2-pyridinylethylcarboxamide derivatives and their use as fungicides

1. A compound of formula (I)

in which:

n is 1, 2 or 3;

R a is a C 1 -C 6 -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 C 1 -C 6 -alkyl, and a C 1 -C 6 -halogenoalkyl;

R 1 , R 2 , R 3 and R 4 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)-C 1 -C 6 -alkyl group, a C 1 -C 6 -alkyl, a C 2 -C 6 -alkenyl, a C 2 -C 6 -alkynyl, a C 1 -C 6 -alkylamino, a di-C 1 -C 6 -alkylamino, a C 1 -C 6 -alkoxy, a C 1 -C 6 -halogenoalkyl having 1 to 5 halogen atoms, a C 1 -C 6 -halogenoalkoxy having 1 to 5 halogen atoms, a C 1 -C 6 -alkylsulfanyl, a C 1 -C 6 -halogenoalkylsulfanyl having 1 to 5 halogen atoms, a C 2 -C 6 -alkenyloxy, a C 2 -C 6 -halogenoalkenyloxy having 1 to 5 halogen atoms, a C 3 -C 6 -alkynyloxy, a C 3 -C 6 -halogenoalkynyloxy having 1 to 5 halogen atoms, a C 3 -C 6 -cycloalkyl, a C 3 -C 6 -halogenocycloalkyl having 1 to 5 halogen atoms, a C 1 -C 6 -alkylcarbonyl, a C 1 -C 6 -halogenoalkylcarbonyl having 1 to 5 halogen atoms, a C 1 -C 6 -alkylcarbamoyl, a di-C 1 -C 6 -alkylcarbamoyl, a N—C 1 -C 6 -alkyloxycarbamoyl, a C 1 -C 6 -alkoxycarbamoyl, a N—C 1 -C 6 -alkyl-C 1 -C 6 -alkoxycarbamoyl, a C 1 -C 6 -alkoxycarbonyl, a C 1 -C 6 -halogenoalkoxycarbonyl having 1 to 5 halogen atoms, a C 1 -C 6 -alkylcarbonyloxy, a C 1 -C 6 -halogenoalkylcarbonyloxy having 1 to 5 halogen atoms, a C 1 -C 6 -alkylcarbonylamino, a C 1 -C 6 -halogenoalkylcarbonylamino having 1 to 5 halogen atoms, a C 1 -C 6 -alkylaminocarbonyloxy, a di-C 1 -C 6 -alkylaminocarbonyloxy, a C 1 -C 6 -alkyloxycarbonyloxy, a C 1 -C 6 -alkylsulfenyl, a C 1 -C 6 -halogenoalkylsulfenyl having 1 to 5 halogen atoms, a C 1 -C 6 -alkylsulfinyl, a C 1 -C 6 -halogenoalkylsulfinyl having 1 to 5 halogen atoms, a C 1 -C 6 -alkylsulfonyl, a C 1 -C 6 -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 R 1 and R 2 may form together a cyclopropyl, a cyclobutyl, a cyclopentyl or a cyclohexyl;

with the proviso that when three of the four substituents R 1 , R 2 , R 3 and R 4 are a hydrogen atom, then the fourth substituent is not a hydrogen atom;

R 5 is selected from the group consisting of a hydrogen atom, a cyano group, a formyl group, a hydroxy group, a C 1 -C 6 -alkyl, a C 1 -C 6 -halogenoalkyl having 1 to 5 halogen atoms, a C 1 -C 6 -alkoxy, a C 1 -C 6 -halogenoalkoxy having 1 to 5 halogen atoms, a C 3 -C 6 -cycloalkyl, a C 3 -C 6 -halogenocycloalkyl having 1 to 5 halogen atoms, a C 2 -C 6 -alkenyl, a C 2 -C 6 -alkynyl, a C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, a C 1 -C 6 -cyanoalkyl, a C 1 -C 6 -aminoalkyl, a C 1 -C 6 -alkylamino-C 1 -C 6 -alkyl, a di-C 1 -C 6 -alkylamino-C 1 -C 6 -alkyl, a C 1 -C 6 -alkylcarbonyl, a C 1 -C 6 -halogenalkylcarbonyl having 1 to 5 halogen atoms, a C 1 -C 6 -alkyloxycarbonyl, a C 3 -C 7 -cycloalkyl, a C 3 -C 7 -halogenocycloalkyl having 1 to 5 halogen atoms, a C 3 -C 7 -cycloalkyl-C 1 -C 6 -alkyl, a C 1 -C 6 -benzyloxycarbonyl, a C 1 -C 6 -alkoxy-C 1 -C 6 -alkylcarbonyl, a C 1 -C 6 -alkylsulfonyl, and a C 1 -C 6 -halogenoalkylsulfonyl having 1 to 5 halogen atoms; and

Het is a substituted thiophene linked by a carbon atom selected from the group consisting of:

wherein:

R 14 and R 15 are independently selected from the group consisting of a hydrogen atom, a halogen atom, a C 1 -C 4 -alkyl, a C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, a C 1 -C 4 -alkylthio, a C 1 -C 4 -alkylsulphonyl, a phenyl optionally substituted by a halogen atom or a C 1 -C 4 -alkyl, and a pyridyl optionally substituted by a halogen atom or a C 1 -C 4 -alkyl;

R 16 is selected from the group consisting of a halogen atom, a cyano group, a C 1 -C 4 -alkyl, a C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, and a C 1 -C 4 -halogenoalkoxy having 1 to 5 halogen atoms;

R 17 and R 18 are independently selected from the group consisting of a hydrogen atom, a halogen atom, a C 1 -C 4 -alkyl, a C 1 -C 4 -alkyloxy, and a C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms; and

R 19 is selected from the group consisting of a hydrogen atom, a halogen atom, a C 1 -C 4 -alkyl, and a C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms;

provided that R 18 and R 19 are not both a hydrogen atom;

or a salt, N-oxide, or optically active isomer thereof.

2. The compound of claim 1 wherein n is 1 or 2.

3. The compound of claim 1 wherein X is a halogen atom.

4. The compound of claim 3 wherein X is chlorine.

5. The compound of claim 1 wherein R a is —CF 3 .

6. The compound of claim 1 wherein the 2-pyridyl is substituted in the 3- and/or in the 5-position.

7. The compound of claim 6 wherein the 2-pyridyl is substituted in the 3-position by X and in the 5-position by R a .

8. The compound of claim 1 wherein the 2-pyridyl is substituted in the 3-position by —Cl and in the 5-position by —CF 3 .

9. The compound of claim 1 wherein R 1 and R 2 are independently selected from the group consisting of a hydrogen atom, a halogen atom, a cyano group, a hydroxy group, a C 3 -C 6 -alkyl, a C 1 -C 6 -halogenoalkyl having 1 to 5 halogen atoms, a C 2 -C 6 -alkenyl, a C 1 -C 6 -alkoxy, a C 1 -C 6 -alkylsulfanyl, a C 1 -C 6 -alkylsulfenyl, a C 1 -C 6 -alkylsulfinyl, a C 1 -C 6 -alkoxycarbonyl, a C 1 -C 6 -alkylcarbonylamino, a C 1 -C 6 -alkoxycarbonyloxy, a C 1 -C 6 -alkoxycarbonylamino, and a phenyl group.

10. The compound of claim 9 wherein R 1 and R 2 are independently selected from the group consisting of a halogen atom, a C 1 -C 6 -alkyl, a C 1 -C 6 -halogenoalkyl having 1 to 5 halogen atoms, and a C 1 -C 6 -alkylcarbonylamino.

11. The compound of claim 1 wherein R 3 and R 4 are independently selected from the group consisting of a hydrogen atom, a halogen atom, a cyano group, a C 1 -C 6 -alkyl, a C 1 -C 6 -halogenoalkyl having 1 to 5 halogen atoms, a C 1 -C 6 -alkylcarbonylamino, and a phenyl group.

12. The compound of claim 11 wherein R 3 and R 4 are independently selected from the group consisting of a halogen atom, a C 1 -C 6 -alkyl, a C 1 -C 6 -halogenoalkyl having 1 to 5 halogen atoms, and a phenyl group.

13. The compound of claim 1 wherein R 5 is selected from the group consisting of a hydrogen atom, and a C 3 -C 7 -cycloalkyl.

14. A fungicidal composition comprising an effective amount of a compound according to claim 1 and an agriculturally acceptable support.

15. A method for combating the phytopathogenic fungi of crops, wherein an effective and non-phytotoxic amount of a composition according to claim 14 is applied to the plant seeds or to the plant leaves and/or to the fruits of the plants or to the soil in which the plants are growing or in which it is desired to grow them.