Abstract: A process for producing 2,6-difluorobenzonitrile comprises reducing a chloro fluorobenzonitrile selected from 3-chloro-2,6-difluorobenzonitrile, 3,5-dichloro-2,6-difluorobenzonitrile or a mixture thereof by hydrogen gas in the presence of a palladium or platinum catalyst at a temperature of 0.degree. to 200.degree. C.
Abstract: 4-(.alpha.-alkyl-.alpha.-cyano-methyl)2,6-di-substituted phenols having the formula ##STR1## wherein R is methyl, ethyl, n-propyl or isopropyl are prepared by reacting a di-substituted phenol, such as 2,6-di-tertiary-butyl phenol, with a Friedel-Crafts addition agent in the presence of a Friedel-Crafts catalyst such as aluminum chloride to form the corresponding 4-(.alpha.-alkyl-.alpha.-oxo-methyl)2,6-di-substituted phenol. The 4-(.alpha.-alkyl -.alpha.-oxo-methyl)2,6-di-substituted phenol thus formed readily can be reduced to form the corresponding 4-(.alpha.-alkyl-.alpha.-hydroxy-methyl)2,6-di-substituted phenol which thereafter can be reacted with an alkali metal or an alkaline earth metal cyanide to form the desired 4-(.alpha.-alkyl-.alpha.-cyano-methyl)2,6-di-substituted phenol. This can be converted by hydrolysis into the corresponding .alpha.-alkyl-4-hydroxyphenylacetic acid. These acids are well-known insecticidal and acaricidal intermediates.
Abstract: A method for the preparation of certain difluoromethoxyaromatic compounds useful as intermediates in the preparation of pyrethroid pesticides. The method comprises alkylating a p-substituted phenol with excess chlorodifluoromethane at atmospheric or superatmospheric pressures in the presence of a base, water, and an inert water miscible organic solvent or solvent mixtures.
Abstract: Polyisocyanates are prepared by reacting a polyamine solution with a phosgene solution. Excess phosgene and hydrogen chloride formed during the reaction are removed from the reaction mixture. The solvent is subsequently removed from the reaction mixture (e.g., by evaporation and condensation) and treated with a compound containing isocyanate reactive hydrogen atoms to convert any isocyanates present into urethanes and/or ureas. The thus-treated solvent may then be reused, preferably after any urethanes and/or ureas present in the solvent have been removed.
Type:
Grant
Filed:
July 12, 1982
Date of Patent:
September 20, 1983
Assignee:
Bayer Aktiengesellschaft
Inventors:
Gerhard Wegener, Hartmut Knofel, Gunther Ellendt, Marcel Petinaux
Abstract: Fluorine-containing phenylacetic acid esters of the formula ##STR1## in which R represents the radical of an alcohol customary in the case of pyrethroids,R.sup.1 represents C.sub.2-4 -alkyl, C.sub.2-4 -alkenyl or cyclopropyl,X represents H, halogen, alkyl, alkoxy, OCHF.sub.2, SCHF.sub.2, SCClF.sub.2 or SCF.sub.3 andX.sup.1 can vary widely or form a fused ring with X,the overall compound necessarily containing a fluorine atom, which compounds possess arthropodicidal properties. Intermediates therefor and an overall synthesis from an alcohol of the formula ROH and a toluene of the formula ##STR2## are also shown.
Type:
Grant
Filed:
May 3, 1982
Date of Patent:
September 20, 1983
Assignee:
Bayer Aktiengesellschaft
Inventors:
Rainer Fuchs, Erich Klauke, Ingeborg Hammann, Bernhard Homeyer, Wolfgang Behrenz, Wilhelm Stendel, Reinhard Lantzsch, Albrecht Marhold
Abstract: A method for the preparation of certain difluoromethoxyaromatic compounds which are useful intermediates for the preparation of pyrethroid pesticides. The method comprises alkylating a p-substituted phenol with excess chlorodifluoromethane at atmospheric and superatomspheric pressures in the presence of a base, acetone, benzyltriethylammonium chloride, and water.
Abstract: Novel 3-(buta-1',3'-dienyl)-cyclopropane-1-carboxylic acid compounds of the formula ##STR1## wherein X.sub.1 and X.sub.2 are individually a halogen and A is selected from the group consisting of (A) benzyl optionally substituted (B) ##STR2## wherein R.sub.1 is selected from the group consisting of hydrogen and --CH.sub.3 and R.sub.2 is selected from the group consisting of aryl and --CH.sub.2 --C.tbd.CH, (C) ##STR3## wherein R.sub.3 is an aliphatic of 2 to 6 carbon atoms containing at least one carbon-carbon unsaturation, (D) ##STR4## wherein R'.sub.1 and R'.sub.2 are individually selected from the group consisting of hydrogen, halogen, alkyl of 1 to 6 carbon atoms, aryl of 6 to 10 carbon atoms, alkoxycarbonyl of 2 to 5 carbon atoms and cyano and R.sub.3 has the above definition, (E) ##STR5## wherein R.sub.4 is selected from the group consisting of hydrogen, --CN, --CH.sub.3, --CONH.sub.2, --CSNH.sub.2 and --C.tbd.CH, R.sub.5 is selected from the group consisting of chlorine and --CH.sub.
Type:
Grant
Filed:
January 26, 1981
Date of Patent:
August 30, 1983
Assignee:
Roussel Uclaf
Inventors:
Jacques Martel, Jean Tessier, Pierre Girault
Abstract: Compounds, such as 5-(2-chloro-4-trifluoromethylphenoxy)-2-nitroacetophenone oxime-O-(acetic acid, methyl ester) and 5-(2-chloro-4-trifluoromethylphenoxy)-2-chloroacetophenone oxime-O-(acetic acid, methyl ester), are useful for postemergence and preemergence control of weeds, and are represented by Formula I of the application.
Abstract: An improved process for preparation of arylisocyanide dichloride by chlorinating N-arylformamide in the presence of thionyl chloride wherein the improvement comprises preparing the N-arylformamide by formylation of an arylamine having 6 to 12 aryl carbon atoms with a formylating agent in an inert solvent.removing excess formylating agent and by-products of the formylation thereby leaving the N-arylformamide in the form of a solution or suspension in the inert solvent and chlorinating the N-arylformamide in solution or suspension with a chlorinating agent in the presence of thionyl chloride.
Abstract: The m-Cyanoalkoxy-phenylureas of the formula I ##STR1## wherein X is hydrogen or halogen, Y--O is a preferably branched-chain cyanoalkoxy group, and --NR.sub.1 R.sub.2 is a primary, secondary or heterocyclic amino group, exhibit surprisingly good herbicidal activity against mono- and dicotyledonous plants, with a selective action in crops of maize, cereals, cotton and soya bean, and in the case of some of these compounds also in rape crops.
Abstract: A process for the production of tertiary alkyl isocyanates, such as tetramethylxylylene diisocyanates, is disclosed in which the corresponding tertiary alkyl halide is reacted with an alkali metal cyanate utilizing a zinc-pyridine complex as a catalyst which has been prereacted with the cyanate before reaction with the halide.
Abstract: A process for the production of tertiary alkyl isocyanates, such as tetramethylxylylene diisocyanate, is disclosed in which the corresponding tertiary alkyl halide is reacted with an alkali metal cyanate in the presence of water in an amount between 0.02 and 0.2 percent based on the weight of the reaction mixture.
Abstract: 2-Vinyl- and 2-ethylcyclopropanes having an aryl group and a nitrogen-containing radical substituted at the 1-position on the ring are provided. The novel 1,1-disubstituted 2-vinylcyclopropane and 2-ethylcyclopropane compounds of this invention have utility in herbicidal applications and are useful reactants. The 2-vinylcyclopropane derivatives are useful monomers for anionic and radical polymerizations.
Type:
Grant
Filed:
February 22, 1982
Date of Patent:
August 16, 1983
Assignee:
National Distillers and Chemical Corporation
Abstract: A process for production of tertiary aralkyl isocyanates by reaction at low temperatures of the corresponding halides with an excess of isocyanic acid. Manufacture of TMXDI is specifically contemplated.
Type:
Grant
Filed:
March 8, 1982
Date of Patent:
July 26, 1983
Assignee:
American Cyanamid Company
Inventors:
William A. Henderson, Jr., Balwant Singh
Abstract: A process is disclosed for alkylation of benzenes with lower olefins which comprises contacting the benzene and lower olefin with a rare earth exchanged X or Y zeolite catalyst in the presence of sulfur dioxide.
Abstract: 3-Phenoxy-.alpha.-phenoxy-alkanecarboxylic acid derivatives of the formula ##STR1## Wherein Hal is a halogen atom, n is an integer from 1 to 3, R is an acid function and Z is hydrogen or C.sub.1 -C.sub.4 alkyl, are disclosed as possessing a surprising selective herbicidal activity. Methods are disclosed for combatting weeds in mono- and dicotyledonous cultures such as cereals, corn, rice, soya and cotton, which comprise applying to the locus to be protected from weeds a dosage of from 0.1 to 10.0 kilograms per hectare of the above compounds.
Type:
Grant
Filed:
May 14, 1981
Date of Patent:
July 19, 1983
Assignee:
Ciba-Geigy Corporation
Inventors:
Otto Rohr, Georg Pissiotas, Beat Bohner, Kurt Burdeska
Abstract: Sulfur-containing oxime compounds of the formula I given herein are suitable for protecting cultivated plants against the phytotoxic action of aggressive agricultural chemicals, particularly herbicides. There are described methods for producing sulfur-containing oxime compounds of this type, and examples are given illustrating the application of these compounds.
Type:
Grant
Filed:
May 4, 1981
Date of Patent:
July 19, 1983
Assignee:
Ciba-Geigy Corporation
Inventors:
Elmar Sturm, Heinrich Schempp, Henry Martin
Abstract: 2-(3-phenoxy-phenyl)-propionic acid or its pharmaceutical treatments, are prepared by hydrolyzing and partially decarboxylating ##STR1## wherein R=C.sub.1 -C.sub.6 alkyl or amino, the latter compounds being themselves new and, where R=C.sub.1 -C.sub.6 alkyl, have antiinflammatory pharmaceutical properties.
Type:
Grant
Filed:
August 12, 1981
Date of Patent:
July 12, 1983
Assignee:
Chinoin Gyogyszer Es Vegyeszeti Termekek Gyara Rt
Inventors:
Endre Palosi, Gergely Heja, Dezso Korbonits, Pal Kiss, Csaba Gunczi, Judit Cser, Ida Szvoboda, Gabor Szabo, Tamas Kallay, Laszlo Ledniczky, Maria Szomor
Abstract: Compounds of the formula ##STR1## wherein ring A is saturated or aromatic and a saturated ring A which may be present is trans-linked with the second ring; R.sup.1 is a straight-chain alkyl or alkoxy group containing 1 to 11 carbon atoms; R.sup.2 is cyano, a straight-chain alkyl group containing 1 to 11 carbon atoms, an ester group of the formula ##STR2## or, when ring A is saturated, additionally a straight-chain alkoxy group containing 1 to 11 carbon atoms; in the ester group of formula II ring B is either aromatic and X is oxygen or sulfur and R.sup.3 is cyano or a straight-chain alkyl or alkoxy group containing 1 to 10 carbon atoms, or ring B is a trans-1,4-disubstituted cyclohexane ring and X is oxygen and R.sup.3 is cyano or a straight-chain alkyl group containing 1 to 10 carbon atoms; and the total number of carbon atoms in the alkyl and/or alkoxy groups amounts to at most 12, are described. The compounds of formula I are useful in liquid crystal mixtures.
Type:
Grant
Filed:
August 3, 1981
Date of Patent:
July 5, 1983
Assignee:
Hoffmann-La Roche Inc.
Inventors:
Arthur Boller, Martin Schadt, Alois Villiger