Patents Represented by Attorney, Agent or Law Firm Clark R. Carpenter
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Patent number: 6057477Abstract: 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 trichlorolsocyanuric 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 16, 1999Date of Patent: May 2, 2000Assignee: Rohm and Haas CompanyInventor: Heather Lynnette Rayle
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Patent number: 6057365Abstract: The present invention relates to fungicidal compositions and their use as a method for controlling phytopathogenic fungi comprising the application of a selected fungicidally active N-acetonylbenzamide compound and a second fungicidally active compound which is [2-methyl-1-[1-(4-methylphenyl)-ethylaminocarbonyl]-propyl]-carbamic acid, isopropyl ester to plant seed, to plant foliage or to a plant growth medium. The compositions and method of use provide higher fungicidal activity than separate use of the same compounds.Type: GrantFiled: December 22, 1998Date of Patent: May 2, 2000Assignee: Rohm and Haas CompanyInventors: David Hamilton Young, Willie Joe Wilson, Anne Ritchie Egan, Enrique Luis Michelotti
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Patent number: 6057356Abstract: The present invention relates to fungicidal compositions and their use as a method for controlling phytopathogenic fungi comprising the application of a selected fungicidally active N-acetonylbenzamide compound and a second fungicidally active compound selected from the group consisting of an inhibitor of respiration at cytochrome complex III, ziram, fluazinam, zarilamide, chlorothalonil, propamocarb, folpet, fosetyl-aluminum or a fungitoxic metabolite thereof, a triphenyltin type fungicide and a copper containing fungicide to plant seed, to plant foliage or to a plant growth medium. The compositions and method of use provide higher fungicidal activity than separate use of the same compounds.Type: GrantFiled: November 4, 1999Date of Patent: May 2, 2000Assignee: Rohm and Haas CompanyInventors: David Hamilton Young, Willie Joe Wilson, Anne Ritchie Egan, Enrique Luis Michelotti
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Patent number: 6054583Abstract: This invention relates to a process for preparing 2-substituted pyridines via metal halogen exchange with sec-butyllithium on optionally substituted 2-bromo or 2-iodopyridines. The resulting lithopyridine intermediate is reacted with an electrophile to provide the desired 2-substituted pyridine. The substitution of sec-butyllithium for n-butyllithium in such a process results in an enhanced yield and purity of the desired 2-substituted pyridine.Type: GrantFiled: May 5, 1999Date of Patent: April 25, 2000Assignee: Rohm and Haas CompanyInventors: Martha Jean Kelly, Damian Gerard Weaver
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Patent number: 6054582Abstract: 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: December 8, 1998Date of Patent: April 25, 2000Assignee: Rohm and Haas CompanyInventors: Ping Zhou, Edward Curtis Taylor, Colin Michael Tice
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Patent number: 6051710Abstract: 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: December 8, 1998Date of Patent: April 18, 2000Assignee: Rohm and Haas CompanyInventors: Ping Zhou, Edward Curtis Taylor, Colin Michael Tice
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Patent number: 6025301Abstract: This invention relates to an indanone herbicidal composition comprising a compound having the general formula ##STR1## wherein Y is an oxygen atom or a hydrazono group,R is alkyl or substituted alkyl,X is a hydrogen atom or is one to three substituents independently selected from the group consisting of halo, alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxy, alkylthio, alkylsulfonyl, alkylsulfinyl, phenyl, phenalkyl, phenalkenyl, phenalkynyl, cyano, haloalkoxy, 1,3-dioxalan-2-yl, hydroxyimino and nitro, andan agronomically acceptable carrier.The invention also discloses a method of use of these compositions.Type: GrantFiled: March 2, 1998Date of Patent: February 15, 2000Assignee: Rohm and Haas CompanyInventors: Ernest Leroy Burdge, Manuel Victor Nunez, Lori Ann Spangler
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Patent number: 6013836Abstract: This invention relates to N'-substituted-N,N'-disubstitutedhydrazines of formula I ##STR1## wherein X and X' are independently O, S, or NR; A' and B' are independently substituted or unsubstituted aryl or aromatic heterocycle; wherein F is alkyl, alkenyl, or aralkyl; and wherein E is a tertiary carbon containing organic radical having a total of at least four carbon and halogen atoms but not more than six halogen atoms, or a non-tertiary carbon containing non-haloalkyl organic or organometallic radical having at least five atoms other than hydrogen, oxygen and halogen which are useful as insecticides, compositions containing those compounds, methods of producing the compounds, and methods of their use. More particularly, the invention relates to insect growth regulating compounds and compositions, and methods of using such compounds and compositions. Compounds of the present invention are particularly suitable for controlling plant-destructive insects in crops of cultivated plants, ornamentals and forestry.Type: GrantFiled: May 22, 1995Date of Patent: January 11, 2000Assignee: Rohm and Haas CompanyInventors: Adam Chi-Tung Hsu, Harold Ernest Aller, Dat Phat Le, Donald Wesley Hamp, Barry Weinstein, Raymond August Murphy
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Patent number: 6011065Abstract: The present invention relates to fungicidal compositions and their use as a method for controlling phytopathogenic fungi comprising the application of a selected fungicidally active N-acetonylbenzamide compound and a second fungicidally active compound selected from an acylalanine type fungicide to plant seed, to plant foliage or to a plant growth medium. The compositions and method of use provide higher fungicidal activity than separate use of the same compounds.Type: GrantFiled: September 4, 1998Date of Patent: January 4, 2000Assignee: Rohm and Haas CompanyInventors: David Hamilton Young, Willie Joe Wilson, Anne Ritchie Egan, Enrique Luis Michelotti
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Patent number: 6004947Abstract: The present invention relates to fungicidal compositions and their use as a method for controlling phytopathogenic fungi comprising the application of a selected fungicidally active N-acetonylbenzamide compound and a second fungicidally active compound selected from the group consisting of an inhibitor of respiration at cytochrome complex III, ziram, fluazinam, zarilamide, chlorothalonil, propamocarb, folpet, fosetyl-aluminum or a fungitoxic metabolite thereof, a triphenyltin type fungicide and a copper containing fungicide to plant seed, to plant foliage or to a plant growth medium. The compositions and method of use provide higher fungicidal activity than separate use of the same compounds.Type: GrantFiled: September 4, 1998Date of Patent: December 21, 1999Assignee: Rohm and Haas CompanyInventors: David Hamilton Young, Willie Joe Wilson, Anne Ritchie Egan, Enrique Luis Michelotti
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Patent number: 5977368Abstract: 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: October 13, 1998Date of Patent: November 2, 1999Assignee: Rohm and Haas CompanyInventors: Heather Lynnette Rayle, Renee Caroline Roemmele, Randall Wayne Stephens
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Patent number: 5969200Abstract: 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: October 22, 1998Date of Patent: October 19, 1999Assignee: Rohm and Haas CompanyInventors: Enrique Luis Michelotti, Heather Lynnette Rayle, Randall Wayne Stephens, William Joseph Zabrodski
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Patent number: 5965766Abstract: Nucleophilic substitution reactions on halobenzenes or triflyl substituted benzenes are carried out in the presence of catalysts. In particular the present invention provides a process leading to optionally substituted hydroxybenzoic, alkanoyloxybenzoic, formyloxybenzoic and alkoxybenzoic acids and optionally substituted hydroxybenzonitriles and alkoxybenzonitriles from substituted 2,6-dihalobenzenes, 2-halo-6-triflylbenzene and 2,6-ditriflylbenzenes.Type: GrantFiled: February 2, 1998Date of Patent: October 12, 1999Assignee: Rohm and Haas CompanyInventors: Joshua Anthony Chong, Fereydon Abdesaken, Charles Chao Wu
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Patent number: 5958426Abstract: A process for novel sphingolipids and other secondary sphingosine-based compounds is provided which comprises the culturing of an appropriate fungus, harvesting mycelium from the fungus and isolating the sphingolipid from the mycelium. The sphingosine-based materials inhibit protein kinase C, provide an anti-inflammatory effect or provide an anti-tumor effect; furthermore, these sphingosine-based materials provide protection for plants against pathogenic microorganisms.Type: GrantFiled: March 24, 1997Date of Patent: September 28, 1999Assignees: The United States of America as represented by the Secretary of Agriculture, Rohm and Haas Company,Inventors: Robert Arthur Moreau, David Hamilton Young, Ronald Ross, Jr.
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Patent number: 5959114Abstract: 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: October 13, 1998Date of Patent: September 28, 1999Assignee: Rohm and Haas CompanyInventors: Heather Lynnette Rayle, Renee Caroline Roemmele, Randall Wayne Stephens
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Patent number: 5945565Abstract: 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: October 22, 1998Date of Patent: August 31, 1999Assignee: Rohm and Haas CompanyInventors: Enrique Luis Michelotti, Heather Lynnette Rayle, Randall Wayne Stephens, William Joseph Zabrodski
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Patent number: 5942621Abstract: 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: October 13, 1998Date of Patent: August 24, 1999Assignee: Rohm and Haas CompanyInventors: Heather Lynnette Rayle, Renee Caroline Roemmele, Randall Wayne Stephens
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Patent number: 5936096Abstract: 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: October 13, 1998Date of Patent: August 10, 1999Assignee: Rohm and Haas CompanyInventors: Heather Lynnette Rayle, Renee Caroline Roemmele, Randall Wayne Stephens
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Patent number: 5932738Abstract: 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: October 13, 1998Date of Patent: August 3, 1999Assignee: Rohm and Haas CompanyInventors: Heather Lynnette Rayle, Renee Caroline Roemmele, Randall Wayne Stephens
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Patent number: 5929287Abstract: This invention relates to a process for the selective monochlorination or dichlorination of certain substituted alkenes using trichloroisocyanuric acid. The chlorinated alkenes can be easily hydrolyzed to provide .alpha.-monochloroketones or .alpha.,.alpha.-dichloroketones with a high degree of selectivity. The resulting .alpha.-monochloroketones or .alpha.,.alpha.-dichloroketones have utility as fungicides or function as useful intermediates for fungicides.Type: GrantFiled: April 13, 1998Date of Patent: July 27, 1999Assignee: Rohm and Haas CompanyInventors: Renee Caroline Roemmele, Heather Lynnette Rayle