# US 10,246,420 B2 · Pyrazole derivatives

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- Number: US 10,246,420 B2
- Document ID: US10246420B2
- Status: Granted
- Kind: B2
- Application number: 15/327,531
- Filed: 2015-07-21
- Published: 2017-06-22
- Granted: 2019-04-02
- Earliest claimed: 2014-07-24
- Assignees: Bayer CropScience AG
- Applicants: Bayer Cropscience Aktiengesellschaft
- Inventors: Joachim Telser; Peter Dahmen; Ulrike Wachendorff-Neumann; Pierre Cristau; Philippe Rinolfi
- Web page: https://patentgrep.com/patent/US10246420B2

## CPC

- C07D 231/38: Nitrogen atoms (nitro radicals C07D231/16)
- A01N 43/56: 1,2-Diazoles; Hydrogenated 1,2-diazoles
- C07C 217/76: having amino groups bound to carbon atoms of six-membered aromatic rings and etherified hydroxy groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C 331/28: having isothiocyanate groups bound to carbon atoms of six-membered aromatic rings
- C07D 401/04: directly linked by a ring-member-to-ring-member bond
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- 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
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

The present invention relates to novel pyrazole derivatives, to processes for preparing these compounds, to compositions comprising these compounds, and to the use thereof as biologically active compounds, especially for controlling harmful microorganisms in crop protection and in the protection of materials. Further, the present invention also relates to certain intermediates useful for producing said novel pyrazole derivatives.

## Claims

### Claim 1

A compound of formula (I)
and/or one or more tautomers and/or salts thereof, wherein
R1 is H, CH3, F, Cl, Br, or C1-C4 alkoxy,
R2 is methyl or ethyl,
X is a structure element selected from the group consisting of NH, N(CH3), O, S, CH2, CH(OH), and CH(CH3),
Q1 is a 5- to 7-membered carbocyclic ring, optionally substituted with up to 5 independently selected substituents RQ1;
or a 5- to 7-membered heterocyclic ring containing ring members selected from the group consisting of C, N, O and S, and containing up to 3 heteroatom ring members independently selected from the group O, S, and N, wherein the heterocyclic ring contains as heteroatom ring members up to 1 O atom, up to 1 S atom, and up to 3 N atoms,
wherein optionally up to 3 carbon ring members are independently selected from C(═O) and C(═S), and, if present, the sulfur atom ring members are independently selected from S, S(O), or S(O)2,
wherein the heterocyclic ring is optionally substituted with up to 5 substituents RQ1 on carbon atom heterocyclic ring members and optionally substituted with substituents RN on nitrogen atom heterocyclic ring members, if present, each RQ1 is independently selected from the group consisting of halogen, cyano, nitro, amino, hydroxy, formyl, C1-C6 alkyl, C1-C6haloalkyl, C3-C6 cycloalkyl, C3-C7 halocycloalkyl, C3-C6 heterocyclyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C2-C6 alkenyl, C3-C7 alkenylalkoxy, C2-C6 alkenyloxy, C2-C6 alkynyl, C3-C7 alkynylalkoxy, C3-C7 alkynyloxy, C3-C7 cycloalkoxy, C3-C6 halocycloalkoxy, C3-C6 heterocyclyloxy, C1-C3 alkylthio, C1-C3 haloalkylthio, C1-C3 alkylsulfinyl, C1-C3haloalkylsulfinyl, C1-C3 alkylsulfonyl, C1-C3 haloalkylsulfonyl, C1-C2 alkylsulfonyloxy, C1-C2 haloalkylsulfonyloxy, C4-C7 alkylcycloalkyl, C4-C6 cycloalkylalkyl, C2-C3 alkylcarbonyl, C2-C3 alkylcarbonyloxy, C1-C4 alkanoylamino, C2-C3 alkylcarbonylamino, (C1-C6 alkoxy)iminocarbonyl, tri(C1-C4-alkyl)silyl, SCF3, SF5, SCN, isonitrile, CRC═NO—C1-C4 alkyl, —NR1NR2N and optionally substituted phenyl,
Q2 is a 5- or 6-membered carbocyclic ring, [optionally] substituted with 1 [up] to 5 substituents RQ2;
or a 5- to 7-membered heterocyclic ring containing ring members selected from the group consisting of C, N, O and S, and containing up to 3 heteroatom ring members independently selected from the group O, S, and N, wherein the heterocyclic ring contains as heteroatom ring members up to 1 O atom, up to 1 S atom, and up to 3 N atoms, wherein optionally up to 3 carbon ring members are independently selected from C(═O) and C(═S), and, if present, the sulfur atom ring members are independently selected from S, S(O), or S(O)2,
wherein the heterocyclic ring is [optionally] substituted with [up] 1 to 5 substituents RQ2 on carbon atom heterocyclic ring members and optionally substituted with substituents RN on nitrogen atom heterocyclic ring members, if present,
each RQ2 is independently selected from the group consisting of halogen, cyano, nitro, amino, hydroxy, formyl, C1-C6 alkyl, C1-C6haloalkyl, C3-C6 cycloalkyl, C3-C7 halocycloalkyl, C3-C6 heterocyclyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C2-C6 alkenyl, C3-C7 alkenylalkoxy, C2-C6 alkenyloxy, C2-C6 alkynyl, C3-C7 alkynylalkoxy, C3-C7 alkynyloxy, C3-C7 cycloalkoxy, C3-C6 halocycloalkoxy, C3-C6 heterocyclyloxy, C1-C3 alkylthio, C1-C3 haloalkylthio, C1-C3 alkylsulfinyl, C1-C3haloalkylsulfinyl, C1-C3 alkylsulfonyl, C1-C3 haloalkylsulfonyl, C1-C2 alkylsulfonyloxy, C1-C2 haloalkylsulfonyloxy, C4-C7 alkylcycloalkyl, C4-C6 cycloalkylalkyl, C2-C3 alkylcarbonyl, C2-C3 alkylcarbonyloxy, C1-C4 alkanoylamino, C2-C3 alkylcarbonylamino, (C1-C6 alkoxy)iminocarbonyl, tri(C1-C4-alkyl)silyl, SCF3, SF5, SCN, isonitrile, CRC═NO—C1-C4 alkyl, —NR1NR2N and optionally substituted phenyl,
wherein each RN is independently selected from the group consisting of cyano, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C1-C6alkoxy, C2-C6 alkoxyalkyl, C2-C6 alkylcarbonyl, C2-C6 alkoxycarbonyl, C2-C6 alkylaminoalkyl and C3-C6 dialkylaminoalkyl, C1-C6 aminoalkyl, benzyl, and SO2RS,
wherein each RC is independently selected from the group consisting of H and C1-C4 alkyl,
wherein R1N and R2N each are independently selected from C1-C4 alkyl and C3-C6 cycloalkyl,
wherein each RS is independently selected from C1-C4 alkyl, C1-C4 haloalkyl, and C3-C6 cycloalkyl,
wherein each optionally substituted phenyl is independently selected from phenyl substituted with up to 5 radicals selected from the group consisting of halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, (C1-C4)-alkoxy-(C1-C4)-alkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, (C1-C4)-alkoxy-(C1-C4)-alkoxy, (C1-C4) alkylthio and nitro,
provided that at least one substituent RQ2 that is present is C3-C7 alkenylalkoxy or C3-C7 alkynylalkoxy.

### Claim 2 (depends on 1)

A compound of formula (I) according to claim 1, and/or one or more tautomers and/or salts thereof, wherein
R1 is H, CH3, F, Cl, Br, or OCH3,
R2 is methyl or ethyl,
X is a structure element selected from the group consisting of NH, N(CH3), O, S, CH2, CH(OH), and CH(CH3),
Q1 is a 5- to 7-membered fully saturated carbocyclic ring or a fully unsaturated 6-membered carbocyclic ring, optionally substituted with up to 5 substituents RQ1; or a 5- to 7-membered fully saturated heterocyclic ring or a fully unsaturated 5- or 6-membered heterocyclic ring containing ring members selected from the group consisting of C, N, O and S, and containing up to 3 heteroatom ring members independently selected from the group O, S, and N, wherein the heterocyclic ring contains as heteroatom ring members up to 1 O atom, up to 1 S atom, and up to 3 N atoms, wherein the heterocyclic ring is optionally substituted with up to 3 substituents RQ1 on carbon atom heterocyclic ring members and optionally substituted with substituents RN on nitrogen atom heterocyclic ring members, if present,
each RQ1 is independently selected from the group consisting of halogen, cyano, nitro, amino, hydroxy, formyl, C1-C6 alkyl, C1-C6haloalkyl, C3-C6 cycloalkyl, C3-C7 halocycloalkyl, C3-C6 heterocyclyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C2-C6 alkenyl, C3-C7 alkenylalkoxy, C2-C6 alkenyloxy, C2-C6 alkynyl, C3-C7 alkynylalkoxy, C3-C7 alkynyloxy, C3-C7 cycloalkoxy, C3-C6 halocycloalkoxy, C3-C6 heterocyclyloxy, C1-C3 alkylthio, C1-C3 haloalkylthio, C1-C3 alkylsulfinyl, C1-C3haloalkylsulfinyl, C1-C3 alkylsulfonyl, C1-C3 haloalkylsulfonyl, C1-C2 alkylsulfonyloxy, C1-C2 haloalkylsulfonyloxy, C4-C7 alkylcycloalkyl, C4-C6 cycloalkylalkyl, C2-C3 alkylcarbonyl, C2-C3 alkylcarbonyloxy, C1-C4 alkanoylamino, C2-C3 alkylcarbonylamino, (C1-C6 alkoxy)iminocarbonyl, tri(C1-C4-alkyl)silyl, SCF3, SF5, SCN, isonitrile, CH═NO—C1-C4 alkyl, —NR1NR2N and optionally substituted phenyl,
Q2 is a fully unsaturated or a fully saturated 5- or 6-membered carbocyclic ring, [optionally] substituted with [up] 1 to 5 substituents RQ2;
or is a fully unsaturated or a fully saturated 5- or 6-membered heterocyclic ring, wherein the heterocyclic ring is [optionally] substituted with [up] 1 to 5 substituents RQ2 on carbon atom heterocyclic ring members and optionally substituted with substituents RN on nitrogen atom heterocyclic ring members, if present,
each RQ2 is independently selected from the group consisting of halogen, cyano, nitro, amino, hydroxy, formyl, C1-C6 alkyl, C1-C6haloalkyl, C3-C6 cycloalkyl, C3-C7 halocycloalkyl, C3-C6 heterocyclyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C2-C6 alkenyl, C3-C7 alkenylalkoxy, C2-C6 alkenyloxy, C2-C6 alkynyl, C3-C7 alkynylalkoxy, C3-C7 alkynyloxy, C3-C7 cycloalkoxy, C3-C6 halocycloalkoxy, C3-C6 heterocyclyloxy, C1-C3 alkylthio, C1-C3 haloalkylthio, C1-C3 alkylsulfinyl, C1-C3 haloalkylsulfinyl, C1-C3 alkylsulfonyl, C1-C3 haloalkylsulfonyl, C1-C2 alkylsulfonyloxy, C1-C2 haloalkylsulfonyloxy, C4-C7 alkylcycloalkyl, C4-C6 cycloalkylalkyl, C2-C3 alkylcarbonyl, C2-C3 alkylcarbonyloxy, C1-C4 alkanoylamino, C2-C3 alkylcarbonylamino, (C1-C6 alkoxy)iminocarbonyl, tri(C1-C4-alkyl)silyl, SCF3, SF5, SCN, isonitrile, CH═NO—C1-C4 alkyl, —NR1NR2N and optionally substituted phenyl,
wherein each RN is independently selected from the group consisting of cyano, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C1-C6alkoxy, C2-C6 alkoxyalkyl, C2-C6 alkylcarbonyl, C2-C6 alkoxycarbonyl, C2-C6 alkylaminoalkyl and C3-C6 dialkylaminoalkyl, C1-C6 aminoalkyl, benzyl, SO2RS, wherein R1N and R2N each are independently selected from C1-C4 alkyl and C3-C6 cycloalkyl,
wherein each RS is independently selected from C1-C4 alkyl, C1-C4 haloalkyl, and C3-C6 cycloalkyl,
wherein each optionally substituted phenyl is independently selected from phenyl substituted with up to 5 radicals selected from the group consisting of halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, (C1-C4)-alkoxy-(C1-C4)-alkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, (C1-C4)-alkoxy-(C1-C4)-alkoxy, (C1-C4) alkylthio and nitro
provided that at least one substituent RQ2 is C3-C7 alkenylalkoxy or C3-C7 alkynylalkoxy.

### Claim 3 (depends on 1)

A compound of formula (I) according to claim 1, and/or one or more tautomers and/or salts thereof, wherein
R1 is H, CH3, F, Cl or Br,
R2 is CH3,
X is a structure element selected from the group consisting of NH, N(CH3), O, S, CH2, CH(OH), and CH(CH3),
Q1 is a ring selected from the group consisting of phenyl, 5- or 6-membered heteroaromatic rings, 5- to 7-membered fully saturated heterocyclic rings, and 5- to 7-membered fully saturated carbocyclic rings, wherein Q1 is optionally substituted with up to 5 substituents RQ1;
wherein each RQ1 is independently selected from the group consisting of halogen, cyano, nitro, amino, hydroxy, formyl, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C7 halocycloalkyl, C3-C6 heterocyclyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C2-C6 alkenyl, C3-C7 alkenylalkoxy, C2-C6 alkenyloxy, C2-C6 alkynyl, C3-C7 alkynylalkoxy, C3-C7 alkynyloxy, C3-C7 cycloalkoxy, C3-C6 halocycloalkoxy, C3-C6 heterocyclyloxy, C1-C3 alkylthio, C1-C3 haloalkylthio, C1-C3alkylsulfinyl, C1-C3 haloalkylsulfinyl, C1-C3 alkylsulfonyl, C1-C3 haloalkylsulfonyl, C1-C2 alkylsulfonyloxy, C1-C2 haloalkylsulfonyloxy, C4-C7 alkylcycloalkyl, C4-C6 cycloalkylalkyl, C2-C3 alkylcarbonyl, C2-C3 alkylcarbonyloxy, C1-C4 alkanoylamino, C2-C3 alkylcarbonylamino, (C1-C6 alkoxy)iminocarbonyl, tri(C1-C4-alkyl)silyl, SCF3, SF5, SCN, isonitrile, CH═NO—C1-C4 alkyl, —NR1NR2N and optionally substituted phenyl,
Q2 is a fully unsaturated or a fully saturated 5- or 6-membered carbocyclic or heterocyclic ring, [optionally] substituted with [up] 1 to 5 substituents RQ2; wherein each RQ2 is independently selected from the group consisting of halogen, cyano, nitro, amino, hydroxy, formyl, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C7 halocycloalkyl, C3-C6 heterocyclyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C2-C6 alkenyl, C3-C7 alkenylalkoxy, C2-C6 alkenyloxy, C2-C6 alkynyl, C3-C7 alkynylalkoxy, C3-C7 alkynyloxy, C3-C7 cycloalkoxy, C3-C6 halocycloalkoxy, C3-C6 heterocyclyloxy, C1-C3 alkylthio, C1-C3 haloalkylthio, C1-C3alkylsulfinyl, C1-C3 haloalkylsulfinyl, C1-C3 alkylsulfonyl, C1-C3 haloalkylsulfonyl, C1-C2 alkylsulfonyloxy, C1-C2 haloalkylsulfonyloxy, C4-C7 alkylcycloalkyl, C4-C6 cycloalkylalkyl, C2-C3 alkylcarbonyl, C2-C3 alkylcarbonyloxy, C1-C4 alkanoylamino, C2-C3 alkylcarbonylamino, (C1-C6 alkoxy)iminocarbonyl, tri(C1-C4-alkyl)silyl, SCF3, SF5, SCN, isonitrile, CH═NO—C1-C4 alkyl, —NR1NR2N and optionally substituted phenyl,
wherein R1N and R2N are independently selected from C1-C4 alkyl and C3-C6 cycloalkyl,
wherein each optionally substituted phenyl is independently selected from phenyl substituted with up to 5 radicals selected from the group consisting of halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, (C1-C4)-alkoxy-(C1-C4)-alkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, (C1-C4)-alkoxy-(C1-C4)-alkoxy, (C1-C4) alkylthio and nitro,
provided that at least one substituent RQ2 is C3-C7 alkenylalkoxy or C3-C7 alkynylalkoxy.

### Claim 4 (depends on 1)

A compound of formula (I) according to claim 1, and/or one or more tautomers and/or salts thereof, wherein
R1 is CH3 or C1,
R2 is CH3,
X is a structure element selected from the group consisting of NH, N(CH3), O, S, CH2, CH(OH), and CH(CH3),
Q1 is a ring selected from the group consisting of phenyl, 5- or 6-membered heteroaromatic rings, 5- to 7-membered fully saturated heterocyclic rings, and 5- or 6-membered fully saturated carbocyclic rings, wherein Q1 is optionally substituted with up to 5 substituents RQ1;
wherein each RQ1 is independently selected from the group consisting of halogen, cyano, nitro, amino, hydroxy, formyl, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C7 halocycloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C2-C6 alkenyl, C3-C7 alkenylalkoxy, C2-C6 alkynyl, C3-C7 alkynylalkoxy, C3-C7 alkynyloxy, C3-C7 cycloalkoxy, C3-C6 halocycloalkoxy, C4-C7 alkylcycloalkyl, C4-C6 cycloalkylalkyl, C1-C4 alkanoylamino, SF5, SCN, isonitrile, CH═NO—C1-C4 alkyl, —NR1NR2N and optionally substituted phenyl,
Q2 is a ring selected from the group consisting of phenyl, 5-membered heteroaromatic rings and 6-membered heteroaromatic rings, wherein Q2 is [optionally] substituted with [up] 1 to 5 substituents RQ2;
wherein each RQ2 is independently selected from the group consisting of halogen, cyano, nitro, amino, hydroxy, formyl, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C7 halocycloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C2-C6 alkenyl, C3-C4 alkenylalkoxy, C2-C6 alkynyl, C3-C7 alkynylalkoxy, C3-C7 alkynyloxy, C3-C7 cycloalkoxy, C3-C6 halocycloalkoxy, C4-C7 alkylcycloalkyl, C4-C6 cycloalkylalkyl, C1-C4 alkanoylamino, SF5, SCN, isonitrile, CH═NO—C1-C4 alkyl, —NR1NR2N and optionally substituted phenyl,
wherein R1N and R2N are independently selected from C1-C4 alkyl and C3-C6 cycloalkyl,
wherein each optionally substituted phenyl is independently selected from phenyl substituted with up to 5 radicals selected from the group consisting of halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, (C1-C4)-alkoxy-(C1-C4)-alkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, (C1-C4)-alkoxy-(C1-C4)-alkoxy, (C1-C4) alkylthio and nitro,
provided that at least one substituent RQ2 is C3-C7 alkenylalkoxy or C3-C7 alkynylalkoxy.

### Claim 5 (depends on 1)

A compound of formula (I) according to claim 1, and/or one or more tautomers and/or salts thereof, wherein
R1 is CH3 or C1,
R2 is CH3,
X is a structure element selected from the group consisting of NH, N(CH3), O, S, CH2, CH(OH), and CH(CH3),
Q1 is a ring selected from the group consisting of phenyl, 5- or 6-membered heteroaromatic rings, 5- to 7-membered fully saturated heterocyclic rings, and 5- or 6-membered fully saturated carbocyclic rings, wherein Q1 is optionally substituted with up to 5 substituents RQ1;
wherein each RQ1 is independently selected from the group consisting of halogen, cyano, nitro, amino, hydroxy, formyl, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C7 halocycloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C2-C6 alkenyl, C3-C7 alkenylalkoxy, C2-C6 alkynyl, C3-C7 alkynylalkoxy, C3-C7 alkynyloxy, C3-C7 cycloalkoxy, C3-C6 halocycloalkoxy, C4-C7 alkylcycloalkyl, C4-C6 cycloalkylalkyl, C1-C4 alkanoylamino, SF5, SCN, isonitrile, CH═NO—C1-C4 alkyl, —NR1NR2N and optionally substituted phenyl,
wherein R1N and R2N are independently selected from C1-C4 alkyl and C3-C6 cycloalkyl,
wherein optionally substituted phenyl is phenyl substituted with up to 5 radicals selected from the group consisting of halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, (C1-C4)-alkoxy-(C1-C4)-alkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, (C1-C4)-alkoxy-(C1-C4)-alkoxy, (C1-C4) alkylthio and nitro,
Q2 is a ring selected from the group consisting of phenyl or pyridinyl, wherein Q2 is [optionally] substituted with one or more substituents RQ2;
wherein each RQ2 is independently selected from the group consisting of halogen, cyano, nitro, amino, hydroxy, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C7 alkenylalkoxy, C2-C6 alkynyl, C3-C7 alkynylalkoxy, and C3-C7 alkynyloxy,
provided that at least one substituent RQ2 is propargyloxy or allyloxy.

### Claim 6 (depends on 1)

A compound of formula (I) according to claim 1, and/or one or more tautomers and/or salts thereof, wherein
R1 is CH3 or C1,
R2 is CH3,
X is a structure element selected from the group consisting of NH, N(CH3), O, S, CH2, CH(OH), and CH(CH3),
Q1 is a ring selected from the group consisting of phenyl, furanyl, pyridinyl, piperidinyl, azepanyl and morpholinyl, wherein Q1 is optionally substituted with up to 5 substituents RQ1;
wherein each RQ1 is independently selected from the group consisting of halogen, cyano, nitro, amino, hydroxy, formyl, C1-C6 alkyl, C1-C6haloalkyl, C3-C6 cycloalkyl, C3-C7 halocycloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C2-C6 alkenyl, C3-C7 alkenylalkoxy, C2-C6 alkynyl, C3-C7 alkynylalkoxy, C3-C7 alkynyloxy, C3-C7 cycloalkoxy, C3-C6 halocycloalkoxy, C4-C7 alkylcycloalkyl, C4-C6 cycloalkylalkyl, C1-C4 alkanoylamino, SF5, SCN, isonitrile, and —NR1NR2N, wherein
R1N and R2N are independently selected from C1-C4 alkyl and C3-C6 cycloalkyl, provided that at least one of the substituents RQ1 is selected from the group consisting of halogen, cyano, nitro, amino, hydroxy, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C2-C6 alkynyl, C3-C7 alkynylalkoxy, and C3-C7 alkynyloxy,
Q2 is a phenyl ring substituted with one, two, three or four substituents RQ2; wherein each RQ2 is independently selected from the group consisting of halogen, cyano, nitro, amino, hydroxy, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C7 alkenylalkoxy, C2-C6 alkynyl, C3-C7 alkynylalkoxy, and C3-C7 alkynyloxy,
provided that one, two or three substituents RQ2 are propargyloxy or allyloxy.

### Claim 7 (depends on 1)

A compound of formula (I) according to claim 1,
and/or one or more tautomers and/or salts thereof, wherein
R1 is CH3 or C1,
R2 is CH3,
X is NH or O,
Q1 is a phenyl or a furanyl ring, wherein Q1 is optionally substituted with one or more substituents RQ1 selected from the group consisting of F, Cl, Br, I, cyano, nitro, amino, hydroxy, C1-C6 alkyl, C1-C6haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C6 alkenylalkoxy, C2-C6 alkynyl, C3-C7 alkynylalkoxy, and C3-C7 alkynyloxy,
Q2 is a phenyl ring substituted with one, two, three or four substituents RQ2; wherein each RQ2 is independently selected from the group consisting of F, Cl, Br, I, cyano, hydroxy, C1-C6 alkyl, C1-C6haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C6 alkenylalkoxy, C3-C7 alkynylalkoxy, and C3-C7 alkynyloxy,
provided that one, two or three substituents RQ2 are propargyloxy or allyloxy.

### Claim 8 (depends on 1)

A compound of formula (I) according to claim 1, and/or one or more tautomers and/or salts thereof, wherein
R1 is CH3 or C1,
R2 is CH3,
X is NH or O,
Q1 is a phenyl ring substituted with one or more substituents RQ1 selected from the group consisting of F, Cl, Br, I, cyano, nitro, amino, hydroxy, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C3-C6 alkenylalkoxy, C3-C7 alkynylalkoxy, and C3-C6 alkynyloxy,
Q2 is a phenyl ring substituted with one, two, three or four substituents RQ2; wherein each RQ2 is independently selected from the group consisting of F, Cl, Br, I, cyano, hydroxy, C1-C4 alkyl, C1-C4haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C3-C6 alkenylalkoxy, C3-C7 alkynylalkoxy, and C3-C6 alkynyloxy,
provided that one, two or three substituents RQ2 are propargyloxy or allyloxy.

### Claim 9 (depends on 1)

A composition comprising
(a) a fungicidally effective amount of a compound as defined in claim 1,
and one or more further constituents selected from the group consisting of groups (b) and (c):
(b) agrochemically acceptable adjuvants and
(c) other pesticidally active ingredients.

### Claim 10 (depends on 1)

A method for controlling one or more plant diseases caused by fungal plant pathogens, comprising
(i) providing a compound of the formula (I) as defined in claim 1, and
(ii) applying to the plant, to a portion of the plant or to plant seeds a fungicidally effective amount the compound provided in (i).

### Claim 11 (depends on 1)

A product comprising a compound of the formula (I) as defined in claim 1 for controlling fungi in plants or plant seeds.

### Claim 12 (depends on 1)

A method for producing a compound of formula (I) as defined in claim 1, comprising:
(i) providing a compound of formula (Z-ix)
(ii) providing a compound of formula (Z-x)
R2NH—NH2 (Z-x)
(iii) reacting compounds (Z-ix) and (Z-x), thereby obtaining a compound of formula (I).

### Claim 13 (depends on 9)

A composition according to claim 9, comprising one or more of a surfactant, liquid diluent, or solid diluent.

### Claim 14 (depends on 1)

A compound of formula (I) according to claim 1, which comprises at least one RQ2 substituent which is propargyloxy.

### Claim 15 (depends on 1)

A compound of formula (I) according to claim 1, which comprises at least one RQ2 substituent which is allyloxy.