Microbiocidal thiazole derivatives

1. A compound of formula (I):

wherein,

R 1 is halogen, cyano, C 1 -C 6 alkyl or C 1 -C 6 alkoxy, wherein C 1 -C 6 alkyl and C 1 -C 6 alkoxy are optionally substituted with 1 to 3 groups represented by R 6 ;

R 2 and R 4 are independently hydrogen, C 1 -C 6 alkyl, C 1 -C 6 alkoxy or C 3 -C 6 cycloalkyl,

wherein C 1 -C 6 alkyl, C 1 -C 6 alkoxy and C 3 -C 6 cycloalkyl are optionally substituted with 1 to 3 groups represented by R 6 ;

R 3 is halogen, C 1 -C 6 alkyl, C 1 -C 6 alkoxy or C 3 -C 6 cycloalkyl, wherein C 1 -C 6 alkyl, C 1 -C 6 alkoxy and C 3 -C 6 cycloalkyl are optionally substituted with 1 to 3 groups represented by R 6 ;

R 5 is C 1 -C 10 alkyl, C 3 -C 10 cycloalkyl, C 3 -C 10 cycloalkenyl, C 3 -C 10 cycloalkylC 1 -C 2 alkyl, C 2 -C 10 alkenyl, C 2 -C 10 alkynyl, aryl, heteroaryl wherein the heteroaryl is a 5- or 6-membered aromatic monocyclic ring comprising 1, 2, 3 or 4 heteroatoms individually selected from nitrogen, oxygen and sulfur, heterocyclyl wherein the heterocyclyl is a 4-, 5- or 6-membered non-aromatic monocyclic ring comprising 1, 2 or 3 heteroatoms individually selected from nitrogen, oxygen and sulfur, heterocyclylC 1 -C 2 alkyl, or a 5- to 10-membered non-aromatic annulated or spirocyclic carbobicyclyl ring system optionally comprising 1, 2, 3, 4 or 5 heteroatoms individually selected from nitrogen, oxygen and sulfur, and optionally bonded to the rest of the molecule through a C 1 -C 2 alkylene linker;

wherein any of said C 1 -C 10 alkyl, C 3 -C 10 cycloalkyl, C 1 -C 10 cycloalkenyl, C 2 -C 10 alkenyl and C 2 -C 10 alkynyl moieties are optionally substituted with 1 to 4 groups represented by R 7 or 1 group represented by R 8 ; or

wherein any of said aryl, heteroaryl and heterocyclyl moieties are optionally substituted with 1 to 3 groups represented by R 9 or 1 group represented by R 10 , or are optionally substituted with 1 or 2 groups represented by R 9 and 1 group represented by R 10 ; or

wherein the annulated or spirocyclic carbobicyclyl ring system is optionally substituted with 1 to 3 groups represented by R 7 , or the annulated carbobicyclyl ring system is optionally substituted by C 3 -C 6 cycloalkyl to form a spirocyclyl moiety,

R 6 is independently selected from halogen, cyano, hydroxyl, C 1 -C 6 alkoxy, and C 3 -C 6 cycloalkyl;

R 7 is independently selected from halogen, cyano, hydroxyl, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 alkoxyC 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkylC 1-2 alkyl, C 2 -C 6 acyl, C 2 -C 6 acyloxy, C 2 -C 6 acyloxyC 1 -C 6 alkyl and C 1 -C 4 alkoxycarbonyl;

wherein when R 7 is C 3 -C 6 cycloalkylC 1-2 alkyl, the C 3 -C 6 cycloalkyl moiety is optionally substituted with 1 or 2 groups independently selected from halogen and C 1 -C 6 alkyl;

R 8 is aryl, aryloxy, arylC 1 -C 6 alkyl, heteroaryl wherein the heteroaryl is a 5- or 6-membered aromatic monocyclic ring comprising 1, 2, 3 or 4 heteroatoms individually selected from nitrogen, oxygen and sulfur, heteroaryloxy or heteroarylC 1 -C 6 alkyl, wherein aryl and heteroaryl are optionally substituted with 1 to 3 groups represented by R 9 or 1 group represented by R 10 ;

R 9 is independently selected from halogen, cyano, hydroxyl, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 alkylthio, C 2 -C 6 alkenyl, C 2 -C 6 alkenyloxy, C 2 -C 6 alkynyl, C 2 -C 6 alkynyloxy,

wherein C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 alkylthio, C 2 -C 6 alkenyl, C 2 -C 6 alkenyloxy, C 2 -C 6 alkynyl, C 2 -C 6 alkynyloxy, are optionally substituted with 1 to 3 groups represented by R 11 ;

R 10 is selected from C 3 -C 6 cycloalkyl, C 3 -C 8 cycloalkoxy, C 3 -C 6 cycloalkylthio, aryl, aryloxy, arylthio, arylC 1 -C 6 alkyl, heteroaryl wherein the heteroaryl is a 5- or 6-membered aromatic monocyclic ring comprising 1, 2, 3 or 4 heteroatoms individually selected from nitrogen, oxygen and sulfur, heteroaryloxy, heteroarylthio, heteroarylC 1 -C 6 alkyl, heterocyclyl wherein the heterocyclyl is a 4-, 5- or 6-membered non-aromatic monocyclic ring comprising 1, 2 or 3 heteroatoms individually selected from nitrogen, oxygen and sulfur, heterocyclyloxy, heterocyclylthio or heterocyclylC 1 -C 6 alkyl,

wherein C 3 -C 6 cycloalkyl, C 3 -C 8 cycloalkoxy, C 3 -C 6 cycloalkylthio, aryl, aryloxy, arylthio, arylC 1 -C 6 alkyl, heteroaryl, heteroaryloxy, heteroarylthio, heteroarylC 1 -C 6 alkyl, heterocyclyl, heterocyclyloxy, heterocyclylthio and heterocyclylC 1 -C 6 alkyl are optionally substituted with 1 to 3 groups represented by R 11 ;

R 11 is independently selected from halogen and methyl;

X is N;

or a salt or an N-oxide thereof.

2. The compound according to claim 1 , wherein R 1 is halogen, cyano, methyl, trifluoromethyl, methoxy or trifluoromethoxy.

3. The compound according to claim 1 , wherein R 2 is hydrogen.

4. The compound according to claim 1 , wherein R 3 is halogen or C 1 -C 4 alkyl.

5. The compound according to claim 1 , wherein R 4 is hydrogen.

6. The compound according to claim 1 , wherein:

R 5 is C 1 -C 7 alkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkylC 1 -C 2 alkyl, C 3 -C 6 cycloalkenyl, C 2 -C 6 alkenyl, C 2 -C 7 alkynyl, phenyl, heteroaryl wherein the heteroaryl is a 5- or 6-membered aromatic monocyclic ring comprising 1, 2, 3 or 4 heteroatoms individually selected from nitrogen, oxygen and sulfur, heterocyclyl wherein the heterocyclyl is a 4-, 5- or 6-membered non-aromatic monocyclic ring comprising 1, 2 or 3 heteroatoms individually selected from nitrogen, oxygen and sulfur, heterocyclylC 1 -C 2 alkyl, or a 5- to 10-membered non-aromatic annulated or spirocyclic carbobicyclyl ring system optionally comprising 1, 2 or 3 heteroatoms individually selected from nitrogen, oxygen and sulfur, and optionally bonded to the rest of the molecule through a C 1 -C 2 alkylene linker;

wherein any of said C 1 -C 7 alkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkenyl, C 2 -C 6 alkenyl and C 2 -C 7 alkynyl moieties are optionally substituted with 1 to 4 groups represented by R 7 or 1 group represented by R 8 ; or

wherein any of said phenyl, heteroaryl and heterocyclyl moieties are optionally substituted with 1 to 3 groups represented by R 9 or 1 group represented by R 10 , or are optionally substituted with 1 or 2 groups represented by R 9 and 1 group represented by R 10 ; or

wherein the annulated or spirocyclic carbobicyclyl ring is optionally substituted with 1 to 3 groups represented by R 7 , or the annulated carbobicyclyl ring system is optionally substituted by C 3 -C 6 cycloalkyl to form a spirocyclyl moiety.

7. The compound according to claim 1 , wherein:

R 5 is C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, C 3 -C 5 cycloalkylC 1-2 alkyl, C 2 -C 6 alkynyl, phenyl, heterocyclyl, wherein the heterocyclyl is a 4- or 6-membered non-aromatic monocyclic ring comprising I oxygen atom, heterocyclylC 1 alkyl, or a 5- to 9-membered non-aromatic annulated or spirocyclic carbobicyclyl ring system optionally comprising 1 oxygen atom, and optionally bonded to the rest of the molecule through a methylene linker;

wherein any of said C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl and C 2 -C 6 alkynyl, moieties are optionally substituted with 1 to 4 groups represented by R 7 or 1 group represented by R 8 ; or

wherein any of said phenyl or heterocyclyl moieties are optionally substituted with 1 or 2 groups represented by R 9 or 1 group represented by R 10 , or are optionally substituted with 1 or 2 groups represented by R 9 and 1 group represented by R 10 ; or

wherein the annulated or spirocyclic carbobicyclyl ring system is optionally substituted with 1 or 2 groups represented by R 7 , or the annulated carbobicyclyl ring system is optionally substituted by C 4 -C 5 cycloalkyl to form a spirocycle.

8. The compound according to claim 1 , wherein:

R 5 is C 1 -C 6 alkyl, C 2 -C 6 alkynyl, C 3 -C 6 cycloalkyl or C 3 -C 6 cycloalkylC 1 -C 2 alkyl, wherein any of the C 1 -C 6 alkyl, C 2 -C 6 alkynyl and C 3 -C 6 cycloalkyl moieties are optionally substituted with 1 to 4 groups represented by R 7 or 1 group represented by R 8 , wherein R 7 is independently selected from halogen, cyano, hydroxyl, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkoxyC 1 -C 4 alkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkylC 1-2 alkyl, and C 1 -C 3 alkoxycarbonyl, and R 8 is phenyl, benzyl or isoxazole optionally substituted with 1 to 3 groups represented by R 9 or 1 group represented by R 10 , and wherein

R 9 is halogen and R 10 is phenyl optionally substituted by 1 to 3 groups represented by R 11 which is halogen;

or

R 5 is phenyl, oxetanyl, tetrahydrofuranyl or tetrahydropyranyl each optionally substituted with 1 to 3 groups represented by R 9 or 1 group represented by R 10 , or 1 or 2 groups represented by R 9 and 1 group represented by R 10 , wherein

R 9 is independently selected from halogen and C 1 -C 4 alkyl, and R 10 is selected from phenyl, benzyl or C 6 -C 8 cycloalkoxy each optionally substituted by 1 to 3 groups represented by R 11 ;

or

R 5 is an annulated or spirocyclic ring system selected from:

each optionally substituted by 1 to 3 groups represented by R 7 independently selected from C 1 -C 4 alkyl and C 2 -C 4 acyloxyC 1 -C 4 alkyl.

9. The compound according to claim 1 , wherein:

R 5 is C 1 -C 4 alkyl optionally substituted by 1 group represented by R 7 selected from C 3 -C 6 cycloalkyl; or

R 5 is an annulated or spirocyclic ring system selected from:

each optionally substituted by 1 to 3 groups represented by R 5 independently selected from C 1 -C 4 alkyl.

10. The compound according to claim 9 , wherein R 5 is an annulated or spirocyclic ring system substituted by 1 to 3 groups represented by R 7 , and R 7 is methyl.

11. An agrochemical composition comprising a fungicidally effective amount of a compound of formula (I) according to claim 1 .

12. The composition according to claim 11 , further comprising at least one additional active ingredient and/or an agrochemically-acceptable diluent or carrier.

13. A method of controlling or preventing infestation of useful plants by phytopathogenic microorganisms, wherein a fungicidally effective amount of a compound of formula (I) according to claim 1 , or a composition comprising this compound as active ingredient, is applied to the plants, to parts thereof or the locus thereof.

14. The compound according to claim 1 , R 5 is substituted by R 7 or 1 group represented by R 8 .

15. The compound according to claim 14 , wherein R S is C 1 -C 10 alkyl, C 3 -C 10 cycloalkyl, C 3 -C 10 cycloalkenyl, C 3 -C 10 cycloalkylC 1 -C 2 alkyl, C 2 -C 10 alkenyl, or C 2 -C 10 alkynyl.

16. The compound according to claim 15 , wherein R 1 is halogen.

17. The compound according to claim 16 , wherein R 5 is cyclobutyl.

18. The compound according to claim 1 , R 5 is an annulated or spirocyclic ring system selected from:

each optionally substituted by 1 to 3 groups represented by R 7 independently selected from C 1 -C 4 alkyl and C 2 -C 4 acyloxyC 1 -C 4 alkyl.

19. The compound according to claim 1 , wherein R 4 is C 1 -C 6 alkyl, C 1 -C 6 alkoxy or C 3 -C 6 cycloalkyl, wherein C 1 -C 6 alkyl, C 1 -C 6 alkoxy and C 3 -C 6 cycloalkyl are optionally substituted with 1 to 3 groups represented by R 6 .