# US 10,477,864 B2 · Microbiocidal quinoline (thio)carboxamide derivatives

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- Number: US 10,477,864 B2
- Document ID: US10477864B2
- Status: Granted
- Kind: B2
- Application number: 16/083,844
- Filed: 2017-03-07
- Published: 2019-03-07
- Granted: 2019-11-19
- Earliest claimed: 2016-03-10
- Assignees: Syngenta Participations AG
- Applicants: Syngenta Participations AG
- Inventors: Matthias Weiss; Farhan Bou Hamdan; Laura Quaranta
- Web page: https://patentgrep.com/patent/US10477864B2

## CPC

- A01N 43/42: condensed with carbocyclic rings
- C07D 215/54: attached in position 3
- 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)

## Abstract

Compounds of the formula (I) wherein the substituents are as defined in claim 1. Furthermore, the present invention relates to agrochemical compositions which comprise compounds of formula (I), to preparation of these compositions, and to the use of the compounds or compositions in agriculture or horticulture for combating, preventing or controlling infestation of plants, harvested food crops, seeds or non-living materials by phytopathogenic microorganisms, in particular fungi.

## Claims

### Claim 1

A compound of formula (I):
wherein
X is O or S;
R1 is hydrogen, halogen, methyl, methoxy or cyano;
R2 and R3 are each independently hydrogen, halogen or methyl;
R4 is hydrogen, cyano, C1-C4 alkyl, or C3-C4 cycloalkyl, wherein the alkyl and cycloalkyl, may be optionally substituted with 1 to 3 substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3 alkoxy and C1-C3 alkylthio;
R5 and R6 are each independently selected from hydrogen, halogen, C1-C4 alkyl, C1-C4 alkoxy and C1-C4 alkylthio; or
R5 and R6 together with the carbon atom to which they are attached represent C═O, C═NORc, C3-C5 cycloalkyl or C2-C5 alkenyl, wherein the cycloalkyl and alkenyl may be optionally substituted with 1 to 3 substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3 alkoxy and C1-C3 alkylthio;
R7 is hydrogen, C1-C5 alkyl, C3-C5 cycloalkyl, C2-C5 alkenyl, C3-C5 cycloalkenyl, or C2-C5 alkynyl, wherein the alkyl, cycloalkyl, alkenyl, alkynyl, cycloalkenyl may be optionally substituted with 1 to 4 substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3 alkoxy, hydroxyl and C1-C3 alkylthio;
R8 and R9 are each independently selected from hydrogen, halogen, C1-C4 alkyl and C1-C4 alkoxy; or
R8 and R9 together with the carbon atom to which they are attached represent C3-C5 cycloalkyl, wherein the cycloalkyl may be optionally substituted with 1 to 3 substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3 alkoxy and C1-C3 alkylthio;
each R10 independently represents halogen, nitro, cyano, formyl, C1-C5 alkyl, C2-C5 alkenyl, C2-C5 alkynyl, C3-C6 cycloalkyl, C1-C5 alkoxy, C3-C5 alkenyloxy, C3-C5 alkynyloxy, C1-C5 alkylthio, —C(═NORc)C1-C5 alkyl, or C1-C5 alkylcarbonyl, wherein the alkyl, cycloalkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy and alkylthio may be optionally substituted with 1 to 5 substituents independently selected from halogen, C1-C3 alkyl, C1-C3 alkoxy, cyano and C1-C3 alkylthio; n is 0, 1, 2, 3, 4 or 5;
each Rc is independently selected from hydrogen, C1-C4 alkyl, C2-C4 alkenyl, C3-C4 alkynyl, C3-C4 cycloalkyl(C1-C2)alkyl and C3-C4 cycloalkyl, wherein the alkyl, cycloalkyl, alkenyl and alkynyl groups may be optionally substituted with 1 to 3 substituents independently selected from halogen and cyano;
R11 is hydrogen, halogen, methyl, methoxy or cyano;
R12 and R13 are each independently selected from hydrogen, halogen, methyl, methoxy or hydroxyl;
and salts and/or N-oxides thereof;
provided that the compound is not one of the following compounds:
, or
a compound wherein R1 is hydrogen, R2 is hydrogen, R3 is methyl, R4 is hydrogen, R5 is hydrogen, R6 is hydrogen, R7 is hydrogen, R8 is hydrogen, R9 is hydrogen, n is 1, R10 is 2-methyl, R11 is fluoro, R12 is hydrogen, R13 is hydrogen, and X is O.

### Claim 2 (depends on 1)

A compound according to claim 1 wherein R1 is hydrogen, fluoro, chloro, methyl, or cyano.

### Claim 3 (depends on 1)

A compound according to claim 1 wherein R2 and R3 are each independently hydrogen or methyl.

### Claim 4 (depends on 1)

A compound according to claim 1, wherein R4 is hydrogen, cyano, C1-C3 alkyl, or cyclopropyl, wherein the alkyl and cycloalkyl, may be optionally substituted with 1 to 3 substituents independently selected from fluoro, chloro, cyano, methyl, methoxy and methylthio.

### Claim 5 (depends on 1)

A compound according to claim 1, wherein R5 and R6 are each independently selected from hydrogen, fluoro, C1-C2 alkyl, C1-C2 alkoxy and C1-C2 alkylthio; or R5 and R6 together with the carbon atom to which they are attached represent C═O or cyclopropyl, wherein the cyclopropyl may be optionally substituted with 1 to 2 substituents independently selected from fluoro, methyl and cyano.

### Claim 6 (depends on 1)

A compound according to claim 1, wherein R7 is C1-C4 alkyl, C3-C4 cycloalkyl, C2-C4 alkenyl, or C2-C3 alkynyl, wherein the alkyl, cycloalkyl, alkenyl, alkynyl, may be optionally substituted with 1 to 3 substituents independently selected from fluoro, chloro, cyano, methyl, hydroxyl and methylthio.

### Claim 7 (depends on 1)

A compound according to claim 1 wherein R8 and R9 are each independently selected from hydrogen, fluoro, C1-C2 alkyl and C1-C2 alkoxy; or R8 and R9 together with the carbon atom to which they are attached represent cyclopropyl, wherein the cyclopropyl may be optionally substituted with 1 to 2 substituents independently selected from fluoro, cyano, and methyl.

### Claim 8 (depends on 1)

A compound according to claim 1 wherein each R10 independently represents halogen, cyano, C1-C3 alkyl, C2-C3 alkenyl, C2-C3 alkynyl, cyclopropyl, methoxy, allyloxy, propargyloxy, or C1-C2 alkylthio, wherein the alkyl, cyclopropyl, alkenyl, alkynyl, methoxy, allyloxy, propargyloxy and alkylthio may be optionally substituted with 1 to 3 substituents independently selected from fluoro, chloro, methyl, and cyano; n is 0, 1, 2 or 3.

### Claim 9 (depends on 1)

A compound according to claim 1 wherein R11 is hydrogen, fluoro, chloro, methyl or cyano; and R12 and R13 are each independently selected from hydrogen, fluoro, methyl and hydroxyl.

### Claim 10 (depends on 1)

A compound according to claim 1 wherein X is O or S; R1 is hydrogen, fluoro, chloro, methyl, or cyano; R2 and R3 are each independently hydrogen or methyl; R4 is hydrogen, cyano, C1-C3 alkyl, or cyclopropyl, wherein the alkyl and cycloalkyl, may be optionally substituted with 1 to 3 substituents independently selected from fluoro, chloro, cyano, methyl, methoxy, and methylthio; R5 and R6 are each independently selected from hydrogen, fluoro, C1-C2 alkyl, C1-C2 alkoxy and C1-C2 alkylthio; or R5 and R6 together with the carbon atom to which they are attached represent C═O or cyclopropyl, wherein the cyclopropyl may be optionally substituted with 1 to 2 substituents independently selected from fluoro, methyl and cyano; R7 is C1-C4 alkyl, C3-C4 cycloalkyl, C2-C4 alkenyl, or C2-C3 alkynyl, wherein the alkyl, cycloalkyl, alkenyl, alkynyl, may be optionally substituted with 1 to 3 substituents independently selected from fluoro, chloro, cyano, methyl, hydroxyl and methylthio; R8 and R9 are each independently selected from hydrogen, fluoro, C1-C2 alkyl and C1-C2 alkoxy; or R8 and R9 together with the carbon atom to which they are attached represent cyclopropyl, wherein the cyclopropyl may be optionally substituted with 1 to 2 substituents independently selected from fluoro, cyano, and methyl; each R10 independently represents halogen, cyano, C1-C3 alkyl, C2-C3 alkenyl, C2-C3 alkynyl, cyclopropyl, methoxy, allyloxy, propargyloxy, or C1-C2 alkylthio, wherein the alkyl, cyclopropyl, alkenyl, alkynyl, methoxy, allyloxy, propargyloxy and alkylthio may be optionally substituted with 1 to 3 substituents independently selected from fluoro, chloro, methyl, and cyano; n is 0, 1, 2 or 3; R11 is hydrogen, fluoro, chloro, methyl or cyano; and R12 and R13 are each independently selected from hydrogen, fluoro, methyl and hydroxyl; or a salt or N-oxide thereof.

### Claim 11 (depends on 1)

A compound according to claim 1 wherein X is 0 or S; R1 is hydrogen, fluoro, methyl, or cyano; R2 is hydrogen and R3 is hydrogen or methyl; or R2 is hydrogen or methyl and R3 is hydrogen; R4 is hydrogen, cyano, methyl or ethyl, wherein the methyl and ethyl may be optionally substituted with 1 to 3 substituents independently selected from fluoro and methoxy; R5 and R6 are each independently selected from hydrogen, fluoro, methyl, methoxy and methylthio; or R5 and R6 together with the carbon atom to which they are attached represent cyclopropyl; R7 is C1-C4 alkyl, C3-C4 cycloalkyl, or C2-C4 alkenyl, wherein the alkyl, cycloalkyl and alkenyl may be optionally substituted with 1 to 3 substituents independently selected from fluoro, chloro, hydroxyl, cyano and methyl; R8 and R9 are each independently selected from hydrogen, fluoro and methyl; or R8 and R9 together with the carbon atom to which they are attached represent cyclopropyl; each R10 independently represents fluoro, chloro, cyano, methyl, cyclopropyl, methoxy or methylthio, wherein the methyl, cyclopropyl, methoxy and methylthio may be optionally substituted with 1 to 3 substituents independently selected from fluoro and chloro; n is 0, 1 or 2; R11 is hydrogen, fluoro, methyl or chloro; and R12 and R13 are each independently selected from hydrogen, fluoro and methyl; or a salt or N-oxide thereof.

### Claim 12 (depends on 1)

A compound according to claim 1 wherein X is O or S; R1 is hydrogen or fluoro; R2 and R3 are both hydrogen; R4 is methyl or ethyl (wherein the methyl and ethyl may be optionally substituted with 1 to 3 fluoro substituents); R5 and R6 are each independently selected from hydrogen and fluoro; R7 is methyl, ethyl, n-propyl, iso-propyl, sec-butyl, tert-butyl, C3-C4 cycloalkyl, or C2-C4 alkenyl, wherein the methyl, ethyl, n-propyl, iso-propyl, sec-butyl, tert-butyl, cycloalkyl and alkenyl may be optionally substituted with 1 to 3 substituents independently selected from fluoro, chloro and methyl; R8 and R9 are each independently selected from hydrogen or fluoro; each R10 independently represents fluoro, chloro, cyano or methyl, wherein the methyl may be optionally substituted with 1 to 3 fluoro substituents; n is 0, 1 or 2; and R11 is hydrogen or fluoro; R12 and R13 are both hydrogen; or a salt or N-oxide thereof.

### Claim 13 (depends on 1)

A compound according to claim 1 wherein X is O.

### Claim 14 (depends on 1)

A composition comprising a fungicidally effective amount of a compound of formula (I) as defined in claim 1.

### Claim 15 (depends on 14)

A composition according to claim 14, wherein the composition further comprises at least one additional active ingredient and/or a diluent.

### Claim 16 (depends on 1)

A method of combating, preventing or controlling phytopathogenic diseases which comprises applying to a phytopathogen, to the locus of a phytopathogen, or to a plant susceptible to attack by a phytopathogen, or to propagation material thereof, a fungicidally effective amount of a compound of formula (I) as defined in claim 1 or a composition comprising a fungicidally effective amount of a compound of formula (I) as defined in claim 1.

### Claim 17 (depends on 1)

A compound according to claim 1 selected from:
N-[1-benzyl-1-2-(1-methylcyclopropyl)ethyl]-8-fluoro-quinoline-3-carboxamide (compound E-47),
N-1-benzyl-3,3,3-trifluoro-1-methyl-propyl)-8-methyl-quinoline-3-carboxamide (compound E-61),
N-1-benzyl-3,3,3-trifluoro-1-methyl-propyl)-8-chloro-quinoline-3-carboxamide (compound E-60),
N-1-benzyl-3,3,3-trifluoro-1-methyl-propyl)-8-fluoro-quinoline-3-carboxamide (compound E-39),
N-1-benzyl-3,3,3-trifluoro-1-methyl-propyl)-7,8-difluoro-quinoline-3-carboxamide (compound E-102),
N-(1-benzyl-1,3-dimethyl-butyl)-7,8-difluoro-quinoline-3-carboxamide (compound E-48),
N-(1-benzyl-1,3-dimethyl-butyl)-8-difluoro-quinoline-3-carboxamide (compound E-35),
N-(1-benzyl-1,3-dimethyl-butyl)-7,8-difluoro-quinoline-3-carboxamide (compound E-55),
8-fluoro-N-1-N-[1-[(3-fluorophenyl)methyl]-1,3-dimethyl-butyl]quinoline- 3-carboxamide (compound E-26),
8-fluoro-N-[3,3,3,-trifluoro-1-[(3-fluorophenyl)methyl]-1-methyl-propyl]quinoline-3-carboxamide (compound E-99),
N-(1-benzyl-3,3-difluoro-1-methyl-butyl)-8-fluoro-quinoline-3-carboxamide (compound E-50),
N-(1-benzyl-3-fluoro-1,3-methyl-butyl)-8-fluoro-quinoline-3-carboxamide (compound E-56),
N-(1-benzyl-1,3,3-trimethyl-butyl)-8-fluoro-quinoline-3-carboxamide (compound E-34),
N-(1-benzyl-1,3-dimethyl-butyl)-8-fluoro-quinoline-3-carboxamide (compound E-6),
N-(1-benzyl-1,3-dimethyl-butyl)-8-methyl-quinoline-3-carboxamide (compound E-20),
N-(1-benzyl-1,3-dimethyl-butyl)-8-chloro-quinoline-3-carboxamide (compound E-14), and
N-(1-benzyl-1,3-dimethyl-butyl)quinoline-3-carboxamide (compound E-13).