Patents by Inventor Michael D. Broadhurst

Michael D. Broadhurst has filed for patents to protect the following inventions. This listing includes patent applications that are pending as well as patents that have already been granted by the United States Patent and Trademark Office (USPTO).

  • Patent number: 5266552
    Abstract: Novel herbicides have the formula ##STR1## in which R is halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 alkylcarbamoyl, C.sub.1 -C.sub.4 mono- or dialkylamino, phenoxy or nitro;n is 0, 1 or 2;X is oxygen or sulfur;R.sub.1 is C.sub.2 -C.sub.8 alkyl, C.sub.3 -C.sub.6 cycloalkyl, phenyl, 2-trifluoromethylphenyl, 3-trifluoromethoxyphenyl, 4-methoxyphenyl, 4-nitrophenyl, 3,4-dichlorophenyl or benzyl;R.sub.2 is hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.6 cycloalkyl, phenyl, C.sub.3 -C.sub.6 alkenyl or C.sub.3 -C.sub.6 alkynyl; andR.sub.3 is C.sub.2 -C.sub.6 alkyl, C.sub.3 -C.sub.6 cycloalkyl, phenyl, phenyl(C.sub.1 -C.sub.2)-alkyl, 3,4-methylenedioxyphenyl or pyridyl; orR.sub.2 and R.sub.3 taken together with the nitrogen atom form a 4-7 member ring;provided that:a) if X is sulfur, R.sub.2 is not hydrogen;b) if R.sub.2 is hydrogen, R.sub.3 is alkyl, cycloalkyl or phenylalkyl.
    Type: Grant
    Filed: November 12, 1991
    Date of Patent: November 30, 1993
    Assignee: Imperial Chemical Industries PLC
    Inventors: Michael D. Broadhurst, Harry Tilles
  • Patent number: 5232895
    Abstract: Herbicides have the formula ##STR1## in which R.sub.1 is C.sub.2 -C.sub.8 alkyl or C.sub.5 -C.sub.8 cycloalkyl;R.sub.2 is hydrogen or C.sub.1 -C.sub.4 alkyl;R.sub.3 is phenyl, optionally substituted by C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 haloalkoxy, one or more halogens, one or two C.sub.1 -C.sub.4 alkoxy groups, one C.sub.1 -C.sub.4 alkyl and one C.sub.1 -C.sub.4 alkoxy groups, or if R.sub.2 is C.sub.1 -C.sub.4 alkyl, R.sub.3 may also be phenyl substituted by two C.sub.1 -C.sub.4 haloalkyl groups; pyridyl or tolylsulfonyl;R.sub.4 and R.sub.5 are independently C.sub.2 -C.sub.6 alkyl.
    Type: Grant
    Filed: November 12, 1991
    Date of Patent: August 3, 1993
    Assignee: Imperial Chemical Industries plc
    Inventors: Michael D. Broadhurst, Tsze H. Tsang
  • Patent number: 5205852
    Abstract: Herbicidal compounds have the formula ##STR1## in which R is C.sub.3 -C.sub.6 alkyl or C.sub.3 -C.sub.6 cycloalkyl;X is oxygen or sulfur;R.sub.1 is C.sub.1 -C.sub.12 alkyl, C.sub.3 -C.sub.6 cycloalkyl optionally substituted with up to two C.sub.1 -C.sub.3 alkyl groups, phenyl, or substituted phenyl having from 1 to 2 substituents selected from halo, nitro, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 thioalkyl, C.sub.3 -C.sub.4 alkenyl, C.sub.1 -C.sub.4 alkoxycarbonyl, and phenyl;R.sub.2 is hydrogen, C.sub.1 -C.sub.6 alkyl or C.sub.3 -C.sub.6 cycloalkyl; andR.sub.3 is C.sub.2 -C.sub.6 alkyl, C.sub.3 -C.sub.6 cycloalkyl, phenyl or substituted phenyl having from 1 to 2 substituents selected from C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkyl and halogen;provided that if R.sub.2 is hydrogen, R.sub.3 is not phenyl or substituted phenyl;or R.sub.2 and R.sub.3 taken together with the nitrogen atom form a 4-8 membered ring, optionally including an oxygen heteroatom.
    Type: Grant
    Filed: November 12, 1991
    Date of Patent: April 27, 1993
    Assignee: Imperial Chemical Industries PLC
    Inventors: Michael D. Broadhurst, Tsze H. Tsang
  • Patent number: 5189060
    Abstract: Novel insecticides have the formula ##STR1## in which R.sub.1 is hydrogen, halogen, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 haloalkoxy or C.sub.1 -C.sub.4 haloalkylthio;R.sub.2 is hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 haloalkoxy or C.sub.1 -C.sub.4 haloalkylthio;R.sub.3 is hydrogen, halogen or C.sub.1 -C.sub.4 haloalkyl; orR.sub.1 and R.sub.2 taken together are C.sub.1 -C.sub.4 alkylenedioxy or halo-C.sub.1 -C.sub.3 alkylenedioxy; provided that R.sub.1, R.sub.2 and R.sub.3 are not all hydrogen;R.sub.4 is methyl, ethyl, n-propyl, C.sub.3 -C.sub.7 branched alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.2 -C.sub.4 alkenyl; or cyclopropyl, optionally substituted by up to 4 methyl groups or up to 2 halogens;R.sub.5 is: ##STR2## R.sub.6 is phenyl, benzyl, C.sub.3 -C.sub.4 alkenyl, or C.sub.3 alkynyl; R.sub.7, R.sub.8, R.sub.10 and R.sub.11 are each halogen; andR.sub.
    Type: Grant
    Filed: November 30, 1990
    Date of Patent: February 23, 1993
    Assignee: Imperial Chemical Industries PLC
    Inventors: David B. Kanne, Karl J. Fisher, Michael D. Broadhurst
  • Patent number: 5186733
    Abstract: Herbicides have the formula ##STR1## in which R is hydrogen, mono- or poly-halo, mono- or di-(C.sub.1 -C.sub.4 alkyl), C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, phenoxy or nitro;R.sub.1 is hydrogen or C.sub.1 -C.sub.4 alkyl;R.sub.3 is C.sub.1 -C.sub.6 alkyl;R.sub.2 is C.sub.2 -C.sub.4 alkyl, C.sub.3 -C.sub.6 cycloalkyl, phenyl, optionally substituted by C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 haloalkoxy, one or more halogens, or two C.sub.1 -C.sub.4 alkoxy groups, or one C.sub.1 -C.sub.4 alkyl and one C.sub.1 -C.sub.4 alkoxy group, phenyl-(C.sub.1 -C.sub.2)alkyl or pyridyl; orR.sub.1 and R.sub.2, and/or R.sub.3 and R.sub.4 respectively, taken together with the nitrogen atom, form a 4-8 member ring, optionally including an oxygen heteroatom;and R.sub.4 is C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.6 cycloalkyl, phenyl, optionally substituted by C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 haloalkoxy, one or more halogens, or two C.sub.1 -C.sub.
    Type: Grant
    Filed: November 12, 1991
    Date of Patent: February 16, 1993
    Assignee: Imperial Chemical Industries PLC
    Inventors: Michael D. Broadhurst, Tsze H. Tsang, John Tomko
  • Patent number: 5070097
    Abstract: Insecticides of the general formula ##STR1## wherein R.sub.1 is an optionally substituted 5- to 10-member heterocyclic moiety; R.sub.2 is an optionally substituted alkyl, cycloalkyl or alkenyl moiety; X is oxygen, sulfur or --NH--; and R.sub.3 is: (a) an optionally substituted 3-phenoxyphenalkyl, 3-phenoxypyridylalkyl, 3-(pyridyloxy)phenalkyl, 3-phenylaminophenalkyl, 3-benzylphenalkyl or 3-benzyloxyphenalkyl moiety; (b) a benzylfuranylmethyl moiety; (c) a 3- or 4-substituted benzyl or tetrafluorobenzyl moiety; (d) 4-phenoxy-20-butyn-2-yl; or (e) 2-methyl-3-phenylbenzyl.
    Type: Grant
    Filed: October 19, 1990
    Date of Patent: December 3, 1991
    Assignee: ICI Americas Inc.
    Inventor: Michael D. Broadhurst
  • Patent number: 5070210
    Abstract: A series of novel imidate insecticides distinguished by the general formula ##STR1## in which R.sub.1 is an optionally substituted aryl group in which the substituents are halo, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkylthio, C.sub.3 -C.sub.6 cycloalkyl, nitro, C.sub.1 -C.sub.4 haloalkyl, C.sub.2 -C.sub.5 carboalkoxy, C.sub.1 -C.sub.4 alkylthio, cyano, C.sub.1 -C.sub.4 alkylsulfonyl, C.sub.1 -C.sub.4 haloalkylsulfonyl; C.sub.2 -C.sub.5 alkylcarbonyl, C.sub.2 -C.sub.4 alkyleneoxy, C.sub.1 -C.sub.4 alkylenedioxy, C.sub.1 -C.sub.3 halo-substituted alkylenedioxy, phenyl, mono-substituted phenyl, pyridyloxy, C.sub.2 -C.sub.4 alkylene, C.sub.2 -C.sub.4 alkenyl, and/or amido;R.sub.2 is C.sub.1 -C.sub.7 alkyl, C.sub.1 -C.sub.6 haloalkyl, cyclopropyl, cyclobutyl, mono- or poly- halo- or methyl-substituted cyclopropyl, cyano, C.sub.2 -C.sub.4 alkoxyalkyl, C.sub.2 -C.sub.6 haloalkenyl or C.sub.2 -C.sub.6 alkenyl; andR.sub.
    Type: Grant
    Filed: May 7, 1990
    Date of Patent: December 3, 1991
    Assignee: ICI Americas Inc.
    Inventors: Michael D. Broadhurst, Thomas H. Cormartie, Karl J. Fisher, William G. Haag, David B. Kanne, Michael R. Leadbetter
  • Patent number: 5064846
    Abstract: Insecticides of the general formula ##STR1## wherein R.sub.1 is an optionally substituted 5- to 10-member heterocyclic moiety; R.sub.2 is an optionally substituted alkyl, cycloalkyl or alkenyl moiety; X is oxygen, sulfur or --NH--; and R.sub.3 is: (a) an optionally substituted 3-phenoxyphenalkyl, 3-phenoxypyridylalkyl, 3-(pyridyloxy)phenalkyl, 3-phenylaminophenalkyl, 3-benzylphenalkyl or 3-benzyloxyphenalkyl moiety; (b) a benzylfuranylmethyl moiety; (c) a 3- or 4-substituted benzyl or tetrafluorobenzyl moiety; (d) 4-phenoxy-2-butyn-2-yl; or (e) 2-methyl-3-phenylbenzyl.
    Type: Grant
    Filed: August 24, 1990
    Date of Patent: November 12, 1991
    Assignee: ICI Americas Inc.
    Inventor: Michael D. Broadhurst
  • Patent number: 5045566
    Abstract: A series of novel imidate insecticides distinguished by the general formula ##STR1## in which R.sub.1 is an optionally substituted aryl group in which the substituents are halo, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkylthio, C.sub.3 -C.sub.6 cycloalkyl, nitro, C.sub.1 -C.sub.4 haloalkyl, C.sub.2 -C.sub.5 carboalkoxy, C.sub.1 -C.sub.4 alkylthio, cyano, C.sub.1 -C.sub.4 alkylsulfonyl, C.sub.2 -C.sub.4 haloalkylsulfonyl; C.sub.2 -C.sub.5 alkylcarbonyl, C.sub.2 -C.sub.4 alkyleneoxy, C.sub.1 -C.sub.2 perhaloalkyleneoxy; C.sub.1 -C.sub.4 alkylendioxy, C.sub.1 -C.sub.3 halo-substituted alkylenedioxy, phenyl, mono-substituted phenyl, pyridyloxy, C.sub.2 -C.sub.4 alkylene, C.sub.2 -C.sub.4 alkenyl, C.sub.3 -haloalkenoxy; and/or amido;R.sub.2 is C.sub.1 -C.sub.7 alkyl, C.sub.1 -C.sub.6 haloalkyl, cyclopropyl, cyclobutyl, mono- or poly- halo- or methyl-substituted cyclopropyl, cyano, C.sub.2 -C.sub.4 alkoxyalkyl, C.sub.2 -C.sub.6 haloalkenyl or C.sub.2 -C.
    Type: Grant
    Filed: April 27, 1989
    Date of Patent: September 3, 1991
    Assignee: ICI Americas Inc.
    Inventors: Michael D. Broadhurst, Thomas H. Cromartie, Karl J. Fisher, William G. Haag
  • Patent number: 4994488
    Abstract: A series of novel imidate insecticides distinguished by the general formula ##STR1## in which R.sub.1 is an optionally substituted aryl group in which the substituents are halo, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkylthio, C.sub.3 -C.sub.6 cycloalkyl, nitro, C.sub.1 -C.sub.4 haloalkyl, C.sub.2 -C.sub.5 carboalkoxy, C.sub.1 -C.sub.4 alkylthio, cyano, C.sub.1 -C.sub.4 alkylsulfonyl, C.sub.1 -C.sub.4 haloalkylsulfonyl, C.sub.2 -C.sub.5 alkylcarbonyl, C.sub.2 -C.sub.4 alkyleneoxy, C.sub.1 -C.sub.2 perhaloalkyleneoxy, C.sub.1 -C.sub.4 alkylenedioxy, C.sub.1 -C.sub.3 halo-substituted alkylenedioxy, phenyl, mono-substituted phenyl, pyridyloxy, C.sub.2 -C.sub.4 alkylene, C.sub.2 -C.sub.4 alkenyl, C.sub.3 -haloalkenoxy, and/or amido;R.sub.2 is cyclopropyl or mono- or poly- halo- or methyl-substituted cyclopropyl; andR.sub.
    Type: Grant
    Filed: April 27, 1989
    Date of Patent: February 19, 1991
    Assignee: ICI Americas Inc.
    Inventors: Michael D. Broadhurst, Karl J. Fisher, William G. Haag, Michael R. Leadbetter
  • Patent number: 4994473
    Abstract: Insecticides of the general formula ##STR1## wherein R.sub.1 is an optionally substituted 5- to 10-member heterocyclic moiety; R.sub.2 is an optionally substituted alkyl, cycloalkyl or alkenyl moiety; X is oxygen, sulfur or --NH--; and R.sub.3 is: (a) an optionally substituted 3-phenoxyphenalkyl, 3-phenoxypyridylalkyl, 3-(pyridyloxy)phenalkyl, 3-phenylaminophenoalkyl, 3-benzylphenalkyl or 3-benzyloxyphenalkyl moiety; (b) a benzylfuranylmethyl moiety; (c) a 3- or 4-substituted benzyl or tetrafluorobenzyl moiety; (d) 4-phenoxy-2-butyn-2-yl; or (e) 2-methyl-3-phenylbenzyl.
    Type: Grant
    Filed: October 31, 1988
    Date of Patent: February 19, 1991
    Assignee: ICI Americas Inc.
    Inventor: Michael D. Broadhurst
  • Patent number: 4992453
    Abstract: Insecticidal compounds having the formula ##STR1## in which R is an optionally substituted aryl moiety; R.sub.2 is an optionally substituted alkyl, cycloalkyl or alkenyl moiety, X is sulfur, amino or C.sub.1 -C.sub.4 monoalkylamino; and R.sub.3 is: (a) an optionally substituted 3-phenoxyphenalkyl, 3-phenoxypyridylalkyl or 3-(4-pyridyloxy)phenalkyl moiety; (b) pentafluorobenzyl; or (c) 2-methyl-3-phenylbenzyl.
    Type: Grant
    Filed: January 22, 1990
    Date of Patent: February 12, 1991
    Assignee: ICI Americas Inc.
    Inventors: Michael D. Broadhurst, Thomas H. Cromartie
  • Patent number: 4931448
    Abstract: Insecticidal compounds having the formula ##STR1## in which R is an optionally substituted aryl moiety; R.sub.2 is an optionally substituted alkyl, cycloalkyl or alkenyl moiety, X is sulfur, amino or C.sub.1 -C.sub.4 monoalkylamino; and R.sub.3 is: (a) an optionally substituted 3-phenoxyphenalkyl, 3-phenoxypyridylalkyl or 3-(4-pyridyloxy)phenalkyl moiety; (b) pentafluorobenzyl; or (c) 2-methyl-3-phenylbenzyl.
    Type: Grant
    Filed: November 17, 1987
    Date of Patent: June 5, 1990
    Assignee: ICI Americas Inc.
    Inventors: Michael D. Broadhurst, Thomas H. Cromartie
  • Patent number: 4645843
    Abstract: Production of N-arylhalopyrrolidones by intramolecular cyclization of an .alpha.-halogen-N-2-alkenylamide is conducted in the presence of a copper-containing catalyst and a primary or secondary aliphatic amine.
    Type: Grant
    Filed: February 25, 1985
    Date of Patent: February 24, 1987
    Assignee: Stauffer Chemical Company
    Inventors: Michael D. Broadhurst, Richard D. Gless, Jr.
  • Patent number: 4431594
    Abstract: A process for the preparation of sulfonium or sulfoxonium salts of N-phosphonomethylglycine which comprises:(1) reacting N-phosphonomethylglycine, a compound of the formula ##STR1## with a compound selected from the group consisting of those having the formula ##STR2## wherein R.sub.1, R.sub.2 and R.sub.3 are the same or different and are alkyl groups having from 1 to 4 carbon atoms or aromatic alkyl groups, X is chloride, bromide or iodide and Z is an electron pair or oxygen, or ##STR3## wherein R.sub.1, R.sub.2 and R.sub.3 are the same or different and are alkyl groups having from 1 to 4 carbon atoms and are the same as in (a) above, R.sub.4 is an alkyl group having from 1 to 12 carbon atoms, aromatic or aromatic alkyl groups, X is chlorine or iodine, and Y is nitrogen or phosphorus, said reaction being conducted in the presence of a trialkylamine of the formula(R).sub.
    Type: Grant
    Filed: January 13, 1983
    Date of Patent: February 14, 1984
    Assignee: Stauffer Chemical Company
    Inventors: Michael D. Broadhurst, James B. Heather
  • Patent number: 4132713
    Abstract: A novel process is disclosed herein for the preparation of N-substituted halopyrrolidones of the formula ##STR1## in which X is selected from the group consisting of hydrogen, chlorine, and methyl;Y is selected from the group consisting of hydrogen, chlorine, and bromine;Z is selected from the group consisting of chlorine and bromine;R.sup.1 is selected from the group consisting of hydrogen and C.sub.1 -C.sub.4 alkyl; andR.sup.2 is selected from the group consisting of C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.6 alkenyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.3 -C.sub.7 cycloalkyl, C.sub.4 -C.sub.8 cycloalkylalkyl, benzyl, chlorobenzyl, and ##STR2## in which R.sup.3 is selected from the group consisting og hydrogen, C.sub.1 -C.sub.4 alkyl, acetyl, chlorine, bromine, fluorine, iodine, trifluoromethyl, nitro, cyan, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 alkylsulfinyl, C.sub.1 -C.sub.
    Type: Grant
    Filed: December 23, 1977
    Date of Patent: January 2, 1979
    Assignee: Stauffer Chemical Company
    Inventor: Michael D. Broadhurst