Piperidine pyrazoles as fungicides

Compound of formula (XIII),

• in which
• W7 is chlorine, bromine, iodine, p-toluenesulphonyloxy or methylsulphonyloxy and
• Y is oxygen or sulphur,
• R2 is hydrogen or halogen
• Q is
• where the bond identified by “x” is bonded directly to the thiazole and the bond identified by “y” is bonded directly to L1 or R1,
• R5 is hydrogen, cyano, C1-C3 alkyl or C1-C3 haloalkyl,
• L1 is a direct bond, —CH2—, —(C═O)—, sulphur or oxygen,
• R1 is phenyl which contains at least one substituent Z4 and additionally two, three or four further substituents which independently are selected from Z4 and Z1,
• or
• R1 is naphthyl, dihydronaphthalenyl, tetrahydronaphthalenyl, hexahydronaphthalenyl, octahydronaphthalenyl or indenyl which contains at least one substituent Z5 and additionally contains two, three or four further substituents which independently are selected from Z5 and Z1,
• or
• R1 is an optionally benzo-fused, substituted 5- or 6-membered heteroaryl which contains at least one substituent Z6 and additionally contains two, three or four further substituents which on the carbon are selected independently of one another from Z6 and Z1 and on the nitrogen are selected independently of one another from Z6 and Z2,
• or
• R1 is a C3-C8 cycloalkyl or is a C5-C8 cycloalkenyl which contains at least one substituent Z7 and additionally contains two, three or four further substituents which independently of one another are selected from Z7 and Z1,
• Z1 is hydrogen, halogen, hydroxyl, nitro, cyano, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, halocycloalkyl, alkoxy, alkoxyalkyl, hydroxyalkyl, haloalkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcycloalkyl, cycloalkoxyalkyl, cycloalkylamino, alkylthio, haloalkylthio, cycloalkylthio, cycloalkylalkyl, alkylcarbonyloxy, alkylcarbonylamino, haloalkylcarbonylamino, alkylcarbonylthio, alkylsulphinyl, haloalkylsulphinyl, alkylsulphonyloxy, haloalkylsulphonyloxy, alkylcycloalkylalkyl, —C(═O)NR3R4, —NR3R4, tri(C1-C2 alkyl)silyl, or -L3Z3,
• Z2 is hydrogen, halogen, hydroxyl, nitro, cyano, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, halocycloalkyl, alkoxy, alkoxyalkyl, hydroxyalkyl, haloalkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcycloalkyl, cycloalkoxyalkyl, cycloalkylamino, alkylthio, haloalkylthio, cycloalkylthio, cycloalkylalkyl, alkylcarbonyloxy, alkylcarbonylamino, haloalkylcarbonylamino, alkylcarbonylthio, alkylsulphinyl, haloalkylsulphinyl, alkylsulphonyloxy, haloalkylsulphonyloxy, alkylcycloalkylalkyl, —C(═O)NR3R4, —NR3R4 or tri(C1-C2 alkyl)silyl,
• Z3 is a phenyl radical, naphthalenyl radical or a 5- or 6-membered heteroaryl radical which in each case may contain 0, 1, 2 or 3 substituents, the substituents being selected independently of one another from the following list:
• Substituents on the carbon:
• halogen, cyano, nitro, hydroxyl, amino, —SH, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, halocycloalkyl, alkoxyalkyl, alkylcarbonyl, haloalkylcarbonyl, alkoxycarbonyl, alkoxy, haloalkoxy, cycloalkoxy, halocycloalkoxy, alkenyloxy, alkynyloxy, alkoxyalkoxy, alkylamino, dialkylamino, alkylthio, haloalkylthio, alkylsulphinyl, haloalkylsulphinyl, alkylsulphonyl, haloalkylsulphonyl, trisilylalkyl or phenyl,
• Substituents on the nitrogen:
• hydrogen, —C(═O)H, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, halocycloalkyl, alkylcycloalkyl, cycloalkylalkyl, alkoxyalkyl, alkylsulphonyl, haloalkylsulphonyl, cycloalkylsulphonyl, phenylsulphonyl, alkylcarbonyl, haloalkylcarbonyl, alkoxycarbonyl, haloalkoxycarbonyl, cycloalkoxycarbonyl, —C(═O)NR3R4, phenyl or benzyl,
• Z4 is SH, C(═O)H, C7-C8 cycloalkyl, C7-C8 halocycloalkyl, cycloalkylcycloalkyl, halocycloalkylalkyl, cycloalkenyl, halocycloalkenyl, C5-C6 alkoxyalkyl, alkoxyalkoxyalkyl, alkylthioalkyl, alkylsulphinylalkyl, alkylsulphonylalkyl, alkylaminoalkyl, dialkylaminoalkyl, haloalkylaminoalkyl, cycloalkylaminoalkyl, C5-C6 alkylcarbonyl, haloalkylcarbonyl, cycloalkylcarbonyl, cycloalkoxycarbonyl, cycloalkylalkoxycarbonyl, cycloalkylaminocarbonyl, haloalkoxyalkyl, C5-C6 hydroxyalkyl, C5-C6 alkoxy, C5-C6 haloalkoxy, cycloalkoxy, halocycloalkoxy, cycloalkylalkoxy, alkenyloxy, haloalkenyloxy, alkynyloxy, haloalkynyloxy, alkoxyalkoxy, haloalkylcarbonyloxy, cycloalkylcarbonyloxy, alkylcarbonylalkoxy, C5-C6 alkylthio, C5-C6 haloalkylthio, C5-C6 alkylsulphinyl, C5-C6 haloalkylsulphinyl, alkylsulphonyl, C1-C4 haloalkylsulphonyl, cycloalkylsulphonyl, tri(C3-C4 alkyl)silyl, alkylsulphonylamino or haloalkylsulphonylamino,
• Z5 is tri(C2-C4 alkyl)silyl, benzyl, phenyl, SH, C5-C6 alkoxy, C5-C6 haloalkoxy, C2-C6 alkenyloxy, C2-C6 alkenyloxy, C5-C6 alkylthio or C5-C6 haloalkylthio,
• Z6 is
• Substituents on the carbon:
• SH, cycloalkylcycloalkyl or tri(C3-C4 alkyl)silyl,
• Substituents on the nitrogen:
• alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, halocycloalkyl, alkylcycloalkyl, cycloalkylalkyl, cycloalkylcycloalkyl, alkylsulphonyl, C(═O)H, benzyl or phenyl,
• Z7 is cyano, halogen, hydroxyl, oxo, C1-C4 alkyl, C1-C4 haloalkyl, alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, C1-C4 haloalkylthio or phenyl,
• L3 is a direct bond, —CH2— —C═O— sulphur, oxygen, —C(═O)O—, —C(═O)NH—, —OC(═O)— or —NHC(═O)—,
• R3 and R4, identically or differently and independently of one another, are hydrogen, alkyl, alkenyl, alkynyl, haloalkyl, cycloalkyl, benzyl or phenyl,
• and/or a salt, metal complex and/or N-oxide thereof.

Compound of formula (II),

• in which
• W8 is acetyl, C1-C4 alkoxycarbonyl, benzyl or benzyloxycarbonyl and
• Y is oxygen or sulphur,
• R2 is hydrogen or halogen
• Q is
• where the bond identified by “x” is bonded directly to the thiazole and the bond identified by “y” is bonded directly to L1 or R1,
• R5 is hydrogen, cyano, C1-C3 alkyl or C1-C3 haloalkyl,
• L1 is a direct bond, —CH2—, —(C═O)—, sulphur or oxygen,
• R1 is phenyl which contains at least one substituent Z4 and additionally two, three or four further substituents which independently are selected from Z4 and Z1,
• or
• R1 is naphthyl, dihydronaphthalenyl, tetrahydronaphthalenyl, hexahydronaphthalenyl, octahydronaphthalenyl or indenyl which contains at least one substituent Z5 and additionally contains two, three or four further substituents which independently are selected from Z5 and Z1
• or
• R1 is an optionally benzo-fused, substituted 5- or 6-membered heteroaryl which contains at least one substituent Z6 and additionally contains two, three or four further substituents which on the carbon are selected independently of one another from Z6 and Z1 and on the nitrogen are selected independently of one another from Z6 and Z2,
• or
• R1 is a C3-C8 cycloalkyl or is a C5-C8 cycloalkenyl which contains at least one substituent Z7 and additionally contains two, three or four further substituents which independently of one another are selected from Z7 and Z1,
• Z1 is hydrogen, halogen, hydroxyl, nitro, cyano, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, halocycloalkyl, alkoxy, alkoxyalkyl, hydroxyalkyl, haloalkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcycloalkyl, cycloalkoxyalkyl, cycloalkylamino, alkylthio, haloalkylthio, cycloalkylthio, cycloalkylalkyl, alkylcarbonyloxy, alkylcarbonylamino, haloalkylcarbonylamino, alkylcarbonylthio, alkylsulphinyl, haloalkylsulphinyl, alkylsulphonyloxy, haloalkylsulphonyloxy, alkylcycloalkylalkyl, —C(═O)NR3R4, —NR3R4, tri(C1-C2 alkyl)silyl, or -L3Z3,
• Z2 is hydrogen, halogen, hydroxyl, nitro, cyano, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, halocycloalkyl, alkoxy, alkoxyalkyl, hydroxyalkyl, haloalkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcycloalkyl, cycloalkoxyalkyl, cycloalkylamino, alkylthio, haloalkylthio, cycloalkylthio, cycloalkylalkyl, alkylcarbonyloxy, alkylcarbonylamino, haloalkylcarbonylamino, alkylcarbonylthio, alkylsulphinyl, haloalkylsulphinyl, alkylsulphonyloxy, haloalkylsulphonyloxy, alkylcycloalkylalkyl, —C(═O)NR3R4, —NR3R4 or tri(C1-C2 alkyl)silyl,
• Z3 is a phenyl radical, naphthalenyl radical or a 5- or 6-membered heteroaryl radical which in each case may contain 0, 1, 2 or 3 substituents, the substituents being selected independently of one another from the following
• Substituents on the carbon:
• halogen, cyano, nitro, hydroxyl, amino, —SH, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, halocycloalkyl, alkoxyalkyl, alkylcarbonyl, haloalkylcarbonyl, alkoxycarbonyl, alkoxy, haloalkoxy, cycloalkoxy, halocycloalkoxy, alkenyloxy, alkynyloxy, alkoxyalkoxy, alkylamino, dialkylamino, alkylthio, haloalkylthio, alkylsulphinyl, haloalkylsulphinyl, alkylsulphonyl, haloalkylsulphonyl, trisilylalkyl or phenyl,
• Substituents on the nitrogen:
• hydrogen, —C(═O)H, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, halocycloalkyl, alkylcycloalkyl, cycloalkylalkyl, alkoxyalkyl, alkylsulphonyl, haloalkylsulphonyl, cycloalkylsulphonyl, phenylsulphonyl, alkylcarbonyl, haloalkylcarbonyl, alkoxycarbonyl, haloalkoxycarbonyl, cycloalkoxycarbonyl, —C(═O)NR3R4, phenyl or benzyl,
• Z4 is SH, C(═O)H, C7-C8 cycloalkyl, C7-C8 halocycloalkyl, cycloalkylcycloalkyl, halocycloalkylalkyl, cycloalkenyl, halocycloalkenyl, C5-C6 alkoxyalkyl, alkoxyalkoxyalkyl, alkylthioalkyl, alkylsulphinylalkyl, alkylsulphonylalkyl, alkylaminoalkyl, dialkylaminoalkyl, haloalkylaminoalkyl, cycloalkylaminoalkyl, C5-C6 alkylcarbonyl, haloalkylcarbonyl, cycloalkylcarbonyl, cycloalkoxycarbonyl, cycloalkylalkoxycarbonyl, cycloalkylaminocarbonyl, haloalkoxyalkyl, C5-C6 hydroxyalkyl, C5-C6 alkoxy, C5-C6 haloalkoxy, cycloalkoxy, halocycloalkoxy, cycloalkylalkoxy, alkenyloxy, haloalkenyloxy, alkynyloxy, haloalkynyloxy, alkoxyalkoxy, haloalkylcarbonyloxy, cycloalkylcarbonyloxy, alkylcarbonylalkoxy, C5-C6 alkylthio, C5-C6 haloalkylthio, C5-C6 alkylsulphinyl, C5-C6 haloalkylsulphinyl, alkylsulphonyl, C1-C4 haloalkylsulphonyl, cycloalkylsulphonyl, tri(C3-C4 alkyl)silyl, alkylsulphonylamino or haloalkylsulphonylamino,
• Z5 is tri(C2-C4 alkyl)silyl, benzyl, phenyl, SH, C5-C6 alkoxy, C5-C6 haloalkoxy, C2-C6 alkenyloxy, C2-C6 alkynyloxy, C5-C6 alkylthio or C5-C6 haloalkylthio,
• Z6 is
• Substituents on the carbon:
• SH, cycloalkylcycloalkyl or tri(C3-C4 alkyl)silyl,
• Substituents on the nitrogen:
• alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, halocycloalkyl, alkylcycloalkyl, cycloalkylalkyl, cycloalkylcycloalkyl, alkylsulphonyl, C(═O)H, benzyl or phenyl,
• Z7 is cyano, halogen, hydroxyl, oxo, C1-C4 alkyl, C1-C4 haloalkyl, alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, C1-C4 haloalkylthio or phenyl,
• L3 is a direct bond, —CH2—, —C(═O)—, sulphur, oxygen, —C(═O)O—, —C(═O)NH—, —OC(═O)— or —NHC(═O)—,
• R3 and R4, identically or differently and independently of one another, are hydrogel alkynyl, haloalkyl, cycloalkyl, benzyl or phenyl,
• and/or a salt, metal complex and/or N-oxide thereof.

Compound of formula (III),

• in which
• Y is oxygen or sulphur,
• R2 is hydrogen or halogen
• Q is
• where the bond identified by “x” is bonded directly to the thiazole and the bond identified by “y” is bonded directly to L1 or R1,
• R5 is hydrogen, cyano, C1-C3 alkyl or C1-C3 haloalkyl,
• L1 is a direct bond, —CH2—, —(C═O)—, sulphur or oxygen,
• R1 is phenyl which contains at least one substituent Z4 and additionally two, three or four further substituents which independently are selected from Z4 and Z1,
• or
• R1 is naphthyl, dihydronaphthalenyl, tetrahydronaphthalenyl, hexahydronaphthalenyl, octahydronaphthalenyl or indenyl which contains at least one substituent Z5 and additionally contains two, three or four further substituents which independently are selected from Z5 and Z1
• or
• R1 is an optionally benzo-fused, substituted 5- or 6-membered heteroaryl which contains at least one substituent Z6 and additionally contains two, three or four further substituents which on the carbon are selected independently of one another from Z6 and Z1 and on the nitrogen are selected independently of one another from Z6 and Z2,
• or
• R1 is a C3-C8 cycloalkyl or is a C5-C8 cycloalkenyl which contains at least one substituent Z7 and additionally contains two, three or four further substituents which independently of one another are selected from Z7 and Z1,
• Z1 is hydrogen, halogen, hydroxyl, nitro, cyano, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, halocycloalkyl, alkoxy, alkoxyalkyl, hydroxyalkyl, haloalkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcycloalkyl, cycloalkoxyalkyl, cycloalkylamino, alkylthio, haloalkylthio, cycloalkylthio, cycloalkylalkyl, alkylcarbonyloxy, alkylcarbonylamino, haloalkylcarbonylamino, alkylcarbonylthio, alkylsulphinyl, haloalkylsulphinyl, alkylsulphonyloxy, haloalkylsulphonyloxy, alkylcycloalkylalkyl, —C(═O)NR3R4, —NR3R4, tri(C1-C2 alkyl)silyl, or -L3Z3,
• Z2 is hydrogen, halogen, hydroxyl, nitro, cyano, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, halocycloalkyl, alkoxy, alkoxyalkyl, hydroxyalkyl, haloalkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcycloalkyl, cycloalkoxyalkyl, cycloalkylamino, alkylthio, haloalkylthio, cycloalkylthio, cycloalkylalkyl, alkylcarbonyloxy, alkylcarbonylamino, haloalkylcarbonylamino, alkylcarbonylthio, alkylsulphinyl, haloalkylsulphinyl, alkylsulphonyloxy, haloalkylsulphonyloxy, alkylcycloalkylalkyl, —C(═O)NR3R4, —NR3R4 or tri(C1-C2 alkyl)silyl,
• Z3 is a phenyl radical, naphthalenyl radical or a 5- or 6-membered heteroaryl radical which in each case may contain 0, 1, 2 or 3 substituents, the substituents being selected independently of one another from the following
• Substituents on the carbon:
• halogen, cyano, nitro, hydroxyl, amino, —SH, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, halocycloalkyl, alkoxyalkyl, alkylcarbonyl, haloalkylcarbonyl, alkoxycarbonyl, alkoxy, haloalkoxy, cycloalkoxy, halocycloalkoxy, alkenyloxy, alkynyloxy, alkoxyalkoxy, alkylamino, dialkylamino, alkylthio, haloalkylthio, alkylsulphinyl, haloalkylsulphinyl, alkylsulphonyl, haloalkylsulphonyl, trisilylalkyl or phenyl,
• Substituents on the nitrogen:
• hydrogen, —C(═O)H, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, halocycloalkyl, alkylcycloalkyl, cycloalkylalkyl, alkoxyalkyl, alkylsulphonyl, haloalkylsulphonyl, cycloalkylsulphonyl, phenylsulphonyl, alkylcarbonyl, haloalkylcarbonyl, alkoxycarbonyl, haloalkoxycarbonyl, cycloalkoxycarbonyl, —C(═O)NR3R4, phenyl or benzyl,
• Z4 is SH, C(═O)H, C7-C8 cycloalkyl, C7-C8 halocycloalkyl, cycloalkylcycloalkyl, halocycloalkylalkyl, cycloalkenyl, halocycloalkenyl, C5-C6 alkoxyalkyl, alkoxyalkoxyalkyl, alkylthioalkyl, alkylsulphinylalkyl, alkylsulphonylalkyl, alkylaminoalkyl, dialkylaminoalkyl, haloalkylaminoalkyl, cycloalkylaminoalkyl, C5-C6 alkylcarbonyl, haloalkylcarbonyl, cycloalkylcarbonyl, cycloalkoxycarbonyl, cycloalkylalkoxycarbonyl, cycloalkylaminocarbonyl, haloalkoxyalkyl, C5-C6 hydroxyalkyl, C5-C6 alkoxy, C5-C6 haloalkoxy, cycloalkoxy, halocycloalkoxy, cycloalkylalkoxy, alkenyloxy, haloalkenyloxy, alkynyloxy, haloalkynyloxy, alkoxyalkoxy, haloalkylcarbonyloxy, cycloalkylcarbonyloxy, alkylcarbonylalkoxy, C5-C6 alkylthio, C5-C6 haloalkylthio, C5-C6 alkylsulphinyl, C5-C6 haloalkylsulphinyl, alkylsulphonyl, haloalkylsulphonyl, cycloalkylsulphonyl, tri(C3-C4 alkyl)silyl, alkylsulphonylamino or haloalkylsulphonylamino,
• Z5 is tri(C2-C4 alkyl)silyl, benzyl, phenyl, SH, C5-C6 alkoxy, C5-C6 haloalkoxy, C2-C6 alkenyloxy, C2-C6 alkynyloxy, C5-C6 alkylthio or C5-C6 haloalkylthio,
• Z6 is
• Substituents on the carbon:
• SH, cycloalkylcycloalkyl or tri(C3-C4 alkyl)silyl,
• Substituents on the nitrogen:
• alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, halocycloalkyl, alkylcycloalkyl, cycloalkylalkyl, cycloalkylcycloalkyl, alkylsulphonyl, C(═O)H, benzyl or phenyl,
• Z7 is cyano, halogen, hydroxyl, oxo, C1-C4 alkyl, C1-C4 haloalkyl, alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, C1-C4 haloalkylthio or phenyl,
• L3 is a direct bond, —CH2— —C═O— sulphur, oxygen, —C(═O)O—, —C(═O)NH—, —OC(═O), or —NHC(═O)—,
• R3 and R4, identically or differently and independently of one another, are hydrogen, alkyl, alkenyl, alkynyl, haloalkyl, cycloalkyl, benzyl or phenyl,
• and/or a salt, metal complex and/or N-oxide thereof.