Patents Represented by Attorney D. Wendell Osborne
  • Patent number: 6114580
    Abstract: 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: Grant
    Filed: November 13, 1997
    Date of Patent: September 5, 2000
    Assignee: Dow AgroSciences LLC
    Inventors: James W. Ringer, Douglas L. Pearson, Carmen A. Scott, Anne P. Wallin
  • Patent number: 6017559
    Abstract: 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: Grant
    Filed: October 30, 1997
    Date of Patent: January 25, 2000
    Assignee: Dow AgroSciences LLC
    Inventors: Patrick J. Mulqueen, Steven D. Lubetkin, Geoffrey W. Smith, Eric S. Paterson
  • Patent number: 6015911
    Abstract: 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: Grant
    Filed: March 24, 1998
    Date of Patent: January 18, 2000
    Assignee: Dow AgroSciences LLC
    Inventors: Thomas L. Siddall, Mark V. M. Emonds, Karl L. Krumel, Jennifer M. Schomaker, Mark W. Zettler
  • Patent number: 6010981
    Abstract: 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: Grant
    Filed: May 18, 1998
    Date of Patent: January 4, 2000
    Assignee: Dow AgroSciences LLC
    Inventors: 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: 6005108
    Abstract: 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: Grant
    Filed: July 31, 1998
    Date of Patent: December 21, 1999
    Inventors: 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: 5973148
    Abstract: 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: Grant
    Filed: December 23, 1998
    Date of Patent: October 26, 1999
    Assignee: Dow AgroSciences LLC
    Inventors: James W. Ringer, Carmen A. Scott, Douglas L. Pearson, Anne P. Wallin
  • Patent number: 5973153
    Abstract: 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: Grant
    Filed: January 15, 1998
    Date of Patent: October 26, 1999
    Inventors: 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: 5962690
    Abstract: 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: Grant
    Filed: July 24, 1998
    Date of Patent: October 5, 1999
    Assignee: Dow AgroSciences LLC
    Inventors: Zoltan L. Benko, James A. Turner, Gail M. Garvin, Johnny L. Jackson, Sharon L. Shinkle
  • Patent number: 5959106
    Abstract: 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: Grant
    Filed: January 25, 1999
    Date of Patent: September 28, 1999
    Assignee: Dow AgroSciences LLC
    Inventors: Douglas L. Pearson, Timothy J. Adaway
  • Patent number: 5925464
    Abstract: 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: Grant
    Filed: August 8, 1997
    Date of Patent: July 20, 1999
    Assignee: Dow AgroSciences LLC
    Inventors: Patrick Joseph Mulqueen, Geoff Smith, Steven D. Lubetkin
  • Patent number: 5858924
    Abstract: 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: Grant
    Filed: September 23, 1997
    Date of Patent: January 12, 1999
    Assignee: Dow AgroSciences LLC
    Inventors: 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: 5824802
    Abstract: 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: Grant
    Filed: March 24, 1998
    Date of Patent: October 20, 1998
    Assignee: Dow AgroSciences LLC
    Inventors: Zoltan L. Benko, James A. Turner, Monte R. Weimer, Gail M. Garvin, Johnny L. Jackson, Sharon L. Shinkle, Jeffery D. Webster
  • Patent number: 5780465
    Abstract: 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: Grant
    Filed: April 3, 1997
    Date of Patent: July 14, 1998
    Assignee: Dow AgroSciences LLC
    Inventors: 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: 5763359
    Abstract: 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: Grant
    Filed: August 28, 1996
    Date of Patent: June 9, 1998
    Assignee: Dow AgroSciences LLC
    Inventors: Mark J. Costales, William A. Kleschick, Robert J. Ehr, Monte R. Weimer
  • Patent number: 5700940
    Abstract: 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: Grant
    Filed: September 6, 1996
    Date of Patent: December 23, 1997
    Assignee: DowElanco
    Inventors: 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: 5614469
    Abstract: 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: Grant
    Filed: June 6, 1995
    Date of Patent: March 25, 1997
    Assignee: DowElanco
    Inventors: Kim E. Arndt, William A. Kleschick, Walter Reifschneider, Beth A. Swisher, Robert J. Ehr, John J. Jachetta, John C. Van Heertum
  • Patent number: 5602075
    Abstract: 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: Grant
    Filed: July 11, 1994
    Date of Patent: February 11, 1997
    Assignee: DowElanco
    Inventors: Zoltan Benko, John J. Jachetta, Mark J. Costales, Kim E. Arndt
  • Patent number: 5571775
    Abstract: 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: Grant
    Filed: June 6, 1995
    Date of Patent: November 5, 1996
    Assignee: DowElanco
    Inventors: 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: 5563269
    Abstract: 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: Grant
    Filed: May 5, 1995
    Date of Patent: October 8, 1996
    Assignee: DowElanco
    Inventors: Jon A. Orvik, Dawn Shiang
  • Patent number: 5560909
    Abstract: 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: Grant
    Filed: July 26, 1991
    Date of Patent: October 1, 1996
    Assignee: DowElanco
    Inventors: Lisa J. Rheaume, Julia A. Gegner, James J. Jakubowski, Daniel H. Haigh, James Peters