Chalcogen Bonded Directly To Triazine Ring Carbon Patents (Class 544/218)
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Patent number: 5959106Abstract: N-(substituted aryl)?1,2,4!triazoloazinesulfonamide compounds, such as N-(2,6-difluorophenyl)-8-fluoro-5-methoxy?1,2,4!triazolo?1,5-c!pyrimidine- 2-sulfonamide, were prepared at a good reaction rate and in good yield by the reaction of a chlorosulfonyl?1,2,4!triazoloazine compound, such as 2-chlorosulfonyl-8-fluoro-5-methoxy?1,2,4!triazolo?1,5-c!pyrimidine, and an arylamine compound, such as 2,6-difluoroaniline, in an organic medium containing a relatively acidic alcohol, such as propylene glycol or 2,2,2-trifluoroethanol.Type: GrantFiled: January 25, 1999Date of Patent: September 28, 1999Assignee: Dow AgroSciences LLCInventors: Douglas L. Pearson, Timothy J. Adaway
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Patent number: 5942509Abstract: Fungicidal compounds having the formula (I): ##STR1## in which any two of K, L and M are nitrogen and the other is CA wherein A is H, halogen, C.sub.1-4 alkyl, cyano, nitro or trifluoromethyl; X is a linking group other than oxygen; T is oxygen or sulphur; and Z is an optionally substituted carbocyclic or heterocyclic ring.Type: GrantFiled: January 31, 1997Date of Patent: August 24, 1999Assignee: Zeneca LimitedInventors: John Martin Clough, Christopher Richard Ayles Godfrey, Paul John De Fraine, Ian Thomas Streeting, Gordon Richard Munns
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Patent number: 5925597Abstract: Compounds of the formula (I) and their salts as defined in claim 1, ##STR1## in which R.sup.1 is CO--Q--R.sup.8, where R.sup.8 =H or RR.sup.2 and R.sup.3 are H or (C.sub.1 -C.sub.4)alkyl,R.sup.4 is H, R, RO, OH, RCO, RSO.sub.2, PhSO.sub.2R.sup.5 is RSO.sub.2, PhSO.sub.2, PhCO, RNHSO.sub.2, R.sub.2 NSO.sub.2, RCO, CHO, COCOR', CW--T--R.sup.9, CW--NR.sup.10 R.sup.11, CW--N(R.sup.12).sub.2 orR.sup.4 and R.sup.5 together are the chain (CH.sub.2).sub.m B or --B.sup.1 --(CH.sub.2).sub.m1 B-- where B=SO.sub.2, CO; m=3, 4; m.sup.1 =2, 3;T and W=O, S; Q=O, S, NR.sup.13 where R.sup.13 =H, R;R.sup.6 =H, R, RO, RCO, ROCO, Hal, NO.sub.2, CN;R.sup.7 =H, CH.sub.3 ; R.sup.9 =R; R.sup.10, R.sup.11 =H, R; N(R.sup.12).sub.2 =heterocycleA=pyrimidinyl and triazinyl radical or an analog thereof,where R=(substituted) aliphatic hydrocarbon radical, are suitable as selective herbicides. They are prepared by analogous processes via sulfonamides, some of which are new, of the formula (II).Type: GrantFiled: March 31, 1997Date of Patent: July 20, 1999Assignee: Hoechst Schering AgrEvo GmbHInventors: Klaus Lorenz, Lothar Willms, Klaus Bauer, Hermann Bieringer
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Patent number: 5922710Abstract: Iminooxybenzylcrotonate esters of the formula I ##STR1## where the index and the substituents have the following meanings: n is 0, 1, 2, 3 or 4;R is nitro, cyano, halogen,unsubst. or subst. alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy orin the case where n is 2, additionally an unsubst. or subst. bridge bonded to two adjacent ring atoms;R.sup.1 is C.sub.1 -C.sub.4 -alkyl;R.sup.2 is hydrogen or C.sub.1 -C.sub.4 -alkyl;R.sup.3 is hydrogen, cyano, halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio or cycloalkyl;R.sup.4 is a 5 to 10-membered mono- or bicyclic, substituted heteroaromatic ring system,processes for their preparation and their use are described.Type: GrantFiled: May 22, 1997Date of Patent: July 13, 1999Assignee: BASF AktiengesellschaftInventors: Bernd Muller, Wassilios Grammenos, Hubert Sauter, Franz Rohl, Eberhard Ammermann, Gisela Lorenz, Norbert Gotz
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Patent number: 5885935Abstract: Herbicidal sulfonamides of the formula: ##STR1## and salts thereof, where: A represents a substituted or unsubstituted benzene ring, or a 5- or 6-membered substituted or unsubstituted heteroaromatic ring; Q is --O--, --S-- or a group --CXX'--; X and X', which may be the same or different, are each hydrogen, halogen, cyano, an optionally-substituted alkyl group, or a group --OR.sup.a, --SR.sup.a, or --COR.sup.b ; or one of X and X' represents hydroxy and the other is as defined above; or X and X' together represent .dbd.O or .dbd.S; R.sup.a is an optionally-substituted alkyl, aryl or acyl group; R.sup.b is an optionally-substituted alkyl or aryl group, or a group --OR.sup.c or --NR.sup.c R.sup.d ; R.sup.c and R.sup.d, which may be the same or different, are each hydrogen, or an optionally-substituted alkyl or aryl group; Y is nitrogen or a group CR.sup.9 ; R.sup.1 is an optionally-substituted alkyl, alkenyl, alkynyl, cycloalkyl, aryl, heterocyclyl, benzoheterocyclyl or amino group; R.sup.Type: GrantFiled: June 21, 1996Date of Patent: March 23, 1999Assignee: Agrevo UK LimitedInventors: Peter Stuart Gates, Graham Peter Jones, David Edward Saunders
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Patent number: 5770544Abstract: A condensed heterocyclic derivative of the formula ##STR1## (wherein R is a hydroxyl group, R.sup.3 or R.sup.4 is an alkoxy group, W is an oxygen atom, Yn is a hydrogen atom, Z is a methine group, and A is a 5- or 6-membered heterocyclic ring which may be substituted, and a herbicide, are presented. When used for paddy field treatment, upland soil treatment and foliage treatment, the condensed heterocyclic derivative of the present invention exhibits excellent herbicidal activities against gramineous and non-gramineous weeds without adversely affecting crop plants.Type: GrantFiled: October 9, 1996Date of Patent: June 23, 1998Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.Inventors: Sumio Yokota, Masafumi Matsuzawa, Nobuyuki Ohba, Toshihiro Nagata, Shigehiko Tachikawa, Takeshige Miyazawa, Katsutada Yanagisawa
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Patent number: 5760227Abstract: The compounds of the s-triazine series of formula I ##STR1## wherein the symbols R.sub.1, R.sub.2, R.sub.3, X and n possess the significances given in claim 1, are eminently suitable, when applied to textile material, as UV-absorbers, as resist agents for anionic dyes, and as stain blockers.Type: GrantFiled: July 31, 1996Date of Patent: June 2, 1998Assignee: Clariant Finance (BVI) LimitedInventor: Jean-Luc Mura
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Patent number: 5700295Abstract: The invention relates to compounds of formula ##STR1## wherein the variables have the meanings given in the claims. The compounds are suitable for use as UV absorbers for the photochemical stabilisation of undyed, dyed or printed textile fiber materials and for enhancing the sun protection factor thereof.Type: GrantFiled: October 11, 1995Date of Patent: December 23, 1997Assignee: Ciba Specialty Chemicals CorporationInventors: Francesco Fuso, Gerhard Reinert
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Patent number: 5696262Abstract: The invention relates to novel water-soluble triazines of formula ##STR1## wherein the variables are as defined in the claims, to a process for their preparation and to the use thereof for the photochemical and thermal stabilisation of dyed or undyed polyamide fiber materials.Type: GrantFiled: August 22, 1995Date of Patent: December 9, 1997Assignee: Ciba Specialty Chemicals CorporationInventors: Francesco Fuso, Gerhard Reinert
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Patent number: 5661106Abstract: 3-(Het)aryloxy(thio)carboxylic acid derivatives of the formula I ##STR1## where R.sup.1 is hydrogen, COOH or a radical which can be hydrolyzed to give COOH;R.sup.2 and R.sup.3 are each halogen, alkyl, haloalkyl, alkoxy, haloalkoxy or alkylthio;X is nitrogen or CR.sup.14, where R.sup.14 is hydrogen or, together with R.sup.3, forms a 3-membered or 4-membered alkylene or alkenylene chain, in each of which a methylene group is replaced by oxygen;R.sup.4 is alkyl, cycloalkyl, cycloalkenyl, alkenyl or alkynyl, each of which is unsubstituted or substituted;an unsubstituted or substituted five-membered or six-membered heteroaromatic structure containing one to three nitrogen atoms or one sulfur or oxygen atom;unsubstituted or substituted phenyl or naphthyl;R.sup.4 and R.sup.5, together with the neighboring carbon atom, form a 3-membered to 8-membered ring which may contain an oxygen or sulfur atom and which is unsubstituted or substituted;R.sup.Type: GrantFiled: October 19, 1995Date of Patent: August 26, 1997Assignee: BASF AktiengesellschaftInventors: Ernst Baumann, Joachim Rheinheimer, Uwe Josef Vogelbacher, Matthias Bratz, Norbert Meyer, Matthias Gerber, Karl-Otto Westphalen, Helmut Walter, Wilhelm Rademacher
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Patent number: 5612338Abstract: Compounds of the formula ##STR1## wherein R.sub.1 is hydrogen or methyl,R.sub.2 is hydrogen, halogen, OCH.sub.3, SCH.sub.3 or CN,R.sub.3, R.sub.4, R.sub.5 are each independently of one another hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.2 -C.sub.5 alkoxycarbonyl, C.sub.1 -C.sub.5 alkanoyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 haloalkoxy, CN, NO.sub.2, or wherein two of those substituents are adjacent to each other and together are a methylenedioxy or difluoromethylenedioxy radical,K, L, M are each independently of one another CH or N (=nitrogen atom), but at least one of these three substituents is N, andY is oxygen or sulfur,are effective microbicides for controlling fungal diseases. They can be used for plant protection by themselves or as formulated compositions.Type: GrantFiled: July 28, 1995Date of Patent: March 18, 1997Assignee: Ciba-Geigy CorporationInventor: Stephan Trah
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Patent number: 5585422Abstract: s-Triazine UV absorbers substituted by a benzotriazolyl or benzophenonyl moiety exhibit unexpectedly improved UV absorption characteristics and outstanding efficacy in protecting organic substances from the deleterious effects of actinic radiation as well as good resistance to loss by volatilization during processing of stabilized compositions at elevated temperatures.Type: GrantFiled: September 20, 1995Date of Patent: December 17, 1996Assignee: Ciba-Geigy CorporationInventors: Robert A. Falk, Tyler A. Stevenson, Gregory R. Coughlin
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Patent number: 5563266Abstract: Disubstituted monochlorotriazines such as 2-chloro-4-mesitoxy-6-glycidoxy-1,3,5-triazine are prepared in organic solution by first combining a monoorganoxy dichlorotriazine with an aqueous alkali metal hydroxide solution in a specific concentration and molar ratio, and adding to the mixture thus produced a hydroxyaliphatic or hydroxyaromatic compound, preferably glycidol, in the presence of at least one hydrophilic phase transfer catalyst such as tetra-n-butylammonium bromide. The reaction can be integrated with either or both of a prior step of dichlorotriazine preparation and a subsequent step of capping a hydroxy-terminated polymer, especially a polyphenylene ether.Type: GrantFiled: June 2, 1995Date of Patent: October 8, 1996Assignee: General Electric CompanyInventors: Thomas J. Stanley, Sterling B. Brown, Paul E. Howson
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Patent number: 5545835Abstract: There are provided 5,6-disubstituted-3-pyridylmethyl ammonium halide compounds, a method for the preparation thereof and the use thereof for the preparation of 5-(substituted methyl)-2,3-pylidinedicarboxylic acids.Type: GrantFiled: November 4, 1994Date of Patent: August 13, 1996Assignee: American Cyanamid CompanyInventor: Henry L. Strong
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Patent number: 5482920Abstract: Pyrimidinyloxy- and triazinyloxy- and pyrimidinylthio- and triazinylthio-butyric acid derivatives of formula I ##STR1## wherein Q is ##STR2## A is hydroxy or a group ##STR3## and the other substituents are as described in patent claim 1, and salts of compounds of formula I, have herbicidal action and are suitable as active ingredients in weed control compositions.Type: GrantFiled: February 15, 1994Date of Patent: January 9, 1996Assignee: Ciba-Geigy CorporationInventor: Christoph Luthy
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Patent number: 5464809Abstract: Fungicidal new 2-methoximinocarboxylic esters of the general formula (I) ##STR1## in which Ar represents one of the radicals ##STR2## and A represents one of the radicals --CH.sub.2 --; ##STR3## where Y represents one of the radicals ##STR4## --O--CH.sub.2 --; --CH.sub.2 --O--; --S--CH.sub.2 --; ##STR5## --SO.sub.2 --CH.sub.2 --; --O--; --CH.dbd.CH-- or --CH.sub.2 --CH.sub.2 --,n represents the number 0 or 1,R represents alkyl, halogenoalkyl, alkenyl, halogenoalkenyl, or represents optionally substituted cycloalkyl, or represents optionally substituted aryl or represents optionally substituted heteroaryl, and, moreover, in the event that n is 0, also represents halogen, andX.sup.1, X.sup.2, X.sup.3 and X.sup.4 independently of one another in each case represent hydrogen, halogen, hydroxyl or methoxy, but where, in the event that X.sup.2 represents bromine, X.sup.3 does not simultaneously represent hydroxyl or methoxy.Type: GrantFiled: September 12, 1994Date of Patent: November 7, 1995Assignee: Bayer AktiengesellschaftInventors: Wolfgang Kramer, Dieter Berg, Heinz-Wilhelm Dehne, Stefan Dutzmann
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Patent number: 5446155Abstract: Disubstituted monochlorotriazines such as 2-chloro-4-mesitoxy-6-glycidoxy-1,3,5-triazine are prepared in organic solution by first combining a monoorganoxy dichlorotriazine with an aqueous alkali metal hydroxide solution in a specific concentration and molar ratio, and adding to the mixture thus produced a hydroxyaliphatic or hydroxyaromatic compound, preferably glycidol, in the presence of at least one hydrophilic phase transfer catalyst such as tetra-n-butylammonium bromide. The reaction can be integrated with either or both of a prior step of dichlorotriazine preparation and a subsequent step of capping a hydroxy-terminated polymer, especially a polyphenylene ether.Type: GrantFiled: August 30, 1994Date of Patent: August 29, 1995Assignee: General Electric CompanyInventors: Thomas J. Stanley, Sterling B. Brown, Paul E. Howson
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Patent number: 5428002Abstract: The invention relates to compounds of formula ##STR1## wherein W, X, Y.sup.1, Y.sup.2, Z, R.sup.1, R.sup.2 and R.sup.14 are as defined in the description, and to the preparation thereof, to weed control compositions and plant-growth-regulating compositions comprising such compounds as active ingredients, and to the use of the active ingredients or compositions for controlling weeds and for regulating plant growth.Type: GrantFiled: May 13, 1994Date of Patent: June 27, 1995Assignee: Ciba-Geigy CorporationInventors: Christoph Luthy, Jean-Pierre Obrecht
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Patent number: 5418212Abstract: The present invention provides a novel alkanoic acid amide derivative of the formula, ##STR1## (wherein R.sup.1 is a hydrogen atom, an alkyl group or an alkoxyalkoxy group, R.sup.2 is a group of --SO.sub.2 R or a hydroxyl group, R.sup.5 is an alkyl group, R.sup.3 is an alkyl group, a cycloalkyl group, a cycloalkenyl group or a phenyl group, R.sup.4 is a hydrogen atom or an alkyl group, X and Y may be the same or different and are an alkoxy group, an alkylamino group or a dialkylamino group, and Z is a methine group or a nitrogen atom) and its salt, a process for preparing the same and a herbicidal composition containing the same as an effective ingredient.This compound kills annual and perennial weeds grown in paddy fields and upland fields at a small dose, and is safe to a useful crop plant.Type: GrantFiled: April 27, 1993Date of Patent: May 23, 1995Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.Inventors: Takumi Yoshimura, Keiji Toriyabe, Katsumi Masuda, Ryo Hanai
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Patent number: 5378843Abstract: There are provided 5,6-disubstituted-3-pyridylmethyl ammonium halide compounds, a method for the preparation thereof and the use thereof for the preparation of 5-(substituted methyl)-2,3-pyridinedicarboxylic acids.Type: GrantFiled: November 22, 1993Date of Patent: January 3, 1995Assignee: American Cyanamid CompanyInventor: Henry L. Strong
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Patent number: 5354779Abstract: New oxime ether amides of the formula (I) ##STR1## in which R has the meaning given in the description, and a plurality of processes for their preparation were described.The new oxime ether amides are used as pesticides.Type: GrantFiled: November 30, 1992Date of Patent: October 11, 1994Assignee: Bayer AktiengesellschaftInventors: Wolfgang Kramer, Dieter Berg, Heinz-Wilhelm Dehne, Stefan Dutzmann, Christoph Erdelen
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Patent number: 5342940Abstract: High purity polyethylene glycol derivatives of formula (I) are useful as protein modifiers of interferons, t-PA, EGF, various hormones, etc. The thus modified protein has minimized antigenicity, prolonged plasma half life, or improved transfer to tissue. A novel process for preparing high purity polyethylene glycol derivatives is also disclosed.Type: GrantFiled: September 13, 1993Date of Patent: August 30, 1994Assignees: Sumitomo Pharmaceuticals Company, Limited, Seikagaku CorporationInventors: Keiichi Ono, Yoshiyuki Kai, Hiroo Maeda
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Patent number: 5312918Abstract: Halo-displacement reaction products of aliphatic hydroxy compounds and chloro- or bromo-substituted aromatic nitrogen-heterocyclic compounds are conducted under alkaline conditions in the presence of a phase transfer catalyst, in the substantial absence of water inorganic salts other than those formed in the reaction. The method is particularly useful for the preparation of substituted chlorotriazines. In a preferred embodiment, the reagents constitute at least about 25% by weight of the organic phase of the reaction mixture.Type: GrantFiled: May 24, 1993Date of Patent: May 17, 1994Assignee: General Electric CompanyInventors: John C. Schmidhauser, Kathryn L. Longley, William L. Gately
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Patent number: 5300502Abstract: Phenoxyalkyl-substituted heteroaromatics of the general formulae Ia and Ib ##STR1## where A is an unsubstituted or substituted heteroaromatic radical having 6 5 ring members and 1, 2 or 3 nitrogen atoms in the ring, R.sup.1 is hydrogen, halogen or C.sub.1 -C.sub.3 -alkyl. R.sup.2 is hydrogen or C.sub.1 -C.sub.4 -alkyl. Q.sub.a is an unsubstituted or substituted azole radical and Q.sub.b is a substituted or unsubstituted heteroaromatic radical which has a five-membered ring,and their use for combating pests.Type: GrantFiled: July 8, 1993Date of Patent: April 5, 1994Assignee: BASF AktiengesellschaftInventors: Joachim Leyendecker, Hans-Juergen Neubauer, Uwe Kardorff, Christoph Kuenast, Peter Hofmeister, Wolfgang Krieg
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Patent number: 5290931Abstract: Water-insoluble naphthalic acid imide dyestuffs of the following formula: ##STR1## wherein D is ##STR2## wherein R.sup.1 is C.sub.1 -C.sub.8 alkyl which may be substituted, R.sup.2 is hydrogen, halogen, lower alkyl, lower alkoxy or cyano, X is oxygen or sulfur, and m is 0 or 1; A is phenylene, alkylene, aralkylene or --C.sub.2 H.sub.4 OC.sub.2 H.sub.4 --; B is oxygen, sulfur or ##STR3## wherein R.sup.3 is hydrogen or lower alkyl; Y is a 6-membered nitrogen-containing heterocyclic ring having at least one active halogen atom; and n is 0 or 1.Type: GrantFiled: September 4, 1992Date of Patent: March 1, 1994Assignee: Hoechst Mitsubishi Kasei Co., Ltd.Inventors: Kiyoshi Himeno, Toshio Hihara
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Patent number: 5288866Abstract: There are provided 5,6-disubstituted-3-pyridylmethyl ammonium halide compounds, a method for the preparation thereof and the use thereof for the preparation of 5-(substituted methyl)-2,3-pyridinedicarboxylic acids.Type: GrantFiled: October 14, 1992Date of Patent: February 22, 1994Assignee: American Cyanamid CompanyInventor: Henry L. Strong
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Patent number: 5283363Abstract: The invention relates to a new process for the preparation of (hetero)arylalk(en/in)ylamines of the formula (I) ##STR1## in which A represents ethane-1,2-diyl (ethylene, dimethylene, --CH.sub.2 --CH.sub.2 --) or represents ethene-1,2-diyl (ethenylene, vinylene, --CH.dbd.CH--) or represents ethine-1,2-diyl (ethinylene, --C.ident.C--),characterized in that(a) in the event that, in formula (I), A represents ethine-1,2-diyl, halogeno(hetero)aryl compounds of the general formula (II)Ar--X (II)are reacted with aminoalkinyl compounds of the general formula (III) ##STR2## and, if appropriate, (b) in the event that, in formula (I), A represents ethane-1,2-diyl or ethene-1,2-diyl, the new (hetero)aralkinylamines which are obtained by the process step described under (a), of the general formula (Ia), ##STR3## are reacted with a hydrogenating agent, if appropriate in the presence of a catalyst and if appropriate in the presence of a diluent, the definitions applying to Ar, R.sup.1, R.sup.Type: GrantFiled: January 16, 1992Date of Patent: February 1, 1994Assignee: Bayer AktiengesellschaftInventors: Dietmar Kuhnt, Thomas Himmler, Heinz Ziemann
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Patent number: 5280118Abstract: Trifluoro- and chlorodifluoromethoxy-1,3,5-triazines of the formula I ##STR1## where R.sup.1 and R.sup.2 are each, independently of one another, hydrogen, halogen or C.sub.1 -C.sub.4 -haloalkyl, and R.sup.1 is also trifluoro- or chlorodifluoromethoxy, and n is 0 or 1, excepting 2,4-dichloro-6-trifluoromethoxy-1,3,5-triazine, are prepared as described.Type: GrantFiled: December 3, 1992Date of Patent: January 18, 1994Assignee: BASF AktiengesellschaftInventors: Gerhard Hamprecht, Horst Mayer, Hans-Josef Wolf
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Patent number: 5276033Abstract: Compounds having the formula (I) ##STR1## wherein: R.sup.1 is methyl, ethyl or isopropyl; R.sup.2 is alkyl, aralkyl, cycloalkyl, cycloalkylmethyl, aryl, heterocyclic, or heterocyclic-substituted thio; R.sup.3 is hydrogen, methyl or ethyl; or R.sup.2 together with R.sup.3 is --(CH.sub.2).sub.n --, wherein n is 3,4 or 5; and A is aromatic heterocyclic; and salts thereof, are valuable agricultural and horticultural anthelmintic, acaricidal and insecticidal agents.Type: GrantFiled: December 17, 1992Date of Patent: January 4, 1994Assignee: Sankyo Company, LimitedInventors: Toshiaki Yanai, Soji Sugai, Hideo Takeshiba, Junzo Tobitsuka, Kazuo Sato, Shinji Yokoi, Shinya Niimi, Akio Saito
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Patent number: 5270289Abstract: The invention relates to new substituted .alpha.-pyrimidinyloxy(thio)- and .alpha.-triazinyloxy(thio)carboxylic acid derivatives of general formula I ##STR1## in which A, R.sup.1-3, X and Y have the meanings given in the description, processes for their preparation and their use as herbicides, fungicides and plant growth regulants.Type: GrantFiled: April 1, 1992Date of Patent: December 14, 1993Assignee: Schering AktiengesellschaftInventors: Christoph Harde, Erhard Nordhoff, Anita Kruger, Gabriele Kruger, Gerhard Tarara, Peter Wegner, Nikolaus Heinrich, Clemens Kotter, Gerhard Johann, Richard Rees
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Patent number: 5252760Abstract: A method of phosphorylating a nucleoside or an oligonucleotide chain having a free 2', 3' or 5' hydroxyl moiety is provided. The method involves the use of a phosphorylating reagent which is selected such that the extent of phosphorylation can be monitored colorimetrically, easily and accurately. The phosphorylating reagent contains an aromatic species such as a dimethoxytrityl group that is cleavable with acid and colorimetrically detectable upon release.Type: GrantFiled: August 18, 1987Date of Patent: October 12, 1993Assignee: Chiron CorporationInventors: Michael S. Urdea, Thomas Horn
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Patent number: 5236923Abstract: New substituted pyrimidylamide oximes of the general formula (I) ##STR1## in which R.sup.1, R.sup.2, R.sup.3, A and Ar have the meanings given in the description, new intermediates for their preparation, and their use for combating pests.The new compounds of the formula (I) can be prepared by analogous processes, for example by reacting suitable pyrimidylamide oximes with suitable alkylating agents. The starting compounds which are also new, namely the pyrimidylamide oximes of the formula (II) in which --A--Ar represents hydrogen, can be prepared from suitable cynaopyrimidines with hydroxylamine or its acid adducts.Type: GrantFiled: November 26, 1991Date of Patent: August 17, 1993Assignee: Bayer AktiengesellschaftInventors: Rolf Kirsten, Hilmar Wolf, Gerd Hanssler, Heinz-Wilhelm Dehne, Stefan Dutzmann
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Patent number: 5232896Abstract: 2-(Phenoxy or phenylthio)-2-(pyrimidinyloxy or 1,3,5-triazinyloxy)alkanoic acid compounds, such as ethyl 2-(2-fluorophenoxy)-2-(4,6-dimethylpyrimidin-2-yloxy)-acetate, were prepared by the reaction of a phenol or thiophenol compound with a 2-chloro-2-(pyrimidinyloxy or 1,3,5-triazinyloxy)alkanoate ester compound or by the reaction of a pyrimidinol or 1,3,5-triazinol with a 2-bromo-2-(phenoxy or phenylthio)alkanoate ester. These compounds, and, especially, agriculturally acceptable salts, esters, and amides of these compounds, were found to have herbicidal utility.Type: GrantFiled: May 6, 1992Date of Patent: August 3, 1993Assignee: DowElancoInventors: Michael G. Smith, William C. Lo, Wendy S. Jacks, Robert J. Ehr
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Patent number: 5229513Abstract: Substituted dichlorotriazines are prepared by the reaction of a suitable hydroxy compound with cyanuric chloride in a substantially non-polar organic solvent, in the presence of an aqueous alkali metal hydroxide solution having a concentration in the range of about 1-20% by weight and a phase transfer catalyst. The phase transfer catalyst employed is a tetraalkylammonium or tetraalkylphosphonium salt free from aromatic substituents and wherein the alkyl groups contain 3-5 carbon atoms. Hydrophilic phase transfer catalysts, in which the alkyl groups contain up to about 5 carbon atoms, are preferred.Type: GrantFiled: September 17, 1992Date of Patent: July 20, 1993Assignee: General Electric CompanyInventors: Sterling B. Brown, Thomas J. Stanley
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Patent number: 5194610Abstract: Trifluoro- and chlorodifluoromethoxy-1,3,5-triazines of the formula I ##STR1## where R.sup.1 and R.sup.2 are each, independently of one another, hydrogen, halogen or C.sub.1 -C.sub.4 -haloalkyl, and R.sup.1 is also trifluoro- or chlorodifluoromethoxy, and n is 0 or 1, excepting 2,4-dichloro-6-trifluoromethoxy-1,3,5-triazine, are prepared as described.Type: GrantFiled: July 26, 1991Date of Patent: March 16, 1993Assignee: BASF AktiengesellschaftInventors: Gerhard Hamprecht, Horst Mayer, Hans-Josef Wolf
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Patent number: 5186736Abstract: Compounds of the formula I or salts thereof ##STR1## where R.sup.1 is H or an aliphatic radical; R.sup.2 and R.sup.3 are H, alkyl or phenyl; W is O, S, NR.sup.4 or NOR.sup.4 ; X is CHR.sup.2, O or NR.sup.4 ; L is a (substituted) phenyl, naphthyl or monocyclic heteroaryl radical, A is a (substituted) pyrimidyl, triazinyl, triazolyl or bicyclic heteroaryl radical, and m and n are 0 or 1, have advantageously herbicidal or plant growth-regulating properties.Type: GrantFiled: July 11, 1991Date of Patent: February 16, 1993Assignee: Hoechst AktiengesellschaftInventors: Oswald Ort, Lothar Willms, Klaus Bauer, Hermann Bieringer, Arno Schulz
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Patent number: 5186734Abstract: Herbicidal bisazinyl compounds of the formula ##STR1## in which A.sup.1 and A.sup.2 are identical or different and represent nitrogen or a C--X group, X representing hydrogen, halogen, alkyl or alkoxy, andQ.sup.1 and Q.sup.2 are identical or different and represent oxygen, sulphur, NH or N-alkyl,(the substituents R, X.sup.1, X.sup.2, Y.sup.1, Y.sup.2 and Z representing a variety of organic radicals).The compounds of the formulas ##STR2## are also new.Type: GrantFiled: September 11, 1991Date of Patent: February 16, 1993Assignee: Bayer AktiengesellschaftInventors: Roland Andree, Mark W. Drewes, Hans-Joachim Santel, Klaus Lurssen, Robert R. Schmidt
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Patent number: 5185027Abstract: Salicylaldehyde derivatives and salicylic acid derivatives of the formula I ##STR1## where A is an unsubstituted or substituted phenyl radical, an unsubstituted or substituted 5-membered heteroaromatic radical having from 2 to 4 nitrogen atoms or two nitrogen atoms and additionally one sulfur or oxygen atom or an unsubstituted or substituted thienyl, pyridyl, naphthyl, quinolyl, indazolyl or benzotriazolyl radical, X is oxygen or sulfur, and the radicals R.sup.1 to R.sup.4 have the meanings given in the specification, processes and intermediates for their production, and their use as herbicides and bioregulators.Type: GrantFiled: November 7, 1991Date of Patent: February 9, 1993Assignee: BASF AktiengesellschaftInventors: Uwe J. Vogelbacher, Karl Eicken, Joachim Rheinheimer, Norbert Goetz, Albrecht Harreus, Gerhard Paul, Karl-Otto Westphalen, Bruno Wuerzer
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Patent number: 5159075Abstract: Substituted alkoxy- or alkylthiochlorotriazines wherein the substituents on the alkoxy groups are chlorine, bromine or dialkylphosphato are useful as capping agents for polyphenylene ethers. The capped polyphenylene ethers form copolymers with other polymers containing nucleophilic groups, including polyesters, polyamides and functionalized olefin polymers. Such copolymers serve as compatibilizers in the formation of blends having high impact strength.Type: GrantFiled: February 11, 1991Date of Patent: October 27, 1992Assignee: General Electric CompanyInventors: Otto Phanstiel, Sterling B. Brown
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Patent number: 5158954Abstract: Fungicidal compounds of the formula (I): ##STR1## and stereoisomers thereof, wherein K is oxygen or sulphur; Z is optionally substituted aryl or optionally substituted heteroaryl; X is O, S(O).sub.n, NR.sup.4, CR.sup.1 R.sup.2, CHR.sup.5, CO, CR.sup.1 (OR.sup.2), C.dbd.CR.sup.1 R.sup.2, CHR.sup.1 CHR.sup.2, CR.sup.1 .dbd.CR.sup.2, CHR.sup.1 CR.sup.2 .dbd.CH, C.dbd.C, OCHR.sup.1, CHR.sup.1 O, OCHR.sup.1 O, S(O).sub.n CHR.sup.1, S(O).sub.n CHR.sup.1 O, CHR.sup.1 S(O).sub.n, CHR.sup.1 OSO.sub.2, NR.sup.4 CHR.sup.1, CHR.sup.1 NR.sup.4, CO.sub.2, O.sub.2 C, SO.sub.2 O, OSO.sub.2, CO.CO, COCHR.sup.1, COCHR.sup.1 O, CHR.sup.1 CO, CHOH.CHR.sup.1, CHR.sup.1.CHOH, ##STR2## CONR.sup.4, OCONR.sup.4, NR.sup.4 CO, CSNR.sup.4, OCS.NR.sup.4, SCO.NR.sup.4, NR.sup.4 CO.sub.2, NR.sup.4 CS, NR.sup.4 CSO, NR.sup.4 COS, NR.sup.4 CONR.sup.4, S(O).sub.n NR.sup.4, NR.sup.4 S(O).sub.n, CS.sub.2, S.sub.2 C, CO.S, SCO, N.dbd.N, N.dbd.CR.sup.1, CR.sup.1 .dbd.N, CHR.sup.1 CHR.sup.2 CH(OH), CHR.sup.1 OCO, CHR.sup.1 SCO, CHR.sup.1 NR.sup.Type: GrantFiled: October 15, 1990Date of Patent: October 27, 1992Assignee: Imperial Chemical Industries PLCInventors: John M. Clough, Christopher R. A. Godfrey, Stephen P. Heaney, Kenneth Anderton
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Patent number: 5142049Abstract: Ortho ester-substituted chlorotriazines are prepared by the reaction of a dichlorotriazine with a reactive compound containing an ortho ester group, preferably a 4-(2-methoxy-2-methyl-1,3-dioxolan-4-yl)methyl group. They are useful as capping agents for polyphenylene ethers. The capped polyphenylene ethers form copolymer-containing compositions with polyesters, polyamides and other polymers containing carboxylic acid or amine groups.Type: GrantFiled: August 15, 1990Date of Patent: August 25, 1992Assignee: General Electric CompanyInventors: Farid F. Khouri, John T. Jackman, Otto Phanstiel, IV
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Patent number: 5124329Abstract: Fungicidal compounds having the formula (I): ##STR1## in which any two of K, L and M are nitrogen and the other is CY wherein Y is H, halogen, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, cyano, nitro or trifluoromethyl; n is 0 or 1 and X is an optionally substituted aromatic or heteroaromatic ring.Type: GrantFiled: June 28, 1990Date of Patent: June 23, 1992Assignee: Imperial Chemical Industries PLCInventors: John M. Clough, Ian T. Streeting, Christopher R. A. Godfrey
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Patent number: 5120843Abstract: The aromatic amines (I), alkyl amines (II), bicyclic amines (III). ##STR1## cycloalkyl amines (IV), aromatic bicyclic amines (V), hydroquinone amines (VI), quinone amines (VII), amino-ethers (VIII) and bicyclic amino ethers (IX) are useful as pharmaceutical agents for treating a number of conditions including spinal trauma, mild and/or moderate to severe head injury, etc. Also disclosed is a method of treatment using the 3,4-dihydrobenzopyrans (XI).Type: GrantFiled: October 23, 1989Date of Patent: June 9, 1992Assignee: UpjohnInventors: John M. McCall, Donald E. Ayer, E. Jon Jacobsen, Frederick J. VanDoornik, John R. Palmer
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Patent number: 5098465Abstract: The invention relates to new 2-pyrimidinyl- and 2-triazinylacetic acid derivatives of general formula I ##STR1## in which A, R.sup.2-5 and X have the meanings given in the description, processes for their preparation and their use as herbicides, fungicides and plant growth regulants.Type: GrantFiled: October 1, 1990Date of Patent: March 24, 1992Assignee: Shering AktiengesellschaftInventors: Gabriele Kruger, Christoph Harde, Nikolaus Heinrich, Anita Kruger, Erhard Nordhoff, Gerhard Tarara, Peter Wegner, Clemens Kotter, Gerhard Johann, Richard Rees, Graham P. Jones
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Patent number: 5089044Abstract: The invention relates to new substituted pyrimidinyloxy(thio)- and triazinyloxy(thio)acrylic acid derivative of general formula I ##STR1## in which A, G, R.sup.1-3, X and Y have the meanings given in the description, processes for their preparation and their use as herbicides, fungicides and plant growth regulants.Type: GrantFiled: July 19, 1990Date of Patent: February 18, 1992Assignee: Schering AktiengesellschaftInventors: Christoph Harde, Erhard Nordhoff, Anita Kruger, Gabriele Kruger, Gerhard Tarara, Peter Wegner, Nikolaus Heinrich, Clemens Kotter, Gerhard Johann, Richard Rees
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Patent number: 5087289Abstract: A herbicidal alkanoic acid derivative of the formula: ##STR1## wherein R.sup.3 is a hydrogen atom, a halogen atom, a halogen-substituted alkyl group, an alkyl group, a cycloalkyl group, an alkylthioalkyl group, a hydroxyalkyl group, a hydroxyl group, a cyano group, an acyloxyalkyl group, a thienyl group, a naphthyl group, a dihydronaphthyl group ##STR2## wherein R.sup.8 is a hydrogen atom, a halogen atom, a nitro group, an alkyl group, an alkoxy group or --S(O).sub.n R.sup.9 wherein R.sup.9 is an alkyl group, and n is an integer of from 0 to 2, m is an integer of from 0 to 2, each of R.sup.2 and R.sup.4 which may be the same or different is a hydrogen atom or an alkyl group, or R.sup.2 and R.sup.4 form together with the adjacent carbon atom a 3-, 4-, 5- or 6-membered ring which may contain an oxygen atom and may be substituted by one or two alkyl groups, each of R.sup.5 and R.sup.6 which may be the same or different is a hydrogen atom or an alkyl group, R.sup.7 is an alkyl group or a phenyl group, or R.sup.Type: GrantFiled: August 23, 1990Date of Patent: February 11, 1992Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.Inventors: Koichiro Kaku, Nobuhide Wada, Akira Takeuchi, Yasufumi Toyokawa, Takeshige Miyazawa, Ryo Yoshida, Kazuhiko Sugiyama
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Patent number: 5084459Abstract: There is provided a pest control composition containing a compound represented by the formula, ##STR1## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are the same or different and independently mean a hydrogen atom, a hydrocarbon group which may be substituted or a heterocyclic group which may be substituted and X means an electron attracting group or a salt thereof.The compounds are of minimal toxicity to man, domestic animals and fish and selectively display remarkable control effect on pests.Type: GrantFiled: October 25, 1989Date of Patent: January 28, 1992Assignee: Takeda Chemical Industries, Ltd.Inventors: Hideki Uneme, Isao Minamida, Tetsuo Okauchi, Noriko Higuchi
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Patent number: 5075316Abstract: Novel compounds of the formula ##STR1## in which: R.sub.1 and R.sub.2 independently of one another are hydrogen, halogen, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.2 halogenoalkyl, C.sub.1 -C.sub.3 alkoxy or C.sub.1 -C.sub.3 halogenoalkoxy; R.sub.3 is C.sub.3 -C.sub.6 cycloalkyl or C.sub.3 -C.sub.6 cycloalkyl which is substituted by up to three identical or different methyl or halogen groups; R.sub.4 is halogen, thiocyano, --OR.sub.5, --SR.sub.5 or --NR.sub.5 R.sub.6, in which R.sub.5 and R.sub.6 are halogen groups; R.sub.4 is halogen, thiocyano, --OR.sub.5, --SR.sub.5 or --NR.sub.5 R.sub.6, in which R.sub.5 and R.sub.6 are as defined herein, are novel active compounds for preventing attack of plants by microorganisms. The compounds can be employed as microbicides as such or in the form of suitable agents.Type: GrantFiled: March 20, 1990Date of Patent: December 24, 1991Assignee: Ciba-Geigy CorporationInventor: Adolf Hubele
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Patent number: 5062882Abstract: Triazine herbicides of the general formula I ##STR1## wherein R.sup.1 and R.sup.2 each independently represent a hydrogen or halogen atom, or an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, alkoxy, alkenyloxy, alkynyloxy, aryloxy, alkylthio, alkenylthio, alkynylthio, arylthio or amino group, or a formyl, optionally substituted alkylcarbonyl, cyano, carboxy, optionally substituted alkoxycarbonyl, dialkylaminoxy, dialkyliminoxy or azido group;X represents an oxygen or sulphur atom or a group --SO.sub.2 --, --SO--, or --NR.sup.4 --where R.sup.Type: GrantFiled: March 16, 1989Date of Patent: November 5, 1991Assignee: Shell International Research Maatschappij B. V.Inventors: Trevor W. Newton, Alastair McArthur
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Patent number: 5043443Abstract: Novel aminomethyloxooxazolidinyl arylbenzene derivatives, wherein the aryl includes the phenyl, substituted phenyl, pyridyl, and substituted pyridyl groups, such as (l)-N-{3-[4- (4'-pyridyl)phenyl]-2-oxooxazolidin-5-ylmethyl}acetamide, possess useful antibacterial activity.Type: GrantFiled: July 24, 1990Date of Patent: August 27, 1991Assignee: Du Pont Merck Pharmaceutical CompanyInventors: Randall K. Carlson, Chung-Ho Park, Walter A. Gregory