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).
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Patent number: 5266552Abstract: 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: GrantFiled: November 12, 1991Date of Patent: November 30, 1993Assignee: Imperial Chemical Industries PLCInventors: Michael D. Broadhurst, Harry Tilles
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Patent number: 5232895Abstract: 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: GrantFiled: November 12, 1991Date of Patent: August 3, 1993Assignee: Imperial Chemical Industries plcInventors: Michael D. Broadhurst, Tsze H. Tsang
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Patent number: 5205852Abstract: 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: GrantFiled: November 12, 1991Date of Patent: April 27, 1993Assignee: Imperial Chemical Industries PLCInventors: Michael D. Broadhurst, Tsze H. Tsang
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Patent number: 5189060Abstract: 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: GrantFiled: November 30, 1990Date of Patent: February 23, 1993Assignee: Imperial Chemical Industries PLCInventors: David B. Kanne, Karl J. Fisher, Michael D. Broadhurst
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Patent number: 5186733Abstract: 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: GrantFiled: November 12, 1991Date of Patent: February 16, 1993Assignee: Imperial Chemical Industries PLCInventors: Michael D. Broadhurst, Tsze H. Tsang, John Tomko
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Patent number: 5070097Abstract: 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: GrantFiled: October 19, 1990Date of Patent: December 3, 1991Assignee: ICI Americas Inc.Inventor: Michael D. Broadhurst
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Patent number: 5070210Abstract: 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: GrantFiled: May 7, 1990Date of Patent: December 3, 1991Assignee: ICI Americas Inc.Inventors: Michael D. Broadhurst, Thomas H. Cormartie, Karl J. Fisher, William G. Haag, David B. Kanne, Michael R. Leadbetter
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Patent number: 5064846Abstract: 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: GrantFiled: August 24, 1990Date of Patent: November 12, 1991Assignee: ICI Americas Inc.Inventor: Michael D. Broadhurst
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Patent number: 5045566Abstract: 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: GrantFiled: April 27, 1989Date of Patent: September 3, 1991Assignee: ICI Americas Inc.Inventors: Michael D. Broadhurst, Thomas H. Cromartie, Karl J. Fisher, William G. Haag
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Patent number: 4994488Abstract: 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: GrantFiled: April 27, 1989Date of Patent: February 19, 1991Assignee: ICI Americas Inc.Inventors: Michael D. Broadhurst, Karl J. Fisher, William G. Haag, Michael R. Leadbetter
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Patent number: 4994473Abstract: 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: GrantFiled: October 31, 1988Date of Patent: February 19, 1991Assignee: ICI Americas Inc.Inventor: Michael D. Broadhurst
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Patent number: 4992453Abstract: 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: GrantFiled: January 22, 1990Date of Patent: February 12, 1991Assignee: ICI Americas Inc.Inventors: Michael D. Broadhurst, Thomas H. Cromartie
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Patent number: 4931448Abstract: 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: GrantFiled: November 17, 1987Date of Patent: June 5, 1990Assignee: ICI Americas Inc.Inventors: Michael D. Broadhurst, Thomas H. Cromartie
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Patent number: 4645843Abstract: 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: GrantFiled: February 25, 1985Date of Patent: February 24, 1987Assignee: Stauffer Chemical CompanyInventors: Michael D. Broadhurst, Richard D. Gless, Jr.
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Patent number: 4431594Abstract: 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: GrantFiled: January 13, 1983Date of Patent: February 14, 1984Assignee: Stauffer Chemical CompanyInventors: Michael D. Broadhurst, James B. Heather
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Patent number: 4132713Abstract: 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: GrantFiled: December 23, 1977Date of Patent: January 2, 1979Assignee: Stauffer Chemical CompanyInventor: Michael D. Broadhurst