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.
Abstract: A plant fungicide method comprises applying to the locus of a plant pathogen a fungicidally effective amount of a compound of formula (I) ##STR1## or a salt or a complex thereof, wherein: R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, and R.sup.8 are independently H, halo, NO.sub.2, (C.sub.1 -C.sub.4) alkyl, or halo(C.sub.1 -C.sub.4) alkyl;R.sup.3', R.sup.4', R.sup.5', R.sup.3", R.sup.4", and R.sup.5" are independently H, halo, OH, or CH.sub.3, provided that at least one is OH;R.sup.6 ' and R.sup.6 " are independently H or OH.
Type:
Grant
Filed:
October 4, 1993
Date of Patent:
September 5, 1995
Assignee:
DowElanco
Inventors:
Deirdre M. Sinnott, Hak-Fun Chow, Robert J. Ehr, Steven D. Lubetkin, Stephen E. Bales, Muthiah N. Inbasekaran
Abstract: Substituted N-indazolyl[1,2,4]triazolo[1,5]-c-pyrimidine-2-sulfonamide compounds, such as N-(4-fluoro-1-methyl-3-indazolyl)-5-ethoxy-7-fluoro[1,2,4]triazolo[1,5-c]p yrimidine-2-sulfonamide, were prepared by condensation of a 2-chlorosulfonyl[1,2,4]triazolo[1,5-c]pyrimidine compound, such as 2-chlorosulfonyl-5-ethoxy-7-fluoro[1,2,4]triazolo[1,5-c]pyrimidine, with a substituted 3-aminoindazole compound, such as 3-amino-4-fluoro-1-methylindazole, and found to possess herbicidal utility.
Type:
Grant
Filed:
July 11, 1994
Date of Patent:
September 5, 1995
Assignee:
DowElanco
Inventors:
Mark J. Costales, Robert J. Ehr, William A. Kleschick, John C. Van Heertum, Walter Reifschneider
Abstract: Agricultural formulations of fluroxypyr that contain an ester of fluroxypyr that is liquid at ambient temperatures, such as the 1-butoxy-2-propyl ester or the 2-ethylhexyl ester, and that contain a reduced amount of organic solvent or no organic solvent are disclosed. The formulations have good physical properties and are highly effective herbicides.
Type:
Grant
Filed:
April 26, 1994
Date of Patent:
July 25, 1995
Assignee:
DowElanco
Inventors:
Patrick J. Mulqueen, Graham Banks, John Davies, Eileen A. Paterson, Marten Snel
Abstract: Hydroxycornexistin (1), the free dibasic acid thereof (2) ##STR1## agronomically acceptable bis-ester, monoester, monoamide, and monothioesters thereof, and agronomically acceptable salts thereof are selective herbicides for broad spectrum broadleaf and grass weed control in corn.
Type:
Grant
Filed:
March 1, 1994
Date of Patent:
June 13, 1995
Assignee:
DowElanco
Inventors:
Stephen C. Fields, B. Clifford Gerwick, III, Linda C. Mireles-Lo
Abstract: 3,4,N-Trisubstituted-4,5-dihydro-1H-pyrazole-1-carboxamide compounds wherein the substituent in the 4-position is a 5-membered heterocyclic ring moiety containing one ring oxygen or sulfur atom and one or two ring nitrogen atoms and the substituents in the 3-posit ion and the N-position are optionally substituted phenyl moieties, such as 4,5-dihydro-3-(4-fluorophenyl)-N-(4-trifluoromethylphenyl)-4-(2-trifluorom ethyl-5-thiazolyl)-1H-pyrazole-1-carboxamide were prepared from appropriate 3,4-disubstituted-4,5-dihydro-1H-pyrazole compounds, such as 4,5-dihydro-3-(4-fluorophenyl)-4-(2-trifluoromethyl-5-thiazolyl)-1H-pyrazo le and phenyl is ocyanates and isothiocyanates, such as 4-(trifluoromethyl)phenyl isocyanate. The compounds are insecticidal.
Abstract: Substituted quinazolines of the formula (1): ##STR1## wherein: R.sup.1 to R.sup.4 are independently H, halo, (C.sub.1 -C.sub.4) alkyl, branched (C.sub.3 -C.sub.4) alkyl, halo (C.sub.1 -C.sub.4) alkyl, (C.sub.1 -C.sub.4) alkoxy, NO.sub.2, or NH.sub.2,provided thatat least two of R.sup.1 to R.sup.4 are H;Y is H, Cl, X--W--Ar, or O--Alk;X is O, NR.sup.7, or CR.sup.8 R.sup.9 ;Z is H, Cl, OCH.sub.3, CH.sub.3, or --NR.sup.7 --W--Ar, provided that Z can be --NR.sup.7 --W--Ar only if Y is H, Cl, or NR.sup.7 --W--Ar and Z must be --NR.sup.7 --W--Ar if Y is H or Cl, which are plant fungicides, miticides, and insecticides.
Type:
Grant
Filed:
July 19, 1993
Date of Patent:
May 2, 1995
Assignee:
DowElanco
Inventors:
Barry A. Dreikorn, Glen P. Jourdan, Robert G. Suhr
Abstract: 5-Acylamino-1,2,4-triazole-3-sulfonamides, which are useful intermediates for the preparation of 1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamide herbicides are prepared from 5-amino-3-mercapto-1,2,4-triazole by sequential acylation to 5-acylamino-3-mercapto-1,2,4-triazoles, chlorination to 5-acylamino-3-chlorosulfonyl-1,2,4-triazoles, and condensation with substituted anilines to 5-acylamino-1,2,4-triazole-3-sulfonamides. 5-Acylamino-3-chlorosulfonyl-1,2,4-triazole compounds are key intermediates in the process.
Type:
Grant
Filed:
September 1, 1993
Date of Patent:
April 25, 1995
Assignee:
DowElanco
Inventors:
Jack C. Little, Mark J. Costales, Ravi B. Shankar, R. Garth Pews
Abstract: A bait station comprises a base having first and second side walls connected together along a corner and extending preferably at about a 90.degree. angle to one another, and a cover secured to the side walls to form a triangular unit. A pair of mutually-facing, C-shaped projections extend into the interior chamber of the bait station from the corner between the side walls at an angle of 45.degree. to each side wall. (In one embodiment, top projections extend downwardly from the cover adjacent the base projections.) A bait material is positioned in the station between the C-shaped base projections. The bait station is advantageously positioned on a surface adjacent a wall, and insects and the like crawling along the wall are directed into the station and to the bait. The design of the bait station makes it useful with either of the side walls placed as the bottom of the unit.
Type:
Grant
Filed:
February 7, 1994
Date of Patent:
April 18, 1995
Assignee:
DowElanco
Inventors:
Brian M. Schneider, Anton Arnoldy, Brian L. Bret, Kevin J. Burns, James E. King
Abstract: N-(4-Pyridyl or 4-quinolinyl) arylacetamides, for example N-((3-chloro-2-ethyl)-4-pyridyl)(4-(4-chlorophenoxy) phenyl)-acetamide, and 4-(aralkyoxy or aralkylamino)pyridines, for example 4-[2-[4-(2,2,2-trifluoroethoxy)phenyl]ethoxy]pyridine, are active against nematodes, insects, mites, and plant pathogens.
Type:
Grant
Filed:
August 19, 1992
Date of Patent:
March 21, 1995
Assignee:
DowElanco
Inventors:
Ronald E. Hackler, Glen P. Jourdan, Peter L. Johnson, Brian R. Thoreen, Jack G. Samaritoni
Abstract: The present disclosure is directed to substituted cyclohexanedione compounds, the preparation of said compounds, compositions containing said compounds and the use of said compositions in the selective pre- and postemergent kill and control of grassy weeds in the presence of various broad-leafed and grassy crop plants.
Type:
Grant
Filed:
December 20, 1993
Date of Patent:
March 21, 1995
Assignee:
DowElanco
Inventors:
Christopher T. Hamilton, Lowell D. Markley, Todd C. Geselius
Abstract: Insects, especially sucking insects, such as brown planthoppers, and phytophageous mites, such as two-spotted spider mites, are controlled by applying an triazole or tetrazole compound substituted on a carbon atom by an aliphatic nitrogen heterocyclic moiety composed of at least one five or six membered ring. The compound exo-3-(5-aminotetrazol-2-yl)-1-azabicyclo[2.2.1]heptane is typical.
Abstract: 5-Acylamino-1,2,4-triazole-3-sulfonamides, which are useful intermediates for the preparation of 1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamide herbicides are prepared from 5-amino-3-mercapto-1,2,4-triazole by sequential acylation to 5-acylamino-3-mercapto-1,2,4-triazoles, chlorination to 5-acylamino-3-chlorosulfonyl-1,2,4-triazoles, and condensation with substituted anilines to 5-acylamino-1,2,4-triazole-3-sulfonamides. 5-Acylamino-3-chlorosulfonyl-1,2,4-triazole compounds are key intermediates in the process.
Type:
Grant
Filed:
December 19, 1988
Date of Patent:
February 21, 1995
Assignee:
DowElanco
Inventors:
Jack C. Little, Mark J. Costales, Ravi B. Shankar, R. Garth Pews, Kidisti G. Mariam, Susan D. Thompson
Abstract: 5-Amino-l,2,4-triazole-3-sulfonamides, which are intermediates for substituted 1,2,4-triazolo-[1,5-a]pyrimidine-2-sulfonamide herbicides are prepared in two steps from 5-amino-3-mercapto-1,2,4-triazole by chlorination in a medium containing an aqueous acid to obtain 5-amino-3-chlorosulfonyl-1,2,4-triazole and subsequent condensation of this intermediate with substituted anilines. The condensation reaction takes place either in the presence or absence of an acid scavenging base.
Type:
Grant
Filed:
December 19, 1988
Date of Patent:
January 17, 1995
Assignee:
DowElanco
Inventors:
Jack C. Little, Mariam G. Kidisti, Patricia A. Thibos, Susan D. Thompson
Abstract: The present invention relates to novel substituted guanidine and amidine compounds, their preparation and their use in the kill and control of fungal organisms which infest plants.
Abstract: Agricultural formulations of fluroxypyr that contain an ester of fluroxypyr that is liquid at ambient temperatures, such as the 1-butoxy-2-propyl ester or the 2-ethylhexyl ester, and that contain a reduced amount of organic solvent or no organic solvent are disclosed. The formulations have good physical properties and are highly effective herbicides.
Type:
Grant
Filed:
April 23, 1993
Date of Patent:
December 20, 1994
Assignee:
DowElanco
Inventors:
Patrick J. Mulqueen, Graham Banks, John Davies, Eileen A. Paterson, Marten Snel
Abstract: Fermentation product A83543, comprising major components A83543A and A83543D and minor components A83543B, A83543C, A83543E, A983543F, A83543G, A83543H and A83543J, is produced by a newly described species, Saccharopolyspora spinosa. The A83543 components and their acid-addition salts (A83543 compounds) are useful as insecticides, particularly against Lepidoptera and Diptera species. Insecticidal, miticidal or ecto-parasiticidal combinations, compositions and methods are provided.
Type:
Grant
Filed:
October 10, 1991
Date of Patent:
November 8, 1994
Assignee:
DowElanco
Inventors:
LaVerne D. Boeck, Hang Chio, Tom E. Eaton, Otis W. Godfrey, Jr., Karl H. Michel, Walter M. Nakatsukasa, Raymond C. Yao
Abstract: 5-Amino-1,2,4-triazole-3-sulfonamides, which are intermediates for substituted 1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamide herbicides are prepared in two steps from 5-amino-3-mercapto-1,2,4-triazole by chlorination in a medium containing an aqueous acid to obtain 5-amino-3-chlorosulfonyl-1,2,4-triazole and subsequent condensation of this intermediate with substituted anilines. The condensation reaction takes place either in the presence or absence of an acid scavenging base.
Type:
Grant
Filed:
May 14, 1993
Date of Patent:
October 25, 1994
Assignee:
DowElanco
Inventors:
Jack C. Little, Patricia A. Thibos, Mariam G. Kidisti, Susan D. Thompson
Abstract: 4-substituted-pyrido[3,2-d]pyridmidine, -pyrido[4,3-d]pyrimidine, -pyrido[3,4-d]pyrimidine, pyrido[2,3-d]pyrimidine, -pteridine, -pyrimido[4,5-d]pyrimidine, -pyrimido[4,5-c]pyridazine, -pyrimido[5,4-d]pyrimidine, -pyrimido[5,4-c]pyridazine, pyrimido[4,5-d]pyridazine, and pyrimido[5,4-e]-1,2,4-triazine derivatives, for example 4-[2-(4-chlorophenyl)ethoxy]pyrido[2,3-d]pyrimidine, are useful as fungicides, inseciticides and miticides.
Abstract: 3,4,N-Trisubstituted-4,5-dihydro-1H-pyrazole-1-carboxamide compounds wherein the substituent in the 4-position is a 5-membered heterocyclic ring moiety containing one ring oxygen or sulfur atom and one or two ring nitrogen atoms and the substituents in the 3-position and the N-position are optionally substituted phenyl moieties, such as 4,5-dihydro-3-(4-fluorophenyl)-N-(4-trifluoromethylphenyl)-4-(2-trifluorom ethyl-5-thiazolyl)-1H-pyrazole-1-carboxamide were prepared from appropriate 3,4-disubstituted-4,5-dihydro-1H-pyrazole compounds, such as 4,5-dihydro-3-(4-fluorophenyl)-4-(2-trifluoromethyl-5-thiazolyl)-1H-pyrazo le and phenyl isocyanates and isothiocyanates, such as 4-(trifluoromethyl)phenyl isocyanate. The compounds are insecticidal.