Substituted trifluoromethyloxadiazoles 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 heterocycle include besides carbon atoms 1, 2, 3 or 4 heteroatoms selected from N, O and S as ring member atoms with the provision that the heterocycle cannot contain 2 contiguous atoms selected from O and S;
• and wherein the phenyl ring or the aromatic heterocycle is unsubstituted or substituted with 1, 2, 3 or 4 identical or different groups RA;
• wherein
• RA is halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy or C1-C6-haloalkoxy;
• L is —C(═O)— or —C(═S)—;
• R1 is a saturated or partially unsaturated monocyclic 3- to 8-membered carbocycle;
• wherein 1 or 2 ring member atoms of the carbocycle are substituted with radicals independently selected from the group consisting of R11, R12, R13 and R14;
• wherein R11 is #═N—O—R3;
• R12 is #═N—N(R4)2;
• R13 is #—C(═N—O—R3)R5;
• R14 is #—C(═N—N(R4)2)R5;
• and wherein # indicates the position which is attached to the ring member atom of the carbocycle;
• and wherein the ring member atoms of the carbocycle are further unsubstituted or further substituted with additional 1, 2, 3, 4 or up to the maximum possible number of identical or different radicals R1a;
• 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, formyl, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy or C3-C8-cycloalkyl;
• R3 is independently selected from the group consisting of hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C8-cycloalkyl, C3-C8-cycloalkenyl, phenyl, phenyl-C1-C4-alkyl, heteroaryl-C1-C4-alkyl, or a 3- to 10-membered saturated, partially unsaturated or aromatic mono- or bicyclic heterocycle;
• and wherein the ring member atoms of said 3- to 10-membered saturated, partially unsaturated or aromatic mono- or bicyclic heterocycle include besides carbon atoms 1, 2 or 3 heteroatoms selected from N, O and S as ring member atoms with the provision that the heterocycle cannot contain 2 contiguous atoms selected from O and S;
• 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 radicals selected from the group consisting of halogen, C1-C6-alkyl and C3-C8-cycloalkyl;
• R4 is independently selected from the group consisting of hydrogen, halogen, cyano, formyl, C1-C6-alkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkenyl, C(═O)—(C1-C6-alkyl), C(═O)—(C1-C6-alkoxy), phenyl-C1-C4-alkyl, heteroaryl-C1-C4-alkyl, phenyl, naphthyl, a 3- to 10-membered saturated, partially unsaturated or aromatic mono- or bicyclic heterocycle and a 3- to 10-membered saturated or partially unsaturated bicyclic carbocycle;
• wherein the heteroaryl group in heteroaryl-C1-C4-alkyl is a 5- or 6-membered aromatic heterocycle, wherein the ring member atoms of said 5- or 6-membered aromatic heterocycle include besides carbon atoms 1, 2 or 3 heteroatoms selected from N, O and S as ring member atoms with the provision that the aromatic heterocycle cannot contain 2 contiguous atoms selected from O and S;
• and wherein the ring member atoms of said 3- to 10-membered saturated, partially unsaturated or aromatic mono- or bicyclic heterocycle include besides carbon atoms further 1, 2 or 3 heteroatoms selected from N, O and S as ring member atoms with the provision that the heterocycle cannot contain 2 contiguous atoms selected from O and S;
• 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 any of the above-mentioned aliphatic or cyclic groups are unsubstituted or substituted with 1, 2, 3, 4 or up to the maximum possible number of identical or different radicals selected from the group consisting of halogen, C1-C6-alkyl and C3-C8-cycloalkyl;
• R5 is hydrogen, C1-C6-alkyl, amino, cyano, C1-C4-alkylamino, diC1-C4-alkylamino, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkenyl, C(═O)—(C1-C6-alkyl), C(═O)—(C1-C6-alkoxy), phenyl-C1-C4-alkyl, heteroaryl-C1-C4-alkyl, phenyl, naphthyl, a 3- to 10-membered saturated, partially unsaturated or aromatic mono- or bicyclic heterocycle or a 3- to 10-membered saturated or partially unsaturated bicyclic carbocycle;
• wherein the heteroaryl group in heteroaryl-C1-C4-alkyl is a 5- or 6-membered aromatic heterocycle, wherein the ring member atoms of said 5- or 6-membered aromatic heterocycle include besides carbon atoms 1, 2 or 3 heteroatoms selected from N, O and S as ring member atoms with the provision that the aromatic heterocycle cannot contain 2 contiguous atoms selected from O and S;
• and wherein the ring member atoms of said 3- to 10-membered saturated, partially unsaturated or aromatic mono- or bicyclic heterocycle include besides carbon atoms further 1, 2 or 3 heteroatoms selected from N, O and S as ring member atoms with the provision that the heterocycle cannot contain 2 contiguous atoms selected from O and S;
• 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 any of the above-mentioned aliphatic or cyclic groups are unsubstituted or substituted with 1, 2, 3, 4 or up to the maximum possible number of identical or different radicals selected from the group consisting of halogen, C1-C6-alkyl and C3-C8-cycloalkyl;
• with the exception of compounds, wherein the group —NR2— and a radical selected from the group consisting of R13 and R14 are attached to the same ring member atom of the carbocycle of R1.