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).
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Patent number: 5925795Abstract: This invention relates to processes for the preparation of aryl-.beta.-diketones and aryl-pyrimidine ketones. In addition, this invention relates to the preparation of aryl-.beta.-triketones and dimethyl aminomethylene .beta.-diketones, which are useful as crop protection intermediates.Type: GrantFiled: September 16, 1996Date of Patent: July 20, 1999Assignee: Zeneca LimitedInventors: Raymond A. Felix, Hsiao-Ling M. Chin, Frank X. Woolard, David L. Lee
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Patent number: 5786301Abstract: This invention relates to substituted N-benzotriazoles of the formula ##STR1## in which: R.sup.1, R.sup.2, R.sup.3,R.sup.4, R.sup.5,R.sup.6, R.sup.7, X are as defined in the specification. The compounds exhibit herbicidal activity.Type: GrantFiled: August 8, 1996Date of Patent: July 28, 1998Assignee: Zeneca LimitedInventors: Donald R. James, Raymond A. Felix
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Patent number: 5707930Abstract: Herbicidal 4-cycloalkyl-5-substituted pyrimidine compounds of the formula ##STR1## are described. Herbicidal compositions containing such substituted-pyrimidinyl compounds and methods of controlling undesirable vegetation employing these compounds are also disclosed. The compounds in which XR, is hydroxyl are also useful as intermediates for producing the disclosed substituted-pyrimidinyl derivatives.Type: GrantFiled: September 16, 1996Date of Patent: January 13, 1998Assignee: Zeneca LimitedInventors: Raymond A. Felix, Hsiao-Ling M. Chin, Frank X. Woolard, David L. Lee, David B. Kanne
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Patent number: 5369086Abstract: Substituted N-benzotriazoles of the general formula ##STR1## exhibit herbicidal activity. Herbicidal compositions and related methods of using the substituted N-benzotriazoles are also disclosed.Type: GrantFiled: April 28, 1993Date of Patent: November 29, 1994Assignee: Zeneca LimitedInventors: Donald R. James, Raymond A. Felix
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Patent number: 5350856Abstract: This invention relates to a process for producing a compound of the formula ##STR1## comprising reacting a compound having the formula ##STR2## with cyanogen chloride or cyanogen bromide.Type: GrantFiled: January 10, 1990Date of Patent: September 27, 1994Assignee: ICI Americas Inc.Inventor: Raymond A. Felix
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Patent number: 5234895Abstract: Compounds having the formula ##STR1## in which: R.sub.1 is hydrogen or fluoro;R.sub.2 is halo, trihalomethyl, pentahaloethyl, mono- or difluoromethyl, di-, tri- or tetrafluoroethyl, C.sub.1 -C.sub.2 fluoroalkylthio, C.sub.1 -C.sub.2 fluoroalkoxy, methylthio, methylsulfonyl, halomethylsulfonyl, C.sub.1 -C.sub.2 alkyl or methoxy;R.sub.3 is hydrogen or halo;R.sub.4 is hydrogen, C.sub.1 -C.sub.4 alkyl; C.sub.2 -C.sub.4 alkenyl; C.sub.2 -C.sub.4 alkynyl; C.sub.1 -C.sub.4 haloalkyl; C.sub.2 -C.sub.4 haloalkenyl; C.sub.1 -C.sub.4 alkoxy; C.sub.2 -C.sub.4 alkoxyalkyl, 3-trifluoromethylphenyl, or --(CH.sub.2).sub.n Y;R.sub.5 and R.sub.6 are hydrogen, or R.sub.5 and R.sub.6 together form a bond;R.sub.7 is C.sub.1 -C.sub.4 alkyl;R.sub.8 and R.sub.9 are hydrogen, or R.sub.8 and R.sub.9 together form a bond;Y is cyano; 4-chlorophenyl; C.sub.3 -C.sub.6 cycloalkyl, furyl or tetrahydrofuryl optionally substituted by halo or C.sub.1 -C.sub.4 alkyl; or COR.sub.10 in which R.sub.10 is hydroxy, C.sub.1 -C.sub.5 alkoxy, C.sub.Type: GrantFiled: June 19, 1992Date of Patent: August 10, 1993Assignee: Imperial Chemical Industries PLCInventor: Raymond A. Felix
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Patent number: 5011990Abstract: Compounds having the formula ##STR1## wherein R is an aromatic or aliphatic group; R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are independently hydrogen, C.sub.1-4 alkyl or phenyl; X is halogen; and Y is halogen or an aromatic group; are prepared in a regioselective manner by treating a compound having the formula ##STR2## with a catalytic amount of a palladium(O) or a palladium(II) transition metal catalyst.Type: GrantFiled: December 27, 1988Date of Patent: April 30, 1991Inventor: Raymond A. Felix
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Patent number: 4913722Abstract: 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: GrantFiled: November 15, 1988Date of Patent: April 3, 1990Assignee: ICI Americas Inc.Inventors: Raymond A. Felix, Jeffery T. Springer, Eugene G. Teach, Frank X. Woolard
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Patent number: 4911745Abstract: Novel herbicides are 3-(substituted) phenyl-2-(substituted imino)-1,3,4-dihydrothiadiazoles. Also disclosed are intermediates for such compounds, and processes for producing the herbicidal compounds and their intermediates.Type: GrantFiled: July 8, 1988Date of Patent: March 27, 1990Assignee: ICI Americas Inc.Inventor: Raymond A. Felix
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Patent number: 4900351Abstract: 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: GrantFiled: March 14, 1988Date of Patent: February 13, 1990Assignee: ICI Americas Inc.Inventor: Raymond A. Felix
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Patent number: 4806653Abstract: 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: GrantFiled: October 17, 1986Date of Patent: February 21, 1989Assignee: Stauffer Chemical CompanyInventor: Raymond A. Felix
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Patent number: 4724261Abstract: A process for the preparation of cyclic urea compounds in which a substituted anilino alkanone is reacted with an arylsubstituted isocyanate to form an intermediate imidazoline compound, and said imidazoline compound is hydrogenated in the presence of suitable catalyst to form an imidazolidine of the formula ##STR1## wherein X, X', Y and Y' are the same or different and are selected from the group consisting of trifluoromethyl, chloro, bromo, fluoro, hydrogen, cyano, nitro, alkyl, thioalkyl, halothioalkyl, alkoxy and sulfonylalkyl wherein the alkyl groups have from 1 to 4 carbon atoms; and R is selected from the group consisting of hydrogen and alkyl having from 1 to about 4 carbon atoms. Also included are intermediate anilino alkanones and the process of making them.Type: GrantFiled: November 24, 1986Date of Patent: February 9, 1988Assignee: Stauffer Chemical CompanyInventor: Raymond A. Felix
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Patent number: 4654072Abstract: Compounds having the formula ##STR1## in which R is hydrogen, cyano or --COOR.sub.2 ; R.sub.1 is hydrogen or C.sub.1 -C.sub.4 alkyl; R.sub.2 is hydrogen or C.sub.1 -C.sub.4 alkyl; and Z is ##STR2## in which A is halogen, B is halogen or hydrogen and Y is nitrogen or --CH--, are herbicides.Type: GrantFiled: September 17, 1985Date of Patent: March 31, 1987Assignee: Stauffer Chemical CompanyInventor: Raymond A. Felix
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Patent number: 4650512Abstract: A substituted oxazolidone compound having the formula ##STR1## wherein Ar.sup.1 and Ar.sup.2 are the same or different and are aromatic or a substituted aromatic group wherein the substituent is selected from chlorine, bromine, chloride or trifluoromethyl, and R is lower alkyl having from 1 to 6 carbon atoms.Type: GrantFiled: September 27, 1984Date of Patent: March 17, 1987Assignee: Stauffer Chemical CompanyInventors: Raymond A. Felix, Eugene G. Teach
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Patent number: 4629499Abstract: Herbicidally active thiolcarbamates are employed in combination with certain allyl amine salts of thiocarbamic acid compounds having the formula ##STR1## wherein R.sub.4 and R.sub.5 are independently selected from the group consisting of allyl, alkyl substituted allyl, and lower alkyl groups having from about 1 to about 6 carbon atoms;R.sub.6 and R.sub.7 are independently selected from the group consisting of allyl, alkyl substituted allyl, and lower alkyl groups having from about 1 to about 6 carbon atoms; andX is oxygen or sulfur wherein at least one of R.sub.4 and R.sub.5 and at least one of R.sub.6 and R.sub.7 is an allyl group. In a typical application, the allyl amine salt of thiocarbamic acid compound 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 single application of the herbicide effective over a longer period of time.Type: GrantFiled: March 15, 1984Date of Patent: December 16, 1986Assignee: Stauffer Chemical CompanyInventors: Raymond A. Felix, Joanna K. Hsu
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Patent number: 4589907Abstract: Compounds having the formula ##STR1## in which Z is ##STR2## wherein X is hydrogen or halogen and Y is --CH or N; R is alkyl, phenyl, trihalomethylphenyl, cyanomethyl, carboalkoxymethyl, ##STR3## alkenyl; and R.sub.1 is hydrogen, lower alkyl, halo-(lower alkyl), or Z; and intermediate alkyl onium salts of the type ##STR4## in which R.sub.3 is C.sub.1 -C.sub.8 alkyl, G is nitrogen or phosphorus and Z' is ##STR5## wherein X is hydrogen or halogen and Y is --CH or N; are herbicides.Type: GrantFiled: September 17, 1985Date of Patent: May 20, 1986Assignee: Stauffer Chemical CompanyInventor: Raymond A. Felix
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Patent number: 4569802Abstract: A method of preparing N-phosphonomethylglycine comprising; (a) reacting N-hydroxymethyl haloacetamide with a chlorinating agent, preferably thionyl chloride to form N-chloromethyl haloacetamide; (b) reacting N-chloromethyl haloacetamide with a phosphite to form N-haloacetylaminomethyl phosphonate; (c) reacting the phosphonate with derivative of haloacetic acid to form N-haloacyl-N-(cyanomethyl or carboalkoxymethyl) phosphonate; and (d) hydrolyzing this later phosphonate to yield N-phosphonomethylglycine.Type: GrantFiled: June 27, 1983Date of Patent: February 11, 1986Assignee: Stauffer Chemical CompanyInventor: Raymond A. Felix
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Patent number: 4559082Abstract: Herbicidally active thiocarbamates are employed in combination with certain unsaturated aryl sulfides, sulfoxides or sulfones having the formula ##STR1## in which R.sup.4 is hydrogen, halogen, C.sub.1 -C.sub.6 alkyl or C.sub.1 -C.sub.6 alkoxy; R.sup.5 is C.sub.2 -C.sub.6 haloalkenyl or C.sub.2 -C.sub.6 alkynyl; and n equals 0 or 2. In a typical application, the unsaturated aryl sulfide, sulfoxide or sulfone is included in sufficient quantity to lessen the rate of soil degradation of the thiocarbamate. As a result, the herbicidal effectiveness of the thiocarbamate is enhanced and prolonged, rendering a single application of the herbicide effective over a longer period of time.Type: GrantFiled: August 12, 1983Date of Patent: December 17, 1985Assignee: Stauffer Chemical Co.Inventors: Raymond A. Felix, Joanna K. Hsu
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Patent number: 4552968Abstract: 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: GrantFiled: February 15, 1985Date of Patent: November 12, 1985Assignee: Stauffer Chemical CompanyInventor: Raymond A. Felix
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Patent number: 4535181Abstract: 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: GrantFiled: May 14, 1984Date of Patent: August 13, 1985Assignee: Stauffer Chemical CompanyInventor: Raymond A. Felix