Halogen Attached Directly To The 1,2-diazine Ring By Nonionic Bonding Patents (Class 544/241)
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Patent number: 4910201Abstract: Novel 3(2H)-pyridazinone derivatives of the formula (I): ##STR1## wherein, X represents a halogen, an alkyl, a haloalkyl, a haloalkoxy atoms, NO.sub.2, an alkoxy or ##STR2## (wherein, R represents an alkyl); n is 1 to 4;A represents hydrogen, a halogen, an alkyl or an alkoxy;B represents CX.sub.1 (wherein, X.sub.1 represents H or a halogen) or N;R.sup.1 and R.sup.2 represent each independently H or an alkyl;E represents H, a halogen, an alkoxy or --OH; andQ represents: ##STR3## (wherein, Y represents a halogen, an alkyl, an alkoxy, a haloalkyl, a haloalkoxy, CN, ##STR4## (wherein, Z represents a halogen, an alkyl, an alkoxy or a haloalkyl atoms, and l is 0, 1 to 5, said Z being the same or different when l is 2 to 5); and m is 1 to 5, said Y being the same or different when n is 2 to 4. A process for preparation of said derivatives is also provided. These derivatives are useful as an active ingredient of insecticidal composition.Type: GrantFiled: July 20, 1987Date of Patent: March 20, 1990Assignee: Nissan Chemical Industries, Ltd.Inventors: Yasuo Kawamura, Tomoyuki Ogura, Yasuo Kawamura, Masayoshi Hirose, Kiminori Hirata, Masaki Kudo, Toshiro Miyake
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Patent number: 4906627Abstract: Compounds of the following formula: ##STR1## wherein Z.sup.3 represents halogen atom, straight or branched chain alkyl group having 1 to 10 carbon atoms, alkoxy group having 1 to 10 carbon atoms, alkylcarbonyl having 2 to 10 carbon atoms, alkoxyalkyl group having 2 to 4 carbon atoms, ##STR2## W represents halogen atom, alkyl group having 1 to 4 carbon atoms, alkoxy group having 1 to 4 carbon atoms, haloalkyl group having 1 to 4 carbon atoms, or nitro group, m is 0 or an integer of 1 to 2, and when m is 2, W may be same or different, and compositions for controlling insects, acari and nemati which contain such compound.Type: GrantFiled: May 6, 1988Date of Patent: March 6, 1990Assignee: Nissan Chemical Industries, Ltd.Inventors: Yasuyuki Nakajima, Yasuo Kawamura, Tomoyuki Ogura, Takahiro Makabe, Kiminori Hirata, Masaki Kudo, Yoshinori Ochiai, Masayoshi Hirose
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Patent number: 4892947Abstract: A 3(2H)pyridazinone of the formula: ##STR1## wherein R.sub.1 is hydrogen, methyl, C.sub.3 -C.sub.6 alkenyl, C.sub.5 or C.sub.6 cycloalkyl, benzyl, phenyl, --(CH.sub.2).sub.m CO.sub.2 R.sub.3 (wherein R.sub.3 is hydrogen or C.sub.1 -C.sub.5 alkyl, and m is an integer of from 1 to 4), --(CH.sub.2).sub.n A (wherein A is --OH or --N(R.sub.4).sub.2 wherein R.sub.4 is C.sub.1 -C.sub.3 alkyl, and n is an integer of from 2 to 6) or --CH.sub.2 CF.sub.3 ; R.sub.2 is chlorine or bromine; each of Y.sub.1 and Y.sub.2 which may be the same or different, is hydrogen, C.sub.1 -C.sub.5 alkyl, C.sub.2 -C.sub.8 alkenyl, halogen, --OR.sub.5 (wherein R.sub.5 is hydrogen, C.sub.1 -C.sub.8 alkyl or ##STR2## wherein q is an integer of from 1 to 4), --CO.sub.2 R.sub.6 (wherein R.sub.6 is hydrogen or C.sub.1 -C.sub.5 alkyl), --N(R.sub.7).sub.2 (wherein R.sub.7 is C.sub.1 -C.sub.4 alkyl) or --SR.sub.8 (wherein R.sub.8 is C.sub.1 -C.sub.4 alkyl); and Y.sub.3 is C.sub.1 -C.sub.5 alkyl, C.sub.2 -C.sub.8 alkenyl, halogen, --OR.sub.Type: GrantFiled: April 22, 1986Date of Patent: January 9, 1990Assignee: Nissan Chemical Industries Ltd.Inventors: Motoo Mutsukado, Keizo Tanikawa, Ken-ichi Shikada, Ryozo Sakoda
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Patent number: 4868183Abstract: Disclosed are compounds of the formula ##STR1## wherein: R.sup.1 is a lower alkyl group;R.sup.2 and R.sup.3 are each hydrogen or lower alkyl or R.sup.2 and R.sup.3 taken together may form --(CH.sub.2 (.sub.4)-- or --CH.dbd.CH--CH.dbd.CH--;.alpha. is a 5- or 6-membered heteroaromatic ring group containing 1 to 3 hetero-atoms selected from the group consisting of nitrogen, oxygen and sulfur, or a pyrazine-N-oxide ring, pyridazine-N-oxide ring or pyrimidine-N-oxide ring group, wherein each of these heteroaromatic ring groups may optionally have 1 to 3 substituents selected from the group consisting of a lower alkyl, halogen, phenyl, lower alkoxycarbonyl, amino, lower alkoxy and hydroxy-lower alkyl, with the proviso that said 5- or 6-membered heteroaromatic ring group is not thiazolyl, isothiazolyl, pyridyl or 1,3,5-triazinyl group; or salts thereof. These compounds and salts thereof have anti-inflammatory activity and lipoxygenase-inhibitory activity.Type: GrantFiled: July 20, 1987Date of Patent: September 19, 1989Assignee: Otsuka Pharmaceutical Factory, Inc.Inventors: Kenichi Kanai, Kiyoto Goto, Kinji Hashimoto
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Patent number: 4863924Abstract: An N-benzoyl urea compound having the formula: ##STR1## wherein X is a hydrogen atom, a halogen atom or a nitro group, n is an integer of from 1 to 3, and Q is ##STR2## wherein Y.sub.1 is an unsubstituted or substituted alkyl group, or an alkoxy or alkoxycarbonyl group with its alkyl moiety unsubstituted or substituted, Y.sub.2 is a hydrogen atom, a halogen atom, a nitro group, an unsubstituted or substituted alkyl group, or an alkoxy or alkoxycarbonyl group with its alkyl moiety unsubstituted or substituted, Z is a hydrogen atom, a halogen atom, a trifluoromethyl group or a nitro group, and each of A and B is .dbd.CH-- or a nitrogen atom, provided that one of A and B is .dbd.CH-- and the other is a nitrogen atom, with the provisos (1) that when Q is ##STR3## where when X is a hydrogen atom and Y.sub.1 is an alkyl group, Z is not a hydrogen atom, a halogen atom nor a trifluoromethyl group, and (2) that when Q is ##STR4## wherein A is a nitrogen atom and Y.sub.1 is a trifluoromethyl group, Y.sub.Type: GrantFiled: December 8, 1986Date of Patent: September 5, 1989Assignee: Ishihara Sangyo Kaisha Ltd.Inventors: Takahiro Haga, Nobutoshi Yamada, Hideo Sugi, Toru Koyanagi, Hiroshi Okada
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Patent number: 4851032Abstract: Cyclohexane-1,3-dione derivatives of the formula ##STR1## where R.sup.1, R.sup.2, R.sup.3 and R.sup.4 have the meanings given in the disclosure, and the use thereof for combating unwanted plants, especially Gramineae.Type: GrantFiled: February 9, 1987Date of Patent: July 25, 1989Assignee: BASF AktiengesellschaftInventors: Dieter Jahn, Rainer Becker, Norbert Goetz, Bruno Wuerzer
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Patent number: 4845093Abstract: An N-benzoyl-N'-pyridazinyloxyphenyl urea compound having the formula: ##STR1## wherein each of X.sub.1 and X.sub.2 is a hydrogen atom, a halogen atom or a nitro group, Y is a hydrogen atom, a halogen atom or a methyl group which may be substituted by fluorine, and Z is a hydrogen atom, a halogen atom or a trifluoromethyl group, provided that when X.sub.1 is a hydrogen atom and X.sub.2 is a hydrogen atom or a halogen atom, Y is a methyl group which may be substituted by fluorine and/or Z is a hydrogen atom or a trifluoromethyl group. The compound is useful as an active ingredient for an antitumorous composition.Type: GrantFiled: October 19, 1987Date of Patent: July 4, 1989Assignee: Ishihara Sangyo Kaisha Ltd.Inventors: Takahiro Haga, Nobutoshi Yamada, Hideo Sugi, Toru Koyanagi, hiroshi Okada
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Patent number: 4837217Abstract: A 3(2H)-pyridazinone derivative of the general formula (I): ##STR1## wherein R is a straight or branched C.sub.2 -C.sub.6 alkyl,A is a straight or branched C.sub.1 -C.sub.6 alkyl or a halogen atom,X is --O-- or --S--,R.sup.1 and R.sup.2 are each independently hydrogen atom or C.sub.1 -C.sub.3 alkyl,B is --CH.dbd.CH--, --N.dbd.CH--, --N.dbd.N--, --S--, --O-- or ##STR2## wherein R.sup.3 is hydrogen or C.sub.1 -C.sub.3 alkyl, Y is a halogen atom, a straight or branched C.sub.1 -C.sub.6 alkyl, a C.sub.3 -C.sub.6 cycloalkyl or cycloalkoxy, and other substituents,n is 0 or an integer of 1 to 3, and when n is 2 or 3, Y may be same or different, with the proviso that when B is --CH.dbd.CH--, n is an integer of 1 to 3 and at least one of Y is --O--W, as this term is defined in the specification.A process for the preparation of said derivatives is also provided.Type: GrantFiled: April 11, 1986Date of Patent: June 6, 1989Assignee: Nissan Chemical Industries, Ltd.Inventors: Tomoyuki Ogura, Yasuo Kawamura, Masatoshi Baba, Shigeru Ishii, Kiminori Hirata, Masaki Kudo, Yoshinori Ochiai, Masayoshi Hirose
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Patent number: 4834904Abstract: Optically active nitrogen-containing heterocycles of the formula I according to claim 1 are suitable as components for ferroelectric liquid crystalline materials.Type: GrantFiled: December 24, 1986Date of Patent: May 30, 1989Assignee: Merck Patent Gesellschaft mit Beschrankter HaftungInventors: Joachim Krause, Rudolf Eidenschink, Klaus Bofinger, Bernhard Scheuble, Thomas Geelhaar
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Patent number: 4826845Abstract: The invention relates to novel 3(2H)-pyridazinone-derivatives of the general formula (I), pharmaceutical compositions containing them and process for their preparation. In the general formula (I) ##STR1## stands for an ethyl or propyl group substituted by a terminal halogen atom or a hydroxyl or NR.sup.1 R.sup.2 group, whereinR.sup.1 represents hydrogen atom or an unsubstituted or optionally substituted benzyl group;R.sup.2 represents hydrogen atom or an unsubstituted or optionally substituted benzo[1,4]dioxan-2-yl-methyl or -ethyl group or a (CH.sub.2).sub.n --R.sup.3 group, whereinn is 2 or 3; andR.sup.3 stands for an unsubstituted or optionally substituted phenoxy or phenylthio group; andX stands for a hydrogen or halogen atom or an unsubstituted or optionally substituted, saturated or unsaturated 5- or 6-membered heterocyclic group containing a nitrogen atom and optionally an additional heteroatom, e.g.Type: GrantFiled: October 29, 1986Date of Patent: May 2, 1989Assignee: Richter Gedeon Vegyeszeti Gyar T.R.Inventors: Endre Kasztreiner, Gyorgy Rablocsky, Nandor Makk, Laszlo Jaszlits, Peter Matyus, Gyorgy Cseh, Ildiko Pribusz nee Rapp, Klara Czako, Eszter Diesler, Istvan Elekes, Laszlo Kaufer, Maria Kuhar nee Kurthy, Judit Kincsessy, Judit Kosary, Gyongyi Nagy nee Csokas
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Patent number: 4820839Abstract: Nitrogen-containing heterocyclic esters of the formula I,R.sup.1 -A.sup.1 -Z.sup.1 -A.sup.2 -[Z.sup.2 -A.sup.3 ].sub.m -R.sup.2 Iin which R.sup.1, R.sup.2, A.sup.1, A.sup.2, A.sup.3, Z.sup.1, Z.sup.2 and m have the meaning specified in patent claim 1, are suitable as components of smectic liquid-crystalline phases.Type: GrantFiled: January 23, 1987Date of Patent: April 11, 1989Assignee: Merck Patent Gesellschaft Mit Beschrankter HaftungInventors: Joachim Krause, Andreas Wachtler, Volker Reiffenrath, Bernhard Scheuble, Reinhard Hittich
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Patent number: 4762932Abstract: Compounds useful for inhibiting gastric acid secretion and for the treatment of peptic ulcers caused or exacerbated by gastric acidity having the following formula (I): ##STR1## in which R.sup.1 and R.sup.2, are H, C.sub.1-10 alkyl, C.sub.3-8 cycloalkyl or cycloalkylalkyl in which the alkyl part is C.sub.1-6 and the cycloalkyl part is C.sub.3-8, each of the alkyl, cycloalkyl and cycloalkylalkyls being optionally substituted by one or more halogens selected from F, Cl and Br, provided that at least one of R.sup.1 and R.sup.2 is a halogen substituted alkyl, cycloalkyl or cycloalkylalkyl and provided that there is no halogen substituent on the carbon directly attached to the nitrogen; and X, m, Y, n and R.sup.3 are as described in the specification; and the pharmaceutically-acceptable acid-addition salts thereof.Type: GrantFiled: June 2, 1986Date of Patent: August 9, 1988Assignees: Imperial Chemical Industries, Ltd., ICI Americas, Inc.Inventors: Tobias O. Yellin, Philip N. Edwards, Michael S. Large
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Patent number: 4753940Abstract: The invention relates to novel phenylcarbamoylbarbituric acid derivatives of the general formula ##STR1## wherein R.sub.1 is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.3 alkoxy, allyl or C.sub.3 -C.sub.6 cycloalkyl,R.sub.2 is C.sub.1 -C.sub.4 alkyl or allyl,R.sub.3 is an unsubstituted or substituted heteroaromatic 6-membered ring which contains 2 or 3 nitrogen atoms, or is an unsubstituted or substituted heteroaromatic 6-membered ring which is fused to a benzene ring and which contains 1 to 3 nitrogen atoms,R.sub.4 and R.sub.5 are each independently of the other hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy or C.sub.1 -C.sub.3 haloalkyl andX is an oxygen or sulfur atom,and to the tautomers and salts thereof.These compounds may be used for controlling helminths which are parasites of animals.Type: GrantFiled: February 7, 1986Date of Patent: June 28, 1988Assignee: Ciba-Geigy CorporationInventors: Elmar Sturm, Jean J. Gallay, Georg Pissiotas
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Patent number: 4748165Abstract: This invention relates to amidine derivatives which are histamine H-2 antagonists and which inhibit gastric acid secretion. According to the invention there is provided a guanidine derivative of the formula I: ##STR1## in which R.sup.1 is hydrogen or a 1-10C alkyl, 3-8C cycloalkyl, 4-14C cycloalkylalkyl, 3-6C alkenyl, 3-6C alkynyl, 1-6C alkanoyl, 6-10C aryl, 7-11C aralkyl or 7-11C aroyl radical, the latter three being optionally substituted; ring X is a heterocyclic ring as defined in the specification; A is phenylene or 5-7C cycloalkylene or a 1-8C alkylene chain into which is optionally inserted one or two groups; and R.sup.2 and R.sup.3 are a variety of radicals described in the specification: and the pharmaceutically-acceptable acid-addition salts thereof. Manufacturing processes and pharmaceutical compositions are also described.Type: GrantFiled: May 11, 1982Date of Patent: May 31, 1988Assignee: Imperial Chemical Industries PLCInventors: Derrick F. Jones, Keith Oldham
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Patent number: 4740505Abstract: Organic phosphates of the formula: ##STR1## wherein R.sup.1 and R.sup.2 are respectively an alkyl group; R.sup.3 is a phenyl group which is substituted at least by a pyridazinyloxy or pyridazinylthio group in which the pyridazinyl group may be substituted; and X is an oxygen or sulfur atom, or a salt thereof, have marked insecticidal-acaricidal activity against plant pests and mites, household pests, with very low toxicity to warm-blooded animals and fish.Type: GrantFiled: February 18, 1986Date of Patent: April 26, 1988Assignees: Takeda Chemical Industries, Ltd., Nippon Chemical Industrial Co., Ltd.Inventors: Kazuo Kamei, Nobuo Matsumoto, Yasuo Sato
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Patent number: 4735650Abstract: Pyridazinylurea N-oxide plant regulators of the formula ##STR1## and acid addition salts thereof; wherein R is alkyl, cycloalkyl or phenyl optionally substituted with halogen; R.sup.1 is hydrogen or alkyl; each X independently is halogen, alkoxy, alkylthio or alkylsulfonyl; p is 0, 1 or 2; and wherein the NHCONRR.sup.1 group is bonded to the pyridazinyl ring in the 3- or 4-position; provided that (a) when X is halogen, p is 1 or 2 and the NHCONRR.sup.1 group is in the 4-position, the halogen is in at least one of the 5- and 6-positions, and (b) when X is halogen, p is 1 or 2 and the NHCONRR.sup.1 group is in the 3-position, the halogen is in at least one of the 4- and 5-positions.Type: GrantFiled: October 10, 1985Date of Patent: April 5, 1988Assignee: FMC CorporationInventor: Robert N. Henrie, II
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Patent number: 4728355Abstract: Pyridazinylurea plant regulators of the formula ##STR1## and acid addition salts thereof; wherein R is alkyl or cycloalkyl, R.sup.1 is hydrogen or alkyl, each X independently is halogen, alkoxy, alkylthi or alkylsulfonyl, and p is 0, 1 or 2.Type: GrantFiled: October 10, 1985Date of Patent: March 1, 1988Assignee: FMC CorporationInventor: Robert N. Henrie, II
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Patent number: 4723005Abstract: New anisotropic compounds of the formula (1) are useful in liquid crystal mixtures for electrooptical displays; at least one of the end groups of the compounds (1) is an alkyl group which carries cyano or halogen in a terminal or non-terminal position. This offers advantages for longitudinal polarization and/or cross-polarization of the anisotropic compounds with the aid of the comparatively highly polarizing cyano or halogen substituents, in particular high clear points, low .DELTA..epsilon./.epsilon..perp. values and/or negative .DELTA..epsilon. values.Type: GrantFiled: September 10, 1984Date of Patent: February 2, 1988Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Tuong Huynh-Ba, Maged A. Osman
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Patent number: 4713197Abstract: Nitrogen-containing heterocyclic compounds of the formula IR.sup.I --(A--Z).sub.n --A--R.sup.2 Iwherein R.sup.1 and R.sup.2 in each case independently of one another are alkyl group with 1-15 C atoms, wherein one or two non-adjacent CH.sub.2 groups can also be replaced by 0 atoms and/or --CO-- group and/or --O--CO-- groups and/or --CO--O-- groups, and one of the radicals R.sup.1 and R.sup.2 can also be H, CN, F, Cl or Br, the groups A in each case independently of one another are a 1,4-phenylene group, wherein one or two CH groups can also be replaced by N atoms, a 1,4-cyclohexylene group, wherein one or two CH.sub.2 groups which are not adjacent can be replaced by 0 atoms, a 1,3-dithiane-2,5-diyl group, a 1,4-bicyclo(2,2,2)-octylene group, a decahydronapthalene-2,6-diyl group or a 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, the group Z in each case independently of one another are --CO--O--, --O--CO--, --CH.sub.2 CH.sub.2 --, --OCH.sub.2 --, --CH.sub.Type: GrantFiled: January 17, 1985Date of Patent: December 15, 1987Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Rudolf Eidenschink, Joachim Krause, Reinhard Hittich, Eike Poetsch, Bernhard Scheuble, Georg Weber, Ludwig Pohl
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Patent number: 4707551Abstract: Novel pyrazinyl sulfonamides of the formulaQ--SO.sub.2 --NH.sub.2wherein Q is a substituted pyrazine group are intermediates for the production of sulfonylureas and suflonylthioureas which are useful in controlling weeds or selectively influencing plant growth.Type: GrantFiled: March 21, 1986Date of Patent: November 17, 1987Assignee: CIBA-GEIGY CorporationInventors: Beat Bohner, Werner Fory, Rolf Schurter, Georg Pissiotas
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Patent number: 4678499Abstract: Benzenesulfonamide compounds such as N-[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]-1,4-dihydro-3-methyl-4 -oxo-1-phenyl-indeno[1,2-C]-pyrazole-5-sulfonamide and N-[(4-methoxy-6-methyl-pyrimidin-2-yl)aminocarbonyl]-1,4-dihydro-3-methyl- 4-oxo-1-phenyl-indeno[1,2-C]pyrazole-5-sulfonamide, agricultural compositions containing them, and their herbicidal utility are disclosed.Type: GrantFiled: January 30, 1986Date of Patent: July 7, 1987Assignee: E. I. Du Pont de Nemours and CompanyInventors: Robert J. Pasteris, Ramaurthi Muthukrishnan
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Patent number: 4676604Abstract: Compounds of the formula ##STR1## wherein R.sup.1 is hydrogen or straight-chain alkyl; R.sup.2 is --CN, --R, --COR, --COOR or when R.sup.2 is positioned on an aromatic ring R.sup.2 also can be --OR, --OOCR or --F; R is alkyl; A is a group with 1 to 4 six-membered rings, these rings being linked directly with one another and with ring B in each case via a single covalent bond or being linked at one or two positions also via --COO--, --OOC-- or --CH.sub.2 CH.sub.Type: GrantFiled: March 5, 1984Date of Patent: June 30, 1987Assignee: Hoffmann-La Roche Inc.Inventor: Martin Petrzilka
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Patent number: 4677199Abstract: Compounds of the general formula I ##STR1## wherein R.sup.1 is hydrogen, fluorine, chlorine or bromine, R.sup.2 is hydrogen, fluorine, chlorine, bromine, or nitro, B is aliphatic or a sulfo-substituted phenylene radical, and X is a dye radical, are useful for dyeing hydroxyl-containing textile material, in particular cotton.Type: GrantFiled: September 19, 1985Date of Patent: June 30, 1987Assignee: BASF AktiengesellschaftInventors: Dietmar Augart, Heinz Eilingsfeld, Heinz Krueger, Hartmut Lardon, Ortwin Schaffer, Guenther Seybold
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Patent number: 4677111Abstract: An N-benzoyl-N'-(3-nitrophenyl) urea compound having the formula ##STR1## wherein each of X.sub.1 and X.sub.2 is a hydrogen atom, a halogen atom, a trifluoromethyl group or a nitro group, and Y is ##STR2## (wherein R is a hydrogen atom, a halogen atom or a tirfluoromethyl group), provided that when Y is ##STR3## X.sub.1 and/or X.sub.2 is a nitro group. The compound is useful as an active ingredient of an antitumorous composition.Type: GrantFiled: October 1, 1985Date of Patent: June 30, 1987Assignee: Ishihara Sangyo Kaisha Ltd.Inventors: Takahiro Haga, Nobutoshi Yamada, Hideo Sugi, Toru Koyanagi, Hiroshi Okada
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Patent number: 4659502Abstract: Ethane derivatives of the formula IR.sup.1 --A.sup.1 --CH.sub.2 CH.sub.2 --A.sup.2 --(A.sup.3).sub.n --R.sup.2 IwhereinR.sup.1 is H, an alkyl group with 1-12 C atoms, in which one or two non adjacent CH.sub.2 groups can also be replaced by O atoms and/or CO groups and/or --O--CO-- groups and/or --CO--O groups, F, Cl, Br or R.sup.3 --A.sup.4 --Z.sup.1 --,R.sup.2 is --CN or --Z.sup.2 --A.sup.4 --CN,A.sup.1 is --A--, --A--A.sup.5 -- or --A.sup.5 --A--,A.sup.2 is an 1,4-phenylene group which is unsubstituted or substituted by one or two F and/or Cl atoms and/or CH.sub.3 groups and/or CN groups and in which one or two CH groups can also be replaced by N atoms,A is a 1,4-cyclohexylene group, in which one or two non adjacent CH.sub.2 groups can also be replaced by O atoms, or is a 1,3-dithiane-2,5-diyl group or 1,4-bicyclo(2,2,2)-octylene group,A.sup.3, A.sub.4 are each a 1,4-cyclohexylene group, in which one or two non adjacent CH.sub.Type: GrantFiled: January 17, 1985Date of Patent: April 21, 1987Assignee: Merck Patent Gesellschaft mit Beschrankter HaftungInventors: Julie E. Fearon, Wendy E. Smith, George W. Gray, David Lacey, Kenneth J. Toyne, Georg Weber
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Patent number: 4628088Abstract: A novel process is described for preparing substituted pyridazines, where a less substituted pyridazine is reacted with a carboxylic acid in the presence of a silver ion as catalyst, using peroxydisulfate ion. The reaction is run at a temperature from about 40.degree. to 80.degree. C. in an aqueous solvent system and mineral acid. The substituted pyridazines are useful as intermediates to herbicidal and fungicidal compounds.Type: GrantFiled: July 17, 1984Date of Patent: December 9, 1986Assignee: Eli Lilly and CompanyInventor: Jack G. Samaritoni
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Patent number: 4623376Abstract: This invention relates to a method for controlling undesirable monocotyledonous and dicotyledonous plant species by applying to the foliage thereof or to soil containing seeds or other propagating organs of said plant species, a herbicidally-effective amount of a pyridazine compound. The invention also relates to novel herbicidally-effective pyridazine compounds.Type: GrantFiled: April 16, 1984Date of Patent: November 18, 1986Assignee: American Cyanamid CompanyInventors: Laurine M. Speltz, Bryant L. Walworth
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Patent number: 4622163Abstract: New anisotropic compounds with a cross-polarizing substituent have the formula (1) ##STR1## The increase in .epsilon..perp. is achieved by the polarizing group X, preferably the cyano group or a halogen atom, which is not laterally on the ring, as with the known compounds, but is on the bridge, that is to say is part of the main bridge bonding rings A and B to one another. Ring A has the formula (1a) or (1b) given herein and is always cycloaliphatic, while ring B can be identical to ring A or is an aromatic ring of the formula (1c) or (1d) herein. R.sup.1 and R.sup.2 are identical or different end groups of the formula (1e) herein. The radical X on the bridge causes less widening of the molecule than a radical X on a ring, which provides comparatively higher clear points and moreover enables aromatic rings to be omitted from the anisotropic compounds.Type: GrantFiled: September 10, 1984Date of Patent: November 11, 1986Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Tuong Huynh-Ba, Maged A. Osman
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Patent number: 4619686Abstract: This invention describes noval pyridazinylurea compounds, which are useful as herbicides.Type: GrantFiled: July 17, 1984Date of Patent: October 28, 1986Assignee: Eli Lilly and CompanyInventors: Riaz F. Abdulla, Jack G. Samaritoni
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Patent number: 4604465Abstract: Compounds useful for inhibiting gastric acid secretion and for the treatment of peptic ulcers caused or exacerbated by gastric acidity having the following formula (I): ##STR1## in which R.sup.1 and R.sup.2, are H, C.sub.1-10 alkyl, C.sub.3-8 cycloalkyl or cycloalkylalkyl in which the alkyl part is C.sub.1-6 and the cycloalkyl part is C.sub.3-8, each of the alkyl, cycloalkyl and cycloalkylalkyls being optionally substituted by one or more halogens selected from F, Cl and Br, provided that at least one of R.sup.1 and R.sup.2 is a halogen substituted alkyl, cycloalkyl or cycloalkylalkyl and provided that there is no halogen substituent on the carbon directly attached to the nitrogen; and X, m, Y, n and R.sup.3 are as described in the specification; and the pharmaceutically-acceptable acid-addition salts thereof.Type: GrantFiled: September 21, 1982Date of Patent: August 5, 1986Assignees: ICI Americas, Inc., Imperial Chemical Industries, LimitedInventors: Tobias O. Yellin, Philip N. Edwards, Michael S. Large
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Patent number: 4604127Abstract: This invention describes novel pyridazinylimidazolidinone compounds, which are useful as herbicides.Type: GrantFiled: May 15, 1985Date of Patent: August 5, 1986Assignee: Eli Lilly and CompanyInventors: Riaz F. Abdulla, Jack G. Samaritoni
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Patent number: 4593028Abstract: Cardiotonic 5-heteroaryl-substituted-2-pyridone compounds, pharamaceutical compositions, and a method for the treatment of congestive heart failure.Type: GrantFiled: April 19, 1984Date of Patent: June 3, 1986Assignee: William H. Rorer, Inc.Inventor: Henry F. Campbell
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Patent number: 4569934Abstract: This invention concerns novel imidazo[1,2-b]-pyridazines and their use as agents for treating anxiety.Type: GrantFiled: October 9, 1984Date of Patent: February 11, 1986Assignee: American Cyanamid CompanyInventors: Daniel B. Moran, Dennis W. Powell, Jay D. Albright
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Patent number: 4539321Abstract: 5-Diaza-aryl-3-substituted-2-pyridone compounds useful for increasing cardiac contractility, pharmaceutical compositions and a method for the treatment of congestive heart failure comprising the use of said compounds.Type: GrantFiled: May 10, 1983Date of Patent: September 3, 1985Assignee: William H. Rorer, Inc.Inventor: Henry F. Campbell
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Patent number: 4532239Abstract: Basically-substituted pyridazines of the formula: ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3, independently of one another, denote hydrogen, halogen, hydroxyl, nitro, trifluoromethyl, alkyl, alkoxyalkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, phenyl, alkoxy, hydroxyalkoxy, alkoxy-alkoxy, alkenyloxy, alkynyloxy, cycloalkoxy, phenalkoxy, alkanoyl, alkanoylamino and --NH--CO--R.sup.9, R.sup.9 representing morpholino, piperidino or 1-pyrrolididinyl, or an optionally substituted ureido radical, R.sup.4 denotes hydrogen or lower alkyl and W denotes hydrogen, chlorine or bromine; and the acid-addition salts thereof are useful alone or in pharmaceutical preparations for treating cardiac complaints, circulatory complaints and high blood pressure. Several methods for preparing the basically-substituted pyridazines are also provided.Type: GrantFiled: December 20, 1983Date of Patent: July 30, 1985Assignee: Cassella AktiengesellschaftInventors: Thomas Raabe, Helmut Bohn, Piero A. Martorana, Rolf-Eberhard Nitz
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Patent number: 4478999Abstract: A process for the preparation of O-[3-phenyl-6-chloro-4-pyridazinyl] S-(alkyl) thiocarbonates by reaction of alkali metal salts of 3-phenyl-4-hydroxy-6-chloropyridazine with alkyl thiochloroformates in a water/acetone solution.Type: GrantFiled: April 13, 1983Date of Patent: October 23, 1984Assignee: Chemie Linz AktiengesellschaftInventor: Franz Raninger
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Patent number: 4454318Abstract: 4-Chloro-5-amino-2-phenyl-3(2H)-pyridazinone is prepared from 4,5-dichloro-2-phenyl-3(2H)-pyridazinone and ammonia in high yield and substantially free from 4-amino-5-chloro-2-phenyl-3(2 H)-pyridazinone in a method comprising reacting 4,5-dichloro-2-phenyl-3(2H)-pyridazinone with aqueous ammonia in the presence of a catalyst which is capable of selectively exchanging the 5-chlorine atom in 4,5-dichloro-2-phenyl-3(2H)-pyridazinone with a leaving group of such a nature that the resulting intermediate compound is capable of alkylating ammonia to 4-chloro-5-amino-2-phenyl-3(2H)-pyridazinone in high yield in the reaction medium, thereby regenerating the catalyst. The end product is isolated by filtration after the reaction and washed with water, and the mother liquor plus the wash water are used as reaction medium for the next batch.Type: GrantFiled: April 16, 1981Date of Patent: June 12, 1984Assignee: BASF AktiengesellschaftInventors: Niels Clauson-Kaas, Gert Jansen, Erik Olsen
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Patent number: 4428953Abstract: Novel pleuromutilin derivatives of formula I, ##STR1## in which R.sub.1 is ethyl or vinyl,m is 0 or 1, andR.sub.2 is a heterocyclic radical, in which a 5- or 6-membered, unsaturated or saturated heterocyclic ring containing one or more hetero atoms selected from oxygen, sulphur and nitrogen, is attached to the --S(CH.sub.2).sub.m --group,provided that when m is 0, R.sub.2 is other than pyridyl,their production and use as antimicrobial agents are described.Type: GrantFiled: March 8, 1982Date of Patent: January 31, 1984Assignee: Sandoz, Ltd.Inventors: Heinz Berner, Friederike Turnowsky, Georg Laber, Johannes Hildebrandt
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Patent number: 4413999Abstract: The invention provides amidoxime derivatives of the general formula ##STR1## wherein R.sub.1 is an alkyl group of 1 to 8 carbon atoms, phenyl, a heterocyclic ring structure of 5 to 8 atoms containing one or more nitrogen or oxygen atoms or combinations thereof or a bicyclic condensed ring system optionally containing at least one heterocyclic ring which groups may each be optionally substituted. R.sub.2 is a mono or bicyclic heterocyclic radical containing at least two nitrogen atoms which radical is also optionally substituted. R.sub.3 and R.sub.4 are independently H, or an alkyl of 1 to 4 carbon atoms or one, but not both, is ##STR2## and the other, H, wherein R.sub.5 or R.sub.6 are alkyls of 2 to 5 carbon atoms optionally substituted by R.sub.1, or a phenyl optionally substituted by R.sub.1 or R.sub.5 or R.sub.6 is combined with R.sub.1 to jointly form cyclic imidoximes or imidedioximes.Type: GrantFiled: March 5, 1982Date of Patent: November 8, 1983Assignee: Research Products Rehovot Ltd.Inventors: Charles Linder, Gershon Aviv
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Patent number: 4360672Abstract: Substituted pyridazones of the general formula ##STR1## where R.sup.2 is halogen or alkoxy, R.sup.1 is amino, alkylamino, dialkylamino, alkoxyamino, alkylalkoxyamino, halogen, alkoxy, trimethyleneimino or acylated amino, X is unsubstituted or substituted phenoxy of the formula ##STR2## where R.sup.3, R.sup.4 and R.sup.5 are each, independently of one another, hydrogen, halogen, nitro, cyano, carboxyl, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylmercapto, haloalkylmercapto, alkylsulfinyl or alkylsulfonyl and Y is hydrogen, cyano, haloalkyl, halogen or nitro, and herbicides which contain these compounds.Type: GrantFiled: March 26, 1981Date of Patent: November 23, 1982Assignee: BASF AktiengesellschaftInventors: Adolf Parg, Gerhard Hamprecht, Bruno Wuerzer
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Patent number: 4345077Abstract: Certain N-(meta-(6-chloro-3-pyridazinyloxy)phenyl)trifluoromethanesulfonamides and their use as herbicides.Type: GrantFiled: February 4, 1980Date of Patent: August 17, 1982Assignee: Shell Oil CompanyInventor: Kurt H. Pilgram
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Patent number: 4345076Abstract: Certain N-(para-(6-chloro-3-pyridazinyloxy)phenyl)trifluoromethanesulfonamides and their use as herbicides.Type: GrantFiled: February 4, 1980Date of Patent: August 17, 1982Assignee: Shell Oil CompanyInventors: Kurt H. Pilgram, Richard D. Skiles
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Patent number: 4297493Abstract: The manufacture of substantially pure 4-amino-5-chloro-1-phenylpyridaz-6-one by reaction of 4,5-dichloro-1-phenylpyridaz-6-one with ammonia in the presence of phenol-4-sulfonic acid.Type: GrantFiled: September 8, 1980Date of Patent: October 27, 1981Assignee: BASF AktiengesellschaftInventors: Winfried Richarz, Helmut Froehlich, Harald Schroeder
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Patent number: 4286092Abstract: The compound 5-amino-4-chloro-2-phenyl-3(2H)-pyridazinone free from 5-chloro-4-amino-2-phenyl-3(2H)-pyridazinone is used as selective weed-killer in a remarkably more efficacious and remarkably less phytotoxical way than the presently known "pyrazon" (mixture of 5-amino-4-chloro-2-phenyl-3(2H)-pyridazinone and 5-chloro-4-amino-2-phenyl-3(2H)-pyridazinone). The 5-amino-4-chloro-2-phenyl-3(2H)-pyridazinone is obtained from pyrazon by treating said pyrazon with a mineral acid of pre-fixed concentration, obtaining a suspension and filtering such a suspension. The use thereof as weed-killer is carried out in suitable formulations.Type: GrantFiled: June 19, 1979Date of Patent: August 25, 1981Assignee: Oxon Italia S.p.A.Inventor: Raimondo Motta
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Patent number: 4264769Abstract: A novel process for the preparation of a hydroxyphenyl ether compound of the formula ##STR1## in which R represents a radical of the formula ##STR2## wherein R.sup.1, R.sup.2 and R.sup.3 are independently selected from hydrogen, halogen, haloalkyl, nitro or cyano; orR represents a heterocyclic radical which optionally carries one or more substituents selected from halogen, halogenoalkyl, alkoxy, nitro and cyano and which can contain an optionally substituted fused benzene ring,which process comprises reacting a halogen compound of the formulaR--Hal (II)in whichR is defined as above, andHal is fluorine, chlorine or bromine,with a dihydroxybenzene of the formula ##STR3## in the presence of calcium hydroxide and in the presence of a polar diluent, at a temperature of from 20.degree. C. to 200.degree. C.Type: GrantFiled: February 2, 1979Date of Patent: April 28, 1981Assignee: Bayer AktiengesellschaftInventor: Heinz Forster
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Patent number: 4259328Abstract: Pyridazinylhydrazones capable of lowering blood pressure having the formula ##STR1## wherein R.sup.1 is hydrogen, chlorine, alkyl having from 1 to 4 carbon atoms, methoxy, hydroxyl, carbamoyl or cyano;R.sup.2 is morpholino; andK is a group having the formula ##STR2## wherein one of R.sup.3, R.sup.4, R.sup.5 or R.sup.6 is carboxyl or alkoxycarbonyl.Type: GrantFiled: June 12, 1978Date of Patent: March 31, 1981Assignee: Richter Gedeon Vegyeszeti Gyar RtInventors: Geza Szilagyi, Endre Kasztreiner, Judit Kosary, Peter Matyus, Zsuzsa Huszti, Gyorgy Cseh, Agnes Kenessey, Laszlo Tardos, Edit Kosa, Laszlo Jaszlits, Sandor Elek, Istvan Elekes, Istvan Polgari
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Patent number: 4255425Abstract: The compounds are sulphoxides of heterocyclicthioalkylthioureas, ureas and guanidines which are useful to produce inhibition of histamine H-2 receptors.Type: GrantFiled: November 13, 1978Date of Patent: March 10, 1981Assignee: Smith Kline & French Laboratories LimitedInventor: George R. White
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Patent number: 4255571Abstract: Pyridazones are prepared by heating 4,5-dihydro-3-pyridazones in the liquid phase in the presence of a dehydrogenation catalyst. The reaction temperature is in the range of from 150.degree. to 350.degree. C. The dehydrogenation catalyst contains a noble metal of subgroup 8 of the periodic table, which is generally supported on a carrier. The reaction is preferably carried out in the presence of a solvent.Type: GrantFiled: December 20, 1978Date of Patent: March 10, 1981Assignee: Hoechst AktiengesellschaftInventor: Werner H. Muller
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Patent number: 4237287Abstract: In a process for obtaining 4,5-dichloro-2-phenyl-3(2H)-pyridazinone from 5-chloro-4-amino-2-phenyl-3(2H)-pyridazinone the 5-chloro-4-amino-2-phenyl-3(2H)-pyridazinone is diazotized in a first stage in accordance with the following reaction: ##STR1## the compound (I) being obtained by dilution with water and filtration. In a second stage of the process the compound (I) is reacted with thionyl chloride in accordance with the following reaction: ##STR2## the 4,5-dichloro-2-phenyl-3(2H)-pyridazinone being obtained by dilution with water and filtration.Type: GrantFiled: July 10, 1979Date of Patent: December 2, 1980Assignee: Oxon Italia S.p.A.Inventor: Raimondo Motta
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Patent number: 4229205Abstract: New pyridaz-6-ones having a good herbicidal action, herbicides containing these compounds, and a process for controlling unwanted plant growth with these compounds.Type: GrantFiled: April 30, 1979Date of Patent: October 21, 1980Assignee: BASF AktiengesellschaftInventors: Hans Theobald, Bruno Wuerzer, Karl Kiehs