Fungicide N-6-membered fused (hetero) aryl-methylene-N-cycloalkyl carboxamide derivatives

1. A compound of formula (I)

wherein

A is selected from the group consisting of:

wherein:

V 1 is selected from the group consisting of O, 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 3 -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;

B is selected from the group consisting of

wherein

W 1 through W 5 are independently selected from the group consisting of N and CR b1 ;

Y 1a , Y 2a , Y 3a and Y 3b are independently selected from the group consisting of NR b2 and CR b3 ;

Y 2b is selected from the group consisting of O, S, and NR b2 ;

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

Z 1 is selected from the group consisting a non-substituted C 3 -C 7 -cycloalkyl or a C 3 -C 7 -cycloalkyl substituted by up to ten atoms or groups independently selected from the group consisting of 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;

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;

each R b1 and R b3 is 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;

each 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 can be substituted by up to 5 groups Q; and benzyl 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 1 -C 8 )alkylsilyl; tri(C 1 -C 8 )alkylsilyl-C 1 -C 8 -alkyl; C 1 -C 8 -alkoxyimino; (C 1 -C 8 -alkoxyimino)-C 1 -C 8 -alkyl;

or a 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 A 5 ;

V 1 represents NR a1 ;

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

R a2 and R a3 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; or

A is A 4 ;

V 1 is S;

R a2 is selected from the group consisting of C 1 -C 8 -alkyl and 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.

4. The compound of claim 1 wherein

B is B 1 or B 2 ; W 1 through W 5 are independently selected from the group consisting of CR b1 , and Y 1a , Y 2a , Y 3a and Y 3b are independently selected from the group consisting of CR b3 ; or

B is B 5 or B 6 ; W 1 through W 5 are independently selected from the group consisting of CR b1 , Y 1a and Y 3a are independently selected from the group consisting of CR b3 ; and Y 2b is S.

5. The compound of claim 1 wherein T is selected from the group consisting of O and S.

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 a 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. A compound of the structural formula:

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 compound of claim 12 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. 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.