IP Library Granted Patent US 9,006,266
Granted Patent B2
US 9,006,266 · App. 13/993,262 · Granted Apr 14, 2015

Heteroarylpiperidine and -piperazine derivatives as fungicides

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Quick Facts
Patent No.
US 9,006,266
App. No.
13/993,262
Granted
Apr 14, 2015
Kind
B2
Abstract

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).

Claims (209)

1. A compound of the formula (I)

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 which may contain up to 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, thiol, 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, thiol, 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, haloalkylsulphonylamino, 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 9 ) 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 9 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, benzyl, naphthalenyl, an optionally benzofused, substituted 5- or 6-membered heteroaryl, each of which is substituted at least once by a substituent Z 4 and may otherwise be further unsubstituted or substituted, where the substituents are each independently selected from Z 4 and optionally from Z 1 ,

or

R 1 is a 5- to 8-membered nonaromatic (saturated or partially saturated) carbocyclic ring, a 5-, 6- or 7-membered nonaromatic heterocyclyl radical or an 8- to 11-membered carbocyclic or heterocyclic bicyclic ring, each of which is substituted at least once by a substituent Z 4 and may otherwise be unsubstituted or substituted, where the substituents are each independently selected from Z 4 and optionally from oxo, thio or Z 1 ,

Z 1 is hydrogen, halogen, hydroxyl, —SH, nitro, cyano, C(═O)H, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, cycloalkenyl, halocycloalkyl, halocycloalkenyl, hydroxyalkyl, alkoxyalkyl, haloalkoxyalkyl, cycloalkoxyalkyl, alkylthioalkyl, alkylsulphinylalkyl, alkylaminoalkyl, haloalkylaminoalkyl, cycloalkylaminoalkyl, dialkylaminoalkyl, alkylsulphonylalkyl, alkylcycloalkyl, alkoxy, alkylcycloalkylalkyl, halocycloalkoxy, alkylthio, haloalkylthio, cycloalkylthio, alkenyloxy, alkynyloxy, haloalkoxy, haloalkenyloxy, haloalkynyloxy, cycloalkoxy, alkoxyalkoxy, cycloalkylalkoxy, alkylcarbonyloxy, haloalkylcarbonyloxy, cycloalkylcarbonyloxy, cycloalkylamino, alkylsulphonylamino, haloalkylsulphonylamino, cycloalkylalkyl, halocycloalkylalkyl, cycloalkylcycloalkyl, alkoxyalkoxyalkyl, alkylcarbonylalkoxy, cycloalkylaminocarbonyl, cycloalkylalkoxycarbonyl, alkylcarbonylthio, alkylsulphinyl, haloalkylsulphinyl, alkylsulphonyl, haloalkylsulphonyl, cycloalkylsulphonyl, alkylcarbonyl, haloalkylcarbonyl, cycloalkylcarbonyl, alkoxycarbonyl, cycloalkoxycarbonyl, trialkylsilyl, —NR 3 R 4 , —C(═O)NR 3 R 4 or -L 3 Z 3 ,

R 7 is hydrogen, alkyl, haloalkyl, benzyl or Z 3 ,

R 8 is hydrogen, alkyl, haloalkyl, cycloalkylalkyl, cycloalkyl, alkylcycloalkyl, haloalkylcycloalkyl, alkoxylalkyl, haloalkoxyalkyl, benzyl or phenyl,

L 3 is a direct bond, —CH 2 —, —C(═O)—, sulphur, oxygen, —C(═O)O—, —C(═O)NH—, —OC(═O)— or —NHC(═O)—,

or

L 3 is —NR 20 —, —C(═S)—, —S(O) m —, —CHR 20 —, —CHR 20 —CHR 20 —, —CR 20 ═CR 20 —, —OCHR 20 , CHR 20 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 —NHCN, —SO 2 NHCN, —C(═O)OH, —C(═O)NH 2 , —C(═S)NR 3 R 4 , —C(═O)NHCN, cyanoalkyl, alkenylcarbonyloxy, alkoxyalkylthio, haloalkenylcarbonyloxy, alkoxycarbonylalkyl, alkoxyalkynyl, alkynylthio, halocycloalkylcarbonyloxy, alkenylamino, alkynylamino, haloalkylamino, cycloalkylalkylamino, alkoxyamino, haloalkoxyamino, alkylcarbonylamino, haloalkylcarbonylamino, alkoxycarbonylamino, alkylcarbonyl(alkyl)amino, haloalkylcarbonyl(alkyl)amino, alkoxycarbonyl(alkyl)amino, —NR 3 SO 2 Z 3 , alkenylthio, haloalkoxycarbonyl, alkoxyalkylcarbonyl, —SF 5 , haloalkoxycarbonylamino, —NHC(═O)H, di(haloalkyl)aminoalkyl, halocycloalkenyloxyalkyl, alkoxy(alkyl)aminocarbonyl, haloalkylsulphonylaminocarbonyl, alkoxycarbonylalkoxy, alkylaminothiocarbonylamino, cycloalkylalkylaminoalkyl, —C(═NOR 7 )R 8 , alkylthiocarbonyl, cycloalkenyloxyalkyl, alkoxyalkoxycarbonyl, dialkylaminothiocarbonylamino, alkylsulphonylaminocarbonyl, haloalkoxyhaloalkoxy, halocycloalkoxyalkyl, —N═C(R 9 ) 2 , dialkylaminocarbonylamino, alkoxyalkenyl, alkoxyhaloalkoxy, alkylthiocarbonyloxy, haloalkoxyalkoxy, —OSO 2 Z 3 , haloalkylsulphonyloxy, alkylsulphonyloxy, alkoxyhaloalkyl, di(haloalkyl)amino, —SO 2 NR 3 R 4 , —O(C═S)NR 3 R 4 , —O(C═S)SR 9 , dialkoxyalkyl, alkylaminocarbonylamino, haloalkoxyhaloalkyl, alkylaminocarbonylalkylamino, trialkylsilylalkynyloxy, trialkylsilyloxy, trialkylsilylalkynyl or -L 4 Z 3 ,

or

Z 4 is cyano(alkoxy)alkyl, dialkylthioalkyl, —O(C═O)H, —SCN, alkoxysulphonyl, cycloalkylsulphinyl, —NR 11 R 12 , —C(═O)NR 11 R 12 , —SO 2 NR 11 R 12

or

Z 4 is alkyl which may contain 1 or 2 substituents, where the substituents are each independently selected from the following list:

cyano, alkoxycarbonyl, —C(═N—R 9 )R 8 , —C(═N—NR 3 R 4 )R 8 , alkylcarbonylamino, haloalkylcarbonylamino, dialkylcarbonylamino, alkylcarbonyloxy, —C(═O)H, benzyloxy, benzoyloxy, —C(═O)OH, alkenyloxy, alkynyloxy, haloalkenyloxy, haloalkynyloxy, halocycloalkoxy, alkoxyamino, alkenylthio, alkynylthio, cycloalkylthio, haloalkoxyamino, haloalkylthio, alkenylsulphinyl, alkynylsulphinyl, cycloalkylsulphinyl, haloalkylsulphinyl, alkenylsulphonyl, alkynylsulphonyl, cycloalkylsulphonyl, haloalkylsulphonyl, alkoxycarbonyloxy, alkylcarbonyloxy, cycloalkylcarbonyloxy, haloalkylcarbonyloxy, haloalkenylcarbonyloxy, —SCN, alkylaminocarbonyloxy, alkylcarbonyl(alkyl)amino, alkoxycarbonyl(alkyl)amino, alkylaminocarbonylamino, alkylsulphonyloxy, haloalkoxycarbonylamino, haloalkylcarbonyl(alkyl)amino, haloalkylsulphonyloxy, alkylsulphonylamino, haloalkylsulphonylamino, alkylthiocarbonyloxy, cyanoalkoxy, cycloalkylalkoxy, benzyloxyalkoxy, alkoxyhaloalkoxy, alkoxyalkylthio, alkoxyalkylsulphinyl, alkoxyalkylsulphonyl, alkoxyalkylcarbonyloxy, cycloalkoxyalkoxy, haloalkoxyalkoxy, haloalkoxyhaloalkoxy, alkoxycarbonylalkoxy, alkylcarbonylalkoxy, alkylthioalkoxy, dialkylaminocarbonylamino, alkoxyalkoxyalkoxy, trialkylsilyloxy, trialkylsilylalkynyloxy, alkynylcycloalkyloxy, cycloalkylalkynyloxy, alkoxycarbonylalkynyloxy, arylalkynyloxy, alkylaminocarbonylalkynyloxy, dialkylaminocarbonylalkynyloxy, alkenylcarbonyloxy, alkynylcarbonyloxy, haloalkynylcarbonyloxy, cyanoalkylcarbonyloxy, cycloalkylsulphonyloxy, cycloalkylalkylsulphonyloxy, halocycloalkylsulphonyloxy, alkenylsulphonyloxy, alkynylsulphonyloxy, cyanoalkylsulphonyloxy, haloalkenylsulphonyloxy, haloalkynylsulphonyloxy, dialkylaminocarbonyloxy, haloalkylaminocarbonyloxy, N-alkyl-N-haloalkylaminocarbonyloxy, alkenyloxycarbonyl, alkynyloxycarbonyl, haloalkynyloxycarbonyl, cyanoalkyloxycarbonyl, alkenyloxysulphonyl, alkynyloxysulphonyl,

or

Z 4 is alkenyl which may contain 1 or 2 substituents, where the substituents are each independently selected from the following list:

trialkylsilyl, cycloalkyl, cyclopropylidenyl, alkoxy, trialkylsilyloxy, alkylcarbonyloxy

or

Z 4 is alkynyl which may contain 1 or 2 substituents, where the substituents are each independently selected from the following list:

cycloalkyl, cyclopropylidenyl,

or

Z 4 is alkoxy which may contain 1 or 2 substituents, where the substituents are each independently selected from the following list:

alkoxycarbonyl, cycloalkoxy, alkylcarbonyloxy, —O(C═O)H, alkylthio, hydroxyalkyl, trialkylsilyl, cycloalkylsulphonyl, haloalkylsulphonyl, benzyloxy, alkoxyalkoxy, alkylsulphonyl, cyano,

or

Z 4 is alkenyloxy which may contain 1 or 2 substituents, where the substituents are each independently selected from the following list:

cycloalkyl, hydroxyl, alkoxy, alkenyloxy, alkynyloxy, haloalkoxy, haloalkenyloxy, haloalkynyloxy, cycloalkoxy, cyclohaloalkoxy, alkoxycarbonyl, haloalkoxycarbonyl, cycloalkoxycarbonyl, alkenyloxycarbonyl, haloalkenyloxycarbonyl, alkynyloxycarbonyl, haloalkynyloxycarbonyl, alkylcarbonyl, haloalkylcarbonyl, cycloalkylcarbonyl, cyclohaloalkylcarbonyl, alkenylcarbonyl, haloalkenylcarbonyl, alkynylcarbonyl, haloalkynylcarbonyl,

or

Z 4 is alkynyloxy which may contain 1 or 2 substituents, where the substituents are each independently selected from the following list:

cycloalkyl, alkoxycarbonyl, —Z 3 , alkylaminocarbonyl, dialkylaminocarbonyl

or

Z 4 is a substituted hydroxyl, where the substituent is selected from the following list:

alkynylcarbonyl, haloalkynylcarbonyl, cyanocarbonyl, cyanoalkylcarbonyl, cycloalkylsulphonyl, cycloalkylalkylsulphonyl, halocycloalkylsulphonyl, alkenylsulphonyl, alkynylsulphonyl, cyanoalkylsulphonyl, haloalkenylsulphonyl, haloalkynylsulphonyl, alkynylcycloalkyl, cyanoalkenyl, cyanoalkynyl, alkoxycarbonyl, alkenyloxycarbonyl, alkynyloxycarbonyl, alkoxyalkylcarbonyl, —C(═O)NR 3 R 4 , —C(═O)NR 11 R 12 ,

or

Z 4 is a substituted carbonyl, where the substituent is selected from the following list:

halocycloalkoxy, alkylcycloalkyl, halocycloalkyl, alkenyloxy, alkynyloxy, cyanoalkoxy, alkylthioalkoxy,

R 11 is alkenyl, alkynyl, alkoxyalkyl, cyanoalkyl, formyl, haloalkyl, benzyl, phenyl, alkylcarbonyl, cycloalkoxycarbonyl, alkoxycarbonyl, alkenyloxycarbonyl, alkynyloxycarbonyl, haloalkylcarbonyl, halocycloalkylcarbonyl, cycloalkoxycarbonyl, cycloalkylcarbonyl, dialkylaminocarbonyl, dialkylaminothiocarbonyl,

R 12 is alkenyl, alkynyl, alkoxyalkyl, cyanoalkyl, formyl, hydrogen, haloalkyl, benzyl, phenyl, alkylcarbonyl, cycloalkoxycarbonyl, alkoxycarbonyl, alkenyloxycarbonyl, alkynyloxycarbonyl, haloalkylcarbonyl, halocycloalkylcarbonyl, cycloalkoxycarbonyl, cycloalkylcarbonyl, dialkylaminocarbonyl, dialkylaminothiocarbonyl,

L 4 is —C(═O)O—, —C(═O)NR 3 —, —OC(═O)—, —NR 3 C(═O)—, —OCH 2 C≡C— or —OCH 2 CH═CH—,

and/or a salt, metal complex and N-oxide thereof.

2. A compound according to claim 1 , in which

A is phenyl which may contain up to 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, hydroxyl-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 may contain up 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.

3. A compound according to claim 1 , in which p is 0 to 1.

4. A compound of the formula (I) according to claim 1 , in which 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.

5. A compound of the formula (I) according to claim 1 , in which Q is

where the bond identified by “*” is bonded directly to G or L 2 , and where the bond identified by “#” is bonded directly to L 2 or G, or where the bond identified by “*” is bonded directly to L 2 , and the bond identified by “#” is at the same time bonded directly to G.

6. A compound according to claim 1 , in which

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.

7. A compound according to claim 1 , in which

L 2 is a direct bond, —C(═O)—, —CHR 20 — or —NR 21 —, and optionally a direct bond,

R 1 is C 5 -C 6 -cycloalkenyl or C 3 -C 8 -cycloalkyl, where the C 5 -C 6 -cycloalkenyl or C 3 -C 8 -cycloalkyl is in each case substituted at least once by a substituent Z 4 and may otherwise be unsubstituted or substituted, where the substituents are each independently selected from Z 4 and optionally from Z 1-1 , and optionally substituted cyclopentenyl, cyclohexenyl, cyclopentyl, cyclohexyl or cycloheptyl, each of which may contain 1 or 2 substituents, where the substituents are each independently selected at least once from Z 4 and optionally from the following list: methyl, ethyl, methoxy, ethoxy, trifluoromethoxy, ethynyl, 2-propenyloxy, 2-propynyloxy, methylcarbonyloxy, ethylcarbonyloxy, trifluorocarbonyloxy, methylthio, ethylthio or trifluoromethylthio, or

R 1 is phenyl which is substituted at least once by a substituent Z 4 and may otherwise be unsubstituted or substituted, where the substituents are each independently selected from Z 4 and optionally from Z 1-2 , and optionally phenyl which may contain 1, 2 or 3 substituents, where the substituents are each independently selected at least once from Z 4 and optionally 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, trifluoromethylcarbonyloxy, chloromethylcarbonyloxy, methylthio, ethylthio, methylsulphonyl, methylsulphonylamino, trifluoromethylsulphonylamino or -L 3 R 3 , and optionally phenyl which may contain one substituent, where the substituent is selected from the following list:

N-methoxy-n-methylaminocarbonyl, —C(═NOH)H, —C(═NOCH 3 )H, —C(═NOCH 2 CH 3 )H, —C(═NOCH(CH 3 )CH 3 )H, —C(═NOH)CH 3 , —C(═NOCH 3 )CH 3 , —C(═NOCH 2 CH 3 )CH 3 , —C(═NOCH(CH 3 )CH 3 )CH 3 , dimethylaminosulphonyl, C(═O)NH 2 , ethylaminosulphonyl, trimethylsilylethynyl, diethylaminosulphonyl, methylaminosulphonyl, trimethylsilyloxy, trimethylsilylethynyloxy, trifluoromethylamino, dimethylaminocarbonylamino, C(═O)OH, 1,1-dimethylethylcarbonylamino, chloromethylcarbonylamino, trifluoromethylcarbonylamino, 1,1-dimethylethoxycarbonylamino, ethylcarbonylamino, 1-methylethoxycarbonylamino, trifluoromethylcarbonylamino, methylcarbonylamino, 1-methylethylcarbonylamino, trifluoromethylsulphonyloxy, methylsulphonyloxy or phenylsulphonylamino, 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 substituent Z 4 and may otherwise be unsubstituted or substituted, where the substituents are each independently selected from Z 4 and optionally from Z 1-3 .

8. A compound according to claim 1 , in which

Z 4 is —C(═O)OH, —C(═O)NH 2 , —C(═S)NR 3 R 4 , cyano-C 1 -C 6 -alkyl, C 2 -C 6 -alkenylcarbonyloxy, C 2 -C 6 -alkynylthio, C 3 -C 8 -halocycloalkylcarbonyloxy, C 2 -C 6 -alkenylamino, C 2 -C 6 -alkynylamino, C 1 -C 6 -haloalkylamino, C 3 -C 8 -cycloalkyl-C 1 -C 6 -alkylamino, C 1 -C 6 -alkoxyamino, C 1 -C 6 -haloalkoxyamino, C 1 -C 6 -alkylcarbonylamino, C 1 -C 6 -haloalkylcarbonylamino, C 1 -C 6 -alkoxycarbonylamino, C 1 -C 6 -alkylcarbonyl(C 1 -C 6 -alkyl)amino, C 1 -C 6 -haloalkylcarbonyl(C 1 -C 6 -alkyl)amino, C 1 -C 6 -alkoxycarbonyl(C 1 -C 6 -alkyl)amino, —NR 3 SO 2 Z 3 , C 2 -C 6 -alkenylthio, C 1 -C 6 -haloalkoxycarbonyl, C 1 -C 6 -alkoxy-C 1 -C 4 -alkylcarbonyl, —SF 5 , C 1 -C 6 -haloalkoxycarbonylamino, —NHC(═O)H, C 1 -C 6 -alkoxy(C 1 -C 4 -alkyl)aminocarbonyl, C 1 -C 6 -alkoxycarbonyl-C 1 -C 6 -alkoxy, —C(═NOR 7 )R 8 , —N═C(R 9 ) 2 , di(C 1 -C 6 -alkyl)aminocarbonylamino, di(C 1 -C 6 -alkyl)aminosulphonyl, di(C 1 -C 6 -haloalkyl)amino, C 1 -C 6 -alkylaminosulphonyl, C 1 -C 6 -alkylaminocarbonylamino, tri(C 1 -C 4 -alkyl)silyloxy, C 1 -C 6 -haloalkylsulphonyloxy, C 1 -C 6 -alkylsulphonyloxy, tri(C 1 -C 4 -alkyl)silyl—C 2 -C 4 -alkynyloxy, tri(C 1 -C 4 -alkyl)silyl-C 2 -C 4 -alkynyl or -L 4 Z 3 , and optionally —C(═O)OH, —C(═O)NH 2 , —NHC(═O)H, —C(═S)NR 3 R 4 , cyanomethyl, cyanoethyl, propenoyloxy, but-2-enoyloxy, propyn-2-ylthio, propen-2-ylamino, propyn-2-ylamino, trifluoromethylamino, difluoromethylamino, methoxyamino, ethoxyamino, propoxyamino, 1-methylethoxyamino, methoxycarbonylamino, ethoxycarbonylamino, 1-methylethoxycarbonylamino, 1,1-dimethylethoxycarbonylamino, trifluoromethylcarbonylamino, methylcarbonylamino, ethylcarbonylamino, 1-methylethylcarbonylamino, 1,1-dimethylethylcarbonylamino, phenylsulphonylamino, propen-2-ylthio, N-methoxy-N-methylaminocarbonyl, methoxycarbonylmethoxy, ethoxycarbonylmethoxy, propoxycarbonylmethoxy, 1-methylethoxycarbonylmethoxy, 1,1-dimethylethylcarbonylmethoxy, —C(═NOR 7 )R 8 , dimethylaminocarbonylamino, diethylaminocarbonylamino, dimethylaminosulphonyl, diethylaminosulphonyl, methylaminosulphonyl, ethylaminosulphonyl, propylaminosulphonyl, 1-methylethylaminosulphonyl, 1,1-dimethylethylaminosulphonyl, methylaminocarbonylamino, ethylaminocarbonylamino, propylaminocarbonylamino, 1-methylethylaminocarbonylamino, 1,1-dimethylethylaminocarbonylamino, 2-methylpropylaminocarbonylamino, 1-chlorocyclopropylcarbonyloxy, 1-fluorocyclopropylcarbonyloxy, trifluoromethylsulphonyloxy, trimethylsilyloxy, chloromethylcarbonylamino, trifluoromethylcarbonylamino, methylsulphonyloxy, ethylsulphonyloxy, trimethylsilylethynyloxy, trimethylsilylethynyl or -L 4 Z 3 ,

Z 4 is —NR 11 R 12 , —C(═O)NR 11 R 12 , —SO 2 NR 11 R 12 , —O(C═O)H, —SCN, C 1 -C 3 -alkoxysulphonyl, C 3 -C 8 -cycloalkylsulphinyl, cyano(C 1 -C 3 -alkoxy)-C 1 -C 3 -alkyl or

Z 4 is C 1 -C 3 -alkyl which may contain 1 or 2 substituents, where the substituents are each independently selected from the following list:

cyano, —C(═O)H, C 2 -C 4 -alkenyloxy, C 2 -C 4 -alkynyloxy, C 2 -C 4 -alkenylthio, C 2 -C 4 alkynylthio, C 1 -C 3 -haloalkylthio, C 2 -C 4 -alkenylsulphinyl, C 2 -C 4 -alkynylsulphinyl, C 1 -C 3 -haloalkylsulphinyl, C 2 -C 4 -alkenylsulphonyl, C 2 -C 4 -alkynylsulphonyl, C 1 -C 3 -haloalkylsulphonyl, C 1 -C 3 -alkylcarbonyloxy, C 1 -C 3 -haloalkylcarbonyloxy, C 1 -C 3 -alkylaminocarbonyloxy, C 1 -C 3 -alkylcarbonylamino, C 1 -C 3 -alkylaminocarbonylamino, C 1 -C 3 -haloalkylcarbonylamino, C 1 -C 3 -alkylsulphonylamino, C 1 -C 3 -haloalkylsulphonylamino, C 1 -C 3 -alkylthiocarbonyloxy, cyano-C 1 -C 3 -alkoxy, C 3 -C 8 -cycloalkyl-C 1 -C 3 -alkoxy, C 1 -C 3 alkoxy-C 1 -C 3 -alkylthio, C 1 -C 3 -alkoxy-C 1 -C 3 -alkylsulphinyl, C 1 -C 3 -alkoxy-C 1 -C 3 -alkylsulphonyl, C 1 -C 3 -haloalkoxy-C 1 -C 3 -alkoxy, C 1 -C 3 -alkylcarbonyl-C 1 -C 3 -alkoxy, C 2 -C 4 -alkylthio-C 1 -C 3 -alkoxy, di(C 1 -C 3 -alkyl)aminocarbonylamino, tri(C 1 -C 4 -alkyl)silyloxy,

or

Z 4 is C 1 -C 3 -alkoxy which may contain 1 or 2 substituents, where the substituents are each independently selected from the following list:

C 1 -C 3 -alkylcarbonyloxy C 1 -C 3 -alkoxycarbonyl, C 3 -C 8 -cycloalkoxy, C 1 -C 3 -alkylcarbonyloxy, —O(C═O)H, C 1 -C 3 -alkylthio, hydroxyl-C 1 -C 3 -alkyl, C 3 -C 8 -cycloalkylsulphonyl, C 1 -C 3 -haloalkylsulphonyl, C 1 -C 3 -alkoxy-C 1 -C 3 -alkoxy, C 1 -C 3 -alkylsulphonyl, or

Z 4 is C 2 -C 4 -alkenyloxy which may contain 1 or 2 substituents, where the substituents are each independently selected from the following list:

C 3 -C 8 -cycloalkyl, hydroxyl, C 1 -C 3 -alkoxy, C 1 -C 3 -alkoxycarbonyl, C 1 -C 3 -alkylcarbonyl, or

Z 4 is C 2 -C 4 -alkynyloxy which may contain 1 or 2 substituents, where the substituents are each independently selected from the following list:

C 3 -C 8 -cycloalkyl, —Z 3 , or

Z 4 is a substituted hydroxyl, where the substituents are each selected from the following list:

C 2 -C 4 -alkynylcarbonyl, cyano-C 1 -C 3 -alkylcarbonyl, C 3 -C 8 -cycloalkylsulphonyl, C 3 -C 8 -halocycloalkylsulphonyl, C 2 -C 4 -alkenylsulphonyl, C 1 -C 3 -alkylaminocarbonyl, C 2 -C 4 -alkynyl-C 3 -C 8 -cycloalkyl, cyanocarbonyl, cyano-C 2 -C 4 -alkenyl, —C(═O)NR 3 R 4 .

9. 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.

10. A composition for controlling phytopathogenic harmful fungi, comprisining at least one compound according to claim 1 , in addition to one or more extenders and/or surfactants.

11. A bis(difluoromethyl)pyrazole derivative which is a compound according to claim 1 that is capable of controlling phytopathogenic harmful fungi.

12. A process for producing compositions for controlling phytopathogenic harmful fungi, comprising mixing a bis(difluoromethyl)pyrazole derivative which is a compound according to claim 1 with one or more extenders and/or surfactants.

13. A compound according to claim 1 that is capable of being used for treating a transgenic plant.

14. A compound according to claim 1 , in which

A is pyrazol-1-yl which may contain up to two substituents, where the substituents are each independently selected from the following list:

methyl, ethyl, chloring, bromine, fluorine, difluoromethyl, or trifluoromethyl,

or

A is phenyl which may contain up to two substituents, where the substituents are each independently selected from the following list:

methyl, ethyl, iodine, chlorine, bromine, fluorine, methoxy, ethoxy, difluoromethyl, or trifluoromethyl,

R 3 and R 4 are hydrogen, methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, or 1,1-dimethylethyl,

L 1 is CH 2 ,

R L11 is hydrogen or methyl,

R L12 is hydrogen,

R 9 is hydrogen, methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, or 1,1-dimethylethyl,

Y is oxygen,

X is carbon,

R 2 is hydrogen or fluorine,

R 10 is fluorine,

p is 0,

G is

where the bond identified by “v” is bonded directly to X and where the bond identified at “w” is bonded directly to Q,

R G1 is hydrogen,

Q is

where the bond identified by “x” is bonded directly to G and where the bond identified by “y” is bonded directly to L 2 ,

R 5 is hydrogen,

L 2 is a direct bond,

m is 0 or 2,

R 20 is hydrogen, methyl, ethyl, or trifluoromethyl,

R 21 is hydrogen or methyl,

R 1 is substituted cyclopentenyl, cyclogexenyl, cyclopentyl, cyclohexyl, or cycloheptyl, each of which may contain 1 or 2 substituents, where the substituents are each independently selected at least once from Z 4 and optionally from the following list:

methyl, ethyl, methoxy, ethoxy, trifluoromethoxy, ethynyl, 2-propenyloxy, 2-propynyloxy, methylcarbonyloxy, ethylcarbonyloxy, trifluorocarxonyloxy, methylthio, ethylthio, or trifluoromethylthio,

or

R 1 is phenyl which contains one substituent, where the substituent is selected from the following list:

N-methoxy-N-methylaminocarbonyl, —C(═NOH)H, —C(═NOCH 3 )H, —C(═NOCH 2 CH 3 )H, —C(═NOCH(CH 3 )CH 3 )H, —C(═NOH)CH 3 , —C(═NOCH 3 )CH 3 , —C(═NOCH 2 CH 3 )CH 3 , —C(NOCH(CH 3 )CH 3 )CH 3 , dimethylaminosulphonyl, C(═O)NH 2 , ethylaminosulphonyl, trimethylsilylethynyl, diethylaminosulphonyl, methylaminosulphonyl, trimethylsilyloxy, trimethylsilylethynyloxy, trifluoromethylamino, dimethylaminocarbonylamino, C(═O)OH, 1,1-dimethylethylcarbonylamino, chloromethylcarbonylamino, trifluoromethylcarbonylamino, 1,1-dimethylethoxycarbonylamino, ethylcarbonylamino, 1-methylethoxycarbonylamino, trifluoromethylcarbonylamino, methylcarbonylamino, 1-methylethylcarbonylamino, trifluromethylcarbonylami no, methylcarbonylamino, 1-methylethylcarbonylamino, trifluoromethylsulphonyloxy, methylsulphonyloxy, or phenylsulphonylamino,

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-3y1,1H-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 substituent Z 4 and may otherwise contain up to three substituents each independently selected from Z 4 and optionally 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-3y1, 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, pyradin-4,yl, pyradazin-3-yl, pyridazin-4-yl, pyramidin-2-yl, pyramidin-4-yl, pyrimidin-5-yl, or pyrazin-2-yl, each of which may contain 1 or 2 substituents, where the substituents are each independently selected at least once from Z 4 and optionally from the following list:

substituents on carbon:

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, trifluoromethylcarbonyloxy, chloromethylcarbonyloxy, methylcarbonylamino, trifluoromethylcarbonylamino, chloromethylcarbonylamino, methylthio, ethylthio, methylsulphinyl, methylsulphonyl, methylsulphonyloxy, trifluoromethylsulphonyloxy, 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 piperidin-1-yl, piperidin-2-yl, piperidin-3-yl, piperidin-4-yl, piperazin-1-yl, piperazin-2-yl, piperazin-3-yl, morpholin-1-yl, morpholin-2-yl, morpholin-3-yl, tetrahydropyran-2-yl, tetrahydropyran-3-yl, tetrahydropyran-4-yl, 1,2,3,4-tetrahydroquinolin-1-yl, 1,2,3,4-tetrahydroisoquinolin-2-yl, 1,2,3,4-tetrahydroquinoxalin-1-yl, indolin-1-yl, isoindolin-2-yl, decahydroquinolin-1-yl or decahydroisoquinolin-2-yl, each of which may contain 1 or 2 substituents, where the substituents are each independently selected at least once from Z4 and optionally from the following list:

substituents on carbon:

fluorine, chlorine, bromine, iodine, methyl, methoxy, 2-propynyloxy, 2-propenyloxy, substituents on nitrogen:

methyl, ethyl, n-propyl, —C(═O)H, methylcarbonyl, trifluoromethylcarbonyl, chloromethylcarbonyl, methylsulphonyl, trifluoromethylsulphonyl, phenylsulphonyl, phenyl or 2-propynyl,

Z 1-3 and Z 1-5 are the same or different and are each independently hydrogen, halogen, cyano, nitro, —C(═O)H, —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 -alkylcarbonyl, 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, C 1 -C 4 -haloalkylthio, C 1 -C 4 -alkylsulphonyl, C 1 -C 4 -haloalkylsulphonyl, or C 1 -C 6 -haloalkylcarbonyloxy,

Z 1-4 is hydrogen, halogen, cyano, hydroxyl, —SH, nitro, —C(═O)H, —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 3 -C 8 -cycloalkenyl, C 3 -C 8 -halocycloalkenyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkylcarbonyl, C 3 -C 8 -cycloalkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, C 3 -C 8 -cycloalkoxycarbonyl, C 3 -C 8 -cycloalkylaminocarbonyl, C 1 -C 6 -alkoxy, C1-C 6 -haloalkoxy, C 3 -C 8 -cycloalkoxy, C 3 -C 8 -halocycloalkoxy, C2-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, C 1 -C 6 -alkylcarbonyloxy, C 1 -C 6 -haloalkylcarbonyloxy, C 3 -C 8 -cycloalkylcarbonyloxy, C 1 -C 6 -alkylcarbonyl-C 1 -C 4 -alkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -haloalkylthio, C 3 -C 6 -cycloalkylthio, C 1 -C 6 -alkylsulphonyl, C 1 -C 6 -haloalkylsulphonyl, C 3 -C 8 -cycloalkylsulphonyl, C 1 -C 6 -alkylsulphonylamino or C 1 -C 6 -haloalkylsulphonylamino,

Z 1-6 are the same or different and are each independently hydrogen, cyano, halogen, —C(═O)H 2 , —C(═O)NR 3 R 4 , phenyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -cycloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyloxy, C 2 -C 6 -alkynyloxy, C 1 -C 6 -alkylthio, —NR 3 R 4 , C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkylcarbonyloxy or C1-C 6 -haloalkylthio,

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,

R 7 is hydrogen, methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1,1-dimethylethyl or 2-methylpropyl,

R 8 is hydrogen, methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1,1-demethylethyl or 2-methylpropyl,

L 3 is a direct bond,

Z 3 is a phenyl radical which may contain up to two substituents, where the substituents are each independently selected from the following list:

chlorine, bromine, iodine, fluorine, cyano, nitro, hydroxyl, amino, —SH, methyl, ethyl, n-propyl, 1-methylethyl, 1,1-dimethylethyl, ethenyl, propen-2-yl, ethynyl, propyn-2-yl, trifluoromethyl, difluoromethyl, methoxymethyl, methylcarbonyl, ethylcarbonyl, trifluoromethylcarbonyl, methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, 1-methylethoxycarbonyl, 1,1-dimethylethoxycarbonyl, methoxy, ethoxy, n-propoxy, 1-methylethoxy, 1,1-dimethylethoxy, trifluoromethoxy, ethenyloxy, 2-propenyloxy, ethynyloxy, 2-propynyloxy, methylthio, ethylthio, trifluoromethylthio, methylsulphonyl, ethylsulphonyl, propylthionyl, 1-methylethylthio, trifluoromethylsulphonyl, methylamino, ethylamino, n-propylamino, 1-methylethylamino, 1,1-dimethylethylamino or dimethylamino,

or

Z 3 is naphthalenyl,

Z 4 is —C(═O)OH, —C(═O)NH 2 , —NHC(═O)H, —C(═S)NR 3 R 4 , cyanomethyl, cyanoethyl, propenoyloxy, but-2-enoyloxy, propyn-2-ylthio, propen-2-ylamino, propyn-2-ylamino, trifluoromethylamino, difluoromethylamino, methoxyamino, ethoxyamino, propoxyammo, 1-methylethoxyamino, methoxycarbonylamino, ethoxycarbonylamino, 1-methylethoxycarbonylam ino, 1,1-dimethylethoxycarbonylamino, trifluoromethylcarbonylamino, methylcarbonylamino, ethylcarbonylamino, 1-methylethylcarbonylamino, phenylsulphonylamino, 1,1-dimethylethylcarbonylamino, propen-2-ylthio, N-methoxy-N-methylaminocarbonyl, methoxycarbonylmethoxy, ethoxycarbonylmethoxy, propoxycarbonylmethoxy, 1-methylethoxycarbonylmethoxy, 1,1-dimethylethylcarbonylmethoxy, —C(═NOR 7 )R 8 , dimethylaminocarbonylamino, diethylaminocarbonylamino, dimethylaminosulphonyl, diethylaminosulphonyl, methylaminosulphonyl, ethylaminosulphonyl, propylaminosulphonyl, 1-methylethylaminosulphonyl, 1,1-dimethylethylaminosulphonyl, methylaminocarbonylamino, ethylaminocarbonylamino, propylaminocarbonylamino, 1-methylethylaminocarbonylamino, 1,1-dimethylethylaminocarbonylamino, 2-methylpropylaminocarbonylamino, 1-chlorocyclopropylcarbonyloxy, 1-fluorocyclopropylcarbonyloxy, trifluoromethylsulphonyloxy, trimethylsilyloxy, chloromethylcarbonylamino, trifluoromethylcarbonylamino, methylsulohonyloxy, ethylsulphonyloxy, trimethylsilylethynyloxy, trimethylsilylethynyl, or -L 4 Z 3 ,

or

Z 4 is —NR 11 R 12 , —C(═O)NR 11 ,R 12 , —SO 2 NR 11 R 12 , —O(C═O)H, —SCN, C 1 -C 3 -alkoxysulphonyl, C 3 -C 8 -cycloalkylsulphinyl, cyano(C 1 -C 3 -alkoxy)-C 1 -C 3 -alkyl,

or

Z 4 is C 1 -C 3 -alkyl which may contain 1 or 2 substituents, where the substituents are each independently selected from the following list:

cyano, —C(═O)H, C 2 -C 4 -alkenyloxy, C 2 -C 4 -alkynyloxy, C 2 -C 4 -alkenylthio, C 2 -C 4 -alkynylthio, C 1 -C 3 -haloalkylthio, C 2 -C 4 -alkenylsulphinyl, C 2 -C 4 -alkynylsulphinyl, C 1 -C 3 -haloalkylsulphinyl, C 2 -C 4 -alkenylsulphonyl, C 2 -C 4 -alkynylsulphonyl, C 1 -C 3 -haloalkylsulphonyl, C 1 -C 3 -alkylcarbonyloxy, C 1 -C 3 -haloalkylcarbonyloxy, C 1 -C 3 -alkylaminocarbonyloxy, C 1 -C 3 -alkylcarbonylamino, C 1 -C 3 -alkylaminocarbonylamino, C 1 -C 3 -haloalkylcarbonylamino, C 1 -C 3 -alkylsulphonylamino, C 1 -C 3 -haloalkylsulphonylamino, C 1 -C 3 -alkylthiocarbonyloxy, cyano-C 1 -C 3 -alkoxy, C 3 -C 8 -cycloalkyl-C 1 -C 3 -alkoxy, C 1 -C 3 -alkoxy-C 1 -C 3 -alkylthio, C 1 -C 3 -alkoxy-C 1 -C 3 -alkylsulphinyl, C 1 -C 3 -alkoxy-C 1 -C 3 -alkylsulphonyl, C 1 -C 3 -haloalkoxy-C 1 -C 3 -alkoxy, C 1 -C 3 -alkylcarbonyl-C 1 -C 3 -alkoxy, C 2 -C 4 -alkylthio-C 1 -C 3 -alkoxy, di(C 1 -C 3 -alkyl)aminocarbonylamino, or, tri(C 1 -C 4 -alkyl)silyloxy,

or

Z 4 is C 1 -C 3 -alkoxy which may contain 1 or 2 substituents, where the substituents are each independently selected from the following list:

cyano, C 1 -C 3 -alkylcarbonyloxy, C 1 -C 3 -alkoxycarbonyl, C 3 -C 8 -cycloalkoxy, C 1 -C 3 -alkylcarbonyloxy, —O(C═O)H, C 1 -C 3 -alkylthio, hydroxy-C 1 -C 3 -alkyl, C 3 -C 8 -cycloalkylsulphonyl, C 1 -C 3 -haloalkylsulphonyl, C1-C 3 -alkoxy-C 1 -C 3 -alkoxy, C 1 -C 3 -alkylsulphonyl,

or

Z 4 is C 2 -C 4 -alkenyloxy which may contain 1 or 2 substituents, where the substituents are each independently selected from the following list:

C 3 -C 8 -cycloalkyl, hydroxyl, C 1 -C 3 -alkoxy, C 1 -C 3 -alkoxycarbonyl, C 1 -C 3 -alkylcarbonyl,

or

Z 4 is C 2 -C 4 -alkynyloxy which may contain 1 or 2 substituents, where the substituents are each independently selected from the following list:

C 3 -C 8 -cycloalkyl or —Z3,

or

Z 4 is substituted hydroxyl, where the substituents are each selected from the following list:

C 2 -C 4 -alkynylcarbonyl, cyano-C 1 -C 3 -alkylcarbonyl, C 3 -C 8 -cycloalkylsulphonyl, C 3 -C 8 -halocycloalkylsulphonyl, C 2 -C 4 -alkenylsulphonyl, C 1 -C 3 -alkylaminocarbonyl, C 2 -C 4 -alkynyl-C 3 -C 8 -cycloalkyl, cyanocarbonyl, cyano-C 2 -C 4 -alkenyl, —C(═O)NR 3 R 4 ,

R 11 is C 3 -C 4 -alkenyl, C 3 -C 4 -alkynyl, cyano-C 1 -C 3 -alkyl, formyl, C 1 -C 3 -haloalkyl, benzyl, phenyl, C 1 -C 3 -alkylcarbonyl, C 3 -C 8 -cycloalkoxycarbonyl, C 1 -C 3 -alkoxycarbonyl, C 3 -C 4 -alkenyloxycarbonyl, C 3 -C 4 -alkynyloxycarbonyl, C 1 -C 3 -haloalkylcarbonyl, C 3 -C 8 -halocycloalkylcarbonyl, C 3 -C 8 -cycloalkoxycarbonyl, C 3 -C 8 -cycloalkylcarbonyl, di(C 1 -C 3 -alkyl)aminocarbonyl,

R 12 is hydrogen, C 3 -C 4 -alkenyl, C 3 -C 4 -alkynyl, cyano-C 1 -C 3 -alkyl, formyl, C 1 -C 3 -haloalkyl, benzyl, phenyl, C 1 -C 3 -alkylcarbonyl, C 3 -C 8 -cycloalkoxycarbonyl, C 1 -C 3 -alkoxycarbonyl, C 3 -C 4 -alkenyloxycarbonyl, C 3 -C 4 -alkynyloxycarbonyl, C 1 -C 3 -haloalkylcarbonyl, C 3 -C 8 -halocycloalkylcarbonyl, C 3 -C 8 -cycloalkoxycarbonyl, C 3 -C 8 -cycloalkylcarbonyl, di(C 1 -C 3 -alkyl)aminocarbonyl, and

L4 is —OCH 2 C≡C—or —C(═O)O—,

and/or a salt, metal complex and N-oxide thereof.

15. A compound according to claim 1 , in which

A is 3,5-bis(difluoromethyl)-1H-pyrazol-1-yl, 5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl, 5-choro-2-methylphenyl, 3-(difluoromethyl)-5-methyl-1H-pyrazol-1-yl, 2,5-dimethylphenyl, 5-(difluoromethyl)-3-methyl-1H-pyrazol-1-yl, or 2,5-bis(difluoromethyl)phenyl,

L 1 is —CH 2 — or —NH—,

Y is oxygen,

G is G 1 ,

R G1 is hydrogen,

Q is Q 24 −3 or Q 11 −1,

R 5 is hydrogen or methyl,

L 2 is a direct bond, and

R 1 is 2-{[3-(trimethylsilyl)pro-2-yn-1-yl]oxy}phenyl, 2-[(1 E/Z)-N-hydroxyethanimidol]phenyl, 3-{(E/Z)-[(propan-2-yloxy)imino]methyl]phenyl, 3-[(E/Z)-ethoxyimino)methy]phenyl, 3-[(1 E/Z)-N-(propan-2-yloxy)ethanimidoyl]phenyl, 3-[(E/Z)-(methoxyimino)methyl]phenyl, 3-[(E/Z)-(hydroxyimino)methyl]phenyl, 2-{(E/Z)-[(propan-2-yloxy)imino]methyl}phenyl, 3-[(1 E/Z)-N-hydroxyethanimidoyl]phenyl, 3-[(1 E/Z)-N-methoxyethanimidoyl]phenyl, 4-(acetylamino)phenyl, 2-[(1 E/Z)-N-(propan-2-yloxy)ethanimidoyl]phenyl, 2-([3-(naphthalen-1-yl)prop-2-yn-1-yl]oxy}phenyl, 2-[(E/Z)-(methoxyimino)methyl]phenyl, 2-[(E/Z)-(ethoxyimino)methyl]phenyl, 2-[1 E/Z)-N-methoxyethanimidoyl]phenyl, 3-[(1 E/Z)-N-ethoxyethanimidoyl]phenyl, 4-[(tert-butoxycarbonyl)amino]phenyl, 2-[(E/Z)-(hydroxyimino)methyl]phenyl, 4,5-dimethyl-2-[(methylsulphonyl)oxy]phenyl, 2-carboxyphenyl, 2-[(ethylsulphonyl)oxy]phenyl, 4-[(methylsulphonyl)oxy]phenyl, 2-formamidophenyl, 4-(2-methoxy-2-oxoethoxy)phenyl, 2-[(allyloxy)methyl]phenyl, 3-(cyanomethoxy)-2,6-difluorophenyl, 2-{[(2-methoxyethyl)sulphinyl]methyl}phenyl, 2-(acetoxymethyl) -6-fluorophenyl, 4-[(cyclopropylsulphonyl)oxy]phenyl, 3-chloro-2-(cyanomethoxy)phenyl, 2-[(4-fluorobenzoyl)oxy]phenyl, 3-fluoro-2-[(methylsulphonyl)oxy]phenyl, 2,3-dimethoxy-6-[(methylsulphonyl)oxy]phenyl, 2-{[(trifluoromethyl)sulphonyl]oxy}phenyl, 2-[(2E)-but-2-enoyloxy]phenyl, 2-fluoro-6-[(prop-2-yn-1-yloxy)methyl]phenyl, 2-[(ethylcarbamoyl)oxy]phenyl, 5-chloro-2-[(methylsulphonyl)oxy]phenyl, 2-[(2-fluorobenzoyl)oxy]phenyl, 2-[formyl(prop-2-yn-1-yl)amino]phenyl, 2-{[(1-chlorocyclopropyl)carbonyl]oxy}phenyl, 4-methyl-2-[(methylsulphonyl)oxy]phenyl, 4-chloro-2-[(methylsulphonyl)oxy]phenyl, 2-[(methylsulphonyl)oxy]phenyl, 2-fluoro-6-[(E/Z)-(methoxyimino)methyl]phenyl, 2-[(cyclopropylsulphonyl)oxy]-3-fluorophenyl, 2-(cyanomethoxy)-4-methylphenyl, 2-[(prop-2-yn-1-yloxy)methyl]phenyl, 2-[(methylsulphanyl)methoxy]phenyl, 2-(cyanomethoxy)-3-fluorophenyl, 2-methoxy-6-[(methylsulphonyl)oxy]phenyl, 2-(acryloyloxy)phenyl, 3-chloro-2-[(methylsulphonyl)oxy]phenyl, 2-[(trimethylsilyl)ethynyl]phenyl, 3-[(cyclopropylsulphonyl)oxy]phenyl, 2-[(3-fluorobenzoyl)oxy]phenyl, 2-[(cyclopropylsulphonyl)oxy]-5-fluorophenyl, 1-(2-cyanoethyl)-1H-pyrrol-2-yl, 2-(benzoyloxy)phenyl, 4-(cyanomethoxy)phenyl, 2-(dimethylcarbamothioyl)phenyl, 5-chloro -2-(cyanomethoxy)phenyl, 2-(cyanomethoxy)-6-fluorophenyl, 2-[(cyclopropylsulphonyl)oxy]phenyl, 2-{[(2-methoxyethyl)sulphonyl]methyl}phenyl, 2-chloro-6-[(methylsulphonyl)oxy]phenyl, 4-chloro-2-(cyanomethoxy)phenyl, 3-{[3-(1-naphthyl)prop-2-yn-1-yl]oxy}phenyl, 4-[(ethylsulphonyl)oxy]phenyl, 3-[(ethylsulphonyl)oxy]phenyl, 2-{[(2-methoxyethyl)sulphanyl]methyl}phenyl, 2,6-difluoro-3-[(methylsulphonyl)oxy]phenyl, 5-methyl-2-[(methylsulphonyl)oxy]phenyl, 2-(cyanomethoxy)phenyl, 2-(cyanomethoxy)-5-methylphenyl, 2-{[(4-methylphenyl)sulphonyl]oxy}phenyl, 2-(acetoxymethyl)phenyl, 2-[cyanomethyl)(formyl)amino]phenyl, 3-(cyanomethoxy)phenyl, or 2-chloro-6-(cyanomethoxy)phenyl,

and/or a salt, metal complex and N-oxide thereof.

16. A compound according claim 1 , wherein the compound is

and/or a salt, metal complex and N-oxide thereof.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 2, 2018
From: BAYER INTELLECTUAL PROPERTY GMBH
To: BAYER CROPSCIENCE AKTIENGESELLSCHAFT
Reel/Frame 047403/0243 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 16, 2013
From: TSUCHIYA, TOMOKI; WASNAIRE, PIERRE; HOFFMANN, SEBASTIAN; CRISTAU, PIERRE; SEITZ, THOMAS; KLUTH, JOACHIM; HILLEBRAND, STEFAN; BENTING, JUERGEN; PORTZ, DANIELA; WACHENDORFF-NEUMANN, ULRIKE
To: BAYER INTELLECTUAL PROPERTY GMBH
Reel/Frame 030806/0164 →