# US 10,499,641 B2 · Heteroarylpiperidine and -piperazine derivatives as fungicides

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- Number: US 10,499,641 B2
- Document ID: US10499641B2
- Status: Granted
- Kind: B2
- Application number: 15/714,109
- Filed: 2017-09-25
- Published: 2018-01-11
- Granted: 2019-12-10
- Earliest claimed: 2010-08-25
- Assignees: Bayer CropScience AG
- Applicants: Bayer Cropscience AG
- Inventors: Tomoki Tsuchiya; Pierre Wasnaire; Sebastian Hoffmann; Pierre Cristau; Thomas Seitz; Joachim Kluth; Stefan Hillebrand; Juergen Benting; Daniela Portz; Ulrike Wachendorff-Neumann
- Web page: https://patentgrep.com/patent/US10499641B2

## CPC

- A01N 43/80: five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
- A01N 43/78: 1,3-Thiazoles; Hydrogenated 1,3-thiazoles
- A01N 47/22: O-Aryl or S-Aryl esters thereof
- A01N 47/38: containing the group >N—CO—N< where at least one nitrogen atom is part of a heterocyclic ring; Thio analogues thereof
- A01N 55/00: Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur (containing organo-phosphorus compounds A01N57/00)
- C07D 417/14: containing three or more hetero rings
- C07F 7/0812: {comprising a heterocyclic ring}
- A01N: PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF (preservation of food or foodstuff A23); BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES (preparations for medical, dental or toiletry purposes which kill or prevent the growth or proliferation of unwanted organisms A61K); PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)

## Abstract

Heteroarylpiperidine and -piperazine derivatives of the formula (I) in which the symbols A, X, Y, L1, L2, G, Q, p, R1, R2 and R10 are each as defined in the description, and salts, metal complexes and N-oxides of the compounds of the formula (I), and the use thereof for controlling phytopathogenic harmful fungi and processes for preparing compounds of the formula (I).

## Claims

### Claim 1

A compound of formula (I)
A is pyrazol-1-yl which may contain up to two substituents, where the substituents are each independently selected from the following list:
halogen, cyano, hydroxyl, nitro, —NR3R4, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, C3-C6-halocycloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, C1-C4-alkylsulphonyl, C1-C4-haloalkylthio, C1-C4-haloalkylsulphonyl, C1-C4-alkoxy-C1-C4-alkyl, hydroxy-C1-C4-alkyl, C1-C6-alkylcarbonyl, C1-C6-alkoxycarbonyl, C1-C6-alkylcarbonyloxy or phenyl,
R3 and R4 are the same or different and are each independently hydrogen, alkyl, alkenyl, alkynyl, haloalkyl, cycloalkyl, benzyl or phenyl,
L1 is NH or CH2,
Y is oxygen,
X is carbon,
R2 is hydrogen,
R10 is oxo, alkyl, alkenyl, haloalkyl, alkoxy, halogen, cyano or hydroxyl,
p is 0,
G is
where the bond identified by “v” is bonded directly to X and where the bond identified by “w” is bonded directly to Q,
RG1 is hydrogen or halogen,
Q is
where the bond identified by “*” is bonded directly to G or L2, and where the bond identified by “#” is bonded directly to L2 or G, or where the bond identified by “*” is bonded directly to L2, and the bond identified by “#” is at the same time bonded directly to G,
R5 is hydrogen,
L2 is a direct bond,
R1 is phenyl which contains 1, 2 or 3 substituents, where the substituents are each independently selected at least once from Z4 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 -L3R3,
L3 is a direct bond, —CH2—, —C(═O)—, sulphur, oxygen, —C(═O)O—, —C(═O)NH—, —OC(═O)—or —NHC(═O)—,
Z3 is a phenyl radical, naphthalenyl or a 5- or 6-membered heteroaryl radical which may contain up to two substituents, where the substituents are each independently selected from the following list:
substituents on carbon: halogen, cyano, nitro, hydroxyl, amino, —SH, C1-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, C1-C4-haloalkyl, C2-C4-haloalkenyl, C2-C4-haloalkynyl, C2-C4-alkoxyalkyl, C1-C6-alkylcarbonyl, C1-C6-haloalkylcarbonyl, C1-C6-alkoxycarbonyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C1-C4-alkylthio, C1-C4-haloalkylthio, C1-C4-alkylsulphonyl, C1-C4-haloalkylsulphonyl or C1-C4-alkylamino, or di(C1-C4-alkyl)amino,
substituents on nitrogen: C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, C1-C4-alkoxy-C1-C4-alkyl, phenyl, benzyl, C1-C4-haloalkylsulphonyl, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, phenylsulphonyl, C1-C4-alkylsulphonyl, —C(=O)H, or C1-C3-alkylcarbonyl,Z4 is cyano-C1-C6-alkyl, C2-C6-alkenylcarbonyloxy, C2-C6-alkynylthio, C3-C8-halocycloalkylcarbonyloxy, C2-C6-alkenylamino, C2-C6-alkynylamino, C1-C6-haloalkylamino, C3-C8-cycloalkyl-C1-C6-alkylamino, C1-C6-alkoxyamino, C1-C6-haloalkoxyamino, C1-C6-alkylcarbonylamino, C1-C6-haloalkylcarbonylamino, C1-C6-alkoxycarbonylamino, C1-C6-alkylcarbonyl(C 1-C6-alkyl)amino, C1-C6-haloalkylcarbonyl(C1-C6-alkyl)amino, C1-C6-alkoxycarbonyl(C1-C6-alkyl)amino, —NR3SO2Z3, C2-C6-alkenylthio, C1-C6-haloalkoxycarbonyl, C1-C6-alkoxy-C1-C4-alkylcarbonyl, -SF5, C1-C6-haloalkoxycarbonylamino, —NHC(═O)H, C1-C6-alkoxy(C1-C4-alkyl)aminocarbonyl, C1-C6-alkoxycarbonyl-C1-C6-alkoxy, —C(═NOR7)R8, —N=C(R9)2, di(C1-C6-alkyl)aminocarbonylamino, di(C1-C6-alkyl)aminosulphonyl, di(C1-C6-haloalkyl)amino, C1-C6-alkylaminosulphonyl, C1-C6-alkylaminocarbonylamino, tri(C1-C4-alkyl)silyloxy, C1-C6-haloalkylsulphonyloxy, C1-C6-alkylsulphonyloxy, tri(C1-C4-alkyl)silyl-C2-C4-alkynyloxy, tri(C1-C4-alkyl)silyl-C2-C4-alkynyl or -L4Z3,
Z4 is cyano-C1-C6-alkyl, C2-C6-alkenylcarbonyloxy, C2-C6-alkynylthio, C3-C8-halocyclo-alkylcarbonyloxy, C2-C6-alkenylamino, C2-C6-alkynylamino, C1-C6-haloalkylamino, C3-C8-cycloalkyl-C1-C6-alkylamino, C1-C6-alkoxyamino, C1-C6-haloalkoxyamino, C1-C6-alkyl-carbonylamino, C1-C6-haloalkylcarbonylamino, C1-C6-alkoxycarbonylamino, C1-C6-alkylcarbonyl(C1-C6-alkyl)amino, C1-C6-haloalkylcarbonyl(C1-C6-alkyl)amino, C1-C6-alkoxycarbonyl(C1-C6-alkyl)amino, -NR3SO2Z3, C2-C6-alkenylthio, C1-C6-haloalkoxycarbonyl, C1-C6-alkoxy-C1-C4-alkylcarbonyl, -SF5, C1-C6-haloalkoxycarbonylamino, —NHC(═O)H, C1-C6-alkoxy(C1-C4-alkyl)aminocarbonyl, C1-C6-alkoxycarbonyl-C1-C6-alkoxy, —C(═NOR7)R8, —N═C(R9)2, di(C1-C6-alkyl)aminocarbonylamino, di(C1-C6-alkyl)aminosulphonyl, di(C1-C6-haloalkyl)amino, C1-C6-alkylaminosulphonyl, C1-C6-alkylaminocarbonylamino, tri(C1-C4-alkyl)silyloxy, C1-C6-haloalkylsulphonyloxy, C1-C6-alkylsulphonyloxy, tri(C1-C4-alkyl)silyl-C2-C4-alkynyloxy, tri(C1-C4-alkyl)silyl-C2-C4-alkynyl or -L4Z3,
or
Z4 is —C(═O)NR11R12, —SO2NR11R12, -SCN, C1-C3-alkoxysulphonyl, C3-C8-cycloalkylsulphinyl or cyano(C1-C3-alkoxy)-C1-C3-alkyl,
or
Z4 is C1-C3-alkyl which contains 1 or 2 substituents, where the substituents are each independently selected from the following list:
C2-C4-alkenyloxy, C2-C4-alkynyloxy, C2-C4-alkenylthio, C2-C4-alkynylthio, C1-C3-alkoxy-C1-C3-alkylthio, C1-C3-alkoxy-C1-C3-alkylsulphinyl, C1-C3-alkoxy-C1-C3-alkylsulphonyl, C1-C3-alkylcarbonyloxy or C1-C3-halocarbonyloxy,
or
Z4 is substituted hydroxyl, where the substituents are each selected from the following list:
C3-C8-cycloalkylsulphonyl, C3-C8-halocycloalkylsulphonyl, C2-C4-alkenylsulphonyl or C(═O)NR3R4, or
Z4 is C1-C3-alkoxy which contains 1 or 2 substituents, where the substituents are each independently selected from the following list:
cyano, C1-C3-alkylcarbonyloxy, C1-C3-alkoxycarbonyl, C3-C8-cycloalkoxy, C1-C3-alkylcarbonyloxy, —O(C═O)H, C1-C3-alkylthio, hydroxy-C1-C3-alkyl, C3-C8-cycloalkylsulphonyl, C1-C3-haloalkylsulphonyl, C1-C3-alkoxy-C1-C3-alkoxy, C1-C3-alkylsulphonyl,
R7is hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, benzyl or Z3,
R8 is hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C3-C8-cycloalkyl-C1-C4-alkyl, C3-C8-cycloalkyl, C1-C4-alkyl-C3-C8-cycloalkyl, C1-C4-haloalkyl-C3-C8-cycloalkyl, C1-C4-alkoxy-C1-C4-alkyl, C1-C4-haloalkoxy-C1-C4-alkyl, benzyl or phenyl,
R9 is the same or different and is independently C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C3-C8-cycloalkyl, benzyl or phenyl,
R11 is C3-C4-alkenyl, C3-C4-alkynyl, cyano-C1-C3-alkyl, formyl, C1-C3-haloalkyl, benzyl, phenyl, C1-C3-alkylcarbonyl, C3-C8-cycloalkoxycarbonyl, C1-C3-alkoxycarbonyl, C3-C4-alkenyloxycarbonyl, C3-C4-alkynyloxycarbonyl, C1-C3-haloalkylcarbonyl, C3-C8-halocycloalkylcarbonyl, C3-C8-cycloalkoxycarbonyl, C3-C8-cycloalkylcarbonyl, or di(C1-C3-alkyl)aminocarbonyl,
R12 is hydrogen, C3-C4-alkenyl, C3-C4-alkynyl, cyano-C1-C3-alkyl, formyl, C1-C3-haloalkyl, benzyl, phenyl, C1-C3-alkylcarbonyl, C3-C8-cycloalkoxycarbonyl, C1-C3-alkoxycarbonyl, C3-C4-alkenyloxycarbonyl, C3-C4-alkynyloxycarbonyl, C1-C3-haloalkylcarbonyl, C3-C8-halocycloalkylcarbonyl, C3-C8-cycloalkoxycarbonyl, C3-C8-cycloalkylcarbonyl, or di(C1-C3-alkyl)aminocarbonyl,
L4 is —C(═O)O—, —C(═O)NH—, —OC(═O)—, —NHC(═O)— or —OCH2C≡C—,
or a salt, metal complex and/or N-oxide of the compound of formula (I).

### Claim 2 (depends on 1)

The compound of the formula (I) according to claim 1, in which
Q is
where the bond identified by “x” is bonded directly to G and where the bond identified by “y” is bonded directly to L2
and
R5 is hydrogen.

### Claim 3 (depends on 1)

The compound of the formula (I) 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, chlorine, bromine, fluorine, difluoromethyl or trifluoromethyl.

### Claim 4 (depends on 1)

The compound of the formula (I) according to claim 1, in which L1 is CH2.

### Claim 5 (depends on 1)

The compound of the formula (I) according to claim 1, in which
Z3 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, ethyl sulphonyl, propylthionyl, 1-methylethylthio, trifluoromethylsulphonyl, methylamino, ethylamino, n-propylamino, 1-methylethylamino, 1,1-dimethylethylamino or dimethylamino,
or
Z3 is naphthalenyl.

### Claim 6 (depends on 1)

A compound of the formula (I) according to claim 1, in which
Z4 is C1-C6-haloalkylsulphonyloxy or C1-C6-alkylsulphonyloxy.

### Claim 7 (depends on 1)

A compound of the formula (I) according to claim 1, in which
Z4 is 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-dimethyl-ethylcarbonylmethoxy, —C(═NOR7)R8, dimethylaminocarbonylamino, diethyl-aminocarbonylamino, dimethylaminosulphonyl, diethylaminosulphonyl, methyl-aminosulphonyl, ethylaminosulphonyl, propylaminosulphonyl, 1-methylethyl-aminosulphony, 1,1-dimethylethylaminocarbonylamino, methylaminocarbonlamino, ethylaminocarbonylamino, propylaminocarbonylamino, 1-methlethylaminocarbonylamino, 1,1-dimethylethylaminocarbonylamino, 2-methylpropylaminocarbonylamino, 1-chlorocyclopropylcarbonyloxy, 1-fluoro-cyclopropylcarbonyloxy, trifluoromethylsulphonyloxy, trimethylsilyloxy, chloro-methylcarbonylamino, trifluoromethylcarbonylamino, methylsulphonyloxy, ethyl-sulphonyloxy, trimethylsilylethynyloxy, trimethylsilylethynyl or -L4Z3,
R7 is hydrogen, methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1,1-dimethylethyl or 2-methylpropyl,
R8 is hydrogen, methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1,1-dimethylethyl or 2-methylpropyl.

### Claim 8 (depends on 1)

A compound of the formula (I) according to claim 1, in which
R1- is 2-{[3-(trimethylsilyl)prop-2-yn-1-yl]oxy}phenyl or
R1- is 2-[(1E/Z)-N-hydroxyethanimidoyl]phenyl or
R1- is 3-{(E/Z)-[(propan-2-yloxy)imino]methyl}phenyl or
R1- is 3-[(E/Z)-(ethoxyimino)methyl]phenyl or
R1- is 3-1E/Z)-N-(propan-2-yloxy)ethanimidoyl]phenyl or
R1- is 3-[(E/Z)-(methoxyimino)methyl]phenyl or
R1- is 3-[(E/Z)-(hydroxyimino)methyl]phenyl or
R1- is 2-{(E/Z)-[(propan-2-yloxy)imino]methyl}phenyl or
R1- is 3-[(1E/Z)-N-hydroxyethanimidoyl]phenyl or
R1- is 3-[(1E/Z)-N-methoxyethanimidoyl]phenyl or
R1- is 4-(acetylamino)phenyl or
R1- is 2-[(1E/Z)-N-(propan-2-yloxy)ethanimidoyl]phenyl or
R1- is 2- { [3 -(naphthalen-l-yl)prop-2-yn-l-yl]oxy }phenyl or
R1- is 2-[(E/Z)-(methoxyimino)methyl]phenyl or
R1- is 2-[(E/Z)-(ethoxyimino)methyl]phenyl or
R1- is 2-[(1E/Z)-N-methoxyethanimidoyl]phenyl or
R1- is 3-[(1E/Z)-N-ethoxyethanimidoyl]phenyl or
R1- is 4-[(tert-butoxycarbonyl)amino]phenyl or
R1- is 2-[(E/Z)-(hydroxyimino)methyl]phenyl or
R1- is 4,5-dimethyl-2-[(methylsulphonyl)oxy]phenyl or
R1- is 2-[(ethylsulphonyl)oxy]phenyl or
R1- is 4-[(methylsulphonyl)oxy]phenyl or
R1- is 2-formamidophenyl or
R1- is 4-(2-methoxy-2-oxoethoxy)phenyl or
R1- is 2-[(allyloxy)methyl]phenyl or
R1- is 3-(cyanomethoxy)-2,6-difluorophenyl or
R1- is 2-{[(2-methoxyethyl)sulphinyl]methyl}phenyl or
R1- is 4-[(cyclopropylsulphonyl)oxy]phenyl or
R1- is 3-chloro-2-(cyanomethoxy)phenyl or
R1- is 2-[(4-fluorobenzoyl)oxy]phenyl or
R1- is 3-fluoro-2-[(methylsulphonyl)oxy]phenyl or
R1- is 2,3-dimethoxy-6-[(methylsulphonyl)oxy]phenyl or
R1- is 2-{[(trifluoromethyl)sulphonyl]oxy}phenyl or
R1- is 2-[(2E)-but-2-enoyloxy]phenyl or
R1- is 2-fluoro-6-[(prop-2-yn-1-yloxy)methyl]phenyl or
R1- is 2-[(ethylcarbamoyl)oxy]phenyl or
R1- is 5-chloro-2-[(methylsulphonyl)oxy]phenyl or
R1- is 2-[formyl(prop-2-yn-1-yl)amino]phenyl or
R1- is 2-{[(1-chlorocyclopropyl)carbonyl]oxy}phenyl or
R1- is 4-methyl-2-[(methylsulphonyl)oxy]phenyl or
R1- is 4-chloro-2-[(methyl sulphonyl)oxy]phenyl or
R1- is 2-fluoro-6-[(E/Z)-(methoxyimino)methyl]phenyl or
R1- is 2-[(cyclopropylsulphonyl)oxy]-3-fluorophenyl or
R1- is 2-(cyanomethoxy)-4-methylphenyl or
R1- is 2-[(prop-2-yn-1-yloxy)methyl]phenyl or
R1- is 2-[(methylsulphanyl)methoxy]phenyl or
R1- is 2-(cyanomethoxy)-3-fluorophenyl or
R1- is 2-methoxy-6-[(methylsulphonyl)oxy]phenyl or
R1- is 2-(acryloyloxy)phenyl or
R1- is 3-chloro-2-[(methylsulphonyl)oxy]phenyl or
R1- is 2-[(trimethylsilyl)ethynyl]phenyl or
R1- is 3-[(cyclopropylsulphonyl)oxy]phenyl or
R1- is 2-[(cyclopropylsulphonyl)oxy]-5-fluorophenyl or
R1- is 4-(cyanomethoxy)phenyl or
R1- is 2-(dimethylcarbamothioyl)phenyl or
R1- is 5-chloro-2-(cyanomethoxy)phenyl or
R1- is 2-(cyanomethoxy)-6-fluorophenyl or
R1- is 2-[(cyclopropylsulphonyl)oxy]phenyl or
R1- is 2-{[(2-methoxyethyl)sulphonyl]methyl}phenyl or
R1- is 2-chloro-6-[(methyl sulphonyl)oxy]phenyl or
R1- is 4-chloro-2-(cyanomethoxy)phenyl or
R1- is 3- { [3-(1-naphthyl)prop-2-yn-l-yl]oxy }phenyl or
R1- is 4-[(ethylsulphonyl)oxy]phenyl or
R1- is 3-[(ethylsulphonyl)oxy]phenyl or
R1- is 2-{[(2-methoxyethyl)sulphanyl]methyl}phenyl or
R1- is 2,6-difluoro-3-[(methylsulphonyl)oxy]phenyl or
R1- is 5-methyl-2-[(methylsulphonyl)oxy]phenyl or
R1- is 2-(cyanomethoxy)phenyl or
R1- is 2-(cyanomethoxy)-5-methylphenyl or
R1- is 2-{[(4-methylphenyl)sulphonyl]oxy}phenyl or
R1- is 2-[(cyanomethyl)(formyl)amino]phenyl or
R1- is 3-(cyanomethoxy)phenyl or
R1- is 2-chloro-6-(cyanomethoxy)phenyl.

### Claim 9 (depends on 1)

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

### Claim 10 (depends on 1)

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

### Claim 11 (depends on 1)

A process for producing compositions for controlling phytopathogenic harmful fungi, comprising mixing one or more compounds of the formula (I) according to claim 1 with extenders and/or surfactants.

### Claim 12 (depends on 9)

The method according to claim 9, comprising treatment of transgenic plants.