Patents Represented by Attorney Norman L. Craig
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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: 5407808Abstract: 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: GrantFiled: December 20, 1993Date of Patent: April 18, 1995Assignee: FMC CorporationInventors: Blaik P. Halling, Debra A. Yuhas
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Patent number: 5322702Abstract: 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: GrantFiled: June 15, 1992Date of Patent: June 21, 1994Assignee: FMC CorporationInventors: Edward Selinger, Thomas R. Laaman
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Patent number: 5298502Abstract: 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: GrantFiled: December 23, 1991Date of Patent: March 29, 1994Assignee: FMC CorporationInventors: Blaik P. Halling, Debra A. Witkowski
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Patent number: 5256793Abstract: 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: GrantFiled: May 13, 1992Date of Patent: October 26, 1993Assignee: FMC CorporationInventors: Allan R. Bailey, Marc Halfon, Eric W. Sortore
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Patent number: 5223536Abstract: 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: GrantFiled: July 23, 1991Date of Patent: June 29, 1993Assignee: FMC CorporationInventors: Thomas G. Cullen, Scott McN. Sieburth, Gary A. Meier, John F. Engel
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Patent number: 5217520Abstract: 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: GrantFiled: March 16, 1992Date of Patent: June 8, 1993Assignee: FMC CorporationInventor: Kathleen M. Poss
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Patent number: 5208212Abstract: 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: GrantFiled: October 30, 1992Date of Patent: May 4, 1993Assignee: FMC CorporationInventors: Kathleen M. Poss, Frederick W. Hotzman, Jacques Meyer
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Patent number: 5149357Abstract: 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: GrantFiled: June 19, 1990Date of Patent: September 22, 1992Assignee: FMC CorporationInventors: John A. Dixson, Natesan Murugesan, Keith D. Barnes
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Patent number: 5125958Abstract: 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: GrantFiled: March 5, 1991Date of Patent: June 30, 1992Assignee: FMC CorporationInventor: Kathleen M. Poss
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Patent number: 5105012Abstract: 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: GrantFiled: October 11, 1990Date of Patent: April 14, 1992Assignee: FMC CorporationInventor: George Theodoridis
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Patent number: 5084085Abstract: 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: GrantFiled: August 3, 1990Date of Patent: January 28, 1992Assignee: FMC CorporationInventor: George Theodoridis
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Patent number: 5081287Abstract: 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: GrantFiled: June 30, 1989Date of Patent: January 14, 1992Assignee: FMC CorporationInventors: Clinton J. Peake, Thomas G. Cullen, Anthony J. Martinez
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Patent number: 5073564Abstract: 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: GrantFiled: July 6, 1990Date of Patent: December 17, 1991Assignee: FMC CorporationInventors: David M. Roush, Steven G. Davis, Kathryn A. Lutomski, Gary A. Meier, Richard B. Phillips, Susan E. Burkart
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Patent number: 5015765Abstract: 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: GrantFiled: September 20, 1989Date of Patent: May 14, 1991Assignee: FMC CorporationInventors: Gerald J. Murphy, John W. Ager, Matthew I. Levinson
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Patent number: 4997855Abstract: 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: GrantFiled: September 15, 1988Date of Patent: March 5, 1991Assignee: FMC CorporationInventor: Clinton J. Peake