2-alkyl-cycloalk(en)yl-carboxamides
View Patent ↗Novel 2-alkylcycloalk(en)ylcarboxamides of the formula (I) in which X, s, R 1 , L, R 2 and A are as defined in the description, a plurality of processes for preparing these compounds and their use for controlling unwanted microorganisms, and also novel intermediates and their preparation.
1. A compound of the formula (I)
in which
X represents —SiR 49 R 50 R 51 ,
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 -halalkylsulphonyl, 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 -alkyl) carbonyl, or (C 3 -C 8 -cycloalkyl)carbonyl;
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 L 1 or L 2 ,
L 1 represents C 3 -C 7 -cycloalkyl-1,2-ene which is optionally mono- to tetrasubstituted by identical or different substituents selected from the group consisting of fluorine, chlorine, C 1 -C 4 -alkyl and C 1 -C 4 -haloalkyl,
L 2 represents cyclohexenylene which is optionally mono-to tetrasubstituted by identical or different substituents selected from the group consisting of fluorine, chlorine, C 1 -C 4 -alkyl and C 1 -C 4 -haloalkyl,
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 49 and R 50 independently of one another represent hydrogen, C 1 -C 8 -alkyl, C 1 -C 8 -alkoxy, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkylthio-C 1 -C 4 -alkyl or C 1 -C 6 -haloalkyl,
R 51 represents hydrogen, C 1 -C 8 -alkyl, C 1 -C 8 -alkoxy, C 1 -C 4 -alkoxy-C 1-C 4 -alkyl, C 1 -C 4 -alkylthio-C 1 -C 4 -alkyl, C 2 -C 8 -alkenyl, C 2 -C 8 -alkynyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -haloalkynyl, C 3 -C 6 -cycloalkyl, or represents in each case optionally substituted phenyl or phenylalkyl,
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, C 1 -C 8 -haloalkyl, 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 (A1)
in which
R 12 represents hydrogen, cyano, halogen, nitro, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylthio, or C 3 -C 6 -cycloalkyl;
represents 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
represents aminocarbonyl or aminocarbonyl-C 1 -C 4 -alkyl,
R 13 represents hydrogen, halogen, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -alkylthio,
R 14 represents hydrogen, C 1 -C 4 -alkyl, hydroxy-C 1 -C 4 -alkyl, C 2 -C 6 -alkenyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -alkylthio-C 1 -C 4 -alkyl, or C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl;
represents C 1 -C 4 -haloalkyl, C 1 -C 4 -haloalkylthio-C 1 -C 4 -alkyl, or C 1 -C 4 -haloalkoxy-C 1 -C 4 -alkyl, having in each case 1 to 5 halogen atoms; or
represents phenyl,
or
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 -haloalky, having 1 to 5 halogen atoms,
or
A represents a radical of the formula (A4)
in which
R21 represents hydrogen, halogen, hydroxyl, cyano, C 1 -C 6 -alkyl, C 1 -C4-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 (A5)
in which
R 22 represents halogen, hydroxyl, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, or C 1 -C 4 -alkylthio; or
represents C 1 -C 4 -haloalkyl, C 1 -C 4 -haloalkylthio or C 1 -C 4 -haloalkoxy, having in each case 1 to 5 halogen atoms,
R 23 represents hydrogen, halogen, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylthio C 1 -C 4 -alkysulphinyl or C 1 -C 4 -alkylsulphonyl; 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 (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 or 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 (A10)
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 5 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 (A15)
in which
R 41 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 (A16)
in which
R 42 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 (A17)
in which
R 43 represents halogen, hydroxyl, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, or C 1 -C 4 -alkylthio, C 1 -C 4 -haloalkylthio or C 1 -C 4 haloalkoxy, having in each case 1 to 5 halogen atoms,
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 -alkylcarbony, 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 -haloalky 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 composition for controlling unwanted microorganisms, comprising at least one compound according to claim 1 , and an extender, a surfactant, or a combination thereof.
3. A method for controlling unwanted microorganisms, comprising contacting a compound according to claim 1 with microorganisms or their habitat.
4. 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.