Patents Represented by Attorney H. Robinson Ertelt
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Patent number: 5756755Abstract: An improved process for the difluoromethylation of a 1-(optionally substituted)phenyl-1H-1,2,4-triazol-5-one at the 4-position of the triazole ring with chlorodifluoromethane significantly reduces the cycle time required for the reaction. The improvement comprises reacting the triazolinone with potassium carbonate in a glyme solvent, heating one molar equivalent of a sodium or potassium salt of the triazolinone with 0.1 to 1 molar equivalent of potassium carbonate and 1.5 to 1.8 molar equivalents of chlorodifluoromethane in a glyme solvent, the concentration the triazolinone in the glyme being in the range of 5 to 15 percent weight/volume, at a temperature in the range of 165.degree. to 200.degree. C. for 5 to 30 minutes, with a 10 to 15 percent molar excess of chlorodifluoromethane, either at atmospheric pressure under an inert atmosphere or in a sealed autoclave, and recovering the difluoromethylated triazolinone.Type: GrantFiled: May 30, 1997Date of Patent: May 26, 1998Assignee: FMC CorporationInventor: Jaidev S. Goudar
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Patent number: 5753595Abstract: Herbicidal 3-(substituted benzoxazol-7-yl) and 3-(substituted benzothiazol-7-yl)-1 -substituted-6-trifluoromethyl-2,4-(1H,3H)pyrimidinediones, compositions containing them, and methods of using them to control undesired plant growth are disclosed, as are novel intermediates used in the preparation of these compounds. The herbicidal compounds of the present invention are defined by the following generic structure: ##STR1## in which R is selected from a variety of substituents, including halogen, alkyl, alkenyl, alkynyl, phenyl, phenylalkyl, alkylphenylalkyl, haloalkyl, hydroxy, alkoxy, hydroxyalkyl, halophenyl, halophenylalkyl, alkoxyphenyl, sulfhydryl, alkylthio, piperidinyl, alkylamino, alkoxyalkyl, phenoxy, amino, alkylsulfonylamino, phenylsulfonylamino, and carboxy; R.sup.1 is alkyl or amino; R.sup.Type: GrantFiled: July 31, 1996Date of Patent: May 19, 1998Assignee: FMC CorporationInventors: Scott D. Crawford, Lester L. Maravetz, George Theodoridis
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Patent number: 5683966Abstract: Herbicidal 3-(substituted-benzyl)-1-methyl-6-trifluoromethyluracils, compositions containing them, and methods of using them to control undesired plant growth, including use to control weeds in certain crops, are disclosed.Type: GrantFiled: June 10, 1996Date of Patent: November 4, 1997Assignee: FMC CorporationInventor: Marvin J. Konz
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Patent number: 5674810Abstract: Herbicidal compounds, compositions containing them, and a method for controlling weeds by application of the compositions are disclosed. The herbicidal compounds are 2-?(4-heterocyclic-phenoxymethyl)phenoxy!alkanoates of the formula ##STR1## in which A is a derivative of an alkanoate bonded to the phenoxy oxygen at the alpha carbon; X is hydrogen, methyl, fluorine, or chlorine; Y is hydrogen; W is oxygen or sulfur; Z is hydrogen, fluorine, chlorine, bromine, lower alkyl, or methoxy; Z' is hydrogen, fluorine, or chlorine; and the group AO-- may be in the 2, 3, or 4-position of the phenyl ring.Type: GrantFiled: September 5, 1995Date of Patent: October 7, 1997Assignee: FMC CorporationInventor: George Theodoridis
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Patent number: 5661108Abstract: Herbicidal 3-(bicyclic nitrogen-containing heterocycle)-substituted-1-methyl-6-trifluoromethyluracils, compositions containing them, and methods of using them to control undesired plant growth are disclosed. The herbicidal compounds of the present invention are defined by the following generic structure: ##STR1## in which V is N or C--R.sup.1 ; R is hydrogen, straight or branched chain alkyl, alkenyl, alkynyl, hydroxyalkyl, alkoxyalkyl, haloalkyl, alkoxycarbonylalkyl, arylalkyl, optionally substituted with halogen, or aminocarbonylalkyl in which the amino nitrogen is substituted with arylalkyl or one or two alkyl; R.sup.1 is hydrogen, alkyl, haloalkyl, or cyano; R.sup.2 is lower alkyl or amino; and X is hydrogen or halogen, with the proviso that each aliphatic component has not more than six carbon atoms.Type: GrantFiled: January 18, 1995Date of Patent: August 26, 1997Assignee: FMC CorporationInventors: Scott D. Crawford, Lester L. Maravetz, George Theodoridis
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Patent number: 5639763Abstract: Compounds of the following structure, the corresponding N-oxides and agriculturally acceptable salts, are disclosed as effective insecticides: ##STR1## in which U is selected from --(CH.sub.2).sub.n -- and ethylidene; Q is selected from hydrogen, hydroxy, sulfhydryl, and fluorine; R is ##STR2## in which V is selected from hydrogen, halogen, alkyl, haloalkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsilyloxy, dialkylamino, cyano, nitro, hydroxy, and phenyl; Y and Z are independently selected from hydrogen and alkoxy; W and X taken together is --OCH.sub.2 CH.sub.2 O--, --CH.sub.2 C(CH.sub.3).sub.2 O--, --OC(CH.sub.3).sub.2 O--, or --N.dbd.C(C.sub.2 H.sub.5)O--; R.sup.1 and R.sup.2 are independently selected from phenyl substituted with halogen, alkyl, haloalkyl, haloalkoxy, alkoxyalkyl, hydroxy, arylthio, alkoxy, dialkylamino, dialkylaminosulfonyl, hydroxyalkylaminocarbonyl, alkylsulfonyloxy, and haloalkylsulfonyloxy; and n is 1, 2, or 3.Type: GrantFiled: February 16, 1995Date of Patent: June 17, 1997Assignee: FMC CorporationInventors: Ian R. Silverman, Daniel H. Cohen, John W. Lyga, Steven W. Szczepanski, Syed F. Ali
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Patent number: 5621112Abstract: A process is disclosed for the preparation of the herbicide ethyl .alpha.-2-dichloro-5-[4-(difluoromethyl)-4,5-dihydro-3-methyl-5-oxo-1H-1,2 ,4-triazol-1-yl]-4-fluorobenzenepropionate by the simultaneous diazotization of 4-difluoromethyl-4,5-dihydro-3-methyl-5-oxo-1-(5-amino-2-fluoro-4-chloro-p henyl)-1H-1,2,4-triazole (the Amine) and arylation of ethyl acrylate with the diazotized Amine. In the process the following reagents are added in sequence and, under specified conditions, to a cooled, stirred solution of the Amine in acetone: cuprous chloride, hydrochloric acid, ethyl acrylate, and sodium nitrite.Type: GrantFiled: July 18, 1996Date of Patent: April 15, 1997Assignee: FMC CorporationInventors: John W. Ager, Craig A. Polsz
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Patent number: 5597780Abstract: An herbicidal composition containing from 1 to 4 pounds of clomazone per gallon of formulation and having a clomazone volatility less than fifty percent of that of an emulsifiable concentrate containing four pounds of clomazone per gallon of formulation is prepared by the interfacial reaction of polymethylene polyphenyl isocyanate with a polyfunctional amine selected from ethylenediamine, diethylenetriamine, triethylenetetramine, 1,6-hexanediamine, and their mixtures in an aqueous phase optionally containing from 0.05 to 0.25 weight percent of a xanthan gum viscosity modified/stabilizer. Several such formulations and the method of their preparation are described.Type: GrantFiled: September 21, 1995Date of Patent: January 28, 1997Assignee: FMC CorporationInventors: Fui-Tseng H. Lee, Paul Nicholson
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Patent number: 5569664Abstract: Compounds of the following structure, the corresponding N-oxides and agriculturally acceptable salts, are disclosed as effective insecticides: ##STR1## in which U is selected from ##STR2## Q is selected from hydrogen, hydroxy, sulfhydryl, and fluorine; R is selected from a heterocycle having 5 or 6 ring atoms, optionally fused to a benzene ring, and ##STR3## wherein V, W, X, Y, Z are as defined in the specification.Type: GrantFiled: May 19, 1995Date of Patent: October 29, 1996Assignee: FMC CorporationInventors: Ian R. Silverman, Daniel H. Cohen, John W. Lyga, Steven W. Szczepanski, Syed F. Ali
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Patent number: 5521147Abstract: Herbicidal 3-(benzofuran-7-yl)-6-haloalkyluracils of the formula ##STR1## in which M is fluoroalkyl (C.sub.1-6); D is hydrogen, alkyl (C.sub.1-6), or alkoxy(C.sub.1-6)-carbonyl; E is hydrogen or alkyl (C.sub.1-6), or D and E taken together are --CH.sub.2 CH.sub.2 --; R is hydrogen, amino, alkyl (C.sub.1-6), 2-alkenyl (C.sub.3-6), 2-alkynyl (C.sub.3-6), alkoxy(C.sub.1-6)methyl, benzyl, amino, fluoroalkyl (C.sub.1-6), alkoxy (C.sub.1-6)-carbonylmethyl; or cyanoalkyl (C.sub.1-6) having preferably one cyano group; X is hydrogen, fluorine, chlorine, bromine, cyano, alkyl(C.sub.1-6), haloalkyl(C.sub.1-6), haloalkoxy(C.sub.1-6), or alkoxy(C.sub.1-6); Y is hydrogen, alkyl (C.sub.1-6), fluorine, chlorine, or bromine; and Z is CH.sub.2, C.dbd.O, C.dbd.S, --CH(OH)--, --CH.sub.2 CH.sub.2 --, --CH.dbd.CH--, --(C.dbd.O)CH.sub.2 --; or C.dbd.N--O--R' wherein R' is alkyl(C.sub.1-6).Type: GrantFiled: February 3, 1995Date of Patent: May 28, 1996Assignee: FMC CorporationInventor: George Theodoridis
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Patent number: 5472700Abstract: Combinations of bifenthrin with azadirachtin-containing neem seed extracts are synergistic in controlling acarids, especially pyrethroid-resistant mites, over a wide range of azadirachtin to bifenthrin ratios. The combinations are also used for the control of ectoparasites on animals.Type: GrantFiled: October 3, 1994Date of Patent: December 5, 1995Assignee: FMC CorporationInventors: Charles A. Staetz, H. Robinson Ertelt, Gert P. Volpp
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Patent number: 5468868Abstract: This invention provides a process for optimizing the yield of a 1-(2,4-dichlorophenyl)-4,5-dihydro-1H-1,2,4-triazol-5-one by the chlorination in two steps of a 4,5-dihydro-1-phenyl-1H-1,2,4-triazol-5-one. The critical first step is the selective chlorination of the phenyl ring in the 4-position by addition of chlorine to a solution of the 4,5-dihydro-1-phenyl-1H-1,2,4-triazol-5-one in N,N-dimethylformamide. Chlorination of the product of the first step in acetic acid/water yields the 1-(2,4-dichlorophenyl)-4,5-dihydro-1H-1,2,4-triazol-5-one in high yield.Type: GrantFiled: December 16, 1993Date of Patent: November 21, 1995Assignee: FMC CorporationInventors: Marc Halfon, Craig A. Polsz, John H. Hoare
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Patent number: 5441925Abstract: Herbicidal 1-Amino-3-(bicyclic heterocyclyl)-6-fluoroalkyluracils of the formula ##STR1## in which M is fluoroalkyl(C.sub.1-6); R.sup.1 is hydrogen or alkyl(C.sub.1-6); R.sup.2 is hydrogen or alkyl (C.sub.1-6); Y is hydrogen, fluorine, chlorine, or bromine; X is hydrogen, fluorine, chlorine, bromine, cyano, alkyl(C.sub.1-6), or fluoroalkyl(C.sub.1-6); and n is 0 or 1.Type: GrantFiled: June 28, 1994Date of Patent: August 15, 1995Assignee: FMC CorporationInventor: George Theodoridis
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Patent number: 5440045Abstract: A process for the production of an aryl triazolinones of the formula ##STR1## wherein R is lower alkyl and:X.sub.n is 2,4-dichloro-5-methylsulfonylamino; 2-chloro-5-methylsulfonylamino; 4-chloro-5-methylsulfonylamino; 3-methylsulfonylamino; 4-chloro; 2-chloro; 3-nitro; 4-chloro-3-nitro; 2-chloro-5-nitro; 2,4-dichloro-5-nitro; 2-fluoro; 2-4-chloro; 2,4-dichloro; 4-alkoxy; or 4-alkoxy-2-fluoro;which comprises treating, in a tert-butanol medium, an aryl hydrazine of the formula ##STR2## sequentially with (i) a C.sub.1 -C.sub.3 aldehyde, (ii) a cyanate and weak organic acid, and (iii) a hypohalous acid, a salt thereof, or a halogen.Type: GrantFiled: December 28, 1994Date of Patent: August 8, 1995Assignee: FMC CorporationInventors: Allan R. Bailey, Marc Halfon, Eric W. Sortore
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Patent number: 5438149Abstract: An improved process for the difluoromethylation of a 1-phenyl-1H-1,2,4-triazol-5-one at the 4-position of the triazole ring with chlorodifluoromethane significantly reduces the amount of base required for the process, thereby reducing the environmental impact of the process by reducing the amount of by-product salts in the waste stream. The improvement comprises reacting the triazolinone with potassium carbonate in a solvent such as dimethylformamide, at a carbonate to triazolinone ratio in the range of about 0.55 to 1.0; reducing the water content of the reaction mixture to below about 2400 ppm by distillation; heating the reaction mixture in a sealed autoclave to 110.degree. to 180.degree. C., adding a 10 to 15 percent molar excess of chlorodifluoromethane, heating the reaction mixture at a temperature of 140.degree. to 210.degree. C. for 5 to 60 minutes, and recovering the difluoromethylated triazolinone.Type: GrantFiled: May 27, 1994Date of Patent: August 1, 1995Assignee: FMC CorporationInventors: Marc Halfon, Eric W. Sortore
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Patent number: 5428957Abstract: A device is disclosed for shutting off the flow of exhaust gases from the exhaust outlet of a diesel engine having a substantially vertical exhaust stack. The device is especially useful for stopping the flow from one of twin diesel stacks when a tractor or truck having twin stacks from a single manifold is undergoing maintenance in an indoor facility. The device permits an operator standing on the floor to position a resilient pad in sealing engagement with a stack outlet twelve feet or more above floor level and lock the pad into position and to remove the device, again from ground level, when maintenance has been completed and the engine shut down.Type: GrantFiled: March 11, 1994Date of Patent: July 4, 1995Inventor: Richard L. Keates
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Patent number: 5399543Abstract: The present application discloses herbicidal 3-[4-(phenylmethoxy)phenyl]-1-substituted-6-haloalkyluracils of the formula ##STR1## in which M is lower alkyl, lower 2-alkenyl, lower 2-alkynyl, lower alkoxymethyl or lower haloalkyl; T is lower haloalkyl; and U, V, W, X, Y, and Z are independently hydrogen, halogen, lower alkyl, lower haloalkyl, lower alkoxy, lower haloalkoxy, cyano or nitro; compositions thereof and use thereof to control unwanted plant growth.Type: GrantFiled: April 21, 1993Date of Patent: March 21, 1995Assignee: FMC CorporationInventor: George Theodoridis
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Patent number: 5391541Abstract: Herbicidal 3-(substituted-benzyl)-1-methyl-6-trifluoromethyluracils, compositions containing them, and methods of using them to control undesired plant growth, including use to control weeds in certain crops, are disclosed. The herbicidal compounds of the present invention are defined by the following generic structure: ##STR1## in which V is hydrogen or halogen; W is hydrogen, halogen, lower alkoxy, lower alkylaminocarbonyl, propargyloxy, or cyano; X is hydrogen or chlorine; and Y is hydrogen, halogen, cyano, lower alkylaminocarbonyl, or carboxy.Type: GrantFiled: April 8, 1994Date of Patent: February 21, 1995Assignee: FMC CorporationInventor: Marvin J. Konz
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Patent number: 5352672Abstract: Combinations of bifenthrin with azadirachtin-containing neem seed extracts are synergistic in controlling acarids, especially pyrethroid-resistant mites, over a wide range of azadirachtin to bifenthrin ratios.Type: GrantFiled: October 20, 1993Date of Patent: October 4, 1994Assignee: FMC CorporationInventors: Charles A. Staetz, H. Robinson Ertelt, Gert P. Volpp
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Patent number: H2007Abstract: Compounds of the following structure are disclosed as effective insecticides: in which: A and B are independently lower alkyl; U is lower alkylidene, lower alkenylidene, or CH—Z, where Z is hydrogen, lower alkyl, lower cycloalkyl, or phenyl; R is phenyl or a dibenzocyclo(C5-8)alkyl, each optionally substituted, or where R3 and R4 are independently selected from phenyl, optionally substituted with, halogen, lower alkyl, lower haloalkyl, lower alkoxy, lower haloalkoxy, lower alkenyl, or phenyl; R1 is selected from a variety of substituents, including 3-R2, where R2 is where D, E, and G are hydrogen, hydroxy, halogen, cyano, hydroxy, lower alkyl, lower haloalkyl, lower alkoxy, nitro, lower haloalkylsuffonyloxy, lower alkylcarboxylato, lower alkylcarbonylamino, lower alkylcarbonyl, lower alkoxycarbonyl, arylcarbonylamino; D and E taken together may form the group —O(CH2)O—; J is hydrogen or lower alkyl; m is 2 or 3, n is 1, 2, or 3; and halogType: GrantFiled: January 9, 1997Date of Patent: December 4, 2001Assignee: FMC CorporationInventors: Ian R. Silverman, Syed F. Ali, Daniel H. Cohen, John W. Lyga, Kirk A. Simmons, Thomas G. Cullen