Patents by Inventor Raymond A. Felix

Raymond A. Felix 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: 4444693
    Abstract: A method of preparing N-phosphonomethylglycine comprising: (a) reacting O,O-dialkylaminomethylphosphonate with formaldehyde to produce a triazine compound; (b) reacting the triazine formed in step (a) with an acyl cyanide to form the O,O-dialkyl-N-phosphonomethyl-N-cyanomethyl amide; and (c) hydrolyzing the amide formed in step (b) to yield N-phosphonomethylglycine.
    Type: Grant
    Filed: September 7, 1982
    Date of Patent: April 24, 1984
    Assignee: Stauffer Chemical Company
    Inventor: Raymond A. Felix
  • Patent number: 4429124
    Abstract: A method for preparing N-phosphonomethylglycine comprising (a) O,O-dialkylaminomethylphosphonate with formaldehyde to produce a triazine; (b) reacting the triazine formed in step (a) with an acyl halide to form the O,O-dialkyl-N-phosphonomethyl-N-chloromethyl acetamide of the acyl halide; (c) reacting the amide formed in step (b) with metal cyanide to form O,O-dialkyl-N-cyanomethyl-N-acetamide; and (d) hydrolyzing the acetamide formed in step (c) to yield N-phosphonomethylglycine.
    Type: Grant
    Filed: August 23, 1982
    Date of Patent: January 31, 1984
    Assignee: Stauffer Chemical Company
    Inventor: Raymond A. Felix
  • Patent number: 4427599
    Abstract: A method of preparing N-phosphonomethylglycine comprising (a) reacting a triazine with an acyl halide to form the N-cyanomethyl-N-halomethyl amide of the acyl halide; reacting the said amide with a phosphite to form a phosphonate compound; and hydrolyzing said phosphonate to yield N-phosphonomethylglycine.
    Type: Grant
    Filed: February 14, 1983
    Date of Patent: January 24, 1984
    Assignee: Stauffer Chemical Company
    Inventor: Raymond A. Felix
  • Patent number: 4425283
    Abstract: A process for preparing N-phosphonomethylglycine which comprises:(1) reacting a primary amine with formaldehyde to produce N,N', N"-tris-substituted-hexahydro-s-triazine;(2) reacting the triazine with an haloacetyl halide, preferably chloroacetyl chloride, to form the N-(substituted)-N-halomethyl acetamide of the haloacetyl halide;(3) reacting the amide with O,O-di-(substituted)-aminomethylphosphonate to form O,O-di-(substituted)-1-phosphonomethyl-3-(substituted)-1,3-imidazol-4-one; and(4) hydrolyzing the 1,3-imadazol-4-one to yield N-phosphonomethylglycine.
    Type: Grant
    Filed: November 17, 1982
    Date of Patent: January 10, 1984
    Assignee: Stauffer Chemical Company
    Inventor: Raymond A. Felix
  • Patent number: 4425284
    Abstract: A method of preparing N-phosphonomethylglycine comprising (a) reacting a substituted triazine with an acyl halide to form the N-carboalkoxymethyl-N-halomethyl amide of the acyl halide; reacting the said amide with a phosphite to form a phosphonate compound; and hydrolyzing said phosphonate to yield N-phosphonomethylglycine.
    Type: Grant
    Filed: August 30, 1982
    Date of Patent: January 10, 1984
    Assignee: Stauffer Chemical Company
    Inventor: Raymond A. Felix
  • Patent number: 4400204
    Abstract: An herbicide antidote having the formula ##STR1## in which X is selected from the group consisting of hydrogen and halogen wherein the halogen is chlorine, bromine or iodine.
    Type: Grant
    Filed: March 16, 1981
    Date of Patent: August 23, 1983
    Assignee: Stauffer Chemical Company
    Inventor: Raymond A. Felix
  • Patent number: 4396419
    Abstract: Herbicide antidote compounds having the formula ##STR1## in which R is selected from the group consisting of alkenyl having 2-12 carbon atoms, inclusive; and alkylalkoxy having 1-8 carbon atoms, inclusive.
    Type: Grant
    Filed: March 16, 1981
    Date of Patent: August 2, 1983
    Assignee: Stauffer Chemical Company
    Inventor: Raymond A. Felix
  • Patent number: 4380468
    Abstract: Herbicidally active thiolcarbamates are employed in combination with certain substituted phenyl isonitriles having the formula ##STR1## in which R.sup.1 is selected from the group consisting of C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 alkylthio, phenyl, halogen, benzylthio, and p-chlorobenzylthio, andR.sup.2 is selected from the group consisting of hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, and halogen.In a typical application, the isonitrile is included in sufficient quantity to lessen the rate of soil degradation of the thiolcarbamate. As a result, the herbicidal effectiveness of the thiolcarbamate is enhanced and prolonged, rendering a single application of the herbicide effective over a longer period of time.
    Type: Grant
    Filed: October 2, 1981
    Date of Patent: April 19, 1983
    Assignee: Stauffer Chemical Company
    Inventor: Raymond A. Felix
  • Patent number: 4361438
    Abstract: Compounds having the formula ##STR1## in which X and Y are halogen; R is cyano, halogen, thio-C.sub.1 -C.sub.4 alkyl, phenyl, pyridyl, hydroxy, or OR.sub.1 ; R.sub.1 is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 mono- or di-alkylcarbamyl, C.sub.2 -C.sub.6 alkoxyalkyl, phenylcarbamyl, C.sub.1 -C.sub.6 alkanoyl or C.sub.1 -C.sub.6 haloalkanoyl; and n is: (a) 1 or 2 if R is thioalkyl, cyano or phenyl; and (b) 2 if R is otherwise as defined, are herbicides.
    Type: Grant
    Filed: January 21, 1981
    Date of Patent: November 30, 1982
    Assignee: Stauffer Chemical Company
    Inventor: Raymond A. Felix
  • Patent number: 4356026
    Abstract: Compounds having the formula ##STR1## in which R.sub.1 is alkyl, lower alkenyl, chloro-lower alkyl, lower cycloalkyl, lower alkoxy, thio-lower alkyl, or ##STR2## R.sub.2 is hydrogen, lower alkoxyalkyl or lower alkanoyl; R.sub.3 and R.sub.4 are independently hydrogen, lower alkyl or lower alkoxy; X and Y are independently chloro, fluoro or bromo; Z is hydrogen, methyl, dimethyl or one methyl and one chloro substituent; and n is 0 or 1. The compounds have utility as herbicides, particularly as post-emergence herbicides.
    Type: Grant
    Filed: January 23, 1980
    Date of Patent: October 26, 1982
    Assignee: Stauffer Chemical Company
    Inventor: Raymond A. Felix
  • Patent number: 4351665
    Abstract: Sulfinoate compounds have the formula ##STR1## in which R and R.sub.1 are each haloalkyl having 1-4 carbon atoms. The compounds have utility as herbicidal antidotes for the protection of crops from thiocarbamate or trifluralin herbicidal injury.
    Type: Grant
    Filed: March 9, 1981
    Date of Patent: September 28, 1982
    Assignee: Stauffer Chemical Company
    Inventor: Raymond A. Felix
  • Patent number: 4336062
    Abstract: Novel compounds having the formula ##STR1## in which X is (H).sub.2 or (CH.sub.3).sub.2 ; Y is oxygen or sulfur; R.sub.1 is alkyl, lower alkenyl, cyclopropyl, lower alkoxy, thio-lower alkyl or ##STR2## R.sub.2 and R.sub.3 are independently hydrogen, lower alkyl, lower alkenyl, or lower alkoxy and n is 0 or 1. The compounds have been found to possess herbicidal activity.
    Type: Grant
    Filed: May 16, 1978
    Date of Patent: June 22, 1982
    Assignee: Stauffer Chemical Company
    Inventor: Raymond A. Felix
  • Patent number: 4336058
    Abstract: An herbicide antidote compound having the formula ##STR1## and herbicide antidote compositions comprising (a) an herbicidally effective amount of a thiocarbamate compound of the formula: ##STR2## in which R.sub.1 is alkyl having 1-6 carbon atoms, inclusive; R.sub.2 is selected from the group consisting of alkyl having 1-6 carbon atoms, inclusive; and cyclohexyl; or R.sub.1 and R.sub.2 form indistinguishable parts of a single alkylene ring having 4-10 carbon atoms, inclusive; and R.sub.
    Type: Grant
    Filed: February 6, 1981
    Date of Patent: June 22, 1982
    Assignee: Stauffer Chemical Company
    Inventor: Raymond A. Felix
  • Patent number: 4314838
    Abstract: Novel biocidal compounds having the general structural formula ##STR1## wherein R is selected from the group consisting of C.sub.1 -C.sub.4 alkyl, including ethyl, ethyl, propyl and butyl, ##STR2## phenyl, or substituted phenyl wherein the substituents are selected from the group comprising --CH.sub.3, --CF.sub.3, --NO.sub.2, bromine and chlorine.
    Type: Grant
    Filed: March 2, 1981
    Date of Patent: February 9, 1982
    Assignee: Stauffer Chemical Company
    Inventor: Raymond A. Felix
  • Patent number: 4308050
    Abstract: Novel biocidal compounds having the general structural formula ##STR1## wherein R and R' are independently selected from the group consisting of C.sub.1 -C.sub.4 alkyl including methyl, ethyl, propyl and butyl, C.sub.2 -C.sub.4 alkenyl including ethenyl, propenyl and butenyl, phenyl, and substituted phenyl wherein the substituents are selected from the group consisting of NO.sub.2, CH.sub.3, CF.sub.3, Cl and Br.
    Type: Grant
    Filed: March 2, 1981
    Date of Patent: December 29, 1981
    Assignee: Stauffer Chemical Company
    Inventor: Raymond A. Felix
  • Patent number: 4282231
    Abstract: Novel biocidal compounds having the general structural formula ##STR1## wherein X is selected from the group consisting of --H, halogen, including --Br, --Cl and --F, C.sub.1 -C.sub.4 alkyl, including methyl, ethyl, propyl and butyl.
    Type: Grant
    Filed: July 25, 1980
    Date of Patent: August 4, 1981
    Assignee: Stauffer Chemical Company
    Inventor: Raymond A. Felix
  • Patent number: 4269988
    Abstract: Novel biocidal compounds having the general structural formula ##STR1## wherein R and R' are independently selected from the group consisting of C.sub.1 -C.sub.4 alkyl including methyl, ethyl, propyl and butyl, C.sub.2 -C.sub.4 alkenyl including ethenyl, propenyl and butenyl, phenyl, and substituted phenyl wherein the substituents are selected from the group consisting of NO.sub.2, CH.sub.3, CF.sub.3, Cl and Br.
    Type: Grant
    Filed: July 25, 1980
    Date of Patent: May 26, 1981
    Assignee: Stauffer Chemical Company
    Inventor: Raymond A. Felix
  • Patent number: 4269984
    Abstract: Novel biocidal compounds having the general structural formula ##STR1## wherein R is selected from the group consisting of C.sub.1 --C.sub.4 alkyl, including methyl, ethyl, propyl and butyl, ##STR2## phenyl, substituted phenyl wherein the substituents are selected from the group comprising --CH.sub.3, --CF.sub.3, --NO.sub.2, bromine and chlorine.
    Type: Grant
    Filed: July 25, 1980
    Date of Patent: May 26, 1981
    Assignee: Stauffer Chemical Company
    Inventor: Raymond A. Felix
  • Patent number: 4265658
    Abstract: Compounds having the formula ##STR1## in which X is hydrogen, chloro or bromo; R is hydrogen or lower alkanoyl; R.sub.1 is lower alkyl, cyclopropyl or NR.sub.3 R.sub.4 ; R.sub.2 is hydrogen or lower alkanoyl; and R.sub.3 and R.sub.4 are independently hydrogen or lower alkyl, are useful as herbicides, primarily for post-emergent application.
    Type: Grant
    Filed: September 20, 1978
    Date of Patent: May 5, 1981
    Assignee: Stauffer Chemical Company
    Inventor: Raymond A. Felix
  • Patent number: 4238405
    Abstract: Novel biocidal compounds have the general structural formula ##STR1## wherein n is 0, 1, or 2 and R is alkyl, alkylcarbalkoxy, cyclohexyl, halophenyl, benzyl, N,N-di-lower alkyl carbamoyl, hexamethyleneimino carbonyl, pyrimidyl, lower alkyl substituted pyrimidyl, benzimidazole, lower alkyl substituted imidazole, benzothiazole and O,O-di-lower alkyl thiophosphoryl; with the proviso that when n is 0, R is other than alkyl or cyclohexyl.
    Type: Grant
    Filed: September 19, 1977
    Date of Patent: December 9, 1980
    Assignee: Stauffer Chemical Company
    Inventor: Raymond A. Felix