Patents Represented by Attorney D. Wendell Osborne
-
Patent number: 6114580Abstract: N-arylsulfilimine compounds, such as S,S-dimethyl-N-(2,6-dichlorophenyl)sulfilimine, were prepared and found to catalyze the reaction of aromatic sulfonyl chloride compounds, such as 2-chlorosulfonyl-7-fluoro-5-ethoxy[1,2,4]triazolo[1,5-c]pyrimidine, with aromatic amine compounds, such as 2,6-dichloroaniline, to form N-arylarylsulfonamide compounds, such as N-(2,6-dichlorophenyl)-7-fluoro-5-ethoxy[1,2,4]triazolo[1,5-c]pyrimidine-2 -sulfonamide. The aryl moiety of the N-arylsulfilimine catalyst and the aryl moiety of the aromatic amine compound were generally chosen to be identical.Type: GrantFiled: November 13, 1997Date of Patent: September 5, 2000Assignee: Dow AgroSciences LLCInventors: James W. Ringer, Douglas L. Pearson, Carmen A. Scott, Anne P. Wallin
-
Patent number: 6017559Abstract: A method of controlling the particle size and particle size distribution of an aqueous emulsion having a non-aqueous disperse phase during the production thereof, in which the production of the emulsion is carried out in the presence of a dispersion of a templating agent, such as a polymer latex, and surfactantParticle size and particle size distribution of the dispersion is controlled by selecting the templating agent and surfactant such as to cause deposition of the disperse phase on particles of the dispersed templating agent, such that the particle size distribution of the templating agent provides a template for the particle size distribution of the final emulsion.Type: GrantFiled: October 30, 1997Date of Patent: January 25, 2000Assignee: Dow AgroSciences LLCInventors: Patrick J. Mulqueen, Steven D. Lubetkin, Geoffrey W. Smith, Eric S. Paterson
-
Patent number: 6015911Abstract: Herbicidal 1-alkyl-4-(2-chloro-3-alkoxy-4-alkylsulfonylbenzoyl)-5-hydroxypyrazole compounds, as well as 1-halo-2-chloro-3-alkoxy-4-alkylsulfonylbenzene compounds and 2-chloro-3-alkoxy-4-alkylsulfonylbenzoic acid compounds, were prepared in good yield by the reaction of the corresponding 3-chloro compound with an alkali metal alkoxide compound. 1-Halo-2-chloro-3-alkoxy-4-alkylsulfonylbenzene and 1-halo-2,3-dichloro-4-alkylsulfonylbenzene compounds were converted to compounds having hydroxycarbonyl, alkoxycarbonyl, or 1-alkyl-5-hydroxypyrazole-4-carbonyl substituents in place of the 1-halo substituent by reaction with carbon monoxide and water, an alcohol, or a 1-alkyl-5-hydroxypyrazole compound, respectively, in the presence of a palladium II salt:trihydrocarbylphosphine complex type catalyst.Type: GrantFiled: March 24, 1998Date of Patent: January 18, 2000Assignee: Dow AgroSciences LLCInventors: Thomas L. Siddall, Mark V. M. Emonds, Karl L. Krumel, Jennifer M. Schomaker, Mark W. Zettler
-
Patent number: 6010981Abstract: 1-Alkyl-4-benzoyl-5-hydroxypyrazole compounds in which the benzoyl moiety is substituted in the 2-position with a halo, alkyl, or alkoxy group, in the 4-position with an alkylsulfonyl group, and in the 3-position with an optionally substituted phenyl group, for example, 1-(1,1-dimethylethyl)-4-(2-methyl-4-methylsulfonyl-3-(4-methoxyphenyl)benz oyl-5-hydroxypyrazole, were prepared and found to be useful for the control of a variety of broadleaf and grassy weeds. The compounds can be applied either preemergently or postemergently and can be used to control undesirable vegetation selectively in small grain crops and turf or non-selectively.Type: GrantFiled: May 18, 1998Date of Patent: January 4, 2000Assignee: Dow AgroSciences LLCInventors: Thomas L. Siddall, Zoltan L. Benko, Gail M. Garvin, Johnny L. Jackson, Jeffrey M. McQuiston, David G. Ouse, Thomas D. Thibault, James A. Turner, John C. Van Heertum
-
Patent number: 6005108Abstract: N-(Triazoloazinyl)arylsulfonamide compounds, such as 2,6-dimethoxy-N-(8-chloro-5-methoxy[1,2,4]-triazolo[1,5-c]pyrimidin-2-yl)b enzenesulfonamide, 2-methoxy-4-(trifluoromethyl)-N-(5,8-dimethoxy[1,2,4]-triazolo[1,5-c]pyrim idin-2-yl)pyridine-3-sulfonamide, and 2-methoxy-6-methoxycarbonyl-N-(5,8-dimethoxy[1,2,4]triazolo[1,5-a]pyridin- 2-yl)benzenesulfonamide were prepared from appropriately substituted 2-amino[1,2,4]triazolo-[1,5-c]pyrimidine and 2-amino[1,2,4]triazolo[1,5-a]-pyridine compounds and appropriately substituted benzenesulfonyl chloride and pyridine-3-sulfonyl chloride compounds. The compounds were found to be useful as herbicides.Type: GrantFiled: July 31, 1998Date of Patent: December 21, 1999Inventors: Timothy C. Johnson, Robert J. Ehr, Richard D. Johnston, William A. Kleschick, Mark A. Pobanz, Richard K. Mann, Timothy P. Martin, John C. Van Heertum
-
Patent number: 5973148Abstract: N-arylsulfilimine compounds, such as S,S-dimethyl-N-(2,6-dichlorophenyl)sulfilimine, were prepared and found to catalyze the reaction of aromatic sulfonyl chloride compounds, such as 2-chlorosulfonyl-7-fluoro-5-ethoxy[1,2,4]triazolo[1,5-c]pyrimidine, with aromatic amine compounds, such as 2,6-dichloroaniline, to form N-arylarylsulfonamide compounds, such as N-(2,6-dichlorophenyl)-7-fluoro-5-ethoxy[1,2,4]triazolo[1,5-c]-pyrimidine- 2-sulfonamide. The aryl moiety of the N-arylsulfilimine catalyst and the aryl moiety of the aromatic amine compound were generally chosen to be identical.Type: GrantFiled: December 23, 1998Date of Patent: October 26, 1999Assignee: Dow AgroSciences LLCInventors: James W. Ringer, Carmen A. Scott, Douglas L. Pearson, Anne P. Wallin
-
Patent number: 5973153Abstract: The present invention relates to a new improved, simplified process for the preparation of halo-4-phenoxyquinolines, whereby thionyl chloride is used as the chlorinating agent to prepare the corresponding chloroquinoline intermediate prior to the final coupling reaction, and a single, inert high boiling polyether solvent is used throughout the entire reaction procedure.Type: GrantFiled: January 15, 1998Date of Patent: October 26, 1999Inventors: Tim J. Adaway, Jeff T. Budd, Ian R. King, Karl L. Krumel, Larry D. Kershner, Julie L. Maurer, Thomas A. Olmstead, Gary A. Roth, Jimmy J. Tai, Mark A. Hadd
-
Patent number: 5962690Abstract: 1-Alkyl-4-benzoyl-5-hydroxy-1H-pyrazole compounds in which the benzoyl moiety is substituted in the 2-position with groups such as halo or alkyl, in the 4-position with an alkylsulfonyl group, and in the 3-position with an acyclic or cyclic derivatized amino group, such as 1-ethyl-4-(2-chloro-4-methylsulfonyl-3-(morpholin-4-yl)benzoyl-5-hydroxy-1 H-pyrazole, were prepared and found to be useful for the control of a variety of broadleaf and grassy weeds. The compounds can be applied either preemergently or postemergently and can be used to control undesirable vegetation in corn, rice, and wheat crops.Type: GrantFiled: July 24, 1998Date of Patent: October 5, 1999Assignee: Dow AgroSciences LLCInventors: Zoltan L. Benko, James A. Turner, Gail M. Garvin, Johnny L. Jackson, Sharon L. Shinkle
-
Patent number: 5959106Abstract: N-(substituted aryl)?1,2,4!triazoloazinesulfonamide compounds, such as N-(2,6-difluorophenyl)-8-fluoro-5-methoxy?1,2,4!triazolo?1,5-c!pyrimidine- 2-sulfonamide, were prepared at a good reaction rate and in good yield by the reaction of a chlorosulfonyl?1,2,4!triazoloazine compound, such as 2-chlorosulfonyl-8-fluoro-5-methoxy?1,2,4!triazolo?1,5-c!pyrimidine, and an arylamine compound, such as 2,6-difluoroaniline, in an organic medium containing a relatively acidic alcohol, such as propylene glycol or 2,2,2-trifluoroethanol.Type: GrantFiled: January 25, 1999Date of Patent: September 28, 1999Assignee: Dow AgroSciences LLCInventors: Douglas L. Pearson, Timothy J. Adaway
-
Patent number: 5925464Abstract: Microencapsulated compositions, useful, for example, as pesticidal formulations, were prepared a process in which the microcapsules containing the encapsulated material are formed in an interfacial polycondensation reaction carried out in the presence of one polyvinylalcohol, a different polyvinylalcohol is added, and the resulting mixture is spray dried.Type: GrantFiled: August 8, 1997Date of Patent: July 20, 1999Assignee: Dow AgroSciences LLCInventors: Patrick Joseph Mulqueen, Geoff Smith, Steven D. Lubetkin
-
Patent number: 5858924Abstract: N-(Triazoloazinyl)arylsulfonamide compounds, such as 2,6-dimethoxy-N-(8-chloro-5-methoxy?1,2,4!-triazolo?1,5-c!pyrimidin-2-yl)b enzenesulfonamide, 2-methoxy-4-(trifluoromethyl)-N-(5,8-dimethoxy?1,2,4!-triazolo?1,5-c!pyrim idin-2-yl)pyridine-3-sulfonamide, and 2-methoxy-6-methoxycarbonyl-N-(5,8-dimethoxy?1,2,4!triazolo?1,5-a!pyridin- 2-yl)benzenesulfonamide were prepared from appropriately substituted 2-amino?1,2,4!triazolo-?1,5-c!pyrimidine and 2-amino?1,2,4!triazolo?1,5-a!-pyridine compounds and appropriately substituted benzene-sulfonyl chloride and pyridine-3-sulfonyl chloride compounds. The compounds were found to be useful as herbicides.Type: GrantFiled: September 23, 1997Date of Patent: January 12, 1999Assignee: Dow AgroSciences LLCInventors: Timothy C. Johnson, Robert J. Ehr, Richard D. Johnston, William A. Kleschick, Timothy P. Martin, Mark A. Pobanz, John C. Van Heertum, Richard K. Mann
-
Patent number: 5824802Abstract: 1-Alkyl-4-benzoyl-5-hydroxy-1H-pyrazole compounds in which the benzoyl moiety is substituted in the 2-position with groups such as halo or alkyl, in the 4-position with an alkylsulfonyl group, and in the 3-position with an acyclic or cyclic derivatized amino group, such as 1-ethyl-4-(2-chloro-4-methylsulfonyl-3-(morpholin-4-yl)benzoyl-5-hydroxy-1 H-pyrazole, were prepared and found to be useful for the control of a variety of broadleaf and grassy weeds. The compounds can be applied either preemergently or postemergently and can be used to control undesirable vegetation in corn, rice, and wheat crops.Type: GrantFiled: March 24, 1998Date of Patent: October 20, 1998Assignee: Dow AgroSciences LLCInventors: Zoltan L. Benko, James A. Turner, Monte R. Weimer, Gail M. Garvin, Johnny L. Jackson, Sharon L. Shinkle, Jeffery D. Webster
-
Patent number: 5780465Abstract: 4-Substituted 5-polycyclylpyrimidine compounds in which the 5-substituent is polycyclic and is attached to the pyrimidine moiety through an aliphatic carbon atom, such as 5-(2,2-dimethylindan-1-yl)-4-methylthiopyrimidine, were prepared and found to possess excellent herbicidal activity. The compounds are especially useful for the control of undesirable vegetation in paddy rice.Type: GrantFiled: April 3, 1997Date of Patent: July 14, 1998Assignee: Dow AgroSciences LLCInventors: Lowell D. Markley, Kim E. Arndt, Patricia G. Ray, Terry W. Balko, Erik N. K. Cressman, David G. Ouse, Johnny L. Jackson, Jacob Secor
-
Patent number: 5763359Abstract: Substituted N-(1-ethyl-4-pyrazolyl)triazoloazinesulfonamide compounds, such as N-(1-ethyl-5-methyl-3-(trifluoromethyl)-4-pyrazoyl)-5-methoxy-7-methyl-?1, 2,4!triazolo?1,5-c!pyrimidine-2-sulfonamide and N-(1-ethyl-5-methyl-3-(trifluoromethyl)-4-pyrazolyl)-5-methoxy-7-methyl?1, 2,4!triazolo?1,5-a!pyridine-2-sulfonamide, were prepared and found to possess selective herbicidal utility.Type: GrantFiled: August 28, 1996Date of Patent: June 9, 1998Assignee: Dow AgroSciences LLCInventors: Mark J. Costales, William A. Kleschick, Robert J. Ehr, Monte R. Weimer
-
Patent number: 5700940Abstract: Substituted N-aryl?1,2,4!triazolo?1,5-a!pyridine-2-sulfonamide compounds, such as N-(2,6-difluorophenyl)-5-methoxy-7-methyl?1,2,4!triazolo?1,5-a!pyridine-2- sulfonamide, N-(4-bromo-1-methyl-3-pyrazolyl)-8-chloro-5-methoxy?1,2,4!triazolo?1,5-a!p yridine-2-sulfonamide, and N-(2-fluoro-4-methyl-3-pyridinyl)-8-ethoxy-6-chloro?1,2,4!triazolo?1,5-a!p yridine-2-sulfonamide, were prepared by condensation of a 2-chlorosulfonyl?1,2,4!triazolo?1,5-a!pyridine compound with an aryl amine. The compounds prepared were found to possess excellent herbicidal activity on a broad spectrum of vegetation at low application rates.Type: GrantFiled: September 6, 1996Date of Patent: December 23, 1997Assignee: DowElancoInventors: John C. Van Heertum, William A. Kleschick, Kim E. Arndt, Mark J. Costales, Robert J. Ehr, Kimberly Brubaker Bradley, Walter Reifschneider, Zoltan Benko, Mary Lynne Ash, John J. Jachetta
-
Patent number: 5614469Abstract: Substituted N-pyridinyl[1,2,4]triazolo[1,5-c]-pyrimidine-2-sulfonamide compounds, such as N-(2-fluoro-4-methyl)-7-fluoro-5-methoxy[1,2,4]triazolo[1,5-c]pyrimidine-2 -sulfonamide, were prepared bycondensation of a 2-chlorosulfonyl[1,2,4]triazolo[1,5-c]pyrimidine compound, such as 2-chlorosulfonyl-7-fluoro-5-methoxy[1,2,4]triazolo[1,5-c]pyrimidine, with a substituted 3-aminopyridine compound, such as 3-amino-2-fluoro-4-methylpyridine, and found to possess herbicidal utility.Type: GrantFiled: June 6, 1995Date of Patent: March 25, 1997Assignee: DowElancoInventors: Kim E. Arndt, William A. Kleschick, Walter Reifschneider, Beth A. Swisher, Robert J. Ehr, John J. Jachetta, John C. Van Heertum
-
Patent number: 5602075Abstract: Substituted N-aryl[1,2,4]triazolo[1,5-a]-pyrazine-2-sulfonamide compounds, such as 5-bromo-N-(2,6-dichlorophenyl)-8-methoxy[1,2,4]triazolo[1,5-a]-pyrazine-2- sulfonamide, were prepared by condensation of a substituted 2-chlorosulfonyl[1,2,4]triazolo[1,5-a]pyrazine compound, such as 5-bromo-2-chlorosulfonyl-8-methoxy[1,2,4]triazolo[1,5-a]pyrazine with a substituted arylamine compound, such as 2,6-dichloroaniline, and found to possess herbicidal utility.Type: GrantFiled: July 11, 1994Date of Patent: February 11, 1997Assignee: DowElancoInventors: Zoltan Benko, John J. Jachetta, Mark J. Costales, Kim E. Arndt
-
Patent number: 5571775Abstract: Substituted N-aryl[1,2,4]triazolo[1,5-a]pyridine-2-sulfonamide compounds, such as N-(2,6-difluorophenyl)-5-methoxy-7-methyl[1,2,4]triazolo[1,5-a]pyridine-2- sulfonamide, N-(4-bromo-1-methyl-3-pyrazoly)-8-chloro-5-methoxy[1,2,4]triazolo[1,5-a]py ridine-2-sulfonamide, and N-(2-fluoro-4-methyl-3-pyridinyl)-8-ethoxy-6-chloro[1,2,4]triazolo[1,5-a]- pyridine-2-sulfonamide, were prepared by condensation of a 2-chlorosulfonyl[1,2,4]triazolo[1,5-a]pyridine compound with an aryl amine. The compounds prepared were found to possess excellent herbicidal activity on a broad spectrum of vegetation at low application rates.Type: GrantFiled: June 6, 1995Date of Patent: November 5, 1996Assignee: DowElancoInventors: John C. Van Heertum, William A. Kleschick, Kim E. Arndt, Mark J. Costales, Robert J. Ehr, Kimberly B. Bradley, Walter Reifschneider, Zolt an Benk o, John J. Jachetta
-
Patent number: 5563269Abstract: 5-Alkoxy-1,2,4-triazolo[4,3-c]pyrimidine-3(2H)-thione compounds, such as 5-ethoxy-8-fluoro-1,2,4-triazolo[4,3-c]pyrimidine-3(2H)-thione, were prepared by cyclization of 2-alkoxy-4-hydrazinopyrimidine compounds, such as 2-ethoxy-5-fluoro-4-hydrazinopyrimidine, with carbon disulfide and hydrogen peroxide. The reaction can be carried out in the presence of a trialkylamine, such as triethylamine, in which case a trialkylammonium salt is obtained. The products are useful intermediates in the preparation of 5-alkoxy[1,2,4]triazolo[1,5-c]-pyrimidine-2-sulfonamide herbicides.Type: GrantFiled: May 5, 1995Date of Patent: October 8, 1996Assignee: DowElancoInventors: Jon A. Orvik, Dawn Shiang
-
Patent number: 5560909Abstract: The invention concerns certain insecticidal compositions of ingestible insecticides selected from the group consisting of DNA viruses, RNA viruses and bacteria of the order Bacillus such as, for example, Bacillus thuringiensis var. israelensis entrapped by a suitable charged polymer. The invention also concerns a process for the preparation of and the use of such insecticidal compositions.Type: GrantFiled: July 26, 1991Date of Patent: October 1, 1996Assignee: DowElancoInventors: Lisa J. Rheaume, Julia A. Gegner, James J. Jakubowski, Daniel H. Haigh, James Peters