Microbiocidal quinoline (thio)carboxamide derivatives

Patent metadata

Field	Value
Publication number	US-10477864-B2
Application number	US-201716083844-A
Country	US
Kind code	B2
Filing date	Mar 7, 2017
Priority date	Mar 10, 2016
Publication date	Nov 19, 2019
Grant date	Nov 19, 2019

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.

First claim

The invention claimed is:

1. A compound of formula (I):

wherein
X is O or S;
R 1 is hydrogen, halogen, methyl, methoxy or cyano;
R 2 and R 3 are each independently hydrogen, halogen or methyl;
R 4 is hydrogen, cyano, C 1 -C 4 alkyl, or C 3 -C 4 cycloalkyl, wherein the alkyl and cycloalkyl, may be optionally substituted with 1 to 3 substituents independently selected from halogen, cyano, C 1 -C 3 alkyl, C 1 -C 3 alkoxy and C 1 -C 3 alkylthio;
R 5 and R 6 are each independently selected from hydrogen, halogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy and C 1 -C 4 alkylthio; or
R 5 and R 6 together with the carbon atom to which they are attached represent C═O, C═NOR c , C 3 -C 5 cycloalkyl or C 2 -C 5 alkenyl, wherein the cycloalkyl and alkenyl may be optionally substituted with 1 to 3 substituents independently selected from halogen, cyano, C 1 -C 3 alkyl, C 1 -C 3 alkoxy and C 1 -C 3 alkylthio;
R 7 is hydrogen, C 1 -C 5 alkyl, C 3 -C 5 cycloalkyl, C 2 -C 5 alkenyl, C 3 -C 5 cycloalkenyl, or C 2 -C 5 alkynyl, wherein the alkyl, cycloalkyl, alkenyl, alkynyl, cycloalkenyl may be optionally substituted with 1 to 4 substituents independently selected from halogen, cyano, C 1 -C 3 alkyl, C 1 -C 3 alkoxy, hydroxyl and C 1 -C 3 alkylthio;
R 8 and R 9 are each independently selected from hydrogen, halogen, C 1 -C 4 alkyl and C 1 -C 4 alkoxy; or
R 8 and R 9 together with the carbon atom to which they are attached represent C 3 -C 5 cycloalkyl, wherein the cycloalkyl may be optionally substituted with 1 to 3 substituents independently selected from halogen, cyano, C 1 -C 3 alkyl, C 1 -C 3 alkoxy and C 1 -C 3 alkylthio;
each R 10 independently represents halogen, nitro, cyano, formyl, C 1 -C 5 alkyl, C 2 -C 5 alkenyl, C 2 -C 5 alkynyl, C 3 -C 6 cycloalkyl, C 1 -C 5 alkoxy, C 3 -C 5 alkenyloxy, C 3 -C 5 alkynyloxy, C 1 -C 5 alkylthio, —C(═NOR c )C 1 -C 5 alkyl, or C 1 -C 5 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, C 1 -C 3 alkyl, C 1 -C 3 alkoxy, cyano and C 1 -C 3 alkylthio; n is 0, 1, 2, 3, 4 or 5;
each R c is independently selected from hydrogen, C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 3 -C 4 alkynyl, C 3 -C 4 cycloalkyl(C 1 -C 2 )alkyl and C 3 -C 4 cycloalkyl, wherein the alkyl, cycloalkyl, alkenyl and alkynyl groups may be optionally substituted with 1 to 3 substituents independently selected from halogen and cyano;
R 11 is hydrogen, halogen, methyl, methoxy or cyano;
R 12 and R 13 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 R 1 is hydrogen, R 2 is hydrogen, R 3 is methyl, R 4 is hydrogen, R 5 is hydrogen, R 6 is hydrogen, R 7 is hydrogen, R 8 is hydrogen, R 9 is hydrogen, n is 1, R 10 is 2-methyl, R 11 is fluoro, R 12 is hydrogen, R 13 is hydrogen, and X is O.

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

3. A compound according to claim 1 wherein R 2 and R 3 are each independently hydrogen or methyl.

4. A compound according to claim 1 , wherein R 4 is hydrogen, cyano, C 1 -C 3 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.

5. A compound according to claim 1 , wherein R 5 and R 6 are each independently selected from hydrogen, fluoro, C 1 -C 2 alkyl, C 1 -C 2 alkoxy and C 1 -C 2 alkylthio; or R 5 and R 6 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.

6. A compound according to claim 1 , wherein R 7 is C 1 -C 4 alkyl, C 3 -C 4 cycloalkyl, C 2 -C 4 alkenyl, or C 2 -C 3 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.

7. A compound according to claim 1 wherein R 8 and R 9 are each independently selected from hydrogen, fluoro, C 1 -C 2 alkyl and C 1 -C 2 alkoxy; or R 8 and R 9 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.

8. A compound according to claim 1 wherein each R 10 independently represents halogen, cyano, C 1 -C 3 alkyl, C 2 -C 3 alkenyl, C 2 -C 3 alkynyl, cyclopropyl, methoxy, allyloxy, propargyloxy, or C 1 -C 2 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.

9. A compound according to claim 1 wherein R 11 is hydrogen, fluoro, chloro, methyl or cyano; and R 12 and R 13 are each independently selected from hydrogen, fluoro, methyl and hydroxyl.

10. A compound according to claim 1 wherein X is O or S; R 1 is hydrogen, fluoro, chloro, methyl, or cyano; R 2 and R 3 are each independently hydrogen or methyl; R 4 is hydrogen, cyano, C 1 -C 3 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; R 5 and R 6 are each independently selected from hydrogen, fluoro, C 1 -C 2 alkyl, C 1 -C 2 alkoxy and C 1 -C 2 alkylthio; or R 5 and R 6 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; R 7 is C 1 -C 4 alkyl, C 3 -C 4 cycloalkyl, C 2 -C 4 alkenyl, or C 2 -C 3 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; R 8 and R 9 are each independently selected from hydrogen, fluoro, C 1 -C 2 alkyl and C 1 -C 2 alkoxy; or R 8 and R 9 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 R 10 independently represents halogen, cyano, C 1 -C 3 alkyl, C 2 -C 3 alkenyl, C 2 -C 3 alkynyl, cyclopropyl, methoxy, allyloxy, propargyloxy, or C 1 -C 2 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; R 11 is hydrogen, fluoro, chloro, methyl or cyano; and R 12 and R 13 are each independently selected from hydrogen, fluoro, methyl and hydroxyl; or a salt or N-oxide thereof.

11. A compound according to claim 1 wherein X is 0 or S; R 1 is hydrogen, fluoro, methyl, or cyano; R 2 is hy

Assignees

• Syngenta Participations Ag

Inventors

• Weiss Matthias
• Bou Hamdan Farhan
• Quaranta Laura

Classifications

• A01N43/42 Primary

  condensed with carbocyclic rings · CPC title

• C07D215/54 Primary

  attached in position 3 · CPC title