WO2001002385A1 - 1-(quinolin-4-yl)-1h-pyrazole derivatives and their use as fungicides - Google Patents

Abstract

The invention concerns compounds of general formula (I) wherein R1, R2, are different, their use as fungicides, in particular in the form of fungicidal compositions, and the methods for controlling phytopathogenic fungi using said compounds and compositions.

Description

DERIVATIVES OF 1- (QUIN0LIN-4 -YL) - IH- PYRAZOLE AND THEIR USE AS FUNGICIDES

5 Field of the invention

The present invention relates to new compounds comprising a pyrazole group, their method of preparation, their use as fungicides, in particular in the form of fungicidal compositions, as well as the methods for controlling phytopathogenic fungi in crops using these compounds or these compositions.

State of the art

Very many compounds comprising a pyrazole group are already known and widely illustrated in the literature. For example, the patent

US 4,622,330 describes pyrazole derivatives having anti-parasitic activities.

More specifically, US patents 5,760,056 and WO-A-97/17064 describe quinolyl-pyrazole derivatives having an adamantylcarboxylic group

20 and useful in the therapeutic treatment of disorders of the central nervous system.

Patent applications EP-A-0703234 and DE-A-19636509 describe in particular fungicidal compounds having a quinolyl-pyrazole structure, the pyrazole ring of which optionally carries a single substituent.

The known quinolyl-pyrazole derivatives, and in particular those known for their fungicidal activity, however have many drawbacks, well known to the user of such compounds, that is to say that faced with the problems of control. against fungal plant diseases: low activity, compounds effective on a relatively small range of fungal diseases, low selectivity, toxicity, even

30 ecotoxicity.

In other words, the known fungicidal compounds are weakly active and / or have a relatively narrow spectrum of activity. In order to eradicate all the different species of fungi attacking plants, the user must for example use several products, of which he must know exactly the spectrum and the

35 application doses. The use of several products goes against the methods of treatment of crops recommended today, where the application doses must be as low as possible, with the obvious aim of protecting the environment. In addition, the use of large quantities of products and / or several different fungicide products are very often harmful to crops (product toxicity). The use of large quantities of products in the treatment of fungal diseases leads in certain cases to the appearance of fungal strains resistant to these products. This is the reason why it is always necessary to offer the user new anti-fungal molecules.

An object of the present invention is to provide a new family of compounds having a broad spectrum of action on phytopathogenic fungi in cultures.

Another object of the present invention is to propose a new family of compounds having a broad spectrum of action on phytopathogenic fungi of cultures making it possible to solve the specific problems encountered.

Another object of the present invention is to provide a new family of compounds active at low doses on phytopathogenic fungi in cultures. Another object of the present invention is to provide a new family of compounds having a broad spectrum of improved action on phytopathogenic fungi in crops.

Another object of the present invention is to provide a new family of compounds having a broad spectrum of action improved on phytopathogenic fungi of cultures and having reduced toxicity and / or ecotoxicity. Another object of the present invention is to provide a new family of compounds having a broad spectrum of improved action on phytopathogenic fungi of crops such as cereals, rice, corn, sunflowers, fruit trees, forest trees, vines, oilseed crops, vegetable crops, solaneas, beets, etc.

General definition of the invention:

Quite surprisingly, it has been found that these objects can be produced in whole or in part, by compounds comprising a quinolyl-pyrazole unit, in which the pyrazole comprises at least two different substituents. The present invention relates to compounds of general formula (I)

compounds of formula (I) in which: • R, and R ₂ are different and are chosen from an alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkoxysulfonyl, alkenyl, alkynyl, alkenyloxy, alkynyloxy, alkenylthio, alkynylthio, cycloalkyl, heterocyclyl radical , cycloalkylalkyl, heterocyclylalkyl, alkylcarbonyl, alkenylcarbonyl, alkynylcarbonyl, alkylcarbonyloxy, alkénylcarbonyloxy, alkynylcarbonyloxy, alkoxy carbonyl, alkoxyalkylcarbonyle, alkenyloxycarbonyl, alkynyloxycarbonyl, cycloalkyl-carbonyl, heterocyclylcarbonylaminoalkyl, cycloalkyl-oxycarbonyl, cycloalkylalkyloxycarbonyl, heterocyclyl-oxycarbonyl, hétérocyclylalkoxycarbonyle, thioalkylthiocarbonyle, alkoxythiocarbonyle, thioalkyl, an aryl, heteroaryl, arylcarbonyl, heteroarylcarbonyl radical, the hydroxy radical, the mercapto radical, the carboxy radical, the nitro radical, the cyano radical, the thiocyanato radical, the azido radical, a NR ₄ R ₅ radical, C (= O) NR ₄ R ₅ , C (= S) NR ₄ R ₅ , u n radical C (= NR ₄ ) R ₅ , a halogen atom, the sulfonyl radical, the sulfinyl radical, the sulfanyl radical, the phosphoryl radical and the phosphone radical,

or,

R, and R ₂ can together form a ring of 4 to 7 atoms, containing 2 to 3 atoms of oxygen and / or nitrogen, optionally substituted by one or more radicals chosen from halogen, alkyl, haloalkyl, alkoxy, amino and NR ₄ R ₅ ;

R ₃ is chosen from hydrogen, an alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkoxysulfonyl, alkenyl, alkynyl radical, alkenyloxy, alkynyloxy, alkenylthio, alkynylthio, cycloalkyl, heterocyclyl, cycloalkylcarbonyl, heterocyclylcarbonylaminoalkyl, cycloalkylalkyl, heterocyclylalkyl, alkylcarbonyl, alkenylcarbonyl, alkynylcarbonyl, alkylcarbonyloxy, alkénylcarbonyloxy, alkynylcarbonyloxy, alkoxycarbonyl, alkenyloxycarbonyl, alkynyloxycarbonyl, cycloalkyl-oxycarbonyl, cycloalkylalkyloxycarbonyl, heterocyclyloxycarbonyl, hétérocyclylalkoxycarbonyle a radical aryl, heteroaryl, arylcarbonyl, heteroarylcarbonyl, hydroxy radical, mercapto radical, carboxy radical, nitro radical, cyano radical, thiocyanato radical, azido radical, NR ₄ R ₅ radical,

C (= O) NR ₄ R ₅ , C (= S) NR ₄ R ₅ and a radical C (= NR ₄ ) R ₅ ,

• R ₄ and R ₅ , identical or different, are chosen from hydrogen, an alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkoxysulfonyl, alkenyl, alkynyl, alkenyloxy, alkynyloxy, alkenylthio, alkynylthio, cyanoalkyl, alkoxyalkyl, alkoxycarbonylalkyl radical cycloalkyl, heterocyclyl, cycloalkylalkyl, heterocyclylalkyl, alkylcarbonyl, alkenylcarbonyl, alkynylcarbonyl, alkoxycarbonyl, alkenyloxycarbonyl, alkynyloxycarbonyl, cycloalkyloxycarbonyl, cycloalkylalkyloxycarbonyl, heterocyclyloxycarbonyl, hétérocyclylalkoxycarbonyle, aryl, heteroaryl, arylcarbonyl, heteroarylcarbonyl, arylalkyl, heteroarylalkyl, the mercapto radical, the carboxy radical, the nitro radical, the cyano radical, the thiocyanato radical, the azido radical, an ORe, amino, alkylamino, dialkylamino, aminoalkyl, alkylaminoalkyl and dialkylaminoalkyl, hydrazino radical,

or, R ₄ and R ₅ can together form a ring of 4 to 7 atoms, containing 2 to 3 atoms of oxygen and / or nitrogen, optionally substituted by one or more radicals chosen from halogen, alkyl, haloalkyl, alkoxy , amino and NR ₇ R ₈ ;

Ru represents hydrogen, an alkyl, aryl, heteroaryl, arylalkyl, hetertoarylalkyl, cycloalkyl, cycloalkylalkyl, heterocyclyl, heterocyclyalkyl and alkoxycarbonylalkyl radical, • R ₇ and R ₈ , identical or different, are chosen from hydrogen, an alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkoxysulfonyl, alkenyl, alkynyl, alkenyloxy, alkynyloxy, alkenylthio, alkynylthio, cyanoalkyl, alkoxyalkyl, alkoxycarbonylalkyl radical cycloalkyl, heterocyclyl, cycloalkylalkyl, heterocyclylalkyl, alkylcarbonyl, alkenylcarbonyl, alkynylcarbonyl, alkoxycarbonyl, alkenyloxycarbonyl, alkynyloxycarbonyl, cycloalkyloxycarbonyl, cycloalkylalkyloxycarbonyl, heterocyclyloxycarbonyl, hétérocyclylalkoxycarbonyle, aryl, heteroaryl, arylcarbonyl, heteroarylcarbonyl, arylalkyl, heteroarylalkyl, the mercapto radical, the carboxy radical, the nitro radical, the cyano radical, the thiocyanato radical, the azido radical, an ORg radical, amino, alkylamino, dialkylamino, aminoalkyl, alkylaminoalkyl and dialkylaminoalkyl, hydrazino,

or,

R ₇ and R ₈ can together form a ring of 4 to 7 atoms, containing 2 to 3 atoms of oxygen and / or nitrogen, optionally substituted by one or more radicals chosen from halogen, alkyl, haloalkyl, alkoxy and amino;

• the radicals Y ,, Y ₂ , Y ₃ , Y ₄ , Y ₅ and Y ₆ are chosen independently of each other from the hydrogen atom, a halogen atom; the hydroxy, mercapto, nitro, thiocyanato, azido, cyano or pentafluorosulfonyl radical, an alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkoxyalkyl, haloalkoxyalkyl, alkylthioalkyl, haloalkylthioalkyl, cyanoalkyl, cyanoalkylalkylalkylalkyl, alkylalkyl, alkylalkyl, alkylalkyl, alkylalkyl, alkylalkyl, alkylalkyl, cyanoalkyl, alkyl, alkyl haloalkylsulfonyl, alkoxysulfonyl,

a cycloalkyl, halocycloalkyl, alkenyl, alkynyl, alkenyloxy, alkynyloxy, alkenylthio, alkynylthio group, an optionally substituted aryl or heteroaryl radical, an amino, N-alkylamino, N, N-dialkylamino, acylamino, aminoalkyl, N-alkylaminoalkyl radical, N, N-dialkylaminoalkyl, acylaminoalkyl, the carboxy radical, the carbamoyl radical, an N-alkylcarbamoyl, N, N-dialkylcarbamoyl, alkoxycarbonyl and an alkylcarbonyl radical,

or two adjacent radicals chosen from Y „Y ₂ , Y ₃ , Y ₄ , Y ₅ and Y ₆ can also form, together and with the two carbon atoms which carry them, a 6-membered aromatic ring, or two adjacent radicals chosen from Y ,, Y ₂ , Y ₃ , Y ₄ , Y ₅ and Y ₆ can also together form a divalent methylene-di-oxy radical;

• all of the radicals defined above and having a hydrocarbon chain (alkyl, alkoxy, cycloalkyl, heterocycloalkyl, alkenyl, alkynyl, etc.) may optionally be substituted by one or more groups or radicals, identical or different, chosen from hydroxy , mercapto, NR ₄ R ₅ , cyano, nitro, alkyl, alkoxyalkyl, aryl, heteroaryl, halogen, alkoxy, alkylthio, alkylcarbonyl, alkylcarbonyloxy, alkenylcarbonyl, alkenylcarbonyloxy, alkynylcarbonyl, alkynylcarbonyloxy, arylcarbonyl, arylcarbonyloxycarbonyl arylcarbonyloxycarbonylarbonyloxycarbonylarbonyloxy heteroaryloxy, heteroarylthio, haloalkoxy, perhalogénoalkoxy, cyanoalkylcarbonyloxy, cycloalkyl, heterocyclyl, cycloalkylcarbonyl, cycloalkylcarbonyloxy, heterocyclylcarbonyl, heterocyclylcarbonyloxy, aryloxyalkylcarbonyloxy, alkylcarbonylalkylcarbonyloxy, alkoxycarbonylalkylcarbonyloxy, arylcarbonylcarbonyloxy, hétéroarylcarbonylcarbonyloxy, alkoxyalkoxyalky lcarbonyloxy and alkylthioalkylcarbonyloxy,

• all of the aryl and heteroaryl radicals defined above may optionally be substituted by one or more groups or radicals, identical or different, chosen from hydroxy, mercapto, oxo, cyano, nitro, cyanato, thiocyanato, formyl, propylene-diyl , amino, alkylamino, dialkylamino, pentafluorosulfonyl, aryl, heteroaryl, halogen, alkyl, haloalkyl, perhaloalkyl, alkenyl, alkynyl, alkoxy, alkylthio, haloalkoxy, perhaloalkoxy, alkoxyalkyl, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxycarbonyl, alkylcarbonyloxy , arylcarbonyloxy, heteroarylcarbonyl, heteroarylcarbonyloxy, aryloxy, arylthio, heteroaryloxy, heteroarylthio, cycloalkyl, heterocyclyl, cycloalkylcarbonyl and heterocyclylcarbonyl, their possible geometric and / or optical isomers, their possible tautomeric forms, as well as the salts, N-oxides and the metal and metalloid complexes of the compounds of formula (I) as they have just been defined.

In the preceding definitions of the radicals R, to R ₈ and Y, to Y ₆ , it should be understood that:

- alkyl, alkenyl, alkynyl radicals or groups (as well as derivative radicals, such as alkoxy, alkoxycarbonyl, etc.) contain from 1 to 6 carbon atoms (from 2 to 6 for alkenyl and alkynyl radicals) in a linear chain or branched;

the cycloalkyl radicals contain from 3 to 7 carbon atoms, the rings being partially or completely saturated, for example cyclopropyl, cyclopentyl, cyclopentenyl, cyclohexyl, cyclohexenyl; - the heterocyclyl radicals contain from 3 to 7 atoms, among which 1, 2 or 3 are chosen from nitrogen, oxygen and sulfur, the others being carbon atoms, the rings being partially or completely saturated, for example aziridyl, morpholyl, thiomorpholyl , piperidyl, piperazinyl, pyrrolidinyl, imidazolidinyl, thioimidazolidinyl, isoxazolyl, isothiazolyl, tetrahydropyridinyl, 1,3-dioxolyl;

- By aryl radical means the phenyl radical or the naphthyl radical;

- By heteroaryl radical means a heteroaromatic mono or bicyclic radical of 3 to 10 members which may contain up to 3 identical or different heteroatoms and chosen from nitrogen, oxygen and sulfur. Examples of aromatic radicals are the pyridyl, quinolyl, quinoxalyl, furyl, thienyl, pyrrolyl, pyrazinyl, pyridazinyl radical,

[0008] Furthermore, the following generic terms are used with the following meanings: - halogen means fluorine, chlorine, bromine or iodine;

- the halogen radicals may contain one or more identical or different halogen atoms;

- the acyl radical signifies alkylcarbonyl, or cycloalkylcarbonyl;

- when a radical is disubstituted, the two substituents can be identical or different;

- when the amino radical is disubstituted, the two substituents can constitute a saturated or unsaturated nitrogen heterocycle, of 4 or 6 atoms; - When the carbamoyl radical is disubstituted, the two substituents can constitute a saturated or unsaturated nitrogen heterocycle, of 4 or 6 atoms;

Preferred embodiments of the invention are those where the products of formula (I) also have one and / or the other of the following characteristics, taken individually or in combination:

• R _[ and R ₂ are different and are chosen from an alkyl, alkoxyalkyl, alkylthioalkylke, hydroxyalkyl, aminoalkoxyalkyl, N-alkylaminoalkoxy-alkyl, N, N-dialkylaminoalkoxyalkyl, aminoalkylthioalkyl, N-alkyl-aminoalkyl-thioalkyl radical,

N, N-dialkylaminoalkylthioalkyl, alkenyl, cycloalkyl, cycloalkylcarbonyl, heterocyclylcarbonyl, heterocyclyl, cycloalkylalkyl, heterocyclylalkyl, alkylcarbonyl, alkylcarbonyloxy, alkylcarbonyloxyalkyl, alkenylcarbonyloxyoxycarbonyloxy

aryl, heteroaryl, arylalkyl, heteroarylalkyl, aryloxyalkyl, heteroaryloxyalkyl, arylcarbonyl, heteroarylcarbonyl, alkyl arylcarbonyloxy-, hétéroarylcarbonyloxyalkyle, the hydroxy radical, carboxy radical, the nitro radical, the cyano radical, a radical NR ₄ R _5, CH ₂ NR ₄ R ₅ , C (= O) NR ₄ R ₅ , and a radical C (= NR ₄ ) R ₅ ,

R ₃ is chosen from hydrogen, an alkyl, alkoxy, alkoxyalkyl, alkylthio, alkenyl, alkynyl, cycloalkyl, heterocyclyl, cycloalkylalkyl, heterocyclylalkyl, alkylcarbonyl, alkylcarbonyl, alkoxycarbonyl radical,

the hydroxy radical, the mercapto radical, the carboxy radical, and a NR ₄ R ₅ radical,

• R ₄ and R ₅ , identical or different, are chosen from hydrogen, an alkyl, alkoxy, alkoxyalkyl, alkylthio, alkenyl, alkynyl, alkenyloxy, alkynyloxy, cyanoalkyl, alkoxyalkyl, alkoxycarbonylalkyl, cycloalkyl, heterocyclyl, cycloalkylalkyl, heterocyclylalkyl alkylcarbonyl, alkoxycarbonyl, an aryl, heteroaryl, arylalkyl, heteroarylalkyl radical, the mercapto radical, the cyano radical, an ORβ radical, amino, alkylamino, dialkylamino, aminoalkyl, alkylaminoalkyl and dialkylaminoalkyl, Rg represents hydrogen, an alkyl, aryl, heteroaryl, arylalkyl, hetertoarylalkyl, cycloalkyl, cycloalkylalkyl, heterocyclyl, heterocyclyalkyl, and alkoxycarbonylalkyl radical,

• the radicals Y ,, Y ₂ , Y ₃ , Y ₄ , Y ₅ and Y ₆ are chosen independently of one another from the hydrogen atom, a halogen atom, the hydroxy, mercapto, nitro, cyano radical or pentafluorosulfonyl, an alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkoxyalkyl, haloalkoxyalkyl, cyanoalkyl, cyanoalkoxy, cyanoalkylthio radical, an alkenyl, alkynyl, alkenyloxy, alkynyloxy, alkenylthio, alkynyl, alkyl , N-dialkylamino, aminoalkyl,

N-alkylaminoalkyl, N, N-dialkylaminoalkyl, the carboxy radical, alkoxycarbonyl and an alkylcarbonyl radical,

or else two adjacent radicals chosen from Y ,, Y ₂ , Y ₃ , Y ₄ , Y ₅ and Y ₆ can also form, together and with the two carbon atoms which carry them, a 6-membered aromatic ring,

• all of the radicals defined above and having a hydrocarbon chain (alkyl, alkoxy, cycloalkyl, heterocycloalkyl, alkenyl, alkynyl, etc.) may optionally be substituted by one or more groups or radicals, identical or different, chosen from hydroxy , mercapto, amino, N-alkylamino, N, N-dialkylamino, cyano, nitro, aryl, heteroaryl, halogen, alkoxy, alkylthio, aryloxy, arylthio, heteroaryloxy, heteroarylthio, haloalkoxy, perhaloalkoxy, cyanoalkylcarbonylcycloalkyl , cycloalkylcarbonyloxy, heterocyclylcarbonyl, heterocyclylcarbonyloxy, aryloxyalkylcarbonyloxy, alkylcarbonylalkylcarbonyloxy, alkoxycarbonylalkylcarbonyloxy, arylcarbonylcarbonyloxy, heteroarylcarbonylcarbonyloxy, alkoxyalkoxyalkylcarbonyloxycarbonyloxy

• all of the aryl and heteroaryl radicals defined above may optionally be substituted by one or more groups or radicals, identical or different, chosen from oxo, cyano, nitro, formyl, propylene-diyl, amino, N-alkylamino, N , N-dialkylamino, aryl, heteroaryl, halogen, alkyl, haloalkyl, perhaloalkyl, alkoxy, alkylthio, haloalkoxy, perhaloalkoxy, alkoxyalkyl, alkylcarbonyl, alkoxycarbonyl, aryloxy, cycloalkyl and heterocyclyl,

their possible geometric and / or optical isomers, their possible tautomeric forms, as well as the salts, N-oxides and the metal and metalloid complexes of the compounds of formula (I) as they have just been defined.

Advantageously, the compounds of formula (I) which have the following characteristics taken alone or in combination are still preferred:

• R, and R ₂ are different and are chosen from an alkyl, alkoxyalkyl, alkylthioalkylke, hydroxyalkyl, aminoalkoxyalkyl, N-alkylaminoalkoxy-alkyl, N, N-dialkylaminoalkoxyalkyl, aminoalkyl-thioalkyl, N-alkylaminoalkyl-thioalkyl, N, N radical. dialkylaminoalkylthioalkyle, alkenyl, cycloalkylcarbonyl, heterocyclylcarbonylaminoalkyl, cycloalkylalkyl, heterocyclylalkyl, alkylcarbonyl, alkylcarbonyloxy, alkylcarbonyl oxyalkyl, alkoxycarbonyl, cycloalkylalkoxycarbonyle, aryl, heteroaryl, arylalkyl, heteroarylalkyl, aryloxyalkyl, heteroaryloxyalkyl, arylcarbonyl, heteroarylcarbonyl, carboxy radical, a radical NR ₄ R ₅ , CH ₂ NR ₄ R ₅ , C (= O) NR ₄ R ₅ , and a radical C (= NR ₄ ) R ₅ ,

R ₃ is chosen from hydrogen, an alkyl, alkoxy, alkoxyalkyl, alkylthio, cycloalkyl, heterocyclyl, cycloalkylalkyl, heterocyclylalkyl, alkoxycarbonyl, carboxy radical, and a radical NR ₄ R ₅ ,

• R ₄ and R ₅ , identical or different, are chosen from hydrogen, an alkyl, alkoxy, alkoxyalkyl, alkoxyalkyl, alkoxycarbonylalkyl, cycloalkyl, heterocyclyl, cycloalkylalkyl, heterocyclylalkyl, aryl, heteroaryl, arylalkyl, heteroarylalkyl radical, and a radical OR _e ,,

• Rβ represents hydrogen, an aryl, heteroaryl, arylalkyl, hetertoarylalkyl, cycloalkyl, cycloalkylalkyl, heterocyclyl, and heterocyclyalkyl radical, The radicals Y „Y ₂ , Y ₃ , Y ₄ , Y ₅ and Y ₆ are chosen independently of one another from the hydrogen atom, a halogen atom, the hydroxy radical, an alkyl or haloalkyl radical, alkoxy, haloalkoxy, alkoxyalkyle and haloalkoxyalkyle,

• all of the radicals defined above and having a hydrocarbon chain (alkyl, alkoxy, cycloalkyl, heterocycloalkyl, alkenyl, alkynyl, etc.) may optionally be substituted by one or more groups or radicals, identical or different, chosen from hydroxy , halogen, alkoxy and haloalkoxy,

• all of the aryl and heteroaryl radicals defined above may optionally be substituted by one or more groups or radicals, identical or different, chosen from oxo, halogen, alkyl, haloalkyl, perhaloalkyl, alkoxy, haloalkoxy, perhaloalkoxy, alkoxyalkyl, alkylcarbonyl , alkoxycarbonyl and aryloxy,

their possible geometric and / or optical isomers, their possible tautomeric forms, as well as the salts, N-oxides and the metal and metalloid complexes of the compounds of formula (I) as they have just been defined.

Particularly advantageously, the compounds of formula (I) are further preferred having the following characteristics taken individually or in combination:

• R, and R ₂ are different and are chosen from an alkyl, alkoxyalkyl, hydroxyalkyl, cycloalkylcarbonyl, heterocyclylcarbonyl, alkylcarbonyl, alkylcarbonyloxy, alkylcarbonyloxyalkyl, alkoxycarbonyl, cycloalkylalkoxycarbonyl, aryl, heteroaryl, arylalkyl, heteroalkyl, arylalkylalkyl, hydroxyalkyl, arylalkyl, hydroxyalkyl, alkyl group carboxy and a radical C (= O) NR ₄ R ₅ ,

• R ₃ represents hydrogen,

• R ₄ and R ₅ , identical or different, are chosen from hydrogen, a radical alkyl, alkoxy and alkoxycarbonylalkyle,

the radicals Y „Y ₂ , Y ₃ , Y ₄ , Y ₅ and Y ₆ are chosen independently of one another from the hydrogen atom, a halogen atom, an alkyl, haloalkyl and alkoxy radical,

all the radicals defined above and having a hydrocarbon chain (alkyl, alkoxy, cycloalkyl, heterocycloalkyl, alkenyl, alkynyl, etc.) may optionally be substituted by one or more groups or radicals, identical or different, chosen from hydroxy, halogen, alkoxy and haloalkoxy,

all of the aryl and heteroaryl radicals defined above may optionally be substituted by one or more groups or radicals, identical or different, chosen from oxo, halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, perhaloalkoxy and alkoxycarbonyl,

their possible geometric and / or optical isomers, their possible tautomeric forms, as well as the salts, N-oxides and the metal and metalloid complexes of the compounds of formula (I) as they have just been defined.

Finally, the compounds of formula (I) chosen from among the:

1 - (7-chloro-4-quinolyl) -5- (methoxymethyl) -1 methyl H-pyrazole-4-carboxylate;

Methyl 3- (methoxymethyl) -1- [8- (trifluoromethyl) -4-quinolyl] -1H-pyrazole-4-carboxylate; 1- (7-chloro-4-quinolyl) -5- (3-nitrophenyl) -1H-pyrazole-4-carboxylate methyl; 1- (7-chloro-4-quinolyl) -N, N-diethyl-5- (methoxymethyl) -1H-pyrazole-4-carboxamide; 1- (7-chloro-4-quinolyl) -N-methoxy-5- (methoxymethyl) -N-methyl-1H-pyrazole-4-carboxamide;

Methyl 1 - (7-chloro-4-quinolyl) -5- (2-methoxyethyl) - 1 H-pyrazole-4-carboxylate;

Methyl 5- (2-methoxyethyl) -1- (7-methoxy-4-quinolyl) -1H-pyrazole-4-carboxylate; 1- [2,8-bis (trifluoromethyl) -4-quinolyl-N-methoxy-3- (methoxymethyl) -N-methyl-1H-pyrazole-4-carboxamide;

1 - (7-chloro-4-quinolyl) -3 - (methyl methoxymethy) - 1 H-pyrazole-4-carboxylate; methyl 1- (6-fluoro-4-quinolyl) -5- (methoxymethyl) -1H-pyrazole-4-carboxylate; 1- (7-chloro-4-quinolyl) -5- (methoxymethyl) -1H-pyrazole-4-carboxylate 2-ethoxyethyl;

N-methoxy-3- (methoxymethyl) -N-methyl- 1 - [8 (trifluoromethyl) -4-quinolyl] - 1H-pyrazole-4-carboxamide;

[1- (7-chloro-4-quinolyl) -5- (methoxymethyl) -1H-pyrazole-4-yl] (1,3-thiazolidin-3-yl) methanone;

2- [1- (7-chloro-4-quinolyl) -5- (methoxymethyl) -1H-pyrazol-4-yl] -2-propanol;

1 - (7-chloro-4-quinolyl) -N-methoxy-5- (methoxymethyl) -N-propyl-1 H-pyrazole-4-carboxamide;

Dimethyl 5 - ({4-methoxycarbonyl) -1- [8- (trifluoromethyl) -4-quinolyl] -1H-pyrazol-5-yl} methoxy) isophthalate;

1 - (7-chloro-4-quinolyl) -N-isopropyl-N-methoxy-5- (methoxymethyl) - 1 H-pyrazole-4-carboxamide;

Methyl 4 - [[[1- (7-chloro-4-quinolyl) -5- (methoxymethyl) -1H-pyrazole-4-yl] carbonyl} (methoxy) amino] butanoate;

Methyl 5 - [(heptanoyloxy) methyl] -1- [8- (trifluoromethyl) -4-quinolyl] - H-pyrazole-4-carboxylate; 7-chloro-4- {5-methoxymethyl) -4- [5-trifluoromethyl) -1,2,4-oxadiazol-3-yl] -lΗ-pyrazol-l-yl}; quinoline methyl l- (7- chloro-4-quinolinyl) -5 - {[(l; l-dimethylethyl) sulfanyl] methyl} - 1H-pyrazole-4-carboxylate; 1- (7-chloro-4-quinolinyl) -5 - [(methyloxy) methyl] -1H-pyrazole-4-carbaldehyde;

[1 - (7-chloro-4-quinoliny l) -4- (1 -phenylethenyl) - 1 H-py razol-5 -yl] methyl methyl ether; l- {3 - [(methyloxy) methyl] -l- [8- (trifluoromethyl) -4-quinolinyl] -lH- pyrazol-4-yl} ethanone; methyl 3 - [(methyloxy) methyl] -5- (methylsulfanyl) -l- [8- (trifluoromethyl) -4- quinolinyl] -l H-pyrazole-4-carboxylate; methyl 5-chloro-3 - [(methyloxy) methyl] -l- [8- (trifluoromethyl) -4- quinolinyl] - 1 H-pyrazole-4-carboxylate;

(1 E) - 1 - {1 - (7-chloro-4-quinolinyl) -5 - [(methyloxy) methyl] - 1 H-pyrazol-4-yl} ethanone oxime;

1 - (2; 7-dimethyl-4-quinolinyl) -N-methyl-N- (methyloxy) -5- [(methyloxy) methyl] - 1 H-pyrazole-4-carboxamide;

N-methyl-l- [2-methyl-8- (l-methylethyl) -4-quinolinyl] -N- (methyloxy) -5- [(methyloxy) methyl] -1 H-pyrazole-4-carboxamide;

N-methyl-N- (methyloxy) -5 - [(methyloxy) methyl] - 1 - [2-methyl-7- (trifluoromethyl) -4-quinolinyl] - 1 H-pyrazole-4-carboxamide;

N-methyl-N- (methyloxy) -5 - [(methyloxy) methyl] - 1 - (2; 5; 7-trimethyl-4-quinolinyl) - 1 H-pyrazole-4-carboxamide; 1- (7-chloro-2; 8-dimethyl-4-quinolinyl) -N-methyl-N- (methyloxy) -5- [(methyloxy) methyl] - 1 H-pyrazole-4-carboxamide; 1- (6; 8-dichloro-2-methyl-4-quinolinyl) -N-methyl-N- (methyloxy) -5- [(methyloxy) methyl] -1 H-pyrazole-4-carboxamide;

N-methyl-N- (methyloxy) -5 - [(methyloxy) methyl] -1- (8-methyl-4-quinolinyl) - 1 H-pyrazole-4-carboxamide;

1 - (2; 8-dimethyl-4-quinolinyl) -N-methyl-N- (methyloxy) -5- [(methyloxy) methyl] - 1 H-pyrazole-4-carboxamide;

N-methyl-N- (methyloxy) -5 - [(methyloxy) methyl] -l- [2-methyl-8- (trifluoromethyl) -4-quinolinyl] - 1 H-pyrazole-4-carboxamide; 1- (6-chloro-2; 8-dimethyl-4-quinolinyl) -N-methyl-N- (methyloxy) -5- [(methyloxy) methyl] - 1 H-pyrazole-4-carboxamide;

N-methyl-N- (methyloxy) -5 - [(methyloxy) methyl] -1- (2-methyl-4-quinolinyl) - 1 H-pyrazole-4-carboxamide;

N-methyl-1- [2-methyl-8- (methyloxy) -4-quinolinyl] -N- (methyloxy) -5- [(methyloxy) methyl] -1 H-pyrazole-4-carboxamide;

N-methyl-N- (methyloxy) -5 - [(methyloxy) methyl] -1 - (2; 6; 8-trimethyl-4-quinolinyl) - 1 H-pyrazole-4-carboxamide; l- [5-chloro-2-methyl-8- (methyloxy) -4-quinolinyl] -N-methyl-N- (methyloxy) -5 - [(methyloxy) methyl] - 1 H-pyrazole-4-carboxamide;

1 - (5; 7-dichloro-4-quinolinyl) -N-methyl-N- (methyloxy) -5- [(methyloxy) methyl] -1 H-pyrazole-4-carboxamide;

5- (hydroxymethyl) -N-methyl-N- (methyloxy) -l- [8- (trifluoromethyl) -4-quinolinyl] -lH-pyrazole-4-carboxamide;

1 - (6-chloro-2; 8-dimethyl-4-quinolinyl) -N-methyl-N- (methyloxy) -5- [2- (methyloxy) ethyl] - 1 H-pyrazole-4-carboxamide; N-methyl-N- (methyloxy) -5 - [2- (methy loxy) ethy 1] - 1 - [8- (trifluoromethyl) -4- quinolinyl] - 1 H-pyrazole-4-carboxamide;

N-methyl-N- (methyloxy) -5- [2- (methyloxy) ethyl] -1- [7- (trifluoromethyl) -4-quinolinyl] -1H-pyrazole-4-carboxamide;

N; 5-dimethyl-N- (methyloxy) - 1 - [2-methyl-8- (trifluoromethyl) -4-quinolinyl] - 1 H-pyrazole-4-carboxamide;

1 - (7-chloro-4-quinolinyl) -5 - [(methyloxy) methyl] - 1 H-pyrazole-4-carbaldehyde O-methyloxime;

5- (bromomethyl) - 1 - (5; 7-dichloro-4-quinolinyl) -N-methyl-N- (methyloxy) - 1 H-pyrazole-4-carboxamide; 1- (7-chloro-4-quinolinyl) -3- (dibromomethyl) -N-methyl-N- (methyloxy) - 1H-pyrazole-4-carboxamide;

1 - {1 - (7-chloro-4-quinolinyl) -5 - [(methyloxy) methyl] - 1 H-pyrazol-4-yl} ethanol;

(1 E) - 1 - {3 - [(methyloxy) methyl] - 1 - [8- (trifluoromethyl) -4-quinolinyl] - 1 H- pyrazol-4-yl} ethanone O- (cyclopropylmethyl) oxime; N-methyl-N- (methyloxy) -3 - [(methyloxy) methyl] -1- [7- (trifluoromethyl) -4-quinolinyl] -lH-pyrazole-4-carboxamide;

N-methyl-N- (methyloxy) -3 - [(methyloxy) methyl] -1- [2- (trifluoromethyl) -4-quinolinyl] - 1 H-pyrazole-4-carboxamide;

1 - (7-chloro-4-quinolinyl) -N-methyl-N- (methyloxy) -3 - [(methyloxy) methyl] - 1 H-pyrazole-4-carboxamide; methyl 3 - {1 - (7-chloro-4-quinolinyl) -5- [(methyloxy) methyl] - 1 H-pyrazol-4- yl} -4; 5-dihydro-5-isoxazolecarboxylate; 1- (7-chloro-4-quinolinyl) -N- (cyclopropylcarbonyl) -N- (methyloxy) -5- [(methyloxy) methyl] -1 H-pyrazole-4-carboxamide; ethyl 3- {1- (7-chloro-4-quinolinyl) -5 - [(methyloxy) methyl] -1H-pyrazol-4- yl} -3-oxoρropanoate; 1- (7-chloro-4-quinolinyl) -N-methyl-N- (methyldisulfanyl) -5- [(methyloxy) methyl] -1 H-pyrazole-4-carboxamide; 1- (7-chloro-4-quinolinyl) -N- (ethyldisulfanyl) -N-methyl-5- [(methyloxy) methyl] -1 H-pyrazole-4-carboxamide;

1 - (7-chloro-4-quinolinyl) -N-methy l-N - [(1 -methylethyl) disulfanyl] -5- [(methyloxy) methyl] - 1 H-pyrazole-4-carboxamide; ethyl 1- (7-chloro-4-quinolinyl) -N- (methyloxy) -5 - [(methyloxy) methyl] -1H-pyrazole-4-carbimidothioate;

(1 E) - 1 - {1 - (7-chloro-4-quinolinyl) -5 - [(methyloxy) methyl] - 1 H-pyrazol-4- yl} -l-propanone O-methyloxime;

(3E) -4- {1- (7-chloro-4-quinolinyl) -5 - [(methyloxy) methyl] -1H-pyrazol-4-yl} -3-buten-2-one; ethyl (2Z; 4E) -5- {1- (7-chloro-4-quinolinyl) -5 - [(methyloxy) methyl] -H-pyrazol-4-yl} -3-hydroxy-2; 4-pentadienoate;

2-propenyl (2E) -3- {1- (7-chloro-4-quinolinyl) -5 - [(methyloxy) methyl] -1H-pyrazol-4-yl} -2-propenoate; 1- (7-chloro-4-quinolinyl) -N- (ethyloxy) -N-methyl-5 - [(methyloxy) methyl] - 1H-pyrazole-4-carboxamide;

4- (3 - [(methyloxy) methyl] -4- {5 - [(methyloxy) methyl] -3-isoxazolyl} -lH- pyrazol-1 -yl) -8- (trifluoromethyl) quinoline;

7-chloro-4- {4 - [(ethyloxy) methyl] -5 - [(methyloxy) methyl] -lH-pyrazol-1-yl} quinoline;

(Z) - {1- (7-chloro-4-quinolinyl) -5 - [(methyloxy) methyl] -1H-pyrazol-4- yl} [(methyloxy) imino] methyl methanesulfonate; 1- (7-chloro-4-quinolinyl) -N-methyl-5 - [(methyloxy) methyl] -N- (methylsulfanyl) - 1 H-pyrazole-4-carboxamide; 1- (7-chloro-4-quinolinyl) -N- (ethylsulfanyl) -N-methyl-5- [(methyloxy) methyl] -1 H-pyrazole-4-carboxamide; {1 - (7-chloro-4-quinolinyl) -5 - [(methyloxy) methyl] - 1 H-pyrazol-4- yl} acetonitrile;

3- (hydroxymethyl) -N; N-dimethyl-1- [8- (trifluoromethyl) -4-quinolinyl] -1H-pyrazole-4-carboxamide;

{1 - (7-chloro-4-quinolinyl) -4- [3- (4-fluorophenyl) -1; 2; 4-oxadiazol-5-yl] - 1H-pyrazol-5-yl} methyl methyl ether; 1- (7-chloro-4-quinolinyl) -N- (methyloxy) -N; 5-bis [(methyloxy) methyl] -1H-pyrazole-4-carboxamide;

[1 - (7-chloro-4-quinoliny l) -4- (3 -phenyl- 1; 2; 4-oxadiazol-5-yl) - 1 H-pyrazol- 5-yl] methyl methyl ether;

2-oxiranylmethyl 1 - (7-chloro-4-quinolinyl) -N- (methyloxy) -5-

[(methyloxy) methylj- 1 H-pyrazole-4-carboximidoate; l- (7-chloro-4-quinolinyl) -N '- [(cyclopropylmethyl) oxy] -5- [(methyloxy) methyl] - 1 H-pyrazole-4-carboximidamide; l- (7-chloro-4-quinolinyl) -N- (methyloxy) -5 - [(methyloxy) methyl] -lH- pyrazole-4-carboximidoyl chloride;

3- {1 - (7-chloro-4-quinolinyl) -5 - [(methyloxy) methyl] - 1 H-pyrazol-4-yl} - N; N-dimethyl-4; 5-dihydro-5-isoxazolecarboxamide; (1 Z) - 1 - {1 - (7-chloro-4-quinolinyl) -5 - [(methyloxy) methyl] - 1 H-pyrazol-4- yl} ethanone O- (2-methylpropanoyl) oxime;

(1 E) - 1 - {1 - (7-chloro-4-quinolinyl) -5 - [(methyloxy) methyl] - 1 H-pyrazol-4-yl} ethanone O- (cyclopropylcarbonyl) oxime; 1- (8-fluoro-4-quinolinyl) -N-methyl-N- (methyIoxy) -3 - [(methyloxy) methyl] - 1H-pyrazole-4-carboxamide;

N-methyl-N- (methyloxy) -3 - [(methyloxy) methyl] - 1 - (7-methyl-4-quinolinyl) - 1 H-pyrazole-4-carboxamide;

1 - (7-chloro-4-quinolinyl) -N-methyl-N- (methyloxy) -5- ({[2- (methyloxy) -5- nitropheny l] oxy} methyl) - 1 H-pyrazole-4- carboxamide;

5 - {[(2-bromo-3-pyridinyl) oxy] methyl} -N-methyl-N- (methyloxy) -l- [8- (trifluoromethyl) -4-quinolinyl] - 1 H-pyrazole-4-carboxamide ;

5 - {[(4'-bromo [1; 1 '-bipheny l] -4-yl) oxy] methyl} -N-methyl-N- (methyloxy) - 1 - [8- (trifluoromethyl) -4-quinolinyl ] - 1 H-pyrazole-4-carboxamide;

5-chloro-N-methyl-N- (methyloxy) -3 - [(methyloxy) methyl] -1- [8- (trifluoromethyl) -4-quinol inyl] - 1 H-pyrazole-4-carboxamide; methyl {[({1 - (7-chloro-4-quinolinyl) -5 - [(methyloxy) methyl] - 1 H-pyrazol-4-yl} carbonyl) (methyl) amino] oxy} (oxo) acetate;

1 - {1 - (7-fluoro-4-quinolinyl) -5 - [(methyloxy) methyl] - 1 H-pyrazol-4-yl} - 1 - propanone;

(1 E) - 1 - {1 - (7-chloro-4-quinolinyl) -5 - [(methyloxy) methyl] - 1 H-pyrazol-4- yl} ethanone O- [2- (methyloxy) acetyl] oxime ;

4- {1- (7-chloro-4-quinolinyl) -5 - [(methyloxy) methyl] -1H-pyrazol-4- yl} benzaldehyde; l- (7-chloro-4-quinolinyl) -5 - ({[2- (ethylsulfanyl) phenyl] oxy} methyl) -N- methyl-N- (methy loxy) - 1 H-pyrazole-4-carboxamide; l- (7-chloro-4-quinolinyl) -N-methyl-5 - [(methyloxy) methyl] -N- (propyloxy) - 1 H-pyrazole-4-carboxamide; 1- (7-chloro-4-quinolinyl) -N-methyl-5 - [(methyloxy) methyl] -N- (2-propenyloxy) - 1 H-pyrazole-4-carboxamide; l- (7-chloro-4-quinolinyl) -N-methyl-5 - [(methyloxy) methyl] -N - [(l-methylpropyl) oxy] - 1 H-pyrazole-4-carboxamide; l- (7-chloro-4-quinolinyl) -N-methyl-N - [(l-methylethyl) oxy] -5- [(methyloxy) methyl] - 1 H-pyrazole-4-carboxamide; methyl 4 - {[({1- (7-chloro-4-quinolinyl) -5 - [(methyloxy) methyl] -1H-pyrazol-4-y 1} carbonyl) (methy l) amino] oxy} butanoate;

N- (3-butenyloxy) -l- (7-chloro-4-quinolinyl) -N-methyl-5- [(methy loxy) methy 1] - 1 H-pyrazole-4-carboxamide; 1- (7-chloro-4-quinolinyl) -5 - [(ethyloxy) methyl] -N-methyl-N- (methyloxy) - 1H-pyrazole-4-carboxamide;

4- {4- {4; 5-bis [(methyloxy) methyl] -3-isoxazolyl} -5 - [(methyloxy) methyl] - 1 H-pyrazol- 1 -yl} -7-bromoquinoline;

(3- {1- (6-fluoro-4-quinolinyl) -5 - [(methyloxy) methyl] -1H-pyrazol-4-yl} -5- isoxazolyl) methyl acetate;

4- {4- {4; 5-bis [(methyloxy) methyl] -3-isoxazolyl} -5 - [(methyloxy) methyl] - 1 H-pyrazol- 1 -yl} -6-fluoroquinoline;

7-ethy l-4- (5 - [(methy loxy) methy 1] -4- {5 - [(tetrahy dro-2H-pyran-2- y loxy) methyl] -3 -isoxazolyl} - 1 H-pyrazol - 1 -yl) quinoline; 4- {4- {4; 5-bis [(methyloxy) methyl] -3-isoxazolyl} -5 - [(methyloxy) methyl] - 1 H-pyrazol- 1 -yl} -7-ethylquinoline;

3 - {[(3- {1- (7-chloro-4-quinolinyl) -5 - [(methyloxy) methyl] -1H-pyrazol-4-yl} -5-isoxazolyl) methyl] oxy} propanenitrile; methyl 3- {1 - (7-chloro-4-quinolinyl) -5 - [(methyloxy) methyl] - 1 H-pyrazol-4- yl} -4-methyl-5-isoxazolecarboxylate;

1; l-dimethylethyl 3- {l- (7-chloro-4-quinolinyl) -5 - [(methyloxy) methyl] - 1H-pyrazol-4-yl} -5-isoxazolecarboxylate;

3 - {[(3- {1- (7-ethyl-4-quinolinyl) -5 - [(methyloxy) methyl] -lH-pyrazol-4-yl} - 5 -isoxazolyl) methy 1] oxy} propanenitri le;

{1 - (7-chloro-4-quinolinyl) -4- [2- (trifluoromethyl) phenyl] - 1 H-pyrazol-5-yl} methyl methyl ether;

7-chloro-4- (5 - [(methyloxy) methyl] -4- {4 - [(trifluoromethyl) oxy] phenyl} - 1 H-pyrazol-1-yl) quinoline; methyl 5 - [(methyloxy) methyl] -l- (6; 7; 8-trichloro-4-quinolinyl) -lH- pyrazole-4-carboxylate;

1 - (7-chloro-4-quinolinyl) -N-methyl-5- {[(1 -methylethy l) oxy] methyl} -N- (methyloxy) - 1 H-pyrazole-4-carboxamide; methyl 3 - [(methyloxy) methyl] -5- (2-thienyl) -l- [8- (trifluoromethyl) -4- quinolinyl] - 1 H-pyrazole-4-carboxylate;

7-chloro-4- (5 - [(methyloxy) methyl] -4- {3 - [(methyloxy) methyl] -l; 2; 4- oxadiazol-5-yl} -l H-pyrazol- 1 -yl) quinoline;

[1- (7-chloro-4-quinolinyl) -4- (1; 3-thiazol-2-yl) -1H-pyrazol-5-yl] methyl methyl ether;

[1- (7-chloro-4-quinolinyl) -4- (4; 5-dihydro-1; 3-thiazol-2-yl) -lH-pyrazol-5-yl] methyl methyl ether; 1; 1 -dimethylethyl 1 - (7-chloro-4-quinolinyl) -5 - [(methy loxy) methyl] - 1 H-pyrazole-4-carboxylate; l- (7-cyano-4-quinolinyl) -N-methyl-N- (methyloxy) -5 - [(methyloxy) methyl] - 1H-pyrazole-4-carboxamide;

[4- [5- (bromomethyl) -3-isoxazolyl] -1- (7-bromo-4-quinolinyl) -1H-pyrazol-5-yl] methyl methyl ether; l- (7-chloro-4-quinolinyl) -N'-methyl-5 - [(methyloxy) methyl] -N'-phenyl-1H-pyrazole-4-carbohydrazide;

1 - (7-chloro-4-quinolinyl) -N '- (2; 5-dichlorophenyl) -5 - [(methyloxy) methyl] - 1H-pyrazole-4-carbohydrazide; l- (7-chloro-4-quinolinyl) -N '- (l; l-dimethylethyl) -5 - [(methyloxy) methyl] - 1H-pyrazole-4-carbohydrazide;

(1 - (7-chloro-4-quinolinyl) -4- {[methyl (methy loxy) amino] carbony 1} - 1 H-pyrazol-5-yl) methyl 2-methylpropanoate;

N-ethyl-1- (6-fluoro-4-quinolinyl) -N-methyl-5 - [(methyloxy) methyl] -1H-pyrazole-4-carboxamide; 1- (7-chloro-4-quinolinyl) -N- (cyclopropylmethyl) -N-methyl-5- [(methyloxy) methyl] -1 H-pyrazole-4-carboxamide;

3- {l- (7-chloro-4-quinolinyl) -5 - [(methyloxy) methyl] -lH-pyrazol-4-yl} - 4; 6-dimethyl-4H-l; 2; 4-oxadiazin-5 (6H) -one;

N- (4-chloro-2-butynyl) -1- (7-chloro-4-quinolinyl) -5 - [(methyloxy) methyl] -1H-pyrazole-4-carboxamide; methyl 1- (7-chloro-4-quinolinyl) -5- (methyloxy) -1H-pyrazole-4-carboxylate; 1- (7-chloro-4-quinolinyl) -5- (ethylsulfanyl) -N-methyl-N- (methyloxy) -1H-pyrazole-4-carboxamide; 1- (7-chloro-4-quinolinyl) -5 - [(methyloxy) methyl] -N- (4-morpholinyl) -1H-pyrazole-4-carboxamide;

1 - (7-chloro-4-quinolinyl) -N-methyl-N- (methyloxy) -5- (methylsulfanyl) - 1 H-pyrazole-4-carboxamide;

(1 - (7-chloro-4-quinolinyl) -4- {[methyl (methyloxy) amino] carbonyl} - 1 H-pyrazol-5-yl) methyl cyclopropanecarboxylate;

(1 - (7-chloro-4-quinolinyl) -4- {[methyl (methyloxy) amino] carbonyl} - 1 H-pyrazol-5-yl) methyl 2-thienylacetate;

7-chloro-4- (5 - [(methyloxy) methyl] -4- {1- [3- (methyloxy) propyl] -lH-imidazol-5-yl} - 1 H-pyrazol-1 -yl) quinoline;

[1 - (7-chloro-4-quinolinyl) -4- (1 -methyl- 1 H-imidazol-5-yl) - 1 H-pyrazol-5- yljmethyl methyl ether;

{1 - (7-chloro-4-quinolinyl) -5 - [(methyloxy) methyl] - 1 H-pyrazol-4- yl} [(trimethylsilyl) oxy] acetonitrile;

[1 - (7-bromo-4-quinolinyl) -4- (1 -piperidinylcarbonyl) - 1 H-pyrazol-5-yljmethyl methyl ether; methyl {4- (1-piperidinylcarbonyl) -l- [7- (trifluoromethyl) -4-quinolinyl] -lH- pyrazol-5-yl} methyl ether;

5 -amino- 1 - (7-chloro-4-quinolinyl) - 1 H-pyrazole-4-carbonitrile;

3- {1- (7-chloro-4-quinolinyl) -5 - [(methyloxy) methyl] -1H-pyrazol-4-yl} -2-thiophenecarbaldehyde;

[1- (7-chloro-4-quinolinyl) -4- (5-ethenyl-l; 3-oxazol-2-yl) -lH-pyrazol-5-yl] methyl methyl ether; 1- (2- {1- (7-chloro-4-quinolinyl) -5 - [(methyloxy) methyl] -1H-pyrazol-4-yl} - 1; 3-oxazol-5-yl) ethyl acetate;

[1- (7-bromo-4-quinolinyl) -4- (2-isoxazolidinylcarbonyl) -1H-pyrazol-5-yl] methyl methyl ether;

{4- (2-isoxazolidinylcarbonyl) -l- [7- (trifluoromethyl) -4-quinolinyl] -H-pyrazol-5-yl} methyl methyl ether;

[1- (7-ethyl-4-quinolinyl) -4- (2-isoxazolidinylcarbonyl) -1H-pyrazol-5-yl] methyl methyl ether;

[1 - (6-fluoro-4-quinolinyl) -4- (2-isoxazolidinylcarbonyl) - 1 H-pyrazol-5-yl] methyl methyl ether;

N '- (2-chlorophenyl) -1- (7-chloro-4-quinolinyl) -5 - [(methyloxy) methyl] -1H-pyrazole-4-carbohydrazide;

1 - (7-chloro-4-quinolinyl) -N '- (2; 4-dichloroρhenyl) -5 - [(methyloxy) methyl] - 1 H-pyrazole-4-carbohydrazide;

1 - (7-chloro-4-quinolinyl) -N '- (2; 6-dichlorophenyl) -5 - [(methyloxy) methyl] - 1H-pyrazole-4-carbohydrazide; 1- (7-chloro-4-quinolinyl) -5 - [(methyloxy) methyl] -N '- (3-methylphenyl) -1H-pyrazole-4-carbohydrazide;

N '- (3-chlorophenyl) -1- (7-chloro-4-quinolinyl) -5 - [(methyloxy) methyl] -1H-pyrazole-4-carbohydrazide;

N '- (3-chloro-4-methylphenyl) -l- (7-chloro-4-quinolinyl) -5- [(methyloxy) methyl] - 1 H-pyrazole-4-carbohydrazide; l- (7-chloro-4-quinolinyl) -N '- (3; 4-dichlorophenyl) -5 - [(methyloxy) methyl] - 1H-pyrazole-4-carbohydrazide;

1 - (7-chloro-4-quinolinyl) -N '- (4-cyanophenyl) -5 - [(methyloxy) methyl] - 1 H- pyrazole-4-carbohydrazide;

(3- {1- (7-chloro-4-quinolinyl) -5 - [(methyloxy) methyl] -1H-pyrazol-4-yl} -5- isoxazolyl) methyl phenyl sulfone;

(3- {1- (7-chloro-4-quinolinyl) -5 - [(methyloxy) methyl] -1H-pyrazol-4-yl} -5- isoxazolyl) methyl ethyl sulfoxide;

[4- (4-chlorophenyl) - 1 - (7-chloro-4-quinolinyl) - 1 H-pyrazol-5 -yljmethyl methyl ether;

1 - {1 - (7-chloro-4-quinoliny l) -5- [(methyloxy) methyl] - 1 H-pyrazol-4-yl} -3 - phenyl-2-propyn-l-one;

N - ({l- (7-chloro-4-quinolinyl) -5 - [(methyloxy) methyl] -lH-pyrazol-4- yl} methyl) -3- (methyloxy) -l-propanamine,

as well as their possible tautomeric forms, their salts, N-oxides and metal and metalloid complexes.

Among the compounds of formula (I) as they have just been defined, a group of particularly advantageous compounds consists of the compounds of general formula (IV):

cas particulier des composés de formule (I) pour lesquels R₃ représente l'hydrogène et R, et R₂ sont respectivement en position 4 et 5 du noyau pyrazole, R₂, Y,, Y₂, Y₃, Y₄, Y₅ et Y₆ étant tels que définis précédemment, et R, représente un groupe carboxy, carbamoyle, N-alkylcarbamoyle, N,N- dialkylcarbamoyle, N-alkyl,N-alkoxyalkylcarbamoyle, N-alkoxycarbamoyle, N- alkyl-N-aminoalkylcarbamoyle, N,N-diaminoalkylcarbamoyle, alkoxycarbonyle inférieur; un nitrile, un groupe acyle inférieur.

special case of the compounds of formula (I) for which R ₃ represents hydrogen and R, and R ₂ are respectively in position 4 and 5 of the pyrazole ring, R ₂ , Y ,, Y ₂ , Y ₃ , Y ₄ , Y ₅ and Y ₆ being as defined above, and R represents a carboxy, carbamoyl, N-alkylcarbamoyl, N, N-dialkylcarbamoyl, N-alkyl, N-alkoxyalkylcarbamoyl, N-alkoxycarbamoyl, N-alkyl-N-aminoalkylcarbamoyl group, N, N-diaminoalkylcarbamoyl, lower alkoxycarbonyl; a nitrile, a lower acyl group.

The compounds of general formulas (I) and (IV) as well as the compounds which may be used as intermediates in the preparation processes, and which will be defined when describing these processes, may exist under one or more forms of optical or chiral isomers depending on the number of asymmetric centers of the compound. The invention therefore relates to all optical isomers as well as their racemic or scalemic mixtures (scalemic is a mixture of enantiomers in different proportions), as well as mixtures of all possible stereoisomers in all proportions. The separation of diastereoisomers and / or optical isomers can be carried out according to methods known per se (E.Eliel ibid.).

The preparation of the reagents used in one or other of the following preparation methods, is usually known per se and is usually described specifically in the prior art or in such a way that the man of the art can adapt it to the desired goal.

The prior art which can be used by those skilled in the art to establish the conditions for the preparation of the reagents, can be found in numerous general works of chemistry such as "Advanced Organic Chemistry" by J. March, Ed. Wiley (1992),

"Methoden der organischen Chemie" (Houben-Weyl), Ed. Georg Thieme Verlag or the "Chemical Abstracts" Ed. American Chemical Society as well as in computer databases accessible to the public.

The compounds of the present invention of general formulas (I) and (IV) as well as the compounds which may be used as intermediates in the preparation processes, can be prepared according to the following process:

composés de formules (I), (II) et (III), dans lesquelles X représente un halogène et R„ R₂, R₃, Y,, Y₂, Y₃, Y₄, Y₅ et Y₆ sont tels que définis précédemment,

compounds of formulas (I), (II) and (III), in which X represents a halogen and R „R ₂ , R ₃ , Y ,, Y ₂ , Y ₃ , Y ₄ , Y ₅ and Y ₆ are such that previously defined,

the reaction being carried out in the presence of an organic or inorganic base, in the absence or in the presence of a solvent.

This reaction is generally carried out at a temperature between -80 ° C and 180 ° C (preferably between 0 ° C and 150 ° C) or at the boiling point of the solvent used. The suitable solvent for this reaction can be an aliphatic hydrocarbon such as pentane, hexane, heptane, octane; an aromatic hydrocarbon such as benzene, toluene, xylenes, halobenzenes; an ether such as diethyl ether, diisopropyl ether, tetrahydrofuran, dioxane, dimethoxyethane; a halogenated hydrocarbon such as dichloromethane, chloroform, 1,2-dichloroethane, 1,1,1-trichloroethane; an ester such as methyl acetate, ethyl acetate, a nitrile such as acetonitrile, propionitrile, benzonitrile; a dipolar aprotic solvent such as dimethylformamide, dimethylacetamide, N-methylpyrrolidone, dimethylprolyleneurea, dimethylsulfoxide, or water. Mixtures of these different solvents can also be used.

The reaction time depends on the conditions used and is generally between 0.1 to 48 h.

There is no strict limitation on the relative proportions of the compounds of formula (II) and of formula (III). It is however advantageous to choose a molar ratio (III) / (II) of between 0.1 and 10, preferably 0.5 to 2. As the organic or inorganic base suitable for this reaction, mention may be made of hydroxides alkali and alkaline earth metals such as sodium, potassium, cesium or calcium hydroxide; alkali and alkaline earth metal alcoholates such as potassium tert-butoxide, alkali and alkaline earth metal hydrides such as sodium, potassium or cesium hydride; carbonates and bicarbonates of alkali and alkaline earth metals such as sodium, potassium, calcium carbonate or sodium, potassium or calcium bicarbonate; organic bases, preferably nitrogenous, such as pyridine, alkylpyridines, alkylamines such as trimethylamine, triethylamine or di-isopropylethylamine, aza derivatives such as 1,5-diazabicyclo [4.3.0] non-5-ene or l, 8-diazabicyclo [5.4.0] undec-7-ene, phosphazenes such as l-terbutyl-2,2,4,4,4-pentakis- (dimethylamino) -2λ ⁵ , 4λ ⁵ - catenadi (phosphazene ).

For references on this reaction, we can cite: Advances in Heterocyclic Chemistry, Volume 6, pages 414-416, for a very general reference on the preparation of the compounds of formula (III), we can cite Houben-Weyl, band E8b , Hetarene III, Teil 2 pages 408-704, for the compounds of formula (II) may be cited: Tetrahedron (1985) 41, 3033-3036 and Organic Synthesis, Col. Flight. 3, 272 (1955).

The compounds of formula (IV)

cas particulier des composés de formule (I) pour lesquels R₃ représente l'hydrogène et R, et R₂ sont respectivement en position 4 et 5 du noyau pyrazole, R₂, Y„ Y₂, Y₃, Y₄, Y₅ et Y₆ étant tels que définis précédemment, et R, représente un groupe carboxy, carbamoyle, N-alkylcarbamoyle, N,N- dialkylcarbamoyle, N-alkyl,N-alkoxyalkylcarbamoyle, N-alkoxycarbamoyle, N- alkyl-N-aminoalkylcarbamoyle, N,N-diaminoalkylcarbamoyle, alkoxycarbonyle inférieur; un nitrile, un groupe acyle inférieur, peuvent avantageusement être préparés selon la réaction suivante (cf. Houben-Weyl, band E8b, Hetarene III, Teil 2 pages 450-472) :

special case of the compounds of formula (I) for which R ₃ represents hydrogen and R, and R ₂ are respectively in position 4 and 5 of the pyrazole ring, R ₂ , Y „Y ₂ , Y ₃ , Y ₄ , Y ₅ and Y ₆ being as defined above, and R represents a carboxy, carbamoyl, N-alkylcarbamoyl, N, N-dialkylcarbamoyl, N-alkyl, N-alkoxyalkylcarbamoyl, N-alkoxycarbamoyl, N-alkyl-N-aminoalkylcarbamoyl, N group , N-diaminoalkylcarbamoyl, lower alkoxycarbonyl; a nitrile, a lower acyl group, can advantageously be prepared according to the following reaction (cf. Houben-Weyl, band E8b, Hetarene III, Teil 2 pages 450-472):

where X 'represents a halogen atom, N, N-dialkylamino or alkoxy, R ,, R ₂ and Y, with Y ₆ being as defined for the compounds of formula (IV) above.

The compounds of formula (VII) can advantageously be prepared from the compounds of formula (II) defined above by reaction with hydrazine according to conventional techniques known to those skilled in the art. Once the construction of the pyrazole is complete, conventional transformations can be made on the functional groups of the substituents as described in numerous general works of chemistry such as "Advanced Organic Chemistry" by J. March, Ed. Wiley (1992), " Methoden der organischen Chemie "(Houben-Weyl), Ed. Georg Thieme Verlag or the" Chemical Abstracts "Ed. American Chemical Society as well as in computer databases accessible to the public or more precisely on pyrazoles as described in Houben -Weyl, band E8b, Hetarene III, Teil 2 pages 580-656.

The invention also relates to fungicidal compositions comprising an effective amount of at least one active material of formula (I).

The fungicidal compositions according to the invention comprise a compound of formula (I) or of formula (IV) or a salt thereof acceptable in agriculture or a metal or metalloid complex of this compound, in combination with a solid or liquid support, acceptable in agriculture and / or a surfactant also acceptable in agriculture. In particular, the usual inert supports and the usual surfactants can be used. These compositions cover not only the compositions 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 the concentrated commercial compositions which must be diluted before application to Culture.

These fungicidal compositions according to the invention can also contain all kinds of other ingredients such as, for example, protective colloids, adhesives, thickeners, thixotropic agents, penetration agents, stabilizers, sequestrants, etc. More generally, the active ingredients can be combined with any solid or liquid additive corresponding to the usual techniques of formulation.

In general, the compositions according to the invention usually contain from 0.05 to 95% (by weight) of active material, one or more solid or liquid supports and, optionally, one or more surfactants.

By the term "support", in the present description, is meant an organic or mineral, natural or synthetic material, with which the active material is combined to facilitate its application on the parts of the plant. This support is therefore generally inert and it must be acceptable in agriculture. The support can be solid (clays, natural or synthetic silicates, silica, resins, waxes, solid fertilizers, etc.) or liquid (water, alcohols, in particular butanol etc.).

The surfactant can be an emulsifying, dispersing or wetting agent of ionic or nonionic type or a mixture of such surfactants. Mention may be made, for example, of salts of polyacrylic acids, salts of lignosulfonic acids, salts of phenolsulfonic or naphthalene sulfonic acids, polycondensates of ethylene oxide on fatty alcohols or on fatty acids or on fatty amines , substituted phenols (in particular alkylphenols or arylphenols), ester salts of sulfosuccinic acids, taurine derivatives (in particular alkyltaurates), phosphoric esters of polyoxyethylated alcohols or phenols, esters of acids fatty acids and polyols, the derivatives containing sulfates, sulfonates and phosphates of the preceding compounds. The presence of at least one surfactant is generally essential when the active material and / or the inert support are not soluble in water and the vector agent for the application is water.

Thus, the compositions for agricultural use according to the invention can contain the active material within very wide limits, ranging from 0.05% to 95% (by weight). Their surfactant content is advantageously between 5% and 40% by weight. Unless otherwise indicated, the percentages given in this description are percentages by weight.

These compositions according to the invention are themselves in fairly diverse forms, solid or liquid.

As forms of solid compositions, mention may be made of powders for dusting (with active material content of up to 100%) and granules, in particular those obtained by extrusion, by compacting, by impregnation of a granulated support, by granulation from a powder (the active material content in these granules being between 0.5 and 80% for the latter cases).

The fungicidal compositions according to the invention can also be used in the form of powders for dusting; one can also use compositions comprising 50 g of active material and 950 g of talc; one can also use compositions comprising 20 g of active material, 10 g of finely divided silica and 970 g of talc; these constituents are mixed and ground and the mixture is applied by dusting.

As forms of liquid compositions or intended to constitute liquid compositions during application, there may be mentioned solutions, in particular water-soluble concentrates, emulsions, concentrated suspensions, wettable powders (or spray powder).

The concentrated suspensions, applicable in spraying, are prepared so as to obtain a stable fluid product which does not deposit and they usually contain from 10 to 75% of active material, from 0.5 to 15% of surfactants, 0.1 to 10% of thixotropic agents, 0 to 10% of suitable additives, such as defoamers, corrosion inhibitors, stabilizers, penetrating agents and adhesives and, as support, water or an organic liquid in which the active ingredient is sparingly or not very soluble: certain organic solids or mineral salts can be dissolved in the support to help prevent sedimentation or as antifreeze for water.

As an example, here is a concentrated suspension composition:

Example SC 1:

- active ingredient 500 g

- polyethoxylated tristyrylphenol phosphate 50 g - polyethoxylated alkylphenol 50 g

- sodium polycarboxylate 20 g

- ethylene glycol 50 g

- organopolysiloxane oil (antifoam) 1 g

- polysaccharide 1.5 g - water 316.5 g

Wettable powders (or spray powder) are usually prepared so that they contain 20 to 95% of active material, and they usually contain, in addition to the solid support, from 0 to 30% of an agent wetting, from 3 to 20% of a dispersing agent, and, when necessary, from 0.1 to 10% of one or more stabilizers and / or other additives, such as penetrating agents, adhesives, or anti-caking agents, dyes, etc.

To obtain the sprayable powders or wettable powders, the active ingredients are intimately mixed in the appropriate mixers with the additional substances and ground with mills or other suitable grinders. This gives sprayable powders whose wettability and suspension are advantageous; they can be suspended with water at any concentration desired and these suspensions can be used very advantageously in particular for application for example on the leaves of plants or on seeds.

As an example, here are various compositions of wettable powders (or spray powders):

Example PM 1

- active ingredient 50%

- ethoxylated fatty alcohol (wetting agent) 2.5% - ethoxylated phenylethylphenol (dispersing agent) 5%

- chalk (inert support) 42.5%

Example PM 2:

- active material 10% - branched type oxo synthetic alcohol, in Cl 3 ethoxylated with 8 to 10 ethylene oxide

(wetting agent) 0.75%

- neutral calcium lignosulfonate (dispersing agent) 12%

- calcium carbonate (inert filler) q.s.p. 100%

Example PM 3:

This wettable powder contains the same ingredients as in the previous example, in the proportions below:

- active ingredient 75%

- wetting agent 1.50% - dispersing agent 8%

- calcium carbonate (inert filler) q.s.p. 100%

Example PM 4:

- active ingredient 90% - ethoxylated fatty alcohol (wetting agent) 4%

- ethoxylated phenylethylphenol (dispersing agent) 6%

Example PM 5:

- active ingredient 50% - mixture of anionic and nonionic surfactants (wetting agent) 2.5%

- sodium lignosulfonate (dispersing agent) 5%

- kaolin clay (inert support) 42.5% Aqueous dispersions and emulsions, for example the compositions obtained by diluting a wettable powder according to the invention with water, are included in the general scope of the present invention. The emulsions can be of the water-in-oil or oil-in-water type and they can have a thick consistency like that of a "mayonnaise".

The fungicidal compositions according to the invention can be formulated in the form of water dispersible granules also included in the context of the invention.

These dispersible granules, of apparent density generally comprised between approximately 0.3 and 0.6 have a particle size generally comprised between approximately 150 and 2000 and preferably between 300 and 1500 microns.

The active material content of these granules is generally between approximately 1% and 90%, and preferably between 25% and 90%.

The rest of the granule is essentially composed of a solid filler and optionally surfactant additives giving the granule properties of dispersibility in water. These granules can be essentially of two distinct types depending on whether the selected filler is soluble or not in water. When the filler is water-soluble, it can be mineral or, preferably, organic. Excellent results have been obtained with urea. In the case of an insoluble filler, it is preferably mineral, such as for example kaolin or bentonite. It is then advantageously accompanied by surfactants (at a rate of 2 to 20% by weight of the granule) of which more than half is, for example, constituted by at least one dispersing agent, essentially anionic, such as a polynaphthalene alkaline or alkaline earth sulfonate or an alkaline or alkaline earth lignosulfonate, the remainder being nonionic or anionic wetting agents such as an alkali or alkaline earth alkyl naphthalene sulfonate. Furthermore, although this is not essential, other adjuvants can be added such as anti-foaming agents.

The granule according to the invention can be prepared by mixing the necessary ingredients then granulation according to several techniques known per se (bezel, fluid bed, atomizer, extrusion, etc.). It generally ends with a crushing followed by sieving to the particle size chosen within the limits mentioned above. It is also possible to use granules obtained as above and then impregnated with a composition containing the active material. Preferably, it is obtained by extrusion, operating as indicated in the examples below.

Example GDI: Dispersible granules In a mixer, 90% by weight of active material and 10% urea in beads are mixed. The mixture is then ground in a pin mill. A powder is obtained which is moistened with approximately 8% by weight of water. The wet powder is extruded in a perforated roller extruder. A granule is obtained which is dried, then crushed and sieved, so as to keep respectively only the granules of a size between 150 and 2000 microns.

Example GD2: Dispersible granules

In a mixer, the following constituents are mixed:

- active ingredient 75% - wetting agent (sodium alkylnaphthalene sulfonate) 2%

- dispersing agent (sodium polynaphthalene sulfonate) 8%

- inert filler insoluble in water (kaolin) 15%

This mixture is granulated in a fluid bed, in the presence of water, then dried, crushed and sieved so as to obtain granules of size between 0.15 and 0.80 mm.

These granules can be used alone, in solution or dispersion in water so as to obtain the desired dose. They can also be used to prepare combinations with other active materials, in particular fungicides, the latter being in the form of wettable powders, or aqueous granules or suspensions.

The compounds of the invention can also be mixed with one or more insecticides, fungicides, bactericides, acaricides, arthropodicides, nematocides, attractants or pheromones or other compounds with biological activity. The mixtures thus obtained have a broad spectrum activity. Mixtures with other fungicides are particularly advantageous, for example mixtures with fungicides of the triazole family, derivatives of strobilurin etc. The compounds of the present invention can advantageously be used in combination with azoxystrobin, kresoxym-methyl, discostrobin, carbendazim, thiram, diethofencarb, dodine, maneb, mancozeb, diflumetorim, ethirimol, benomyl, cymoxanil, fenpropidine, fenpropimorph, triadimefon, captane, captafol, folpel, thiophanate, thiabendazole, phosphoric acid and its derivatives such as phosetyl-Al, chlorothalonil, copper fungicidal compositions, dichloran, metalaxyl, iprodione, fenamidone, oxadixyl, vinchlozoline, tebuconazole, bromuconazole, triticonazole, difenconazole, diniconazole, metconazole, penconazole, propiconazole, prochloraz, fenarimol, triadimen copper derivatives such as hydroxide and oxychloride, probenazole, epoxyconazole, famoxadone, picoxystrobin, fludioxonyl, pyrimethanil, mepanipyrim, cyprodinyl, quinoxyfen, ferimzone, fluazinam, trifloxystrobin, dimethomorph, benalaxyl, blasticidin-S, fluquinconazole, tricyclazole, fluzilazole, valinamide derivatives, such as for example iprovalicarb, flutolanil, guazatin, hexaconazole, hymexazol , isoprothiolane, kazugamycin, pencycuron, phthalide, pyroquilon, tetraconazole, thifluzamide and carboxin.

The compositions according to the invention are also useful for treating seeds, for example cereals (wheat, rye, triticale and barley in particular), potato, cotton, peas, rapeseed, corn, flax or even the seeds of forest trees (especially conifers). It will be noted in this connection that in the jargon of a person skilled in the art, the term seed treatment actually refers to the treatment of seeds. The application techniques are well known to those skilled in the art and they can be used without disadvantage in the context of the present invention. Mention may be made, for example, of film-coating or coating.

It has been discovered quite surprisingly that the compounds of formula (I) according to the invention are fungicidal compounds active on a very wide range of phytopathogenic fungi in cultures. This activity was revealed during preventive treatments, but also during curative treatments. In addition, this activity has been shown to be very interesting even when using low doses of compounds of formula (I).

Quite surprisingly for compounds having such activity (broad spectrum of action and low doses used), these compounds of formula (I) are not or very weakly phytotoxic. That is to say that they have a very good selectivity with respect to the treated plants.

Finally, the compounds of formula (I) have a very favorable behavior with regard to the environment in the sense that they are not or very weakly ecotoxic. Thus, the invention also relates to a method of combating, for curative or preventive purposes, against phytopathogenic fungi of crops, characterized in that the seeds, leaves or trunks of plants or the soils where are likely to grow these plants are treated by application, spraying or injection of an effective (agronomically effective) and non-phytotoxic amount of an active material of formula (I) or one of its acceptable salts in agriculture or a metallic or metalloid complex of this compound also acceptable in agriculture, preferably in the form of a fungicidal composition according to the invention.

By "effective and non-phytotoxic amount" means an amount of composition according to the invention sufficient to allow the control or destruction of fungi present or likely to appear on crops, and resulting in said cultures no notable symptom of phytotoxicity. Such an amount is likely to vary within wide limits depending on the fungus to be combated, the type of crop, the climatic conditions, and the compounds included in the fungicidal composition according to the invention. This quantity can be determined by systematic field tests, within the reach of those skilled in the art.

The dose of composition applied is, in general, advantageously such that the dose of active material is between 2 and 200 g of active material per 100 kg of seed, preferably between 3 and 150 g per 100 kg in the case of seed treatments.

In the case of plant treatments, doses of 10 to 800 g / ha, preferably 50 to 300 g / ha are generally applied as a foliar treatment. It should be understood that these doses are given purely by way of illustration for the purposes of the present invention.

Thus, a person skilled in the art will be able to evaluate the precise doses of active materials to be applied, according to the nature and the degree of development of the cultures, according to the nature of the diseases to be eradicated and their stage of infestation, as well as edaphic and climatic conditions present in the field at the time or before or after the treatment (s).

Similarly, the number and frequency of treatments may vary according to the same criteria mentioned above. Thus, a person skilled in the art will see fit to carry out one or more treatments in a preventive manner, that is to say before the appearance of diseases, associated or not with one or more curative treatments, intended to eradicate the diseases already appeared.

The invention finally relates to a method of protection for preventive or curative of plant propagation products, as well as plants resulting therefrom, against fungal diseases, characterized in that said products are covered with a dose effective and non-phytotoxic of a composition according to the invention.

Among the multiplication products of the plants concerned, mention may in particular be made of seeds or seeds, and tubers.

As indicated above, the procedures for recovering plant propagating products, in particular seeds, are well known in the art and make use in particular of film-coating or coating techniques.

The products and compositions according to the invention can also be applied as a foliar application on plant crops.

Among the plants targeted by the method according to the invention, there may be mentioned as non-limiting examples:

- wheat, as regards the fight against the following seed diseases: fusarium wilt (Microdochium nivale and Fusarium roseum), caries (Tilletia caries, Tilletia controversa or Tilletia indica), septoria leaf spot (Septoria nodorum);

- wheat, with regard to the fight against the following diseases of the aerial parts of the plant: foot rot (Pseudocercosporella herpotrichoïdes), foot scald (Gaeumannomyces graminis), fusarium wilt (F. culmorum, F. graminearum), Fusarium head blight (F. culmorum, F. graminearum, Microdochium nivale), helminthosporiosis (Pyrenophora tritici-repentis) rhizoctone (Rhizoctonia cerealis), powdery mildew (Erysiphe graminis forma specie tritici), rust Puccinia striiformis and Puccinia recondita) and septoria (Septoria tritici and Septoria nodorum); :

- wheat and barley, as regards the fight against bacterial and viral diseases, for example the dwarfing jaundice of barley.

- barley, with regard to the control of the following seed diseases: helminthosporioses (Pyrenophora graminea, Pyrenophora teres and Cochliobolus sativus), naked smut (Ustilago nuda) and fusarium wilt (Microdochium nivale and Fusarium roseum), - barley, with regard to the fight against the following diseases of the aerial parts of the plant: foot rot (Pseudocercosporella herpotrichoïdes), helminthosporioses (Pyrenophora teres and Cochliobolus sativus), powdery mildew (Erysiphe graminis forma specie hordei), dwarf rust (Puccinia hordei) and rhynchosporiosis (Rhynchosporium secalis);

- potato, as regards the fight against tubercle diseases (in particular Helminthosporium solani, Phoma tuberosa, Rhizoctonia solani, Fusarium solani)), downy mildew (Phytopthora infestons) and certain viral diseases (virus Y);

- the potato with regard to the fight against the following foliage diseases: alternaria (Alternaria solani), downy mildew (Phytophthora infestons);

- cotton, with regard to the fight against the following diseases of young plants grown from seed: seedlings and necrosis of the crown (Rhizoctonia solani, Fusarium oxysporum), black root rot (Thielaviopsis basicola);

- protein crops, for example peas, as regards the fight against the following seed diseases: anthracnose (Ascochyta pisi, Mycosphaerella pinodes), fusarium wilt (Fusarium oxysporum), gray mold (Botrytis cinered), downy mildew (Peronospora pisi);

- oil crops, for example rapeseed, as regards the control of the following seed diseases: Phoma lingam alternaria brassicae; Sclerotinia sclerotiorum,

- maize, as regards the fight against seed diseases: (Rhizopus sp., Penicillium sp., Trichoderma sp., Aspergillus sp. and Gibberella fujikuroï);

- flax, as regards the fight against seed disease: Alternaria linicola;

- forest trees, with regard to the control of seedling huts (Fusarium oxysporum, Rhizoctonia solani). - vegetable crops with regard to the fight against the following diseases of seedlings or young plants derived from seeds: seedlings and neck necrosis (Fusarium oxysporum, Fusarium roseum, Rhizoctonia solani, Pythium sp.)

- vegetable crops with regard to the control of the following diseases of the aerial parts: gray mold (Botrytis sp.), powdery mildew

(in particular Erysiphe cichoracearum, Sphaerotheca fuliginea, Leveillula laurica), fusarioses (Fusarium oxysporum, Fusarium roseum), cladosporioses (Cladosporium sp.), alternarioses (Alternaria sp.), anthracnoses (Colletotrichum sp;), septoria sp.), rhizoctonia (Rhizoctonia solani), downy mildew (e.g. Bremia lactucae, Perosonospora sp., Pseudoperonospora sp, Phytophthora sp).

- fruit trees with regard to diseases of the aerial parts: moniliosis (Monilia fructigenά), scab (Venturia inaequalis), powdery mildew (Sphaerothecafructigena)

- the vine with regard to diseases of the foliage: in particular gray rot (Botrytis cinerea), powdery mildew (Uncinula necator), black-rot (Guignardia biwelli), downy mildew (Plasmopara vitivola)

- beet for the following diseases of the aerial parts: Sigatoka (Cercospora beticola), powdery mildew (Erysiphe beticola), ramulariasis (Ramularia beticola)

Wheat and barley are the preferred plants for the implementation of the method according to the invention.

The present invention also relates to the treatment of genetically modified plants with the compounds according to the invention or the agrochemical compositions according to the invention. Genetically modified plants are plants in the genome of which a heterologous gene coding for a protein of interest has been stably integrated.

By heterologous gene coding for a protein of interest is essentially meant according to the invention the genes conferring on the transformed plant new agronomic properties, or the genes for improving the agronomic quality of the transformed plant.

Among the genes conferring new agronomic properties on transformed plants, there may be mentioned the genes conferring tolerance to certain herbicides, those conferring resistance to certain insects, those conferring tolerance to certain diseases, etc. Such genes are described in particular in patent applications WO 91/02071 and WO 95/06128.

Among the genes conferring tolerance to certain herbicides, mention may be made of the Bar gene conferring tolerance to bialaphos, the gene coding for an appropriate EPSPS conferring resistance to herbicides having EPSPS as target such as glyphosate and its salts ( US 4,535,060, US 4,769,061, US 5,094,945, US 4,940,835, US 5,188,642, US 4,971,908, US 5,145,783, US 5,310,667, US 5,312,910, US 5,627,061, US 5,633,435, FR 2,736,926), the gene encoding glyphosate 5,4 , or a gene coding for a HPPD conferring tolerance to herbicides targeting HPPD such as isoxazoles, in particular isoxafutole (FR 95 06800, FR 95 13570), diketonitriles (EP 496 630, EP 496 631) or triketones, in particular sulcotrione (EP 625 505, EP 625 508, US 5,506,195). Such genes coding for HPPD conferring tolerance to herbicides targeting HPPD are described in patent application WO 96/38567.

In the case of genes coding for EPSPS or HPPD, and more particularly for the above genes, the sequence coding for these enzymes is advantageously preceded by a sequence coding for a transit peptide, in particular for the transit peptide called peptide of optimized transit described in US patents 5,510,471 or US 5,633,448.

Among the genes conferring new insect resistance properties, there will be mentioned more particularly the genes coding for the Bt proteins widely described in the literature and well known to those skilled in the art. Mention will also be made of the genes coding for proteins extracted from bacteria such as Photorabdus (WO 97/17432 & WO 98/08932).

Among the genes conferring new disease resistance properties, mention will be made in particular of the genes coding for chitinases, glucanases, oxalate oxidase, all these proteins and their coding sequences being widely described in the literature, or also the genes encoding antibacterial and / or antifungal peptides, in particular peptides of less than 100 amino acids rich in cysteines such as thionines or plant defensins, and more particularly lytic peptides of all origins comprising one or more disulfide bridges between cysteines and regions comprising basic amino acids, in particular the following lytic peptides: androctonine (WO 97/30082 and PCT / FR98 / 01814, deposited on August 18, 1998) or drosomicine (PCT / FR98 / 01462, deposited on July 8

1998). Mention will also be made of the genes coding for fungal eliciting peptides, in particular elicitins (Kamoun & al., 1993; Panabières & al., 1995).

Among the genes modifying the constitution of modified plants, mention may be made in particular of genes modifying the content and quality of certain essential fatty acids (EP 666 918) or also the content and quality of proteins, in particular in leaves and / or seeds of said plants. Mention will in particular be made of the genes coding for proteins enriched in sulfur amino acids (Korit, AA & al., Eur. J. Biochem. (1991) 195, 329-334; WO 98/20133; WO 97/41239; WO 95 / 31554; The present invention relates more particularly to the treatment of genetically modified plants comprising a heterologous gene conferring on the plant properties of resistance to diseases. Preferably, the heterologous gene confers on the genetically modified plant a spectrum of activity complementary to the spectrum of activity of the compounds according to the invention.

By complementary spectrum is meant according to the invention an activity spectrum for the heterologous gene distinct from the activity spectrum of the compounds according to the invention, or an activity spectrum relating to identical infectious agents but allowing identical control or improved for lower doses of application of compounds according to the invention.

The following table illustrates in a nonlimiting manner a few examples of fungicidal compounds according to the invention (the various compounds were analyzed by mass spectrometry; the "Observed mass" column provides the mass + 1 or the mass -1 of the peak molecular observed):

u u

> *

D σ

O

-01 oo m o m oo co co co

u where

X. X. X.

σ> o N o lO m -n

The procedures presented below illustrate methods of preparing some of these compounds.

It is understood that the methods which follow are directly transposable to the synthesis of all of the compounds of the present invention. In addition, other synthetic routes, easily accessible to those skilled in the art, can be used to access the compounds of the invention.

Example 1: Preparation of Compound No. 11

Preparation of methyl 3- (methoxymethyl) - 1 - [8- (trifluoromethyl) -4-quinolyl] - 1H-pyrazole-4-carboxylate. Step 1 :

50 g of methyl 4-methoxy-3-oxobutanoate are dissolved in 500 ml of toluene, then 77.3 g of N, N-dimethylformamide dimethyl acetal are added and the mixture is heated at 90 ° C. for 5 hours while distilling off using a Dean-Stark the methanol that forms. The reaction medium is then evaporated under vacuum and the crude methyl 3- (dimethylamino) -2 (2-methoxyacetyl) -2-propenoate obtained as is used is used. Step 2: 40 g of methyl 3- (dimethylamino) -2 (2-methoxyacetyl) -2-propenoate are dissolved in 100 ml of acetic acid and 9.6 ml of hydrazine are added slowly. Then heated for 3 hours at 90 ° C. The mixture is allowed to return to room temperature, 11 liters of water are added and the acetic acid is neutralized by gently pouring potassium bicarbonate until the end of the gaseous evolution. Then extracted with ethyl acetate, washing the organic phase with water. It is then dried over magnesium sulfate and evaporated to obtain 28.7 g of methyl 5- (methoxymethyl) -1H-pyrazole-4-carboxylate in the form of a brown solid which is used as it is by the following. Step 3: 5.7 g of methyl 5- (methoxymethyl) -1H-pyrazole-4-carboxylate are dissolved in 60 ml of dimethylformamide and 17 ml of a 2M solution of 1-terbutyl-2,2 are added, 4,4,4-pentakis- (dimethylamino) -2λ ⁵ , 4λ ⁵ -catenadi (phosphazene) in tetrahydrofuran. The solution is stirred for 10 minutes and then 7.74 g of 4-chloro-8-trifluoromethylquinoline are added and the mixture is heated for 4 hours at 70 ° C. The reaction mixture is then allowed to return to room temperature, extracted with ethyl acetate, the organic phase is washed with a saturated solution of lithium chloride and then with water. The organic phase is dried over magnesium sulfate, evaporated and the crude product obtained is purified by flash chromatography with successively 15 then 30 then 40% ethyl acetate in heptane to obtain 8 g of a beige solid. This product can be recrystallized from diisopropyl ether to obtain methyl 3- (methoxymethyl) -1- [8- (trifluoromethyl) -4-quinolyl] -1H-pyrazole-4-carboxylate in the form of a white solid. F = 138 ° C (this expression denotes the melting point)

Example 2: Preparation of compound n ° 6

Preparation of methyl 1 - (7-chloro-4-quinolyl) -5- (methoxymethyl) -1H-pyrazole-4-carboxylate 15 g of 3- (dimethylamino) -2 (2-methoxyacetyl) -2-propenoate are dissolved of methyl in 100 ml of acetic acid and 14.4 g of 7-chloro-4-hydrazinoquinoline are added and the mixture is heated to 90 ° C. After one hour, the mixture is allowed to return to ambient temperature and an additional 100 ml of acetic acid are added. The mixture is further heated for 3 hours at 90 ° C. then allowed to return to ambient temperature, poured into 11 of water and then filters the brown precipitate which forms. Heptane is added to the precipitate, the solvents are evaporated and 15.7 g of a beige solid are obtained. Mp 123 ° C.

Example 3; Preparation of Compound No. 61 Preparation of 1- (7-chloro-4-quinolyl) -N, N-diethyl-5- (methoxymethyl) -1H-pyrazole- 4-carboxamide

To a suspension of 6.6 ml of Ν, Ν-diethylamine in 70 ml of 1,2-dichloroethane, 425 ml of a 2M solution of trimethylaluminum in hexane is slowly added at 0 ° C and then stirred at room temperature for 20 minutes. Then 7g of methyl 1- (7-chloro-4-quinolyl) -5- (methoxymethyl) -1H-pyrazole-4-carboxylate are added and the reaction mixture is heated at 75 ° C for 20 hours. The mixture is cooled to 0 ° C and gently hydrolyzed with a 1 molar hydrochloric acid solution until the evolution of gas is completed and extracted with dichloromethane. After drying and evaporation of the organic phase, 6.84 g of a brown oil are obtained which is purified by flash chromatography with an eluent of 70/30 ethyl acetate / heptane then 100% ethyl acetate to obtain 3.1 g of a solid brown. M = 1 14 ° C.

Examples of Biological Activities of the Compounds of the Invention

Example A: In vivo test on Septoria nodorum (wheat septoria): An aqueous suspension, with a concentration of 2 g / 1, of the active ingredient tested is obtained by fine grinding thereof in the following mixture:

- water,

- Tween 80 surfactant (oleate of polyoxyethylene derivative of sorbitan) diluted to 10% in water: 5 ml / mg of active material,

- clay: inert support qs 100%.

This aqueous suspension is then diluted with water so as to obtain the desired concentration of active material. Wheat plants (Scipion variety) in pots, sown on a 50/50 peat soil-pozzolan substrate and cultivated at 12 ° C., are treated at the 1 leaf stage (10 cm in height) by spraying with the aqueous suspension described above. above.

Plants, used as controls, are treated with an aqueous solution not containing the active ingredient. After 24 hours, the plants are contaminated by spraying with an aqueous suspension of spores (500,000 spores per cm ³ ) of Septoria nodorum. The spores are harvested from a seven-day-old culture.

Contaminated wheat plants are incubated for 72 hours at around 18 ° C, in a humid atmosphere, then for 14 days at 90% relative humidity. The grading is carried out 15 to 20 days after the contamination, in comparison with the control plants.

Under these conditions, at the dose of 500 g / ha, good (at least 50%) or total protection is observed with the compounds described in Examples 11, 135, 136, 287, and 387.

Example B: In vivo test on Erisyphe graminis f. sp. tritici (wheat powdery mildew):

An aqueous suspension, with a concentration of 2 g / 1, of the active ingredient tested is obtained by fine grinding thereof in the following mixture: - water

- Tween 80 surfactant (oleate of polyoxyethylene derivative of sorbitan) diluted to 10% in water: 5 ml / mg of active ingredient

- clay: inert support qs 100%.

This aqueous suspension is then diluted with water so as to obtain the desired concentration of active material.

Wheat plants (Audace variety) in pots, sown on a 50/50 peat soil-puzzolan substrate and cultivated at 12 ° C, are treated at the 1 leaf stage (10 cm height) by spraying the aqueous suspension described above. Plants, used as controls are treated with an aqueous solution not containing the active ingredient.

After 24 hours, the plants are contaminated by dusting with spores of Erisyphe graminis f. sp. tritici, dusting being carried out using diseased plants.

Scoring is carried out 7 to 14 days after contamination, in comparison with the control plants.

Under these conditions, at the dose of 500 g / ha, good (at least 50%) or total protection is observed with the compounds described in examples 6, 11, 61, 67, 136, 163, 170, 215, 217 and 430.

Example C: In vivo test on Erisyphe graminis f. sp. hordei (barley powdery mildew):

An aqueous suspension, with a concentration of 2 g / 1, of the active ingredient tested is obtained by fine grinding thereof in the following mixture:

- water

- Tween 80 surfactant (oleate of polyoxyethylene derivative of sorbitan) diluted to 10% in water: 5 ml / mg of active material - clay: inert support qs 100%.

This aqueous suspension is then diluted with water so as to obtain the desired concentration of active material.

Barley plants (Express variety) in pots, sown on a 50/50 peat earth-pozzolan substrate and cultivated at 12 ° C, are treated at the 1 leaf stage (10 cm in height) by spraying with the aqueous suspension described above -above.

Plants, used as controls are treated with an aqueous solution not containing the active ingredient.

After 24 hours, the plants are contaminated by dusting with spores of Erisyphe graminis f. sp. hordei, dusting being carried out using diseased plants.

Scoring is carried out 7 to 14 days after contamination, in comparison with the control plants.

Under these conditions, at the dose of 500 g / ha, good (at least 50%) or total protection is observed with the compounds described in examples 1 1, 41, 61, 67, 91, 1 19, 163, 170 , 215, 217, 306, 310 and 430.

Example D: In vivo test on Puccinia recondita (brown wheat rust): An aqueous suspension, with a concentration of 2 g / 1, of the active ingredient tested is obtained by fine grinding thereof in the following mixture:

- water - Tween 80 surfactant (oleate of polyoxyethylene derivative of sorbitan) diluted to 10% in water: 5 ml / mg of active ingredient

- clay: inert support qs 100%.

This aqueous suspension is then diluted with water so as to obtain the desired concentration of active material. Wheat plants (Scipion variety) in pots, sown on a 50/50 peat soil-pozzolan substrate and cultivated at 12 ° C., are treated at the 1 leaf stage (10 cm in height) by spraying with the aqueous suspension described above. above.

Plants, used as controls are treated with an aqueous solution not containing the active ingredient. After 24 hours, the plants are contaminated by spraying with an aqueous suspension of spores (100,000 spores per cm ³ ) of Puccinia recondita. Spores are harvested from diseased plants.

Contaminated wheat plants are incubated for 24 hours at around 18 ° C, in a humid atmosphere, then for 7 to 14 days at 60% relative humidity. The grading is carried out 8 to 15 days after the contamination, in comparison with the control plants.

Under these conditions, at the dose of 500 g / ha, good (at least 50%) or total protection is observed with the compounds described in Examples 11, 88, 119, 136 and 155.

Example E: In vivo test on Pyrenophora teres (barley helminthosporiosis):

An aqueous suspension, with a concentration of 2 g / 1, of the active ingredient tested is obtained by fine grinding thereof in the following mixture: - water

- Tween 80 surfactant (oleate of polyoxyethylene derivative of sorbitan) diluted to 10% in water: 5 ml / mg of active ingredient

- clay: inert support qs 100%.

This aqueous suspension is then diluted with water so as to obtain the desired concentration of active material.

Barley plants (Express variety) in pots, sown on a 50/50 peat soil-pozzolan substrate and cultivated at 12 ° C, are treated at the 1 leaf stage (10 cm height) by spraying the aqueous suspension described above.

Plants, used as controls are treated with an aqueous solution not containing the active ingredient.

After 24 hours, the plants are contaminated by spraying with an aqueous suspension of spores (10,000 spores per cm ³ ) of Pyrenophora teres. The spores are harvested from a 10 day old culture.

Contaminated barley plants are incubated for 24 hours at around 18 ° C, in a humid atmosphere, then for 7 to 14 days at 80% relative humidity.

The grading is carried out 8 to 15 days after the contamination, in comparison with the control plants.

Under these conditions, at the dose of 500 g / ha, good (at least 50%) or total protection is observed with the compounds described in examples 11, 41, 61, 1 19,

136, 155, 163, 170 and 430.

Example F: Curative in vivo test on Erisyphe graminis f. sp. tritici (wheat powdery mildew):

Wheat plants (Audace variety) in pots, sown on a 50/50 peat earth-pozzolan substrate and cultivated at 12 ° C, are contaminated at the 1 leaf stage (10 cm high) by dusting with spores of Erisyphe graminis f. sp. tritici, dusting being carried out using diseased plants.

An aqueous suspension, with a concentration of 2 g / 1, of the active ingredient tested is obtained by fine grinding thereof in the following mixture:

- water

- Tween 80 surfactant (oleate of polyoxyethylene derivative of sorbitan) diluted to 10% in water: 5 ml / mg of active ingredient

- clay: inert support qs 100%.

This aqueous suspension is then diluted with water so as to obtain the desired concentration of active material.

Contaminated wheat plants (Audace variety) are treated 48, 72 and 96 hours after contamination by spraying with the aqueous suspension described above.

Plants, used as controls are treated with an aqueous solution not containing the active ingredient.

Scoring is carried out 7 to 14 days after contamination, in comparison with the control plants. Under these conditions, at the dose of 500 g / ha, good (at least 50%) or total protection is observed with the compound described in Example 67. Example G: In vivo test on Erisyphe graminis f. sp. tritici (wheat powdery mildew):

An aqueous suspension, with a concentration of 2 g / 1, of the active ingredient tested is obtained by fine grinding thereof in the following mixture: - water

- specific mixture based on Soprophor BS4, cyclohexanone, N-methyl pyrolidone and N-octyl pyrolidone at a rate of 100 μl for 10 mg of active ingredient.

This aqueous suspension is then diluted with water so as to obtain the desired concentration of active material. Wheat plants (Audace variety) in pots, sown on a 50/50 peat soil-pozzolan substrate and cultivated at 12 ° C, are treated at the 1 leaf stage (10 cm in height) by spraying with the aqueous suspension described above. above.

Plants, used as controls are treated with an aqueous solution not containing the active ingredient. After 24 hours, the plants are contaminated by dusting with spores of

Erysiphe graminis f. sp. tritici, dusting being carried out using diseased plants.

Scoring is carried out 7 to 14 days after contamination, in comparison with the control plants. Under these conditions, at the dose of 250 g / ha, good (at least 50%) or total protection is observed with the compounds described in examples 31, 34, 41, 43, 53, 78, 93, 94, 101 , 738.

Example H: In vivo test on Erysiphe graminis s f. sp. hordei (barley powdery mildew)

An aqueous suspension, with a concentration of 2 g / 1, of the active ingredient tested is obtained by fine grinding thereof in the following mixture:

- water

- specific mixture based on Soprophor BS4, cyclohexanone, N-methyl pyrolidone and N-octyl pyrolidone at a rate of 100 μl for 10 mg of active ingredient.

This aqueous suspension is then diluted with water so as to obtain the desired concentration of active material.

Barley plants (Express variety) in pots, sown on a 50/50 peat earth-pozzolan substrate and cultivated at 12 ° C, are treated at the 1 leaf stage (10 cm in height) by spraying with the aqueous suspension described above -above.

Plants, used as controls are treated with an aqueous solution not containing the active ingredient.

After 24 hours, the plants are contaminated by dusting with spores of Erysiphe graminis f. sp. hordei, dusting being carried out using diseased plants.

Scoring is carried out 7 to 14 days after contamination, in comparison with the control plants.

Under these conditions, at the dose of 250 g / ha, good (at least 50%) or total protection is observed with the compounds described in examples 31, 34, 41, 43, 53,

78, 93, 94, 101, 738.

Example I: Curative in vivo test on Erysiphe graminis f. sp. tritici (wheat powdery mildew):

Wheat plants (Audace variety) in pots, sown on a 50/50 peat earth-pozzolan substrate and cultivated at 12 ° C, are contaminated at the 1 leaf stage (10 cm in height) by dusting with spores of Erysiphe graminis f . sp. tritici, dusting being carried out using diseased plants. An aqueous suspension, with a concentration of 2 g / 1, of the active ingredient tested is obtained by fine grinding thereof in the following mixture:

- water

- specific mixture based on Soprophor BS4, cyclohexanone, N-methyl pyrolidone and N-octyl pyrolidone at a rate of 100 μl for 10 mg of active ingredient. This aqueous suspension is then diluted with water so as to obtain the desired concentration of active material.

Contaminated wheat plants (Audace variety) are treated 48 hours after contamination by spraying the aqueous suspension described above.

Plants, used as controls are treated with an aqueous solution not containing the active ingredient.

Scoring is carried out 7 to 14 days after contamination, in comparison with the control plants.

Under these conditions, at the dose of 250 g / ha, good (at least 50%) or total protection is observed with the compound described in examples 31, 34, 67.

Example J: In vivo test on Uncinula necator (powdery mildew)

An aqueous suspension, with a concentration of 2 g / 1, of the active ingredient tested is obtained by fine grinding thereof in the following mixture: - water

- specific mixture based on Soprophor BS4, cyclohexanone, N-methyl pyrolidone and N-octyl pyrolidone at a rate of 100 μl for 10 mg of active ingredient. This aqueous suspension is then diluted with water so as to obtain the desired concentration of active ingredient.

Vine plants (Chardonnay variety) in pots are treated at the 5-6 leaf stage (6 weeks after cuttings) by spraying the aqueous suspension described above. Plants, used as controls are treated with an aqueous solution not containing the active ingredient.

After 24 hours, the plants are contaminated by dusting with spores of Uncinula necator, the dusting being carried out using diseased plants. The grading is carried out 30 days after contamination, in comparison with the control plants.

Under these conditions, at the dose of 250 g / ha, good (at least 50%) or total protection is observed with the compounds described in the examples Examples 31, 34, 43, 67.

Example K: In vivo test on Sphaerotheca fuliginea (powdery mildew of cucurbits):

An aqueous suspension, with a concentration of 2 g / 1, of the active ingredient tested is obtained by fine grinding thereof in the following mixture:

- water - specific mixture based on Soprophor BS4, cyclohexanone, N-methyl pyrolidone and N-octyl pyrolidone at a rate of 100 μl for 10 mg of active ingredient.

This aqueous suspension is then diluted with water so as to obtain the desired concentration of active material.

Cucumbers (Marketer variety) in pots are treated at the 2-leaf spread stage by spraying the aqueous suspension described above.

Plants, used as controls are treated with an aqueous solution not containing the active ingredient.

After 24 hours, the plants are contaminated by dusting with spores

Sphaerotheca fuliginea, dusting being carried out using diseased plants. Scoring is carried out 3 weeks after contamination, in comparison with the control plants.

Under these conditions, at the dose of 250 g / ha, good (at least 50%) or total protection is observed with the compounds described in examples 31, 34, 41, 67.

Example L: In vivo test on Venturia inaequalis (apple scab):

An aqueous suspension, of concentration 2 g / 1, of the active ingredient tested is obtained by fine grinding thereof in the following mixture:

- water

- specific mixture based on Soprophor BS4, cyclohexanone, N-methyl pyrolidone and N-octyl pyrolidone at a rate of 100 μl for 10 mg of active ingredient. This aqueous suspension is then diluted with water so as to obtain the desired concentration of active material.

Apple trees (Golden variety) in pots are treated at the 5-6 leaf stage (4 to 6 weeks after sowing) by spraying with the aqueous suspension described above.

Plants, used as controls are treated with an aqueous solution not containing the active ingredient.

After 24 hours, the plants are contaminated with an aqueous solution of Venturia inaequalis (suspension at 150,000 spores / ml).

The grading is carried out 15 to 20 days after the contamination, in comparison with the control plants. Under these conditions, at the dose of 250 g / ha, good (at least 50%) or total protection is observed with the compounds described in Examples 31, 34 and 67.

Claims

Compounds of general formula (I)

in which : • R and R ₂ are different and are chosen from an alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkoxysulfonyl, alkenyl, alkynyl, alkenyloxy, alkynyloxy, alkenylthio, alkynylthio, cycloalkyl, heterocyclyl, cycloalkylalkyl, alkylcarbonylcarbonyl radical alkynylcarbonyl, alkylcarbonyloxy, alkénylcarbonyloxy, alkynylcarbonyloxy, alkoxycarbonyl, alkoxyalkylcarbonyle, alkenyloxycarbonyl, alkynyloxycarbonyl, cycloalkyl-carbonyl, heterocyclylcarbonylaminoalkyl, cycloalkyl-oxycarbonyl, cycloalkylalkyloxycarbonyl, heterocyclyl-oxycarbonyl, hétérocyclylalkoxycarbonyle, thioalkylthiocarbonyle, alkoxythiocarbonyle, thioalkyl, aryl, heteroaryl, arylcarbonyl, heteroarylcarbonyl, the hydroxy radical, the mercapto radical, the carboxy radical, the nitro radical, the cyano radical, the thiocyanato radical, the azido radical, a NR ₄ R ₅ , C (= O) NR ₄ R ₅ , C (= S) radical NR ₄ R ₅ , a radical C (= NR ₄ ) R ₅ , a halog atom ene, the sulfonyl radical, the sulfinyl radical, the sulfanyl radical, the phosphoryl radical and the phosphone radical, or R, and R ₂ can together form a ring of 4 to 7 atoms, containing 2 to 3 atoms of oxygen and / or nitrogen, optionally substituted by one or more radicals chosen from halogen, alkyl, haloalkyl, alkoxy, amino and NR ₄ R ₅ ; • R ₃ is chosen from hydrogen, an alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkoxysulfonyl, alkenyl, alkynyl, alkenyloxy, alkynyloxy, alkenylthio, alkynylthio, cycloalkyl, heterocyclyl, cycloalkylcarbonyl, heterocycylalkylalkylcarbonyl, alkyl alkenylcarbonyl, alkynylcarbonyl, alkylcarbonyloxy, alkénylcarbonyloxy, alkynylcarbonyloxy, alkoxycarbonyl, alkenyloxycarbonyl, alkynyloxycarbonyl, cycloalkyl-oxycarbonyl, cycloalkylalkyloxycarbonyl, heterocyclyl-oxycarbonyl, heterocyclylalkoxy-carbonyl, aryl, heteroaryl, arylcarbonyl, heteroarylcarbonyl, hydroxyl radical, the mercapto radical, the radical carboxy, the nitro radical, the cyano radical, the thiocyanato radical, the azido radical, a radical NR ₄ R ₅ , C (= O) NR ₄ R ₅ , C (= S) NR ₄ R ₅ and a radical C (= NR ₄ ) R ₅ , • R ₄ and R ₅ , identical or different, are chosen from hydrogen, an alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkoxysulfonyl, alkenyl, alkynyl, alkenyloxy, alkynyloxy, alkenylthio, alkynylthio, cyanoalkyl, alkoxyalkyl, alkoxycarbonylalkyl cycloalkyl, heterocyclyl, cycloalkylalkyl, heterocyclylalkyl, alkylcarbonyl, alkenylcarbonyl, alkynylcarbonyl, alkoxycarbonyl, alkenyloxycarbonyl, alkynyloxycarbonyl, cycloalkyloxycarbonyl, cycloalkylalkyloxycarbonyl, heterocyclyloxycarbonyl, hétérocyclylalkoxycarbonyle, aryl, heteroaryl, arylcarbonyl, heteroarylcarbonyl, arylalkyl, heteroarylalkyl, the mercapto radical, the carboxy radical, the nitro radical, the cyano radical, the thiocyanato radical, the azido radical, an OR _é radical, amino, alkylamino, dialkylamino, aminoalkyl, alkylaminoalkyl and dialkylaminoalkyl, hydrazino, or R ₄ and R5 can together form a ring of 4 to 7 atoms, containing 2 to 3 atoms of oxygen and / or nitrogen, optionally substituted by one or more radicals chosen from halogen, alkyl, haloalkyl, alkoxy, amino and NR ₇ R ₈ ; • R ^ represents hydrogen, an alkyl, aryl, heteroaryl, arylalkyl radical, hetertoarylalkyl, cycloalkyl, cycloalkylalkyl, heterocyclyl, heterocyclyalkyl and alkoxycarbonylalkyle, • R ₇ and R _g , identical or different, are chosen from hydrogen, an alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkoxysulfonyl, alkenyl, alkynyl, alkenyloxy, alkynyloxy, alkenylthio, alkynylthio, cyanoalkyl, alkoxyalkyl, alkoxycarbonylalkyl cycloalkyl, heterocyclyl, cycloalkylalkyl, heterocyclylalkyl, alkylcarbonyl, alkenylcarbonyl, alkynylcarbonyl, alkoxycarbonyl, alkenyloxycarbonyl, alkynyloxycarbonyl, cycloalkyloxycarbonyl, cycloalkylalkyloxycarbonyl, heterocyclyloxycarbonyl, hétérocyclylalkoxycarbonyle, aryl, heteroaryl, arylcarbonyl, heteroarylcarbonyl, arylalkyl, heteroarylalkyl, the mercapto radical, the carboxy radical, the nitro radical, the cyano radical, the thiocyanato radical, the azido radical, an OR radical ;, amino, alkylamino, dialkylamino, aminoalkyl, alkylaminoalkyl and dialkylaminoalkyl, hydrazino, or, R ₇ and R ₈ can together form a ring of 4 to 7 atoms, containing 2 to 3 atoms of oxygen and / or nitrogen, optionally substituted by one or more radicals chosen from halogen, alkyl, haloalkyl, alkoxy and amino; • the radicals Y ,, Y ₂ , Y ₃ , Y ₄ , Y ₅ and Y ₆ are chosen independently of each other from the hydrogen atom, a halogen atom; the hydroxy, mercapto, nitro, thiocyanato, azido, cyano or pentafluorosulfonyl radical, an alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkoxyalkyl, haloalkoxyalkyl, alkylthioalkyl, haloalkylthioalkyl, cyanoalkyl, cyanoalkylalkylalkylalkyl, alkylalkyl, alkylalkyl, alkylalkyl, alkylalkyl, alkylalkyl, alkylalkyl, cyanoalkyl, alkyl, alkyl haloalkylsulfonyl, alkoxysulfonyl, a cycloalkyl, halocycloalkyl, alkenyl, alkynyl, alkenyloxy, alkynyloxy, alkenylthio, alkynylthio group, an optionally substituted aryl or heteroaryl radical, an amino, N-alkylamino, N, N-dialkylamino, acylamino, aminoalkyl, N-alkylaminoalkyl radical, N, N-dialkylaminoalkyl, acylaminoalkyl, the carboxy radical, the carbamoyl radical, an N-alkylcarbamoyl, N, N-dialkylcarbamoyl, alkoxycarbonyl and an alkylcarbonyl radical, or two adjacent radicals chosen from Y „Y ₂ , Y ₃ , Y ₄ , Y ₅ and Y ₆ can also form, together and with the two carbon atoms which carry them, a 6-membered aromatic ring, or two adjacent radicals chosen from Y ,, Y ₂ , Y ₃ , Y ₄ , Y ₅ and Y ₆ can also together form a divalent methylene-di-oxy radical; • all of the radicals defined above and having a hydrocarbon chain (alkyl, alkoxy, cycloalkyl, heterocycloalkyl, alkenyl, alkynyl, etc.) may optionally be substituted by one or more groups or radicals, identical or different, chosen from hydroxy , mercapto, NR ₄ R ₅ , cyano, nitro, alkyl, alkoxyalkyl, aryl, heteroaryl, halogen, alkoxy, alkylthio, alkylcarbonyl, alkylcarbonyloxy, alkenylcarbonyl, alkenylcarbonyloxy, alkynylcarbonyl, alkynylcarbonyloxy, arylcarbonyl, arylcarbonyloxycarbonyl arylcarbonyloxycarbonylarbonyloxycarbonylarbonyloxy heteroaryloxy, heteroarylthio, haloalkoxy, perhaloalkoxy, cyanoalkylcarbonyloxy, cycloalkyl, heterocyclyl, cycloalkylcarbonyl, cycloalkylcarbonyloxy, heterocyclyloxycarbonoxycarbonoxycarbonyloxycarbonyloxycarbonyloxycarbonyloxycarbonyloxycarbonyloxycarbonyloxycarbonyloxy kylcarbonyloxy and alkylthioalkylcarbonyloxy, • all of the aryl and heteroaryl radicals defined above may optionally be substituted by one or more groups or radicals, identical or different, chosen from hydroxy, mercapto, oxo, cyano, nitro, cyanato, thiocyanato, formyl, propylene-diyl , amino, alkylamino, dialkylamino, pentafluorosulfonyl, aryl, heteroaryl, halogen, alkyl, haloalkyl, perhaloalkyl, alkenyl, alkynyl, alkoxy, alkylthio, haloalkoxy, perhaloalkoxy, alkoxyalkyl, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxycarbonyl, alkylcarbonyloxy , arylcarbonyloxy, heteroarylcarbonyl, heteroarylcarbonyloxy, aryloxy, arylthio, heteroaryloxy, heteroarylthio, cycloalkyl, heterocyclyl, cycloalkylcarbonyl and heterocyclylcarbonyl, their possible geometric and / or optical isomers, their possible tautomeric forms, as well as the salts, N-oxides and the metal and metalloid complexes of the compounds of formula (I) as they have just been defined _Λ with the exception of the following compounds: trans - (+/-) - 6- [2- [l- (9-acridinyl) -5- (4-fluorophenyl) -3- (l-methylethyl) - lH-pyrazol-4-yl ] ethyl] tetrahydro-4-hydroxy-2H-pyran-2-one; trans - (+/-) - 6- [2- [l- (9-acridinyl) -5- (4-fluorophenyl) -3- (l-methylethyl) - 1 H-pyrazol-4-yl] ethenyl] tetrahydro-4-hydroxy-2H-pyran-2-one; • 3-methyl-1- (4-methylquinolin-2-yl) -5-trifluoromethylpyrazole; 3-trifluoromethyl- 1 - (4-methylquinolin-2-yl) -5-trifluoromethylpyrazole; 3-phenyl-1- (4-methylquinolin-2-yl) -5-trifluoromethylpyrazole; 3- (2-thienyl) - 1 - (4-methylquinolin-2-yl) -5-trifluoromethylpyrazole; 1 - (methy 1-quinolin-4-yl) -3 -methy 1-5 -trifluoromethylpyrazoles; • l- (trifluoromethyl-quinolin-4-yl) -3-methyl-5-trifluoromethylpyrazoles; 1- (phenyl-quinolin-4-yl) -3-methyl-5-trifluoromethylpyrazoles; 1 - [(2-thienyl) -quinolin-4-yl] -3-methyl-5-trifluoromethylpyrazoles; endo- 1 - (7-chloro-4-quinolinyl) -5-methyl-N- (9-azabicyclo [3,3,1] non-3 -yl) - 1H-pyrazole-3-carboxamide; • 5-amino-1- (7-chloro-4-quinolinyl) -1H-pyrazole-4-carbonitrile; 4-acetyl-1- (7-chloro-4-quinolinyl) -5-methyl-1H-pyrazole; 5-methyl-1- (4-quinolinyl) -1H-pyrazole-4-carboxylic acid; 5-cyclopropyl- 1 - (4-quinolinyl) - 1H-pyrazole-4-carboxylic acid. 2. Compounds according to claim 1 having one and / or the other of the following characteristics taken individually or in combination: • R and R ₂ are different and are chosen from an alkyl, alkoxyalkyl, alkylthioalkylke, hydroxyalkyl, aminoalkoxyalkyl, N- alkylaminoalkoxyalkyl, N, N-dialkylaminoalkoxyalkyl, aminoalkyl-thioalkyl, N-alkylaminoalkyl-thioalkyl, N, N-dialkylamylalkyl radical alkenyl, cycloalkyl, cycloalkylcarbonyl, heterocyclylcarbonyl, heterocyclyl, cycloalkylalkyl, heterocyclylalkyl, alkylcarbonyl, alkylcarbonyloxy, alkylcarbonyloxyalkyl, alkenylcarbonyloxyalkyl, alkynylcarbonyloxyalkyl, alkoxycarbonyl an aryl, heteroaryl, arylalkyl, heteroarylalkyl, aryloxyalkyl, heteroaryloxyalkyl, arylcarbonyl, heteroarylcarbonyl, arylcarbonyl- radical oxyalkyl, heteroarylcarbonyloxyalkyle, hydroxy radical, carboxy radical, nitro radical, cyano radical, NR ₄ R ₅ , CH ₂ NR ₄ R ₅ , C (= O) NR ₄ R ₅ , and a C (= NR ₄ ) R ₅ , R ₃ is chosen from hydrogen, an alkyl, alkoxy, alkoxyalkyl, alkylthio, alkenyl, alkynyl, cycloalkyl, heterocyclyl, cycloalkylalkyl, heterocyclylalkyl, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, hydroxy radical, mercapto radical, carboxy radical, and a radical NR ₄ R ₅ , • R ₄ and R ₅ , identical or different, are chosen from hydrogen, an alkyl, alkoxy, alkoxyalkyl, alkylthio, alkenyl, alkynyl, alkenyloxy, alkynyloxy, cyanoalkyl, alkoxyalkyl, alkoxycarbonylalkyl, cycloalkyl, heterocyclyl, cycloalkylalkyl, heterocyclylalkyl alkylcarbonyl, alkoxycarbonyl, an aryl, heteroaryl, arylalkyl, heteroarylalkyl radical, mercapto radical, cyano radical, OR _< ; radical, amino, alkylamino, dialkylamino, aminoalkyl, alkylaminoalkyl and dialkylaminoalkyl, R ^ represents hydrogen, an alkyl, aryl, heteroaryl, arylalkyl, hetertoarylalkyl, cycloalkyl, cycloalkylalkyl, heterocyclyl, heterocyclyalkyl, and alkoxycarbonylalkyl radical, • the radicals Y ,, Y ₂ , Y ₃ , Y ₄ , Y ₅ and Y ₆ are chosen independently of one another from the hydrogen atom, a halogen atom, the hydroxy, mercapto, nitro, cyano radical or pentafluorosulfonyl, an alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkoxyalkyl, haloalkoxyalkyl, cyanoalkyl, cyanoalkoxy, cyanoalkylthio radical, an alkenyl, alkynyl, alkenyloxy, alkynyloxy, alkenylthio, alkynyl, alkyl , N-dialkylamino, aminoalkyl, N-alkylaminoalkyl, N, N-dialkylaminoalkyl, the carboxy radical, alkoxycarbonyl and an alkylcarbonyl radical, or two adjacent radicals chosen from Y ,, Y ₂ , Y ₃ , Y ₄ , Y ₅ and Y ₆ can also form, together and with the two carbon atoms which bear, a 6-link aromatic cycle, • all of the radicals defined above and having a hydrocarbon chain (alkyl, alkoxy, cycloalkyl, heterocycloalkyl, alkenyl, alkynyl, etc.) may optionally be substituted by one or more groups or radicals, identical or different, chosen from hydroxy , mercapto, amino, N-alkylamino, N, N-dialkylamino, cyano, nitro, aryl, heteroaryl, halogen, alkoxy, alkylthio, aryloxy, arylthio, heteroaryloxy, heteroarylthio, haloalkoxy, perhaloalkoxy, cyanoalkylcarbonylcycloalkyl , cycloalkylcarbonyloxy, heterocyclylcarbonyl, heterocyclylcarbonyloxy, aryloxyalkylcarbonyloxy, alkylcarbonylalkylcarbonyloxy, alkoxycarbonylalkylcarbonyloxy, arylcarbonylcarbonyloxy, heteroarylcarbonylcarbonyloxy, alkoxyalkoxyalkylcarbonyloxycarbonyloxy • all of the aryl and heteroaryl radicals defined above may optionally be substituted by one or more groups or radicals, identical or different, chosen from oxo, cyano, nitro, formyl, propylene-diyl, amino, N-alkylamino, N , N-dialkylamino, aryl, heteroaryl, halogen, alkyl, haloalkyl, perhaloalkyl, alkoxy, alkylthio, haloalkoxy, perhaloalkoxy, alkoxyalkyl, alkylcarbonyl, alkoxycarbonyl, aryloxy, cycloalkyl and heterocyclyl, their possible geometric and / or optical isomers, their possible tautomeric forms, as well as the salts, N-oxides and the metallic and metalloid complexes of these compounds. 3. Compounds according to one of the preceding claims, having one and / or the other of the following characteristics, taken individually or in combination: • R, and R ₂ are different and are chosen from an alkyl, alkoxyalkyl, alkylthioalkylke, hydroxyalkyl, aminoalkoxyalkyle, N-alkylaminoalkoxyalkyle, N, N-dialkylaminoalkoxyalkyle, aminoalkyl-thioalkyle, N-alkylaminoalkyl-thioalkyl, N, N-dialkylaminoalkyl radical alkenyl, cycloalkylcarbonyl, heterocyclylcarbonyl, cycloalkylalkyl, heterocyclylalkyl, alkylcarbonyl, alkylcarbonyloxy, alkylcarbonyloxyalkyl, alkoxycarbonyl, cycloalkylalkoxycarbonyle, aryl, heteroaryl, arylalkyl, heteroarylalkyl, aryloxyalkyl, heteroaryloxyalkyl, arylcarbonyl, heteroarylcarbonyl, carboxy radical, a radical NR ₄ R _5, CH ₂ NR ₄ R _5, C (= O) NR ₄ R ₅ , and a radical C (= NR ₄ ) R ₅ , R ₃ is chosen from hydrogen, an alkyl, alkoxy, alkoxyalkyl, alkylthio, cycloalkyl, heterocyclyl, cycloalkylalkyl, heterocyclylalkyl, alkoxycarbonyl, carboxy radical, and a radical NR ₄ R ₅ , • R ₄ and R ₅ , which may be identical or different, are chosen from hydrogen, an alkyl, alkoxy, alkoxyalkyl, alkoxyalkyl, alkoxycarbonylalkyl, cycloalkyl, heterocyclyl, cycloalkylalkyl, heterocyclylalkyl radical, an aryl, heteroaryl, arylalkyl, heteroarylalkyl radical and radical OR _é , R ^ represents hydrogen, an aryl, heteroaryl, arylalkyl, hetertoarylalkyl, cycloalkyl, cycloalkylalkyl, heterocyclyl, and heterocyclyalkyl radical, • the radicals Y ,, Y ₂ , Y ₃ , Y ₄ , Y ₅ and Y ₆ are chosen independently of one another from the hydrogen atom, a halogen atom, the hydroxy radical, an alkyl or haloalkyl radical , alkoxy, haloalkoxy, alkoxyalkyle and haloalkoxyalkyle, • all of the radicals defined above and having a hydrocarbon chain (alkyl, alkoxy, cycloalkyl, heterocycloalkyl, alkenyl, alkynyl, etc.) may optionally be substituted by one or more groups or radicals, identical or different, chosen from hydroxy , halogen, alkoxy and haloalkoxy, • all of the aryl and heteroaryl radicals defined above may optionally be substituted by one or more groups or radicals, identical or different, chosen from oxo, halogen, alkyl, haloalkyl, perhaloalkyl, alkoxy, haloalkoxy, perhaloalkoxy, alkoxyalkyl, alkylcarbonyl , alkoxycarbonyl and aryloxy, their possible geometric and or optical isomers, their possible tautomeric forms, as well as the salts, N-oxides and the metallic and metalloid complexes of these compounds. 4, Compounds according to one of the preceding claims, having one and / or the other of the following characteristics, taken individually or in combination: • R, and R ₂ are different and are chosen from an alkyl, alkoxyalkyl, hydroxyalkyl, cycloalkylcarbonyl, heterocyclylcarbonyl, alkylcarbonyl, alkylcarbonyloxy, alkylcarbonyloxyalkyl, alkoxycarbonyl, cycloalkylalkoxycarbonyl, aryl, heteroaryl, arylalkyl, heteroalkyl, arylalkylalkyl, hydroxyalkyl, arylalkyl, hydroxyalkyl, alkyl group carboxy and a radical C (= O) NR ₄ R ₅ , • R ₃ represents hydrogen, R ₄ and R ₅ , identical or different, are chosen from hydrogen, an alkyl, alkoxy and alkoxycarbonylalkyl radical, The radicals Y ,, Y ₂ , Y ₃ , Y ₄ , Y ₅ and Y ₆ are chosen independently of one another from the hydrogen atom, a halogen atom, an alkyl, haloalkyl and alkoxy radical, • all of the radicals defined above and having a hydrocarbon chain (alkyl, alkoxy, cycloalkyl, heterocycloalkyl, alkenyl, alkynyl, etc.) may optionally be substituted by one or more groups or radicals, identical or different, chosen from hydroxy , halogen, alkoxy and haloalkoxy, All of the aryl and heteroaryl radicals defined above may optionally be substituted by one or more groups or radicals, identical or different, chosen from oxo, halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, perhaloalkoxy and alkoxycarbonyl, their possible geometric and / or optical isomers, their possible tautomeric forms, as well as the salts, N-oxides and the metal and metalloid complexes of these compounds. 5. Compounds according to one of the preceding claims, chosen from the 1 - (7-chloro-4-quinolyl) -5- (methoxymethyl) -1 methyl H-pyrazole-4-carboxylate; Methyl 3- (methoxymethyl) -1- [8- (trifluoromethyl) -4-quinolyl] -1H-pyrazole-4-carboxylate; 1 - (7-chloro-4-quinolyl) -5- (3-nitrophenyl) - 1 H-pyrazole-4-carboxylate methyl; 1- (7-chloro-4-quinolyl) -N, N-diethyl-5- (methoxymethyl) -1H-pyrazole-4-carboxamide; 1 - (7-chloro-4-quinolyl) -N-methoxy-5- (methoxymethyl) -N-methyl-1 H-pyrazole-4-carboxamide; methyl 1- (7-chloro-4-quinolyl) -5- (2-methoxyethyl) -1H-pyrazole-4-carboxylate; Methyl 5- (2-methoxyethyl) -1- (7-methoxy-4-quinolyl) -1H-pyrazole-4-carboxylate; 1- [2,8-bis (trifluoromethyl) -4-quinolyl-N-methoxy-3- (methoxymethyl) -N-methyl-1H-pyrazole-4-carboxamide; Methyl 1 - (7-chloro-4-quinolyl) -3- (methoxymethyl) -1H-pyrazole-4-carboxylate; Methyl 1 - (6-fluoro-4-quinolyl) -5- (methoxymethyl) - 1 H-pyrazole-4-carboxylate; 1- (7-chloro-4-quinolyl) -5- (methoxymethyl) -1H-pyrazole-4-carboxylate 2-ethoxyethyl; N-methoxy-3- (methoxymethyl) -N-methyl- 1 - [8 (trifluoromethyl) -4-quinolyl] -1H-pyrazole-4-carboxamide; [1 - (7-chloro-4-quinolyl) -5- (methoxymethyl) -1 H-pyrazole-4-yl] (1, 3-thiazolidin-3-yl) methanone; 2- [1- (7-chloro-4-quinolyl) -5- (methoxymethyl) -1H-pyrazol-4-yl] -2-propanol; 1- (7-chloro-4-quinolyl) -N-methoxy-5- (methoxymethyl) -N-propyl-1H-pyrazole-4-carboxamide; 5 - ({4-methoxycarbonyl) -l- [8- (trifluoromethyl) -4-quinolyl] H -pyrazol-5- yl} dimethyl methoxy) isophthalate; 1- (7-chloro-4-quinolyl) -N-isopropyl-N-methoxy-5- (methoxymethyl) ~ 1H-pyrazole-4-carboxamide; Methyl 4- [{[1 - (7-chloro-4-quinolyl) -5- (methoxymethyl) - 1 H-pyrazole-4-yl] carbonyl} (methoxy) amino] butanoate; Methyl 5 - [(heptanoyloxy) methyl] -1- [8- (trifluoromethyl) -4-quinolyl] - H-pyrazole-4-carboxylate; 7-chloro-4- {5-methoxymethyl) -4- [5-trifluoromethyl) -1,2,4-oxadiazol-3-yl] -1H-pyrazol-1-yl} quinoline; methyl 1 - (7-chloro-4-quinolinyl) -5- {[((1; 1 -dimethylethyl) sulfanyl] methyl} - lΗ-pyrazole-4-carboxylate; 1- (7-chloro-4-quinolinyl) -5 - [(methyloxy) methyl] -1H-pyrazole-4-carbaldehyde; [1 - (7-chloro-4-quinolinyl) -4- (1 -pheny lethenyl) - 1 H-pyrazol-5 -yl] methyl methyl ether; 1 - {3 - [(methy loxy) methy 1] - 1 - [8- (trifluoromethy 1) -4-quinoliny 1] - 1 H-pyrazol-4-yl} ethanone; methyl 3 - [(methyloxy) methyl] -5- (methylsulfanyl) - 1 - [8- (trifluoromethyl) -4- quinolinyl] - 1 H-pyrazole-4-carboxylate; methyl 5-chloro-3 - [(methyloxy) methyl] - 1 - [8- (trifluoromethyl) -4-quinolinyl] - 1 H-pyrazole-4-carboxylate; (1 E) - 1 - {1 - (7-chloro-4-quinolinyl) -5 - [(methyloxy) methyl] - 1 H-pyrazol-4-yl} ethanone oxime; 1 - (2; 7-dimethyl-4-quinolinyl) -Ν-methyl-Ν- (methyloxy) -5- [(methyloxy) methyl] - 1 H-pyrazole-4-carboxamide; N-methyl-l- [2-methyl-8- (l-methylethyl) -4-quinolinyl] -N- (methyloxy) -5- [(methyloxy) methyl] -1 H-pyrazole-4-carboxamide; N-methyl-N- (methyloxy) -5 - [(methyloxy) methyl] -1- [2-methyl-7- (trifluoromethyl) -4-quinolinyl] - 1 H-pyrazole-4-carboxamide; N-methyl-N- (methyloxy) -5 - [(methyloxy) methyl] -1- (2; 5; 7-trimethyl-4-quinolinyl) - 1 H-pyrazole-4-carboxamide; 1 - (7-chloro-2; 8-dimethyl-4-quinolinyl) -N-methyl-N- (methyloxy) -5- [(methyloxy) methyl] - 1 H-pyrazole-4-carboxamide; 1- (6; 8-dichloro-2-methyl-4-quinolinyl) -N-methyl-N- (methyloxy) -5- [(methyloxy) methyl] -1 H-pyrazole-4-carboxamide; N-methyl-N- (methyloxy) -5 - [(methyloxy) methyl] - 1 - (8-methyl-4-quinolinyl) - 1 H-pyrazole-4-carboxamide; 1 - (2; 8-dimethyl-4-quinolinyl) -N-methyl-N- (methyloxy) -5- [(methyloxy) methyl] - 1 H-pyrazole-4-carboxamide; N-methyl-N- (methyloxy) -5 - [(methyloxy) methyl] -l- [2-methyl-8- (trifluoromethyl) -4-quinolinyl] - 1 H-pyrazole-4-carboxamide; 1 - (6-chloro-2; 8-dimethyl-4-quinolinyl) -N-methyl-N- (methyloxy) -5- [(methyloxy) methyl] -1 H-pyrazole-4-carboxamide; N-methyl-N- (methyloxy) -5 - [(methyloxy) methyl] -1- (2-methyl-4-quinolinyl) - 1 H-pyrazole-4-carboxamide; N-methyl- 1- [2 -methyl-8- (methyloxy) -4-quinolinyl] -N- (methyloxy) -5- [(methyloxy) methyl] -1 H-pyrazole-4-carboxamide; N-methyl-N- (methyloxy) -5 - [(methyloxy) methyl] -1 - (2; 6; 8-trimethyl-4-quinolinyl) - 1 H-pyrazole-4-carboxamide; l- [5-chloro-2-methyl-8- (methyloxy) -4-quinolinyl] -N-methyl-N- (methyloxy) -5 - [(methyloxy) methyl] - 1 H-pyrazole-4-carboxamide; 1 - (5; 7-dichloro-4-quinolinyl) -N-methyl-N- (methyloxy) -5- [(methyloxy) methyl] - 1 H-pyrazole-4-carboxamide; 5- (hydroxymethyl) -N-methyl-N- (methyloxy) -l- [8- (trifluoromethyl) -4-quinolinyl] - 1 H-pyrazole-4-carboxamide; 1- (6-chloro-2; 8-dimethyl-4-quinolinyl) -N-methyl-N- (methyloxy) -5- [2- (methyloxy) ethyl] - 1 H-pyrazole-4-carboxamide; N-methyl-N- (methyloxy) -5- [2- (methyloxy) ethyl] -1- [8- (trifluoromethyl) -4-quinolinyl] - 1 H-pyrazole-4-carboxamide; N-methyl-N- (methyloxy) -5- [2- (methyloxy) ethyl] -1- [7- (trifluoromethyl) -4-quinolinyl] - 1 H-pyrazole-4-carboxamide; N; 5-dimethyl-N- (methyloxy) - 1 - [2-methyl-8- (trifluoromethyl) -4-quinolinyl] -1H-pyrazole-4-carboxamide; 1- (7-chloro-4-quinolinyl) -5 - [(methyloxy) methyl] -1H-pyrazole-4-carbaldehyde O-methyloxime; 5- (bromomethyl) -l- (5; 7-dichloro-4-quinolinyl) -N-methyl-N- (methyloxy) - 1 H-pyrazole-4-carboxamide; 1- (7-chloro-4-quinolinyl) -3- (dibromomethyl) -N-methyl-N- (methyloxy) - 1H-pyrazole-4-carboxamide; 1 - {1 - (7-chloro-4-quinolinyl) -5 - [(methyloxy) methyl] - 1 H-pyrazol-4-yl} ethanol; (lE) -l- {3 - [(methyloxy) methyl] -l- [8- (trifluoromethyl) -4-quinolinyl] -lH- pyrazol-4-yl} ethanone O- (cyclopropylmethyl) oxime; N-methyl-N- (methyloxy) -3 - [(methyloxy) methyl] -l- [7- (trifluoromethyl) -4 quinolinyl] -1 H-pyrazole-4-carboxamide; N-methyl-N- (methyloxy) -3 - [(methyloxy) methyl] -l- [2- (trifluoromethyl) -4-quinolinyl] -lH-pyrazole-4-carboxamide; 1 - (7-chloro-4-quinolinyl) -N-methyl-N- (methyloxy) -3 - [(methyloxy) methyl] -1H-pyrazole-4-carboxamide; methyl 3 - {1 - (7-chloro-4-quinoliny l) -5 - [(methy loxy) methyl] - 1 H-pyrazol-4- yl} -4; 5-dihydro-5-isoxazolecarboxylate; 1- (7-chloro-4-quinolinyl) -N- (cyclopropylcarbonyl) -N- (methyloxy) -5- [(methy loxy) methy 1] - 1 H-pyrazole-4-carboxamide; ethyl 3- {1- (7-chloro-4-quinolinyl) -5 - [(methyloxy) methyl] -1H-pyrazol-4- yl} -3-oxopropanoate; 1- (7-chloro-4-quinolinyl) -N-methyl-N- (methyldisulfanyl) -5- [(methy loxy) methy 1] - 1 H-pyrazole-4-carboxamide; 1- (7-chloro-4-quinolinyl) -N- (ethyldisulfanyl) -N-methyl-5- [(methyloxy) methyl] -1 H-pyrazole-4-carboxamide; l- (7-chloro-4-quinolinyl) -N-methyl-N - [(l-methylethyl) disulfanyl] -5- [(methyloxy) methyl] - 1 H-pyrazole-4-carboxamide; ethyl 1- (7-chloro-4-quinolinyl) -N- (methyloxy) -5 - [(methyloxy) methyl] -1H-pyrazole-4-carbimidothioate; (1 E) - 1 - {1 - (7-chloro-4-quinolinyl) -5 - [(methyloxy) methyl] - 1 H-pyrazol-4- yl} -l-propanone O-methyloxime; (3E) -4- {1 - (7-chloro-4-quinolinyl) -5- [(methy loxy) methyl] - 1 H-pyrazol-4-yl} -3-buten-2-one; ethyl (2Z; 4E) -5- {1- (7-chloro-4-quinolinyl) -5 - [(methyloxy) methyl] -H-pyrazol-4-yl} -3-hydroxy-2; 4-pentadienoate; 2-propenyl (2E) -3- {1- (7-chloro-4-quinolinyl) -5 - [(methyloxy) methyl] -1H-pyrazol-4-yl} -2-propenoate; 1- (7-chloro-4-quinolinyl) -N- (ethyloxy) -N-methyl-5 - [(methyloxy) methyl] - 1H-pyrazole-4-carboxamide; 4- (3 - [(methyloxy) methyl] -4- {5 - [(methyloxy) methyl] -3-isoxazolyl} -lH- pyrazol-1 -yl) -8- (trifluoromethyl) quinoline; 7-chloro-4- {4 - [(ethyloxy) methyl] -5 - [(methyloxy) methyl] -l H-pyrazol- 1 - yl} quinoline; (Z) - {1- (7-chloro-4-quinolinyl) -5 - [(methyloxy) methyl] -1H-pyrazol-4- yl} [(methyloxy) imino] methyl methanesulfonate; 1- (7-chloro-4-quinolinyl) -N-methyl-5 - [(methyloxy) methyl] -N- (methylsulfanyl) - 1 H-pyrazole-4-carboxamide; 1- (7-chloro-4-quinolinyl) -N- (ethylsulfanyl) -N-methyl-5- [(methyloxy) methyl] -1 H-pyrazole-4-carboxamide; {1- (7-chloro-4-quinolinyl) -5 - [(methyloxy) methyl] -1H-pyrazol-4- yl} acetonitrile; 3- (hydroxymethyl) -N; N-dimethyl- 1 - [8- (trifluoromethyl) -4-quinolinyl] - 1 H- pyrazole-4-carboxamide; {1- (7-chloro-4-quinolinyl) -4- [3- (4-fluorophenyl) -1; 2; 4-oxadiazol-5-yl] - 1H-pyrazol-5-yl} methyl methyl ether; 1 - (7-chloro-4-quinolinyl) -N- (methyloxy) -N; 5-bis [(methyloxy) methyl] - 1 H- pyrazole-4-carboxamide; [1 - (7-chloro-4-quinoliny l) -4- (3 -phenyl- 1; 2; 4-oxadiazol-5-yl) - 1 H-pyrazol- 5-yl] methyl methyl ether; 2-oxiranylmethyl 1 - (7-chloro-4-quinolinyl) -N- (methyloxy) -5- [(methyloxy) methyl] -1 H-pyrazole-4-carboximidoate; l- (7-chloro-4-quinolinyl) -N '- [(cyclopropylmethyl) oxy] -5- [(methyloxy) methyl] - 1 H-pyrazole-4-carboximidamide; 1 - (7-chloro-4-quinolinyl) -N- (methyloxy) -5 - [(methyloxy) methyl] - 1 H- pyrazole-4-carboximidoyl chloride; 3- {1- (7-chloro-4-quinolinyl) -5 - [(methyloxy) methyl] -1H-pyrazol-4-yl} - N; N-dimethyl-4; 5-dihydro-5-isoxazolecarboxamide; (lZ) -1- {1- (7-chloro-4-quinolinyl) -5 - [(methyloxy) methyl] -1H-pyrazol-4-yl} ethanone O- (2-methylpropanoyl) oxime; (1 E) - 1 - {1 - (7-chloro-4-quinolinyl) -5 - [(methyloxy) methyl] - 1 H-pyrazol-4-yl} ethanone O- (cyclopropylcarbonyl) oxime; 1 - (8-fluoro-4-quinolinyl) -N-methyl-N- (methyloxy) -3 - [(methyloxy) methyl] - 1H-pyrazole-4-carboxamide; N-methyl-N- (methyloxy) -3 - [(methyloxy) methyl] -1- (7-methyl-4-quinolinyl) - 1 H-pyrazole-4-carboxamide; 1- (7-chloro-4-quinolinyl) -N-methyl-N- (methyloxy) -5 - ({[2- (methyloxy) -5- nitrophenyljoxy} methyl) - 1 H-pyrazole-4-carboxamide; 5 - {[(2-bromo-3-pyridinyl) oxy] methyl} -N-methyl-N- (methyloxy) -l- [8- (trifluoromethyl) -4-quinolinyl] - 1 H-pyrazole-4-carboxamide ; 5 - {[(4'-bromo [l; l'-biphenyl] -4-yl) oxy] methyl} -N-methyl-N- (methyloxy) - 1 - [8- (trifluoromethyl) -4-quinolinyl] -1 H-pyrazole-4-carboxamide; 5-chloro-N-methyl-N- (methyloxy) -3 - [(methyloxy) methyl] -l- [8- (trifluoromethyl) -4-quinoliny 1] - 1 H-pyrazole-4-carboxamide; methyl {[({l- (7-chloro-4-quinolinyl) -5 - [(methyloxy) methyl] -lH-pyrazol-4- yl} carbonyl) (methyl) amino] oxy} (oxo) acetate; 1 - {1 - (7-fluoro-4-quinolinyl) -5 - [(methyloxy) methylj- 1 H-pyrazol-4-yl} - 1 - propanone; (1 E) - 1 - {1 - (7-chloro-4-quinolinyl) -5 - [(methyloxy) methyl] - 1 H-pyrazol-4- yl} ethanone O- [2- (methyloxy) acetyl] oxime ; 4- {1- (7-chloro-4-quinolinyl) -5 - [(methyloxy) methyl] -1H-pyrazol-4- yl} benzaldehyde; 1- (7-chloro-4-quinolinyl) -5 - ({[2- (ethylsulfanyl) phenyl] oxy} methyl) -N- methyl-N- (methyloxy) - 1 H-pyrazole-4-carboxamide; l- (7-chloro-4-quinolinyl) -N-methyl-5 - [(methyloxy) methyl] -N- (propyloxy) - 1H-pyrazole-4-carboxamide; 1- (7-chloro-4-quinolinyl) -N-methyl-5 - [(methyloxy) methyl] -N- (2-propenyloxy) - 1 H-pyrazole-4-carboxamide; l- (7-chloro-4-quinolinyl) -N-methyl-5 - [(methyloxy) methyl] -N - [(l-methylpropy l) oxy] - 1 H-pyrazole-4-carboxamide; 1 - (7-chloro-4-quinolinyl) -N-methyl-N - [(l -methylethyl) oxy] -5- [(methyloxy) methyl] - 1 H-pyrazole-4-carboxamide; methyl 4 - {[({1- (7-chloro-4-quinolinyl) -5 - [(methyloxy) methyl] -lH-pyrazol-4-y 1} carbony l) (methyl) amino] oxy} butanoate; N- (3-butenyloxy) -1- (7-chloro-4-quinolinyl) -N-methyl-5- [(methyloxy) methyl] -1 H-pyrazole-4-carboxamide; 1- (7-chloro-4-quinolinyl) -5 - [(ethyloxy) methyl] -N-methyl-N- (methyloxy) - 1H-pyrazole-4-carboxamide; 4- {4- {4; 5-bis [(methyloxy) methyl] -3-isoxazolyl} -5 - [(methyloxy) methyl] - 1 H-pyrazol- 1 -yl} -7-bromoquinoline; (3- {1- (6-fluoro-4-quinolinyl) -5 - [(methyloxy) methyl] -1H-pyrazol-4-yl} -5- isoxazolyl) methyl acetate; 4- {4- {4; 5-bis [(methyloxy) methyl] -3-isoxazolyl} -5 - [(methyloxy) methyl] - 1 H-pyrazol- 1 -y 1} -6-fluoroquinoline; 7-ethyl-4- (5 - [(methyloxy) methyl] -4- {5 - [(tetrahydro-2H-pyran-2- yloxy) methyl] -3-isoxazolyl} - 1 H-pyrazol- 1 -yl) quinoline; 4- {4- {4; 5-bis [(methyloxy) methyl] -3-isoxazolyl} -5 - [(methyloxy) methyl] - 1 H-pyrazol- 1 -y 1} -7-ethylquinoline; 3 - {[(3 - {1 - (7-chloro-4-quinolinyl) -5 - [(methy loxy) methyl] - 1 H-pyrazol-4-yl} -5-isoxazolyl) methyl] oxy} propanenitrile; methyl 3- {1- (7-chloro-4-quinolinyl) -5 - [(methyloxy) methyl] -1H-pyrazol-4- yl} -4-methyl-5-isoxazolecarboxylate; 1; 1 -dimethylethyl 3- {1- (7-chloro-4-quinolinyl) -5 - [(methyloxy) methyl] - 1 H-pyrazol-4-y 1} -5-isoxazolecarboxylate; 3 - {[(3- {1- (7-ethyl-4-quinolinyl) -5 - [(methyloxy) methyl] -lH-pyrazol-4-yl} - 5-isoxazolyl) methyl] oxy} propanenitrile; {1- (7-chloro-4-quinolinyl) -4- [2- (trifluoromethyl) phenyl] -lH-pyrazol-5-yl} methyl methyl ether; 7-chloro-4- (5 - [(methyloxy) methyl] -4- {4 - [(trifluoromethyl) oxy] phenyl} - 1 H-pyrazol-1-yl) quinoline; methyl 5 - [(methyloxy) methyl] -l- (6; 7; 8-trichloro-4-quinolinyl) -lH- pyrazole-4-carboxylate; 1 - (7-chloro-4-quinolinyl) -N-methyl-5- {[(1 -methylethyl) oxy] methyl} -N- (methyloxy) - 1 H-pyrazole-4-carboxamide; methyl 3 - [(methyloxy) methyl] -5- (2-thienyl) -l- [8- (trifluoromethyl) -4- quinolinyl] - 1 H-pyrazole-4-carboxylate; • 7-chloro-4- (5 - [(methyloxy) methyl] -4- {3 - [(methyloxy) methyl] -l; 2; 4- oxadiazol-5-yl} -lH-pyrazol-l -yl) quinoline; [1 - (7-chloro-4-quinolinyl) -4- (1; 3 -thiazol-2-yl) - 1 H-pyrazol-5-yl] methyl methyl ether; [1- (7-chloro-4-quinolinyl) -4- (4; 5-dihydro-1; 3-thiazol-2-yl) -lH-pyrazol-5-yljmethyl methyl ether; 1; 1 -dimethylethyl 1 - (7-chloro-4-quinolinyl) -5 - [(methyloxy) methyl] - 1 H-pyrazole-4-carboxylate; l- (7-cyano-4-quinolinyl) -N-methyl-N- (methyloxy) -5 - [(methyloxy) methyl] - 1H-pyrazole-4-carboxamide; • [4- [5- (bromomethyl) -3-isoxazolyl] - 1 - (7-bromo-4-quinolinyl) - 1 H-pyrazol- 5-yl] methyl methyl ether; l- (7-chloro-4-quinolinyl) -N'-methyl-5 - [(methyloxy) methyl] -N'-phenyl-1H-pyrazole-4-carbohydrazide; 1 - (7-chloro-4-quinolinyl) -N '- (2; 5-dichlorophenyl) -5 - [(methyloxy) methyl] - 1H-pyrazole-4-carbohydrazide; l- (7-chloro-4-quinolinyl) -N '- (l; l-dimethylethyl) -5 - [(methyloxy) methyl] - 1H-pyrazole-4-carbohydrazide; (1 - (7-chloro-4-quinoliny l) -4- {[methy l (methyloxy) amino] carbonyl} - 1 H-pyrazol-5-yl) methyl 2-methylpropanoate; • N-ethyl-1- (6-fluoro-4-quinolinyl) -N-methyl-5 - [(methyloxy) methyl] -1H-pyrazole-4-carboxamide; l- (7-chloro-4-quinolinyl) -N- (cyclopropylmethyl) -N-methyl-5- [(methy loxy) methyl] - 1 H-pyrazole-4-carboxamide; 3- {1 - (7-chloro-4-quinolinyl) -5 - [(methyloxy) methyl] - 1 H-pyrazol-4-yl} - 4; 6-dimethyl-4H-1; 2; 4-oxadiazin- 5 (6H) -one; N- (4-chloro-2-butynyl) -1- (7-chloro-4-quinolinyl) -5 - [(methyloxy) methyl] -1H-pyrazole-4-carboxamide; methyl 1 - (7-chloro-4-quinolinyl) -5 - (methy loxy) - 1 H-pyrazole-4-carboxylate; 1 - (7-chloro-4-quinolinyl) -5- (ethylsulfanyl) -N-methyl-N- (methyloxy) - 1 H-pyrazole-4-carboxamide; 1- (7-chloro-4-quinolinyl) -5 - [(methyloxy) methyl] -N- (4-morpholinyl) -1H-pyrazole-4-carboxamide; 1- (7-chloro-4-quinolinyl) -N-methyl-N- (methyloxy) -5 - (methy Isulfanyl) -1H-pyrazole-4-carboxamide; (1 - (7-chloro-4-quinoliny l) -4- {[methyl (methyloxy) amino] carbonyl} - 1 H-pyrazol-5-yl) methyl cyclopropanecarboxylate; (1 - (7-chloro-4-quinoliny l) -4- {[methyl (methy loxy) amino] carbony 1} - 1 H-pyrazol-5-yl) methyl 2-thienylacetate; 7-chloro-4- (5- [(methy loxy) methy 1] -4- {1 - [3 - (methy loxy) propyl] - 1 H- imidazol-5-y 1} - 1 H-pyrazol- 1 -yl) quinoline; [1 - (7-chloro-4-quinolinyl) -4- (1 -methyl-1 H-imidazol-5-yl) - 1 H-pyrazol-5-yljmethyl methyl ether; {1- (7-chloro-4-quinolinyl) -5 - [(methyloxy) methyl] -1H-pyrazol-4- yl} [(trimethylsilyl) oxy] acetonitrile; [1- (7-bromo-4-quinolinyl) -4- (l-piperidinylcarbonyl) -1H-pyrazol-5-yl] methyl methyl ether; methyl {4- (1-piperidinylcarbonyl) -l- [7- (trifluoromethyl) -4-quinolinyl] -lH- pyrazol-5-yl} methyl ether; 5-amino- 1 - (7-chloro-4-quinolinyl) - 1 H-pyrazole-4-carbonitrile; 3- {1- (7-chloro-4-quinolinyl) -5 - [(methyloxy) methyl] -1H-pyrazol-4-yl} -2-thiophenecarbaldehyde; [1- (7-chloro-4-quinolinyl) -4- (5-ethenyl-l; 3-oxazol-2-yl) -lH-pyrazol-5-yljmethyl methyl ether; 1 - (2- {1 - (7-chloro-4-quinolinyl) -5- [(methy loxy) methyl] - 1 H-pyrazol-4-yl} - 1; 3-oxazol-5-yl) ethyl acetate ; [1- (7-bromo-4-quinolinyl) -4- (2-isoxazolidinylcarbonyl) -1H-pyrazol-5-yljmethyl methyl ether; {4- (2-isoxazolidinylcarbonyl) - 1 - [7- (trifluoromethyl) -4-quinolinyl] - 1 H- pyrazol-5-yl} methyl methyl ether; [1- (7-ethyl-4-quinolinyl) -4- (2-isoxazolidinylcarbonyl) -1H-pyrazol-5-yl] methyl methyl ether; [1 - (6-fluoro-4-quinolinyl) -4- (2-isoxazolidinylcarbonyl) - 1 H-pyrazol-5-yljmethyl methyl ether; N '- (2-chlorophenyl) - 1 - (7-chloro-4-quinolinyl) -5 - [(methyloxy) methyl] - 1 H-pyrazole-4-carbohydrazide; 1- (7-chloro-4-quinolinyl) -N '- (2; 4-dichlorophenyl) -5 - [(methyloxy) methyl] - 1H-pyrazole-4-carbohydrazide; l- (7-chloro-4-quinolinyl) -N '- (2; 6-dichlorophenyl) -5 - [(methyloxy) methyl] - 1H-pyrazole-4-carbohydrazide; 1- (7-chloro-4-quinolinyl) -5 - [(methyloxy) methyl] -N '- (3-methylphenyl) -1H-pyrazole-4-carbohydrazide; N '- (3 -chlorophenyl) - 1 - (7-chloro-4-quinolinyl) -5 - [(methyloxy) methyl] - 1 H- pyrazole-4-carbohydrazide; N '- (3-chloro-4-methylphenyl) - 1 - (7-chloro-4-quinolinyl) -5- [(methyloxy) methyl] - 1 H-pyrazole-4-carbohydrazide; 1 - (7-chloro-4-quinolinyl) -N '- (3; 4-dichlorophenyl) -5 - [(methyloxy) methyl] - 1H-pyrazole-4-carbohydrazide; 1 - (7-chloro-4-quinolinyl) -N '- (4-cyanophenyl) -5 - [(methyloxy) methyl] - 1 H-pyrazole-4-carbohydrazide; (3- {1- (7-chloro-4-quinolinyl) -5 - [(methyloxy) methyl] -1H-pyrazol-4-yl} -5- isoxazolyl) methyl phenyl sulfone; (3- {1- (7-chloro-4-quinolinyl) -5 - [(methyloxy) methyl] -1H-pyrazol-4-yl} -5- isoxazolyl) methyl ethyl sulfoxide; [4- (4-chlorophenyl) - 1 - (7-chloro-4-quinolinyl) - 1 H-pyrazol-5-yl] methyl methyl ether; 1- (1- (7-chloro-4-quinolinyl) -5 - [(methyloxy) methyl] -1H-pyrazol-4-yl} -3-phenyl-2-propyn-1-one; N - ({l- (7-chloro-4-quinolinyl) -5 - [(methyloxy) methyl] -lH-pyrazol-4- yl} methyl) -3- (methyloxy) -l-propanamine, as well as their possible tautomeric forms, their salts, N-oxides and metal and metalloid complexes. 6. Compounds according to any one of claims 1 to 4 of general formula (IV):

special case of the compounds of formula (I) for which R ₃ represents hydrogen and R, and R ₂ are respectively in position 4 and 5 of the pyrazole ring, R ₂ , Y ,, Y ₂ , Y ₃ , Y ₄ , Y ₅ and Y ₆ being as defined in any one of claims 1 to 4, and R represents a carboxy, carbamoyl, N-alkylcarbamoyl, N, N-dialkylcarbamoyl, N-alkyl, N-alkoxyalkylcarbamoyl, N-alkoxycarbamoyl group , N-alkyl-N-aminoalkylcarbamoyl, N, N-diaminoalkylcarbamoyl, lower alkoxycarbonyl; a nitrile, or a lower acyl group. 7. Process for the preparation of the compounds according to one of claims 1 to 6, characterized by the reaction:

formulas (I), (II) and (III), in which X represents a halogen and R ,, R ₂ , R ₃ , Y ,, Y ₂ , Y ₃ , Y ₄ , Y ₅ and Y ₆ are as defined in claim 1, the reaction being carried out in the presence of an organic or inorganic base, in the absence or in the presence of a solvent, at a temperature between -80 ° C and 180 ° C or at the boiling point of the solvent used. 8. Process for the preparation of the compounds according to claim 6, characterized by the reaction:

where X 'represents a halogen atom, N, N-dialkylamino or alkoxy, R ,, R ₂ and Y, with Y ₆ being as defined for the compounds of formula (IV) above. 9. Fungicidal compositions comprising as active material an effective amount of at least one compound according to any one of claims 1 to 6 or one of its salts acceptable in agriculture or a metal or metalloid complex of this compound also acceptable in agriculture. 10. Fungicidal compositions according to claim 9 comprising, in addition to the active material according to any one of claims 1 to 6 or one of its acceptable salts in agriculture or a metallic or metalloid complex of this compound also acceptable in agriculture, a solid support or liquid, acceptable in agriculture and / or a surfactant also acceptable in agriculture. 11. Fungicidal compositions according to one of claims 9 or 10 comprising from 0.05 to 95% by weight of active material. 12. A preventive or curative method of combating phytopathogenic fungi in cultures, characterized in that the leaves, the trunks of plants or the soils where these plants grow or are likely to grow are treated by application, spraying or injection of an agronomically effective and non-phytotoxic amount of at least one compound according to any one of claims 1 to 6 or one of its acceptable salts in agriculture or a metal or metalloid complex of this compound also acceptable in agriculture or of a fungicidal composition comprising an active material according to any one of claims 1 to 6 and / or at least one of the following compounds: trαw - (+/-) - 6- [2- [l- (9-acridinyl) -5- (4-fluorophenyl) -3- (l-methylethyl) - lH- pyrazol-4-yl] ethyl] tetrahydro-4-hydroxy-2H-pyran-2-one; trα "5 - (+/-) - 6- [2- [l- (9-acridinyl) -5- (4-fluorophenyl) -3- (l-methylethyl) - 1H-pyrazol-4-yl] ethenyl ] tetrahydro-4-hydroxy-2H-pyran-2-one; 3-methyl-1- (4-methylquinolin-2-yl) -5-trifluoromethylpyrazole; 3-trifluoromethyl- 1 - (4-methylquinolin-2-yl) -5-trifluoromethylpyrazole; 3-phenyl-1 - (4-methylquinolin-2-yl) -5-trifluoromethylpyrazole; 3- (2-thienyl) - 1 - (4-methylquinolin-2-yl) -5-trifluoromethylpyrazole; 1 - (methyl-quinolin-4-yl) -3-methyl-5-trifluoromethylpyrazoles; 1 - (trifluoromethyl-quinolin-4-yl) -3-methyl-5-trifluoromethylpyrazoles; 1- (phenyl-quinolin-4-yl) -3-methyl-5-trifluoromethylpyrazoles; l - [(2-thienyl) -quinolin-4-yl] -3-methyl-5-trifluoromethylpyrazoles; endo-1- (7-chloro-4-quinolinyl) -5-methyl-N- (9-azabicyclo [3,3, l] non-3-yl) - 1H-pyrazole-3-carboxamide; 5-amino-1- (7-chloro-4-quinolinyl) -1H-pyrazole-4-carbonitrile; 4-acetyl-1- (7-chloro-4-quinolinyl) -5-methyl-1H-pyrazole; 5-methyl-1- (4-quinolinyl) -1H-pyrazole-4-carboxylic acid; 5-cyclopropyl-1 - (4-quinolinyl) - 1 H-pyrazole-4-carboxylic acid. 13. Process for the preventive or curative treatment of plant multiplication products, as well as of the resulting plants, against fungal diseases, characterized in that said products are covered with an effective and non-phytotoxic amount of compound or of composition according to one of the preceding claims and / or of at least one of the following compounds: trans - (+/-) - 6- [2- [1 - (9-acridinyl) -5 - (4-fluorophenyl ) -3 - (1 -methylethyl) - 1 H-pyrazol-4-yl] ethyl] tetrahydro-4-hydroxy-2H-pyran-2-one; trans - (+/-) - 6- [2- [1 - (9-acridiny l) -5 - (4-fluorophenyl) -3 - (1 -methylethy 1) - 1 H-pyrazol-4-yl] ethenyl] tetrahydro-4-hydroxy-2H-pyran-2-one; 3-methyl-1- (4-methylquinolin-2-yl) -5-trifluoromethylpyrazole; 3-trifluoromethyl-1- (4-methylquinolin-2-yl) -5-trifluoromethylpyrazole; 3 -phenyl- 1 - (4-methylquinolin-2-yl) -5 -trifluoromethylpyrazole; 3- (2-thienyl) - 1 - (4-methylquinolin-2-yl) -5-trifluoromethylpyrazole; l- (methyl-quinolin-4-yl) -3-methyl-5-trifluoromethylpyrazoles; 1 - (trifluoromethyl-quinolin-4-yl) -3-methyl-5-trifluoromethylpyrazoles; • l- (phenyl-quinolin-4-yl) -3-methyl-5-trifluoromethylpyrazoles; • l - [(2-thienyl) -quinolin-4-yl] -3-methyl-5-trifluoromethylpyrazoles; • endo-1- (7-chloro-4-quinolinyl) -5-methyl-N- (9-azabicyclo [3.3, l] non-3-yl) - 1H-pyrazole-3-carboxamide; 5-amino-1- (7-chloro-4-quinolinyl) -1H-pyrazole-4-carbonitrile; • 4-acetyl-1- (7-chloro-4-quinolinyl) -5-methyl-1H-pyrazole; • 5-methyl-1- (4-quinolinyl) -1H-pyrazole-4-carboxylic acid; • 5-cyclopropyl-1- (4-quinolinyl) -1H-pyrazole-4-carboxylic acid. w 14. Method according to one of claims 12 or 13 in which cereals, rice, fruit trees, forest trees, vines, oilseeds, vegetable crops, solaneas or beet are treated. 15. Method according to one of claims 12 to 14 in which rice, wheat, barley, rye, triticale, fruit trees, corn, cotton, flax, rapeseed, vine, forest trees, peas, potatoes or beets. 16. Method according to any one of claims 12 to 15 in which wheat or barley is treated. 20 17. Method according to any one of claims 13 to 16 in which the seeds of cereals, potato, cotton, peas, rapeseed, corn, flax or even seeds of forest trees are treated. 18. Method according to any one of claims M a he characterized in that the plants are genetically modified plants. 19. Method according to any one of claims 12 to 18 in which the dose of active material applied is between 10 and 800 g of active material per 30 hectare, preferably between 50 and 300 g of active ingredient per hectare in the case of foliar treatments. 20. Method according to any one of claims 13 to 18 in which the dose of active material applied is between 2 and 200 g of active material per 35 100 kg of seed, preferably between 3 and 150 g per 100 kg in the case of seed treatments.