Patents Represented by Attorney H. Robinson Ertelt
  • Patent number: 5756755
    Abstract: 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: Grant
    Filed: May 30, 1997
    Date of Patent: May 26, 1998
    Assignee: FMC Corporation
    Inventor: Jaidev S. Goudar
  • Patent number: 5753595
    Abstract: 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: Grant
    Filed: July 31, 1996
    Date of Patent: May 19, 1998
    Assignee: FMC Corporation
    Inventors: Scott D. Crawford, Lester L. Maravetz, George Theodoridis
  • Patent number: 5683966
    Abstract: 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: Grant
    Filed: June 10, 1996
    Date of Patent: November 4, 1997
    Assignee: FMC Corporation
    Inventor: Marvin J. Konz
  • Patent number: 5674810
    Abstract: 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: Grant
    Filed: September 5, 1995
    Date of Patent: October 7, 1997
    Assignee: FMC Corporation
    Inventor: George Theodoridis
  • Patent number: 5661108
    Abstract: 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: Grant
    Filed: January 18, 1995
    Date of Patent: August 26, 1997
    Assignee: FMC Corporation
    Inventors: Scott D. Crawford, Lester L. Maravetz, George Theodoridis
  • Patent number: 5639763
    Abstract: 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: Grant
    Filed: February 16, 1995
    Date of Patent: June 17, 1997
    Assignee: FMC Corporation
    Inventors: Ian R. Silverman, Daniel H. Cohen, John W. Lyga, Steven W. Szczepanski, Syed F. Ali
  • Patent number: 5621112
    Abstract: 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: Grant
    Filed: July 18, 1996
    Date of Patent: April 15, 1997
    Assignee: FMC Corporation
    Inventors: John W. Ager, Craig A. Polsz
  • Patent number: 5597780
    Abstract: 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: Grant
    Filed: September 21, 1995
    Date of Patent: January 28, 1997
    Assignee: FMC Corporation
    Inventors: Fui-Tseng H. Lee, Paul Nicholson
  • Patent number: 5569664
    Abstract: 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: Grant
    Filed: May 19, 1995
    Date of Patent: October 29, 1996
    Assignee: FMC Corporation
    Inventors: Ian R. Silverman, Daniel H. Cohen, John W. Lyga, Steven W. Szczepanski, Syed F. Ali
  • Patent number: 5521147
    Abstract: 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: Grant
    Filed: February 3, 1995
    Date of Patent: May 28, 1996
    Assignee: FMC Corporation
    Inventor: George Theodoridis
  • Patent number: 5472700
    Abstract: 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: Grant
    Filed: October 3, 1994
    Date of Patent: December 5, 1995
    Assignee: FMC Corporation
    Inventors: Charles A. Staetz, H. Robinson Ertelt, Gert P. Volpp
  • Patent number: 5468868
    Abstract: 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: Grant
    Filed: December 16, 1993
    Date of Patent: November 21, 1995
    Assignee: FMC Corporation
    Inventors: Marc Halfon, Craig A. Polsz, John H. Hoare
  • Patent number: 5441925
    Abstract: 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: Grant
    Filed: June 28, 1994
    Date of Patent: August 15, 1995
    Assignee: FMC Corporation
    Inventor: George Theodoridis
  • Patent number: 5440045
    Abstract: 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: Grant
    Filed: December 28, 1994
    Date of Patent: August 8, 1995
    Assignee: FMC Corporation
    Inventors: Allan R. Bailey, Marc Halfon, Eric W. Sortore
  • Patent number: 5438149
    Abstract: 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: Grant
    Filed: May 27, 1994
    Date of Patent: August 1, 1995
    Assignee: FMC Corporation
    Inventors: Marc Halfon, Eric W. Sortore
  • Patent number: 5428957
    Abstract: 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: Grant
    Filed: March 11, 1994
    Date of Patent: July 4, 1995
    Inventor: Richard L. Keates
  • Patent number: 5399543
    Abstract: 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: Grant
    Filed: April 21, 1993
    Date of Patent: March 21, 1995
    Assignee: FMC Corporation
    Inventor: George Theodoridis
  • Patent number: 5391541
    Abstract: 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: Grant
    Filed: April 8, 1994
    Date of Patent: February 21, 1995
    Assignee: FMC Corporation
    Inventor: Marvin J. Konz
  • Patent number: 5352672
    Abstract: 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: Grant
    Filed: October 20, 1993
    Date of Patent: October 4, 1994
    Assignee: FMC Corporation
    Inventors: Charles A. Staetz, H. Robinson Ertelt, Gert P. Volpp
  • Patent number: H2007
    Abstract: 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 halog
    Type: Grant
    Filed: January 9, 1997
    Date of Patent: December 4, 2001
    Assignee: FMC Corporation
    Inventors: Ian R. Silverman, Syed F. Ali, Daniel H. Cohen, John W. Lyga, Kirk A. Simmons, Thomas G. Cullen