2-pyridinylethylcarboxamide derivatives and their use as fungicides

A compound of formula (I)

• wherein:
• n is 1, 2 or 3;
• Ra is a C1-C6-halogenoalkyl having 1 to 5 halogen atoms;
• each substituent X is independently selected from the group consisting of a hydrogen atom, a halogen atom, a C1-C6-alkyl, and a C1-C6-halogenoalkyl;
• R1, R2, R3 and R4 are independently selected from the group consisting of a hydrogen atom, a halogen atom, a cyano group, a hydroxy group, an amino group, a sulfanyl group, a formyl group, a formyloxy group, a formylamino group, a carboxy group, a carbamoyl group, a N-hydroxycarbamoyl group, a carbamate group, a (hydroxyimino)-C1-C6-alkyl group, a C1-C6 alkyl, a C2-C6-alkenyl, a C2-C6-alkynyl, a C1-C6-alkylamino, a di-C1-C6-alkylamino, a C1-C6-alkoxy, a C1-C6-halogenoalkyl having 1 to 5 halogen atoms, a C1-C6-halogenoalkoxy having 1 to 5 halogen atoms, a C1-C6-alkylsulfanyl, a C1-C6-halogenoalkylsulfanyl having 1 to 5 halogen atoms, a C2-C6-alkenyloxy, a C2-C6-halogenoalkenyloxy having 1 to 5 halogen atoms, a C3-C6-alkynyloxy, a C3-C6-halogenoalkynyloxy having 1 to 5 halogen atoms, a C3-C6-cycloalkyl, a C3-C6-halogenocycloalkyl having 1 to 5 halogen atoms, a C1-C6-alkylcarbonyl, a C1-C6-halogenoalkylcarbonyl having 1 to 5 halogen atoms, a C1-C6-alkylcarbamoyl, a di-C1-C6-alkylcarbamoyl, a N—C1-C6-alkyloxycarbamoyl, a C1-C6-alkoxycarbamoyl, a N—C1-C6-alkyl-C1-C6-alkoxycarbamoyl, a C1-C6-alkoxycarbonyl, a C1-C6-halogenoalkoxycarbonyl having 1 to 5 halogen atoms, a C1-C6-alkylcarbonyloxy, a C1-C6-halogenoalkylcarbonyloxy having 1 to 5 halogen atoms, a C1-C6-alkylcarbonylamino, a C1-C6-halogenoalkylcarbonylamino having 1 to 5 halogen atoms, a C1-C6-alkylaminocarbonyloxy, a di-C1-C6-alkylaminocarbonyloxy, a C1-C6-alkyloxycarbonyloxy, a C1-C6-alkylsulfenyl, a C1-C6-halogenoalkylsulfenyl having 1 to 5 halogen atoms, a C1-C6-alkylsulfinyl, a C1-C6-halogenoalkylsulfinyl having 1 to 5 halogen atoms, a C1-C6-alkylsulfonyl, a C1-C6-halogenoalkylsulfonyl having 1 to 5 halogen atoms, a benzyl, a benzyloxy, a benzylsulfanyl, a benzylsulfinyl, a benzylsulfonyl, a benzylamino, a phenoxy, a phenylsulfanyl, a phenylsulfinyl, a phenylsulfonyl, a phenylamino, a phenylcarbonylamino, a 2,6 dichlorophenyl-carbonylamino group, and a phenyl group;
• or R1 and R2 may form together a cyclopropyl, a cyclobutyl, a cyclopentyl or a cyclohexyl;
• with the proviso that when three of the four substituents R1, R2, R3 and R4 are a hydrogen atom, then the fourth substituent is not a hydrogen atom;
• R5 is selected from the group consisting of a hydrogen atom, a cyano group, a formyl group, a hydroxy group, a C1-C6-alkyl, a C1-C6-halogenoalkyl having 1 to 5 halogen atoms, a C1-C6-alkoxy, a C1-C6-halogenoalkoxy having 1 to 5 halogen atoms, a C3-C6-cycloalkyl, a C3-C6-halogenocycloalkyl having 1 to 5 halogen atoms, a C2-C6-alkenyl, a C2-C6-alkynyl, a C1-C6-alkoxy-C1-C6-alkyl, a C1-C6-cyanoalkyl. a C1-C6-aminoalkyl, a C1-C6-alkylamino-C1-C6-alkyl, a di-C1-C6-alkylamino-C1-C6-alkyl, a C1-C6-alkylcarbonyl, a C1-C6-halogenalkylcarbonyl having 1 to 5 halogen atoms, a C1-C6-alkyloxycarbonyl, a C3-C7-cycloalkyl, a C3-C7-halogenocycloalkyl having 1 to 5 halogen atoms, a C3-C7-cycloalkyl-C1-C6-alkyl, a C1-C6-benzyloxycarbonyl, a C1-C6-alkoxy-C1-C6-alkylcarbonyl, a C1-C6-alkylsulfonyl, and a C1-C6-halogenoalkylsulfonyl having 1 to 5 halogen atoms;
• and
• Het is a substituted pyrazole linked by a carbon atom selected from the group consisting of:
• wherein:
• R36 is selected from the group consisting of a halogen atom, a cyano group, a nitro group, a C1-C4-alkyl, a C1-C4-halogenoalkyl having 1 to 5 halogen atoms, a C3-C6-cycloalkyl, a C1-C4-alkoxy, a C1-C4-halogenoalkoxy having 1 to 5 halogen atoms, a C1-C4-alkylthio, a C1-C4-halogenoalkylthio having 1 to 5 halogen atoms, an aminocarbonyl group, and an aminocarbonyl-C1-C4-alkyl;
• R37 is selected from the group consisting of a hydrogen atom, a halogen atom, a cyano group, a nitro group, a C1-C4-alkyl, a C1-C4-alkoxy, and a C1-C4-alkylthio;
• and
• R38 is selected from the group consisting of a hydrogen atom, a phenyl, a C1-C4-alkyl, a C1-C4-halogenoalkyl having 1 to 5 halogen atoms, a hydroxy-C1-C4-alkyl, a C2-C6-alkenyl, a C3-C6-cycloalkyl, a C1-C4-alkylthio-C1-C4-alkyl, a C1-C4-halogenoalkylthio-C1-C4-alkyl having 1 to 5 halogen atoms, a C1-C4-alkoxy-C1-C4-alkyl, and a C1-C4-halogenoalkoxy-C1-C4-alkyl having 1 to 5 halogen atoms;
• wherein:
• R39 is selected from the group consisting of a hydrogen atom, a halogen atom, a cyano group, a nitro group, a C1-C4-alkyl, a C1-C4-halogenoalkyl having 1 to 5 halogen atoms, a C3-C6-cycloalkyl, a C1-C4-alkoxy, a C1-C4-halogenoalkoxy having 1 to 5 halogen atoms, a C1-C4-alkylthio, a C1-C4-halogenoalkylthio having 1 to 5 halogen atoms, an aminocarbonyl, and an aminocarbonyl-C1-C4-alkyl;
• R40 is selected from the group consisting of a hydrogen atom, a halogen atom, a cyano group, a C1-C4-alkyl, a C1-C4-alkoxy, a C1-C4-halogenoalkoxy having 1 to 5 halogen atoms, and a C1-C4-alkylthio;
• and
• R41 is selected from the group consisting of a hydrogen atom, a C1-C4-alkyl, a C1-C4-halogenoalkyl having 1 to 5 halogen atoms, a hydroxy-C1-C4-alkyl, a C2-C6-alkenyl, a C3-C6-cycloalkyl, a C1-C4-alkylthio-C1-C4-alkyl, a C1-C4-halogenoalkylthio-C1-C4-alkyl having 1 to 5 halogen atoms, a C1-C4-alkoxy-C1-C4-alkyl, a C1-C4-halogenoalkoxy-C1-C4-alkyl having 1 to 5 halogen atoms, and a phenyl optionally substituted by a halogen atom, a C1-C4-alkyl, a C1-C4-alkoxyalkyl or a nitro group;
• provided that the R39 and R40 are not both a hydrogen atom;
• and
• wherein:
• R42 is selected from the group consisting of a hydrogen atom, a halogen atom, a cyano group, a nitro group, a C1-C4-alkyl, a C1-C4-halogenoalkyl having 1 to 5 halogen atoms, a C3-C6-cycloalkyl, a C1-C4-alkoxy, a C1-C4-halogenoalkoxy having 1 to 5 halogen atoms, a C1-C4-alkylthio, a C1-C4-halogenoalkylthio having 1 to 5 halogen atoms, an aminocarbonyl, and an aminocarbonyl-C1-C4-alkyl;
• R43 is selected from the group consisting of a hydrogen atom, a halogen atom, a cyano group, a C1-C4-alkyl, a C1-C4-alkoxy, a C1-C4-alkylthio, and a C1-C4-halogenoalkyl having 1 to 5 halogen atoms;
• R44 is selected from the group consisting of a hydrogen atom, a phenyl, a benzyl, a C1-C4-alkyl, a C1-C4-halogenoalkyl having 1 to 5 halogen atoms, a hydroxy-C1-C4-alkyl, a C2-C6-alkenyl, a C3-C6-cycloalkyl, a C1-C4-alkylthio-C1-C4-alkyl, a C1-C4-halogenoalkylthio-C1-C4-alkyl having 1 to 5 halogen atoms, a C1-C4-alkoxy-C1-C4-alkyl, and a C1-C4-halogenoalkoxy-C1-C4-alkyl having 1 to 5 halogen atoms;
• provided that R43 and R44 are not both a hydrogen atom;
• or a salt, N-oxide, or optically active isomer thereof.