2-alkyl-cycloalk(en)yl-carboxamides

1. A compound of the formula (I)

in which

X represents —CR 3 R 4 R 5 ,

s represents 1 or 2,

R 1 represents hydrogen, C 1 -C 8 -alkyl, C 1 -C 6 -alkylsulphinyl, C 1 -C 6 -alkylsulphonyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 3 -C 8 -cycloalkyl, C 1 -C 6 -haloalkyl, C 1 -C 4 -haloalkylthio, C 1 -C 4 -haloalkylsulphinyl, C 1 -C 4 -haloalkylsulphonyl, halo-C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, or C 3 -C 8 -halocycloalkyl, having in each case 1 to 9 fluorine, chlorine or bromine atoms;

represents formyl, formyl-C 1 -C 3 -alkyl, (C 1 -C 3 -alkyl)carbonyl-C 1 -C 3 -alkyl, or (C 1 -C 3 -alkoxy)carbonyl-C 1 -C 3 -alkyl;

represents halo-(C 1 -C 3 -alkyl)carbonyl-C 1 -C 3 -alkyl, or halo-(C 1 -C 3 -alkoxy)carbonyl-C 1 -C 3 -alkyl, having in each case 1 to 13 fluorine, chlorine or bromine atoms;

represents (C 1 -C 8 -alkyl)carbonyl, (C 1 -C 8 -alkoxy)carbonyl, (C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl)carbonyl, or (C 3 -C 8 -cycloalkylcarbonyl;

represents (C 1 -C 6 -haloalkyl)carbonyl, (C 1 -C 6 -haloalkoxy)carbonyl, (halo-C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl)carbonyl, or (C 3 -C 8 -halocycloalkyl)carbonyl having in each case 1 to 9 fluorine, chlorine or bromine atoms; or

represents —C(═O)C(═O)R 6 , —CONR 7 R 8 or —CH 2 NR 9 R 10 ,

L represents

in which

n represents 0, 1, 2, 3, or 4,

Y 1 represents fluorine, chlorine, methyl, ethyl, n- or isopropyl, n-, iso-, sec- or tert-butyl, trifluoromethyl or difluoromethyl, wherein Y 1 is identical or different if n is greater than 1,

R 2 represents hydrogen, halogen, C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl having 1 to 9 fluorine, chlorine or bromine atoms,

R 3 represents halogen, C 1 -C 8 -alkyl or C 1 -C 6 -haloalkyl, having 1 to 13 fluorine, chlorine or bromine atoms,

R 4 represents halogen, C 1 -C 8 -alkyl or C 1 -C 6 -haloalkyl, having 1 to 13 fluorine, chlorine or bromine atoms,

R 5 represents hydrogen, halogen, C 1 -C 8 -alkyl or C 1 -C 6 -haloalkyl, having 1 to 13 fluorine, chlorine or bromine atoms, or

R 3 and R 4 together with the carbon atom to which they are attached form a 3- to 6-membered carbocyclic, heterocyclic, saturated or unsaturated ring, each of which is optionally substituted by halogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkyl or C 1 -C 4 -haloalkoxy,

R 6 represents hydrogen, C 1 -C 8 -alkyl, C 1 -C 8 -alkoxy, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 3 -C 8 -cycloalkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -haloalkoxy, halo-C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, or C 3 -C 8 -halocycloalkyl, having in each case 1 to 9 fluorine, chlorine or bromine atoms,

R 7 and R 8 independently of one another each represent hydrogen, C 1 -C 8 -alkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, or C 3 -C 8 -cycloalkyl, halo-C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, or C 3 -C 8 -halocycloalkyl, having in each case 1 to 9 fluorine, chlorine or bromine atoms, or

R 7 and R 8 together with the nitrogen atom to which they are attached form a saturated heterocycle having 5 to 8 ring atoms which is optionally mono- or polysubstituted by identical or different substituents selected from the group consisting of halogen and C 1 -C 4 -alkyl, where the heterocycle optionally further contains 1 or 2 non-adjacent heteroatoms selected from the group consisting of oxygen, sulphur and NR 11 ,

R 9 and R 10 independently of one another represent hydrogen, C 1 -C 8 -alkyl, or C 3 -C 8 -cycloalkyl;

represents C 1 -C 8 -haloalkyl or C 3 -C 8 -halocycloalkyl, having in each case 1 to 9 fluorine, chlorine or bromine atoms, or

R 9 and R 10 together with the nitrogen atom to which they are attached form a saturated heterocycle having 5 to 8 ring atoms which is optionally mono- or polysubstituted by identical or different substituents selected from the group consisting of halogen and C 1 -C 4 -alkyl, where the heterocycle optionally further contains 1 or 2 non-adjacent heteroatoms selected from the group consisting of oxygen, sulphur and NR 11 ,

R 11 represents hydrogen or C 1 -C 6 -alkyl,

A represents a radical of the formula (A2)

in which

R 15 and R 16 independently of one another represent hydrogen, halogen, C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms,

R 17 represents halogen, cyano or C 1 -C 4 -alkyl; or

represents C 1 -C 4 -haloalkyl or C 1 -C 4 -haloalkoxy having in each case 1 to 5 halogen atoms,

or

A represents a radical of the formula (A3)

in which

R 18 and R 19 independently of one another represent hydrogen, halogen, C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms,

R 20 represents hydrogen, halogen, C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl, having 1 to 5 halogen atoms,

or

A represents a radical of the formula (A4)

in which

R 21 represents hydrogen, halogen, hydroxyl, cyano, C 1 -C 4 -haloalkyl, C 1 -C 4 -haloalkoxy or C 1 -C 4 -haloalkylthio, having in each case 1 to 5 halogen atoms,

or

A represents a radical of the formula (A6)

in which

R 24 represents C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms,

R 25 represents C 1 -C 4 alkyl,

Q 1 represents S (sulphur), O (oxygen), SO, SO 2 or CH 2 ,

p represents 0, 1 or 2,

provided that when p is 2, R 25 represents identical different radicals,

or

A represents a radical of the formula (A7)

in which

R 26 represents C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms,

or

A represents a radical of the formula (A8)

in which

R 27 represents C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms,

or

A represents a radical of the formula (A9)

in which

R 28 and R 29 independently of one another represent hydrogen, halogen, amino, C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl, having 1 to 5 halogen atoms,

R 30 represents hydrogen, halogen, C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms,

or

A represents a radical of the formula (A 10)

in which

R 31 and R 32 independently of one another represent hydrogen, halogen, amino, nitro, C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms,

R 33 represents hydrogen, halogen, C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms,

or

A represents a radical of the formula (A11)

in which

R 34 represents hydrogen, halogen, amino, C 1 -C 4 -alkylamino, di-(C 1 -C 4 alkyl)amino, cyano, C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms,

R 35 represents halogen, C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms,

or

A represents a radical of the formula (A12)

in which

R 36 represents hydrogen, halogen, amino, C 1 -C 4 -alkylamino, di-(C 1 -C 4 -alkyl)amino, cyano, C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms,

R 37 represents halogen, C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms,

or

A represents a radical of the formula (A13)

in which

R 38 represents halogen, C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl having 1 to halogen atoms,

or

A represents a radical of the formula (A14)

in which

R 39 represents hydrogen or C 1 -C 4 -alkyl,

R 40 represents halogen or C 1 -C 4 -alkyl,

or

A represents a radical of the formula (A18)

in which

R 44 represents hydrogen, cyano, C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, hydroxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkylsulphonyl, di(C 1 -C 4 -alkyl)aminosulphonyl, C 1 -C 6 -alkylcarbonyl, or in each case optionally substituted phenylsulphonyl or benzoyl,

R 45 represents hydrogen, halogen, C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms,

R 46 represents hydrogen, halogen, cyano, C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms,

R 47 represents hydrogen, halogen, C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms,

or

A represents a radical of the formula (A19)

in which

R 48 represents C 1 -C 4 -alkyl.

2. A process for preparing the compound according to claim 1 , comprising reacting

(a) a carboxylic acid derivative of the formula (II)

in which

A is as defined in claim 1 and

X 1 represents halogen or hydroxyl,

with an aniline derivative of the formula (III)

in which

R 1 , L, R 2 , R 3 , R 4 and R 5 are as defined in claim 1 ,

optionally in the presence of a catalyst, optionally in the presence of a condensing agent, optionally in the presence of an acid binder and optionally in the presence of a diluent, or

(b) a compound of the formula (I-a)

in which

L, R 2 , R 3 , R 4 , R 5 and A are as defined in claim 1 ,

with a halide of the formula (IV)

R 1A —X 2   (IV)

in which

R 1A represents C 1 -C 8 -alkyl, C 1 -C 6 -alkylsulphinyl, C 1 -C 6 -alkylsulphonyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, or C 3 -C 8 -cycloalkyl;

represents C 1 -C 6 -haloalkyl, C 1 -C 4 -haloalkylthio, C 1 -C 4 -haloalkylsulphinyl, C 1 -C 4 -haloalkylsulphonyl, halo-C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, or C 3 -C 8 -halocycloalkyl, having in each case 1 to 9 fluorine, chlorine or bromine atoms;

represents formyl, formyl-C 1 -C 3 -alkyl, (C 1 -C 3 -alkyl)-carbonyl-C 1 -C 3 -alkyl, (C 1 -C 3 -alkoxy)carbonyl-C 1 -C 3 -alkyl, halo-(C 1 -C 3 -alkyl)carbonyl-C 1 -C 3 -alkyl or halo-(C 1 -C 3 -alkoxy)carbonyl-C 1 -C 3 -alkyl, having in each case 1 to 13 fluorine, chlorine or bromine atoms;

represents (C 1 -C 8 -alkyl)carbonyl, (C 1 -C 8 -alkoxy)carbonyl, (C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl)-carbonyl, (C 3 -C 8 -cycloalkyl)carbonyl, (C 1 -C 6 -haloalkyl)carbonyl, (C 1 -C 6 -haloalkoxy)carbonyl, (halo-C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl)carbonyl, or (C 3 -C 8 -halocycloalkyl)carbonyl, having in each case 1 to 9 fluorine, chlorine or bromine atoms; or

represents —C(═O)C(═O)R 6 , —CONR 7 R 8 or —CH 2 NR 9 R 10 ,

R 6 , R 7 , R 8 , R 9 and R 10 are as defined in claim 1 ,

X 2 represents chlorine, bromine or iodine,

in the presence of a base and a diluent.

3. A composition for controlling unwanted microorganisms, comprising at least one compound according to claim 1 , and an extender, a surfactant, or a combination thereof.

4. A method for controlling unwanted microorganisms, comprising applying 2-alkylcycloalk(en)ylcarboxamides of the formula (I) according to claim 1 to plants and plant parts directly or to their environment, habitat, or store.

5. A method for controlling unwanted microorganisms, comprising contacting a compound according to claim 1 with the microorganisms or their habitat.

6. A process for preparing compositions for controlling unwanted microorganisms, comprising mixing a compound according to claim 1 with an extender, a surfactant or a combination thereof.

7. The compound of the formula (I) according to claim 1 , wherein

R 1 represents hydrogen, methyl, methoxymethyl, formyl, —CH 2 —CHO, —(CH 2 ) 2 —CHO, —CH 2 —CO—CH 3 , —CH 2 —CO—CH 2 CH 3 , —CH 2 —CO—CH(CH 3 ) 2 , —C(═O)CHO, —C(═O)C(═O)CH 3 , —C(═O)C(═O)CH 2 OCH 3 , —C(═O)CO 2 CH 3 , or C(═O)CO 2 CH 2 CH 3 ,

R 2 represents hydrogen, fluorine, chlorine, methyl, ethyl, or trifluoromethyl,

R 3 represents chlorine, methyl, ethyl, isopropyl, or trifluoromethyl,

R 4 represents chlorine, methyl, ethyl, isopropyl, or trifluoromethyl, and

R 5 represents hydrogen, chlorine, methyl, ethyl, isopropyl, or trifluoromethyl.

8. The compound according to claim 1 is Compound I-c-4:

9. The method for controlling unwanted microorganisms according to claim 5 , wherein the compound is Compound I-c-4:

10. The process for preparing the composition according to claim 6 , wherein the compound is Compound I-c-4: