Abstract: 3,4-Diaryl-4,5-dihydro-1H-pyrazole compounds having a selected 5- or 6-membered aromatic heterocyclic moiety in the 4-position and an optionally substituted phenyl moiety in the 3-position, such as 4,5-dihydro-3-(4-fluorophenyl)-4-(5-trifluoromethyl-2-pyridinyl)-1H-pyrazo le were prepared as intermediates in the preparation of insecticidal 3,4,N-triaryl-4,5-dihydro-1H-pyrazole-1-carboxamide compounds. The 3,4-diaryl-4,5-dihydro-1H-pyrazole compounds can be prepared from appropriate 1,2-diarylethanone compounds by successive treatments with N,N,N',N'-tetramethyldiaminomethane in dichloromethane in the presence of acetic anhydride (to form a Mannich adduct) and hydrazine in the presence of a catalytic amount of trifluoroacetic acid.
Type:
Grant
Filed:
August 17, 1992
Date of Patent:
June 28, 1994
Assignee:
DowElanco
Inventors:
James M. Renga, Kevin L. McLaren, James T. Pechacek, Michael J. Ricks, Yulan C. Tong
Abstract: A stabilized water dilutable pesticidal composition prepared by forming a solution of a pesticidal substance in a water-immiscible solvent, and combining the solution with an emulsifier and a polymer latex to form a dispersion in water of particles comprising the pesticidal substance wherein the pesticidal substance and the water-immiscible solvent together comprise at least 10 percent by weight of the composition.
Type:
Grant
Filed:
April 5, 1990
Date of Patent:
June 14, 1994
Assignee:
DowElanco
Inventors:
Geoffrey W. Smith, Patrick J. Mulqueen, Eric S. Paterson, John Cuffe
Abstract: 2,3,5,6-Tetrachloropyridine, and 2,3-dichloro-5-(trichloromethyl)pyridine are prepared by selectively chlorinating polychlorinated .beta.-picolines in the vapor phase between about 250.degree. and 450.degree. C. in the presence of specific Lewis acid halide catalysts on an inorganic support. The gamma position on the pyridine ring is usually not chlorinated in the starting material or reaction products. These compounds are useful intermediates to produce insecticides and herbicides.
Type:
Grant
Filed:
November 26, 1991
Date of Patent:
June 7, 1994
Assignee:
DowElanco
Inventors:
Clark P. Allphin, Michael A. DesJardin, Arnold D. Harley
Abstract: A highly active water-dispersible pesticide formulation is prepared by dissolving at least a part of a benzoyl phenyl urea series insecticidal compound in an organic solvent, contacting the so obtained mixture with a carrier material, and pulverizing the resulting mixture. The pesticidal formulation obtained has higher pesticidal activity than formulations prepared by a conventional dry methods.
Type:
Grant
Filed:
July 7, 1989
Date of Patent:
November 23, 1993
Assignee:
DowElanco
Inventors:
Tetsuya Shibahara, Naohiko Kondo, Jun Kato
Abstract: Disclosed are herbicidal concentrate formulation compositions having reduced crop plant phytotoxicity comprising N-(2,6-difluorophenyl)-5-methyl-1,2,4-triazolo(1,5-a) pyrimidine-2-sulfonamide or an amine salt thereof in admixture with one or more amine salts of 2,4-D; also disclosed is the preparation of said compositions and the pre- and post-emergent agricultural uses thereof in water diluted form.
Abstract: A controlled release and delivery system for a hydrophobic, water sensitive herbicide is produced by:(a) dissolving the herbicide in a volatile water-immiscible solvent;(b) introducing the solvent containing the herbicide dissolved therein to a latex dispersion comprising an aqueous continuous phase and polymeric discrete phase;(c) agitating the resultant mixture until the polymeric particles of the discrete phase absorb the herbicide; and(d) removing the solvent from the resultant mixture at reduced pressure.
Abstract: The present invention is directed to novel substituted aniline compounds, the optically active isomers of said compounds, compositions containing said compounds, and the use of these compounds in the selective kill and control of grassy weeds in the presence of valuable crop plants, especially corn plants.
Type:
Grant
Filed:
June 27, 1991
Date of Patent:
October 5, 1993
Assignee:
DowElanco
Inventors:
James A. Turner, Wendy S. Jacks, Paul S. Zorner, Susan K. Moore
Abstract: 3,4,N-triaryl-4,5-dihydro-1H-pyrazole-1-carboxamide compounds having an aryl moiety in the 4-position that is an optionally substituted pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, or quinolinyl moiety and aryl moieties in the 3-position and the N-position that are optionally substituted phenyl, pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, or quinolinyl moieties, such as N-(4-chlorophenyl)-4,5- -dihydro-3-(4-fluorophenyl)-4-(5-trifluoromethyl-2- -pyridinyl)-1H-pyrazole-1-carboxamide, were prepared and found to possess insecticidal utility. 1,2-Diarylethanone compounds were converted to 1,2-diaryl-2-propen-1-one compounds by treatment with bis(dimethylamino)methane, the 1,2-diaryl-2-propen-1-one compounds were converted to 3,4-diaryl-4,5-dihydro-1H-pyrazole compounds by treatment with hydrazine, and the 3,4-diaryl-4,5-dihydro-1H-pyrazole compounds were converted to the insecticidal subject compounds by treatment with an aryl isocyanate.
Type:
Grant
Filed:
February 27, 1992
Date of Patent:
October 5, 1993
Assignee:
DowElanco
Inventors:
Kevin L. McLaren, Mark B. Hertlein, James T. Pechacek, Michael J. Ricks, Yulan C. Tong, Laura L. Karr
Abstract: The present invention is directed to a ribosome inactivating protein from maize. The protein is characterized by being in a single chain proRIP inactive form that can be converted into an active form by cleavage with proteases.
Type:
Grant
Filed:
June 11, 1990
Date of Patent:
September 28, 1993
Assignee:
DowElanco
Inventors:
Terence A. Walsh, Timothy D. Hey, Alice E. R. Morgan
Abstract: Insects, especially sucking insects, such as brown planthoppers, and phytophageous mites, such as two-spotted spider mites, are controlled by applying an oxadiazole or thiadiazole compound substituted on a carbon atom by an aliphatic nitrogen heterocyclic moiety composed of at least one five or six membered ring. The compound 3-(3-amino-1,2,4-oxadiazol-5-yl)-1-azabicyclo[2,2,2]octane is typical.
Type:
Grant
Filed:
January 23, 1992
Date of Patent:
September 14, 1993
Assignee:
DowElanco
Inventors:
Michael R. Dick, Chi-Ping Chang, James E. Dripps, Susan Wollowitz
Abstract: The coupling of 4-haloquinolines with phenolic nucleophiles is accelerated by performing the reaction in the presence of a cata1ytic amount of 4-dialkylaminopyridine.
Type:
Grant
Filed:
May 7, 1992
Date of Patent:
September 14, 1993
Assignee:
DowElanco
Inventors:
Roger L. Robey, Charles A. Alt, Carl V. DeAmicis
Abstract: Substituted naphthyridines of the formula (1): ##STR1## wherein one of A, B, C, or D is N, and the others are CR.sup.1 ;R.sup.1 and R.sup.2 are independently H or halo.X, Y and Z are defined in the specification.
Type:
Grant
Filed:
March 4, 1992
Date of Patent:
August 31, 1993
Assignee:
DowElanco
Inventors:
Blake A. Caley, Michael J. Coghlan, Leon N. Davis, Barry A. Dreikorn
Abstract: Fungicidal compositions comprise a combination of two fungicides, one of which is a quinoline or cinnoline compound of the formula (1) ##STR1## the substituents being as described in the specification.
Type:
Grant
Filed:
May 12, 1992
Date of Patent:
August 31, 1993
Assignee:
DowElanco
Inventors:
Wendell R. Arnold, Michael J. Coghlan, Glen P. Jourdan, Eriks V. Krumkalns, Robert G. Suhr
Abstract: Disclosed are herbicidal concentrate formulation compositions having reduced grass crop plant phytotoxicity comprising certain sulfonamide or sulfonylurea herbicides in admixture with a herbicidal organic acid from the group consisting of clopyralid, 2,4-D, 2,4-DP, dicamba, dichlorprop-P, fluroxypyr MCPA, MCPP, mecoprop-P, picloram, triclopyr or mixtures of said acids; also disclosed is the preparation of said compositions and the pre- and post-emergent agricultural uses thereof in water diluted form.
Abstract: 2-(Phenoxy or phenylthio)-2-(pyrimidinyloxy or 1,3,5-triazinyloxy)alkanoic acid compounds, such as ethyl 2-(2-fluorophenoxy)-2-(4,6-dimethylpyrimidin-2-yloxy)-acetate, were prepared by the reaction of a phenol or thiophenol compound with a 2-chloro-2-(pyrimidinyloxy or 1,3,5-triazinyloxy)alkanoate ester compound or by the reaction of a pyrimidinol or 1,3,5-triazinol with a 2-bromo-2-(phenoxy or phenylthio)alkanoate ester. These compounds, and, especially, agriculturally acceptable salts, esters, and amides of these compounds, were found to have herbicidal utility.
Type:
Grant
Filed:
May 6, 1992
Date of Patent:
August 3, 1993
Assignee:
DowElanco
Inventors:
Michael G. Smith, William C. Lo, Wendy S. Jacks, Robert J. Ehr
Abstract: Polychlorodipyridoimidazolium tetrachloroferrate compounds, such as 1,2,3,4,11-pentachloro-8-(trichloromethyl)dipyrido[1,2-a:1',2'-]imidazol-1 0-ium tetrachloroferrate, which are obtained as by-products in the preparation of polychloropyridine and polychloropicoline compounds by chlorination of many chloro(trichloromethyl)pyridine compounds in the presence of ferric chloride catalyst and can be prepared by heating a mixture of a chloro-2-(trichloromethyl)pyridine compound with a 2-chloro-5-(trichloromethyl)pyridine compound, can be converted to pentachloropyridine by chlorination at temperatures above about 230.degree. C. and pressures above about 300 psig (2.17 mPa).
Type:
Grant
Filed:
October 22, 1991
Date of Patent:
July 20, 1993
Assignee:
DowElanco
Inventors:
Richard K. Helling, Kent P. Steele, Terrill E. Applebury