WO2010015680A1 - Fungicide oxyalkylamide derivatives - Google Patents

Abstract

The present invention relates to fungicide oxyalkylamide derivatives of formula (I), their process of preparation, their use as fungicides, particularly in the form of fungicidal compositions and methods for the control of phytopathogenic fungi of plants using these compounds or their compositions. Formula (I) wherein Q¹ to Q³, R¹ to R³ and L represent various substituents.

Description

FUNGICIDE OXYALKYLAMIDE DERIVATIVES

DESCRIPTION

The present invention relates to oxyalkylamide derivatives, 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.

In international patent application WO 2008/028624, there are disclosed certain sulphur- substituted quinolyloxyalkanoϊc acid amides derivatives of the following chemical structure:

wherein R¹ represents an alkyl group, an alkenyl group, an alkynyl group or a cycloakyl group. The compounds disclosed in this document do not prove to provide a comparable utility than the compounds according to the invention.

It is always of high-interest in agriculture to use novel pesticide compounds in order to avoid or to control the development of resistant strains to the active ingredients. It is also of high- interest to use novel compounds being more active than those already known, with the aim of decreasing the amounts of active compound to be used, whilst at the same time maintaining effectiveness at least equivalent to the already known compounds. We have now found a new family of compounds which possess the above mentioned effects or advantages.

Accordingly, the present invention provides a oxyalkylamide derivative of formula (I)

(I) wherein

Q¹ and Q² independently represent a hydrogen atom, a halogen atom, a nitro group, a hydroxy group, a cyano group, an amino group, a sulphenyl group, a formyl group, a substituted or non-substituted carbaldehyde O-(C-ι-C₈-alkyl)oxime, a formyloxy group, a formylamino group, a carbamoyl group, a N-hydroxycarbamoyl group, a pentafluoro-λ⁶-sulphenyl group, substituted or non-substituted C-ι-C₈-alkoxyamino group, substituted or non-substituted N-C-ι-C₈-alkyl-(C-ι-C₈-alkoxy)-amino group, substituted or non-substituted (C-ι-C₈-alkylamino)-amino group, substituted or non- substituted N-C-ι-C₈-alkyl-(C-ι-C₈-alkylamino)-amino group, a substituted or non- substituted (hydroxyimino)-C-ι-C₆-alkyl group, substituted or non-substituted C₁-C₈- alkyl, substituted or non-substituted tri(C-ι-C₈-alkyl)silyl, substituted or non- substituted tri(Ci-C₈-alkyl)silyl-Ci-C₈-alkyl, substituted or non-substituted C₁-C₈- cycloalkyl, substituted or non-substituted tri(Ci-C₈-alkyl)silyl-Ci-C₈-cycloalkyl, substituted or non-substituted Ci-C₈-halogenoalkyl having 1 to 5 halogen atoms, substituted or non-substituted Ci-C₈-halogenocycloalkyl having 1 to 5 halogen atoms, a C₂-C₈-alkenyl, substituted or non-substituted C₂-C₈-alkynyl, substituted or non-substituted Ci-C₈-alkylamino, substituted or non-substituted di-C-ι-C₈- alkylamino, substituted or non-substituted Ci-C₈-alkoxy, substituted or non- substituted d-C₈-halogenoalkoxy having 1 to 5 halogen atoms, substituted or non- substituted d-C₈-alkylsulphenyl, substituted or non-substituted C₁-C₈- halogenoalkylsulphenyl having 1 to 5 halogen atoms, substituted or non-substituted C₂-C₈-alkenyloxy, substituted or non-substituted C₂-C₈-halogenoalkenyloxy having 1 to 5 halogen atoms, substituted or non-substituted C₃-C₈-alkynyloxy, substituted or non-substituted C₃-C₈-halogenoalkynyloxy having 1 to 5 halogen atoms, substituted or non-substituted d-C₈-alkylcarbonyl, substituted or non-substituted C₁-C₈- halogenoalkylcarbonyl having 1 to 5 halogen atoms, substituted or non-substituted C-i-Cs-alkylcarbamoyl, substituted or non-substituted di-C-i-Cs-alkylcarbamoyl, substituted or non-substituted N-C-i-Cs-alkyloxycarbamoyl, substituted or non- substituted C-i-Cs-alkoxycarbamoyl, substituted or non-substituted N-C-i-Cs-alkyl-C-i- C₈-alkoxycarbamoyl, substituted or non-substituted C-i-Cs-alkoxycarbonyl, substituted or non-substituted C-i-Cs-halogenoalkoxycarbonyl having 1 to 5 halogen atoms, substituted or non-substituted d-Cs-alkylcarbonyloxy, substituted or non- substituted C-i-Cs-halogenoalkylcarbonyloxy having 1 to 5 halogen atoms, substituted or non-substituted d-Cs-alkylcarbonylamino, substituted or non- substituted C-i-Cs-halogenoalkylcarbonylamino having 1 to 5 halogen atoms, substituted or non-substituted d-Cs-alkylcarbamoylannino, substituted or non- substituted C-i-Cs-halogenoalkylcarbamoylamino having 1 to 5 halogen atoms, substituted or non-substituted di-d-Cs-alkylcarbamoylannino, substituted or non- substituted di-C-i-Cs-halogenoalkylcarbamoylamino having 1 to 5 halogen atoms , substituted or non-substituted N-Ci-C₈-alkyl-(Ci-C₈-alkylcarbamoyl)amino, substituted or non-substituted N-Ci-C₈-alkyl-(Ci-C₈-halogenoalkylcarbamoyl)amino having 1 to 5 halogen atoms, substituted or non-substituted N-d-C₈-alkyl-(di-d-C₈- alkylcarbamoyl)amino, substituted or non-substituted N-d-C₈-alkyl-(di-d-C₈- halogenoalkylcarbamoyl)amino having 1 to 5 halogen atoms, substituted or non- substituted Ci-C₈-alkylaminocarbonyloxy, substituted or non-substituted di-d-C₈- alkylaminocarbonyloxy, substituted or non-substituted Ci-C₈-alkylcarbamothioyl, substituted or non-substituted di-Ci-C₈-alkylcarbamothioyl, substituted or non- substituted N-C-i-C₈-alkyloxycarbamothioyl, substituted or non-substituted C₁-C₈- alkoxycarbamothioyl, substituted or non-substituted N-C₁ -C₈-alkyl-d -C₈- alkoxycarbamothioyl, substituted or non-substituted d-C₈-alkylthioylannino, substituted or non-substituted C-ι-C₈-halogenoalkylthioylamino having 1 to 5 halogen atoms, substituted or non-substituted (d-C₈-alkyl-carbamothioyl)-oxy, substituted or non-substituted substituted or non-substituted (di-d-C₈-alkyl-carbannothioyl)-oxy, substituted or non-substituted d-C₈-alkylsulphinyl, substituted or non-substituted C₁- C₈-halogenoalkylsulphinyl having 1 to 5 halogen atoms, substituted or non- substituted d-C₈-alkylsulphonyl, substituted or non-substituted d-C₈-halogenoalkyl- sulphonyl having 1 to 5 halogen atoms, substituted or non-substituted C₁-C₈- alkylaminosulfamoyl, substituted or non-substituted di-d-C₈-alkylaminosulfannoyl, substituted or non-substituted (d-C₆-alkoxyinnino)-d-C₆-alkyl, substituted or non- substituted (d-C₆-alkenyloxyinnino)-d-C₆-alkyl, substituted or non-substituted (C₁- C₆-alkynyloxyimino)-d-C₆-alkyl, substituted or non-substituted (benzyloxyimino)-d- C₆-alkyl, substituted or non-substituted benzyloxy, substituted or non-substituted benzylsulphenyl, substituted or non-substituted benzylamino, substituted or non- substituted phenoxy, substituted or non-substituted phenylsulphenyl, substituted or non-substituted phenylamino, substituted or non-substituted aryl, substituted or non- substituted aryl-[d-C₈]-alkyl, substituted or non-substituted tri(d-C₈-alkyl)-silyloxy, substituted or non-substituted C-ι-C₈-alkylsulfenylamino, substituted or non- substituted d-Cs-halogenoalkylsulphinylamino having 1 to 5 halogen atoms, substituted or non-substituted d-C₈-alkylsulphonylannino, substituted or non- substituted d-Cs-halogenoalkylsulphonylamino having 1 to 5 halogen atoms, substituted or non-substituted d-C₈-alkoxysulphonylannino, substituted or non- substituted C-rCs-halogenoxysulphonylamino having 1 to 5 halogen atoms, substituted or non-substituted (C-ι-C₆-alkylideneamino)oxy, substituted or non- substituted (C-ι-C₆-alkenylideneamino)oxy, substituted or non-substituted (C₁-C₆- alkynylideneamino)oxy, substituted or non-substituted (benzylideneamino)oxy; substituted or non-substituted, saturated or unsaturated A-, 5-, 6- or 7-membered heterocyclyl comprising up to 4 heteroatoms selected in the list consisting of N, O, S; substituted or non-substituted, saturated or unsaturated A-, 5-, 6- or 7-membered heterocyclyl-[Ci-C₈]-alkyl comprising up to 4 heteroatoms selected in the list consisting of N, O, S;

• Q³ represents a halogen atom, a nitro group, a hydroxy group, a cyano group, an amino group, a sulphenyl group, a formyl group, a substituted or non-substituted carbaldehyde O-(C-ι-C₈-alkyl)oxime, a formyloxy group, a formylamino group, a carbamoyl group, a N-hydroxycarbamoyl group, a pentafluoro-λ⁶-sulphenyl group, substituted or non-substituted C-ι-C₈-alkoxyamino group, substituted or non- substituted N-C-ι-C₈-alkyl-(C-ι-C₈-alkoxy)-amino group, substituted or non-substituted (C-ι-C₈-alkylamino)-amino group, substituted or non-substituted N-d-C₈-alkyl-(d-C₈- alkylamino)-amino group, a substituted or non-substituted (hydroxyimino)-C-ι-C₆-alkyl group, substituted or non-substituted C-ι-C₈-alkyl, substituted or non-substituted tri(Ci-C₈-alkyl)silyl, substituted or non-substituted tri(C₁-C₈-alkyl)silyl-C₁-C₈-alkyl, substituted or non-substituted Ci-C₈-cycloalkyl, substituted or non-substituted tri(Ci- C₈-alkyl)silyl-Ci-C₈-cycloalkyl, substituted or non-substituted Ci-C₈-halogenoalkyl having 1 to 5 halogen atoms, substituted or non-substituted Ci-C₈- halogenocycloalkyl having 1 to 5 halogen atoms, a C₂-C₈-alkenyl, substituted or non- substituted C₂-C₈-alkynyl, substituted or non-substituted Ci-C₈-alkylamino, substituted or non-substituted di-Ci-C₈-alkylamino, substituted or non-substituted Ci-C₈-alkoxy, substituted or non-substituted Ci-C₈-halogenoalkoxy having 1 to 5 halogen atoms, substituted or non-substituted d-C₈-alkylsulphenyl, substituted or non-substituted C-i-C₈-halogenoalkylsulphenyl having 1 to 5 halogen atoms, substituted or non-substituted C₂-C₈-alkenyloxy, substituted or non-substituted C₂- C₈-halogenoalkenyloxy having 1 to 5 halogen atoms, substituted or non-substituted C₃-C₈-alkynyloxy, substituted or non-substituted C₃-C₈-halogenoalkynyloxy having 1 to 5 halogen atoms, substituted or non-substituted d-C₈-alkylcarbonyl, substituted or non-substituted d-Cs-halogenoalkylcarbonyl having 1 to 5 halogen atoms, substituted or non-substituted d-Cs-alkylcarbamoyl, substituted or non-substituted di-d-Cs-alkylcarbamoyl, substituted or non-substituted N-d-Cs-alkyloxycarbamoyl, substituted or non-substituted d-Cs-alkoxycarbamoyl, substituted or non-substituted N-Ci-C₈-alkyl-Ci-C₈-alkoxycarbannoyl, substituted or non-substituted C₁-C₈- alkoxycarbonyl, substituted or non-substituted d-Cs-halogenoalkoxycarbonyl having 1 to 5 halogen atoms, substituted or non-substituted d-Cs-alkylcarbonyloxy, substituted or non-substituted d-Cs-halogenoalkylcarbonyloxy having 1 to 5 halogen atoms, substituted or non-substituted d-Cs-alkylcarbonylamino, substituted or non-substituted d-Cs-halogenoalkylcarbonylamino having 1 to 5 halogen atoms, substituted or non-substituted d-Cs-alkylcarbamoylamino, substituted or non- substituted d-Cs-halogenoalkylcarbamoylamino having 1 to 5 halogen atoms, substituted or non-substituted di-d-Cs-alkylcarbamoylamino, substituted or non- substituted di-d-Cs-halogenoalkylcarbamoylamino having 1 to 5 halogen atoms , substituted or non-substituted N-d-C₈-alkyl-(d-C₈-alkylcarbamoyl)amino, substituted or non-substituted N-d-C₈-alkyl-(d-C₈-halogenoalkylcarbamoyl)amino having 1 to 5 halogen atoms, substituted or non-substituted N-d-C₈-alkyl-(di-d-C₈- alkylcarbamoyl)amino, substituted or non-substituted N-d-C₈-alkyl-(di-d-C₈- halogenoalkylcarbamoyl)amino having 1 to 5 halogen atoms, substituted or non- substituted d-C₈-alkylaminocarbonyloxy, substituted or non-substituted di-d-C₈- alkylaminocarbonyloxy, substituted or non-substituted d-C₈-alkylcarbamothioyl, substituted or non-substituted di-d-Cs-alkylcarbamothioyl, substituted or non- substituted N-d-Cs-alkyloxycarbamothioyl, substituted or non-substituted C₁-C₈- alkoxycarbamothioyl, substituted or non-substituted N-C₁ -C₈-alkyl-d -C₈- alkoxycarbamothioyl, substituted or non-substituted C-ι-C₈-alkylthioylamino, substituted or non-substituted C-ι-C₈-halogenoalkylthioylamino having 1 to 5 halogen atoms, substituted or non-substituted (d-C₈-alkyl-carbamothioyl)-oxy, substituted or non-substituted substituted or non-substituted (di-d-C₈-alkyl-carbannothioyl)-oxy, substituted or non-substituted d-C₈-alkylsulphinyl, substituted or non-substituted C₁- C₈-halogenoalkylsulphinyl having 1 to 5 halogen atoms, substituted or non- substituted d-C₈-alkylsulphonyl, substituted or non-substituted d-C₈-halogenoalkyl- sulphonyl having 1 to 5 halogen atoms, substituted or non-substituted C₁-C₈- alkylaminosulfamoyl, substituted or non-substituted di-d-C₈-alkylaminosulfannoyl, substituted or non-substituted (d-C₆-alkoxyinnino)-d-C₆-alkyl, substituted or non- substituted (d-C₆-alkenyloxyinnino)-d-C₆-alkyl, substituted or non-substituted (C₁- C₆-alkynyloxyimino)-d-C₆-alkyl, substituted or non-substituted (benzyloxyimino)-d- C₆-alkyl, substituted or non-substituted benzyloxy, substituted or non-substituted benzylsulphenyl, substituted or non-substituted benzylamino, substituted or non- substituted phenoxy, substituted or non-substituted phenylsulphenyl, substituted or non-substituted phenylamino, substituted or non-substituted aryl, substituted or non- substituted aryl-[d-C₈]-alkyl, substituted or non-substituted tri(d-C₈-alkyl)-silyloxy, substituted or non-substituted C-ι-C₈-alkylsulfenylamino, substituted or non- substituted d-Cs-halogenoalkylsulphinylamino having 1 to 5 halogen atoms, substituted or non-substituted d-C₈-alkylsulphonylamino, substituted or non- substituted C-rCs-halogenoalkylsulphonylamino having 1 to 5 halogen atoms, substituted or non-substituted C-ι-C₈-alkoxysulphonylamino, substituted or non- substituted C-ι-C₈-halogenoxysulphonylamino having 1 to 5 halogen atoms, substituted or non-substituted (C-ι-C₆-alkylideneamino)oxy, substituted or non- substituted (C-ι-C₆-alkenylideneamino)oxy, substituted or non-substituted (C₁-C₆- alkynylideneamino)oxy, substituted or non-substituted (benzylideneamino)oxy; substituted or non-substituted, saturated or unsaturated A-, 5-, 6- or 7-membered heterocyclyl comprising up to 4 heteroatoms selected in the list consisting of N, O, S; substituted or non-substituted, saturated or unsaturated A-, 5-, 6- or 7-membered heterocyclyl-[Ci-C₈]-alkyl comprising up to 4 heteroatoms selected in the list consisting of N, O, S; • R¹ represents a hydrogen atom, a hydroxy group, a cyano group, an amino group, a substituted or non-substituted carbaldehyde O-(C-ι-C₈-alkyl)oxime, a formyloxy group, a formylamino group, substituted or non-substituted Ci-C₈-alkoxyamino group, substituted or non-substituted N-Ci-C₈-alkyl-(Ci-C₈-alkoxy)-amino group, a substituted or non-substituted (hydroxyimino)-Ci-C₆-alkyl group, substituted or non- substituted Ci-C₈-alkyl, substituted or non-substituted tri(C₁-C₈-alkyl)silyl, substituted or non-substituted tri(C₁-C₈-alkyl)silyl-Ci-C₈-alkyl, substituted or non-substituted C₁-

C₈-cycloalkyl, substituted or non-substituted tri(Ci-C₈-alkyl)silyl-Ci-C₈-cycloalkyl, substituted or non-substituted Ci-C₈-halogenoalkyl having 1 to 5 halogen atoms, substituted or non-substituted d-C₈-halogenocycloalkyl having 1 to 5 halogen atoms, a C₂-C₈-alkenyl, substituted or non-substituted C₂-C₈-alkynyl, substituted or non-substituted d-C₈-alkylamino, substituted or non-substituted CIi-C₁-C₈- alkylamino, substituted or non-substituted d-C₈-alkoxy, substituted or non- substituted d-C₈-halogenoalkoxy having 1 to 5 halogen atoms, substituted or non- substituted C₂-C₈-alkenyloxy, substituted or non-substituted C₂-C₈- halogenoalkenyloxy having 1 to 5 halogen atoms, substituted or non-substituted C₃- C₈-alkynyloxy, substituted or non-substituted C₃-C₈-halogenoalkynyloxy having 1 to

5 halogen atoms, substituted or non-substituted Ci-C₈-alkylcarbonyloxy, substituted or non-substituted Ci-C₈-halogenoalkylcarbonyloxy having 1 to 5 halogen atoms, substituted or non-substituted Ci-C₈-alkylcarbonylamino, substituted or non- substituted Ci-C₈-halogenoalkylcarbonylamino having 1 to 5 halogen atoms, substituted or non-substituted (d-C₆-alkoxyimino)-d-C₆-alkyl, substituted or non- substituted (d-C₆-alkenyloxyimino)-d-C₆-alkyl, substituted or non-substituted (C₁- C₆-alkynyloxyimino)-d-C₆-alkyl, substituted or non-substituted (benzyloxyimino)-d- C₆-alkyl, substituted or non-substituted benzyloxy, substituted or non-substituted benzylsulphenyl, substituted or non-substituted benzylamino, substituted or non- substituted phenoxy, substituted or non-substituted phenylsulphenyl, substituted or non-substituted phenylamino, substituted or non-substituted aryl, substituted or non- substituted aryl-[C-ι-C₈]-alkyl, substituted or non-substituted tri(C-ι-C₈-alkyl)-silyloxy; substituted or non-substituted, saturated or unsaturated A-, 5-, 6- or 7-mennbered heterocyclyl comprising up to 4 heteroatoms selected in the list consisting of N, O, S; substituted or non-substituted, saturated or unsaturated A-, 5-, 6- or 7-mennbered heterocyclyl-[C-ι-C₈]-alkyl comprising up to 4 heteroatoms selected in the list consisting of N, O, S; • R² represents a hydrogen atom, a hydroxy group, a cyano group, substituted or non-substituted C-ι-C₈-alkyl, substituted or non-substituted tri(C-ι-C₈-alkyl)silyl, substituted or non-substituted tri(C-ι-C₈-alkyl)silyl-C-ι-C₈-alkyl, substituted or non- substituted d-C₈-cycloalkyl, substituted or non-substituted tri(d-C₈-alkyl)silyl-d-C₈- cycloalkyl, substituted or non-substituted d-C₈-halogenoalkyl having 1 to 5 halogen atoms, substituted or non-substituted d-C₈-halogenocycloalkyl having 1 to 5 halogen atoms, a C₂-C₈-alkenyl, substituted or non-substituted C₂-C₈-alkynyl, substituted or non-substituted d-C₈-alkoxy, substituted or non-substituted benzyloxy:

• R³ represents -(CR^aR^b)p-R⁴, wherein: o R^a and R^b represent independently a hydrogen atom, substituted or non- substituted Ci-C₈-alkyl, a halogen atom, a cyano group, a hydroxy group, substituted or non-substituted Ci-C₈-alkoxy or substituted or non-substituted Ci-C₈-alkoxycarbonyl, or

° R^a and R^b form a 3- to 8-membered carbocyclic or heterocyclic ring comprising a heteroatom selected from sulfur, oxygen and NR⁰ wherein R⁰ represents a hydrogen atom or substituted or non-substituted d-C₈-alkyl; o R⁴ represents a halogen atom, substituted or non-substituted d-C₈-alkyl, substituted or non-substituted d-C₈-alkenyl, substituted or non-substituted d-C₈-alkyloxy-d-C₈-alkyl, substituted or non-substituted aryloxy or substituted or non-substituted heteroaryloxy, -C≡C-R⁵ wherein R⁵ represents a hydrogen atom , a halogen atom, substituted or non-substituted C₁-C₈- alkyl, substituted or non-substituted C₃-C₈-cycloalkyl, substituted or non- substituted d-C₈-alkyloxy-d_|-C₈-alkyl, substituted or non-substituted aryl, substituted or non-substituted aryl-[Ci-C₈]-alkyl, substituted or non- substituted tri(Ci-C₈-alkyl)-silyl; substituted or non-substituted, saturated or unsaturated A-, 5-, 6- or 7-membered heterocyclyl comprising up to 4 heteroatoms selected in the list consisting of N, O, S; substituted or non- substituted, saturated or unsaturated A-, 5-, 6- or 7-membered heterocyclyl- [Ci-C₈]-alkyl comprising up to 4 heteroatoms selected in the list consisting of N, O, S, wherein the N atom is substituted or unsubstituted with substituted or non-substituted C-ι-C₈-alkyl, substituted or non-substituted C₃-C₈- cycloalkyl, substituted or non-substituted d-Cs-alkyloxy-d-Cs-alkyl, substituted or non-substituted aryl, substituted or non-substituted aryl-[d-

C₈]-alkyl, substituted or non-substituted tri(C-ι-C₈-alkyl)-silyl: o p is 0 or 1

• L represents a sulfur atom or an oxygen atom as well as salts, N-oxides, metallic complexes and metalloidic complexes thereof.

Any of the compounds according to the invention can exist as one or more stereoisomers depending on the number of stereogenic units (as defined by the IUPAC rules) in the compound. The invention thus relates equally to all the stereoisomers, and to the mixtures of all the possible stereoisomers, in all proportions. The stereoisomers can be separated according to the methods which are known per se by the man ordinary skilled in the art.

According to the invention, the following generic terms are generally used with the following meanings:

• halogen means fluorine, chlorine, bromine or iodine ; • heteroatom can be nitrogen, oxygen or sulphur ;

• unless indicated otherwise, a group or a substituent that is substituted according to the invention can be substituted by one or more of the following groups or atoms: a halogen atom, a nitro group, a hydroxy group, a cyano group, an amino group, a sulphenyl group, a pentafluoro-λ⁶-sulphenyl group, a formyl group, a substituted or non-substituted carbaldehyde O-(Ci-C₈-alkyl)oxime, a formyloxy group, a formylamino group, a carbamoyl group, a N-hydroxycarbamoyl group, a (hydroxyimino)-Ci-C₆-alkyl group, a Ci-C₈-alkyl, a tri(C₁-C₈-alkyl)silyl-C₁-C₈-alkyl, d- C₈-cycloalkyl, tri(C₁-C₈-alkyl)silyl-C₁-C₈-cycloalkyl, a C_rC₈-halogenoalkyl having 1 to 5 halogen atoms, a Ci-C₈-halogenocycloalkyl having 1 to 5 halogen atoms, a C₂-C₈- alkenyl, a C₂-C₈-alkynyl, a C₂-C₈-alkenyloxy, a C₂-C₈-alkynyloxy, a Ci-C₈-alkylamino, a di-Ci-C₈-alkylamino, a Ci-C₈-alkoxy, a Ci-C₈-halogenoalkoxy having 1 to 5 halogen atoms, a d-C₈-alkylsulphenyl, a d-C₈-halogenoalkylsulphenyl having 1 to 5 halogen atoms, a C₂-C₈-alkenyloxy, a C₂-C₈-halogenoalkenyloxy having 1 to 5 halogen atoms, a C₃-C₈-alkynyloxy, a C₃-C₈-halogenoalkynyloxy having 1 to 5 halogen atoms, a d-C₈-alkylcarbonyl, a d-C₈-halogenoalkylcarbonyl having 1 to 5 halogen atoms, a d-C₈-alkylcarbamoyl, a di-d-C₈-alkylcarbamoyl, a N-C₁-C₈- alkyloxycarbamoyl, a d-C₈-alkoxycarbamoyl, a N-d-C₈-alkyl-d-C₈- alkoxycarbamoyl, a d-C₈-alkoxycarbonyl, a d-C₈-halogenoalkoxycarbonyl having 1 to 5 halogen atoms, a C-i-Cs-alkylcarbonyloxy, a C-i-Cs-halogenoalkylcarbonyloxy having 1 to 5 halogen atoms, a C-i-Cs-alkylcarbonylamino, a C₁-C₈- halogenoalkylcarbonylamino having 1 to 5 halogen atoms, substituted or non- substituted C-i-Cs-alkoxycarbonylamino, substituted or non-substituted C₁-C₈- halogenoalkoxycarbonylamino having 1 to 5 halogen atoms, a C₁-C₈- alkylaminocarbonyloxy, a di-C-i-Cs-alkylaminocarbonyloxy, a C₁-C₈- alkyloxycarbonyloxy, a C-ι-C₈-alkylsulphenyl, a C-i-Cs-halogenoalkylsulphenyl having 1 to 5 halogen atoms, a C-ι-C₈-alkylsulphinyl, a C-i-Cs-halogenoalkylsulphinyl having 1 to 5 halogen atoms, a C-ι-C₈-alkylsulphonyl, a C-i-Cs-halogenoalkylsulphonyl having 1 to 5 halogen atoms, a C-i-Cs-alkylaminosulfamoyl, a CIi-C₁-C₈- alkylaminosulfamoyl, a (C-i-Ce-alkoxyimino^C-i-Cβ-alkyl, a (C-ι-C₆-alkenyloxyimino)- C-ι-C₆-alkyl, a (C-i-Ce-alkynyloxyimino^C-i-Ce-alkyl, (benzyloxyimino)-C-ι-C₆-alkyl, C₁- C₈-alkoxyalkyl, C-ι-C₈-halogenoalkoxyalkyl having 1 to 5 halogen atoms, benzyloxy, benzylsulphenyl, benzylamino, phenoxy, phenylsulphenyl, or phenylamino ; • the term "aryl" means phenyl or naphthyl.

Preferred compounds of formula (I) according to the invention are those wherein Q¹ and Q² independently represent a hydrogen atom, a halogen atom, a cyano group, substituted or non-substituted C-ι-C₈-alkyl, substituted or non-substituted tri(C-ι-C₈-alkyl)silyl, substituted or non-substituted tri(C₁-C₈-alkyl)silyl-C₁-C₈-alkyl, substituted or non-substituted C₁-C₈- cycloalkyl, substituted or non-substituted C-ι-C₈-halogenoalkyl having 1 to 5 halogen atoms, substituted or non-substituted C-ι-C₈-alkoxy, substituted or non-substituted C₁-C₈- halogenoalkoxy having 1 to 5 halogen atoms, substituted or non-substituted C₁-C₈- alkylsulphenyl, substituted or non-substituted C₃-C₈-alkynyloxy, substituted or non- substituted phenoxy, substituted or non-substituted aryl, substituted or non-substituted aryl- [C-ι-C₈]-alkyl, substituted or non-substituted tri(C-ι-C₈-alkyl)-silyloxy, substituted or non- substituted, saturated or unsaturated A-, 5-, 6- or 7-membered heterocyclyl comprising up to 4 heteroatoms selected in the list consisting of N, O, S; substituted or non-substituted, saturated or unsaturated A-, 5-, 6- or 7-membered heterocyclyl-[C-ι-C₈]-alkyl comprising up to 4 heteroatoms selected in the list consisting of N, O, S.

More preferred compounds of formula (I) according to the invention are those wherein Q¹ and Q² independently represent a hydrogen atom, a halogen atom, substituted or non- substituted C-ι-C₈-alkyl.

Other preferred compounds of formula (I) according to the invention are those wherein Q³ represents a halogen atom, a cyano group, substituted or non-substituted C-ι-C₈-alkyl, substituted or non-substituted tri(C-ι-C₈-alkyl)silyl, substituted or non-substituted C₁-C₈- cycloalkyl, substituted or non-substituted Ci-C₈-halogenoalkyl having 1 to 5 halogen atoms, substituted or non-substituted C-ι-C₈-alkoxy.

Other more preferred compounds of formula (I) according to the invention are those wherein Q³ represents a halogen atom, substituted or non-substituted C-ι-C₈-alkyl.

Other preferred compounds of formula (I) according to the invention are those wherein R¹ represents a hydrogen atom, a hydroxy group, a substituted or non-substituted carbaldehyde O-(Ci-C₈-alkyl)oxime, a formyloxy group, substituted or non-substituted Ci-C₈-alkoxyamino group, substituted or non-substituted N-Ci-C₈-alkyl-(Ci-C₈-alkoxy)-amino group, a substituted or non-substituted (hydroxyimino)-Ci-C₆-alkyl group, substituted or non- substituted Ci-C₈-alkyl, substituted or non-substituted tri(Ci-C₈-alkyl)silyl, substituted or non- substituted tri(Ci-C₈-alkyl)silyl-Ci-C₈-alkyl, substituted or non-substituted Ci-C₈-cycloalkyl, substituted or non-substituted tri(Ci-C₈-alkyl)silyl-Ci-C₈-cycloalkyl, substituted or non- substituted Ci-C₈-halogenoalkyl having 1 to 5 halogen atoms, substituted or non-substituted Ci-C₈-halogenocycloalkyl having 1 to 5 halogen atoms, a C₂-C₈-alkenyl, substituted or non- substituted C₂-C₈-alkynyl, substituted or non-substituted d-C₈-alkoxy, substituted or non- substituted d-C₈-halogenoalkoxy having 1 to 5 halogen atoms, substituted or non- substituted C₂-C₈-alkenyloxy, substituted or non-substituted C₃-C₈-alkynyloxy, substituted or non-substituted d-Cs-alkylcarbonyloxy, substituted or non-substituted (d-C₆-alkoxyimino)- C-ι-C₆-alkyl, substituted or non-substituted (C-ι-C₆-alkenyloxyimino)-C-ι-C₆-alkyl, substituted or non-substituted (C-ι-C₆-alkynyloxyimino)-C-ι-C₆-alkyl, substituted or non-substituted (benzyloxyimino)-C-ι-C₆-alkyl, substituted or non-substituted benzyloxy, substituted or non- substituted benzylsulphenyl, substituted or non-substituted phenoxy, substituted or non- substituted phenylsulphenyl, substituted or non-substituted aryl, substituted or non- substituted aryl-[Ci-C₈]-alkyl, substituted or non-substituted tri(Ci-C₈-alkyl)-silyloxy.

Other more preferred compounds of formula (I) according to the invention are those wherein R¹ represents a hydrogen atom, a hydroxy group, substituted or non-substituted Ci-C₈-alkyl, substituted or non-substituted C₃-C₈-Cy cloa Iky I, substituted or non-substituted Ci-C₈- halogenoalkyl having 1 to 5 halogen atoms, a C₂-C₈-alkenyl, substituted or non-substituted C₂-C₈-alkynyl, substituted or non-substituted d-C₈-alkoxy, substituted or non-substituted C₁- C₈-halogenoalkoxy having 1 to 5 halogen atoms, substituted or non-substituted C₂-C₈- alkenyloxy, substituted or non-substituted C₃-C₈-alkynyloxy, substituted or non-substituted d-C₈-alkylcarbonyloxy, substituted or non-substituted benzylsulphenyl, substituted or non- substituted phenoxy, substituted or non-substituted phenylsulphenyl, substituted or non- substituted aryl, substituted or non-substituted aryl-[d-C₈]-alkyl. Even more preferred compounds of formula (I) according to the invention are those wherein R¹ represents a hydrogen atom, a hydroxy group, substituted or non-substituted C-ι-C₈-alkyl, substituted or non-substituted C₃-C₈-cycloalkyl, substituted or non-substituted C₁-C₈- halogenoalkyl having 1 to 5 halogen atoms, substituted or non-substituted d-C₈-alkoxy, substituted or non-substituted d-C₈-halogenoalkoxy having 1 to 5 halogen atoms.

Other preferred compounds of formula (I) according to the invention are those wherein R² represents a hydrogen atom, substituted or non-substituted d-C₈-alkyl, substituted or non-substituted Ci-C₈-cycloalkyl.

Other preferred compounds of formula (I) according to the invention are those wherein R³ represents -(CR^aR^b)p-R⁴ and:

° R^a and R^b represent independently a hydrogen atom, substituted or non-substituted C₁- C₈-alkyl, a halogen atom, a substituted or non-substituted d-C₈-alkoxy, or R^a and R^b, form a 3- to 8-membered carbocyclic; o R⁴ represents a halogen atom, substituted or non-substituted Ci-C₈-alkyl, substituted or non-substituted d-C₈-alkenyl, substituted or non-substituted d-C₈-alkyloxy-d-C₈-alkyl, -C≡C-R⁵ wherein R⁵ represents a hydrogen atom, a halogen atom, substituted or non- substituted d-C₈-alkyl, substituted or non-substituted C₃-C₈-cycloalkyl, substituted or non-substituted d-Cs-alkyloxy-d-Cs-alkyl, substituted or non-substituted aryl, substituted or non-substituted aryl-[d-C₈]-alkyl, substituted or non-substituted tri(d-C₈- alkyl)-silyl; substituted or non-substituted, saturated or unsaturated A-, 5-, 6- or 7- membered heterocyclyl comprising up to 4 heteroatoms selected in the list consisting of N, O, S; substituted or non-substituted, saturated or unsaturated A-, 5-, 6- or 7- membered heterocyclyl-[Ci-C₈]-alkyl comprising up to 4 heteroatoms selected in the list consisting of N, O, S, wherein the N atom is substituted or unsubstituted with substituted or non-substituted Ci-C₈-alkyl, substituted or non-substituted C₃-C₈-cycloalkyl, substituted or non-substituted d-C₈-alkyloxy-Ci-C₈-alkyl, substituted or non-substituted aryl, substituted or non-substituted aryl-[Ci-C₈]-alkyl; o p is 0 or 1.

Even more preferred compounds of formula (I) are those wherein R³ represents -(CR^aR^b)p- R⁴ and: o R^a and R^b represent independently a hydrogen atom, a substituted or non-substituted C₁- C₈-alkyl, or

R^a and R^b, form a 3- to 8-membered carbocyclic; o R⁴ represents substituted or non-substituted d-Cs-alkyloxy-d-Cs-alkyl, -C=C-R⁵ wherein R⁵ represents a hydrogen atom, a halogen atom, substituted or non-substituted Ci-C₈-alkyl, substituted or non-substituted d-Cs-alkyloxy-C-i-Cs-alkyl, substituted or non- substituted, saturated or unsaturated 5 or 6 membered heterocyclyl comprising up to 4 heteroatoms selected in the list consisting of N, O, S; wherein the N atom is substituted or unsubstituted with substituted or non-substituted C-ι-C₈-alkyl, o p is 0 or 1

Other preferred compounds of formula (I) according to the invention are those wherein L represents an oxygen atom.

The above mentioned preferences with regard to the substituents of the compounds of formula (I) according to the invention can be combined in various manners. These combinations of preferred features thus provide sub-classes of compounds according to the invention. Examples of such sub-classes of preferred compounds according to the invention can combine:

- preferred features of Q¹ with preferred features of Q², Q³, R¹ to R³ and L;

- preferred features of Q² with preferred features of Q¹, Q³, R¹ to R³ and L;

- preferred features of Q³ with preferred features of Q¹, Q², R¹ to R³ and L; - preferred features of R¹ with preferred features of Q¹ to Q³, R² and R³ and L;

- preferred features of R¹ with preferred features of Q¹ to Q³, R², R³ and L;

- preferred features of R² with preferred features of Q¹ to Q³, R¹, R³ and L;

- preferred features of R³ with preferred features of Q¹ to Q³, R¹, R² and L;

- preferred features of L with preferred features of Q¹ to Q³ and R¹ to R³. In these combinations of preferred features of the substituents of the compounds according to the invention, the said preferred features can also be selected among the more preferred features of each of Q¹ to Q³, R¹ to R³ and L, so as to form most preferred subclasses of compounds according to the invention.

The present invention also relates to a process for the preparation of compounds of formula

(I)-

Thus, according to a further aspect of the present invention, there is a provided process P1 for the preparation of compounds of formula (Ia), as herein-defined and illustrated by the following reaction scheme:

Process P1 by reacting a compound of formula (II) , wherein LG represents a leaving group, Q¹, Q², Q³ and R¹, being as herein-defined with a compound of formula (III) wherein R², R³ are as herein-defined; optionally in the presence of a base such as an inorganic or an organic base; notably an alkaline earth metal or an alkali metal hydride, hydroxide, amide, alcoholate, acetate, carbonate or hydrogen carbonate, such as sodium hydride, sodium amide, lithiium diisopropylamide, sodium methanolate, sodium ethanolate, potassium tert-butanolate, sodium acetate, potassium acetate, calcium acetate, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, potassium bicarbonate, sodium bicarbonate, cesium carbonate or ammonium carbonate; and also tertiary amines, such as trimethylamine, triethylamine (TEA), tributylamine, N,N-dimethylaniline, N,N-dimethyl-benzylamine, N, N- diisopropyl-ethylamine (DIPEA), pyridine, N-methylpiperidine, N-methylmorpholine, N, N- dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyclononene (DBN) or diazabicycloundecene (DBU), optionally in the presence of an acid such as a Lewis acid; notably metal or metalloid halides such as aluminium trichloride, zinc dichloride, magnesium bromide, boron tribromide; or such as a Bronstedt acid; notably a mineral acid such as sulphuric acid, chlorhydric acid, ammonium chloride, phosphoric acid, or an organic acid, such as acetic acid, para-toluenesulphonic acid, optionally in the presence of a condensing agent such as acid halide former, notably phosgene, phosphorous tribromide, phosphorous trichloride, phosphorous pentachloride, phosphorous trichloride oxide or thionyl chloride; such as an anhydride former, notably ethyl chloroformate, methyl chloroformate, isopropyl chloroformate, isobutyl chloroformate, 2,2-dimethylpropionyl chloride or methanesulfonyl chloride; notably carbodiimides, such as N,N'-dicyclohexylcarbodiimide (DCC) or such as other customary condensing agents, notably phosphorous pentoxide, polyphosphoric acid, N,N'-carbonyldiimidazole, 2-ethoxy-N-ethoxycarbonyl-1 ,2-dihydroquinoline (EEDQ), triphenylphosphine/tetrachloromethane or bromo-tripyrrolidinophosphonium- hexafluorophosphate, optionally in the presence of a catalyst notably a transition metal catalyst, such as palladium salts or complexes for example palladium (II) chloride, palladium (II) acetate, tetrakis-(triphenylphosphine) palladium(O), bis-(triphenylphosphine) palladium dichloride (II), tris(dibenzylideneacetone) dipalladium(O), bis(dibenzylideneacetone) palladium(O), or 1 ,1'-bis(diphenylphosphino)ferrocene-palladium (II) chloride. As an alternative the palladium complex is directly generated in the reaction mixture by separately adding to the reaction mixture a palladium salt and a complex ligand such as a phosphine, for example triethylphosphine, tri-tert-butylphosphine, tricyclohexylphosphine, 2- (dicyclohexylphosphine)biphenyl, 2-(di-tert-butylphosphin)biphenyl, 2-

(dicyclohexylphosphine)-2'-(N,N-dimethylamino)-biphenyl, triphenylphosphine, tris-(o- tolyl)phosphine, sodium 3-(diphenylphosphino)benzolsulfonate, tris-2-

(methoxyphenyl)phosphine, 2,2'-bis-(diphenylphosphine)-1 , 1 '-binaphthyl, 1 ,4-bis-

(diphenylphosphine)butane, 1 ,2-bis-(diphenylphosphine)ethane, 1 ,4-bis-

(dicyclohexylphosphine)butane, 1 ,2-bis-(dicyclohexylphosphine)ethane, 2-

(dicyclohexylphosphine)-2'-(N,N-dimethylamino)-biphenyl, bis(diphenylphosphino)ferrocene, tris-(2,4-tert-butylphenyl)-phosphite, (R)-(-)-1-[(S)-2-(diphenylphosphino)ferrocenyl]ethyldi- tert-butylphosphine, (S)-(+)-1-[(R)-2-

(diphenylphosphino)ferrocenyl]ethyldicyclohexylphosphine, (R)-(-)-1-[(S)-2-

(diphenylphosphino)ferrocenyl]ethyldicyclohexylphosphine, (S)-(+)-1-[(R)-2-

(diphenylphosphino)ferrocenyl]ethyldi-t-butylphosphine; in one or a different-pot conditions.

Suitable leaving groups LG can be selected in the list consisting of a halogen atom or other customary nucleofugal groups such as alcoolate, hydroxide or cyanide.

For the compounds of formula (Ia) according to the invention when L represents an oxygen atom, process P1 according to the invention can be completed by a further step comprising the additional modification of this group, notably by a reaction of thiocarbonylation in the presence of a thiocarbonylating agent such as 2,4-bis(4-methoxyphenyl)-1 , 3,2,4- dithiadiphosphetane 2,4-disulfide, phosphorus pentasulfide, sulphur to yield to a compound of formula (Ib), according to known methods. In such a case there is provided a process P2 according to the invention and such a process P2 can be illustrated by the following reaction scheme :

(Ia)

(Ib)

Process P2

According to the invention, processes P1 and P2 can be performed if appropriate in the presence of a solvent or a base. According to the invention, processes P1 can be performed if appropriate in the presence of a catalyst. Suitable catalyst can be chosen as being 4-dimethyl-anninopyridine, 1-hydroxy- benzotriazole or dimethylformannide.

In case LG represents a hydroxy group, the process P2 according to the present invention can be performed in the presence of condensing agent. Suitable condensing agent can be chosen as being acid halide former, such as phosgene, phosphorous tri-bro-mide, phosphorous trichloride, phosphorous pentachloride, phosphorous trichloride oxide or thionyl chloride; anhydride former, such as ethyl chloroformate, methyl chloroformate, isopropyl chloroformate, isobutyl chloroformate or methanesulfonyl chloride; carbodiimides, such as N.N'-dicyclohexylcarbodiimide (DCC) or other customary condensing agents, such as phosphorous pentoxide, polyphosphoric acid, N,N'-carbonyl-diimidazole, 2-ethoxy-N- ethoxycarbonyl-1 ,2-dihydroquinoline (EEDQ), triphenylphosphine/tetrachloromethane, 4- (4,6-dimethoxy[1.3.5]triazin-2-yl)-4-methylmorpholinium chloride hydrate or bromo- tripyrrolidino-phosphonium-hexafluorophosphate.

Suitable solvents for carrying out processes P1 to P2 according to the invention are customary inert organic solvents. Preference is given to using optionally halogenated aliphatic, alicyclic or aromatic hydrocarbons, such as petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin ; chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichlorethane or trichlorethane ; ethers, such as diethyl ether, diisopropyl ether, methyl tert-butyl ether, methyl tert-amyl ether, dioxane, tetrahydrofuran, 1 ,2-dimethoxyethane, 1 ,2-diethoxyethane or anisole ; nitriles, such as acetonitrile, propionitrile, n- or iso-butyronitrile or benzonitrile ; amides, such as Λ/,Λ/-dimethylformamide, Λ/,Λ/-dimethylacetamide, Λ/-methylformanilide, N- methylpyrrolidone or hexamethylphosphoric triamide ; esters, such as methyl acetate or ethyl acetate, sulphoxides, such as dimethyl sulphoxide, or sulphones, such as sulpholane.

Suitable bases for carrying out processes P1 and P2 according to the invention are inorganic and organic bases which are customary for such reactions. Preference is given to using alkaline earth metal, alkali metal hydride, alkali metal hydroxides or alkali metal alkoxides, such as sodium hydroxide, sodium hydride, calcium hydroxide, potassium hydroxide, potassium tert-butoxide or other ammonium hydroxide, alkali metal carbonates, such as sodium carbonate, potassium carbonate, potassium bicarbonate, sodium bicarbonate, cesium carbonate, alkali metal or alkaline earth metal acetates, such as sodium acetate, potassium acetate, calcium acetate, and also tertiary amines, such as trimethylamine, triethylamine, diisopropylethylamine, tributylamine, Λ/,Λ/-dimethylaniline, pyridine, Λ/-methylpiperidine, Λ/,Λ/-dimethylaminopyridine, 1 ,4-diazabicyclo[2.2.2]octane (DABCO), 1 ,5-diazabicyclo[4.3.0]non-5-ene (DBN) or 1 ,8-diazabicyclo[5.4.0]undec-7-ene (DBU). When carrying out processes P1 to P2 according to the invention, the reaction temperature can independently be varied within a relatively wide range. Generally, processes P1to P2 according to the invention are carried out at temperatures between -8O⁰C and 16O⁰C.

Processes P1 to P2 according to the invention are generally independently carried out under atmospheric pressure. However, it is also possible to operate under elevated or reduced pressure.

Work-up is carried out by customary methods. Generally, the reaction mixture is treated with water and the organic phase is separated off and, after drying, concentrated under reduced pressure. If appropriate, the remaining residue can be freed by customary methods, such as chromatography or recrystallization, from any impurities that may still be present.

Compounds according to the invention can be prepared according to the above described processes. It will nevertheless be understood that, on the basis of his general knowledge and of available publications, the skilled worker will be able to adapt these processes according to the specifics of each of the compounds according to the invention that is desired to be synthesised.

In a further aspect, the present invention also relates to a fungicide composition comprising an effective and non-phytotoxic amount of an active compound of formula (I). The expression "effective and non-phytotoxic amount" means an amount of composition according to the invention that is sufficient to control or destroy the fungi present or liable to appear on the crop sand that does not entail any appreciable symptom of phytotoxicity for the said crops. Such an amount can vary within a wide range depending on the fungus to be controlled, the type of crop, the climatic conditions and the compounds included in the fungicide composition according to the invention. This amount can be determined by systematic field trials, that are within the capabilities of a person skilled in the art.

Thus, according to the invention, there is provided a fungicide composition comprising, as an active ingredient, an effective amount of a compound of formula (I) as herein-defined and an agriculturally acceptable support, carrier or filler.

According to the invention, the term "support" denotes a natural or synthetic, organic or inorganic compound with that the active compound of formula (I) is combined or associated to make it easier to apply, notably to the parts of the plant. This support is thus generally inert and should be agriculturally acceptable. The support can be a solid or a liquid. Examples of suitable supports include clays, natural or synthetic silicates, silica, resins, waxes, solid fertilisers, water, alcohols, in particular butanol, organic solvents, mineral and plant oils and derivatives thereof. Mixtures of such supports can also be used.

The composition according to the invention can also comprise additional components. In particular, the composition can further comprise a surfactant. The surfactant can be an emulsifier, a dispersing agent or a wetting agent of ionic or non-ionic type or a mixture of such surfactants. Mention can be made, for example, of polyacrylic acid salts, lignosulphonic acid salts, phenolsulphonic or naphthalenesulphonic acid salts, polycondensates of ethylene oxide with fatty alcohols or with fatty acids or with fatty amines, substituted phenols (in particular alkylphenols or arylphenols), salts of sulphosuccinic acid esters, taurine derivatives (in particular alkyl taurates), phosphoric esters of polyoxyethylated alcohols or phenols, fatty acid esters of polyolsand derivatives of the above compounds containing sulphate, sulphonate and phosphate functions. The presence of at least one surfactant is generally essential when the active compound and/or the inert support are water-insoluble and when the vector agent for the application is water. Preferably, surfactant content can be comprised from 5% to 40% by weight of the composition.

Optionally, additional components can also be included, e.g. protective colloids, adhesives, thickeners, thixotropic agents, penetration agents, stabilisers, sequestering agents. More generally, the active compounds can be combined with any solid or liquid additive, that complies with the usual formulation techniques.

In general, the composition according to the invention can contain from 0.05 to 99% by weight of active compound, preferably 10 to 70% by weight.

Compositions according to the invention can be used in various forms such as aerosol dispenser, capsule suspension, cold fogging concentrate, dustable powder, emulsifiable concentrate, emulsion oil in water, emulsion water in oil, encapsulated granule, fine granule, flowable concentrate for seed treatment, gas (under pressure), gas generating product, granule, hot fogging concentrate, macrogranule, microgranule, oil dispersible powder, oil miscible flowable concentrate, oil miscible liquid, paste, plant rodlet, powder for dry seed treatment, seed coated with a pesticide, soluble concentrate, soluble powder, solution for seed treatment, suspension concentrate (flowable concentrate), ultra low volume (ULV) liquid, ultra low volume (ULV) suspension, water dispersible granules or tablets, water dispersible powder for slurry treatment, water soluble granules or tablets, water soluble powder for seed treatment and wettable powder. These compositions include not only compositions that are ready to be applied to the plant or seed to be treated by means of a suitable device, such as a spraying or dusting device, but also concentrated commercial compositions that must be diluted before application to the crop.

The compounds according to the invention can also be mixed with one or more insecticide, fungicide, bactericide, attractant, acaricide or pheromone active substance or other compounds with biological activity. The mixtures thus obtained have normally a broadened spectrum of activity. The mixtures with other fungicide compounds are particularly advantageous.

Examples of suitable fungicide mixing partners can be selected in the following lists:

(1 ) Inhibitors of the nucleic acid synthesis, for example benalaxyl, benalaxyl-M, bupirimate, clozylacon, dimethirimol, ethirimol, furalaxyl, hymexazol, metalaxyl, metalaxyl-M, ofurace, oxadixyl and oxolinic acid.

(2) Inhibitors of the mitosis and cell division, for example benomyl, carbendazim, chlorfenazole, diethofencarb, ethaboxam, fuberidazole, pencycuron, thiabendazole, thiophanate, thiophanate-methyl and zoxamide.

(3) Inhibitors of the respiration, for example diflumetorim as Cl-respiration inhibitor; bixafen, boscalid, carboxin, fenfuram, flutolanil, fluopyram, furametpyr, furmecyclox, isopyrazam (mixture of syn-epimeric racemate 1 RS, 4SR, 9RS and anti-epimeric racemate 1 RS, 4SR, 9SR), isopyrazam (syn epimeric racemate 1 RS,4SR,9RS), isopyrazam (syn- epimeric enantiomer 1 R,4S,9R), isopyrazam (syn-epimeric enantiomer 1 S,4R,9S), isopyrazam (anti-epimeric racemate 1 RS,4SR,9SR), isopyrazam (anti-epimeric enantiomer 1 R,4S,9S), isopyrazam (anti-epimeric enantiomer 1S,4R,9R), mepronil, oxycarboxin, penflufen, penthiopyrad, sedaxane, thifluzamide as Cll-respiration inhibitor; amisulbrom, azoxystrobin, cyazofamid, dimoxystrobin, enestroburin, famoxadone, fenamidone, fluoxastrobin, kresoxim-methyl, metominostrobin, orysastrobin, picoxystrobin, pyraclostrobin, pyraoxystrobin, pyrametostrobin, pyribencarb, trifloxystrobin as Clll-respiration inhibitor.

(4) Compounds capable to act as an uncoupler, like for example binapacryl, dinocap, fluazinam and meptyldinocap.

(5) Inhibitors of the ATP production, for example fentin acetate, fentin chloride, fentin hydroxide, and silthiofam. (6) Inhibitors of the amino acid and/or protein biosynthesis, for example andoprim, blasticidin-S, cyprodinil, kasugamycin, kasugamycin hydrochloride hydrate, mepanipyrim and pyrimethanil.

(7) Inhibitors of the signal transduction, for example fenpiclonil, fludioxonil and quinoxyfen.

(8) Inhibitors of the lipid and membrane synthesis, for example biphenyl, chlozolinate, edifenphos, etridiazole, iodocarb, iprobenfos, iprodione, isoprothiolane, procymidone, propamocarb, propamocarb hydrochloride, pyrazophos, tolclofos-m ethyl and vinclozolin.

(9) Inhibitors of the ergosterol biosynthesis, for example aldimorph, azaconazole, bitertanol, bromuconazole, cyproconazole, diclobutrazole, difenoconazole, diniconazole, diniconazole- M, dodemorph, dodemorph acetate, epoxiconazole, etaconazole, fenarimol, fenbuconazole, fenhexamid, fenpropidin, fenpropimorph, fluquinconazole, flurprimidol, flusilazole, flutriafol, furconazole, furconazole-cis, hexaconazole, imazalil, imazalil sulfate, imibenconazole, ipconazole, metconazole, myclobutanil, naftifine, nuarimol, oxpoconazole, paclobutrazol, pefurazoate, penconazole, piperalin, prochloraz, propiconazole, prothioconazole, pyributicarb, pyrifenox, quinconazole, simeconazole, spiroxamine, tebuconazole, terbinafine, tetraconazole, triadimefon, triadimenol, tridemorph, triflumizole, triforine, triticonazole, uniconazole, viniconazole and voriconazole.

(10) Inhibitors of the cell wall synthesis, for example benthiavalicarb, dimethomorph, flumorph, iprovalicarb, mandipropamid, polyoxins, polyoxorim, prothiocarb, validamycin A, and valifenalate.

(11 ) Inhibitors of the melanine biosynthesis, for example carpropamid, diclocymet, fenoxanil, phthalide, pyroquilon and tricyclazole.

(12) Compounds capable to induce a host defence, like for example acibenzolar-S-methyl, probenazole, and tiadinil.

(13) Compounds capable to have a multisite action, like for example bordeaux mixture, captafol, captan, chlorothalonil, copper naphthenate, copper oxide, copper oxychloride, copper preparations such as copper hydroxide, copper sulphate, dichlofluanid, dithianon, dodine, dodine free base, ferbam, fluorofolpet, folpet, guazatine, guazatine acetate, iminoctadine, iminoctadine albesilate, iminoctadine triacetate, mancopper, mancozeb, maneb, metiram, metiram zinc, oxine-copper, propamidine, propineb, sulphur and sulphur preparations including calcium polysulphide, thiram, tolylfluanid, zineb and ziram. (14) Further compounds like for example 2,3-dibutyl-6-chlorothieno[2,3-d]pyrimidin-4(3H)- one, ethyl (2Z)-3-amino-2-cyano-3-phenylprop-2-enoate, N-[2-(1 ,3-dimethylbutyl)phenyl]-5- fluoro-1 ,3-dimethyl-1 H-pyrazole-4-carboxamide, 3-(difluoromethyl)-1-methyl-N-(3',4',5'- trifluorobiphenyl-2-yl)-1 H-pyrazole-4-carboxamide, 3-(difluoromethyl)-N-[4-fluoro-2- (1 ,1 ,2,3,3,3-hexafluoropropoxy)phenyl]-1-methyl-1 H-pyrazole-4-carboxamide, (2E)-2-(2-{[6- (3-chloro-2-methylphenoxy)-5-fluoropyrimidin-4-yl]oxy}phenyl)-2-(methoxyimino)-N- methylethanamide, (2E)-2-{2-[({[(2E,3E)-4-(2,6-dichlorophenyl)but-3-en-2- ylidene]amino}oxy)methyl]phenyl}-2-(methoxyimino)-N-methylethanamide, 2-chloro-N-(1 ,1 ,3- trimethyl-2,3-dihydro-1 H-inden-4-yl)pyridine-3-carboxamide, N-(3-ethyl-3,5,5- trimethylcyclohexyl)-3-(formylamino)-2-hydroxybenzamide, 5-methoxy-2-methyl-4-(2-{[({(1 E)- 1-[3-(trifluoromethyl)phenyl]ethylidene}amino)oxy]methyl}phenyl)-2,4-dihydro-3H-1 ,2,4- triazol-3-one, (2E)-2-(methoxyimino)-N-methyl-2-(2-{[({(1 E)-1-[3- (trifluoromethyl)phenyl]ethylidene}amino)oxy]methyl}phenyl)ethanamide, (2E)-2- (methoxyimino)-N-methyl-2-{2-[(E)-({1-[3- (trifluoromethyl)phenyl]ethoxy}imino)methyl]phenyl}ethanamide, (2E)-2-{2-[({[(1 E)-1-(3-{[(E)- 1-fluoro-2-phenylethenyl]oxy}phenyl)ethylidene]amino}oxy)methyl]phenyl}-2-(methoxyimino)- N-methylethanamide, 1-(4-chlorophenyl)-2-(1 H-1 ,2,4-triazol-1-yl)cycloheptanol, methyl 1- (2,2-dimethyl-2,3-dihydro-1 H-inden-1-yl)-1 H-imidazole-5-carboxylate, N-ethyl-N-methyl-N'- {2-methyl-5-(trifluoromethyl)-4-[3-(trimethylsilyl)propoxy]phenyl}imidoformamide, N'-{5- (difluoromethyl)-2-methyl-4-[3-(trimethylsilyl)propoxy]phenyl}-N-ethyl-N- methylimidoformamide, O-{1-[(4-methoxyphenoxy)methyl]-2,2-dimethylpropyl} 1 H-imidazole- 1-carbothioate, N-[2-(4-{[3-(4-chlorophenyl)prop-2-yn-1-yl]oxy}-3-methoxyphenyl)ethyl]-N²- (methylsulfonyl)valinamide, 5-chloro-7-(4-methylpiperidin-1-yl)-6-(2,4,6- trifluorophenyl)[1 ,2,4]triazolo[1 ,5-a]pyrimidine, 5-amino-1 ,3,4-thiadiazole-2-thiol, propamocarb-fosetyl, 1-[(4-methoxyphenoxy)methyl]-2,2-dimethylpropyl 1 H-imidazole-1- carboxylate, 1-methyl-N-[2-(1 ,1 ,2,2-tetrafluoroethoxy)phenyl]-3-(trifluoromethyl)-1 H-pyrazole- 4-carboxamide, 2,3,5,6-tetrachloro-4-(methylsulfonyl)pyridine, 2-butoxy-6-iodo-3-propyl-4H- chromen-4-one, 2-phenylphenol and salts, 3-(difluoromethyl)-1-methyl-N-[2-(1 , 1 ,2,2- tetrafluoroethoxy)phenyl]-1 H-pyrazole-4-carboxamide, 3,4,5-trichloropyridine-2,6- dicarbonitrile, 3-[5-(4-chlorophenyl)-2,3-dimethylisoxazolidin-3-yl]pyridine, 3-chloro-5-(4- chlorophenyl)-4-(2,6-difluorophenyl)-6-methylpyridazine, 4-(4-chlorophenyl)-5-(2,6- difluorophenyl)-3,6-dimethylpyridazine, quinolin-8-ol, quinolin-8-ol sulfate (2:1 ) (salt), tebufloquin, 5-methyl-6-octyl-3,7-dihydro[1 ,2,4]triazolo[1 ,5-a]pyrimidin-7-amine, 5-ethyl-6- octyl-3,7-dihydro[1 ,2,4]triazolo[1 ,5-a]pyrimidin-7-amine, ametoctradin, benthiazole, bethoxazin, capsimycin, carvone, chinomethionat, chloroneb, cufraneb, cyflufenamid, cymoxanil, cyprosulfamide, dazomet, debacarb, dichlorophen, diclomezine, dicloran, difenzoquat, difenzoquat methylsulphate, diphenylamine, ecomate, ferimzone, flumetover, fluopicolide, fluoroimide, flusulfamide, flutianil, fosetyl-aluminium, fosetyl-calcium, fosetyl- sodium, hexachlorobenzene, irumamycin, isotianil, methasulfocarb, methyl (2E)-2-{2- [({cyclopropyl[(4-methoxyphenyl)imino]methyl}thio)methyl]phenyl}-3-methoxyacrylate, methyl isothiocyanate, metrafenone, (5-chloro-2-methoxy-4-methylpyridin-3-yl)(2,3,4-trimethoxy-6- methylphenyl)methanone, mildiomycin, tolnifanide, N-(4-chlorobenzyl)-3-[3-methoxy-4- (prop-2-yn-1-yloxy)phenyl]propanamide, N-[(4-chlorophenyl)(cyano)methyl]-3-[3-methoxy-4- (prop-2-yn-1-yloxy)phenyl]propanamide, N-[(5-bromo-3-chloropyridin-2-yl)methyl]-2,4- dichloropyridine-3-carboxamide, N-[1-(5-bromo-3-chloropyridin-2-yl)ethyl]-2,4- dichloropyridine-3-carboxamide, N-[1-(5-bromo-3-chloropyridin-2-yl)ethyl]-2-fluoro-4- iodopyridine-3-carboxamide, N-{(Z)-[(cyclopropylmethoxy)imino][6-(difluoromethoxy)-2,3- difluorophenyl]methyl}-2-phenylacetamide, N-{(E)-[(cyclopropylmethoxy)imino][6- (difluoromethoxy)-2,3-difluorophenyl]methyl}-2-phenylacetamide, natamycin, nickel dimethyldithiocarbamate, nitrothal-isopropyl, octhilinone, oxamocarb, oxyfenthiin, pentachlorophenol and salts, phenazine-1-carboxylic acid, phenothrin, phosphorous acid and its salts, propamocarb fosetylate, propanosine-sodium, proquinazid, pyrrolnitrine, quintozene, S-prop-2-en-1-yl 5-amino-2-(1-methylethyl)-4-(2-methylphenyl)-3-oxo-2,3- dihydro-1 H-pyrazole-1-carbothioate, tecloftalam, tecnazene, triazoxide, trichlamide, 5-chloro- N'-phenyl-N'-prop-2-yn-1-ylthiophene-2-sulfonohydrazide, zarilamid, N-methyl-2-(1-{[5- methyl-3-(trifluoromethyl)-1 H-pyrazol-1-yl]acetyl}piperidin-4-yl)-N-[(1 R)-1 , 2,3,4- tetrahydronaphthalen-1-yl]-1 ,3-thiazole-4-carboxamide, N-methyl-2-(1-{[5-methyl-3- (trifluoromethyl)-1 H-pyrazol-1-yl]acetyl}piperidin-4-yl)-N-(1 ,2,3,4-tetrahydronaphthalen-1-yl)- 1 ,3-thiazole-4-carboxamide, 3-(difluoromethyl)-N-[4-fluoro-2-(1 ,1 ,2,3,3,3- hexafluoropropoxy)phenyl]-1-methyl-1 H-pyrazole-4-carboxamide and pentyl {6-[({[(1-methyl- 1 H-tetrazol-5-yl)(phenyl)methylidene]amino}oxy)methyl]pyridin-2-yl}carbamate.

The composition according to the invention comprising a mixture of a compound of formula (I) with a bactericide compound can also be particularly advantageous. Examples of suitable bactericide mixing partners can be selected in the following list: bronopol, dichlorophen, nitrapyrin, nickel dimethyldithiocarbamate, kasugamycin, octhilinone, furancarboxylic acid, oxytetracycline, probenazole, streptomycin, tecloftalam, copper sulphate and other copper preparations.

The compounds of formula (I) and the fungicide composition according to the invention can be used to curatively or preventively control the phytopathogenic fungi of plants or crops. Thus, according to a further aspect of the invention, there is provided a method for curatively or preventively controlling the phytopathogenic fungi of plants or crops characterised in that a compound of formula (I) or a fungicide composition according to the invention is applied to the seed, the plant or to the fruit of the plant or to the soil wherein the plant is growing or wherein it is desired to grow. The method of treatment according to the invention can also be useful to treat propagation material such as tubers or rhizomes, but also seeds, seedlings or seedlings pricking out and plants or plants pricking out. This method of treatment can also be useful to treat roots. The method of treatment according to the invention can also be useful to treat the overground parts of the plant such as trunks, stems or stalks, leaves, flowers and fruit of the concerned plant.

Among the plants that can be protected by the method according to the invention, mention can be made of cotton; flax; vine; fruit or vegetable crops such as Rosaceae sp. (for instance pip fruit such as apples and pears, but also stone fruit such as apricots, almonds and peaches), Ribesioidae sp., Juglandaceae sp., Betulaceae sp., Anacardiaceae sp., Fagaceae sp., Moraceae sp., Oleaceae sp., Actinidaceae sp., Lauraceae sp., Musaceae sp. (for instance banana trees and plantins), Rubiaceae sp., Theaceae sp., Sterculiceae sp., Rutaceae sp. (for instance lemons oranges and grapefruit); Solanaceae sp. (for instance tomatoes), ϋliaceae sp., Asteraceae sp. (for instance lettuces), Umbelliferae sp., Cruciferae sp., Chenopodiaceae sp., Cucurbitaceae sp., Papilionaceae sp. (for instance peas), Rosaceae sp. (for instance strawberries); major crops such as Graminae sp. (for instance maize, lawn or cereals such as wheat, rye, rice, barley and triticale), Asteraceae sp. (for instance sunflower), Cruciferae sp. (for instance colza), Fabacae sp. (for instance peanuts), Papilionaceae sp. (for instance soybean), Solanaceae sp. (for instance potatoes), Chenopodiaceae sp. (for instance beetroots), Elaeis sp. (for instance oil palm); horticultural and forest crops; as well as genetically modified homologues of these crops.

The method of treatment according to the invention can be used in the treatment of genetically modified organisms (GMOs), e.g. plants or seeds. Genetically modified plants (or transgenic plants) are plants in which a heterologous gene has been stably integrated into the genome. The expression "heterologous gene" essentially means a gene which is provided or assembled outside the plant and when introduced in the nuclear, chloroplastic or mitochondrial genome gives the transformed plant new or improved agronomic or other properties by expressing a protein or polypeptide of interest or by down regulating or silencing other gene(s) which are present in the plant (using for example, antisense technology, co suppression technology or RNA interference - RNAi - technology). A heterologous gene that is located in the genome is also called a transgene. A transgene that is defined by its particular location in the plant genome is called a transformation or transgenic event.

Depending on the plant species or plant cultivars, their location and growth conditions (soils, climate, vegetation period, diet), the treatment according to the invention may also result in superadditive ("synergistic") effects. Thus, for example, reduced application rates and/or a widening of the activity spectrum and/or an increase in the activity of the active compounds and compositions which can be used according to the invention, better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering performance, easier harvesting, accelerated maturation, higher harvest yields, bigger fruits, larger plant height, greener leaf color, earlier flowering, higher quality and/or a higher nutritional value of the harvested products, higher sugar concentration within the fruits, better storage stability and/or processability of the harvested products are possible, which exceed the effects which were actually to be expected.

At certain application rates, the active compound combinations according to the invention may also have a strengthening effect in plants. Accordingly, they are also suitable for mobilizing the defense system of the plant against attack by unwanted phytopathogenic fungi and/ or microorganisms and/or viruses. This may, if appropriate, be one of the reasons of the enhanced activity of the combinations according to the invention, for example against fungi. Plant-strengthening (resistance-inducing) substances are to be understood as meaning, in the present context, those substances or combinations of substances which are capable of stimulating the defense system of plants in such a way that, when subsequently inoculated with unwanted phytopathogenic fungi and/ or microorganisms and/or viruses, the treated plants display a substantial degree of resistance to these unwanted phytopathogenic fungi and/ or microorganisms and/or viruses. In the present case, unwanted phytopathogenic fungi and/ or microorganisms and/or viruses are to be understood as meaning phytopathogenic fungi, bacteria and viruses. Thus, the substances according to the invention can be employed for protecting plants against attack by the abovementioned pathogens within a certain period of time after the treatment. The period of time within which protection is effected generally extends from 1 to 10 days, preferably 1 to 7 days, after the treatment of the plants with the active compounds.

Plants and plant cultivars which are preferably to be treated according to the invention include all plants which have genetic material which impart particularly advantageous, useful traits to these plants (whether obtained by breeding and/or biotechnological means).

Plants and plant cultivars which are also preferably to be treated according to the invention are resistant against one or more biotic stresses, i.e. said plants show a better defense against animal and microbial pests, such as against nematodes, insects, mites, phytopathogenic fungi, bacteria, viruses and/or viroids. Plants and plant cultivars which may also be treated according to the invention are those plants which are resistant to one or more abiotic stresses. Abiotic stress conditions may include, for example, drought, cold temperature exposure, heat exposure, osmotic stress, flooding, increased soil salinity, increased mineral exposure, ozon exposure, high light exposure, limited availability of nitrogen nutrients, limited availability of phosphorus nutrients, shade avoidance.

Plants and plant cultivars which may also be treated according to the invention, are those plants characterized by enhanced yield characteristics. Increased yield in said plants can be the result of, for example, improved plant physiology, growth and development, such as water use efficiency, water retention efficiency, improved nitrogen use, enhanced carbon assimilation, improved photosynthesis, increased germination efficiency and accelerated maturation. Yield can furthermore be affected by improved plant architecture (under stress and non-stress conditions), including but not limited to, early flowering, flowering control for hybrid seed production, seedling vigor, plant size, internode number and distance, root growth, seed size, fruit size, pod size, pod or ear number, seed number per pod or ear, seed mass, enhanced seed filling, reduced seed dispersal, reduced pod dehiscence and lodging resistance. Further yield traits include seed composition, such as carbohydrate content, protein content, oil content and composition, nutritional value, reduction in anti-nutritional compounds, improved processability and better storage stability.

Plants that may be treated according to the invention are hybrid plants that already express the characteristic of heterosis or hybrid vigor which results in generally higher yield, vigor, health and resistance towards biotic and abiotic stress factors. Such plants are typically made by crossing an inbred male-sterile parent line (the female parent) with another inbred male-fertile parent line (the male parent). Hybrid seed is typically harvested from the male sterile plants and sold to growers. Male sterile plants can sometimes (e.g. in corn) be produced by detasseling, i.e. the mechanical removal of the male reproductive organs (or males flowers) but, more typically, male sterility is the result of genetic determinants in the plant genome. In that case, and especially when seed is the desired product to be harvested from the hybrid plants it is typically useful to ensure that male fertility in the hybrid plants is fully restored. This can be accomplished by ensuring that the male parents have appropriate fertility restorer genes which are capable of restoring the male fertility in hybrid plants that contain the genetic determinants responsible for male-sterility. Genetic determinants for male sterility may be located in the cytoplasm. Examples of cytoplasmic male sterility (CMS) were for instance described in Brassica species (WO 1992/005251 , WO 1995/009910, WO 1998/27806, WO 2005/002324, WO 2006/021972 and US 6,229,072). However, genetic determinants for male sterility can also be located in the nuclear genome. Male sterile plants can also be obtained by plant biotechnology methods such as genetic engineering. A particularly useful means of obtaining male-sterile plants is described in WO 1989/10396 in which, for example, a ribonuclease such as barnase is selectively expressed in the tapetum cells in the stamens. Fertility can then be restored by expression in the tapetum cells of a ribonuclease inhibitor such as barstar (e.g. WO 1991/002069).

Plants or plant cultivars (obtained by plant biotechnology methods such as genetic engineering) which may be treated according to the invention are herbicide-tolerant plants, i.e. plants made tolerant to one or more given herbicides. Such plants can be obtained either by genetic transformation, or by selection of plants containing a mutation imparting such herbicide tolerance.

Herbicide-tolerant plants are for example glyphosate-tolerant plants, i.e. plants made tolerant to the herbicide glyphosate or salts thereof. Plants can be made tolerant to glyphosate through different means. For example, glyphosate-tolerant plants can be obtained by transforming the plant with a gene encoding the enzyme 5-enolpyruvylshikimate-3- phosphate synthase (EPSPS). Examples of such EPSPS genes are the AroA gene (mutant CT7) of the bacterium Salmonella typhimuήum (Comai et al., Science (1983), 221 , 370-371 ), the CP4 gene of the bacterium Agrobacterium sp. (Barry et al., Curr. Topics Plant Physiol. (1992), 7, 139-145), the genes encoding a Petunia EPSPS (Shah et al., Science (1986), 233, 478-481 ), a Tomato EPSPS (Gasser et al., J. Biol. Chem. (1988),263, 4280-4289), or an Eleusine EPSPS (WO 2001/66704). It can also be a mutated EPSPS as described in for example EP-A 0837944, WO 2000/066746, WO 2000/066747 or WO 2002/026995. Glyphosate-tolerant plants can also be obtained by expressing a gene that encodes a glyphosate oxido-reductase enzyme as described in US 5,776,760 and US 5,463,175. Glyphosate-tolerant plants can also be obtained by expressing a gene that encodes a glyphosate acetyl transferase enzyme as described in for example WO 2002/036782, WO 2003/092360, WO 2005/012515 and WO 2007/024782. Glyphosate-tolerant plants can also be obtained by selecting plants containing naturally-occurring mutations of the above- mentioned genes, as described in for example WO 2001/024615 or WO 2003/013226. Other herbicide resistant plants are for example plants that are made tolerant to herbicides inhibiting the enzyme glutamine synthase, such as bialaphos, phosphinothricin or glufosinate. Such plants can be obtained by expressing an enzyme detoxifying the herbicide or a mutant glutamine synthase enzyme that is resistant to inhibition. One such efficient detoxifying enzyme is an enzyme encoding a phosphinothricin acetyltransferase (such as the bar or pat protein from Streptomyces species). Plants expressing an exogenous phosphinothricin acetyltransferase are for example described in US 5,561 ,236; US 5,648,477; US 5,646,024; US 5,273,894; US 5,637,489; US 5,276,268; US 5,739,082; US 5,908,810 and US 7,112,665. Further herbicide-tolerant plants are also plants that are made tolerant to the herbicides inhibiting the enzyme hydroxyphenylpyruvatedioxygenase (HPPD).

Hydroxyphenylpyruvatedioxygenases are enzymes that catalyze the reaction in which para- hydroxyphenylpyruvate (HPP) is transformed into homogentisate. Plants tolerant to HPPD- inhibitors can be transformed with a gene encoding a naturally-occurring resistant HPPD enzyme, or a gene encoding a mutated HPPD enzyme as described in WO 1996/038567, WO 1999/024585 and WO 1999/024586. Tolerance to HPPD-inhibitors can also be obtained by transforming plants with genes encoding certain enzymes enabling the formation of homogentisate despite the inhibition of the native HPPD enzyme by the HPPD-inhibitor. Such plants and genes are described in WO 1999/034008 and WO 2002/36787. Tolerance of plants to HPPD inhibitors can also be improved by transforming plants with a gene encoding an enzyme prephenate dehydrogenase in addition to a gene encoding an HPPD- tolerant enzyme, as described in WO 2004/024928. Still further herbicide resistant plants are plants that are made tolerant to acetolactate synthase (ALS) inhibitors. Known ALS-inhibitors include, for example, sulfonylurea, imidazolinone, triazolopyrimidines, pyrimidinyloxy(thio)benzoates, and/or sulfonylaminocarbonyltriazolinone herbicides. Different mutations in the ALS enzyme (also known as acetohydroxyacid synthase, AHAS) are known to confer tolerance to different herbicides and groups of herbicides, as described for example in Tranel and Wright, Weed Science (2002), 50, 700-712, but also, in US 5,605,011 , US 5,378,824, US 5,141 ,870, and US 5,013,659. The production of sulfonylurea-tolerant plants and imidazolinone-tolerant plants is described in US 5,605,011 ; US 5,013,659; US 5,141 ,870; US 5,767,361 ; US 5,731 ,180; US 5,304,732; US 4,761 ,373; US 5,331 ,107; US 5,928,937; and US 5,378,824; and international publication WO 1996/033270. Other imidazolinone-tolerant plants are also described in for example WO 2004/040012, WO 2004/106529, WO 2005/020673, WO 2005/093093, WO 2006/007373, WO 2006/015376, WO 2006/024351 , and WO 2006/060634. Further sulfonylurea- and imidazolinone-tolerant plants are also described in for example WO 2007/024782. Other plants tolerant to imidazolinone and/or sulfonylurea can be obtained by induced mutagenesis, selection in cell cultures in the presence of the herbicide or mutation breeding as described for example for soybeans in US 5,084,082, for rice in WO 1997/41218, for sugar beet in US 5,773,702 and WO 1999/057965 , for lettuce in US 5,198,599, or for sunflower in WO 2001/065922.

Plants or plant cultivars (obtained by plant biotechnology methods such as genetic engineering) which may also be treated according to the invention are insect-resistant transgenic plants, i.e. plants made resistant to attack by certain target insects. Such plants can be obtained by genetic transformation, or by selection of plants containing a mutation imparting such insect resistance.

An "insect-resistant transgenic plant", as used herein, includes any plant containing at least one transgene comprising a coding sequence encoding: 1 ) an insecticidal crystal protein from Bacillus thuringiensis or an insecticidal portion thereof, such as the insecticidal crystal proteins listed by Crickmore et al., Microbiology and Molecular Biology Reviews (1998), 62, 807-813, updated by Crickmore et al. (2005) at the Bacillus thuringiensis toxin nomenclature, online at: http://www.lifesci.sussex.ac.uk/Home/Neil_Crickmore/Bt/), or insecticidal portions thereof, e.g., proteins of the Cry protein classes CrylAb, CryiAc, Cry1 F, Cry2Ab,

Cry3Aa, or Cry3Bb or insecticidal portions thereof; or

2) a crystal protein from Bacillus thuringiensis or a portion thereof which is insecticidal in the presence of a second other crystal protein from Bacillus thuringiensis or a portion thereof, such as the binary toxin made up of the Cry34 and Cry35 crystal proteins (Moellenbeck et al., Nat. Biotechnol. (2001 ), 19, 668-72;

Schnepf et al., Applied Environm. Microbiol. (2006), 71 , 1765-1774); or

3) a hybrid insecticidal protein comprising parts of different insecticidal crystal proteins from Bacillus thuringiensis, such as a hybrid of the proteins of 1 ) above or a hybrid of the proteins of 2) above, e.g., the Cry1A.1O5 protein produced by corn event MON98034 (WO 2007/027777); or

4) a protein of any one of 1 ) to 3) above wherein some, particularly 1 to 10, amino acids have been replaced by another amino acid to obtain a higher insecticidal activity to a target insect species, and/or to expand the range of target insect species affected, and/or because of changes introduced into the encoding DNA during cloning or transformation, such as the Cry3Bb1 protein in corn events MON863 or

MON88017, or the Cry3A protein in corn event MIR604;

5) an insecticidal secreted protein from Bacillus thuringiensis or Bacillus cereus, or an insecticidal portion thereof, such as the vegetative insecticidal (VIP) proteins listed at: http://www.lifesci.sussex.ac.uk/home/Neil_Crickmore/Bt/vip.html, e.g., proteins from the VIP3Aa protein class; or

6) a secreted protein from Bacillus thuringiensis or Bacillus cereus which is insecticidal in the presence of a second secreted protein from Bacillus thuringiensis or β. cereus, such as the binary toxin made up of the VIP1A and VIP2A proteins (WO 1994/21795); or

7) a hybrid insecticidal protein comprising parts from different secreted proteins from Bacillus thuringiensis or Bacillus cereus, such as a hybrid of the proteins in 1 ) above or a hybrid of the proteins in 2) above; or 8) a protein of any one of 1 ) to 3) above wherein some, particularly 1 to 10, amino acids have been replaced by another amino acid to obtain a higher insecticidal activity to a target insect species, and/or to expand the range of target insect species affected, and/or because of changes introduced into the encoding DNA during cloning or transformation (while still encoding an insecticidal protein), such as the

VIP3Aa protein in cotton event COT102.

Of course, an insect-resistant transgenic plant, as used herein, also includes any plant comprising a combination of genes encoding the proteins of any one of the above classes 1 to 8. In one embodiment, an insect-resistant plant contains more than one transgene encoding a protein of any one of the above classes 1 to 8, to expand the range of target insect species affected when using different proteins directed at different target insect species, or to delay insect resistance development to the plants by using different proteins insecticidal to the same target insect species but having a different mode of action, such as binding to different receptor binding sites in the insect.

Plants or plant cultivars (obtained by plant biotechnology methods such as genetic engineering) which may also be treated according to the invention are tolerant to abiotic stresses. Such plants can be obtained by genetic transformation, or by selection of plants containing a mutation imparting such stress resistance. Particularly useful stress tolerance plants include:

a. plants which contain a transgene capable of reducing the expression and/or the activity of poly(ADP-ribose)polymerase (PARP) gene in the plant cells or plants as described in WO 2000/004173 or WO2006/045633 or PCT/EP07/004142.

b. plants which contain a stress tolerance enhancing transgene capable of reducing the expression and/or the activity of the PARG encoding genes of the plants or plants cells, as described e.g. in WO 2004/090140.

c. plants which contain a stress tolerance enhancing transgene coding for a plant-functional enzyme of the nicotinamide adenine dinucleotide salvage synthesis pathway including nicotinamidase, nicotinate phosphoribosyltransferase, nicotinic acid mononucleotide adenyl transferase, nicotinamide adenine dinucleotide synthetase or nicotine amide phosphoribosyltransferase as described e.g. in WO2006/032469 or WO 2006/133827 or PCT/EP07/002433. Plants or plant cultivars (obtained by plant biotechnology methods such as genetic engineering) which may also be treated according to the invention show altered quantity, quality and/or storage-stability of the harvested product and/or altered properties of specific ingredients of the harvested product such as : 1 ) transgenic plants which synthesize a modified starch, which in its physical- chemical characteristics, in particular the amylose content or the amylose/amylopectin ratio, the degree of branching, the average chain length, the side chain distribution, the viscosity behaviour, the gelling strength, the starch grain size and/or the starch grain morphology, is changed in comparison with the synthesised starch in wild type plant cells or plants, so that this is better suited for special applications. Said transgenic plants synthesizing a modified starch are disclosed, for example, in EP 0571427, WO 1995/004826, EP 0719338, WO 1996/15248, WO 1996/19581 , WO 1996/27674, WO 1997/11188, WO 1997/26362, WO 1997/32985, WO 1997/42328, WO 1997/44472, WO 1997/45545, WO 1998/27212, WO 1998/40503, WO99/58688, WO 1999/58690, WO 1999/58654,

WO 2000/008184, WO 2000/008185, WO 2000/008175, WO 2000/28052, WO 2000/77229, WO 2001/12782, WO 2001/12826, WO 2002/101059, WO 2003/071860, WO 2004/056999, WO 2005/030942, WO 2005/030941 , WO 2005/095632, WO 2005/095617, WO 2005/095619, WO 2005/095618, WO 2005/123927, WO 2006/018319, WO 2006/103107, WO 2006/108702, WO

2007/009823, WO 2000/22140, WO 2006/063862, WO 2006/072603, WO 2002/034923, EP 06090134.5, EP 06090228.5, EP 06090227.7, EP 07090007.1 , EP 07090009.7, WO 2001/14569, WO 2002/79410, WO 2003/33540, WO 2004/078983, WO 2001/19975, WO 1995/26407, WO 1996/34968, WO 1998/20145, WO 1999/12950, WO 1999/66050, WO 1999/53072, US 6,734,341 , WO 2000/11 192,

WO 1998/22604, WO 1998/32326, WO 2001/98509, WO 2001/98509, WO 2005/002359, US 5,824,790, US 6,013,861 , WO 1994/004693, WO 1994/009144, WO 1994/11520, WO 1995/35026, WO 1997/20936. 2) transgenic plants which synthesize non starch carbohydrate polymers or which synthesize non starch carbohydrate polymers with altered properties in comparison to wild type plants without genetic modification. Examples are plants producing polyfructose, especially of the inulin and levan-type, as disclosed in EP 0663956, WO 1996/001904, WO 1996/021023, WO 1998/039460, and WO 1999/024593, plants producing alpha 1 ,4 glucans as disclosed in WO 1995/031553, US 2002/031826, US 6,284,479, US 5,712,107, WO 1997/047806, WO 1997/047807,

WO 1997/047808 and WO 2000/014249, plants producing alpha-1 ,6 branched alpha-1 ,4-glucans, as disclosed in WO 2000/73422, plants producing alternan, as disclosed in WO 2000/047727, EP 06077301.7, US 5,908,975 and EP 0728213, 3) transgenic plants which produce hyaluronan, as for example disclosed in WO 2006/032538, WO 2007/039314, WO 2007/039315, WO 2007/039316, JP 2006/304779, and WO 2005/012529.

Plants or plant cultivars (that can be obtained by plant biotechnology methods such as genetic engineering) which may also be treated according to the invention are plants, such as cotton plants, with altered fiber characteristics. Such plants can be obtained by genetic transformation, or by selection of plants contain a mutation imparting such altered fiber characteristics and include: a) Plants, such as cotton plants, containing an altered form of cellulose synthase genes as described in WO 1998/000549 b) Plants, such as cotton plants, containing an altered form of rsw2 or rsw3 homologous nucleic acids as described in WO2004/053219 c) Plants, such as cotton plants, with increased expression of sucrose phosphate synthase as described in WO 2001/017333 d) Plants, such as cotton plants, with increased expression of sucrose synthase as described in WO02/45485 e) Plants, such as cotton plants, wherein the timing of the plasmodesmatal gating at the basis of the fiber cell is altered, e.g. through downregulation of fiberselective β 1 ,3-glucanase as described in WO2005/017157 f) Plants, such as cotton plants, having fibers with altered reactivity, e.g. through the expression of N-acteylglucosaminetransferase gene including nodC and chitinsynthase genes as described in WO2006/136351

Plants or plant cultivars (that can be obtained by plant biotechnology methods such as genetic engineering) which may also be treated according to the invention are plants, such as oilseed rape or related Brassica plants, with altered oil profile characteristics. Such plants can be obtained by genetic transformation or by selection of plants contain a mutation imparting such altered oil characteristics and include: a) Plants, such as oilseed rape plants, producing oil having a high oleic acid content as described e.g. in US 5,969,169, US 5,840,946 or US 6,323,392 or US 6,063,947 b) Plants such as oilseed rape plants, producing oil having a low linolenic acid content as described in US 6,270828, US 6,169,190 or US 5,965,755 c) Plant such as oilseed rape plants, producing oil having a low level of saturated fatty acids as described e.g. in US 5,434,283 Particularly useful transgenic plants which may be treated according to the invention are plants which comprise one or more genes which encode one or more toxins, such as the following which are sold under the trade names YIELD GARD® (for example maize, cotton, soya beans), KnockOut® (for example maize), BiteGard® (for example maize), Bt-Xtra® (for example maize), StarLink® (for example maize), Bollgard® (cotton), Nucotn® (cotton), Nucotn 33B®(cotton), NatureGard® (for example maize), Protecta® and NewLeaf® (potato). Examples of herbicide-tolerant plants which may be mentioned are maize varieties, cotton varieties and soya bean varieties which are sold under the trade names Roundup Ready® (tolerance to glyphosate, for example maize, cotton, soya bean), Liberty Link® (tolerance to phosphinotricin, for example oilseed rape), IMI® (tolerance to imidazolinones) and STS® (tolerance to sulphonylureas, for example maize). Herbicide-resistant plants (plants bred in a conventional manner for herbicide tolerance) which may be mentioned include the varieties sold under the name Clearfield® (for example maize).

Particularly useful transgenic plants which may be treated according to the invention are plants containing transformation events, or combination of transformation events, that are listed for example in the databases from various national or regional regulatory agencies (see for example http://gmoinfo.jrc.it/gmp_browse.aspx and http://www.agbios.com/dbase.php).

The composition according to the invention may also be used against fungal diseases liable to grow on or inside timber. The term "timber" means all types of species of wood, and all types of working of this wood intended for construction, for example solid wood, high-density wood, laminated wood, and plywood. The method for treating timber according to the invention mainly consists in contacting one or more compounds according to the invention or a composition according to the invention; this includes for example direct application, spraying, dipping, injection or any other suitable means.

Among the diseases of plants or crops that can be controlled by the method according to the invention, mention can be made of :

• Powdery mildew diseases such as :

Blumeria diseases, caused for example by Blumeha graminis ; Podosphaera diseases, caused for example by Podosphaera leucothcha ; Sphaerotheca diseases, caused for example by Sphaerotheca fuliginea ; Uncinula diseases, caused for example by Uncinula necator ;

• Rust diseases such as :

Gymnosporangium diseases, caused for example by Gymnosporangium sabinae ; Hemileia diseases, caused for example by Hemileia vastathx ; Phakopsora diseases, caused for example by Phakopsora pachyrhizi or Phakopsora meibomiae ;

Puccinia diseases, caused for example by Puccinia recondita ;

Uromyces diseases, caused for example by Uromyces appendiculatus ; • Oomycete diseases such as :

Albugo diseases caused for example by Albugo Candida;

Bremia diseases, caused for example by Bremia lactucae ;

Peronospora diseases, caused for example by Peronospora pisior P. brassicae ;

Phytophthora diseases, caused for example by Phytophthora infestans ; Plasmopara diseases, caused for example by Plasmopara viticola ;

Pseudoperonospora diseases, caused for example by Pseudoperonospora humulior

Pseudoperonospora cubensis ;

Pythium diseases, caused for example by Pythium ultimum ;

• Leafspot, leaf blotch and leaf blight diseases such as : Alternaria diseases, caused for example by Alternaha solani ;

Cercospora diseases, caused for example by Cercospora beticola ;

Cladiosporum diseases, caused for example by Cladiospohum cucumeήnum ;

Cochliobolus diseases, caused for example by Cochliobolus sativus ;

Colletotrichum diseases, caused for example by Colletotrichum lindemuthanium ; Cycloconium diseases, caused for example by Cycloconium oleaginum ;

Diaporthe diseases, caused for example by Diaporthe citri ;

Drechslera, Syn: Helminthosporium) or Cochliobolus miyabeanus;

Elsinoe diseases, caused for example by Elsinoe fawcettii ;

Gloeosporium diseases, caused for example by Gloeosporium laeticolor ; Glomerella diseases, caused for example by Glomerella cingulata ;

Guignardia diseases, caused for example by Guignardia bidwelli ;

Leptosphaeria diseases, caused for example by Leptosphaeria maculans ; Leptosphaeria nodorum ;

Magnaporthe diseases, caused for example by Magnaporthe grisea ; Mycosphaerella diseases, caused for example by Mycosphaerella graminicola ;

Mycosphaerella arachidicola ; Mycosphaerella fijiensis ;

Phaeosphaeria diseases, caused for example by Phaeosphaeha nodorum ;

Pyrenophora diseases, caused for example by Pyrenophora teres ;

Ramularia diseases, caused for example by Ramularia collo-cygni ; Rhynchosporium diseases, caused for example by Rhynchosporium secalis ;

Septoria diseases, caused for example by Septoria apiior Septoria lycopercisi ;

Typhula diseases, caused for example by Typhula incarnata ;

Venturia diseases, caused for example by Venturia inaequalis ; • Root and stem diseases such as :

Corticium diseases, caused for example by Corticium graminearum ;

Fusarium diseases, caused for example by Fusarium oxysporum ;

Gaeumannomyces diseases, caused for example by Gaeumannomyces graminis ; Rhizoctonia diseases, caused for example by Rhizoctonia solani ;

Sarocladium diseases caused for example by Sarocladium oryzae;

Sclerotium diseases caused for example by Sclerotium oryzae;

Tapesia diseases, caused for example by Tapesia acuformis ;

Thielaviopsis diseases, caused for example by Thielaviopsis basicola ; • Ear and panicle diseases including maize cob, such as :

Alternaria diseases, caused for example by Alternaria spp. ;

Aspergillus diseases, caused for example by Aspergillus flavus ;

Cladosporium diseases, caused for example by Cladosporium spp. ;

Claviceps diseases, caused for example by Claviceps purpurea ; Fusarium diseases, caused for example by Fusarium culmorum ;

Gibberella diseases, caused for example by Gibberella zeae ;

Monographella diseases, caused for example by Monographella nivalis ;

• Smut and bunt diseases such as :

Sphacelotheca diseases, caused for example by Sphacelotheca reiliana ; Tilletia diseases, caused for example by Tilletia caries ;

Urocystis diseases, caused for example by Urocystis occulta ; Ustilago diseases, caused for example by Ustilago nuda ;

• Fruit rot and mould diseases such as : Aspergillus diseases, caused for example by Aspergillus flavus ; Botrytis diseases, caused for example by Botrytis cinerea ;

Penicillium diseases, caused for example by Penicillium expansum ; Rhizopus diseases caused by example by Rhizopus stolonifer Sclerotinia diseases, caused for example by Sclerotinia sclerotiorum ; Verticilium diseases, caused for example by Verticilium alboatrum ; • Seed and soil borne decay, mould, wilt, rot and damping-off diseases such as :

Alternaria diseases, caused for example by Alternaria brassicicola Aphanomyces diseases, caused for example by Aphanomyces euteiches Ascochyta diseases, caused for example by Ascochyta lentis Aspergillus diseases, caused for example by Aspergillus flavus Cladosporium diseases, caused for example by Cladosporium herbarum

Cochliobolus diseases, caused for example by Cochliobolus sativus (Conidiaform: Drechslera, Bipolaris Syn: Helminthosporium); Colletotrichum diseases, caused for example by Colletotrichum coccodes; Fusarium diseases, caused for example by Fusarium culmorum;

Gibberella diseases, caused for example by Gibberella zeae;

Macrophomina diseases, caused for example by Macrophomina phaseolina

Monographella diseases, caused for example by Monographella nivalis; Penicillium diseases, caused for example by Penicillium expansum

Phoma diseases, caused for example by Phoma lingam

Phomopsis diseases, caused for example by Phomopsis sojae;

Phytophthora diseases, caused for example by Phytophthora cactorum;

Pyrenophora diseases, caused for example by Pyrenophora graminea Pyricularia diseases, caused for example by Pyricularia oryzae;

Pythium diseases, caused for example by Pythium ultimum;

Rhizoctonia diseases, caused for example by Rhizoctonia solani;

Rhizopus diseases, caused for example by Rhizopus oryzae

Sclerotium diseases, caused for example by Sclerotium rolfsii; Septoria diseases, caused for example by Septoria nodorum;

Typhula diseases, caused for example by Typhula incarnata;

Verticillium diseases, caused for example by Verticillium dahliae ;

• Canker, broom and dieback diseases such as : Nectria diseases, caused for example by Nectria galligena ; • Blight diseases such as :

Monilinia diseases, caused for example by Monilinia laxa ;

• Leaf blister or leaf curl diseases such as :

Exobasidium diseases caused for nexample by Exobasidium vexans;

Taphrina diseases, caused for example by Taphrina deformans ; • Decline diseases of wooden plants such as :

Esca diseases, caused for example by Phaemoniella clamydospora, Phaeomoniella clamydospora, Phaeoacremonium aleophilum and Fomitiporia mediterranea ;

Eutypa dyeback, caused for example by Eutypa lata ;

Dutch elm disease, caused for example by Ceratocystsc ulmi ; Ganoderma diseases caused by example by Ganoderma boninense;

• Diseases of flowers and Seeds such as : Botrytis diseases, caused for example by Botrytis cinerea ;

• Diseases of tubers such as :

Rhizoctonia diseases, caused for example by Rhizoctonia solani Helminthosporium diseases, caused for example by Helminthosporium solani.

• Diseases of Tubers such as

Rhizoctonia diseases caused for example by Rhizoctonia solani ; Helminthosporium diseases caused for example by Helminthosporium solani ; • Club root diseases such as

Plasmodiophora diseases, caused for example by Plamodiophora brassicae ;

• Diseases caused by Bacterial Organisms such as Xanthomanas species for example Xanthomonas campestris pv. oryzae; Pseudomonas species for example Pseudomonas syhngae pv. lachrymans;

Erwinia species for example Erwinia amylovora.

The fungicide composition according to the invention can also be used against fungal diseases liable to grow on or inside timber. The term "timber" means all types of species of wood and all types of working of this wood intended for construction, for example solid wood, high-density wood, laminated wood and plywood. The method for treating timber according to the invention mainly consists in contacting one or more compounds according to the invention, or a composition according to the invention ; this includes for example direct application, spraying, dipping, injection or any other suitable means.

The dose of active compound usually applied in the method of treatment according to the invention is generally and advantageously from 10 to 800 g/ha, preferably from 50 to 300 g/ha for applications in foliar treatment. The dose of active substance applied is generally and advantageously from 2 to 200 g per 100 kg of seed, preferably from 3 to 150 g per 100 kg of seed in the case of seed treatment.

It is clearly understood that the doses indicated herein are given as illustrative examples of the method according to the invention. A person skilled in the art will know how to adapt the application doses, notably according to the nature of the plant or crop to be treated.

The fungicide composition according to the invention can also be used in the treatment of genetically modified organisms with the compounds according to the invention or the agrochemical compositions according to the invention. Genetically modified plants are plants into genome of that a heterologous gene encoding a protein of interest has been stably integrated. The expression "heterologous gene encoding a protein of interest" essentially means genes that give the transformed plant new agronomic properties, or genes for improving the agronomic quality of the modified plant.

The compounds or mixtures according to the invention can also be used for the preparation of composition useful to curatively or preventively treat human or animal fungal diseases such as, for example, mycoses, dermatoses, trichophyton diseases and candidiases or diseases caused by Aspergillus spp., for example Aspergillus fumigatus. The various aspects of the invention will now be illustrated with reference to the following table 1 of compound examples and the following preparation or efficacy examples.

The following table 1 illustrates in a non limiting manner examples of compounds according to the invention.

Table 1

Measurement of logP values was performed according EEC directive 79/831 Annex V.A8 by HPLC (High Performance Liquid Chromatography) on reversed phase columns with the following methods:

'measurement of LC-MS was done at pH 2,7 with 0,1 % formic acid in water and with acetonitrile (contains 0,1 % formic acid) as eluent with a linear gradient from 10 % acetonitrle to 95 % acetonitrile.

Calibration was done with not branched alkan2-ones (with 3 to 16 carbon atoms) with known logP-values (measurement of logP values using retention times with linear interpolation between successive alkanones).. lambda-maX-values were determined using UV-spectra from 200 nm to 400 nm and the peak values of the chromatographic signals.

In table 1 , M+H (or M H) means the molecular ion peak, plus or minus 1 a.m.u. (atomic mass unit) respectively, as observed in mass spectroscopy and M (Apcl+) means the molecular ion peak as it was found via positive atmospheric pressure chemical ionisation in mass spectroscopy.

VO

The present invention also relates to a process for the preparation of compounds of formula (I). The process according to the invention can be carried according to the following schemes and reaction conditions. Specific steps and particular conditions can be adapted by the skilled person in order to prepare the compounds of formula (I) according to the invention.

Scheme 2

The methoxyquinoline derivatives are prepared starting from methoxyaniline derivatives and 2.2.3-tribromopropionaldehyde under the conditions previously described in the literature (US4489098, J. Am. Chem. Soc 1950, 72, 393-395, WO2008028624). The ether can be removed under a variety of conditions (W. Greene et al Protective groups in organic synthesis, Wiley Interscience). The hydroxyquinoline derivatives are then alkylated with ester derivatives having a halogen atom or a leaving group in presence of an inorganic base, like lithium hydoxid, sodium hydroxid, potassium hydroxid, lithium carbonate, sodium carbonate, calcium carbonate, potassium carbonate or cesium carbonate, or sodium hydride or potassium hydride.

The amides are prepared directly from the ester derivatives and amines and a Lewis acid (AlMe3, MgBr2, MgC12, Mg(O Ac)2, MC12, SnC12...), or from the carboxylic acids obtained by hydrolysis of the parent esters under usual conditions, where the ester in an inert solvent is treated with bases and amines with a coupling reagent (DCC, EDCI, HATU, PYBOP... not exhaustive examples), or the carboxylic acids are first transformed into acid halides before reacting with amines . The thioamides are prepared from the amides and the Lawesson's reagents, P2S5.

In the following examples, M+H (or M-H) means the molecular ion peak, plus or minus 1 a.m.u. (atomic mass unit) respectively, as observed in mass spectroscopy and M (Apcl+) means the molecular ion peak as it was found via positive atmospheric pressure chemical ionisation in mass spectroscopy. The lambda max values were determined in the maxima of the chromatographic signals using the UV spectra from 190 nm to 400 nm.

Abbreviations and acronyms:

AlMe₃ trimethylaluminium

AcOEt Ethyl acetate DMF dimethylformamide

DMSO dimethylsulfoxide

DMC methylenechloride

EDCI 1 -ethyl-3 -(3 ' -dimethylaminopropyl)carbodiimide

HATU O-(7- Azabenzotriazo 1- 1 -yl)-N,N,N'N'-tetramethyluronium hexafluorophsphate

HOBT 1 -hydroxybenzotriazo Ie

K2CO3 Potassium carbonate MS Mass spectroscopy

LiCl Lithium chloride

MeCN Acetonitrile

MeOH Methanol MgSO₄ Magnesium sulfate

NaHCOs Sodium hydrogenocarbonate

NEt₃ Triethylamine

PYBOP ( 1 H-benzotriazol- 1 -yloxy)(tripyrro lidin- 1 -yl)phosphonium hexafluorophosphate rt Room temperature

Example 1

Preparation of the compound 2-[(3-bromo-7-fluoroquinolin-6-yl)oxy]-N-[(l- ethyl-lH-pyrazol-4-yl)methyl]butanamide (compound 48)

Stepl

92 g of 3-fluoro-4-methoxyaniline was dissolved in AcOH (1 L.), 202 g of 2,2,3- tribromo propanal was added over 15mn at rt (gradual exotherm -> 36°C), after several minutes stirring a precipitate began to form. The reaction was stirred at rt for 2.5 hours, poured in 4 L water, extraction with DCM (2 x 2 L), the organic phase was washed with 2N NaOH (2.5 L) then water (3 L), dried over MgSO₄ and concentrated under reduced pressure to give 129 g of an oil. Two purifications on silica were necessary to deliver 10.8 g of 3-bromo-7-fluoro-6-methoxyquinoline. 5.2 g of 7- fluoro-6-methoxyquinoline as by-product was also isolated.

3-bromo-7-fluoro-6-methoxyquinoline MS : m/z = 256 [M+H]⁺

LogP = 2.75

7-fluoro-6-methoxyquinoline MS : m/z = 178 [M+H]⁺ LogP = 2.26 Step2

A mixture of 3-bromo-7-fluoro-6-methoxyquinoline (10.8 g) and hydrobromic acid

(200 rnL) was heated to 104⁰C for 72 hours. The reaction was cooled to rt and 400 mL of ice + water was added. The mixture was neutralised by NaHCOs to pH 8, extracted with AcOEt (2 x 200 mL). The extracts are combined, dried over MgSO4, filtered and concentrated under reduced pressure to furnished 8.2 g of 3-bromo-7- fluoroquino lin-6-o 1.

MS : m/z = 242 [M+H]⁺ LogP = 1.92

Step 3

To a mixture of 3-bromo-7-fluoroquinolin-6-ol from step 2 (6.0 g) and potassium carbonate (6.4 g) in DMF (70 mL) at rt was added a solution of methyl 2- bromobutanoate (4.7 g) in DMF (15 mL) dropwise. The mixture is stirred 2h at rt, then diluted with water and extracted with AcOEt. The extracts are combined, washed with a saturated solution of LiCl followed by brine, and dried with MgSO₄, filtered and concentrated under reduced pressure. The crude material is then purified by chromatography (silica; AcOEt/n-heptane 1 :9 to 2:3 by volume) to deliver methyl 2- [(3 -bromo-7-fluoroquino lin-6-yl)oxy]butanoate : MS : m/z =342.0 [M+H]⁺ LogP = 3.46

Step 4

1 -(I -ethyl- lH-pyrazol-4-yl)methanamine (146.0 mg) was dissolved in toluene under Argon, Trimethylaluminum (88.0 mg) was added dropwise, stirred for 15 minutes, then methyl 2-[(3-bromo-7-fluoroquinolin-6-yl)oxy]butanoate from step 3 (200.0 mg) was added, reaction heated at 100⁰C for 15 minutes in a micro-wave oven. Reaction is quenched by dropwise addition of IM HCl (some gas evolution), loaded onto a Chemelut cartridge, washed with AcOEt and solvent evaporated affording compound 48, 2-[(3-bromo-7-fluoroquinolin-6-yl)oxy]-N-[(l-ethyl-lH-pyrazol-4- yl)methyl]butanamide : MS : m/z =435 [M+H]⁺ LogP = 2.5

Example 2

Preparation of the compound 2-[(3-bromo-7-fluoroquinolin-6-yl)oxy]-N-[(l-ethyl- lH-pyrazol-4-yl)methyl]butanethioamide (compound 60).

To a mixture of 2-[(3-bromo-7-fluoroquinolin-6-yl)oxy]-N-[(l-ethyl-lH-pyrazol-4- yl)methyl]butanamide (100.0 mg) in dioxane (2.5 mL), phosphorus pentasulfϊde (200.0 mg) was added at rt followed by sodium hydrogencarbonate (77.0 mg). Reaction was heated to reflux and maintained for 4 hours. Reaction was cooled, diluted with water, extracted with AcOEt (2 x 10 mL), organic layers were combined, washed with water and brine, then dried over MgSO₄ and solvent was evaporated under reduced pressure. Residue was loaded onto a 12 g Redisep cartridge and purified by column chromatography to give compound 60, 2-[(3-bromo-7- fluoroquino lin-6-yl)oxy] -N- [( 1 -ethyl- 1 H-pyrazol-4-yl)methyl]butanethioamide :

MS : m/z =451 [M+H]⁺ LogP = 3.5

Example 3

Preparation of the compound 2-[(3-bromo-7-fluoroquinolin-6-yl)oxy]-N-[(l-ethyl- lH-pyrazol-4-yl)methyl]-2-methoxyacetamide (compound 64)

Step 1, 2

Same procedure as example 1 Step 3 Methyl [(3-bromo-7-fluoroquinolin-6-yl)oxy](methoxy)acetate was prepared under similar procedure as example 1, step 3: MS: m/z =344 [M+H]⁺ LogP = 2.8

Step 4

Step 4

To a mixture of methyl [(3-bromo-7-fluoroquinolin-6-yl)oxy](methoxy)acetate (655.0 mg) in MeOH (2 mL), NaOH (260.0 mg) was added. The reaction was stirred at 70⁰C for lhour. After evaporation of the solvent, the residue was treated with water and HCl until pH = 1. The precipitate was filtered and dried to give [(3-bromo- 7-fluoroquinolin-6-yl)oxy](methoxy)acetic acid.

MS : m/z =330 [M+H]" LogP = 1.9

Step 4a

[(3-bromo-7-fluoroquinolin-6-yl)oxy](methoxy)acetic acid (132.0 mg)was dissolved in DMF (3 mL) under nitrogen. 1 -(I -ethyl- lH-pyrazol-4-yl)methanamine (71.0 mg) was added followed by HOBT (174.0 mg), EDCI (218.5 mg) and NEt3 (115.3 mg). The reaction was stirred at 80⁰C for lhour. The reaction was diluted with AcOEt (3 x 5 mL) and washed with H₂O and a saturated LiCl solution, dried over MgSO₄ and concentrated under reduced pressure. The mixture was purified on basic alumina to give the title compound 64, 2-[(3-bromo-7-fluoroquinolin-6-yl)oxy]-N-[(l-ethyl-lH- pyrazol-4-yl)methyl]-2-methoxyacetamide.

MS : m/z =437 [M+H]⁺ LogP = 2.2 Biological Examples:

Cell test on Botrytis cinerea

The compounds tested are solubilized in DMSO and added to sterile liquid glucose/mycopeptone medium (14.6 g/l of D-glucose, 7.1 g/l of mycological peptone (Oxoid) and 1.4 g/l of yeast extract (Merck)) at a concentration of 2 ppm. The medium is inoculated with cryopreserved Botrytis cinerea spore suspension at a concentration of 500 spores per ml. The efficacy of the active ingredient is assessed by OD measurement at 620 nm after 5 days at 2O⁰C in comparison with a control.

Under these conditions, good (at least 70 %) or total protection is observed at the dose of 2 ppm for the following compounds: 4, 5, 6, 7, 11 , 17, 22, 23, 26, 27, 29, 30, 33, 39, 42, 43, 44, 45, 50, 52, 56, 59, 63, 64 and 65.

Cell test on Mycosphaerella graminicola

The compounds tested are solubilized in DMSO and added to sterile liquid glucose/bactopeptone medium (14.6 g/l of D-glucose, 7.1 g/l of bactopeptone (Oxoid) and 1.4 g/l of yeast extract (Merck)) at a concentration of 2 ppm. The medium is inoculated with cryopreserved Mycosphaerella graminicola spore suspension at a concentration of 30000 spores per ml. The efficacy of the active ingredient is assessed by OD measurement at 405 nm after 6 days at 2O⁰C in comparison with a control.

Under these conditions, good (at least 70 %) or total protection is observed at the dose of 2 ppm for the following compounds: 6, 7, 11 , 22, 30, 33, 29, 39, 42, 44, 56 and 63.

Claims

1. A compound of formula (I)

(I) wherein

Q¹ and Q² independently represent a hydrogen atom, a halogen atom, a nitro group, a hydroxy group, a cyano group, an amino group, a sulphenyl group, a formyl group, a substituted or non-substituted carbaldehyde O-(Ci-C₈-alkyl)oxime, a formyloxy group, a formylamino group, a carbamoyl group, a N-hydroxycarbamoyl group, a pentafluoro-λ⁶-sulphenyl group, substituted or non-substituted C-ι-C₈-alkoxyamino group, substituted or non-substituted N-C-ι-C₈-alkyl-(C-ι-C₈-alkoxy)-amino group, substituted or non-substituted (C-ι-C₈-alkylamino)-amino group, substituted or non- substituted N-Ci-C₈-alkyl-(Ci-C₈-alkylamino)-amino group, a substituted or non- substituted (hydroxyimino)-Ci-C₆-alkyl group, substituted or non-substituted Ci-C₈- alkyl, substituted or non-substituted tri(C₁-C₈-alkyl)silyl, substituted or non- substituted tri(Ci-C₈-alkyl)silyl-Ci-C₈-alkyl, substituted or non-substituted Ci-C₈- cycloalkyl, substituted or non-substituted tri(Ci-C₈-alkyl)silyl-Ci-C₈-cycloalkyl, substituted or non-substituted Ci-C₈-halogenoalkyl having 1 to 5 halogen atoms, substituted or non-substituted Ci-C₈-halogenocycloalkyl having 1 to 5 halogen atoms, a C₂-C₈-alkenyl, substituted or non-substituted C₂-C₈-alkynyl, substituted or non-substituted Ci-C₈-alkylamino, substituted or non-substituted di-Ci-C₈- alkylamino, substituted or non-substituted Ci-C₈-alkoxy, substituted or non- substituted Ci-C₈-halogenoalkoxy having 1 to 5 halogen atoms, substituted or non- substituted Ci-C₈-alkylsulphenyl, substituted or non-substituted Ci-C₈- halogenoalkylsulphenyl having 1 to 5 halogen atoms, substituted or non-substituted C₂-C₈-alkenyloxy, substituted or non-substituted C₂-C₈-halogenoalkenyloxy having 1 to 5 halogen atoms, substituted or non-substituted C₃-C₈-alkynyloxy, substituted or non-substituted C₃-C₈-halogenoalkynyloxy having 1 to 5 halogen atoms, substituted or non-substituted Ci-C₈-alkylcarbonyl, substituted or non-substituted Ci-C₈- halogenoalkylcarbonyl having 1 to 5 halogen atoms, substituted or non-substituted Ci-C₈-alkylcarbamoyl, substituted or non-substituted di-Ci-C₈-alkylcarbamoyl, substituted or non-substituted N-Ci-C₈-alkyloxycarbamoyl, substituted or non- substituted d-C₈-alkoxycarbamoyl, substituted or non-substituted N-d-C₈-alkyl-d- Cs-alkoxycarbamoyl, substituted or non-substituted C-ι-C₈-alkoxycarbonyl, substituted or non-substituted d-Cs-halogenoalkoxycarbonyl having 1 to 5 halogen atoms, substituted or non-substituted d-Cs-alkylcarbonyloxy, substituted or non- substituted d-Cs-halogenoalkylcarbonyloxy having 1 to 5 halogen atoms, substituted or non-substituted d-Cs-alkylcarbonylamino, substituted or non- substituted d-Cs-halogenoalkylcarbonylamino having 1 to 5 halogen atoms, substituted or non-substituted d-Cs-alkylcarbamoylamino, substituted or non- substituted d-Cs-halogenoalkylcarbamoylamino having 1 to 5 halogen atoms, substituted or non-substituted di-d-Cs-alkylcarbamoylamino, substituted or non- substituted di-d-Cs-halogenoalkylcarbamoylamino having 1 to 5 halogen atoms , substituted or non-substituted N-d-C₈-alkyl-(d-C₈-alkylcarbamoyl)amino, substituted or non-substituted N-d-C₈-alkyl-(d-C₈-halogenoalkylcarbamoyl)amino having 1 to 5 halogen atoms, substituted or non-substituted N-d-C₈-alkyl-(di-d-C₈- alkylcarbamoyl)amino, substituted or non-substituted N-d-C₈-alkyl-(di-d-C₈- halogenoalkylcarbamoyl)amino having 1 to 5 halogen atoms, substituted or non- substituted d-Cs-alkylaminocarbonyloxy, substituted or non-substituted di-d-C₈- alkylaminocarbonyloxy, substituted or non-substituted d-Cs-alkylcarbamothioyl, substituted or non-substituted di-d-Cs-alkylcarbamothioyl, substituted or non- substituted N-d-Cs-alkyloxycarbamothioyl, substituted or non-substituted C₁-C₈- alkoxycarbamothioyl, substituted or non-substituted N-C₁ -C₈-alkyl-d -C₈- alkoxycarbamothioyl, substituted or non-substituted C-ι-C₈-alkylthioylamino, substituted or non-substituted C-ι-C₈-halogenoalkylthioylamino having 1 to 5 halogen atoms, substituted or non-substituted (d-C₈-alkyl-carbamothioyl)-oxy, substituted or non-substituted substituted or non-substituted (di-d-C₈-alkyl-carbannothioyl)-oxy, substituted or non-substituted d-C₈-alkylsulphinyl, substituted or non-substituted C₁- C₈-halogenoalkylsulphinyl having 1 to 5 halogen atoms, substituted or non- substituted d-C₈-alkylsulphonyl, substituted or non-substituted d-C₈-halogenoalkyl- sulphonyl having 1 to 5 halogen atoms, substituted or non-substituted C₁-C₈- alkylaminosulfamoyl, substituted or non-substituted di-d-C₈-alkylaminosulfannoyl, substituted or non-substituted (d-C₆-alkoxyinnino)-d-C₆-alkyl, substituted or non- substituted (d-C₆-alkenyloxyinnino)-d-C₆-alkyl, substituted or non-substituted (C₁- C₆-alkynyloxyimino)-d-C₆-alkyl, substituted or non-substituted (benzyloxyimino)-d- C₆-alkyl, substituted or non-substituted benzyloxy, substituted or non-substituted benzylsulphenyl, substituted or non-substituted benzylamino, substituted or non- substituted phenoxy, substituted or non-substituted phenylsulphenyl, substituted or non-substituted phenylamino, substituted or non-substituted aryl, substituted or non- substituted aryl-[d-C₈]-alkyl, substituted or non-substituted tri(d-C₈-alkyl)-silyloxy, substituted or non-substituted d-Cs-alkylsulfenylamino, substituted or non- substituted C-i-Cs-halogenoalkylsulphinylannino having 1 to 5 halogen atoms, substituted or non-substituted d-C₈-alkylsulphonylamino, substituted or non- substituted C-rCs-halogenoalkylsulphonylamino having 1 to 5 halogen atoms, substituted or non-substituted C-ι-C₈-alkoxysulphonylamino, substituted or non- substituted C-i-C₈-halogenoxysulphonylamino having 1 to 5 halogen atoms, substituted or non-substituted (C-ι-C₆-alkylideneamino)oxy, substituted or non- substituted (C-ι-C₆-alkenylideneamino)oxy, substituted or non-substituted (C₁-C₆- alkynylideneamino)oxy, substituted or non-substituted (benzylideneamino)oxy; substituted or non-substituted, saturated or unsaturated A-, 5-, 6- or 7-membered heterocyclyl comprising up to 4 heteroatoms selected in the list consisting of N, O, S; substituted or non-substituted, saturated or unsaturated A-, 5-, 6- or 7-membered heterocyclyl-[Ci-C₈]-alkyl comprising up to 4 heteroatoms selected in the list consisting of N, O, S; • Q³ represents a halogen atom, a nitro group, a hydroxy group, a cyano group, an amino group, a sulphenyl group, a formyl group, a substituted or non-substituted carbaldehyde O-(Ci-C₈-alkyl)oxime, a formyloxy group, a formylamino group, a carbamoyl group, a N-hydroxycarbamoyl group, a pentafluoro-λ⁶-sulphenyl group, substituted or non-substituted d-C₈-alkoxyamino group, substituted or non- substituted N-C-ι-C₈-alkyl-(C-ι-C₈-alkoxy)-amino group, substituted or non-substituted (Ci-C₈-alkylamino)-amino group, substituted or non-substituted N-Ci-C₈-alkyl-(d-C₈- alkylamino)-amino group, a substituted or non-substituted (hydroxyimino)-Ci-C₆-alkyl group, substituted or non-substituted Ci-C₈-alkyl, substituted or non-substituted tri(Ci-C₈-alkyl)silyl, substituted or non-substituted tri(C₁-C₈-alkyl)silyl-C₁-C₈-alkyl, substituted or non-substituted Ci-C₈-cycloalkyl, substituted or non-substituted tri(Ci- C₈-alkyl)silyl-Ci-C₈-cycloalkyl, substituted or non-substituted Ci-C₈-halogenoalkyl having 1 to 5 halogen atoms, substituted or non-substituted Ci-C₈- halogenocycloalkyl having 1 to 5 halogen atoms, a C₂-C₈-alkenyl, substituted or non- substituted C₂-C₈-alkynyl, substituted or non-substituted d-C₈-alkylamino, substituted or non-substituted di-d-C₈-alkylamino, substituted or non-substituted d-C₈-alkoxy, substituted or non-substituted d-C₈-halogenoalkoxy having 1 to 5 halogen atoms, substituted or non-substituted d-C₈-alkylsulphenyl, substituted or non-substituted d-C₈-halogenoalkylsulphenyl having 1 to 5 halogen atoms, substituted or non-substituted C₂-C₈-alkenyloxy, substituted or non-substituted C₂- C₈-halogenoalkenyloxy having 1 to 5 halogen atoms, substituted or non-substituted C₃-C₈-alkynyloxy, substituted or non-substituted C₃-C₈-halogenoalkynyloxy having 1 to 5 halogen atoms, substituted or non-substituted Ci-C₈-alkylcarbonyl, substituted or non-substituted Ci-C₈-halogenoalkylcarbonyl having 1 to 5 halogen atoms, substituted or non-substituted d-Cs-alkylcarbamoyl, substituted or non-substituted di-C-i-Cs-alkylcarbannoyl, substituted or non-substituted N-d-Cs-alkyloxycarbamoyl, substituted or non-substituted d-C₈-alkoxycarbamoyl, substituted or non-substituted N-C-i-Cs-alkyl-C-i-Cs-alkoxycarbannoyl, substituted or non-substituted C₁-C₈- alkoxycarbonyl, substituted or non-substituted d-Cs-halogenoalkoxycarbonyl having

1 to 5 halogen atoms, substituted or non-substituted d-Cs-alkylcarbonyloxy, substituted or non-substituted d-Cs-halogenoalkylcarbonyloxy having 1 to 5 halogen atoms, substituted or non-substituted d-Cs-alkylcarbonylamino, substituted or non-substituted d-Cs-halogenoalkylcarbonylamino having 1 to 5 halogen atoms, substituted or non-substituted d-Cs-alkylcarbamoylamino, substituted or non- substituted d-Cs-halogenoalkylcarbamoylamino having 1 to 5 halogen atoms, substituted or non-substituted di-d-Cs-alkylcarbamoylamino, substituted or non- substituted di-d-Cs-halogenoalkylcarbamoylamino having 1 to 5 halogen atoms , substituted or non-substituted N-d-C₈-alkyl-(d-C₈-alkylcarbamoyl)amino, substituted or non-substituted N-d-C₈-alkyl-(d-C₈-halogenoalkylcarbamoyl)amino having 1 to 5 halogen atoms, substituted or non-substituted N-d-C₈-alkyl-(di-d-C₈- alkylcarbamoyl)amino, substituted or non-substituted N-d-C₈-alkyl-(di-d-C₈- halogenoalkylcarbamoyl)amino having 1 to 5 halogen atoms, substituted or non- substituted d-Cs-alkylaminocarbonyloxy, substituted or non-substituted di-d-C₈- alkylaminocarbonyloxy, substituted or non-substituted d-C₈-alkylcarbamothioyl, substituted or non-substituted di-d-C₈-alkylcarbamothioyl, substituted or non- substituted N-d-C₈-alkyloxycarbamothioyl, substituted or non-substituted C₁-C₈- alkoxycarbamothioyl, substituted or non-substituted N-C₁ -C₈-alkyl-d -C₈- alkoxycarbamothioyl, substituted or non-substituted C-ι-C₈-alkylthioylamino, substituted or non-substituted d-C₈-halogenoalkylthioylannino having 1 to 5 halogen atoms, substituted or non-substituted (d-C₈-alkyl-carbamothioyl)-oxy, substituted or non-substituted substituted or non-substituted (di-d-C₈-alkyl-carbannothioyl)-oxy, substituted or non-substituted d-C₈-alkylsulphinyl, substituted or non-substituted C₁- C₈-halogenoalkylsulphinyl having 1 to 5 halogen atoms, substituted or non- substituted d-C₈-alkylsulphonyl, substituted or non-substituted d-C₈-halogenoalkyl- sulphonyl having 1 to 5 halogen atoms, substituted or non-substituted C₁-C₈- alkylaminosulfamoyl, substituted or non-substituted di-C-ι-C₈-alkylaminosulfamoyl, substituted or non-substituted (d-C₆-alkoxyinnino)-d-C₆-alkyl, substituted or non- substituted (d-C₆-alkenyloxyinnino)-d-C₆-alkyl, substituted or non-substituted (C₁- C₆-alkynyloxyimino)-d-C₆-alkyl, substituted or non-substituted (benzyloxyimino)-d- C₆-alkyl, substituted or non-substituted benzyloxy, substituted or non-substituted benzylsulphenyl, substituted or non-substituted benzylamino, substituted or non- substituted phenoxy, substituted or non-substituted phenylsulphenyl, substituted or non-substituted phenylamino, substituted or non-substituted aryl, substituted or non- substituted aryl-[C-ι-C₈]-alkyl, substituted or non-substituted tri(C-ι-C₈-alkyl)-silyloxy, substituted or non-substituted d-C₈-alkylsulfenylamino, substituted or non- substituted C-i-Cs-halogenoalkylsulphinylannino having 1 to 5 halogen atoms, substituted or non-substituted d-C₈-alkylsulphonylamino, substituted or non- substituted C-rCs-halogenoalkylsulphonylamino having 1 to 5 halogen atoms, substituted or non-substituted C-ι-C₈-alkoxysulphonylamino, substituted or non- substituted C-i-C₈-halogenoxysulphonylamino having 1 to 5 halogen atoms, substituted or non-substituted (d-C₆-alkylideneamino)oxy, substituted or non- substituted (d-C₆-alkenylideneamino)oxy, substituted or non-substituted (Ci-C₆- alkynylideneamino)oxy, substituted or non-substituted (benzylideneamino)oxy; substituted or non-substituted, saturated or unsaturated A-, 5-, 6- or 7-membered heterocyclyl comprising up to 4 heteroatoms selected in the list consisting of N, O, S; substituted or non-substituted, saturated or unsaturated A-, 5-, 6- or 7-membered heterocyclyl-[Ci-C₈]-alkyl comprising up to 4 heteroatoms selected in the list consisting of N, O, S;

• R¹ represents a hydrogen atom, a hydroxy group, a cyano group, an amino group, a substituted or non-substituted carbaldehyde O-(Ci-C₈-alkyl)oxime, a formyloxy group, a formylamino group, substituted or non-substituted Ci-C₈-alkoxyamino group, substituted or non-substituted N-Ci-C₈-alkyl-(Ci-C₈-alkoxy)-amino group, a substituted or non-substituted (hydroxyimino)-Ci-C₆-alkyl group, substituted or non- substituted Ci-C₈-alkyl, substituted or non-substituted tri(C₁-C₈-alkyl)silyl, substituted or non-substituted tri(C-ι-C₈-alkyl)silyl-C-ι-C₈-alkyl, substituted or non-substituted C₁- C₈-cycloalkyl, substituted or non-substituted tri(C-ι-C₈-alkyl)silyl-C-ι-C₈-cycloalkyl, substituted or non-substituted d-C₈-halogenoalkyl having 1 to 5 halogen atoms, substituted or non-substituted d-Cs-halogenocycloalkyl having 1 to 5 halogen atoms, a C₂-C₈-alkenyl, substituted or non-substituted C₂-C₈-alkynyl, substituted or non-substituted d-C₈-alkylamino, substituted or non-substituted di-d-C₈- alkylamino, substituted or non-substituted d-C₈-alkoxy, substituted or non- substituted d-C₈-halogenoalkoxy having 1 to 5 halogen atoms, substituted or non- substituted C₂-C₈-alkenyloxy, substituted or non-substituted C₂-C₈- halogenoalkenyloxy having 1 to 5 halogen atoms, substituted or non-substituted C₃- C₈-alkynyloxy, substituted or non-substituted C₃-C₈-halogenoalkynyloxy having 1 to 5 halogen atoms, substituted or non-substituted Ci-C₈-alkylcarbonyloxy, substituted or non-substituted Ci-C₈-halogenoalkylcarbonyloxy having 1 to 5 halogen atoms, substituted or non-substituted Ci-C₈-alkylcarbonylamino, substituted or non- substituted d-C₈-halogenoalkylcarbonylamino having 1 to 5 halogen atoms, substituted or non-substituted (d-C₆-alkoxyimino)-d-C₆-alkyl, substituted or non- substituted (Ci-C₆-alkenyloxyimino)-Ci-C₆-alkyl, substituted or non-substituted (d- C₆-alkynyloxyimino)-C"rC₆-alkyl, substituted or non-substituted (benzyloxyimino)-C-i- C₆-alkyl, substituted or non-substituted benzyloxy, substituted or non-substituted benzylsulphenyl, substituted or non-substituted benzylamino, substituted or non- substituted phenoxy, substituted or non-substituted phenylsulphenyl, substituted or non-substituted phenylamino, substituted or non-substituted aryl, substituted or non- substituted aryl-[C-ι-C₈]-alkyl, substituted or non-substituted tri(C-ι-C₈-alkyl)-silyloxy; substituted or non-substituted, saturated or unsaturated A-, 5-, 6- or 7-mennbered heterocyclyl comprising up to 4 heteroatoms selected in the list consisting of N, O, S; substituted or non-substituted, saturated or unsaturated A-, 5-, 6- or 7-mennbered heterocyclyl-[Ci-C₈]-alkyl comprising up to 4 heteroatoms selected in the list consisting of N, O, S;

• R² represents a hydrogen atom, a hydroxy group, a cyano group, substituted or non-substituted C-ι-C₈-alkyl, substituted or non-substituted tri(C-ι-C₈-alkyl)silyl, substituted or non-substituted tri(C-ι-C₈-alkyl)silyl-C-ι-C₈-alkyl, substituted or non- substituted d-C₈-cycloalkyl, substituted or non-substituted tri(C-ι-C₈-alkyl)silyl-C-ι-C₈- cycloalkyl, substituted or non-substituted d-C₈-halogenoalkyl having 1 to 5 halogen atoms, substituted or non-substituted Ci-C₈-halogenocycloalkyl having 1 to 5 halogen atoms, a C₂-C₈-alkenyl, substituted or non-substituted C₂-C₈-alkynyl, substituted or non-substituted Ci-C₈-alkoxy, substituted or non-substituted benzyloxy:

• R³ represents -(CR^aR^b)p-R⁴, wherein: o R^a and R^b represent independently a hydrogen atom, substituted or non- substituted d-C₈-alkyl, a halogen atom, a cyano group, a hydroxy group, substituted or non-substituted d-C₈-alkoxy or substituted or non-substituted

C-rCs-alkoxycarbonyl, or

° R^a and R^b form a 3- to 8-membered carbocyclic or heterocyclic ring comprising a heteroatom selected from sulfur, oxygen and NR⁰ wherein R⁰ represents a hydrogen atom or substituted or non-substituted C-ι-C₈-alkyl; o R⁴ represents a halogen atom, substituted or non-substituted d-C₈-alkyl, substituted or non-substituted d-C₈-alkenyl, substituted or non-substituted d-Cs-alkyloxy-d-Cs-alkyl, substituted or non-substituted aryloxy or substituted or non-substituted heteroaryloxy, -C≡C-R⁵ wherein R⁵ represents a hydrogen atom , a halogen atom, substituted or non-substituted Ci-C₈- alkyl, substituted or non-substituted C₃-C₈-cycloalkyl, substituted or non- substituted d-C₈-alkyloxy-d-C₈-alkyl, substituted or non-substituted aryl, substituted or non-substituted aryl-[Ci-C₈]-alkyl, substituted or non- substituted tri(Ci-C₈-alkyl)-silyl; substituted or non-substituted, saturated or unsaturated A-, 5-, 6- or 7-nnennbered heterocyclyl comprising up to 4 heteroatoms selected in the list consisting of N, O, S; substituted or non- substituted, saturated or unsaturated A-, 5-, 6- or 7-mennbered heterocyclyl- [C-ι-C₈]-alkyl comprising up to 4 heteroatoms selected in the list consisting of N, O, S, wherein the N atom is substituted or unsubstituted with substituted or non-substituted C-ι-C₈-alkyl, substituted or non-substituted C₃-C₈- cycloalkyl, substituted or non-substituted C-ι-C₈-alkyloxy-C-ι-C₈-alkyl, substituted or non-substituted aryl, substituted or non-substituted aryl-[d- C₈]-alkyl, substituted or non-substituted tri(Ci-C₈-alkyl)-silyl: o p is 0 or 1

• L represents a sulfur atom or an oxygen atom as well as salts, N-oxides, metallic complexes and metalloidic complexes thereof.

2. A compound according to claim 1 wherein Q¹ and Q² independently represent a hydrogen atom, a halogen atom, a cyano group, substituted or non-substituted d-C₈-alkyl, substituted or non-substituted tri(C₁-C₈-alkyl)silyl, substituted or non-substituted tri(Ci-C₈- alkyl)silyl-Ci-C₈-alkyl, substituted or non-substituted Ci-C₈-cycloalkyl, substituted or non- substituted Ci-C₈-halogenoalkyl having 1 to 5 halogen atoms, substituted or non-substituted Ci-C₈-alkoxy, substituted or non-substituted Ci-C₈-halogenoalkoxy having 1 to 5 halogen atoms, substituted or non-substituted Ci-C₈-alkylsulphenyl, substituted or non-substituted C₃-C₈-alkynyloxy, substituted or non-substituted phenoxy, substituted or non-substituted aryl, substituted or non-substituted aryl-[Ci-C₈]-alkyl, substituted or non-substituted tri(Ci-C₈- alkyl)-silyloxy, substituted or non-substituted, saturated or unsaturated A-, 5-, 6- or 7- membered heterocyclyl comprising up to 4 heteroatoms selected in the list consisting of N, O, S; substituted or non-substituted, saturated or unsaturated A-, 5-, 6- or 7-membered heterocyclyl-[d-C₈]-alkyl comprising up to 4 heteroatoms selected in the list consisting of N, O, S.

3. A compound according to claim 2 wherein Q¹ and Q² independently represent a hydrogen atom, a halogen atom, substituted or non-substituted d-C₈-alkyl.

4. A compound according to claims 1 to 3 wherein Q³ represents a halogen atom, a cyano group, substituted or non-substituted Ci-C₈-alkyl, substituted or non-substituted tri(Ci-C₈- alkyl)silyl, substituted or non-substituted Ci-C₈-cycloalkyl, substituted or non-substituted d- C₈-halogenoalkyl having 1 to 5 halogen atoms, substituted or non-substituted Ci-C₈-alkoxy.

5. A compound according to claim 4 wherein Q³ represents a halogen atom, substituted or non-substituted d-C₈-alkyl.

6. A compound according to claims 1 to 5 wherein R¹ represents a hydrogen atom, a hydroxy group, a substituted or non-substituted carbaldehyde O-(C-ι-C₈-alkyl)oxime, a formyloxy group, substituted or non-substituted C-ι-C₈-alkoxyamino group, substituted or non-substituted N-C-ι-C₈-alkyl-(C-ι-C₈-alkoxy)-amino group, a substituted or non-substituted (hydroxyimino)-C-ι-C₆-alkyl group, substituted or non-substituted C-ι-C₈-alkyl, substituted or non-substituted tri(C-ι-C₈-alkyl)silyl, substituted or non-substituted tri(d-C₈-alkyl)silyl-d-C₈- alkyl, substituted or non-substituted C-ι-C₈-cycloalkyl, substituted or non-substituted tri(d-C₈- alkyl)silyl-Ci-C₈-cycloalkyl, substituted or non-substituted Ci-C₈-halogenoalkyl having 1 to 5 halogen atoms, substituted or non-substituted Ci-C₈-halogenocycloalkyl having 1 to 5 halogen atoms, a C₂-C₈-alkenyl, substituted or non-substituted C₂-C₈-alkynyl, substituted or non-substituted Ci-C₈-alkoxy, substituted or non-substituted Ci-C₈-halogenoalkoxy having 1 to 5 halogen atoms, substituted or non-substituted C₂-C₈-alkenyloxy, substituted or non- substituted C₃-C₈-alkynyloxy, substituted or non-substituted d-Cs-alkylcarbonyloxy, substituted or non-substituted (Ci-C₆-alkoxyimino)-Ci-C₆-alkyl, substituted or non-substituted (C-rC₆-alkenyloxyinnino)-Ci-C₆-alkyl, substituted or non-substituted (d-C₆-alkynyloxyimino)- C-ι-C₆-alkyl, substituted or non-substituted (benzyloxyimino)-C-ι-C₆-alkyl, substituted or non- substituted benzyloxy, substituted or non-substituted benzylsulphenyl, substituted or non- substituted phenoxy, substituted or non-substituted phenylsulphenyl, substituted or non- substituted aryl, substituted or non-substituted aryl-[C-ι-C₈]-alkyl, substituted or non- substituted tri(C-ι-C₈-alkyl)-silyloxy.

7. A compound according to claim 6 wherein R¹ represents a hydrogen atom, a hydroxy group, substituted or non-substituted d-C₈-alkyl, substituted or non-substituted C₃-C₈- cycloalkyl, substituted or non-substituted Ci-C₈-halogenoalkyl having 1 to 5 halogen atoms, a C₂-C₈-alkenyl, substituted or non-substituted C₂-C₈-alkynyl, substituted or non-substituted Ci-C₈-alkoxy, substituted or non-substituted Ci-C₈-halogenoalkoxy having 1 to 5 halogen atoms, substituted or non-substituted C₂-C₈-alkenyloxy, substituted or non-substituted C₃-C₈- alkynyloxy, substituted or non-substituted Ci-C₈-alkylcarbonyloxy, substituted or non- substituted benzylsulphenyl, substituted or non-substituted phenoxy, substituted or non- substituted phenylsulphenyl, substituted or non-substituted aryl, substituted or non- substituted aryl-[d-C₈]-alkyl.

8. A compound according to claim 7 wherein R¹ represents a hydrogen atom, a hydroxy group, substituted or non-substituted d-C₈-alkyl, substituted or non-substituted C₃-C₈- cycloalkyl, substituted or non-substituted d-C₈-halogenoalkyl having 1 to 5 halogen atoms, substituted or non-substituted d-C₈-alkoxy, substituted or non-substituted C₁-C₈- halogenoalkoxy having 1 to 5 halogen atoms.

9. A compound according to claims 1 to 8 wherein R² represents a hydrogen atom, substituted or non-substituted C-ι-C₈-alkyl, substituted or non-substituted C-i-C₈-cycloalkyl.

10. A compound according to claims 1 to 9 wherein R³ represents -(CR^aR^b)p-R⁴ and: o R^a and R^b represent independently a hydrogen atom, substituted or non- substituted C-ι-C₈-alkyl, a halogen atom, a substituted or non-substituted C-ι-C₈-alkoxy, or ° R^a and R^b, form a 3- to 8-membered carbocyclic;

R⁴ represents a halogen atom, substituted or non-substituted Ci-C₈-alkyl, substituted or non-substituted d-C₈-alkenyl, substituted or non-substituted

C-i-Cs-alkyloxy-C-i-Cs-alkyl, -C≡C-R⁵ wherein R⁵ represents a hydrogen atom, a halogen atom, substituted or non-substituted C-ι-C₈-alkyl, substituted or non-substituted C₃-C₈-Cy cloa Iky I, substituted or non-substituted C₁-C₈- alkyloxy-d-C₈-alkyl, substituted or non-substituted aryl, substituted or non- substituted aryl-[d-C₈]-alkyl, substituted or non-substituted tri(d-C₈-alkyl)- silyl; substituted or non-substituted, saturated or unsaturated A-, 5-, 6- or 7- membered heterocyclyl comprising up to 4 heteroatoms selected in the list consisting of N, O, S; substituted or non-substituted, saturated or unsaturated A-, 5-, 6- or 7-membered heterocyclyl-[Ci-C₈]-alkyl comprising up to 4 heteroatoms selected in the list consisting of N, O, S, wherein the N atom is substituted or unsubstituted with substituted or non-substituted d- C₈-alkyl, substituted or non-substituted C₃-C₈-cycloalkyl, substituted or non- substituted d-C₈-alkyloxy-d_|-C₈-alkyl, substituted or non-substituted aryl, substituted or non-substituted aryl-[Ci-C₈]-alkyl; p is 0 or 1.

11. A compound according to claim 10 wherein R³ represents -(CR^aR^b)p-R⁴ and: o R^a and R^b represent independently a hydrogen atom, a substituted or non- substituted Ci-C₈-alkyl, or ° R^a and R^b, form a 3- to 8-membered carbocyclic; o R⁴ represents substituted or non-substituted d-C₈-alkyloxy-d-C₈-alkyl, - C≡C-R⁵ wherein R⁵ represents a hydrogen atom, a halogen atom, substituted or non-substituted Ci-C₈-alkyl, substituted or non-substituted d- C₈-alkyloxy-Ci-C₈-alkyl, substituted or non-substituted, saturated or unsaturated 5 or 6 membered heterocyclyl comprising up to 4 heteroatoms selected in the list consisting of N, O, S; wherein the N atom is substituted or unsubstituted with substituted or non-substituted Ci-C₈-alkyl, Λ p is 0 or 1

12. A compound according to claims 1 to 11 wherein L represents an oxygen atom.

13. A fungicide composition comprising, as an active ingredient, an effective amount of a compound of formula (I) according to claims 1 to 12 and an agriculturally acceptable support, carrier or filler.

14. A method for controlling phytopathogenic fungi of crops, characterized in that an agronomically effective and substantially non-phytotoxic quantity of a compound according to claims 1 to 12 or a composition according to claim 13 is applied to the soil where plants grow or are capable of growing, to the leaves or the fruit of plants or to the seeds of plants.