Microbiocidal oxadiazole derivatives

1. A compound of formula (I):

wherein

n is 1 or 2;

A 1 represents N or CR 1 , wherein R 1 is hydrogen, halogen, methyl, ethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, or difluoromethoxy;

A 2 represents N or CR 2 , wherein R 2 is hydrogen, halogen, methyl, ethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, or difluoromethoxy;

A 3 represents N or CR 3 , wherein R 3 is hydrogen or halogen;

A 4 represents N or CR 4 , wherein R 4 is hydrogen or halogen; and

wherein 0, 1 or 2 of A 1 , A 2 , A 3 and A 4 are N;

R 5 and R 6 are independently selected from hydrogen, C 1-4 alkyl, halogen, cyano, trifluoromethyl and difluoromethyl, or R 5 and R 6 together with the carbon atom they share form a cyclopropyl;

R 7 is hydroxy, C 1-4 alkyl, C 1-4 haloalkyl, C 1-4 alkoxy, hydroxyC 1-4 alkyl, C 1-2 alkoxyC 1-4 alkyl, C 1-2 haloalkoxyC 1-4 alkyl, C 3-6 alkenyl, C 3-4 alkynyl, C 3-6 alkenyloxy, C 3-6 alkynyloxy, C 3-6 haloalkenyl, C 3-6 haloalkenyloxy, C 1-4 alkylcarbonyloxy, C 1-4 haloalkylcarbonyloxy, C 1-4 alkoxycarbonyloxy, C 1-4 alkylcarbonyloxyC 1-4 alkyl, C 1-4 haloalkylcarbonyloxyC 1-4 alkyl or C 1-4 alkoxycarbonyloxyC 1-4 alkyl; or

R 7 is C 3-6 cycloalkyl, C 3-6 cycloalkylC 1-2 alkyl, C 3-6 cycloalkylC 1-2 alkoxy, phenylC 1-2 alkyl, phenylC 1-2 alkoxy, heteroaryl, heteroarylC 1-2 alkyl, heteroarylC 1-2 alkoxy, heterocyclyl, heterocyclylC 1-2 alkyl, heterocyclylC 1-2 alkoxy, C 3-6 cycloalkylcarbonyloxy, heterocyclylcarbonyloxy, phenylcarbonyloxy, C 3-6 cycloalkylcarbonyloxyC 1-4 alkyl, heterocyclylcarbonyloxyC 1-4 alkyl or phenylcarbonyloxyC 1-4 alkyl, wherein the heteroaryl moiety is a 5- or 6-membered monocyclic aromatic ring which comprises 1, 2, 3 or 4 heteroatoms individually selected from N, O and S, the heterocyclyl moiety is a 4- to 6-membered non-aromatic ring which comprises 1 or 2 heteroatoms individually selected from N, O and S, and wherein any of said cycloalkyl, phenyl, heteroaryl and heterocyclyl moieties are optionally substituted by 1 or 2 substituents selected from cyano, fluoro, chloro, bromo, methyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, or difluoromethoxy;

R 8 is —NR 14 R 15 , wherein R 14 is hydrogen, cyano, C 1-6 alkyl, C 1-6 alkoxy, C 2-6 alkenyl, C 2-6 alkynyl, C 3-6 alkenyloxy, C 3-6 alkynyloxy, cyanoC 1-6 alkyl, C 1-6 haloalkyl, C 1-6 haloalkenyl, hydroxyC 1-6 alkyl, C 1-4 alkoxyC 1-6 alkyl, C 1-4 haloalkoxyC 1-6 alkyl, C 1-4 alkoxyC 1-4 alkoxyC 1-6 alkyl, aminoC 1-6 alkyl, N—C 1-4 alkylaminoC 1-6 alkyl, C 1-6 alkylcarbonylC 1-6 alkyl, C 1-6 alkylcarbonylC 2-6 alkenyl, C 1-6 alkoxycarbonylC 1-6 alkyl, C 1-6 alkylcarbonyloxyC 1-6 alkyl, N—C 1-4 alkylaminocarbonylC 1-6 alkyl, N,N-diC 1-4 alkylaminocarbonylC 1-6 alkyl, C 1-4 alkylsulfanylC 1-6 alkyl, C 1-6 alkylsulfonylC 1-6 alkyl or C 1-6 alkylsulfonylaminoC 1-6 alkyl; or

R 14 is C 3-8 cycloalkyl, C 3-8 cycloalkylC 1-6 alkyl, C 3-8 cycloalkylC 1-6 alkoxy, C 3-6 cycloalkyloxy, wherein the cycloalkyl moiety is optionally partially unsaturated, phenyl, phenylC 1-6 alkyl, phenylC 1-6 alkoxy, heteroaryl, heteroarylC 1-6 alkyl, heteroarylC 1-6 alkoxy, wherein the heteroaryl moiety is a 5- or 6-membered monocyclic aromatic ring which comprises 1, 2, 3 or 4 heteroatoms individually selected from N, O and S, heterocyclyl, heterocyclylC 1-6 alkyl or heterocyclylC 1-6 alkoxy wherein the heterocyclyl moiety is a 4- to 6-membered non-aromatic ring which comprises 1, 2 or 3 heteroatoms individually selected from N, O and S,

wherein for R 14 , any cycloalkyl, phenyl, heteroaryl, heterocyclyl moiety is optionally substituted by 1, 2 or 3 substituents, which may be the same or different, selected from R 16 ; wherein

R 16 is cyano, halogen, hydroxy, C 1-4 alkyl, C 2-4 alkenyl, C 2-4 alkynyl, C 1-4 haloalkyl, C 2-4 haloalkenyl, C 1-4 alkoxy, C 1-2 alkoxyC 1-2 alkyl, C 1-4 haloalkoxy, C 3-4 alkenyloxy, C 3-4 alkynyloxy, N—C 1-4 alkylamino, N,N-diC 1-4 alkylamino, C 1-4 alkylcarbonyl, C 1-4 alkoxycarbonyl, carbonylamino, N—C 1-4 alkylaminocarbonyl, N,N-diC 1-4 alkylaminocarbonyl or C 1-4 alkoxycarbonylamino;

and wherein, when R 14 is substituted C 3-8 cycloalkyl, C 3-8 cycloalkylC 1-6 alkyl, C 3-8 cycloalkylC 1-6 alkoxy, heterocyclyl, heterocyclylC 1-6 alkyl or heterocyclylC 1-6 alkoxy, R 16 may also represent oxo on the C 3-8 cycloalkyl or heterocyclyl moiety;

R 15 is hydrogen, C 1-4 alkyl, C 3-4 alkynyl, C 1-4 alkoxyC 1-4 alkyl, cyanoC 1-4 alkyl, C 3-6 cycloalkyl or C 3-6 cycloalkylC 1-2 alkyl; or

R 14 and R 15 , together with the nitrogen atom to which they are bonded, form a 4-, 5- or 6-membered cycle optionally containing an additional heteroatom or group selected from O, S, S(O) 2 , oxo (═O) and NR 17 ; wherein

R 17 is hydrogen, methyl, methoxy, formyl or acyl; or

a salt or an N-oxide thereof.

2. The compound according to claim 1 , wherein R 7 is hydroxy, C 1-4 alkyl, C 2-4 haloalkyl, C 1-2 alkoxy, C 3-4 alkenyl, C 3-4 alkynyl or cyclopropyl.

3. The compound according to claim 1 , wherein

R 14 is hydrogen, cyano, C 1-6 alkyl, C 1-6 alkoxy, C 2-6 alkenyl, C 2-6 alkynyl, cyanoC 1-6 alkyl, C 1-6 haloalkyl, C 1-4 alkoxyC 1-6 alkyl, C 1-6 alkoxycarbonylC 1-6 alkyl, or C 3-8 cycloalkyl, C 3-8 cycloalkylC 1-6 alkyl, phenyl or heteroarylC 1-6 alkyl, wherein the heteroaryl moiety is a 5-membered monocyclic aromatic ring which comprises 1, 2, 3 or 4 heteroatoms individually selected from N, O and S, wherein any cycloalkyl, phenyl or heteroaryl moiety is optionally substituted by 1 or 2 substituents, which may be the same or different, selected from R 16 , wherein R 16 is cyano, halogen, hydroxy, C 1-4 alkyl, C 1-4 haloalkyl, C 1-4 alkoxy, C 1-4 haloalkoxy and C 1-4 alkoxycarbonyl; and

R 15 is hydrogen, methyl, ethyl, C 3-4 alkynyl or methoxyethyl.

4. The compound according to claim 1 , wherein R 14 is hydrogen, C 1-6 alkyl, C 1-6 alkoxy, C 2-4 alkenyl, C 2-4 alkynyl, C 1-2 haloalkyl or C 3-6 cycloalkyl.

5. The compound according to claim 1 , wherein R 15 is hydrogen, methyl or ethyl.

6. The compound according to claim 1 , said compound being selected from:

7. The compound according to claim 1 , wherein A 1 is CR 1 and A 2 is CR 2 , wherein R 1 and R 2 are independently selected from hydrogen and halogen.

8. The compound according to claim 1 , wherein A 1 , A 2 , A 3 and A 4 are C—H.

9. The compound according to claim 1 , wherein n is 1.

10. The compound according to claim 1 , wherein R 5 and R 6 are hydrogen and n is 1.

11. An agrochemical composition comprising a fungicidally effective amount of a compound of formula (I) according to claim 1 and at least one additional active ingredient and/or an agrochemically-acceptable diluent or carrier.

12. A compound of formula (I):

wherein

n is 1 or 2

A 1 represents N or CR 1 , wherein R 1 represents hydrogen, halogen, methyl, ethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, or difluoromethoxy;

A 2 represents N or CR 2 , wherein R 2 represents hydrogen, halogen, methyl, ethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, or difluoromethoxy;

A 3 represents N or CR 3 , wherein R 3 represents hydrogen or halogen;

A 4 represents N or CR 4 , wherein R 4 represents hydrogen or halogen; and

wherein no more than two of A 1 to A 4 are N;

R 5 and R 6 are independently selected from hydrogen, C 1-4 alkyl, halogen, cyano, trifluoromethyl and difluoromethyl, or R 5 and R 6 together with the carbon atom they share form a cyclopropyl;

R 7 represents C 1-4 alkyl, C 2-4 haloalkyl, C 1-4 alkoxy, C 1-2 alkoxyC 1-4 alkyl, C 1-2 haloalkoxyC 1-4 alkyl, C 3-4 alkynyl, C 3-6 alkenyl, C 3-6 alkenyloxy, C 3-6 alkynyloxy, C 3-6 haloalkenyl, C 3-6 haloalkenyloxy or

R 7 represents C 3-6 cycloalkyl, C 3-6 cycloalkylC 1-2 alkyl, C 3-6 cycloalkylC 1-2 alkoxy, phenyl, phenylC 1-2 alkyl, phenylC 1-2 alkoxy, heteroaryl, heteroarylC 1-2 alkyl, heteroarylC 1-2 alkoxy, heterocyclyl, heterocyclylC 1-2 alkyl, or heterocyclylC 1-2 alkoxy, wherein the heteroaryl moiety is a 5- or 6-membered monocyclic aromatic ring which comprises 1, 2, 3 or 4 heteroatoms individually selected from N, O and S, the heterocyclyl moiety is a 4- to 6-membered non-aromatic ring which comprises 1 or 2 heteroatoms individually selected from N, O and S, and wherein any of said cycloalkyl, phenyl, heteroaryl and heterocyclyl moieties are optionally substituted by 1 or 2 substituents selected from hydrogen, cyano, fluoro, chloro, bromo, methyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, or difluoromethoxy;

R 8 represents —NR 15 R 16 , wherein R 15 represents hydrogen, C 1-6 alkyl, C 1-6 alkoxy, C 2-6 alkenyl, C 2-6 alkynyl, cyanoC 1-6 alkyl, C 1-6 haloalkyl, C 1-6 haloalkenyl, hydroxyC 1-6 alkyl, C 1-4 alkoxyC 1-6 alkyl, C 1-4 haloalkoxyC 1-6 alkyl, C 1-4 alkoxyC 1-4 alkoxyC 1-6 alkyl, aminoC 1-6 alkyl, N—C 1-4 alkylaminoC 1-6 alkyl, N,N-diC 1-4 alkylaminoC 1-6 alkyl, C 1-6 alkylcarbonylC 1-6 alkyl, C 1-6 alkylcarbonylC 2-6 alkenyl, C 1-6 alkoxycarbonylC 1-6 alkyl, C 1-6 alkylcarbonyloxyC 1-6 alkyl, N—C 1-4 alkylaminocarbonylC 1-6 alkyl, N,N-diC 1-4 alkylaminocarbonylC 1-6 alkyl, C 1-4 alkylsulfanylC 1-6 alkyl, C 1-6 alkylsulfonylC 1-6 alkyl, C 1-6 alkylsulfonylaminoC 1-6 alkyl; or

R 15 represents C 3-8 cycloalkyl, C 3-8 cycloalkylC 1-6 alkyl, C 3-8 cycloalkylC 1-6 alkoxy wherein the cycloalkyl moiety is optionally partially unsaturated, phenyl, phenylC 1-6 alkyl, phenylC 1-6 alkoxy, heteroaryl, heteroarylC 1-6 alkyl, heteroarylC 1-6 alkoxy, wherein the heteroaryl moiety is a 5- or 6-membered monocyclic aromatic ring which comprises 1, 2, 3 or 4 heteroatoms individually selected from N, O and S, heterocyclyl, heterocyclylC 1-6 alkyl, heterocyclylC 1-6 alkoxy wherein the heterocyclyl moiety is a 4- to 6-membered non-aromatic ring which comprises 1, 2 or 3 heteroatoms individually selected from N, O and S;

wherein for R 15 , any of C 3-8 cycloalkyl, C 3-8 cycloalkylC 1-6 alkyl, C 3-8 cycloalkylC 1-6 alkoxy, phenyl, phenylC 1-6 alkyl, phenylC 1-6 alkoxy, heteroaryl, heteroarylC 1-6 alkyl, heteroarylC 1-6 alkoxy, heterocyclyl, heterocyclylC 1-6 alkyl and heterocyclylC 1-6 alkoxy moieties are optionally substituted by 1, 2 or 3 substituents, which may be the same or different, selected from R 17 ; wherein

R 17 represents cyano, halogen, hydroxy, C 1-4 alkyl, C 2-4 alkenyl, C 2-4 alkynyl, C 1-4 haloalkyl, C 2-4 haloalkenyl, C 1-4 alkoxy, C 1-4 haloalkoxy, C 3-4 alkenyloxy, C 3-4 alkynyloxy, N—C 1-4 alkylamino, N,N-diC 1-4 alkylamino, C 1-4 alkylcarbonyl, C 1-4 alkoxycarbonyl, carbonylamino, N—C 1-4 alkylaminocarbonyl, N,N-diC 1-4 alkylaminocarbonyl or C 1-4 alkoxycarbonylamino;

and wherein R 15 is substituted C 3-8 cycloalkyl, C 3-8 cycloalkylC 1-6 alkyl, C 3-8 cycloalkylC 1-6 alkoxy, heterocyclyl, or heterocyclylC 1-6 alkyl, heterocyclylC 1-6 alkoxy, R 17 may also represent oxo on the C 3-8 cycloalkyl or heterocyclyl moiety;

R 16 is hydrogen or C 1-4 alkyl, C 1-4 alkoxyC 1-4 alkyl, cyanoC 1-4 alkyl; or

R 15 and R 16 , together with the nitrogen atom to which they are bonded, form a 4-, 5- or 6-membered cycle optionally containing an additional heteroatom selected from O, S or NR 18 ; wherein

R 18 is hydrogen, methyl, methoxy, formyl or acyl; or

a salt or an N-oxide thereof.

13. The compound according to claim 12 , wherein A 1 is CR 1 and A 2 is CR 2 , wherein R 1 and R 2 are independently selected from hydrogen and halogen.

14. The compound according to claim 12 , wherein A 1 , A 2 , A 3 and A 4 are C—H.

15. The compound according to claim 12 , wherein n is 1.

16. The compound according to claim 12 , wherein R 5 and R 6 are hydrogen and n is 1.

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

18. A method of controlling or preventing infestation of useful plants by phytopathogenic microorganisms, comprising applying to the plants, to parts thereof or the locus thereof a fungicidally effective amount of a compound of formula (I) according to claim 6 , or a composition comprising the compound of formula (I) compound as an active ingredient.

19. An agrochemical composition comprising a fungicidally effective amount of a compound of formula (I) according to claim 6 and at least one additional active ingredient and/or an agrochemically-acceptable diluent or carrier.

20. A method of controlling or preventing infestation of useful plants by phytopathogenic microorganisms, comprising applying to the plants, to parts thereof or the locus thereof a fungicidally effective amount of a compound of formula (I) according to claim 12 , or a composition comprising the compound of formula (I) compound as an active ingredient.