Microbiocidal quinoline (thio)carboxamide derivatives

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.

What is claimed is: 
     
         1 . A compound of formula (I) 
       
         
           
           
               
               
           
         
         wherein 
         X is O or S; 
         R 1  is hydrogen, halogen, methyl or cyano; 
         R 2  and R 3  are each independently selected from hydrogen, halogen, methoxy and methyl; 
         R 4  is hydrogen, C 1 -C 4  alkyl, C 1 -C 2  haloakyl, C 2 -C 4  alkenyl or C 3 -C 6  cycloalkyl, wherein the alkyl, alkenyl 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  is hydrogen, cyano or C 1 -C 4  alkyl; 
         R 6  is C 1 -C 5  alkyl, C 3 -C 7  cycloalkyl, C 3 -C 5  alkenyl, C 3 -C 6  cycloalkenyl, C 3 -C 5  alkynyl, a C 5 -C 10  saturated or partially unsaturated bicyclic carbocycle, aryl, aryl(C 1 -C 4 )alkyl, a saturated or partially unsaturated heterocycle or heteroaryl, wherein the alkyl, cycloalkyl, alkenyl, cycloalkenyl, carbocycle, alkynyl, may be optionally substituted with one or more substituents independently selected from halogen, cyano, C 1 -C 3  alkyl, C 1 -C 3  alkoxy, C 1 -C 3  alkylthio, C 1 -C 3  haloalkoxy, C 1 -C 3  haloalkylthio, C 3 -C 5  cycloalkyl or phenyl, and wherein the aryl, heterocycle or heteroaryl may be optionally substituted with one or more substituents independently selected from halogen, cyano, C 1 -C 3  alkyl, C 1 -C 3  alkoxy, C 1 -C 3  alkylthio, C 1 -C 3  haloalkoxy, C 1 -C 3  haloalkylthio or C 3 -C 5  cycloalkyl; and 
         R 11  is hydrogen, methyl or halogen; or a salt, enantiomer or N-oxide thereof. 
       
     
     
         2 . A compound, or a salt, enantiomer or N-oxide thereof, according to  claim 1  wherein R 1  is hydrogen, fluoro, chloro, bromo or methyl. 
     
     
         3 . A compound, or a salt, enantiomer or N-oxide thereof, according to  claim 1  wherein R 2  and R 3  are each independently selected from hydrogen, chloro and methyl. 
     
     
         4 . A compound, or a salt, enantiomer or N-oxide thereof, according to  claim 1  wherein R 4  is C 1 -C 4  alkyl, C 1 -C 2  haloakyl, C 2 -C 4  alkenyl or C 3 -C 6  cycloalkyl, wherein the alkyl, alkenyl and cycloalkyl may be optionally substituted with 1 to 3 substituents independently selected from fluoro, cyano, methyl, methoxy and methylthio. 
     
     
         5 . A compound, or a salt, enantiomer or N-oxide thereof, according to  claim 1  wherein R 5  is hydrogen or C 1 -C 3  alkyl. 
     
     
         6 . A compound, or a salt, enantiomer or N-oxide thereof, according to  claim 1  wherein R 6  is C 1 -C 5  alkyl, C 3 -C 7  cycloalkyl, C 3 -C 5  alkenyl, C 3 -C 6  cycloalkenyl, C 3 -C 5  alkynyl, a C 5 -C 10  saturated bicyclic carbocycle, a C 5 -C 10  partially unsaturated bicyclic carbocycle, phenyl, phenyl(C 1 -C 3 )alkyl, oxetanyl, tetrahydrofuranyl, tetrahydropyranyl, pyridinyl, thiophenyl, thiazolyl, oxazolyl or pyrazolyl, wherein the alkyl, cycloalkyl, alkenyl, cycloalkenyl, carbocycle and alkynyl may be optionally substituted with one or more substituents independently selected from fluoro, chloro, cyano, methyl, methoxy, methylthio; C 1 -C 2  fluoroalkoxy, C 1 -C 2  fluoroalkylthio, cyclopropyl and cyclobutyl, and wherein the phenyl, oxetanyl, tetrahydrofuranyl, tetrahydropyranyl, pyridinyl, thiophenyl, thiazolyl, oxazolyl and pyrazolyl may be optionally substituted with one or more substituents independently selected from fluoro, chloro, cyano, methyl, methoxy, methylthio; C 1 -C 2  fluoroalkoxy, C 1 -C 2  fluoroalkylthio, cyclopropyl and cyclobutyl. 
     
     
         7 . A compound, or a salt, enantiomer or N-oxide thereof, according to  claim 1  wherein R 11  is hydrogen, methyl, chloro or fluoro. 
     
     
         8 . A compound, or a salt, enantiomer or N-oxide thereof, according to  claim 1  wherein R 1  is fluoro, chloro or methyl; R 2  and R 3  are each independently selected from hydrogen and methyl; R 4  is C 1 -C 4  alkyl, C 1 -haloakyl, C 2 -C 4  alkenyl or C 3 -C 4  cycloalkyl, wherein the alkyl, alkenyl and cycloalkyl may be optionally substituted with 1 to 3 substituents independently selected from fluoro, cyano and methyl; R 5  is hydrogen, methyl or ethyl; and R 11  is hydrogen or fluoro. 
     
     
         9 . A compound, or a salt, enantiomer or N-oxide thereof, according to  claim 1  wherein R 6  is C 1 -C 5  alkyl, C 3 -C 7  cycloalkyl, C 3 -C 4  alkenyl, C 3 -C 6  cycloalkenyl, a C 6 -C 8  saturated bicyclic carbocycle, a C 6 -C 8  partially unsaturated bicyclic carbocycle, phenyl, phenyl(C 1 -C 3 )alkyl, pyridinyl, thiophenyl, thiazolyl, oxazolyl and pyrazolyl wherein the alkyl, cycloalkyl, alkenyl, cycloalkenyl and carbocycle may be optionally substituted with 1 to 3 substituents independently selected from fluoro, chloro, cyano, methyl, methoxy, methylthio, cyclopropyl and cyclobutyl, and wherein the phenyl, pyridinyl, thiophenyl, thiazolyl, oxazolyl and pyrazolyl may be optionally substituted with 1 to 3 of substituents independently selected from fluoro, chloro, cyano, methyl and cyclopropyl. 
     
     
         10 . A compound according to  claim 1  wherein X is O or S; R 1  is fluoro, chloro or methyl; R 2  is methyl and R 3  is hydrogen; or R 2  is hydrogen and R 3  is methyl; or R 2  is hydrogen and R 3  is hydrogen; R 4  is C 1 -C 4  alkyl, C 1 -haloakyl, C 2 -C 4  alkenyl or C 3 -C 4  cycloalkyl, wherein the alkyl, alkenyl and cycloalkyl may be optionally substituted with 1 to 3 substituents independently selected from fluoro, cyano and methyl; R 5  is hydrogen, methyl or ethyl; R 6  is C 1 -C 5  alkyl, C 3 -C 7  cycloalkyl, C 3 -C 4  alkenyl, C 3 -C 6  cycloalkenyl, a C 6 -C 8  saturated bicyclic carbocycle, a C 6 -C 8  partially unsaturated bicyclic carbocycle, phenyl, phenyl(C 1 -C 3 )alkyl, pyridinyl, thiophenyl, thiazolyl, oxazolyl and pyrazolyl wherein the alkyl, cycloalkyl, alkenyl, cycloalkenyl and carbocycle may be optionally substituted with 1 to 3 substituents independently selected from fluoro, chloro, cyano, methyl, methoxy, methylthio, cyclopropyl and cyclobutyl, and wherein the phenyl, pyridinyl, thiophenyl, thiazolyl, oxazolyl and pyrazolyl may be optionally substituted with 1 to 3 of substituents independently selected from fluoro, chloro, cyano, methyl and cyclopropyl; and R 11  is hydrogen or fluoro; or a salt, enantiomer or N-oxide thereof. 
     
     
         11 . A compound according to  claim 1  wherein X is O or S; R 1  is fluoro or methyl; R 2  and R 3  are both hydrogen; R 4  is C 1 -C 4  alkyl, trifluoromethyl, C 2 -C 4  alkenyl or C 3 -C 4  cycloalkyl, wherein the alkyl, alkenyl and cycloalkyl may be optionally substituted with 1 to 3 fluorine atoms or a methyl; R 5  is methyl; R 6  is C 3 -C 5  alkyl, C 3 -C 7  cycloalkyl, C 3 -C 4  alkenyl, a C 6 -C 8  saturated bicyclic carbocycle, phenyl or phenyl(C 1 -C 2 )alkyl, wherein the alkyl, cycloalkyl, alkenyl and carbocycle may be optionally substituted with 1 to 3 substituents independently selected from fluoro and methyl or 1 or 2 substituents independently selected from cyclopropyl and cyclobutyl, and wherein the phenyl may be optionally substituted with 1 to 2 substituents independently selected from fluoro, chloro and methyl; and R 11  is hydrogen; or a salt, enantiomer or N-oxide thereof. 
     
     
         12 . A 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 in  claim 1 . 
     
     
         14 . A 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 any of  claims 1 - 12  or a composition comprising a fungicidally effective amount of a compound of formula (I) as defined in  claim 1 .