Having -c(=x)-, Wherein X Is Chalcogen, Bonded Directly To The Five-membered Hetero Ring Patents (Class 504/287)
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Patent number: 5554581Abstract: The present invention relates to 3,4,5,6-tetrahydrophthalamide derivatives and 3,4,5,6-tetrahydroisophthalimide derivatives having excellent effects as effective active ingredients of herbicides, and processes for preparing the same, and provides the compounds having a more efficient herbicidal activity, and efficient and industrial processes for the preparation thereof.More specifically, the tetrahydrophthalimide derivative obtained by reacting a halogen-substituted 5-cycloalkyloxyaniline derivative with a 3,4,5,6-tetrahydrophthalic anhydride, or the tetrahydroisophthalimide derivative of the present invention is reacted with various types of amines to prepare a tetrahydrophthalamide derivative represented by the general formula (I): ##STR1## These tetrahydrophthalamide derivatives and the tetrahydroisophthalimide derivatives exhibit excellent herbicidal activities in the soil treatment in the paddy field and field and the stem-foliar treatment.Type: GrantFiled: May 25, 1995Date of Patent: September 10, 1996Assignees: Sagami Chemical Research Center, Kaken Pharmaceutical Co., Ltd.Inventors: Kenji Hirai, Tomoko Matsukawa, Tomoyuki Yano, Emiko Ejiri, Kiyomi Aizawa, Koichi Shikakura, Tomoko Yoshii, Sadayuki Ugai, Osamu Yamada, Shigeki Kishi
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Patent number: 5512537Abstract: Herbicidal compounds have the formula ##STR1## in which R.sub.1 is hydrogen, methyl, ethyl, phenyl, 2-methylphenyl, 3-trifluoromethylphenyl, benzyl, 2-methylbenzyl or vinyl;R.sub.2 is hydrogen, methyl, ethyl or chloro;R.sub.3 is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkyl, nitro, p-tolyloxy or p-chlorophenoxy;R.sub.4 is hydrogen or a methyl, methoxy, trifluoromethoxy or halo group at the 2, 4- or 5-position;m is --CH or N; andX is O or NOR.sub.5 in which R.sub.5 is methyl or ethyl; provided that:(a) when R.sub.1 is methyl, and(i) R.sub.3 is methyl, then R.sub.4 is 4-methyl, 4-methoxy or chloro;(ii) R.sub.3 is nitro, then R.sub.4 is methoxy;(b) when R.sub.1 is ethyl, R.sub.3 is methyl or methoxy;(c) when R.sub.2 is chloro, R.sub.3 and R.sub.4 are independently C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 haloalkoxy or C.sub.1 -C.sub.4 alkoxy;(d) when R.sub.2 is methyl or ethyl, R.sub.1 is hydrogen;(e) when R.sub.3 is hydrogen, R.sub.Type: GrantFiled: March 2, 1994Date of Patent: April 30, 1996Assignee: Zeneca LimitedInventor: Tsze H. Tsang
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Patent number: 5506190Abstract: The present invention relates to 3,4,5,6-tetrahydrophthalamide derivatives and 3,4,5,6-tetrahydroisophthalimide derivatives having excellent effects as effective active ingredients of herbicides, and processes for preparing the same, and provides the compounds having a more efficient herbicidal activity, and efficient and industrial processes for the preparation thereof.More specifically, the tetrahydrophthalimide derivative obtained by reacting a halogen-substituted 5-cycloalkyloxyaniline derivative with a 3,4,5,6-tetrahydrophthalic anhydride, or the tetrahydroisophthalimide derivative of the present invention is reacted with various types of amines to prepare a tetrahydrophthalamide derivative represented by the general formula (I): ##STR1## These tetrahydrophthalamide derivatives and the tetrahydroisophthalimide derivatives exhibit excellent herbicidal activities in the soil treatment in the paddy field and field and the stem-foliar treatment.Type: GrantFiled: September 19, 1994Date of Patent: April 9, 1996Assignees: Sagami Chemical Research Center, Kaken Pharmaceutical Co. Ltd.Inventors: Kenji Hirai, Tomoko Matsukawa, Tomoyuki Yano, Emiko Ejiri, Kiyomi Aizawa, Koichi Shikakura, Tomoko Yoshii, Sadayuki Ugai, Osamu Yamada, Shigeki Kishi
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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: 5426091Abstract: A compound of formula (I): ##STR1## or a salt, enamine or the like, acylate, sulphonate, carbamate or ether derivative thereof; wherein X, X.sup.1 and X.sup.2 are independently oxygen or sulphur, R.sup.1 is an optionally substituted heterocyclic or cycloalkyl group, and Y is an optionally substituted C.sub.2 -C.sub.4 alkylene group which is optionally interposed by an oxygen atom, a group ##STR2## or an optionally mono-substituted nitrogen atom, wherein p is 0, 1 or 2, s is 0 or 1 and R.sup.b is alkyl or alkoxy; provided that when X, X.sup.1 and X.sup.2 are oxygen, R.sup.1 is not pyridyl or pyrimidinyl. Processes for the preparation of these compounds and herbicidal compositions containing them are also described and claimed.Type: GrantFiled: August 4, 1993Date of Patent: June 20, 1995Assignee: Zeneca LimitedInventors: John E. D. Barton, David Cartwright, John M. Cox, Glynn Mitchell, Charles G. Carter, David L. Lee, Francis H. Walker, Frank X. Woolard
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Patent number: 5312799Abstract: This invention described in this patent application relates to novel amides of the formula (I) ##STR1## wherein the substituents are as defined in the disclosure, intermediates for such amides, synthesis thereof and their use for the control of weeds.Type: GrantFiled: May 8, 1992Date of Patent: May 17, 1994Assignee: Sandoz Ltd.Inventors: Karl Seckinger, Karlheinz Milzner, Fred Kuhnen, Sasank S. Mohanty
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Patent number: 5312800Abstract: Pyrrolidinones of formula I ##STR1## wherein R is hydrogen, C.sub.1 -C.sub.4 alkyl, or phenyl unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 alkyl or by C.sub.1 -C.sub.4 haloalkyl, or is fluorine, chlorine or bromine;R.sub.0 is hydrogen or halogen;R.sub.1 and R.sub.2 independently of one another are hydrogen or C.sub.1 -C.sub.4 alkyl;X is hydrogen, flourine, chlorine, bromine, cyano, --COOR.sub.1, --CONR.sub.1 R.sub.2, --NH.sub.2 or --NHCOR.sub.3, wherein R.sub.1 and R.sub.2 are as defined, and R.sub.3 is C.sub.1 -C.sub.4 alkyl; andY is hydrogen, chlorine or bromine; andthe diastereoisomeric forms thereof, exhibit pre- and post-emergence herbicidal properties. The preparation of those compounds and their use as herbicidal active ingredients are described.Type: GrantFiled: May 20, 1993Date of Patent: May 17, 1994Assignee: Ciba-Geigy CorporationInventor: Hermann Rempfler
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Patent number: 5288694Abstract: The invention relates to new N-aryl-nitrogen heterocycles of the general formula (I) ##STR1## in which R.sup.1 represents hydrogen or halogen,R.sup.2 represents hydrogen or an in each case optionally substituted, straight-chain or branched radical from the series comprising alkyl, alkenyl or cycloalkyl andA represents one of the radicals or ##STR2## where R.sup.3 represents alkyl,R.sup.4 represents alkyl andR.sup.5 represents hydrogen or alkyl,a plurality of processes for their preparation, and their use as herbicides.Type: GrantFiled: November 23, 1992Date of Patent: February 22, 1994Assignee: Bayer AtkiengesellschaftInventors: Otto Schallner, Klaus Lurssen, Hans-Joachim Santel, Robert R. Schmidt, Renate Vosswinkel
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Patent number: 5258357Abstract: Carboxamides of the formulae Ia to Ic ##STR1## where X is oxygen or sulfur;R.sup.1 is hydrogen or substituted or unsubstituted cycloalkyl or alkyl;R.sup.2 is hydroxy, alkoxy, cyanoalkyl, substituted or unsubstituted alkenyl, alkynyl, phenyl or naphthyl, a substituted or unsubstituted 5- to 6-membered heterocyclic structure or one of the groups stated for R.sup.1, orR.sup.1 and R.sup.2 together are a 4- to 7-membered chain which contains, in addition to methylene groups, one of the following groups as ring member: oxygen, sulfur, N-methyl or carbonyl;R.sup.3 and R.sup.4 are each nitro, cyano, halogen, substituted or unsubstituted amino, alkoxy, alkylthio, a substituted or unsubstituted 5- to 6 -membered heterocyclic structure, substituted or unsubstituted alkenyl, alkynyl, phenyl, phenoxy or phenylthio, or one of the groups stated for R.sup.1 ;R.sup.5 is formyl, 4,5-dihydrooxazol-2-yl or COYR.sup.6 (Y=O,S);R.sup.Type: GrantFiled: September 21, 1992Date of Patent: November 2, 1993Assignee: BASF AktiengesellschaftInventors: Peter Muenster, Gerd Steiner, Wolfgang Freund, Bruno Wuerzer, Karl-Otto Westphalen
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Patent number: 5244893Abstract: New compounds of the formula (I) ##STR1## in which R.sup.1 -R.sup.6 have the meanings given in the description, their preparation and use in plant protection, the protection of materials and in the field of human and veterinary medicine.Formula (I) gives a definition of the compounds which can be prepared by analogous processes, for example from suitable benzothiophene derivatives by oxidation.Type: GrantFiled: April 29, 1992Date of Patent: September 14, 1993Assignee: Bayer AktiengesellschaftInventors: Hans-Ludwig Elbe, Dieter Berg, Heinz-Wilhelm Dehne, Stefan Dutzmann, Georg-Wilhelm Ludwig, Manfred Plempel
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Patent number: 5228899Abstract: Plant growth regulators comprising, as an active ingredient, a substituted dicarboxylic acid derivative having the formula: ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, D and G are the same as defined in the present specification, the substituted dicarboxylic acid derivatives, and processes for preparing the same, are disclosed. The plant growth regulators provided according to the present invention have a regulating activity on plant growth; more specifically, an action thereof of lowering the content of endogenous ethylene in a plant is utilized.Type: GrantFiled: August 24, 1990Date of Patent: July 20, 1993Assignee: Sumitomo Chemical Company LimitedInventors: Yoshikazu Itoh, Akio Manabe, Masato Mizutani, Naonori Hirata, Sachiko Uwayokote, Kazuo Izumi, Kenji Arai
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Patent number: 5192498Abstract: It has now been discovered that the undesirable odor in thiocarbamate compounds can be suppressed or mostly eliminated by the process of this invention. Generally, the process of this invention involves mixing an aqueous solution of sodium hypochlorite, calcium hypochlorite or chloramine-B with the odorous thiocarbamate compound for a sufficient period of time, followed by a second step of mixing citric acid, maleic acid or oxalic acid with the treated thiocarbamate compound to eliminate chlorodialkylamine compounds produced in the first step.Type: GrantFiled: October 11, 1991Date of Patent: March 9, 1993Assignee: Imperial Chemical Industries plcInventors: Chia-Chung Chen, Ray J. Lo
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Patent number: 5191089Abstract: Herbicidal 4-alkoxy- and 4-(substituted)amino-arylpyrrolinone derivatives of the formula ##STR1## in which X and Y independently of one another represent hydrogen, halogen, alkyl, alkoxy, halogenoalkyl or in each case unsubstituted or substituted aryloxy or arylthio,Z represents halogen, alkyl or alkoxy,n represents the number 0, 1, 2 or 3,A represents in each case unsubstituted or in each case halogen-substituted alkyl, alkenyl, alkynyl, alkoxyalkyl, polyalkoxyalkyl or alkylthioalkyl, cycloalkyl which is optionally interrupted by hetero atoms, arylalkyl which is unsubstituted or substituted by halogen, alkyl, halogenoalkyl, alkoxy and/or nitro, unsubstituted aryl or aryl substituted by a member selected from the group consisting of halogen, alkyl, alkoxy, halogenoalkyl, halogenoalkoxy and phenoxy or phenylthio which are in each case unsubstituted or substituted by halogen, alkyl, alkoxy, halogenoalkyl and/or halogenoalkoxy,B represents hydroxyl, alkoxy, halogenoalkoxy or cycloalkoxy, the cycloalkyl radical bType: GrantFiled: August 9, 1990Date of Patent: March 2, 1993Assignee: Bayer AktiengesellschaftInventors: Bernd Baasner, Reiner Fischer, Klaus Lurssen, Hans-Joachim Santel, Robert R. Schmidt
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Patent number: 5189145Abstract: Flower-inducing substances containing protein or peptide materials and obtained by extraction of plant materials with water.Type: GrantFiled: September 19, 1990Date of Patent: February 23, 1993Assignees: Ajinomoto Co., Inc., Go TakebaInventor: Go Takeba
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Patent number: 5180418Abstract: Cycloalkanecarboxylic acid derivatives of formula I ##STR1## wherein W is ##STR2## and A is CO--R.sub.3 or CN; R.sub.1 is hydrogen or fluorine; R.sub.2 is halogen or cyano; R.sub.3 is chlorine, X--R.sub.5, amino, C.sub.1 -C.sub.4 alkylamino, d-C.sub.1 -C.sub.4 alkylamino, C.sub.2 -C.sub.4 haloalkylamino, di-C.sub.2 -C.sub.4 haloalkylamino, C.sub.1 -C.sub.4 hydroxyalkylamino, di-C.sub.1 -C.sub.4 hydroxyalkylamino, C.sub.3 -C.sub.4 alkenylamino, diallylamino, --N-pyrrolidino, --N-piperidino, --N-morpholino, --N-thiomorpholino, --N-piperidazino, the group --O--N.dbd.C--(R.sub.9)R.sub.10 or the group --N--R.sub.6 (OR.sub.6); each of R.sub.4 and R.sub.14, independently of the other, is hydrogen, fluorine, chlorine, bromine, C.sub.1 -C.sub.4 alkyl or trifluoromethyl; R.sub.5 is hydrogen, C.sub.1 -C.sub.10 alkyl, C.sub.1 -C.sub.4 alkoxy-C.sub.1 -C.sub.4 alkyl, halo-C.sub.1 -C.sub.8 alkyl, C.sub.1 -C.sub.10 alkylthio-C.sub.1 -C.sub.4 alkyl, di-C.sub.1 -C.sub.4 alkylamino-C.sub.1 -C.sub.4 alkyl, cyano-C.sub.1 -C.sub.Type: GrantFiled: July 19, 1991Date of Patent: January 19, 1993Assignee: Ciba-Geigy CorporationInventors: Georg Pissiotas, Hans Moser, Hans-Georg Brunner, Eginhard Steiner
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Patent number: 5176738Abstract: A method of controlling plant growth is provided comprising applying to the plants or to a habitat thereof a herbicidally effective amount of a compound having the structure: ##STR1## wherein R.sup.1 is selected from the group consisting of carboxy, cyano, ester ##STR2## wherein R.sup.2 is selected from the group consisting of a straight-chained alkyl group or a branched-chained alkyl group, of about 1 to 8 carbon atoms.R.sup.3 and R.sup.4 are selected from the group consisting of hydrogen, alkyl of about 1 to 8 carbon atoms, cycloalkyl of about 5 to 6 carbon atoms, and heterocyclyl of about 5 to 6 carbon and hetero atoms, or,R.sup.3 and R.sup.4 taken together with the nitrogen atoms to which they are attached form a heterocyclyl group having 5 to 6 carbon and hetero atoms. Also, novel compounds having the above structure are provided.Type: GrantFiled: October 1, 1991Date of Patent: January 5, 1993Assignee: Eastman Kodak CompanyInventor: Thomas R. Welter