HETEROARYL PIPERIDINE AND HETEROARYL PIPERAZINE DERIVATIVES AS FUNGICIDES
Heteroarylpiperidine and -piperazine derivatives of the formula (I) in which the symbols A, X, Y, L 1 , L 2 , G, Q, p, R 1 , R 2 and R 10 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).
1 . A compound of formula (I)
wherein the radicals are each defined as follows:
A is phenyl which may contain up to five substituents,
where the substituents are each independently selected from Z A-1 ,
or
A is an optionally benzofused, unsubstituted or substituted 5- or 6-membered heteroaryl optionally comprising no more than four substituents, where the substituents on carbon are each independently selected from Z A-2 and the substituents on nitrogen are each independently selected from Z A-3 ,
Z A-1 are the same or different and are each independently hydrogen, halogen, hydroxyl, thioxyl, nitro, cyano, —C(═O)H, —C(═O)OH, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, cycloalkenyl, halocycloalkyl, halocycloalkenyl, hydroxyalkyl, cyanoalkyl, formylalkyl, alkoxyalkyl, haloalkoxyalkyl, cycloalkoxyalkyl, alkynyloxyalkyl, alkylthioalkyl, alkylsulphinylalkyl, alkylaminoalkyl, haloalkylaminoalkyl, cycloalkylaminoalkyl, dialkylaminoalkyl, alkylcarbonylalkyl, alkylsulphonylalkyl, alkylcycloalkyl, alkylcycloalkenyl, alkoxy, alkylcycloalkylalkyl, halocycloalkoxy, alkylthio, haloalkylthio, cycloalkylthio, alkynylthio, alkenyloxy, alkynyloxy, haloalkoxy, haloalkenyloxy, haloalkynyloxy, cycloalkoxy, alkoxyalkoxy, cycloalkylalkoxy, alkylcarbonyloxy, haloalkylcarbonyloxy, cycloalkylcarbonyloxy, cycloalkylamino, alkylcarbonylamino, cycloalkylcarbonylamino, alkoxycarbonylamino, alkylsulphonylamino, haloalkylsulphonylamino, phenylsulphonylamino, cycloalkylalkyl, halocycloalkylalkyl, cycloalkylcycloalkyl, alkoxyalkoxyalkyl, alkylaminocarbonyloxy, alkylcarbonylalkoxy, cycloalkylaminocarbonyl, cycloalkylalkoxycarbonyl, alkylsulphinyl, haloalkylsulphinyl, alkylsulphonyl, haloalkylsulphonyl, cycloalkylsulphonyl, alkylcarbonyl, haloalkylcarbonyl, cycloalkylcarbonyl, alkoxycarbonyl, cycloalkoxycarbonyl, trialkylsilyl, —SF 5 , phenyl, —C(═O)NR 3 R 4 or —NR 3 R 4 ,
Z A-2 and R G1 are the same or different and are each independently hydrogen, halogen, hydroxyl, thioxyl, nitro, cyano, —C(═O)H, —C(═O)OH, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, halocycloalkyl, hydroxyalkyl, formylalkyl, alkoxyalkyl, alkylcarbonylalkyl, alkylcycloalkyl, alkoxy, alkylcycloalkylalkyl, alkylthio, haloalkylthio, alkynylthio, alkenyloxy, alkynyloxy, haloalkoxy, alkoxyalkoxy, alkylcarbonyloxy, haloalkylcarbonyloxy, cycloalkylcarbonylamino, alkylsulphonylamino, halo alkylsulphonylamino, phenylsulphonylamino, cycloalkylalkyl, halocycloalkylalkyl, cycloalkylcycloalkyl, alkoxycarbonyloxy, alkylcarbonylthio, alkylsulphinyl, haloalkylsulphinyl, alkylsulphonyl, haloalkylsulphonyl, alkylcarbonyl, haloalkylcarbonyl, alkoxycarbonyl, alkylaminocarbonyloxy, —C(═O)NR 3 R 4 or —NR 3 R 4 ,
Z A-3 , R G2 and Z 2 are the same or different and are each independently hydrogen, —C(═O)H, —C(═O)NR 3 R 4 , alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, halocycloalkyl, alkylcycloalkyl, cycloalkylalkyl, alkoxyalkyl, alkylsulphonyl, haloalkylsulphonyl, cycloalkylsulphonyl, phenylsulphonyl, alkylcarbonyl, haloalkylcarbonyl, alkoxycarbonyl, haloalkoxycarbonyl, cycloalkoxycarbonyl, phenyl or benzyl,
R 3 and R 4 are the same or different and are each independently hydrogen, alkyl, alkenyl, alkynyl, haloalkyl, cycloalkyl, benzyl or phenyl,
L 1 is NR L12 or C(R L11 ) 2 ,
R L11 is the same or different and is independently hydrogen, halogen, hydroxyl, cyano, —C(═O)H, —C(═O)OH, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxyalkyl, alkylthioalkyl, alkylaminoalkyl, dialkylaminoalkyl, alkoxy, alkylthio, haloalkylthio, haloalkoxy, alkylcarbonyloxy, alkylcarbonylamino, alkylcarbonylthio, alkylsulphonyl, haloalkylsulphonyl, alkylcarbonyl, haloalkylcarbonyl, alkoxycarbonyl, trialkylsilyloxy, —NR 3 R 4 or —C(═O)NR 3 R 4 ,
or the two R L11 radicals, together with the carbon atom to which they are bonded, form a cyclopropyl ring, or
the two R L11 radicals are ═CH 2 , ═COR 3 , ═NOR 3 or ═CHN(R 7 ) 2 ,
R L12 is hydrogen, —C(═O)H, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, halocycloalkyl, alkylcycloalkyl, cycloalkylalkyl, cycloalkylaminocarbonyl, haloalkylaminocarbonyl, alkylsulphonyl, haloalkylsulphonyl, cycloalkylsulphonyl, alkylcarbonyl, haloalkylcarbonyl, alkoxycarbonyl, haloalkoxycarbonyl, cycloalkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, phenyl or benzyl,
R 7 is alkyl, alkenyl, alkynyl, haloalkyl, cycloalkyl, benzyl or phenyl,
Y is sulphur or oxygen,
X is carbon or nitrogen,
R 2 is hydrogen, alkyl, alkenyl, haloalkyl, alkoxy, halogen, cyano or hydroxyl,
R 10 is oxo, alkyl, alkenyl, haloalkyl, alkoxy, halogen, cyano or hydroxyl,
p is 0, 1 or 2,
G is 5-membered heteroaryl which is substituted by Q and may otherwise be unsubstituted or substituted, where the substituents on carbon are each independently selected from R G1 and the substituents on nitrogen are each independently selected from R G2 ,
Q is saturated or partly or fully unsaturated 5-membered heterocyclyl which is substituted by L 2 -R 1 and may otherwise be unsubstituted or substituted, where the substituents are each independently selected from R 5 ,
R 5 is the same or different and is independently:
bonded to carbon of the 5-membered heterocyclyl of Q:
hydrogen, oxo, halogen, cyano, hydroxyl, nitro, —CHO, —C(═O)OH, —C(═O)NH 2 , —C(═O)NR 3 R 4 , —NR 3 R 4 , alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, halocycloalkyl, alkylcycloalkyl, cycloalkylalkyl, cycloalkylcycloalkyl, halocycloalkylalkyl, alkylcycloalkylalkyl, cycloalkenyl, halocycloalkenyl, alkoxyalkyl, haloalkoxyalkyl, cycloalkoxyalkyl, alkoxyalkoxyalkyl, alkylthioalkyl, formylalkyl, alkylcarbonylalkyl, alkylsulphinylalkyl, alkylsulphonylalkyl, alkylaminoalkyl, dialkylaminoalkyl, haloalkylaminoalkyl, cycloalkylaminoalkyl, alkylcarbonyl, haloalkylcarbonyl, cycloalkylcarbonyl, alkoxycarbonyl, cycloalkoxycarbonyl, cycloalkylalkoxycarbonyl, cycloalkylaminocarbonyl, hydroxyalkyl, alkoxy, haloalkoxy, cycloalkoxy, halocycloalkoxy, cycloalkylalkoxy, alkenyloxy, haloalkenyloxy, alkynyloxy, haloalkynyloxy, alkoxyalkoxy, alkylcarbonyloxy, haloalkylcarbonyloxy, cycloalkylcarbonyloxy, alkylcarbonylalkoxy, alkylthio, haloalkylthio, cycloalkylthio, alkylsulphinyl, haloalkylsulphinyl, alkylsulphonyl, haloalkylsulphonyl, cycloalkylsulphonyl, trialkylsilyl, alkylsulphonylamino, haloalkylsulphonylamino,
bonded to nitrogen of the 5-membered heterocyclyl of Q:
hydrogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, halocycloalkyl, alkylcycloalkyl, cycloalkylalkyl, phenyl, benzyl, alkylsulphonyl, —C(═O)H, alkoxycarbonyl or alkylcarbonyl,
L 2 is a direct bond, O, C(═O), S(O) m , CHR 20 or NR 21 ,
m is 0, 1 or 2,
R 20 is hydrogen, alkyl or haloalkyl,
R 21 is hydrogen, alkyl, haloalkyl, cycloalkyl, alkylcarbonyl, haloalkylcarbonyl, alkoxycarbonyl or haloalkoxycarbonyl,
R 1 is phenyl which is substituted once by a Z 4 substituent and may additionally optionally have further substitution, where these additional substituents are each independently selected from Z 4 and Z 1 ,
or
R 1 is naphthyl, dihydronaphthalenyl, tetrahydronaphthalenyl, hexahydronaphthalenyl, octahydronaphthalenyl or indenyl which is substituted once by a Z 5 substituent and may additionally optionally comprise further substitution, where additional substituents are each independently selected from Z 5 and Z 1 ,
or
R 1 is an optionally benzofused, substituted 5- or 6-membered heteroaryl which is substituted once by a substituent, either on a carbon by Z 6 or on a nitrogen by Z 7 , and may additionally optionally have further substitution, where additional substituents on carbon are each independently selected from Z 1 and Z 6 , and the additional substituents on nitrogen are each independently selected from Z 2 and Z 7 ,
Z 1 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)NR 3 R 4 , —NR 3 R 4 , or -L 3 Z 3 ,
L 3 is a direct bond, —CH 2 —, —C(═O)—, sulphur, oxygen, —C(═O)O—, —C(═O)NH—, —OC(═O)— or —NHC(═O)—,
Z 3 is a phenyl radical, naphthalenyl radical or a 5- or 6-membered heteroaryl radical, each of which may contain 0, 1, 2 or 3 substituents, where the substituents are each independently selected from the following list:
substituents on 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 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)NR 3 R 4 , phenyl or benzyl,
Z 4 is SH, C(═O)H, C 7 -C 8 -cycloalkyl, C 7 -C 8 -halocycloalkyl, cycloalkylcycloalkyl, halocycloalkylalkyl, cycloalkenyl, halocycloalkenyl, C 4 -C 6 -alkoxy-C 1 -C 4 -alkyl, C 3 -alkoxy-C 2 -C 4 -alkyl, alkoxyalkoxyalkyl, alkylthioalkyl, alkylsulphinylalkyl, alkylsulphonylalkyl, alkylaminoalkyl, dialkylaminoalkyl, haloalkylaminoalkyl, cycloalkylaminoalkyl, C 4 -C 6 -alkylcarbonyl, haloalkylcarbonyl, cycloalkylcarbonyl, cycloalkoxycarbonyl, cycloalkylalkoxycarbonyl, cycloalkylaminocarbonyl, haloalkoxyalkyl, C 5 -C 6 -hydroxyalkyl, C 5 -C 6 -alkoxy, C 5 -C 6 -haloalkoxy, cycloalkoxy, halocycloalkoxy, cycloalkylalkoxy, alkenyloxy, haloalkenyloxy, alkynyloxy, haloalkynyloxy, alkoxyalkoxy, cyanoalkoxy, haloalkylcarbonyloxy, cycloalkylcarbonyloxy, alkylcarbonylalkoxy, C 5 -C 6 -alkylthio, C 5 -C 6 -haloalkylthio, C 5 -C 6 -alkylsulphinyl, C 5 -C 6 -haloalkylsulphinyl, C 5 -C 6 -alkylsulphonyl, C 5 -C 6 -haloalkylsulphonyl, cycloalkylsulphonyl, tri(C 3 -C 4 -alkyl)silyl, alkylsulphonylamino or haloalkylsulphonylamino,
Z 5 is tri(C 2 -C 4 -alkyl)silyl, benzyl, phenyl, SH, C 5 -C 6 -alkoxy, C 5 -C 6 -haloalkoxy, C 2 -C 6 -alkenyloxy, C 2 -C 6 -alkynyloxy, C 5 -C 6 -alkylthio or C 5 -C 6 -haloalkylthio,
Z 6 is SH, cycloalkylcycloalkyl or tri(C 3 -C 4 -alkyl)silyl,
Z 7 is alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, halocycloalkyl, alkylcycloalkyl, cycloalkylalkyl, cycloalkylcycloalkyl, alkylsulphonyl, C(═O)H, benzyl or phenyl,
and/or a salt, metal complex and/or an N-oxide thereof,
with the proviso that the following compounds are excluded:
in which the symbols are each defined as follows:
Y is oxygen or sulphur,
R 2 is hydrogen or halogen,
Q is
R 5 is hydrogen, cyano, C 1 -C 3 -alkyl or C 1 -C 3 -haloalkyl,
L 2 is a direct bond and
R 1 is as defined above, wherein, when R 1 is substituted phenyl, naphthyl, dihydronaphthalenyl, tetrahydronaphthalenyl, hexahydronaphthalenyl, octahydronaphthalenyl or indenyl or an optionally benzofused, 5- or 6-membered heteroaryl, not more than two substituents are present on the carbocycles or heterocycles mentioned.
2 . The compound of formula (I) 1 and/or salt, metal complex and/or an N-oxide thereof according to claim 1 , wherein the radical definitions are as follows:
A is phenyl which optionally comprise no more than two substituents, where the substituents are each independently selected from the following list:
halogen, cyano, hydroxyl, —NR 3 R 4 , —C(═O)NR 3 R 4 , nitro, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 8 -cycloalkyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -haloalkynyl, C 3 -C 6 -halocycloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkenyloxy, C 1 -C 4 -alkynyloxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulphonyl, C 1 -C 4 -haloalkylthio, C 1 -C 4 -haloalkylsulphonyl, C 1 -C 4 -alkoxy-C 1 -C 6 -alkyl, hydroxy-C 1 -C 4 -alkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkylcarbonyloxy or —C(═O)H, or
A is a heteroaromatic radical selected from the following group: furan-2-yl, furan-3-yl, thiophen-2-yl, thiophen-3-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, pyrrol-1-yl, pyrrol-2-yl, pyrrol-3-yl, oxazol-2-yl, oxazol-4-yl, oxazol-5-yl, thiazol-2-yl, thiazol-4-yl, thiazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, pyrazol-1-yl, pyrazol-3-yl, pyrazol-4-yl, imidazol-1-yl, imidazol-2-yl, imidazol-4-yl, 1,2,3-triazol-1-yl, 1,2,4-triazol-1-yl, pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, pyridazin-3-yl, pyridazin-4-yl, pyrazin-2-yl, pyrazin-3-yl, pyrimidin-2-yl, pyrimidin-4-yl or pyrimidin-5-yl which optionally comprise no more than to two substituents, where the substituents are each independently selected from the following list:
substituents on carbon:
halogen, cyano, hydroxyl, nitro, —NR 3 R 4 , C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -haloalkynyl, C 3 -C 6 -halocycloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulphonyl, C 1 -C 4 -haloalkylthio, C 1 -C 4 -haloalkylsulphonyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, hydroxy-C 1 -C 4 -alkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkylcarbonyloxy or phenyl,
substituents on nitrogen:
C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -haloalkynyl, C 3 -C 10 -cycloalkyl-C 1 -C 6 -alkyl, C 1 -C 6 -haloalkylcarbonyl, phenyl, benzyl, C 1 -C 4 -alkylsulphonyl, C 1 -C 4 -haloalkylsulphonyl, phenylsulphonyl, —C(═O)H, or C 1 -C 6 -alkylcarbonyl,
L 1 is CHR L11 or NR L12 ,
R L11 is hydrogen, methyl, ethyl or cyclopropyl,
R L12 is hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 3 -C 8 -cycloalkyl, C 1 -C 4 -alkylsulphonyl, C 1 -C 4 -alkoxycarbonyl,
Y is oxygen,
X is carbon,
R 2 is hydrogen, fluorine, chlorine, bromine or hydroxyl,
R 10 is oxo, C 1 -C 4 -alkyl, C 1 -C 4 -alkenyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, halogen, cyano or hydroxyl,
p is 0 or 1,
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,
R G1 is hydrogen or halogen,
Q is
where the bond identified by “*” is bonded directly to G, and where the bond identified by “#” is bonded directly to L 2 ,
or
where the bond identified by “*” is bonded directly to L 2 , and where the bond identified by “#” is bonded directly to G,
R 5 is the same or different and is independently:
bonded to carbon of the 5-membered heterocyclyl of Q:
hydrogen, cyano, —NR 3 R 4 , C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -haloalkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 3 -C 8 -halocycloalkyl, C 1 -C 4 -alkyl-C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkyl-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 3 -C 8 -cycloalkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkylthio-C 1 -C 4 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 3 -C 8 -cycloalkoxy, C 3 -C 8 -halocycloalkoxy, C 3 -C 8 -cycloalkyl-C 1 -C 4 -alkoxy, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkynyloxy, C 2 -C 6 -haloalkynyloxy, C 1 -C 6 -alkoxy-C 1 -C 4 -alkoxy, C 1 -C 6 -alkylcarbonyloxy, C 1 -C 6 -haloalkylcarbonyloxy, C 3 -C 8 -cycloalkylcarbonyloxy, C 1 -C 6 -alkylcarbonyl-C 1 -C 6 -alkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -haloalkylthio, C 3 -C 8 -cycloalkylthio,
bonded to nitrogen of the 5-membered heterocyclyl of Q:
hydrogen, —C(═O)H, C 1 -C 3 -alkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkoxycarbonyl or benzyl,
L 2 is a direct bond, —C(═O)—, —CHR 20 — or —NR 21 —,
R 20 is hydrogen, methyl, ethyl, trifluoromethyl,
R 21 is hydrogen or methyl,
R 1 is phenyl which is substituted once by a Z 4 substituent and may additionally optionally comprise further substitution, where additional substituents are each independently selected from Z 4 and Z 1-1 or
R 1 is naphthalen-1-yl, naphthalen-2-yl, 1,2,3,4-tetrahydronaphthalen-1-yl, 1,2,3,4-tetrahydronaphthalen-2-yl, 5,6,7,8-tetrahydronaphthalen-1-yl, 5,6,7,8-tetrahydronaphthalen-2-yl, decalin-1-yl, decalin-2-yl, 1H-inden-1-yl, 2,3-dihydro-1H-inden-1-yl, 1H-inden-2-yl, 1H-inden-3-yl, 1H-inden-4-yl, 1H-inden-5-yl, 1H-inden-6-yl, 1H-inden-7-yl, indan-1-yl, indan-2-yl, indan-3-yl, indan-4-yl or indan-5-yl,
where each is substituted once by a Z 5 substituent and may additionally optionally comprise further substitution, where additional substituents are each independently selected from Z 5 and Z 1-2 , or
R 1 is a 5- or 6-membered heteroaryl radical which is substituted once by a substituent, either on a carbon by Z 6 or on a nitrogen by Z 7 , and may additionally optionally comprise further substitution, where additional substituents on carbon are each independently selected from Z 1-3 and Z 6 , and additional substituents on nitrogen are each independently selected from Z 2 , or
R 1 is benzofused substituted 5- or 6-membered heteroaryl which is substituted by one Z 4 substituent and may additionally optionally comprise further substitution, where additional substituents on carbon are each independently selected from Z 1-2 , and additional substituents on nitrogen are each independently selected from Z 2 ,
Z 1-1 is hydrogen, halogen, cyano, hydroxyl, nitro, —C(═O)NR 3 R 4 , —NR 3 R 4 , C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -haloalkynyl, C 3 -C 6 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 6 -alkylcarbonyloxy, C 1 -C 4 -alkylthio, C 1 -C 4 -haloalkylthio, C 3 -C 6 -cycloalkylthio or -L 3 Z 3 ,
Z 1-2 are the same or different and are each independently hydrogen, halogen, cyano, nitro, —NR 3 R 4 , —C(═O)NR 3 R 4 , C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -haloalkynyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 6 -alkylcarbonyloxy, C 1 -C 6 -alkylcarbonylthio, C 1 -C 4 -alkylthio or C 1 -C 4 -haloalkylthio,
Z 1-3 is hydrogen, halogen, cyano, hydroxyl, nitro, —C(═O)NR 3 R 4 , —NR 3 R 4 , C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -haloalkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkoxy, C 1 -C 6 -halo alkoxy, C 1 -C 6 -alkylcarbonyloxy, C 1 -C 6 -alkylthio, C 1 -C 6 -haloalkylthio or C 3 -C 6 -cycloalkylthio,
Z 2 is the same or different and is independently hydrogen, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -haloalkynyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, phenyl, benzyl, C 1 -C 4 -haloalkylsulphonyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, phenylsulphonyl, C 1 -C 4 -alkylsulphonyl, —C(═O)H, C 1 -C 3 -haloalkylcarbonyl or C 1 -C 3 -alkylcarbonyl,
L 3 is a direct bond, —CH 2 —, sulphur, oxygen,
Z 3 is a phenyl radical, naphthalenyl or a 5- or 6-membered heteroaryl radical which optionally comprise no more than 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, C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, C 1 -C 4 -haloalkyl, C 2 -C 4 -haloalkenyl, C 2 -C 4 -haloalkynyl, C 2 -C 4 -alkoxyalkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 2 -C 6 -alkenyloxy, C 2 -C 6 -alkynyloxy, C 1 -C 4 -alkylthio, C 1 -C 4 -haloalkylthio, C 1 -C 4 -alkylsulphonyl, C 1 -C 4 -haloalkylsulphonyl or C 1 -C 4 -alkylamino, di(C 1 -C 4 -alkyl)amino,
substituents on nitrogen: C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -haloalkynyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, phenyl, benzyl, C 1 -C 4 -haloalkylsulphonyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, phenylsulphonyl, C 1 -C 4 -alkylsulphonyl, —C(═O)H, or C 1 -C 3 -alkylcarbonyl,
Z 4 is C(═O)H, C 7 -C 8 -cycloalkyl, C 3 -C 6 -cycloalkyl-C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 4 -C 6 -alkoxy-C 1 -C 4 -alkyl, C 4 -C 6 -alkoxy-C 1 -C 4 -alkyl, C 3 -alkoxy-C 2 -C 4 -alkyl, C 1 -C 3 -alkoxy-C 2 -C 3 -alkoxy-C 1 -C 3 -alkyl, C 1 -C 4 -alkylthio-C 1 -C 2 -alkyl, C 1 -C 4 -alkylsulphinyl-C 1 -C 2 -alkyl, C 1 -C 4 -alkylsulphonyl-C 1 -C 2 -alkyl, C 1 -C 4 -alkylamino-C 1 -C 2 -alkyl, C 1 -C 2 -dialkylamino-C 1 -C 2 -alkyl, C 1 -C 4 -haloalkylamino-C 1 -C 2 -alkyl, C 3 -C 6 -cycloalkylamino-C 1 -C 2 -alkyl, C 4 -C 6 -alkylcarbonyl, C 1 -C 4 -haloalkylcarbonyl, C 3 -C 6 -cycloalkylcarbonyl, C 3 -C 6 -cycloalkoxycarbonyl, C 3 -C 6 -cycloalkyl-C 1 -C 2 -alkoxycarbonyl, C 3 -C 6 -cycloalkylaminocarbonyl, C 1 -C 4 -haloalkoxy-C 1 -C 2 -alkyl, C 5 -C 6 -hydroxyalkyl, C 5 -C 6 -alkoxy, C 5 -C 6 -haloalkoxy, C 3 -C 6 -cycloalkoxy, C 3 -C 6 -halocycloalkoxy, C 3 -C 6 -cycloalkylalkoxy, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkynyloxy, C 2 -C 6 -haloalkynyloxy, C 1 -C 4 -alkoxy-C 1 -C 4 -alkoxy, cyano-C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkylcarbonyloxy, C 3 -C 6 -cycloalkylcarbonyloxy, C 1 -C 4 -alkylcarbonyl-C 1 -C 4 -alkoxy, C 5 -C 6 -alkylthio, C 5 -C 6 -haloalkylthio, C 5 -C 6 -alkylsulphinyl, C 5 -C 6 -haloalkylsulphinyl, C 5 -C 6 -alkylsulphonyl, C 5 -C 6 -haloalkylsulphonyl, C 3 -C 6 -cycloalkylsulphonyl, tri(C 3 -C 4 -alkyl)silyl, C 1 -C 4 -alkylsulphonylamino or C 1 -C 4 -haloalkylsulphonylamino,
Z 5 is benzyl, phenyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -alkynyloxy, C 5 -C 6 -alkylthio or C 5 -C 6 -haloalkylthio,
Z 6 is C 3 -C 6 -cycloalkylcyclopropyl, C 3 -C 6 -cycloalkylcyclohexyl or tri(C 3 -C 4 -alkyl)silyl,
Z 7 is C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -alkyl-C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkylcyclopropyl, C 3 -C 6 -cycloalkylcyclohexyl, cycloalkylalkyl, C 1 -C 4 -alkylsulphonyl, C(═O)H, benzyl or phenyl.
3 . The compound of formula (I) and/or salt, metal complex and/or an N-oxide thereof according to claim 1 , wherein the radical definitions are each as follows:
A is phenyl which optionally comprise no more than two substituents, where the substituents are each independently selected from the following list:
methyl, ethyl, iodine, chlorine, bromine, fluorine, methoxy, ethoxy, difluoromethyl or trifluoromethyl or
A is pyrazol-1-yl which optionally comprise no more than two substituents, where the substituents are each independently selected from the following list:
methyl, ethyl, chlorine, bromine, fluorine or trifluoromethyl.
4 . The compound of formula (I) and/or salt, metal complex and/or an N-oxide thereof according to claim 1 , wherein the radical definitions are each as follows:
G is G 1 , G 2 or G 3 and especially G 1 ,
R G1 is hydrogen.
5 . The compound of formula (I) and/or salt, metal complex and/or an N-oxide thereof according to claim 1 , wherein the radical definitions are each as follows:
Q is
where the bond identified by “x” is bonded directly to G, and the bond identified by “y” is bonded directly to L 2 .
6 . The compound of the formula (I) and/or salt, metal complex and/or an N-oxide thereof according to claim 1 , wherein the radical definitions are each as follows:
R 1 is phenyl which optionally comprise no more than 3 substituents, where one substituent is selected from Z 4 and any further substituents are selected from the following list: fluorine, chlorine, bromine, iodine, cyano, nitro, hydroxyl, amino, —SH, —C(═O)H, methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1,1-dimethylethyl, 1,2-dimethylethyl, ethenyl, ethynyl, trifluoromethyl, difluoromethyl, trichloromethyl, dichloromethyl, cyclopropyl, methoxy, ethoxy, n-propoxy, 1-methylethoxy, 1,1-dimethylethoxy, methylcarbonyl, ethylcarbonyl, trifluoromethylcarbonyl, methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, 1-methylethoxycarbonyl, 1,1-dimethylethoxycarbonyl, 1-ethenyloxy, 2-propenyloxy, 2-propynyloxy, methylcarbonyloxy, trifluoroalkylcarbonyloxy, chloromethylcarbonyloxy, methylthio, ethylthio, methylsulphonyl, methylsulphonylamino, trifluoromethylsulphonylamino or -L 3 R 3 , or
R 1 is naphthalen-1-yl, naphthalen-2-yl, 1,2,3,4-tetrahydronaphthalen-1-yl, 1,2,3,4-tetrahydronaphthalen-2-yl, 5,6,7,8-tetrahydronaphthalen-1-yl, 5,6,7,8-tetrahydronaphthalen-2-yl, decalin-1-yl, decalin-2-yl, 1H-inden-1-yl, 2,3-dihydro-1H-inden-1-yl, 1H-inden-2-yl, 1H-inden-3-yl, 1H-inden-4-yl, 1H-inden-5-yl, 1H-inden-6-yl, 1H-inden-7-yl, indan-1-yl, indan-2-yl, indan-3-yl, indan-4-yl or indan-5-yl, where these are each substituted at least once by a Z 5 substituent and may optionally additionally comprise further substitution, where the additional substituents are each independently selected from Z 5 and the group consisting of methyl, methoxy, cyano, fluorine, chlorine, bromine and iodine, or
R 1 is furan-2-yl, furan-3-yl, thiophen-2-yl, thiophen-3-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, pyrrol-1-yl, pyrrol-2-yl, pyrrol-3-yl, oxazol-2-yl, oxazol-4-yl, oxazol-5-yl, thiazol-2-yl, thiazol-4-yl, thiazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, pyrazol-1-yl, pyrazol-3-yl, pyrazol-4-yl, imidazol-1-yl, imidazol-2-yl, imidazol-4-yl, 1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl, 1,3,4-oxadiazol-2-yl, 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl, 1,3,4-thiadiazol-2-yl, 1,2,3-triazol-1-yl, 1,2,3-triazol-2-yl, 1,2,3-triazol-4-yl, 1,2,4-triazol-1-yl, 1,2,4-triazol-3-yl, 1,2,4-triazol-4-yl, pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, pyridazin-3-yl, pyridazin-4-yl, pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl or pyrazin-2-yl, each of which may contain 1 or 2 substituent(s), where one substituent is either on a carbon and is selected from Z 6 or is on a nitrogen and is selected from Z 7 , and any further substituent is selected from the following list:
substituents on carbon: fluorine, chlorine, bromine, iodine, cyano, nitro, hydroxyl, methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1,1-dimethylethyl, 1,2-dimethylethyl, ethenyl, ethynyl, trifluoromethyl, difluoromethyl, trichloromethyl, dichloromethyl, cyclopropyl, methoxy, ethoxy, n-propoxy, 1-methylethoxy, 1,1-dimethylethoxy, methylcarbonyl, ethylcarbonyl, trifluoromethylcarbonyl, methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, 1-methylethoxycarbonyl, 1,1-dimethylethoxycarbonyl, 1-ethenyloxy, 2-propenyloxy, 2-propinyloxy, methylcarbonyloxy, trifluoroalkylcarbonyloxy, chloromethylcarbonyloxy, methylcarbonylamino, trifluoroalkylcarbonylamino, chloromethylcarbonylamino, methylthio, ethylthio, methylsulphinyl, methylsulphonyl, methylsulphonyloxy, trifluoroalkylsulphonyloxy, methylsulphonylamino or trifluoromethylsulphonylamino,
substituents on nitrogen: methyl, ethyl, n-propyl, —C(═O)H, methylcarbonyl, trifluoromethylcarbonyl, chloromethylcarbonyl, methylsulphonyl, trifluoromethylsulphonyl, phenylsulphonyl, phenyl or 2-propynyl, or
R 1 is indol-1-yl, indol-2-yl, indol-3-yl, indol-4-yl, indol-5-yl, indol-6-yl, indol-7-yl, benzimidazol-1-yl, benzimidazol-2-yl, benzimidazol-4-yl, benzimidazol-5-yl, indazol-1-yl, indazol-3-yl, indazol-4-yl, indazol-5-yl, indazol-6-yl, indazol-7-yl, indazol-2-yl, 1-benzofuran-2-yl, 1-benzofuran-3-yl, 1-benzofuran-4-yl, 1-benzofuran-5-yl, 1-benzofuran-6-yl, 1-benzofuran-7-yl, 1-benzothiophen-2-yl, 1-benzothiophen-3-yl, 1-benzothiophen-4-yl, 1-benzothiophen-5-yl, 1-benzothiophen-6-yl, 1-benzothiophen-7-yl, 1,3-benzothiazol-2-yl, 1,3-benzothiazol-4-yl, 1,3-benzothiazol-5-yl, 1,3-benzothiazol-6-yl, 1,3-benzothiazol-7-yl, 1,3-benzoxazol-2-yl, 1,3-benzoxazol-4-yl, 1,3-benzoxazol-5-yl, 1,3-benzoxazol-6-yl, 1,3-benzoxazol-7-yl, quinolin-2-yl, quinolin-3-yl, quinolin-4-yl, quinolin-5-yl, quinolin-6-yl, quinolin-7-yl, quinolin-8-yl, isoquinolin-1-yl, isoquinolin-3-yl, isoquinolin-4-yl, isoquinolin-5-yl, isoquinolin-6-yl, isoquinolin-7-yl or isoquinolin-8-yl, which is substituted by a substituent, either on a carbon by Z 6 or on a nitrogen by Z 7 , and additionally optionally bears a further substituent selected from the following list:
substituents on carbon: fluorine, chlorine, bromine, iodine, methyl, methoxy,
substituents on nitrogen: methyl, ethyl, n-propyl, —C(═O)H, methylcarbonyl, trifluoromethylcarbonyl, chloromethylcarbonyl, methylsulphonyl, trifluoromethylsulphonyl, phenylsulphonyl, phenyl or 2-propynyl.
7 . The compound of formula (I) and/or salt, metal complex and/or an N-oxide thereof according to claim 1 , wherein the radical definitions are each as follows:
A is 5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl, 5-chloro-2-methylphenyl or 2,5-bis(difluoromethyl)phenyl,
L 1 is —CH 2 — or —NH—,
L 2 is a direct bond,
Y is oxygen,
X is carbon,
p is 0,
G is G 1 ,
R G1 is hydrogen,
Q is Q 24 -3,
R 2 is hydrogen,
R 5 is hydrogen,
R 1 is 3-formylphenyl, 2-formylphenyl or 2-[(methylsulphonyl)amino]phenyl.
8 . A compound of formula (VII)
and/or a salt, metal complex and/or N-oxides thereof, wherein
A is phenyl which may contain up to five substituents,
where the substituents are each independently selected from Z A-1 ,
or
A is an optionally benzofused, unsubstituted or substituted 5- or 6-membered heteroaryl optionally comprising no more than four substituents, where the substituents on carbon are each independently selected from Z A-2 and the substituents on nitrogen are each independently selected from Z A-3 ,
Z A-1 are the same or different and are each independently hydrogen, halogen, hydroxyl, thioxyl, nitro, cyano, —C(═O)H, —C(═O)OH, alkyl, alkenyl, alkenyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, cycloalkenyl, halocycloalkyl, halocycloalkenyl, hydroxyalkyl, cyanoalkyl, formylalkyl, alkoxyalkyl, haloalkoxyalkyl, cycloalkoxyalkyl, alkynyloxyalkyl, alkylthioalkyl, alkylsulphinylalkyl, alkylaminoalkyl, haloalkylaminoalkyl, cycloalkylaminoalkyl, dialkylaminoalkyl, alkylcarbonylalkyl, alkylsulphonylalkyl, alkylcycloalkyl, alkylcycloalkenyl, alkoxy, alkylcycloalkylalkyl, halocycloalkoxy, alkylthio, haloalkylthio, cycloalkylthio, alkynylthio, alkenyloxy, alkynyloxy, haloalkoxy, haloalkenyloxy, haloalkynyloxy, cycloalkoxy, alkoxyalkoxy, cycloalkylalkoxy, alkylcarbonyloxy, haloalkylcarbonyloxy, cycloalkylcarbonyloxy, cycloalkylamino, alkylcarbonylamino, cycloalkylcarbonylamino, alkoxycarbonylamino, alkylsulphonylamino, haloalkylsulphonylamino, phenylsulphonylamino, cycloalkylalkyl, halocycloalkylalkyl, cycloalkylcycloalkyl, alkoxyalkoxyalkyl, alkylaminocarbonyloxy, alkylcarbonylalkoxy, cycloalkylaminocarbonyl, cycloalkylalkoxycarbonyl, alkylsulphinyl, haloalkylsulphinyl, alkylsulphonyl, haloalkylsulphonyl, cycloalkylsulphonyl, alkylcarbonyl, haloalkylcarbonyl, cycloalkylcarbonyl, alkoxycarbonyl, cycloalkoxycarbonyl, trialkylsilyl, —SF, phenyl, —C(═O)NR 3 R 4 or —NR 3 R 4 ,
Z A-2 and R G1 are the same or different and are each independently hydrogen, halogen, hydroxyl, thioxyl, nitro, cyano, —C(═O)H, —C(═O)OH, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, halocycloalkyl, hydroxyalkyl, formylalkyl, alkoxyalkyl, alkylcarbonylalkyl, alkylcycloalkyl, alkoxy, alkylcycloalkylalkyl, alkylthio, haloalkylthio, alkynylthio, alkenyloxy, alkynyloxy, haloalkoxy, alkoxyalkoxy, alkylcarbonyloxy, haloalkylcarbonyloxy, cycloalkylcarbonylamino, alkylsulphonylamino, halo alkylsulphonylamino, phenylsulphonylamino, cycloalkylalkyl, halocycloalkylalkyl, cycloalkylcycloalkyl, alkoxycarbonyloxy, alkylcarbonylthio, alkylsulphinyl, haloalkylsulphinyl, alkylsulphonyl, haloalkylsulphonyl, alkylcarbonyl, haloalkylcarbonyl, alkoxycarbonyl, alkylaminocarbonyloxy, —C(═O)NR 3 R 4 or —NR 3 R 4 ,
Z A-3 , R G2 and Z 2 are the same or different and are each independently hydrogen, —C(═O)H, —C(═O)NR 3 R 4 , alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, halocycloalkyl, alkylcycloalkyl, cycloalkylalkyl, alkoxyalkyl, alkylsulphonyl, haloalkylsulphonyl, cycloalkylsulphonyl, phenylsulphonyl, alkylcarbonyl, haloalkylcarbonyl, alkoxycarbonyl, haloalkoxycarbonyl, cycloalkoxycarbonyl, phenyl or benzyl,
R 3 and R 4 are the same or different and are each independently hydrogen, alkyl, alkenyl, alkynyl, haloalkyl, cycloalkyl, benzyl or phenyl,
L 1 is NR L12 or C(R L11 ) 2 ,
R L11 is the same or different and is independently hydrogen, halogen, hydroxyl, cyano, —C(═O)H, —C(═O)OH, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxyalkyl, alkylthioalkyl, alkylaminoalkyl, dialkylaminoalkyl, alkoxy, alkylthio, haloalkylthio, haloalkoxy, alkylcarbonyloxy, alkylcarbonylamino, alkylcarbonylthio, alkylsulphonyl, haloalkylsulphonyl, alkylcarbonyl, haloalkylcarbonyl, alkoxycarbonyl, trialkylsilyloxy, —NR 3 R 4 or —C(═O)NR 3 R 4 ,
or the two R L11 radicals, together with the carbon atom to which they are bonded, form a cyclopropyl ring, or
the two R L11 radicals are ═CH 2 , ═COR 3 , ═NOR 3 or ═CHN(R 7 ) 2 ,
R L12 is hydrogen, —C(═O)H, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, halocycloalkyl, alkylcycloalkyl, cycloalkylalkyl, cycloalkylaminocarbonyl, haloalkylaminocarbonyl, alkylsulphonyl, haloalkylsulphonyl, cycloalkylsulphonyl, alkylcarbonyl, haloalkylcarbonyl, alkoxycarbonyl, haloalkoxycarbonyl, cycloalkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, phenyl or benzyl,
R 7 is alkyl, alkenyl, alkynyl, haloalkyl, cycloalkyl, benzyl or phenyl,
Y is sulphur or oxygen,
X is carbon or nitrogen,
R 2 is hydrogen, alkyl, alkenyl, haloalkyl, alkoxy, halogen, cyano or hydroxyl, R 10 is oxo, alkyl, alkenyl, haloalkyl, alkoxy, halogen, cyano or hydroxyl,
p is 0, 1 or 2,
G is 5-membered heteroaryl which is substituted by Q and may otherwise be unsubstituted or substituted, where the substituents on carbon are each independently selected from R G1 and the substituents on nitrogen are each independently selected from R G2 ,
Q is saturated or partly or fully unsaturated 5-membered heterocyclyl which is substituted by L 2 -R 1 and may otherwise be unsubstituted or substituted, where the substituents are each independently selected from R 5 ,
R 5 is the same or different and is independently:
bonded to carbon of the 5-membered heterocyclyl of Q:
hydrogen, oxo, halogen, cyano, hydroxyl, nitro, —CHO, —C(═O)OH, —C(═O)NH 2 , —C(═O)NR 3 R 4 , —NR 3 R 4 , alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, halocycloalkyl, alkylcycloalkyl, cycloalkylalkyl, cycloalkylcycloalkyl, halocycloalkylalkyl, alkylcycloalkylalkyl, cycloalkenyl, halocycloalkenyl, alkoxyalkyl, haloalkoxyalkyl, cycloalkoxyalkyl, alkoxyalkoxyalkyl, alkylthioalkyl, formylalkyl, alkylcarbonylalkyl, alkylsulphinylalkyl, alkylsulphonylalkyl, alkylaminoalkyl, dialkylaminoalkyl, haloalkylaminoalkyl, cycloalkylaminoalkyl, alkylcarbonyl, haloalkylcarbonyl, cycloalkylcarbonyl, alkoxycarbonyl, cycloalkoxycarbonyl, cycloalkylalkoxycarbonyl, cycloalkylaminocarbonyl, hydroxyalkyl, alkoxy, haloalkoxy, cycloalkoxy, halocycloalkoxy, cycloalkylalkoxy, alkenyloxy, haloalkenyloxy, alkynyloxy, haloalkynyloxy, alkoxyalkoxy, alkylcarbonyloxy, haloalkylcarbonyloxy, cycloalkylcarbonyloxy, alkylcarbonylalkoxy, alkylthio, haloalkylthio, cycloalkylthio, alkylsulphinyl, haloalkylsulphinyl, alkylsulphonyl, haloalkylsulphonyl, cycloalkylsulphonyl, trialkylsilyl, alkylsulphonylamino, haloalkylsulphonylamino,
bonded to nitrogen of the 5-membered heterocyclyl of Q:
hydrogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, halocycloalkyl, alkylcycloalkyl, cycloalkylalkyl, phenyl, benzyl, alkylsulphonyl, —C(═O)H, alkoxycarbonyl or alkylcarbonyl,
L 2 is a direct bond, O, C(═O), S(O) m , CHR 20 or NR 21 ,
m is 0, 1 or 2,
R 20 is hydrogen, alkyl or haloalkyl,
R 21 is hydrogen, alkyl, haloalkyl, cycloalkyl, alkylcarbonyl, haloalkylcarbonyl, alkoxycarbonyl or haloalkoxycarbonyl,
R 1 is phenyl which is substituted once by a Z 4 substituent and may additionally optionally have further substitution, where these additional substituents are each independently selected from Z 4 and Z 1 ,
or
R 1 is naphthyl, dihydronaphthalenyl, tetrahydronaphthalenyl, hexahydronaphthalenyl, octahydronaphthalenyl or indenyl which is substituted once by a Z 5 substituent and may additionally optionally comprise further substitution, where additional substituents are each independently selected from Z 5 and Z 1 ,
or
R 1 is an optionally benzofused, substituted 5- or 6-membered heteroaryl which is substituted once by a substituent, either on a carbon by Z 6 or on a nitrogen by Z 7 , and may additionally optionally have further substitution, where additional substituents on carbon are each independently selected from Z 1 and Z 6 , and the additional substituents on nitrogen are each independently selected from Z 2 and Z 7 ,
Z 1 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)NR 3 R 4 , —NR 3 R 4 , or -L 3 Z 3 ,
L 3 is a direct bond, —CH 2 —, —C(═O)—, sulphur, oxygen, —C(═O)O—, —C(═O)NH—, —OC(═O)— or —NHC(═O)—,
Z 3 is a phenyl radical, naphthalenyl radical or a 5- or 6-membered heteroaryl radical, each of which may contain 0, 1, 2 or 3 substituents, where the substituents are each independently selected from the following list:
substituents on 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 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)NR 3 R 4 , phenyl or benzyl,
Z 4 is SH, C(═O)H, C 7 -C 8 -cycloalkyl, C 7 -C 8 -halocycloalkyl, cycloalkylcycloalkyl, halocycloalkylalkyl, cycloalkenyl, halocycloalkenyl, C 4 -C 6 -alkoxy-C 1 -C 4 -alkyl, C 3 -alkoxy-C 2 -C 4 -alkyl, alkoxyalkoxyalkyl, alkylthioalkyl, alkylsulphinylalkyl, alkylsulphonylalkyl, alkylaminoalkyl, dialkylaminoalkyl, haloalkylaminoalkyl, cycloalkylaminoalkyl, C 4 -C 6 -alkylcarbonyl, haloalkylcarbonyl, cycloalkylcarbonyl, cycloalkoxycarbonyl, cycloalkylalkoxycarbonyl, cycloalkylaminocarbonyl, haloalkoxyalkyl, C 5 -C 6 -hydroxyalkyl, C 5 -C 6 -alkoxy, C 5 -C 6 -haloalkoxy, cycloalkoxy, halocycloalkoxy, cycloalkylalkoxy, alkenyloxy, haloalkenyloxy, alkynyloxy, haloalkynyloxy, alkoxyalkoxy, cyanoalkoxy, haloalkylcarbonyloxy, cycloalkylcarbonyloxy, alkylcarbonylalkoxy, C 5 -C 6 -alkylthio, C 5 -C 6 -haloalkylthio, C 5 -C 6 -alkylsulphinyl, C 5 -C 6 -haloalkylsulphinyl, C 5 -C 6 -alkylsulphonyl, C 5 -C 6 -haloalkylsulphonyl, cycloalkylsulphonyl, tri(C 3 -C 4 -alkyl)silyl, alkylsulphonylamino or haloalkylsulphonylamino,
Z 5 is tri(C 2 -C 4 -alkyl)silyl, benzyl, phenyl, SH, C 5 -C 6 -alkoxy, C 5 -C 6 -haloalkoxy, C 2 -C 6 -alkenyloxy, C 2 -C 6 -alkynyloxy, C 5 -C 6 -alkylthio or C 5 -C 6 -haloalkylthio,
Z 6 is SH, cycloalkylcycloalkyl or tri(C 3 -C 4 -alkyl)silyl,
Z 7 is alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, halocycloalkyl, alkylcycloalkyl, cycloalkylalkyl, cycloalkylcycloalkyl, alkylsulphonyl, C(═O)H, benzyl or phenyl,
and W 13 is a leaving group.
9 . A compound of formula (XVIId)
and/or a salt, metal complex and/or N-oxide thereof, in which wherein the symbol W 6 is acetyl, C 1 -C 4 alkoxycarbonyl, benzyl or benzyloxycarbonyl and
A is phenyl which may contain up to five substituents,
where the substituents are each independently selected from Z A-1 ,
or
A is an optionally benzofused, unsubstituted or substituted 5- or 6-membered heteroaryl optionally comprising no more than four substituents, where the substituents on carbon are each independently selected from Z A-2 and the substituents on nitrogen are each independently selected from Z A-3 ,
Z A-1 are the same or different and are each independently hydrogen, halogen, hydroxyl, thioxyl, nitro, cyano, —C(═O)H, —C(═O)OH, alkyl, alkenyl, alkenyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, cycloalkenyl, halocycloalkyl, halocycloalkenyl, hydroxyalkyl, cyanoalkyl, formylalkyl, alkoxyalkyl, haloalkoxyalkyl, cycloalkoxyalkyl, alkynyloxyalkyl, alkylthioalkyl, alkylsulphinylalkyl, alkylaminoalkyl, haloalkylaminoalkyl, cycloalkylaminoalkyl, dialkylaminoalkyl, alkylcarbonylalkyl, alkylsulphonylalkyl, alkylcycloalkyl, alkylcycloalkenyl, alkoxy, alkylcycloalkylalkyl, halocycloalkoxy, alkylthio, haloalkylthio, cycloalkylthio, alkynylthio, alkenyloxy, alkynyloxy, haloalkoxy, haloalkenyloxy, haloalkynyloxy, cycloalkoxy, alkoxyalkoxy, cycloalkylalkoxy, alkylcarbonyloxy, haloalkylcarbonyloxy, cycloalkylcarbonyloxy, cycloalkylamino, alkylcarbonylamino, cycloalkylcarbonylamino, alkoxycarbonylamino, alkylsulphonylamino, haloalkylsulphonylamino, phenylsulphonylamino, cycloalkylalkyl, halocycloalkylalkyl, cycloalkylcycloalkyl, alkoxyalkoxyalkyl, alkylaminocarbonyloxy, alkylcarbonylalkoxy, cycloalkylaminocarbonyl, cycloalkylalkoxycarbonyl, alkylsulphinyl, haloalkylsulphinyl, alkylsulphonyl, haloalkylsulphonyl, cycloalkylsulphonyl, alkylcarbonyl, haloalkylcarbonyl, cycloalkylcarbonyl, alkoxycarbonyl, cycloalkoxycarbonyl, trialkylsilyl, —SF 5 , phenyl, —C(═O)NR 3 R 4 or —NR 3 R 4 ,
Z A-2 and R G1 are the same or different and are each independently hydrogen, halogen, hydroxyl, thioxyl, nitro, cyano, —C(═O)H, —C(═O)OH, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, halocycloalkyl, hydroxyalkyl, formylalkyl, alkoxyalkyl, alkylcarbonylalkyl, alkylcycloalkyl, alkoxy, alkylcycloalkylalkyl, alkylthio, haloalkylthio, alkynylthio, alkenyloxy, alkynyloxy, haloalkoxy, alkoxyalkoxy, alkylcarbonyloxy, haloalkylcarbonyloxy, cycloalkylcarbonylamino, alkylsulphonylamino, halo alkylsulphonylamino, phenylsulphonylamino, cycloalkylalkyl, halocycloalkylalkyl, cycloalkylcycloalkyl, alkoxycarbonyloxy, alkylcarbonylthio, alkylsulphinyl, haloalkylsulphinyl, alkylsulphonyl, haloalkylsulphonyl, alkylcarbonyl, haloalkylcarbonyl, alkoxycarbonyl, alkylaminocarbonyloxy, —C(═O)NR 3 R 4 or —NR 3 R 4 ,
Z A-3 , R G2 and Z 2 are the same or different and are each independently hydrogen, —C(═O)H, —C(═O)NR 3 R 4 , alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, halocycloalkyl, alkylcycloalkyl, cycloalkylalkyl, alkoxyalkyl, alkylsulphonyl, haloalkylsulphonyl, cycloalkylsulphonyl, phenylsulphonyl, alkylcarbonyl, haloalkylcarbonyl, alkoxycarbonyl, haloalkoxycarbonyl, cycloalkoxycarbonyl, phenyl or benzyl,
R 3 and R 4 are the same or different and are each independently hydrogen, alkyl, alkenyl, alkynyl, haloalkyl, cycloalkyl, benzyl or phenyl,
L 1 is NR L12 or C(R L11 ) 2 ,
R L11 is the same or different and is independently hydrogen, halogen, hydroxyl, cyano, —C(═O)H, —C(═O)OH, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxyalkyl, alkylthioalkyl, alkylaminoalkyl, dialkylaminoalkyl, alkoxy, alkylthio, haloalkylthio, haloalkoxy, alkylcarbonyloxy, alkylcarbonylamino, alkylcarbonylthio, alkylsulphonyl, haloalkylsulphonyl, alkylcarbonyl, haloalkylcarbonyl, alkoxycarbonyl, trialkylsilyloxy, —NR 3 R 4 or —C(═O)NR 3 R 4 ,
or the two R L11 radicals, together with the carbon atom to which they are bonded, form a cyclopropyl ring, or
the two R L11 radicals are ═CH 2 , ═COR 3 , ═NOR 3 or ═CHN(R 7 ) 2 ,
R L12 is hydrogen, —C(═O)H, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, halocycloalkyl, alkylcycloalkyl, cycloalkylalkyl, cycloalkylaminocarbonyl, haloalkylaminocarbonyl, alkylsulphonyl, haloalkylsulphonyl, cycloalkylsulphonyl, alkylcarbonyl, haloalkylcarbonyl, alkoxycarbonyl, haloalkoxycarbonyl, cycloalkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, phenyl or benzyl,
R 7 is alkyl, alkenyl, alkynyl, haloalkyl, cycloalkyl, benzyl or phenyl,
Y is sulphur or oxygen,
X is carbon or nitrogen,
R 2 is hydrogen, alkyl, alkenyl, haloalkyl, alkoxy, halogen, cyano or hydroxyl,
R 10 is oxo, alkyl, alkenyl, haloalkyl, alkoxy, halogen, cyano or hydroxyl,
p is 0, 1 or 2,
G is 5-membered heteroaryl which is substituted by Q and may otherwise be unsubstituted or substituted, where the substituents on carbon are each independently selected from R G1 and the substituents on nitrogen are each independently selected from R G2 ,
Q is saturated or partly or fully unsaturated 5-membered heterocyclyl which is substituted by L 2 -R 1 and may otherwise be unsubstituted or substituted, where the substituents are each independently selected from R 5 ,
R 5 is the same or different and is independently:
bonded to carbon of the 5-membered heterocyclyl of Q:
hydrogen, oxo, halogen, cyano, hydroxyl, nitro, —CHO, —C(═O)OH, —C(═O)NH 2 , —C(═O)NR 3 R 4 , —NR 3 R 4 , alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, halocycloalkyl, alkylcycloalkyl, cycloalkylalkyl, cycloalkylcycloalkyl, halocycloalkylalkyl, alkylcycloalkylalkyl, cycloalkenyl, halocycloalkenyl, alkoxyalkyl, haloalkoxyalkyl, cycloalkoxyalkyl, alkoxyalkoxyalkyl, alkylthioalkyl, formylalkyl, alkylcarbonylalkyl, alkylsulphinylalkyl, alkylsulphonylalkyl, alkylaminoalkyl, dialkylaminoalkyl, haloalkylaminoalkyl, cycloalkylaminoalkyl, alkylcarbonyl, haloalkylcarbonyl, cycloalkylcarbonyl, alkoxycarbonyl, cycloalkoxycarbonyl, cycloalkylalkoxycarbonyl, cycloalkylaminocarbonyl, hydroxyalkyl, alkoxy, haloalkoxy, cycloalkoxy, halocycloalkoxy, cycloalkylalkoxy, alkenyloxy, haloalkenyloxy, alkynyloxy, haloalkynyloxy, alkoxyalkoxy, alkylcarbonyloxy, haloalkylcarbonyloxy, cycloalkylcarbonyloxy, alkylcarbonylalkoxy, alkylthio, haloalkylthio, cycloalkylthio, alkylsulphinyl, haloalkylsulphinyl, alkylsulphonyl, haloalkylsulphonyl, cycloalkylsulphonyl, trialkylsilyl, alkylsulphonylamino, haloalkylsulphonylamino,
bonded to nitrogen of the 5-membered heterocyclyl of Q:
hydrogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, halocycloalkyl, alkylcycloalkyl, cycloalkylalkyl, phenyl, benzyl, alkylsulphonyl, —C(═O)H, alkoxycarbonyl or alkylcarbonyl,
L 2 is a direct bond, O, C(═O), S(O) m , CHR 20 or NR 21 ,
m is 0, 1 or 2,
R 20 is hydrogen, alkyl or haloalkyl,
R 21 is hydrogen, alkyl, haloalkyl, cycloalkyl, alkylcarbonyl, haloalkylcarbonyl, alkoxycarbonyl or haloalkoxycarbonyl,
R 1 is phenyl which is substituted once by a Z 4 substituent and may additionally optionally have further substitution, where these additional substituents are each independently selected from Z 4 and Z 1 ,
or
R 1 is naphthyl, dihydronaphthalenyl, tetrahydronaphthalenyl, hexahydronaphthalenyl, octahydronaphthalenyl or indenyl which is substituted once by a Z 5 substituent and may additionally optionally comprise further substitution, where additional substituents are each independently selected from Z 5 and Z 1 ,
or
R 1 is an optionally benzofused, substituted 5- or 6-membered heteroaryl which is substituted once by a substituent, either on a carbon by Z 6 or on a nitrogen by Z 7 , and may additionally optionally have further substitution, where additional substituents on carbon are each independently selected from Z 1 and Z 6 , and the additional substituents on nitrogen are each independently selected from Z 2 and Z 7 ,
Z 1 is hydrogen, halogen, hydroxyl, nitro, cyano, alkyl, alkenyl, alkyl, 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)NR 3 R 4 , —NR 3 R 4 , or -L 3 Z 3 ,
L 3 is a direct bond, —CH 2 —, —C(═O)—, sulphur, oxygen, —C(═O)O—, —C(═O)NH—, —OC(═O)— or —NHC(═O)—,
Z 3 is a phenyl radical, naphthalenyl radical or a 5- or 6-membered heteroaryl radical, each of which may contain 0, 1, 2 or 3 substituents, where the substituents are each independently selected from the following list:
substituents on carbon: halogen, cyano, nitro, hydroxyl, amino, —SH, alkyl, alkenyl, alkyl, 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 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)NR 3 R 4 , phenyl or benzyl,
Z 4 is SH, C(═O)H, C 7 -C 8 -cycloalkyl, C 7 -C 8 -halocycloalkyl, cycloalkylcycloalkyl, halocycloalkylalkyl, cycloalkenyl, halocycloalkenyl, C 4 -C 6 -alkoxy-C 1 -C 4 -alkyl, C 3 -alkoxy-C 2 -C 4 -alkyl, alkoxyalkoxyalkyl, alkylthioalkyl, alkylsulphinylalkyl, alkylsulphonylalkyl, alkylaminoalkyl, dialkylaminoalkyl, haloalkylaminoalkyl, cycloalkylaminoalkyl, C 4 -C 6 -alkylcarbonyl, haloalkylcarbonyl, cycloalkylcarbonyl, cycloalkoxycarbonyl, cycloalkylalkoxycarbonyl, cycloalkylaminocarbonyl, haloalkoxyalkyl, C 5 -C 6 -hydroxyalkyl, C 5 -C 6 -alkoxy, C 5 -C 6 -haloalkoxy, cycloalkoxy, halocycloalkoxy, cycloalkylalkoxy, alkenyloxy, haloalkenyloxy, alkynyloxy, haloalkynyloxy, alkoxyalkoxy, cyanoalkoxy, haloalkylcarbonyloxy, cycloalkylcarbonyloxy, alkylcarbonylalkoxy, C 5 -C 6 -alkylthio, C 5 -C 6 -haloalkylthio, C 5 -C 6 -alkylsulphinyl, C 5 -C 6 -haloalkylsulphinyl, C 5 -C 6 -alkylsulphonyl, C 5 -C 6 -haloalkylsulphonyl, cycloalkylsulphonyl, alkylsulphonylamino or haloalkylsulphonylamino,
Z 5 is tri(C 7 -C 4 -alkyl)silyl, benzyl, phenyl, SH, C 5 -C 6 -alkoxy, C 5 -C 6 -haloalkoxy, C 2 -C 6 -alkenyloxy, C 2 -C 6 -alkynyloxy, C 5 -C 6 -alkylthio or C 5 -C 6 -haloalkylthio,
Z 6 is SH, cycloalkylcycloalkyl or tri(C 3 -C 4 -alkyl)silyl,
Z 7 is alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, halocycloalkyl, alkylcycloalkyl, cycloalkylalkyl, cycloalkylcycloalkyl, alkylsulphonyl, C(═O)H, benzyl or phenyl.
10 . A compound of formula (XIIIa)
and/or a salt, metal complex and/or N-oxide thereof, wherein
A is phenyl which may contain up to five substituents,
where the substituents are each independently selected from Z A-1 ,
or
A is an optionally benzofused, unsubstituted or substituted 5- or 6-membered heteroaryl optionally comprising no more than four substituents, where the substituents on carbon are each independently selected from Z A-2 and the substituents on nitrogen are each independently selected from Z A-3 ,
Z A-1 are the same or different and are each independently hydrogen, halogen, hydroxyl, thioxyl, nitro, cyano, —C(═O)H, —C(═O)OH, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, cycloalkenyl, halocycloalkyl, halocycloalkenyl, hydroxyalkyl, cyanoalkyl, formylalkyl, alkoxyalkyl, haloalkoxyalkyl, cycloalkoxyalkyl, alkynyloxyalkyl, alkylthioalkyl, alkylsulphinylalkyl, alkylaminoalkyl, haloalkylaminoalkyl, cycloalkylaminoalkyl, dialkylaminoalkyl, alkylcarbonylalkyl, alkylsulphonylalkyl, alkylcycloalkyl, alkylcycloalkenyl, alkoxy, alkylcycloalkylalkyl, halocycloalkoxy, alkylthio, haloalkylthio, cycloalkylthio, alkynylthio, alkenyloxy, alkynyloxy, haloalkoxy, haloalkenyloxy, haloalkynyloxy, cycloalkoxy, alkoxyalkoxy, cycloalkylalkoxy, alkylcarbonyloxy, haloalkylcarbonyloxy, cycloalkylcarbonyloxy, cycloalkylamino, alkylcarbonylamino, cycloalkylcarbonylamino, alkoxycarbonylamino, alkylsulphonylamino, haloalkylsulphonylamino, phenylsulphonylamino, cycloalkylalkyl, halocycloalkylalkyl, cycloalkylcycloalkyl, alkoxyalkoxyalkyl, alkylaminocarbonyloxy, alkylcarbonylalkoxy, cycloalkylaminocarbonyl, cycloalkylalkoxycarbonyl, alkylsulphinyl, haloalkylsulphinyl, alkylsulphonyl, haloalkylsulphonyl, cycloalkylsulphonyl, alkylcarbonyl, haloalkylcarbonyl, cycloalkylcarbonyl, alkoxycarbonyl, cycloalkoxycarbonyl, trialkylsilyl, —SF 5 , phenyl, —C(═O)NR 3 R 4 or —NR 3 R 4 ,
Z A-2 and R G1 are the same or different and are each independently hydrogen, halogen, hydroxyl, thioxyl, nitro, cyano, —C(═O)H, —C(═O)OH, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, halocycloalkyl, hydroxyalkyl, formylalkyl, alkoxyalkyl, alkylcarbonylalkyl, alkylcycloalkyl, alkoxy, alkylcycloalkylalkyl, alkylthio, haloalkylthio, alkynylthio, alkenyloxy, alkynyloxy, haloalkoxy, alkoxyalkoxy, alkylcarbonyloxy, haloalkylcarbonyloxy, cycloalkylcarbonylamino, alkylsulphonylamino, halo alkylsulphonylamino, phenylsulphonylamino, cycloalkylalkyl, halocycloalkylalkyl, cycloalkylcycloalkyl, alkoxycarbonyloxy, alkylcarbonylthio, alkylsulphinyl, haloalkylsulphinyl, alkylsulphonyl, haloalkylsulphonyl, alkylcarbonyl, haloalkylcarbonyl, alkoxycarbonyl, alkylaminocarbonyloxy, —C(═O)NR 3 R 4 or —NR 3 R 4 ,
Z A-3 , R G2 and Z 2 are the same or different and are each independently hydrogen, —C(═O)H, —C(═O)NR 3 R 4 , alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, halocycloalkyl, alkylcycloalkyl, cycloalkylalkyl, alkoxyalkyl, alkylsulphonyl, haloalkylsulphonyl, cycloalkylsulphonyl, phenylsulphonyl, alkylcarbonyl, haloalkylcarbonyl, alkoxycarbonyl, haloalkoxycarbonyl, cycloalkoxycarbonyl, phenyl or benzyl,
R 3 and R 4 are the same or different and are each independently hydrogen, alkyl, alkenyl, alkynyl, haloalkyl, cycloalkyl, benzyl or phenyl,
L 1 is NR L12 or C(R L11 ) 2 ,
R L11 is the same or different and is independently hydrogen, halogen, hydroxyl, cyano, —C(═O)H, —C(═O)OH, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxyalkyl, alkylthioalkyl, alkylaminoalkyl, dialkylaminoalkyl, alkoxy, alkylthio, haloalkylthio, haloalkoxy, alkylcarbonyloxy, alkylcarbonylamino, alkylcarbonylthio, alkylsulphonyl, haloalkylsulphonyl, alkylcarbonyl, haloalkylcarbonyl, alkoxycarbonyl, trialkylsilyloxy, —NR 3 R 4 or —C(═O)NR 3 R 4 ,
or the two R L11 radicals, together with the carbon atom to which they are bonded, form a cyclopropyl ring, or
the two R L11 radicals are ═CH 2 , ═COR 3 , ═NOR 3 or ═CHN(R 7 ) 2 ,
R L12 is hydrogen, —C(═O)H, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, halocycloalkyl, alkylcycloalkyl, cycloalkylalkyl, cycloalkylaminocarbonyl, haloalkylaminocarbonyl, alkylsulphonyl, haloalkylsulphonyl, cycloalkylsulphonyl, alkylcarbonyl, haloalkylcarbonyl, alkoxycarbonyl, haloalkoxycarbonyl, cycloalkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, phenyl or benzyl,
R 7 is alkyl, alkenyl, alkynyl, haloalkyl, cycloalkyl, benzyl or phenyl,
Y is sulphur or oxygen,
X is carbon or nitrogen,
R 2 is hydrogen, alkyl, alkenyl, haloalkyl, alkoxy, halogen, cyano or hydroxyl,
R 10 is oxo, alkyl, alkenyl, haloalkyl, alkoxy, halogen, cyano or hydroxyl,
p is 0, 1 or 2,
G is 5-membered heteroaryl which is substituted by Q and may otherwise be unsubstituted or substituted, where the substituents on carbon are each independently selected from R G1 and the substituents on nitrogen are each independently selected from R G2 ,
Q is saturated or partly or fully unsaturated 5-membered heterocyclyl which is substituted by L 2 -R 1 and may otherwise be unsubstituted or substituted, where the substituents are each independently selected from R 5 ,
R 5 is the same or different and is independently:
bonded to carbon of the 5-membered heterocyclyl of Q:
hydrogen, oxo, halogen, cyano, hydroxyl, nitro, —CHO, —C(═O)OH, —C(═O)NH 2 , C(═O)NR 3 R 4 , —NR 3 R 4 , alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, halocycloalkyl, alkylcycloalkyl, cycloalkylalkyl, cycloalkylcycloalkyl, halocycloalkylalkyl, alkylcycloalkylalkyl, cycloalkenyl, halocycloalkenyl, alkoxyalkyl, haloalkoxyalkyl, cycloalkoxyalkyl, alkoxyalkoxyalkyl, alkylthioalkyl, formylalkyl, alkylcarbonylalkyl, alkylsulphinylalkyl, alkylsulphonylalkyl, alkylaminoalkyl, dialkylaminoalkyl, haloalkylaminoalkyl, cycloalkylaminoalkyl, alkylcarbonyl, haloalkylcarbonyl, cycloalkylcarbonyl, alkoxycarbonyl, cycloalkoxycarbonyl, cycloalkylalkoxycarbonyl, cycloalkylaminocarbonyl, hydroxyalkyl, alkoxy, haloalkoxy, cycloalkoxy, halocycloalkoxy, cycloalkylalkoxy, alkenyloxy, haloalkenyloxy, alkynyloxy, haloalkynyloxy, alkoxyalkoxy, alkylcarbonyloxy, haloalkylcarbonyloxy, cycloalkylcarbonyloxy, alkylcarbonylalkoxy, alkylthio, haloalkylthio, cycloalkylthio, alkylsulphinyl, haloalkylsulphinyl, alkylsulphonyl, haloalkylsulphonyl, cycloalkylsulphonyl, trialkylsilyl, alkylsulphonylamino, haloalkylsulphonylamino,
bonded to nitrogen of the 5-membered heterocyclyl of Q:
hydrogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, halocycloalkyl, alkylcycloalkyl, cycloalkylalkyl, phenyl, benzyl, alkylsulphonyl, —C(═O)H, alkoxycarbonyl or alkylcarbonyl,
L 2 is a direct bond, O, C(═O), S(O) m , CHR 20 or NR 21 ,
m is 0, 1 or 2,
R 20 is hydrogen, alkyl or haloalkyl,
R 21 is hydrogen, alkyl, haloalkyl, cycloalkyl, alkylcarbonyl, haloalkylcarbonyl, alkoxycarbonyl or haloalkoxycarbonyl,
R 1 is phenyl which is substituted once by a Z 4 substituent and may additionally optionally have further substitution, where these additional substituents are each independently selected from Z 4 and Z 1 ,
or
R 1 is naphthyl, dihydronaphthalenyl, tetrahydronaphthalenyl, hexahydronaphthalenyl, octahydronaphthalenyl or indenyl which is substituted once by a Z 5 substituent and may additionally optionally comprise further substitution, where additional substituents are each independently selected from Z 5 and Z 1 ,
or
R 1 is an optionally benzofused, substituted 5- or 6-membered heteroaryl which is substituted once by a substituent, either on a carbon by Z 6 or on a nitrogen by Z 7 , and may additionally optionally have further substitution, where additional substituents on carbon are each independently selected from Z 1 and Z 6 , and the additional substituents on nitrogen are each independently selected from Z 2 and Z 7 ,
Z 1 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)NR 3 R 4 , —NR 3 R 4 , or -L 3 Z 3 ,
L 3 is a direct bond, —CH 2 —, —C(═O)—, sulphur, oxygen, —C(═O)O—, —C(═O)NH—, —OC(═O)— or —NHC(═O)—,
Z 3 is a phenyl radical, naphthalenyl radical or a 5- or 6-membered heteroaryl radical, each of which may contain 0, 1, 2 or 3 substituents, where the substituents are each independently selected from the following list:
substituents on 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 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)NR 3 R 4 , phenyl or benzyl,
Z 4 is SH, C(═O)H, C 7 -C 8 -cycloalkyl, C 7 -C 8 -halocycloalkyl, cycloalkylcycloalkyl, halocycloalkylalkyl, cycloalkenyl, halocycloalkenyl, C 4 -C 6 -alkoxy-C 1 -C 4 -alkyl, C 3 -alkoxy-C 2 -C 4 -alkyl, alkoxyalkoxyalkyl, alkylthioalkyl, alkylsulphinylalkyl, alkylsulphonylalkyl, alkylaminoalkyl, dialkylaminoalkyl, haloalkylaminoalkyl, cycloalkylaminoalkyl, C 4 -C 6 -alkylcarbonyl, haloalkylcarbonyl, cycloalkylcarbonyl, cycloalkoxycarbonyl, cycloalkylalkoxycarbonyl, cycloalkylaminocarbonyl, haloalkoxyalkyl, C 5 -C 6 -hydroxyalkyl, C 5 -C 6 -alkoxy, C 5 -C 6 -haloalkoxy, cycloalkoxy, halocycloalkoxy, cycloalkylalkoxy, alkenyloxy, haloalkenyloxy, alkynyloxy, haloalkynyloxy, alkoxyalkoxy, cyanoalkoxy, haloalkylcarbonyloxy, cycloalkylcarbonyloxy, alkylcarbonylalkoxy, C 5 -C 6 -alkylthio, C 5 -C 6 -haloalkylthio, C 5 -C 6 -alkylsulphinyl, C 5 -C 6 -haloalkylsulphinyl, C 5 -C 6 -alkylsulphonyl, C 5 -C 6 -haloalkylsulphonyl, cycloalkylsulphonyl, tri(C 3 -C 4 -alkyl)silyl, alkylsulphonylamino or haloalkylsulphonylamino,
Z 5 is tri(C 7 -C 4 -alkyl)silyl, benzyl, phenyl, SH, C 5 -C 6 -alkoxy, C 5 -C 6 -haloalkoxy, C 2 -C 6 -alkenyloxy, C 2 -C 6 -alkynyloxy, C 5 -C 6 -alkylthio or C 5 -C 6 -haloalkylthio,
Z 6 is SH, cycloalkylcycloalkyl or tri(C 3 -C 4 -alkyl)silyl,
Z 7 is alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, halocycloalkyl, alkylcycloalkyl, cycloalkylalkyl, cycloalkylcycloalkyl, alkylsulphonyl, C(═O)H, benzyl or phenyl.
11 . A method for controlling phytopathogenic harmful fungi, comprising applying a compound according to claim 1 to the phytopathogenic harmful fungi and/or a habitat thereof.
12 . A composition for controlling phytopathogenic harmful fungi, comprising at least one compound according to claim 1 , in addition to and one or more extenders and/or surfactants.
13 . The compound according to claim 1 , capable of being used for controlling phytopathogenic harmful fungi.
14 . A process for producing compositions for controlling phytopathogenic harmful fungi, comprising mixing a compound of according to claim 1 , with one or more extenders and/or surfactants.
15 . The compound according to claim 1 , capable of being used for treatment of transgenic plants.