Fungicidal N-cycloalkyl-carboxamide derivatives

1. A compound of formula (I)

wherein

R 1 is C 1 -C 8 -alkyl;

R 2 and R 3 are independently selected from the group consisting of a hydrogen atom; a halogen atom; C 1 -C 8 -alkyl; and C 1 -C 8 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different;

T is selected from the group consisting of O, S, N—R a , N—OR a , N—NR a R b , and N—CN;

R a and R b are independently selected from the group consisting of a hydrogen atom;

C 1 -C 8 -alkyl; C 1 -C 8 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different; C 1 -C 8 -alkoxy-C 1 -C 8 -alkyl; C 2 -C 8 -alkenyl; C 2 -C 8 -halogenoalkenyl comprising up to 9 halogen atoms that can be the same or different; C 2 -C 8 -alkynyl; C 2 -C 8 -halogenoalkynyl comprising up to 9 halogen atoms that can be the same or different; C 3 -C 7 -cycloalkyl;

C 3 -C 7 -cycloalkyl-C 1 -C 8 -alkyl; C 3 -C 7 -halogenocycloalkyl comprising up to 9 halogen atoms that can be the same or different; formyl; C 1 -C 8 -alkylcarbonyl; C 1 -C 8 -halogenoalkylcarbonyl comprising up to 9 halogen atoms that can be the same or different; C 1 -C 8 -alkylsulfonyl;

C 1 -C 8 -halogenoalkylsulfonyl comprising up to 9 halogen atoms that can be the same or different;

phenyl that can be substituted by up to 5 groups Q; naphthyl that can be substituted by up to 6 groups Q; phenylmethylene that can be substituted by up to 5 groups Q; phenylsulfonyl that can be substituted by up to 5 groups Q;

B represents a carbo-linked, unsaturated, 5-membered heterocyclyl group that can be substituted by up to four groups X;

Z 1 is selected from the group consisting of a non-substituted C 3 -C 7 -cycloalkyl and a C 3 -C 7 -cycloalkyl substituted by up to 10 atoms or groups that can be the same or different and are selected from the group consisting of a halogen atom; cyano; C 1 -C 8 -alkyl; C 1 -C 8 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different; C 1 -C 8 -alkoxy;

C 1 -C 8 -halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different;

C 1 -C 8 alkoxycarbonyl; and C 1 -C 8 -halogenoalkoxycarbonyl comprising up to 9 halogen atoms that can be the same or different;

Z 2 and Z 3 are independently selected from the group consisting of a hydrogen atom; a halogen atom; C 1 -C 8 -alkyl; C 1 -C 8 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different; C 2 -C 8 -alkenyl; C 2 -C 8 -alkynyl; cyano; nitro; C 1 -C 8 -alkoxy;

C 2 -C 8 -alkenyloxy; C 2 -C 8 -alkynyloxy; C 3 -C 7 -cycloalkyl; C 1 -C 8 -alkylsulphenyl; amino;

C 1 -C 8 -alkylamino; di-C 1 -C 8 -alkylamino; C 1 -C 8 -alkoxycarbonyl; C 1 -C 8 alkylcarbonyl;

C 1 -C 8 -alkylcarbamoyl; di-C 1 -C 8 -alkylcarbamoyl; and N—C 1 -C 8 -alkyl-C 1 -C 8 -alkoxycarbamoyl; or

Z 2 and Z 3 together with the carbon atom to which they are linked can form a substituted or non-substituted C 3 -C 7 -cycloalkyl;

each X is independently selected from the group consisting of a hydrogen atom; a halogen atom; nitro; cyano; hydroxyl; sulfanyl; amino; pentafluoro-λ 6 -sulfanyl; C 1 -C 8 -alkyl;

C 1 -C 8 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different;

C 1 -C 8 -alkylamino; di-C 1 -C 8 -alkylamino; C 1 -C 8 -alkoxy; C 1 -C 8 -halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different; C 1 -C 8 -alkoxy-C 1 -C 8 -alkyl; C 1 -C 8 -alkylsulfanyl;

C 1 -C 8 -halogenoalkylsulfanyl comprising up to 9 halogen atoms that can be the same or different;

C 1 -C 8 -alkylsulfenyl; C 1 -C 8 -halogenoalkylsulfenyl comprising up to 9 halogen atoms that can be the same or different, C 1 -C 8 -alkylsulfinyl; C 1 -C 8 -halogenoalkylsulfinyl comprising up to 9 halogen atoms that can be the same or different; C 1 -C 8 -alkylsulfonyl;

C 1 -C 8 -halogenoalkylsulfonyl comprising up to 9 halogen atoms that can be the same or different;

C 2 -C 8 -alkenyl; C 2 -C 8 -halogenoalkenyl comprising up to 9 halogen atoms that can be the same or different; C 2 -C 8 -alkynyl; C 2 -C 8 -halogenoalkynyl comprising up to 9 halogen atoms that can be the same or different; C 2 -C 8 -alkenyloxy; C 2 -C 8 -halogenoalkenyloxy comprising up to 9 halogen atoms that can be the same or different; C 2 -C 8 -alkynyloxy; C 2 -C 8 -halogenoalkynyloxy comprising up to 9 halogen atoms that can be the same or different; C 3 -C 7 -cycloalkyl;

C 3 -C 7 -cycloalkyl-C 1 -C 8 -alkyl; C 3 -C 7 -halogenocycloalkyl comprising up to 9 halogen atoms that can be the same or different; formyl; formyloxy; formylamino; carboxy; carbamoyl;

N-hydroxycarbamoyl; carbamate; (hydroxyimino)-C 1 -C 8 -alkyl; C 1 -C 8 -alkylcarbonyl;

C 1 -C 8 -halogenoalkylcarbonyl comprising up to 9 halogen atoms that can be the same or different;

N—C 1 -C 8 -alkyl-C 1 -C 8 -alkoxycarbamoyl; C 1 -C 8 -alkylcarbonyloxy;

C 1 -C 8 -halogenoalkylcarbonyloxy comprising up to 9 halogen atoms that can be the same or different; C 1 -C 8 -alkylcarbonylamino; C 1 -C 8 -alkylaminocarbonyloxy;

di-C 1 -C 8 -alkylaminocarbonyloxy; C 1 -C 8 -alkyloxycarbonyloxy; C 1 -C 8 -alkoxyimino;

(C 1 -C 8 -alkoxyimino)-C 1 -C 8 -alkyl; (C 1 -C 8 -alkenyloxyimino)-C 1 -C 8 -alkyl;

(C 1 -C 8 -alkynyloxyimino)-C 1 -C 8 -alkyl; (benzyloxyimino)-C 1 -C 8 -alkyl; tri(C 1 -C 8 -alkyl)silyl;

tri(C 1 -C 8 -alkyl)silyl-C 1 -C 8 -alkyl; phenyl that can be substituted by up to 5 groups Q; benzyloxy that can be substituted by up to 5 groups Q; benzylsulfanyl that can be substituted by up to 5 groups Q; benzylamino that can be substituted by up to 5 groups Q; phenoxy that can be substituted by up to 5 groups Q; phenylamino that can be substituted by up to 5 groups Q;

phenylsulfanyl that can be substituted by up to 5 groups Q; benzyl that can be substituted by up to 5 groups Q; pyridinyl that can be substituted by up to four groups Q; and pyridinyloxy that can be substituted by up to four groups Q;

each Q is independently selected from the group consisting of a halogen atom; cyano; nitro; C 1 -C 8 -alkyl; C 1 -C 8 -alkoxy; C 1 -C 8 -alkylsulfanyl; C 1 -C 8 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different; C 1 -C 8 -halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different; tri(C 1 -C 8 )alkylsilyl;

tri(C 1 -C 8 )alkylsilyl-C 1 -C 8 -alkyl; C 1 -C 8 -alkoxyimino; and (C 1 -C 8 -alkoxyimino)-C 1 -C 8 -alkyl;

as well as salts, N-oxides, and optically active or geometric isomers thereof.

2. The compound of claim 1 wherein B is

wherein:

-* represents the bond to the methylene group;

W 2 is selected from the group consisting of O, S, and NX 1 ;

X 1 is selected from the group consisting of a hydrogen atom; C 1 -C 8 -alkyl;

C 1 -C 8 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different; and

C 1 -C 8 -alkoxy-C 1 -C 8 -alkyl;

each X 2 is independently selected from the group consisting of a hydrogen atom; a halogen atom; cyano; C 1 -C 8 -alkyl; C 1 -C 8 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different; C 1 -C 8 -alkoxy; C 1 -C 8 -halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different; C 3 -C 7 -cycloalkyl; phenyl that can be substituted by up to 5 groups Q; phenoxy that can be substituted by up to 5 groups Q; benzyl that can be substituted by up to 5 groups Q; C 1 -C 8 -alkoxyimino; and (C 1 -C 8 -alkoxyimino)-C 1 -C 8 -alkyl; and

n=1, 2 or 3.

3. The compound of claim 2 wherein W 2 is sulfur.

4. The compound of claim 1 wherein said compound is

5. The compound of claim 1 wherein B is selected in the group consisting of:

wherein:

-* represents the bond to the methylene group;

W 2 is selected from the group consisting of O, S, and NX 1 ;

X 1 is selected from the group consisting of a hydrogen atom;

C 1 -C 8 -alkyl; C 1 -C 8 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different; and C 1 -C 8 -alkoxy-C 1 -C 8 -alkyl;

each X 2 is independently selected from the group consisting of a hydrogen atom; a halogen atom; cyano; C 1 -C 8 -alkyl; C 1 -C 8 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different; C 1 -C 8 -alkoxy;

C 1 -C 8 -halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different;

C 3 -C 7 -cycloalkyl; phenyl that can be substituted by up to 5 groups Q; phenoxy that can be substituted by up to 5 groups Q; benzyl that can be substituted by up to 5 groups Q;

C 1 -C 8 -alkoxyimino; and (C 1 -C 8 -alkoxyimino)-C 1 -C 8 -alkyl; and

n=1, 2 or 3.

6. The compound of claim 1 wherein T is selected from the group consisting of oxygen and sulfur.

7. The compound of claim 1 wherein T is oxygen.

8. The compound of claim 1 wherein Z 1 is cyclopropyl.

9. The compound of claim 1 wherein Z 2 and Z 3 are independently selected from the group consisting of a hydrogen atom and C 1 -C 8 alkyl.

10. A fungicide composition comprising, as an active ingredient, an agronomically effective and substantially non-phytotoxic quantity of a compound of formula (I) according to claim 1 and an agriculturally acceptable support, carrier or filler.

11. A method for controlling phytopathogenic fungi of crops comprising applying an agronomically effective and substantially non-phytotoxic quantity of a compound according to claim 1 to the soil where plants grow or are capable of growing, to the leaves and/or the fruit of plants or to the seeds of plants.

12. A method for controlling phytopathogenic fungi of crops comprising applying an agronomically effective and substantially non-phytotoxic quantity of a composition according to claim 10 to the soil where plants grow or are capable of growing, to the leaves and/or the fruit of plants or to the seeds of plants.