Substituted oxadiazoles for combating phytopathogenic fungi

A compound of formula I,

• or an N-oxide or an agriculturally acceptable salt thereof;
• wherein:
• A is phenyl or a 5- or 6-membered aromatic heterocycle, wherein the ring member atoms of the aromatic heterocycles include besides carbon atoms 1, 2, 3 or 4 heteroatoms selected from N, O and S as ring member atoms;
• and wherein the phenyl ring or the aromatic heterocycles are unsubstituted or substituted with 1, 2, 3 or 4 identical or different groups RA;
• wherein
• RA is halogen, cyano, NO2, OH, SH, NH2, diC1-C6-alkylamino, C1-C6-alkyl, C1-C6-alkoxy, C1-C6-alkylthio, C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C8-cycloalkyl or C3-C8-cycloalkoxy;
• and wherein any of the aliphatic and cyclic moieties are unsubstituted or substituted with 1, 2, 3 or 4 identical or different groups Ra;
• wherein
• Ra is halogen, cyano, NO2, OH, SH, NH2, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio or C3-C8-cycloalkyl or C1-C4-alkoxy-C1-C4-alkyl;
• L is —(C═O)—, —(C═S)— or —S(═O)p—;
• p is 0, 1 or 2;
• R1 is C3-C8-cycloalkyl, C3-C8-cycloalkenyl, C2-C6-alkenyl, C2-C6-alkynyl, phenyl-C1-C4-alkyl, heteroaryl-C1-C4-alkyl, phenyl, naphthyl or a 3- to 10-membered saturated, partially unsaturated or aromatic mono- or bicyclic heterocycle, wherein the ring member atoms of said mono- or bicyclic heterocycle include besides carbon atoms further 1, 2, 3 or 4 heteroatoms selected from N, O and S as ring member atoms and wherein 1 or 2 carbon ring member atoms of the heterocycle may be replaced by 1 or 2 groups independently selected from —C(═O)— and —C(═S)—;
• and wherein the heteroaryl group in heteroaryl-C1-C4-alkyl is a 5- or 6-membered aromatic heterocycle, wherein the ring member atoms of the heterocyclic ring include besides carbon atoms 1, 2, 3 or 4 heteroatoms selected from N, O and S as ring member atoms;
• and wherein any of the above-mentioned aliphatic or cyclic groups are unsubstituted or substituted with 1, 2, 3 or up to the maximum possible number of identical or different groups R1a;
• wherein
• R1a is halogen, oxo, cyano, NO2, OH, SH, NH2, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C3-C8-cycloalkyl, NHSO2—C1-C4-alkyl, (C═O)—C1-C4-alkyl, C(═O)—C1-C4-alkoxy, C1-C6-alkylsulfonyl, hydroxyC1-C4-alkyl, C(═O)—NH2, C(═O)—NH(C1-C4-alkyl), C1-C4-alkylthio-C1-C4-alkyl, aminoC1-C4-alkyl, C1-C4-alkylamino-C1-C4-alkyl, diC1-C4-alkylamino-C1-C4-alkyl, aminocarbonyl-C1-C4-alkyl or C1-C4-alkoxy-C1-C4-alkyl.
• R2 is hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy, C3-C8-cycloalkyl, C3-C8-cycloalkenyl, C3-C8-cycloalkyl-C1-C6-alkyl, phenyl-C1-C4-alkyl, phenyl, C(═O)—C1-C6-alkyl or C(═O)—C1-C6-alkoxy;
• and wherein any of the aliphatic or cyclic groups are unsubstituted or substituted with 1, 2, 3 or up to the maximum possible number of identical or different groups R1a;
• R3, R4 independently of each other are selected from the group consisting of hydrogen, halogen, cyano, C1-C4-alkyl, C1-C4-alkenyl, C1-C4-alkynyl and C1-C4-haloalkyl;
• or R3 and R4 together with the carbon atom to which they are bound form a 3- to 7-membered carbocycle or a saturated 3- to 6-membered heterocycle, wherein the heterocycle includes beside carbon atoms 1, 2 or 3 heteroatoms independently selected from N—RN, S, —S(═O)—, —S(═O)2— and O as ring member atoms;
• wherein
• RN is H, C1-C6-alkyl, SO2CH3, SO2C6H4CH3 or SO2-aryl;
• and wherein one or two CH2 groups of the carbocycle or heterocycle may be replaced by one or two groups independently selected from the group of —C(═O)— and —C(═S)—;
• and wherein the carbocycle, the heterocycle and aryl is unsubstituted or substituted with 1, 2, 3, 4 or up to the maximum possible number of identical or different groups R3a;
• wherein
• R3a is halogen, cyano, NO2, OH, SH, NH2, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C3-C8-cycloalkyl, NHSO2—C1-C4-alkyl, (C═O)—C1-C4-alkyl, C(═O)—C1-C4-alkoxy or C1-C6-alkylsulfonyl;
• with the exception of 5-ethyl-2,4-dimethyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrazole-3-carboxamide, 5-ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrazole-3-carboxamide, 4-chloro-2,5-dimethyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrazole-3-carboxamide, 4-bromo-5-ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrazole-3-carboxamide and 4-chloro-5-ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrazole-3-carboxamide.