# US 11,440,888 B2 · Microbiocidal quinoline carboxamide derivatives

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- Number: US 11,440,888 B2
- Document ID: US11440888B2
- Status: Granted
- Kind: B2
- Application number: 17/276,644
- Filed: 2019-09-16
- Published: 2021-09-02
- Granted: 2022-09-13
- Earliest claimed: 2018-09-19
- Assignees: Syngenta Crop Protection AG
- Applicants: Syngenta Crop Protection AG
- Inventors: Matthias Weiss; Farhan Bou Hamdan; Laura Quaranta
- Web page: https://patentgrep.com/patent/US11440888B2

## CPC

- C07D 215/38: Nitrogen atoms (nitro radicals C07D215/18)
- A01N 43/42: condensed with carbocyclic rings
- 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

## 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
R1 is hydrogen, halogen, methyl, cyano or methoxy;
R2 and R3 are each independently hydrogen, halogen, methoxy or methyl;
R4 is hydrogen, C1-C5 alkyl, C1-C5 haloalkyl, C3-C5 cycloalkyl, C2-C5 alkenyl, C2-C5 haloalkenyl, C3-C5 cycloalkenyl, —C(═O)C1-C4 alkyl, —CH(═NORc), —C(═NORc)C1-C4 alkyl, or C2-C5 alkynyl, wherein the cycloalkyl, cycloalkenyl may be optionally substituted with 1 to 4 substituents independently selected from halogen, cyano, methyl and C1-C3 alkoxy;
R5 and R6 are each independently selected from hydrogen, halogen and C1-C4 alkyl;
each R7 independently represents halogen, nitro, cyano, 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 cyano, halogen, C1-C3 alkyl and C1-C3 alkoxy, 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;
or a salt, enantiomer or N-oxide thereof.

### Claim 2 (depends on 1)

The compound according to claim 1, wherein R1 is hydrogen, halogen, methyl or cyano.

### Claim 3 (depends on 1)

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

### Claim 4 (depends on 1)

The compound according to claim 1, wherein R4 is hydrogen, C1-C4 haloalkyl, C2-C4 haloalkenyl, C1-C4 alkyl, C3-C5 cycloalkyl, C2-C5 alkenyl, C3-C5 cycloalkenyl or C2-C4 alkynyl, wherein the cycloalkyl and cycloalkenyl may be optionally substituted with 1 to 3 substituents independently selected from fluoro, chloro, cyano, methyl and C1-C2 alkoxy.

### Claim 5 (depends on 1)

The compound according to claim 1, wherein R5 and R6 are each independently selected from hydrogen, fluoro, chloro, methyl and ethyl.

### Claim 6 (depends on 1)

The compound according to claim 1, wherein each R7 independently represents halogen, nitro, cyano, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C5 cycloalkyl, C1-C4 alkoxy, C3-C4 alkenyloxy, C3-C4 alkynyloxy or C1-C4 alkylthio, wherein the alkyl, cycloalkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy and alkylthio may be optionally substituted with 1 to 2 substituents independently selected from cyano, C1-C3 alkyl, C1-C3 alkoxy, fluoro and chloro or 1 to 3 substituents independently selected from fluoro and chloro; n is 0, 1, 2, 3 or 4.

### Claim 7 (depends on 1)

The compound according to claim 1, wherein R11 is hydrogen, fluoro, chloro or methyl.

### Claim 8 (depends on 1)

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

### Claim 9 (depends on 1)

The compound according to claim 1, wherein R2 and R3 are each independently hydrogen, fluoro, chloro or methyl.

### Claim 10 (depends on 1)

The compound according to claim 1, wherein R1 is hydrogen, halogen, methyl or cyano; R2 and R3 are each independently hydrogen, halogen or methyl; R4 is hydrogen, C1-C4 haloalkyl, C2-C4 haloalkenyl, C1-C4 alkyl, C3-C5 cycloalkyl, C2-C5 alkenyl, C3-C5 cycloalkenyl or C2-C4 alkynyl, wherein the cycloalkyl and cycloalkenyl may be optionally substituted with 1 to 3 substituents independently selected from fluoro, chloro, cyano, methyl and C1-C2 alkoxy; R5 and R6 are each independently selected from hydrogen, fluoro, chloro, methyl and ethyl; each R7 independently represents halogen, nitro, cyano, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C5 cycloalkyl, C1-C4 alkoxy, C3-C4 alkenyloxy, C3-C4 alkynyloxy or C1-C4 alkylthio, wherein the alkyl, cycloalkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy and alkylthio may be optionally substituted with 1 to 2 substituents independently selected from cyano, C1-C3 alkyl, C1-C3 alkoxy, fluoro and chloro or 1 to 3 substituents independently selected from fluoro and chloro; n is 0, 1, 2, 3 or 4; and R11 is hydrogen, fluoro, chloro or methyl; or a salt, enantiomer or N-oxide thereof.

### Claim 11 (depends on 1)

The compound according to claim 1, wherein R1 is hydrogen, fluoro, chloro or methyl; R2 and R3 are each independently hydrogen, fluoro, chloro or methyl; R4 is C1-C3 haloalkyl, C2-C3 haloalkenyl, C1-C4 alkyl, cyclopropyl, cyclobutyl or C2-C4 alkenyl, wherein the cyclopropyl and cyclobutyl may be optionally substituted with 1 to 2 substituents independently selected from fluoro, chloro, cyano, methyl and methoxy; R5 and R6 are each independently selected from hydrogen, fluoro and methyl;
each R7 independently represents fluoro, chloro, bromo, C1-C3 alkyl, C3-C5 cycloalkyl, C1-C2 alkoxy or C1-C2 alkylthio, wherein the alkyl, cycloalkyl, alkoxy and alkylthio may be optionally substituted with 1 to 2 substituents independently selected from C1-C2 alkyl, C1-C2 alkoxy and fluoro or 1 to 3 fluoro substituents; n is 0, 1, 2 or 3; and R11 is hydrogen, fluoro or chloro; or a salt, enantiomer or N-oxide thereof.

### Claim 12 (depends on 1)

The compound according to claim 1, wherein wherein R1 is hydrogen, fluoro or methyl; R2 and R3 are each independently hydrogen, fluoro or methyl; R4 is C1-C2 haloalkyl, C2-C3 haloalkenyl, ethyl, isopropyl, tert-butyl, sec-butyl, cyclopropyl, cyclobutyl or C2-C4 alkenyl, wherein the cyclopropyl and cyclobutyl may be optionally substituted with 1 to 2 substituents independently selected from fluoro, chloro, methyl and methoxy; R5 and R6 are each independently selected from hydrogen and fluoro; each R7 independently represents fluoro, chloro, C1-C2 alkyl, cyclopropyl, or C1-C2 alkoxy, wherein the alkyl, cyclopropyl and alkoxy may be optionally substituted with 1 to 2 substituents independently selected from methyl, methoxy and fluoro or 1 to 3 fluoro substituents; n is 0, 1 or 2; and Ru is hydrogen; or a salt, enantiomer or N-oxide thereof.

### Claim 13 (depends on 1)

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

### Claim 14 (depends on 13)

The composition according to claim 13, wherein the composition further comprises at least one additional active ingredient and/or a diluent.

### Claim 15 (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.