Patents by Inventor Werner Topfl
Werner Topfl 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: 5342823Abstract: N-Arylsulfonyl-N'-pyrimidinyl-and N'-triazinylureas of formula I ##STR1## wherein Q is ##STR2## R is hydrogen or methyl; R.sub.1 is hydrogen, fluoro, chloro, C.sub.1 -C.sub.4 alkyl or methoxy;R.sub.2 is hydrogen, fluoro or chloro;R.sub.3, R.sub.4, R.sub.5, R.sub.6 and R.sub.7 are each independently of one another hydrogen or C.sub.1-C.sub.4 alkyl;R.sub.8, R.sub.9, R.sub.10, R.sub.11 and R.sub.12 are each independently of one another hydrogen or C.sub.1 -C.sub.4 alkyl;R.sub.13, R.sub.14, R.sub.15, R.sub.16 and R.sub.17 are each independently of one another hydrogen or C.sub.1 -C.sub.4 alkyl;Z is methyl or 2-pyridyl;E is methine or nitrogen;X is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 haloalkylthio, C.sub.1 -C.sub.4 alkylthio,C.sub.2 -C.sub.5 alkoxyalkyl, C.sub.2 -C.sub.5 alkoxyalkoxy, C.sub.2 -C.sub.5 alkylthioalkyl or cyclopropyl;Y is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.Type: GrantFiled: February 17, 1993Date of Patent: August 30, 1994Assignee: Ciba-Geigy CorporationInventors: Rainer Kuhlmeyer, Werner Topfl, Werner Fory
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Patent number: 5215570Abstract: The N-acylsulfamoylphenylureas of formula I below are suitable as counter-agents (antidotes or safeners) for protecting cultivated plants from the phytotoxic action of herbicides. Suitable crops are preferably cereals, soybeans, sorghum, maize and rice, and suitable herbicides are sulfonylureas, chloroacetanilides and aryloxyphenoxypropionic acid derivatives.The N-acylsulfamoylphenylureas have the formula I ##STR1## wherein A is a radical selected from the group ##STR2## R.sub.1 is C.sub.1 -C.sub.4 -alkoxy or each of R.sub.1 and R.sub.2, independently of the other, is hydrogen, C.sub.1 -C.sub.8 alkyl, C.sub.3 -C.sub.8 cycloalkyl, C.sub.3 -C.sub.6 alkenyl, C.sub.3 -C.sub.6 alkynyl, ##STR3## or C.sub.1 -C.sub.4 alkyl substituted by C.sub.1 -C.sub.4 alkoxy or by ##STR4## or R.sub.1 and R.sub.2 together form a C.sub.4 -C.sub.6 alkylene bridge, or a C.sub.4 -C.sub.6 alkylene bridge interrupted by oxygen, sulfur, SO, SO.sub.2, NH or by --N(C.sub.1 -C.sub.4 alkyl)-, R.sub.3 is hydrogen or C.sub.1 -C.sub.4 alkyl, R.Type: GrantFiled: January 3, 1991Date of Patent: June 1, 1993Assignee: Ciba-Geigy CorporationInventors: Urs Burckhardt, Raafat Soliman, Werner Topfl, Hans-Rudolf Waespe
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Patent number: 5135927Abstract: A microbicidal composition contains as active ingredient 2-chloro-4-trifluoromethylthiazol-5-carboxylic acid derivatives of the formula I ##STR1## R is an organic radical with up to 40 carbon atoms, which optionally contains nitrogen, oxygen or sulfur atoms and which can be transformed by hydrolosis or oxydation into the directly to the thiazol ring bound carboxyl rest.These compounds have good microbicidal activity and are used for the control and prevention of infestation of plants by phytophathogenic microorganismes.Type: GrantFiled: November 26, 1990Date of Patent: August 4, 1992Assignee: Ciba-Geigy CorporationInventors: Werner Topfl, Robert Nyfeler, Werner Fory
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Patent number: 4992434Abstract: A microbicidal compostion contains as active ingredient 2-chloro-4-trifluoromethylthiazol-5-carbonic acid derivatives of the formula I ##STR1## R is organic radical with up to 40 carbon atoms, which optionally contains nitrogen, oxygen or sulfur atoms and which can be transformed by hydrolosis or oxydation into the directly to the thiazol ring bound carboxyl rest. These compounds have good microbicidal activity and are used for the control and prevention of infestation of plants by phytophathogenic microorganisms.Type: GrantFiled: April 11, 1989Date of Patent: February 12, 1991Assignee: Ciba-Geigy CorporationInventors: Werner Topfl, Robert Nyfeler, Werner Fory
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Patent number: 4992549Abstract: Aminotriazines of the formula ##STR1## wherein E is nitrogen,Z is oxygen or sulfur,R.sup.3 is hydrogen, C.sub.1 -C.sub.4 -alkyl, C.sub.3 -C.sub.4 -alkenyl or C.sub.1 -C.sub.4 -alkoxy,R.sup.4 is hydrogen, halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.2 -C.sub.4 alkoxyalkyl, C.sub.2 -C.sub.4 -alkoxyalkoxy, cyclopropyl, -NH.sub.2, C.sub.1 -C.sub.4 -alkylamino, di-C.sub.1 -C.sub.4 -alkylamino, or a saturated 5- to 7-membered nitrogen heterocycle bound by way of the nitrogen atom and selected from pyrrolidine, piperidine, morpholine, thiomorpholine, piperazine and hexamethyleneimine,R.sup.5 is cyano, --CZ--R.sup.Type: GrantFiled: December 15, 1989Date of Patent: February 12, 1991Assignee: Ciba-Geigy CorporationInventor: Werner Topfl
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Patent number: 4978383Abstract: N-phenylsulfonyl-N'-triazinylureas of the general formula ##STR1## and the salts of these compounds with amines, alkali metal bases and alkaline earth metal bases or with quaternary ammonium bases, have good selective herbicidal and plant growth regulating properties when applied pre- and postemergence.In the formulaR.sub.1 is hydrogen, halogen, nitro, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.2 -C.sub.5 alkenyl or C.sub.1 -C.sub.4 alkoxycarbonyl,R.sub.2 is C.sub.1 -C.sub.3 alkyl or C.sub.1 -C.sub.3 alkoxy, each unsubstituted or substituted by 1 to 3 halogen atoms,R.sub.3 is halogen, hydrogen, --NR.sub.4 R.sub.5, C.sub.1 -C.sub.3 alkyl, unsubstituted or substituted by 1 to 3 halogen atoms or C.sub.1 -C.sub.4 alkoxy, or is C.sub.1 -C.sub.3 alkoxy, unsubstituted or substituted by methoxy, ethoxy, or 1 to 3 halogen atoms,R.sub.4 is hydrogen or methyl,R.sub.5 is hydrogen, C.sub.1 -C.sub.2 alkyl or methoxy,A is C.sub.1 -C.sub.4 alkylene or C.sub.2 -C.sub.Type: GrantFiled: September 19, 1985Date of Patent: December 18, 1990Assignee: Ciba-Geigy CorporationInventors: Erfinders K. Gass, Werner Fory, Willy Meyer, Werner Topfl
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Patent number: 4940792Abstract: Novel substituted N-sulfonyl-N'-pyrimidinylureas or N-sulfonyl-N'-triazinylureas of the formula I ##STR1## have good pre- and postemergence selective herbicidal and growth regulating properties.In this formulaE is nitrogen or --CH.dbd.,the group ##STR2## is a phenyl, naphthyl, furyl, thiophenyl, pyrrole or pyridinyl radical which is substituted in accordance with the definitions ofR.sup.1 and R.sup.2,R.sup.3 and R.sup.4 are hydrogen, lower alkyl or lower alkoxy, or one of R.sup.3 and R.sup.4 may also be halogen, lower alkenyl, lower haloalkenyl, lower haloalkoxy, amino, lower alkylamino, --CH(OCH.sub.3).sub.2, a cyclized ketal group or a saturated 5- or 7-membered heterocycle which is bound through the nitrogen atom,R.sup.5 is hydrogen, lower alkyl, lower haloalkyl, or an unsubstituted or substituted phenyl, benzyl or naphthyl radical, andR.sup.Type: GrantFiled: December 4, 1987Date of Patent: July 10, 1990Assignee: Ciba-Geigy CorporationInventors: Werner Topfl, Willy Meyer, Hans-Dieter Schneider
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Patent number: 4921955Abstract: The invention relates to a process for the preparation of 1,5-disubstituted imidazoles of the formula ##STR1## by alkylation of an N-cyanoformamidine of the formula IIX--NH--CH.dbd.N--CH (II)to form an N,N-disubstituted N'-cyanoformamidine of the formula ##STR2## which is cyclised under the action of bases to form a 4-aminoimidazole of the formula ##STR3## and then reduced to form the product of the formula I. The invention relates also to a special process for the reduction of the aminoimidazole V to I, and to intermediate compounds for carrying out this process and to processes for the preparation of the intermediate compounds.The meaning of the substituents X and L is explained in detail in the text.Type: GrantFiled: December 18, 1987Date of Patent: May 1, 1990Assignee: Ciba-Geigy CorporationInventor: Werner Topfl
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Patent number: 4904300Abstract: Imidazole derivatives of formula I ##STR1## and the stereochemically isomeric forms thereof, and salts thereof, have useful herbicidal properties. The substituents R.sup.1, L and X have the meanings defined herein.Type: GrantFiled: August 17, 1988Date of Patent: February 27, 1990Assignee: Ciba-Geigy Corp.Inventors: Hans-Dieter Schneider, William R. Lutz, Henry Szczepanski, Werner Topfl
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Patent number: 4904783Abstract: N-Arylsulfonyl-N'-(4-mercaptomethyl-pyrimidinyl)-ureas of the formula ##STR1## (symbols in this formula defined herein) and the salts of these compounds with amines, alkali metal bases or alkaline-earth metal bases or with ammonium bases, have good pre- and post-emergence-selective, herbicidal and growth-regulating properties.Type: GrantFiled: September 19, 1988Date of Patent: February 27, 1990Assignee: Ciba-Geigy CorporationInventor: Werner Topfl
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Patent number: 4902336Abstract: N-Arylsulfonyl-N'-(4-mercaptomethyl-pyrimidinyl-ureas of the formula ##STR1## (symbols in this formula defined herein) and the salts of these compounds with amines, alkali metal bases or alkaline-earth metal bases or with ammonium bases, have good pre- and post-emergence-selective, herbicidal and growth-regulating properties.Type: GrantFiled: September 19, 1988Date of Patent: February 20, 1990Assignee: Ciba-Geigy CorporationInventor: Werner Topfl
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Patent number: 4835311Abstract: N-Phenylsulfonyl-N'-pyrimidinylureas and -N'-triazinylureas of the general formula ##STR1## and the salts of these compounds with amines, alkali metal bases and alkaline earth metal bases or with quaternary ammonium bases, have good selective herbicidal and plant growth regulating properties when applied pre- and postemergence.In the formulaR.sub.1 is hydrogen, halogen, nitro, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.2 -C.sub.5 alkenyl or C.sub.1 -C.sub.4 alkoxycarbonyl,R.sub.2 is C.sub.1 -C.sub.3 alkyl or C.sub.1 -C.sub.3 alkoxy, each unsubstituted or substituted by 1 to 3 halogen atoms,R.sub.3 is halogen, hydrogen, --NR.sub.4 R.sub.5, C.sub.1 -C.sub.3 alkyl, unsubstituted or substituted by 1 to 3 halogen atoms of C.sub.1 -C.sub.4 alkoxy, or is C.sub.1 -C.sub.3 alkoxy, unsubstituted or substituted by methoxy, ethoxy, or 1 to 3 halogen atoms,R.sub.4 is hydrogen or methyl,R.sub.5 is hydrogen, C.sub.1 -C.sub.2 alkyl or methoxy,A is C.sub.1 -C.sub.4 alkylene or C.sub.Type: GrantFiled: January 11, 1988Date of Patent: May 30, 1989Assignee: Ciba-Geigy CorporationInventors: Karl Gass, Werner Fory, Willy Meyer, Werner Topfl
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Patent number: 4833252Abstract: Substituted N-phenylsulfonyl-N'-pyrimidinylureas and N-phenylsulfonyl-N'-triazinylureas of the general formula ##STR1## and the salts thereof with amines, alkali metal bases or alkaline earth metal bases, or with quaternary ammonium bases, have good pre- and postemergence selective herbicidal and growth regulating properties.In the above formula the symbols have the following meanings:R.sup.1 is hydrogen, halogen, nitro, cyano, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 alkylsulfonyl, C.sub.1 -C.sub.4 alkylsulfinyl, --CO--R.sup.8, --NR.sup.9 R.sup.10, --CO--NR.sup.11 R.sup.12 or --SO.sub.2 --NR.sup.13 R.sup.14,R.sup.2 is hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 alkylsulfinyl or C.sub.1 -C.sub.4 alkylsulfonyl,R.sup.3 is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl or cyano,R.sup.4 is hydrogen or C.sub.1 -C.sub.4 alkyl,R.sup.5 is hydrogen, C.sub.Type: GrantFiled: September 28, 1988Date of Patent: May 23, 1989Assignee: Ciba-Geigy CorporationInventors: Werner Topfl, Georg Pissiotas
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Patent number: 4786315Abstract: N-Arylsulfonyl-N'-(4-mercaptomethyl-pyrimidinyl- and -triazinyl)-ureas of the formula: ##STR1## and the salts of these compounds with amines, alkali metal bases or alkaline-earth metal bases or with ammonium bases, have good pre- and post-emergence-selective, herbicidal and growth-regulating properties.Type: GrantFiled: November 24, 1986Date of Patent: November 22, 1988Assignee: Ciba-Geigy CorporationInventor: Werner Topfl
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Patent number: 4785109Abstract: These is described a process for producing sulfonylureas of the formula ##STR1## wherein G is an unsubstituted or substituted furanyl, thienyl, pyrrolyl, pyridinyl or phenyl radical,X is alkyl, haloalkyl, alkoxy, alkylthio, halogen, haloalkoxy, alkylamino or dialkylamino,Y is alkyl, alkoxy or haloalkoxy,Z is a nitrogen atom or the methyne group --CH.dbd..This novel process comprises reacting a sulfonamide of the formulaG--SO.sub.2 --NH.sub.2,in the presence of a base, with a chloroformic acid ester of the formulaCl--CO--Q--T,or a sulfonyl chloride of the formulaG--SO.sub.2 Cl,in the presence of a base, with a urethane of the formulaH.sub.2 N--CO--Q--T;and converting the formed carbamate of the formulaG--SO.sub.2 --NH--CO--Q--Tby reaction with an amine of the formula ##STR2## into the sulfonylurea of the above formula. There are also described novel sulfonylcarbamates of the above formula as intermediates.Type: GrantFiled: January 30, 1987Date of Patent: November 15, 1988Assignee: Ciba-Geigy CorporationInventors: Willy Meyer, Werner Fory, Werner Topfl
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Patent number: 4764203Abstract: Novel substituted N-sulfonyl-N'-pyrimidinylureas or N-sulfonyl-N'-triazinylureas of the formula I ##STR1## have good pre- and postemergence selective herbicidal and growth regulating properties.In this formulaE is nitrogen or --CH.dbd.,the group ##STR2## is a phenyl, naphthyl, furyl, thiophenyl, pyrrole or pyridinyl radical which is substituted in accordance with the definitions of R.sup.1 and R.sup.2,R.sup.3 and R.sup.4 are hydrogen, lower alkyl or lower alkoxy, or one of R.sup.3 and R.sup.4 may also be halogen, lower alkenyl, lower haloalkenyl, lower haloalkoxy, amino, lower alkylamino, --CH(OCH.sub.3).sub.2, a cyclized ketal group or a saturated 5- to 7-membered heterocycle which is bound through the nitrogen atom,R.sup.5 is hydrogen, lower alkyl, lower haloalkyl, or an unsubstituted or substituted phenyl, benzyl or naphthyl radical, andR.sup.Type: GrantFiled: May 26, 1987Date of Patent: August 16, 1988Assignee: Ciba-Geigy CorporationInventors: Werner Topfl, Willy Meyer, Hans-Dieter Schneider
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Patent number: 4740236Abstract: N-Sulfonyliminothiocarbonic acid diesters protect rice crops from phytotoxic damage caused by herbicides.Type: GrantFiled: November 23, 1983Date of Patent: April 26, 1988Assignee: Ciba-Geigy CorporationInventor: Werner Topfl
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Patent number: 4739068Abstract: N-Phenylsulfonyl-N'-pyrimidinylureas and --N'-triazinylureas of the general formula ##STR1## and the salts of these compounds with amines, alkali metal bases and alkaline earth metal bases or with quaternary ammonium bases, have good selective herbicidal and plant growth regulating properties when applied pre- and postemergence.In the formulaR.sub.1 is hydrogen, halogen, nitro, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.2 -C.sub.5 alkenyl or C.sub.1 -C.sub.4 alkoxycarbonyl,R.sub.2 is C.sub.1 -C.sub.3 alkyl or C.sub.1 -C.sub.3 alkoxy, each unsubstituted or substituted by 1 to 3 halogen atoms,R.sub.3 is halogen, hydrogen, --NR.sub.4 R.sub.5, C.sub.1 -C.sub.3 alkyl, unsubstituted or substituted by 1 to 3 halogen atoms or C.sub.1 -C.sub.4 alkoxy, or is C.sub.1 -C.sub.3 alkoxy, unsubstituted or substituted by methoxy, ethoxy, or 1 to 3 halogen atoms,R.sub.4 is hydrogen or methyl,R.sub.5 is hydrogen, C.sub.1 -C.sub.2 alkyl or methoxy,A is C.sub.1 -C.sub.4 alkylene or C.sub.Type: GrantFiled: July 21, 1986Date of Patent: April 19, 1988Assignee: Ciba-Geigy CorporationInventors: Karl Gass, Werner Fory, Willy Meyer, Werner Topfl
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Patent number: 4726836Abstract: N-Phenylsulfonyl-N'-pyrimidinylureas and -N'-triazinylureas of the general formula ##STR1## and the salts of these compounds with amines, alkali metal bases and alkaline earth metal bases or with quaternary ammonium bases, have good selective herbicidal and plant growth regulating properties when applied pre- and postemergence.In the formulaR.sub.1 is hydrogen, halogen, nitro, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.2 -C.sub.5 alkenyl or C.sub.1 -C.sub.4 alkoxycarbonyl,R.sub.2 is C.sub.1 -C.sub.2 alkyl or C.sub.1 -C.sub.3 alkoxy, each unsubstituted or substituted by 1 to 3 halogen atoms,R.sub.3 is halogen, hydrogen, --NR.sub.4 R.sub.5, C.sub.1 -C.sub.3 alkyl, unsubstituted or substituted by 1 to 3 halogen atoms or C.sub.1 -C.sub.4 alkoxy, or is C.sub.1 -C.sub.3 alkoxy, unsubstituted or substituted by methoxy, ethoxy, or 1 to 3 halogen atoms,R.sub.4 is hydrogen or methyl,R.sub.5 is hydrogen, C.sub.1 -C.sub.2 alkyl or methoxy,A is C.sub.1 -C.sub.4 alkylene or C.sub.Type: GrantFiled: July 21, 1986Date of Patent: February 23, 1988Assignee: Ciba-Geigy CorporationInventors: Karl Gass, Werner Fory, Willy Meyer, Werner Topfl
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Patent number: 4701206Abstract: Substituted N-phenylsulfonyl-N'-pyrimidinylureas and N-phenylsulfonyl-N'-triazinylureas of the general formula ##STR1## and the salts thereof with amines, alkali metal bases or alkaline earth metal bases, or with quaternary ammonium bases, have good pre- and postemergence selective herbicidal and growth regulating properties.In the above formula the symbols have the following meanings:R.sup.1 is hydrogen, halogen, nitro, cyano, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 alkylsulfonyl, C.sub.1 -C.sub.4 alkylsulfinyl, --CO--R.sup.8, --NR.sup.9 R.sup.10, --CO--NR.sup.11 R.sup.12 or --SO.sub.2 --NR.sup.13 R.sup.14,R.sup.2 is hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 alkylsulfinyl or C.sub.1 -C.sub.4 alkylsulfonyl,R.sup.3 is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl or cyano,R.sup.4 is hydrogen or C.sub.1 -C.sub.4 alkyl,R.sup.5 is hydrogen, C.sub.Type: GrantFiled: April 25, 1986Date of Patent: October 20, 1987Assignee: Ciba-Geigy CorporationInventors: Werner Topfl, Georg Pissiotas