Carbamoyl carboxylic acid amides

Details Carbamoyl carboxylic acid amides Carbamoyl carboxylic acid amides

1998-02-17

1999-07-13

Geist, Gary

Organic compounds -- part of the class 532-570 series

Organic compounds

Carboxylic acid esters

C07C26100

Patent

active

059228997

DESCRIPTION:

BRIEF SUMMARY
The present invention relates to carbamoylcarboxamides of the general formula I ##STR2## in an isomeric purity of more than 90% by weight where the variables have the following meanings: -C.sub.8 -alkynyl, and/or to have attached to them one to three of the following groups: cyano, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -alkoxycarbonyl, C.sub.3 -C.sub.7 -cycloalkyl, C.sub.3 -C.sub.7 -cycloalkenyl, aryl, aryloxy and hetaryl, turn, to have attached to them one to three of the following substituents: halogen, cyano, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxyalkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -alkoxycarbonyl, aryl, aryloxy and hetaryl; C.sub.1 -C.sub.4 -alkoxyalkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -haloalkylthio, or a phenyl group bonded via oxygen or sulfur which is unsubstituted or can have attached to it one to three of the following substituents: halogen, C.sub.1 -C.sub.4 -alkyl and C.sub.1 -C.sub.4 -alkoxy.
(S) represents the S configuration, (R) the R configuration of the asymmetric carbon atom thus marked, in accordance with the IUPAC nomenclature. In particular, the configuration of the S center in the compounds of the general formula I corresponds to the configuration of L-valine. For the sake of simplicity, the configuration of the compounds I will be termed (SR) configuration hereafter.
"Isomeric purity" refers to the percentage of a compound I (configuration (SR)) of the totality of the four diastereomers of these compounds I which are possible ((SR), (RS), (RR), (SS)).
Furthermore, the invention relates to processes for the preparation of the compounds I. The invention also relates to compositions which comprise the compounds I, to a process for the preparation of such compositions, and to a method of controlling harmful fungi and to the use of the compounds I or the compositions for this purpose.
Racemic mixtures of fungicidal compounds of the type I are disclosed mainly in DE-A 43 21 897 and in the earlier German Application P 44 31 467.1.
However, these mixtures are not yet satisfactory with a view to their fungicidal activity.
It is an object of the present invention to provide novel carbamoylcarboxamides with high isomeric purity which have an improved activity against harmful fungi.
We have found that this object is achieved by the compounds I defined at the outset and by compositions comprising them.
We have furthermore found processes for the preparation of the compounds I and of the compositions comprising them, and also a method of controlling harmful fungi and the use of the compounds I or the compositions for this purpose.
The compounds I can be prepared in a manner known per se starting from the corresponding carbamoylcarboxylic acids II which are based on L-valine. The compounds I are preferably obtainable by processes A and B described hereinbelow (the references "Houben-Weyl" refer to: Houben-Weyl, Methoden verlag, Stuttgart).
The carbamoylcarboxamides I are obtained by reacting the carbamoylcarboxylic acids II with the amines III. ##STR3##
Those carbamoylcarboxylic acids II which are not already known can be prepared by known methods, especially starting from the amino acid L-valine (cf. "Houben-Weyl", Volume 15/1, page 46 to page 305, especially page 117 to page 125).
Equally, those amines III which are not already known can be obtained Deutscher Verlag der Wissenschaften, 15th Edition, Berlin, 1977, page 610 et seq.; "Houben-Weyl", Volume 15/1, pages 648-665; Indian J. Chem. 10, page 366 (1972); J. Am. Chem. Soc. 58, pages 1808-1811 (1936)).
The R isomer can be separated from the racemates of the amines III in a manner known per se, for example by fractional crystallization with optically active tartaric acid or, preferably, by means of enzyme-catalyzed esterification followed by hydrolysis (cf., for example, WO

REFERENCES:
Indian Journal of Chem. vol. 10, 1972, pp. 366-369.
Jrl. Am. Chem.Soc., vol. LVIII, Jul.-Dec., 1936, pp. 1808-1811.

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