IP Library › Granted Patent US 8,088,927

Granted Patent B2

US 8,088,927 · App. 12/223,105 · Granted Jan 3, 2012

Fungicide N-cycloalkyl-benzyl-amide derivatives

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Quick Facts

Patent No.: US 8,088,927
App. No.: 12/223,105
Granted: Jan 3, 2012
Kind: B2

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Abstract

The present invention relates to N-cycloalkyl-benzyl-amide derivatives of formula (I) wherein the substituents are as in the description, their process of preparation, their use as fungicide active agents, particularly in the form of fungicide compositions, and methods for the control of phytopathogenic fungi, notably of plants, using these compounds or compositions:

Claims (141)

1. A compound of formula (I)

wherein

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

Z 1 represents a non substituted C 3 -C 7 -cycloalkyl or a C 3 -C 7 cycloalkyl substituted by up to 10 atoms or groups which can be the same or different and which can be 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 which can be the same or different; C 1 -C 8 -alkoxy; C 1 -C 8 -halogenoalkoxy comprising up to 9 halogen atoms which can be the same or different; C 1 -C 8 -alkoxycarbonyl; C 1 -C 8 -halogenoalkoxycarbonyl comprising up to 9 halogen atoms which can be the same or different; C 1 -C 8 -alkylaminocarbonyl and di-C 1 -C 8 -alkylaminocarbonyl;

Z 2 and Z 3 , which can be the same or different, represent a hydrogen atom; C 1 -C 8 -alkyl; C 2 -C 8 -alkenyl; C 2 -C 8 -alkynyl; cyano; nitro; a halogen atom; 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 -alkylcarbamoyl; di-C 1 -C 8 -alkylcarbamoyl; 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;

X, which can be the same or different, represents a halogen atom; nitro; cyano; hydroxyl; sulfanyl; amino; pentafluoro-λ6-sulfanyl; C 1 -C 8 -alkyl; C 1 -C 8 -halogenoalkyl comprising up to 9 halogen atoms which 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 which 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 which can be the same or different; C 2 -C 8 -alkenyl; C 2 -C 8 -halogenoalkenyl comprising up to 9 halogen atoms which can be the same or different; C 2 -C 8 -alkynyl; C 2 -C 8 -halogenoalkynyl comprising up to 9 halogen atoms which can be the same or different C 2 -C 8 -alkenyloxy; C 2 -C 8 -halogenoalkenyloxy comprising up to 9 halogen atoms which can be the same or different; C 2 -C 8 -alkinyloxy; C 2 -C 8 -halogenoalkinyloxy comprising up to 9 halogen atoms which 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 which 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 which can be the same or different; C 1 -C 8 -alkylcarbamoyl; di-C 1 -C 8 -alkylcarbamoyl; N—C 1 -C 8 -alkyloxycarbamoyl; C 1 -C 8 -alkoxycarbamoyl; 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 which can be the same or different; C 1 -C 8 -alkylaminocarbonyl; di-C 1 -C 8 -alkylaminocarbonyl; C 1 -C 8 -alkylcarbonyloxy; C 1 -C 8 -halogenoalkylcarbonyloxy comprising up to 9 halogen atoms which can be the same or different; C 1 -C 8 -alkylcarbonylamino; C 1 -C 8 -halogenoalkylcarbonylamino comprising up to 9 halogen atoms which can be the same or different; C 1 -C 8 -alkylaminocarbonyloxy; alkylaminocarbonyloxy C 1 -C 8 -alkyloxycarbonyloxy, alkylsulphenyl, C 1 -C 8 -halogenoalkylsulphenyl comprising up to 9 halogen atoms which can be the same or different, C 1 -C 8 -alkylsulphinyl, C 1 -C 8 -halogenoalkylsulphinyl comprising up to 9 halogen atoms which can be the same or different, C 1 -C 8 -alkylsulphonyl, C 1 -C 8 -halogenoalkylsulphonyl comprising up to 9 halogen atoms which can be the same or different, 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, a (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; benzyloxy which can be substituted by up to 5 groups Q; benzylsulfanyl which can be substituted by up to 5 groups Q; benzylamino which can be substituted by up to 5 groups Q; naphthyl which can be substituted by up to 6 groups Q; phenoxy which can be substituted by up to 5 groups Q; phenylamino which can be substituted by up to 5 groups Q; phenylsulfanyl which can be substituted by up to 5 groups Q; phenylmethylene which can be substituted by up to 5 groups Q; pyridinyl which can be substituted by up to four groups Q and pyridinyloxy which can be substituted by up to four groups Q;

two substituents X together with the consecutive carbon atoms to which they are linked can form a 5- or 6-membered, saturated, carbo- or hetero-cycle, which can be substituted by up to four groups Q which can be the same or different;

n represents 1, 2, 3, 4 or 5;

R, which can be the same or different, represent hydrogen atom; halogen atom; cyano; nitro; amino; sulfanyl; pentafluoro-λ-6-sulfanyl; C 1 -C 8 -alkylamino; di-C 1 -C 8 -alkylamino; tri(C 1 -C 8 -alkyl)silyl; C 1 -C 8 -alkylsulfanyl; C 1 -C 8 -halogenoalkylsulfanyl comprising up to 9 halogen atoms which can be the same or different; C 1 -C 8 -alkyl; C 1 -C 8 -halogenoalkyl comprising up to 9 halogen atoms which can be the same or different; C 2 -C 8 -alkenyl; C 2 -C 8 -halogenoalkenyl comprising up to 9 halogen atoms which can be the same or different; C 2 -C 8 -alkynyl; C 2 -C 8 -halogenoalkynyl comprising up to 9 halogen atoms which can be the same or different; C 1 -C 8 -alkoxy; C 1 -C 8 -halogenoalkoxy comprising up to 9 halogen atoms which can be the same or different; C 2 -C 8 -alkenyloxy; C 2 -C 8 -alkynyloxy; C 3 -C 7 -cycloalkyl; C 3 -C 7 -cycloalkyl-C 1 -C 8 -alkyl; C 1 -C 8 -alkylsulphinyl; C 1 -C 8 -alkylsulphonyl; C 1 -C 8 alkoxyimino; (C 1 -C 8 -alkoxyimino)-C 1 -C 8 -alkyl; (benzyloxyimino)-C 1 -C 8 -alkyl; phenoxy; benzyloxy; benzylsulfanyl; benzylamino; naphtyl; halogenophenoxy comprising up to 9 halogen atoms which can be the same or different; C 1 -C 8 -alkylcarbonyl; C 1 -C 8 -halogenoalkylcarbonyl comprising up to 9 halogen atoms which can be the same or different; C 1 -C 8 -alkoxycarbonyl; C 1 -C 8 -halogenoalkoxycarbonyl comprising up to 9 halogen atoms which can be the same or different; C 1 -C 8 -alkylaminocarbonyl; di-C 1 -C 8 -alkylaminocarbonyl;

Q, which can be the same or different, represents 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 which can be the same or different; C 1 -C 8 -halogenoalkoxy comprising up to 9 halogen atoms which can be the same or different; tri(C 1 -C 8 )alkylsilyl and tri(C 1 -C 8 )alkylsilyl-C 1 -C 8 -alkyl;

as well as salts, N-oxydes, metallic complexes, metalloidic complexes and optically active or geometric isomers thereof; with the exception of 2-furancarboxamide, N-(1,3-benzodioxol-5-ylmethyl)-N-cyclopentyl-5-methyl and 2-furancarboxamide, N-(1,3-benzodioxol-5-ylmethyl)-N-cyclopentyl-2,5-dimethyl.

2. A compound according to claim 1 wherein A is selected in the list consisting of:

a heterocycle of formula (A 1 )

wherein:

R 1 to R 3 which can be the same or different represent a hydrogen atom; a halogen atom; C 1 -C 5 -alkyl; C 1 -C 5 -halogenoalkyl comprising up to 9 halogen atoms which can be the same or different; C 1 -C 5 -alkoxy or C 1 -C 5 -halogenoalkoxy comprising up to 9 halogen atoms which can be the same or different;

a heterocycle of formula (A 2 )

wherein:

R 4 to R 6 which can be the same or different represent a hydrogen atom; a halogen atom; C 1 -C 5 -alkyl; C 1 -C 5 -halogenoalkyl comprising up to 9 halogen atoms which can be the same or different; C 1 -C 5 -alkoxy or C 1 -C 5 -halogenoalkoxy comprising up to 9 halogen atoms which can be the same or different;

a heterocycle of formula (A 3 )

wherein:

R 7 represents a hydrogen atom; a halogen atom; C 1 -C 5 -alkyl; C 1 -C 5 -halogenoalkyl comprising up to 9 halogen atoms which can be the same or different; C 1 -C 5 -alkoxy or C 1 -C 5 -halogenoalkoxy comprising up to 9 halogen atoms which can be the same or different;

R 8 represents a hydrogen atom or a C 1 -C 5 -alkyl;

a heterocycle of formula (A 4 )

wherein:

R 9 to R 11 which can be the same or different represent a hydrogen atom; a halogen atom; C 1 -C 5 -alkyl; amino; C 1 -C 5 -alkoxy; C 1 -C 5 -alkylthio C 1 -C 5 -halogenoalkyl comprising up to 9 halogen atoms which can be the same or different or C 1 -C 5 -halogenoalkoxy comprising up to 9 halogen atoms which can be the same or different;

a heterocycle of formula (A 5 )

wherein:

R 12 and R 13 which can be the same or different represent a hydrogen atom; a halogen atom; C 1 -C 5 -alkyl; C 1 -C 5 -alkoxy; amino; C 1 -C 5 -halogenoalkyl comprising up to 9 halogen atoms which can be the same or different or C 1 -C 5 -halogenoalkoxy comprising up to 9 halogen atoms which can be the same or different;

R 14 represents a hydrogen atom; a halogen atom; C 1 -C 5 -alkyl; C 1 -C 5 -alkoxy; amino; C 1 -C 5 -halogenoalkyl comprising up to 9 halogen atoms which can be the same or different or C 1 -C 5 -halogenoalkoxy comprising up to 9 halogen atoms which can be the same or different;

a heterocycle of formula (A 6 )

wherein:

R 15 represents a hydrogen atom; a halogen atom; a cyano; C 1 -C 5 -alkyl; C 1 -C 5 -alkoxy; C 1 -C 5 -halogenoalkoxy comprising up to 9 halogen atoms which can be the same or different or C 1 -C 5 -halogenoalkyl comprising up to 9 halogen atoms which can be the same or different;

R 16 and R 18 which can be the same or different represent a hydrogen atom; a halogen atom; C 1 -C 5 -alkoxycarbonyl; C 1 -C 5 -alkyl; C 1 -C 5 -halogenoalkoxy comprising up to 9 halogen atoms which can be the same or different or C 1 -C 5 -halogenoalkyl comprising up to 9 halogen atoms which can be the same or different;

R 17 represent a hydrogen atom or C 1 -C 5 -alkyl;

a heterocycle of formula (A 7 )

wherein:

R 19 represents a hydrogen atom or a C 1 -C 5 -alkyl;

R 20 to R 22 which can be the same or different represent a hydrogen atom; a halogen atom; C 1 -C 5 -alkyl or C 1 -C 5 -halogenoalkyl comprising up to 9 halogen atoms which can be the same or different;

a heterocycle of formula (A 8 )

wherein:

R 23 represents a hydrogen atom; a halogen atom; C 1 -C 5 -alkyl or C 1 -C 5 -halogenoalkyl comprising up to 9 halogen atoms which can be the same or different;

R 24 represents a hydrogen atom or C 1 -C 5 -alkyl or C 1 -C 5 -halogenoalkyl comprising up to 9 halogen atoms which can be the same or different;

a heterocycle of formula (A 9 )

wherein:

R 25 represents a hydrogen atom; a halogen atom; C 1 -C 5 -alkyl or C 1 -C 5 -halogenoalkyl comprising up to 9 halogen atoms which can be the same or different;

R 26 represents a hydrogen atom; C 1 -C 5 -alkyl or C 1 -C 5 -halogenoalkyl comprising up to 9 halogen atoms which can be the same or different;

a heterocycle of formula (A 10 )

wherein:

R 27 represents a hydrogen atom; a halogen atom; C 1 -C 5 -alkyl or C 1 -C 5 -halogenoalkyl comprising up to 9 halogen atoms which can be the same or different;

R 28 represents a hydrogen atom; a halogen atom; amino; C 1 -C 5 -alkyl or C 1 -C 5 -halogenoalkyl comprising up to 9 halogen atoms which can be the same or different;

a heterocycle of formula (A 11 )

wherein:

R 29 represents a hydrogen atom; a halogen atom; C 1 -C 5 -alkyl; C 1 -C 5 -alkoxy; C 1 -C 5 -halogenoalkoxy comprising up to 9 halogen atoms which can be the same or different or C 1 -C 5 -halogenoalkyl comprising up to 9 halogen atoms which can be the same or different;

R 30 represents a hydrogen atom; a bromine atom; a fluorine atom; an iodine atom; C 1 -C 5 -alkyl; C 1 -C 5 -halogenoalkyl comprising up to 9 halogen atoms which can be the same or different; C 1 -C 5 -halogenoalkoxy comprising up to 9 halogen atoms which can be the same or different; amino; C 1 -C 5 -alkylamino or di-C 1 -C 5 -alkylamino;

a heterocycle of formula (A 12 )

wherein:

R 31 represents a hydrogen atom; a halogen atom or a C 1 -C 5 -alkyl;

R 32 represents a hydrogen atom; a halogen atom; C 1 -C 5 -alkyl or C 1 -C 5 -halogenoalkyl comprising up to 9 halogen atoms which can be the same or different;

R 33 represents a hydrogen atom; a halogen atom; a nitro; C 1 -C 5 -alkyl; C 1 -C 5 -alkoxy; C 1 -C 5 -halogenoalkoxy comprising up to 9 halogen atoms which can be the same or different or C 1 -C 5 -halogenoalkyl comprising up to 9 halogen atoms which can be the same or different;

a heterocycle of formula (A 13 )

wherein:

R 34 represents a hydrogen atom; a halogen atom; C 1 -C 5 -alkyl; C 3 -C 5 -cycloalkyl; C 1 -C 5 -halogenoalkyl comprising up to 9 halogen atoms which can be the same or different; C 1 -C 5 -alkoxy; C 2 -C 5 -alkynyloxy or C 1 -C 5 -halogenoalkoxy comprising up to 9 halogen atoms which can be the same or different;

R 35 represents a hydrogen atom; a halogen atom; C 1 -C 5 -alkyl; a cyano; C 1 -C 5 -alkoxy; C 1 -C 5 -alkylthio; C 1 -C 5 -halogenoalkyl comprising up to 9 halogen atoms which can be the same or different; C 1 -C 5 -halogenoalkoxy comprising up to 9 halogen atoms which can be the same or different; amino; C 1 -C 5 -alkylamino or di(C 1 -C 5 -alkyl)amino;

R 36 represents a hydrogen atom or C 1 -C 5 -alkyl;

a heterocycle of formula (A 14 )

wherein:

R 37 and R 39 which can be the same or different represent a hydrogen atom; a halogen atom; C 1 -C 5 -alkyl or C 1 -C 5 -halogenoalkyl comprising up to 9 halogen atoms which can be the same or different;

R 38 represents a hydrogen atom or C 1 -C 5 -alkyl;

a heterocycle of formula (A 15 )

wherein:

R 40 and R 41 which can be the same or different represent a hydrogen atom; a halogen atom; C 1 -C 5 -alkyl or C 1 -C 5 -halogenoalkyl comprising up to 9 halogen atoms which can be the same or different;

a heterocycle of formula (A 16 )

wherein:

R 42 and R 43 which can be the same or different represent a hydrogen atom; a halogen atom; C 1 -C 5 -alkyl; C 1 -C 5 -halogenoalkyl comprising up to 9 halogen atoms which can be the same or different or amino;

a heterocycle of formula (A 17 )

wherein:

R 44 and R 45 which can be the same or different represent a hydrogen atom; a halogen atom; C 1 -C 5 -alkyl or C 1 -C 5 -halogenoalkyl comprising up to 9 halogen atoms which can be the same or different;

R 46 represents a hydrogen atom or C 1 -C 5 -alkyl;

a heterocycle of formula (A 18 )

wherein:

R 47 represents a hydrogen atom; a halogen atom; C 1 -C 5 -alkyl or C 1 -C 5 -halogenoalkyl comprising up to 9 halogen atoms which can be the same or different;

R 48 represents a hydrogen atom; a halogen atom; C 1 -C 5 -alkyl; C 1 -C 5 -halogenoalkyl comprising up to 9 halogen atoms which can be the same or different or C 1 -C 5 -alkylsulfanyl;

a heterocycle of formula (A 19 )

wherein:

R 49 and R 50 which can be the same or different represent a hydrogen atom; a halogen atom; C 1 -C 5 -alkyl; C 1 -C 5 -alkoxy; C 1 -C 5 -halogenoalkoxy comprising up to 9 halogen atoms which can be the same or different or C 1 -C 5 -halogenoalkyl comprising up to 9 halogen atoms which can be the same or different;

a heterocycle of formula (A 20 )

wherein:

R 51 represents a hydrogen atom; a halogen atom; C 1 -C 5 -alkyl or C 1 -C 5 -halogenoalkyl comprising up to 9 halogen atoms which can be the same or different;

a heterocycle of formula (A 21 )

wherein:

R 52 and R 53 which can be the same or different represent a hydrogen atom; a halogen atom; C 1 -C 5 -alkyl; C 1 -C 5 -halogenoalkyl comprising up to 9 halogen atoms which can be the same or different; C 1 -C 5 -alkoxy or a C 1 -C 5 -alkylthio;

R 54 represents a hydrogen atom or C 1 -C 5 -alkyl;

a heterocycle of formula (A 22 )

wherein:

R 55 and R 56 which can be the same or different represent a hydrogen atom; a halogen atom; C 1 -C 5 -alkyl or C 1 -C 5 -halogenoalkyl comprising up to 9 halogen atoms which can be the same or different;

R 57 represents a hydrogen atom or C 1 -C 5 -alkyl.

3. A compound according to claim 2 wherein A is selected in the list consisting of A 2 ; A 6 ; A 10 and A 13 .

4. A compound according to claim 3 wherein A is A 13 , and R 34 represents C 1 -C 5 -alkyl C 1 -C 5 -halogenoalkyl comprising up to 9 halogen atoms which can be the same or different; R 35 represents a hydrogen or a fluorine atom; R 36 represents methyl.

5. A compound according to claim 1 wherein Z 1 represents a non substituted C 3 -C 7 -cycloalkyl.

6. A compound according to claim 1 wherein Z 1 represents cyclopropyl.

7. A compound according to claim 1 wherein Z 1 represents a C 3 -C 7 cycloalkyl substituted by up to 10 groups or atoms which can be the same or different and which can be selected ion in the list consisting of halogen atoms; C 1 -C 8 -alkyl; C 1 -C 8 -halogenoalkyl comprising up to 9 halogen atoms which can be the same or different; C 1 -C 8 -alkoxy or C 1 -C 8 -halogenoalkoxy comprising up to 9 halogen atoms which can be the same or different.

8. A compound according to claim 1 wherein X, which can be the same or different, represents a halogen atom; C 1 -C 8 -alkyl; C 1 -C 8 -halogenoalkyl comprising up to 9 halogen atoms which can be the same or different; C 1 -C 8 -alkoxy or C 1 -C 8 -halogenoalkoxy comprising up to 9 halogen atoms which can be the same or different.

9. A compound according to claim 1 wherein two consecutive substituents X together with the phenyl ring form a substituted or non substituted 1,3-benzodioxolyl; 1,2,3,4-tetrahydro-quinoxalinyl; 3,4-dihydro-2H-1,4-benzoxazinyl; 1,4-benzodioxanyl; indanyl; 2,3-dihydrobenzofuranyl; indolinyl.

10. A compound according to claim 1 wherein R which can be the same or different, represents a hydrogen atom; halogen atom; cyano; C 1 -C 8 -alkylamino; di-C 1 -C 8 -alkylamino; tri(C 1 -C 8 -alkyl)silyl; C 1 -C 8 -alkyl; C 1 -C 8 -halogenoalkyl comprising up to 9 halogen atoms which can be the same or different; C 1 -C 8 -alkoxy; C 1 -C 8 -halogenoalkoxy comprising up to 9 halogen atoms which can be the same or different; C 1 -C 8 -alkylsulfanyl; amino, hydroxyl; nitro; C 1 -C 8 -alkoxycarbonyl; C 2 -C 8 -alkynyloxy.

11. A fungicide composition comprising, as an active ingredient, an effective amount of a compound of formula (I) according to claim 1 and an agriculturally acceptable support, carrier or filler.

12. A process for the preparation of a compound of formula (I) according to claim 1 according to the following scheme:

wherein

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

Z 1 represents a non substituted C 3 -C 7 -cycloalkyl or a C 3 -C 7 cycloalkyl substituted by up to 10 atoms or groups which can be the same or different and which can be selected from the group consisting of halogen atoms; cyano; C 1 -C 8 -halogenoalkyl comprising up to 9 halogen atoms which can be the same or different; C 1 -C 8 -alkoxy; C 1 -C 8 -halogenoalkoxy comprising up to 9 halogen atoms which can be the same or different; C 1 -C 8 -alkoxycarbonyl; C 1 -C 8 -halogenoalkoxycarbonyl comprising up to 9 halogen atoms which can be the same or different; C 1 -C 8 -alkylaminocarbonyl and di-C 1 -C 8 -alkylaminocarbonyl;

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;

X, which can be the same or different, represents a halogen atom; nitro; cyano; hydroxyl; sulfanyl; amino; pentafluoro-λ6-sulfanyl; C 1 -C 8 -alkyl; C 1 -C 8 -halogenoalkyl comprising up to 9 halogen atoms which 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 which 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 which can be the same or different; C 2 -C 8 -alkenyl; C 2 -C 8 -halogenoalkenyl comprising up to 9 halogen atoms which can be the same or different; C 2 -C 8 -alkynyl; C 2 -C 8 -halogenoalkynyl comprising up to 9 halogen atoms which can be the same or different C 2 -C 8 -alkenyloxy; C 2 -C 8 -halogenoalkenyloxy comprising up to 9 halogen atoms which can be the same or different; C 2 -C 8 -alkinyloxy; C 2 -C 8 -halogenoalkinyloxy comprising up to 9 halogen atoms which 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 which 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 which can be the same or different; C 1 -C 8 -alkylcarbamoyl; di-C 1 -C 8 -alkylcarbamoyl; N—C 1 -C 8 -alkyloxycarbamoyl; C 1 -C 8 -alkoxycarbamoyl; 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 which can be the same or different; C 1 -C 8 -alkylaminocarbonyl; di-C 1 -C 8 -alkylaminocarbonyl; C 1 -C 8 -alkylcarbonyloxy; C 1 -C 8 -halogenoalkylcarbonyloxy comprising up to 9 halogen atoms which can be the same or different; C 1 -C 8 -alkylcarbonylamino; C 1 -C 8 -halogenoalkylcarbonylamino comprising up to 9 halogen atoms which can be the same or different; C 1 -C 8 -alkylaminocarbonyloxy; di-C 1 -C 8 -alkylaminocarbonyloxy; C 1 -C 8 -alkyloxycarbonyloxy, C 1 -C 8 -alkylsulphenyl, C 1 -C 8 -halogenoalkylsulphenyl comprising up to 9 halogen atoms which can be the same or different, C 1 -C 8 -alkylsulphinyl, C 1 -C 8 -halogenoalkylsulphinyl comprising up to 9 halogen atoms which can be the same or different, C 1 -C 8 -alkylsulphonyl, C 1 -C 8 -halogenoalkylsulphonyl comprising up to 9 halogen atoms which can be the same or different, 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, a (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; benzyloxy which can be substituted by up to 5 groups Q; benzylsulfanyl which can be substituted by up to 5 groups Q; benzylamino which can be substituted by up to 5 groups Q; naphthyl which can be substituted by up to 6 groups Q; phenoxy which can be substituted by up to 5 groups Q; phenylamino which can be substituted by up to 5 groups Q; phenylsulfanyl which can be substituted by up to 5 groups Q; phenylmethylene which can be substituted by up to 5 groups Q; pyridinyl which can be substituted by up to four groups Q and pyridinyloxy which can be substituted by up to four groups Q;

n represents 1, 2, 3, 4 or 5; and

Y 1 represents a halogen or a hydroxyl.

13. A process for the preparation of a compound of formula (I) according to claim 1 according to the following scheme:

wherein;

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

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;

X, which can be the same or different, represents a halogen atom; nitro; cyano; hydroxyl; sulfanyl; amino; pentafluoro-λ6-sulfanyl; C 1 -C 8 -alkyl; C 1 -C 8 -halogenoalkyl comprising up to 9 halogen atoms which 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 which 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 which can be the same or different; C 2 -C 8 -alkenyl; C 2 -C 8 -halogenoalkenyl comprising up to 9 halogen atoms which can be the same or different; C 2 -C 8 -alkynyl; C 2 -C 8 -halogenoalkynyl comprising up to 9 halogen atoms which can be the same or different C 2 -C 8 -alkenyloxy; C 1 -C 8 -halogenoalkenyloxy comprising up to 9 halogen atoms which can be the same or different; C 2 -C 8 -alkinyloxy; C 2 -C 8 -halogenoalkinyloxy comprising up to 9 halogen atoms which 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 which 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 which can be the same or different; C 1 -C 8 -alkylcarbamoyl; di-C 1 -C 8 -alkylcarbamoyl; N—C 1 -C 8 -alkyloxycarbamoyl; C 1 -C 8 -alkoxycarbamoyl N—C 1 -C 8 -alkyl-C 1 -C 8 -alkoxycarbamoyl; C 1 -C 8 -alkoxycarbonyl; halogenoalkoxycarbonyl comprising up to 9 halogen atoms which can be the same or different; C 1 -C 8 -alkylaminocarbonyl; di-C 1 -C 8 -alkylaminocarbonyl; C 1 -C 8 -alkylcarbonyloxy C 1 -C 8 -halogenoalkylcarbonyloxy comprising up to 9 halogen atoms which can be the same or different; C 1 -C 8 -alkylcarbonylamino; C 1 -C 8 -halogenoalkylcarbonylamino comprising up to 9 halogen atoms which can be the same or different; C 1 -C 8 -alkylaminocarbonyloxy; di-C 1 -C 8 -alkylaminocarbonyloxy; C 1 -C 8 -alkyloxycarbonyloxy, C 1 -C 8 -alkylsulphenyl, C 1 -C 8 -halogenoalkylsulphenyl comprising up to 9 halogen atoms which can be the same or different, C 1 -C 8 -alkylsulphinyl, C 1 -C 8 -halogenoalkylsulphinyl comprising up to 9 halogen atoms which can be the same or different, C 1 -C 8 -alkylsulphonyl, C 1 -C 8 -halogenoalkylsulphonyl comprising up to 9 halogen atoms which can be the same or different, 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, a (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; benzyloxy which can be substituted by up to 5 groups Q; benzylsulfanyl which can be substituted by up to 5 groups Q; benzylamino which can be substituted by up to 5 groups Q; naphthyl which can be substituted by up to 6 groups Q; phenoxy which can be substituted by up to 5 groups Q; phenylamino which can be substituted by up to 5 groups Q; phenylsulfanyl which can be substituted by up to 5 groups Q; phenylmethylene which can be substituted by up to 5 groups Q; pyridinyl which can be substituted by up to four groups Q and pyridinyloxy which can be substituted by up to four groups Q;

n represents 1, 2, 3, 4 or 5;

Y 1 represents a halogen or a hydroxyl; and

Y 2 represents a halogen or a leaving group like a tosylate group.

14. A process for the preparation of a compound of formula (I) according to claim 1 according to the following scheme:

wherein

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

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;

X, which can be the same or different, represents a halogen atom; nitro cyano; hydroxyl; sulfanyl; amino; pentafluoro-λ6-sulfanyl; C 1 -C 8 -alkyl; C 1 -C 8 -halogenoalkyl comprising up to 9 halogen atoms which 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 which 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 which can be the same or different; C 2 -C 8 -alkenyl; C 2 -C 8 -halogenoalkenyl comprising up to 9 halogen atoms which can be the same or different; C 2 -C 8 -alkynyl; C 2 -C 8 -halogenoalkynyl comprising up to 9 halogen atoms which can be the same or different C 2 -C 8 -alkenyloxy; C 2 -C 8 -halogenoalkenyloxy comprising up to 9 halogen atoms which can be the same or different; C 2 -C 8 -alkinyloxy; C 2 -C 8 -halogenoalkinyloxy comprising up to 9 halogen atoms which 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 which 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 which can be the same or different; C 1 -C 8 -alkylcarbamoyl; di-C 1 -C 8 -alkylcarbamoyl; N—C 1 -C 8 -alkyloxycarbamoyl; C 1 -C 8 -alkoxycarbamoyl; 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 which can be the same or different; C 1 -C 8 -alkylaminocarbonyl; di-C 1 -C 8 -alkylaminocarbonyl C 1 -C 8 -alkylcarbonyloxy; C 1 -C 8 -halogenoalkylcarbonyloxy comprising up to 9 halogen atoms which can be the same or different; C 1 -C 8 -alkylcarbonylamino; C 1 -C 8 -halogenoalkylcarbonylamino comprising up to 9 halogen atoms which can be the same or different; C 1 -C 8 -alkylaminocarbonyloxy; di-C 1 -C 8 -alkylaminocarbonyloxy; C 1 -C 8 -alkyloxycarbonyloxy, C 1 -C 8 -alkylsulphenyl, C 1 -C 8 -halogenoalkylsulphenyl comprising up to 9 halogen atoms which can be the same or different, C 1 -C 8 -alkylsulphinyl, C 1 -C 8 -halogenoalkylsulphinyl comprising up to 9 halogen atoms which can be the same or different; C 1 -C 8 -alkylsulphonyl, C 1 -C 8 -halogenoalkylsulphonyl comprising up to 9 halogen atoms which can be the same or different, 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, a (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; benzyloxy which can be substituted by up to 5 groups Q; benzylsulfanyl which can be substituted by up to 5 groups Q; benzylamino which can be substituted by up to 5 groups Q; naphthyl which can be substituted by up to 6 groups Q; phenoxy which can be substituted by up to 5 groups Q; phenylamino which can be substituted by up to 5 groups Q; phenylsulfanyl which can be substituted by up to 5 groups Q; phenylmethylene which can be substituted by up to 5 groups Q; pyridinyl which can be substituted by up to four groups Q and pyridinyloxy which can be substituted by up to four groups Q;

n represents 1, 2, 3, 4 or 5;

Y 3 represents a halogen atom; and

Y 4 represents sulphur, oxygen or C 1 -C 5 -alkylamino.

15. A method for controlling phytopathogenic fungi of crops, characterized in that an agronomically effective and substantially non-phytotoxic quantity of a compound according to claim 1 is applied 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.

16. A method for controlling phytopathogenic fungi of crops, characterized in that an agronomically effective and substantially non-phytotoxic quantity of a composition according to claim 11 is applied 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.

Assignments (5)

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 11, 2019

From: BAYER INTELLECTUAL PROPERTY GMBH

To: BAYER CROPSCIENCE AKTIENGESELLSCHAFT

Reel/Frame 049359/0698 →

NUNC PRO TUNC ASSIGNMENT Recorded Feb 3, 2016

From: BAYER CROPSCIENCE AG

To: BAYER INTELLECTUAL PROPERTY GMBH

Reel/Frame 037689/0656 →

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 20, 2010

From: BAYER CROPSCIENCE SA

To: BAYER CROPSCIENCE AG

Reel/Frame 025161/0521 →

CORRECTIVE ASSIGNMENT TO CORRECT THE SERIAL NO., FILING DATE AND TITLE PREVIOUSLY RECORDED ON REEL 021694 FRAME 0256. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Recorded Dec 17, 2008

From: MANSFIELD, DARREN; COQUERON, PIERRE-YVES; DESBORDES, PHILIPPE; VILLIER, ALAIN; GROSJEAN-COURNOYER, MARIE-CLAIRE; GARY, STEPHANIE; CARBONNE, STEPHANE; DUNKEL, RALF; TUCH, AROUNARITH; VORS, JEAN-PIERRE

To: BAYER CROPSCIENCE SA

Reel/Frame 021993/0575 →

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 10, 2008

To: BAYER CROPSCIENCE S.A.

Reel/Frame 021694/0256 →