Patents by Inventor Karl Hoegerle
Karl Hoegerle has filed for patents to protect the following inventions. This listing includes patent applications that are pending as well as patents that have already been granted by the United States Patent and Trademark Office (USPTO).
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Patent number: 5037449Abstract: Reactive dyes of the formula ##STR1## in which Fa is the radical of an organic dye of the monoazo or polyazo, metal complex azo, anthraquinone, phthalocyanine, formazan, azomethine, dioxazine, phenazine, stilbene, triphenylmethane, xanthene, thioxanthone, nitroaryl, naphthoquinone, pyrenequinone or perylene-tetracarbimide series, X.sub.1 and X.sub.2, independently of one another, are each halogen, R.sub.1 is hydrogen or substituted or unsubstituted C.sub.1 -C.sub.4 alkyl, R.sub.2 is substituted or unsubstituted C.sub.1 -C.sub.4 alkyl and r is the number 1 or 2, produce on hydroxyl- or nitrogen-containing textile materials dyeings which have good fastness properties.Type: GrantFiled: August 23, 1989Date of Patent: August 6, 1991Assignee: Ciba-Geigy CorporationInventors: Karl Hoegerle, Urs Lehmann
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Patent number: 4999027Abstract: In the process for the trichromatic dyeing or printing of natural and synthetic polyamide fibre materials, mixtures of reactive dyes, wherein blue-dyeing reactive dyes of the formula ##STR1## in which X is halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, cyano or nitro, n is the number 0, 1 or 2, q is the number 0 or 1, m is the number 1, 2 or 3, Z is halogen and Y is a CN, CHO or S(O).sub.p R group in which p is the number 0, 1 or 2 and R is substituted or unsubstituted C.sub.1 -C.sub.8 alkyl or phenyl, are used together with sulfo-containing yellow- or orange-dyeing reactive dyes and sulfo-containing red-dyeing reactive dyes, have a uniform color build-up in combination with shade constancy in different concentrations and good compatibility.Type: GrantFiled: August 23, 1989Date of Patent: March 12, 1991Assignee: Ciba-Geigy CorporationInventors: Urs Lehmann, Karl Hoegerle
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Patent number: 4968781Abstract: A reactive dye of the formula ##STR1## in which Fa is the radical of an organic dye of the monoazo, polyazo, metal complex azo, anthraquinone, phthalocyanine, formazan, azomethine, dioxazine, phenazine, stilbene, triphenylmethane, xanthene, thioxanthone, nitroaryl, naphthoquinone, pyrenequinone or perylenetetracarbimide series, T is a negative substituent, one X is a detachable substituent and the other X is a group of the formula ##STR2## A is arylene, V is hydrogen, a substituted or unsubstituted C.sub.1 -C.sub.4 alkyl radical or a radical of the formula --(CH.sub.2).sub.q --SO.sub.2 --Z, Z is a --CH.dbd.CH.sub.2 or CH.sub.2 --Y radical and Y is an inorganic or organic radical which is detachable under alkaline conditions, q, m and n are independently of one another an integral number from 2 to 6, R and R' are independently of one another hydrogen or substituted or unsubstituted C.sub.1 -C.sub.4 alkyl, and r is 1 or 2.Type: GrantFiled: March 28, 1988Date of Patent: November 6, 1990Assignee: Ciba-Geigy CorporationInventors: Karl Seitz, Karl Hoegerle
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Patent number: 4968344Abstract: A process for immunizing healthy plants against plant diseases which process comprises the dressing and/or coating of seeds or the treatment of plants and/or their environment by using active ingredients of the formula ##STR1## in which Hal is halogen,X is oxygen or sulfur, andR is hydrogen, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -alkyl which interrupted by an oxygen or sulfur atom, C.sub.1 -C.sub.6 -alkyl which is substituted by halogen, cyano or the COO--C.sub.1 -C.sub.6 -alkyl radical, C.sub.3 -C.sub.5 -alkenyl which is unsubstituted or substituted by halogen, C.sub.3 -C.sub.5 -alkynyl which is unsubstituted or substituted by halogen, C.sub.3 -C.sub.6 -cycloalkyl which is unsubstituted or substituted by halogen or methyl, or a normal equivalent of a cation which is formed from a base or a basic compound.Type: GrantFiled: October 31, 1989Date of Patent: November 6, 1990Assignee: Ciba-Geigy CorporationInventors: Walter Kunz, Theodor Staub, Jean-Pierre M e/ traux, Karl Hoegerle, Robert Nyfeler, Patricia A. Ahl Goy
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Patent number: 4952679Abstract: Reactive dyes suitable for dyeing and printing cellulosic fiber materials by the cold pad-batch process having the formula ##STR1## wherein Fa is a monoazo or polyazo, metal complex azo, anthraquinone, phthalocyanine, formazane, azomethine, dioxazine, phenazine, stilbene, triphenylmethane, xanthene, thioxanthone, nitroaryl, naphthoquinone, pyrenequinone or perylenetetracarbimide dye radical, X.sub.1 is halogen, C.sub.1 -C.sub.4 -alkylsulfonyl, phenylsulfonyl, a sulfonic acid or phosphoric acid group or a quaternized ammonium group, X.sub.2 independently has the meaning of X.sub.1 or is C.sub.1 -C.sub.4 -alkyl which is unsubstituted or substituted by halogen, hydroxy, cyano, carboxyl, sulfo, sulfato, C.sub.1 -C.sub.4 -alkoxycarbonyl or C.sub.1 -C.sub.4 alkoxy, R is hydrogen or C.sub.1 -C.sub.4 -alkyl which is unsubstituted or substituted by halogen, hydroxy, cyano, carboxyl, sulfo, sulfato, C.sub.1 -C.sub.4 -alkoxycarbonyl or C.sub.1 -C.sub.4 -alkoxy, and r is 1 or 2.Type: GrantFiled: August 19, 1988Date of Patent: August 28, 1990Assignee: Ciba-Geigy CorporationInventor: Karl Hoegerle
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Patent number: 4918169Abstract: Reactive dyes suitable for dyeing and printing cellulosic fiber materials by the cold pad-batch process having the formula ##STR1## wherein Fa is a monoazo or polyazo, metal complex azo, anthraquinone, phthalocyanine, formazane, azomethine, dioxazine, phenazine, stilbene, triphenylmethane, xanthene, thioxanthone, nitroaryl, napthoquinone, pyrenequinone or perylene-tetracarbimide dye radical, X is halogen, C.sub.1 -C.sub.4 -alkylsulfonyl, phenylsulfonyl, a sulfonic acid or phosphonic acid group or a quaternized ammonium group, r is 1 or 2, R is hydrogen or C.sub.1 -C.sub.4 alkyl which is unsubstituted or substituted by halogen, hydroxyl, cyano, carboxyl, sulfo, sulfato, C.sub.1 -C.sub.4 -alkoxycarbonyl, C.sub.1 -C.sub.4 -alkoxy or phenyl, and A is a radical of the formula ##STR2## wherein R' is hydrogen, C.sub.1 -C.sub.4 alkyl which is unsubstituted or substituted by halogen, hydroxyl, cyano, carboxyl, sulfo, sulfato, C.sub.1 -C.sub.4 -alkoxycarbonyl, C.sub.1 -C.sub.4 -alkoxy or phenyl, C.sub.5 -C.sub.Type: GrantFiled: August 19, 1988Date of Patent: April 17, 1990Assignee: Ciba-Geigy CorporationInventor: Karl Hoegerle
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Patent number: 4741760Abstract: N-Pyrimidin-4-yl-N'-sulfonylureas of the formula I and the basic addition salts thereof have herbicidal properties and properties for regulating, especially inhibiting, plant growth: ##STR1## the symbols in this formula having the following meanings: Q is halogen, lower alkyl, lower haloalkyl, lower alkoxy, lower haloalkoxy, nitro, amino, lower alkyl or dialkylamino, lower alkoxycarbonyl, formyl, lower alkoxyalkyl, lower alkoxyalkoxy, lower alkylthio, lower alkylsulfinyl or alkylsulfonyl, C.sub.1 -C.sub.4 -alkenyl or C.sub.1 -C.sub.4 -alkynyl,R.sub.1 is hydrogen, halogen, nitro, a ketal radical, a carbonyl radical substituted by allyl, haloalkyl, alkoxy or cycloalkyl, or is an oxime radical, a lower alkoxy, lower alkylthio, lower alkyl, lower alkylsulfinyl or sulfonyl group,R.sub.2 and R.sub.Type: GrantFiled: December 5, 1986Date of Patent: May 3, 1988Assignee: Ciba-Geigy CorporationInventors: Willy Meyer, Karl Hoegerle, Rudolph C. Thummel, Hans Tobler, Beat Bohner
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Patent number: 4686294Abstract: Compounds of the formula ##STR1## are described in which R.sub.1 represents a perfluoroalkyl radical of from 1 to 2 carbon atoms, and at least one of R.sub.2 and R.sub.3 represents hydrogen, and the other, or both represent lower alkyl, and R.sub.4 represents a lower alkyl radical which may be unsubstituted or bear certain substitution, and which are useful as herbicides in a method for controlling weeds and wild grasses. Compositions containing such compounds are also described. Finally, novel fluoro-thio semicarbazides are described which are useful intermediates in the production of the compounds of Formula I.Type: GrantFiled: December 20, 1968Date of Patent: August 11, 1987Assignee: Ciba-Geigy CorporationInventors: Karl Hoegerle, Hans J. Cellarius, Paul Rathgeb, Jurg Rumpf
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Patent number: 4680384Abstract: Dyes of the formula ##STR1## in which D is the radical of an organic dye, R is hydrogen or a low molecular weight alkyl group, X is an unsubstituted or substituted alklyl or alkenyl radical, one Y is halogen and the other Y is a substituent.Type: GrantFiled: July 19, 1984Date of Patent: July 14, 1987Assignee: Ciba-Geigy CorporationInventors: Karl Seitz, Henri Riat, Karl Hoegerle
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Patent number: 4560402Abstract: The invention relates to novel 2,4-diamino-5-alkylsulfinyl- or -alkylsulfonyl-6-halopyrimidines of the formula ##STR1## wherein n is 1 or 2, R.sub.1 is C.sub.1 -C.sub.4 alkyl, each of R.sub.2 and R.sub.3 is hydrogen, C.sub.1 -C.sub.6 alkyl or C.sub.3 -C.sub.6 cycloalkyl and X is chlorine, bromine or fluorine. These compounds have selective herbicidal action and inhibit plant growth. They are obtained by amination of halogen-substituted or hydroxyl-substituted amino-5-alkylsulfinyl- and -sulfonylpyrimidines. The invention also relates to the production of 5-sulfinylpyrimidine intermediates.Type: GrantFiled: August 4, 1980Date of Patent: December 24, 1985Assignee: Ciba Geigy CorporationInventors: Karl Hoegerle, Hans Tobler
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Patent number: 4507146Abstract: 2,4-Diamino-6-halo-5-trifluoromethylpyrimidines of the formula ##STR1## wherein X is a halogen atom, especially chlorine or fluorine, and R.sub.1 and R.sub.2 independently of one another are each hydrogen, C.sub.1 -C.sub.6 -alkyl or C.sub.3 -C.sub.6 -cycloalkyl, or together form a C.sub.3 -C.sub.7 -alkylene bridge, have outstanding selective-herbicidal properties, and are suitable for controlling weeds in crops of cultivated plants, such as maize, cereal or soya-bean. They are produced by aminating 2,4,6-trihalo-5-trifluoromethylpyrimidine, which for its part is obtainable by fluorination of 2,4,6-trihalopyrimidine-5-carboxylic acid. The 2,4,6-trihalo-5-carboxylic acids are novel intermediates, and are obtained by oxidizing 2,4,6-trihalo-2-methyl-, -halomethyl- or -formyl-pyrimidine in sulfuric acid by means of chromium trioxide.Type: GrantFiled: December 19, 1983Date of Patent: March 26, 1985Assignee: Ciba-Geigy CorporationInventors: Hans Tobler, Karl Hoegerle
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Patent number: 4490375Abstract: 4-N,N-Dimethylcarbamoyloxy-6-aminopyrimidines, and salts thereof, of the formula ##STR1## wherein R.sub.1 and R.sub.2 independently of one another are each hydrogen, C.sub.1 -C.sub.5 -alkyl, C.sub.1 -C.sub.5 -haloalkyl, C.sub.3 -C.sub.6 -cycloalkyl, C.sub.2 -C.sub.5 -alkenyl or C.sub.2 -C.sub.5 -alkynyl, or together they are a C.sub.2 -C.sub.5 -alkylene group, R.sub.3 is halogen or C.sub.1 -C.sub.5 -alkyl, and R.sub.4 is C.sub.1 -C.sub.5 -alkyl, or R.sub.3 is hydrogen and R.sub.4 is C.sub.2 -C.sub.5 -alkyl.There are described a process for producing these pyrimidines, their use for combating pests, and also the intermediates of the formula ##STR2## wherein R.sub.1 and R.sub.2 independently of one another are each hydrogen, C.sub.1 -C.sub.5 -alkyl, C.sub.1 -C.sub.5 -haloalkyl, C.sub.3 -C.sub.6 -cycloalkyl, C.sub.2 -C.sub.5 -alkenyl or C.sub.2 -C.sub.5 -alkynyl, or together they are a C.sub.2 -C.sub.5 -alkylene group, R.sub.3 is halogen or C.sub.1 -C.sub.5 -alkyl, and R.sub.4 is C.sub.1 -C.sub.5 -alkyl, or R.Type: GrantFiled: November 18, 1982Date of Patent: December 25, 1984Assignee: Ciba-Geigy CorporationInventors: Karl Hoegerle, Laurenz Gsell, Rudolf Wehrli
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Patent number: 4413124Abstract: The invention discloses novel 2-alkyl-5-alkylsulfonyl-4,6-dihalopyrimidines of the formula I ##STR1## wherein each of R.sup.1 and R.sup.2 independently is straight chain or branched chain C.sub.1 -C.sub.5 alkyl, and each of Y and Y.sup.1 is chlorine, fluorine or bromine. The compounds of the formula (I) can be obtained e.g. by reacting a 2-alkyl-4,6-dihydroxypyrimidine, in the presence of a chlorinating, brominating and/or fluorinating agent, with a dialkyl sulfoxide, and then oxidizing the compound obtained. The compounds of the formula (I) are valuable intermediates which are suitable e.g. for the manufacture of reactive dyes.Type: GrantFiled: September 16, 1982Date of Patent: November 1, 1983Assignee: Ciba-Geigy CorporationInventors: Karl Hoegerle, Kurt Ohnemus
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Patent number: 4412074Abstract: The invention discloses novel 2-alkyl-5-alkylsulfonyl-4,6-dihalopyrimidines of the formula I ##STR1## wherein each of R.sup.1 and R.sup.2 independently is straight chain or branched chain C.sub.1 -C.sub.5 alkyl, and each of Y and Y.sup.1 is chlorine, fluorine or bromine. The compounds of the formula (I) can be obtained e.g. by reacting a 2-alkyl-4,6-dihydroxypyrimidine, in the presence of a chlorinating, brominating and/or fluorinating agent, with a dialkyl sulfoxide, and then oxidizing the compound obtained. The compounds of the formula (I) are valuable intermediates which are suitable e.g. for the manufacture of reactive dyes.Type: GrantFiled: December 10, 1981Date of Patent: October 25, 1983Assignee: Ciba-Geigy CorporationInventors: Karl Hoegerle, Kurt Ohnemus
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Patent number: 4391810Abstract: 2-Methyl-4-N,N-dimethylcarbamoyloxy-6-amino-pyrimidines, and salts thereof, of the formula ##STR1## wherein R.sub.1 and R.sub.2 are each hydrogen, C.sub.1 -C.sub.5 -alkyl, C.sub.3 -C.sub.6 -cycloalkyl, C.sub.2 -C.sub.5 -alkenyl or C.sub.2 -C.sub.5 -alkynyl, or together they are a C.sub.2 -C.sub.5 -alkylene group; a process for producing these pyrimidines; and their use for combating pests.Type: GrantFiled: December 30, 1981Date of Patent: July 5, 1983Assignee: Ciba-Geigy CorporationInventors: Karl Hoegerle, Laurenz Gsell, Rudolf Wehrli
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Patent number: 4325869Abstract: Dyes of the formula ##STR1## in which D is the radical of an organic dye, R is hydrogen or a low molecular weight alkyl group, X is an unsubstituted or substituted alkyl or alkenyl radical, one Y is halogen and the other Y is a substituent.Type: GrantFiled: January 17, 1980Date of Patent: April 20, 1982Assignee: Ciba-Geigy CorporationInventors: Karl Seitz, Henri Riat, Karl Hoegerle
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Patent number: 4287342Abstract: There are described compounds of the formulae I and II ##STR1## and also salts of compounds of the formula I, wherein X represents optionally substituted alkyl or alkenyl, and the Y's represent identical or different halogen atoms. The compounds of the formulae I and II are valuable intermediates which are suitable for producing, e.g., fibre-reactive dyes.Type: GrantFiled: August 10, 1979Date of Patent: September 1, 1981Assignee: Ciba-Geigy CorporationInventor: Karl Hoegerle
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Patent number: 4188483Abstract: There are described compounds of the formulae I and II ##STR1## and also salts of compounds of the formula I, wherein X represents optionally substituted alkyl or alkenyl, and the Y's represent identical or different halogen atoms. The compounds of the formulae I and II are valuable intermediates which are suitable for producing, e.g., fiber-reactive dyes.Type: GrantFiled: May 8, 1978Date of Patent: February 12, 1980Assignee: Ciba-Geigy CorporationInventor: Karl Hoegerle
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Patent number: 4082535Abstract: This invention relates to new pyrimidine derivatives with herbicidal activity corresponding to formula I ##STR1## wherein X is halogen, lower alkoxy or lower alkylthio Y is hydrogen or halogen and ##STR2## are aliphatic amino radicals, one or both of which contain the cyclopropyl ring. A process for their manufacture is given. Herbicidal compositions which contain these new pyrimidine derivatives as active component and their use for the post-emergent total or selective combating of weeds are also disclosed.Type: GrantFiled: June 30, 1976Date of Patent: April 4, 1978Assignee: Ciba-Geigy CorporationInventors: Karl Hoegerle, Dagmar Berrer
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Patent number: 4029785Abstract: Compounds of formula ##STR1## wherein X represents chlorine, bromine or iodine,R.sub.1 represents a C.sub.1 -C.sub.12 -alkyl group optionally substituted by hydroxy, C.sub.1 -C.sub.4 -alkoxy, amino or mono- or di-C.sub.1 -C.sub.2 -alkylamino; or a C.sub.3 -C.sub.4 -alkenyl group, C.sub.3 -C.sub.8 -cycloalkyl group, benzyl group, p-acetylbenzyl group or phenethyl group, andR.sub.2 represents hydrogen or a C.sub.1 -C.sub.4 -alkyl group or a C.sub.3 -C.sub.4 -alkenyl group, orR.sub.1 and R.sub.2 together represent a 5- to 7-membered heterocyclic group, which optionally can additionally contain an oxygen atom,As well as their salts with organic and inorganic bases which are useful as bactericides and fungicides.Type: GrantFiled: December 12, 1974Date of Patent: June 14, 1977Assignee: Ciba-Geigy CorporationInventors: Karl Gatzi, Karl Hoegerle