Patents Represented by Attorney Joel G. Ackerman
  • Patent number: 4913722
    Abstract: A 2-iminophenyl thiazolidine having the formula ##STR1## wherein R is hydrogen or methyl; R.sub.1 is halo, nitro, cyano, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, perhalomethyl, difluoromethyl, pentafluoroethyl, trifluoromethylthhio, difluoromethoxy, trifluoromethoxy, tetrafluoroethoxy, methylsulfonyl, C.sub.1 -C.sub.4 alkyloxyiminomethyl, benzyloxyiminomethyl, 1-(C.sub.1 -C.sub.4 alkyl)-oxyiminoethyl or 1-benzyloxyiminoethyl; R.sub.2 is hydrogen or halo; R.sub.3 and R.sub.4 are independently hydrogen, halo, nitro, cyano, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 fluoroalkoxy, C.sub.1 -C.sub.4 alkoxy or C.sub.1 -C.sub.4 alkylthio; and X is hydrogen or halogen.Also disclosed is a process for making the compounds and a method of use which comprises applying the compound or composition to the locus where control is desired.
    Type: Grant
    Filed: November 15, 1988
    Date of Patent: April 3, 1990
    Assignee: ICI Americas Inc.
    Inventors: Raymond A. Felix, Jeffery T. Springer, Eugene G. Teach, Frank X. Woolard
  • Patent number: 4900758
    Abstract: Novel insecticides have the formula ##STR1## in which R.sub.1 is hydrogen, fluoro or trifluoromethyl;R.sub.2 is(a) halogen, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 haloalkyl, C.sub.1 -C.sub.2 alkoxy or C.sub.1 -C.sub.2 haloalkoxy if R.sub.1 is hydrogen or fluoro; or(b) hydrogen if R.sub.1 is trifluoromethyl;R.sub.3 is hydrogen or halogen; andR.sub.4 is hydrogen or mono- or poly-halogen.
    Type: Grant
    Filed: May 11, 1989
    Date of Patent: February 13, 1990
    Assignee: ICI Americas Inc.
    Inventor: Karl J. Fisher
  • Patent number: 4900351
    Abstract: An iminooxazolidine having the formula ##STR1## wherein X and Y are the same or different and are selected from the group consisting of cyano, halogen, acyl, alkyl, alkylthio, haloalkyl, trihalomethylthio, alkylsulfenyl, alkoxy, carboalkoxy and trihalomethyl wherein the alkyl groups have from 1 to 5 carbon atoms;m is 1 or 2;n is 0, 1 or 2; andR is hydrogen or a lower alkyl group having from 1 to 3 carbon atoms, preferably an ethyl group, and herbicidally effective salts thereof.
    Type: Grant
    Filed: March 14, 1988
    Date of Patent: February 13, 1990
    Assignee: ICI Americas Inc.
    Inventor: Raymond A. Felix
  • Patent number: 4886936
    Abstract: Ortho-nitrobenzonitriles are produced from the corresponding ortho-nitrochlorobenzenes by reaction with cuprous cyanide and an alkali metal bromide, an alkaline earth metal bromide, or zinc bromide or with a combination of lithium cyanide and cuprous bromide, optionally in the presence of a solvent.
    Type: Grant
    Filed: August 15, 1988
    Date of Patent: December 12, 1989
    Assignee: ICI Americas Inc.
    Inventor: Stephen E. Dinizo
  • Patent number: 4877880
    Abstract: A process for the preparation of certain iminothiazolidines of the formula ##STR1## in which R is halo, nitro, cyano, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, pentahalomethyl, difluoromethyl, pentafluoroethyl, trifluoromethylthio, difluoromethoxy, trifluoromethoxy, tetrafluoroethoxy, methylsulfonyl, C.sub.1 -C.sub.4 alkyloxyiminomethyl, benzyloxyiminomethyl, 1-(C.sub.1 -C.sub.4)alkyl oxyiminoethyl or 1-benzyloxyiminoethyl; R.sub.1 is hydrogen or halo; R.sub.2 is hydrogen, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 haloalkyl; and R.sub.3 and R.sub.4 are independently hydrogen, halo, nitro, cyano, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 fluoroalkoxy or C.sub.1 -C.sub.4 alkylthio, by reacting a thiourea with methanesulfonic acid or trifluoromethanesulfonic acid in an aprotic solvent for a period of time and at a temperature sufficient to achieve cyclization of the thiourea to form said iminothiazolidine.
    Type: Grant
    Filed: December 9, 1988
    Date of Patent: October 31, 1989
    Assignee: ICI Americas Inc.
    Inventor: Frank X. Woolard
  • Patent number: 4867782
    Abstract: Compounds having the formula ##STR1## in which R.sub.1 is C.sub.1 -C.sub.6 alkyl; C.sub.1 -C.sub.6 alkoalkyl; C.sub.2 -C.sub.6 alkenyl; mono- or di- (C.sub.1 -C.sub.4)alkylamino; phenyl; benzyl; or para-substituted phenyl or benzyl in which the substituent is halogen, cyano, nitro, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio or trifluoromethyl; R.sub.2 is hydrogen, methyl, ethyl or chloromethyl; X is hydrogen, halogen, nitro, cyano, perhalomethyl, difluoro-methyl, pentafluoroethyl, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, trifluoromethylthio, difluoromethoxy, trifluoromethoxy, tetrafluoroethoxy, methylsulfonyl, trifluoromethylsulfonyl, phenoxy, pyridyloxy, halo-substituted-phenoxy or -pyridyloxy, trifluoromethyl-substituted-phenoxy or -pyridyloxy, C.sub.1 -C.sub.4 alkyloximinomethyl, benzyloximinomethyl, 1-(C.sub.1 -C.sub.4 alkyl)oximinoethyl and 1-benzyloximinoethyl; Y is hydrogen, halogen, nitro, cyano, perhalomethyl, difluoromethyl, pentafluoroethyl, C.sub.1 -C.sub.
    Type: Grant
    Filed: July 1, 1988
    Date of Patent: September 19, 1989
    Assignee: ICI Americas Inc.
    Inventor: Frank X. Woolard
  • Patent number: 4868333
    Abstract: 2-Nitro-4-trifluoromethylbenzoic acid is produced by hydrolysis of 2-nitro-4-trifluoromethylbenzonitrile in the presence of relatively concentrated hydrochloric or hydrobromic acid under reflux temperature.
    Type: Grant
    Filed: November 16, 1987
    Date of Patent: September 19, 1989
    Assignee: ICI Americas Inc.
    Inventors: Stephen E. Dinizo, Richard D. Gless, Jr.
  • Patent number: 4867780
    Abstract: Herbicidal compounds have the formula ##STR1## in which W is oxygen or sulfur; X is hydrogen, halogen, nitro, cyano, perhalomethyl, difluoromethyl, pentafluoroethyl, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, trifluoromethylthio, difluoromethoxy, trifluoromethoxy, tetrafluoroethoxy, methylsulfonyl, trifluoromethylsulfonyl, phenoxy, pyridyloxy, halo-substituted-phenoxy or -pyridyloxy, trifluoromethyl-substituted-phenoxy or -pyridyloxy, C.sub.1 -C.sub.4 alkyloximinomethyl, benzyloximinomethyl, 1-(C.sub.1 -C.sub.4 alkyl)-oximinoethyl and 1-benzyloximinoethyl; Y is hydrogen, halogen, nitro, cyano, perhalomethyl, difluoromethyl, pentafluoroethyl, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, trifluoromethylthio, trifluoromethoxy, tetrafluoroethoxy, methylsulfonyl and trifluoromethylsulfonyl; Z is hydrogen or fluoro if Y is hydrogen, or hydrogen if Y is other than hydrogen; R.sub.1 is hydrogen, methyl, ethyl or chloromethyl; A is oxygen, sulfur, ##STR2## in which R.sub.3 and R.sub.
    Type: Grant
    Filed: July 1, 1988
    Date of Patent: September 19, 1989
    Assignee: ICI Americas, Inc.
    Inventor: Frank X. Woolard
  • Patent number: 4855478
    Abstract: An N,N-diaryl-N-alkylurea having the formula ##STR1## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are the same or different and are selected from the group consisting of hydrogen, halogen, cyano, trifluoromethyl, trifluoromethylthio, trifluoromethyl thionyl, trifluoromethane sulfonyl, sulfonamido, substituted phenoxy and substituted pyridyloxy groups wherein the substituent is any one of halogen, cyano, trifluoromethyl, trifluoromethylthio, trifluoromethyl thionyl, trifluoromethane sulfonyl, sulfonamido; andR.sub.5 is selected from the group consisting of alkyl, alkenyl, haloalkyl, haloalkenyl, hydroxyalkyl, hydroxylalkenyl, acetoxyalkyl, acetoxyalkenyl, mercaptoalkyl, and mercaptoalkenyl, wherein the alkyl or alkenyl group in each alkyl- or alkenyl-containing moiety has from 3 to 6 carbon atoms;X is oxygen or sulfur;and agriculturally acceptable salts thereof.Also disclosed is an herbicidal composition and method of treating weeds.
    Type: Grant
    Filed: November 30, 1987
    Date of Patent: August 8, 1989
    Assignee: ICI Americas Inc.
    Inventor: Frank X. Woolard
  • Patent number: 4853483
    Abstract: The present invention relates to a process for the preparation of alkyl semicarbazides by reaction of a dithiocarbamate and hydrazine in a weakly basic reaction media using a metal rearrangement catalyst.
    Type: Grant
    Filed: September 17, 1987
    Date of Patent: August 1, 1989
    Assignee: ICI Americas Inc.
    Inventor: Danielle A. Bright
  • Patent number: 4837209
    Abstract: Compounds and compositions containing them, for insecticidal control, particularly for use as soil and/or foliar insecticides, have the formula ##STR1## in which R.sub.1 is methyl or ethyl;R.sub.2 is C.sub.1 -C.sub.6 alkyl; andR.sub.3 is C.sub.3 -C.sub.6 cycloakyl.
    Type: Grant
    Filed: July 6, 1987
    Date of Patent: June 6, 1989
    Assignee: Stauffer Chemical Company
    Inventor: Charles G. Chavdarian
  • Patent number: 4833250
    Abstract: Carboxylic acid or carboxylic acid halide groups on aryl or heterocyclic aryl rings are directly converted to trihalomethyl groups by using a phenylhalophosphorane, optionally generated in situ by reaction of a phenylphosphonous halide and chlorine.
    Type: Grant
    Filed: March 24, 1988
    Date of Patent: May 23, 1989
    Assignee: ICI Americas Inc.
    Inventor: Elliott Bay
  • Patent number: 4806653
    Abstract: A process of the preparation of iminooxazolidines which comprises (a) reacting a urea alcohol of the formula ##STR1## X, Y, n and R are as defined, with a dehydrating agent to form an intermediate salt compound of the formula ##STR2## wherein X, Y, n and R are as previously defined and X.degree.
    Type: Grant
    Filed: October 17, 1986
    Date of Patent: February 21, 1989
    Assignee: Stauffer Chemical Company
    Inventor: Raymond A. Felix
  • Patent number: 4774360
    Abstract: Enol ester precursors of benzoyl-1,3-cycloalkyldiones (e.g., the enol ester precursors of 2-(2'-nitrobenzoyl)-1,3-cyclohexanedione compounds) are converted to the desired benzoyl-1,3-cycloalkyldiones by heating the precursor in the presence of base and a catalytic amount of a trialkylsilylcyanohydrin as a cyanide source.
    Type: Grant
    Filed: June 29, 1987
    Date of Patent: September 27, 1988
    Assignee: Stauffer Chemical Company
    Inventor: Elliott Bay
  • Patent number: 4754072
    Abstract: Thiophenols are formed from phenols by first reacting a phenol with thiophosgene to form an aryl chlorothionoformate which is subjected to a halogen exchange reaction using an alkali metal fluoride to yield the corresponding fluorothionoformate. This fluorothionoformate is then rearranged to the corresponding fluorothiolformate by heating and the resulting fluorothiolformate is then hydrolyzed to yield the desired thiophenol.
    Type: Grant
    Filed: March 9, 1987
    Date of Patent: June 28, 1988
    Assignee: Stauffer Chemical Company
    Inventor: Elliott Bay
  • Patent number: 4752604
    Abstract: Compounds having the formula ##STR1## in which R is methyl or ethyl, Y is sulfur or oxygen, and R.sub.1 and R.sub.2 are the same or different tertiary alkyl groups each having from 4 to 6 carbon atoms, are insecticides and nematicides, especially for control of soil insects and nematodes.Symmetrical compounds (R.sub.1 .dbd.R.sub.2) may be prepared by reaction of an alkali metal mercaptide with an alkyl (thio) phosphonic dihalide. The alkali metal mercaptide may be prepared by reaction of a tertiary alkyl mercaptan with an alkali metal or alkali metal hydride.
    Type: Grant
    Filed: July 3, 1986
    Date of Patent: June 21, 1988
    Assignee: Stauffer Chemical Company
    Inventors: Charles G. Chavdarian, Lydia L. Chang, Bruce C. Onisko, Jonathan P. Earhart
  • Patent number: 4748245
    Abstract: A process for the preparation of phenylthiopyrimidines which comprises: (a) reacting a thiopyrimidine; with sulfuryl chloride in the presence of a suitable solvent to form the sulfenyl chloride of said thiopyrimidine; (b) reacting said sulfenyl chloride of said thiopyrimidine with a phenol or substituted phenol, optionally in the presence of a Friedal-Crafts catalyst, to form a thiopyrimidinyl phenol; and (c) reacting said thiopyrimidinylphenol formed in step (b) with a base and an alkylating agent to form the end product.
    Type: Grant
    Filed: March 20, 1986
    Date of Patent: May 31, 1988
    Assignee: Stauffer Chemical Company
    Inventor: Donald R. James
  • Patent number: 4739057
    Abstract: A process for converting organic hydroxyl-containing compounds to halides which comprises reacting the hydroxyl-containing compound with a phosphorushalide reagent of formula: R.sub.n PX.sub.5-n wherein n is selected from 1, 2 and 3; R is selected from the group consisting of C-6 to C-10 aryl and substituted aryl wherein the substituents are selected from the group consisting of straight and branched chain alkyl, alkoxy, and haloalkyl, halogen, sulfonate and mixtures thereof; and X is a halogen. It is preferred to carry out the reaction in the presence of an arylphosphorusoxydihalide solvent. The use of an arylphosphorustetrahalide and particularly phenylphosphorustetrachloride is preferred. The arylphoshorustetrahalide can be prepared in situ by contacting a solution of the corresponding arylphosphorusdihalide in an arylphosphorusoxydihalide solvent with a halogen. The process can further comprise the step of heating the reaction mixture. Maintaining a reaction temperature of from about 0.degree. C.
    Type: Grant
    Filed: June 30, 1986
    Date of Patent: April 19, 1988
    Assignee: Stauffer Chemical Co.
    Inventors: Andrea Leone-Bay, Elliott Bay, Peter E. Timony
  • Patent number: 4737490
    Abstract: Compounds and compositions containing them, for insecticidal control, particularly for use as soil and/or foliar insecticides, have the formula ##STR1## in which R.sub.1 is methyl or ethyl;R.sub.2 is secondary butyl or tertiary butyl;R.sub.3 is hydrogen or methyl;R.sub.4 is hydrogen, methyl or fluoro; andR.sub.5 and R.sub.6 are either both hydrogen or both fluoro.
    Type: Grant
    Filed: November 21, 1986
    Date of Patent: April 12, 1988
    Assignee: Stauffer Chemical Company
    Inventors: Charles G. Chavdarian, Valerie F. Heusinkveld
  • Patent number: 4727051
    Abstract: Compositions having the formulaX.sub.n Mg(OR).sub.2-nin which X is chloro, bromo or iodo; R is a C.sub.1 -C.sub.10 alkyl group and n is a value from about 0.2 to about 1.9 are produced by a process comprising preparing an alkanol adduct of a magneisum halide, reacting the product of this step with metallic magnesium, and drying the product. The compositions are useful as olefin polymerization catalyst components and supports.
    Type: Grant
    Filed: December 15, 1986
    Date of Patent: February 23, 1988
    Assignee: Stauffer Chemical Company
    Inventors: Michael J. Breen, Dennis B. Malpass