FR2834288A1 - New 5-amino-1-phenylpyrazole derivatives, useful as parasiticides and insecticides, e.g. for treating animals, in plant protection and protecting stored foods - Google Patents

Abstract

Synthesis of 5-substituted-1-phenylpyrazole derivatives (I) by reacting the 5-amino compound with (thio)phosgene or thionyl chloride, in inert solvent and in presence of acid acceptor, at -78 to 25degreesC to form the 5-(iso(thio)cyanato or sulfinylamino) compound. Synthesis of 5-substituted-1-phenylpyrazole derivatives of formula (I) by reacting the 5-amino compound (II) with (thio)phosgene or thionyl chloride, in inert solvent and in presence of acid acceptor, at -78 to 25degreesC to form the 5-(iso(thio)cyanato or sulfinylamino) compound. A and B = hydrogen or a wide range of substituents; R1-R5 = hydrogen, halo, or 1-6C alkyl, alkoxy or alkylthio (all linear, branched or cyclic, saturated or unsaturated, and optionally substituted by one or more halo); Z = NCO, NCS, NSO, NHC(=X)R6, NHC(=O)XR6, NHC(=S)XR6, NHC(=X)NR7R8, -N=C=N-Het (where Het is a second heterocycle of the same formula) or 1,2-thiazin-1-oxide-2-yl group (optionally substituted by 1-7C (halo)alkyl, linear, branched or cyclic, saturated or unsaturated); X = oxygen or sulfur; R6 = 1-12C alkyl, alkenyl or alkynyl, optionally substituted by one or more halo, or 1-6C alkoxy, alkylthio or alkoxycarbonyl (all groups linear, branched or cyclic); phenyl, phenyl(1-4C)alkyl or 4-7 membered heterocycle (1-3 heteroatoms; nitrogen, sulfur, oxygen or silicon), optionally ring-substituted by one or more of halo, (halo)alkyl, haloalkoxy, haloalkylthio, (thio)cyano, nitro, amino(thio)carbonyl (optionally substituted by 1 or 2 alkyl), haloalkylsulfinyl or haloalkylsulfonyl, where alkyl is 1-4C linear, branched or cyclic, saturated or unsaturated, and heterocycles may also be subbstituted by phenyl, itself optionally substituted as above; R7 and R8 = hydrogen, R6, or Het in which Z = bond . The full definitions are given in the DEFINITIONS (Full Definitions) Field. Independent claims are also included for the following: (1) Several methods for converting (I) with Z = iso(thio)cyanato or -NSO to those with other values of Z; and (2) (I) as new compounds.

Description

of ligand in a metal complex.

  The present invention relates to a process for the preparation of new N-substituted 5-amino-phenylpyrazole derivatives, new N-substituted 5-amino-phenylpyrazole derivatives and their use as parasiticidal agents.

and / or insecticides.

  It is known from the prior art that 1-phenyl-5-amino structures

  pyrazole show parasiticidal and insecticidal activity.

  International Application WO 87/03781 describes a method for the control of arthropods, nematodes and helminths using 1-phenyl-3,4-substituted-5-aminopyrazole derivatives, in particular fipronil, 1 (2,6-dichloro 4-trifluoromethylphenyl) -3-cyano-4-aminopyrazole-trifluorométhylsulfinyl5. European Application EP 0418016 discloses 1-phenyl-3cyano

  S-aminopyrazoles having insecticidal activity. -

  European Applications EP 0231510, EP 0216102 and US Pat. No. 4,895,957 describe numerous 1-phenyl-3-methyl-5-aminopyrazoles,

  These derivatives possess parasiticidal properties.

  US Patents US 4931461 and US 4808623 respectively disclose 1-phenyl-5-methylaminopyrole structures, variously substituted, having pesticidal activity and 1-phenyl-3-haloalkyl-5 structures.

  aminopyrazole and their uses as insecticides.

  German Application DE 19650197 also describes derivatives

  1-phenyl-3-thiocarbamoyl-5-aminopyrazole having similar activity.

  On the other hand, it has been shown in the Applications and Patents: WO 87/03781, US 4931461, US 4812165 and EP 0201852, that the acylation of 1-phenyl-5-aminopyrazole derivatives by acid halides and derivatives leads to N-acyl, N-aroyl or N-alkoxycarbonyl derivatives of 1-phenyl-5-aminopyrazole, having good insecticidal activity. However, the nitrogen reactivity at the 5-position for the substituted l-phenyl-5-aminopyrazole derivatives is considerably reduced by the presence, on the pyrazole ring, of electron-withdrawing substituents, such as cyano, trifluoroalkyl or trifluoromethylsulfinyl groups by example. As a result, 1-phenyl-5-N-carbamoylaminopyrazoles are difficult to obtain, according to this method,

with satisfactory performance.

: /, g

  In addition, the prior art does not teach that 5-isocyanato

  pyrazole, 5-isothiocyanatopyrazole and 5- (N-sulfinylamino) pyrazole, variously substituted: - possess parasiticidal and / or insecticidal activity and can be prepared and used as intermediates for the synthesis of a broad group of amides, thioamides, urethanes, ureas, thioureas, alkylamines, 172-thiazine-1-oxides and carbodiimides having a pyrazole moiety bearing various substituents and in particular electroattractant substituents, which possess

  also a parasiticidal and / or insecticidal activity.

  Such compounds which possess parasiticidal and / or insecticidal activity are useful for killing arthropods, plant parasitic nematodes, helminths, both for agricultural or horticultural use.

  to be administered to warm-blooded vertebrates.

  The object of the present invention is therefore: to provide a process for the preparation of N-substituted derivatives of 5-amino-1-phenylpyrazoles;

  - to propose new products distinguished by their characteristics

  properties and properties; to propose a composition containing at least one product according to

  invention, in combination with one or more diluents, fillers, adjuvants,

  tible and acceptable for the intended use; and - to provide a method for the control and control of arthropods, nematodes, helminths and the treatment of infections for which they are responsible. The present invention therefore relates to a new process for the synthesis of N-substituted derivatives of S-amino-1-phenylpyrazole corresponding to the general formula (I): ABZN 1 's 1 <R 3 I 1) in which: A and B represent, independently of one another: - a hydrogen atom; a linear, branched or cyclic alkyl, alkenyl or alkynyl radical comprising from 1 to 12, preferably from 1 to 6 carbon atoms, the carbine chain of these radicals being capable of being substituted by one or more chosen groups; among the radicals: halo, alkyloxy, alkylthio, alkyloxycarbonyl, the alkyl residue of these radicals, linear, branched or cyclic comprising from ol to 6 carbon atoms; a halogen atom chosen from fluorine, chlorine, bromine or iodine; a cyano, thiocyano, nitro, sulphonamido, alkylamino, dialkylamino, aminocarbouyl, aminothiocarbonyl, alkylaminocarbonyl, alkylamino thiocarbonyl, dialkylaminocarbonyl, dialkylaminothiocarbonyl or alkyl carbouylamino or alkylthiocarbonylamino radical and of which each alkyl radical, linear, branched or cyclic, saturated or unsaturated, comprises from 1 to 6 carbon atoms; a radical of general formula -S (O), R, in which n is equal to 0, 1 or 2, and R represents an alkyl radical, linear, branched or cyclic, saturated or unsaturated, comprising from 1 to 6 atoms of carbon optionally substituted by one or more identical or different halogen atoms; a phenyl or phenylalkyl radical or a heterocycle comprising from 4 to 7 ring members, and from 1 to 3 heteroatoms chosen from nitrogen, sulfur, oxygen or silicon, the straight or branched chain alkyl part having from one to four carbon atoms and the phenyl or heterocycle portion being optionally substituted by one or more groups selected from halogens, alkyls, haloalkyls, haloalkoxy, haloalkylthio, cyano, thiocyano, nitro, sultamido, amino carbonyl , aminocarbonyl, alkyl aminocarbonyl, alkyl aminothio carbonyl, dialkylaminocarbonyl, dialkylaminothiocarbouyl, the linear, branched or cyclic, saturated or unsaturated, alkyl moiety comprising from 1 to 6 carbon atoms. R 'R. R3 R4 and R5 represent, independently of each other: - a hydrogen atom; a halogen atom;

  an alkyl, alkoxy, alkylthio, haloalkyl or halogenoalkyl radical;

  o alkoxy, haloalkylthio, and whose linear, branched or cyclic, saturated or unsaturated, alkyl residue contains from 1 to 6 carbon atoms optionally substituted with one or

  several identical or different halogen atoms. - -

  Z represents a radical chosen from the groups: -N = C = O, -N = C = S or N = S = O, -NHC (= X) -R6, -NHC (= O) -X-R6, - NHC (= S) -X-R6, -NHC (= X) NR7Rs, wherein X represents an atom selected from oxygen or sulfur, Et6 represents a linear, branched or cyclic alkyl, alkenyl or alkynyl radical, comprising from 1 to 12, preferably from 1 to 6, carbon atoms, the carbon chain of these radicals being capable of being substituted by one or more groups chosen from the radicals: halo, alkyloxy, alkylthio, alkyloxycarbonyl, the alkyl radical of these radicals, linear, branched or cyclic comprising from 1 to 6 carbon atoms; a phenyl or phenylalkyl radical or a heterocycle having from 4 to 7 members, and from 1 to 3 heteroatoms chosen from nitrogen, sulfur, oxygen or silicon, the straight or branched chain alkyl part having from one to four atoms carbon, the phenyl or heterocyclic portion being optionally substituted by one or more groups selected from halogens, alkyls, haloalkyls, haloalkoxy,

  haloalkylthio, cyano, thiocyano, nitro, aminocarbonyl, aminothio-

  carbonyl, alkylamino carbonyl, alkylaminothiocarbonyl, dialkylaminocarbonyl, dialkylaminothiocarbonyl, haloalkylsulfonyl, or haloalkylsulphinyl and wherein the straight, branched or cyclic, saturated or unsaturated alkyl moiety comprises from one to four carbon atoms and the heterocyclic moiety is optionally substituted by a phenyl radical, itself substituted by one or more identical or different groups chosen from halogens, alkyls, haloalkyls, and the like; haloc, enoalkoxy, haloalkylthio, cyano, thiocyano, nitro, aminocarbonyl, aminothiocarbonyl, alkylaminocarbonyl, alkylaminothiocarbonyl, dialkylaminocarbonyl, dialkylaminothiocarbonyl haloalkylsulfonyl or haloalkylsulfinyl radical, the alkyl radical of these branched or cyclic linear radicals comprising from 1 to 6 carbon atoms; R7 and Rs represent, independently one

  on the other: a hydrogen atom, the radical R6 previously defined, a heterocycle -

  Het of general formula (I) wherein A, R, R2, R3, 1, and R have the same definition as above, while Z represents a bond. Z may also represent the sequence -N = C = N-Het, in which Het represents a heterocyclic O corresponding to the general formula (I) in which Z is this time a bond and A, B. R R2 R3 R4 and R.sub.2 are as defined above; Z may also represent the 1,2-thiazine-1-oxide-2-yl unit, optionally substituted with alkyl or haloalkyl units, the linear, branched or cyclic alkyl radical of which is saturated; or unsaturated, comprises 1 to 7 carbon atoms, which process is characterized in that it comprises at least one step in which a 1-phenyl-5-amino-pyrazole derivative having the formula II): AB H2NN

R1, R5

  Wherein R 1, R 2, R 3, R 4 and R 4 are as defined above, with at least one reagent selected from the group consisting of phosgene, thiophosgene and thionyl chloride, in an inert solvent, in the presence of an acid trap and at a temperature of between -78 ° C. and + 25 ° C., to obtain a compound corresponding to formula (I) in which Z represents a radical chosen from the groups:

-N = C = O, -N = C = S, -N = S = O.

  Pyrazole derivatives, useful as starting materials for

  2s in the work of the method according to the present invention, are known (see for example C.L.

  DICKINSON et al., J. ORG. CHEM. (1964), 29, p 1915, and patent applications

AT..., ?,

  EP 0216102, WO87 / 03781), or obtainable by known methods. Phosgene, thiophosgene and thionyl chloride are reagents well

known in organic synthesis.

  It is also known to those skilled in the art that iso (thio) cyanates, aromatic or heterocyclic are generally obtained by using the

  hydrochloride of the corresponding amine with phosgene (thiophosgene) in a

  inert, high boiling point, such as toluene or chlorobenzene, at

  temperatures between + 80 and + 140 C. However, 1-phenyl derivatives

  iso (thio) cyanatopyrazoles of general formula (I) can not be obtained by this process, because of the low basicity of the amino group in the starting products of general formula (II), which do not form addition salts with mineral acids

  such as hydrochloric acid or sulfuric acid.

  The Applicant has found, surprisingly, that it was

  possible to obtain the products according to the general formula (I), for which Z represents

  Sentimentally-N = C = 0 or -N = C = S, with optimal purity and quantitative yield, slowly adding the combination of a pyrazole derivative according to the general formula (II) and a trap. acid to an excess of phosgene or, respectively, of thiophosgene in solution in an inert organic solvent, the reaction medium

  being at a temperature between - 78 C and + 25 C.

  In order to carry out the process according to the present invention, for 1 mole of derivative according to general formula (II), 1.0 to 2.5 moles of phosgene or thiophosgene, more specifically 1.8 to 2.0 moles, and generally preferably 2.05 moles of acid trap. The solvents to be used for carrying out the process according to the present invention are to be chosen from inert organic solvents, alone or as a mixture. More specifically, aliphatic, alicyclic or aromatic hydrocarbons such as hexane, heptane, benzene and toluene may be mentioned. It is also possible to mention substituted hydrocarbons, in particular by

  halogen, preferably chlorobenzene, chloroform, dichloro

  methane or carbon tetrachloride; ethers such as diethyl ether, tetrahydrofuran. More particularly toluene or the toluene / dichloromethane mixture. The acid traps to be retained are acid acceptors usually used in organic synthesis, for example organic or inorganic bases, to be used conventionally. Tertiary amines, more specifically pyridine, N, N-dimethylamine or triethylamine, are particularly suitable. The reaction mixture and the corresponding products are treated and isolated according to a procedure conventionally used in organic synthesis, with

  For example, the following statement: filtration of tertiary amine hydrochloride, eli-

  removal of the organic solvent and drying of the product under vacuum.

  It has been found that the products according to the general formula (I), for which Z represents the sequence -N = S = O, can be prepared by reaction of the compound corresponding to the general formula (II) with thiouyl chloride . The traditional methods of synthesizing Nsulfinylamines described in the literature (see, for example, G. KRESZE et al., Angew Chem Int.Eng., (1963), 1, p. call for the reaction of thionyl chloride on the hydrochlorides of amines at high temperature. It has been found that 1-phenyl-5-sulfinylamino pyrazoles can be prepared in quantitative yield, under mild conditions, from a compound of the general formula (II), with thionyl chloride and a

  catalytic amount of N, N dimethylformamide (DMF). To implement this

  When used, it is recommended to add the thionyl chloride at a temperature between -10 and + 25 ° C to the 1-phenyl-5-aminopyrazole derivative in the presence of DMF (1 to 5 mol%). It is desirable to employ 1.5 to 10 moles of thionyl chloride per mole of the compound of the general formula (II), preferably 2.5 to 5.0 moles. For example, the following procedure can be proposed: After stirring for 1 hour

  At room temperature, the excess of thionyl chloride is removed under pressure.

  The reaction product is reduced and the reaction product is treated and isolated with optimum yield by conventional methods in organic synthesis. Depending on the compound used as the starting material, those skilled in the art will adapt the parameters of the reaction to

  from the indications given above.

  The present invention relates more particularly to the preparation of the 5-amino-1-phenylpyrazole derivatives, the pyrazole ring of which contains substituents (A and B in formulas (I) and (II) above) electroattractants. The presence of

  these substituents decreases the reactivity of the amine function at the 5-position of the pyridine ring.

  zole. The phenyl ring, optionally substituted, at the 1-position of the pyrazole ring is part of the electron-withdrawing radicals, but NO 2 radicals can also be mentioned,

  CN, alkylsulfonyl, alkyloxycarbouyl or haloalkylsulphonyl.

  In this case, the method which is the subject of the invention makes it possible to obtain products which could not be prepared until today, by processes of the prior art, or which could not be prepared under satisfactory conditions (renders

ment, purity ...).

  The present invention also relates to products according to general formula (I) for which Z represents a radical selected from: - NC = O, -N = C = S, -N = S = O, and their implementation for obtaining the products according to general formula (I), for which A, B, R, R3, R4 and R5 are as defined above and Z represents a radical chosen from the groups: -NHC (= X); R6-, NHC (= O) -X-R6, -NHC (= S) -X-R6, -NHC (= X) NR7R8, -N = C = N-Het in which X is, R6 R7 Rs and Het have the same meaning as before, or Z represents the

1,2-thiazine-1-oxide-2-yl radical.

  The products corresponding to formula (I), in which Z represents a radical chosen from the groups: -N = C = O, -N = C = S, -N = S = O are particularly interesting because: have a parasiticidal and / or insecticidal activity, - they provide a route of access to numerous N-substituted 5-amino-1-phenylpyrazole derivatives, the efficacy of which has been demonstrated to be parasitic.

ticides and / or insecticides.

  The invention also relates to a process for the preparation of a compound corresponding to the general formula (III) (DERTVES AMTDES OR THTOAMTDES), X A B

É ,, 5

  wherein R 1, R 2, R 3, R 4 and R 5 are as defined above, X is oxygen or sulfur, which process is characterized by reacting a product corresponding to general formula (I), wherein Z represents the sequence -N = C = O or -N = C = S, with a compound of general formula R6M,

  wherein R6 has the same meaning as above and M represents an alkali metal

  lin like lithium or an alkaline earth metal salt such as MgBr, MgCl, MgI.

  To carry out this process, 1.0 to 125 mol of the compound according to the general formula R 6 M will preferably be employed per mole of the 1-phenyl-5- derivative.

  iso (thio) cyanatopyrazole, corresponding to the general formula (I). The reaction is usual-

  carried out at a temperature between -78 ° C and + 25 ° C, in a medium

  polar organic solvent. It is preferable to retain a solvent from tetrahydro-

  furan, diethyl ether, methyl tert-butyl ether, dimethyl ether,

o ethylene glycol.

  For example, if 1- (2,6-dichloro-4-trifluoromethylphenyl) 3-

  cyano-5-isocyanatopyrazole and phenylmagnesium bromide are used as reagents, the reaction can be schematized according to the following equation (eq.1)

CF3 53

    ## EQU1 ## and the resulting product isolated according to conventionally used methods.

in organic synthesis.

  The subject of the present invention is also the products corresponding to the general formula (III) in which:

  A and 11 represent, independently of one another: a hydrogen atom; a radical

  linear, branched or cyclic alkyl, alkenyl or alkynyl chain comprising from 1 to 12, preferably from 1 to 6, carbon atoms, the carbon chain of these radicals being

  which may be substituted by one or more groups selected from

  halo, alkyloxy, alkylthio, alkyloxycarbouyl, the alkyl radical of these radicals.

  caux, linear, branched or cyclic comprising from 1 to 6 carbon atoms; a halogen atom 2s chosen from fluorine, chlorine, bromine or iodine, a cyano radical, thio

  cyano, nitro, sulLamido, alkylamino, dialkylamino, aminocarbonyl, aminothio-

  carbouyl, alkylaminocarbouyl, alkylaminothiocarbonyl, dialkylaminocarbonyl, dialkylaminothiocarbonyl or alkylcarbouylamino or alkylthiocarbonylamino and wherein each alkyl radical, linear, branched or cyclic, saturated or unsaturated, comprises from 1 to 6 carbon atoms; a radical of general formula -S (O) "R in which n is equal to 0, 1 or 2, and R represents an alkyl radical, linear, branched or cyclic, saturated or unsaturated, comprising from 1 to 6 carbon atoms optionally substituted by one or more identical or different halogen atoms, with the proviso that A does not represent a group S (O) nR, a phenyl or phenylalkyl radical or a hetero ring containing from 4 to 7 ring members, and from 1 to 3 heteroatoms selected from nitrogen, sulfur, oxygen or silicon, the straight or branched chain alkyl moiety having from one to four carbon atoms and the phenyl or heterocycle portion being optionally substituted by one or more selected groups among the halogens, alkyls, haloalkyls, haloalkoxy, haloalkylthio, cyano, thio cyano, nitro, sultamido, aminocarbonyl, aminothiocarbonyl, alkylaminocarbonyl, alkylaminothiocarbonyl, dialkylaminocarbonyl radical, kylaminothiocarbonyl, in which the linear, branched or cyclic, saturated or unsaturated alkyl moiety comprises from 1 to 6 carbon atoms; R '. R :. R3. R. and Rs represent, independently of each other, an atom

  o hydrogen; a halogen atom; an alkyl, alkoxy, alkylthio, halogeno

  alkyl, haloalkoxy, haloalkylthio, and whose alkyl radical, linear, branched or

  cyclic, saturated or unsaturated, contains from 1 to 6 carbon atoms

  with one or more identical or different halogen atoms, X represents oxygen or sulfur, provided that:

  s When X = S; RG represents an alkyl, alkenyl or alkynyl radical, linear or branched

  embedded image, comprising from 5 to 12 carbon atoms, the carbon chain of these radicals being

  which may be substituted by one or more groups selected from

  halo, alkyloxy, alkylthio, alkyloxycarbouyl, the alkyl radical of these radicals.

  linear, branched or cyclic caux comprising 1 to 6 carbon atoms; and when X = O, A does not represent the hydrogen atom and R6 represents a linear, branched or cyclic alkyl, alkenyl or alkynyl radical comprising from 8 to 12 carbon atoms, the carbon chain of these radicals being capable of to be 1 1 substituted by one or more groups selected from the radicals: halo, alkyloxy, alkylthio, alkyloxycarbonyl, the alkyl radical of these radicals, linear, branched or cyclic comprising from 1 to 6 carbon atoms; a phenylalkyl radical comprising at least eight carbon atoms or a heterocycle having from 4 to 7 ring members, and from 1 to 3 heteroatoms selected from nitrogen, sulfur, oxygen or silicon, the straight chain alkyl part or branched having two to four carbon atoms? The phenyl or heterocyclic moiety being optionally substituted by one or more groups selected from halogen, alkyl, haloalkyl, haloalkoxy, haloalkylthio, cyano, thiocyano, nitro, aminocarbonyl, aminothiocarbonyl, alkylaminocarbonyl, alkylaminothiocarbonyl, dialkylaminocarbouyl, dialkylaminothiocarbonyl , halo, alkylsulfonyl or haloalkylsulfinyl and wherein the saturated or unsaturated, straight chain, branched or cyclic alkyl moiety comprises from one to four carbon atoms and the heterocyclic moiety optionally substituted with a phenyl radical itself substituted with. n or more identical or different groups chosen from halogen, alkyl, haloalkyl, haloalkoxy, haloalkylthio, cyano, thiocyano, nitro, aminocarbonyl, aminothiocarbonyl, alkylaminocarbonyl, alkylaminothiocarbonyl, dialkylaminocarbonyl, dialkylaminothiocarbonyl,

  haloalkylsulfonyl or haloalkylsulfinyl.

  The subject of the invention is also a process for the preparation of pyrazole derivatives having a (thio) urethane function in the 5-position, and corresponding to the general formula (IV) (URETHANE OR THIOURETHANES DERIVATIVES): ## STR2 ## in which A, B, R 1, R 3 and R 4 R "R 6 are as previously defined, and X and Y 2 are, independently of one another, oxygen or sulfur, which process is characterized in that a product having the general formula (I), wherein Z is -N = C = O or -N = C = S, is reacted with a compound of

general formula R6YH.

  The compounds according to the general formula R 6 YH, Y representing oxygen or sulfur, are known or can be prepared according to methods conventionally used in organic synthesis. The reaction can be conducted in the presence or absence of an inert organic solvent, at a temperature between -68 C and + C. To implement the process, it is advisable to employ 1.0 to 1.5 mole prêtreence of the compound according to the formula R6YH, per mole of the compound 1-phenyl-5-iso (thio) cyanatopyrazole corresponding to the formula (I), or more precisely 1.1 to 1.25

  moles per mole according to a purported embodiment of the invention. -

  For example, if 1- (2,6-dichloro-4-trifluoromethyl)

  phenyl) -3-cyano-5-isothiocyanatopyrazole and 2,2,2-trifluoroethanol, the reaction can be schematized according to equation 2 (eq.2):

_CN CF3CH2O-C _

  SCN N + CF3CH2OH H N (eq.2) a:, cl a:, a

CF3 CF3

  The products of the reaction are isolated and purified according to techniques known to those skilled in the art, for example by washing the reaction medium with water, removal of the organic solvent, recrystallization and drying of the product under

partial vacuum.

  The subject of the present invention is also the products corresponding to formula IV above, in which: A and B represent, independently of one another: a hydrogen atom; a linear, branched or cyclic alkyl, alkenyl or alkynyl radical comprising from 1 to 12, preferably from 1 to 6, carbon atoms, the carbon chain of these radicals being capable of being substituted by one or more chosen groups among the radicals: halo, alkyloxy, alkylthio, alkyloxycarbonyl, the alkyl radical of these radicals, linear, branched or cyclic comprising from 1 to 6 carbon atoms; an atom

  halogen selected from fluorine, chlorine, bromine or iodine; a cyano radical, thio-

  cyano, nitro, sulfamido, alkylamino, dialkylamino, aminocarbonyl, aminothio-

  carbonyl, alkylaminocarbonyl, alkylaminothiocarbonyl, dialkylaminocarbonyl, dialkylaminothiocarbonyl or alkylcarbonylamino or alkylthiocarbonylamino and wherein each alkyl radical, linear, branched or cyclic, saturated or unsaturated, comprises from 1 to

  6 carbon atoms; a phenyl or phenylalkyl radical or a heterocycle comprising

  from 4 to 7 members, and from 1 to 3 heteroatoms selected from nitrogen, sulfur, oxygen or silicon, the straight or branched chain alkyl portion having from one to four carbon atoms and the phenyl or heterocycle being optionally substituted with one or more groups chosen from halogens, alkyls,

  haloalkyls, haloalkoxy, haloalkylthio, cyano radical, thioalkyl

  cyano, nitro, sulfamido, aminocarbonyl, aminothiocarbonyl, alkylaminocarboyyl, alkylaminothiocarbonyl, dialkylaminocarbonyl, dialkylaminothiocarbonyl, the linear, branched or cyclic alkyl moiety of which, saturated or unsaturated, comprises from 1 to 6 carbon atoms, B may also represent a radical of formula general S (O) nR wherein n is 0, 1 or 2, and R represents an alkyl radical, linear, branched or cyclic, saturated or unsaturated, comprising from 1 to 6 carbon atoms optionally substituted by one or more atoms identical or different halogen; R, R, R3. 1 and R. represent, independently of each other, an atom

  hydrogen; a halogen atom; an alkyl, alkoxy, alkylthio, halogeno

  alkyl, haloalkoxy, haloalkylthio, and the alkyl radical, linear, branched or

  cyclic, saturated or unsaturated, contains from 1 to 6 carbon atoms

  with one or more identical or different halogen atoms, X and Y are chosen so that: (X = O and Y = S) or (X = S and Y = O) and R D represents an alkyl radical, alkenyl or alkynyl, linear, branched or cyclic, comprising from 1 to 12, preferably from 1 to 6, carbon atoms, the carbon chain of these radicals being capable of being substituted by one or more groups chosen from the radicals: halo alkyloxy, alkylthio, alkyloxycarbonyl, the alkyl radical of these radicals, linear, branched or cyclic comprising from 1 to 6 carbon atoms; a phenyl or phenylalkyl radical or a heterocycle having from 4 to 7 shafts, and from 1 to 3 heteroatoms selected from nitrogen, sulfur, oxygen or silicon, the straight or branched chain alkyl moiety having from one to four atoms carbon, the phenyl or heterocyclic portion being optionally substituted by one or more groups selected from halogens, alkyls, haloalkyls, halo-enoalkoxy, halo-genoalkylthio, radially cyano, thiocano, nitro, amino -

  carbonyl, aminothiocarbonyl, alkylaminocarbouyl, alkylaminothiocarbonyl, dialkyl,

  kylaminocarbonyl, dialkylaminothiocarbonyl, halo, alkylsulfonyl or haloalkyl

  genoalkylsulfinyl and of which the straight-chain, branched or cyclic alkyl moiety

  The unsaturated or unsaturated group comprises from one to four carbon atoms and the hetero-cyclic portion optionally substituted by a phenyl radical itself substituted with one or more identical or different groups chosen from halogens, alkyls, and the like.

  haloalkyls, haloalkoxy, haloalkylthio, cyano radical, -thio-

  cyano, nitro, aminocarbonyl, aminothiocarbonyl, alkylaminocarbonyl, alkylamino

  thiocarbouyl, dialkylaminocarbonyl, dialkylaminothiocarbonyl, haloalkylsulioyl or haloalkylsulfinyl, that is (X = O and Y = O) and R represents a linear, branched or cyclic alkyl, alkenyl or alkynyl radical comprising from 8 to 12 carbon atoms, the carbon chain these radicals being capable of being substituted by one or more groups chosen from the radicals: halo, alkyloxy, alkylthio, alkyloxycarbonyl, the alkyl radical of these radicals, linear, branched or cyclic comprising from 1 to 6 carbon atoms; a phenyl or phenylalkyl radical or a heterocycle having from 4 to 7 shafts, and from 1 to 3 heteroatoms selected from nitrogen, sulfur, oxygen or silicon, the straight or branched chain alkyl portion having from one to four atoms carbon, the phenyl or heterocyclic portion being optionally substituted by one or more groups selected from halogens, alkyls, haloalkyls, haloalkoxy, lalogenoalkylthio, cyano, thiocyano, nitro, aminocarbonyl,

  aminothiocarbonyl, alkylaminocarbouyl, alkylaminothiocarbonyl, dialkyl-

  aminocarbonyl, dialkylaminothiocarbonyl, halo, alkylsulfonyl or halo

  o genoalkylsulfinyl and whose straight-chain, branched or cyclic alkyl part, saturated

  of 1 to 4 carbon atoms and the hetero

  cyclic optionally substituted with a phenyl radical itself substituted by one or more identical or different groups chosen from halogens, alkyls,

  haloalkyls, haloalkoxy, haloalkylthio, cyano, thio-

  cyano, nitro, aminocarbonyl, aminothiocarbonyl, alkylaminocarbonyl, alkylamino

  thiocarbonyl, dialkylaminocarbonyl, dialkylaminothiocarbouyl, haloalkyl

  sulfonyl or haloalkylsulfinyl.

  The subject of the invention is also a process for the preparation of phenylpyrazole derivatives having a (thio) urea function at the 5-position and corresponding to the general formula (V) (UERED DERIVATIVES or THIOURES): X A s

R7-N H'N

Rs R 'R,

R2 R4

  R3 o wherein A, B. R1 R2. R 3 R 4 R 5, R 7 and R 8 are as defined above, and X represents oxygen or sulfur, this process being characterized in that a product corresponding to the general formula (I), in which Z represents chaining-N = C = 0 or -N = C = S, with a compound of general formula

R7RgNH.

  To carry out the process, it is preferable to employ 1.0 to 1.25 moles of the compound according to the general formula R7RgNH per mole of the 1-phenyl-5-iso (thio) cyanatopyrazole derivative corresponding to the general formula (I). The reaction is advantageously carried out in an inert organic solvent, preferably chosen from toluene, dichloromethane, dichloroethane and chlorobenzene, used alone or in combination, at a temperature of between -78 ° C. and + 100 ° C., and advantageously between -20 C and +50 C according to a preferred embodiment

of the invention.

  For example, the commitment of 1- (2,6-dichloro-4-trifluoromethyl) -3-cyano-trifluoromethylthio-5-isocyanatopyrazole and ammonia according to the above-mentioned reaction can be schematized according to Equation 3 (eq. 3): F; iCF3

CN CN

N + NH, H H <N (eq., CI4c '1' CI:, c '

CF3 CF3

  According to a particular embodiment of the present invention, the compounds corresponding to the general formula (V) for which R7 is hydrogen and Rs represents the 1-phenyl-pyrazol-5-yl unit, may advantageously be prepared by reacting the 1-phenyl-5iso (thio) cyanatopyrol derivatives corresponding to the general formula (I) with a 1-phenyl-5-amino-pyrazole compound corresponding to the general formula (II). N. N'-bis (1-phenyl-pyrazol-5-yl) ureas are new products and constitute a new class of pyrazole derivatives with parasiticidal activity and

  insecticide. For example, N. N'-bis [1- (2,6-dichloro-4-trifluoromethylphenyl) -3-

  cyano-4-trifluoromethylsulfinyl) pyrazol-5-ylurea may be prepared according to the process according to the present invention, according to the reaction shown schematically according to equation 4 (eq.

F3 ICF3 ICF3 ICF3

  o =: CN o =: CN CN / S = 0 O-CN OCN N + H2N N N N N eq.4

N N N C N

c ':, c' c'4, c C'43, C '0 c'Cll, a

CF3 CF3 CF3 CF3

  According to a purported embodiment of the present invention, the

  reaction is carried out without isolating the 1-phenyl-5-iso (thio) cyanatopyrazole derivative

  Formula (I), casting a solution of the pyrazole derivative according to formula (II), in the presence of an acid acceptor, in an inert high boiling solvent, preferably toluene or chlorobenzene. , on a refrigerant solution of phosgene or thiophosgene in the same solvent. After maintaining stirring for 1 hour at room temperature, the excess of (thio) phosgene is removed under reduced pressure and a suitable amount of 1-phenyl-5-aminopyrazole derivative, corresponding to the general formula (II) is added to the reaction mixture. The resulting product can be isolated and purified by methods conventionally used by those skilled in the art, and this with

  a virtually quantitative yield.

  According to a particular embodiment of the present invention, the salts such as that exemplified can be easily prepared by the reaction of two

  equivalents of compounds according to general formula (I), for which Z represents -

  N = C = 0 or -N = C = S with one equivalent of pyridine, followed by hydrolysis of the intermediate addition compound (eq.5): CN CN NC NCCN H, O OCNN ## STR2 ## ## STR2 ##

F F3 F3 F3

O O

NC H C 'CN

N N!, 1;> py - =

Cl <> CI ô CI (, C '-

CF3 CF3

  The present invention also relates to the products of general formula (V), as defined above, in which: A and B represent, independently of one another: a hydrogen atom; a linear, branched or cyclic alkyl, alkenyl or alkynyl radical comprising from 1 to 12, preferably from 1 to 6, carbon atoms, the carbon chain of these radicals being

  t5 may be substituted by one or more groups selected from among the radi-

  halo, alkyloxy, alkylthio, alkyloxycarbonyl, the alkyl radical of these radicals.

  caux, linear, branched or cyclic comprising from 1 to 6 carbon atoms; an atom

  halogen selected from fluorine, chlorine, bromine or iodine; a cyano radical, thio-

  cyano, nitro, sulfamido, alkylamino, dialkylamino, aminocarbonyl, aminothiocarbo

  alkylaminocarbonyl, alkylaminothiocarbonyl, dialkylaminocarbonyl, dialkylaminocarbonyl,

  kylaminothiocarbouyl or alkylcarbonylamino or alkylthiocarbonylamino and whose claque remains alkyl, linear, branched or cyclic, saturated or unsaturated, comprises from 1 to

  6 carbon atoms; a phenyl or phenylalkyl radical or a heterocycle comprising

  from 4 to 7 chain members, and from 1 to 3 heteroatoms selected from nitrogen, sulfur, oxygen or silicon, the straight or branched chain alkyl portion having from one to

  four carbon atoms and the phenyl or heterocycle portion being optionally

  substituted with one or more groups selected from halogens, alkyls,

  hal o genoalkyl es, halo genoalkoxy, halo genoalkylthi o, rad cyano, thio -

  cyano, nitro, sulfamido, aminocarbonyl, aminothiocarbonyl, alkylaminocarbouyl, alkylaminothiocarbonyl, dialkylaminocarbonyl, dialkylaminothiocarbonyl, whose linear, branched or cyclic alkyl moiety, saturated or unsaturated, comprises from 1 to 6 carbon atoms, B may also represent a radical of general formula -S (O) nR in which n is equal to 0, 1 or 2, and R represents a saturated or unsaturated, linear, branched or cyclic alkyl radical comprising from 1 to 6 carbon atoms optionally substituted with one or several identical or different halogen atoms; R ', R2, R3' R4 and R; represent, independently of each other, an atom

  hydrogen; a halogen atom; an alkyl, alkoxy, alkylthio, halogeno

  alkyl, haloalkoxy, haloalkylthio, and the alkyl radical, linear, branched or

  cyclic, saturated or unsaturated, contains from 1 to 6 carbon atoms

  When taken together with one or more identical or different halogen atoms, R7 and R5 represent, independently of one another, the hydrogen atom or a linear, branched or cyclic alkyl, alkenyl or alkynyl radical comprising from 1 to 12, preferably from 1 to 6, carbon atoms, the carbon chain of these radicals being capable of being substituted by one or more groups chosen from the radicals: halo, alkyloxy, alkylthio, alkyloxycarbouyl, the alkyl radical of these o radicals, linear, branched or cyclic comprising from 1 to 6 carbon atoms; a phenyl or phenylalkyl radical or a heterocycle having from 4 to 7 members, and from 1 to 3 heteroatoms selected from nitrogen, sulfur, oxygen or silicon, the straight or branched alkyl portion having from one to four atoms carbon, the phenyl or heterocyclic portion being optionally substituted by one or more groups selected from halogens, alkyls, haloalkyls, haloalkoxy, haloalkylthio, cyano, thiocyano, nitro, aminocarbonyl,

  aminotliocarbonyl, alkylaminocarbonyl, alkylaminothiocarbonyl, dialkyl-

  aminocarbouyl, dialkylaminothiocarbonyl, halo, alkylsulfonyl or halogeno

  alkylsulfinyl and whose straight chain, branched or cyclic, saturated or unsaturated alkyl part comprises from one to four carbon atoms and the heterocyclic part

  optionally substituted with a phenyl radical itself substituted by one or more

  the same or different groups selected from halogens, alkyls, haloalkyls, haloalkoxy, haloalkylthio, cyano, thio cyano, nitro, aminocarbonyl, aminothiocarbonyl, alkylaminocarbonyl, alkylaminothiocarbonyl, alkylaminocarbonyl, dialkyaminothiocarbonyl, halo The present invention further relates to the products of general formula (V), as defined above, in which: A and B represent, independently of each other: an atom of at least one carbon atom; hydrogen; a linear, branched or cyclic alkyl, alkenyl or alkynyl radical comprising from 1 to 12, preferably from 1 to 6, carbon atoms, the carbon chain of these radicals being capable of being substituted by one or more groups selected from the radicals: halo, alkyloxy, alkylthio, alkyloxycarbonyl, the alkyl radical of these radicals, linear, branched or cyclic comprising from 1 to 6 carbon atoms; a halogen atom selected from fluorine, chlorine, bromine or iodine; a cyano, thio cyano, nitro, sultamido, alkylamino, dialkylamino, aminocarbonyl, aminothiocarbonyl, alkylaminocarbonyl, alkylaminothiocarbonyl, dialkylaminocarbonyl, dialkylaminothiocarbonyl or alkylcarbonylamino or alkylthiocarbonylamino radical and each of which is linear, branched or cyclic, saturated or unsaturated, 1 to 6 carbon atoms; a radical of general formula S (O) nR in which n is equal to O. 1 or 2, and R represents an alkyl radical, linear, branched or cyclic, saturated or unsaturated, comprising from 1 to 6 carbon atoms optionally substituted by one or more identical or different halogen atoms; a phenyl or phenylalkyl radical or a heterocycle comprising from 4 to 7 members, and from 1 to 3 heteroatoms chosen from nitrogen, sulfur, oxygen or silicon, the straight or branched alkyl portion having from one to four carbon atoms and the phenyl or heterocycle part being optionally substituted with one or more groups selected from halogens, alkyls, haloalkyls, haloalkoxy, haloalkylthio, cyano, thiocyano, nitro, sulfamido, aminocarbonyl, aminothiocarbonyl, alkylaminocarbonyl radical, alkylaminothiocarbonyl, dialkylaminocarbonyl, dialkylaminothiocarbonyl, whose linear, branched or cyclic, saturated or unsaturated alkyl moiety comprises from 1 to 6 carbon atoms, R 'R', R3, R '; and Rs represent, independently of one another, a hydrogen atom; a halogen atom; an alkyl, alkoxy, alkylthio, haloalkyl, haloalkoxy or haloalkylthio radical, and whose alkyl radical, linear, branched or

  cyclic, saturated or unsaturated, contains from 1 to 6 carbon atoms

  with one or more identical or different halogen atoms, R7 represents the hydrogen atom and Rs represents a heterocycle of the general formula s (I) in which A, B, R, R2, R3, R4, and Rs have the same definition as above,

  while Z represents a bond.

  The subject of the invention is also a process for the preparation of pyrazole derivatives incorporating a carbodiimide functionality and corresponding to the general formula (VI) (N.sup. N '(PYR.ZOL-5-YL) CARBODIII \ IIDES), in which formula A, B, R R, R2 R3 R4 and Rs are as previously defined ::

B: A A B

R1 C R5 q R1

R3 R3

  (VI) wherein said process is characterized by reacting a product of the general formula (I) wherein Z is-N = C = O or -N = C = S, together with

  3-methyl-1-phenyl-3-phospholene-1 -oxide.

  To implement the process, which proceeds via an imino-de-oxo

  The bisubstitution will preferably involve 1.0 to 1.20 moles of the compound of the above general formula (I) in an inert atmosphere with 0.04 to 0.06 moles of the phospholene derivative. The reaction is usually carried out at a temperature of between + 20 ° C. and + 80 ° C., preferably around + 50 ° C. It should be noted that the same products according to the general formula (VI) are accessible from the products corresponding to general structure (V) by dehydration or desulfurisatrion conducted with name,. many reagents such as metal oxides, sodium hypochlorite, pentachloride

  phosphorus, paratoluenesulfonic acid chloride.

  For example, if 1- (2,6-dichloro-4-trifluoromethylphenyl) -3-

  cyano-4-trifluoromethylsulfinyl-5-isocyanatopyrazole is used with the phosphonyl derivative

  In the abovementioned pholene, the reaction can be schematized according to the following equation (eq 6):

0 0 0

  F3C p NC CF3 F3C CN): ## STR1 ##

F3C CF3 CF3

  (Eq 6) The invention further relates to pyrazole derivatives incorporating a carbodiimide functionality and corresponding to the general formula (VI), in which formula A, B, R 2, R 3, R 4 and R 4 are as defined above. These compounds

  are new and particularly interesting as parasiticides and / or insecticides.

  cides. The subject of the invention is also a process for the preparation of N-alkylsulfinyl, N-phenylsulphinyl, N-heteroalkylsulfinyl derivatives, variously substituted for 1-phenyl-5-aminopyrazoles, these derivatives corresponding to formula (VII)

  (ALKYL (PHENYL, HETERYL) SULFINYLAMINO-1-PHENYL PYRAZOLE DERIVATIVES)

  below, in which A, B, R, R3, R4, R5 and R6 are as previously defined: A B

R6 S N / N

R -, R5

R2 \ R4

  R3 (VII) s this process being characterized by reacting a product of the general formula (I) wherein Z represents the sequence -N = S = O, with a compound of the general formula R6M, formula in which M represents an alkali metal such as

* lithium or an alkaline earth metal salt such as MgBr, MgCl, MgI.

  The organometallic compounds of general formula R6M are

  known or can be obtained by conventional methods in Organic Synthesis.

  The corresponding perfluoroalkyl derivatives are particularly useful for the synthesis of compounds of general formula (VII) and can be readily prepared by methods described in the literature (see, for example, D. BURTON et al., "Fluorinated Organometallics", in Tetrahedron, 48, p. 189, (1992)). To carry out the process, it is desirable to bind 1.0 to 1.25 moles of the compound of the general formula R 6 M to 1 mole of the 1-phenyl-5- (N-sulfinylamino) pyrazole derivative according to the general formula (I). . The reaction is. preferably, carried out at a temperature of between -78 ° C. and + 25 ° C., in polar preference solvents and chosen from tetrahydrofuran, ethers, such as diethyl ether, methyl tert-butyl ether and methyl diethyl ether. ethylene glycol. For example, the reaction between [1- (2,6-dichloro-4-trifluoromethylphenyl) -3-cyano-5- (N-sulfinylamino) pyrazole and iodide of heptafluoropropyl magnesium may be represented by the equation following (eq.7):

CN O CN

/ \ / N F3CF2CF2C \ NH

OSN N N

  C1 Cl CF3cF2cF2MglCl1C CF3 (Eq.7) CF3 The reaction product is isolated and purified by the techniques

known to those skilled in the art.

  The subject of the present invention is also the products corresponding to the general formula (VII) as defined above, in which: A and B represent, independently of one another: a hydrogen atom; a linear, branched or cyclic alkyl, alkenyl or alkynyl radical comprising from 1 to 12, preferably from 1 to 6, carbon atoms, the carbon chain of these radicals being

  which may be substituted by one or more groups selected from

  halo, alkyloxy, alkylthio, alkyloxycarbonyl, the alkyl radical of these radiocals, linear, branched or cyclic comprising from 1 to 6 carbon atoms; an atom

  halogen selected from fluorine, chlorine, bromine or iodine; a cyano radical, thio-

  cyano, nitro, sulLamido, alkylamino, dialkylamino, aminocarbonyl, aminothiocarbo-

  ilyl, alkylaminocarbonyl, alkylaminothiocarbonyl, dialkylaminocarbonyl, dialkylaminothiocarbonyl or alkylcarbonylamino or alkylthiocarbonylamino and wherein each alkyl radical, linear, branched or cyclic, saturated or unsaturated, comprises from 1 to 6 carbon atoms; a radical of general formula S (O) nR in which n is equal to 0, 1 or 2, and R represents a saturated or unsaturated, linear, branched or cyclic alkyl radical comprising from 1 to 6 carbon atoms optionally substituted with one or more identical or different halogen atoms; a phenyl or phenyl radical

  o alkyl or a heterocycle comprising from 4 to 7 members, and from 1 to 3 heteroatoms selected

  Nitrogen, sulfur, oxygen or silicon, the straight or branched chain alkyl portion having one to four carbon atoms and the phenyl or heterocycle portion

  being optionally substituted by one or more groups selected from

  genes, alkyls, haloalkyls, haloalkoxy, haloalkylthio, cyano, thiocyano, nitro, sulfamido, aminocarbouyl, aminothiocarbonyl,

  alkylaminocarbonyl, alkylaminothiocarbonyl, dialkylaminocarbonyl, dialkyl-

  aminothiocarbonyl, wherein the linear, branched or cyclic, saturated or unsaturated, alkyl moiety comprises from 1 to 6 carbon atoms, R, R2, R3, R3 and R5 are, independently of one another, an atom

  hydrogen; a halogen atom; an alkyl, alkoxy, alkylthio, halogeno

  alkyl, haloalkoxy, haloalkylthio, and the alkyl radical, linear, branched or

  cyclic, saturated or unsaturated, contains from 1 to 6 carbon atoms

  by one or more identical or different halogen atoms, Rc represents a linear, branched or cyclic alkyl, alkenyl or alkynyl radical comprising from 1 to 12, preferably from 1 to 6, carbon atoms, the carbon chain one of these radicals being capable of being substituted by one or more groups chosen from the radicals: halo, alkyloxy, alkylthio, alkyloxycarbonyl, the alkyl radical of these radicals, linear, branched or cyclic comprising from 1 to 6 carbon atoms ; a phenyl or phenylalkyl radical or a heterocycle having from 4 to 7 shafts, and from 1 to 3 heteroatoms selected from nitrogen, sulfur, oxygen or silicon, the straight or branched chain alkyl moiety having from one to four atoms carbon, the phenyl or heterocyclic portion being optionally substituted by one or more groups selected from halogens, alkyls, haloalkyls,

  haloalkoxy, haloalkylthio, cyano, thiocyano, nitro, amino-

  carbonyl, aminothiocarbonyl, alkylaminocarbonyl, alkylaminothiocarbonyl,

  dialkylaminocarbonyl, dialkylaminothiocarbonyl halogenoalkylsulphonyl, or halogenated

  genoalkylsulfinyl and of which the straight, branched or cyclic alkyl moiety

  The unsaturated or unsaturated group comprises from one to four carbon atoms and the hetero ring part optionally substituted by a phenyl radical itself substituted by one or more identical or different groups chosen from halogens, alkyls,

  haloalkyls, haloalkoxy, haloalkylthio, cyano radical, thioalkyl

  cyano, nitro, aminocarbonyl, aminothiocarbouyl, alkylaminocarbonyl, alkyl

  aminothiocarbonyl, dialkylaminocarbonyl, dialkylaminothiocarbouyl, halo

  o alkylsulfonyl or haloalkylsulfinyl.

  The subject of the invention is also a process for the preparation of 3,6-dihydro-N- (1-phenylpyrazol-5-yl) -1,2-thiazine-1-oxide derivatives corresponding to

  general formula (VIII) (3,6-DIHYDRO-N (1-PHENYLPYRAZOL-5- DERIVATIVES

  YL) 1,2-THIAZINE-1-OXYDE) in which A, B.sub.R.sub.2 R.sub.3 R.sub.3 R.sub.Rs are as previously defined and R.sub.2, R.sub.2, R.sub.2 and R.sub.2 represent, independently of each other: hydrogen ; a linear, branched or cyclic, optionally unsaturated, alkyl radical containing from 1 to 12, preferably from 1 to 6, carbon atoms; a halo radical o A B

-:/ NOT-

<10 / l

R2 R4

R3

(VIII)

  genoalkyl whose branched or cyclic linear alkyl moiety, optionally unsaturated, having from 1 to 12, preferably from 1 to 6, carbon atoms; an alkoxyl radical whose branched or cyclic linear alkyl moiety, optionally unsaturated, contains from 1 to 12, preferably from 1 to 6, carbon atoms, this process being characterized in that a product corresponding to the general formula (I) in which Z represents the sequence -N = S = O with a compound of formula

general R9CH = CRo - CR = CHR2.

  Derivatives of general formula R9CH = CR'o-CR = CR2 are

  known or can be obtained according to techniques known to those skilled in the art.

  To carry out the process, it is preferable to engage 1.0 to 3.0 moles of the compound of the general formula RgCH = CRo-CR = CR'2 for 1.0 mole of the 1-phenyl-5- (N) derivative. -sulfinylamino) pyrole according to general formula (I). The reaction is preferably carried out at a temperature of from + 25 ° C to + 120 ° C in inert solvents selected from dichloroethane, toluene or chlorobenzene.

  For example, the reaction between 1- (2,6-dichloro-4-trifluoromethyl)

  phenyl) -3-cyano-4-trifluoromethylsulfinyl-5- (N-sulfinylamino) pyrazole and 2,3-dimethylbutadiene can be schematized according to the following equation (eq 8): ## STR2 ## GN ,: F3C-; l H3C '-C i 1 (Eq. e}

  The invention furthermore relates to 3,6-dihydro-N- (1-

  phenylpyrazol-5-yl) -1,2-thiazine-1-oxide having the general formula (VIII) in

  wherein A, B, R, R, R, R, R, R, R and R are as previously defined.

  These compounds are new and particularly interesting as parasiticides

and / or insecticides.

  The invention also relates to a process for the preparation of 1-phenyl-5- (alkylamino) -pyrazole derivatives corresponding to the general formula (IX)

  (1-PHENYL-5- (N-ALKYLAMINO) PYRAZOLES DERIVATIVES):

/

R12 R10 R1, R5

  Wherein R 1, R 2, R 3, R 4, R 5 and R 6, R 10, R 1 and R 12 are as defined above, which process is characterized in that the alkaline hydrolysis is carried out 'a

  compound of the general formula (VIII) defined above.

  To carry out the process, it is preferable to use 1.0 to 2.5 moles of sodium hydroxide per mole of compound according to general formula (VII). The reaction is preferably carried out at a temperature of between + 20 ° C. and + 75 ° C., in polar preterence solvents, such as, for example, the tetra

  hydrofuran, dioxane, ethanol or water and mixtures thereof.

  For example, the reaction retaining 3,4-dihydro-4,5-dimethyl-N- [1 (2,6-dichloro-4-trifluoromethylphenyl) -3-cyano-4- (trifluoromethylsulphenyl) pyrazol-yl) -1 2-thiazine-1-oxide as starting material can be schematized according to the following equation (eq 9): ## STR2 ## ## STR2 ##

CH3 CF3

  CF3 (Eq.9) The reaction products are generally treated; isolated and sealed by the techniques known to those skilled in the art, for example by washing with water the reaction mixture, removal of the organic solvent, drying under pressure

reduced, and recrystallization.

  The subject of the present invention is also the compounds of formula (IX) in which: A, R, R 2, R 3, R 4, R 4 and R 6 are as defined above, wherein R ', R', R '' and R '2 represent, independently of one another: hydrogen; a linear, branched or cyclic, optionally unsaturated, alkyl radical containing from 1 to 12, preferably from 1 to 6, carbon atoms; a haloalkyl radical whose branched or cyclic linear alkyl moiety, optionally unsaturated, having from 1 to 12, preferably from 1 to 6, carbon atoms; an alkoxyl radical whose branched or cyclic linear alkyl moiety, optionally unsaturated, having from 1 to 12, preferably from 1 to 6, carbon atoms; At least one of R9, Ro, R and R2 is alkyl or haloalkyl and the sum of the number of carbon atoms of the radicals is alkyl or halo;

  alkyl is greater than or equal to 3.

  The present Application also relates to new products obtained in this process and to their use for their insecticidal and anti-parasitic activities. The present Application also relates to new products obtelus by such a method. Among these products corresponding to the general formula (I), the preferred compounds are those for which: A represents a halogen or an alkylthio / alkylsulfinyl / alkylsulfonyl group, unsubstituted or substituted, preferably with halogens. More particularly, the trifluoromethylthio and trifluoromethylsulfinyl groups,

  B represents a cyano, carboxamido, thiocarboxamido, methyl or tri-

  fluoromethyl, - Z represents a group -N = C = O or a group -N = C = S, o - the substituents R, R2 R3 R4, Rs determine in position 1 of the pyrazole structure the

  substituted 2,4,6-trichlorophenyl, 2,6-dichloro-4-trifluoromethylphenyl, 2, -6-

  dichloro-4-trifluoromethyloxyphenyl and 2,6-dichloro-4-trifluoromethylthiophenyl.

  Among the so-called precursor compounds thus defined, intermediate products as functionalised products at the 5-position of the pyrazole ring, the following products can be detailed:

  product 1: 1- (2,6-dichloro-4-trifluoromethylphenyl) -3-cyano-4-trifluoro-

  methylsulfinyl -5-isocyanato-pyrazole;

  product 2: 1- (2,6-dichloro-4-trifluoromethylphenyl) -3-cyano-4-trifluoro-

  methylsulfenyl-1-isocyanato-pyrazole; o - product 3: 1- (2,6-dichloro-4-trifluoromethylphenyl) -3-methyl-4-trifluoromethylsulfenyl-5-isocyanatopyrazole; product 4: 1- (2,6-dichloro-4-trifluoromethylphenyl) -3-methyl-4-trifluoromethylsulfinyl-5-isocyanato-pyrazole; product 5: 1- (2,6-dichloro-4-trifluoromethylphenyl) -3-cyano-4-trifluoromethylsulphonylamine; product 6: 1- (2,6-dichloro-4-trifluoromethylphenyl) -3-cyano-4-trifluoromethyl-5-isocyanato-pyrazole; product 7: 1- (2,6-dichloro-4-trifluoromethylphenyl) -3-trifluoromethyl-4-trifluoromethylsulfenyl-5-isocyanato-pyrazole; 8: 1- (2,6-dichloro-4-trifluoromethylphenyl) -3-trifluoromethyl-4-trifluoromethylsulfinyl-5-isocyanato-pyrazole; product 9: 1- (2,4,6-trichlorophenyl) -3-cyano-4-trifluoromethylsulfinyl-5-isocyanato pyrazole; product 1 0: 1- (2,4,6-trichlorophenyl) -3-cyano-4-trifluoromethylsulfenyl-5-isocyanato-pyrazole; s - 1: 1- (2,6-dichloro-4-trifluoromethylphenyl) -3-cyano-4-chloro-5-isocyanato-pyrazole; 1: 2 - (2,4,6-trichlorophenyl) -3-cyano-4-bromo-5- (N-sulphinylamino) pyrazole; product 1 3: 1- (2,4,6-trichlorophenyl) -3-cyano-4-trifluoromethylthio-5- (N-sulphinylamino) -pyrazole; product 1 4: 1- (2,6-dichloro-4-trifluoromethylphenyl) -3-cyano-4-chloro-5- (N)

sulfinylamino) -pyrazole; - = -

  product 1,5: 1- (2,6-dichloro-4-trifluoromethylphenyl) -3-cyano-4-bromo-5- (N-sulfinylamino) pyrazole; 16: 1- (2,6-dichloro-4-trifluoromethylphenyl) -3-cyano-4-trifluoromethylthio- (N-sulfinylamino) pyrazole product; 17: 1- (2,6-dichloro-4-trifluoromethylphenyl) -cycyano-4-trifluoromethylsulfinyl-5- (N-sulfinylamino) pyrazole; - product 18: N, N, -dimethyl-N '[1- (2,6-dichloro-4-trifluoromethylphenyl) -3-cyanopyrazol-5-yl] thiourea; product 19: N- (3,5-bis (trifluoromethyl) phenyl) -N '- [1- (2,6-dichloro-4-trifluoromethylphenyl) -3-cyanopyrazol-5-yl] urea; product 20: N- (2,6-dichloro-4-trifluoromethylphenyl) -N '- [1- (2,6-dichloro-4-trifluoromethylphenyl) -3-cyanopyrazol-5-yl] urea; 2s - product 2 1: N- (2-trifluoromethyl-4-nitrophenyl) -N '- [1- (2,6-dichloro-4-trifluoromethylphenyl) -3-cyanopyrazol-5-yl] urea; product 22: N, N'bis [1- (2,6-dichloro-4-trifluoromethylphenyl) -3-cyano-4-trifluoromethylpyrazol-5-yl] urea; product 23: N, N '[1- (2,6-dichloro-4-trifluoromethylphenyl) -3-cyano-4-trifluoromethylsulphinylpyrazol-5-yl] carbodiimide; product 24: 1- (2,6-dichloro-4-trifluoromethylphenyl) -3-cyano-5- (N-heptafluoropropylsulfinylamino) -pyrazole; product 25: 3,6-dihydro-4,5-dimethyl-N- (1- (2,6-dichloro-4-trifluoromethylphenyl) -3-cyano-4-trifluoromethylsulfinyl-pyrazol-5-yl) -1,2-thiazine-1 -oxide; 26: 3,6-dihydro-4,5-dimethyl-N- (1- (2,4,6-trichlorophenyl) -3-cyanopyrazol-yl) -1,2-thiazine-1 -oxide; s - product 27: 3,6-dihydro-4,5-dimethyl-N- (1- (2,4,6-trichlorophenyl) -3-cyano-4-bromopyrazol-5-yl) 1,2-thiazine-1 -oxide; product 28: 3,6-dihydro-4,5-dimethyl-N- (1- (2,4,6-trichlorophenyl) -3-cyano-4-trifluoromethylthiopyrazol-5-yl) 1,2-thiazine-1 -oxide ; 29: 3,6-dihydro-4,5-dimethyl-N- (1- (2,6-dichloro-4-trifluoromethyl-phenyl) -3-cyanopyrazol-5-yl) -1,2-thiazine-1 -oxide; product 30: 3,6-dihydro-4,5-dimethyl-N- (1- (2,6-dichloro-4-trifluoromethylphenyl)

  3-cyano-4-bromopyrazol-5-yl) -1,2-thiazine-1 -oxide; = -

  product 31: 3,6-dihydro-4,5-dimethyl-N- (1- (2,6-dichloro-4-trifluoromethylphenyl) 3 -cyano-4- (trifluoromethylthio) pyrazol-5-yl) 1,2-thiazine; 1 -oxide; product 32: 1- (2,6-dichloro-4-trifluoromethylphenyl) -3-cyano-5- (2,3-dimethylbut-3-enyl) aminopyrazole; 3: 1 (2,6-dichloro-4-trifluoromethylphenyl) -3-cyano-4- (trifluoromethylsulphinyl) -5- (2,3-dimethylbut-3-en-1-yl) aminopyrazole; 34: 1- (2,6-dichloro-4-trifluoromethylphenyl) -3-cyano-4- (trifluoromethylthio) -5- (2,3-dimethylbut-3-en-1-yl) aminopyrazole; These processes, the products corresponding to the general formula (I), as well as their uses, will be described and exemplified. It should be remembered that, in the description of the processes, it is not essential to isolate the reaction intermediates to carry out the synthesis of the 1-phenylpyrazole derivatives described. Moreover, he

  It must be kept in mind that the following descriptions are presented so that the pre

  This invention is better understood and should in no way limit its scope.

  Various modifications and arrangements can be considered without altering the spirit. The compounds according to the invention can be used in all types of compositions known to those skilled in the art and usable for the administration of product (s) active (s) to vertebrates, more particularly the bred to warm-blooded such as the cattle, sheep, goats, equines, pigs,

  fish and pets such as dogs and cats.

  The methods to be favored for the administration cover in parti-

  but without restriction, oral administration, topical administration and parenteral administration. The corresponding formulations are prepared

  according to techniques known from the prior art and usually practiced.

  The compositions for oral administration comprise one or more compounds according to the present invention, in combination with pharmaceutically acceptable inert fillers or diluents. They may be presented by

  for example, in the form of tablets, cachets, capsules, pills, pastes, gels or

  controlled release systems. The tablets may for example be prepared by

  mixing an active product with an adjuvant or diluent comprising a disintegrating agent

  and a binder such as starch, lactose, talc and magnesium stearate. Mention may also be made of drinkable compositions, in which one or more compounds according to the invention are dissolved or suspended in a suitable medium, food premixes or concentrates containing one or more compounds according to the invention for the preparation of medicated feeds, additional drinking water,

  or for direct incorporation into the low feed of the animal.

  Compositions for parenteral administration include

  solutions, emulsions or suspensions, subcutaneous implants

  born solid or semi-solid capable of releasing in a controlled manner the active (s) according to the invention, in and with any carrier, diluent or pharmaceutically acceptable vehicle. Injectable formulations may be prepared and sterile by any means known to those skilled in the art. The acceptable liquid carriers are preferably selected from vegetable oils, such as sesame oil, glycerides such as triacetin, esters such as benzyl benzoate,

  Isopropylmyristate and fatty acid esters of propylene glycol, organic solvents

  such as glycerolformal, glycofurol, propylene glycol.

  Compositions for percutaneous or topical administration include sprays, powders, baths, showers, shampoos, creams, preparations for on or spot on, devices such as necklaces or

  oricular attachments capable of providing local or systematic control of arthropods.

  The formulations for on or spot one are more particularly solutions containing

  additives such as agents allowing a transcutaneous penetration, agents providing a good spread on the skin, film-forming agents ensuring a good adhesion and chosen from cellulose derivatives, alginates, gelatin, polyvinylpyrrolidone, polyvinyl alcohol, polyethylene glycols, surfactants such as emulsifiers and humectants, chosen from anionic, cationic, amphoteric or nonionic derivatives, stabilizers such as antioxidants,

  dyes. These agents can be taken separately or in combination.

  The present invention also relates to a means of controlling 0 arthropods and nematodes parasitic animals and plants which consists of applying to animals or plants or more generally to the surrounding environment,

  an effective amount of a compound according to the present invention.

  The parasites that can be combated by the compounds according to the invention and the places, zones or objects thus protected are detailed and in a nonlimiting manner. Examples include flies, ticks, fleas, endoparasites infesting livestock, and pets such as dogs and cats. Examples include arachnids, ticks, mites, weevils, moths, foodstuffs, cereals, seeds or flours, woods, carpets and carpets. We can mention the control of cockroaches, ants and arthropods simi lar in industrial or domestic places, mosquito larvae around water points, the fight against the various forms of Lepidoptera, beetles against hemiptera, nematodes that attack plants and trees either directly or by carrying bacteria, viruses or fungal diseases, nematodes

  lesions, dagger nematodes, stem eels and bulbs.

  The compounds according to the invention may be applied to the soil or more generally to the targeted site in the form of solid or liquid compositions. They have the particular interest of being able to control pests that feed on plant parts located at a certain distance from the application area of the products and to be able to limit the aggressions on the plants by unappetising and repulsive characteristics. The compounds according to the present invention are particularly useful for the protection of fields, forages, plantations, greenhouses,

  orchards, vineyards, forests.

  The compositions incorporating the compounds according to the invention, in combination with inert fillers and diluents, with possibly a substance capable of causing consumption by arthropods, are generally solid or liquid baits. The solid compositions are, for example, granules, pellets, briquettes, capsules, powders. The preparation is generally carried out by impregnating a solid diluent with a solution of one or more compounds according to the invention in a volatile solvent, by evaporating the solvent and transforming the product thus obtained by conventional methods to give granules or wettable powders, pellets, briquettes. Wettable powders can be suspended in water before use to give ready-to-use suspensions. The liquid compositions comprise water-miscible concentrates, soluble powders, aqueous or non-aqueous solutions or dispersions.

  may be presented as aerosol sprays.

  The compositions for the control of arthropods and nematodes generally contain from 0.00001 to 90% and more specifically from 0.005 to 50% by weight of one or more compounds according to the invention. The percentages will vary according to the destination and the aim of the corresponding composition. For the treatment of woods, plants, stored products; articles of the house, for topical applications on animals, the compositions will preferably contain 0, 00005 to 90% and more specifically 0.01 to 10% by weight of one or more of the compounds according to

1 invention.

  For oral or parenteral administration to animals, a concentration of 0.1 to 90% by weight, from 0.01 to 3% by weight for medicated feeds, of from 5 to 50% by weight for concentrates, is preferred. and 2s supplements for administration in foods. The dosage to be used for administration to the animals will depend on the species, the age and the degree of infestation, and will preferably be for a single dosage of 0.1 to 100 mg, preferably 2 to 20 mg per kilo. live weight, and for prolonged administration, 0, 0 1

  at 20mg per pound of live weight per day.

  For the treatment of soils and plantations by the farmer or horticulturist, the compounds according to the invention can be applied at a rate of 0.005 kg to about 20 kg of active ingredient per hectare, preferably at the rate of 0.02 to 1 kg

per hectare.

  The following examples 1 to 10 illustrate the preparation of the compounds of general formula (I) for which Z represents the sequence -N = C = O, N = C = S s and -N = S = O, and their use for the synthesis of parasiticidal pyrazole derivatives and insecticides of general formulas (IV), (V), (VI) (VII) and (VIII). Examples 11 to 21 illustrate compositions for the control of arthropods, plant parasitic nematodes, helminths, which contain as an active ingredient compounds of the general formulas (I), (III), (IV), (III), V), (VI) (VII) (VIII) and (IX). The compositions detailed in Examples 11 to 13 may be diluted to provide a sprayable composition at an optimum concentration for use in agriculture, horticulture, the environment. Examples 22 and 23 detail the duration of the tests used for the evaluation and determination of insecticidal activity and

  parasiticide compounds according to the invention.

  All these examples are indicative only to illustrate the in

  and in no way constitute a limitation of its scope.

EXAMPLE 1

  1- (2,6-Dichloro-4-trifluoromethylphenyl) -3-cyano-5-isocvanatoprazole CNR: OCN NN CICI CF3 To a solution of phosgene (0.93 g, 9.4 moles) in dry toluene (25 ml with stirring and kept at 0 ° C., a solution of 1- (2,6-dichloro-4-trifluoromethylphenyl) -3-cyano-5-aminopyrazole is added over about 10 minutes.

  (l, Sg, 4.7 moles) and pyridine (0.75 mL, 9.4 moles) in dry toluene (25 mL).

  Stirring is maintained for one hour at room temperature and the excess phosgene is then removed under reduced pressure (12 mbar). The pyridine hydrochloride is filtered, the filtrate concentrated under reduced pressure (0.1 mbar) to obtain the title product in the form of a yellow oil sensitive to moisture, with a

95% yield.

  9F NMR (C6D6, CF3COOH): 12.3 ppm IR (toluene): v (NCO): 2266 cm -1 MS (IE): m / z 346 (M-1.56%), 71 (100) %) The following 1-phenyl-5-iso (thio) cyanate pyrazoles having various substitutions at position -3, 4 on the pyrazole ring and on the aromatic ring at the 1-position and corresponding to the general formula (I) are similarly obtained: B: A

XCN- /: /

N Ar A B XAr MS IR (NCO)

CH3 H 0 199 (M) 2272

CF3 CN OF3C 414 (M) 2268

CF3 CF3S (0) 0F3C 486 (M + CF3) 2261

  Embedded image CN CF3S OCl 414 (M) 2263 CN CF (0) OF3C i6 7 iM C + 4 Cl CN Cl OF 380 (M) 2266

CN H _

EXAMPLE 2

  1- (2,6-Dichloro-4-trifluoromethylphenyl) -3-cyano-5- (N-sulBlnVlamino) pYrazole CN

OSN-, N

N Cl: 3'C

CF3

  The reaction is conducted under a nitrogen atmosphere in Schlenck tube. 1- (2,6-Dichloro-4-trifluoromethylphenyl) -3-cyano-5-amino pyrazole (2.28 g, 7.1 mmol) and N, N-dimethylformamide (DMF) (5 mol%) are cooled to 0 ° C. with an ice bath and thionyl chloride (6.5 g, 55 mmol) added via a syringe with vigorous stirring. After stirring for 30 minutes at 0 ° C. and 1 hour at room temperature, the excess of thionyl chloride is

  removed under reduced pressure. The residue is washed 3 times with anhydrous pentane (3 × 10 ml).

  Evaporation of the solvent under reduced pressure leads to derivative N

sulfinylamno (2.24 g, 86%).

  m.p. NMR (C6 D6): 7.02 s (2H, Ar), 7.23 s (1H, pyr) 9F NMR (C6 D6): 611.0 ppm MS (EI): m / z 366 (M +); 1) + The following 1-phenyl-5- (N-sulfinylamino) pyrazoles, having various substitutions in the 4-position on the pyrazole ring and on the aromatic ring in the -1-position, and corresponding to the general formula (I), are similarly obtained: Ar B MS (IE): m / z (M) 9R NMR, mp, C (dec) ua -.

H 334 126-130

F, C H 366 11.7 119-121

  ci Br 412 132-135 to Cl 402 12.0 131-134 F3C; u Br 446 12.0 134- 137

F3CS 434 33.6 129-131

F3CÉ-.

\ = (u F3CS 467 32.6; 12.3 i71-174

F3C5 =:

Cl F3CS (O) 483 -0.4; 11.9 178-183

EXAMPLE 3

  1- (2,6-Dichloro-4-trifluoromethylphenyl) -3-cyano-4- (trifluoromethylsulfonyl) pvrazol-yl-O- (2,2,2-trifluoromethyl) urethane (R) N, CN

F3CH2CO C / - N

  To a solution of phosgene (0.918, 9.2 mmol) in anhydrous toluene (10 ml), with stirring and maintained at 0.degree. 6-dichloro-4-trifluoromethylphenyl) -3-cyano-4-trifluoromethylsulfinyl-5-aminopyrazole (2.0 g, 4.6 mmol) and pyridine (0.75 ml;

  mmol) in a 2/3 volume mixture of toluene and dichloromethane (50 ml).

  The reaction mixture is stirred at room temperature for 1 hour, and then excess phosgene removed under reduced pressure (12 mbar). The mixture is heated to 0-5 ° C., and a solution of 2,2,2-trifluoroethanol (0.5 g, 5.0 mmol) in dichloromethane (5 ml) added dropwise. The resulting suspension is stirred overnight, the solid filtered and removed, the filtrate washed with water (20 ml x 3), dried, concentrated under reduced pressure to give a whitish solid product (2.4 g). The product is purified on gel

  of silica (MERCK, 230-400 mesh) with chloroform as eluent.

m.p. 79-81 C.

  H NMR (CDCl3): 4.40 qd, 3J (HF) 7.2 Hz (2H, CH2), 7.77 m (2H, H arom) F NMR (C6D6, CF3 COOH): 1.13 s (CF3 CH2), 3.82 s (CF3S), 12.18 s (CF3 arom) MS (IE): m / z 563 (M +, <1%), 393 (100%), calcd for C15H5Cl2F9N4O3S: 563

EXAMPLE 4

  N, N-Dimethyl-N'-1- (2,6-dichloro-4-trifluoromethylphenyl) -3cvanonVrazole-5-

vllThiourée S CN

H'N N'N

  CIC CF3 To a solution of thiophosgene (1.07, 9.3 mmol) in toluene (20 ml), in Schlenck tube, and maintained at a temperature between 0 and: C, A = is added dropwise, in about 15 minutes, a solution of 1- (2,6-dichloro-4-trifluoromethylphenyl) -3-cyano-5-aminopyrazole (3.0 g, 9.3 mmol) and pyridine o (1.83 g, 23.2 mmol) in toluene (50 ml). After stirring for 45 minutes at room temperature, the residual thiophosgene is removed under reduced pressure, the reaction mixture is cooled to 0.degree. C. and a solution of diethylamine (1.8 g, 27.9 mmol) in toluene (15 g) is added. ml) added. The mixture is stirred for 45 minutes at ambient temperature and then concentrated under reduced pressure. The residue is taken up in dichloromethane (60 ml), the corresponding solution washed with 2N hydrochloric acid (2 × 25 ml) and with water (2 × 25 ml). After drying on sodium sultate, the solvent is removed under reduced pressure to give a purified solid by washing with ether.

diethyl (l, Sg, 40%).

  m.p. 173- 176 MS (IE): m / z 407 (M +), calcd for C4HoCl2F3N5S: 407.0H NMR (CDCl3): 3.10 (6H, (CH3) 2N), 6.86 (1H, NH), 7H NMR (CDCl3):? , 73 (s (2H, arom) 19 NMR (CDCl3): 12.42 s (CF3, arom)

EXAMPLE 5

  N- [1- (2,6-Dichloro-4-trifluoromethylphenyl) -3-cyano-4-trifluoromethylthio] urea F;

H-N - N

  A solution of 1- (2,6-dichloro-4-trifluoromethylphenyl) -cycyano-4-trifluoromethylthio-5-isocyanatopyrazole (2.85 mmol), prepared according to the same procedure as that set forth in US Pat. Example 3, from the corresponding amino derivative (2.5 g, 2.85 mmol), phosgene (5.70 mmol) and pyridine (5.70 mmol) in a 2/3 mixture of toluene / dichloromethane ( ml) is treated at 0 ° C with an excess of ammonia. After 20 minutes, the reaction mixture is poured onto a 2M aqueous solution of hydrochloric acid (100 ml). The organic phase is washed with water (50 ml x 3), dried over anhydrous sodium sulphate, concentrated under reduced pressure to give the product represented above in the form of a powder.

  white, 2.7 g, for a yield of 75%.

  m.p. 192 - 196 CH NMR (d6-acetone): 55.59 s (1H, NH), 8.95 s (2H, ArF), 8.80 s (2H, NH2) 9F NMR (d6-acetone): 512.45s (Ar, CF 3), 31.35 s (CF 3 S) MS (IE): m / z 463 (M +), calculated for C 3 H 5 Cl 2 F 6 NSos: 463 In the same manner, N, N-dimethyl-N-1 was prepared. (2,6-dichloro-4-trifluoromethylphenyl) -3-cyano-pyrazol-5-yl] urea from 1 (2,6-dichloro-4-trifluoromethylphenyl) -3-cyano-5-isocyanatopyrazole and dimethylamine.

m.p. 213-217 C.

  MS (EI): m / z 391 (M +), calcd for C14H10Cl2F3N5O: 391 H NMR (d6-DMSO): 2.78 s (6H, CH3), 6.97 s (1H, Pyr), 8.25 s (2H, Ar), 9.04 s

(1H, NH)

  19F NMR (d6-acetone): 12.55 s (CF3).

  By proceeding in the same manner, N- [3,5 bis (trifluoromethyl) phenyl] -N '- [1- (2,6-dichloro-4-trifluoromethylphenyl) -3-cyano-

  pyrazol-5-yl] urea from 1- (2,6-dichloro-4-trifluoromethylphenyl) -3-cyano-5-iso

  cyanatopyrazole and 3,5-bis (trifluoromethyl) aniline.

m.p. 230-233 C.

  MS (IE): m / z 575 (M +), calcd for C20H8Cl2F9NSO: 575O1H NMR (deacetone): 7.20 s (1H, Pyr), 7.65 s (2H, Ar)

  19 F NMR (d6-acetone): 12.41 br.s (CF3).

  By proceeding in the same manner, N- (2,6-dichloro-4-trifluoromethylphenyl) -N '- [1- (2,6-dichloro-4-trifluoromethylphenyl) -3-cyano-pyrazol-5-yl is prepared in the same manner. -)] urea from 1- (2,6-dichloro-4-trifluoromethylphenyl) -3-cyano-5-isocya-natopyrazole and 2,6-dichloro-4-trifluoromethylaniline.

m.p. 212-214 C.

  MS (IE): m / z 577 (M +), calcd for C19H7Cl4F6NSO: 577, IH NMR (deacetone): 7.10 s (1H, Pyr), 7.84 s (2H, H arom), 7.90 br s (1H, NH) 8.16 s (2H, H arom), 9.25 br s (1H, NH);

  19 NMR (d6-acetone): 12.54 s, 12.75 s.

  By proceeding in the same manner, N, N-dimethyl-N '[1- (2,6-dichloro-4-trifluoromethylphenyl) -3-cyano-4-trifluoromethylthio-pyrazol-5-yl] urea is prepared from 1- (2,6-dichloro-4-trifluoromethylphenyl) -3-cyano-4trifluo

  romethylthio-5-isocyanatopyrazole and dimethylamine.

m.p. 193-197 C.

  MS (EI): m / z 491 (M +), calcd for C 1 SH9C12F6NSOS: 491; 1H NMR (deacetone): 2.86 s (6H, Me2N), 8.09 s (2H, H arom); 19F NMR (d6-acetone): 12. 43 s (Ar-CF3), 31.63 s (CF3S In the same manner, N- [1- (2,6-dichloro-4-trifluoromethylphenyl) -3- cyano-4trifluoromethylsulfinyl-pyrazol-5-yl] urea from 1- (2,6-dichloro-4-trifluoromethylphenyl) -3-cyano-4-trifluoromethylsulfinyl-5-iso cyanatopyrazole and ammonia

m.p. 208-210 C.

  MS (EI): m / z 479 (M +), calcd for C13H5Cl2F6N5O2S: 479; 1H NMR (deacetone): 6.22 br s (2H, NH 2), 8.18 s (2H, H arom);

  19F NMR (d6-acetone): 3.90 s (CF3SO), 12.40 s (Ar-CF3).

  In the same manner, N, N-dimethyl) -N '[1- (2,6-dichloro-4-trifluoromethylphenyl) -3-cyano-4-trifluoromethylsulfinyl pyrazol-yl] urea is prepared from 1 - (2,6-dichloro-4-trifluoromethylphenyl) 4-trifluo -3cyano-

  romethylsulphinyl-5-isocyanatopyrazole and dimethylamine.

m.p. 122-126 C.

  MS (IE): m / z 507 (M +), calculated for ClSH9Cl2F6N5O2S: 507; 1H NMR (d6acetone): 2.88 s (6H, Me2N), 8.16 s (2H, Harom); 19F NMR (d6-acetone): 4. 23 s (CF3SO), 12.43 (Ar-CF3) - In the same manner, N- (2-trifluoromethyl-4-nitrophenyl) -N 'is prepared. [1- (2,6-Dichloro-4-trifluoromethylphenyl) -3-cyano-4-trifluoromethylsulfinyl-pyrazol-5-yl] urea from 1- (2,6-dichloro-4-trifluoromethylphenyl) -3- cyano-4-trifluoromethylsulphinyl-5-isocyanato-pyraZole and 2-trifluoro-methyl-4-nitroaniline.

m.p. 218-220 C.

  MS (EI): m / z 614 (M + NO2), calcd for C20H7Cl2F9N6O4S: 668; 1H NMR (deacetone): 3.17 br s (1H, NH), 8.25 s (2H, H arom), 8.32-8.56 (3H, H arom), 9.94 br (1H, NH);

  19 F NMR (d6-acetone): 3.89 s (CF3SO), 12.38 s (Ar-CF3), 13.89 s (Ar-CF3).

EXAMPLE 6

  N, N'-bis 11 - (2,6-dichloro-4-trifluoromethylphenyl) -3-cyano-4-trifluoromethyl-sulfinyl-n-vrazol-5-yl

CF3 CF3

CN t = 0 0 - CN C Cl4Cl OCI: C

CF3 CF3

  A solution of 1- (2,6-dichloro-4-trifluoromethylphenyl) -3-cyano-4-trifluoromethylsulfinyl-5-aminopyrazole (1.0 g, 2.3 mmol) and pyridine (0) is added dropwise. 40 g, 5 mmol) in a mixture of dichloromethane and toluene (respectively 15 and 5 ml), in approximately 10 minutes, to a solution of phos

  10 gene (6.8 mmol) in toluene (4 ml), at a temperature between 0 and 5C.

  After 45 minutes, the reaction mixture is brought to room temperature and the excess plosgene removed under reduced pressure. It is returned to 0 ° C. to pour a solution of the same pyrazole derivative (1.0 g, 2.3 mmol) in dichloromethane (20 ml). The mixture is stirred for 48 hours at room temperature, then poured into water (50 ml) and the organic phase washed with dilute sodium bicarbonate and finally with water (30 ml). After drying over sodium sulfate, the solvent is removed under reduced pressure to give a purified whitish solid by repeated washing with diethyl ether. There is thus obtained 1.9 g (92%) of a product which has the following characteristics: MS (IE): m / z 883 (M + CF 3), calculated for C 2, H 6 C 14 Fr 2 NO 3 S 2: 900 H NMR (d 6 -acetone): 8. 17 s (Harom) i9F NMR (d6-acetone): 3.83 s (CF3SO), 12.26 s (Ar-CF3) 4s

EXAMPLE 7

NCwH>: N u:, a 11 a, g, c

CF3 CF3

  To a solution of 1- (2,6-dichloro-4-trifluoromethylphenyl) -3-cyano aminopyrazole (3.0 g, 9.3 mmol) and pyridine (1.83 g, 23.2 mmol) in toluene ( 50 ml), stirred at 0 ° C., a solution of phosgene (1.38 g, 13.9 mmol) in toluene (7 ml) is added dropwise over approximately 15 minutes. After stirring for 1 hour at room temperature, excess phosgene is removed under reduced pressure. The reaction mixture is cooled to 0 ° C. and the water (15 ml) is added dropwise. The solid is filtered, washed with water

  o iced; 1.9 g (52%) of the pyridine salt represented above is thus recovered.

  H NMR (d6-acetone): 7.09 s (1H, Pyr), 7.90 s (2H, H arom), 8.33 - 9.00 m (Py), 10.66 br s (NH) t9F NMR (d6-acetone): 11 , 82 s (CF3)

EXAMPLE 8

  1- (26-Dichloro-4-trifluoromethylphenyl) -3-cyano-s- (N-heptafluoropropyl sulphinylamino) ovrazole 0 C N

F3C F2C F2C-S.

  ## STR5 ## To a solution of phenylmagnesium bromide (2.6 mmol) in diethyl ether in a 100 ml Schlenck tube maintained at -40.degree.

  Heptafluoro-1-iodopropane (2.6 mmol) is administered via a syringe.

  The resulting solution is stirred for 30 minutes before pouring a solution of 1- (2,6-dichloro-4-trifluoromethylphenyl) -3-cyano-5- (Nsulfinylamino) pyrazole (0.87 g, 2.4 mmol) into the solution. ether (20 ml). After stirring for 1 hour at -40 ° C., then 3 hours at 0 ° C., the reaction mixture is poured onto an aqueous solution of ammonium chloride (50 ml). The organic phase is extracted with water (3 × 1 ml), dried over sodium sulphate, filtered and evaporated under reduced pressure. The crude residue is purified

  by column chromatography on silica gel, eluted with a dichloromethane mixture

  methane-hexane (1/1), then with chloroform. The selection of the fractions and the corresponding evaporation makes it possible to recover 0.69 g (54%) of the title product,

in the form of a yellow oil.

  o H NMR (CDCl 3): δ 5.90 s (1H, Pyr), 7.75 s (2H, Ar) 19F NMR (CDCl 3): δ 48.9 d, 2 ΔF 245 Hz (FAFBCS), -41.9 δ 2 ΔF 245 Hz

  (FAFBCS), -6.8 t, 3ff 8.5 Hz (CF3), 11.2 m (CF2), 11.4 s (CF3 / Ar) - -

EXEMPT 9:

  36-Dihydro-4,5-dimethyl-N-1- (2,6-dichloro-4-trifluoromethylphenyl) -3-cyan-4-trifluoromethyl-1-pyrazol-5-yl-1,2-thiazine-1-oxido

F3C -4 C N

  The mixture in anhydrous toluene (20 ml) of 1- (2,6-dichloro-4-trifluoromethylphenyl) -3-cyano-4 (trifluoromethylsulphinyl) -5- is added to the mixture in anhydrous toluene (20 ml). (Sulfinylamino) pyrazole (1.2 g, 2.75 mmol) and 2,3-dimethylbutadiene (0.68 g, 8.25 mmol) is brought to C for 12 hours. The solvent is removed under reduced pressure, the residue is taken up in dichloromethane (25 ml), the corresponding solution washed with water (3 × ml), dried over sodium sulphate and concentrated in vacuo to give a purified solid by recrystallization. in an ethanol / water mixture. This gives 1.gig (77%) of the title product having the following characteristics: m.p. 145-148 ° C (dec) 1H NMR (CDCl3): 1.66 br s (6H, CH3), 3.09-4.02 m (4H, CH2), 7.78 s (2H, Ar)

  NMR (CDCl3): 4.26 (F3CSO), 12.35 (F3C / Ar).

* In the same manner, 3,6-Dihydro-4,5-dimethyl-N [1- (2,4,6-trichlorophenyl) -3-cyanopyrazol-5-yl] -1,2-thiazine is prepared. 1-oxide from 1- (2,4,6-trichlorophenyl) -3-cyano-5- (N-sulfinylamino) pyrazole and dimethylbutadiene. m.p. 198-201 C (dec) MS (IE): m / z 416 (M +), calcd for C16H13Cl3N4O4: 416 1H NMR (CDCl3): 1.71 br s (6H, CH3), 2.944.10 m (4H, CH2) ), 6.73 s (1H, Pyr),

7.50 s (2H, Ar).

  By proceeding in the same manner, 3,6-dihydro-4,5-dimethyl-N- [1- (2,4,6-trichlorophenyl) -3-cyano-4-bromopyrazol-5-yl] is prepared. 1,2thiazine oxide from 1- (2,4,6-trichlorophenyl) -3-cyano-4-bromo-5 (N-sulfinyl)

  amino) pyrazole and dimethylbutadiene. -

  m.p. 166-169 ° C (dec) MS (IE): m / z 494 (M +), calcd for C16H12BrCl3N4O4: 494.6 1H NMR (CDCl3): 1.70 s (3H, CH3), 1.74 s (3H, CH3), 3.04- 3.46 m (4H, CH 2), 7.50 s (2H, Ar) In the same manner, 3,6-dihydro-4,5-dimethyl-N- [1- (2,4,6-trichlorophenyl) is prepared. 3-cyano-4-trifluoromethylthiopyrazol-5-yl] o 1,2-thiazine-1-oxide from 1- (2,4,6-trichlorophenyl) -3-cyano-4-trifluoromethyl

  thio-5- (N-sulfinylarnino) pyrazole and dimethylbutadiene.

  m.p. 164-167 ° C (dec) 1H NMR (CDCl3): 1.63 s (3H, CH3), 1.75 s (3H, CH3), 2.98-4.12 m (4H, CH2), 7.54s (2H, Ar). By proceeding in the same manner, 3,6-dihydro-4,5-dimethyl-N- [1- (2,6-dichloro-4-trifluoromethylphenyl) -3-cyanopyrazol-5-yl] -1,2-thia is prepared. zine-1 -oxide from 1 - (2,6-dichloro-4-trifluoromethylphenyl) -3-cyano-5- (N)

  sulfinylamino) pyrazole and dimethylbutadiene.

  m.p. 201-203 C (dec) MS (IE): m / z 448 (M-1) +, calcd for C17H13Cl2F3N4O4: 449.3 1H NMR (CDCl3): 1.69 br s (6H, CH3), 3.00-4.10 m ( 4H, CH 2), 6.75 s (1H, Pyr), 7.72sand7.74s (2H, Ar)

19F NMR (CDCl3): 12.46 s (F3C / Ar).

  By proceeding in the same manner, 3,6-dihydro-4,5-dimethyl-N [1- (2,6-dichloro-4-trifluoromethylphenyl) -3-cyano-4-bromopyrazol-5-yl is prepared. 1.2-thiazine-1-oxide from 1- (2,6-dichloro-4-trifluoromethylphenyl) 3-cyano-4

  bromo-5- (N-sulfinylamino) pyrazole and dimethylbutadiene.

  m.p. 166-169 ° C (dec) MS (IE): m / z 528 (M +), calcd for C17H12BrCl2F3N4O5: 528.2 1H NMR (CDCl3): 1.71 br s (6H, CH3), 3.04-4.41m (4H, CH2) 7.75 s and 7.74 s (2H, Ar) -19 NMR (CDCl3): 12.4 s (F3C / Ar) In the same manner, 3,6-Dihydro-4,5-dimethyl-N [1 is prepared. - (2,6-Dichloro-4-trifluoromethylphenyl) -3-cyano-4- (trifluoro-romethylthio) pyrazol-5-yl] -1,2-thiazine-1 -oxide from 1 - (2,6-dichloro-4) trifluoromethylthio) -5- (N-sulphinylamino) pyrazole and dimethylbutadiene. m.p. 148-151 ° C (dec) MS (IE): m / z 549 (M +), calcd for C18H12Cl2F6N4O5: 549.3 1H NMR (CDCl3): 1. 66 s (3H, CH3), 1.69 s (3H, CH3), 3.02-4.42 m (4H, CH 2), 7.77 s (2H, Ar)

  19F NMR (CDCl3): 12.31 s (C F3 / Ar), 32.8 s (CF3S).

EXAMPLE 10

  1- (2,6-Dichloro-4-trifluoromethyl) phenyl) -3-cyano-4- (trifluoromethylthio) 5- (2,3-dimethylbut-3-en-1-yllamino ovrazole CN

F 3 C S

  A solution of 3,4-dihydro-4,5-dimethyl-N- [1- (2,6-dichloro-4-trifluoromethylphenyl) -3-cyano-4 (trifluoromethylthio) pyrazol) is prepared. 5-yl] 1,2thiazine-1-oxide (3.3 g, 6 mmol) in a mixture of tetrahydrofuran and water (35 and 10 ml, respectively). Sodium hydroxide (0.5 g, 12.5 mmol) is added and the reaction mixture is left at room temperature for 24 hours. The excess sodium hydroxide is neutralized with 2N hydrochloric acid, dichloromethane (20 ml), the organic phase is separated and washed with water (3 x ml). After removing the solvents under reduced pressure, the crude residue is recrystallized from ethanol / water to give 2.2 g (73%) of the title product.

m.p. 153-157 C.

  1H NMR (CDCl3): 0.97 d, 3HHH 8.0 Hz (3H, CH3), 1.59 s (3H, CH3), 2.35 m (1H,

  CH), 3.10 m (2H, CH 2), 4.61 and 4.75 m (2H, H 2 C =), 7.79 (2H, Ar).

  19F NMR (CDCl3): 12.28 s (F3C / Ar), 30.41 s (CF3S).

  By proceeding in the same manner, 1- (2,6-dichloro-4-trifluoromethylphenyl) -3-cyano-5- (2,3-dimethylbut-3-en-1-yl) aminopyrazole is prepared from - 374-dihydro-4,5-dimethyl-N- [1- (2,6-dichloro-4-trifluoromethylphenyl)) - 3

  cyanopyrazol-5-yl) - 1,2-thiazine-1 -oxide.

m.p. 127-130 C.

  MS (IE): m / z 402 (M-1) +, calculated for C17H1SCI2F3N4: 403.2 1H NMR (CDCl3): 1.02 d, 3HHH 8.0 Hz (3H, CH3), 1.62 s (3H, CH3), 2.42 m ( 1H,

  CH), 3.02 m (2H, CH 2), 4.63 and 4.73 m (2H, H 2 C =), 5.86 s (1H, Pyr), 7.76 (2H, Ar).

19F NMR (CDCl3): 12.36 s (F3C / Ar).

  By proceeding in the same manner, 1- (2,6-dichloro-4-trifluoromethylphenyl) -3-cyano-4- (trifluoromethylsulfinyl) -5- (2,3-dimethylbut-3-en-1-yl) aminopyrazole is prepared from 3,4-Dihydro-4,5-dimethyl-N- [1- (2,6-dichloro-4-trifluoromethylphenyl) -3-cyano-4 (trifluoromethylsulphinyl) pyrazol-5-yl) -1,2-thiazine oxide.

m.p. 165- 167 C.

  2s MS (IE): m / z 518 (M-1) +, calculated for C18H14Cl2F6N4O5: 519.3

  19FNMR (CDCl3): 1.47 (CF3SO), 12.31s (F3C / Ar).

EXAMPLE 11

  A concentrate for aqueous dilution is prepared according to the following percentage composition: Active: 5% w / v, n / a Nonylphenyl / ethylene oxide condensate (9): 10% w / v N-methyl pyrrolidone: q To a solution of the ethoxylated surfactant in a large proportion of N-methylpyrrolidone, the active ingredient is added and stirred until completely dissolved. The

  The corresponding solution is adjusted to the volume with the solvent.

EXAMPLE 12

  A wettable powder is prepared corresponding to the following one-hundred-percent composition: Active: 40% mlm Sodium dodecylbenzene sultonate: 2% w / w Sodium alpha-oletine sulphonate: 6% w / w Silicate magnesium: 100 wt% qs ingredients are thoroughly mixed and milled to yield a homogeneous blend of particle size less than 40 μm. The powder can be easily diluted with water to obtain a formulation containing 0.02% O.sub.2 SO.sub.4.

weight / volume of active ingredient.

EXAMPLE 13

  A water-dispersible granule is prepared according to the following percentage composition: Active: 30% w / w Sodium α-olefin sulphonate: 12% w / w Sodium dodecylbenzene sultonate: 12% w / w Silicate magnesium: qs 100% by weight The ingredients are thoroughly mixed and granulated with a

  minimum of water. The corresponding granules are dried in a fluidized air bed.

EXAMPLE 14

  A formulation is prepared to correspond to the following percentage composition: Active: 1% rn / v Polyoxyethylenated C6 / Cs triglycerides (60E): 65% v / v Miglyol 840: 25% v / v Ethanol anhydrous: qs 100% by volume The active ingredient is solubilized in triglycerides, and the corresponding solution

  volume adjusted with anhydrous ethanol.

EXAMPLE 15

  A formulation is prepared to meet the following percentage composition: Active: 1% w / v Cetearyl octanoate: 10% v / v Isopropylmyristate: 1% v / v Isopropyl alcohol: qs 100% by volume o The active ingredient is solubilized in a sufficient quantity of isopropyl alcohol, the other ingredients incorporated, and the corresponding solution brought to the

  volume with the balance of isopropyl alcohol.

EXAMPLE 16

  A spot formulation is prepared according to the following percentage composition: Active: 10% w / v Polyvinylpyrrolidone (Kollidon K17): 5% w / v Ethyl ether diethylene glycol: qs 100% by volume The active ingredient is solubilized in a proportion sufficient solution of polyvinylpyrrolidone in the solvent, and the corresponding solution adjusted to the volume

with the balance of the solvent.

EXAMPLE 17

  An implant for subcutaneous administration is prepared according to the following percentage composition: Active: 25% mlm Sodium salt of starch glycolate: 5% m / m Magnesium stearate: 3% m / m Lactose: qs 100% by weight weight The ingredients, with the exception of magnesium stearate, are thoroughly mixed, the mixture being calibrated. To the corresponding mixture is added half of the magnesium stearate. After homogenization, the whole is compressed, the corresponding tablets converted into granules to retain the granulosic fraction 2 of between 200 and 355 m. The balance of magnesium stearate is then

  added and the mixture compressed to give implants.

EXAMPLE 18

  A gradual release granulate is prepared corresponding to the following percentage formula: Active: 20% w / w PEG4000: 20% w / w PEG20000: qs 100% by weight The granules are prepared by granulation from the molten mixture 0 of the ingredients ( melt granulation). The release rate of the active solution in the polyethoxylated vector can be modulated by selecting the polymer composition.

EXAMPLE 19

  An injectable formulation having the following composition is prepared: Active: 1% w / v Ethyl oleate: 30% v / v Sesame oil: qs 100% by volume The active ingredient is solubilized in ethyl oleate and the corresponding solution is volume adjusted with sesame oil. The solution is sterilized by

  membrane filtration and sterilely conditioned.

EXAMPLE 20

  Tablets are prepared corresponding to the following percentage composition: Active: 50% w / w Methacrylic acid / ethyl methacrylate copolymer: 15% w / w Talc: 1.3% w / w magnesium stearate: 0, ; % m / m Calcium phosphate: qs 100% by weight The ingredients, with the exception of magnesium stearate, are intimately mixed, granulated with a solution of methacrylic copolymer, the resulting composition is dried and calibrated, the magnesium stearate incorporated , and the

  resulting homogeneous mixture subjected to compression.

EXAMPLE 21

  A shampoo is prepared according to the following percentage composition: Active: 0.5% w / v Sodium lauryl ether sulfate: 25% w / v Diethanolamine Lauramide: 5% v / v Cocoamidopropylbetane: 10% w / v 0 Hydrogenated castor oil polyoxyethylenated (400E): 3% w / v Imidazolidinyl urea: 0.5% w / v: Sodium chloride: 2% w / v - = Water: qs 100% by volume The preservative is dissolved in a sufficient quantity of water and the sodium chloride, and then introduced into the resulting solution lauryl ether sulLate

  of sodium, and then the betane derivative, to end with the addition of the lauramide of di-

  ethanolamine. To the corresponding aqueous solution, the solution of the active ingredient is added to the polyoxyethylenated hydrogenated castor oil. The composition is adjusted

to volume with water.

EXAMPLE 22

  The activity of the compounds according to the invention against flies of the STOMOXYS CALCITRANS species is demonstrated by the results of the following test: 20 flies of the aforementioned species are placed in petri dishes containing a saturated device, one day. before the start of the test, by a determined volume (1 ml) of a composition of the active agent tested. To prepare this composition, the active ingredient corresponding to the general formulas (I), (III), (IV) or (V), is dissolved in polyoxyethylenated hydrogenated castor oil (400E) in the respective proportions 1/2. The concentrate thus obtained is diluted with water to go as desired to the desired concentration. After 12 hours, the activity of the committed compound is evaluated at each of the concentrations tested, counting the number of flies alive. 100% indicates that all flies have been killed and 0% none of them are

:., .. ^

  . .. dead. The compounds corresponding to the general formulas (I), (III), (IV) (V) (VI) (VII) (VIII) and (IX) prove to give rise to mortality for a dosage ranging between 0.1 and 30.

microgram per fly.

EXAMPLE 23

  The activity of the compounds according to the invention against adult fleas and ticks (respectively Ctenolcephalides felis and Rhipiaphalus sanguineus) is evaluated in vitro according to the following protocol: Fleas: 10 adult fleas are placed in tubes (1 / diam = / 16 mm) equipped with a device to prevent leakage. They are exposed in this environment to a paper previously loaded with active from a stock solution to ensure a concentration of 0.0005% to 0.5%. Mortality is monitored at 24 and 48 hours beyond the beginning of the exposure and -the test repeated 6

  fo i s, so it 60 chips exposed to the same concentration.

  Ticks: 10 ticks are placed in a Pasteur pipette (I = 150 mm), previously charged with active ingredients by the introduction of the same volume of a

  concentration solution varying between 0.00001 and 0.01%, followed by evaporation.

  Each pipette is sealed with cotton. The pipettes are placed in a humidity-laden environment and controlled at 27 C. Tick mortality is monitored at 24 and 48 hours, each test repeated 5 times, ie 50 ticks exposed to

the same concentration.

  For fleas as well as for ticks, a check is made with tubes not loaded with active ingredients and tests for which the mortality is less than

% are not taken into account.

ss

Claims (23)

  1. Process for the synthesis of N-substituted derivatives of 5-amino-1   phenylpyrazole corresponding to the general formula (I): A B N R I R f R R (I1 s in which - -   A and B represent, independently of each other: - a hydrogen atom; a linear, branched or cyclic alkyl, alkenyl or alkynyl radical comprising from 1 to 12, preferably from 1 to 6 carbon atoms, the chain   0 carbuncle of these radicals being capable of being substituted by one or more groups   selected from the radicals: halo, alkyloxy, alkylthio, alkyloxycarbouyl, the alkyl radical of these radicals, linear, branched or cyclic comprising from 1 to 6 carbon atoms; a halogen atom chosen from fluorine, chlorine, bromine or iodine;   a cyano, thiocyano, nitro, sulLamido or alkylamino radical,   alkylamino, aminocarbonyl, aminothiocarbonyl, alkylaminocarbonyl, alkyl   aminothiocarbonyl, dialkylaminocarbonyl, dialkylaminothiocarbonyl or alkyl   carbonylamino or alkylthiocarbonylamino and wherein each alkyl radical, linear, branched or cyclic, saturated or unsaturated, comprises from 1 to 6 carbon atoms; a radical of general formula -S (O) nR, in which n is equal to 0, 1 or 2, and R represents an alkyl radical, linear, branched or cyclic, saturated or unsaturated, comprising from 1 to 6 carbon atoms optionally substituted with one or more identical or different halogen atoms; a phenyl or phenylalkyl radical or a heterocycle comprising from 4 to 7 shafts, and from 1 to 3 heteroatoms chosen from nitrogen, sulfur, oxygen or silicon, the straight or branched chain alkyl moiety having from one to four carbon atoms and the phenyl or heterocycle portion being optionally substituted by one or more groups selected from halogens, alkyls, haloalkyls, haloalkoxy, haloalkylthio, cyano, thiocyano, nitro, sulfamido, aminocarbonyl, aminothiocarbonyl radical, alkylaminocarbonyl, alkylaminothiocarbonyl, dialkyl aminocarbonyl, dialkylaminothiocarbonyl, including the linear alkyl moiety,   branched or cyclic, saturated or unsaturated, comprises from 1 to 6 carbon atoms.   R 3 R 3 R 3 and R 5 represent, independently of one another: a hydrogen atom; a halogen atom;   an alkyl, alkoxy, alkylthio, haloalkyl or halogenoalkyl radical;   alkoxy, haloalkylthio, and whose linear, branched or cyclic, saturated or unsaturated alkyl radical contains from 1 to 6 carbon atoms optionally substituted with one or   several identical or different halogen atoms.   Z represents a radical chosen from the groups: -N = C = O, -N = C = S, N = S = O, -   NHC (= X) -R6, -NHC (= O) -X-R6, -NHC (= S) -X-Et6, -NHC (= X) NR7Rg, wherein X represents an atom selected from oxygen or S, R represents a linear, branched or cyclic alkyl, alkenyl or alkynyl radical comprising from 1 to 12, preferably from 1 to 6, carbon atoms, the carbon chain of these radicals being   which may be substituted by one or more groups selected from   halo, alkyloxy, alkylthio, alkyloxycarbouyl, the alkyl radical of these radicals.   caux, linear, branched or cyclic comprising from 1 to 6 carbon atoms; a phenyl or phenylalkyl radical or a heterocycle having from 4 to 7 members, and from 1 to 3 heteroatoms chosen from nitrogen, sulfur, oxygen or silicon, the alkyl moiety with straight or branched ring having from one to four atoms carbon, the phenyl or heterocyclic portion being optionally substituted by one or more groups selected from halogens, alkyls, haloalkyls, haloalkyls, halo   genoalkylthio, cyano, thiocyano, nitro, aminocarbonyl, aminothio-   carbonyl, alkylaminocarbouyl, alkylaminothiocarbonyl, dialkylaminocarbouyl, dialkylaminothiocarbonyl, haloalkylsulfonyl, or haloalkylsulfinyl and whose straight, branched or cyclic, saturated or unsaturated alkyl part comprises from one to four carbon atoms and the heterocyclic part is optionally substituted with a phenyl radical, itself substituted by one or more identical or different groups selected from halogens, alkyls, haloalkyls, haloalkoxy, haloalkylthio, cyano, thiocyano, nitro, amino carbonyl, aminothiocarbonyl, alkylamino carbyl, alkylaminothiocarbonyl and dialkylaminocarbonyl radicals. dialkylaminothiocarbonyl haloalkylsulfonyl or haloalkylsulfinyl, the alkyl radical of these branched or cyclic linear radicals comprising from 1 to 6 carbon atoms; R7 and R5 are, independently of one another: a hydrogen atom; the R6 radical previously defined; a heterocycle -Het of the general formula (I) in which A, B, R ', R2, R3, R4, and R have the same definition as above, while Z represents a bond; Z can represent the sum -N = C = N-Het, in which Het represents a heterocyclic corresponding to the general formula (I) in which Z corresponds to a bond and A, B. R '' R., R3 R4 and R4 are as previously defined; or Z represents the 1,2-thiazine-1-oxide-2-yl unit, optionally substituted by alkyl or haloalkyl units, the saturated or unsaturated, linear, branched or cyclic alkyl radical comprising from 1 to 7 carbon atoms, process is characterized in that it comprises at least one step in which a 1-phenyl-5-amino pyrazole derivative corresponding to formula (II) is reacted: H2N R ': R5 R2 R4   Wherein R 1, R 2, R 3, R 4 and R 5 are as defined above, with at least one reagent selected from: phosgene, thiophosgene and thionyl chloride, in an inert solvent, in the presence of an acid trap and at a temperature of -78 ° C to + 25 ° C, to obtain a compound of formula (I) in   which Z represents a radical chosen from the groups: -N = C = O, N = C = S, - N = S = O.   2. Method according to claim 1, characterized in that when Z represents the sequence-N = C = 0 or -N = C = S, for 1 mole of derivative according to general formula (II), 1.0 is used. to 2.5 moles of phosgene or thiophosgene, and 2.05 moles of acid trap, in a solvent selected from inert organic solvents such as aliphatic, alicyclic or aromatic hydrocarbons, halogen-substituted hydrocarbons, ethers and their mixtures, the trap to   o acid being selected from tertiary amines such as pyridine, N. N-   dimethylamine or triethylamine.   3. Process according to claim 1, for which Z represents the sequence -N = S = O, characterized in that thionyl chloride is added to a compound according to general formula (II) in the presence of a quantity. catalytic   is N, N dimethyliormamide at a temperature between - 10 C and + 25 C.   4. Method according to claim 3, characterized in that for one mole of the compound according to general formula (II) is introduced from 1.5 to 10 moles of thionyl chloride, preferably from 2.5 to 5.0 moles, in the presence of 1 to 5 mol% of N, N dimethylformamide.   5. Process according to any one of claims 1 to 4, characterized   in that the pyrazole ring has substituents A and B in the formulas   (I) and (II) selected from the electron-withdrawing substituents.   6. Process according to claim 5, characterized in that the substitutions   A and B in formulas (I) and (II) are selected from radicals: NO2, CN,   alkylsulphonyl, alkyloxycarbonyl, haloalkylsulphonyl.   7. Products according to general formula (I): A B Z R: 1 'R5 Rs I) in which:   A and B represent, independently of one another: a hydrogen atom; a radical   linear, branched or cyclic alkyl, alkenyl or alkynyl group comprising from 1 to 12, preferably from 1 to 6, carbon atoms, the carbon chain of these radicals being capable of being substituted by one or more groups selected from the group consisting of radi   o halo, alkyloxy, alkylthio, alkyloxycarbonyl, the alkyl radical of these radicals   caux, linear, branched, or cyclic comprising from 1 to 6 carbon atoms; an atom   halogen selected from fluorine, chlorine, bromine or iodine; a cyano radical, thio-   cyano, nitro, sulfamido, alkylamino, dialkylamino, aminocarbonyl, aminothio-   carbonyl, alkylaminocarbonyl, alkylaminothiocarbonyl, dialkylaminocarbonyl, dialkylaminothiocarbonyl or alkylcarbonylarnino or alkylthiocarbonylamino and wherein each alkyl radical, linear, branched or cyclic, saturated or unsaturated, comprises from 1 to 6 carbon atoms; a radical of general formula -S (O) nR in which n is equal to O. I or 2, and R represents an alkyl radical, linear, branched or cyclic, saturated or unsaturated, comprising from 1 to 6 optionally substituted carbon atoms by one or   several identical or different halogen atoms; a phenyl or phenyl radical   alkyl or a heterocycle comprising from 4 to 7 members, and from 1 to 3 heteroatoms selected   one of nitrogen, sulfur, oxygen or silicon, the straight or branched chain alkyl portion having from one to four carbon atoms and the phenyl or heterocycle portion being optionally substituted by one or more groups selected from halo genes, alkyls, haloalkyls, haloalkyls, haloalkylthio, cyano, thiocyano, nitro, sulfamido, aminocarbonyl, aminothiocarbonyl, alkylaminocarbonyl, alkylaminothiocarbonyl, dialkylaminocarbonyl, dialkylaminothiocarbonyl radicals, of which the linear, branched or cyclic alkyl moiety is saturated or s unsaturated, includes 1 to 6 carbon atoms, RR? R3 R. and R represent, independently of each other, a hydrogen atom; a halogen atom; an alkyl, alkoxy, alkylthio, haloalkyl or haloalkoxy radical; haloalkylthio, and whose linear, branched or cyclic, saturated or unsaturated alkyl radical contains from 1 to 6 carbon atoms, optionally substituted with one or more identical or different halogen atoms, and   Z represents a radical chosen from the groups: -N = C = O, -N = C = S, N = S = O.   8. Product according to claim 7, characterized in that in formula (I): A represents a halogen or an alkylthio / alkylsulphinyl / alkylsulphonyl group, unsubstituted or substituted, preferably with halogens, - B represents a radical; cyano, carboxarnido, thiocarboxamido, methyl or trifluoromethyl; represents a group -N = C = O or a group -N = C = S, - the substituents R R. R3 R4, Rs determine in position 1 of the pyrazole structure the 2,4,6-trichlorophenyl substitution, 2,6 4-dichloro-4-trifluoromethylphenyl, 2,6-dichloro-4-trifluoromethyloxyphenyl and 2,6-dichloro-4-trifluoromethylthiophenyl 9. Product according to claim 8, characterized in that in formula (I): A is chosen from trifluoromethylthio and trifluoromethylsulfinyl groups; ,   10. Product according to any one of claims 7 to 9, characterized   in that the product of formula (I) is selected from the following products: - product 1: 1- (2,6-dichloro-4-trifluoromethylphenyl) -3-cyano-4-trifluoromethylsulphinyl-5-isocyanato-pyrazole; product 2: 1- (2,6-dichloro-4-trifluoromethylphenyl) -3-cyano-4-trifluoromethylsulfenyl-5isocyanato-pyrazole; product 3: 1- (2,6-dichloro-4-trifluoromethylphenyl) -3-methyl-4-trifluoromethylsulfenyl-5-isocyanato-pyrazole; product 4: 1- (2,6-dichloro-4-trifluoromethylphenyl) -3-methyl-4-trifluoromethylsulphinyl-5-isocyanato-pyrazole; product 5: 1- (2,6-dichloro-4-trifluoromethylphenyl) -3-cyano-4-trifluoromethylsulfinyl-5isothiocyanato-pyrazole; s - 6: 1- (2,6-dichloro-4-trifluoromethylphenyl) -3-cyano-4-trifluoromethyl-5-isocyanato-pyrazole; 7: 1- (2,6-dichloro-4-trifluoromethylphenyl) -3-trifluoromethyl-4-trifluoromethylsulfenyl-5-isocyanato-pyrazole; product 8: 1- (2,6-dichloro-4-trifluoromethylphenyl) -3-trifluoromethyl-4-trifluoromethylsulfinyl-5-isocyanato-pyrazole; product 9: 1- (2,4,6-trichlorophenyl) -3-cyano-4-trifluoromethylsulfinyl-5-isocyanato pyrazole; -   product I 0: 1- (2,4,6-trichlorophenyl) -3-cyano-4-trifluoromethyl-5-sulfenyl isocyanato-pyrazole; S - product 1 1: 1- (2,6-dichloro-4-trifluoromethylphenyl) -3-cyano-4-chloro-5-isocyanato-pyrazole; 1: 2 - (2,4,6-trichlorophenyl) -3-cyano-4-bromo-5- (N-sulphinylamino) pyrazole; - product 1 3: 1- (2,4,6-trichlorophenyl) -3cyano-4-trifluoromethylthio-5- (N-sulfinylamino) -pyrazole; product 14: 1 (2,6-dichloro-4-trifluoromethylphenyl) -3-cyano-4-chloro-5- (N-sulfinylamino) -pyrazole; product 5: 1- (2,6-dichloro-4-trifluoromethylphenyl) -3-cyano-4-bromo-5- (N-sulfinylamino) pyrazole; 16: 1- (2,6-dichloro-4-trifluoromethylphenyl) -3-cyano-4-trifluoromethylthio- (N-sulfinylamino) pyrazole; 17: 1 - (2,6-dichloro-4-trifluoromethylphenyl) -3-cyano-4-trifluoromethylsulphinyl-5- (Nsulfinylamino) pyrazole; product 18: N, N, dimethyl-N '[1- (2,6-dichloro-4-trifluoromethylphenyl) -3-cyanopyrazol-5-yl] thiourea; product 19: N- (3,5-bis (trifluoromethyl) phenyl) -N '- [1- (2,6-dichloro-4-trifluoromethylphenyl) -3-cyanopyrazol-5-yl] urea; product 20: N- (2,6-dichloro-4-trifluoromethylphenyl) -N '- [1- (2,6-dichloro-4-trifluoromethylphenyl) -3-cyanopyrazol-5-yl] urea; product 2 1: N- (2-trifluoromethyl-4-nitrophenyl) -N '- [1- (2,6-dichloro-4-trifluoromethylphenyl) -3-cyanopyrazol-5-yl] urea; product 22: N, N'-bis [1- (2,6-dichloro-4-trifluoromethylphenyl) -3-cyano] trifluoromethyl-pyrazol-5-yl] urea; product 23: N, N '[1- (2,6-dichloro-4-trifluoromethylphenyl) -3-cyano-4-trifluoromethylsulphinylpyrazol-5-yl] carbodiimide; product 24: 1- (2,6-dichloro-4-trifluoromethylphenyl) -3-cyano-5- (N-heptafluoropropylsulphinylamino) -pyrazole; product 25: 3,6-dihydro-4,5-dimethyl-N- (1- (2,6-dichloro-4-trifluoromethylphenyl) -3-cyano-4-trifluoromethylsulfinyl-pyrazol-5-yl) 1,2 thiazine-1 -oxide; 26: 3,6-dihydro-4,5-dimethyl-N- (1- (2,4,6-trichlorophenyl) -3-cyanopyrazolyl) -1,2-thiazine-1 -oxide; I - product 27: 3,6-dihydro-4,5-dimethyl-N- (1- (2,4,6-trichlorophenyl) -3-cyano-4-bromopyrazol-5-yl) -1,2-thiazine 1 oxide; product 28: 3,6-dihydro-4,5-dimethyl-N- (1- (2,4,6-trichlorophenyl) -3-cyano-4-trifluoromethylthiopyrazol-5-yl) -1,2-thiazine-1 -oxide; 29: 3,6-Dihydro-4,5-dimethyl-N- (1- (2,6-dichloro-4-trifluoromethyl-phenyl) -3-cyalopyrazol-5-yl) -1,2-thiazine-1 -oxide; 30: 3,6-Dihydro-4,5-dimethyl-N- (1- (2,6-dichloro-4-trifluoromethyl-phenyl) -3-cyano-4-bromopyrazol-5-yl) -1,2-thiazine-1 oxide; product 31: 3,6-dihydro-4,5-dimethyl-N- (1- (2,6-dichloro-4-trifluoromethylphenyl) -3-cyano-4- (trifluoromethylthio) pyrazol-5-yl) -1,2-thiazine- 1 -oxide; 32: 1- (2,6-dichloro-4-trifluoromethylphenyl) -3-cyano-5- (2,3-dimethylbut-3-er-1-yl) aminopyrazole; product 33: 1- (2,6-dichloro-4-trifluoromethylphenyl) -3-cyano-4- (trifluoromethylsulfinyl) 5- (2,3-dimethylbut-3-en-1-yl) aminopyrazole; product 34: 1- (2,6-dichloro-4-trifluoromethylphenyl) -3-cyano-4- (trifluoromethylthio) -5- (2,3-dimethylt-3-en-1-yl) aminopyrazole; 11. Process for the preparation of a compound corresponding to the general formula (III), X A B 6 H N R2 R4 R3 I III I   in which A, B, X, R, R 2, R 3, R 3 and R 5 have the same meaning as in claim 1, said process being characterized in that a   product according to any one of claims 7 to 10, corresponding to the formula   (I), in which Z represents the -N = C = O or -N = C = S, with a   compound of general formula R6M, wherein R6 has the same meaning as above   and M represents an alkali metal such as lithium or an alkali metal salt   noterreux. 12. Process according to claim 11, characterized in that 1.0 to 1.25 moles of the compound according to the general formula R 6 M are reacted per mole of the 1-phenyl-5-iso (thio) cyanatopyrazole derivative. which corresponds to the general formula (I) at a temperature of between -78 and + 25 ° C. in a polar organic solvent medium, such as tetrahydrofuran, diethyl ether, methyl tert-butyl ether, dimethyl ether of ethylene glycol. 13. Products according to general formula (III) X A B H. In which: A and B represent, independently of one another: a hydrogen atom, a linear, branched or cyclic alkyl, alkenyl or alkynyl radical comprising from 1 to 12, preferably from 1 to 6 carbon atoms, the carbon chain of these radicals being   which may be substituted by one or more groups selected from   caux: halo. alkyloxy alkylthio. alkyloxycarbonyl, the alkyl radical of these radicals   caux, linear, branched or cyclic comprising from 1 to 6 carbon atoms; an atom   halogen selected from fluorine, chlorine, bromine or iodine; a cyano radical, thio-   cyano, nitro, sulfamido, alkylamino, dialkylamino, aminocarbonyl, aminothiocarbo-   alkyl, alkyl aminocarbonyl, alkylaminothiocarbonyl, dialkylaminocarbonyl, dial   alkylaminothiocarbonyl or alkylcarbonylamino or alkylthiocarbouylamino and wherein each alkyl residue linear, branched or cyclic? saturated or unsaturated, comprises from 1 to 6 carbon atoms; a radical of general formula S (O) nR in which n is equal to 0, 1 or 2, and R represents a saturated or unsaturated, linear, branched or cyclic alkyl radical comprising from 1 to 6 carbon atoms optionally substituted with one or   several identical or different halogen atoms, provided that A does not represent   does not feel a group -S (0), R; a phenyl or phenylalkyl radical or a heterocycle o comprising from 4 to 7 members, and from 1 to 3 heteroatoms chosen from nitrogen, sulfur, oxygen or silicon, the straight or branched alkyl part having from one to four carbon atoms and the phenyl or heterocycle part being optionally substituted by one or more groups chosen from halogens, alkyls, haloalkyls, haloalkoxy radicals, haloalkylthio radicals, cyano, thio cyano, nitro, sulfamido, aminocarbonyl, aminothiocarbonyl radical, alkylaminocarbonyl, alkylaminothiocarbonyl, dialkylaminocarbonyl, dialkylaminothiocarbonyl, in which the linear, branched or cyclic, saturated or unsaturated alkyl moiety comprises 1 to 6 carbon atoms; R ', R. R3, R. and R. represent, independently of one another, an atom   s of hydrogen; a halogen atom; an alkyl, alkoxy, alkylthio, halogeno   alkyl, haloalkoxy, haloalkylthio, and whose alkyl radical, linear, branched or   cyclic, saturated or unsaturated, contains from 1 to 6 carbon atoms   with one or more identical or different halogen atoms, X represents oxygen or sulfur, provided that:   o When X = S; R6 represents an alkyl, alkenyl or alkynyl radical, linear or branched   embedded image, comprising from 5 to 12 carbon atoms, the carbon chain of these radicals being   likely to be substituted by one or more groups selected from among the   halo, alkyloxy, alkylthio, alkyloxycarbonyl, the alkyl radical of these radicals.   caux, linear, branched or cyclic comprising from 1 to 6 carbon atoms; and when X = O, is not hydrogen, and RG is linear, branched or cyclic alkyl, alkenyl or alkynyl having from 8 to 12 carbon atoms, the carbon chain of these radicals being capable of being substituted by one or more groups chosen from the radicals: halo, alkyloxy, alkylthio, alkyloxycarbonyl, the alkyl radical of these radicals, linear, branched or cyclic comprising from 1 to 6 carbon atoms; a phenylalkyl radical comprising at least eight carbon atoms or a heterocycle having from 4 to 7 ring members, and from 1 to 3 heteroatoms chosen from nitrogen, sulfur, oxygen or silicon, the straight or branched chain alkyl part having two to four carbon atoms, the phenyl or heterocyclic moiety being optionally substituted by one or two groups selected from halogens, alkyls, haloalkyls, lalogenoalkoxy, haloalkylthio, cyano, thiocyano, nitro, amino carboxy , aminothiocarbonyl, alkylamino carbonyl, alkylaminothiocarbonyl, dialkylaminocarbonyl, dialkylaminothiocarbouyl, halogeno, alkylsulfonyl or haloalkylsulfinyl and wherein the linear, branched or cyclic, saturated or unsaturated alkyl moiety comprises from one to four carbon atoms and the heterocyclic moiety optionally substituted by a phenyl radical itself substituted by one or more groups identical or different selected from halogens,. alkyl halides, halo-genoalkyls, halo-genoalkoxy, halo-genoalkylthio, cyano, thiocyano, nitro, aminocarbonyl, aminothiocarbonyl, alkylaminocarbouyl, alkylaminothiocarbonyl, dialkylaminocarbonyl, dialkylaminothiocarbouyl,   haloalkylsulfonyl or haloalkylsulfinyl.   14. Process for the preparation of pyrazole derivatives having a (thio) urethane function at the 5-position, and corresponding to the general formula (IV)   (URETHAN OR THIOURETHANES DERIVATIVES):   Wherein R 1, R 5, R 4, R "R 6 have the same meaning as in claim 1, and X and Y are independently of one another , Oxygen or sulfur, which process is characterized in that a product is reacted according to one of   any of claims 7 to 10, having the general formula (I), in   Z represents the sequence -N = C = O or -N = C = S, with a compound of general formula R, YH.   15. Process according to claim 14, characterized in that the reaction is carried out in the presence or absence of an inert organic solvent, at a temperature of between -68 ° C. and + 150 ° C., using from 1.0 to 1, 5 mol, preferably from 1.1 to 1.25, of the compound according to the formula R 6 YH, per mole of the 1-phenyl-5 compound   iso (thio) cyanatopyrazole corresponding to formula (I).   16. Products corresponding to formula IV as defined in claim 14, wherein: A and B represent, independently of one another: a hydrogen atom; a linear, branched or cyclic alkyl, alkenyl or alkynyl radical comprising from 1 to 12, preferably from 1 to 6, carbon atoms, the carbon chain of these radicals being capable of being substituted by one or more groups chosen from the radi Y, j,   halo, alkyloxy, alkylthio, alkyloxycarbonyl, the alkyl radical of these radicals.   linear, branched or cyclic cales comprising from 1 to 6 carbon atoms; an atom   halogen selected from fluorine, chlorine, bromine or iodine; a cyano radical, thio-   cyano, nitro, sulfamido, alkylamino, dialkylamino, aminocarbouyl, aminothio carbonyl, alkylaminocarbonyl, alkylaminothiocarbouyl, dialkylaminocarbonyl, dialkylaminothiocarbonyl or alkylcarbonylamino or alkylthiocarbonylamino and wherein each alkyl radical, linear, branched or cyclic, saturated or unsaturated, comprises from 1 to   6 carbon atoms; a phenyl or phenylalkyl radical or a heterocycle comprising   from 4 to 7 members, and from 1 to 3 heteroatoms selected from nitrogen, sulfur, oxygen or silicon, the straight or branched chain alkyl portion having from one to four carbon atoms and the phenyl portion or heterocycle being optionally substituted by one or more groups selected from halogens, alkyls   haloalkyls, haloalkoxy, haloalkylthio, cyano radical, thioalkyl   cyano, nitro, sulphamido, aminocarbonyl, aminothiocarbouyl, alkylaminocarbouyl,> alkylaminothiocarbonyl, dialkylaminocarbonyl, dialkylaminothiocarbonyl, whose linear, branched or cyclic, saturated or unsaturated, alkyl moiety comprises from 1 to 6 carbon atoms, B may also represent a radical of general formula S (O) nR wherein n is 0, 1 or 2, and R represents a saturated or unsaturated, linear, branched or cyclic alkyl radical comprising from 1 to 6 carbon atoms optionally substituted by one or more halogen atoms, identical or different; R, R2, R3 'R and R5 represent, independently of one another, an atom   dhydrogène; a halogen atom; an alkyl, alkoxy, alkylthio, halogeno   alkyl, haloalkoxy, haloalkylthio, and the alkyl radical, linear, branched or   2> cyclic, saturated or unsaturated, contains from 1 to 6 carbon atoms optionally sub-   Stated with one or more identical or different halogen atoms, X and Y are chosen such that: either (X = O and Y = S) or (X = S and Y = O) and R 1 represents a radical alkyl. alkenyl or alkynyl, linear, branched or cyclic, o comprising from 1 to 12, preferably from 1 to 6, carbon atoms, the carbon chain of these radicals being capable of being substituted by one or more groups chosen from the radicals: halo, alkyloxy, alkylthio, alkyloxycarbouyl, the alkyl residue of these radicals, linear, branched or cyclic comprising from 1 to 6 carbon atoms; a phenyl or phenylalkyl radical or a heterocycle having from 4 to 7 shafts, and from 1 to 3 heteroatoms selected from nitrogen, sulfur, oxygen or silicon, the straight or branched chain alkyl moiety having from one to four atoms carbon, the phenyl or heterocyclic portion being optionally substituted by one or more groups selected from halogens, alkyls, haloalkyls,   haloalkoxy, haloalkylthio, cyano, thiocyano, nitro, amino-   carbonyl, aminothiocarbonyl, alkylaminocarbonyl, alkylaminothiocarbonyl e, dial -   kylaminocarbonyl, dialkylaminothiocarbouyl, halo, alkylsulphonyl or halo   o genoalkylsulfinyl and whose straight chain, branched or cyclic alkyl part, saturated   or unsaturated comprises from one to four carbon atoms and the hetero-   cyclic optionally substituted with a phenyl radical which is itself substituted with one or more identical or different groups chosen from halogens, alkyls, haloalkyls, haloalkoxy radicals, haloalkylthio radicals, cyano radical, thio radical;   s cyano, nitro, aminocarbouyl, aminothiocarbouyl, alkylaminocarbonyl, alkyl-   aminothiocarbonyl, dialkylaminocarbonyl, dialkylaminothiocarbonyl, halogeno   alkylsulfonyl or haloalkylsulfinyl, that is (X = O and Y = O) and RG represents a linear, branched or cyclic alkyl, alkenyl or alkynyl radical comprising from 8 to 12 carbon atoms, the carbon chain of these radicals being capable of be substituted by one or more groups chosen from the radicals: halo, alkyloxy, alkylthio, alkyloxycarbonyl, the alkyl radical of these radicals, linear, branched or cyclic comprising from 1 to 6 carbon atoms; a phenyl or phenylalkyl radical or a heterocycle having from 4 to 7 members, and from 2 to 1 to 3 heteroatoms selected from nitrogen, sulfur, oxygen or silicon, the straight or branched alkyl portion having one to four carbon atoms, the phenyl or heterocyclic portion being optionally substituted by one or more groups chosen from halogens, alkyls, haloalkyls, haloalkoxy radicals, haloalkylthio radicals, cyano, thiocyano, nitro, aminocarbonyl radical,   aminothiocarbonyl alkylaminocarbonyl, alkylaminothiocarbonyl, dialkyl-   aminocarbonyl, dialkylaminothiocarbonyl, halo, alkylsulphonyl or halo   genoalkylsulfinyl and whose straight chain, branched or cyclic alkyl part, saturation   of 1 to 4 carbon atoms and the hetero   cyclic ring optionally substituted by a phenyl radical itself substituted by one or more identical or different groups chosen from halogens, alkyls, haloalkyls, haloalkoxy radicals, haloalkylthio radicals, cyano radical, thio radical;   s cyano, nitro, aminocarbonyl, aminothiocarbonyl, alkylaminocarbonyl, alkylamino-   thiocarbonyl, dialkylaminocarbonyl, dialkylaminothiocarbonyl, haloalkyl-   sulfouyl or haloalkylsulfinyl.   17. Process for the preparation of a compound corresponding to the general formula (V), wherein R, R, R, R, R, R, R, R, same meaning as in claim 1, and X represents oxygen or sulfur, this process being characterized in   reacting a product according to any one of claims 7 to 10,   having the general formula (I), wherein Z represents chaining   -N = C = O or -N = C = S, with a compound of general formula R7RaNH.   18. Process according to claim 17, characterized in that 1.0 to 1.25 moles of the compound according to the general formula R7RNH are used per mole of the 1-phenyl-5-iso (thio) cyanatopyrazole derivative corresponding to the general formula (I), in an inert organic solvent, chosen preferably from toluene, dichloromethane, dichloroethane, chlorobenzene, used alone or in combination, at a temperature   between -78 C and +100 C, and advantageously between -20 C and +50 C.   19. A product of general formula (V) as defined in claim 17, wherein:   A and B represent, independently of one another: a hydrogen atom; a radical   alkyl, alkenyl or alkynyl, linear, branched or cyclic, comprising from 1 to 12, preferably from 1 to 6, carbon atoms, the carbonne chain of these radicals being capable of being substituted by one or more groups chosen from radiaux: halo, alkyloxy, alkylthio, alkyloxycarbonyl, the alkyl radical of these radicals, linear, branched or cyclic comprising from 1 to 6 carbon atoms; an atom   halogen selected from fluorine, chlorine, bromine or iodine; a cyano radical, thio-   cyano, nitro, sultamido, alkylamino, dialkylamino, aminocarbonyl, aminothio-   carbonyl, alkylaminocarbonyl, alkylaminothiocarbonyl, dialkylaminocarbonyl, dialkylaminothiocarbonyl or alkylcarbonylamino or alkylthiocarbonylamino and wherein each alkyl radical, linear, branched or cyclic, saturated or unsaturated, comprises from 1 to 6 carbon atoms; a phenyl or phenylalkyl radical or a heterocycle comprising from 4 to 7 shafts, and from 1 to 3 heteroatoms selected from nitrogen, sulfur, oxygen or silicon, the straight or branched alkyl moiety having from one to four carbon atoms and the phenyl or heterocycle part being optionally substituted by one or more groups chosen from halogens, alkyls,   halo-genoalkyls, haloalkoxy, halo-genoalkylthio, cyano radical, thio-   cyano, nitro, sulfamido, aminocarbonyl, aminothiocarbouyl, alkylaminocarbonyl, alkylaminothiocarbonyl, dialkylaminocarbonyl, dialkylaminothiocarbouyl, whose linear, branched or cyclic alkyl moiety, saturated or unsaturated, comprises from 1 to 6 carbon atoms, B may also represent a radical of formula general -S (O) nR wherein n is 0, 1 or 2, and R represents a saturated or unsaturated, linear, branched or cyclic alkyl radical comprising from 1 to 6 carbon atoms optionally substituted by one or more halogen atoms, identical or different; R '' R. ' R3, R4 and R represent, independently of one another, an atom   hydrogen; a halogen atom; an alkyl, alkoxy, alkylthio, halogeno   alEyl, haloalkoxy, haloalkylthio, and whose linear, branched or cyclic alkyl radical, saturated or unsaturated, contains from 1 to 6 carbon atoms optionally substituted by one or more identical or different halogen atoms, R7 and Rs represent, independently of one another, the hydrogen atom or a linear, branched or cyclic alkyl, alkenyl or alkynyl radical comprising from 1 to 12, preferably from 1 to 6, carbon atoms, the carbon chain these radicals being capable of being substituted by one or more groups chosen from the radicals: halo, alkyloxy, alkylthio, alkyloxycarbonyl, the alkyl radical of these radicals, linear, branched or cyclic comprising from 1 to 6 carbon atoms; a phenyl or phenylalkyl radical or a heterocycle having from 4 to 7 members, and from 1 to 3 heteroatoms selected from nitrogen, sulfur, oxygen or silicon, the straight or branched chain alkyl moiety having one to four carbon atoms, the phenyl or heterocyclic portion being optionally substituted by one or more groups chosen from halogens, alkyls, haloalkyls, haloalkoxy, haloalkylthio, cyano, thiocyano, nitro, aminocarbouyl, aminothiocarbonyl, alkylaminocarbonyl, alkylaminothiocarbonyl radical; dialkylaminocarbouyl, dialkylaminothiocarbouyl, halo, alkylsulfonyl or haloalkylsulfinyl and wherein the straight, branched or cyclic, saturated or unsaturated alkyl moiety comprises from one to four carbon atoms and the hetero ring moiety optionally substituted by a phenyl radical itself substituted by one or more identical or different groups chosen among the halogens, the alkyls,   haloalkyls, haloalkoxy, haloalkylthio, cyano, thio-   cyano, nitro, aminocarbonyl, aminothiocarbouyl, alkylaminocarbouyl, alkyl-   aminothiocarbouyl, dialkylaminocarbouyl, dialkylaminothiocarbonyl, haloalkylsulfonyl or haloalkylsulphinyl, 20. products of general formula (V), as defined in claim 17, wherein:   A and B represent, independently of one another: a hydrogen atom; a radical   linear, branched or cyclic alkyl, alkenyl or alkynyl chain comprising from 1 to 12, preferably from 1 to 6, carbon atoms, the carbon chain of these radicals being   which may be substituted by one or more groups selected from   halo, alkyloxy, alkylthio, alkyloxycarbonyl, the alkyl radical of these radicals.   caux, linear, branched or cyclic comprising from 1 to 6 carbon atoms; a halogen atom selected from fluorine, chlorine, bromine or iodine; a cyano radical, thio   cyano, nitro, sulfamido, alkylamino, dialkylamino, aminocarbouyl, aminothiocarbo-   alkylaminocarbonyl, alkylaminothiocarbouyl, dialkylaminocarbonyl, dialkylaminocarbonyl,   kylaminothiocarbonyl or alkylcarbouylamino or alkylthiocarbonylamino and wherein each alkyl radical, linear, branched or cyclic, saturated or unsaturated, comprises from 1 to 6 carbon atoms; a radical of general formula -S (O), 1R in which n is 0, 1 or 2. and R represents an alkyl radical, linear, branched or cyclic, saturated or unsaturated, containing from 1 to 6 atoms of optionally substituted with one or more identical or different halogen atoms; a phenyl or phenylalkyl radical or a heterocycle comprising from 4 to 7 members, and from 1 to 3 heteroatoms chosen from nitrogen, sulfur, oxygen or silicon, the straight or branched alkyl part having from one to four carbon atoms and the phenyl or heterocycle part being optionally substituted by one or more selected groups among halogens, alkyls, haloalkyls, haloalkoxy, haloalkylthio, cyano, thiocyano, nitro, sulLamido, aminocarbonyl, aminothiocarbonyl, alkylaminocarbonyl radical; , alkylaminothiocarbiyl, dialkylaminocarbouyl, dialkylaminothiocarbonyl, the linear, branched or cyclic, saturated or unsaturated alkyl moiety of which 1 to 6 carbon atoms, R '' R 'R3, R4 and Rs independently of one another atom   hydrogen; a halogen atom; an alkyl, alkoxy, alkylthio, halogeno   alkyl, haloalkoxy, haloalkylthio, and the alkyl radical, linear, branched or   cyclic, saturated or unsaturated, contains from 1 to 6 carbon atoms   with one or more identical or different halogen atoms, R7 represents the hydrogen atom and Rs represents a heterocycle of general formula (I) in which A, B, R, R2, R3, R4, and R5 have the same definition as above,   while Z represents a bond.   21. Process for the preparation of a compound corresponding to the general formula (VI): B A A B R1 CR5 R1 R3 R3 (Vl)   in which A, B, R, and R3 R4 R "have the same meaning as in the   1, which process is characterized in that a product is reacted according to   Any of claims 7 to 10, having the general formula (I) in   which Z represents the sequence -N = C = O or -N = C = S, with 3-methyl-1 phenyl-3-phospholene-1 -oxide.   22. Process according to claim 21, characterized in that the use   1.0 to 1.20 mol of the compound of the general formula (I), in an inert atmosphere, with 0.04 to 0.06 mol of the phospholene derivative, at a temperature between   +20 C and +80 C, preferably around +50 C.   23. Product of general formula (VI): B A A B N NN / R1 R5 R1   R3 R3 (VI) wherein: A and B represent, independently of one another: a hydrogen atom; a linear, branched or cyclic alkyl, alkenyl or alkynyl radical comprising from 1 to 12, preferably from 1 to 6, carbon atoms, the carbon chain of these radicals being capable of being substituted by one or more chosen groups among the radicals: halo, alkyloxy, alkylthio, alkyloxycarbonyl, the alkyl residue of these radicals, linear, branched, or cyclic comprising from 1 to 6 carbon atoms; a halogen atom selected from fluorine, choline, bromine or iodine; a cyano radical,   thiocyano, nitro, sulfamido, alkylamino, dialkylamino, aminocarbonyl, aminothio-   carbouyl, alkylaminocarbonyl, alkylaminothiocarbonyl, dialkylaminocarbonyl, dialkylaminothiocarbonyl or alkylcarbonylamino or alkylthiocarbouylamino and wherein each alkyl radical, linear, branched or cyclic, saturated or unsaturated, comprises from 1 to 6 carbon atoms; a radical of general formula S (O) nR in which n is equal to 0, 1 or 2, and R represents a saturated or unsaturated, linear, branched or cyclic alkyl radical comprising from 1 to 6 carbon atoms optionally substituted with one or   several identical or different halogen atoms; a phenyl or phenyl radical   alkyl or a heterocycle comprising from 4 to 7 shafts, and from 1 to 3 heteroatoms selected   Nitrogen, sulfur, oxygen or silicon, straight or branched chain alkyl of one to four carbon atoms and phenyl or heterocycle   being optionally substituted by one or more groups selected from halo   genes, alkyls, haloalkyls, haloalkoxy, haloalkylthio, cyano, thiocyano, nitro, sulfamido, aminocarbouyl, aminothiocarbonyl, ..   alkylaminocarbonyl, alkylaminothiocarbonyl, dialkylaminocarbonyl, dialkyl-   aminothiocarbonyl, whose linear, branched or cyclic, saturated or unsaturated, alkyl moiety comprises 1 to 6 carbon atoms, R ', R 2, R 3, R and Rs independently of one another   s of hydrogen; a halogen atom; an alkyl, alkoxy, alkylthio, halogeno   alkyl, haloalkoxy, haloalkylthio, and the alkyl radical, linear, branched or   cyclic, saturated or unsaturated, contains from 1 to 6 carbon atoms   by one or more identical or different halogen atoms.   24. A process for the preparation of a compound corresponding to the general formula (VII): ## STR2 ## in which A, B.sub.2 R.sub.2, R.sup.3 R.sub.4 R.sub.4 and R.sub.6 have the same meaning as in claim 1: R6 / H N B C 1 R1 R5 R21 R4 R3 - (VII)   this process being characterized in that a product is reacted according to any one of   Claims 7 to 10, having the general formula (I) in which Z represents   Sense the sequence -N = S = O, with a compound of general formula R6M, formula   wherein M represents an alkali metal or an alkaline earth metal salt.   25. Process according to claim 24, characterized in that 1.0 to 1.25 moles of the compound of general formula Et6M are reacted for 1 mole of the derivative.   1-phenyl-5- (N-sulfinylamino) pyrazole according to the general formula (I) at a temperature of   between -78 ° C. and + 25 ° C. in polar solvents and preferably   among the tetrahydrofuran, ethers, such as diethyl ether, methyl tertiary   butyl ether, the ethylene glycol methylether.   26. Products of the general formula (V1I) as defined in claim 24, wherein:   A and B represent, independently of one another: a hydrogen atom; a radical   alkyl cal. alkenyl or alkynyl, linear, branched or cyclic, comprising from 1 to 12, preferably from 1 to 6, carbon atoms, the carbon chain of these radicals being   which may be substituted by one or more groups selected from   halo, alkyloxy, alkylthio, alkyloxycarbonyl, the alkyl radical of these radicals.   caux, linear, branched or cyclic comprising from 1 to 6 carbon atoms; a halogen atom selected from fluorine,. chlorine, bromine or iodine; a cyano radical, thio   o cyano, nitro, sulfamido, alkylamino, dialkylamino, aminocarbonyl, aminothiocarbo-   alkyl, alkylaminocarbonyl, alkylaminothiocarbonyl, dialkylaminocarbonyl, dialkylaminothiocarbonyl or alkylcarbonylamino or alkylthiocarbonylamino and wherein each alkyl radical, linear, branched or cyclic, saturated or unsaturated, comprises from 1 to 6 carbon atoms; a radical of general formula S (O) nR wherein n is 0, 1 or 2, and R represents a linear, branched or cyclic alkyl radical, saturated or unsaturated, containing from 1 to 6 carbon atoms, if appropriate; substituted by one or   several identical or different halogen atoms; a phenyl or phenyl radical   alkyl or a heterocycle comprising from 4 to 7 members, and from 1 to 3 heteroatoms selected   one of nitrogen, sulfur, oxygen or silicon, straight or branched chain alkyl having from one to four carbon atoms and phenyl or heterocycle part   being optionally substituted by one or more groups selected from   genes, alkyls, haloalkyls, haloalkoxy, haloalkylthio, cyano, thiocyano, nitro, sultamido, aminocarbonyl, aminothiocarbouyl, alkylamino carboyl, alkylaminothiocarbonyl, dialkylaminocarbouyl. dialkyl aminothiocarbonyl, the linear, branched or cyclic, saturated or unsaturated alkyl moiety thereof having 1 to 6 carbon atoms, R ', R2, R3, R3 and R3 independently of one another   hydrogen; a halogen atom; an alkyl, alkoxy, alkylthio, halogeno   alkyl, haloalkoxy, haloalkylthio, and the alkyl radical, linear, branched or   cyclic, saturated or unsaturated, contains from 1 to 6 carbon atoms optionally   with one or more identical or different halogen atoms, R6 represents a linear, branched or cyclic alkyl, alkenyl or alkynyl radical comprising from 1 to 12, preferably from 1 to 6, carbon atoms, the carbon chain of these radicals being capable of being substituted by one or more groups chosen from the radicals: halo, alkyloxy, alkylthio, alkyloxycarbonyl, the alkyl radical of these radicals, linear, branched or cyclic comprising from 1 to 6 carbon atoms; a phenyl or phenylalkyl radical or a heterocycle having from 4 to 7 members, and from 1 to 3 heteroatoms selected from nitrogen, sulfur, oxygen or silicon, the straight or branched alkyl portion having one to four atoms carbon, the phenyl or heterocyclic portion being optionally substituted by one or more groups selected from halogens, alkyls, haloalkyls, haloalkoxy, haloalkylthio, cyano, thiocyano, nitro, amino carbonyl, aminothiocarbonyl, alkylaminocarbonyl, alkylaminothiocarbyl radical; dialkylaminothiocarbonyl haloalkylsulphonyl or haloalkylsulphinyl and whose straight chain, branched or cyclic, saturated or unsaturated alkyl part comprises from one to four carbon atoms and the heterocyclic part optionally substituted by a phenyl radical itself substituted by a or more identical or different groups selected from halogens, alkyls,   hal o geno alkyls, halo genoalkoxy, halo genoalkylthio, cyano radical, thio -   cyano 'nitro, aminocarbonyl, aminothiocarbonyl, alkylaminocarbonyl, alkyl   aminothiocarbouyl, dialkylaminocarbonyl, dialkylaminothiocarbonyl, halogeno   alkylsulfouyl or haloalkylsulfinyl: 27. A process for the preparation of derivatives corresponding to the general formula (VIII): ## STR2 ## (VIII)   in which A, B, R, R3, R4, R5 have the same meaning as in the claim * s 1 and R9? Ro, R 1 and R 2 represent, independently of each other: a hydrogen atom; a branched or cyclic linear alkyl radical, optionally unsaturated,   preferably 1 to 12, preferably 1 to 6, carbon atoms; a halogen radical   genoalkyl, the alkyl moiety of which is linear, branched or cyclic, optionally unsaturated, having from 1 to 12, preferably from 1 to 6, carbon atoms; a radical to alkoxyl, the branched or cyclic linear alkyl moiety, optionally unsaturated, having from 1 to 12, preferably from 1 to 6, carbon atoms, this process   characterized in that a product is reacted according to any one of the   Claims 7 to 10, having the general formula (I) in which Z represents the sequence -N = S = O with a compound of the general formula R9CH = CR'o-CR = CHR2. 28. The process according to Claim 27, characterized in that reacting from 1.0 to 3.0 moles of the compound of the general formula R9CH = CRo-CR = CR2 for 1.0 mole of the 1-phenyl-5- (Nsulfinylamino) pyrazole derivative according to the general formula ( I) at a temperature of between + 25 ° C. and + 120 ° C. in solvents   o inert chosen from dichloroethane, toluene or chlorobenzene.   29. Product of general formula (VIII): R9 R5 R2 R4 R3 (VIII)   wherein: wherein A and B represent, independently of one another: a hydrogen atom; an alkyl, alkenyl or alkynyl radical, linear, branched or cyclic, comprising from 1 to 12, preferably from 1 to 6, carbon atoms, the carbon chain of these radicals being capable of being substituted by one or more groups selected from the radicals: halo, alkyloxy, alkylthio, alkyloxycarbonyl, the alkyl radical of these radicals, linear, branched, or cyclic comprising from 1 to 6 carbon atoms; a halogen atom selected from fluorine, chlorine, bromine or iodine; a cyano, thiocyano, nitro, sulfamido, alkylamino, dialkylamino or aminocarbonyl radical,   aminothiocarbonyl, alkylaminocarbonyl, alkylaminothiocarbonyl, dialkylamino   carbonyl, dialkylaminothiocarbonyl or alkylcarbonylamino or alkylthiocarbouyl-   amino and each of which linear, branched or cyclic, saturated or unsaturated, alkyl radical contains from 1 to 6 carbon atoms; a radical of general formula S (O) nR in which n is equal to 0, 1 or 2, and R represents an alkyl radical, linear, branched or cyclic, saturated or unsaturated, comprising from 1 to 6 carbon atoms optionally substituted by one or more identical or different halogen atoms; a phenyl or phenylalkyl radical or a heterocycle comprising from 4 to 7 links, and from 1 to 3 heteroatoms chosen from nitrogen, sulfur, oxygen or silicon, the straight or branched chain alkyl moiety having from one to four carbon atoms and the phenyl or heterocycle portion being optionally substituted by one or more selected groups   among the halogens, alkyls, haloalkyls, haloalkoxys, halogens,   genoalkylthio, the cyano, thiocyano, nitro, sulfamido, aminocarbonyl, amino-   thiocarbonyl, alkylaminocarbouyl, alkylaminothiocarbonyl, dialkylamino ...: ..   carbonyl, dialkylaminothiocarbouyl, in which the linear, branched or cyclic, saturated or unsaturated, alkyl moiety comprises from 1 to 6 carbon atoms, R 2 R 3, R 3 and R 5 represent, independently of one another, a hydrogen atom; a halogen atom; an alkyl, alkoxy, alkylthio, haloalkyl radical; haloalkoxy, haloalkylthio, and whose linear, branched or cyclic alkyl radical, saturated or unsaturated, contains from 1 to 6 carbon atoms optionally substituted by one or more identical or different halogen atoms, R ', R'o, R 'and R2 represent, independently of each other: hydrogen; a linear, branched or cyclic, optionally unsaturated, alkyl radical containing from 1 to 10 12, preferably from 1 to 6, carbon atoms; a haloalkyl radical the branched linear or cyclic alkyl moiety, optionally unsaturated, having from 1 to 12, preferably from 1 to 6, carbon atoms; an alkoxyl radical of the alkyl moiety is linear branched or cyclic, optionally unsaturated, comprising   from 1 to 12, preferably from 1 to 6, carbon atoms.   30. Process for the preparation of derivatives corresponding to the general formula (IX): Ri, Rg A B | H N R12 R10 R1 R5 R2 R4 R3 (IX)   in which A, B, R 2, R 3, R 4 R 4, have the same meaning as in claim 1 and R 9, Ro, R and R 2 represent, independently of each other: hydrogen a linear alkyl radical branched or cyclic, optionally unsaturated, having from 1 to 12, preferably from 1 to 6, carbon atoms; a haloalkyl radical   the alkyl moiety is linear branched or cyclic, optionally unsaturated, comprising   from 1 to 12, preferably from 1 to 6, carbon atoms; an alkoxyl radical whose branched or cyclic, optionally unsaturated, linear alkyl radical has from 1 to 12, preferably from 1 to 6, carbon atoms, this process being characterized in   alkaline hydrolysis of a compound according to claim 28.   31. A method according to claim 30, characterized in that one uses   1.0 to 2.5 moles of sodium hydroxide per mole of compound according to the general formula (VII), at a temperature of between + 20 ° C and + 75 ° C, in preferably polar solvents, such as tetrahydrofuran, dioxane, ethanol or water and their mixtures.   32. Compounds of formula (IX), as defined in the claim wherein: A, B, R ', R3, R4, R and R6 are as defined above, R9, Ro, R' and R2 represent, independently of each other: hydrogen; a branched or cyclic linear alkyl radical, optionally unsaturated, comprising 1 to 12, preferably 1 to 6, carbon atoms; a haloalkyl radical in which the alkyl moiety is branched or cyclic linear, optionally unsaturated, having from 1 to 12, preferably from 1 to 6, carbon atoms; an alkoxyl radical whose branched or cyclic linear alkyl moiety, optionally unsaturated, having from 1 to 12, preferably from 1 to 6, carbon atoms; At least one of Rg, Ro, R 'and R2 represents an alkyl or haloalkyl radical and the sum of the number of carbon atoms of the radicals representing an alkyl or a halo   alkyl is greater than or equal to 3.   33. Composition intended for the elimination of pests and / or insects, characterized in that it comprises at least one effective amount of a   compound according to one of claims 7 to 10, 13, 16, 19, 23, 26, 29 and 32 in a ... please, please.   34. Method of control of arthropods and plant parasitic nematodes which consists in applying to plants or more generally to the environment envi   an effective amount of a compound according to one of claims 7 to 10, 13,