Ring In Alcohol Moiety Patents (Class 560/31)
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Patent number: 4786652Abstract: Psoriasis in mammals is relieved by topically administering naphthalenes of the formula: ##STR1## wherein: R.sup.1 is lower alkoxy or optionally substituted phenoxy,R.sup.2 is the same as R.sup.1, or R.sup.2 is hydrogen, lower alkyl, optionally substituted phenyl or optionally substituted phenylalkyl,R.sup.3 is hydrogen, lower alkyl, lower alkoxy, halo, optionally substituted phenyl, optionally substituted phenyl-lower-alkyl or optionally substituted phenyl-lower-alkoxy, and m is 1 or 2;X is the same and is either --C(O)OR.sup.4 or --C(O)NR.sup.5 R.sup.6,whereinR.sup.4 is alkyl, phenyl or benzyl optionally substituted with one or two lower alkyl groups, lower alkoxy groups or halo; andR.sup.5 and R.sup.6 are independently hydrogen, lower alkyl, cycloalkyl or phenyl optionally substituted with one or two lower alkyl groups, lower alkoxy groups or halo.Type: GrantFiled: March 9, 1987Date of Patent: November 22, 1988Assignee: Syntex (U.S.A.) Inc.Inventor: Michael C. Venuti
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Patent number: 4767447Abstract: Compounds of the formula ##STR1## wherein R is halogen; C.sub.1 -C.sub.2 alkyl; C.sub.1 -C.sub.2 alkoxy; trifluoromethoxy or difluoromethoxy; nitro; cyano; C.sub.1 -C.sub.2 haloalkyl; R.sup.a SO.sub.n -- wherein n is 0 or 2 and R.sup.a is C.sub.1 -C.sub.2 alkyl, trifluoromethyl or difluoromethyl;R.sup.1 is hydrogen or C.sub.1 -C.sub.4 alkyl;R.sup.2 is hydrogen or C.sub.1 -C.sub.4 alkyl; orR.sup.1 and R.sup.2 together are C.sub.2 -C.sub.5 alkylene;R.sup.3 is hydrogen or C.sub.1 -C.sub.4 alkyl;R.sup.4 is hydrogen or C.sub.1 -C.sub.4 alkyl; orR.sup.3 and R.sup.4 together are C.sub.2 -C.sub.5 alkylene;R.sup.5, R.sup.6, R.sup.7 and R.sup.8 independently are (1) hydrogen; (2) halogen; (3) C.sub.1 -C.sub.4 alkyl; (4) C.sub.1 -C.sub.4 alkoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C.sub.1 -C.sub.4 haloalkyl; (9) R.sup.b SO.sub.n -- wherein n is the integer 0, 1 or 2; and R.sup.b is (a) C.sub.1 -C.sub.4 alkyl; (b) C.sub.1 -C.sub.4 alkyl substituted with halogen or cyano; (c) phenyl; or (d) benzyl; (10) --NR.Type: GrantFiled: September 12, 1986Date of Patent: August 30, 1988Assignee: Stauffer Chemical CompanyInventors: David L. Lee, William J. Michaely
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Patent number: 4760057Abstract: This invention relates to novel (acyloxyalkoxy)carbonyl derivatives as bioreversible prodrug moieties for primary and secondary amine functions in drugs having a primary or secondary amine function thereon. Hydrolytic enzymes are used to trigger the regeneration of the parent amine drug of the carbamate prodrug moiety. The case also contains pharmaceutical composition, method of treatment and process claims.Type: GrantFiled: April 22, 1985Date of Patent: July 26, 1988Assignee: Merck & Co., Inc.Inventor: Jose Alexander
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Patent number: 4758587Abstract: Psoriasis in mammals is relieved by topically administering naphthalenes of the formula: ##STR1## wherein: R.sup.1 is lower alkoxy or optionally substituted phenoxy;R.sup.2 is hydrogen, lower alkyl, optionally substituted phenyl or optionally substituted phenylalkyl;R.sup.3 is hydrogen, lower alkyl, lower alkoxy, halo, optionally substituted phenyl, optionally substituted phenyl-lower-alkyl or optionally substituted phenyl-lower-alkoxy, and m is 1 or 2;X and Y are different and are either R.sup.4 or --C(O)W whereinR.sup.4 is lower alkyl or optionally substituted phenyl-lower-alkyl;W is --OR.sup.5 or --NR.sup.6 R.sup.7,whereinR.sup.5 is alkyl, optionally substituted phenyl or optionally substituted benzyl; andR.sup.6 and R.sup.7 are independently hydrogen, lower alkyl, cycloalkyl or optionally substituted phenyl.Type: GrantFiled: March 9, 1987Date of Patent: July 19, 1988Assignee: Syntex (U.S.A.) Inc.Inventor: Michael C. Venuti
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Patent number: 4752615Abstract: A compound of the formula: ##STR1## useful as a fungicidal agent against phytopathogenic fungi, particularly their strains resistant to benzimidazole, thiophanate and/or cyclic imide fungicides.Type: GrantFiled: November 13, 1986Date of Patent: June 21, 1988Assignee: Sumitomo Chemical Company, LimitedInventors: Junya Takahashi, Toshiro Kato, Hiroshi Noguchi, Yukio Oguri, Shigeo Yamamoto, Katsuzo Kamoshita
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Patent number: 4694097Abstract: Carbamate esters are produced by reacting at ambient or elevated temperature an amine with carbon monoxide and an alcohol in the presence of a protonic acid, a dehydrating agent, for example a molecular sieve, and a catalyst comprising (a) at least one metal selected from the group palladium, rhodium, ruthenium, iridium and cobalt, and (b) at least one of the metals copper, molybdenum and iron, the components (a) and (b) being in the form of elemental metals or compounds thereof. The presence of the dehydrating agent reduces the formation of by-product carbon dioxide.Type: GrantFiled: April 25, 1986Date of Patent: September 15, 1987Assignee: The British Petroleum Company p.l.c.Inventors: Howard Alper, David J. H. Smith
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Patent number: 4687872Abstract: A process for preparing urethanes by reacting a solution of a nitrogen-containing organic compound and a hydroxyl-containing organic compound with carbon monoxide in the presence of a catalyst comprising rhodium, as a metal or compound, is disclosed. In the process of this invention, the rate of conversion and selectivity to urethane is increased by providing a rhodium catalyst comprising a polyamino ligand having at least two tertiary amino groups capable of coordinating with rhodium.Type: GrantFiled: December 9, 1985Date of Patent: August 18, 1987Assignees: Catalytica Associates, Haldor Topsoe A/SInventors: John H. Grate, David R. Hamm
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Patent number: 4678856Abstract: The present invention relates to a method of manufacturing aromatic urethane, an aromatic mononitro-compound, an aromatic primary amine, and carbon monoxide being reacted using a catalyst containing a platinum group metal-containing compound as a major constituent to prepare N,N'-di-substituted urea. The resultant N,N'-di-substituted urea is reacted with a hydroxyl group-containing organic compound to prepare an aromatic primary amine and aromatic urethane, and the aromatic primary amine is separated to obtain aromatic urethane.Type: GrantFiled: September 2, 1986Date of Patent: July 7, 1987Assignee: Nippon Kokan Kabushiki KaishaInventors: Takao Ikariya, Masanori Itagaki, Masatsugu Mizuguchi, Itaru Sakai, Osamu Tajima
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Patent number: 4665193Abstract: Compounds of the formula ##STR1## wherein A is ##STR2## intervene in the conversion of angiotensinogen to angiotensin II by inhibiting renin and thus are useful as anti-hypertensive agents.Type: GrantFiled: June 27, 1986Date of Patent: May 12, 1987Assignee: E. R. Squibb & Sons, Inc.Inventors: Denis E. Ryono, Edward W. Petrillo, Jr.
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Patent number: 4610985Abstract: Allophanate derivatives of the formula ##STR1## in which R.sup.1 and R.sup.2 can be identical or different and represent an aliphatic, cycloaliphatic, araliphatic or aromatic radical each of which is optionally monosubstituted or polysubstituted by identical or different substituents andR.sup.3 represents the radical --XR.sup.4 or --NR.sup.5 R.sup.6,whereinR.sup.4 represents alkyl, alkoxyalkyl, or aryl which is optionally monosubstituted or polysubstituted by identical or different substituents, X represents oxygen or sulphur andR.sup.5 and R.sup.6 are identical or different and represent hydrogen, alkyl, or aryl which is optionally monosubstituted or polysubstituted by identical or different substituents, orR.sup.5 and R.sup.6, together with the nitrogen atom on which they stand, form a saturated heterocyclic radical which is optionally monosubstituted or polysubstituted by identical or different substituents and can be interrupted by further hetero-atoms,which possess fungicidal activity.Type: GrantFiled: April 10, 1985Date of Patent: September 9, 1986Assignee: Bayer AktiengesellschaftInventors: Wolfgang Fuhrer, Engelbert Kuhle, Gerd Hanssler
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Patent number: 4602033Abstract: Aryl N-oxalyl-N-methyl-carbamates of the general formula ##STR1## in which X represents an alkoxy, alkenoxy, alkinoxy, aryloxy, alkylthio, alkenylthio, alkinylthio or arylthio radical, each of which may be optionally substituted or represents a radical of the general formula --N R.sup.3 R.sup.4, wherein R.sup.3 and R.sup.4 are identical or different and represent a hydrogen atom or an alkyl, alkenyl, alkinyl, cycloalkyl, cycloalkenyl or aryl radical, each of which may be optionally substituted, or the radicals R.sup.3 and R.sup.4, together with the N atom to which they are bonded, form an optionally substituted heterocyclic ring, andR.sup.1 represents an aryl radical which is optionally substituted,are novel and find use as pesticides, especially for combating insects, acarids and nematodes.Type: GrantFiled: January 3, 1985Date of Patent: July 22, 1986Assignee: Bayer AktiengesellschaftInventors: Gerhard Heywang, Engelbert Kuhle, Wolfgang Behrenz, Ingeborg Hammann, Bernhard Homeyer
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Patent number: 4594441Abstract: A process for the preparation of urethanes. Urethanes having the general formula R.sub.1 (NHCOOR.sub.2).sub.n are reacted with an alcohol at a temperature of 120.degree. to 400.degree. C. in amounts such that, for every mol of the urethane, at least one mol of the alcohol is present. R.sub.1 is a radical obtained by removing the isocyanate groups from an n-functional organic isocyanate, which isocyanate has a boiling point greater than 100.degree. C. at atmospheric pressure. R.sub.2 is a radical obtained by removing the hydroxyl group from a monohydric alcohol which has a boiling point greater than 140.degree. C. at atmospheric pressure.Type: GrantFiled: May 14, 1984Date of Patent: June 10, 1986Assignee: Bayer AktiengesellschaftInventors: Kurt Findeisen, Klaus Konig, Rudolf Fauss, Peter Heitkamper
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Patent number: 4507292Abstract: Aryl N-oxalyl-N-methyl-carbamates of the general formula ##STR1## in which X represents an alkoxy, alkenoxy, alkinoxy, aryloxy, alkylthio, alkenylthio, alkinylthio or arylthio radical, each of which may be optionally substituted, or represents a radical of the general formula --N R.sup.3 R.sup.4, wherein R.sup.3 and R.sup.4 are identical or different and represent a hydrogen atom or an alkyl, alkenyl, alkinyl, cycloalkyl, cycloalkenyl or aryl radical, each of which may be optionally substituted,or the radicals R.sup.3 and R.sup.4, together with the N atom to which they are bonded, form an optionally substituted heterocyclic ring, andR.sup.1 represents an aryl radical which is optionally substituted,are novel and find use as pesticides, especially for combating insects, acarids and nematodes.Type: GrantFiled: January 27, 1983Date of Patent: March 26, 1985Assignee: Bayer AktiengesellschaftInventors: Gerhard Heywang, Engelbert Kuhle, Wolfgang Behrenz, Ingeborg Hammann, Bernhard Homeyer
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Patent number: 4491671Abstract: The present invention relates to a process for the preparation of N-substituted imido-dicarboxylic acid diaryl ester compound of the formulaR.sup.1 --N(CO--OR.sup.2).sub.2 (I)whereinR.sup.1 is an optionally substituted aliphatic, cycloaliphatic, araliphatic, aromatic or heterocyclic radical; andR.sup.2 is an optionally substituted aryl radical, which are useful as intermediates for the production of known herbicides, which process comprises reacting a primary amine of the formulaR.sup.1 --NH.sub.2 (II)with a carbonic acid aryl ester halide of the formulaX--CO--OR.sup.2 (III)wherein X is a halogen atom, at a temperature between 100.degree. and 300.degree. C.Type: GrantFiled: June 10, 1982Date of Patent: January 1, 1985Assignee: Bayer AktiengesellschaftInventors: Karlfried Dickore, Engelbert Kuhle
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Patent number: 4486447Abstract: Bis-sulfenylated bis-carbamate compounds exhibit activity against insect and mite pests.Type: GrantFiled: June 24, 1983Date of Patent: December 4, 1984Assignee: Union Carbide CorporationInventor: Themistocles D. J. D'Silva
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Patent number: 4474806Abstract: Sulfonyl or carbonyl derivatives of inositols are found to be effective phospholipase C inhibitors and thereby potent anti-inflammatory and analgesic agents. These inositol derivatives are prepared by condensation of a protected inositol with a substituted sulfonic or carboxylic acid derivative followed by removal of protecting groups.Type: GrantFiled: May 10, 1982Date of Patent: October 2, 1984Assignee: Merck & Co., Inc.Inventors: Thomas R. Beattie, Shu S. Yang
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Patent number: 4474807Abstract: This invention is directed to novel antimicrobial agents. More particularly, this invention is directed to 2-(3-iodo-2-propynyloxy)-ethyl carbamates of the formula ##STR1## wherein R is hydrogen, linear or branched alkyl of from 1 to 12 carbon atoms, cycloalkyl of from 4 to 8 carbon atoms, aryl, substituted aryl, aralkyl, or arylsulfonyl;R.sup.1 and R.sup.2, which may be the same or different, each are hydrogen, linear or branched alkyl or alkenyl of from 1 to 6 carbon atoms, or cycloalkyl of from 5 to 7 carbon atoms, or R.sup.1 and R.sup.2, taken together, represent --(CH.sub.2).sub.m --, in which m is an integer of from 4 to 6; andR.sup.3, R.sup.4, R.sup.5, and R.sup.6, which may be the same or different, each represent hydrogen, alkyl of from 1 to 4 carbon atoms, or aryl, or CCl.sub.3, or R.sup.3 and R.sup.5 or R.sup.4 and R.sup.6, taken together, represent --(CH.sub.2).sub.n --, in which n is an integer of from 3 to 5,as well as a process for their preparation and their use as antimicrobial agents.Type: GrantFiled: September 29, 1982Date of Patent: October 2, 1984Assignees: Henkel Kommandigesellschaft auf Aktien, Montedison S.p.A.Inventors: Werner Gerhardt, Rudolf Lehmann
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Patent number: 4451406Abstract: Novel N-substituted imido-dicarboxylic acid diaryl ester compounds of the general formula ##STR1## in which R.sup.1 represents an optionally substituted aliphatic, cycloaliphatic, araliphatic, aromatic, heterocyclic radical andR.sup.2 and R.sup.3 can be identical or different and represent an optionally substituted aryl radical,and a process for their preparation characterized in that a carbamic acid aryl ester of the general formula:R.sup.1 --NH--CO--OR.sup.2 (II)in which R.sup.1 and R.sup.2 have the abovementioned meanings, is reacted with a carbonic acid aryl ester halide of the general formulaX--CO--OR.sup.3 (III)in whichR.sup.3 has the abovementioned meaning andX represents a halogen atom, optionally in the presence of a diluent, optionally at a temperature between 100.degree. and 300.degree. C.The new compounds (I) can be used as intermediate products for the preparation of known herbicidal active compounds from the 1,3,5-triazine,2,4-(1H,3H)-dione series.Type: GrantFiled: August 5, 1983Date of Patent: May 29, 1984Assignee: Bayer AktiengesellschaftInventors: Karlfried Dickore, Engelbert Kuhle
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Patent number: 4447635Abstract: Novel N-substituted imido-dicarboxylic acid diaryl ester compounds of the general formula ##STR1## in which R.sup.1 represents an optionally substituted aliphatic, cycloaliphatic, araliphatic, aromatic, heterocyclic radical andR.sup.2 and R.sup.3 can be identical or different and represent an optionally substituted aryl radical, and a process for their preparation characterized in that a carbamic acid aryl ester of the general formulaR.sup.1 --NH--CO--OR.sup.2 (II)in which R.sup.1 and R.sup.2 have the abovementioned meanings, is reacted with a carbonic acid aryl ester halide of the general formulaX--CO--OR.sup.3 (III)in whichR.sup.3 has the abovementioned meaning andX represents a halogen atom, optionally in the presence of a diluent, optionally at a temperature between 100.degree. and 300.degree. C.The new compounds (I) can be used as intermediate products for the preparation of known herbicidal active compounds from the 1,3,5-triazine,2,4-(1H,3H)-dione series.Type: GrantFiled: June 30, 1982Date of Patent: May 8, 1984Assignee: Bayer AktiengesellschaftInventors: Karlfried Dickore, Engelbert Kuhle
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Patent number: 4442117Abstract: There are described novel homoserine derivatives of the formula (I) ##STR1## which possess valuable microbicidal properties. In the formula: Ar is substituted phenyl or naphthyl; R.sub.1 is C.sub.2 -C.sub.6 alkyl optionally interrupted by oxygen or sulfur, 2-furyl, 2-tetrahydrofuryl, 1H-1,2,4-triazolylmethyl, 1-imidazolylmethyl, 1-pyrazolylmethyl, C.sub.2 -C.sub.4 alkenyl or cyclopropyl, each of which is optionally substituted by halogen; R.sub.2 is hydrogen or methyl; R.sub.3 is hydrogen or C.sub.1 -C.sub.4 alkyl; and B is halogen or an ester, thioester, sulfonic acid ester or sulfonic acid amide group. Additionally, where B is halogen, R.sub.1 may be halomethyl. The novel derivatives can be used for combating microorganisms harmful to plants, particularly for combating phytopathogenic fungi, and they have for practical requirements a very favorable curative and protective action for protecting cultivating plants, without the plants being impaired as a result of undesirable secondary effects.Type: GrantFiled: October 23, 1980Date of Patent: April 10, 1984Assignee: Ciba-Geigy CorporationInventors: Walter Kunz, Wolfgang Eckhardt, Adolf Hubele, Peter Riebli
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Patent number: 4430262Abstract: Isocyanates and derivatives thereof are prepared by oxidative conversion of compounds having at least one group ##STR1## wherein X represents OY or ##STR2## wherein Y is H, a metal ion or group NR.sup.3 R.sup.4 R.sup.5 R.sup.6 wherein each of R.sup.3, R.sup.4, R.sup.5 and R.sup.6 which may be the same or different, is H, alkyl or (substituted) (alk)aryl and Z is a (substituted) alkyl or aryl group. Phenyl isocyanate and derivatives thereof are preferably prepared electrochemically from the corresponding oxamides and oxanilides.Type: GrantFiled: March 11, 1982Date of Patent: February 7, 1984Assignee: Shell Oil CompanyInventors: Rainer Engels, Jan H. H. Meurs
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Process for the preparation of N,O-disubstituted urethanes useful for the preparation of isocyanates
Patent number: 4430505Abstract: A process for the preparation of N,O-disubstituted urethanes. Urea or polyurets, primary amines and alcohols are reacted at 120.degree.-350.degree. C. in the presence of N-substituted urethanes and/or N-mono- or N,N'-disubstituted ureas or polyureas. In a preferred embodiment, the reactants further include catalysts known to be useful in esterification of carboxylic acids. The urethanes produced in accordance with this process are particularly useful as starting materials for preparation of isocyanates.Type: GrantFiled: October 15, 1980Date of Patent: February 7, 1984Assignee: Bayer AktiengesellschaftInventors: Peter Heitkamper, Klaus Konig, Kurt Findeisen, Rudolf Fauss, Rudolf Sundermann -
Patent number: 4426222Abstract: Novel carbaminic acid phenyl esters of the general formula ##STR1## are described, in which R.sub.1 is C.sub.1 -C.sub.2 -alkoxy-C.sub.1 -C.sub.2 -alkyl, di-C.sub.1 -C.sub.2 -alkoxy-C.sub.1 -C.sub.2 -alkyl, cyano-C.sub.1 -C.sub.2 -alkyl, halogen-C.sub.1 -C.sub.2 -alkyl, phenyl-C.sub.1 -C.sub.2 -alkyl, 1,3-dioxolan-2-yl-methyl, 2-methyl-1,3-dioxolan-4-yl-methyl, 2,2-dimethyl-1,3-dioxolan-4-yl-methyl or aminocarbonylmethyl;R.sub.2 is phenyl optionally mono- or disubstituted by one or more substituents selected from the group consisting of halogen, methyl and methoxy; andR.sub.3 is C.sub.1 -C.sub.8 alkyl, C.sub.2 -C.sub.8 alkenyl, cyclopropyl or trichloromethyl, or R.sub.1 is methyl or ethyl, R.sub.2 is .alpha.-cyanobenzyl or 1-cyano-2-phenylethyl and R.sub.3 is ethyl.Type: GrantFiled: January 4, 1982Date of Patent: January 17, 1984Assignee: Schering AktiengesellschaftInventors: Gerhard Boroschewski, Ludwig Nusslein, Friedrich Arndt
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Patent number: 4425361Abstract: Formamido-carbamates of the formula ##STR1## wherein R.sub.1 is ##STR2## R.sub.2 is ##STR3## or R.sub.4 --CH.sub.2 --CH.sub.2 --, R.sub.3 is hydrogen, ##STR4## R.sub.4 is ##STR5## R.sub.5, R.sub.6 and R.sub.7 independently of one another are each hydrogen, halogen or C.sub.1 -C.sub.4 -alkyl,processes for producing them and their use for combating pests are described.Type: GrantFiled: November 18, 1981Date of Patent: January 10, 1984Assignee: Ciba-Geigy CorporationInventors: Dieter Lohmann, Christian d'Hondt, Guenter Rist
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Patent number: 4388238Abstract: A process for the preparation of N,O-disubstituted urethanes. Primary amines and alcohols are reacted with organic compounds having carbonyl groups at 120.degree. to 350.degree. C. Suitable carbonyl-containing compounds include N-unsubstituted urethanes. N-mono-substituted, N,N'-disubstituted ureas, or polyureas may be used in combination with the N-unsubstituted urethane. The product urethanes are particularly suitable for the preparation of isocyanates.Type: GrantFiled: October 15, 1980Date of Patent: June 14, 1983Assignee: Bayer AktiengesellschaftInventors: Peter Heitkamper, Klaus Konig, Rudolf Fauss, Kurt Findeisen
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Patent number: 4375000Abstract: A process for the preparation of an aryl mono-, di-, and/or polyurethane comprising the steps of A. reacting a primary aromatic mono-, di-, and/or polyamine with an O-alkyl carbamate in the presence of an alcohol at temperatures greater than 160.degree. C., andB. separating the ammonia and other by-products from the aryl mono-, di-, and/or polyurethane.The reaction is preferably carried out in the presence of urea. The aryl mono-, di-, and/or polyurethanes produced are valuable end and intermediate products. They can be transferred into the corresponding isocyanates which can then be used for the preparation of polyurethanes.Type: GrantFiled: March 31, 1980Date of Patent: February 22, 1983Assignee: BASF AktiengesellschaftInventors: Franz Merger, Friedrich Towae, Wolfgang Harder
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Patent number: 4373105Abstract: New m-anilide-urethanes, processes for their manufacture, herbicides containing these compounds, and processes for controlling unwanted plant growth with these compounds.Type: GrantFiled: March 11, 1981Date of Patent: February 8, 1983Assignee: BASF AktiengesellschaftInventors: Wolfgang Rohr, Ulrich Schirmer, Bruno Wuerzer
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Patent number: 4370497Abstract: The present invention relates to the use of telluroxides as mild and selective oxidizing agents serving to oxidize certain functions, notably >C.dbd.S groups, in the presence of other relatively easily oxidized functions which remain unaffected; telluroxides of interest as oxidizing agents include, for example, compounds of the formula: ##STR1## wherein R and R.sup.1, which may be the same or different, each represent an optionally substituted aryl or heterocyclic group; or R and R.sup.1 together with the tellurium atom therebetween represent a heterocyclic ring, which may contain one or more further heteroatoms, and which may carry substituents and/or fused aromatic rings.Type: GrantFiled: August 7, 1980Date of Patent: January 25, 1983Inventors: Derek H. R. Barton, Steven V. Ley, Clive A. Meerholz
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Patent number: 4362888Abstract: Dimethacrylates are provided having the following chemical structure: ##STR1## where ##STR2##is a saturated, 6 membered, monocyclic, hydrocarbyl ring system;R.sub.1, R.sub.2 and R.sub.3 are the same or different and are hydrogen or alkyl or alkoxy groups having 1 to 12 carbon atoms; andR.sub.4 and R.sub.5 are the same or different and are hydrogen or groups of the formula: ##STR3## where R.sub.6 is an aliphatic, aromatic or cycloaliphatic group having 1 to 14 carbon atoms, provided that at least one of the groups R.sub.4 and R.sub.5 is a group of the formula: ##STR4## These compounds are useful in dental material which cures to form polymers having high mechanical strength, low water sorption, resistance to staining, good color stability when exposed to short-wave radiation (e.g., sunlight) and good chemical resistance to the oral environment. Also provided are a method for polymerizing this compound in situ on teeth and a tooth comprising a polymer of this compound.Type: GrantFiled: September 15, 1980Date of Patent: December 7, 1982Assignee: Scientific Pharmaceuticals, Inc.Inventors: Jan A. Orlowski, David V. Butler, Patrick D. Kidd
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Patent number: 4358606Abstract: Novel esters of phenylalkyloxy- or phenylalkylthioacylamino acids and pyridylalkyloxy- or pyridylalkylthioacylamino acids, synthesis thereof, intermediates therefor, and the use of said esters for the control of weeds.Type: GrantFiled: June 19, 1981Date of Patent: November 9, 1982Assignee: Zoecon CorporationInventors: Shy-Fuh Lee, Clive A. Henrick
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Patent number: 4347377Abstract: The invention concerns a new process for the preparation of polyhalogenphenyl carbamates of the formula (I)R.sup.2 -OCONHR.sup.1 (I)whereinR.sup.1 is alkyl, aralkyl or aryl, where the aromatic rings may optionally be substituted; andR.sup.2 is phenyl substituted with three, four or five halogens, through intermediates of the formula (IV)(R.sup.2 --O).sub.2 C.dbd.NR.sup.1 (IV)wherein R.sup.1 and R.sup.2 are as defined above.The compounds of the formula (I) are valuable acylating agents. The intermediates of the formula (IV) are new compounds, which are also encompassed by the invention.Type: GrantFiled: September 19, 1980Date of Patent: August 31, 1982Assignee: Chinoin Gyogyszer es Vegyeszeti Termekek Gyara R.T.Inventors: Istvan Bitter, Rudolf Soos, Geza Toth, Laszlo Toke, Gabor Szabo
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Patent number: 4340739Abstract: Novel valuable N-chloromethyl-carboxylic acid anilides, a process for their preparation, and their use for the preparation of novel valuable N-carboxylic acid anilides.Type: GrantFiled: November 30, 1979Date of Patent: July 20, 1982Assignee: BASF AktiengesellschaftInventors: Peter Plath, Karl Eicken, Wolfgang Rohr
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Patent number: 4339592Abstract: A urethane is produced by reacting an organic nitro compound with carbon monoxide and an organic compound containing at least one hydroxyl group in the presence of a catalyst and a co-catalyst. This reaction is conducted in the liquid phase at elevated temperature and pressure. The catalyst employed is an element and/or compound of an element from the group of noble metals of the 8th Secondary Group of the Periodic Table. The co-catalyst used is formed from (1) a component taken from the group consisting of iron oxychloride, a mixture of iron compounds containing iron oxychloride and oxide-chloride combinations and (2) metallic iron or an iron alloy in finely divided or high surface form. The oxides which may be used in the oxide-chloride combinations of co-catalyst component (1) are the oxides and/or oxide hydrates of tetravalent tin, trivalent chromium, hexavalent molybdenum, hexavalent tungsten, pentavalent vanadium, divalent iron and trivalent iron.Type: GrantFiled: February 26, 1981Date of Patent: July 13, 1982Assignee: Bayer AktiengesellschaftInventors: Robert Becker, Christian Rasp, Gunter Stammann, Johann Grolig
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Patent number: 4335138Abstract: Novel carbamates derived from substituted cyclic .beta.-keto-alcohols, their preparation, and pharmaceutical formulations which contain these compounds and which may be used as hypnotics in the treatment of sleep disturbance and as sedatives.Type: GrantFiled: September 15, 1980Date of Patent: June 15, 1982Assignee: BASF AktiengesellschaftInventors: Walter-Wielant Wiersdorff, Karl-Heinz Geiss, Harald Weifenbach, Wolfgang Worstmann, Dieter Lenke, Rolf Kretzschmar
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Patent number: 4335246Abstract: Substituted arylamine dye intermediates and their preparation are disclosed.Type: GrantFiled: September 24, 1979Date of Patent: June 15, 1982Assignee: Aziende Colori Nazionali Affini ACNA S.p.A.Inventors: Francesco De Feo, Giovanni Burei, Roberto Cipolli
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1H-Inden-1-one derivatives, their use in microbicidal compositions, and for combating microorganisms
Patent number: 4333949Abstract: 2,3-Dichloro-7-hydroxy-1H-inden-1-one derivatives of the formula I ##STR1## wherein R.sub.1 is hydrogen or one of the groups ##STR2## R.sub.2 and R.sub.3 independently of one another are each hydrogen, fluorine, chlorine, bromine, C.sub.1 -C.sub.4 -alkyl, trifluoromethyl or nitro,R.sub.4 is hydrogen, C.sub.1 -C.sub.6 -alkyl or C.sub.2 -C.sub.4 -alkenyl, each of which is unsubstituted or substituted by halogen, or R.sub.4 is phenyl which is unsubstituted or is substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, halogen, trifluoromethyl, cyano or nitro, or it is a C.sub.3 -C.sub.6 -cycloalkyl group, andR.sub.5 is C.sub.1 -C.sub.6 -alkyl, C.sub.3 -C.sub.6 -cycloalkyl or C.sub.2 -C.sub.4 -alkenyl.These compounds exhibit a microbicidal action against in particular phytopathogenic fungi and bacteria.Type: GrantFiled: June 5, 1981Date of Patent: June 8, 1982Assignee: Ciba-Geigy CorporationInventors: Elmar Sturm, Robert Nyfeler -
Patent number: 4328165Abstract: Novel phenylcarbamic acid chlorides, and their preparation by reacting N-mono-substituted phenylenediamines with excess phosgene and then reacting the products with thioalcohols, alcohols, hydroxylamines or amines.The novel phenylcarbamic acid chlorides of the formula I obtainable by the process of the invention are valuable intermediates for the preparation of crop protection agents, especially herbicides.Type: GrantFiled: February 12, 1980Date of Patent: May 4, 1982Assignee: BASF AktiengesellschaftInventor: Ulrich Schirmer
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Patent number: 4304922Abstract: Production of urethanes by the oxycarbonylation reaction of N,N'-disubstituted ureas and organic compounds containing at least one hydroxyl group with carbon monoxide in the presence of molecular oxygen and/or organic nitro compounds and a catalyst system comprising (a) a noble metal and/or noble metal compound of the eighth subgroup of the periodic system of elements and (b) a compound of an element and/or elements of the third to fifth main group and/or first to eighth subgroup of the periodic system of elements characterized in that said compounds are capable of undergoing Redox reactions under the reaction conditions.Type: GrantFiled: February 27, 1980Date of Patent: December 8, 1981Assignee: Bayer AktiengesellschaftInventors: Robert Becker, Johann Grolig, Christian Rasp, Gunter Stammann
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Patent number: 4291061Abstract: 2,3-Dichloro-7-hydroxy-1H-inden-1-one derivatives of the formula I ##STR1## wherein R.sub.1 is hydrogen or one of the groups ##STR2## R.sub.2 and R.sub.3 independently of one another are each hydrogen, fluorine, chlorine, bromine, C.sub.1 -C.sub.4 -alkyl, trifluoromethyl or nitro,R.sub.4 is hydrogen, C.sub.1 -C.sub.6 -alkyl or C.sub.2 -C.sub.4 -alkenyl, each of which is unsubstituted or substituted by halogen, or R.sub.4 is phenyl which is unsubstituted or is substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, halogen, trifluoromethyl, cyano or nitro, or it is a C.sub.3 -C.sub.6 -cycloalkyl group, andR.sub.5 is C.sub.1 -C.sub.6 -alkyl, C.sub.3 -C.sub.6 -cycloalkyl or C.sub.2 -C.sub.4 -alkenyl.These compounds exhibit a microbicidal action against in particular phytopathogenic fungi and bacteria.Type: GrantFiled: October 31, 1979Date of Patent: September 22, 1981Assignee: Ciba-Geigy CorporationInventors: Elmar Sturm, Robert Nyfeler
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Patent number: 4282368Abstract: p-Substituted, aromatic carbamic acid esters are prepared by reacting an aromatic carbamic acid ester with an olefin in the presence of an inorganic acid or sulfonic acid.The aromatic carbamic acid esters obtainable by the process of the invention are active ingredients for pesticides and drugs, as well as valuable starting materials for the preparation of such ingredients and of dyes.Type: GrantFiled: June 2, 1980Date of Patent: August 4, 1981Assignee: BASF AktiengesellschaftInventors: Franz Merger, Gerhard Nestler
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Patent number: 4278805Abstract: A process for the preparation of an aryl-mono and/or polyurethane comprising the steps ofA. reacting a primary aromatic mono, di-, and/or polyamine with an O-alkyl carbamate in the presence of alcohol and catalysts, andB. separating the ammonia and other by-products from the aliphatic and/or cycloaliphatic di- and/or polyurethane.The reaction is preferably carried out in the presence of urea. The aryl mono-, di-, and/or polyurethanes produced are valuable end and intermediate products. They can be transferred into the corresponding isocyanates which can then be used for the preparation of polyurethanes.Type: GrantFiled: March 31, 1980Date of Patent: July 14, 1981Assignee: BASF AktiengesellschaftInventors: Franz Merger, Friedrich Towae
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Patent number: 4267353Abstract: This invention relates to an improved process for the preparation of urethanes by the reaction of aromatic nitro compounds with alcohols and carbon monoxides in the presence of catalyst systems containing sulphur and/or selenium and/or compounds of these elements.Type: GrantFiled: August 22, 1979Date of Patent: May 12, 1981Assignee: Bayer AktiengesellschaftInventors: Hans-Joachim Scholl, Armin Zenner
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Patent number: 4266070Abstract: A process for the production of urethanes is provided in which an organic primary or secondary amine is contacted, in the substantial absence of reactive oxygen, with a source of carbon monoxide and an organic compound containing at least one hydroxyl group in the presence of a catalyst comprising a member selected from the group consisting of carbonyls of Co, Mo, Ti, Rh, Fe, Ni and mixtures thereof. Urethane yields and selectivities are further improved by conducting the reaction in the additional presence of an organic compound containing at least one C.dbd.N or C.dbd.C group. When such unsaturated organic compounds are employed, the catalyst can additionally comprise iridium carbonyl.Type: GrantFiled: May 25, 1979Date of Patent: May 5, 1981Assignee: Halcon Research and Development Corp.Inventor: David Moy
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Patent number: 4262130Abstract: The present invention relates to an improved process for the production of urethanes (carbamic acid esters) by the reaction of organic nitro compounds with carbon monoxide and organic compounds containing at least one hydroxy group in the presence of palladium and/or palladium compounds and a cocatalyst which consists of a mixture of one or more iron oxides and/or iron hydroxides and activating chloride-containing additives.Type: GrantFiled: January 17, 1980Date of Patent: April 14, 1981Assignee: Bayer AktiengesellschaftInventors: Robert Becker, Johann Grolig, Christian Rasp
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Patent number: 4260781Abstract: A process for the production of carbamates is provided in which an organic primary or secondary amine is contacted, in the substantial absence of reactive oxygen, with a source of carbon monoxide, an organic compound containing at least one hydroxyl group, and a metal reactant comprising at least one member selected from the group consisting of compounds and complexes of Group VIII of the Periodic Table.Type: GrantFiled: May 25, 1979Date of Patent: April 7, 1981Assignee: Halcon Research and Development Corp.Inventor: Robert J. Harvey
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Patent number: 4257804Abstract: Carbamic acid ester of the formula ##STR1## in which R and R.sub.1 are the same or different and are hydrogen, an aliphatic hydrocarbon residue which may also be substituted, a cycloaliphatic hydrocarbon residue which may also be substituted, an aromatic hydrocarbon residue which may also be substituted or a heterocyclic residue or wherein R and R.sub.1 together with the adjoining nitrogen atom form a heterocyclic residue.The compounds of the invention are herbicidal agents of particularly strong activity.Type: GrantFiled: April 10, 1979Date of Patent: March 24, 1981Assignee: Schering AktiengesellschaftInventors: Friedrich Arndt, Ludwig Nusslein
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Patent number: 4258201Abstract: A process for the production of carbamates is provided in which an organic primary or secondary amine is contacted, in the substantial absence of reactive oxygen, with a source of carbon monoxide, an organic compound containing at least one hydroxyl group and a source of sulfur, selenium or tellurium, in the presence of an effective amount of a catalyst selected from the group consisting of non-halide compounds and complexes of metals of Groups IVB, VB, VIB, VIIB, VIII, IB and IIIA of the Periodic Table. Further improved results are obtained by employing in the reaction zone at least one promoter selected from the group consisting of metals of Group IA and IIA of the Periodic Table.Type: GrantFiled: January 29, 1979Date of Patent: March 24, 1981Assignee: Halcon Research and Development Corp.Inventor: David Moy
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Patent number: 4252804Abstract: Compounds of the formula I ##STR1## wherein m and n are 0, 1 or 2, X represents oxygen, imino, benzylimino, or morpholinoethylimino, Y represents CO, CONH, COO or SO.sub.2, and NR.sub.1 R.sub.2 represents a dimethylamino, diethylamino, dipropylamino, dibutylamino, allylamino, isobutenylamino, cyclopentylamino, cyclohexylamino, cycloheptylamino, cyclooctylamino, N-methyl N-cyclopentylamino, N-methyl N-cyclohexylamino, N-allyl N-cyclohexylamino, adamantylamino, diethoxyethylamino, dimethylaminoethylamino, dimethylaminopropylamino, N-methyl N-dimethylaminopropyl-amino, benzylamino, 3,4,5-trimethoxybenzylamino, phenethylamino, p-chlorophenethylamino, tetrahydrofurfurylamino, tetrahydropyranylmethylamino, pyrrolidino, isoxazolidinyl, piperidino, 4-hydroxypiperidino, 4-m-chlorophenyl-4-hydroxypiperidino, homopiperidino, 1,2,3,6-tetrahydropyridyl, morpholino, 2-methylmorpholino, 2,6-dimethylmorpholino, 2-morpholinoethylamino, thiamorpholino, piperazino, 4-methylpiperazino, 4-(.alpha.Type: GrantFiled: January 13, 1978Date of Patent: February 24, 1981Assignee: Metabio-JoullieInventors: Maurice Joullie, Gabriel Maillard, Lucien Lakah, Christian J. M. Warolin
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Patent number: 4251667Abstract: A process for the preparation of aromatic urethanes by reacting an aromatic amine, an alcohol and carbon monoxide in the presence of a catalytic quantity of a copper salt, oxygen and a dehydrating agent is disclosed. The reaction is preferably carried out using a copper halide catalyst and dehydrating agents which combine with water to release the alcohol used in the preparation of the urethane product.Type: GrantFiled: June 6, 1979Date of Patent: February 17, 1981Assignee: Atlantic Richfield CompanyInventor: Haven S. Kesling, Jr.
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Patent number: 4238407Abstract: A process for the preparation of nitro-diphenyl amines is disclosed by decarboxylation of a urethane in the presence of a base at an elevated temperature using tetramethylene sulphone as reaction medium is disclosed. The urethane can be one formed by the reaction of a nitrophenol with an aromatic isocyanate.Type: GrantFiled: November 19, 1979Date of Patent: December 9, 1980Assignee: Bayer AktiengesellschaftInventors: Rudolf Fauss, Kuno Wagner, Jan Mazanek