Microbiocidal quinoline (thio)carboxamide derivatives

Patent metadata

Field	Value
Publication number	US-11185074-B2
Application number	US-201816645398-A
Country	US
Kind code	B2
Filing date	Sep 11, 2018
Priority date	Sep 13, 2017
Publication date	Nov 30, 2021
Grant date	Nov 30, 2021

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 or cyano;
R 2 is hydrogen, methyl or halogen;
R 3 and R 4 are each independently selected from hydrogen, halogen and methyl;
R 5 is C 1 -C 5 alkyl, C 2 -C 5 alkenyl, C 3 -C 5 cycloalkyl(C 1 -C 2 )alkyl or C 3 -C 6 cycloalkyl,
wherein the alkyl, alkenyl and cycloalkyl groups may be optionally substituted with 1 to 3 substituents independently selected from halogen, cyano, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy and C 1 -C 3 alkylthio;
R 6 is hydrogen, cyano or C 1 -C 4 alkyl, wherein the alkyl may be optionally substituted with 1 to 3 substituents independently selected from halogen and C 1 -C 3 alkoxy;
A is a direct bond or CR 8 R 9 ;
R 7 is CF 3 , C 2 -C 5 alkyl, C 3 -C 7 cycloalkyl, C 2 -C 5 alkenyl, C 4 -C 7 cycloalkenyl, wherein the alkyl, cycloalkyl, alkenyl and cycloalkenyl may be optionally substituted with one or more substituents independently selected from halogen, cyano, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 alkylthio, C 1 -C 3 haloalkoxy, C 1 -C 3 haloalkylthio, C 3 -C 7 cycloalkyl and phenyl (which itself may be optionally substituted with 1 to 3 substituents independently selected from halogen, cyano, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 alkylthio, C 1 -C 3 haloalkoxy, C 1 -C 3 haloalkylthio and C 3 -C 5 cycloalkyl); and
R 8 and R 9 are each independently selected from hydrogen, fluoro and methyl; or a salt, enantiomer or N-oxide thereof.

2. The compound, or a salt, enantiomer or N-oxide thereof, according to claim 1 wherein R 1 is hydrogen, fluoro, chloro, methyl or cyano.

3. The compound, or a salt, enantiomer or N-oxide thereof, according to claim 1 wherein R 2 is hydrogen, methyl, chloro or fluoro.

4. The compound, or a salt, enantiomer or N-oxide thereof, according to claim 1 wherein R 3 and R 4 are each independently selected from hydrogen and methyl.

5. The compound, or a salt, enantiomer or N-oxide thereof, according to claim 1 wherein R 5 is C 1 -C 5 alkyl, C 2 -C 4 alkenyl, C 3 -C 5 cycloalkyl-CH 2 - or C 3 -C 5 cycloalkyl, wherein the alkyl, alkenyl and cycloalkyl groups may be optionally substituted with 1 to 3 substituents independently selected from fluoro, chloro and C 1 -C 3 alkyl.

6. The compound, or a salt, enantiomer or N-oxide thereof, according to claim 1 wherein R 6 is hydrogen, or C 1 -C 3 alkyl, wherein the alkyl may be optionally substituted with a methoxy group.

7. The compound, or a salt, enantiomer or N-oxide thereof, according to claim 1 wherein R 7 is CF 3 , C 2 -C 5 alkyl, C 3 -C 7 cycloalkyl, C 2 -C 5 alkenyl, C 4 -C 7 cycloalkenyl, wherein the alkyl, cycloalkyl, alkenyl and cycloalkenyl may be optionally substituted with one or more substituents independently selected from fluoro, chloro, cyano, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 3 -C 4 cycloalkyl and phenyl (which itself may be optionally substituted with 1 to 3 substituents independently selected from fluoro, chloro, methyl and trifluoromethyl).

8. The compound, or a salt, enantiomer or N-oxide thereof, according to claim 1 wherein A is a direct bond or CH 2 .

9. The compound according to claim 1 wherein X is O or S; R 1 is hydrogen, fluoro, chloro or methyl; R 2 is hydrogen, chloro or fluoro; R 3 is methyl and R 4 is hydrogen; or R 3 is hydrogen and R 4 is methyl; or R 3 is hydrogen and R 4 is hydrogen; R 5 is C 1 -C 5 alkyl, C 2 -C 4 alkenyl, C 3 -C 4 cycloalkyl-CH 2 - or C 3 -C 5 cycloalkyl, wherein the alkyl, alkenyl and cycloalkyl groups may be optionally substituted with 1 to 3 substituents independently selected from fluoro, chloro and methyl; R 6 is hydrogen or methyl, wherein the methyl may be optionally substituted with a methoxy group; A is a direct bond or CH 2 ; R 7 is CF 3 , C 2 -C 4 alkyl, C 3 -C 6 cycloalkyl, C 2 -C 4 alkenyl, C 4 -C 6 cycloalkenyl, wherein the alkyl, cycloalkyl, alkenyl and cycloalkenyl may be optionally substituted with 1 to 3 substituents independently selected from fluoro, chloro, methyl, trifluoromethyl and cyclopropyl and/or one phenyl; or a salt, enantiomer or N-oxide thereof.

10. The compound, or a salt, enantiomer or N-oxide thereof, according to claim 1 wherein A is CH 2 .

11. The compound according to claim 1 wherein X is O or S; R 1 is fluoro, chloro or methyl; R 2 is hydrogen or fluoro; R 3 and R 4 are both hydrogen; R 5 is trifluoroethyl, ethyl, isopropyl, iso-butyl, tert-butyl, neo-pentyl, C 2 -C 4 alkenyl or cyclopropyl-CH 2 -, wherein the ethyl, isopropyl, iso-butyl, alkenyl and cyclopropyl groups may be optionally substituted with 1 to 3 substituents independently selected from fluoro and chloro and/or one methyl group; R 6 is methyl; A is CH 2 ; R 7 is CF 3 , ethyl, isopropyl, tert-butyl, C 2 -alkenyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentenyl or cyclohexenyl, wherein the ethyl, isopropyl, alkenyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentenyl and cyclohexenyl may be optionally substituted with 1 to 3 substituents independently selected from fluoro and chloro and/or one or two methyl groups; or a salt, enantiomer or N-oxide thereof.

12. The compound, or a salt, enantiomer or N-oxide thereof, according to claim 1 wherein X is O.

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

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

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

16. A compound selected from the group consisting of:

17. The compound of claim 16 , wherein the compound is selected from the group
consisting of:

Assignees

• Syngenta Participations Ag

Inventors

• Bou Hamdan Farhan
• Weiss Matthias
• Quaranta Laura

Classifications

• C07D215/54

  attached in position 3 · CPC title

• C07D215/16 Primary

  with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms · CPC title

• A01N43/42 Primary

  condensed with carbocyclic rings · CPC title