Basf Aktiengesellschaft

Badische Anilin- & Soda-fabrik Aktiengesellschaft

Basfaktiengesellschaft

Karl-Heinz Koenig

Gerhard Hamprecht

Dietrich Mangold

Karl-Heinz Feuerherd

Heinz-Guenter Oeser

Ernst-Heinrich Pommer

Karl Kiehs

Adolf Fischer

Christian Reitel

Heinrich Adolphi

Volker Schwendemann

Bruno Wuerzer

Wolfgang Rohr

Ulrich Schirmer

Annegrit Baumann

Sabine Thym

Siegfried Kersten

Norbert Goetz

Bernd Zeeh

Walter Himmele

Costin Rentzea

Adolf Parg

Rolf-Dieter Acker

Rainer Buerstinghaus

August Wigger

Gerd Husslein

Albrecht Mueller

Hans-Gert Recker

Guenter Retzlaff

Manfred Gaeng

Karl-Friedrich Jaeger

Kurt Fett

Juergen Kradel

Hans-Dieter Hoffmann

Josef B Pawliczek

Christian Reital

Walter Boehm

Rudolph Kolbinger

Adolph Fischer

Walter Sanne

Rudolf Kolbinger

A compound of the chemical formula (I) ##STR1## in a specific crystalline form, processes for its preparation, and its use for pest control.

Crystalline form and its preparation

A process for the preparation of 2,4-dichloro- or 2-methyl-4-chlorophenoxyacetic acid or .alpha.-2,4-dichloro- or .alpha.-2-methyl-4-chlorophenoxypropionic acid by reacting phenoxyacetic or 2-methylphenoxyacetic acid or .alpha.-phenoxypropionic or .alpha.-2-methylphenoxypropionic acid with chlorine in water, wherein phenoxyacetic acid or phenoxypropionic acid is precipitated from an aqueous solution thereof, chlorine gas is passed into the resulting suspension of phenoxyacetic or 2-methylphenoxyacetic acid or .alpha.-phenoxypropionic or .alpha.-2-methylphenoxypropionic acid in water at from 30.degree. to 70.degree. C. at a rate not exceeding the rate at which it is consumed in the suspension, until from 100 to 110% of the theoretically required amount of chlorine gas has been taken up by the suspension, and the 2,4-dichloro- or 2-methyl-4-chloro-phenoxyacetic acid or .alpha.-2,4-dichloro- or .alpha.-2-methyl-4-chloro-phenoxypropionic acid is isolated from the suspension.

Preparation of chlorinated phenoxyalkanoic acids

N-Arylthiolcarbamates for the formula ##STR1## where R denotes methyl or ethyl, X denotes halogen, Y denotes alkyl, haloalkyl of at least 2 carbon atoms, alkoxyalkyl, cycloalkyl, alkoxy or halomethoxy, and n denotes one of the integers 1 and 2, herbicides containing these compounds, and their use as herbicides.

N-Arylthiolcarbamates, herbicides containing them, and processes for

Alk-1-enyl isocyanates are prepared by reacting a 1-haloalkylcarbamyl halide and/or a 1-haloalkyl isocyanate with a carboxamide, and are useful starting materials for the preparation of pesticides, dyes, drugs, textile water-repellents, detergents, plastics, bleaches and adhesives.

Preparation of alk-1-enyl isocyanates

Halogenated, tertiary diisocyanates and a process for their preparation by reacting tertiary diisocyanates with halogen, sulfuryl chloride and/or sulfuryl bromide. The halogenated, tertiary diisocyanates which can be prepared by the process according to the invention are valuable starting materials for the preparation of pest control agents, fatliquors, drugs, flameproofing agents, lubricating oils, synthetic resins and lubricants.

Halogenated, tertiary diisocyanates and their preparation

A process for the preparation of 1-monochloroethylcarbamyl chloride by chlorinating ethyl isocyanate or ethylcarbamyl chloride. The 1-chloroethylcarbamyl chloride obtainable according to the invention is an important starting material for the preparation of 1-chloroethyl isocyanate and vinyl isocyanate and accordingly a valuable starting material for the preparation of pest control agents, dyes, drugs, textile waterproofing agents, detergents, plastics, bleaching agents and adhesives, since the said isocyanates contain, in addition to a reactive isocyanate group, an activated double bond or an activated .alpha.-carbon atom.

Preparation of 1-monochloroethylcarbamyl chloride

Silyl-benzimidazole-2-carbamic acid esters of the formula I ##STR1## where Y and Z are hydrogen or a silyl radical of the formula ##STR2## where R.sup.1, R.sup.2 and R.sup.3 independently of one another are unsubstituted or halogen-substituted alkyl, alkenyl or alkynyl of up to 12 carbon atoms, cycloalkyl of up to 7 carbon atoms which is unsubstituted or substituted by alkyl or alkynyl of up to 4 carbon atoms, or phenyl which is unsubstituted or substituted by halogen or alkyl of up to 4 carbon atoms, and R is alkyl of up to 4 carbon atoms, with the proviso that Y and Z are not both hydrogen, and their use as fungicides. The new active ingredients are particularly suitable for combating harmful phycomycetes, ascomycetes and fungi imperfecti.

Silyl-benzimidazole-2-carbamic acid esters and their use as fungicides

Halogenated tertiary alkyl isocyanates and a process for their preparation by reacting a tertiary alkyl isocyanate with halogen, sulfuryl chloride and/or sulfuryl bromide. The halogenated tertiary alkyl isocyanates prepared by the process of the invention are valuable starting materials for the preparation of pest control agents, fatliquoring agents, drugs, flameproofing agents, lubricating oils, synthetic resins and slip agents.

Halogenated tertiary alkyl isocyanates and their preparation

Sulfamic acid halides and processes for the preparation of sulfamic acid halides by reaction of monosubstituted sulfamic acid halides with halogen compounds in the presence of specific amounts of a basic compound and in the presence of an organic solvent, if desired with subsequent treatment with water at a pH of at most 7. The compounds obtainable by the process of the invention, some of which are new, are valuable starting materials for the preparation of crop protection agents, dyes and drugs.

Sulfamic acid halides and processes for the preparation of sulfamic acid

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

Novel .alpha.-haloalkylcarbamic acid halides, and a process for the preparation of .alpha.-haloalkylcarbamic acid halides by reacting alkenyl isocyanates with hydrogen halide. The .alpha.-haloalkylcarbamic acid halides obtained by the process of the invention are valuable starting materials for the preparation of surface-coating raw materials, textile coating agents, dyes, drugs and crop protection agents.

Novel .alpha.-haloalkylcarbamic acid halides, and a process for the

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

Aroylureas of the formula ##STR1## where A denotes a phenyl, thienyl or pyridyl-3 radical which is mono- or polysubstituted by halogen, linear or branched alkyl of 1 to 4 carbon atoms, or linear or branched alkoxy of 1 to 4 carbon atoms, R denotes linear or branched alkyl of 1 to 4 carbon atoms or linear or branched alkoxy of 1 to 4 carbon atoms, and n denotes one of the integers 0,1 and 2, which have an insecticidal and acarididal action, and a process for combating insects and mites with these active ingredients.

Aroylureas

A process for the preparation of 2,2-dimethyl-4-cyano-butyraldoxime N-methyl-carbamate wherein 2,2-dimethyl-4-cyano-butyraldoxime is reacted with an at least equimolar amount of methylcarbamic acid chloride in the form of a concentrated solution of at least 8 moles thereof per liter of inert organic solvent, in the presence of from 1.05 to 2 moles of a tertiary aliphatic amine per mole of 2,2-dimethyl-4-cyano-butyraldoxime, at from 0.degree. to 30.degree. C.

Preparation of 2,2-dimethyl-4-cyano-butyraldoxime N-methyl-carbamate

.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.

Growing community of inventors

Frankenthal, Germany

Karl-Heinz Koenig