2 oaryl, which may be substituted by one or more G; C 4 -C 2 oheteroaryl, which may be substituted by one or more G, C 2 - Ci 8 alkenyl, C 2 -Ci 8 alkynyl, C 7 -C 25 aralkyl, or -CO-Ri 7 ; Ci-C 30 mono- or dialkylamino; COR 9 ; COORg; CONR 9 R 10 ; CN; S0 2 R 9 ; OCOOR 9 ; OCOR 9 ; NHCOOR 9 ; NR
  • Ri, R 7 and R 8 independently of one another are hydrogen; Ci-Ci 2 alkyl or C 3 -Ci 2 -cycloalkyl, which may be substituted by one or more E and/or interrupted by one or more D; C 6 - C 20 aryl, which may be substituted by one or more G; C 4 -C 20 heteroaryl, which may be substituted by one or more G, C 2 -Ci 8 alkenyl, C 2 -Ci 8 alkynyl, C 7 -C 25 aralkyl, or COOR 9 ;
  • R 7 and R 8 together form a five or six membered ring
  • R 6 and R 7 together form a five or six membered ring
  • R 9 and R10 independently from each other are hydrogen; Ci-Ci 8 alkyl or C 3 -Ci 2 -cycloalkyl which may be substituted by one or more E and/or interrupted by one or more D; C 6 -
  • C 20 aryl which may be substituted by one or more G
  • C 4 -C 20 heteroaryl which may be substituted by one or more G
  • organosilanyl or
  • R 9 and R 10 together form a five or six membered ring
  • D is -CO-; -COO-; -S-; -SO-; -S0 2 -; -0-; -NR 14 -; -SiR i9 R 2 o-; -PORn-; or
  • E is -OR i8 ; -SRi 8 ; -N R 14 Ri 5 ; -N R 14 CORi 5 ; -CORi 7 ; -COORi 6 ; -CON R 14 R 15 ; -CN ; halogen; or OS0 3 Ri 8 ; S0 3 Ri 8 ; S0 2 Ri 8 ; P0 3 (Ri 8 ) 2 ; OP0 3 (Ri 8 ) 2 ;
  • G is E; CrCi 8 alkyl, which is optionally interrupted by D; Ci-Ci 8 perfluoroalkyl; CrCi 8 alkoxy, which is optionally substituted by E and/or interrupted by D; wherein
  • R12, Ri3, Ri 4 and Ri 5 independently of each other are hydrogen; C 6 -Ci 8 aryl which is optionally substituted by OH , CrCi 8 alkyl or CrCi 8 alkoxy; CrCi 8 alkyl, which is optionally interrupted by -0-; or
  • Ri 4 and R 15 together form a five or six membered ring
  • R16 is hydrogen; C 6 -Ci 8 aryl which is optionally substituted by OH , CrCi 8 alkyl or d- Ci 8 alkoxy; CrCi 8 alkyl which is optionally interrupted by -O-;
  • Ri7 is H ; C 6 -Ci 8 aryl which is optionally substituted by OH , CrCi 8 alkyl or CrCi 8 alkoxy; or d-
  • Ci 8 alkyl which is optionally interrupted by -0-;
  • R18 is hydrogen; C 6 -Ci 8 aryl, which is optionally substituted by OH , CrCi 8 alkyl or d- Ci 8 alkoxy; d-d 8 alkyl, which is optionally interrupted by -O-; and
  • Rig and R 20 independently of each other are hydrogen; d-d 8 alkyl; C 6 -Ci 8 aryl which is optionally substituted by d-d 8 alkyl;
  • antimicrobial and/or preserving agents as antimicrobial and/or preserving agents.
  • Pr ferred are the compounds of formula
  • R21 and R22 independently of one another are hydrogen; OH ; d-doalkyl or d-doalkoxy, which may be substituted by one or more E and/or interrupted by one or more D; Ri , R3, R3, R 4 , R5, Re, E and D are defined as in formula (1 ).
  • R21 is hydrogen or d-doalkyl
  • R22 is hydrogen; d-doalkyl or d-doalkoxy;
  • R21 and R22 independently of one another are hydrogen; OH; d-C 3 oalkyl or CrC 3 oalkoxy, which may be substituted by one or more E and/or interrupted by one or more D; and Ri , R3, R3, R 4 , R5, R6, E and D are defined as in formula (1 ).
  • R21 is hydrogen or CrC 3 oalkyl
  • R22 is hydrogen; CrC 3 oalkyl or CrC 30 alkoxy; CrC 30 alkyl are straight chain or branched radicals like methyl, ethyl, n-propyl, isopropyl, n- butyl, sec-butyl, tert-butyl, amyl, isoamyl or tert-amyl, hexyl, 2-ethylhexyl, heptyl, octyl, isooc- tyl, nonyl, decyl, undecyl, dodecyl, tetradecyl, undecyl, eicosyl, tetracosyl, pentacosyl, hepta- cosyl, octacosyl or triacontyl.
  • CrC 30 alkoxy are straight chain or branched radicals like methoxy, ethoxy, n-propoxy, iso- propoxy, n-butyloxy, sek-butyloxy, tert-butyloxy, amyloxy, isoamyloxy, tert-amyloxy, hexyloxy, 2-ethylhexyloxy, heptyloxy, octyloxy, isooctyloxy, nonyloxy, decyloxy, undecyloxy, dodecy- loxy, tetradecyloxy, undecyloxy eicosyloxy tetracosyloxy, pentacosyloxy, heptacosyloxy, oc- tacosyloxy or triacontyloxy.
  • C 2 -C 30 alkenyl are straight chain or branched radicals like allyl, methallyl, isopropenyl, 2-bu- tenyl, 3-butenyl, isobutenyl, n-penta-2,4-dienyl, 3-methyl-but-2-enyl, n-oct-2-enyl, n-dodec-2- enyl, iso-dodecenyl, n-dodec-2-enyl, n-octadec-4-enyl, eicosenyl, tetracosenyl, pentacoensyl, heptacosenyl, octacosenyl or triacontenyl.
  • C 3 -Ci 2 cycloalkyl is for example cyclopropyl, cyclobutyl, cyclopentyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, cycloundecyl, cyclododecyl and preferably cyclohexyl.
  • Each alkyl or cycloalkyl can be saturated or unsaturated.
  • Each alkyl, cycloalkyi or alkoxy can preferably be substituted by one or more E and/or interrupted by one or more D.
  • Each aryl can be preferably substituted by G.
  • Each heteroaryl can be preferably substituted by G, C 2 -Ci 8 alkenyl, C 2 -Ci 8 alkynyl, C 7 -C 25 aral-
  • the compounds of formula (1 ) and (1 a) and (1 b) can be present in their protonated or depro- tonated form.
  • Ri , R 7 and R 8 are hydrogen
  • R 2 , R3, R 4 , R5 and R 6 are defined as in formula (1 ).
  • R 2 , R 3 , R 4 , R5 and R 6 independently of one another are hydrogen; OH; CrC 3 oalkyl, C 2 -C 30 al- kenyl, CrC 3 oalkoxy, C 3 -Ci 2 cycloalkyl or CrC 30 hydroxyalkyl, which may be substituted by one or more E and/or interrupted by one or more D; COR 9 ; COOR 9 ; CONR 9 R 10 ; S0 2 R 9 ;
  • Ri , R 7 and R 8 independently of one another are hydrogen; Ci-Ci 2 alkyl or C 3 -Ci 2 -cycloalkyl, which may be substituted by one or more E and/or interrupted by one or more D; COR 9 ;
  • R 9 and R10 independently from each other are hydrogen; Ci-Ci 8 alkyl or C 3 -Ci 2 -cycloalkyl which may be substituted by one or more E and/or interrupted by one or more D; C 6 -
  • R 9 and R 10 together form a five or six membered ring
  • D is -CO-; -COO-; -S-; -SO-; -S0 2 -; -0-; -NR 14 -; -SiR i9 R 2 o-; -PORn-; or
  • E is -OR i 8 ; -SR i8 ; -N R 14 R 15 ; -N R 14 CORi 5 ; -COR i 7 ; -COORi 6 ; -CON R 14 R 15 ; -CN ; halogen; or OS0 3 Ri 8 ; S0 3 Ri 8 ; S0 2 Ri 8 ; P0 3 (Ri 8 ) 2 ; OP0 3 (Ri 8 ) 2 ;
  • G is E; CrCi 8 alkyl, which is optionally interrupted by D; CrCi 8 alkoxy, which is optionally substituted by E and/or interrupted by D; wherein Ri 2 , Ri 3 , Ri4 and Ri 5 independently of each other are hydrogen; C 6 -Ci 8 aryl which is optionally substituted by CrCi 8 alkyl or CrCi 8 alkoxy; CrCi 8 alkyl, which is optionally interrupted by -0-; or
  • R-I4 and R 15 together form a five or six membered ring
  • Ri 6 is hydrogen; C 6 -Ci 8 aryl which is optionally substituted by Ci-Ci 8 alkyl or Ci-Ci 8 alkoxy; C Ci 8 alkyl which is optionally interrupted by -0-;
  • Ri 7 is H; C 6 -Ci 8 aryl which is optionally substituted by Ci-Ci 8 alkyl or Ci-Ci 8 alkoxy; or d-
  • Ci 8 alkyl which is optionally interrupted by -0-;
  • Ri 8 is hydrogen; C 6 -Ci 8 aryl, which is optionally substituted by Ci-Ci 8 alkyl or Ci-Ci 8 alkoxy;
  • Rig and R 20 independently of each other are hydrogen; Ci-Ci 8 alkyl; C 6 -Ci 8 aryl which is optionally substituted by Ci-Ci 8 alkyl.
  • R 6 is hydrogen; OH; CrC 3 oalkyl orCrC 3 oalkoxy, which may be substituted by one or more E and/or interrupted by one or more D;
  • R 5 is hydrogen; substituted or unsubstituted Ci-Ci 8 alkyl
  • R 2 and R 4 independently from each other are hydrogen; or substituted or unsubstituted C
  • R 3 is hydrogen; or carboxylate COOX; wherein
  • X is Na, K or NH 4 ;
  • R 2 , R3, R 4 , R5 and R 6 independently of one another are hydrogen; d-C ⁇ alkyl, CrC 3 oalkoxy or CrCi 2 alkenyl substituted by E;
  • E is carboxylate; OCOR 9 ; sulphate; sulphonate; phosphonate; or phosphate; and
  • R 9 is defined as in formula (1 ). Further preferred are compounds of formula (1 ), wherein
  • R 3 is a radical of formula , wherein
  • C 2 alkyl which may be substituted by one or more E and/or interrupted by one or more D
  • C 6 -C 2 oaryl which may be substituted by one or more G
  • C 4 - C 2 oheteroaryl which may be substituted by one or more G, C 2 -Ci 8 alkenyl, C 2 -Ci 8 alkynyl, C 7 -C25aralkyl, or -CO-Ri 7 ;
  • Ri 7 is H; C 6 -Ci 8 aryl which is optionally substituted by CrCi 8 alkyl or Ci-Ci 8 alkoxy; or d- Ci 8 alkyl which is optionally interrupted by -O-; and
  • Ri , R 2 , R 4 , Rs, R6, R7 and R 8 , R 9 , R10, D, G and E are defined as in formula (1 ).
  • R 2 , R3, R 4 , R5, R6, R9, Rio, Rii , and Ri 2 independently of one another are sulphate; sulpho- nate; phosphate; or phosphonate and/or R-i , R 7 and R 8 together with the adjacent oxy- gen independently of one another form a sulphate, sulphonate, phosphate or phosphonate group.
  • R 2 is CrC 3 oalkyl, C 2 -C 3 oalkenyl, CrC 3 oalkoxy, C 3 -Ci 2 -cycloalkyl or CrC 30 hydroxyalkyl, which may be substituted by one or more E and/or interrupted by one or more D; C 6 -
  • C 20 aryl which may be substituted by one or more G; COR 9 ; COOR 9 ; CONR 9 R 10 ;
  • Ri , R 3 , R 4 , R 5 , R6, R7, Re, R9, R10, E, D and G are defined as in formula (1 ).
  • R 2 and R 5 is CrC 30 alkyl, C 2 -C 30 alkenyl, CrC 30 alkoxy, C 3 -Ci 2 -cycloalkyl or d-
  • C 30 hydroxyalkyl which may be substituted by one or more E and/or interrupted by one or more D;
  • C 6 -C 2 oaryl which may be substituted by one or more G;
  • Ri , R 3 , R 4 , R 6 , R7, R 8 , R 9 , Rio, E, D and G are defined as in formula (1 ).
  • the benzotropolone derivatives of formula (1 ) exhibit pronounced antimicrobial action, for example, against pathogenic gram-positive and gram-negative bacteria and against bacteria of the skin and oral flora, and also against yeasts and molds. They are accordingly suitable for disinfection, deodorisation, and for general and antimicrobial treatment of the skin and mucosa and of integumentary appendages (hair), for example, for the disinfection of hands and wounds.
  • antimicrobial active substances and preservatives are accordingly suitable as antimicrobial active substances and preservatives in per- sonal care preparations, for example shampoos, bath additives, hair care preparations, liquid and solid soaps (based on synthetic surfactants and salts of saturated and/or unsaturated fatty acids), lotions and creams, deodorants, other aqueous or alcoholic solutions, e.g. cleansing solutions for the skin, moist cleaning cloths, wet wipes, oils or powders.
  • the antimicrobial compounds of the invention are effective as anti-dandruff agents in shampoos or other products used in hair treatment such as oils, sprays, hair gels.
  • the benzotropolone derivatives of formula (1 ) may be active ingredients in a personal care preparation comprising cosmetically tolerable carriers or adjuvants.
  • the personal care preparation contains from 0.01 to 15 % by weight, for example, from 0.1 to 10 % by weight, based on the total weight of the composition, of the benzotropolone derivatives of formula (1 ), and cosmetically tolerable adjuvants.
  • the personal care preparation may be in the form of a water-in-oil or oil-in-water emulsion, an alcoholic or alcohol-containing formulation, a vesicular dispersion of an ionic or non-ionic ampiphilic lipid, a gel, a solid stick or an aerosol formulation.
  • the cosmetically tolerable adjuvant contains preferably from 5 to 50 % of an oil phase, from 5 to 20 % of an emulsifier and from 30 to 90 % water.
  • the oil phase may comprise any oil suitable for cosmetic formulations, for example one or more hydrocarbon oils, a wax, a natural oil, a silicone oil, a fatty acid ester or a fatty alcohol.
  • Preferred mono- or poly-ols are ethanol, isopropanol, propylene glycol, hexylene glycol, glycerol and sorbitol.
  • Cosmetic formulations according to the invention are used in various fields. There come into consideration, for example, the following preparations:
  • skin-care preparations e.g. skin-washing and cleansing preparations in the form of tab- let-form or liquid soaps, synthetic detergents or washing pastes,
  • bath preparations e.g. liquid (foam baths, milks, shower preparations) or solid bath preparations, e.g. bath cubes and bath salts;
  • skin-care preparations e.g. skin emulsions, multi-emulsions or skin oils
  • cosmetic personal care preparations e.g. facial make-up in the form of day creams or powder creams, face powder (loose or pressed), rouge or cream make-up, eye-care preparations, e.g. eye shadow preparations, mascaras, eyeliners, eye creams or eye-fix creams; lip-care preparations, e.g. lipsticks, lip gloss, lip contour pencils, nail-care preparations, such as nail varnish, nail varnish removers, nail hardeners or cuticle removers; intimate hygiene preparations, e.g. intimate washing lotions or intimate sprays;
  • foot-care preparations e.g. foot baths, foot powders, foot creams or foot balsams, special deodorants and antiperspirants or callus-removing preparations;
  • light-protective preparations such as sun milks, lotions, creams or oils, sun-blocks or tropicals, pre-tanning preparations or after-sun preparations;
  • skin-tanning preparations e.g. self-tanning creams
  • depigmenting preparations e.g. preparations for bleaching the skin or skin-lightening preparations
  • insect-repellents e.g. insect-repellent oils, lotions, sprays or sticks;
  • deodorants such as deodorant sprays, pump-action sprays, deodorant gels, sticks or roll-ons;
  • antiperspirants e.g. antiperspirant sticks, creams or roll-ons
  • preparations for cleansing and caring for blemished skin e.g. synthetic detergents (solid or liquid), peeling or scrub preparations or peeling masks;
  • hair-removal preparations in chemical form e.g. hair-removing powders, liquid hair-removing preparations, cream- or paste-form hair-removing preparations, hair- removing preparations in gel form or aerosol foams;
  • shaving preparations e.g. shaving soap, foaming shaving creams, non-foaming shaving creams, foams and gels, preshave preparations for dry shaving, aftershaves or aftershave lotions;
  • fragrance preparations e.g. fragrances (eau de Cologne, eau de toilette, eau de perfume, perfume de toilette, perfume), perfume oils or perfume creams;
  • denture-care and mouth-care preparations e.g. toothpastes, gel toothpastes, tooth powders, mouthwash concentrates, anti-plaque mouthwashes, denture cleaners or denture fixatives;
  • cosmetic hair-treatment preparations e.g. hair-washing preparations in the form of shampoos and conditioners, hair-care preparations, e.g. pretreatment preparations, hair tonics, styling creams, styling gels, pomades, hair rinses, treatment packs, intensive hair treatments, hair-structuring preparations, e.g. hair-waving preparations for permanent waves (hot wave, mild wave, cold wave), hair-straightening preparations, liquid hair- setting preparations, hair foams, hairsprays, bleaching preparations, e.g.
  • hair-washing preparations in the form of shampoos and conditioners
  • hair-care preparations e.g. pretreatment preparations, hair tonics, styling creams, styling gels, pomades, hair rinses, treatment packs, intensive hair treatments, hair-structuring preparations, e.g. hair-waving preparations for permanent waves (hot wave, mild wave, cold wave), hair-straightening preparations, liquid hair- setting preparations, hair foams, hair
  • An antimicrobial soap has, for example, the following composition: 0.01 to 5 % by weight of at least one of the benzotropolone derivative of formula (1 ), 0.3 to 1 % by weight of titanium dioxide,
  • soap base ad 100 %, e.g. of a sodium salt of tallow fatty acid or coconut fatty acid, or glyc- erol.
  • a shampoo has, for example, the following composition:
  • a deodorant has, for example, the following composition:
  • the invention relates also to an oral composition containing from 0.01 to 15 % by weight, based on the total weight of the composition, of at least one of the benzotropolone derivative of formula (1 ), and orally tolerable adjuvants.
  • the oral composition according to the invention may be, for example, in the form of a gel, a paste, a cream or an aqueous preparation (mouthwash).
  • the oral composition according to the invention may also comprise compounds that release fluoride ions which are effective against the formation of caries, for example inorganic fluoride salts, e.g. sodium, potassium, ammonium or calcium fluoride, or organic fluoride salts, e.g. amine fluorides, which are known under the trade name OLAFLUOR.
  • fluoride ions which are effective against the formation of caries
  • inorganic fluoride salts e.g. sodium, potassium, ammonium or calcium fluoride
  • organic fluoride salts e.g. amine fluorides
  • the antimicrobial compounds of this invention are also used in washing and cleaning formu- lations, e.g. in liquid or powder washing agents or softeners.
  • the antimicrobial compounds of this invention can also be used in household and general- purpose cleaners for cleaning and disinfecting hard surfaces.
  • a cleaning preparation has, for example the following composition:
  • antimicrobial compound 0.01 to 5 % by weight antimicrobial compound
  • Table 2 Examples of combinations of biocides and/or preservatives used as antimicrobial actives in cosmetic products and household products
  • BIOCIDE/PRESERVATIVE 9 Table 2: A B c D E F G H I K L M N 0 P Q R s T u V w
  • BIOCIDE/PRESERVATIVE 52 Table 2: A B c D E F G H I K L M N 0 P Q R s T u V w
  • BIOCIDE/PRESERVATIVE 95 Table 2: A B C D E F G H I K L M N 0 P Q R s T u V w
  • BIOCIDE/PRESERVATIVE 138 Table 2: A B C D E F G H I K L M N 0 P Q R s T u V w
  • BIOCIDE/PRESERVATIVE 181 Table 2: A B C D E F G H I K L M N 0 P Q R s T u V w
  • BIOCIDE/PRESERVATIVE 224 Table 2: A B C D E F G H I K L M N O P Q R s T u V w
  • BIOCIDE/PRESERVATIVE 243 BIOCIDE/PRESERVATIVE 243
  • X represents a specific biocide and/or preservative.
  • concentrations of these biocidal/preservative substances in the blends are between 1 % and 99%, preferably between 10% and 90%.
  • concentration of these blends in household and personal care products is typically in the range of 0.1 % to 5% and preferred 0.2% to 2%.
  • biocide combination examples are the following:
  • biocide combinations listed before the weight ratio of the biocides and or preserva- tives is for combinations of two biocides/preservatives 1 :1 or 1 :2 or 2:1 or 1 :3 or 3:1 .
  • BIOCIDES/PRESERVARTIVES from Table 2 as shown in the following formulation exam- pies:
  • BIOCIDE/PRESERVATIVE may be (as described in Table 2) BIOCIDE/PRESERVATIVE 1 , or BIOCIDE/PRESERVATIVE 2, or BIOCIDE/PRESERVATIVE 3, or BIOCIDE/PRESERVATIVE 4, or BIOCIDE/PRESERVATIVE 5, or BIOCIDE/PRESERVATIVE 6, or BIOCIDE/- PRESERVATIVE 7, or BIOCIDE/PRESERVATIVE 8, or BIOCIDE/PRESERVATIVE 9, or BIOCIDE/PRESERVATIVE 10, or BIOCIDE/PRESERVATIVE 1 1 , or BIOCIDE/PRESERVATIVE 12, or BIOCIDE/PRESERVATIVE 13, or BIOCIDE/PRESERVATIVE 14, or BIOCIDE/- PRESERVATIVE 15, or BIOCIDE/PRESERVATIVE 16, or BIOCIDE/PRESERVATIVE 17, or BIOCIDE/PRESERVATIVE 18, or BIOCIDE/PRESERVATIVE 19, or BIOCIDE/PRESERVATIVE 20, or BIOCIDE/PRESERVATIVE
  • BIOCIDE/PRESERVATIVE 55 or BIOCIDE/PRESERVATIVE 56, or BIOCIDE/PRESERVATIVE 57, or BIOCIDE/PRESERVATIVE 58, or BIOCIDE/PRESERVATIVE 59, or BIOCIDE/- PRESERVATIVE 60, or BIOCIDE/PRESERVATIVE 61 , or BIOCIDE/PRESERVATIVE 62, or BIOCIDE/PRESERVATIVE 63, or BIOCIDE/PRESERVATIVE 64, or BIOCIDE/PRESER- VATIVE 65, or BIOCIDE/PRESERVATIVE 66, or BIOCIDE/PRESERVATIVE 67, or BIOCIDE/PRESERVATIVE 68, or BIOCIDE/PRESERVATIVE 69, or BIOCIDE/PRESERVATIVE 70, or BIOCIDE/PRESERVATIVE 71 , or BIOCIDE/PRESERVATIVE 72, or BIOCIDE/PRESERVATIVE 73, or BIOCIDE/PRESERVATIVE 74,
  • BIOCIDE/PRE-SERVATIVE 81 or BIOCIDE/PRESERVATIVE 82, or BIOCIDE/PRESERVATIVE 83, or BIOCIDE/PRESERVATIVE 84, or BIOCIDE/PRESERVATIVE 85, or BIOCIDE/PRESERVATIVE 86, or BIOCIDE/PRESERVATIVE 87, or BIOCIDE/PRESERVATIVE 88, or BIOCIDE/PRESERVATIVE 89, or BIOCIDE/PRESERVATIVE 90, or BIOCIDE/PRESERVATIVE 91 , or BIOCIDE/PRESERVATIVE 92, or BIOCIDE/PRESERVATIVE 93, or BIOCIDE/PRESERVATIVE 94, or BIOCIDE/PRESERVATIVE 95, or BIOCIDE/PRESERVATIVE 96, or BIOCIDE/PRESERVATIVE 97, or BIOCIDE/PRESERVATIVE 98, or BIOCIDE/PRE-SERVA- TIVE 99, or BIOCIDE/PRESER
  • BIOCIDES/PRESERVATIVES of table 2 are shown:
  • Vitamin E Acetate 0,50 0,50 0,50 0,50 0,50 0,50 0,50 0,50 0,50
  • Emulsifier free face care A B C D E F G H I
  • Vitamin E Acetate 0,20 0,20 0,20 0,20 0,20 0,20 0,20 0,20 0,20 0,20 0,20 oc-Glycosil Rutin 0,30 0,30 0,30 0,30 0,30 0,30 0,30 0,30 0,30 0,30 0,30 0,30 0,30 0,30 0,30 0,30 0,30 0,30 0,30
  • Trisodium EDTA 0,30 0,30 0,30 0,30 0,30 0,30 0,30 0,30 0,30 0,30 0,30 0,30 0,30 0,30 0,30 0,30 0,30 0,30 0,30
  • Trisodium EDTA 0,10 0,10 0,10 0,10 0,10 0,10 0,10 0,10 0,10 0,10 0,10 0,10
  • Pentaerythrityl Tetraisostearate 10,00 10,00 10,00 10,00 10,00 10,00 10,00 10,00 10,00 10,00 10,00 10,00 10,00 10,00 10,00 10,00 10,00
  • BIOCID (Table 2) 0,00 0,00 0,00 0,25 0,25 0,25 0,50 0,50 0,50
  • Glyceryl monoisodecyl ether 0,50 0,50 0,50 0,50 0,50 0,50 0,50 0,50 0,50 0,50
  • Sorbitol 70% 20,00 20,00 20,00 20,00 20,00 20,00 20,00 20,00 20,00 20,00 20,00 20,00 20,00 20,00 20,00 20,00 20,00 20,00
  • Sorbitol 70% 10,0 10,0 10,0 10,0 10,0 10,0 10,0 10,0 10,0
  • Lactic acid (80% solution) 0,01 0,01 0,01 0,01 0,01 0,01 0,01 0,01 0,01 0,01 0,01 0,01 0,01
  • PEG 150 disterarate 1 ,00 1 ,00 1 ,00 1 ,00 1 ,00 1 ,00 1 ,00 1 ,00 1 ,00 1 ,00 1 ,00 1 ,00 1 ,00 1 ,00

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  • Life Sciences & Earth Sciences (AREA)
  • Dentistry (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)
  • Pest Control & Pesticides (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Cosmetics (AREA)

Abstract

Cette invention concerne l'utilisation de dérivés de benzotropolone de Formule (I). Dans la Formule (I), R2, R3, R4, R5 et R6 sont indépendamment les uns des autres un atome d'hydrogène; OH; un alkyle C1-C30, un alcényle C2-C30, un alcoxy C1-C30, un cycloalkyle C3-C12 ou un hydroxyalkyle C1-C30, qui peuvent être substitués par un ou plusieurs E et/ou interrompus par un ou plusieurs D; un aryle C6-C20, qui peut être substitué par un ou plusieurs G; un hétéroaryle C4-C20, qui peut être substitué par un ou plusieurs G, un alcényle C2-C18, un alcynyle C2-C18, un aralkyle C7-C25, ou -CO-R17 ; un mono- ou un dialkylamino C1-C30 ; COR9 ; COOR9 ; CONR9R10 ; CN; SO2R9 ; OCOOR9 ; OCOR9 ; NHCOOR9 ; NR9COR10 ; NH2 ; un sulfate; un sulfonate; un phosphate; un phosphonate; R1, R7 et R8 sont indépendamment les uns des autres un atome d'hydrogène; un alkyle C1-C12 ou un cycloalkyle C3-C12, qui peuvent être substitués par un ou plusieurs E et/ou interrompus par un ou plusieurs D; un aryle C6-C20, qui peut être substitué par un ou plusieurs G; un hétéroaryle C4-C20, qui peut être substitué par un ou plusieurs G, un alcényle C2-C18, un alcynyle C2-C18, un aralkyle C7-C25, ou COOR9 ; COR9 ; CONR9R10 ; SO3R9 ; SO2R9 ; PO3(R9)2 ; PO2(R9)2 ; ou ensemble, R7 et R8 forment un cycle ayant cinq ou six chaînons; ou ensemble, R6 et R7 forment un cycle ayant cinq ou six chaînons; ou R9 et R10 sont indépendamment l'un de l'autre un atome d'hydrogène; un alkyle C1-C18 ou un cycloalkyle C3-C12 qui peut être substitué par un ou plusieurs E et/ou interrompu par un ou plusieurs D; un aryle C6-C20, qui peut être substitué par un ou plusieurs G; un hétéroaryle C4-C20, qui peut être substitué par un ou plusieurs G; un organosilanyle; ou ensemble, R9 et R10 forment un cycle ayant cinq ou six chaînons; D est -CO-; -COO-; -S-; -SO-; -SO2-; -O-; -NR14-; -SiR19R20-; -POR11-; -CR12=CR13-; ou -C≡C-; et E est -OR18 ; -SR18 ; -NR14R15 ; -NR14COR15 ; -COR17 ; -COOR16 ; -CONR14R15 ; -CN; un atome d'halogène; ou OSO3R18 ; SO3R18 ; SO2R18 ; PO3(R18); OPO3(R18)2 ; G est E; un alkyle C1-C18, qui peut être éventuellement interrompu par D; un perfluoroalkyle C1-C18 ; un alcoxy C1-C18, qui est éventuellement substitué par E et/ou interrompu par D; R12, R13, R14 et R15 étant indépendamment les uns des autres un atome d'hydrogène; un aryle C6-C18 qui est éventuellement substitué par OH, un alkyle C1-C18 ou un alcoxy C1-C18 ; un alkyle C1-C18, qui est éventuellement interrompu par -O-; ou ensemble, R14 et R15 forment un cycle ayant cinq ou six chaînons, R16 est un atome d'hydrogène; un aryle C6-C18 qui est éventuellement substitué par OH, un alkyle C1-C18 ou un alcoxy C1-C18 ; un alkyle C1-C18 qui est éventuellement interrompu par -O-; R17 est H; un aryle C6-C18 qui est éventuellement substitué par OH, un alkyle C1-C18 ou un alcoxy C1-C18 ; ou un alkyle C1-C18 qui est éventuellement interrompu par -O-; R18 est un atome d'hydrogène; un aryle C6-C18, qui est éventuellement substitué par OH, un alkyle C1-C18 ou un alcoxy C1-C18 ; un alkyle C1-C18, qui est éventuellement interrompu par -O-; et R19 et R20 sont indépendamment l'un de l'autre un atome d'hydrogène; un alkyle C1-C18 ; un aryle C6-C18 qui est éventuellement substitué par un alkyle C1-C18 ; à titre d'agents antimicrobiens et/ou de conservateurs.
PCT/EP2010/065464 2009-10-23 2010-10-14 Dérivés de benzotropolone à titre d'agents antimicrobiens Ceased WO2011048011A2 (fr)

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Publication number Priority date Publication date Assignee Title
US20150353470A1 (en) * 2009-10-06 2015-12-10 Basf Se Stabilization of household, body-care and food products by using benzotropolone containing plant extracts and/or related benzotropolone derivatives
EP2879669A4 (fr) * 2012-07-29 2016-04-13 Univ Colorado Regents Antagonistes du complexe de récepteur 1/2 de type toll
WO2017079564A1 (fr) * 2015-11-04 2017-05-11 The Penn State Research Foundation Composés, compositions et méthodes pour la coloration de matières comestibles
US11542291B2 (en) 2018-07-16 2023-01-03 The Penn State Research Foundation Compounds, compositions, and methods for coloring edible materials

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JPS5315417A (en) * 1976-07-23 1978-02-13 Nourinshiyou Chiyagiyou Shiken Plant virus inhibitor
WO1999053916A1 (fr) * 1998-04-21 1999-10-28 Mitsui Norin Co., Ltd. Agents anti-chlamidia
DE10221741A1 (de) * 2002-05-16 2003-12-04 Cognis Deutschland Gmbh Antischuppenshampoos
WO2006082151A2 (fr) * 2005-02-02 2006-08-10 Symrise Gmbh & Co. Kg Melanges synergiques d'alcane-diols c6 a c12 et de tropolone (derives)

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Title
GEIGER, POLYMER BULLETIN, vol. 52, 2004, pages 65 - 70

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20150353470A1 (en) * 2009-10-06 2015-12-10 Basf Se Stabilization of household, body-care and food products by using benzotropolone containing plant extracts and/or related benzotropolone derivatives
US9663442B2 (en) * 2009-10-06 2017-05-30 Basf Se Stabilization of household, body-care and food products by using benzotropolone containing plant extracts and/or related benzotropolone derivatives
EP2879669A4 (fr) * 2012-07-29 2016-04-13 Univ Colorado Regents Antagonistes du complexe de récepteur 1/2 de type toll
WO2017079564A1 (fr) * 2015-11-04 2017-05-11 The Penn State Research Foundation Composés, compositions et méthodes pour la coloration de matières comestibles
US11001601B2 (en) 2015-11-04 2021-05-11 The Penn State Research Foundation Compounds, compositions and methods for coloring edible materials
US11542291B2 (en) 2018-07-16 2023-01-03 The Penn State Research Foundation Compounds, compositions, and methods for coloring edible materials

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