Ciba-geigy Corporation

Robert W Lang

Andreas Beck

Konrad Oertle

Pierre Martin

Alfred Sallmann

Andreas Von Sprecher

Paul Wenk

Guido Bold

Peter Herold

Werner Breitenstein

Rudolf Duthaler

Martin Riediker

Bernd Klingert

Odd Kristiansen

Elmar Sturm

Urs Muller

Bruno Schaub

Thomas Allmendinger

Edmond Differding

Substituted alkanophenones of general formula ##STR1## in which R.sub.1 is unsubstituted or fluorinated lower alkyl, R.sub.2 is hydrogen, or unsubstituted or fluorinated lower alkyl or lower alkenyl, X is lower alkylene, oxy, thio or a direct bond, alk is lower alkylene, n is 1 or 2, R.sub.3 is phenyl that is unsubstituted or is substituted by unsubstituted or fluorinated lower alkyl, by etherified or esterified hydroxy, by unsubstituted or lower alkylated amino and/or by free, esterified or amidated carboxy, or is lower alkyl that is unsubstituted, substituted by fluoro and chloro or substituted by free esterified or amidated carboxy, R.sub.4 is free, esterified or amidated carboxy or 5-tetrazolyl, and R.sub.5 is hydrogen or lower alkyl, have leucotriene-antagonistic properties and can be used as anti-allergic active ingredients in medicaments.

Alkanophenones useful for treating allergies

The 1-(3,5-bis-trifluoromethylphenyl)-2-thioxopyrrolidine-4-carboxylic acid derivatives of the formula I below are suitable for protecting crop plants against the phytotoxic action of herbicides and for regulating the plant growth. The 1-(3,5-bis-trifluoromethylphenyl)-2-thioxopyrrolidine-4-carboxylic acid derivatives are those of the formula I ##STR1## wherein A is --COOR.sub.1, --COSR.sub.1, --COO.sup..crclbar. M.sup..sym., --CONR.sub.2 R.sub.3 or --COCl; R.sub.1 is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.6 alkenyl or C.sub.2 -C.sub.6 alkynyl; R.sub.2 and R.sub.3 independently of one another are hydrogen, C.sub.1 -C.sub.4 alkyl or C.sub.3 -C.sub.7 cycloalkyl; or R.sub.2 and R.sub.3 together with the nitrogen atom to which they are bonded are a saturated 3- to 7-membered heterocycle which can contain an additional hetero atom selected from the group comprising O, N and S and which is unsubstituted or up to trisubstituted by C.sub.1 14 C.sub.4 alkyl; and M.sup..sym. is the equivalent of an alkali metal cation or an alkaline earth metal cation or HN.sup..sym. (R.sub.2).sub.3, and their isomers in optically pure or enriched form.

N-phenylpyrrolidines

4-Acylresorcinol ethers of the formula ##STR1## in which R.sub.1 is lower alkyl, R.sub.2 is fluorinated lower alkyl, R.sub.3 is hydrogen, lower alkoxy, trifluoromethyl or halogen, alk is an alkylene or hydroxyalkylene radical which is uninterrupted or interrupted by oxygen, one of the radicals R.sub.4, R.sub.5 and R.sub.7 is a group of the formula --NH--C(.dbd.O)--R.sub.8, a radical R.sub.4 or R.sub.5 which differs from this is a radical R.sub.9 and a radical R.sub.7 which differs from this is a radical R.sub.10, R.sub.6 is hydrogen, lower alkyl, trifluoromethyl, halogen, carboxyl which is free, esterified or amidated, cyano or lower alkanoyl, R.sub.8 is carboxyl which is free, esterified or amidated or 5-tetrazolyl, R.sub.9 is hydrogen, lower alkyl, lower alkoxy, halogen or trifluoromethyl and R.sub.10 is hydrogen, lower alkyl, lower alkoxy, halogen, trifluoromethyl, cyano or carboxyl which is free, esterified or amidated, and their salts have antiallergic and antiinflammatory properties.

Novel fluorinated resorcinol ethers and their use as anti-allergics and

Compounds of formula I ##STR1## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are H, alkyl or aryl, m and n are 0 or 1, and A is a divalent organic radical which, with (CR.sup.1 R.sup.2).sub.m NF--SO.sub.2 (CR.sup.3 R.sup.4).sub.n groups, forms a 5- to 8-membered ring, are admirably suitable fluorinating agents for fluorinating carbon atoms, especially as stereospecific fluorinating agents, when the compounds contain a chiral carbon atom and are in optically active form. The compounds of formula I are prepared by reacting the corresponding silated sulfonamides, wherein the NF group is replaced by an N-SiR.sup.7 R.sup.8 R.sup.9 group and R.sup.7, R.sup.8 R.sup.9 are each independently C.sub.1 -C.sub.12 alkyl, cyclopentyl, cyclohexyl, benzyl or phenyl, with a fluorinating agent.

N-fluorinated sulfonamides

Compounds of the formulae I and Ia ##STR1## in which R.sup.1 is a group which can be transferred to carbonyl or imine compounds, for example alkyl, allyl, vinyl or the radical of an enol or enamine, R.sup.2 is, for example, cyclopentadienyl, R.sup.3 is the radical of an optically active sugar or sugar derivative, Me is Ti, Zr or Hf, x is 0, 1 or 2 and y is 0, 1, 2 or 3, M.sup..sym. is Li.sup..sym., Na.sup..sym., K.sup..sym., MgY.sup..sym., ZnY.sup..sym., CdY.sup..sym., HgY, CuY.sup..sym. or quaternary ammonium, Y being halogen, are suitable for use as chiral reactants for compounds containing aldehyde, keto and/or N-substituted imine groups.

Complexes containing optically active sugar ligands, a process for their

The reaction of allyl bromo- or chloro-difluoroacetates with monochlorisilanes in the presence of zinc with heating gives silyl esters of .alpha.,.alpha.-difluoro-.gamma.,.delta.-pentenoic acids. The free acids, from which acid derivatives can be prepared by conventional methods, are obtained by hydrolysis. The pentenoic acids and pentenoic acid derivatives are suitable for the preparation of polymers and copolymers, from which metal-organic polymers and copolymers having catalytic properties are obtainable.

Process for the preparation of 2,2-difluoropent-4-enoic acids and acid

Process for the preparation of trifluorodichloroethyl-substituted acids

Novel 3-phenylpyrrole derivatives of the formula I ##STR1## wherein R.sup.1 is cyano, trifluoromethyl or C.sub.1 -C.sub.4 -alkoxycarbonyl, R.sup.2 is vinyl or a group --CH.sub.2 --CH.sub.2 --X, in which X is chlorine or bromine, or is cyano, C.sub.1 -C.sub.4 -alkoxycarbonyl, phenylsulfonyl, 4-bromophenylsulfonyl or 4-methylphenylsulfonyl, R is halogen, C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -haloalkyl, and n is zero, one or two, have valuable microbicidal properties for controlling phytopathogenic plant pests, particularly phytopathogenic fungi.

Pesticidal compositions containing 3-phenylpyrrole derivatives

The invention relates to novel N-benzoyl-N,-4-(5-phenylpyrimid-2-yloxy)phenylureas of formula ##STR1## wherein X.sub.1 is hydrogen, halogen, C.sub.1 -C.sub.3 alkoxy or C.sub.1 -C.sub.3 alkylthio,

Substituted benzoylphenylureas compounds useful as pesticides

Compounds of the forulae I and Ia ##STR1## in which R.sup.1 is a group which can be transferred to carbonyl or imine compounds, for example alkyl, allyl, vinyl or the radical of an enol or enamine, R.sup.2 is, for example, cyclopentadienyl, R.sup.3 is the radical of an optically active sugar or sugar derivative, Me is Ti, Zr or Hf, x is 0, 1 or 2 and y is 0, 1, 2 or 3, M.sym. is Li.sym., Na.sym., K.sym., MgY.sym., ZnY.sym., CdY.sym., HgY, CuY.sym. or quaternary ammonium, Y being halogen, are suitable for use as chiral reactants for compounds containing aldehyde, keto and/or N-substituted imine groups.

Metal complexes containing optically active sugar ligands, a process for

There is described a process for producing fungicidally active 4-phenylpyrrole derivatives of the formula I ##STR1## wherein R is halogen, C.sub.1 -C.sub.6 -alkyl or C.sub.1 -C.sub.6 -haloalkyl, and

Novel production processes

4-Acylresorcinol esthers of the formula ##STR1## in which R.sub.1 is lower alkyl, R.sub.2 is fluorinated lower alkyl, R.sub.3 is hydrogen, lower alkoxy, trifluoromethyl or halogen, alk is an alkylene or hydroxyalkylene radical which is uninterrupted or interrupted by oxygen, one of the radicals R.sub.4, R.sub.5 and R.sub.7 is a group of the formula --NH--C(.dbd.O)--R.sub.8, a radical R.sub.4 or R.sub.5 which differs from this is a radical R.sub.9 and a radical R.sub.7 which differs from this is a radical R.sub.10, R.sub.6 is hydrogen, lower alkyl, trifluoromethyl, halogen, carboxyl which is free, esterified or amidated, cyano or lower alkanoyl, R.sub.8 is carboxyl which is free, esterified or amidated or 5-tetrazolyl, R.sub.9 is hydrogen, lower alkyl, lower alkoxy, halogen or trifluoromethyl and R.sub.10 is hydrogen, lower alkyl, lower alkoxy, halogen, trifluoromethyl, cyano or carboxyl which is free, esterified or amidated, and their salts have antiallergic and antiinflammatory properties. They are prepared, for example, by reacting compounds of the formulae ##STR2## in which one of the radicals X.sub.5 and X.sub.6 is hydroxyl which is free or in salt form and the other is an alkoxy radical substituted by reactive esterified hydroxy or epoxy. The invention also relates to intermediates of the formula ##STR3## in which R.sub.2 is fluorinated lower alkyl, R.sub.3 is hydrogen, lower alkoxy, trifluoromethyl or halogen and R.sub.11 is hydrogen or a group of the formula R.sub.1 --C(--O)--, in which R.sub.1 is lower alkyl, and their salts.

Oxaloamino substituted fluorinated resorcinol ethers and anti-allergic

Novel asymmetric thioethers of the formula ##STR1## in which the general symbols have the following meanings: a is an integer of from 1 to 7,

.alpha.-Hydroxy thioethers

Novel asymmetric thioethers of the formula ##STR1## in which the general symbols have the following meanings: R.sup.0 represents hydrogen or C.sub.1-7 -alkanoyl,

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Pratteln, Switzerland

Robert W Lang