Patents Assigned to Uniroyal Chemical Ltd./Ltee
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Patent number: 5211736Abstract: A compound having the structural formula ##STR1##whereR is C.sub.2 -C.sub.8 alkylene having 2 to 4 carbon atoms linking X and Y;R.sup.1 is C.sub.1 -C.sub.8 linear or branched alkylene, C.sub.1 -C.sub.6 oxyalkylene, C.sub.1 -C.sub.6 thioalkylene or C.sub.1 -C.sub.6 aminoalkylene;R.sup.2 and R.sup.3 are the same or different and are hydrogen, halogen, C.sub.1 -C.sub.8 alkyl, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 alkylthio, C.sub.1 -C.sub.6 alkylsulfonyl, phenyl substituted phenyl, phenoxy, substituted phenoxy, cyano, nitro, --OCOR.sup.4, --COOR.sup.5, --CH.sub.m Q.sub.3-m or --OCH.sub.m Q.sub.3-m ;R.sup.4 is C.sub.1 -C.sub.4 alkyl;R.sup.5 is hydrogen or C.sub.1 -C.sub.4 alkyl;Q is halogen;X and Y are the same or different and are oxygen, sulfur, sulfinyl, sulfonyl or if one is NH, the other is sulfur;Z is nitrogen or CH; andm is 1, 2 or 3;and physiologically acceptable salts thereof,is disclosed. A process for synthesizing the compound of this invention is also set forth.Type: GrantFiled: February 7, 1992Date of Patent: May 18, 1993Assignees: Uniroyal Chemical Company, Inc., Uniroyal Chemical Ltd/LteeInventors: Hoi K. Lai, Robert A. Davis, Allen R. Blem
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Patent number: 5145982Abstract: This invention relates to a novel class of azoles of 5,6-dihydro-1,4-oxathiins having fungicidal activity. The class of compounds is represented by formula (I) ##STR1## wherein: R is each independently halogen; trifluoromethyl; C.sub.1 -C.sub.8 alkyl; C.sub.3 -C.sub.6 cycloalkyl; C.sub.1 -C.sub.8 alkoxy; C.sub.1 -C.sub.8 alkoxycarbonyl; amino; substituted amino; aminocarbonyl; aminosulfonyl; C.sub.1 -C.sub.8 alkoxy sulfonyl; phenyl; phenoxy; phenyl or phenoxy mono-, di- or tri-substituted independently with halogen, trifluoromethyl, C.sub.1 -C.sub.8 alkyl or C.sub.1 -C.sub.8 alkoxy; or benzyl;G is Ch or N;m is 0 1 or 2; andn is 0, 1 or 2.Fungicidal compositions, methods of controlling fungi and methods for preparing the compounds are within the scope of the invention.Type: GrantFiled: October 25, 1991Date of Patent: September 8, 1992Assignees: Uniroyal Chemical Company, Inc., Uniroyal Chemical Ltd./LteeInventors: Hoi K. Lai, Robert A. Davis
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Patent number: 5134145Abstract: This invention is related to a novel class of aryl pyrimidine derivatives having insecticidal, miticidal and nematocidal activity at low concentration. The class of compounds is represented by formula (I): ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, X and Z have the significance given in the description.Pesticidal compositions, methods of controlling pests and methods for preparing the compounds are within the scope of the invention.Type: GrantFiled: November 17, 1989Date of Patent: July 28, 1992Assignees: Uniroyal Chemical Company, Inc., Uniroyal Chemical Ltd./LteeInventors: Walter G. Brouwer, Ethel E. Felauer, Paul T. McDonald
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Patent number: 5134144Abstract: This invention is related to a novel class of 3-arylpyrimidine ethers and thioethers having insecticidal, miticidal and nematocidal activity at low concentration. The class of compounds is represented by formula (I): ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, X and Y have the significance given in the description.Pesticidal compositions, methods of controlling pests and methods for preparing the compounds are within the scope of the invention.Type: GrantFiled: November 20, 1989Date of Patent: July 28, 1992Assignees: Uniroyal Chemical Company, Inc., Uniroyal Chemical Ltd./LteeInventors: Walter G. Brouwer, Ethel E. Felauer, Paul T. McDonald, James A. McGuinness, Anupama Mishra
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Patent number: 5081143Abstract: This invention relates to a novel class of azoles of 5,6-dihydro-1,4-oxathiins having fungicidal activity. The class of compounds is represented by formula (I) ##STR1## wherein: R is each independently halogen; trifluoromethyl; C.sub.1 -C.sub.8 alkyl; C.sub.3 -C.sub.6 cycloalkyl; C.sub.1 -C.sub.8 alkoxy; C.sub.1 -C.sub.8 alkoxycarbonyl; amino; substituted amino; aminocarbonyl; aminosulfonyl; C.sub.1 -C.sub.8 alkoxy sulfonyl; phenyl; phenoxy; phenyl or phenoxy mono-, di- or tri-substituted independently with halogen, trifluoromethyl, C.sub.1 -C.sub.8 alkyl or C.sub.1 -C.sub.8 alkoxy; or benzyl;G is CH or N;m is 0 1 or 2; andn is 0, 1 or 2.Fungicidal compositions, methods of controlling fungi and methods for preparing the compounds are within the scope of the invention.Type: GrantFiled: August 10, 1990Date of Patent: January 14, 1992Assignees: Uniroyal Chemical Company, Inc., Uniroyal Chemical Ltd./LteeInventors: Hoi K. Lai, Robert A. Davis
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Patent number: 5071862Abstract: A compound having the structural formula ##STR1## where R and R.sup.1 are the same or different and are hydrogen or C.sub.1 -C.sub.6 alkyl; R.sup.2 is hydrogen, chlorine or bromine; R.sup.3 is hydrogen, C.sub.1- C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, halogen, trihalomethyl, nitro, cyano, phenyl, phenyl subsituted with C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halogen, trihalomethyl, nitro or cyano, phenoxy or phenoxy subsituted with C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halogen, trihalomethyl, nitro or cyano; and n is 0 or 1 is disclosed. A composition which comprises a fungicidally effective amount of the compound and a carrier therefor is also set forth. In addition, a process for controlling phytopathogenic fungi wherein a fungicidally effective amount of the compound is applied to the locus to be protected is described.Type: GrantFiled: October 26, 1990Date of Patent: December 10, 1991Assignees: Uniroyal Chemical Company, Inc., Uniroyal Chemical Ltd./Ltee.Inventors: Barry T. Friedlander, Robert A. Davis
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Patent number: 5039332Abstract: This invention relates to novel imidazole and triazole substituted oxathiolane compounds and compositions containing said compounds having fungicidal and plant growth regulant activity and methods for preparing same.Type: GrantFiled: December 23, 1988Date of Patent: August 13, 1991Assignees: Uniroyal Chemical Company, Inc., Uniroyal Chemical Ltd/Ltee.Inventors: Barry T. Friedlander, Robert A. Davis, Allen R. Blem, David L. Walker
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Patent number: 5010068Abstract: Organophosphorus-substituted oxadiazines are disclosed which exhibit insecticidal, acaricidal and nematicidal activity, as well as compositions including such compounds, and methods for controlling insects, acarids or nematodes employing such compounds and/or compositions. Also disclosed are novel intermediates useful in the preparation of such compounds.Type: GrantFiled: December 21, 1989Date of Patent: April 23, 1991Assignees: Uniroyal Chemical Company, Inc., Uniroyal Chemical Ltd. Ltee.Inventors: Mark A. Dekeyser, Richard C. Moore
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Patent number: 5006153Abstract: The invention relates to compounds useful as fungicides and plant growth regulants represented by the formula ##STR1## in which: R is a substituent or a group of substituents representing halogen, low alkyl of 1 to 6 carbon atoms, phenyl, substituted phenyl, phenoxy, substituted phenoxy, naphthyl, nitro, cyano, low alkoxy, alkoxycarbonyl, or trifluoromethyl;X is single bond, oxygen, sulfur or sulfonyl;G is CH or nitrogen atom;m is an integer from 1 to 4 and a process of making the compound.Type: GrantFiled: November 29, 1989Date of Patent: April 9, 1991Assignees: Uniroyal Chemical Company, Inc., Uniroyal Chemical Ltd./Ltee.Inventors: Hoi K. Lai, Robert A. Davis, Allen R. Blem
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Patent number: 4979982Abstract: Compounds having the structure ##STR1## wherein: R is C.sub.1 -C.sub.12 alkyl, linear or branched; or C.sub.3 -C.sub.12 alkenyl;R.sup.1 is C.sub.1 -C.sub.12 alkyl, linear or branched and can form a carbocycle;X is hydrogen or halogen; andY is hydrogen or halogen;are disclosed which have herbicidal activity. Herbicidal compositions comprising the compounds and a carrier are also disclosed, as are methods for controlling the growth orf undesirable plants utilizing the compounds. Methods for the preparation of such compounds are also disclosed.Type: GrantFiled: February 2, 1990Date of Patent: December 25, 1990Assignees: Uniroyal Chemical Company, Inc., Uniroyal Chemical Ltd./LteeInventors: Walter G. Brouwer, Ethel E. Felauer, Allyn R. Bell
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Patent number: 4966910Abstract: This invention relates to a novel class of azoles of 5,6-dihydro-1,4-oxathins having fungicidal activity. The class of compounds is represented by formula (I) ##STR1## wherein R is each independently halogen; trifluoromethyl; C.sub.1 -C.sub.8 alkyl; C.sub.3 -C.sub.6 cycloalkyl; C.sub.1 -C.sub.8 alkoxy; C.sub.1 -C.sub.8 alkoxycarbonyl; amino; substituted amino; aminocarbonyl; aminosulfonyl; C.sub.1 -C.sub.8 alkoxy sulfonyl; phenyl; phenoxy; phenyl or phenoxy mono-, di- or tri-substituted independently with halogen, trifluoromethyl, C.sub.1 -C.sub.8 alkyl or C.sub.1 -C.sub.8 alkoxy; or benzyl;G is CH or N;m is 0 1 or 2; andn is 0, 1 or 2.Fungicidal compositions, methods of controlling fungi and methods for preparing the compounds are within the scope of the invention.Type: GrantFiled: October 18, 1989Date of Patent: October 30, 1990Assignees: Uniroyal Chemical Company, Inc., Uniroyal Chemical Ltd./LteeInventors: Hoi K. Lai, Robert A. Davis
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Patent number: 4950671Abstract: A heterocyclic compound having the structural formula ##STR1## where R is C.sub.1 -C.sub.8 alkyl, C.sub.3 -C.sub.6 cycloalkyl, trifluoromethyl, phenyl, substituted phenyl, phenoxy, substituted phenoxy, benzyl or substituted benzyl; and R.sup.1 is at least a partially saturated monocyclic or bicyclic heterocycle of nitrogen which may be substituted with lower alkyl and physiologically acceptable salts thereof is disclosed. A process for forming this compound which involves the reaction of an amine of the formula HR.sup.1 where R.sup.1 has the meanings given above with a substituted 2-propenyl halide having the structural formula ##STR2## where R has the meanings given above; and X is a halogen atom is described. The invention embodies the above-mentioned novel 2-propenyl halide utilized as an intermediate in the formation of the heterocyclic compound of this invention.Type: GrantFiled: March 9, 1989Date of Patent: August 21, 1990Assignees: Uniroyal Chemical Company, Inc., Uniroyal Chemical Ltd/LteeInventors: Hoi Kiong Lai, Robert A. Davis
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Patent number: 4943311Abstract: A compound having the structural formula ##STR1## where R is C.sub.2 -C.sub.8 alkylene having 2 to 4 carbon atoms linking X and Y;R.sup.1 is C.sub.1 -C.sub.8 linear or branched alkylene, C.sub.1 -C.sub.6 oxyalkylene, C.sub.1 -C.sub.6 thioalkylene or C.sub.1 -C.sub.6 aminoalkylene;R.sup.2 and R.sup.3 are the same or different and are hydrogen, halogen, C.sub.1 -C.sub.8 alkyl, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 alkylthio, C.sub.1 -C.sub.6 alkylsulfonyl, phenyl, substituted phenyl, phenoxy, substituted phenoxy, cyano, nitro, --OCOR.sup.4, --COOR.sup.5, --CH.sub.m Q.sub.3-m or --OCH.sub.m Q.sub.3-m ;R.sup.4 is C.sub.1 -C.sub.4 alkyl;R.sup.5 is hydrogen or C.sub.1 -C.sub.4 alkyl;Q is halogen;X and Y are the same or different and are oxygen, sulfur, sulfinyl, sulfonyl or if one is NH, the other is sulfur;Z is nitrogen or CH; andm is 1, 2 or 3;and physiologically acceptable salts thereof,is disclosed. A process for synthesizing the compound of this invention is also set forth.Type: GrantFiled: May 9, 1988Date of Patent: July 24, 1990Assignees: Uniroyal Chemical Company, Inc., Uniroyal Chemical Ltd/LteeInventors: Hoi K. Lai, Robert A. Davis, Allen R. Blem
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Patent number: 4927451Abstract: A compound having the structural formula ##STR1## where R.sup.1 is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.6 cycloalkyl, C.sub.3 -C.sub.4 alkenyl or trifluoromethyl; R.sup.2 is C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.6 cycloalkyl, C.sub.3 --C.sub.4 alkenyl, C.sub.7 -C.sub.10 aralkyl or C.sub.7 -C.sub.10 haloaralkyl; R.sup.3 is hydrogen or C.sub.1 -C.sub.4 alkyl; R.sup.4 is hydrogen or C.sub.1 -C.sub.2 alkyl; X is halogen; Y is hydrogen, C.sub.1 -C.sub.4 alkyl or halogen; and Z is oxygen or sulfur is disclosed. In addition, a process for forming the compound is set forth. A method for controlling weeds which comprises applying a herbicidally effective amount of the compound recited above is also described. Finally, a composition, useful as a herbicide, including the compound of this invention and a suitable carrier therefor is taught.Type: GrantFiled: December 30, 1988Date of Patent: May 22, 1990Assignees: Uniroyal Chemical Company, Inc., Uniroyal Chemical Ltd/LteeInventors: Walter G. Brouwer, Ethel Ellen Felauer, Allyn Roy Bell
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Patent number: 4880828Abstract: A new class of 2-(tetrahydro-2-theinyl)phenyl esters of phosphorothioic acid is disclosed. This class of compounds is an effective pesticide and finds particular application as an insecticide. A class of pesticidal compositions employing these compounds in combination with a carrier therefor is also set forth.Type: GrantFiled: January 29, 1988Date of Patent: November 14, 1989Assignees: Uniroyal Chemical, Inc., Uniroyal Chemical Ltd./LteeInventors: Anupama Mishra, Richard C. Moore
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Patent number: 4870094Abstract: A compound of the formula ##STR1## where Z and Z.sup.1 are the same or different and are oxygen, sulfur, SO, SO.sub.2, or NR.sup.3 ; except that Z and Z.sup.1 are not simultaneously oxygen, also, if Z or Z.sup.1 is sulfur then the other of Z and Z.sup.1 cannot be NR.sup.3 ; Y is nitrogen or CH; R is linear or branched C.sub.2 -C.sub.12 alkylene; R.sup.1 is hydrogen, C.sub.1 -C.sub.4 alkyl, benzyl or phenyl; R.sup.2 is phenyl, phenoxy, phenylthio, phenylsulfinyl, phenylsulfonyl, phenylamino, benzyl, phenoxy substituted with halo, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, nitro, cyano, trihalomethyl or mono-, di- or trihalomethoxy or phenyl substituted with halo, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, nitro, cyano, trihalomethyl or mono-, di- or trihalomethoxy; and R.sup.3 is hydrogen or C.sub.1 -C.sub.6 alkyl, is disclosed.A process for forming this compound is also taught. In the process a substituted azole compound of the formula ##STR2## where Y, R.sup.1 and R.sup.Type: GrantFiled: October 30, 1984Date of Patent: September 26, 1989Assignees: Uniroyal Chemical Company, Inc., Uniroyal Chemical LTD/LTEEInventors: Barry T. Friedlander, Robert A. Davis, Allen R. Blem
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Patent number: 4857649Abstract: The invention relates to compounds useful as fungicides and plant growth regulants represented by the formula ##STR1## in which: R is a substituent or a group of substituents representing halogen, lower alkyl of 1 to 6 carbon atoms, phenyl, substituted phenyl, phenoxy, substituted phenoxy, naphthyl, nitro, cyano, lower alkoxy, alkoxycarbonyl, or trifluoromethyl;X is single bond, oxygen, sulfur or sulfonyl;G is CH or nitrogen atom;m is an integer from 1 to 4 and a process of making the compound.Type: GrantFiled: July 21, 1988Date of Patent: August 15, 1989Assignees: Uniroyal Chemical Company, Inc., Uniroyal Chemical LTD/LTEEInventors: Hoi K. Lai, Robert A. Davis, Allen R. Blem
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Patent number: 4845217Abstract: A process is provided for the purification to highly purified states of 5-pyrimidinecarboxamides which are essentially insoluble in both organic and inorganic solvents. The 5-pyrimidinecarboxamide to be purified is contacted with an organic base having a pKa value in excess of 6.95 to form an adduct. The adduct is purified through recrystallization and the desired 5-pyrimidinecarboxamide is regenerated from the adduct in highly purified form with acid. Additionally, an adduct resulting from the combination of a 5-pyrimidinecarboxamide with such an organic base is provided, which adduct is capable of being purified using recrystallization techniques, where the 5-pyrimidinecarboxamide is not itself capable of being so purified due to its relative insolubility in organic and inorganic solvents.Type: GrantFiled: December 8, 1986Date of Patent: July 4, 1989Assignee: Uniroyal Chemical Ltd./LteeInventor: Arthur D. Brewer
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Patent number: 4845236Abstract: A compound having the structural formula ##STR1## where R is C.sub.1 -C.sub.6 alkyl or C.sub.5 -C.sub.6 cycloalkyl; X is hydrogen or methyl;R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are the same or different and are hydrogen, halogen, C.sub.1 -C.sub.8 alkyl, C.sub.1 -C.sub.2 haloalkyl, C.sub.3 -C.sub.6 cycloalkyl, C.sub.7 -C.sub.9 aralkyl, phenyl, nitro, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 alkylthio, C.sub.1 -C.sub.6 alkylsulfinyl, C.sub.1 -C.sub.6 alkylsulfonyl, C.sub.7 -C.sub.9 aralkoxy, phenoxy, phenylthio, phenylsulfinyl, phenylsulfonyl, tetrahydro-2-thienyl, dioxytetrahydro-2-thienyl, alkali metal carboxylate, C.sub.2 -C.sub.5 alkoxycarbonyl, phenoxycarbonyl or N(R.sup.5)R.sup.6 ;R.sup.5 and R.sup.6 are the same or different and are hydrogen or C.sub.1 -C.sub.2 alkyl; andn is 0, 1 or 2 is disclosed. A method for controlling insects using an insecticidally effective amount of this compound is also taught.Type: GrantFiled: August 10, 1988Date of Patent: July 4, 1989Assignees: Uniroyal Chemical Company, Inc., Uniroyal Chemical Ltd./LteeInventors: Anupama Mishra, Richard C. Moore