Basf Aktiengesellschaft

Basfaktiengesellschaft

Heinz-Guenter Oeser

Karl-Heinz Koenig

Dietrich Mangold

Karl-Heinz Feuerherd

Eckhard Hickmann

Karl Eicken

Rainer Becker

Wolfgang Rohr

Heinrich Adolphi

Hans Theobald

Werner Hoffmann

Juergen Varwig

Peter Tonne

Peter Jacobs

Leander Moebius

Diethers of m- or p-hydroxyphenol, as well as the monoethers, are prepared by reacting m- or p-tert.-butoxyphenol of the formula II ##STR1## with a halogen compound in the presence of a hydroxide, carbonate and/or bicarbonate of an alkali metal or alkaline earth metal and an organic solvent which is inert under the reaction conditions, at from 20.degree. C. to 150.degree. C., and, if desired, reacting the resulting diether with a dilute aqueous inorganic acid at from 30.degree. to 100.degree. C. to give the monoether. The end products which can be prepared by the process according to the invention are useful starting materials for the preparation of dyes, drugs and crop protection agents.

Diethers of m- or p-hydroxyphenol

Quinol-4-ylmethane derivatives of the formula I ##STR1## where R.sup.1 is hydrogen or chlorine, R.sup.2 is trifluoromethyl or chlorine, R.sup.3 is a nitrogen-containing, cyclic-unsaturated or acyclic-saturated radical of not more than 6 carbon atoms, R.sup.4 is hydrogen or an anion-stabilizing group and R.sup.5 is hydrogen, an anion center or an acetal radical of not more than 8 carbon atoms, their preparation and their use for the preparation of quinol-4-ylmethane derivatives.

Pyrid-2'-yl-2-trifluoromethyl quinol-4-ylmethanes

Fluorinated anthranilic acid and anthranilonitrile, and a novel process for their preparation by reacting 2,6-difluorobenzonitrile with ammonia and, if the acid is required, hydrolyzing the resulting 6-fluoroanthranilonitrile with a basic compound. The two novel end products are valuable intermediates for the preparation of compounds which are useful for controlling various animal pests and plant pests.

Preparation of fluorinated anthranilic acid and anthranilonitrile

The present invention relates to a simplified process, which avoids organo-lithium intermediates, for the preparation of erythro-.alpha.-piperid-2-yl-2,8-bis-(trifluoromethyl)-quinolin-4-yl-metha nol, wherein 2,8-bis-(trifluoromethyl)-quinoline-4-carboxylic acid or a salt thereof is reacted with a pyrid-2-yl-magnesium halide to give pyrid-2-yl-2,8-bis-(trifluoromethyl)-quinolin-4-yl ketone in the manner of a Grignard reaction, and this product is hydrogenated, in a conventional manner, to give erythro-.alpha.-piperid-2-yl-2,8-bis-(trifluoromethyl)-quinolin-4-yl-metha nol.

Preparation of

6-Fluoropyridyl-(di)(thio)phosphoric acid esters, and their use for combating pests, especially from the classes of insects and Nemathelminthes. The 6-fluoropyridyl-(di)(thio)phosphoric acid esters have the formula ##STR1## where X is oxygen or sulfur, R.sup.1 is linear or branched alkyl of a maximum of 3 carbon atoms and R.sup.2 is linear or branched alkylthio of a maximum of 6 carbon atoms.

6-Fluoropyridyl-(di)(thio)phosphoric acid esters

1-Monohalogenated isocyanates, and a process for the preparation of mixtures of 1-monohalogenated isocyanates and 1,2-unsaturated isocyanates by reacting 1-monohalogenated carbamic acid halides or isocyanates with a halogen-free isocyanate or diisocyanate or by reacting 1,2-unsaturated isocyanates with a carbamic acid halide or a bis-carbamic acid halide. The 1,2-unsaturated isocyanates and 1-monohalogenated isocyanates prepared according to the invention are valuable starting materials for the preparation of pest control agents, dyes, drugs, water-repellent textile finishes, detergents, plastics, bleaches and adhesives.

Preparation of mixtures of 1-monohalogenated isocyanates and

A mixture of an alkyl 3-chloroanthranilate and an alkyl 6-chloroanthranilate, with a particular molar ratio of the components, is prepared by (a) reacting 3-chlorophthalic anhydride with ammonia, an alkali metal hydroxide and an alkali metal hypochlorite or (b) converting 3-chlorophthalic anhydride to 3-chlorophthalimide followed by reaction of the latter with an alkali metal hydroxide and an alkali metal hypochlorite, and, finally, esterifying the mixture of 5-chloroisatoic anhydride and 8-chloroisatoic anhydride, obtained by method (a) or method (b), with an alkanol. The compounds obtainable by the process of the invention are valuable starting materials for the preparation of dyes, crop protection agents and scents.

Preparation of a mixture of an alkyl 3-chloroanthranilate and an alkyl

1-Haloalkyl isocyanates and 1-alkenyl isocyanates are prepared by reacting 1-haloalkylcarbamic acid halides or 1-haloalkyl isocyanates with .alpha.-pinene. The 1-alkenyl isocyanates and 1-haloalkyl isocyanates obtained according to the invention are valuable starting materials for the preparation of pest control agents, dyes, drugs, water-repellent textile finishes, detergents, plastics, bleaches and adhesives.

Preparation of 1-haloalkyl isocyanates and 1-alkenyl isocyanates

.alpha.,.beta.-Dihaloalkyl isocyanates and a process for the preparation of such compounds by reacting .alpha.,.beta.-unsaturated alkyl isocyanates with halogen in the presence of an organic solvent which is inert under the reaction conditions, at from -35.degree. to +90.degree. C. The .alpha.,.beta.-dihaloalkyl isocyanates thus obtainable correspond to the formula ##STR1## where R.sup.1, R.sup.2 and R.sup.3 are identical or different and each is hydrogen, a saturated aliphatic radical of 1 to 10 carbon atoms, a cycloaliphatic radical of 3 to 12 carbon atoms, an araliphatic radical of 7 to 11 carbon atoms or an aromatic radical of 6 to 10 carbon atoms, or R.sup.1 and R.sup.2 together with the carbon atom on which they are present as substituents are cycloalkyl of 3 to 7 ring members, and X is halogen. The compounds are valuable intermediates for the preparation of dyes, surface-coating intermediates, crop protection agents and drugs.

Process for the preparation of .alpha.,.beta.-dihaloalkyl isocyanates

Fluorobenzenes are manufactured by reacting substituted chlorobenzenes with potassium fluoride in the presence of catalytic amounts of cesium fluoride and in the presence of certain solvents; m-nitrofluorobenzenes and m-cyanofluorobenzenes can also be manufactured in the absence of cesium fluoride. The products are starting materials for the manufacture of dyes, pharmaceuticals and pesticides.

Manufacture of substituted fluorobenzenes

A process for the preparation of substituted fluorobenzenes which contain a nitro group or a cyano group and may or may not contain an aliphatic radical or an additional halogen atom, wherein the corresponding substituted chlorobenzene is reacted with potassium fluoride in the presence of a crown ether and a solvent at from 150.degree. to 230.degree. C.

Growing community of inventors

Ludwigshafen, Germany

Heinz-Guenter Oeser