Patents Represented by Attorney H. Robinson Ertelt
  • Patent number: 4997855
    Abstract: Nematodes and insects are controlled by application of vinyl fluorides of the formula ##STR1## where R is CH.sub.2 X--, CHX.sub.2 --, CX.sub.3 --, XCH.dbd.CH--, CH.sub.2 .dbd.CX-- or straight chain alkyl(C.sub.2 -C.sub.8);R.sup.1 is hydrogen, fluoro, chloro, bromo, CH.sub.2 Z--, CHZ.sub.2 -- or CZ.sub.3 --;R.sup.2, X and Z independently are hydrogen, fluoro, chloro or bromo; Y.sup.1, Y.sup.2, Y.sup.3, and Y.sup.4 independently are CH.sub.3 or any value of R.sup.2, X and Z; a is 0-12; n is 7-13; and n is greater than a.Particular species controlled are the root-knot, stunt, lesion, cyst and free-living nematodes, and the southern corn rootworm. The vinyl fluorides also have anthelmintic utility.
    Type: Grant
    Filed: September 15, 1988
    Date of Patent: March 5, 1991
    Assignee: FMC Corporation
    Inventor: Clinton J. Peake
  • Patent number: 4997970
    Abstract: Crystallizable pyrethroid isomers or enantiomer pairs are converted to more pesticidally active isomers by contacting a hydrocarbon slurry of the starting isomers with a base and a catalyst, the catalyst being substantially soluble in the slurry and selected from a quaternary ammonium compound, a quaternary phosphonium compound and a crown ether, agitating the slurry while maintaining a temperature effective for conversion, and recovering the resulting isomers. The tendency to form benzoin ester by-product is reduced by including in the slurry a weak base, an aldehyde scavenger such as a metabisulfite, and/or a tetraalkyl (C.sub.1 -C.sub.5) ammonium halide catalyst dissolved in an aprotic solvent such as an organic nitrile. The process typically is effective for enriching cypermethrin, cyfluthrin and (cyano (3-phenoxyphenyl)methyl 3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropanecarboxylate in the more active species.
    Type: Grant
    Filed: May 23, 1988
    Date of Patent: March 5, 1991
    Assignee: FMC Corporation
    Inventor: John W. Ager, Jr.
  • Patent number: 4994104
    Abstract: Disposed are herbicidal compounds of the formula ##STR1## wherein Q is a heterocyclic ring having 5 to 7 ring atoms and having the formula ##STR2## wherein Z is an oxygen or sulfur atom or a vinylene group, R.sup.4 and R.sup.5 are independently alkylene groups having 1 to 4 carbon atoms, and m and n are each independently an integer of 0 or 1; and in which R.sup.1 is H, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxyalkyl, alkoxyalkoxyalkyl, cycloalkyl, aralkyl, alkylthioalkyl, hydroxy, alkoxy, cyanoalkyl or alkylcarbonylalkyl; R.sup.2 and R.sup.3 are independently H or alkyl; and X is H, Cl or F. Also disclosed are herbicidal compositions and an herbicidal method of use for the herbicidal compounds.
    Type: Grant
    Filed: December 19, 1988
    Date of Patent: February 19, 1991
    Assignee: FMC Corporation
    Inventor: Jun H. Chang
  • Patent number: 4985065
    Abstract: Herbicidal compounds of the formula ##STR1## in which Q is ##STR2## M is CH or N; Z is O, S, NH or alkylamino;R.sup.3 is H, OH, alkoxy, alkenyloxy or alkynyloxy, alkoxyalkoxy, alkenyloxyalkoxy or alkynyloxyalkoxy, alkyl, substituted alkyl, OZ.sup.2 where Z.sup.2 is of a salt-forming group, amino, arylamino, alkylamino, alkenylamino, alkoxyamino, substituted alkoxyamino or --NHSO.sub.2 R.sup.5 where R.sup.5 is alkyl, haloalkyl or aryl;R.sup.1 is H, alkyl, halogen, haloalkyl, nitro, NH.sub.2, lower alkoxy, alkylthio or cyano;R.sup.2 is H, lower alkyl, lower alkenyl, lower alkynyl, halogen, CN, or COR.sup.3 ;R is H, lower alkyl, halogen, or lower alkoxy or R and R.sup.2 together constitute a double bond;R.sup.4 is H, halogen, lower alkyl, lower alkenyl, or lower alkynyl;R.sup.7 is H or lower alkyl; andR.sup.a, X and Y are so chosen that when Q is methoxy or propargyloxy, instead of Q having the formula given above, the compound is a herbicide.
    Type: Grant
    Filed: May 10, 1989
    Date of Patent: January 15, 1991
    Assignee: FMC Corporation
    Inventor: George Theodoridis
  • Patent number: 4982012
    Abstract: 2-Methallyloxyphenol is produced selectively in good yield, high purity and without having to separate and recycle large amounts of catechol, in the reaction of methallyl chloride with catechol, by forming a substantially non-aqueous mixture of an alkali metal catecholate and a molar excess of methallyl chloride perferably in a polar organic solvent in which the methallyl chloride is substantially insoluble, agitating the mixture to produce a two-phase system comprising an organic first phase containing product 2-methallyloxyphenol dissolved in methallyl chloride and a polar second phase containing unreacted catecholate, and recovering product 2-methallyloxyphenol from the first plase. The presence of a quaternary ammonium or phosphonium catalyst in the reaction mixture further reduces undesired ring-alkylated by-products.
    Type: Grant
    Filed: December 18, 1987
    Date of Patent: January 1, 1991
    Assignee: FMC Corporation
    Inventor: John W. Ager, Jr.
  • Patent number: 4980480
    Abstract: Process for the production of an aryl triazolinone of the formula: ##STR1## in which R is halogen, alkyl, haloalkyl, cyanoalkyl, arylalkyl, alkoxyalkyl, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl or phenyl,each X is independently, H, halogen, lower alkyl, lower alkoxy, --NO.sub.2, --OH, --NHSO.sub.2 R', --N(SO.sub.2 R').sub.2 or --N(R')SO.sub.2 R' where R' is lower alkyl, and n is a number from 1 to 3,by treating an aryl triazolidinone of the formula: ##STR2## with a halogen of the group consisting of chlorine, bromine and iodine, or a hypohalous acid of said halogen or a salt of said acid.
    Type: Grant
    Filed: September 8, 1989
    Date of Patent: December 25, 1990
    Assignee: FMC Corporation
    Inventors: George Theodoridis, John W. Lyga
  • Patent number: 4975451
    Abstract: Compounds of the formula ##STR1## in which Ar is substituted or unsubstituted phenyl, naphthyl, or thienyl; and Ar.sup.1 is 3-phenoxyphenyl, 4-fluoro-3-phenoxyphenyl, 2-methyl[1-1'-biphenyl]-3-yl, or 6-phenoxy-2-pyridyl, exhibit pyrethroid-like insecticidal and acaricidal activity and are relatively nontoxic to fish.
    Type: Grant
    Filed: March 2, 1989
    Date of Patent: December 4, 1990
    Assignee: FMC Corporation
    Inventors: Thomas G. Cullen, Scott McN. Sieburth, Gary A. Meier, John F. Engel, Leslie W. Stratton, Alan W. Fritz
  • Patent number: 4960884
    Abstract: Pesticidal mono-, di-, and tri-2-fluoroethyl ethers of the formula R.sup.1 R.sup.2.sub.m Ar(OCH.sub.2 CH.sub.2 F).sub.n, compositions thereof and their insecticidal, acaricidal and nematicidal uses are described and claimed.
    Type: Grant
    Filed: August 28, 1989
    Date of Patent: October 2, 1990
    Assignee: FMC Corporation
    Inventors: David M. Roush, Donald A. Shaw, Michael L. Jones, Jun H. Chang
  • Patent number: 4954159
    Abstract: The present application discloses herbicidal phosphorylaminophenyltetrahydrophthalimides, compositions of them, methods of preparing them, and methods for controlling undesired plant growth by preemergence or postemergence application of the herbicidal compositions to the locus where control is desired. The herbicidal compounds are compounds of the formula ##STR1## in which X and Y are independently F, Cl, or Br; R.sup.1 is selected from lower alkyl, lower haloalkyl, cycloalkyl of 3 to 7 ring carbon atoms, lower alkenyl, lower haloalkenyl, lower alkynyl, lower haloalkynyl, and benzyl which is unsubstituted or substituted on the phenyl ring with one or more substituents selected from halogen, lower alkyl, lower alkoxy, lower alkoxycarbonyl, cyano, and nitro; and R.sup.2 is independently selected from among --OR.sup.1 or is hydroxy, amino, lower alkylamino, or lower dialkylamino; R.sup.3 is H, lower alkyl, or lower alkenyl; or a base addition salt of the compound as defined above in which R.sup.2 is hydroxy.
    Type: Grant
    Filed: March 17, 1989
    Date of Patent: September 4, 1990
    Assignee: FMC Corporation
    Inventor: George Theodoridis
  • Patent number: 4952580
    Abstract: Polyhaloalkene compounds of the formula: ##STR1## wherein X is sulfur, oxygen, or nitrogen, Y.sup.1 and Y.sup.2 are fluorine, Z is hydrogen or the same as Y.sup.1 and Y.sup.2, and n is 1-4; provided that:(A) when X is sulfur, Z is fluorine and R is thienyl or substituted thienyl, thianaphthyl or substituted thianaphthyl, thiazolinyl or substituted thiazolinyl, oxadiazolyl or substituted oxadiazolyl, 3,4,4-trifluoro-3-butenyloxycarbonylmethyl, thiadiazolyl substituted by halogen or R.sup.2 S, wherein R.sup.2 is 3,4,4-trifluoro-3-butenyl or R.sup.2 is phenylmethyl or phenylthiomethyl each optionally substituted by halogen or nitro; or R is thiadiazolyl substituted by R.sup.3, wherein R.sup.3 is substituted aryl, arylalkyl, aryloxyalkyl, alkylthio, haloalkylthio, haloarylthio, cyanoalkylthio, arylalkylthio, aryloxyalkylthio, arylthioalkylthio, heterocycloalkylthio, alkenylthio, haloalkenylthio, halocycloalkylalkenylthio, wherein said aryl or heterocyclic groups of R.sup.
    Type: Grant
    Filed: November 9, 1988
    Date of Patent: August 28, 1990
    Assignee: FMC Corporation
    Inventors: Anthony J. Martinez, Thomas G. Cullen
  • Patent number: 4950666
    Abstract: The present invention discloses compounds of the formula ##STR1## in which R is a 1,1-difluoroalkyl group or a 1,1-difluoroethenyl group having an even numbered carbon chain length of from 4 to 22 carbon atoms, pesticidal compositions thereof; and their use to control plant pests such as insects, acarids, and nematodes.
    Type: Grant
    Filed: March 30, 1989
    Date of Patent: August 21, 1990
    Assignee: FMC Corporation
    Inventors: Clinton J. Peake, Thomas G. Cullen, Anthony J. Martinez
  • Patent number: 4939165
    Abstract: Bithienyl compounds of the following structural formula are phototoxic insecticides and acaricides: ##STR1## wherein R.sub.1 is selected from hydrogen, halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, haloalkenoxy, phenyl, phenoxy, nitro, alkylsulfinyl, alkylsulfonyl, and alkylthio provided R.sub.4 is other than hydrogen;R.sub.2 is selected from hydrogen and halogen, or R.sub.1 and R.sub.2 at adjacent positions are joined to form C.sub.4 H.sub.4 ;R.sub.3 is selected from hydrogen, alkyl, thienyl, and phenyl optionally substituted with alkyl, alkoxy, or 1-2 halogen; andR.sub.4 is selected from hydrogen, halogen, alkyl, haloalkyl, alkoxy, alkylthio, alkylsulfinyl, haloalkenylthio, formyl, alkylcarbonyl, alkoxycarbonyl, phenylcarbonyl, dialkylphosphono, and nitro.
    Type: Grant
    Filed: February 28, 1989
    Date of Patent: July 3, 1990
    Inventors: Susan E. Burkart, Richard B. Phillips, David M. Roush
  • Patent number: 4932996
    Abstract: The present application discloses herbicidal phosphorylaminophenyltetrazolinones, compositions of them, methods of preparing them, and methods for controlling undesired plant growth by preemergence or postemergence application of the herbicidal compositions to the locus where control is desired. The herbicidal compounds are compounds of the formula ##STR1## in which X and Y are independently F, Cl, or Br; R is lower alkyl or lower haloalky; R.sup.1 is selected from lower alkyl, lower haloalkyl, cycloalkyl of 3 to 7 ring carbon atoms, lower alkenyl, lower haloalkenyl, lower alkynyl, lower haloalkynyl, and benzyl which is unsubstituted or substituted on the phenyl ring with one or more substituents selected from halogen, lower alkyl, lower alkoxy, lower alkoxycarbonyl, cyano, and nitro; R.sup.2 is independently selected from among --OR.sup.1 or is hydroxy, amino, lower alkylamino, or lower dialkylamino; R.sup.
    Type: Grant
    Filed: March 7, 1989
    Date of Patent: June 12, 1990
    Assignee: FMC Corporation
    Inventor: George Theodoridis
  • Patent number: 4913723
    Abstract: Disclosed are herbicidal compounds, compositions containing them, and a method of use for the compositions in controlling undesired plant growth. The herbicidal compounds are compounds of the formula ##STR1## in which W is S or O and Z-Ph is a substituted phenyl group in which Z is -C(R).dbd.Q; R is H, lower alkyl, or aryl; Q is NR' or oxygen; R' is alkoxy, hydroxy, alkenyloxy, alkynyloxy, alkylcarbonyloxy, arylcarbonloxy, trialkylsilyloxy, arylalkoxy, aryl, alkyl, cycloalkyl, or a group of the formula --SO.sub.2 R", --OCO.sub.2 R", OC(O)NHR", or --CH.sub.2 CO.sub.2 R"; and R" is lower alkyl or aryl. The phenyl moiety Ph is advantageously multisubstituted.
    Type: Grant
    Filed: August 8, 1988
    Date of Patent: April 3, 1990
    Assignee: FMC Corporation
    Inventor: Jun H. Chang
  • Patent number: 4913724
    Abstract: A herbicidal compound which is a Q-substituted 1-phenyl-4-substituted-1,4-dihydro-5H-tetrazol-5-one in which the Q-substituent is bonded to the ring-carbon atom at the 5-position of the phenyl group and in which:Q is --CH(R.sup.2)C(R.sup.3) (R.sup.4)Q' or --C(R.sup.2).dbd.C(R.sup.4)Q';R.sup.2 and R.sup.3 are each, independently, hydrogen, alkyl, or halogen;R.sup.4 is hydrogen or lower alkyl;Q' is COOH, COOZ, COOR.sup.5, CON(R.sup.6) (R.sup.7), CN, CHO or C(O)R.sup.5 ;Z is a salt-forming cation;R.sup.5 is alkyl, cycloalkyl or aralkyl;each of R.sup.6 and R.sup.7 is, independently, hydrogen, alkyl, cycloalkyl, alkenyl, alkynyl, alkoxy, phenyl, benzyl or SO.sub.2 R.sup.8, or is one of said radicals substituted by halogen, alkyl or cyano, R.sup.8 being the same as R.sup.6 other than hydrogen or SO.sub.2 R.sup.8 ; said compound being one whose 5-Methoxy Analog and 5-Propargyloxy Analog are herbicides.
    Type: Grant
    Filed: April 14, 1989
    Date of Patent: April 3, 1990
    Assignee: FMC Corporation
    Inventor: Kathleen M. Poss
  • Patent number: 4909829
    Abstract: Quinolinone compounds of the formula ##STR1## in which R.sup.2 is H, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, alkoxyalkyl, alkoxyalkoxyalkyl, cycloalkyl, alkylthioalkyl, aralkyl, cyanoalkyl, alkoxycarbonylalkyl, hydroxy, or alkoxy; X is H, halogen, alkyl, or haloalkyl; Y is H, halogen, alkyl, haloalkyl, alkoxycarbonyl, cyano, or nitro; Z is H, halogen, alkyl, haloalkyl, alkoxy, alkenyl, alkynyl, haloalkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkoxycarbonyl, cyano, or nitro; and R.sup.1 is alkyl, alkenyl, alkynyl, haloalkyl, alkoxyalkyl, or haloalkoxyalkyl; and the corresponding 3,4-dihydroquinolinone compounds as herbicides.
    Type: Grant
    Filed: December 29, 1987
    Date of Patent: March 20, 1990
    Assignee: FMC Corporation
    Inventor: George Theodoridis
  • Patent number: 4909831
    Abstract: Crops such as corn and other gramineous plants are protected from phytotoxic injury by the herbicide, 1-[2,4-dichloro-5-(N-methylsulfonylamino)phyenyl]-3-methyl-4-difluoromethy l-.DELTA..sup.2 -1,2,4-triazolin-5-one, by coating the seeds of the crops, prior to planting, with a nonphytotoxic quantity of 1,8-naphthalic anhydride. The crops are safened against phytotoxic injury when the herbicide is applied pre-emergent, post-emergent or in a pre-plant incorporated manner.
    Type: Grant
    Filed: February 6, 1989
    Date of Patent: March 20, 1990
    Assignee: FMC Corporation
    Inventors: David W. Keifer, John M. Tymonko
  • Patent number: 4908357
    Abstract: Thiazole compounds of the following structural formula are photodynamic insecticides and acaricides, as well as nematicides: ##STR1##
    Type: Grant
    Filed: September 22, 1988
    Date of Patent: March 13, 1990
    Assignee: FMC Corporation
    Inventor: Kathryn A. Lutomski
  • Patent number: 4906284
    Abstract: Herbicidal compound of the formula ##STR1## whose Difluoromethyl Analog or Methyl Analog is a herbicide (the Difluoromethyl Analog being identical except that it has a --CHF.sub.2 group instead of the --CH.sub.2 CH.sub.2 CH.sub.2 F group of said compound and the Methyl Analog being identical except that it has a --CH.sub.3 group instead of the --CH.sub.2 CH.sub.2 CH.sub.2 F group of said compound), Ar being an aryl radical.
    Type: Grant
    Filed: August 23, 1988
    Date of Patent: March 6, 1990
    Assignee: FMC Corporation
    Inventor: George Theodoridis
  • Patent number: H806
    Abstract: Synergistic herbicidal effect is obtained in the application of clomazone together with reduction in the rate of clomazone, by combining clomazone with a photosystem II (PS-II) inhibiting herbicide such as atrazine, cyanazine or linuron. Crops such as corn and other gramineous plants are rendered more tolerant to clomazone and to combinations of clomazone with a PS-II inhibiting herbicide by treatment of the crops or crop seeds with a safener such as 1,8-naphthalic anhydride.
    Type: Grant
    Filed: July 16, 1987
    Date of Patent: August 7, 1990
    Assignee: FMC Corporation
    Inventors: David W. Keifer, John M. Tymonko, Earl D. Felix, William A. Van Saun