Patents Represented by Attorney Joel G. Ackerman
  • Patent number: 5182402
    Abstract: A method of killing or controlling unwanted plants by applying to the plant on to a locus thereof an effective amount of a compound of formula (I) ##STR1## or a salt thereof: wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are independently selected from hydrogen, hydroxy, alkyl, alkoxy, alkylcarbonyl, halogen, cyans, nitro, haloalkyl and haloalkoxy; R.sup.6 is hydrogen, hydroxy, amino, lower alkyl, halogen, cyano, haloalkyl, nitro, aryl, or a group C(O).sub.m R.sup.10, wherein R.sup.10 is hydrogen, alkyl, alkenyl, alkynyl or phenyl any of which may be optionally substituted and m is 1 or 2; R.sup.7 is hydrogen, lower alkyl, haloalkyl, C(O).sub.m R.sup.10 or halogen; or R.sup.6 and R.sup.7 together form an optionally substituted alkylene chain of 2 or 3 carbon atoms; R.sup.8 is hydrogen, lower alkyl or halogen or the group R.sup.7 or R.sup.8 together form an oxo group; and the group CZR.sup.9 is carboxy or an ester thereof, or R.sup.9 is a group SR.sup.10 or NR.sup.11 R.sup.12 wherein R.sup.
    Type: Grant
    Filed: September 19, 1991
    Date of Patent: January 26, 1993
    Assignee: Imperial Chemical Industries PLC
    Inventors: Terence Lewis, Harjinder S. Bansal, Raymond L. Sundley, Michael R. Bartley, Walter Hepworth, David J. Gilman, Ian T. Kay, David J. Collins
  • Patent number: 5176737
    Abstract: A herbicidal compound of formula (I): ##STR1## in which Ar is an optionally substituted aryl or heterocyclic ring system:R.sup.1 and R.sup.2 are independently selected from H, optionally substituted alkyl, alkenyl or akynyl, halogen, NR.sup.a R.sup.b, or R.sup.1 and R.sup.2 together with the carbon to which they are attached form an optionally substituted alkenyl or cycloalkyl group;R.sup.3 is CO.sub.2 R.sup.4, CN, COR.sup.4, CH.sub.2 OR.sup.4, CH.sub.4 (OH)R.sup.4, CH(OR.sup.4)R.sup.5, CH.sub.2 OSO.sub.6 R.sup.4, CH.sub.2 OSO.sub.6 R.sub.4, CH.sub.2 ONR.sup.6 R.sup.7, CSNH.sub.2, COSR.sup.4, SCOR.sup.4, COHNSO.sub.2 R.sup.4, CONR.sup.6 R.sup.7, CONHNR.sup.6 R.sup.7, CONHN.sup.+ R.sup.6 R.sup.7 R.sup.8 Y.sup.-2, CO.sub.2.sup.- M.sup.+ or COON.dbd.CR.sup.6 R.sup.7 ;M.sup.+ is an agriculturally acceptable cation;Y.sup.- is an agriculturally acceptable anion;R.sup.4, and R.sup.5 are independently selected from H or an optionally substituted alkyl, aryl, alkenyl or alkynyl group;R.sup.6, R.sup.7, R.sup.8, R.sup.
    Type: Grant
    Filed: February 7, 1991
    Date of Patent: January 5, 1993
    Assignee: Imperial Chemical Industries PLC
    Inventors: Ewan J. T. Chrystal, John E. D. Barton, David Cartwright, Christopher J. Mathews
  • Patent number: 5167696
    Abstract: A compound of formula (I): ##STR1## in which Ar is an optionally substituted aryl or heterocyclic ring system; W is O or NR.sup.1 where R.sup.1 is hydrogen or lower alkyl;A is .dbd.CH or >CH.sub.2 and G is .dbd.C--R.sup.2, >CR.sup.3 R.sup.4 or >C.dbd.R.sup.5 such that --G--A-- is --CR.sup.2 .dbd.CH--, where R.sup.2 is H or CR.sup.6 R.sup.7 XR.sup.8 ; or --G--A-- is CR.sup.3 R.sup.4 --CH.sub.2 where CR.sup.3 R.sup.4 is CH--CR.sup.6 R.sup.7 XR.sup.8, CH--OCR.sup.6 R.sup.7 XR.sup.8, C(R.sup.9)OCOR.sup.10, CR.sup.9 R.sup.10, C(R.sup.9)OR.sup.10, C(OR.sup.9)OR.sup.10, or CH--CH.sub.2 (CO.sub.2 R.sup.11); or --G--A-- is --CR.sup.5 --CH.sub.2 -- where R.sup.5 is .dbd.CR.sup.7 XR.sup.8, .dbd.NOCR.sup.6 R.sup.7 XR.sup.8, .dbd.NOR.sup.11 or .dbd.NOCOR.sup.11 ;X is (CH.sub.2).sub.n, CH.dbd.CH, CH(OR.sup.20)CH.sub.2, or COCH.sub.2 ;n is 0, 1 or 2;R.sup.6 and R.sup.7 are independently selected from H, optionally substituted alkyl, alkenyl or alkynyl, halogen, NR.sup.9 R.sup.10, or R.sup.6 and R.sup.
    Type: Grant
    Filed: February 7, 1991
    Date of Patent: December 1, 1992
    Assignee: Imperial Chemical Industries PLC
    Inventors: Ewan J. T. Chrystal, John E. D. Barton, David Cartwright
  • Patent number: 5160529
    Abstract: Microcapsules containing a substantially water-insoluble liquid material, such as an anilide herbicide, and optionally also a herbicide antidote, within a porous shell to effect a slow rate of release of said herbicide (and optionally said antidote) through said shell, are produced by a process which comprises (a) providing an organic solution comprising said material and an etherified amino resin prepolymer dissolved therein which from about 50% to about 98% of the methylol groups of said prepolymer have been etherified with a C.sub.4 -C.sub.
    Type: Grant
    Filed: February 6, 1991
    Date of Patent: November 3, 1992
    Assignee: Imperial Chemical Industries PLC
    Inventors: Herbert B. Scher, Marius Rodson
  • Patent number: 5133798
    Abstract: A compound of formula (I): ##STR1## in which the dotted lines indicate the presence of two double bonds arranged so as to form a fused hetero-aromatic ring system;Ar is an optionally substituted aryl or heterocyclic ring;W is O or NR.sup.1, where R.sup.1 is hydrogen or lower alkyl;X is (CH.sub.2).sub.n, CH.dbd.CH, CH(OR.sup.5)CH.sub.2, COCH.sub.2 ;where n is O, 1 or 2;R.sup.2 and R.sup.3 are independently selected from H, optionally substituted alkyl, alkenyl or alkynyl, halogen, NR.sup.6 R.sup.7 or R.sup.2 and R.sup.3 together with the carbon to which they are attached form an optionally substituted alkenyl or cycloalkyl group;R.sup.4 is CO.sub.2 R.sup.8, CN, COR.sup.8, CH.sub.2 OR.sup.8, CH(OH)R.sup.8, CH(OR.sup.8)R.sup.9, CSNH.sub.2, COSR.sup.8, CSOR.sup.8, CONHSO.sub.2 R.sup.8, CONR.sup.10 R.sup.11, CONHNR.sup.10 R.sup.11, CONHN.sup.+ R.sup.10 R.sup.11 R.sup.12 R.sup.13-, CO.sub.2.sup.- R.sup.14+ or COON.dbd.CR.sup.10 R.sup.11 ;R.sup.14+ is an agriculturally acceptable cation; and R.sup.
    Type: Grant
    Filed: February 7, 1991
    Date of Patent: July 28, 1992
    Assignee: Imperial Chemical Industries PLC
    Inventors: David P. J. Pearson, John E. D. Barton, David Cartwright, Susan P. Barnett
  • Patent number: 5089623
    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: February 15, 1990
    Date of Patent: February 18, 1992
    Assignee: Imperial Chemical Industries Plc
    Inventor: Karl J. Fisher
  • Patent number: 5084083
    Abstract: A method of killing or controlling unwanted plants by applying to the plant on to a locus thereof an effective amount of a compound of formula (I) ##STR1## or a salt thereof: wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are independently selected from hydrogen, hydroxy, alkyl, alkoxy, alkylcarbonyl, halogen, cyano, nitro, haloalkyl and haloalkoxy; R.sup.6 is hydrogen, hydroxy, amino, lower alkyl, halogen, cyano, haloalkyl, nitro, aryl, or a group C(O).sub.m R.sup.10, wherein R.sup.10 is hydrogen, alkyl, alkenyl, alkynyl or phenyl any of which may be optionally substituted and m is 1 or 2; R.sup.7 is hydrogen, lower alkyl, haloalkyl, C(O).sub.m R.sup.10 or halogen; or R.sup.6 and R.sup.7 together form an optionally substituted alkylene chain of 2 or 3 carbon atoms; R.sup.8 is hydrogen, lower alkyl or halogen or the group R.sup.7 and R.sup.8 together form an oxo group; and the group CZR.sup.9 is carboxy or an ester thereof, or R.sup.9 is a group SR.sup.10 or NR.sup.11 R.sup.12 wherein R.sup.
    Type: Grant
    Filed: November 2, 1989
    Date of Patent: January 28, 1992
    Assignee: Imperial Chemical Industries PLC
    Inventors: Terence Lewis, Harjinder S. Bansal, Raymond L. Sunley, Ian T. Kay
  • Patent number: 5078781
    Abstract: Liquid compositions comprising:(a) a bipyridilium herbicide;(b) a photosynthesis-inhibiting herbicide;(c) a normally water-insoluble oil in which the photosynthesis-inhibiting herbicide (b) is soluble;(d) water; and(e) a surfactant selected from:(i) a polyalkyl glucoside;(ii) a polyoxypropylene-polyoxyethylene block copolymer;(iii) an alkyl trimethyl ammonium salt; and(iv) a mixture of polyvinyl alcohol with a surfactant having an HLB value from about 13 to about 20.
    Type: Grant
    Filed: June 30, 1989
    Date of Patent: January 7, 1992
    Assignee: Imperial Chemical Industries PLC
    Inventor: Charles W. Finch, Jr.
  • 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: 5053516
    Abstract: 3-Methyl-2-alkylamino-1-halo-1-cyano cyclobutanes are cleaved under acid conditions to form 2-halo-4-formylvaleronitrile and 4-formyl-2-pentenonitrile which can be cyclized to form 2-substituted-5-methylpyridine derivatives. These pyridine derivatives are useful as starting materials in the manufacture of herbicides such as fluazifop-butyl.
    Type: Grant
    Filed: March 12, 1990
    Date of Patent: October 1, 1991
    Assignee: ICI Americas Inc.
    Inventors: Ludwig A. Hartmann, John F. Stephen
  • Patent number: 5051125
    Abstract: A synergistic herbicidal composition with residual activity comprises cycloate and cyanazine in a weight ratio of about 2:1 to 4:1, plus preferably a thiocarbamate herbicide antidote.
    Type: Grant
    Filed: June 20, 1990
    Date of Patent: September 24, 1991
    Assignee: ICI Americas Inc.
    Inventors: Bareld E. Groenwold, James L. Ahle
  • 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: 4990648
    Abstract: A process for production of an alkylthiobenzoate comprising reacting a cyclohexenone having the formula ##STR1## in which R.sub.1 is C.sub.1 -C.sub.6 alkyl; X is alkyl or unsubstituted alkyl; and Y is hydrogen, halogen or alkyl, with a mercaptan having the formula R.sub.2 SH in which R.sub.2 is C.sub.1 -C.sub.4 alkyl, preferably in the presence of an acid catalyst, to form a cyclohexadiene thioether, and dehydrogenating the thioether to produce a thioalkylbenzoate.The thioalkylbenzoate may be further converted by oxidation and/or hydrolysis to a corresponding thioalkyl, alkylsulfinyl or alkylsulfonyl benzoic acid.
    Type: Grant
    Filed: January 3, 1990
    Date of Patent: February 5, 1991
    Assignee: ICI Americas Inc.
    Inventor: Richard W. Brown
  • Patent number: 4956487
    Abstract: Thiophosphonate compounds having the formula ##STR1## in which R is alkyl, haloalkyl or aryl; X is chloro or SR.sub.2 ; R.sub.1 is alkyl or aryl; and when X is SR.sub.2 then R.sub.2 is a group identical to R.sub.1, or R.sub.1 and R.sub.2 taken together form an optionally alkyl-substituted polymethylene group, are prepared by reaction of a thiophosphonodichloride with a mercaptan in the presence of a catalytic amount of a quaternary ammonium or phosphonium salt, a tertiary amine or hydrohalide thereof or an alkali metal halide combined with a Crown ether, in the substantial absence of a base.
    Type: Grant
    Filed: December 12, 1988
    Date of Patent: September 11, 1990
    Assignee: ICI Americas Inc.
    Inventors: Jeffrey D. Robbins, Richard D. Gless, Jr.
  • Patent number: 4925970
    Abstract: A process for production of an alkylthiobenzoate comprising reacting a cyclohexenone having the formula ##STR1## in which R.sub.1 is C.sub.1 -C.sub.6 alkyl; X is alkyl or unsubstituted alkyl; and Y is hydrogen, halogen or alkyl, with a mercaptan having the formula R.sub.2 SH in which R.sub.2 is C.sub.1 -C.sub.4 alkyl, preferably in the presence of an acid catalyst, to form a cyclohexadiene thioether, and dehydrogenating the thioether to produce a thioalkylbenzoate.The thioalkylbenzoate may be further converted by oxidation and/or hydrolysis to a corresponding thioalkyl, alkylsulfinyl or alkylsulfonyl benzoic acid.
    Type: Grant
    Filed: December 22, 1988
    Date of Patent: May 15, 1990
    Inventor: Richard W. Brown