Patents Represented by Attorney M. Henry Heines
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Patent number: 4432909Abstract: Herbicidally active thiolcarbamates are employed in combination with certain amine oxanilic acid salts having the formula ##STR1## in which R is selected from the group consisting of C.sub.1 -C.sub.6 alkyl, C.sub.2 -C.sub.6 alkenyl, phenyl and benzyl, and a and b are both integers from zero to four such that the sum of a and b is four. In a typical application, the amine oxanilic acid salts are 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: GrantFiled: December 27, 1982Date of Patent: February 21, 1984Assignee: Stauffer Chemical CompanyInventor: Rayman Y. Wong
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Patent number: 4428767Abstract: Synergistic herbicidal activity is displayed by composition comprising the following two components:(a) a pyrrolidone 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; R.sup.2 is selected from the group consisting of hydrogen, C.sub.1 -C.sub.4 alkyl, acetyl, trifluoromethyl, nitro, cyano, 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.4 alkylsulfonyl, trifluoromethylthio, trifluoromethylsulfinyl, trifluoromethylsulfonyl, pentafluoropropionamido, and 3-methylureido; and R.sup.3 is selected from the group consisting of hydrogen, C.sub.1 -C.sub.4 alkyl, chlorine and trifluoromethyl; and(b) a cyclohexenedione of the formula ##STR2## in which R.sup.Type: GrantFiled: February 11, 1980Date of Patent: January 31, 1984Assignee: Stauffer Chemical CompanyInventor: Gerald H. Thiele
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Patent number: 4416684Abstract: Synergistic herbicidal activity is displayed by compositions comprising the following two components:(a) a pyrrolidone 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; R.sup.2 is selected from the group consisting of hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, acetyl, trifluoromethyl, nitro, cyano, 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.4 alkylsulfonyl, trifluoromethylthio, trifluoromethylsulfinyl, trifluoromethylsulfonyl, pentafluoropropionamido, and 3-methylureido; andR.sup.3 is selected from the group consisting of hydrogen, C.sub.1 -C.sub.4 alkyl, chlorine and trifluoromethyl; and(b) a m-ureidophenyl carbamate of the formula ##STR2## in which R.sup.4 is C.sub.1 -C.Type: GrantFiled: December 31, 1979Date of Patent: November 22, 1983Assignee: Stauffer Chemical CompanyInventor: Gerald H. Thiele
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Patent number: 4386955Abstract: Herbicidally active thiolcarbamates are employed in combination with certain 0-(substituted phenyl) N-methyl carbamates having the formula ##STR1## in which R.sup.4 is selected from the group consisting of ##STR2## R.sup.5 is selected from the group consisting of hydrogen, hydroxy, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 alkoxy, C.sub.2 -C.sub.6 alkylthioalkoxy, and and thiocyanatomethyl,R.sup.6 is selected from the group consisting of hydrogen, C.sub.1 -C.sub.3 alkyl, and C.sub.1 -C.sub.3 alkoxy, and n is zero or one.In a typical application, the O-(substituted phenyl) N-methyl carbamate 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: GrantFiled: April 20, 1981Date of Patent: June 7, 1983Assignee: Stauffer Chemical CompanyInventor: Daniel L. Hyzak
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Patent number: 4381936Abstract: Herbicidally active thiolcarbamates are employed in combination with certain substituted carbamates having the formula ##STR1## in which R.sup.4 and R.sup.5 are each methyl,R.sup.4 and R.sup.5 conjointly form C.sub.1 -C.sub.4 alkylenedioxy,R.sup.4 is --CF.sub.3 and R.sup.5 is hydrogen, orR.sup.4 is --CH.sub.2 Br and R.sup.5 is hydrogen.In a typical application, the carbamate 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: GrantFiled: July 20, 1981Date of Patent: May 3, 1983Assignee: Stauffer Chemical CompanyInventor: Daniel L. Hyzak
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Patent number: 4381195Abstract: Herbicidally active thiolcarbamates are employed in combination with certain N-methylcarbamoyloxy anilides having the formula ##STR1## in which R.sup.4 is selected from the group consisting of hydrogen and carbethoxymethyl,R.sup.5 is selected from the group consisting of C.sub.1 -C.sub.6 alkyl, halogenated C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, C.sub.3 -C.sub.6 cycloalkyl, C.sub.3 -C.sub.5 alkanoylmethyl, C.sub.1 -C.sub.3 alkylamino, C.sub.1 -C.sub.3 dialkylamino, carbamylthiomethyl, and C.sub.2 -C.sub.4 carbalkoxyamino,R.sup.6 is selected from the group consisting of C.sub.1 -C.sub.3 alkyl, C.sub.2 -C.sub.4 alkanoylamino, and halogen,X is selected from the group consisting of oxygen and sulfur, andn is zero or one.In a typical application, the isonitrile is included in sufficient quantity to lessen the rate of soil degradation of the thiolcarbamate.Type: GrantFiled: April 20, 1981Date of Patent: April 26, 1983Assignee: Stauffer Chemical CompanyInventor: Daniel L. Hyzak
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Patent number: 4381196Abstract: Herbicidally active thiolcarbamates are employed in combination with certain O-(substituted phenyl) N-methylcarbamates having the formula ##STR1## in which R.sup.4 is selected from the group consisting of hydrogen and C.sub.1 -C.sub.3 alkyl,R.sup.5 is C.sub.1 -C.sub.3 alkyl,R.sup.6 is selected from the group consisting of hydrogen, formyl, C.sub.1 -C.sub.3 alkoxy, and N-methylcarbamoyloxy, andX is selected from the group consisting of oxygen and sulfur.In a typical application, the N-methylcarbamate 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: GrantFiled: April 20, 1981Date of Patent: April 26, 1983Assignee: Stauffer Chemical CompanyInventor: Daniel L. Hyzak
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Patent number: 4380468Abstract: 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: GrantFiled: October 2, 1981Date of Patent: April 19, 1983Assignee: Stauffer Chemical CompanyInventor: Raymond A. Felix
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Patent number: 4341744Abstract: Soda ash is produced from crude trona ore in a novel process which comprises(a) reducing the ore particle size to a maximum of about 4.0 millimeters in diameter,(b) removing fines from the ore to produce a minimum particle size of about 0.1 millimeter in diameter,(c) differentially electrifying the ore particles according to differences in conductance,(d) segregating the ore particles by electrostatic separation into at least two fractions according to the differences in electrical charge resulting from the electrification of step (c), and(e) calcining the fraction of least conductance to convert the trona contained therein to soda ash,steps (a) through (d) occurring at a temperature not to exceed about 100.degree. C.Type: GrantFiled: November 16, 1979Date of Patent: July 27, 1982Assignee: Stauffer Chemical CompanyInventors: Robert J. Brison, Michael E. Webber
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Patent number: 4317673Abstract: Synergistic herbicidal activity is displayed by a composition comprising the following two components:(a) a pyrrolidone 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; R.sup.2 is selected from the group consisting of hydrogen, C.sub.1 -C.sub.4 alkyl, acetyl, trifluoromethyl, nitro, cyano, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 alkylsulfonyl, C.sub.1 -C.sub.4 alkylsulfinyl, trifluoromethylthio, trifluoromethylsulfinyl, trifluoromethylsulfonyl, pentafluoropropionamido, and 3-methylureido; and R.sup.3 is selected from the group consisting of hydrogen, C.sub.1 -C.sub.4 alkyl, chlorine and trifluoromethyl; and(b) a urea of the formula ##STR2## in which R.sup.Type: GrantFiled: April 8, 1980Date of Patent: March 2, 1982Assignee: Stauffer Chemical CompanyInventor: Gerald H. Thiele
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Patent number: 4315765Abstract: Novel trialkylsulfonium salts of N-phosphonomethylglycine are disclosed herein, having the formula ##STR1## in which R represents C.sub.1 -C.sub.3 alkyl and n is zero or one. The compounds are useful in regulating he natural growth or development of plants and as herbicides.Type: GrantFiled: December 4, 1980Date of Patent: February 16, 1982Assignee: Stauffer Chemical CompanyInventor: George B. Large
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Patent number: 4314841Abstract: The thermal instability and carrier deactivation of a herbicidal benzyl thiocarbamate sulfoxide is reduced by use of a calcium carbonate carrier.Type: GrantFiled: February 17, 1981Date of Patent: February 9, 1982Assignee: Stauffer Chemical CompanyInventor: Herbert B. Scher
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Patent number: 4304587Abstract: A novel composition is disclosed, comprising(a) an aqueous solution of an N-P or N-P-K fertilizer and(b) an attapulgite clay. The composition provides improved emulsion stability when combined with an emulsifiable concentrate of an organophosphorus compound of 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, and C.sub.1 -C.sub.6 alkylthio,R.sup.2 is selected from the group consisting of C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, and C.sub.1 -C.sub.6 alkylthio,R.sup.3 is selected from the group consisting of C.sub.1 -C.sub.6 alkyl, C.sub.2 -C.sub.8 alkylthioalkyl, phenyl, and C.sub.7 -C.sub.12 phenylthioalkyl, the phenyl rings optionally substituted with halogen, C.sub.1 -C.sub.3 alkyl, nitro, or C.sub.1 -C.sub.3 alkylsulfinyl,X is oxygen or sulfur, andY is oxygen or sulfur.Type: GrantFiled: November 5, 1979Date of Patent: December 8, 1981Assignee: Stauffer Chemical CompanyInventor: Gary L. Cummings
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Patent number: 4300945Abstract: Synergistic herbicidal activity is displayed by compositions comprising the following two components:(a) a pyrrolidone of the formula ##STR1## and (b) an acetanilide of the formula ##STR2## in which R.sup.1 is selected from the group consisting of hydrogen, C.sub.1 -C.sub.4 alkyl, and chlorine;R.sup.2 is selected from the group consisting of hydrogen, C.sub.2 -C.sub.6 alkoxyalkyl, and C.sub.3 -C.sub.6 carbalkoxyalkyl;R.sup.3 is selected from the group consisting of hydrogen, C.sub.1 -C.sub.4 alkyl, and chlorine;R.sup.4 is selected from the group consisting of hydrogen, C.sub.1 -C.sub.4 alkyl, and chlorine; andR.sup.5 is selected from the group consisting of hydrogen, C.sub.1 -C.sub.4 alkyl, chlorine, and --NHSO.sub.2 CF.sub.3,at a weight ratio of (a) to (b) of from about 0.1:1 to about 50:1.Type: GrantFiled: February 6, 1980Date of Patent: November 17, 1981Assignee: Stauffer Chemical CompanyInventors: Gerald H. Thiele, Ashley H. Freiberg, Robert L. Skiles, David L. King
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Patent number: 4299616Abstract: Herbicidally active thiolcarbamates are employed in combination with certain substituted carbamates having the formula ##STR1## in which R.sup.4 and R.sup.5 are each methyl,R.sup.4 and R.sup.5 conjointly form C.sub.1 --C.sub.4 alkylenedioxy,R.sup.4 is --CF.sub.3 and R.sup.5 is hydrogen, orR.sup.4 is --CH.sub.2 Br and R.sup.5 is hydrogen.In a typical application, the carbamate 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: GrantFiled: March 31, 1980Date of Patent: November 10, 1981Assignee: Stauffer Chemical CompanyInventor: Daniel L. Hyzak
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Patent number: 4299781Abstract: A low viscosity liquid solution is described, comprising(a) a hydrocarbon-soluble dialkylmagnesium compound of 4 to 20 carbon atoms per molecule(b) a solvent selected from the group consisting of aliphatic, alicyclic, and aromatic hydrocarbons of 5 to 20 carbon atoms, and(c) an organometallic additive selected from the group consisting of R.sub.3 Ga, R.sub.3 In, and RLi, in which R is C.sub.1 -C.sub.12 alkyl or C.sub.5 -C.sub.7 cycloalkyl.Also disclosed is a method of preparing such a solution by in situ generation of the dialkylmagnesium compound via the reaction between metallic magnesium and the appropriate alkyl halide in the presence of both the solvent and the organometallic additive.Type: GrantFiled: May 12, 1980Date of Patent: November 10, 1981Assignee: Texas Alkyls, Inc.Inventors: Loyd W. Fannin, Dennis B. Malpass, Ramiro Sanchez
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Patent number: 4271325Abstract: The dehydrohalogenation of a 1,1,1,3-tetrahalo-4-methylpentane to a 1,1-dihalo-4-methyl-1,3-pentadiene is accomplished in the liquid phase in the presence of a catalytic amount of stannic chloride. The diene is a useful intermediate in the manufacture of insecticidal synthetic pyrethroid esters.Type: GrantFiled: January 9, 1978Date of Patent: June 2, 1981Assignee: Stauffer Chemical CompanyInventor: Harold M. Pitt
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Patent number: 4266965Abstract: A novel aqueous flowable concentrate of the herbicide 2-(.alpha.-naphthoxy)-N,N-diethyl propionamide is disclosed, displaying superior storage stability and dispersion and handling characteristics. The concentrate consists essentially of, by weight of the total concentrate:(a) from 10 to 60% of 2-(.alpha.-naphthoxy)-N,N-diethyl propionamide;(b) from 0.1 to 2.0% of a smectite clay;(c) from 1.0 to 10.0% of a water-soluble nonionic surfactant;(d) from 0.5 to 5.0% of a water-soluble dispersant; and(e) from 1.0 to 20.0% of a water-soluble freezing point depressant;the balance being water; the solid components have an average particle size of from about 5 to about 15 microns.Type: GrantFiled: October 29, 1979Date of Patent: May 12, 1981Assignee: Stauffer Chemical CompanyInventor: Richard W. Simons
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Patent number: 4263038Abstract: Synergistic herbicidal activity is displayed by a composition comprising the following two components:(a) a pyrrolidone 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; R.sup.2 is selected from the group consisting of hydrogen, C.sub.1 -C.sub.4 alkyl, acetyl, trifluoromethyl, nitro, cyano, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 alkylsulfonyl, C.sub.1 -C.sub.4 alkylsulfinyl, trifluoromethylthio, trifluoromethylsulfinyl, trifluoromethylsulfonyl, pentafluoropropionamido, and 3-methylureido; and R.sup.3 is selected from the group consisting of hydrogen, C.sub.1 -C.sub.4 alkyl, chlorine and trifluoromethyl; and(b) 3-amino-1,2,4-triazole,at a weight ratio of (a) to (b) of from about 0.01:1 to about 20:1.Type: GrantFiled: February 29, 1980Date of Patent: April 21, 1981Assignee: Stauffer Chemical CompanyInventor: Gerald H. Thiele
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Patent number: 4263217Abstract: A composition of matter is disclosed comprising a dialkylmagnesium compound of the formulaRMgR'in which R and R' are straight-chain alkyl groups of 1 to 4 carbon atoms each, either identical in length or differing by one carbon atom, and an aluminum diene polymer. The composition is soluble in aliphatic, cycloaliphatic, and aromatic hyrocarbon solvents.Type: GrantFiled: September 24, 1979Date of Patent: April 21, 1981Assignee: Texas Alkyls, Inc.Inventors: Dennis B. Malpass, Loyd W. Fannin