Patents Represented by Attorney Norman L. Craig
  • 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: 5407808
    Abstract: Disclosed is a method and a pharmaceutical composition for killing mammalian tumor cells by subjecting the cells to light in the presence of a light-activatable tetrapyrrole, in which the improvement comprises treating the cells with a compound which inhibits the enzymatic conversion of protoporphyrinogen to protoporphyrin IX by protoporphyrinogen oxidase in the cells thereby causing a buildup of protoporphyrin IX in the cells. Also disclosed is a method for the production of protoporphyrin IX which comprises growing eukaryotic microalgae in the presence of a protoporphyrinogen oxidase inhibitor.
    Type: Grant
    Filed: December 20, 1993
    Date of Patent: April 18, 1995
    Assignee: FMC Corporation
    Inventors: Blaik P. Halling, Debra A. Yuhas
  • Patent number: 5322702
    Abstract: There is disclosed an opacifying material of micrgranular protein opacifying material having a mean particle size distribution of 0.1 microns to 10 microns with fewer than 20% of the total number of particles exceeding 10 microns, which is prepared by wet milling denatured whey protein isolate.
    Type: Grant
    Filed: June 15, 1992
    Date of Patent: June 21, 1994
    Assignee: FMC Corporation
    Inventors: Edward Selinger, Thomas R. Laaman
  • Patent number: 5298502
    Abstract: Disclosed is a method and a pharmaceutical composition for killing mammalian tumor cells by subjecting said cells to light in the presence of a light-activatable tetrapyrrole, in which the improvement comprises treating said cells with a compound which inhibits the enzymatic conversion of protoporphyrinogen to protoporphyrin IX by protoporphyrinogen oxidase in said cells thereby causing a buildup of protoporphyrin IX in said cells. Also disclosed is a method for the production of protoporphyrin IX which comprises growing eukaryotic microalgae in the presence of a protoporphyrinogen oxidase inhibitor.
    Type: Grant
    Filed: December 23, 1991
    Date of Patent: March 29, 1994
    Assignee: FMC Corporation
    Inventors: Blaik P. Halling, Debra A. Witkowski
  • Patent number: 5256793
    Abstract: A process for the production of aryl triazolinones of the formula ##STR1## wherein R is lower alkyl;X is independently halogen, lower alkyl, nitro, hydroxy, NHSO.sub.2 R', --N(SO.sub.2 R').sub.2, --N(R'(SO.sub.2 R' where R' is lower alkyl, and n is an integer from 0 to 3;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 hypochlorite, a salt thereof, or a halogen.
    Type: Grant
    Filed: May 13, 1992
    Date of Patent: October 26, 1993
    Assignee: FMC Corporation
    Inventors: Allan R. Bailey, Marc Halfon, Eric W. Sortore
  • Patent number: 5223536
    Abstract: The 1,4-diaryl-1-cyclopropyl-4-substituted butane pesticides of the following formula are effective as insecticides and acaricides: ##STR1## in which X and Y are independently hydrogen, halogen, alkyl, alkoxy, cycloalkylalkoxy, alkylcarbonyl, alkoxycarbonyl, haloalkyl, haloalkoxy, alkylthio, haloalkylthio, alkylsulfinyl, alkylsulfonyl, trialkylamino, nitro, or cyano; or X and Y together are --OCH.sub.2 O-- or --OCF.sub.2 O-- bridging the 2-3 or 3-4 positions of the phenyl ring; Ar is 3-phenoxyphenyl, 4-fluoro-3-phenoxyphenyl, 6-phenoxypyridin-2-yl, or 2-methyl(1,1'-biphenyl)-3-yl;R is cyano, methyl, trifluoromethyl, alkenyl, alkynyl, or halogen.
    Type: Grant
    Filed: July 23, 1991
    Date of Patent: June 29, 1993
    Assignee: FMC Corporation
    Inventors: Thomas G. Cullen, Scott McN. Sieburth, Gary A. Meier, John F. Engel
  • Patent number: 5217520
    Abstract: A herbicidal compound which is a Q-substituted 1-phenyl-4,5-dihydro-1,2,4-triazol-5(1H)-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 --CH.dbd.C(R.sup.4)Q';R.sup.2 and R.sup.3 are each, independently, H or halogen;R.sup.4 is H 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 group;R.sup.5 is alkyl, alkoxycarbonylalkyl, cycloalkyl or aralkyl;each of R.sup.6 and R.sup.7 is, independently, a radical which is alkyl, cycloalkyl, alkenyl, alkynyl, alkoxy, phenyl, benzyl or SO.sub.2 R.sup.6 or is one of said radicals substituted by halogen, alkyl or cyano; said compound being one whose 5-Methoxy Analogs and 5-Propargyloxy Analog are herbicides.
    Type: Grant
    Filed: March 16, 1992
    Date of Patent: June 8, 1993
    Assignee: FMC Corporation
    Inventor: Kathleen M. Poss
  • Patent number: 5208212
    Abstract: This invention relates to compositions comprising 1-aryl-4,5-dihydro-1,2,4-triazol-5(1H)-ones (triazolinones) in combination with the herbicide (2,4-dichlorophenoxy)acetic acid (2,4-D), or like substituted phenoxyalkanoic acids, or esters, or alkali metal or ammonium salts thereof; or with certain herbicidal sulfonylureas, or mixtures of these classes of compounds, to provide herbicidal compositions which are highly effective against a broad array of crop weeds, particularly broadleaf weeds, in crops such as wheat.
    Type: Grant
    Filed: October 30, 1992
    Date of Patent: May 4, 1993
    Assignee: FMC Corporation
    Inventors: Kathleen M. Poss, Frederick W. Hotzman, Jacques Meyer
  • Patent number: 5149357
    Abstract: Compound of the formula ##STR1## in which A is O, S, or NR.sup.3 ; G is CH or N; R and R.sup.1 are independently alkyl, alkoxy, haloalkoxy or alkylamino; R.sup.2 is phenyl, substituted phenyl, alkyl, cycloalkyl, haloalkyl or --CH.sub.2 [(R.sup.4)C(R.sup.5).sub.n --Z; R.sup.3 and R.sup.7 are, independently, hydrogen, alkyl, --C(O)NH.sub.2 or --C(O)alkyl; R.sup.4 and R.sup.5 are independently hydrogen, alkyl, or halogen; R.sup.6 is halogen, alkyl, alkoxy, haloalkoxy, NO.sub.2, amino, alkyl substituted amino, or acyl substituted amino; n is 0 to 5; Z is cyano, amino, alkylamino, dialkylamino, --NHCO.sub.2 alkyl, alkoxy, alkylthio, alkylsulfonyl, alkenyl, alkynyl, phenyl or substituted phenyl; and Q is hydrogen, halogen, alkyl, alkoxy, haloalkoxy, nitro, amino, haloalkyl, alkythio, alkylsulfonyl, phenyl, substituted phenyl or phenoxy; or a 5 or 6 membered aromatic heterocycle having the formula ##STR2## in which "m" is 0 or 1; A' is O, S, or NR.sup.
    Type: Grant
    Filed: June 19, 1990
    Date of Patent: September 22, 1992
    Assignee: FMC Corporation
    Inventors: John A. Dixson, Natesan Murugesan, Keith D. Barnes
  • Patent number: 5125958
    Abstract: A herbicidal compound which is a Q-substituted 1-phenyl-4,5-dihydro-1,2,4-triazol-5(1H)-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 --CH.dbd.C(R.sup.4)Q';R.sup.2 and R.sup.3 are each, independently, H or halogen;R.sup.4 is H 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 group;R.sup.5 is alkyl, alkoxycarbonylalkyl, cycloalkyl or aralkyl;each of R.sup.6 and R.sup.7 is, independently, a radical which is alkyl, cycloalkyl, alkenyl, alkynyl, alkoxy, phenyl, benzyl or SO.sub.2 R.sup.6 or is one of said radicals substituted by halogen, alkyl or cyano;said compound being one whose 5-Methoxy Analogs and 5-Propargyloxy Analog are herbicides.
    Type: Grant
    Filed: March 5, 1991
    Date of Patent: June 30, 1992
    Assignee: FMC Corporation
    Inventor: Kathleen M. Poss
  • Patent number: 5105012
    Abstract: There is provided an improved process for the reduction of optionally substituted dinitrobenzenes to the corresponding nitroanilines with high yields which comprises contacting the dinitrobenzene with hydrogen in an acidic medium in the presence of a catalytic amount of a combination of a noble metal hydrogenation catalyst, and iron or an iron salt. Isomer specific reductions may be achieved with those compounds containing suitable directing substituents.The 2-halo-5-nitroanilines which may be produced in this process may be converted via a multi-step synthesis to useful 1-aryl-4-substituted 1,4-dihydro-5H-tetrazol-5-one herbicides.
    Type: Grant
    Filed: October 11, 1990
    Date of Patent: April 14, 1992
    Assignee: FMC Corporation
    Inventor: George Theodoridis
  • Patent number: 5084085
    Abstract: Herbicidal aryloxyphenyltriazolinones compounds which are ring-substituted aryloxyphenyltriazolinones, such as compounds of the formula ##STR1## where Z is O, S, NH, or alkylamino; and where R.sup.2 is, for instance, C.sub.2 H.sub.5 OCO--CH(CH.sub.3)--O-- or CH.sub.3 SO.sub.2 --NH--CO--CH(CH.sub.3)--O--.
    Type: Grant
    Filed: August 3, 1990
    Date of Patent: January 28, 1992
    Assignee: FMC Corporation
    Inventor: George Theodoridis
  • Patent number: 5081287
    Abstract: The present invention discloses and exemplifies alcohol, ether and ester derivatives of difluoroalkanes and difluoroalkenylalkanes having the general formula R--(CH.sub.2).sub.m --CR.sup.2 R.sup.3 --OR.sup.1, in which R is a 1,1-difluoroalkyl or a 1,1-difluoroalkenyl group, composition thereof, and use thereof to control agricultural crop pests.
    Type: Grant
    Filed: June 30, 1989
    Date of Patent: January 14, 1992
    Assignee: FMC Corporation
    Inventors: Clinton J. Peake, Thomas G. Cullen, Anthony J. Martinez
  • Patent number: 5073564
    Abstract: Ethynylbenzothiophene compounds of the following formula are effective as pesticides. ##STR1## wherein R is selected from ##STR2## R.sup.1 is selected from hydrogen, halogen, lower alkyl, lower haloalkyl, and phenylethynyl;R.sup.2 is selected from hydrogen, halogen, lower alkyl, lower alkylthio, lower haloalkenyl, haloalkenylthio, phenyl lower alkenyl, formyl, lower alkoxycarbonyl, carboxy lower alkenyl, lower alkoxycarbonyl lower alkenyl, phenyl, 2-thienyl, and methylthien-2-yl;R.sup.3 is selected from alkyl, lower trialkylsilyl, lower haloalkyl, hydroxyalkyl, alkylcarbonyl, methylthien-2-yl, 2-thienyl, and benzothien-2-yl;R.sup.4 is selected from hydrogen, halogen, lower alkyl, lower haloalkyl, lower alkoxy, lower haloalkylthio, lower alkoxycarbonyl, amino, and alkylcarbonylamino; andR.sup.5 is selected from hydrogen, lower alkyl and lower haloalkyl.
    Type: Grant
    Filed: July 6, 1990
    Date of Patent: December 17, 1991
    Assignee: FMC Corporation
    Inventors: David M. Roush, Steven G. Davis, Kathryn A. Lutomski, Gary A. Meier, Richard B. Phillips, Susan E. Burkart
  • Patent number: 5015765
    Abstract: Hydroxamic acids are efficiently isolated from aqueous reaction media in which they are produced as solids by adding to the reaction mixture with agitation, a coalescing amount of a water insoluble organic liquid, such as a light hydrocarbon or halohydrocarbon, which is a non-solvent for the hydroxamic acids. The coalesced particles float to the surface of the medium leaving behind a clear, aqueous phase which can be drained from the reaction vessel to leave the discrete particles of hydroxamic acid. Buoyancy of the particles is assisted by adding hydrogen peroxide to the reaction mixture or by bubbling air therethrough, usually after the coalescence.
    Type: Grant
    Filed: September 20, 1989
    Date of Patent: May 14, 1991
    Assignee: FMC Corporation
    Inventors: Gerald J. Murphy, John W. Ager, Matthew I. Levinson
  • 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