Ciba-geigy Corporation

John G Dingwall

Josef Ehrenfreund

Roger G Hall

James Jack

Hans-Ruedi Kanel

Guido Bold

Hans Allgeier

Rudolf Duthaler

Roland Heckendorn

Christof Angst

Antonio Togni

Derek E Brundish

Graham E Fagg

The compounds of the formula ##STR1## in which one of the groups R.sup.1, R.sup.2 and R.sup.3 represents hydrogen, C.sub.1-8 -alkyl, C.sub.3-6 -cycloalkyl, phenyl optionally substituted by halogeno, C.sub.1-4 -alkyl, C.sub.1-4 -alkoxy and/or trifluoromethyl, or C.sub.7-10 -phenylalkyl optionally substituted in the phenyl moiety by halogeno, C.sub.1-4 -alkyl, C.sub.1-4 -alkoxy and/or trifluormethyl, and the other two are hydrogen, or salts thereof. These compounds have valuable pharmaceutical properties.

Substituted propane-phosponous acid compounds

The invention relates to a process for the preparation of cyclopropanecarbaldehydes of formula ##STR1## in which R.sub.1 is C.sub.1 -C.sub.4 alkyl or benzyl, which comprises a) reacting a tetrahydrofuran of formula ##STR2## with a halogenating agent to form a 1,2,4-trihalobutyl ether of formula ##STR3## in which X is halogen and R.sub.2 is unsubstituted or halo-substituted C.sub.1 -C.sub.10 alkyl, C.sub.3 -C.sub.6 cycloalkyl that is unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 alkyl or by C.sub.1 -C.sub.4 alkoxy, or phenyl or benzyl each of which is unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, nitro or cyano, and

Bisulfite adducts of 2,4-dihalobutraldehyde

The compounds of the formula ##STR1## in which one of the groups R.sup.1, R.sup.2 and R.sup.3 represents hydrogen, C.sub.1 -.sub.8 -alkyl, C.sub.3 -.sub.6 -cycloalkyl, phenyl optionally substituted by halogeno, C.sub.1 -.sub.4 -alkyl, C.sub.1 -.sub.4 -alkoxy and/or trifluoromethyl, or C.sub.7 -.sub.10 -phenylalkyl optionally substituted in the phenyl moiety by halogeno, C.sub.1 -.sub.4 -alkyl, C.sub.1 -.sub.4 -alkoxy and/or trifluormethyl, and the other two are hydrogen, or salts thereof. These compounds have valuable pharmaceutical properties.

Substituted propane-phosphonous acid compounds

1,2,4-Trihalobutyl ethers of the formula ##STR1## in which X is halogen and R.sub.2 is unsubstituted or halo-substituted C.sub.1 -C.sub.10 alkyl, C.sub.3 -C.sub.6 -cycloalkyl that is unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 alkyl or by C.sub.1 -C.sub.4 alkoxy, or phenyl or benzyl each of which is unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, nitro or cyano, which are useful as intermediates for the preparation of cyclopropanecarbaldehydes.

1,2,4-trihalobutyl ethers

The invention relates to unsaturated amino acids of the formula I ##STR1## in which R.sup.1 represents hydroxy or etherified hydroxy, R.sup.2 represents hydrogen, alkyl, hydroxy or etherified hydroxy, R.sup.3 represents hydrogen, alkyl, haloalkyl, hydroxyalkyl, lower alkoxyalkyl, arylalkyl, lower alkenyl, halogen or aryl, R.sup.4 represents hydrogen, alkyl or aryl, R.sup.5 represents hydrogen or alkyl, R.sup.6 represents carboxy or esterified or amidated carboxy, R.sup.7 represents amino or amino substituted by alkyl or acyl, A represents unsubstituted or alkyl-substituted .alpha.,.omega.-alkylene having from 1 to 3 carbon atoms or represents a bond, and B represents methylene or a bond, with the proviso that A is other than a bond when B represents a bond, and salts thereof. They can be manufactured, for example, in accordance with the Michaelis-Arbuzov reaction and can be used as pharmacologically active substances.

Unsaturated amino acids

The compounds of the formula ##STR1## in which one of the groups R.sup.1, R.sup.2 and R.sup.3 represents hydrogen, C.sub.1-8 -alkyl, C.sub.3-6 -cycloalkyl, phenyl optionally substituted by halogeno, C.sub. 1-4 -alkyl, C.sub. -4 -alkoxy and/or trifluoromethyl, or C.sub.7-10 -phenylalkyl optionally substituted in the phenyl moiety by halogeno, C.sub.1-4 -alkyl C.sub.1-4 -alkoxy and/or trifluormethyl, and the other two are hydrogen, or salts thereof. These compounds have valuable pharmaceutical properties.

An alpha amino acid amide of the formula ##STR1## Wherein R.sub.3 and R.sub.4 are defined in the specification. The said compounds are intermediates in the preparation of herbicides.

Alpha amino acid amide compounds which are useful intermediates in the

The invention relates to a process for the preparation of cyclopropanecarbaldehydes of formula ##STR1## in which R.sub.1 is C.sub.1 -C.sub.4 alkyl or benzyl, which comprises (a) reacting a tetrahydrofuran of formula ##STR2## in which X is halogen and R.sub.2 is unsubstituted or halo-substituted C.sub.1 -C.sub.10 alkyl, C.sub.3 -C.sub.6 -cycloalkyl that is unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 alkyl or by C.sub.1 -C.sub.4 alkoxy, or phenyl or benzyl each of which is unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, nitro or cyano, with a halogenating agent to form a 1,2,4-trihalobutyl ether of formula ##STR3## in which X is halogen and R.sub.2 is unsubstituted or halo-substituted C.sub.1 -C.sub.10 alkyl, C.sub.3 -C.sub.6 cycloalkyl that is unsubstituted or substituted by halogen C.sub.1 -C.sub.4 alkyl or by C.sub.1 -C.sub.4 alkoxy, or phenyl or benzyl each of which is unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, nitro or cyano, and

Process for the preparation of substituted cyclopropanecarbaldehydes

The compounds of the formula ##STR1## in which one of the groups R.sup.1, R.sup.2 and R.sup.3 represents hydrogen, C.sub.1 -.sub.8 -alkyl, C.sub.3 -.sub.6 -cycloalkyl, phenyl optionally substituted by halogeno, C.sub.1 -.sub.4 -alkyl, C.sub.1 -.sub.4 -alkoxy and/or trifluoromethyl, or C.sub.7 -.sub.10 -phenylalkyl optionally substituted in the phenyl moiety by halogeno, C.sub.1 -.sub.4 -alkyl, C.sub.1 -.sub.4 -alkoxy and/or trifluoromethyl, and the other two are hydrogen, or salts thereof. These compounds have valuable pharmaceutical properties.

The invention relates to novel herbicidally active compounds of formula I ##STR1## in which B represents an imidazolone of formula ##STR2## or A and B together represent a fused imidazolone of formula ##STR3## and the radicals X, R.sup.1, R.sup.2 and A in addition have the meanings given in the text and R.sup.3 represents C.sub.1 -C.sub.4 -alkyl and R.sup.4 represents a methyl or ethyl group subtituted by from 1 to 5 fluorine atoms, processes for the preparation thereof, compositions containing compounds of formula I, methods of controlling weeds, and novel intermediates for the preparation of the compounds of formula I.

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Nuglar, Switzerland

John G Dingwall