Microbiocidal oxadiazole derivatives
Compounds of the formula (I) wherein the substituents are as defined in claim 1 , useful as a pesticides, especially as fungicides.
1. A compound of formula (I):
wherein
n is 1 or 2;
A 1 represents CR 1 , wherein R 1 is hydrogen, halogen, methyl, ethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, or difluoromethoxy;
A 2 represents CR 2 , wherein R 2 is hydrogen, halogen, methyl, ethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, or difluoromethoxy;
A 3 represents CR 3 , wherein R 3 is hydrogen or halogen;
A 4 represents CR 4 , wherein R 4 is hydrogen or halogen;
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 haloalkyl, hydroxyC 1-4 alkyl, C 1-2 alkoxyC 1-4 alkyl, C 1-2 haloalkoxyC 1-4 alkyl, 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, 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 hydrogen, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, cyanoC 1-6 alkyl, C 1-6 haloalkyl, C 2-6 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, C 2-4 alkynyloxyC 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 1-6 alkylsulfanylC 1-6 alkyl, C 1-6 alkylsulfonylC 1-6 alkyl, C 1-6 alkylsulfonylaminoC 1-6 alkyl, C 1-6 alkyl sulfonylaminoC 2-6 alkynyl, C 2-6 alkynyloxycarbonylaminoC 1-6 alkyl, C 1-4 alkylcarbonylaminoC 1-6 alkyl or C 1-4 alkoxycarbonylaminoC 1-6 alkyl; or
R 8 is C 3-8 cycloalkyl, C 3-8 cycloalkylC 1-6 alkyl, wherein the cycloalkyl moiety is optionally partially unsaturated, phenyl, phenylC 1-6 alkyl, phenylC 2-6 alkenyl, napthyl, naphthylC 1-6 alkyl, heteroaryl, heteroarylC 1-6 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, heterodiaryl, heterodiarylC 1-6 alkyl wherein the heterodiaryl moiety is a 9- or 10-membered bicyclic aromatic system which comprises 1, 2, 3 or 4 heteroatoms individually selected from N, O and S, heterocyclyl, heterocyclylC 1-6 alkyl 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, or C 3-6 cycloalkylcarbonylaminoC 1-6 alkyl,
wherein for R 8 , any cycloalkyl, phenyl, napthyl, heteroaryl, heterodiaryl or heterocyclyl moiety is optionally substituted by 1, 2 or 3 substituents, which may be the same or different, selected from R 9 ; or, additionally, when R 8 is cyclopropyl, the cyclopropyl moiety is substituted by 4 substituents, which may be the same or different, selected from R 9 , with the proviso that at least 2R 9 substituents are the same; wherein
R 9 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 1-4 haloalkoxy, C 3-4 alkynyloxy, N—C 1-4 alkylamino, N,N-diC 1-4 alkylamino, C 1-4 alkylcarbonyl, C 3-6 cycloalkylcarbonyl, 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 8 is substituted C 3-8 cycloalkyl, C 3-8 cycloalkylC 1-6 alkyl, heterocyclyl or heterocyclylC 1-6 alkyl, R 9 may also represent oxo on the C 3-8 cycloalkyl or heterocyclyl moiety; or
wherein for R 8 , any cycloalkyl, phenyl, napthyl, heteroaryl, heterodiaryl or heterocyclyl moiety is optionally substituted by 1 substituent selected from R 10 and further optionally substituted by 1 or 2 substituents selected from R 9 ; wherein
R 10 is C 3-8 cycloalkyl, C 3-8 cycloalkylC 1-2 alkyl, phenyl, phenylC 1-2 alkyl, heteroaryl, heteroarylC 1-2 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, heterocyclyl or heterocyclylC 1-6 alkyl 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, and wherein any of said cycloalkyl, phenyl, heteroaryl and heterocyclyl moieties are optionally substituted by 1, 2 or 3 substituents, which may be the same or different, selected from R 11 ; wherein
R 11 is hydrogen, cyano, fluoro, chloro, bromo, methyl, trifluoromethyl, methoxy and ethoxy; or
a salt or an N-oxide thereof.
2. The compound according to claim 1 , wherein
R 8 is C 1-6 alkyl, C 2-4 alkenyl, C 2-4 alkynyl, cyanoC 1-4 alkyl, C 1-5 haloalkyl, C 2-4 haloalkenyl, hydroxyC 1-4 alkyl, C 1-2 alkoxyC 1-4 alkyl, C 1-2 haloalkoxyC 1-4 alkyl, C 1-2 alkoxyC 1-2 alkoxyC 1-4 alkyl, aminoC 1-4 alkyl, C 1-2 alkylcarbonylC 1-4 alkyl, C 1-4 alkylcarbonylC 2-4 alkenyl, C 1-4 alkylcarbonyloxyC 1-4 alkyl, C 1-4 alkylsulfonylaminoC 2-4 alkynyl, C 1-2 alkylcarbonylaminoC 1-4 alkyl, C 2-4 alkynyloxycarbonylaminoC 1-4 alkyl or C 1-2 alkoxycarbonylaminoC 1-4 alkyl; or
R 8 is C 3-6 cycloalkyl, C 3-6 cycloalkylC 1-2 alkyl, phenyl, phenylC 1-4 alkyl, phenylC 2-4 alkenyl, napthyl, a heteroaryl-containing moiety selected from furanyl, pyrazolyl, imidazolyl, triazolyl, 1,2,3-benzothiadiazole, (pyridinyl)methyl, or a heterocyclyl-containing moiety selected from oxetanyl, pyrrolidinyl, azetidinyl, tetrahydrofuranyl, 1,3-dioxolanyl, thietanyl, 1-oxo-thietan-3-yl, 1,1-dioxo-thietan-3-yl, tetrahydropyranyl, tetrahydrothiopyranyl or C 3-6 cycloalkylcarbonylaminoC 1-4 alkyl,
wherein the cycle of each heteroaryl-containing moiety or heterocyclyl-containing moiety is optionally substituted by 1, 2 or 3 substituents, which may be the same of different, selected from R 9 , or
wherein the cycle of each heteroaryl-containing moiety or heterocyclyl-containing moiety is optionally substituted by 1 substituent selected from R 10 and further optionally substituted by 1 or 2 substituents selected from R 9 ;
R 9 is cyano, methyl, chloro, fluoro, hydroxyl, methoxy, trifluoromethyl, C 2 -haloalkenyl, methylcarbonyl, ethylcarbonyl and carbonylamino;
R 10 is phenyl or pyridinyl, wherein phenyl or pyridinyl is optionally substituted by 1, 2 or 3 substituents, which may be the same or different, selected from R 11 ; and
R 11 is fluoro, chloro, bromo and methoxy.
3. The compound according to claim 2 , wherein R 8 is C 1-6 alkyl, C 1-2 haloalkyl, hydroxyC 1-6 alkyl, C 1-2 alkoxyC 1-4 alkyl, C 3-6 cycloalkyl or heterocyclyl, wherein the heterocyclyl moiety is a 4- or 5-membered non-aromatic ring which comprises 1 or 2 heteroatoms individually selected from N and O, wherein C 3-6 cycloalkyl and heterocyclyl are optionally substituted by 1, 2 or 3 substituents, which may be the same or different, selected from R 9 ; wherein R 9 is cyano, halogen, hydroxy, C 1-4 alkyl, C 2-4 alkenyl, C 2-4 alkynyl, C 1-4 haloalkyl and C 1-4 alkoxy.
4. The compound according to claim 3 , wherein R 8 is C 1-4 alkyl, C 1-2 haloalkyl, hydroxyC 1-4 alkyl, C 1-2 alkoxyC 1-4 alkyl, C 3-6 cycloalkyl or heterocyclyl, wherein the heterocyclyl moiety is a 4- or 5-membered non-aromatic ring which comprises 1 or 2 heteroatoms which are oxygen, wherein C 3-6 cycloalkyl and heterocyclyl are optionally substituted by 1 or 2 substituents, which may be the same or different, selected from R 9 ; wherein R 9 represents cyano, fluoro, chloro, hydroxy, methyl, ethyl, trifluoromethyl and methoxy.
5. The compound according to claim 3 , wherein R 8 is C 1-4 alkyl, 2,2,2-trifluoroethyl, hydroxyC 1-4 alkyl, C 1-2 alkoxyC 1-2 alkyl, cyclopropyl or heterocyclyl, wherein the heterocyclyl moiety is tetrahydrofuran-2-yl, oxetan-3-yl or 1,3-dioxolan-2-yl, wherein cyclopropyl and heterocyclyl are each optionally substituted by 1 or 2 substituents, which may be the same or different, selected from R 9 , wherein R 9 is fluoro, chloro and methyl.
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 .
12. The composition according to claim 6 , further comprising at least one additional active ingredient and/or an agrochemically-acceptable diluent or carrier.
13. 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 C 1-4 haloalkyl, 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 or C 3-6 haloalkenyloxy; or
R 7 is 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 cyano, fluoro, chloro, bromo, methyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, or difluoromethoxy;
R 8 is hydrogen, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, cyanoC 1-6 alkyl, C 1-6 haloalkyl, C 2-6 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, C 2-4 alkynyloxyC 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 1-6 alkylsulfanylC 1-6 alkyl, C 1-6 alkylsulfonylC 1-6 alkyl, C 1-6 alkyl sulfonyl aminoC 1-6 alkyl, C 1-6 alkyl sulfonyl aminoC 2-6 alkynyl or C 2-6 alkynyloxycarbonylaminoC 1-6 alkyl; or
R 8 is C 3-8 cycloalkyl, C 3-8 cycloalkylC 1-6 alkyl, wherein the cycloalkyl moiety is optionally partially unsaturated, phenyl, phenylC 1-6 alkyl, phenylC 2-6 alkenyl, napthyl, naphthylC 1-6 alkyl, heteroaryl, heteroarylC 1-6 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, heterodiaryl, heterodiarylC 1-6 alkyl wherein the heterodiaryl moiety is a 9- or 10-membered bicyclic aromatic system which comprises 1, 2, 3 or 4 heteroatoms individually selected from N, O and S, heterocyclyl, heterocyclylC 1-6 alkyl 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, or C 3-6 cycloalkylcarbonylaminoC 1-6 alkyl,
wherein for R 8 , any cycloalkyl, phenyl, napthyl, heteroaryl, heterodiaryl or heterocyclyl moiety is optionally substituted by 1, 2 or 3 substituents, which may be the same or different, selected from R 9 ; wherein
R 9 is cyano, halogen, hydroxy, C 1-4 alkyl, C 2-4 alkenyl, C 2-4 alkynyl, C 1-4 haloalkyl, C 2 -4haloalkenyl, C 1-4 alkoxy, C 1-4 haloalkoxy, 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 -4alkylaminocarbonyl or C 1-4 alkoxycarbonylamino, and wherein when R 8 is substituted C 3-8 cycloalkyl, C 3-8 cycloalkylC 1-6 alkyl, heterocyclyl or heterocyclylC 1-6 alkyl, R 9 may also represent oxo on the C 3-8 cycloalkyl or heterocyclyl moiety; or
wherein for R 8 , any cycloalkyl, phenyl, napthyl, heteroaryl, heterodiaryl or heterocyclyl moiety is optionally substituted by 1 substituent selected from R 10 and further optionally substituted by 1 or 2 substituents selected from R 9 ; wherein
R 10 is C 3-8 cycloalkyl, C 3-8 cycloalkylC 1-2 alkyl, phenyl, phenylC 1-2 alkyl, heteroaryl, heteroarylC 1-2 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, heterocyclyl or heterocyclylC 1-6 alkyl 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, and wherein any of said cycloalkyl, phenyl, heteroaryl and heterocyclyl moieties are optionally substituted by 1, 2 or 3 substituents, which may be the same or different, selected from R 11 ; wherein
R 11 is hydrogen, cyano, fluoro, chloro, bromo, methyl, trifluoromethyl, methoxy and ethoxy; or
a salt or an N-oxide thereof.
14. The compound according to claim 13 , 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.
15. The compound according to claim 13 , wherein A 1 , A 2 , A 3 and A 4 are C—H.
16. The compound according to claim 13 , wherein n is 1.
17. The compound according to claim 13 , wherein R 5 and R 6 are hydrogen and n is 1.
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 claim 1 , or a composition comprising the compound of formula (I) as an active ingredient.
19. 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 claim 13 , or a composition comprising the compound of formula (I) as an active ingredient.