Patents Represented by Attorney H. Robinson Ertelt

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  • 4-Substituted-2-indanols
    Patent number: 4346251
    Abstract: Novel compounds of the formula ##STR1## are disclosed in which R.sup.1 is a phenyl, phenoxy, phenylthio, benzyl or heterocyclic radical which may be substituted, and R.sup.2 is hydrogen. The compounds are intermediates of cyclopropanecarboxylate and related insecticides.
    Type: Grant
    Filed: October 31, 1980
    Date of Patent: August 24, 1982
    Assignee: FMC Corporation
    Inventor: John F. Engel
  • Process for producing cis-3-(2,2-disubstituted-ethenyl)-2,2-dimethylcyclopropanecarboxylic acid and intermediates
    Patent number: 4344884
    Abstract: Novel intermediates for production of insecticidal cis-3-(2,2-disubstituted-ethenyl)-2,2-dimethylcyclopropanecarboxylates, processes for preparing the intermediates, and processes for preparing the final product insecticides via a novel bicyclic lactone intermediate are described and exemplified.
    Type: Grant
    Filed: June 30, 1980
    Date of Patent: August 17, 1982
    Assignee: FMC Corporation
    Inventors: Kiyoshi Kondo, Toshiyuki Takashima, Minoru Suda
  • Processes for producing pyrethroid insecticide intermediates
    Patent number: 4342694
    Abstract: Processes for producing a (1.alpha., 4.alpha., 5.alpha.)-6,6-dimethyl-4-halo-substituted-methyl-3-oxabicyclo[3.1.0]hexan- 2-one and its novel intermediates from known and inexpensive starting materials are described and exemplified. The halomethyl bicyclic lactone is a useful intermediate for the preparation of insecticidal cis-3-(2,2-dihaloethenyl)-2,2-dimethylcyclopropanecarboxylates or cis-3-(2-halo-2-trihalomethylethenyl)-2,2-dimethylcyclopropanecarboxylates .
    Type: Grant
    Filed: June 23, 1980
    Date of Patent: August 3, 1982
    Assignee: FMC Corporation
    Inventors: Kiyoshi Kondo, Toshiyuki Takashima, Minoru Suda
  • Control of acarids with biphenylmethyl perhaloalkylvinylcyclopropanecarboxylates
    Patent number: 4341796
    Abstract: Acaricidal use is disclosed and exemplified for compounds of the general formula ##STR1## in which one of Y and Z is a trifluoromethyl group, the other is a halogen atom, R.sup.1 is lower alkyl or halogen, R.sup.2 is hydrogen, halogen, or lower alkyl, or R.sup.1 and R.sup.2 are both hydrogen.
    Type: Grant
    Filed: October 8, 1980
    Date of Patent: July 27, 1982
    Assignee: FMC Corporation
    Inventor: John F. Engel
  • 3-(Pyrrol-1-yl)phenylmethyl esters and intermediates
    Patent number: 4339457
    Abstract: 3-(Pyrrol-1-yl)phenylmethyl esters and intermediates having the general formula ##STR1## the use of the esters as pesticides, compositions thereof and a process for preparation are disclosed and exemplified.
    Type: Grant
    Filed: October 20, 1980
    Date of Patent: July 13, 1982
    Assignee: FMC Corporation
    Inventors: Ernest L. Plummer, Raymond M. Palmere
  • Haloethenylthienylethanones for systemic nematode control
    Patent number: 4335137
    Abstract: A method is disclosed for systemic control of nematodes in agricultural crops which comprises applying to the above ground portions of the plants comprising said agricultural crop of a nematicidal amount of a compound of the formula ##STR1## wherein X.sup.1 and X.sup.2 are each halogen atoms selected from bromine, chlorine and fluorine, the same or different. Preparation, formulation and nematicidal utility for the compounds are described and exemplified.
    Type: Grant
    Filed: March 17, 1980
    Date of Patent: June 15, 1982
    Assignee: FMC Corporation
    Inventor: Donald R. James
  • Insecticidal pyrethroid enantiomer pair
    Patent number: 4335252
    Abstract: An insecticidal enantiomer pair consisting essentially of a substantially equimolar mixture of S-4-phenyl-2-indanyl 1R, cis-3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropanecarbox ylate and R-4-phenyl-2-indanyl 1S,cis-3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropanecar boxylate, its preparation by liquid chromatography, and its utility as an insecticide are described and exemplified.
    Type: Grant
    Filed: December 31, 1980
    Date of Patent: June 15, 1982
    Assignee: FMC Corporation
    Inventor: John F. Engel
  • (+)-4-Substituted-2-indanol insecticidal ester derivatives
    Patent number: 4333950
    Abstract: Novel compounds of the formula ##STR1## are disclosed in which R.sup.1 is a phenyl, phenoxy, phenylthio, benzyl or heterocyclic radical which may be substituted, R.sup.2 is hydrogen, a substituted-vinylcyclopropanecarbonyl group, a tetramethylcyclopropanecarbonyl group, or a 1-(substituted-phenyl)-2-methylpropylcarbonyl group, and the isomer of S configuration at C-2 of the indanyl ring is present in an enantiomeric excess over the isomer of R configuration. Also disclosed is a method for preparing the optically active alcohols. The compounds wherein R.sup.2 is other than hydrogen are insecticides.
    Type: Grant
    Filed: December 31, 1980
    Date of Patent: June 8, 1982
    Assignee: FMC Corporation
    Inventor: John F. Engel
  • Insecticidal perhaloalkylvinylcyclopropanecarboxylates
    Patent number: 4332815
    Abstract: Perhaloalkylvinylcyclopropanecarboxylates having the general formula ##STR1## are disclosed wherein one of Y and Z is a perhaloalkyl group. Compounds in which R is hydroxy, halogen or lower alkoxy are novel intermediates for preparation of insecticidal esters in which R is --OR.sup.1 where R.sup.1 is a wide variety of alcohol residues. The insecticidal efficacy and preparation of the compounds and intermediates therefor are described and exemplified.
    Type: Grant
    Filed: July 1, 1980
    Date of Patent: June 1, 1982
    Assignee: FMC Corporation
    Inventor: John F. Engel
  • Insecticidal [1,1'-biphenyl]-3-ylmethyl esters
    Patent number: 4329518
    Abstract: [1,1'-Biphenyl]-3-ylmethyl pyrethroid esters, as well as processes, uses, and intermediates thereto, are disclosed. The [1,1'-biphenyl]-3-ylmethyl pyrethroid esters control a broad spectrum of insects as well as acarids.
    Type: Grant
    Filed: October 2, 1980
    Date of Patent: May 11, 1982
    Assignee: FMC Corporation
    Inventor: Ernest L. Plummer
  • Trialkylamine/sulfur dioxide catalyzed sulfenylation of carbamates
    Patent number: 4329293
    Abstract: An improved process is disclosed for sulfenylating carbamates in the presence of a solvent and acid acceptor, in which the reaction between a carbamate and a sulfenyl halide is conducted in the presence of a catalytic amount of a complex of a lower alkylamine and sulfur dioxide. Several methods for preparing and utilizing the complex in the reaction are disclosed and exemplified.
    Type: Grant
    Filed: October 31, 1980
    Date of Patent: May 11, 1982
    Assignee: FMC Corporation
    Inventors: John W. Ager, Maurice J. C. Harding, Charles E. Hatch, III
  • Plant regulator
    Patent number: 4309566
    Abstract: Novel substituted benzoyloxy compounds exhibit plant regulator activity, retarding or stimulating the growth of a variety of broadleaved plants, while leaving grasses unaffected. The preparation and plant regulator activity of the compounds is exemplified.
    Type: Grant
    Filed: November 5, 1979
    Date of Patent: January 5, 1982
    Assignee: FMC Corporation
    Inventors: Marvin J. Konz, Norman E. Krog
  • Crystalline, insecticidal pyrethroid
    Patent number: 4308279
    Abstract: A crystalline, optically inactive compound, each crystal comprising an equimolar mixture of the isomers (S)-(cyano)(3-phenoxyphenyl)methyl (1R,cis)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate and (R)-(cyano)-(3-phenoxyphenyl)methyl (1S,cis)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate, its preparation by a cyclic crystallization/equilibration process, and its utility as an insecticide are described and exemplified.
    Type: Grant
    Filed: June 30, 1980
    Date of Patent: December 29, 1981
    Assignee: FMC Corporation
    Inventor: Leland A. Smeltz
  • Herbicidal isoxazolidine-3,5-diones
    Patent number: 4302238
    Abstract: 2-Substituted isoxazolidine-3,5-diones and isoxazolidine-3-one-5-thiones exhibit herbicidal activity, controlling effectively the growth of a wide spectrum of grassy and broad-leaved plant species. The preparation and herbicidal activity of the compounds is exemplified.
    Type: Grant
    Filed: August 20, 1980
    Date of Patent: November 24, 1981
    Assignee: FMC Corporation
    Inventor: Marvin J. Konz
  • 4-Substituted-2-indanol insecticidal ester derivatives
    Patent number: 4263319
    Abstract: Novel compounds of the formula ##STR1## are disclosed in which R.sup.1 is a phenyl, phenoxy, phenylthio, benzyl or heterocyclic radical which may be substituted, and R.sup.2 is hydrogen, a substituted-vinylcyclopropanecarbonyl group, a tetramethylcyclopropanecarbonyl group, or a 1-(substituted-phenyl)-2-methylpropylcarbonyl group. The compounds wherein R.sup.2 is other than hydrogen are insecticides.
    Type: Grant
    Filed: May 24, 1979
    Date of Patent: April 21, 1981
    Assignee: FMC Corporation
    Inventor: John F. Engel
  • Process for preparation of a crystalline insecticidal pyrethroid enantiomer pair
    Patent number: 4261921
    Abstract: A crystalline, optically inactive compound comprising an equimolar mixture of the isomers (S)-(cyano) (3-phenoxyphenyl)methyl (1R,cis)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate and (R)-(cyano)-(3-phenoxyphenyl)-methyl (1S,cis)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate, its preparation by a cyclic crystallization/equilibration process, and its utility as an insecticide are described and exemplified.
    Type: Grant
    Filed: June 6, 1979
    Date of Patent: April 14, 1981
    Assignee: FMC Corporation
    Inventor: Leland A. Smeltz
  • Method of reducing the contents of haloethynyl-containing impurities in synthetic dihaloethenyl pyrethroid insecticides or intermediates by reaction with phosphites
    Patent number: 4250326
    Abstract: A method of reducing the content of a haloethynyl-containing impurity in a synthetic dihaloethenylcyclopropanecarboxylate by treatment with a phosphite under condition allowing the haloethynyl-containing impurity and phosphite to chemically interact, and thereafter recovering the dihaloethenylcyclopropanecarboxylate from the reaction mixture is disclosed.
    Type: Grant
    Filed: October 22, 1979
    Date of Patent: February 10, 1981
    Assignee: FMC Corporation
    Inventor: Morris L. Fishman
  • Insecticidal perhaloalkylvinylcyclopropanecarboxylates
    Patent number: 4243677
    Abstract: Perhaloalkylvinylcyclopropanecarboxylates having the general formula ##STR1## are disclosed wherein one of Y and Z is a perhaloalkyl group. Compounds in which R is hydroxy, halogen or lower alkoxy are novel intermediates for preparation of insecticidal esters in which R is --OR.sup.1 where R.sup.1 is a wide variety of alcohol residues. The insecticidal efficacy and preparation of the compounds and intermediates therefor are described and exemplified.
    Type: Grant
    Filed: July 30, 1979
    Date of Patent: January 6, 1981
    Assignee: FMC Corporation
    Inventor: John F. Engel
  • Insecticidal esters of certain substituted 7-oxabicyclo[2.2.1]2,5-heptadiene methanols
    Patent number: 4239773
    Abstract: Novel alcohols of the formula ##STR1## where R.sup.5 is hydrogen are useful intermediates in the preparation of insecticidal esters. The insecticides are compounds in which R.sup.5 is a substituted-vinylcyclopropanecarbonyl group, a tetramethylcyclopropanecarbonyl group, or a chlorophenyl-2-methylpropylcarbonyl group.
    Type: Grant
    Filed: December 17, 1979
    Date of Patent: December 16, 1980
    Assignee: FMC Corporation
    Inventor: William A. Van Saun, Jr.
  • Insecticidal biphenylmethyl perhaloalkylvinylcyclopropanecarboxylates
    Patent number: 4238505
    Abstract: Perhaloalkylvinylcyclopropanecarboxylates having the general formula: ##STR1## wherein one of Y and Z is a perhaloalkyl group and the other is hydrogen, halogen, or lower alkyl; and R is --OR.sup.1 where R.sup.1 is an optionally substituted biphenylmethyl radical are disclosed. The insecticidal efficacy and preparation of the compounds and their intermediates are described and exemplified.
    Type: Grant
    Filed: June 25, 1979
    Date of Patent: December 9, 1980
    Assignee: FMC Corporation
    Inventor: John F. Engel