Cycloalkyl carboxylic acid amides, their production and...

Details Cycloalkyl carboxylic acid amides, their production and... Cycloalkyl carboxylic acid amides, their production and...

2001-02-26

2002-08-27

Davis, Brian J. (Department: 1621)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Nitrogen containing other than solely as a nitrogen in an...

C564S190000

Reexamination Certificate

active

06441044

ABSTRACT:

The present invention relates to novel cycloalkylcarboxamides of the formula I
where:
A is C
3
-C
6
-cycloalkyl which may carry one or more substituents selected from the group consisting of halogen, cyano, C
1
-C
6
-alkyl, C
2
-C
6
-alkenyl, C
1
-C
6
-alkoxy or C
1
-C
6
-alkylthio;
Alk is straight-chain or branched C
1
-C
6
-alkylene;
R
1
is C
1
-C
6
-alkyl or C
2
-C
6
-alkenyl, where these radicals may be partially or fully halogenated and/or may carry one or two of the following groups: C
1
-C
4
-alkoxy, C
1
-C
4
-haloalkoxy, C
1
-C
4
-alkylthio, C
1
-C
4
-alkoxycarbonyl, C
3
-C
6
-cycloalkyl and phenyl, where the phenyl may be partially or fully halogenated and/or may carry one to three of the following radicals: nitro, cyano, C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-haloalkoxy, C
1
-C
4
-alkylthio, C
3
-C
6
-cycloalkyl or heterocyclyl;
R
2
, R
3
are hydrogen, C
1
-C
6
-alkyl or C
2
-C
6
-alkenyl, where these radicals may be partially or fully halogenated;
W is a fused bicyclic ring system having in each case six ring atoms, where one or two carbon ring atoms may be replaced by nitrogen atoms, and where these ring systems may carry one to three of the following groups: nitro, halogen, cyano, C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-haloalkoxy, C
1
-C
4
-alkylthio, C
3
-C
6
-cycloalkyl and C
1
-C
4
-alkoxycarbonyl;
and their agriculturally useful salts.
EP 0 170 842 describes N-benzylcyclopropanecarboxamide derivatives and their use as fungicides in agriculture. The compounds described therein are cyclopropylcarboxamides which carry a phenylalkyl group in the amide moiety and which are substituted in the 2-position of the cyclopropane ring by two chlorine atoms. U.S. Pat. No. 4,988,734 describes the corresponding N-(R)-(1-phenylethyl)-1-alkyl-2,2-dichlorocyclopropanecarboxamide stereoisomers. Furthermore, U.S. Pat. No. 5,034,408 describes further 2,2-dichlorocyclopropanecarboxamides which contain a second carboxamide group in the carboxamide moiety. Furthermore, PCT/EP98/01031 discloses &agr;-halo- and &agr;-cyanosubstituted carboxamides having fungicidal action.
The fungicidal properties of the known compounds are, with respect to their activity against harmful fungi such as, for example,
Pyricularia oryzae
not always entirely satisfactory.
It is an object of the present invention to provide novel carboxamides which are active against harmful fungi.
We have found that this object is achieved by the cycloalkylcarboxamides I defined at the outset. Furthermore, we have found processes for preparing the compounds I and the intermediates of the formula II which are required for their preparation. We have found compositions comprising the compounds I, methods for controlling harmful fungi using the compounds I and, finally, the use of the compounds I for controlling harmful fungi.
Depending on the substitution pattern, the compounds of the formula I may contain one or more chiral centers. In this case, they are present as mixtures of enantiomers or diastereomers. The invention provides both the pure enantiomers or diastereomers and their mixtures.
In the definition of the compounds I given at the outset, collective terms were used for the radicals R
1
to R
3
and A which represent individual enumerations of the specific group members. In each of the abovementioned cases, the radicals alkyl, alkylthio, alkoxy, alkoxycarbonyl and alkenyl may be straight-chain or branched.
The term “partially or fully halogenated” is meant to express that the hydrogen atoms in the groups characterized in this way may be partly or fully replaced by identical or different halogen atoms. In each case, the term “halogen” represents fluorine, chlorine, bromine or iodine.
In the case where W is a naphthyl ring in which one or two carbon ring atoms are replaced by nitrogen atoms, it is to be understood as a quinoline, isoquinoline or naphthyridine system.
Examples of other meanings for each of the abovementioned cases are:
C
1
-C
4
-alkyl, and the alkyl moieties of C
1
-C
4
-alkylthio:
methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl and 1,1-dimethylethyl;
C
1
-C
6
-alkyl:
C
1
-C
6
-alkyl as mentioned above, and also pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1-ethyl-1-methylpropyl and 1-ethyl-3-methylpropyl;
C
1
-C
4
-haloalkyl:
a C
1
-C
4
-alkyl radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example, chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl, 2-fluoropropyl, 3-fluoropropyl, 2,2-difluoropropyl, 2,3-difluoropropyl, 2-chloropropyl, 3-chloropropyl, 2,3-dichloropropyl, 2-bromopropyl, 3-bromopropyl, 3,3,3-trifluoropropyl, 3,3,3-trichloropropyl, 2,2,3,3,3-pentafluoropropyl, heptafluoropropyl, 1-(fluoromethyl)-2-fluoroethyl, 1-(chloromethyl)-2-chloroethyl, 1-(bromomethyl)-2-bromoethyl, 4-fluorobutyl, 4-chlorobutyl, 4-bromobutyl and nonafluorobutyl;
C
1
-C
4
-alkoxy, and the alkoxy moieties of C
1
-C
4
-alkoxycarbonyl:
methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy and 1,1-dimethylethoxy;
C
1
-C
4
-haloalkoxy: a C
1
-C
4
-alkoxy radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, bromodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromomethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, pentafluoroethoxy, 2-fluoropropoxy, 3-fluoropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2-bromopropoxy, 3-bromopropoxy, 2,2-difluoropropoxy, 2,3-difluoropropoxy, 2,3-dichloropropoxy, 3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy, 2,2,3,3,3-pentafluoropropoxy, heptafluoropropoxy, 1-(fluoromethyl)-2-fluoroethoxy, 1-(chloromethyl)-2-chloroethoxy, 1-(bromomethyl)-2-bromoethoxy, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy and nonafluorobutoxy;
C
2
-C
6
-alkenyl: ethylene, prop-1-en-1-yl, prop-2-en-1-yl, 1-methylethenyl, buten-1-yl, buten-2-yl, buten-3-yl, 1-methylprop-1-en-1-yl, 2-methylprop-1-en-1-yl, 1-methylprop-2-en-1-yl and 2-methylprop-2-en-1-yl, penten-1-yl, penten-2-yl, penten-3-yl, penten-4-yl, 1-methylbut-1-en-1-yl, 2-methylbut-1-en-1-yl, 3-methylbut-1-en-1-yl, 1-methylbut-2-en-1-yl, 2-methylbut-2-en-1-yl, 3-methylbut-2-en-1-yl, 1-methylbut-3-en-1-yl, 2-methylbut-3-en-1-yl, 3-methylbut-3-en-1-yl, 1,1-dimethylprop-2-en-1-yl, 1,2-dimethylprop-1-en-1-yl, 1,2-dimethylprop-2-en-1-yl, 1-ethylprop-1-en-2-yl, 1-ethylprop-2-en-1-yl, hex-1-en-1-yl, hex-2-en-1-yl, hex-3-en-1-yl, hex-4-en-1-yl, hex-5-en-1-yl, 1-methylpent-1-en-1-yl, 2-methylpent-1-en-1-yl, 3-methylpent-1-en-1-yl, 4-methylpent-1-en-1-yl, 1-methylpent-2-en-1-yl, 2-methylpent-2-en-1-yl, 3-methylpent-2-en-1-yl, 4-methylpent-2-en-1-yl, 1-methylpent-3-en-1-yl, 2-methylpent-3-en-1-yl, 3-methylpent-3-en-1-yl, 4-methylpent-3-en-1-yl, 1-methylpent-4-en-1-yl, 2-methylpent-4-en-1-yl, 3-methylpent-4-en-1-yl, 4-methylpent-4-en-1-yl, 1,1-dimethylbut-2-en-1-yl, 1,1-dimethylbut-3-en-1-yl, 1,2-dimethylbut-1-en-1-yl, 1,2-dimethylbut-2-en-1-yl, 1,2-dimethylbut-3-en-1-yl, 1,3-dimethylbut-1-en-1-yl, 1,3-dimethylbut-2-en-1-yl, 1,3-dimethylbut-3-en-1-yl, 2,2-dimethylbut-3-en-1-yl, 2,3-dimethylbut-1-en-1-yl, 2,3-dimethylbut-2-en-1-yl, 2,3-dimethylbut-3-en-1-yl, 3,3-dimethylbut-1-en-1-yl,

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