Cycloalkylalkanecarboxamides and their preparation and use

Details Cycloalkylalkanecarboxamides and their preparation and use Cycloalkylalkanecarboxamides and their preparation and use

2001-05-31

2002-06-25

Solola, T A (Department: 1626)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C558S445000

Reexamination Certificate

active

06410486

ABSTRACT:

The present invention relates to novel cycloalkylalkane-carboxamides of the formula I
where the substituents have the following meanings:
A is C
3
-C
6
-cycloalkyl which can have attached to it one to three substituents selected from the group consisting of halogen and C
1
-C
3
-alkyl;
R
1
is C
1
-C
6
-alkyl or C
2
-C
6
-alkenyl, it being possible for these radicals to be partially or fully halogenated and/or to have attached to them 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, it being possible for the phenyl to be partially or fully halogenated and/or have attached to it 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
, R
4
are hydrogen or, independently of this meaning, have one of the meanings of the radical R
1
;
n is 0 or 1;
Y is cyano or halogen;
W is phenyl, naphthyl or heteroaryl, it being possible for these radicals to have attached to them 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,
with the exception of the compounds of the formula I where
n is 0 and
A is cyclopentyl.
&agr;-Halo- and &agr;-cyano-substituted carboxamides have already been disclosed in the literature for controlling harmful fungi, in particular for controlling
Pyricularia oryzae
(JP-A 57 185202, JP-A 57 188552, JP-A 57 188551, JP-A 58 029751, JP-A 58 029752, WO 95/31432, JP-A 07 206608, JP-A 07 330511, JP-A 08 012508 and U.S. Pat. No. 4,946,867). J. Pestic. Sci. 12 (1987), 79-84, compiles work relating to the &agr;-halo-substituted carboxamides published to date. This publication also attempts to establish quantitative relationships between structure and effect for this class of fungicides.
U.S. Pat. No. 4,946,867 mentions a cyanoacetamide derivative with a cyclopentyl group in the &agr;-position, N-[1-(4-chlorophenyl)ethyl]-2-cyano-2-cyclopentylethanamide.
Since the fungicidal properties of the known compounds are not always fully satisfactory regarding their activity against harmful fungi, eg.
Pyricularia oryzae
, it is an object of the present invention to find novel carboxamides which are more active against harmful fungi, eg.
Pyricularia oryzae.
We have found that this object is achieved by the novel cycloalkylalkanecarboxamides I defined at the outset. Moreover, we have found processes for the preparation of the compounds I and the intermediates of the formula II required for their preparation. We have found compositions which comprise the compounds I, methods of 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 exist as enantiomer and diastereomer mixtures. The invention relates to the pure enantiomers and diastereomers and also to mixtures of these.
In the definition of the compounds I given at the outset, collective terms which represent individual enumerations of each of the group members were used for the radicals R
1
to R
4
, A and Z. The radicals alkyl, alkylthio, alkoxy, alkoxycarbonyl and alkenyl can be straight-chain or branched.
The radical cycloalkyl represents the unsubstituted skeleton if no specific substitution of a hydrogen by halogen or C
1
-C
3
-alkyl is mentioned. The radical definition cyclopentyl, for example, corresponds to the empirical formula C
5
H
10
.
The term “partially or fully halogenated” is intended to express that in groups characterized thus some or all of the hydrogen atoms may be replaced by identical or different halogen atoms. The meaning halogen represents in each case fluorine, chlorine, bromine or iodine.
Examples of other meanings 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
4
-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, eg. 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, eg. 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-dimethy

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