Fungicide N-5-membered fused heteroaryl-methylene-N-cycloalkyl-carboxamide derivatives

1. A compound of formula (I)

wherein A is selected in the group consisting of:

wherein:

V 1 is selected from the group consisting of S and NR a1 ;

R a1 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;

R a2 and R a3 are 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; and C 3 -C 7 -cycloalkyl;

R a4 is 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; C 1 -C 8 -alkylsulfanyl; amino; C 1 -C 8 -alkylamino; di-(C 1 -C 8 -alkyl)amino; and C 1 -C 8 -alkyloxycarbonyl;

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

R c and R d 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; and phenylsulfonyl that can be substituted by up to 5 groups Q;

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 atoms; 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; C 1 -C 8 -halogenoalkoxycarbonyl comprising up to 9 halogen atoms that can be the same or different; C 1 -C 8 -alkylaminocarbonyl; and di-(C 1 -C 8 -alkyl)aminocarbonyl;

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 -alkylsulfenyl; amino; C 1 -C 8 -alkylamino; di-(C 1 -C 8 -alkyl)amino; C 1 -C 8 -alkoxycarbonyl; C 1 -C 8 -alkylcarbonyl; C 1 -C 8 -alkylcarbamoyl; di-(C 1 -C 8 -alkyl)carbamoyl; 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;

W 1 , W 2 , W 3 , and W 4 are independently selected from the group consisting of N, O, S, CR b1 , and NR b2 , provided that at least one of W 1 , W 2 , W 3 , and W 4 is a heteroatom;

Y 1 , Y 2 , and Y 3 are independently selected from the group consisting of N and CR b3 ; Y 1 , Y 2 , and Y 3 together with the atoms W n to which they are linked, form an unsaturated 5-membered or 6-membered fused heterocyclyl ring containing up to four heteroatoms, or an unsaturated 6-membered fused carbocyclyl ring;

p is 1 or 2;

R b1 and R b3 are independently selected from the group consisting of a hydrogen atom; 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 -alkyl)amino; 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 -alkoxycarbonyl; C 1 -C 8 -halogenoalkoxycarbonyl comprising up to 9 halogen atoms that can be the same or different; C 1 -C 8 -alkylaminocarbonyl; di-(C 1 -C 8 -alkyl)aminocarbonyl; 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 -alkyl)aminocarbonyloxy; 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;

R b2 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; 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; phenylsulfonyl that can be substituted by up to 5 groups Q; benzyl that can be substituted by up to 5 groups Q; and phenyl that can be substituted by up to 5 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 i -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 any salt, N-oxide, or optically active or geometric isomer thereof.

2. The compound of claim 1 wherein:

R a1 is selected from the group consisting of a hydrogen atom; C 1 -C 8 -alkyl; and C 1 -C 8 -alkoxy-C 1 -C 8 -alkyl;

R a2 is selected from the group consisting of 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;

R a3 is selected from the group consisting of a hydrogen atom; a halogen atom; and C 1 -C 8 -alkyl; and

R a4 is 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.

3. The compound of claim 1 wherein:

A is

V 1 is NR a1;

R a1 is C 1 -C 8 -alkyl; and

R a2 and R a4 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.

4. The compound of claim 1 wherein:

A is

V 1 is S;

R a2 is selected from the group consisting of a C 1 -C 8 -alkyl and a C 1 -C 8 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different; and

R a4 is selected from the group consisting of a hydrogen 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.

5. The compound of claim 1 wherein T is selected from the group consisting of an oxygen atom and a sulfur atom.

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

7. 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.

8. The compound of claim 1 wherein Q is selected from the group consisting of a halogen atom; C 1 -C 8 -alkyl; C 1 -C 8 -alkoxy; C 1 -C 8 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different; and C 1 -C 8 -halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different.

9. A fungicide composition comprising, as an active ingredient, an effective amount of the compound of claim 1 and an agriculturally acceptable support, carrier or filler.

10. A method for controlling phytopathogenic fungi of crops comprising applying an agronomically effective and substantially non-phytotoxic quantity of the compound of 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.

11. A method for controlling phytopathogenic fungi of crops comprising applying an agronomically effective and substantially non-phytotoxic quantity of the composition of claim 9 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. The compound of claim 6 wherein:

V 1 is NR a1 ;

R a1 is C 1 -C 8 -alkyl;

R a2 is selected from the group consisting of a C 1 -C 8 -alkyl; C 1 -C 8 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different;

R a4 is selected from the group consisting of a hydrogen atom and a halogen atom;

T is selected from the group consisting of O and S; and

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

13. A fungicide composition comprising, as an active ingredient, an effective amount of the compound of claim 12 and an agriculturally acceptable support, carrier or filler.

14. A method for controlling phytopathogenic fungi of crops comprising applying an agronomically effective and substantially non-phytotoxic quantity of the composition of claim 13 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.

15. The compound of the formula:

16. A fungicide composition comprising, as an active ingredient, an effective amount of the compound of claim 15 and an agriculturally acceptable support, carrier or filler.

17. A method for controlling phytopathogenic fungi of crops comprising applying an agronomically effective and substantially non-phytotoxic quantity of the composition of claim 16 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.