Derivatives of 5-substituted alkylaminopyrazoles as pesticides

FIELD: chemistry.

SUBSTANCE: described are derivatives of 5-substituted alkylaminopyrazoles of formula (I) , where R1 stands for CN, W stands for C-halogen; R2 stands for halogen, R3 stands for (C1-C3)-halogenoalkyl, R4 stands for (C1-C6)-alkyl, A stands for (C1-C12)-alkylene, R5 stands for (C1-C6)-alkyl, R6 stands for (C1-C6)-halogenoalkyl, n equals 2, or their pesticidely acceptable salts. Compounds demonstrate insecticidal activity and parasiticidal activity. The method of obtaining formula (I) is described, including interaction of compound of formula (II) with compound of formula (III) R5-O-A-NH2 and interaction on compound obtained with compound of formula (V) R4-L1.

EFFECT: obtaining derivatives which can be applied as pesticides.

3 cl, 6 tbl, 18 ex

 

The invention relates to the field of combating pests (including insects, spiders and worms (including nematodes)) derivatives of 5-substituted alkalinisation, to new compounds and compositions on their basis, as well as to methods for their preparation.

The destruction of insects, spiders and worms derivatives of 1-arylpyrazole described, for example, in patent publications WO 93/06089, WO 94/21606, WO 87/03781, EP 0295117, EP 659745, EP 679650, EP 201852 and US 5232940. The destruction of parasites in animals derived 1-arylpyrazole also described, for example, in patent publications WO 00/35884, EP 0846686, WO 98/24769 and WO 97/28126.

In addition, in patent WO 02/066423 described a method of obtaining derivatives of 1-arylpyrazole.

However, the level and/or duration of action of these compounds known from the prior art, is not entirely satisfactory for all applications, in particular against certain organisms or by using low concentrations.

Since modern pesticides must meet wide range of requirements, for example regarding the level, duration and spectrum of action, range of applicability, toxicity, combination with other active substances, the combination with supporting means, of a composition or synthesis, and because of the emergence of resistance, development pointed to by the x substances can never be considered complete, and constantly there is a high need for new compounds which have advantages compared with the known compounds, at least in regard to certain aspects.

The purpose of this invention is to develop compounds that extend the range of pesticides in various aspects, in particular in respect of the destruction of parasites in animals.

This invention relates to a method for the destruction of parasites in the animal body and animal body, introducing the animal number, effective for the destruction of parasites derived 5-substituted acylaminopyrazoles formula (I):

where:

R1denotes CN;

W represents C-halogen, or-CH3;

R2denotes hydrogen, halogen or CH3;

R3means (C1-C3-halogenoalkane,

(C1-C3)-halogenoalkanes or S(O)p-(C1-C3-halogenoalkane;

R4denotes hydrogen, (C2-C6)-alkenyl,

(C2-C6)-halogenoalkanes, (C2-C6)-quinil, (C2-C6-halogenoalkanes, (C3-C7-cycloalkyl, CO-(CH2)q-R7, -COR8, CO-(CH2)q-R9, -CO-(C1-C4)-alkyl-(C1-C6)-alkoxygroup, -CO2-(CH2)q 7, CO2R8, -CO2-(CH2)q-R9, -CO2-(C3-C7-cycloalkyl, -CO2-(C1-C4)-alkyl-(C3-C7-cycloalkyl, -CO2-(C3-C6)-alkenyl, -CO2-(C3-C6)-quinil, CONR10R11, -CH2R7, -CH2R9, OR7, OR8or or9; or (C1-C6)-alkyl, unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C6-alkoxygroup, (C1-C6-halogenoalkanes, (C3-C7)-cycloalkyl, S(O)pR8, CO2-(C1-C6)-alkyl, -O(C=O)-(C1-C6)-alkyl, NR10COR12, NR10R11, CONR10R11, SO2NR10R11, OH, CN, NO2, OR7, NR10SO2R8, COR8and OR9;

A stands for (C1-C12-alkylen [preferably

(C1-C6-alkylen] or (C1-C12-halogenoalkane [preferably (C1-C6-halogenoalkane], in which 2, 3 or 4 adjacent carbon atom may form part (C3-C8)-cycloalkyl ring, which is unsubstituted or substituted by one or more radicals selected from the group consisting of (C1-C6)-alkyl and halogen; or represents (C1-C12 -alkylen or (C1-C12-halogenoalkane, in which last two mentioned groups are methylene parts replaced by a group selected from-C(=O)-, -C(=NH)-, -O-, -S - and-NR15-, provided that the replacing group is not associated with the neighboring atom, O or N; or denotes (C2-C12-albaniles or (C2-C12-halogenoalkanes;

R5denotes H, (C3-C6)-alkenyl, (C3-C6)-halogenoalkanes, (C3-C6)-quinil, (C3-C6-halogenoalkanes, (C3-C7-cycloalkyl, -(CH2)qR7, -(CH2)qR9or NR10R11; or denotes (C1-C6)-alkyl, unsubstituted or substituted by one or more radicals selected from the group consisting of halogen,

(C1-C6-alkoxygroup, (C1-C6-halogenoalkanes,

(C3-C6-alkenylacyl, (C3-C6-halogenoalkanes,

(C3-C6-alkyloxy, (C3-C6-halogenoalkanes,

(C3-C7)-cycloalkyl, S(O)pR8, CN, NO2, OH, COR10, NR10COR12, NR10SO2R8, CONR10R11, NR10R11, S(O)pR7, S(O)pR9, OR7, OR9and CO2R10; or, when a represents (C1-C12)-Alki the EN or (C 1-C12-halogenoalkanes and R5means (C1-C6)-alkyl, unsubstituted or substituted by one or more radicals halogen, one or more of the carbon atoms of R5together with O and one or more carbon atoms And to form a 5 - or 6-membered ring;

R6means (C1-C6)-alkyl, (C1-C6-halogenoalkane,

(C2-C6)-alkenyl, (C2-C6)-halogenoalkanes, (C2-C6)-quinil or

(C2-C6-halogenoalkanes;

R7denotes phenyl, unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C6)-alkyl, (C1-C6)-halogenoalkane, (C1-C6-alkoxygroup, (C1-C6-halogenoalkanes, CN, NO2, S(O)pR8, COR11, COR13, CONR10R11, SO2NR10R11, NR10R11, OH, SO3H and (C1-C6-alkylidene;

R8means (C1-C6)-alkyl or (C1-C6-halogenoalkane;

R9means heterocyclyl, unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C4)-alkyl, (C1-C4)-halogenoalkane, (C1-C4-alkoxy uppy, (C1-C4-halogenoalkanes, NO2CN, CO2-(C1-C6)-alkyl, S(O)pR8, OH and the carbonyl group;

R10and R12independently of one another denote H, (C1-C6)-alkyl, (C1-C6-halogenoalkane, (C3-C6)-alkenyl, (C3-C6)-halogenoalkanes, (C3-C6)-quinil, (C3-C6-halogenoalkanes, (C3-C6-cycloalkyl -(C1-C6)-alkyl-(C3-C6-cycloalkyl, -(CH2)qR13or -(CH2)qR9; or

each of R10and R11and/or R10and R12together with the respectively attached N atom form a five - or six-membered saturated ring which may contain an additional heteroatom in the ring selected from O, S and N, and this ring is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C6)-alkyl and (C1-C6)-halogenoalkane;

R11and R14independently of one another denote H, (C1-C6)-alkyl, (C1-C6-halogenoalkane, (C3-C6-cycloalkyl or -(C1-C6)-alkyl-(C3-C6-cycloalkyl;

R13denotes phenyl, unsubstituted or substituted by one or more radicals selected from the group consisting of g is lagena, (C1-C6)-alkyl, (C1-C6)-halogenoalkane, (C1-C6-alkoxygroup, (C1-C6-halogenoalkanes, CN, NO2, S(O)pR8and NR11R14;

R15means R11or -(CH2)qR13;

n and p independently of each other 0, 1 or 2;

q is 0 or 1; and

each heterocyclyl in the above-mentioned radicals is independently a heterocyclic radical having 3-7 ring atoms and 1, 2 or 3 heteroatoms in the ring selected from the group consisting of N, O and S;

or pesticide acceptable salt.

The following aspect of the invention relates to the use of compounds of formula (I) for the destruction of parasites in the animal body and animal body.

In a further aspect the invention relates to the use of compounds of formula (I) for the manufacture of veterinary medicines, preferably for the destruction of parasites, especially ecto - and endoparasites in the animal body and animal body.

The invention also encompasses all stereoisomers, enantiomers and geometric isomers and mixtures thereof of compounds of formula (I).

The term "pesticide acceptable salt" refers to salts, anions or cations which are known and accepted state of the art for the formation of salts for use as pesticides.

<> Suitable salts with bases, for example, formed by compounds of formula (I)containing a group carboxylic acids are alkali metal salts (e.g. sodium and potassium), alkaline earth metals (e.g. calcium and magnesium), ammonium and amines (for example, diethanolamine, triethanolamine, octylamine, research and dioctylamine). Suitable additive salts with acids, for example, formed by compounds of formula (I)containing an amino group are salts with inorganic acids, such as hydrochloride, sulphates, phosphates and nitrates and salts with organic acids, for example acetic acid.

Note that the above conditions are included only for reasons of chemical instability for specifically excluded members, and not for reasons of their use in the existing level of technology.

In this description and in the accompanying claims, the above substituents have the following meanings.

The halogen atom means fluorine, chlorine, bromine or iodine.

The term "halogen" ("halogeno") before the name of the radical indicates that the specified moiety is partially or fully galogenidov, that is substituted by F, Cl, Br or I in any combination, preferably F or Cl.

Alkyl groups and parts thereof, unless otherwise specified, can be linear or branched.

Pronounced the e "( 1-C6)-alkyl" is to be understood as meaning an unbranched or branched hydrocarbon radical having 1, 2, 3, 4, 5 or 6 carbon atoms, such as, for example, methyl, ethyl, sawn, ISO-propyl, 1-boutigny, 2-boutigny, 2-methylpropyl or tert-botilony radical.

Alkyl radicals, including in complex groups, unless otherwise specified, preferably have 1-4 carbon atoms.

The expression "(1-C6-halogenoalkane" denotes an alkyl group mentioned under the expression "(1-C6)-alkyl"in which one or more hydrogen atoms replaced by the same number of identical or different halogen atoms, such as monohalogenated, perhalogenated, CF3, CHF2CH2F, CHFCH3, CF3CH2, CF3CF2, CHF2CF2CH2FCHCl, CH2Cl, CCl3, CHCl2or CH2CH2Cl.

The expression "(1-C12-alkylen" should be understood as meaning an unbranched or branched saturated carbon chain having 1-12 carbon atoms.

The expression "(1-C12-halogenoalkane" should be understood as meaning an unbranched or branched saturated carbon chain having 1-12 carbon atoms in which one or more hydrogen atoms replaced by the same number of the same sludge is different halogen atoms.

The expression "(2-C12-albaniles" should be understood as meaning an unbranched or branched saturated carbon chain having 2-12 carbon atoms and which contains at least one double bond, which may be located in any position of the corresponding unsaturated radical.

The expression "(1-C6)-alkoxy" denotes alkoxygroup, the carbon chain of which has a value specified for the expression "(1-C6)-alkyl". "Halogenoalkane", for example, indicates OCF3, OCHF2, OCH2F, CF3CF2O, OCH2CF3or OCH2CH2Cl.

The expression "(2-C6)-alkenyl" denotes unbranched or branched acyclic carbon chain with the number of carbon atoms corresponding to the specified interval that contains at least one double bond, which may be located in any position of the corresponding unsaturated radical. "(C2-C6)-alkenyl" respectively denotes, for example, vinyl, allyl, 2-methyl-2-propenyloxy, 2-butenyloxy, pentanediol, 2-methylpentanediol or hexenyl group.

The expression "(2-C6)-quinil" denotes unbranched or branched acyclic carbon chain with the number of carbon atoms, the corresponding decree of the resultant interval, which contains at least one triple bond, which may be located in any position of the corresponding unsaturated radical. "(C2-C6)-quinil" respectively denotes, for example, propargyl, 1-methyl-2-propenyloxy, 2-butenyloxy or 3-butenyloxy group.

Cycloalkyl groups preferably have from three to seven carbon atoms in the ring and may be substituted with halogen or alkyl.

In the compounds of formula (I) given examples of the following radicals:

an example of alkyl, substituted cycloalkyl is cyclopropylmethyl;

an example of alkyl, substituted alkoxygroup is methoxymethyl (CH3Och2-); and

an example of alkyl, substituted alkylthiol is methylthiomethyl (CH3SCH2-).

Group "heterocyclyl" may be saturated, unsaturated or heteroaromatic; preferably it contains a heterocyclic ring one or more, in particular 1, 2 or 3 heteroatoms, preferably selected from the group consisting of N, O and S; it is preferably an aliphatic heterocyclic radical having 3 to 7 atoms in the ring, or heteroaromatic radical having 5-7 atoms in the ring. The heterocyclic radical can be, for example, a heteroaromatic radical or ring (heteroaryl), such as, for example, mono-, bi - or floor is a cyclic aromatic system, in which at least 1 ring contains one or more heteroatoms, for example pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, thienyl, thiazolyl, thiadiazolyl, oxazolyl, isoxazolyl, furyl, pyrrolyl, pyrazolyl, imidazolyl and triazolyl, or is partially or fully hydrogenated radical such as oxiranyl, oxetanyl, oxolane (tetrahydrofuran), oxamyl, pyrrolidyl, piperidyl, piperazinil, DIOXOLANYL, oxazolyl, isoxazolyl, oxazolidinyl, isoxazolidine and morpholinyl. Group "heterocyclyl" may be unsubstituted or substituted by one or more radicals, preferably 1, 2 or 3 radicals selected from the group consisting of halogen, alkoxygroup, halogenoalkanes, allylthiourea, hydroxyl, amino, nitro, carboxyl, ceanography, alkoxycarbonyl, alkylsulphonyl, formyl, carbamoyl, mono - and dialkylaminoalkyl, substituted amino groups, such as alluminare, mono - and dialkylamino, and alkylsulfonyl, halogenoalkane, alkylsulfonyl, halogenoalkanes, alkyl and halogenoalkane and also the carbonyl group. Oxoprop may also be present in those of the heteroatoms of the ring, where there are various oxidation States, for example in the cases of N and S.

The term "pests" means arthropods pests (including on comah and arachnids) and helminths (including nematodes). The term "parasites" covers all types of pests that live in the animal body or on the body of the animal.

A preferred class of compounds of formula (I) for use in this invention is such that:

R1denotes CN;

W represents C-halogen;

R2denotes hydrogen or halogen;

R3means CF3or OCF3;

R4denotes hydrogen, (C2-C6)-alkenyl,

(C2-C6)-halogenoalkanes, (C2-C6)-quinil, (C2-C6-halogenoalkanes, (C3-C7-cycloalkyl, -CO2R8, -CH2R7, -CH2R9, OR7, OR8or or9; or (C1-C6)-alkyl, unsubstituted or substituted by one or more radicals selected from the group consisting of halogen,

(C1-C6-alkoxygroup, (C1-C6-halogenoalkanes,

(C3-C7)-cycloalkyl, S(O)pR8and CO2-(C1-C6)-alkyl;

A stands for (C1-C6-alkylen or (C1-C6-halogenoalkane, in which 2, 3 or 4 adjacent carbon atom may form part (C3-C6)-cycloalkyl ring, which is unsubstituted or substituted by one or more radicals selected from the group consisting of (C1-C6)-alkyl and Gal the gene;

R5means (C3-C6-cycloalkyl, -(CH2)qR7; or (C1-C6)-alkyl, unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C6-alkoxygroup, (C1-C6-halogenoalkanes,

(C3-C6)-cycloalkyl, S(O)pR8and CO2-(C1-C6)-alkyl; or when And indicates (With1-C6)-alkyl or (C1-C6-halogenoalkane and R5means (C1-C6)-alkyl or (C1-C6-halogenoalkane, one or more of the carbon atoms of the group R5together with O and one or more carbon atoms And to form a 5 - or 6-membered ring;

R6and R8independently of one another denote (C1-C6)-alkyl or (C1-C6-halogenoalkane;

R7denotes phenyl, unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C6)-alkyl, (C1-C6)-halogenoalkane,

(C1-C6-alkoxygroup, CN, NO2, S(O)pR8and NR11R12;

R9means heterocyclyl, unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C4)-alkyl is, (C1-C4)-halogenoalkane and (C1-C4-alkoxygroup;

R11and R12independently of one another denote hydrogen,

(C1-C6)-alkyl or (C1-C6-halogenoalkane;

n and p independently of each other 0, 1 or 2; and

q is 0 or 1.

Another preferred class of compounds of formula (I) for use in this invention is such that:

R1denotes CN;

W represents C-halogen;

R2denotes halogen;

R3means CF3or OCF3;

R4denotes hydrogen, (C2-C6)-alkenyl, (C2-C6)-quinil, (C3-C7-cycloalkyl, -CO2-(C1-C3)-alkyl, -CO2-(C3-C6-cycloalkyl, -CO2-(C1-C3)-alkyl-(C3-C6-cycloalkyl, -CH2R7or-CH2R9; or (C1-C4)-alkyl, unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C3-alkoxygroup, (C1-C3-halogenoalkanes, (C3-C6)-cycloalkyl, S(O)pR8, CO2-(C1-C3)-alkyl, -O(C=O)-(C1-C3)-alkyl, NR10R11, OH, CN, NO2, OR7or or9;

A stands for (C1-C9-alkylen or (C1-C9 -halogenoalkane, in which 2, 3 or 4 adjacent carbon atom may form part (C3-C8)-cycloalkyl ring, which is unsubstituted or substituted by one or more radicals selected from the group consisting of (C1-C6)-alkyl and halogen;

R5means (C3-C7-cycloalkyl or -(CH2)qR7or denotes (C1-C6)-alkyl, unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C3-alkoxygroup, (C1-C4-halogenoalkanes, (C3-C7)-cycloalkyl, S(O)pR8, CN, NR10R11, S(O)pR7, S(O)pR9, OR7and OR9;

R6means (C1-C2-halogenoalkane;

R7denotes phenyl, unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C4)-alkyl, (C1-C4)-halogenoalkane,

(C1-C4-alkoxygroup, (C1-C4-halogenoalkanes, CN, NO2, S(O)pR8, COR11, NR10R11and HE;

R8means (C1-C4)-alkyl or (C1-C4-halogenoalkane;

R9means heterocyclyl, unsubstituted or substituted by one or more of the radicals is AMI, selected from the group consisting of halogen, (C1-C4)-alkyl, (C1-C4)-halogenoalkane and (C1-C4-alkoxygroup;

R10denotes H, (C1-C3)-alkyl, (C1-C3-halogenoalkane, (C3-C4)-alkenyl, (C3-C4)-quinil, (C3-C6-cycloalkyl,

-(C1-C6)-alkyl-(C3-C6-cycloalkyl or -(CH2)qR13; or

R10and R11together with the attached N atom form a five - or six-membered saturated ring which may contain an additional heteroatom in the ring selected from O, S and N, and this ring may be unsubstituted or substituted by one or more radicals selected from the group consisting of halogen and (C1-C3)-alkyl;

R11and R14independently of one another denote H, (C1-C3)-alkyl, (C1-C3-halogenoalkane, (C3-C6-cycloalkyl or -(C1-C3)-alkyl-(C3-C6-cycloalkyl;

R13denotes phenyl, unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C3)-alkyl, (C1-C3)-halogenoalkane,

(C1-C3-alkoxygroup, (C1-C3-halogenoalkanes, CN, NO2, S(O)pR8and NR11R 14;

n and p independently of each other 0, 1 or 2;

q is 0 or 1; and

each heterocyclyl in the abovementioned radicals independently is a heteroaromatic radical having 5 or 6 ring atoms and 1, 2 or 3 heteroatoms in the ring selected from the group consisting of N, O and S.

An additional preferred class of compounds of formula (I) for use in this invention is such that:

R1denotes CN;

W denotes C-Cl;

R2denotes chlorine;

R3means CF3or OCF3;

R4denotes hydrogen, CO2-(C1-C3)-alkyl or (C1-C6)-alkyl, unsubstituted or substituted by one or more radicals selected from the group consisting of halogen and

(C1-C3-alkoxygroup;

A stands for (C1-C4-alkylen;

R5means (C3-C6-cycloalkyl, -(CH2)qR7, (C1-C6)-alkyl or (C1-C6-halogenated; or, if R5means (C1-C6)-alkyl, one or more of the carbon atoms of the group R5together with O and one or more carbon atoms And to form a 5 - or 6-membered ring;

R6means CF3, CF2Cl, CFCl2, CBrF2or CHF2;

R7denotes phenyl;

n is 0 or 2; and

q is 0 or 1.

Another preferred class of compounds of formula (I) for use in this invention is such that:

R1denotes CN;

W represents C-halogen;

R2denotes hydrogen or halogen;

R3means CF3or OCF3;

R4denotes hydrogen, (C2-C6)-alkenyl,

(C2-C6)-halogenoalkanes, (C2-C6)-quinil, (C2-C6-halogenoalkanes, (C3-C6-cycloalkyl, -CO2-(C1-C6)-alkyl or-CH2R7; or

(C1-C6)-alkyl, unsubstituted or substituted by one or more radicals selected from the group consisting of halogen,

(C1-C6-alkoxygroup, (C1-C6-halogenoalkanes,

(C3-C6)-cycloalkyl, S(O)pR8and CO2-(C1-C6)-alkyl;

A stands for (C1-C6-alkylen or (C1-C6-halogenoalkane, in which 2, 3 or 4 adjacent carbon atom may form part (C3-C6)-cycloalkyl ring, which is unsubstituted or substituted by one or more radicals selected from the group consisting of (C1-C6)-alkyl and halogen;

R5means (C3-C6-cycloalkyl or -(CH2)qR7;or about who appoints (C 1-C6)-alkyl, unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C6-alkoxygroup, (C1-C6-halogenoalkanes,

(C3-C6)-cycloalkyl, S(O)pR8and CO2-(C1-C6)-alkyl; or when And indicates (With1-C6-alkylen or (C1-C6-halogenoalkanes and R5means (C1-C6)-alkyl, unsubstituted or substituted by one or more radicals halogen, one or more of the carbon atoms of R5together with O and one or more carbon atoms And to form a 5 - or 6-membered ring;

R6and R8independently of one another denote (C1-C6)-alkyl or (C1-C6-halogenoalkane;

R7denotes phenyl, unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C6)-alkyl, (C1-C6)-halogenoalkane, (C1-C6-alkoxygroup, CN, NO2, S(O)pR8and NR10R11;

R10and R11independently of one another denote H, (C1-C6)-alkyl or (C1-C6-halogenoalkane;

n and p independently of each other 0, 1 or 2; and

q is 0 or 1.

Another preferred class of soybeans is ineni formula (I) for use in this invention is such that where:

R1denotes CN;

W represents C-halogen;

R2denotes halogen;

R3means CF3or OCF3;

R4denotes hydrogen, (C2-C6)-alkenyl,

(C2-C6)-halogenoalkanes, (C3-C7-cycloalkyl,

(C1-C4)-alkyl-(C3-C7-cycloalkyl, -CO2-(C1-C6)-alkyl,

(C1-C6)-alkyl or (C1-C6-halogenoalkane;

And means (C1-C12-alkylene, unsubstituted or substituted by one or more radicals selected from the group consisting of (C1-C6)-alkyl and halogen;

R5means (C1-C6)-alkyl;

R6means CF3, CF2Cl, CFCl2, CBrF2or CHF2; and

n is 0, 1 or 2.

Other particularly preferred classes of compounds of formula (I) for use in this invention are those in which there are one or more of the following features:

R4denotes hydrogen, (C1-C4)-alkyl, -CO2-(C1-C4)-alkyl, (C3-C4)-alkenyl, (C1-C2)-alkyl-(C3-C4-cycloalkyl or

(C3-C4-cycloalkyl;

R5means (C1-C2)-alkyl; and

And means (C2-C3-alkylen.

The other person is but a preferred class of compounds for use in this invention is such that where:

R1denotes CN;

R2denotes chlorine;

R3means CF3;

W denotes C-Cl;

R4denotes hydrogen, (C1-C4)-alkyl, -CO2-(C1-C4)-alkyl,

(C3-C4)-alkenyl, (C1-C2)-alkyl-(C3-C4-cycloalkyl or

(C3-C4-cycloalkyl;

R5means (C1-C2)-alkyl;

R6means CF3;

And means (C2-C3-alkylen; and

n is 0, 1 or 2.

Another particularly preferred class of compounds for use in this invention is one where:

R1denotes CN;

R2denotes chlorine;

R3means CF3;

W denotes C-Cl;

R4denotes hydrogen, (C1-C4)-alkyl or-CH2-(C1-C4)-alkoxygroup;

R5denotes hydrogen, (C1-C4)-alkyl or CO2-(C1-C4)-alkyl;

R6means CF3;

And means (C2-C3-alkylen; and

n is 0, 1 or 2.

A more preferred class of compounds of formula (I) for use in this invention is such that:

R1denotes CN; R2denotes chlorine; R3means CF3or OCF3; W denotes C-Cl; R4denotes hydrogen or (C1 6)-alkyl; R5means (C1-C6)-alkyl; R6means CF3; A means (C1-C4-alkylene and n is 0, 1 or 2.

Other particularly preferred classes of compounds of formula (I) for use in this invention are those where one or more of the following features:

W denotes C-Cl;

R2denotes chlorine;

R3means CF3or OCF3;

R4denotes hydrogen, (C1-C6)-alkyl or

(C1-C6-halogenoalkane;

R5means (C1-C6)-alkyl;

R6means (C1-C3-halogenoalkane (R6more preferably denotes CF3); and/or

And means (C1-C6-alkylen (And more preferably denotes (C2-C3-alkylen).

In patent WO 9828278 proposed a number of compounds that conform to formula (I), as intermediate products, but there are no links or assumption that these compounds exhibit parasiticide properties.

Some of the compounds of formula (I) are new and therefore an additional object of the present invention are new compounds of formula (I).

One of the classes of new derivatives of 5-substituted alkalinisation formula (I) or their pestic the bottom acceptable salts is such that where:

R1denotes CN;

W represents C-halogen, or-CH3;

R2denotes hydrogen, halogen or CH3;

R3means (C1-C3-halogenoalkane,

(C1-C3)-halogenoalkanes or S(O)p-(C1-C3-halogenoalkane;

R4means (C2-C6)-alkenyl, (C2-C6)-halogenoalkanes,

(C2-C6)-quinil, (C2-C6-halogenoalkanes, (C3-C7-cycloalkyl,

CO-(CH2)q-R7, CO-(CH2)q-R9, -CO-(C1-C4)-alkyl-(C1-C6)-alkoxygroup, -CO2-(CH2)q-R7, CO2R8, -CO2-(CH2)q-R9, -CO2-(C3-C7- cycloalkyl,

-CO2-(C1-C4)-alkyl-(C3-C7-cycloalkyl, -CO2-(C3-C6)-alkenyl,

-CO2-(C3-C6)-quinil, CONR10R11, -CH2R7, -CH2R9, OR7, OR8or or9; or (C1-C6)-alkyl, substituted by one or more radicals selected from the group consisting of halogen,

(C1-C6-alkoxygroup, (C1-C6-halogenoalkanes,

(C3-C7)-cycloalkyl, S(O)pR8, CO2-(C1-C6)-alkyl,

-O(C=O)-(C1-C6)-is Lila, NR10COR12, NR10R11, CONR10R11, SO2NR10R11, OH, CN, NO2, OR7, NR10SO2R8, COR8and OR9;

A stands for (C1-C12-alkylen [preferably

(C1-C6-alkylen] and (C1-C12-halogenoalkane [preferably

(C1-C6-halogenoalkane], in which 2, 3 or 4 adjacent carbon atom may form part (C3-C8)-cycloalkyl ring, which is unsubstituted or substituted by one or more radicals selected from the group consisting of (C1-C6)-alkyl and halogen; or represents (C1-C12-alkylen or

(C1-C12-halogenoalkane, in which last two mentioned groups are methylene parts replaced by a group selected from the

-C(=O)-, -C(=NH)-, -O-, -S - and-NR15-provided that the replacing group is not associated with the neighboring atom, O or N; or denotes

(C2-C12-albaniles or (C2-C12-halogenoalkanes;

R5denotes H, (C3-C6)-alkenyl, (C3-C6)-halogenoalkanes, (C3-C6)-quinil, (C3-C6-halogenoalkanes, (C3-C7-cycloalkyl, -(CH2)qR7, -(CH2)qR9or NR10R11; or denotes (C1-C6)-alkyl, unsubstituted Il is substituted by one or more radicals, selected from the group consisting of halogen,

(C1-C6-alkoxygroup, (C1-C6-halogenoalkanes,

(C3-C6-alkenylacyl, (C3-C6-halogenoalkanes,

(C3-C6-alkyloxy, (C3-C6-halogenoalkanes,

(C3-C7)-cycloalkyl, S(O)pR8, CN, NO2, OH, COR10, NR10COR12, NR10SO2R8, CONR10R11, NR10R11, S(O)pR7, S(O)pR9, OR7, OR9and CO2R10; or when And indicates (With1-C12-alkylen or

(C1-C12-halogenoalkanes and R5means (C1-C6)-alkyl, unsubstituted or substituted by one or more radicals halogen, one or more of the carbon atoms of R5together with O and one or more carbon atoms And to form a 5 - or 6-membered ring;

R6means (C1-C6)-alkyl, (C1-C6-halogenoalkane,

(C2-C6)-alkenyl, (C2-C6)-halogenoalkanes, (C2-C6)-quinil or

(C2-C6-halogenoalkanes;

R7denotes phenyl, unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C6)-al the sludge, (C1-C6)-halogenoalkane,

(C1-C6-alkoxygroup, (C1-C6-halogenoalkanes, CN, NO2, S(O)pR8, COR11, COR13, CONR10R11, SO2NR10R11, NR10R11, OH, SO3H and

(C1-C6-alkylidene;

R8means (C1-C6)-alkyl or (C1-C6-halogenoalkane;

R9means heterocyclyl, unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C4)-alkyl, (C1-C4)-halogenoalkane, (C1-C4-alkoxygroup, (C1-C4-halogenoalkanes, NO2CN, CO2-(C1-C6)-alkyl, S(O)pR8, OH and the carbonyl group;

R10and R12independently of one another denote H, (C1-C6)-alkyl, (C1-C6-halogenoalkane, (C3-C6)-alkenyl, (C3-C6)-halogenoalkanes, (C3-C6)-quinil, (C3-C6-halogenoalkanes, (C3-C6-cycloalkyl -(C1-C6)-alkyl-(C3-C6-cycloalkyl, -(CH2)qR13or -(CH2)qR9; or

each of R10and R11and/or R10and R12together with the respectively attached N atom form a five - or six-membered n is Susanne ring, which may contain an additional heteroatom in the ring selected from O, S and N, and this ring is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C6)-alkyl and

(C1-C6)-halogenoalkane;

R11and R14independently of one another denote H, (C1-C6)-alkyl, (C1-C6-halogenoalkane, (C3-C6-cycloalkyl or -(C1-C6)-alkyl-(C3-C6-cycloalkyl;

R13denotes phenyl, unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C6)-alkyl, (C1-C6)-halogenoalkane,

(C1-C6-alkoxygroup, (C1-C6-halogenoalkanes, CN, NO2, S(O)pR8and NR11R14;

R15means R11or -(CH2)qR13;

n and p independently of each other 0, 1 or 2;

q is 0 or 1; and

each heterocyclyl in the above-mentioned radicals is independently a heterocyclic radical having 3-7 ring atoms and 1, 2 or 3 heteroatoms in the ring selected from the group consisting of N, O and S.

A preferred class of compounds of formula (I) are those in which:

R1denotes CN;

W represents C-halogen;

R2hereafter which includes hydrogen or halogen;

R3means CF3or OCF3;

R4means (C2-C6)-alkenyl, (C2-C6)-halogenoalkanes, (C2-C6)-quinil, (C2-C6-halogenoalkanes, (C3-C7-cycloalkyl, CO2R8, -CO2-(C3-C6)-alkenyl, -CO2-(C3-C6)-quinil, -CH2R7, -CH2R9, OR7, OR8or or9; or (C1-C6)-alkyl, substituted by one or more radicals selected from the group consisting of halogen, (C1-C6-alkoxygroup, (C1-C6-halogenoalkanes, (C3-C7)-cycloalkyl, S(O)pR8and CO2-(C1-C6)-alkyl;

A stands for (C1-C6-alkylen or (C1-C6-halogenoalkane, in which 2, 3 or 4 adjacent carbon atom may form part (C3-C6)-cycloalkyl ring, which is unsubstituted or substituted by one or more radicals selected from the group consisting of (C1-C6)-alkyl and halogen;

R5means (C3-C6-cycloalkyl, -(CH2)qR7; or (C1-C6)-alkyl, unsubstituted or substituted by one or more radicals selected from the group consisting of halogen,

(C1-C6-alkoxygroup, (C1-C6)-is halogenoalkanes,

(C3-C6)-cycloalkyl, S(O)pR8and CO2-(C1-C6)-alkyl; or when And indicates (With1-C6)-alkyl or (C1-C6-halogenoalkane and R5means (C1-C6)-alkyl or (C1-C6-halogenoalkane, one or more of the carbon atoms of the group R5together with O and one or more carbon atoms And to form a 5 - or 6-membered ring;

R6and R8independently of one another denote (C1-C6)-alkyl or (C1-C6-halogenoalkane;

R7denotes phenyl, unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C6)-alkyl, (C1-C6)-halogenoalkane,

(C1-C6-alkoxygroup, CN, NO2, S(O)pR8and NR11R12;

R9means heterocyclyl, unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C4)-alkyl, (C1-C4)-halogenoalkane and (C1-C4-alkoxygroup;

R11and R12are identical or different and denote hydrogen, (C1-C6)-alkyl or (C1-C6-halogenoalkane;

n and p independently of each other 0, 1 or 2; and

q is 0 or 1.

Another Avenue is pactically class of compounds of formula (I) is such that where:

R1denotes CN;

W represents C-halogen;

R2denotes hydrogen or halogen;

R3means CF3or OCF3;

R4means (C2-C6)-alkenyl, (C2-C6)-halogenoalkanes, (C2-C6)-quinil, (C2-C6-halogenoalkanes, (C3-C6-cycloalkyl, -CO2R8, -CO2-(C3-C6)-quinil or-CH2R7; or (C1-C6)-alkyl, substituted by one or more radicals selected from the group consisting of halogen, (C1-C6-alkoxygroup,

(C1-C6-halogenoalkanes, (C3-C6)-cycloalkyl, S(O)pR8and

CO2-(C1-C6)-alkyl;

A stands for (C1-C6-alkylen or (C1-C6-halogenoalkane, in which 2, 3 or 4 adjacent carbon atom may form part (C3-C6)-cycloalkyl ring, which is unsubstituted or substituted by one or more radicals selected from the group consisting of (C1-C6)-alkyl and halogen;

R5means (C3-C6-cycloalkyl or -(CH2)qR7;or denotes (C1-C6)-alkyl, unsubstituted or substituted by one or more radicals selected from the group consisting of halogen,

(C 1-C6-alkoxygroup, (C1-C6-halogenoalkanes,

(C3-C6)-cycloalkyl, S(O)pR8and CO2-(C1-C6)-alkyl; or when And indicates (With1-C6-alkylen or (C1-C6-halogenoalkanes and R5means (C1-C6)-alkyl, unsubstituted or substituted by one or more radicals halogen, one or more of the carbon atoms of R5together with O and one or more carbon atoms And to form a 5 - or 6-membered ring;

R6and R8independently of one another denote (C1-C6)-alkyl or (C1-C6-halogenoalkane;

R7denotes phenyl, unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C6)-alkyl, (C1-C6)-halogenoalkane,

(C1-C6-alkoxygroup, CN, NO2, S(O)pR8and NR10R11;

R10and R11independently of one another denote H, (C1-C6)-alkyl or (C1-C6-halogenoalkane;

n and p independently of each other 0, 1 or 2; and

q is 0 or 1.

Another preferred class of compounds of formula (I) is such that:

R1denotes CN;

W represents C-halogen;

R2indicates halog is n;

R3means CF3or OCF3;

R4means (C2-C6)-alkenyl, (C2-C6)-quinil,

(C3-C7-cycloalkyl, -CO2R8, -CO2-(C3-C6)-quinil, -CO2-(C3-C6-cycloalkyl, -CO2-(C1-C3)-alkyl-(C3-C6-cycloalkyl, -CH2R7or

-CH2R9; or (C1-C4)-alkyl, substituted by one or more radicals selected from the group consisting of halogen,

(C1-C3-alkoxygroup, (C1-C3-halogenoalkanes,

(C3-C6)-cycloalkyl, S(O)pR8, CO2-(C1-C3)-alkyl,

-O(C=O)-(C1-C3)-alkyl, NR10R11, OH, CN, NO2, OR7and OR9;

A stands for (C1-C9-alkylen or (C1-C9-halogenoalkane, in which 2, 3 or 4 adjacent carbon atom may form part (C3-C8)-cycloalkyl ring, unsubstituted or substituted by one or more radicals selected from the group consisting of (C1-C6)-alkyl and halogen;

R5means (C3-C7-cycloalkyl or -(CH2)qR7; or denotes (C1-C6)-alkyl, unsubstituted or substituted by one or more radicals selected from the gr is PPI, consisting of halogen,

(C1-C3-alkoxygroup, (C1-C4-halogenoalkanes,

(C3-C7)-cycloalkyl, S(O)pR8, CN, NR10N11, S(O)pR7, S(O)pR9, OR7and OR9;

R6means (C1-C2-halogenoalkane;

R7denotes phenyl, unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C4)-alkyl, (C1-C4)-halogenoalkane,

(C1-C4-alkoxygroup, (C1-C4-halogenoalkanes, CN, NO2, S(O)pR8, COR11, NR10R11and HE;

R8means (C1-C4)-alkyl or (C1-C4-halogenoalkane;

R9means heterocyclyl, unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C4)-alkyl, (C1-C4)-halogenoalkane and (C1-C4-alkoxygroup;

R10denotes H, (C1-C3)-alkyl, (C1-C3-halogenoalkane,

(C3-C4)-alkenyl, (C3-C4)-quinil, (C3-C6-cycloalkyl,

-(C1-C6)-alkyl-(C3-C6-cycloalkyl or -(CH2)qR13; or

R10and R11together with connec who authorized the N atom form a five - or six-membered saturated ring, which may contain an additional heteroatom in the ring selected from O, S and N, and this ring is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen and (C1-C3)-alkyl;

R11and R14independently of one another denote H, (C1-C3)-alkyl, (C1-C3-halogenoalkane, (C3-C6-cycloalkyl or -(C1-C3)-alkyl-(C3-C6-cycloalkyl;

R13denotes phenyl, unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C3)-alkyl, (C1-C3)-halogenoalkane,

(C1-C3-alkoxygroup, (C1-C3-halogenoalkanes, CN, NO2, S(O)pR8and NR11R14;

n and p independently of each other 0, 1 or 2;

q is 0 or 1; and

each heterocyclyl in the abovementioned radicals independently is a heteroaromatic radical having 5 or 6 ring atoms and 1, 2 or 3 heteroatoms in the ring selected from the group consisting of N, O and S.

As a preferred class of compounds of formula (I) is such that:

R1denotes CN;

W denotes C-Cl;

R2denotes chlorine;

R3means CF3or OCF3;

R4denotes CO2-(C1 -C3)-alkyl or (C1-C6)-alkyl, substituted by one or more radicals selected from the group consisting of halogen and (C1-C3-alkoxygroup;

A stands for (C1-C4-alkylen;

R5means (C3-C6-cycloalkyl, -(CH2)qR7, (C1-C6)-alkyl or (C1-C6-halogenated; or if R5means (C1-C6)-alkyl, one or more of the carbon atoms of the group R5together with O and one or more carbon atoms And to form a 5 - or 6-membered ring;

R6means CF3, CF2Cl, CFCl2, CBrF2or CHF2;

R7denotes phenyl;

n is 0, 1 or 2; and

q is 0 or 1.

Another preferred class of compounds of formula (I) is such that:

R1denotes CN;

W represents C-halogen;

R2denotes halogen;

R3means CF3or OCF3;

R4means (C2-C6)-alkenyl, (C2-C6)-halogenoalkanes, (C3-C7-cycloalkyl, (C1-C4)-alkyl-(C3-C7-cycloalkyl, -CO2-(C1-C6)-alkyl or (C1-C6-halogenoalkane;

And means (C1-C12-alkylene, unsubstituted or substituted by one or more radicals of the mi, selected from the group consisting of (C1-C6)-alkyl and halogen;

R5means (C1-C6)-alkyl;

R6means CF3, CF2Cl, CFCl2, CBrF2or CHF2; and

n is 0, 1 or 2.

Especially preferred class of compounds of formula (I) is one where:

R1denotes CN;

R2denotes chlorine;

R3means CF3;

W denotes C-Cl;

R4denotes-CO2-(C1-C4)-alkyl, (C3-C4)-alkenyl,

(C1-C2)-alkyl-(C3-C4-cycloalkyl or (C3-C4-cycloalkyl (more preferably R4denotes-CO2-(C1-C4)-alkyl);

R5means (C1-C2)-alkyl;

R6means CF3;

And means (C2-C3-alkylen; and

n is 0, 1 or 2.

Another class of new derivatives of 5-substituted alkalinisation formula (I) or their pesticide acceptable salts is one where:

R1denotes CN;

W represents C-halogen, or-CH3;

R2denotes hydrogen, halogen or CH3;

R3means (C1-C3-halogenoalkane,

(C1-C3)-halogenoalkanes or S(O)p-(C1-C3-halogenoalkane;

R4denotes hydrogen, (C1-C6)-alkyl, or COR 8;

A stands for (C1-C12-alkylen [preferably

(C1-C6-alkylen] and (C1-C12-halogenoalkane [preferably

(C1-C6-halogenoalkane], in which 2, 3 or 4 adjacent carbon atom may form part (C3-C8)-cycloalkyl ring, which is unsubstituted or substituted by one or more radicals selected from the group consisting of (C1-C6)-alkyl and halogen; or represents (C1-C12-alkylen or

(C1-C12-halogenoalkane, in which last two mentioned groups are methylene parts replaced by a group selected from the

-C(=O)-, -C(=NH)-, -O-, -S - and-NR15-, provided that the replacing group is not associated with the neighboring atom, O or N; or denotes

(C2-C12-albaniles or (C2-C12-halogenoalkanes;

R5denotes H, (C3-C6)-alkenyl, (C3-C6)-halogenoalkanes, (C3-C6)-quinil, (C3-C6-halogenoalkanes, (C3-C7-cycloalkyl,

-(CH2)qR7, -(CH2)qR9or NR10R11; or denotes (C1-C6)-alkyl, substituted by one or more radicals selected from the group consisting of halogen, (C1-C6-alkoxygroup,

(C1-C6-halogenoalkanes the group, (C3-C6-alkenylacyl,

(C3-C6-halogenoalkanes, (C3-C6-alkyloxy,

(C3-C6-halogenoalkanes, (C3-C7)-cycloalkyl, S(O)pR8, CN, NO2, OH, COR10, NR10COR12, NR10SO2R8, CONR10R11, NR10R11, S(O)pR7, S(O)pR9, OR7, OR9and CO2R10; or when And indicates (With1-C12-alkylen or (C1-C12-halogenoalkanes and R5means (C1-C6)-alkyl, unsubstituted or substituted by one or more radicals halogen, one or more of the carbon atoms of R5together with O and one or more carbon atoms And to form a 5 - or 6-membered ring;

R6means (C1-C6-halogenoalkane;

R7denotes phenyl, unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C6)-alkyl, (C1-C6)-halogenoalkane,

(C1-C6-alkoxygroup, (C1-C6-halogenoalkanes, CN, NO2, S(O)pR8, COR11, COR13, CONR10R11, SO2NR10R11, NR10R11, OH, SO3H and

(C1-C6-alkylidene;

R8means (C1-C6)-alkyl or (C1-C6-halogenoalkane;

R9means heterocyclyl, unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C4)-alkyl, (C1-C4)-halogenoalkane, (C1-C4-alkoxygroup, (C1-C4-halogenoalkanes, NO2CN, CO2-(C1-C6)-alkyl, S(O)pR8, OH and the carbonyl group;

R10and R12independently of one another denote H, (C1-C6)-alkyl, (C1-C6-halogenoalkane, (C3-C6)-alkenyl, (C3-C6)-halogenoalkanes, (C3-C6)-quinil, (C3-C6-halogenoalkanes, (C3-C6-cycloalkyl -(C1-C6)-alkyl-(C3-C6-cycloalkyl, -(CH2)qR13or -(CH2)qR9; or

each of R10and R11and/or R10and R12together with the respectively attached N atom form a five - or six-membered saturated ring which may contain an additional heteroatom in the ring selected from O, S and N, and this ring is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C6)-alkyl and (C1-C6)-halogenoalkane;

R11and R 14independently of one another denote H, (C1-C6)-alkyl, (C1-C6-halogenoalkane, (C3-C6-cycloalkyl or -(C1-C6)-alkyl-(C3-C6-cycloalkyl;

R13denotes phenyl, unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C6)-alkyl, (C1-C6)-halogenoalkane,

(C1-C6-alkoxygroup, (C1-C6-halogenoalkanes, CN, NO2, S(O)pR8and NR11R14;

R15means R11or -(CH2)qR13;

n and p independently of each other 0, 1 or 2;

q is 0 or 1; and

each heterocyclyl in the above-mentioned radicals is independently a heterocyclic radical having 3-7 ring atoms and 1, 2 or 3 heteroatoms in the ring selected from the group consisting of N, O and S.

A preferred class of compounds of formula (I) is such that:

R1denotes CN;

W represents C-halogen;

R2denotes hydrogen or halogen;

R3means CF3or OCF3;

R4denotes hydrogen, (C1-C6)-alkyl, or COR8;

A stands for (C1-C6-alkylen or (C1-C6-halogenoalkane, in which 2, 3 or 4 adjacent carbon atoms can obrotowy is the substance of part (C 3-C6)-cycloalkyl ring, which is unsubstituted or substituted by one or more radicals selected from the group consisting of (C1-C6)-alkyl and halogen;

R5means (C3-C6-cycloalkyl, -(CH2)qR7; or (C1-C6)-alkyl, substituted by one or more radicals selected from the group consisting of halogen, (C1-C6-alkoxygroup, (C1-C6-halogenoalkanes, (C3-C6)-cycloalkyl, S(O)pR8and CO2-(C1-C6)-alkyl; or when And indicates (With1-C6)-alkyl or (C1-C6-halogenoalkane and R5means (C1-C6-halogenoalkane, one or more of the carbon atoms of the group R5together with O and one or more carbon atoms And to form a 5 - or 6-membered ring;

R6means (C1-C6-halogenoalkane;

R8means (C1-C6)-alkyl or (C1-C6-halogenoalkane;

R7denotes phenyl, unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C6)-alkyl, (C1-C6)-halogenoalkane,

(C1-C6-alkoxygroup, CN, NO2, S(O)pR8and NR11R12;

R9hereafter which includes heterocyclyl, unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C4)-alkyl, (C1-C4)-halogenoalkane and (C1-C4-alkoxygroup;

R11and R12are identical or different and denote hydrogen, (C1-C6)-alkyl or (C1-C6-halogenoalkane;

n and p independently of each other 0, 1 or 2; and

q is 0 or 1.

Another preferred class of compounds of formula (I) is such that:

R1denotes CN;

W represents C-halogen;

R2denotes hydrogen or halogen;

R3means CF3or OCF3;

R4denotes hydrogen, (C1-C6)-alkyl, or COR8;

A stands for (C1-C6-alkylen or (C1-C6-halogenoalkane, in which 2, 3 or 4 adjacent carbon atom may form part (C3-C6)-cycloalkyl ring, which is unsubstituted or substituted by one or more radicals selected from the group consisting of (C1-C6)-alkyl and halogen;

R5means (C3-C6-cycloalkyl or -(CH2)qR7;or denotes (C1-C6)-alkyl, substituted by one or more radicals selected from the group consisting of halogen,

(C1-C -alkoxygroup, (C1-C6-halogenoalkanes,

(C3-C6)-cycloalkyl, S(O)pR8and CO2-(C1-C6)-alkyl; or when And indicates (With1-C6-alkylen or (C1-C6-halogenoalkanes and R5means (C1-C6)-alkyl, substituted by one or more radicals halogen, one or more of the carbon atoms of R5together with O and one or more carbon atoms And to form a 5 - or 6-membered ring;

R6means (C1-C6-halogenoalkane;

R8means (C1-C6)-alkyl or (C1-C6-halogenoalkane;

R7denotes phenyl, unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C6)-alkyl, (C1-C6)-halogenoalkane,

(C1-C6-alkoxygroup, CN, NO2, S(O)pR8and NR10R11;

R10and R11independently of one another denote H, (C1-C6)-alkyl or (C1-C6-halogenoalkane;

n and p independently of each other 0, 1 or 2; and

q is 0 or 1.

Another preferred class of compounds of formula (I) is such that:

R1denotes CN;

W represents C-halogen;

R2denotes halogen;

R 3means CF3or OCF3;

R4denotes hydrogen, (C1-C6)-alkyl, or COR8;

A stands for (C1-C9-alkylen or (C1-C9-halogenoalkane, in which 2, 3 or 4 adjacent carbon atom may form part (C3-C8)-cycloalkyl ring, unsubstituted or substituted by one or more radicals selected from the group consisting of (C1-C6)-alkyl and halogen;

R5means (C3-C7-cycloalkyl or -(CH2)qR7; or denotes (C1-C6)-alkyl, substituted by one or more radicals selected from the group consisting of halogen,

(C1-C3-alkoxygroup, (C1-C4-halogenoalkanes,

(C3-C7)-cycloalkyl, S(O)pR8, CN, NR10N11, S(O)pR7, S(O)pR9, OR7and OR9;

R6means (C1-C2-halogenoalkane;

R7denotes phenyl, unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C4)-alkyl, (C1-C4)-halogenoalkane,

(C1-C4-alkoxygroup, (C1-C4-halogenoalkanes, CN, NO2, S(O)pR8, COR11, NR10R11and HE;

R8about the means (C 1-C4)-alkyl or (C1-C4-halogenoalkane;

R9means heterocyclyl, unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C4)-alkyl, (C1-C4)-halogenoalkane and (C1-C4-alkoxygroup;

R10denotes H, (C1-C3)-alkyl, (C1-C3-halogenoalkane,

(C3-C4)-alkenyl, (C3-C4)-quinil, (C3-C6-cycloalkyl,

-(C1-C6)-alkyl-(C3-C6-cycloalkyl or -(CH2)qR13; or

R10and R11together with the attached N atom form a five - or six-membered saturated ring which may contain an additional heteroatom in the ring selected from O, S and N, and this ring is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen and (C1-C3)-alkyl;

R11and R14independently of one another denote H, (C1-C3)-alkyl, (C1-C3-halogenoalkane, (C3-C6-cycloalkyl or -(C1-C3)-alkyl-(C3-C6-cycloalkyl;

R13denotes phenyl, unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C3)-alkyl, (C 1-C3)-halogenoalkane,

(C1-C3-alkoxygroup, (C1-C3-halogenoalkanes, CN, NO2, S(O)pR8and NR11R14;

n and p independently of each other 0, 1 or 2;

q is 0 or 1; and

each heterocyclyl in the abovementioned radicals independently is a heteroaromatic radical having 5 or 6 ring atoms and 1, 2 or 3 heteroatoms in the ring selected from the group consisting of N, O and S.

As a preferred class of compounds of formula (I) is such that:

R1denotes CN;

W denotes C-Cl;

R2denotes chlorine;

R3means CF3or OCF3;

R4denotes hydrogen, (C1-C6)-alkyl, or COR8;

A stands for (C1-C4-alkylen;

R5means (C3-C6-cycloalkyl, -(CH2)qR7or

(C1-C6-halogenated; or if R5means (C1-C6-halogenoalkane, one or more of the carbon atoms of the group R5together with O and one or more carbon atoms And to form a 5 - or 6-membered ring;

R6means CF3, CF2Cl, CFCl2, CBrF2or CHF2;

R7denotes phenyl;

n is 0, 1 or 2; and

q is 0 or 1.

Another preferred class of compounds is the second of the formula (I) is such that where:

R1denotes CN;

W represents C-halogen;

R2denotes halogen;

R3means CF3or OCF3;

R4denotes hydrogen, (C1-C6)-alkyl, or COR8;

And means (C1-C12-alkylene, unsubstituted or substituted by one or more radicals selected from the group consisting of (C1-C6)-alkyl and halogen;

R5means (C1-C6-halogenoalkane;

R6means CF3, CF2Cl, CFCl2, CBrF2or CHF2; and

n is 0, 1 or 2.

Especially preferred class of compounds of formula (I) is one where:

R1denotes CN;

R2denotes chlorine;

R3means CF3;

W denotes C-Cl;

R4denotes hydrogen, (C1-C6)-alkyl, or COR8;

R5means (C1-C2-halogenoalkane;

R6means CF3;

And means (C2-C3-alkylen; and

n is 0, 1 or 2.

Another class of new derivatives of 5-substituted alkalinisation formula (I) or their pesticide acceptable salts is such that where R1denotes CN; R2denotes chlorine; R3means CF3or OCF3; W denotes C-Cl; R4denotes hydrogen or (C1-C6)-alkyl; R5about the means (C 1-C6)-alkyl; R6means CF3; A means (C1-C4-alkylen (And preferably denotes (C2-C3-alkylen) and n is 0, 1 or 2.

The following specific preferred implementation of this invention relates to new derivatives of 5-substituted alkalinisation formula (I) or their pesticide acceptable salts, where:

R1denotes CN;

W denotes C-Cl;

R2denotes chlorine;

R3means CF3;

R4denotes hydrogen or (C1-C3)-alkyl (more preferably R4denotes hydrogen or methyl);

And denotes-CH2-CH2- or-CH2CH2-CH2-;

R5means (C1-C4)-alkyl (more preferably R5means (C1-C2)-alkyl, most preferably R5denotes methyl);

R6means CF3; and

n is 0, 1 or 2.

Compounds of General formula (I) can be obtained by application or adaptation of known methods (i.e. methods previously used or described in the chemical literature).

In the subsequent description of the methods if the symbols appearing in the formulas are not defined specifically, you should understand that they are "as defined above" in accordance with the first definition of each symbol in the specification.

p> According to a particular case of the compounds according to the invention of formula (I), where R1, R2, R3, R6, W, A and n denote, as defined above, R4and R5denote, as defined above, except hydrogen, and R4denotes H, can be obtained by the coupling of compounds of formula (II):

where R1, R2, R3, R6, W and n are as defined above, and L represents a group to delete, generally halogen and preferably bromine, with a compound of formula (III):

where, as defined above, and R5as defined above, except hydrogen. The reaction is usually carried out in the presence of a base such as a carbonate of an alkali metal, for example potassium carbonate, in a solvent such as dioxane, tetrahydrofuran or N,N-dimethylformamide, at a temperature of from 0°to 100°With (preferably from 0°C to 50°).

In accordance with another particular case of the compounds according to the invention of formula (I), where R1, R2, R3, R4, R6, W, A and n are as defined above, and R4and R5as defined above, except hydrogen, OR7, OR8and OR9and R5as defined above, except H, may be obtained by alkylation or acylation of the corresponding compounds of formula (IV):

where R1, R2, R3, R6, W, A and n are as defined above, and R5as defined above, except hydrogen, the compound of the formula (V):

where R4as defined above, except hydrogen, OR7, OR8and OR9and L1refers to the deleted group, generally halogen and preferably chlorine or iodine in the case of alkylation reactions or preferably chlorine for acylation. The reaction is usually carried out in the presence of a base such as sodium hydride, in a solvent such as dioxane, tetrahydrofuran or N,N-dimethylformamide, at a temperature of from 0°to 100°With (preferably from 0°C to 50°).

According to another particular case of the compounds according to the invention of formula (I), where R1, R2, R3, R4, R6, W, A and n are as defined above, and R5as defined above, except hydrogen, can also be obtained by the coupling of compounds of formula (VI):

where R1, R2, R3, R4, R6, W and n are as defined above, with a compound of formula (VII):

where, as defined above, R5as defined above, except hydrogen, and L2refers to the deleted group, generally halogen and preferably chlorine. The reaction is usually about the W ill result in the presence of a base, such as sodium hydride, in a solvent such as dioxane, tetrahydrofuran or N,N-dimethylformamide, at a temperature of from 0°to 100°With (preferably from 0°C to 50°).

According to another particular case of the compounds according to the invention of formula (I), where R1, R2, R3, R6, W and n are as defined above, R5as defined above, except hydrogen, R4represents hydrogen and a represents-CH2-can be obtained by the coupling of compounds of formula (VIII):

where R1, R2, R3, R6, W and n are as defined above, with a mixture of formaldehyde and compounds of formula (IX):

where R5as defined above, except hydrogen. The reaction can be carried out in the presence or in the absence of a base such as a carbonate of an alkali metal, for example potassium carbonate, in a solvent such as dioxane, tetrahydrofuran or N,N-dimethylformamide, at a temperature of from 0°to 100°With (preferably from 0°C to 50°). Can be used various forms of formaldehyde, such as paraformaldehyde, if the water can also be present in the reaction mixture.

According to another particular case of the compounds according to the invention of formula (I), where R1, R2, R3, R4, R6, A, W and n, as is designated above, R5as defined above, except hydrogen, can be obtained by the coupling of compounds of formula (X):

where R1, R2, R3, R4, A, W and n are as defined above, with a compound of formula (XI):

where R5as defined above, except hydrogen, and L3refers to the deleted group, typically a halogen, for example chlorine, or alkylsulfonates. The reaction is usually carried out using a salt of an alkali metal such as sodium salt, the compounds of formula (X), in an inert solvent, such as tetrahydrofuran, at a temperature of from 0°C to 60°C.

According to another particular case of the compounds according to the invention of formula (I), where R1, R2, R3, R4, R5, R6, A, W and n are as defined above, can be obtained by the coupling of compounds of formula (XII):

where R1, R2, R3, R4, A, W and n are as defined above, and L4refers to the deleted group, typically a halogen, for example chlorine, or alkylsulfonates, with the compound of formula (IX)as defined above. The reaction is usually carried out in the presence of a base, for example alkali metal hydride such as sodium hydride or alcoholate of an alkali metal, such as tert-butyl potassium, inert the solvent, such as tetrahydrofuran, at a temperature of from 0°C to 60°With or carbonate of an alkali metal such as potassium carbonate, in an inert solvent, such as acetone, at temperatures from 0°C to the boiling point of the solvent.

A series of compounds of formula (I), which can be synthesized by the above methods may also be obtained in parallel, which can be carried out manually, semi-automatically or fully automatically. In this case, for example, to automate the process of reaction, processing or cleaning products or intermediate products. In General, it can be considered as the method described, for example, S.H. DeWitt in "Annual Reports in Combinatorial Chemistry and Molecular Diversity: Automated Synthesis", volume 1, published by Escom 1997, S. 69-77.

For the parallel implementation of this reaction and processing can be used a number of commercially available apparatuses as offered, for example, Stem Corporation, Woodrolfe Road, Tollesbury, Essex, CM9 8SE, England or H+P Labortechnik GmbH, Bruckmannring 28, 85764 Oberschleiβheim, Germany, or Both, Shirehill, Saffron Walden, Essex, England. For the parallel purification of compounds of formula (I) or the intermediate products obtained in the preparation of, inter alia, can be used in apparatus for chromatography, such as produced by ISCO, Inc., 4700 Superior Street, Lincoln, NE 68504, USA.

The use of these devices the Veda is to unify the way, where a separate stage of the process is automated, but between the stages of the process must be performed manually operations. This can be avoided by using prointegrirowany or fully integrated automated systems, which automatically blocks are controlled, for example, with the help of robots. Such an automatic system can be obtained, for example, by Zymark Corporation, Zymark Center, Hopkinton, MA 01748, USA.

In addition to these compounds of formula (I) partially or completely can be obtained by solid-phase methods. For this purpose a separate intermediate stage or the intermediate stage of the synthesis or synthesis, adapted to the method must be associated with a synthetic resin. The solid-phase synthesis methods are widely described in the literature, for example, Barry A. Bunin in "The Combinatorial Index, Academic Press, 1998.

The application of the methods of solid-phase synthesis allows you to use a number of methods known from the literature, which, in turn, can be performed manually or automatically. For example, the "Tea-bag method (Houghten, U.S. patent 4631211; Houghten et al., Proc. Natl. Acad. Sci, 1985, 82, 5131-5135), which use the products IRORI, 11149 North Torrey Pines Road, La Jolla, CA 92037, USA, can be semi-automatic. Automation of solid-phase parallel synthesis successfully implemented, for example, in units Argnaut Technologies, Inc., 887 Industrial Road, San Carlos, CA 94070, USA, or MultiSyn Tech GmbH Wullener Feld 4, 58454 Witten, Germany.

The implementation of the methods described here, gives compounds of formula (I) in the form of a series of substances, which are called libraries. This invention also relates to libraries, which contain at least two compounds of formula (I).

Intermediates of formula (II), where L denotes chlorine, bromine or iodine, can be obtained according to known methods, for example as described in patent EP 0295117, by diazotization of the corresponding amine of formula (VIII), usually using Alternaria, such as tert-butylnitrite, in the presence of a suitable halogenation agent, preferably of bromoform, iodine or anhydrous chloride of copper, possibly in the presence of a solvent, such as acetonitrile or chloroform, at temperatures between 0°to 100°C.

Some of the compounds of the formula (IV) and (X) is included in the definition of formula (I) can be obtained by the methods described above whereas the other compounds of the formula (IV) and (X) are known or can be obtained by known methods.

Compounds of formula (II), (III), (V), (VI), (VII), (VIII), (IX), (XI) and (XII) are known or can be obtained by known methods.

The following non-limiting examples illustrate the formation of compounds of formula (I).

Chemical examples

NMR spectra were shot in deutero is hloroform, if not stated otherwise.

In the following examples, the amount (including interest) are in mass units, unless otherwise specified.

Example 1

To a solution of 5-bromo-1-(2,6-dichloro-4-triptoreline)-3-cyano-4-triftormetilfullerenov (2.5 g, 4.8 mmol) in 1,4-dioxane and N,N-dimethylformamide were added 2-methoxyethylamine (0.74 g, 9.7 mmol) and potassium carbonate (1.35 g, 9.7 mmol). The resulting mixture was stirred at 50°4 hours, left to stand overnight, then poured into a mixture of water and dichloromethane. The organic phase is washed with water, dried (sodium sulfate), evaporated. The crude product is recrystallized from diisopropyl ether, obtaining 1-(2,6-dichloro-4-triptoreline)-3-cyano-5-(2-methoxyethylamine)-4-triftormetilfullerenov in the form of a white solid (compound number 1-3, 1.30 grams), TPL 164°C.

Example 2

To a solution of 1-(2,6-dichloro-4-triptoreline)-3-cyano-5-(2-methoxyethylamine)-4-triftormetilfullerenov (1.5 g, 2.9 mmol) in tetrahydrofuran at 20°C in an atmosphere of nitrogen was added sodium hydride (0,38 g, 60%in oil, 9.4 mmol) and stirred for 0.5 hours. Added logmean (1.68 g, 11.7 mmol) and the mixture was stirred 15 hours at 20°C, then heated to 40°8 hours. The mixture was added to ethyl acetate and saturated solution of ammonium chloride. The organic layer was washed with water and brine, dried (sodium sulfate), Aravali and chromatographically on silica gel, elwira a mixture of heptane-ethyl acetate (9:1)to give 1-(2,6-dichloro-4-triptoreline)-3-cyano-5-[N-(2-methoxyethyl)-N-methylamino]-4-triftormetilfullerenov in the form of a white solid (compound number 2-3, 0,78 g), TPL 75°C.

Example 3

Potassium carbonate (6.6 g, and 47.5 mmol) was added to a solution of 5-amino-1-(2,6-dichloro-4-triptoreline)-3-cyano-4-cryptomaterial (5.0 g, 11.87 per mmol) in isopropanol and stirred for five minutes before adding paraformaldehyde (0.75 g). The resulting mixture was stirred at 20°three days, then was diluted with isopropanol (20 ml) and was added to water and ethyl acetate. The organic layer was dried (sodium sulfate) and was evaporated, obtaining 1-(2,6-dichloro-4-triptoreline)-3-cyano-5-isopropylacrylamide-4-cryptomaterial (compound number 1-4, 5.3g).

Example 4

To a solution of 5-bromo-1-(2,6-dichloro-4-triptoreline)-3-cyano-4-triftormetilfullerenov (3.0 g, 5.8 mmol) in 1,4-dioxane was added 1-amino-2-propanol (0.52 g, 7.0 mmol) and triethylamine (0,76 g, 7.0 mmol). The mixture was heated at 100°2 hours. After processing, extraction and recrystallization from a mixture of heptane-ethyl acetate (1:1) was obtained 1-(2,6-dichloro-4-triptoreline)-3-cyano-5-(2-hydroxypropylamino)-4-triftormetilfullerenov (compound number 1-5, 2.67 g). 19F: -64,2; -80,9.

The following comparative examples illustrate the production of intermediate the products, used in the synthesis of the above examples.

Comparative example 1

Tert-butylnitrite (84 ml, to 0.662 mol) was added to a suspension of 5-amino-1-(2,6-dichloro-4-triptoreline)-3-cyano-4-triftormetilfullerenov (100 g, 0,221 mol) in bromoform (320 ml). The resulting mixture was heated to 60-70°3 hours. Added another part of tert-butylnitrite (84 ml, to 0.662 mmol) and the mixture was stirred at 60-70°With another 2.5 hours. Then it was cooled, washed with hexane, hexane-toluene and filtered. The solid is washed with pentane and dried in vacuum, obtaining 5-bromo-1-(2,6-dichloro-4-triptoreline)-3-cyano-4-triftormetilfullerenov in the form of a yellow solid (96,69 g, yield 79%), TPL 142°C.

The following preferred compounds are presented in tables 1-6, are also part of this invention and have been, or could be obtained according to or analogously to the above examples 1-4 or with the above-described General methods. In tables i-Pr represents isopropyl. If atoms are missing indexes, it should be understood that they assumed, for example, denotes CH3 CH3.

The values of the shifts of 19F-NMR spectra are given in ppm

Rooms compounds are listed only for reference purposes.

Table I

The compounds of formula (I), in which estately have the following meanings:

R1= CN, R6means CF3, R4denotes hydrogen, W = C-Cl, R2=Cl, R3= CF3
The connection numberAndR5nTPL(° (C) or NMR (ppm)
1-1SNSNCH30
1-2SNSNCH31
1-3SNSNCH32164
1-4CH2i-Pr0
1-5SNSN(CH3)N219F: -64,2; -80,9
1-6SNSNSNSN2151
1-7SSNSCH31107
Table II

R1= CN, R6= CF3, R4= CH3W = C-Cl, R2= Cl, R3= CF3
The connection numberAndR5nTPL (°C); NMR (ppm)
2-1SNSNCH30
2-2SNSNCH31
2-3SNSNCH3275
2-4CH2SNSN0
2-5CH2SNSN1
2-6CH2i-Pr0
2-7CH2i-Pr1
2-8CH2CH30
2-9CH2CH31
2-10SNSNN2
2-11SSNSN2
2-12SSNSCH3219F: -63,68; -78,57
Table III

R1= CN, R6= CF3, R4= CO2CH2CH3W = C-Cl, R2= Cl, R3= CF3
Room

connection
AndR5nTPL(° (C) NMR (ppm)
3-1SNSNCH30
3-2 SNSNCH31
3-3SNSNCH32
3-4CH2SNSN0
3-5CH2SNSN1
3-6CH2i-Pr0
3-7CH2i-Pr1
3-8CH2CH30
3-9CH2CH31
Table IV

R1= CN, R6= CF3, R4= CH2OCH2CH3W = C-Cl, R2= Cl, R3= CF3
Room

Connection
AndR5nTPL(° (C) or NMR(ppm)
4-1SNSNCH30
4-2SNSNCH31
4-3SNSNCH32
4-4CH2SNSN0
4-5CH2SNSN1
4-6CH2i-Pr0
4-7CH2i-Pr1
4-8CH2CH30
4-9CH2CH31

i-Pr
Table V

R1= CN, R6= CF3, R4= H, W = C-Cl, R2= Cl, R3= OCF3
Room connection.AndR5NTPL(°)
5-1CH2CH2CH30
5-2CH2CH2CH31
5-3CH2CH2CH32
5-4CH2CH2CH30
5-5CH2CH2CH31
5-6CH2i-Pr0
5-7CH21
5-8CH2CH30
5-9CH2CH31
Table VI

R1= CN, R6= CF3, R4= CH3W = C-Cl, R2= Cl, R3= OCF3
Room connection.AndR5NTPL(°)
6-1CH2CH2CH30
6-2CH2CH2CH31
6-3CH2CH2CH32
6-4CH2CH2CH30
6-5CH2CH2CH31
6-6CH2i-Pr0
6-7CH2i-Pr1
6-8CH2CH30
6-9CH2CH31

The term "compound of the invention", as used on the more covers 5-substituted alkylaminocarbonyl formula (I)as defined above, and their pesticide acceptable salt.

In a preferred aspect of this invention the compounds of formula (I) used for the destruction of parasites in animals. Preferably the animal, which must be processed is the pet-companion such as a dog or cat.

The following aspect of the compounds according to the invention of formula (I) or their salts or compositions used to prepare veterinary medicines, preferably for the destruction of parasites, specifically ecto - and endoparasites in the body of the animal and the animal's body.

Compounds according to the invention and methods of their application are especially useful for combating arthropods or helminths, which are harmful or spread or act as vectors of diseases of domestic animals, such as the above, and more specifically, to destroy mites, lice, fleas, midges, or in the treatment of bites, irritations or anamosa (caused by flies). Compounds according to the invention, in particular, can be used for the destruction of arthropods or helminths, which are present inside the home of an animal host or eat in the skin or on the skin or suck the blood of the animal for which they can be administered orally, parenteral is but percutaneous or locally.

Described compositions can usually be used on animals infected with or exposed to infection arthropods or helminths, parenteral, oral, or local introduction of compositions in which the active ingredient has an immediate and/or prolonged action over a period of time against the arthropods or helminths, such as adding in feed or suitable swallow pharmaceuticals, edible baits, salt licking, dietary Supplement, add drugs, sprays, baths, showers, sprays, dusty, greases, shampoos, creams, waxes for application or system Samoobrona animals.

The compounds of formula (I), in particular, can be used for the destruction of parasites in animals by oral administration and in a more preferred aspect of the invention the compounds of formula (I) can be used to destroy parasites in animals by oral administration. The compounds of formula (I) or their salts can be introduced before, during or after feeding. The compounds of formula (I) or their salts can be mixed with a carrier and/or feed.

The compounds of formula (I) or their salts are administered orally to the animals in the dose is usually in the range from 0.1 to 500 mg/kg of the compounds of formula (I) or its salt per kg of body weight is alive is private (mg/kg).

The frequency of treatment of an animal, preferably a pet, which should be treated by a compound of the formula (I) or its salt is usually from about once per week to about once a year, preferably from about once in two weeks to about once every three months.

Compounds according to the invention with the greatest success can be entered with other parasuicide effective substances, such as endoparasiticides and/or ectoparasiticide and/or indecipherability. For example, these compounds include macrocyclic lactones, such as avermectin, or milbemycin, such as ivermectin, pirates, or growth regulator insect, such as lufenuron or methoprene.

According to additional features of the present invention, a method for destroying insects in the locus, which provides for the introduction of an effective amount of the compounds of formula (I) or its salt. For this purpose, the specified connection is usually used in the form of pesticide compositions (i.e. in combination with compatible diluents or carriers and/or surface-active agents suitable for use in pesticide compositions), for example, as described below.

One aspect of this invention, as defined above, is a method for killing pests in locuses includes, for example, the pest (plant, field, forest, garden, waterway, soil, plant product or similar), where the pest occurs, or eats, or place, susceptible to infestation by the pest in the future. The connection according to the invention can therefore be applied directly to the pest, to the place where the pest inhabits or eats, or to place susceptible to infestation by the pest in the future. As can be seen from the previous use of pesticides, this invention provides pesticide active compounds and methods of using these compounds for the destruction of many species of pests, including arthropods, especially insects or mites, or plant nematodes. Compounds according to the invention thus can be used in practice, for example, in veterinary science or animal husbandry, crop production and horticulture, forestry or health. Compounds according to the invention can be used, for example, in the following areas of application against the following pests.

In the field of veterinary medicine or livestock husbandry or in sanitation against arthropods, which are external and internal parasites of vertebrates, particularly warm-blooded vertebrates, for example domestic animals, such as cattle, sheep, goats, horses, pigs, on the domestic birds, dogs and cats, for example Acarina, including ticks (for example, soft ticks, including rogassovich mites, for example Argas spp. and Ornithodorus spp. (e.g., Ornithodorus moubata); hard ticks, including ticks such as Boophilus spp., for example, Boophilus microplus, family rhipicephalus, such as Rhipicephalus appendiculatus and Rhipicephalus sanguineus; ticks (for example, Damalinia spp.); fleas (e.g., Ctenocephalides spp., for example, Ctenocephalides felis (cat flea) and Ctenocephalides canis (dog flea); lice, for example, Menopon spp.; dipterans (e.g., Aedes spp., Anopheles spp., Musca spp., Hypoderma spp.); Heteroptera; Dictyoptera (e.g., Periplaneta spp., Blatella spp.), Hymenoptera; for example against infections of the gastro-intestinal tract caused by parasitic worms, nematodes, such as family members Trichostrogylidae.

For the destruction of soil insects such as root worms grain, termites (especially for protection of structures), grubs, wireworms, skosarev alfalfa, grinders, Cutworm, aphids or larvae. They can also be used to provide activity against pathogenic nematodes of plants, such as causing dematos, cysts, clunker, destruction or nematus stems or bulbs or against ticks. For the destruction of soil pests such as root worms grain, compounds useful to be applied in an effective amount to or injected into the soil in which grain or seeds or roots estudiantine.

Sanitation connection is particularly applicable when the destruction of many insects, especially dung flies or other dipteran pests such as house flies, jagalchi autumn, linki, jagalchi small cow, deer flies, botflies nasopharyngeal horses, black flies, biting midges, black flies or mosquitoes.

When the protection of stored products, for example cereals, including grain and flour, groundnuts, animal feed, wood or household items such as carpets and textiles, the compounds according to the invention is applicable against attack by arthropods, more specifically beetles, including weevils, moths or mites, for example Ephestia spp. (flour moths), Anthrenus spp. (carpet beetles), Tribolium spp. (flour beetles), Sitophilus spp. (grain weevils) or Acarus spp. (ticks).

When you eliminate cockroaches, ants or termites or similar arthropod pests in infested domestic or industrial premises, or upon the destruction of mosquito larvae in waterways, wells, pools, or other flowing or standing water.

For the processing of foundations, structures or soil to prevent attacks on the building of termites, such as Reticulitermes spp., Heterotermes spp., Coptotermes spp.

In agriculture against adult insects, larvae and eggs of Lepidoptera (butterflies and moths), e.g. Heliothis spp., such as Heliothis virescens (:SMOS is AED tobacco), Heliothis armigera and Heliothis zea. Against adults and larvae of Coleoptera (beetles), for example, Anthonomus spp., for example grandis (cotton weevil), Leptinotarsa decemlineata (Colorado potato beetle), Diabrotica spp. (flea dinosau). Against Heteroptera (Hemiptera and Homoptera), for example Psylla spp., Bemisia spp., Trialeurodes spp., family aphid, Myzus spp., Megoura viciae, Phylloxera spp., Nephotettix spp. (insects, jumping in leaves of rice), Nilaparvata spp.

Against flies, for example Musca spp. Against Thysanoptera such as Thrips tabaci. Against Orthoptera such as Locusta and Schistocerca spp. (grasshoppers and crickets), for example Gryllus spp., and Acheta spp., for example Blatta orientalis, Periplaneta americana, Blatella germanica, Locusta migratoria migratorioides and Schistocerca gregaria. Against Collembola, e.g. Periplaneta spp. and Blatella spp. (cockroaches). Against arthropods of agricultural significance such as Acari (mites)such as Tetranychus spp. and Panonychus spp.

Against nematodes which attack plants and trees that are important for agriculture, forestry or horticulture either directly or by spreading bacterial, viral, mycoplasmosis or fungal diseases of plants. For example, nematodes, causing nematus roots, such as Meloidogyne spp. (e.g. M. incognita).

In the practical use for the destruction of arthropods, especially insects and mites, or nematode pests method, for example, involves the application to the plants or to the environment in which they grow, effective Koli is esta compounds according to the invention. For this method of connection according to the invention is usually applied to the locus in which must be liquidated by infecting arthropods or nematodes, in an effective dose in the range of from about 2 g to about 1 kg of active compound per hectare of cultivated locus. In ideal conditions, depending on the pest, which must be destroyed, adequate protection can be achieved at a lower dose. On the other hand, adverse weather conditions, pest resistance, or other factors may require that the active ingredient was used in higher doses. The optimal dose depends on many factors, such as type destroy the pest, type or stage of growth of the infected plants, planting density, or method of application. Preferably the effective interval of the dose of active compound is from about 10 g/ha to about 400 g/ha, more preferably from about 50 g/ha to about 200 g/ha

If the pest is put in the soil, active compound, usually in the composition, uniformly distributed on the square, which must be processed (i.e., for example, a wide processing or processing strips) in any convenient way and put in a dose of from about 10 g/ha to about 400 grams of active ingredient/ha, preferably from about 50 g/ha to use is but 200 g of active ingredient/ha If you contribute to a depth of root sprouts or water drops plant, liquid solution or suspension containing from about 0,075 to about 1000 mg of active ingredient/l, preferably from about 25 to about 200 mg active ingredient/liter Coating can be carried out if desired in the field or area of cultivation of the crop, in whole or near the seed or plants, which must be protected from attack. The connection according to the invention can be washed into the soil by spraying water over the area or can be left to the natural action of rain. During or after application of the composition of the compound can, if desired, be mechanically distributed in the soil, such as plowing, disking, or use of travelling chains. Application may be made before planting, at planting, after planting, but prior to germination or after germination.

The connection according to the invention and the methods of extermination of pests in addition have practical value in the protection of field, forage, plantation, greenhouses, gardens or vineyards, ornamental plantings, tree plantations or forest, for example cereals (such as wheat or rice), cotton, vegetables (such as peppers), field crops (such as sugar beet, soybean or oilseed rape), field or forage crops (such as maize or sorghum), orchards, or groves (such as to the point or one-seeded fruit or citrus), ornamental plants, flowers, or vegetables, or shrubs under glass, or in gardens or parks, or forest trees (both deciduous and evergreen) forests, plantations and nurseries.

They are also valuable in the protection of timber (standing, cut, processed, stored or building) from attack, for example, the carpenter or beetles or termites.

They are applicable for the protection of stored products such as grains, fruits, nuts, spices or tobacco, both whole and ground, or in products, from attack by moths, beetles, mites or grain weevil. Protected are also stored products of animal origin, such as skin, hair, wool or feathers in natural or processed form (e.g., carpets or textiles), from the attacks of beetles, as well as stored meat, fish or grain from attack by beetles, mites or flies.

Described composition for application to growing crops or crops or for seed treatment usually alternatively can be used to protect stored products, household items, property, or areas of the environment. Appropriate means of application of the compounds according to the invention are: for growing crops sprays of leaves (e.g., aerosol spraying in the furrow), dust is, granules, smokes, or foam, or a suspension of finely powdered or encapsulated compositions; for soil or roots of liquid impregnation, dusty, granules, smokes or foam; for the seeds of cereal crops application in the form of the final touches seed liquid suspensions or bustami; for the environment in General or for specific areas where they can hide pests, including stored products, timber, household goods, or domestic or industrial premises, in the form of aerosols, fog, Farrukh Dustov, fumigation, wax-smears, lacquers, granules, or baits or liquid additives to waterways, wells, the reservoirs or flowing or stagnant water.

The compounds of formula (I) can also be used to kill pests in crops of known genetically modified plants or genetically modified plants, which should be developed. As a rule, the transgenic plants have particularly advantageous properties, for example resistance to agents crops protection, resistance to plant diseases or plant diseases caused by pathogenic organisms, such as particular insects or microorganisms such as fungi, bacteria or viruses. Other particular properties relate, for example, post-harvest, in respect of quantity, quality, properties, storing the program, compositions and specific elements. For example, the famous transgenic plants, where the increased content of starch or modified starch quality or where harvested harvested material has a different composition of fatty acids composition.

Preferably use in economically important transgenic crops of useful and ornamental plants, for example cereals such as wheat, barley, rye, oats, millet, rice, manioc and corn, or other crops, sugar beet, cotton, soya, oilseed rape, potatoes, tomatoes, peas and other vegetables.

When used in transgenic crops, in particular such that are resistant to insects, often, in addition to the action against harmful organisms, they should be observed in other cultures that are specific for use in transgenic crops, see the effects, which is specific for use in transgenic crops, in the sense, for example a modified or specifically extended spectrum of pests that can be destroyed, or modified doses coating that can be applied.

The invention therefore also relates to the use of compounds of formula (I) for the destruction of pests in transgenic cultivated plants.

According to additional features of the present invention, it is relative to the Xia to pesticide compositions containing one or more compounds according to the invention, as defined above, in combination with, and preferably homogeneous dispergirovannykh in one or more compatible pesticide acceptable diluents or carriers and/or surface-active agents [i.e. diluents or carriers and/or surface-active agents of the type generally accepted state of the art, suitable for use in pesticide compositions and compatible with the compounds of the invention].

In practice, the compounds according to the invention most often are components of the compositions. These compositions can be used to kill arthropods, especially insects, or plant nematodes or mites. The composition can be of any type known state of the art, suitable for use against the desired pest in any room or the inner or outer space. These compositions contain at least one compound according to the invention as an active ingredient in combination or Association with one or more other compatible components which are, for example, solid or liquid carriers or diluents, additives, surface-active agents or the like, appropriate to the intended application, agronomically or medical is ielemia. These compositions, which may be made by any method known state of the art, are also part of this invention.

Compounds according to the invention in their commercially available formulations and application forms obtained from the above compositions may be present in mixtures with other active substances such as insecticides, attractants, sterilizing agents, acaricides, nematicides, fungicides, growth regulators or herbicides.

Pesticides are, for example, phosphoric esters, carbamates, esters of carboxylic acids, formamidines, tin compounds and substances produced by microorganisms.

Preferred components of the mixtures are:

1) from the group of phosphorus compounds

Arafat, azamethiphos, azinphos-ethyl, azinphos-methyl, bromophos, bromophos-ethyl, cadusafos (F-67825), chlorethoxyfos, Chlorfenvinphos, chlormephos, chlorpyrifos, chlorpyrifos-methyl, demeton, demeton-S-methyl, demeton-S-methylsulfone, dialifos, diazinon, dichlorvos, dicrotophos, dimethoate, disulfoton, EPN, ethion, ethoprophos, etrimfos, Rampur, fenamiphos, fenitrothion, fensulfothion, fenthion, flupirtine, fonofos, formation, fosthiazate, heptenophos, isazofos, isocial, isoxathion, Malathion, methacrifos methamidophos, methidathion, salicion, mevinphos, monocrotophos, naled, omethoate, oxydemeton-methyl, parathas is he, parathion-methyl, pentat, Fort, fosalan, phosfolan, fastcars (BAS-301), phosmet, phosphamidon, phoxim, pirimiphos, pirimiphos-ethyl, pirimiphos-methyl, profenofos, propafol, propetamphos, prothiofos, pyraclofos, peridinin, quinalphos, sulprofos, temephos, terbufos, tebupirimfos, tetrachlorvinphos, thiometon, triazophos, trichlorfon, vamidothion;

2) from the group of the carbamates

alankar (CA-135), aldicarb, 2-second-butylphenylmethyl (VRMS), carbaryl, carbofuran, carbosulfan, cloethocarb, benfuracarb, ethiofencarb, furathiocarb, HCN-801, isoprocarb, methomyl, 5-methyl-meta-kumanivtsi(methyl)carbamate, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, 1-methylthio(ethylidene)-N-methyl-N-(morpholinothio)carbamate (UC 51717), triazamate;

3) from the group of esters of carboxylic acids

acrinathrin, allethrin, alphamethrin, 5-benzyl-3-fulleylove ether (E)-(1R)-CIS-2,2-dimethyl-3-(2-oxathiolan-3-ylidenemethyl)cyclopropanecarbonyl acid, beta-cyfluthrin, alpha-cypermethrin, beta-cypermethrin, bioallethrin, bioallethrin ((S)-cyclopentyloxy isomer), bioresmethrin, bifenthrin, (RS)-1-cyano-1-(6-phenoxy-2-pyridyl)methyl ester of (1RS)-TRANS-3-(4-tert-butylphenyl)-2,2-dimethylcyclopropanecarboxylic acid (NCI 85193), cicloprofen, cyfluthrin, cigalotrin, Caitrin, cypermethrin, cyphenothrin, deltamethrin, empenthrin, esfenvalerate, fenfluthrin, fenpropathrin, fenvalerate, glucotr the NAT, flumethrin, fluvalinate (D-isomer), imiprothrin (S-41311), lambda cigalotrin, permethrin, phenothrin (R-isomer), prallethrin, pyrethrins (natural substances), resmethrin, tefluthrin, tetramethrin, theta-cypermethrin, tralomethrin, transfluthrin, Zeta-cypermethrin (F-56701);

4) from the group amidino

amitraz, Chlordimeform;

5) from the group of compounds of tin

cyhexatin, fenbutatin;

6) other

the abamectin, ABG-9008, acetamiprid, acequinocyl, Anagrapha falcitera, AKD-1022, AKD-3059, ANS-118, azadirachtin, Bacillus thuringiensis, Beauveria bassianea, bensultap, bifenazate, binapacryl, BJL-932, bromopropylate, BTG-504, BTG-505, buprofezin, camphechlor, cartap, Chlorobenzilate, chlorfenapyr, chlorfluazuron, 2-(4-chlorophenyl)-4,5-diphenylthiophene (UBI-T 930), chlorphenesin, chlorphoxim, chromafenozide, clothianidin, 2-naphthylethylenediamine (Ro12-0470), cyromazine dialogen (thiamethoxam), diafenthiuron, DBI-3204, ethyl-2-chloro-N-(3,5-dichloro-4-(1,1,2,3,3,3-hexamer-1 propyloxy)phenyl)carbarnoyl)-2-carboximidic, DDT, dicofol diflubenzuron, N-(2,3-dihydro-3-methyl-1,3-thiazol-2-ilidene)-2,4-xylidine, dihydroxytestosterone, dinobuton, dinocap, giovanola, abamectine, endosulfan, ethiprole (sulfation), etofenprox, etoxazole, fenazaquin, fenoxycarb, fipronil fluazuron, flumet (Florentin, SZI-121), a simple 2-fluoro-5-(4-(4-ethoxyphenyl)-4-methyl-1-pentyl)diphenyl ether (MTI 800), granulosis and nuclear politice is their viruses, fenpyroximate, benthiocarb, flociprin, flibanserin, lubricant, flucycloxuron, flufenoxuron, Florentin, flavandiols, propoxyphen, gamma-HCH, galvanized, halftracks, hexaflumuron (DE_473), hexythiazox, HOI-9004, hydramethylnon (AC 217300), IKI-220, indoxacarb, ivermectin, L-14165, Imidacloprid, indoxacarb (DPX-MP062), kanamit (AKD-2023), lufenuron, M-020 M-020, methoxyfenozide, milbemectin, NC-196, neergard, netinterface, nitenpyram, 2-nitro methyl-4,5-dihydro-6N-thiazin (DS 52618), 2-nitro methyl-3,4-dihydrodiol (SD 35651), 2-nitromethylene-1,2-diazinon-3-ylcarbamate (WL 108477), novaluron, pyridalyl, propargite, protrudent, pymetrozine, pyridaben, pyrimidifen, pyriproxifen, NC-196, NC-1111, NNI-9768, novaluron (MCW-275), OK-9701, OK-9601, OK-9602, OK-9802, R-195, RH-0345, RH-2485, RYI-210, S 1283, S-1833, SI-8601, selflove, Solomatin (CG-177), spinosad, spirodiclofen, SU-9118, tebufenozide, tebufenpyrad, teflubenzuron, tetradifon, tetrasul, thiacloprid, thiocyclam, thiamethoxam, toppenberg, triazamate, triethoxysilane And, triflumuron, verboten, vertalec (mycotal), YI-5301.

The above components for combinations are known active substances, many of which are described in Ch.R. Worthing, S.B.Walker, The Pesticide Manual, 12th edition, British Crop Protection Council, Farnham 2000.

The effective dose of the compounds used according to the invention can vary within wide limits, in particular, depending on the nature of the s pest which must be destroyed, or the degree of contamination, for example, grain crops listed pests. Typically, the compositions corresponding to the invention contain from about 0.05 to about 95 wt.% one or more active ingredients according to the invention from about 1 to about 95% of one or more solid or liquid carriers and, possibly, from about 0.1 to about 50% of one or more other compatible components, such as surface-active agents or the like. In this description, the term "carrier" denotes an organic or inorganic ingredient, natural or synthetic, with which combine active ingredient to facilitate its application, for example, to plant, to seeds or to the soil. The specified media is therefore generally inert and should be acceptable (for example, agronomically acceptable, in particular, for the treated plants).

The carrier may be solid, such as clays, natural or synthetic silicates, silica, resins, waxes, solid fertilizers (e.g. ammonium salts), ground natural minerals, such as kaolin, clay, talc, chalk, quartz, attapulgite, montmorillonite, bentonite or diatomaceous earth, or ground synthetic minerals, such as silica, alumina or silicates, especially silicates of aluminum or magnesium. As the firmness of the respiratory carriers for granules fit the following: crushed or fractionated natural rocks, such as calcite, marble, pumice, thick and dolomite; synthetic granules of inorganic or organic flour; granules of organic material such as sawdust, coconut shell, stalk crops, husk crops or tobacco stems; kieselguhr, tricalcium phosphate, powdered cork or activated carbon; water-soluble polymers, resins, waxes; and solid fertilizers. These solid compositions can, if desired, contain one or more compatible wetting, dispersing, emulsifying or tinted agents which, if solid, can also serve as diluents.

The media can also be a liquid, such as water; alcohols, particularly butanol or glycol as well as their simple or esters, in particular the acetate methylglycol; ketones, in particular acetone, cyclohexanone, methyl ethyl ketone, methyl isobutyl ketone or isophorone; petroleum fractions such as paraffinic or aromatic hydrocarbons, particularly xylenes or alkylnaphthalene; mineral or vegetable oils; aliphatic chlorinated hydrocarbons, particularly trichloroethane or methylene chloride; aromatic chlorinated hydrocarbons, in particular chlorobenzene; water-soluble or strongly polar solvents, such as dimethylformamide, dimethylsulfoxide or N-organic; sireny the gases; or the like or mixtures thereof.

Surface-active agent can be an emulsifier, dispersant or wetting agent of ionic or non-ionic type or a mixture of these surface-active agents. Among them, for example, are salts of polyacrylic acids, salts of lignosulphonic acids, salts of Phenolsulphonic or naphthalenesulfonate acids, polycondensates of ethylene oxide with fatty alcohols or fatty acids or fatty esters or fatty amines, substituted phenols (in particular ALKYLPHENOLS or kilfenora), salts of esters sulfonterol acid derivative taurine (in particular, alliterate), esters of phosphoric acid with alcohols or polycondensate of ethylene oxide with phenols, esters of fatty acids with polyols or sulphate, sulphonate or phosphate functional derivatives of the above compounds. The presence of at least one surface-active agent is usually important if the active ingredient and/or the inert medium is only weakly soluble in water or insoluble in water, and a carrier agent composition for the application is water.

The composition of the invention can optionally contain other additives, such as adhesives or dyes. The compositions can be used such adhesives as carboxymethylcellulose and natural and synthetic polymers in the Orme powder granules or lattices, such as gum Arabic, polyvinyl alcohol or polyvinyl acetate, natural phospholipids, such as capalini or lecithins, and synthetic phospholipids. It is possible to use colorants such as inorganic pigments, for example iron oxides, titanium oxides or Prussian blue; organic dyes such as alizarin dyes, azo dyes or metallophthalocyanine dyes, or trace elements such as salts of iron, manganese, boron, copper, cobalt, molybdenum or zinc.

For use in agriculture compounds according to the invention is therefore usually used in the form of compositions, which are in various solid or liquid forms.

Solid forms of compositions which can be used are sprayed powders (with a content of compounds according to the invention is in the range of up to 80%), wettable powders or granules (including granules, dispersible in water, in particular those which are obtained by extrusion, compacting, impregnation of a granular carrier, or granulation, proceeding from a powder (the content of the compounds according to the invention in the above wettable powders or granules is between about 0.5 and about 80%). Solid homogeneous and heterogeneous compositions containing one or more compounds according to the invention, such as granules, beads, the Rickettas or capsules, can be used for the treatment of standing or flowing water for some period of time. A similar effect can be achieved when using streams or intermittent recharge water dispersible concentrates, as described here.

Liquid compositions, for example, include aqueous or non-aqueous solutions or suspensions (such as emulsifiable concentrates, emulsions, fluid, dispersions or solutions or aerosols. Liquid compositions also contain, in particular, emulsifiable concentrates, dispersions, emulsions, fluid, aerosols, wettable powders (or powders for spraying), dry flowable or paste like form compositions that are liquid or are intended for formation of liquid compositions when applied, for example, in the form of water sprays (including small or after ultra-small volumes) or mists or aerosols.

Liquid compositions, for example, in the form of emulsifiable or soluble concentrates most often contain from about 5 to about 80 wt.% the active ingredient, whereas the emulsion or solution, ready for use, in such cases, contain from about 0.01 to about 20% of the active ingredient. In addition to the solvent emulsifiable or soluble concentrates can contain, if required, from about 2 to about 50% of suitable additives, such as stabilizers, Ernesto-active agents, impregnating agents, corrosion inhibitors, dyes or adhesives. Emulsions of any desired concentration, which, in particular, are suitable for application, for example, plants that can be obtained from these concentrates by dilution with water. These compositions included within the scope of compositions that can be used in this invention. The emulsion can be in the form of type water-in-oil type or oil-in-water, and they can have a thick consistency.

Liquid compositions according to this invention in addition to the usual applications in agriculture can be used, for example, for processing substrates or infected with or susceptible to infection arthropods (or pests, destroying compounds according to this invention), including premises, external or internal storage space or processing containers or standing or flowing water.

All these aqueous dispersions, or emulsions, or sprayable mixtures can be applied, for example, for cereals by any appropriate means, mainly by spraying, according to the norms, which typically are of the order of from about 100 to about 1200 litres of spray mixture per hectare, but can be higher or lower (e.g., low or ultra-low volume) depending on the needs or application technique. The compound or composition of this innovation is the invention it is convenient to use on the vegetation and, in particular, the roots or the leaves affected by pests that need to be resolved. Another way of using compounds or compositions according to this invention is the use of chemicals (chemical substances), i.e. adding a composition containing the active ingredient, to irrigation water. This irrigation can be a sprinkler for deciduous pesticides or soil by irrigation or subsurface irrigation for soil or systemic pesticides.

Concentrated suspensions, which can be applied by spraying, are prepared so as to obtain a stable fluid product which does not asserted (fine grinding) and usually contains from about 10 to about 75 wt.% the active ingredient, from about 0.5 to about 30% surface-active agent, from about 0.1 to about 10% of the thickening agent, from about 0 to about 30% of suitable additives such as defoamers, corrosion inhibitors, stabilizers, penetrating agents, adhesives, and as carrier, water or an organic liquid in which the active ingredient is poorly soluble or insoluble. In the carrier to assist in preventing sedimentation or as antifreeze for water can be dissolved with certain organic solids or inorganic salts.

Wettable powders (or powders for spraying) about what a rule is prepared so so that they contain from about 10 to about 80 wt.% the active ingredient, from about 20 to about 90% solid carrier, from about 0 to about 5% of a humectant, from about 3 to about 10% dispersant and, optionally, from about 0 to about 80% of one or more stabilizers and/or other additives, such as penetrating agents, adhesives, agents against caking, dyes or the like. To obtain these wettable powders, the active ingredient is thoroughly mixed in suitable mixers with the additional substances that can be impregnated on the porous filler and pulverized with the use of mills or other suitable grinders. So, get wettable powders, wettability and suspenderbelt which are preferred. They can be suspended in water to obtain the desired concentration, and this suspension can be very successfully used, in particular, for application to the leaves of the plant. "Granules, dispersible in water (WG)" (granules, which are easily dispersed in water) have compositions that are essentially similar to wettable powders. They can be obtained by granulating compositions described for wettable powders or wet way (by contacting finely ground active ingredient with an inert filler Nebolsin amount of water, for example, 1 to 20 wt.%, or with an aqueous solution of dispersant or a binder, followed by drying and sieving), or dry by pressing, followed by crushing and sieving).

Consumption rates and the concentration is composed of the compositions may vary in accordance with the method of application or the nature of the compositions or their use. Generally speaking, compositions for application to control pests, arthropods, or plant nematodes, usually contain from about 0,00001 to about 95 wt.%, more specifically from about 0.0005 to about 50 wt.% one or more compounds according to the invention or of all active ingredients (that is, the compounds according to the invention together with other substances toxic to arthropods or plant nematodes, synergists, trace elements or stabilizers). Actually used composition and consumption rates will be selected to achieve the desired(s) effect(s) farmer, breeder, a practicing physician or veterinarian, by the operator of the extermination of pests or other specialist in this field.

Solid or liquid compositions for application to animals, timber, stored products or household goods usually contain from about 0,00005 to about 90 wt.%, more preferably from about 0.001 to about 10 wt.% odgovori several compounds according to the invention. For administration to animals orally or parenterally, including percutaneous introduction of solid or liquid compositions they usually contain from about 0.1 to about 90 wt.% one or more compounds according to the invention. Feed containing the medicinal substance, usually contain from about 0.001 to about 3 wt.% one or more compounds according to the invention. Concentrates or additives for mixing with feeds usually contain from about 5 to about 90 wt.%, preferably from about 5 to about 50 wt.%, one or more compounds according to the invention. Mineral salt licking typically contain from about 0.1 to about 10 wt.% one or more compounds of the formula (I) or its pesticide acceptable salts.

Dusty or liquid compositions for application to livestock, goods, premises or outdoor areas may contain from about 0.0001 to about 15 wt.%, more preferably approximately from 0.005 to about 2.0 wt.%, one or more compounds according to the invention. Suitable concentrations during processing water is between about 0.0001 of the ppm and about 20 ppm, more preferably from about 0,001 ppm to about 5,0 ppm, of one or more compounds according to the invention and can be used therapeutically for farmed fish during the relevant periods of exposure. Edible prima the key can contain from about 0.01 to about 5 wt.%, preferably from about 0.01 to about 1.0 wt.%, one or more compounds according to the invention.

With the introduction of vertebrate animals parenteral, oral or percutaneous or by other means, the dosage of the compounds according to the invention will depend on the age or health of vertebrate animal and the nature and extent of actual or potential contamination of arthropods or helminths. For maintenance treatment is usually suitable for oral or parenteral administration of a single dose of from about 0.1 to about 100 mg, preferably from about 2.0 to about 20.0 mg, per kg of animal body weight or dose from about 0.01 to about 20.0 mg, preferably from about 0.1 to about 5.0 mg, per kg weight of the animal per day. When using the compositions or devices with slow release daily dose needed for months, can be combined and fed to the animals periodically.

The following compositions of EXAMPLES 2A-2M illustrate compositions for use against arthropods, especially mites or insects, or plant nematodes, which contain as the active ingredient compounds according to the invention, such as described in the preparative examples. The compositions described in EXAMPLES 2A-2M, can be diluted to obtain raspy aamoi compositions in concentrations suitable for use in the field. General chemical description ingredients (for which all subsequent interest are mass percent)used in the compositions of EXAMPLES 2A-2M below, are the following:

BrandChemical description
Atilan HRVCondensate of Nonylphenol and ethylene oxide
Suprior BSUCondensate of christianfree and ethylene oxide
Aralan SA70% (weight/volume) solution of dodecylbenzenesulfonate calcium
Solvesso 150Light10aromatic solvent
Arylan SDodecylbenzenesulfonate sodium
Darvan NO2Sodium lignosulphonate
Celite PFSynthetic magicality media
Apropos T36Sodium salts of polycarboxylic acids
Redigel 23The polysaccharide xanthan gum
Benton 38Organic derived montmorillonite magnesium
AerosilFine silicon dioxide

EXAMPLE 2A

Water-soluble concentrate is prepared SL is blowing composition:

The active ingredient7%
Atilan HRV10%
N-organic83%

To a solution of Atilano HRV dissolved in part of the N-methylpyrrolidone, add the active ingredient by heating and stirring until complete dissolution. The resulting solution is brought to volume with the remainder of the solvent.

EXAMPLE 2B

Emulsifiable concentrate (EC) is prepared of the following composition:

The active ingredient25% (maximum)
Suprior BSU10%
Aralan SA5%
N-organic50%
Solvesso 15010%

The first three component dissolved in N-organic and then add Solvesso 150 to obtain the final volume.

EXAMPLE 2C

Wettable powder (WP) is prepared of the following composition:

The active ingredient40%
Arylan S2%
Darvan NO25%
Celite PF53%

The ingredients are mixed and milled in a hammer mill into powder with size of the astitsy less than 50 microns.

EXAMPLE 2D

Water-flowing composition is prepared of the following composition:

The active ingredient40,00%
Atilan HRV1,00%
Apropos T0,20%
Ethylene glycolto 5.00%
Redigel 2300,15%
Water53,65%

The ingredients are thoroughly mixed and milled in a bead mill to obtain average particle size less than 3 microns.

EXAMPLE 2E

Concentrate emulsifiable suspension is prepared of the following composition:

The active ingredient30,0%
Atilan HRV10,0%
Benton 380,5%
Solvesso 15059,5%

The ingredients are thoroughly mixed and milled in a bead mill to obtain average particle size less than 3 microns.

EXAMPLE 2F

Dispersible in water, the granules are prepared of the following composition:

The ingredients are mixed, micronizer in the jet mill and then granularit in a rotating granulator with irrigation water (up to 10%). The obtained granules are dried in the dryer fluidized bed to remove excess water.

EXAMPLE 2G

Optimouse powder is prepared of the following composition:

The active ingredient30%
Darvan NO215%
Arylan S8%
Celite PF47%
The active ingredient1-10%
Powder talc superfine99-90%

The components are thoroughly mixed and then optionally milled to obtain a fine powder. Powder can be applied to the locus of infection arthropods, such as landfills, stored products or household items or animals that are infected or at risk of Contracting arthropods, for the destruction of arthropods oral intake of food. Appropriate means of distribution outrivaled powder on the locus of infection arthropods are mechanical ventilators, hand shaking machines or devices for Samoobrona cattle.

EXAMPLE 2N

Edible bait is prepared of the following composition:

The active ingredient0,1-1,0%
Wheat flour80%
Molasses19,9-19%

The ingredients are thoroughly mixed and formed into the desired shape of the lure. Specified edible bait can be distributed in the locus, such as a home or business premises, for example in kitchens, hospitals or stores, or outdoor areas, infected arthropods, such as ants, grasshoppers, cockroaches or flies, for the destruction of arthropods by oral ingestion.

EXAMPLE 2I

The solution composition is prepared of the following composition:

The active ingredient15%
The sulfoxide85%

The active ingredient is dissolved in dimethyl sulfoxide with stirring and heating on demand. The solution can be applied percutaneous, as cast on a pet that is infected arthropods, or after sterilization by filtration through a PTFE membrane (pore size 0.22 micrometer) parenteral injection in a dose of from 1.2 to 12 ml per 100 kg of animal body weight.

EXAMPLE 2J

Wettable powder is prepared of the following composition:

The active ingredient50%
Atilan HRV5%
Aerosil5%
the elite PF 40%

Atilan HRV absorb the Data and then mixed with other ingredients and crushed in a hammer mill, receiving a wettable powder, which may be diluted with water to a concentration of from 0.001 to 2 wt.% active compounds and applied to the locus of infection arthropods, such as Diptera larvae or plant nematodes, by spraying or animals that are infected or at risk of acquiring arthropods, by spraying or immersion or ingestion of drinking water for the destruction of arthropods.

EXAMPLE 2K

The composition in the form of slowly releasing balls produced from granules containing the following components in varying percentages (similar to that described for the previous songs), depending on the needs:

The active ingredient

Agent density

Agent slow release

Binder

The thoroughly mixed ingredients formed into pellets, which are pressed into balls with a specific gravity of 2 or more. They can be administered orally ruminants pet to hold while chewing gum, providing a continuous slow release of the active compound over a prolonged period of time for elimination of infected ruminants arthropods is.

EXAMPLE 2L

Slowly releasing a composition in the form of granules, pills, pellets or the like can be obtained of the following composition:

The active ingredient0,5-25%
Polyvinyl chloride75-99,5%
The dioctylphthalate (plasticizer)

The components are mixed and then formed into a suitable shape by melt extrusion or pressing. This composition is applicable, for example, to add to standing water or for the manufacture of collars or tags to attach to the pet to kill pests slow release.

EXAMPLE 2M

Granules, dispersible in water, receive the following composition:

The active ingredient85% (maximum)
Polyvinylpyrrolidone5%
Attapulgite clay6%
Sodium lauryl sulfate2%
Glycerin2%

The ingredients were mixed in the form of a 45%slurry with water, wet grinded to a particle size of 4 microns and then spray dried to remove the water.

METHODS of APPLICATION of PESTICIDES

To determine parasiticide and pesticidal activity of the compounds according to the invention conducted the following representative test trials with the use of the compounds according to the invention.

Method a: Method of screening for test consistency of compounds against Ctenocephalides felis (cat flea)

The test container was filled with 10 adult Ctenocephalides felis. Glass cylinder closed at one end by parafilm and was placed on the top of the test container. Then the solution of the test compounds measured by the pipette in bovine blood and was added to the glass cylinder. Processed Ctenocephalides felis were subjected to artificial sample on the dog (blood 37°C, relative humidity of 40-60%; Ctenocephalides felis, 20-22°C, relative humidity 40-60%) and assessed after 24 and 48 hours after application. Typical compounds according to the invention gave a good level of destruction Ctenocephalides felis at a test concentration of 5 ppm or less.

METHOD: Screening Diabrotica undecimpunctata (South blascoe dinosau)

Two days before applying corn seeds were soaked with warm water to ensure rapid germination. One day before use eggs Diabrotica undecimpunctata was placed on half Japanese filter paper, placed in a plastic Petri dish. After that sprouted seed corn was placed on the wetted gasket around the filter paper. Three drops 200 microlitres solution of the test compounds was carefully dropping pipette on the egg. The remainder of the solution was placed on the corn and then the Petri dish was closed. Processed the s eggs in Petri dishes were kept in a climatic chamber 6 days. The transfer efficiency (the percentage of dead eggs and/or larvae compared to the untreated control sample) was evaluated at 6 days after application using a binocular microscope.

Typical compounds according to the invention gave a good level of destruction Diabrotica undecimpunctata at a test concentration of 10 ppm

METHOD: Screening Nephotettix Cinciceps (rice leafhopper)

The sheets 12 in rice plants with a stem length of 8 cm was immersed for 5 seconds in an aqueous solution composition of the tested compounds. After the solution was drained away, the rice plants treated in this way were placed in a Petri dish and was inhabited by about 20 larvae (L3 stage) Nephotettix cinciceps. The Petri dish was closed and then kept in a climate chamber (16 hours in the daylight, 25°C, relative humidity 40-60%). After incubation for 6 days determined the mortality of the larvae.

Typical compounds according to the invention gave a good level of larvae Nephotettix cinciceps at a test concentration of 100 ppm

METHOD D: a Method of screening for test contact activity against Ctenocephalides felis (cat flea)

The solutions of the tested compounds was collected on filter paper, dried and filter paper were placed in a test tube and 10 infected individuals Ctenocephalides felis. Processed Ctenocephalides felis was kept in climate Kama is e (26° C, relative humidity 80%) and efficiency in percent was determined after 24 hours and 48 hours after application compared to untreated control sample.

Typical compounds according to the invention gave a good level of contact destruction Ctenocephalides felis at a test concentration of 1000 ppm

METHOD E: Method of screening for test contact activity against Rhipicephalus sanguineus (brown dog tick)

The solutions of the tested compounds was collected on filter paper, dried and put filter paper into a test tube and infected 20-30 larvae (L1) Rhipicephalus sanguineus and the tube was closed with clips. Processed Rhipicephalus sanguineus was kept in a climatic chamber (25°C, relative humidity 90%) and efficiency in percent was determined 24 hours after application compared to untreated control sample.

Typical compounds according to the invention gave a good level of contact destruction Rhipicephalus sanguineus at a test concentration of 100 ppm

1. Derivatives of 5-substituted alkalinisation formula (I)

where R1denotes CN;

W represents C-halogen;

R2denotes halogen;

R3means (C1-C3-halogenoalkane;

R4means (C1-C6)-alkyl;

And means (C1-C12-alkylen;

R5means (C1-C6)-alkyl;

R6means (C1-C6-halogenoalkane;

n is equal to 2;

or pesticide acceptable salt.

2. Derivatives of 5-substituted alkalinisation formula (I) according to claim 1, where

R1denotes CN; R2denotes chlorine; R3means CF3; W denotes C-Cl; R4means (C1-C6)-alkyl; R5means (C1-C6)-alkyl; R6means CF3; And means (C2-C3-alkylene and n is 2 or pesticide acceptable salt.

3. The method of obtaining the compounds of formula (I) or its salt as defined in any one of claims 1 to 2, including:

a) when R1, R2, R3, R4, R5, R6, W, a and n denote, as defined in claim 1,

the interaction of the compounds of formula (II):

where R1, R2, R3, R4, R5, R6, W and n denote, as defined in claim 1, and L denotes the deleted group is halogen with a compound of formula (III):

where And denotes, as defined in claim 1 and R5means as defined in claim 1, with the exception of hydrogen; and

b) interaction of the compounds of formula (IV):

where R1, R2, R3, R4, R5, R6, W, a and n denote, as defined in claim 1, with a compound of formula (V):

where R4means as defined in claim 1, and L1denotes a group to delete a halogen; and

g) if desired, converting the compounds of formula (I) in its pesticide acceptable salt.



 

Same patents:

FIELD: organic chemistry.

SUBSTANCE: invention describes insecticide-acaricide substance used against extoparasites in dogs and cats. Substance represents derivative of phenylpyrazole of the formula (I) wherein in pyrazole structure cyano-group, trifluoromethylsulfenyl group and amino-group are bound at 3, 4 and 5 positions, respectively, and chlorine atoms are bound to phenyl cycle at 2 and 6 positions, and trichlorosilyl group is bound at 4 position. Substance protects dogs and cats against infection with fleas for 65 days after treatment and for 45 days after treatment of cats, and against infection with mites for 35 days, not less. In acute experiment toxicity of substance is characterized by value LD50 above 1300 mg/kg after its administration in stomach to dogs.

EFFECT: valuable properties of substance.

2 ex

FIELD: organic chemistry, agriculture.

SUBSTANCE: invention relates to 5-substituted alkylaminopyrazole derivatives of formula I , wherein R1 is CN; W is C-halogen; R1 is halogen; R3 is C1-C3-haloalkyl, C1-C3-haloalkoxy; R4 is hydrogen, C1-C6-alkenyl, C2-C6-alkynyl, C3-C7-cycloalkyl, COR8; A is C1-C12-alkylene; R5 is hydrogen, C3-C6-alkenyl, -(CH )qR7 or NR10R11; R5 is C1-C6-haloalkyl; as well as method for animal exogenous and endogenous pest controlling; pesticide composition and application of said compounds for production of veterinary drug. 5-Substituted alkylaminopyrazole derivatives are useful in pest controlling, including insects, arachnids and helminthes, such as nematodes.

EFFECT: new pesticide derivatives.

9 cl, 12 tbl, 20 ex

FIELD: organic chemistry, pesticides.

SUBSTANCE: invention relates to production of compounds of formula I

, wherein R1 represents CN or CSNH2; X represents N or CR4; R2 and R4 represent hydrogen or chlorine; and R3 represents halogen, haloalkyl, halooxy or SF5. Claimed method includes reaction of compound of formula II

with aqueous acid solution. Also disclosed are method for production of intermediate of formula II, method for production of compound of formula I including step of production of formula II followed by conversion thereof to target compound. Moreover disclosed are two intermediates for production of target products.

EFFECT: new pesticide compounds and method for production thereof.

13 cl, 2 ex

FIELD: organic chemistry, agriculture.

SUBSTANCE: invention relates to method for production of compounds of general formula I wherein R1 represents CN or CSNH2; X represents N or C each R2 and R4 are independently hydrogen or chlorine; R3 represents halogen, haloalkyl, haloalkoxy or SF3; R5 and R6 are independently alkyl; n = 0, 1 or 2. Claimed method includes reaction of compound of formula II , wherein substituents are as defined above; W represent hydrogen, with metal inorganic salt or organic amine to form salt of compound II as intermediate and further reaction of said salt with alkylating agent of formula III wherein R6 is as defined above; Y represents leaving group. In another embodiment compounds of formula I are obtained by reaction of metal inorganic salt or organic base of formula II with abovementioned alkylating agent of formula III.

EFFECT: essentially decreased formation of side products; target products of high purity.

37 cl, 4 ex

FIELD: organic chemistry, herbicides, agriculture.

SUBSTANCE: invention elates to novel derivatives of uracil of the formula [I] possessing herbicide activity, a herbicide composition based on thereof and to a method for control of weeds. In derivatives of uracil of the formula [I] the group Q-R3 represents a substituted group taken among:

wherein a heterocyclic ring can be substituted with at least a substitute of a single species taken among the group involving halogen atom, (C1-C6)-alkyl-(C1-C6)-alkoxy; Y represents oxygen, sulfur atom, imino-group or (C1-C3)-alkylimino-group; R1 represents (C1-C3)-halogenalkyl; R2 represents (C1-C3)-alkyl; R3 represents OR7, SR8 or N(R9)R10; X1 represents halogen atom, cyano-group, thiocarbamoyl or nitro-group; X2 represents hydrogen or halogen atom wherein each among R7, R8 and R10 represents independently carboxy-(C1-C6)-alkyl and other substitutes given in the invention claim; R9 represents hydrogen atom or (C1-C6)-alkyl. Also, invention relates to intermediate compounds used in preparing uracil derivatives.

EFFECT: improved preparing method, valuable properties of compounds.

40 cl, 16 sch, 12 tbl, 65 ex

The invention relates to 1-methyl-5-alkylsulfonyl-, 1-methyl-5-alkylsulfonyl - 1-methyl-5-alkylthiomethyl pyrazolylborate and herbicide tool based on them

FIELD: organic chemistry, herbicides, agriculture.

SUBSTANCE: invention elates to novel derivatives of uracil of the formula [I] possessing herbicide activity, a herbicide composition based on thereof and to a method for control of weeds. In derivatives of uracil of the formula [I] the group Q-R3 represents a substituted group taken among:

wherein a heterocyclic ring can be substituted with at least a substitute of a single species taken among the group involving halogen atom, (C1-C6)-alkyl-(C1-C6)-alkoxy; Y represents oxygen, sulfur atom, imino-group or (C1-C3)-alkylimino-group; R1 represents (C1-C3)-halogenalkyl; R2 represents (C1-C3)-alkyl; R3 represents OR7, SR8 or N(R9)R10; X1 represents halogen atom, cyano-group, thiocarbamoyl or nitro-group; X2 represents hydrogen or halogen atom wherein each among R7, R8 and R10 represents independently carboxy-(C1-C6)-alkyl and other substitutes given in the invention claim; R9 represents hydrogen atom or (C1-C6)-alkyl. Also, invention relates to intermediate compounds used in preparing uracil derivatives.

EFFECT: improved preparing method, valuable properties of compounds.

40 cl, 16 sch, 12 tbl, 65 ex

FIELD: organic chemistry, agriculture.

SUBSTANCE: invention relates to method for production of compounds of general formula I wherein R1 represents CN or CSNH2; X represents N or C each R2 and R4 are independently hydrogen or chlorine; R3 represents halogen, haloalkyl, haloalkoxy or SF3; R5 and R6 are independently alkyl; n = 0, 1 or 2. Claimed method includes reaction of compound of formula II , wherein substituents are as defined above; W represent hydrogen, with metal inorganic salt or organic amine to form salt of compound II as intermediate and further reaction of said salt with alkylating agent of formula III wherein R6 is as defined above; Y represents leaving group. In another embodiment compounds of formula I are obtained by reaction of metal inorganic salt or organic base of formula II with abovementioned alkylating agent of formula III.

EFFECT: essentially decreased formation of side products; target products of high purity.

37 cl, 4 ex

FIELD: organic chemistry, pesticides.

SUBSTANCE: invention relates to production of compounds of formula I

, wherein R1 represents CN or CSNH2; X represents N or CR4; R2 and R4 represent hydrogen or chlorine; and R3 represents halogen, haloalkyl, halooxy or SF5. Claimed method includes reaction of compound of formula II

with aqueous acid solution. Also disclosed are method for production of intermediate of formula II, method for production of compound of formula I including step of production of formula II followed by conversion thereof to target compound. Moreover disclosed are two intermediates for production of target products.

EFFECT: new pesticide compounds and method for production thereof.

13 cl, 2 ex

FIELD: organic chemistry, agriculture.

SUBSTANCE: invention relates to 5-substituted alkylaminopyrazole derivatives of formula I , wherein R1 is CN; W is C-halogen; R1 is halogen; R3 is C1-C3-haloalkyl, C1-C3-haloalkoxy; R4 is hydrogen, C1-C6-alkenyl, C2-C6-alkynyl, C3-C7-cycloalkyl, COR8; A is C1-C12-alkylene; R5 is hydrogen, C3-C6-alkenyl, -(CH )qR7 or NR10R11; R5 is C1-C6-haloalkyl; as well as method for animal exogenous and endogenous pest controlling; pesticide composition and application of said compounds for production of veterinary drug. 5-Substituted alkylaminopyrazole derivatives are useful in pest controlling, including insects, arachnids and helminthes, such as nematodes.

EFFECT: new pesticide derivatives.

9 cl, 12 tbl, 20 ex

FIELD: organic chemistry.

SUBSTANCE: invention describes insecticide-acaricide substance used against extoparasites in dogs and cats. Substance represents derivative of phenylpyrazole of the formula (I) wherein in pyrazole structure cyano-group, trifluoromethylsulfenyl group and amino-group are bound at 3, 4 and 5 positions, respectively, and chlorine atoms are bound to phenyl cycle at 2 and 6 positions, and trichlorosilyl group is bound at 4 position. Substance protects dogs and cats against infection with fleas for 65 days after treatment and for 45 days after treatment of cats, and against infection with mites for 35 days, not less. In acute experiment toxicity of substance is characterized by value LD50 above 1300 mg/kg after its administration in stomach to dogs.

EFFECT: valuable properties of substance.

2 ex

FIELD: chemistry.

SUBSTANCE: described are derivatives of 5-substituted alkylaminopyrazoles of formula (I) , where R1 stands for CN, W stands for C-halogen; R2 stands for halogen, R3 stands for (C1-C3)-halogenoalkyl, R4 stands for (C1-C6)-alkyl, A stands for (C1-C12)-alkylene, R5 stands for (C1-C6)-alkyl, R6 stands for (C1-C6)-halogenoalkyl, n equals 2, or their pesticidely acceptable salts. Compounds demonstrate insecticidal activity and parasiticidal activity. The method of obtaining formula (I) is described, including interaction of compound of formula (II) with compound of formula (III) R5-O-A-NH2 and interaction on compound obtained with compound of formula (V) R4-L1.

EFFECT: obtaining derivatives which can be applied as pesticides.

3 cl, 6 tbl, 18 ex

FIELD: medicine.

SUBSTANCE: invention is related to antagonists of serotonin 5-HT6 receptors of common formula 1 and their pharmaceutically acceptable salts and/or hydrates, pharmaceutical compositions, dosage forms and methods of production. Invention also includes new compounds of formula 1.1. In formulae 1 and 1.1 , Ar represents aryl, selected from unnecessarily substituted phenyl or unnecessarily substituted 5-6-member heteroaryl, which contains atom of nitrogen or atom of sulfur and heteroatom; R1 represents atom of hydrogen, unnecessarily substituted C1-C5 alkyl; Ar represents aryl, selected from unnecessarily substituted phenyl or unnecessarily substituted 5-6-member heteroaryl, which contains atom of nitrogen or atom of sulfur as heteroatom; R1 represents atom of hydrogen, which is unnecessarily substituted C1-C5 alkyl; R21,R22, R31, R32 independently from each other represent atom of hydrogen or substituent of aminogroup, selected from unnecessarily substituted C1-C4 alkyl, unnecessarily substituted phenyl, or R31 and R32 together with atom of nitrogen, to which they are bound, create unnecessarily substituted saturated 6-member heterocycle, possibly containing atom of nitrogen in cycle; or R1 together with atom of nitrogen, to which it is bound, and R21 and R22 together with atom of nitrogen, to which they are bound, create substituted pyrimidine cycle. In formula 1.1 R4, R5 and R6 independently from each other represent atom of hydrogen, unnecessarily substituted C1-C3 alkyl or phenyl.

EFFECT: compounds of invention may find application for treatment and prevention of development of conditions and disorders of central nervous system.

13 cl, 11 dwg, 4 tbl, 11 ex

FIELD: chemistry.

SUBSTANCE: invention proposes 5-member heterocyclic inhibitors of kinase p38, including kinase p38α and kinase p38β, based on pyrazoles and imidazoles, with the general formula given below , in which ring B is phenyl, and C is a pyrazole or imidazole ring, and the rest of the symbols assume values given in paragraph 1 of the formula of invention.

EFFECT: there are described pharmaceutical compositions containing said compounds, as well as methods of using the compounds and compositions, including a method of treating, preventing or suppressing one or more symptoms of diseases and conditions mediated by kinase p38 which include, but not limited to, inflammatory diseases and conditions.

31 cl, 6 tbl, 175 ex

FIELD: chemistry.

SUBSTANCE: present invention relates to a method of producing a compound (I), where X is N or CR4; R1 is CN or CSNH2; R2 and R4 are independently hydrogen or chlorine; and R3 is halogen, haloalkyl, haloalkoxy or SF5, n equals 0, 1 or 2. The method involves, at the first step, reaction of a compound of formula (IV), where X, R1, R2, R3, R4 and n assume values given above, with formaldehyde or a formaldehyde trimer or chemical equivalent thereof, to obtain an intermediate compound (V), where X, R1, R2, R3, R4 and n assume values given above; and at the second step, reaction of the compound of formula (V) with a reducing agent, preferably sodium borohydride. The invention also relates to an intermediate compound 3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-5-hydroxymethylamino-4-trifluoromethyl thionyl pyrazole.

EFFECT: efficient method of obtaining the compounds.

3 cl, 1 ex

Up!