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US 8,299,047 B2Granted
2-alkyl-cycloalk(en)yl-carboxamides
AssigneeBayer CropScience AG
InventorsRalf Dunkel, Hans-Ludwig Elbe, Jörg Nico Greul, Benoit Hartmann, Herbert Gayer, Thomas Seitz, Ulrike Wachendorff-Neumann, Peter Dahmen, Karl-Heinz Kuck
Life of this patent
Estimating the term…
Abstract
Novel 2-alkylcycloalk(en)ylcarboxamides of the formula (I) in which X, s, R1, L, R2 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.
Claims4
A compound of the formula (I)
- in which
- X represents —SiR49R50R51,
- s represents 1 or 2,
- R1 represents hydrogen, C1-C8-alkyl, C1-C6-alkylsulphinyl, C1-C6-alkylsulphonyl, C1-C4-alkoxy-C1-C4-alkyl, C3-C8-cycloalkyl, C1-C6-haloalkyl, C1-C4-haloalkylthio, C1-C4-haloalkylsulphinyl, C1 -C4-halalkylsulphonyl, halo-C1-C4-alkoxy-C1-C4-alkyl, or C3-C8-halocycloalkyl having in each case 1 to 9 fluorine, chlorine or bromine atoms;
- represents formyl, formyl-C1-C3-alkyl, (C1-C3-alkyl)carbonyl-C1-C3-alkyl, or (C1-C3-alkoxy)carbonyl-C1-C3-alkyl;
- represents halo-(C1-C3-alkyl)carbonyl-C1-C3-alkyl or halo-(C1-C3-alkoxy)carbonyl-C1-C3-alkyl having in each case 1 to 13 fluorine, chlorine or bromine atoms;
- represents (C1-C8-alkyl)carbonyl, (C1-C8-alkoxy)carbonyl, (C1-C4-alkyl) carbonyl, or (C3-C8-cycloalkyl)carbonyl;
- represents (C1-C6-haloalkyl)carbonyl, (C1-C6-haloalkoxy)carbonyl, (halo-C1-C4-alkoxy-C1-C4alkyl)carbonyl, or (C3-C8-halocycloalkyl)carbonyl having in each case 1 to 9 fluorine, chlorine or bromine atoms;
- or
- represents —C(═O)C(═O)R6, —CONR7R8 or —CH2NR9R10 ,
- L represents L1 or L2,
- L1 represents C3-C7-cycloalkyl-1,2-ene which is optionally mono- to tetrasubstituted by identical or different substituents selected from the group consisting of fluorine, chlorine, C1-C4-alkyl and C1-C4-haloalkyl,
- L2 represents cyclohexenylene which is optionally mono-to tetrasubstituted by identical or different substituents selected from the group consisting of fluorine, chlorine, C1-C4-alkyl and C1-C4-haloalkyl,
- R2 represents hydrogen, halogen, C1-C4-alkyl or C1-C4-haloalkyl having 1 to 9 fluorine, chlorine or bromine atoms,
- R49 and R50 independently of one another represent hydrogen, C1-C8-alkyl, C1-C8-alkoxy, C1-C4-alkoxy-C1-C4-alkyl, C1-C4-alkylthio-C1-C4-alkyl or C1-C6-haloalkyl,
- R51 represents hydrogen, C1-C8-alkyl, C1-C8-alkoxy, C1-C4-alkoxy-C1-C4-alkyl, C1-C4-alkylthio-C1-C4-alkyl, C2-C8-alkenyl, C2-C8-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, C3-C6-cycloalkyl, or represents in each case optionally substituted phenyl or phenylalkyl,
- R6 represents hydrogen, C1-C8-alkyl, C1-C8-alkoxy, C1-C4-alkoxy-C1-C4-alkyl, C3-C8-cycloalkyl, C1-C6-haloalkyl, C1-C6-haloalkoxy, halo-C1-C4-alkoxy-C1-C4-alkyl, or C3-C8-halocycloalkyl, having in each case 1 to 9 fluorine, chlorine or bromine atoms,
- R7 and R8 independently of one another each represent hydrogen, C1-C8-alkyl, C1-C4-alkoxy-C1-C4-alkyl, or C3-C8-cycloalkyl, C1-C8-haloalkyl, halo-C1-C4-alkoxy-C1-C4-alkyl, or C3-C8-halocycloalkyl, having in each case 1 to 9 fluorine, chlorine or bromine atoms, or
- R7 and R8 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 C1-C4-alkyl, where the heterocycle optionally further contains 1 or 2 non-adjacent heteroatoms selected from the group consisting of oxygen, sulphur and NR11,
- R9 and R10 independently of one another represent hydrogen, C1-C8-alkyl, or C3-C8-cycloalkyl;
- represents C1-C8-haloalkyl or C3-C8-halocycloalkyl, having in each case 1 to 9 fluorine, chlorine or bromine atoms, or
- R9 and R10 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 C1-C4-alkyl, where the heterocycle optionally further contains 1 or 2 non-adjacent heteroatoms selected from the group consisting of oxygen, sulphur and NR11,
- R11 represents hydrogen or C1-C6-alkyl,
- A represents a radical of the formula (A1)
- in which
- R12 represents hydrogen, cyano, halogen, nitro, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-alkylthio, or C3-C6-cycloalkyl;
- represents C1-C4-haloalkyl, C1-C4-haloalkoxy or C1-C4-haloalkylthio, having in each case 1 to 5 halogen atoms;
- or
- represents aminocarbonyl or aminocarbonyl-C1-C4-alkyl,
- R13 represents hydrogen, halogen, cyano, C1-C4-alkyl, C1-C4-alkoxy or C1-C4-alkylthio,
- R14 represents hydrogen, C1-C4-alkyl, hydroxy-C1-C4-alkyl, C2-C6-alkenyl, C3-C6-cycloalkyl, C1-C4-alkylthio-C1-C4-alkyl, or C1-C4-alkoxy-C1-C4-alkyl;
- represents C1-C4-haloalkyl, C1-C4-haloalkylthio-C1-C4-alkyl, or C1-C4-haloalkoxy-C1-C4-alkyl, having in each case 1 to 5 halogen atoms;
- or
- represents phenyl,
- or
- A represents a radical of the formula (A2)
- in which
- R15 and R16 independently of one another represent hydrogen, halogen, C1-C4-alkyl or C1-C4-haloalkyl having 1 to 5 halogen atoms,
- R17 represents halogen, cyano or C1-C4-alkyl;
- or
- represents C1-C4-haloalkyl or C1-C4-haloalkoxy having in each case 1 to 5 halogen atoms,
- or
- A represents a radical of the formula (A3)
- in which
- R18 and R19 independently of one another represent hydrogen, halogen, C1-C4-alkyl or C1-C4-haloalkyl having 1 to 5 halogen atoms,
- R20 represents hydrogen, halogen, C1-C4-alkyl or C1-C4-haloalky, having 1 to 5 halogen atoms,
- or
- A represents a radical of the formula (A4)
- in which
- R21 represents hydrogen, halogen, hydroxyl, cyano, C1-C6-alkyl, C1-C4-haloalkyl, C1-C4-haloalkoxy or C1-C4-haloalkylthio having in each case 1 to 5 halogen atoms,
- or
- A represents a radical of the formula (A5)
- in which
- R22 represents halogen, hydroxyl, cyano, C1-C4-alkyl, C1-C4-alkoxy, or C1-C4-alkylthio;
- or
- represents C1-C4-haloalkyl, C1-C4-haloalkylthio or C1-C4-haloalkoxy, having in each case 1 to 5 halogen atoms,
- R23 represents hydrogen, halogen, cyano, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-alkylthio C1-C4-alkysulphinyl or C1-C4-alkylsulphonyl;
- or
- represents C1-C4-haloalkyl;
- or C1-C4-haloalkoxy, having in each case 1 to 5 halogen atoms,
- or
- A represents a radical of the formula (A6)
- in which
- R24 represents C1-C4-alkyl or C1-C4-haloalkyl having 1 to 5 halogen atoms,
- R25 represents C1-C4-alkyl,
- Q1 represents S (sulphur), O (oxygen), SO, SO2 or CH2,
- p represents 0, 1 or 2,
- provided that when p is 2, R25 represents identical or different radicals,
- or
- A represents a radical of the formula (A7)
- in which
- R26 represents C1-C4-alkyl or C1-C4-haloalkyl having 1 to 5 halogen atoms,
- or
- A represents a radical of the formula (A8)
- in which
- R27 represents C1-C4-alkyl or C1-C4-haloalkyl having 1 to 5 halogen atoms,
- or
- A represents a radical of the formula (A9)
- in which
- R28 and R29 independently of one another represent hydrogen, halogen, amino, C1-C4-alkyl or C1-C4-haloalkyl, having 1 to 5 halogen atoms,
- R30 represents hydrogen, halogen, C1-C4-alkyl or C1-C4-haloalkyl having 1 to 5 halogen atoms,
- or
- A represents a radical of the formula (A10)
- in which
- R31 and R32 independently of one another represent hydrogen, halogen, amino, nitro, C1-C4-alkyl or C1-C4-haloalkyl having 1 to 5 halogen atoms,
- R33 represents hydrogen, halogen, C1-C4-alkyl or C1-C4-haloalkyl having 1 to 5 halogen atoms,
- or
- A represents a radical of the formula (A11)
- in which
- R34 represents hydrogen, halogen, amino, C1-C4-alkylamino, di-(C1-C4-alkyl)amino, cyano, C1-C4-alkyl or C1-C4-haloalkyl having 1 to 5 halogen atoms,
- R35 represents halogen, C1-C4-alkyl or C1-C4-haloalkyl having 1 to 5 halogen atoms,
- or
- A represents a radical of the formula (A12)
- in which
- R36 represents hydrogen, halogen, amino, C1-C4-alkylamino, di-(C1-C4-alkyl)amino, cyano, C1-C4-alkyl or C1-C4-haloalkyl having 1 to 5 halogen atoms,
- R37 represents halogen, C1-C4-alkyl or C1-C4-haloalkyl having 1 to 5 halogen atoms,
- or
- A represents a radical of the formula (A13)
- in which
- R38 represents halogen, C1-C4-alkyl or C1-C4-haloalkyl having 1 to 5 halogen atoms,
- or
- A represents a radical of the formula (A14)
- in which
- R39 represents hydrogen or C1-C4-alkyl,
- R40 represents halogen or C1-C4-alkyl,
- or
- A represents a radical of the formula (A15)
- in which
- R41 represents C1-C4-alkyl or C1-C4-haloalkyl having 1 to 5 halogen atoms,
- or
- A represents a radical of the formula (A16)
- in which
- R42 represents hydrogen, halogen, C1-C4-alkyl or C1-C4-haloalkyl having 1 to 5 halogen atoms,
- or
- A represents a radical of the formula (A17)
- in which
- R43 represents halogen, hydroxyl, C1-C4-alkyl, C1-C4-alkoxy, or C1-C4-alkylthio, C1-C4-haloalkylthio or C1-C4haloalkoxy, having in each case 1 to 5 halogen atoms,
- or
- A represents a radical of the formula (A18)
- in which
- R44 represents hydrogen, cyano, C1-C4-haloalkyl having 1 to 5 halogen atoms, C1-C4-alkoxy-C1-C4-alkyl, hydroxy-C1-C4-alkyl, C1-C4-alkylsulphonyl, di(C1-C4-alkyl)aminosulphonyl, C1-C6-alkylcarbony, or in each case optionally substituted phenylsulphonyl or benzoyl,
- R45 represents hydrogen, halogen, C1-C4-alkyl or C1-C4-haloalkyl having 1 to 5 halogen atoms,
- R46 represents hydrogen, halogen, cyano, C1-C4-alkyl or C1-C4-haloalkyl having 1 to 5 halogen atoms,
- R47 represents hydrogen, halogen, C1-C4-alkyl or C1-C4-haloalky having 1 to 5 halogen atoms,
- or
- A represents a radical of the formula (A19)
- in which
- R48 represents C1-C4-alkyl.
125 more elements
Dependencies are inferred from the claim text.