Heteroarylpiperidine and -piperazine derivatives as fungicides
AssigneeBayer CropScience AG
InventorsTomoki TSUCHIYA, Pierre WASNAIRE, Sebastian HOFFMANN, Pierre CRISTAU, Thomas SEITZ, Joachim KLUTH, Stefan HILLEBRAND, Juergen BENTING, Daniela PORTZ, Ulrike WACHENDORFF-NEUMANN
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Abstract
Heteroarylpiperidine and -piperazine derivatives of the formula (I) in which the symbols A, X, Y, L1, L2, G, Q, p, R1, R2 and R10 are each as defined in the description, and salts, metal complexes and N-oxides of the compounds of the formula (I), and the use thereof for controlling phytopathogenic harmful fungi and processes for preparing compounds of the formula (I).
Claims16
1-15. (canceled)
A compound of formula (I) and/or a salt, metal complex and/or N-oxide thereof,
- wherein
- A is phenyl which may contain up to two substituents, where the substituents are each independently selected from the following list:
- halogen, cyano, hydroxyl, —NR3R4, —C(═O)NR3R4, nitro, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C8-cycloalkyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, C3-C6-halocycloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkenyloxy, C1-C4-alkynyloxy, C1-C4-alkylthio, C1-C4-alkylsulphonyl, C1-C4-haloalkylthio, C1-C4-haloalkylsulphonyl, C1-C4-alkoxy-C1-C6-alkyl, hydroxyl-C1-C4-alkyl, C1-C6-alkylcarbonyl, C1-C6-alkoxycarbonyl, C1-C6-alkylcarbonyloxy or —C(═O)H, or
- A is pyrazol-1-yl which may contain up to two substituents, where the substituents are each independently selected from the following list:
- halogen, cyano, hydroxyl, nitro, —NR3R4, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, C3-C6-halocycloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, C1-C4-alkylsulphonyl, C1-C4-haloalkylthio, C1-C4-haloalkylsulphonyl, C1-C4-alkoxy-C1-C4-alkyl, hydroxy-C1-C4-alkyl, C1-C6-alkylcarbonyl, C1-C6-alkoxycarbonyl, C1-C6-alkylcarbonyloxy or phenyl,
- R3 and R4 are the same or different and are each independently hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C3-C8-cycloalkyl, benzyl or phenyl,
- L1 is NH or CH2,
- Y is oxygen,
- X is carbon,
- R2 is hydrogen,
- p is 0,
- G is
- where the bond identified by “v” is bonded directly to X and where the bond identified by “w” is bonded directly to Q,
- RG1 is hydrogen or halogen,
- Q is
- where the bond identified by “*” is bonded directly to G or L2, and where the bond identified by “#” is bonded directly to L2 or G, or where the bond identified by “*” is bonded directly to L2, and the bond identified by “#” is at the same time bonded directly to G,
- R5 is hydrogen or C1-C6-alkyl,
- L2 is a direct bond,
- R1 is phenyl which is substituted at least once by a substituent Z4 and may otherwise be unsubstituted or substituted, where the substituents are each independently selected from Z4 and optionally from Z1-2,
- Z1-2 is hydrogen, halogen, cyano, hydroxyl, —SH, nitro, —C(═O)H, —C(═O)NR3R4, —NR3R4, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-halo alkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C3-C8-cycloalkenyl, C3-C8-halocycloalkenyl, C1-C6-alkoxy-C1-C6-alkyl, C1-C6-alkylcarbonyl, C1-C6-haloalkylcarbonyl, C3-C8-cycloalkylcarbonyl, C1-C6-alkoxycarbonyl, C3-C8-cycloalkoxycarbonyl, C3-C8-cycloalkylaminocarbonyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C3-C8-cycloalkoxy, C3-C8-halocycloalkoxy, C2-C6-alkenyloxy, C2-C6-haloalkenyloxy, C2-C6-alkynyloxy, C2-C6-haloalkynyloxy, C1-C4-alkoxy-C1-C4-alkoxy, C1-C6-alkylcarbonyloxy, C1-C6-haloalkylcarbonyloxy, C3-C8-cycloalkylcarbonyloxy, C1-C6-alkylcarbonyl-C1-C4-alkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C3-C6-cycloalkylthio, C1-C6-alkylsulphonyl, C1-C6-haloalkylsulphonyl, C3-C8-cycloalkylsulphonyl, C1-C6-alkylsulphonylamino, C1-C6-haloalkylsulphonylamino, tri(C1-C4-alkyl)silyl, or -L3Z3,
- L3 is a direct bond, —CH2—, —C(═O)—, sulphur, oxygen, —C(═O)O—, —C(═O)NH—, —OC(═O)— or —NHC(═O)—,
- Z3 is a phenyl radical, naphthalenyl radical or a 5- or 6-membered heteroaryl radical, each of which may contain up to two substituents, where the substituents are each independently selected from the following list:
- substituents on carbon:
- halogen, cyano, nitro, hydroxyl, amino, —SH, C1-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, C1-C4-haloalkyl, C2-C4-haloalkenyl, C2-C4-haloalkynyl, C2-C4-alkoxyalkyl, C1-C6-alkylcarbonyl, C1-C6-haloalkylcarbonyl, C1-C6-alkoxycarbonyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C1-C4-alkylthio, C1-C4-haloalkylthio, C1-C4-alkylsulphonyl, C1-C4-haloalkylsulphonyl or C1-C4-alkylamino, di(C1-C4-alkyl)amino,
- substituents on nitrogen:
- C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, C1-C4-alkoxy-C1-C4-alkyl, phenyl, benzyl, C1-C4-haloalkylsulphonyl, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, phenylsulphonyl, C1-C4-alkylsulphonyl, —C(═O)H, or C1-C3-alkylcarbonyl,
- Z4 is —C(═O)OH, —C(═O)NH2, —C(═S)NR3R4, cyano-C1-C6-alkyl, C2-C6-alkenylcarbonyloxy, C2-C6-alkynylthio, C3-C8-halocycloalkylcarbonyloxy, C2-C6-alkenylamino, C2-C6-alkynylamino, C1-C6-haloalkylamino, C3-C8-cycloalkyl-C1-C6-alkylamino, C1-C6-alkoxyamino, C1-C6-haloalkoxyamino, C1-C6-alkylcarbonylamino, C1-C6-haloalkylcarbonylamino, C1-C6-alkoxycarbonylamino, C1-C6-alkylcarbonyl(C1-C6-alkyl)amino, C1-C6-haloalkylcarbonyl(C1-C6-alkyl)amino, C1-C6-alkoxycarbonyl(C1-C6-alkyl)amino, —NR3SO2Z3, C2-C6-alkenylthio, C1-C6-haloalkoxycarbonyl, C1-C6-alkoxy-C1-C4-alkylcarbonyl, —SF5, C1-C6-haloalkoxycarbonylamino, —NHC(═O)H, C1-C6-alkoxy(C1-C4-alkyl)aminocarbonyl, C1-C6-alkoxycarbonyl-C1-C6-alkoxy, —C(═NOR7)R8, —N═C(R9)2, di(C1-C6-alkyl)aminocarbonylamino, di(C1-C6-alkyl)aminosulphonyl, di(C1-C6-haloalkyl)amino, C1-C6-alkylaminosulphonyl, C1-C6-alkylaminocarbonylamino, tri(C1-C4-alkyl)silyloxy, C1-C6-haloalkylsulphonyloxy, C1-C6-alkylsulphonyloxy, tri(C1-C4-alkyl)silyl-C2-C4-alkynyloxy, tri(C1-C4-alkyl)silyl-C2-C4-alkynyl or -L4Z3, or
- Z4 is —C(═O)NR11R12, —SO2NR11R12, —O(C═O)H, —SCN, C1-C3-alkoxysulphonyl, C3-C8-cycloalkylsulphinyl or cyano(C1-C3-alkoxy)-C1-C3-alkyl, or
- Z4 is C1-C3-alkyl which may contain 1 or 2 substituents, where the substituents are each independently selected from the following list:
- C2-C4-alkenyloxy, C2-C4-alkynyloxy, C2-C4-alkenylthio, C2-C4-alkynylthio, C1-C3-alkoxy-C1-C3-alkylthio, C1-C3-alkoxy-C1-C3-alkylsulphinyl, C1-C3-alkoxy-C1-C3-alkylsulphonyl, C1-C3-alkylcarbonyloxy, C1-C3-haloalkylcarbonyloxy, or
- Z4 is a substituted hydroxyl, where the substituents are each selected from the following list:
- C3-C8-cycloalkylsulphonyl, C3-C8-halocycloalkylsulphonyl, C2-C4-alkenylsulphonyl or C(═O)NR3R4,
- R7 is hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, benzyl or Z3,
- R8 is hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C3-C8-cycloalkyl-C1-C4-alkyl, C3-C8-cycloalkyl, C1-C4-alkyl-C3-C8-cycloalkyl, C1-C4-haloalkyl-C3-C8-cycloalkyl, C1-C4-alkoxyl-C1-C4-alkyl, C1-C4-haloalkoxy-C1-C4-alkyl, benzyl or phenyl,
- R9 is the same or different and is independently C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C3-C8-cycloalkyl, benzyl or phenyl,
- R11 is C3-C4-alkenyl, C3-C4-alkynyl, cyano-C1-C3-alkyl, formyl, C1-C3-haloalkyl, benzyl, phenyl, C1-C3-alkylcarbonyl, C3-C8-cycloalkoxycarbonyl, C1-C3-alkoxycarbonyl, C3-C4-alkenyloxycarbonyl, C3-C4-alkynyloxycarbonyl, C1-C3-haloalkylcarbonyl, C3-C8-halocycloalkylcarbonyl, C3-C8-cycloalkoxycarbonyl, C3-C8-cycloalkylcarbonyl or di(C1-C3-alkyl)aminocarbonyl,
- R12 is hydrogen, C3-C4-alkenyl, C3-C4-alkynyl, cyano-C1-C3-alkyl, formyl, C1-C3-haloalkyl, benzyl, phenyl, C1-C3-alkylcarbonyl, C3-C8-cycloalkoxycarbonyl, C1-C3-alkoxycarbonyl, C3-C4-alkenyloxycarbonyl, C3-C4-alkynyloxycarbonyl, C1-C3-haloalkylcarbonyl, C3-C8-halocycloalkylcarbonyl, C3-C8-cycloalkoxycarbonyl, C3-C8-cycloalkylcarbonyl or di(C1-C3-alkyl)aminocarbonyl,
- L4 is —C(═O)O—, —C(═O)NR3-, —OC(═O)—, —NR3C(═O)—, —OCH2C≡C— or —OCH2CH═CH—.
Dependencies are inferred from the claim text.