Patents Represented by Attorney, Agent or Law Firm Clark R. Carpenter
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Patent number: 5925763Abstract: This invention relates to a process for the preparation of an .alpha.-chloroketone compound comprising the steps of(i) cyclizing an alkynyl amide to form a 5-methyleneoxazoline ##STR1## (ii) chlorinating the 5-methyleneoxazoline using trichloroisocyanuric acid to produce a chlorinated oxazoline intermediate ##STR2## and (iii) hydrolyzing the chlorinated oxazoline intermediate with an aqueous acid top produce the desired monochloroketone ##STR3## wherein Z is alkyl or substituted alkyl, aryl or substituted aryl, heteroaryl or substituted heteroaryl or phenylene,R is a hydrogen atom or alkyl, andR.sup.1 and R.sup.2 are each independently an alkyl or substituted alkyl group, or R.sup.1 and R.sup.2 together with the carbon atom to which they are attached form a cyclic structure.Additionally, when R is a hydrogen atom, a dichioroketone can be conveniently formed through adjustment of reaction conditions.Type: GrantFiled: October 13, 1998Date of Patent: July 20, 1999Assignee: Rohm and Haas CompanyInventors: Heather Lynnette Rayle, Renee Caroline Roemmele, Randall Wayne Stephens
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Patent number: 5917079Abstract: Nucleophilic substitution reactions on halobenzenes are carried out in the presence of catalysts. In particular the present invention provides a process leading to optionally substituted hydroxybenzoic and alkoxybenzoic acids and optionally substituted hydroxybenzonitriles and alkoxybenzonitriles from substituted 2,6-dihalobenzenes.Type: GrantFiled: July 1, 1997Date of Patent: June 29, 1999Assignee: Rohm and Haas CompanyInventors: Joshua Anthony Chong, Fereydon Abdesaken, Charles Chao Wu
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Patent number: 5910602Abstract: The present invention relates to methods for preparing 3-amino-4,4,4-trihalocrotonates and their derivatives from a 4,4,4-trihaloacetoacetate derivative and an amine or ammonium salt.Type: GrantFiled: April 29, 1998Date of Patent: June 8, 1999Assignee: Rohm and Haas CompanyInventors: Joshua Anthony Chong, Fereydon Abdesken, Peter Osei-Gyimah
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Patent number: 5889184Abstract: This invention relates to a process for the preparation of pyrimidinone compounds of the formula ##STR1## wherein Ar is an optionally substituted aryl or heteroaromatic moiety,R.sup.3 is an optionally substituted alkyl, alkenyl or alkynyl,R.sup.5 is a hydrogen atom, halo, cyano or an optionally substituted alkyl, alkenyl, alkynyl, alkoxy or alkylthio, andR.sup.6 is a hydrogen atom, cyano, or an optionally substituted alkyl, cycloalkyl, alkenyl, alkynyl, aryl, aralkyl or heteroaryl.The process comprises reaction of an amidine and a malonic acid derivative to give a hydroxypyrimidinone followed by conversion of the resulting hydroxypyrimidinone to a sulfonyloxypyrimidinone followed by reaction of the resulting sulfonyloxypyrimidinone with an organometallic reagent to give the desired pyrimidinone. The hydroxypyrimidinones, wherein R.sup.6 is hydroxy and sulfonyloxypyrimidinones wherein R.sup.Type: GrantFiled: April 2, 1997Date of Patent: March 30, 1999Assignees: Princeton University, Rohm and Haas CompanyInventors: Ping Zhou, Edward Curtis Taylor, Colin Michael Tice
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Patent number: 5886210Abstract: A method for synthesizing aromatic compounds by selectively dehalogenating aromatic starting materials is provided. Compounds may be prepared which are substituted with fluoro, chloro or bromo. The method may be used to remove halogen atoms from sites at which halogenation is not desired, and to form substantially pure halogenated compounds from mixtures of starting materials. The method uses a copper containing dehalogenation agent and an acid with the dehalogenation being controlled by a substituent such as a carboxylic acid, amide, ester, aldehyde, ketone or cyano on the aromatic ring.Type: GrantFiled: June 16, 1997Date of Patent: March 23, 1999Assignee: Rohm and Haas CompanyInventors: Heather Lynnette Rayle, Randall Wayne Stephens
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Patent number: 5883044Abstract: This invention pertains to a method for selectively controlling weeds comprising(i) applying to the desired crop seed a quantity of an oxime ether safener having the general formula ##STR1## wherein A is a hydrogen atom or a halogen atom;Q is cyano or ##STR2## Z is a halogen atom, cyano, haloalkyl, haloalkoxy or nitro; n is 2 or 3;(ii) planting the treated seed;(iii) applying a composition comprising one or more phosphosulfonate herbicides having the general formula ##STR3## wherein Y is an optionally substituted phenyl, naphthyl, benzyl, a (C.sub.5 -C.sub.8)cycloalkyl, a 5-membered heteroaromatic ring, a 6-membered heteraromatic ring, a fused 5,6-membered heteroaromatic ring, or a fused 6,6-membered heteroaromatic ring;X is an oxygen or a sulfur atom; andR.sup.1 and R.sup.Type: GrantFiled: July 17, 1997Date of Patent: March 16, 1999Assignee: Rohm and Haas CompanyInventors: James Delbert Fisher, Ernest Leroy Burdge, Lori Ann Spangler
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Patent number: 5874466Abstract: Novel routes for the preparation of acetonylbenzamides are provided by the reaction of an amine and acyl chloride. Novel routes to various intermediates used in the manufacture of acetonylbenzamides are also disclosed.Type: GrantFiled: June 10, 1997Date of Patent: February 23, 1999Assignee: Rohm and Haas CompanyInventors: Enrique Luis Michelotti, Heather Lynnette Rayle, Randall Wayne Stephens, William Joseph Zabrodski
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Patent number: 5869425Abstract: The present invention relates to compositions, having herbicidal synergistic effects, comprising(i) propanil;(ii) a compound selected from asulam, butamifos and methazole; and(iii) an agronomically acceptable carrierfor the control of various grasses and broadleaf weeds in rice. More particularly, such compositions exhibit synergistic properties for selectively controlling weeds in rice, especially grassy weeds such is Barnyardgrass, Junglerice, Signalgrass and Sprangletop. This invention also relates to a method of controlling weed species in rice comprising applying a herbicidally effective amount of composition comprising (i) propanil, (ii) a compound selected from asulam, butamifos and methazole and (iii) an agronomically acceptable carrier to the weed, to the locus of the weed or to the growth medium of said weed.Type: GrantFiled: May 19, 1997Date of Patent: February 9, 1999Assignee: Rohm and Haas CompanyInventors: James Delbert Fisher, Colin Michael Tice
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Patent number: 5859254Abstract: This invention relates to a process for the preparation of an .alpha.-chloroketone compound comprising the steps of(i) cyclizing an alkynyl amide to form a 5-methyleneoxazoline ##STR1## (ii) chlorinating the 5-methyleneoxazoline using trichloroisocyanuric acid to produce a chlorinated oxazoline intermediate ##STR2## and (iii) hydrolyzing the chlorinated oxazoline intermediate with an aqueous acid to produce the desired monochloroketone ##STR3## wherein Z is alkyl or substituted alkyl, aryl or substituted aryl, heteroaryl or substituted heteroaryl or phenylene,R is a hydrogen atom or alkyl, andR.sup.1 and R.sup.2 are each independently an alkyl or substituted alkyl group, or R.sup.1 and R.sup.2 together with the carbon atom to which they are attached form a cyclic structure.Additionally, when R is a hydrogen atom, a dichloroketone can be conveniently formed through adjustment of reaction conditions.Type: GrantFiled: April 13, 1998Date of Patent: January 12, 1999Assignee: Rohm and Haas CompanyInventors: Heather Lynnette Rayle, Renee Caroline Roemmele, Randall Wayne Stephens
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Patent number: 5798311Abstract: This invention relates to novel N-aryl-3-aryl-4-substituted-4,5-dihydro-1H-pyrazole-1-carboxamide compounds which are useful as pesticides, compositions containing those compounds, methods of controlling pests and processes for preparing these compounds.Type: GrantFiled: June 6, 1995Date of Patent: August 25, 1998Assignee: Rohm and Haas CompanyInventor: Richard Martin Jacobson
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Patent number: 5783736Abstract: The process of this invention comprises a two step sequence wherein an alcohol is converted to an organic chloride through reaction with a chlorinating agent in a first step followed by amination of the organic chloride to the corresponding amine in a second step. In the second step, a surfactant is employed in order to facilitate the reaction.Type: GrantFiled: September 26, 1997Date of Patent: July 21, 1998Assignee: Rohm and Haas CompanyInventors: Randall Wayne Stephens, Renee Caroline Roemmele
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Patent number: 5780651Abstract: This invention relates to an improved process for the preparation of 5-methylchroman-6-carboxylic acid, a useful intermediate in the preparation of chroman-containing diacylhydrazines which are useful as insecticides, by reacting a Hagemann's ester with a propargyl derivative in the presence of a base and a solvent to produce a propargyl ether, rearranging the propargyl ether by application of heat with a suitable catalyst being present, with or without a solvent, to produce a cyclic ether type compound and isomerizing the cyclic ether type compound with a catalyst in a suitable solvent to produce a chroman ester. The propargyl ethers and the cyclic ether type compounds produced by the process of the present invention are new.Type: GrantFiled: July 9, 1997Date of Patent: July 14, 1998Assignee: Rohm and Haas CompanyInventor: Robert Eugene Hormann
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Patent number: 5780652Abstract: This invention relates to an improved process for the preparation of 5-methylchroman-6-carboxylic acid, a useful intermediate in the preparation of chroman-containing diacylhydrazines which are useful as insecticides, by reacting a Hagemann's ester with a propargyl derivative in the presence of a base and a solvent to produce a propargyl ether, rearranging the propargyl ether by application of heat with a suitable catalyst being present, with or without a solvent, to produce a cyclic ether type compound and isomerizing the cyclic ether type compound with a catalyst in a suitable solvent to produce a chroman ester. The propargyl ethers and the cyclic ether type compounds produced by the process of the present invention are new.Type: GrantFiled: July 9, 1997Date of Patent: July 14, 1998Assignee: Rohm and Haas CompanyInventor: Robert Eugene Hormann
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Patent number: 5777154Abstract: The present invention relates to methods for preparing 3-amino-4,4,4-trihalocrotonates and their derivatives from a 4,4,4-trihaloacetoacetate derivative and an amine or ammonium salt.Type: GrantFiled: November 14, 1996Date of Patent: July 7, 1998Assignee: Rohm and Haas CompanyInventors: Joshua Anthony Chong, Fereydon Abdesken, Peter Osei-Gyimah
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Patent number: 5756820Abstract: This invention relates to an improved process for the preparation of 5-methylchroman-6-carboxylic acid, a useful intermediate in the preparation of chroman-containing diacylhydrazines which are useful as insecticides, by reacting a Hagemann's ester with a propargyl derivative in the presence of a base and a solvent to produce a propargyl ether, rearranging the propargyl ether by application of heat with a suitable catalyst being present, with or without a solvent, to produce a cyclic ether type compound and isomerizing the cyclic ether type compound with a catalyst in a suitable solvent to produce a chroman ester. The propargyl ethers and the cyclic ether type compounds produced by the process of the present invention are new.Type: GrantFiled: July 9, 1997Date of Patent: May 26, 1998Assignee: Rohm and Haas CompanyInventor: Robert Eugene Hormann
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Patent number: 5726124Abstract: A class of 2-arylpyrimidines which is useful in the control of weeds of the general formula: ##STR1## wherein R.sup.2 is an optionally substituted aromatic ring; R.sup.3 is a saturated or unsaturated alkyl group; R.sup.5 is selected from acyl, alkoxyalkyl, alkoxyimino, dialkoxyalkyl, formyl, hydroxyalkyl, alkoxyalkoxy, cyanoalkyl and hydroxyimino; R.sup.6 is selected from hydrogen, halo, alkyl, haloalkyl, aryl, and alkoxy; and X is oxygen or sulfur.Type: GrantFiled: October 28, 1994Date of Patent: March 10, 1998Assignee: Rohm and Haas CompanyInventors: Colin Michael Tice, Vincent Angelo Musco, Renee Caroline Roemmele, Harlow Lester Warner
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Patent number: 5723414Abstract: A class of 5-aryl-isoxazolinones and compositions thereof which are useful in the control of weeds is of the general formula ##STR1## wherein Ar is a substituted or unsubstituted aryl or heteroaryl;R.sup.2 is alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl or alkoxyalkyl, all of which may be substituted with one or more halogen atoms;R.sup.4 is alkynyl or alkoxyalkyl, both of which may be substituted with one or more halogen atoms; andX is an oxygen or a sulfur atom.Type: GrantFiled: January 21, 1997Date of Patent: March 3, 1998Assignee: Rohm and Haas CompanyInventor: Colin Michael Tice
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Patent number: 5698716Abstract: This invention relates to an improved process for the preparation of 5-methylchroman-6-carboxylic acid, a useful intermediate in the preparation of chroman-containing diacylhydrazines which are useful as insecticides, by reacting a Hagemann's ester with a propargyl derivative in the presence of a base and a solvent to produce a propargyl ether, rearranging the propargyl ether by application of heat with a suitable catalyst being present, with or without a solvent, to produce a cyclic ether type compound and isomerizing the cyclic ether type compound with a catalyst in a suitable solvent to produce a chroman ester. The propargyl ethers and the cyclic ether type compounds produced by the process of the present invention are new.Type: GrantFiled: November 5, 1996Date of Patent: December 16, 1997Assignee: Rohm and Haas CompanyInventor: Robert Eugene Hormann
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Patent number: 5693590Abstract: This invention pertains to compositions comprising herbicidal phosphosulfonates, having the general formula ##STR1## wherein Y is an optionally substituted phenyl, naphthyl, benzyl, a (C.sub.5 -C.sub.8)cycloalkyl, a 5-membered heteroaromatic ring, a 6-membered heteraromatic ring, a fused 5,6-membered heteroaromatic ring, or a fused 6,6-membered heteroaromatic ring;X is an oxygen or a sulfur atom; andR.sup.1 and R.sup.2 are each independently selected from substituted or unsubstituted alkyl, alkoxy, alkylthio, alkenyloxy, alkynyloxy, haloalkoxy, cyanoalkoxy, alkoxyalkoxy, cycloalkyloxy, cycloalkylalkoxy, alkylideneiminooxy, chloro, amino, phenyl or phenoxy; or R.sup.1 and R.sup.2 are both alkoxy, taken together with the phosphorus atom to form a 6-membered oxygen-containing ring; anddichloroacetamide safeners having the general formula ##STR2## wherein R.sup.a and R.sup.b are each independently selected from alkyl, alkenyl, or alkyl or alkenyl substituted with halo, or R.sup.a and R.sup.Type: GrantFiled: July 20, 1995Date of Patent: December 2, 1997Assignee: Rohm and Haas CompanyInventors: James Delbert Fisher, Ernest Leroy Burdge, Vincent Angelo Musco, Jr., Lori Ann Spangler
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Patent number: 5670691Abstract: A method for making a substituted benzene compound includes reacting a 2-substituted benzenesulfonate or the 2-substituted benzenesulfonate further substituted in the 3, 4 or 5-position with a lithium compound to form an intermediate; and reacting the intermediate with an electrophile to form a 2,6-disubstituted benzenesulfonate or a 2,6-disubstituted benzenesulfonate further substituted in the 3, 4 or 5-position.Type: GrantFiled: September 7, 1995Date of Patent: September 23, 1997Assignee: Rohm and Haas CompanyInventors: Lori Ann Spangler, Damian Gerard Weaver