IP Library Granted Patent US 8,524,743
Granted Patent B2
US 8,524,743 · App. 12/975,150 · Granted Sep 3, 2013

Bis(difluoromethyl)pyrazoles as fungicides

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Quick Facts
Patent No.
US 8,524,743
App. No.
12/975,150
Granted
Sep 3, 2013
Kind
B2
Abstract

Bis(difluoromethyl)pyrazole derivatives of the formula (I) in which the symbols R 1 , X and G are each as defined in the description, and agrochemically active salts, metal complexes and N-oxides thereof, and use thereof for controlling phytopathogenic harmful fungi, and also processes for preparing compounds of the formula (I).

Claims (69)

1. A compound of formula (I)

in which the symbols are each defined as follows:

X is oxygen or sulphur,

R 1 is hydrogen or halogen,

R 2 is a C 3 -C 8 -cycloalkyl which may contain up to two substituents, where the substituents are each independently selected from the group consisting of:

cyano, halogen, hydroxyl, oxo, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -haloalkylthio and phenyl,

or

R 2 is a phenyl which may contain up to two substituents, where the substituents are each independently selected from the group consisting of: amino, halogen, cyano, hydroxyl, SH, nitro, C(═O)H, 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 4 -C 10 -alkyl-cycloalkyl, C 4 -C 10 -cycloalkylalkyl, C 6 -C 14 -cycloalkylcycloalkyl, C 4 -C 10 -halocycloalkylalkyl, C 5 -C 10 -alkylcycloalkylalkyl, C 3 -C 8 -cycloalkenyl, C 3 -C 8 -halocycloalkenyl, C 2 -C 6 -alkoxyalkyl, C 4 -C 10 -cycloalkoxyalkyl, C 3 -C 8 -alkoxyalkoxyalkyl, C 2 -C 6 -alkylthioalkyl, C 2 -C 6 -alkylsulphinylalkyl, C 2 -C 6 -alkylsulphonylalkyl, C 2 -C 6 -alkylaminoalkyl, C 3 -C 8 -dialkylaminoalkyl, C 2 -C 6 -haloalkylaminoalkyl, C 4 -C 10 -cycloalkylaminoalkyl, C 2 -C 6 -alkylcarbonyl, C 2 -C 6 -haloalkylcarbonyl, C 4 -C 8 -cycloalkylcarbonyl, C 2 -C 6 -alkoxycarbonyl, C 4 -C 8 -cycloalkoxycarbonyl, C 5 -C 10 -cycloalkylalkoxycarbonyl, C 2 -C 6 -alkylaminocarbonyl, C 3 -C 8 -dialkylaminocarbonyl, C 4 -C 8 -cycloalkylaminocarbonyl, C 2 -C 6 -halo-alkoxyalkyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 3 -C 8 -cycloalkoxy, C 3 -C 8 -halocycloalkoxy, C 4 -C 10 -cycloalkylalkoxy, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkynyloxy, C 2 -C 6 -haloalkynyl-oxy, C 2 -C 6 -alkoxyalkoxy, C 2 -C 6 -alkylcarbonyloxy, C 2 -C 6 -haloalkyl-carbonyloxy, C 4 -C 8 -cycloalkylcarbonyloxy, C 3 -C 6 -alkylcarbonylalkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -haloalkylthio, C 3 -C 6 -cycloalkylthio, C 1 -C 6 -alkyl-sulphinyl, C 1 -C 6 -haloalkylsulphinyl, C 1 -C 6 -alkylsulphonyl, C 1 -C 6 -halo-alkylsulphonyl, C 3 -C 8 -cycloalkylsulphonyl, tri(C 1 -C 4 -alkyl)silyl, C 1 -C 6 -alkylsulphonylamino, C 1 -C 6 -haloalkylsulphonylamino and -LQ,

or

R 2 is a 5- or 6-membered heteroaryl radical which may contain up to two substituents, where the substituents are each independently selected from the group consisting of:

substituents on carbon: halogen, cyano, nitro, hydroxyl, SH, 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 6 -halocycloalkyl, C 4 -C 10 -alkyl-cycloalkyl, C 4 -C 10 -cycloalkylalkyl, C 6 -C 14 -cycloalkylcycloalkyl, C 5 -C 10 -alkylcycloalkylalkyl, C 2 -C 4 -alkoxyalkyl, C 2 -C 4 -alkylcarbonyl, C 2 -C 6 -alkoxycarbonyl, C 2 -C 6 -alkylaminocarbonyl, C 3 -C 8 -dialkylaminocarbonyl, C 1 -C 4 -hydroxyalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 2 -C 6 -alkyl-carbonyloxy, C 2 -C 6 -alkylcarbonylthio, C 1 -C 4 -alkylthio, C 1 -C 4 -halo-alkylthio, C 1 -C 4 -alkylsulphinyl, C 1 -C 4 -haloalkylsulphinyl, C 1 -C 4 -alkyl-sulphonyl, C 1 -C 4 -haloalkylsulphonyl, tri(C 1 -C 4 -alkyl)silyl, and -LQ, 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 6 -cycloalkyl, C 3 -C 6 -halocycloalkyl, C 4 -C 10 -alkylcycloalkyl, C 4 -C 10 -cycloalkylalkyl, C 1 -C 4 -alkylsulphonyl, C(═O)H, C(═O)Me, C(O)OMe, benzyl and phenyl,

R 3 is hydrogen, cyano, C 1 -C 3 -alkyl or C 1 -C 3 -haloalkyl,

R Tz is halogen or hydrogen

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

Q is a phenyl which may contain up to two substituents, where the substituents are each independently selected from the group consisting of:

halogen, cyano, nitro, hydroxyl, SH, 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 2 -C 6 -alkoxyalkyl, C 2 -C 6 -alkyl-carbonyl, C 2 -C 6 -haloalkylcarbonyl, C 2 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 3 -C 8 -cycloalkoxy, C 3 -C 8 -halocycloalkoxy, C 2 -C 6 -alkenyloxy, C 2 -C 6 -alkynyloxy, C 2 -C 6 -alkoxyalkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -haloalkylthio, C 1 -C 6 -alkylsulphinyl, C 1 -C 6 -haloalkylsulphinyl, C 1 -C 6 -alkylsulphonyl, C 1 -C 6 -haloalkylsulphonyl, tri(C 1 -C 4 -alkyl)silyl and phenyl,

or

Q is a 5- or 6-membered heteroaryl radical which may contain up to two substituents, where the substituents are each independently selected from the group consisting of:

substituents on carbon: halogen, cyano, nitro, hydroxyl, SH, 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 6 -halocycloalkyl, C 4 -C 10 -alkyl-cycloalkyl, C 4 -C 10 -cycloalkylalkyl, C 6 -C 14 -cycloalkylcycloalkyl, C 5 -C 10 -alkylcycloalkylalkyl, C 2 -C 4 -alkoxyalkyl, C 2 -C 4 -alkylcarbonyl, C 2 -C 6 -alkoxycarbonyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 2 -C 6 -alkylcarbonyl-oxy, C 2 -C 6 -alkylcarbonylthio, C 1 -C 4 -alkylthio, C 1 -C 4 -haloalkylthio, C 1 -C 4 -alkylsulphinyl, C 1 -C 4 -haloalkylsulphinyl, C 1 -C 4 -alkylsulphonyl, C 1 -C 4 -haloalkylsulphonyl, tri(C 1 -C 4 -alkyl)silyl, and phenyl,

substituents on nitrogen: 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 3 -C 6 -cycloalkyl, C 1 -C 4 -alkylsulphonyl, C(═O)H, C(═O)Me, C(═O)OMe and phenyl,

and agrochemically active salts, metal complexes and N-oxides thereof.

2. The compound of formula (I) according to claim 1 , in which the symbols are each defined as follows:

X is oxygen,

R 1 is hydrogen or fluorine,

G is G1, G3 or G4,

R 2 is a C 3 -C 8 -cycloalkyl which may contain up to two substituents, where the substituents are each independently selected from the group consisting of:

cyano, halogen, hydroxyl, oxo, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -haloalkylthio and phenyl, or

R 2 is a phenyl which may contain up to two substituents, where the substituents are each independently selected from the group consisting of:

amino, halogen, cyano, hydroxyl, SH, nitro, C(═O)H, 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 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 4 -C 10 -alkyl-cycloalkyl, C 4 -C 10 -cycloalkylalkyl, C 6 -C 14 -cycloalkylcycloalkyl, C 4 -C 10 -halocycloalkylalkyl, C 5 -C 10 -alkylcycloalkylalkyl, C 3 -C 8 -cycloalkenyl, C 3 -C 8 -halocycloalkenyl, C 2 -C 6 -alkoxyalkyl, C 4 -C 10 -cycloalkoxyalkyl, C 3 -C 8 -alkoxyalkoxyalkyl, C 2 -C 6 -alkylthioalkyl, C 2 -C 6 -alkylsulphinylalkyl, C 2 -C 6 -alkylsulphonylalkyl, C 2 -C 6 -alkylaminoalkyl, C 3 -C 8 -dialkyl-aminoalkyl, C 2 -C 6 -haloalkylaminoalkyl, C 4 -C 10 -cycloalkylaminoalkyl, C 2 -C 6 -alkylcarbonyl, C 2 -C 6 -haloalkylcarbonyl, C 4 -C 8 -cycloalkylcarbonyl, C 2 -C 6 -alkoxycarbonyl, C 4 -C 8 -cycloalkoxycarbonyl, C 5 -C 10 -cycloalkyl-alkoxycarbonyl, C 2 -C 6 -alkylaminocarbonyl, C 3 -C 8 -dialkylaminocarbonyl, C 4 -C 8 -cycloalkylaminocarbonyl, C 2 -C 6 -haloalkoxyalkyl, C 1 -C 6 -hydroxy-alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 8 -cycloalkoxy, C 3 -C 8 -halo-cycloalkoxy, C 4 -C 10 -cycloalkylalkoxy, C 2 -C 6 -alkenyloxy, C 2 -C 6 -halo-alkenyloxy, C 2 -C 6 -alkynyloxy, C 2 -C 6 -haloalkynyloxy, C 2 -C 6 -alkoxyalkoxy, C 2 -C 6 -alkylcarbonyloxy, C 2 -C 6 -haloalkylcarbonyloxy, C 4 -C 8 -cyclo-alkylcarbonyloxy, C 3 -C 6 -alkylcarbonylalkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -haloalkylthio, C 3 -C 6 -cycloalkylthio, C 1 -C 6 -alkylsulphinyl, C 1 -C 6 -halo-alkylsulphinyl, C 1 -C 6 -alkylsulphonyl, C 1 -C 6 -haloalkylsulphonyl, C 3 -C 8 -cycloalkylsulphonyl, tri(C 1 -C 4 -alkyl)silyl, C 1 -C 6 -alkylsulphonylamino, C 1 -C 6 -haloalkylsulphonylamino and -LQ, or

R 2 is a 5- or 6-membered heteroaryl radical which may contain up to two substituents, where the substituents are each independently selected from the group consisting of:

substituents on carbon: halogen, cyano, nitro, hydroxyl, SH, 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 6 -halocycloalkyl, C 4 -C 10 -alkyl-cycloalkyl, C 4 -C 10 -cycloalkylcycloalkyl, C 6 -C 14 -cycloalkylcycloalkyl, C 5 -C 10 -alkylcycloalkylalkyl, C 2 -C 4 -alkoxyalkyl, C 2 -C 4 -alkylcarbonyl, C 2 -C 6 -alkoxycarbonyl, C 2 -C 6 -alkylaminocarbonyl, C 3 -C 8 -dialkylaminocarbonyl, C 1 -C 4 -hydroxyalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 2 -C 6 -alkyl-carbonyloxy, C 2 -C 6 -alkylcarbonylthio, C 1 -C 4 -alkylthio, C 1 -C 4 -halo-alkylthio, C 1 -C 4 -alkylsulphinyl, C 1 -C 4 -haloalkylsulphinyl, C 1 -C 4 -alkyl-sulphonyl, C 1 -C 4 -haloalkylsulphonyl, tri(C 1 -C 4 -alkyl)silyl, and -LQ,

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 6 -cycloalkyl, C 3 -C 6 -halocycloalkyl, C 4 -C 10 -alkylcycloalkyl, C 4 -C 10 -cycloalkylalkyl, C 1 -C 4 -alkylsulphonyl, C(═O)H, C═O)Me, C(═O)OMe, benzyl and phenyl,

R 3 is hydrogen, cyano or C 1 -C 3 -alkyl,

L is a direct bond or oxygen,

Q is a phenyl which may contain up to two substituents, where the substituents are each independently selected from the group consisting of:

halogen, cyano, hydroxyl, nitro, SH, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -haloalkylthio and phenyl, or

Q is a 5- or 6-membered heteroaryl radical which may contain up to two substituents, where the substituents are each independently selected from the group consisting of:

substituents on carbon: halogen, cyano, hydroxyl, nitro, SH, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -haloalkylthio, and phenyl,

substituents on nitrogen: C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl and phenyl,

and agrochemically active salts, metal complexes and N-oxides thereof.

3. The compound of formula (I) according to claim 1 , in which the symbols are each defined as follows:

G is G3 or G4,

and agrochemically active salts, metal complexes and N-oxides thereof.

4. The compound of formula (I) according to claim 1 , in which the symbols are each defined as follows:

R 2 is a phenyl which may contain up to two substituents, where the substituents are each independently selected from the group consisting of:

amino, halogen, cyano, nitro, 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 2 -C 6 -alkoxyalkyl, C 2 -C 6 -alkylcarbonyl, C 2 -C 6 -haloalkylcarbonyl, C 2 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 3 -C 8 -cycloalkoxy, C 3 -C 8 -halocycloalkoxy, C 2 -C 6 -alkenyloxy, C 2 -C 6 -alkynyloxy, C 2 -C 6 -alkoxyalkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -haloalkyl-thio, C 1 -C 6 -alkylsulphinyl, C 1 -C 6 -haloalkylsulphinyl, C 1 -C 6 -alkylsulphonyl, C 1 -C 6 -haloalkylsulphonyl, and phenyl,

and agrochemically active salts, metal complexes and N-oxides thereof.

5. The compound of formula (I) according to claim 4 , in which

R 2 is selected from the group consisting of phenyl, 2-fluorophenyl, 2,6-difluorophenyl, 2-acetylphenyl, 3-acetylphenyl, 2-hydroxyphenyl, 2-nitrophenyl, 2-[(2-methoxyethoxy)methyl]phenyl, 2-[(ethylsulphanyl)-methyl]phenyl, 2-[(cyclopropylmethoxy)carbonyl]phenyl, 2-(allyloxy)-phenyl, 3-(but-2-yn-1-yloxy)phenyl, 2-(butoxymethyl)phenyl, 2-fluoro-6-formylphenyl, 2-[(2-methylprop-2-en-1-yl)oxy]phenyl, 2-(2-methoxy-ethoxy)phenyl, 2-[(3-methylbut-2-en-1-yl)oxy]phenyl, 3-(prop-2-yn-1-yloxy)phenyl, 4-(prop-2-yn-1-yloxy)phenyl, 3-formylphenyl, 2-(cyclohexylmethoxy)phenyl, 2-(pent-2-yn-1-yloxy)phenyl, 2-formyl-phenyl, 2-(cyclopropylcarbamoyl)phenyl, 2-(but-2-yn-1-yloxy)-6-fluorophenyl, 2-fluoro-6-(prop-2-yn-1-yloxy)phenyl, 2-[(cyclo-hexylcarbonyl)oxy]phenyl, 2-[(cyclopropylcarbonyl)oxy]phenyl, 3-(pent-2-yn-1-yloxy)phenyl, 2-(but-2-yn-1-yloxy)phenyl, 2-[(3,3,3-trifluoro-propanoyl)oxy]phenyl, 2-[(methylsulphonyl)amino]phenyl, 2-ethynyl-phenyl, 2-(prop-2-yn-1-yloxy)phenyl, 4-[(methylsulphonyl)amino]phenyl, 2-aminophenyl, 3-hydroxyphenyl, 2-(methoxycarbonyl)phenyl, 2-(chloromethyl)phenyl, 4-(pent-2-yn-1-yloxy)phenyl, 4-(but-2-yn-1-yloxy)phenyl, 2-chloro-6-(prop-2-yn-1-yloxy)phenyl, 2-chloro-6-(2-meth-oxyethoxy)phenyl, 2-(allyloxy)-6-chlorophenyl, 2-[(2,2,2-trifluoro-ethoxy)methyl]phenyl, 2-[(ethylsulphonyl)methyl]phenyl and 2-(hydroxymethyl)phenyl,

and agrochemically active salts, metal complexes and N-oxides thereof.

6. The compound of formula (I) according to claim 1 , in which

R 3 is hydrogen,

and agrochemically active salts, metal complexes and N-oxides thereof.

7. The compound of formula (I) according to claim 1 , in which

R Tz is hydrogen

and agrochemically active salts, metal complexes and N-oxides thereof.

8. The compound of formula (I) according to claim 1 , wherein G is G3,

R 2 is a phenyl which may contain up to two substituents, where the substituents are each independently selected from the group consisting of:

amino, halogen, cyano, nitro, 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 2 -C 6 -alkoxyalkyl, C 2 -C 6 -alkylcarbonyl, C 2 -C 6 -haloalkyl-carbonyl, C 2 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 3 -C 8 -cycloalkoxy, C 3 -C 8 -halocycloalkoxy, C 2 -C 6 -alkenyloxy, C 2 -C 6 -alkynyloxy, C 2 -C 6 -alkoxyalkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -haloalkylthio, C 1 -C 6 -alkylsulphinyl, C 1 -C 6 -haloalkylsulphinyl, C 1 -C 6 -alkylsulphonyl, C 1 -C 6 -haloalkylsulphonyl, and phenyl,

and agrochemically active salts, metal complexes and N-oxides thereof.

9. The compound of formula (I) according to claim 8 , wherein

R 2 is selected from the group consisting of phenyl, 2-fluorophenyl, 2,6-difluorophenyl, 2-acetylphenyl, 3-acetylphenyl, 2-hydroxyphenyl, 2-nitrophenyl, 2-[(2-methoxyethoxy)methyl]phenyl, 2-[(ethylsulphanyl)methyl]phenyl, 2-[(cyclopropylmethoxy)carbonyl]phenyl, 2-(allyloxy)phenyl, 3-(but-2-yn-1-yloxy)phenyl, 2-(butoxymethyl)phenyl, 2-fluoro-6-formylphenyl, 2-[(2-methylprop-2-en-1-yl)oxy]phenyl, 2-(2-methoxyethoxy)phenyl, 2-[(3-methylbut-2-en-1-yl)oxy]phenyl, 3-(prop-2-yn-1-yloxy)phenyl, 4-(prop-2-yn-1-yloxy)phenyl, 3-formylphenyl, 2-(cyclohexylmethoxy)phenyl, 2-(pent-2-yn-1-yloxy)phenyl, 2-formylphenyl, 2-(cyclopropylcarbamoyl)phenyl, 2-(but-2-yn-yloxy)-6-fluorophenyl, 2-fluoro-6-(prop-2-yn-1-yloxy)phenyl, [(cyclohexylcarbonyl)oxy]phenyl, 2-[(cyclopropylcarbonyl)oxy]phenyl, 3-(pent-2-yn-1-yloxy)phenyl, 2-(but-2-yn-1-yloxy)phenyl, 2-[(3,3,3-trifluoro-propanoyl)oxy]phenyl, 2-[(methylsulphonyl)amino]phenyl, 2-ethynylphenyl, 2-(prop-2-yn-1-yloxy)phenyl, 4-[(methylsulphonyl)amino]phenyl, 2-aminophenyl, 3-hydroxyphenyl, 2-(methoxycarbonyl)phenyl, 2-(chloromethyl)phenyl, 4-(pent-2-yn-1-yloxy)phenyl, 4-(but-2-yn-1-yloxy)phenyl, 2-chloro-6-(prop-2-yn-1-yloxy)phenyl, 2-chloro-6-(2-methoxyethoxy)phenyl, 2-(allyloxy)-6-chlorophenyl, 2-[(2,2,2-trifluoroethoxy)methyl]phenyl, 2-[(ethylsulphonyl)methyl]phenyl and 2-(hydroxymethyl)phenyl,

and agrochemically active salts, metal complexes and N-oxides thereof.

10. The compound of formula (I) according to claim 9 , wherein R 3 is hydrogen.

11. A composition for controlling phytopathogenic harmful fungi, said composition comprises at least one compound of formula (I) according to claim 1 , in addition to extenders and/or surfactants.

12. A method for controlling phytopathogenic harmful fungi, said method comprises applying one or more compounds of formula (I) according to claim 1 to the phytopathogenic harmful fungi and/or their habitat.

13. A compound of formula (I)

wherein X is oxygen, R 1 is hydrogen, G is G3, R 2 is 2-(prop-2-yn-1-yloxy)phenyl, R 3 is hydrogen, R Tz is hydrogen, and agrochemically active salts, metal complexes and N-oxides thereof.

14. A composition for controlling phytopathogenic harmful fungi, said composition comprises the compound of formula (I) according to claim 13 , in addition to extenders and/or surfactants.

Assignments (5)
NUNC PRO TUNC ASSIGNMENT Recorded Jul 4, 2023
From: BAYER INTELLECTUAL PROPERTY GMBH
To: BAYER CROPSCIENCE AKTIENGESELLSCHAFT
Reel/Frame 064198/0823 →
CHANGE OF ADDRESS Recorded Jun 12, 2023
From: BAYER INTELLECTUAL PROPERTY GMBH
To: BAYER INTELLECTUAL PROPERTY GMBH
Reel/Frame 064021/0344 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 16, 2017
From: HILLEBRAND, STEFAN
To: BAYER INTELLECTUAL PROPERTY GMBH
Reel/Frame 041600/0976 →
CORRECTIVE ASSIGNMENT TO CORRECT THE 1ST AND 2ND INVENTORS EXECUTION DATES PREVIOUSLY RECORDED ON REEL 026246 FRAME 0119. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Recorded Jul 10, 2015
From: CRISTAU, PIERRE; HOFFMANN, SEBASTIAN; KLUTH, JOACHIM; TSUCHIYA, TOMOKI; WASNAIRE, PIERRE; BENTING, JURGEN; PORTZ, DANIELA; WACHENDORFF-NEUMANN, ULRIKE
To: BAYER CROPSCIENCE AG
Reel/Frame 036089/0889 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 23, 2015
From: BAYER CROPSCIENCE AG
To: BAYER INTELLECTUAL PROPERTY GMBH
Reel/Frame 035009/0531 →