5-substituted alkylaminopyrazole derivatives as pesticides

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

 

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

The destruction of insects, spiders and worms using 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 by using derivatives of 1-arylpyrazole described, for example, in patent publications WO 00/35884, EP 0846686, WO 98/24769 and WO 97/28126.

In addition, in 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 some organisms or by using low concentrations.

Since modern pesticides must meet a large 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 or synthesis, and, because of the emergence of resistance, the development of t is such 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, particularly in relation to the destruction of parasites in animals.

This invention relates to a method for the destruction of parasites in the animal body or on the body of the animal, providing for the introduction of animal amount, effective for the destruction of parasites derived 5-substituted acylaminopyrazoles formula (I):

where:

R1denotes CN;

W represents C-halogen,-CH3or N;

R2denotes hydrogen, halogen or CH3;

R3means (C1-C3-halogenated, (C1-C3)-halogenoalkane or S(O)p-(C1-C3-halogenated;

R4denotes hydrogen, (C2-C6)-alkenyl,

(C2-C6)-halogenoalkanes, (C2-C6)-quinil, (C2-C6-halogenoalkanes, (C3-C7-cycloalkyl, CO-(CH2)q-R7, COR8WITH-(CH2)q-R9,

-CO-(C1-C4)-alkyl-(C1-C6)-alkoxy, -CO2-(CH2)q-R7, -CO2R8,

-CO2-(CH2)q-R9, -What about the 2-(C3-C7-cycloalkyl, -CO2-(C1-C4)-alkyl-(C3-C7-cycloalkyl, -CO2-(C3-C6)-alkenyl, -CO2-(C3-C6)-quinil, CO-NR10R11, -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)-alkoxy,

(C1-C6)-halogenoalkane, (C3-C7)-cycloalkyl,

S(O)pR8, CO2-(C1-C6)-alkyl, -O(C=O)-(C1-C6)-alkyl, NR10COR12, NR10R11, CONR10R11, SO2NR10R11HE, CN, NO2, OR7, NR10SO2R8, COR8and OR9;

And means (C1-C12-alkylen [preferably

(C1-C6-alkylen] or (C1-C12-halogenation [preferably

(C1-C6-halogenation], in which 2, 3 or 4 adjacent carbon atoms optionally 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)-halogenation, in the last two mentioned groups are methylene part 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 group S(O)mor N atom; 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 NR10R11provided that the last-mentioned radical m is 2; or denotes (C1-C6)-alkyl, unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C6)-alkoxy, (C1-C6)-halogenoalkane, (C3-C6)-alkenylamine,

(C3-C6)-halogenations, (C3-C6)-alkyloxy,

(C3-C6)-halogenaryloxy, (C3-C7)-cycloalkyl, S(O)pR8, CN, NO2HE, COR10, NR10COR12, NR10SO2R8, CONR10R11, NR10R11, S(O)pR7, S(O)pR9, OR7, OR9and CO2R10; or, when a represents (C1-C12-alkylene or (the 1-C12-halogenation and R5means (C1-C6)-alkyl, unsubstituted or substituted by one or more radicals halogen, one or more of the carbon atoms of R5may, together with S(O)mand one or more carbon atoms, form a 5 - or 6-membered ring;

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

(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)-alkoxy, (C1-C6)-halogenoalkane, CN, NO2, S(O)pR8, COR11, COR13, CONR10R11, SO2NR10R11, NR10R11HE SO3N and (C1-C6)-alkylidene;

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

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, (C1- 4)-halogenoalkane, NO2CN, CO2-(C1-C6)-alkyl, S(O)pR8HE and oxo;

R10and R12each, independently, represent H, (C1-C6)-alkyl, (C1-C6-halogenated, (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

R10and R11and/or R10and R12in each case, independently, together with the corresponding attached N atom form a five - or six-membered saturated ring which optionally contains 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 R14each, independently, represent H, (C1-C6)-alkyl, (C1-C6-halogenated, (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 the th of halogen, (C1-C6)-alkyl, (C1-C6)-halogenoalkane, (C1-C6)-alkoxy, (C1-C6)-halogenoalkane, CN, NO2, S(O)pR8and NR11R14;

R15means R11or -(CH2)qR13;

m, n and p each independently 0, 1 or 2;

q is 0 or 1; and

each heterocyclyl in the abovementioned radicals independently denotes 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 this invention relates to the use of compounds of formula (I) and their pesticide-acceptable salts for the destruction of parasites in animals and animal body.

In another aspect this invention relates to the use of compounds of formula (I) and their pesticide-acceptable salts for the preparation of veterinary medicines, preferably for the treatment of parasites, in particular, ecto - and endoparasites in animals and animal body.

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

The term "pesticide-acceptable salts" means salts, anions or cations which are known and permitted in this area DL the formation of salts for use as pesticides. Suitable salts with bases, e.g. formed by compounds of formula (I)containing a carboxyl group include 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 acid additive salts, e.g. formed by compounds of formula (I)containing an amino group, include salts with inorganic acids, for example, hydrochloride, sulphates, phosphates and nitrates and salts with organic acids, e.g. acetic acid. When in formula (I) m is 0, the term "salt" includes salts of sulfone, for example, halide salts of alkyl - or benzylmorphine, such as chloride salts methylsulfone.

Note that the above conditions are included only for reasons of chemical instability for specifically excluded parts of the molecules, and not because of their use in previous state of the art.

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 this moiety is partially or fully galogenidov the YM, that is substituted by F, Cl, Br or I, in any combination, preferably F or Cl.

Alkyl groups and parts thereof (unless otherwise noted) can be linear or branched.

The expression "(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 radical, ethyl, propyl, isopropyl, 1-butyl, 2-butyl, 2-methylpropyl or tert-butyl.

Alkyl radicals, also in the composite, the composite groups, unless otherwise indicated, preferably have 1-4 carbon atoms.

"(C1-C6-halogenated" denotes an alkyl group, referred to in 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-alkylene" denotes unbranched or branched saturated carbon chain having 1-12 carbon atoms.

The expression "(1-C12-halogenation" denotes unbranched or branched saturated operon the second circuit, having 1-12 carbon atoms in which one or more hydrogen atoms replaced by the same number of identical or different halogen atoms.

The expression "(2-C12-albaniles" denotes unbranched or branched saturated carbon chain having 2-12 carbon atoms, 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 the meaning given in the expression(C1-C6)-alkyl". "Halogenoalkane" denotes, for example, OCF3, OCHF2, OCH2F, CF3CF2O, OCH2CF3or OCH2CH2Cl.

The expression "(2-C6)-alkenyl" denotes unbranched or branched acyclic carbon chain having the number of carbon atoms, which corresponds to this specified range, which contains at least one double bond, which may be located in any position of the corresponding unsaturated radical. Thus, "(2-C6)-alkenyl" denotes, for example, vinyl group, allyl, 2-methyl-2-propenyl, 2-butenyl, pentenyl, 2-methylpentanol or hexenyl.

The expression "(2-C6)-quinil" denoted by the AET unbranched or branched acyclic carbon chain, having the number of carbon atoms, which corresponds to this specified range, which contains at least one triple bond, which may be located in any position of the corresponding unsaturated radical. Thus, "(2-C6)-quinil" denotes, for example, a group of propargyl, 1-methyl-2-PROPYNYL, 2-butynyl or 3-butynyl.

Cycloalkyl groups preferably have three to seven carbon atoms in the ring and optionally 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; examples of alkyl, substituted alkoxy, is methoxymethyl (CH3Och2-); and an example of alkyl, substituted alkylthio is methylthiomethyl (CH3SCH2-).

Group "heterocyclyl" may be saturated, unsaturated or heteroaromatic; preferably, it contains one or more, in particular 1, 2 or 3, heteroatoms in the heterocyclic ring, preferably selected from the group consisting of N, O and S; it is preferably an aliphatic heterocyclic radical having 3-7 ring atoms or a heteroaromatic radical having 5-7 carbon atoms in the ring. The heterocyclic radical can be, for example, heteroaromatic for the crimson or ring (heteroaryl), such as, for example, mono-, bi - or polycyclic 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 it may be partially or fully gidrirovanny 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, alkoxy, halogenoalkane, alkylthio, hydroxyl, amino, nitro, carboxyl, cyano, alkoxycarbonyl, alkylsulphonyl, formyl, carbamoyl, mono - and dialkylaminoalkyl, substituted amino, such as acylamino, mono - and dialkylamino, and alkylsulfonyl, halogenatedsolvents, alkylsulfonyl, halogenallylacetic, alkyl and halogenoalkane and additionally also oxo. Oxoprop may also be present in those of the heteroatoms of the ring, where there are various oxidation States, for example, in the case of N and S.

The term "pests" means arthropods is rediteley (arthropod) (including insects and arachnids) and helminths (including nematodes). The term "parasites" includes all pests that live in the animal body and animal body.

A preferred class of compounds of formula (I) for use in this invention are compounds in which:

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

And means (C1-C6-alkylen or (C1-C6-halogenation, in which 2, 3 or 4 adjacent carbon atoms optionally 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;

R 5means (C3-C6-cycloalkyl, -(CH2)qR7or (C1-C6)-alkyl, unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C6)-alkoxy, (C1-C6)-halogenoalkane, (C3-C6)-cycloalkyl, S(O)pR8and

CO2-(C1-C6)-alkyl; or, when a represents (C1-C6)-alkyl or

(C1-C6-halogenated and R5means (C1-C6)-alkyl or

(C1-C6-halogenated, one or more of the carbon atoms of the group R5may, together with a group S(O)mand one or more carbon atoms, form a 5 - or 6-membered ring;

R6and R8each, independently, represent (C1-C6)-alkyl or

(C1-C6-halogenated;

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)-alkoxy, 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-sub> 4)-halogenoalkane and (C1-C4)-alkoxy;

R11and R12identical or different, represent each hydrogen, (C1-C6)-alkyl or (C1-C6-halogenated;

m, n and p each independently 0, 1 or 2; and

q is 0 or 1.

Another preferred class of compounds of formula (I) for use in this invention are compounds in which:

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)-alkoxy, (C1-C3)-halogenoalkane, (C3-C6)-cycloalkyl, S(O)pR8, CO2-(C1-C3)-alkyl, -O(C=O)-(C1-C3)-alkyl, NR10R11HE, CN, NO2, OR7or or9;

And means (C1-C9-alkylen or (C1-C9-the halogen is kilen, in which 2, 3 or 4 adjacent carbon atoms optionally 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, -(CH2)qR7; or denotes (C1-C6)-alkyl, unsubstituted or substituted by one or more radicals selected from the group consisting of halogen,

(C1-C3)-alkoxy, (C1-C4)-halogenoalkane, (C3-C7)-cycloalkyl, S(O)pR8, CN, NR10R11, S(O)pR7, S(O)pR9, OR7and OR9;

R6means (C1-C2-halogenated;

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)-alkoxy, (C1-C4)-halogenoalkane, CN, NO2, S(O)pR8, COR11, NR10R11and HE;

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

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

R10denotes H, (C1-C3)-alkyl, (C1-C3-halogenated, (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 optionally contains 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 R14each, independently, represent H, (C1-C3)-alkyl, (C1-C3-halogenated, (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)-alkoxy, (C1-C3)-halogenoalkane, CN, NO2, S(O)pR8and NR11R14;

m, n and p each independently 0, 1 or 2;

q is 0 or 1, and

each heterocyclyl in the abovementioned radicals independently denotes 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) for use in this invention are compounds in which:

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)-alkoxy;

And means (C1-C4-alkylen;

R5means (C3-C6-cycloalkyl, -(CH2)qR7, (C1-C6)-alkyl or (C1-C6-halogenated; or, when R5means (C1-C6)-alkyl, one or more of the carbon atoms of the group R5may, together with a group S(O)mand one or more carbon atoms, form a 5 - or 6-membered ring;

R6means CF3, CF2Cl, CFCl2, CBrF2or CHF2;

R7denotes phenyl;

m and n are each independently 0, 1 or 2; and

q is 0 or 1.

Next suppose the equipment class of compounds of formula (I) for use in this invention are compounds in which:

R1denotes CN;

W denotes C-Cl;

R2denotes Cl;

R3means CF3or OCF3;

R4denotes hydrogen, (C2-C6)-alkenyl, (C2-C6)-quinil, (C3-C7-cycloalkyl, COR9(where R9indicates tetrahydrofuryl), the PINES2-(C1-C6)-alkoxy, -CO2-(C1-C6)-alkyl, -CO2-(CH2)q-R7, OR7, OR8or or9(where R9denotes pyridyl); or (C1-C6)-alkyl, unsubstituted or substituted by one or more radicals selected from the group consisting of (C1-C6)-alkoxy, (C3-C7)-cycloalkyl or S(O)pR8;

And means (C1-C6-alkylene, in which 2, 3 or 4 adjacent carbon atoms optionally form part (C3-C6)-cycloalkyl ring;

R5means (C3-C6)-alkenyl, (C3-C7-cycloalkyl, -(CH2)qR7or NR10R11provided that the last-mentioned radical, X denotes SO2; or denotes (C1-C6)-alkyl or (C1-C6-halogenated;

R6means CF3, CF2Cl, CFCl2, CBrF2, CHF2or CH3;

R7denotes phenyl, unsubstituted or substituted by one who does multiple (C 1-C6-alkoxygroup;

R8means (C1-C6)-alkyl;

R10and R11identical or different, denote (C1-C6)-alkyl; or

R10and R11together with the attached N atom form a five - or six-membered saturated ring which optionally contains an additional heteroatom in the ring selected from O, S and N;

m and n are each independently 0, 1 or 2; and

q is 0 or 1.

Another preferred class of compounds of formula (I) for use in this invention are compounds in which:

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

And means (C1-C6)-Ala is flax or (C 1-C6-halogenation, in which 2, 3 or 4 adjacent carbon atoms optionally 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, (C1-C6)-alkoxy, (C1-C6)-halogenoalkane, (C3-C6)-cycloalkyl, S(O)pR8and CO2-(C1-C6)-alkyl; or, when a represents (C1-C6-alkylen or (C1-C6-halogenation and R5means (C1-C6)-alkyl, unsubstituted or substituted by one or more radicals halogen, one or more of the carbon atoms of the group R5may, together with S(O)mand one or more carbon atoms, form a 5 - or 6-membered ring;

R6and R8each, independently, represent (C1-C6)-alkyl or (C1-C6-halogenated;

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

R10and R11each, independently, represent H, (C1-C6)-alkyl or (C1-C6-halogenated;

m, n and p each independently 0, 1 or 2; and

q is 0 or 1.

As a preferred class of compounds of formula (I) for use in this invention are compounds in which:

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-halogenated;

And means (C1-C12-alkylene, which is 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

m and n are each independently 0, 1 or 2.

In addition, especially preferred CL is same compounds of formula (I) for use in this invention are compounds in which there are one or more of the following special cases:

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.

Another particularly preferred class of compounds for use in this invention are compounds in which:

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

m and n are each independently 0, 1 or 2.

A more preferred class of compounds of formula (I) for use in this invention are compounds in which:

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

Further, especially preferred classes of compounds of formula (I) for use in this invention are compounds which contain one or more of the following special cases:

W denotes C-Cl;

R2denotes chlorine;

R3means CF3or OCF3;

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

R5means (C1-C6)-alkyl;

R6means (C1-C3-halogenated (R6indicates more preferably CF3); and/or

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

Some of the compounds of formula (I) are new, and the following special case of the present invention relates, therefore, to new compounds of the formula (I).

One of the classes of new derivatives of 5-substituted alkalinisation formula (I) or their pesticide-acceptable salts are compounds in which:

R1denotes CN;

W represents C-halogen, or-CH3;

R2denotes hydrogen, halogen or CH3;

R3means (C1 3-halogenated, (C1-C3)-halogenoalkane or S(O)p-(C1-C3-halogenated;

R4means (C2-C6)-alkenyl, (C2-C6)-halogenoalkanes, (C2-C6)-quinil, (C2-C6-halogenoalkanes, (C3-C7-cycloalkyl, CO-(CH2)q-R7WITH-(CH2)q-R9- - (C1-C4)-alkyl-(C1-C6)-alkoxy, -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, which is substituted by one or more radicals selected from the group consisting of halogen, (C1-C6)-alkoxy, (C1-C6)-halogenoalkane, (C3-C7)-cycloalkyl, S(O)pR8, CO2-(C1-C6)-alkyl, -O(C=O)-(C1-C6)-alkyl, NR10COR12, NR10R11, CONR10R11, SO2NR10R11HE, CN, NO2, OR7, NR10SO2R8, COR8and OR9;

And means (C1-C12-alkylen [PR doctitle

(C1-C6-alkylen] or (C1-C12-halogenation [preferably

(C1-C6-halogenation], in which 2, 3 or 4 adjacent carbon atoms optionally 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-halogenation, in the last two mentioned groups are methylene part 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 group S(O)mor N atom; 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 NR10R11provided that the last-mentioned radical m is 2; or denotes (C1-C6)-alkyl, unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C6)-alkoxy, (C1-the 6)-halogenoalkane, (C3-C6)-alkenylamine,

(C3-C6)-halogenations, (C3-C6)-alkyloxy,

(C3-C6)-halogenaryloxy, (C3-C7)-cycloalkyl, S(O)pR8, CN, NO2HE, COR10, NR10COR12, NR10SO2R8, CONR10R11, NR10R11, S(O)pR7, S(O)pR9, OR7, OR9and CO2R10; or, when a represents (C1-C12-alkylen or

(C1-C12-halogenation and R5means (C1-C6)-alkyl, unsubstituted or substituted by one or more radicals halogen, one or more of the carbon atoms of R5may, together with S(O)mand one or more carbon atoms, form a 5 - or 6-membered ring;

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

(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)-alkoxy, (C1-C6)-halogenoalkane, CN, NO2, S(O)pR8 , COR11, COR13, CONR10R11, SO2NR10R11, NR10R11HE SO3N and (C1-C6)-alkylidene;

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

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, (C1-C4)-halogenoalkane, NO2CN, CO2-(C1-C6)-alkyl, S(O)pR8HE and oxo;

R10and R12each, independently, represent H, (C1-C6)-alkyl, (C1-C6-halogenated, (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

R10and R11and/or R10and R12in each case, independently, together with the corresponding attached N atom form a five - or six-membered saturated ring which optionally contains an additional heteroatom in the ring selected from O, S and N, and this ring is unsubstituted or samewe what about the one or more radicals, selected from the group consisting of halogen, (C1-C6)-alkyl and (C1-C6)-halogenoalkane;

R11and R14each, independently, represent H, (C1-C6)-alkyl, (C1-C6-halogenated, (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)-alkoxy, (C1-C6)-halogenoalkane, CN, NO2, S(O)pR8and NR11R14;

R15means R11or -(CH2)qR13;

m, n and p each independently 0, 1 or 2;

q is 0 or 1; and

each heterocyclyl in the abovementioned radicals independently denotes 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 compounds in which:

R1denotes CN;

W represents C-halogen;

R2denotes hydrogen or halogen;

R3means CF3or OCF3;

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

And means (C1-C6-alkylen or (C1-C6-halogenation, in which 2, 3 or 4 adjacent carbon atoms optionally 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)qR7or (C1-C6)-alkyl, unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C6)-alkoxy, (C1-C6)-halogenoalkane, (C3-C6)-cycloalkyl, S(O)pR8and

CO2-(C1-C6)-alkyl; or, when a represents (C1-C6)-Alki the or

(C1-C6-halogenated and R5means (C1-C6)-alkyl or

(C1-C6-halogenated, one or more of the carbon atoms of the group R5may, together with a group S(O)mand one or more carbon atoms, form a 5 - or 6-membered ring;

R6and R8each, independently, represent (C1-C6)-alkyl or (C1-C6-halogenated;

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)-alkoxy, 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)-alkoxy;

R11and R12identical or different, represent each hydrogen, (C1-C6)-alkyl or (C1-C6-halogenated;

m, n and p each independently 0, 1 or 2; and

q is 0 or 1.

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

R1denotes CN;

W represents C-halogen;

R2means in the location 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, which is substituted by one or more radicals selected from the group consisting of halogen, (C1-C6)-alkoxy, (C1-C6)-halogenoalkane, (C3-C6)-cycloalkyl, S(O)pR8and CO2-(C1-C6)-alkyl;

A stands for (C1-C6-alkylen or (C1-C6-halogenation, in which 2, 3 or 4 adjacent carbon atoms optionally 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 a (C1-C6)-alkyl, unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C6)-alkoxy, (C1-C6)-halogenoalkane, (C3-C6)-cycloalkyl, S(O)pR8and CO2-(C1-C6)-alkyl; a is Li, when And indicates (C1-C6-alkylen or (C1-C6-halogenation and R5means (C1-C6)-alkyl, unsubstituted or substituted by one or more radicals halogen, one or more of the carbon atoms of the group R5may, together with a group S(O)mand one or more carbon atoms, form a 5 - or 6-membered ring;

R6and R8each, independently, represent (C1-C6)-alkyl or (C1-C6-halogenated;

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)-alkoxy, CN, NO2, S(O)pR8and NR10R11;

R10and R11each, independently, represent H, (C1-C6)-alkyl or (C1-C6-halogenated;

m, n and p are each, independently, 0, 1, or 2; and

q is 0 or 1.

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

R1denotes CN;

W represents C-halogen;

R2denotes halogen;

R3means CF3or OCF3;

R4means (C2-C6)-alkenyl, (C2-C6)-quinil, (C3-C7-cycloalkyl, -CO2R8, -What about the 2-(C3-C6)-quinil, -CO2-(C3-C6-cycloalkyl, -CO2-(C1-C3)-alkyl-(C3-C6-cycloalkyl, -CH2R7or-CH2R9; or (C1-C4)-alkyl, which is substituted by one or more radicals selected from the group consisting of halogen, (C1-C3)-alkoxy, (C1-C3)-halogenoalkane, (C3-C6)-cycloalkyl, S(O)pR8, CO2-(C1-C3)-alkyl, -O(C=O)-(C1-C3)-alkyl, NR10R11HE, CN, NO2, OR7or or9;

And means (C1-C9-alkylen or (C1-C9-halogenation, in which 2, 3 or 4 adjacent carbon atoms optionally 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, -(CH2)qR7; or denotes (C1-C6)-alkyl, unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C3)-alkoxy, (C1-C4)-halogenoalkane, (C3-C7)-cycloalkyl, S(O)pR8, CN, NR10R11, S(O)pR7, S(O)pRsup> 9, OR7and OR9;

R6means (C1-C2-halogenated;

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)-alkoxy, (C1-C4)-halogenoalkane, CN, NO2, S(O)pR8, COR11, NR10R11and HE;

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

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)-alkoxy;

R10denotes H, (C1-C3)-alkyl, (C1-C3-halogenated, (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 optionally contains 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 and the group, consisting of halogen and (C1-C3)-alkyl;

R11and R14each, independently, represent H, (C1-C3)-alkyl, (C1-C3-halogenated, (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)-alkoxy, (C1-C3)-halogenoalkane, CN, NO2, S(O)pR8and NR11R14;

m, n and p each independently 0, 1 or 2;

q is 0 or 1; and

each heterocyclyl in the abovementioned radicals independently denotes 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) are compounds in which:

R1denotes CN;

W denotes C-Cl;

R2denotes chlorine;

R3means CF3or OCF3;

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

And means (C1 4-alkylen;

R5means (C3-C6-cycloalkyl, -(CH2)qR7, (C1-C6)-alkyl or (C1-C6-halogenated; or, when R5means (C1-C6)-alkyl, one or more of the carbon atoms of the group R5may, together with a group S(O)mand one or more carbon atoms, form a 5 - or 6-membered ring;

R6means CF3, CF2Cl, CFCl2, CBrF2or CHF2;

R7denotes phenyl;

m and n are each independently 0, 1 or 2; and

q is 0 or 1.

As a preferred class of compounds of formula (I) are compounds in which:

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-halogenated;

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

R5means (C1-C6)-alkyl;

R6putting the AET CF 3, CF2Cl, CFCl2, CBrF2or CHF2; and

m and n are each independently 0, 1 or 2.

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

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

m and n are each independently 0, 1 or 2.

Another class of new derivatives of 5-substituted alkalinisation formula (I) or their pesticide-acceptable salts are compounds in which:

R1denotes CN;

W represents C-halogen, or-CH3;

R2denotes hydrogen, halogen or CH3;

R3means (C1-C3-halogenated, (C1-C3)-halogenoalkane or S(O)p-(C1-C3-halogenated;

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

And means (C1-C12-alkylen [preferably

(C1-C 6-alkylen] or (C1-C12-halogenation [preferably

(C1-C6-halogenation], in which 2, 3 or 4 adjacent carbon atoms optionally 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-halogenation, in the last two mentioned groups are methylene part 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 group S(O)mor N atom; 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 NR10R11provided that the last-mentioned radical S(O)mmeans SO2; or denotes

(C1-C6)-alkyl, substituted by one or more radicals selected from the group consisting of halogen, (C1-C6)-alkoxy, (C1 -C6)-halogenoalkane, (C3-C6)-alkenylamine,

(C3-C6)-halogenations, (C3-C6)-alkyloxy,

(C3-C6)-halogenaryloxy, (C3-C7)-cycloalkyl, S(O)pR8, CN, NO2HE, COR10, NR10COR12, NR10SO2R8, CONR10R11, NR10R11, S(O)pR7, S(O)pR9, OR7, OR9and CO2R10; or, when a represents (C1-C12-alkylen or (C1-C12-halogenation and R5means (C1-C6)-alkyl, substituted by one or more radicals halogen, one or more of the carbon atoms of R5may, together with S(O)mand one or more carbon atoms, form a 5 - or 6-membered ring;

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

(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)-alkoxy, (C1-C6)-halogenoalkane, CN, NO2, S(O)pR8, COR11, COR 13, CONR10R11, SO2NR10R11, NR10R11HE SO3N and (C1-C6)-alkylidene;

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

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, (C1-C4)-halogenoalkane, NO2CN, CO2-(C1-C6)-alkyl, S(O)pR8HE and oxo;

R10and R12each, independently, represent H, (C1-C6)-alkyl, (C1-C6-halogenated, (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

R10and R11and/or R10and R12in each case, independently, together with the corresponding attached N atom form a five - or six-membered saturated ring which optionally contains an additional heteroatom in the ring selected from O, S and N, and this ring is unsubstituted or substituted by one or a number of the mi radicals, selected from the group consisting of halogen, (C1-C6)-alkyl and (C1-C6)-halogenoalkane;

R11and R14each, independently, represent H, (C1-C6)-alkyl, (C1-C6-halogenated, (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)-alkoxy, (C1-C6)-halogenoalkane, CN, NO2, S(O)pR8and NR11R14;

R15means R11or -(CH2)qR13;

m, n and p each independently 0, 1 or 2;

q is 0 or 1; and

each heterocyclyl in the abovementioned radicals independently denotes 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 compounds in which:

R1denotes CN;

W represents C-halogen;

R2denotes hydrogen or halogen;

R3means CF3or OCF3;

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

And means (C1-C6)-and the kilen or (C 1-C6-halogenation, in which 2, 3 or 4 adjacent carbon atoms optionally 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 denotes (C1-C6)-alkyl, substituted by one or more radicals selected from the group consisting of halogen, (C1-C6)-alkoxy, (C1-C6)-halogenoalkane, (C3-C6)-cycloalkyl, S(O)pR8and CO2-(C1-C6)-alkyl; or, when a represents (C1-C6)-alkyl or (C1-C6-halogenated and R5means (C1-C6-halogenated, one or more of the carbon atoms of the group R5may, together with a group S(O)mand one or more carbon atoms, form a 5 - or 6-membered ring;

R6and R8each, independently, represent (C1-C6)-alkyl or (C1-C6-halogenated;

R7denotes phenyl, unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C6)-alkyl, (C1-C6)-halogenoalkane, (C1-sub> 6)-alkoxy, 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)-alkoxy;

R11and R12identical or different, represent each hydrogen, (C1-C6)-alkyl or (C1-C6-halogenated;

m, n and p each independently 0, 1 or 2; and

q is 0 or 1.

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

R1denotes CN;

W represents C-halogen;

R2denotes hydrogen or halogen;

R3means CF3or OCF3;

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

And means (C1-C6-alkylen or (C1-C6-halogenation, in which 2, 3 or 4 adjacent carbon atoms optionally 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, Sames the config by one or more radicals, selected from the group consisting of halogen, (C1-C6)-alkoxy, (C1-C6)-halogenoalkane, (C3-C6)-cycloalkyl, S(O)pR8and CO2-(C1-C6)-alkyl; or, when a represents (C1-C6-alkylen or (C1-C6-halogenation and R5means (C1-C6)-alkyl, substituted by one or more radicals halogen, one or more of the carbon atoms of the group R5may, together with S(O)mand one or more carbon atoms, form a 5 - or 6-membered ring;

R6and R8each, independently, represent (C1-C6)-alkyl or (C1-C6-halogenated;

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)-alkoxy, CN, NO2, S(O)pR8and NR10R11;

R10and R11each, independently, represent H, (C1-C6)-alkyl or (C1-C6-halogenated;

m, n and p each independently 0, 1 or 2; and

q is 0 or 1.

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

R1denotes CN;

W represents C-halogen;

R2oboznachaemogo;

R3means CF3or OCF3;

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

And means (C1-C9-alkylen or (C1-C9-halogenation, in which 2, 3 or 4 adjacent carbon atoms optionally 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, -(CH2)qR7; or denotes (C1-C6)-alkyl, substituted by one or more radicals selected from the group consisting of halogen, (C1-C3)-alkoxy, (C1-C4)-halogenoalkane, (C3-C7)-cycloalkyl, S(O)pR8, CN, NR10R11and S(O)pR7;

R6means (C1-C2-halogenated;

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)-alkoxy, (C1-C4)-halogenoalkane, CN, NO2, S(O)pR8, COR11, NR10R11and HE;

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

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)-alkoxy;

R10denotes H, (C1-C3)-alkyl, (C1-C3-halogenated, (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 optionally contains 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 R14each, independently, represent H, (C1-C3)-alkyl, (C1-C3-halogenated, (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-Alcock and, (C1-C3)-halogenoalkane, CN, NO2, S(O)pR8and NR11R14;

m, n and p each independently 0, 1 or 2;

q is 0 or 1; and

each heterocyclyl in the abovementioned radicals independently denotes 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) are compounds in which:

R1denotes CN;

W denotes C-Cl;

R2denotes chlorine;

R3means CF3or OCF3;

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

And means (C1-C4-alkylen;

R5means (C3-C6-cycloalkyl, -(CH2)qR7or (C1-C6-halogenated; or, when R5means (C1-C6-halogenated, one or more of the carbon atoms of the group R5may, together with a group S(O)mand one or more carbon atoms, form a 5 - or 6-membered ring;

R6means CF3, CF2Cl, CFCl2, CBrF2or CHF2;

R7denotes phenyl;

m and n are each independently 0, 1 or 2; and

q is 0 or 1.

As a preferred class of compounds of formula (I) are compounds in to the which:

R1denotes CN;

W represents C-halogen;

R2denotes halogen;

R3means CF3or OCF3;

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

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

R5means (C1-C6-halogenated;

R6means CF3, CF2Cl, CFCl2, CBrF2or CHF2; and

m and n are each independently 0, 1 or 2.

Especially preferred class of compounds are compounds in which:

R1denotes CN;

R2denotes chlorine;

R3means CF3;

W denotes C-Cl;

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

R5means (C1-C2-halogenated;

R6means CF3;

And means (C2-C3-alkylen; and

m and n are each independently 0, 1 or 2.

Another class of new derivatives of 5-substituted alkalinisation formula (I) or their pesticide-acceptable salts are compounds in which:

R1denotes CN; R2denotes chlorine; R3means CF3or OCF3; W denotes C-Cl; R denotes hydrogen or (C1-C6)-alkyl; R5means (C1-C6)-alkyl; R6means CF3; And means (C1-C4-alkylen (And preferably denotes (C2-C3-alkylen) and m and n are each independently 0, 1 or 2.

The following are particularly preferred variant of the present invention is new derivatives of 5-substituted alkalinisation formula (I) or their pesticide-acceptable salts, in which:

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

m and n are each independently 0, 1 or 2.

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

In the further description of how, when the symbols appearing in the formulas, not specified OS is Bo, it should be clear that they are such "as defined above", in accordance with the first definition of each symbol in this description.

According to a particular case of this invention, the compounds of formula (I), where R1, R2, R3, R6, W, A and n are as defined above, R4and R5are 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 denotes deleted (tsepliaeva) group, generally halogen and preferably bromine, with a compound of formula (III):

where a and m are as defined above, and R5is the same as defined above, except hydrogen. This reaction is usually carried out in the presence of a base such as a carbonate of an alkali metal, e.g. potassium carbonate, in a solvent such as dioxane, tetrahydrofuran or N,N-dimethylformamide, at temperatures from 0 to 100°With (preferably 0-50°).

According to the following particular case of this invention the compounds of formula (I), where R1, R2, R3, R4, R6W, A, m and n are as defined above, and R4is that what they, as defined above, except hydrogen, OR7, OR8and OR9, R5is as defined above excluding hydrogen, may also be obtained by alkylation or acylation of the corresponding compounds of formula (IV):

where R1, R2, R3, R6W, A, m and n are as defined above, and R5is the same as defined above, except hydrogen, with a compound of formula (V):

where R4is the same as 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, in the case of acylation reactions. This 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 temperatures from 0 to 100°With (preferably 0-50°).

According to the following particular case of this invention, the compounds of formula (I), where R1, R2, R3, R4, R6, W, A, m, and n are as defined above, and R5is the same as defined above, except hydrogen, can be obtained by the interaction between the connect and the ia of the formula (VI):

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

where m and a are as defined above, R5is the same as defined above, except hydrogen, and L2refers to the deleted group, generally halogen and preferably chlorine. This 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 temperatures from 0 to 100°With (preferably 0-50°).

According to the following particular case of this invention, the compounds of formula (I), where R1, R2, R3, R6, W, m, and n are as defined above, R5is the same as defined above, except hydrogen, R4denotes hydrogen; m is 0 and 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 R5is the same as defined above, except hydrogen. This reaction can p is Voditsa in the presence or in the absence of a base, such as a carbonate of an alkali metal, e.g. potassium carbonate, in a solvent such as dioxane, tetrahydrofuran or N,N-dimethylformamide, at temperatures from 0 to 100°With (preferably 0-50°). Can be used various forms of formaldehyde, such as paraformaldehyde, when in the reaction mixture may be present in the water.

According to the following particular case of this invention the compounds of formula (I), where R1, R2, R3, R4, R6And, W and n are as defined above, R5is the same as defined above, except hydrogen, and m is 0, can be obtained by the coupling of compounds of formula (X):

where R1, R2, R3, R4And, W and n are as defined above, with a compound of formula (XI):

R5-L3(XI)

where R5is the same as defined above, except hydrogen, and L3refers to the deleted group, typically a halogen, for example chlorine, or alkylsulfonyl group. This reaction is usually carried out using a salt of an alkali metal, for example, salts of sodium, compound of formula (X), in an inert solvent, such as tetrahydrofuran, at temperatures from 0 to 60°C.

According to the following particular case of this invention the compounds of formula (I), where R1 , R2, R3, R4, R5, R6And, W and n are as defined above, and m is 0, can be also obtained by the interaction of the compounds of formula (XII):

where R1, R2, R3, R4And, W and n are as defined above, and L4refers to the deleted group, typically a halogen, for example chlorine, or alkylsulfonyl group, with a compound of formula (IX)as defined above. This reaction is usually carried out in the presence of a base, for example alkali metal hydride such as sodium hydride, or alkoxide of an alkali metal, such as tert-piperonyl potassium, in an inert solvent, such as tetrahydrofuran, at temperatures from 0 to 60°With or carbonate of an alkali metal such as potassium carbonate, in an inert solvent, such as acetone, at temperatures from 0°to the temperature of reflux distilled solvent.

According to the following particular case of this invention the compounds of formula (I), where R1, R2, R3, R4, R6, W, m, and n are as defined above, R5is the same as defined above, except hydrogen, and a represents (C2-C12-alkylen, douglasiana chain which binds R5S(O)m- , and-NR4groups can also be obtained by the interaction of the compounds of formula(VI), above, where R1, R2, R3, R4, R6, W and n are as defined above, with a compound of formula (XIII):

where R5and m are as defined above, and1means (C2-C12)-alkenylphenol group in which the double bond is adjacent to the group R5S(O)m. This reaction is usually carried out in an organic solvent at a temperature of from 0 to 200°With (preferably 0-100°).

According to the following particular case of this invention, the compounds of formula (I), where R1, R2, R3, R4, R6And, W and n are as defined above, R5denotes hydrogen and m is 0, can be obtained by interaction of the corresponding compounds of formula (XII)as defined above, with a compound of formula (XIV):

where Rameans (C1-C6)-alkyl, to obtain the compounds of formula (XV):

where the various symbols are as defined above. This reaction is usually carried out in the presence of a base such as an alkali metal hydride, e.g. sodium hydride, alkoxide of an alkali metal, such as ethoxide sodium, or triethylamine, in a solvent such as dioxane, tetrahydrofuran or N,N-dimethylfuran the ID, at a temperature of from 0 to 100°C. Then compound of formula (XV) hydrolyzing to obtain the corresponding compounds of formula (I), where R5denotes N. The hydrolysis is usually carried out using a base such as aqueous ammonia or alkali metal hydroxide, such as sodium hydroxide, typically in the presence of co-solvent such as an alcohol, e.g. ethanol, at temperatures from 0 to 100°C. Alternatively, the hydrolysis can be performed in situ without isolation (XV).

According to the following particular case of this invention the compounds of formula (I), where R1, R2, R3, R4, R5, R6, W and a are as defined above, and m and/or n is 1 or 2, can be obtained by oxidation of the corresponding compounds in which m and/or n is 0 or 1. The oxidation is usually using percolate, such as 3-chloroperbenzoic acid, in a solvent such as dichloromethane or 1,2-dichloroethane, at a temperature of from 0°to the temperature of reflux distilled solvent.

A series of compounds of formula (I), which can be synthesized using the above method, can be also obtained in a parallel manner, and this can be done manually, or semi-automatic, or fully automatic. In this case, it is possible, for example, to automate the procedure of reaction, treatment and and 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.

A number of commercially available devices, for example, provide 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, can be used for parallel implementation of this reaction and processing. For the parallel purification of compounds of formula (I) or intermediates formed during retrieval, can be used, among others, the chromatographic apparatus, for example, the apparatus ISCO, Inc., 4700 Superior Street, Lincoln, NE 68504, USA.

Use of these devices leads to unify the way in which the individual stages of the process are automated, but between these stages of the process must be carried out manual operations. This can be avoided by using prointegrirowany or fully integrated automation systems, the automatic units are controlled, for example, robots. Such automation can be obtained, for example, by Zymark Corporation, Zymark Center, Hopkinton, MA 01748, USA.

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

Application of methods of synthesis on solid media allows you to use a number of methods that are known from the literature, and which, in turn, can be manual or automatic. For example, the way "tea bag" ("tea-bag method") (Houghten, US 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 parallel synthesis on solid phase carriers successfully performed, for example, using devices Argonaut Technologies, Inc., 887 Industrial Road, San Carlos, CA 94070, USA or MultiSynTech GmbH Wullener Feld 4, 58454 Witten, Germany.

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

Intermediates of formula (II), where L denotes chlorine, bromine or iodine, can be obtained in accordance with known methods, for example, described in EP 0295117, by diazotization of the corresponding amine is of the formula (VIII), usually using Alternaria, such as tert-butylnitrite, in the presence of a suitable halogenation agent, preferably of bromoform, iodine or anhydrous copper chloride (II), optionally in the presence of a solvent, such as acetonitrile or chloroform, at temperatures from 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.

The compounds of formula (XV) are novel and as such form the following object of the present invention.

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

Chemical examples

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

NMR spectra were taken in deuterium chloroform, unless otherwise noted.

In the following examples, the amount (including interest) are given in terms of weight, unless otherwise indicated.

Example 1

To a solution of 5-bromo-1-(2,6-dichloro-4-triptoreline)-3-cyano-4-triftormetilfullerenov (5.0 g, 9.7 mmol) in 1,4-dioxane (20 ml) and N,N-dimethylformamide (20 ml) was added 3-ethylthiophene (2,306 g, and 19.3 mmol) and potassium carbonate (2.7 g, 19,3 mm is eh). The resulting mixture was stirred at 20°With over 2,75 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 and chromatographically on silica gel with elution with a mixture of heptane-ethyl acetate (4:1) to give 1-(2,6-dichlor-4-triptoreline)-3-cyano-5-(3-ethylthiophenethylamine)-4-triftormetilfullerenov in the form of a yellow solid (compound number 1-14, 4,79 g, yield 86%), TPL 80°C.

Example 2

To a solution of 1-(2,6-dichloro-4-triptoreline)-3-cyano-5-(3-ethylthiophenethylamine)-4-triftormetilfullerenov (2.0 g, 3.6 mmol) in tetrahydrofuran at 20°C in an atmosphere of nitrogen was added sodium hydride (0,461 g, 60% in oil, 11.5 mmol) and was stirred for 0.5 hour. Added logmean (2,065 g, 14.4 mmol) and the mixture was stirred for 4.5 hours at 20°With, then gave it to stand for 2.5 days. This mixture was added to ethyl acetate and saturated solution of ammonium chloride. The organic layer was washed with water and brine, dried (sodium sulfate), evaporated and chromatographically on silica gel with elution with a mixture of heptane-ethyl acetate (3:1) to give 1-(2,6-dichloro-4-triptoreline)-3-cyano-5-[N-(3-ethylthiophen)-N-methylamino]-4-triftormetilfullerenov in the form of a light brown solid (compound number 2-14, 1.3 g,yield 57%), TPL 89°C.

Example 3

m-Chloroperbenzoic acid (0,091 g, 77%, 0.4 mmol) was added to a solution of 1-(2,6-dichloro-4-triptoreline)-3-cyano-5-[N-(3-ethylthiophen)-N-methylamino]-4-triftormetilfullerenov (0,23 g, 0.4 mmol) in 1,2-dichloroethane at 0-5°C. the Mixture was stirred at 0-5°C for 0.5 hour, then poured into saturated sodium bicarbonate solution and ethyl acetate. The organic layer was washed with saline, dried (sodium sulfate), evaporated and chromatographically on silica gel with elution with a mixture of heptane-ethyl acetate (1/1 - 3/7) to obtain 1-(2,6-dichloro-4-triptoreline)-3-cyano-5-[N-(3-ethylsulfonyl)-N-methylamino]-4-triftormetilfullerenov in the form of a light brown oil (compound number 2-15, 0,186 g, 71%), 19F: -63,8, -78,7.

Example 4

Sodium hydride (0.172 g, 4.3 mmol) was added to a solution of 1-(2,6-dichloro-4-triptoreline)-3-cyano-5-N-methylamino-4-cryptomaterial (1.5 g, 3.4 mmol) in tetrahydrofuran, cooled in a bath with a mixture of water with ice. Bath ice was removed and the mixture was stirred at 20°C for 0.75 hour and added chlorodimethylsilyl (0,456 g, 4.5 mmol). The mixture was stirred at 20°C for 6.5 hours and was heated under reflux with reflux distilled for 2 hours, then cooled and added to saturated ammonium chloride and ethyl acetate. The organic layer was washed water is the first and saline, was dried (sodium sulfate), evaporated and chromatographically on silica gel with elution with a mixture of heptane-ethyl acetate (9:1) to give 1-(2,6-dichloro-4-triptoreline)-3-cyano-5-[N-methyl-N-(methylthiomethyl)amino]-4-cryptomaterial in the form of a light yellow oil (compound number 2-25, of 0.59 g, yield 35%), 19F: -43,9, -63,7.

Example 5

Sodium hydride (0,032 g, 60%, 0.8 mmol) was added to a solution of 1-(2,6-dichloro-4-triptoreline)-3-cyano-5-(3-ethylthiophenethylamine)-4-triftormetilfullerenov (0.3 g, 0.54 mmol) in tetrahydrofuran at 20°C in nitrogen atmosphere. The mixture was stirred at 20°C for one hour, then added ethylchloride (0,121 g, 1.1 mmol). The mixture was stirred at 20°C for 5 hours, then poured into saturated ammonium chloride and ethyl acetate. The organic layer was washed with water and brine, dried (sodium sulfate), evaporated and chromatographically on silica gel with elution with a mixture of heptane-ethyl acetate (4:1) to give 1-(2,6-dichloro-4-triptoreline)-3-cyano-5-[N-etoxycarbonyl-N-(3-ethylthiophen)amino]-4-triftormetilfullerenov in the form of oil (compound number 3-14, 0,278 g, yield 81%), 19F: -63,9; -77,9.

Example 6

To a solution of 3-cyano-5-methylamino-1-(2,6-dichloro-4-triptoreline)-4-triftormetilfullerenov (0.5 g, 1.1 mmol) in tetrahydrofuran was added sodium hydride (60%, 0.06 g, 1.4 mmol), then 2-chloroethylenes lfon (0.27 g, 1.3 mmol). The mixture was heated under reflux with reflux distilled within 10 hours. After extraction processing and column chromatography with elution with a mixture of heptane-ethyl acetate (1:1) was obtained 1-(2,6-dichloro-4-triptoreline)-3-cyano-5-N-(2-phenylsulfonyl)-N-methylamino-4-triftormetilfullerenov (compound number 2-38, 0.26 g), 19F: -64,1; -73,0.

Example 7

To a solution of 1-(2,6-dichloro-4-triptoreline)-3-cyano-5-(2-phenylthiomethyl)amino-4-cryptomaterial (0.15 g, 0.27 mmol) in tetrahydrofuran was added ethylchloride (58 g, 0.54 mmol) and diisopropylethylamine (70 mg, 0.54 mmol) and 4-dimethylaminopyridine (10 mg). The mixture was heated under reflux with reflux distilled for 1 hour. After extraction processing and column chromatography with elution with a mixture of heptane-ethyl acetate (1:1) was obtained 1-(2,6-dichloro-4-triptoreline)-3-cyano-5-N-(2-phenylthiomethyl)-N-ethoxycarbonyl-4-cryptomaterial (connection room 3-109, 0.07 g), 19F: -63,7; -70,8.

The following referential example illustrates the production of intermediate products used in the synthesis in the examples above.

Reference 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°With those who tell 3 hours. Added a second portion of tert-butylnitrite (84 ml, to 0.662 mol) and the mixture was stirred at 60-70°even for 2.5 hours. Then it was cooled, washed with hexane, hexane-toluene and then filtered. The solid is washed with pentane and dried in vacuum to obtain 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 1-12, also form part of this invention and have been obtained or can be obtained in accordance with the above-described examples 1 to 7, or the above-described General methods or analogously to the above examples 1-7, or public ways. In these tables, Et denotes ethyl, i-Pr means isopropyl, n-Bu represents n-butyl, t-Bu represents tert-butyl, Ph denotes phenyl, and 2-THF denotes 2-tetrahydrofuryl. In cases where the subscript numbers are missing, it should be clear that they refer to, for example, CH3 means of CH3.

The magnitude of the shift signal 19F-NMR spectra are given in ppm

Rooms compounds are given only for reference purposes.

Table I: Compounds of formula (I)in which the substituents have the following meanings:

R1= CN, R6means CF3, R4denotes hydrogen, W = C-Cl, R2= Cl, R3= CF3.

p>

Table X: the compounds of formula (Ia):

Table XI: the compounds of formula (Ib):

Table XII: the compounds of formula (Ic):

The term "compound in this invention" in the following context includes 5-substituted alkylamines formula (I)defined above, and pesticide-acceptable salt.

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

The following aspect of this invention the compounds of formula (I) or their salts, or compositions used to prepare the veterinary medicinal product, preferably, for the destruction of parasites, in particular, ecto - and endoparasites in the animal body and animal body.

Compounds according to this invention and methods of their application are especially useful for combating arthropods (Arthropoda) or worms that are harmful to Pets or carry diseases, or act as vectors of diseases of domestic animals, for example, mentioned here above, and more specifically, in the control of ticks, mites, lice, fleas, small two-winged insects or stinging, annoying or causing MIAS (entomon) flies. The compounds of this invention are particularly useful in combating arthropods or helminths, which are present inside the pet-owners or eat in the skin or on the skin or suck the blood of the animal, and for this purpose they may be administered orally, parenterally, transdermally, or topically.

Compositions described herein can be, in General, applied to animals infected arthropods or helminths is or exposed to infected arthropods or helminths, by parenteral, oral or topical application of compositions in which the active ingredient exhibits an immediate and/or prolonged action over a period of time against the arthropods or helminths, for example, by inclusion in food or appropriate accept oral pharmaceutical forms, edible baits, salt lisanti, food additives, pour forms, sprays, baths, disinfectants, shower solutions, sprays, dusty, technical greases, shampoos, creams, wax putty or system Samoobrona for farm animals.

The compounds of formula (I) are particularly useful for the destruction of parasites in animals by oral use, and in the following a preferred aspect of this invention the compounds of formula (I) used for the destruction of parasites in animals by oral administration. The compounds of formula (I) or their salts can be administered before, during or after a meal. The compounds of formula (I) or their salts can be mixed with a carrier and/or feed.

The compound of formula (I) or its salt is administered orally at a certain dose animal usually in the dose range of 0.1-500 mg/kg of the compounds of formula (I) or its salt per kilogram of animal body weight (mg/kg).

The frequency processing of the animal, preferably pet, Podles the future treatment of the compound of formula (I) or its salt, is usually from about once per week to about once a year, preferably from about once every two weeks to once every three months.

The compounds of this invention can be administered in the most advantageous way other parasiticide effective material, such as endoparasiticides, and/or ectoparasiticide, and/or endo-ectoparasiticide. For example, such compounds include macrocyclic lactones, such as avermectins or milbemycin, for example, ivermectin, pirates or growth regulator insect, such as lufenuron or methoprene.

According to the next object of the present invention, a method of pest control in the focus of infection, which involves the application 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 a pesticidal composition (i.e. 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 of pest control in the focus of infection. This focus includes, for example, the pest (plant, field, forest, orchard, waterway, soil, p is stitely product or the like), where pests live or eat, or a place susceptible to future infection by the pest. Thus, the connection of the present invention can be applied directly to the pest, to the place where or feed on the pest, or to a place susceptible to future infection by the pest. As can be seen from previous applications of pesticides, this invention relates to pesticide-active compounds and methods of using these compounds to combat a number of kinds of pests, which include arthropods (arthropod), in particular, insects or mites, or plant nematodes. Thus, the connection according to this invention can be advantageously used in practical applications, for example, in veterinary medicine or animal husbandry, in the cultivation of field or horticultural crops, in forestry or public health. Compounds according to this invention can be used, for example, in the following applications and on the following pests:

In the field of veterinary medicine or livestock or for compliance with sanitary and hygienic requirements against arthropods, which are internal or external parasites in vertebrates, particularly warm-blooded vertebrates, such as domestic animals, e.g. cattle the cattle, sheep, goats, horses, pigs, poultry, dogs or cats, for example, against Acarina, including such as pliers (for example, soft ticks, including species of Argasidae, for example, Argas spp. and Ornithodorus spp. (e.g., Ornithodorus moubata); hard ticks, including species of Ixodidae, for example, Boophilus spp., for example, Boophilus microplus, Rhipicephalus spp., for example, Rhipicephalus appendiculatus and Rhipicephalus sanguineus; mites (for example, Damalinia spp.); fleas (e.g., Ctenocephalides spp., for example, Ctenocephalides felis (cat flea) and Ctenocephalides canis (dog flea)); lice, e.g., Menopon spp.; Diptera (e.g., Aedes spp., Anopheles spp., Musca spp., Hypoderma spp.); Hemiptera (Heteroptera bugs); Dictyoptera (e.g., Periplaneta spp., Blatella spp.); Hymenoptera (Hymenoptera); for example against infections of the gastro-intestinal tract caused by parasitic worms nematodes, for example, members of the family Trichostrongylidae.

For controlling soil insects, such as blaska Dlinnaya, termites (in particular, for the protection of buildings), root maggots, wireworms, root weevils, moths, insects, podgryzayuschie plants, root aphids or cerubidine larvae. They can also be used to effect against plant pathogenic nematodes, such as vicegerency (gallogermanate), beet nematode, bungalowene hookworms, nematodes damage or stem or bulb nematodes, or against ticks. To deal with such soil viditel the mi, for example, blascoe dinosau, these compounds are preferably applied to the soil or injected with effective norm in the soil in which it is planted with crops or should be planted crops, or applied to the seeds or the roots of growing plants.

In public health, these compounds are especially useful in the fight against many insects, particularly flies that live in the area of sewage, or other Diptera pests such as house flies, gigalo ordinary, linki, jagalchi small cow, deer flies, small two-winged insects (gnats, midgots), biting midges, black flies or mosquitoes.

For the protection of stored products, for example cereals, including grain and flour, groundnuts, animal feed, timber or things of the household, e.g. carpets and textiles, the compounds of this invention are applicable against invasions of arthropods, more specifically, beetles, including weevils, moths or mites, for example Ephestia spp. (flour moths), Anthrenus spp. (Museum beetles), Tribolium spp. (of larval small flour), Sitophilus spp. (granary weevil) or Acarus spp. (ticks).

In the fight against cockroaches, ants or termites or similar arthropod pests in infested domestic and industrial premises or in the fight against mosquito larvae in photoproto is, wells, reservoirs or other running or standing water.

For the processing of foundations, structures or soil to prevent invasion of building termites, for example, Reticulitermes spp., Heterotermes spp., Coptotermes spp.

In agriculture against adults, larvae and eggs of Lepidoptera (butterflies) (butterflies and moths), e.g., Heliothis spp., such as Heliothis virescens (leaf tobacco), Heliothis armigera and Heliothis zea. Against adults and larvae of Coleoptera (beetles) (beetles), e.g., Anthonomus spp., for example, grandis (weevil cotton), Leptinotarsa decemlineata (Colorado potato beetle), Diabrotica spp. (flea dinosau). Against Heteroptera (Hemiptera and Homoptera), for example, Psylla spp., Bemisia spp., Trialeurodes spp., Aphis spp., Myzus spp., Megoura viciae, Phylloxera spp., Nephotettix spp. (cycatki rice), Nilaparvata spp.

Against Diptera (flies), for example, Musca spp. Against Thysanoptera such as Thrips tabaci (tobacco thrips). Against Orthoptera such as Locusta spp. and Schistocerca spp. (locusts and crickets), for example, Gryllus spp. and Acheta spp., for example, Blatta orientalis, Periplaneta americana, Blatella germanica, Locusta migratoria migratorioides and Schistocerca gregaria. Against springtails, such as Periplaneta spp. and Blatella spp. (such relic species). Against arthropods of agricultural significance such as the Acaria (mites), for example, Tetranychus spp. and Panonychus spp.

Against nematodes that attack plants or trees that are important for agriculture, forestry or horticultural, either directly or through INF the Oia plants bacterial, viral, Mycoplasma or fungal diseases. For example, against nematodes root growths, such as Meloidogyne spp. (e.g. M. incognita).

In practice for combating arthropods, in particular insects or mites or pests nematodes of plants, the method involves, for example, application to the environment in which they grow, the effective amount of the compounds of this invention. For this method, the compound of the present invention is usually applied to the source of infection, where the infection arthropods or nematodes should be controlled, in the effective rate in the range of about 2 grams - approximately 1 kg of active compound per hectare of cultivated islet. Under ideal conditions, depending on the pest, which must be destroyed, a lower rate may provide adequate protection. On the other hand, adverse weather conditions, the stability of a specific pest or other factors may require the application of the active ingredient in the higher standards. Optimal rate usually depends upon a number of factors, such as the type of pest to be destroyed, the type or stage of growth of the infected plants, the distances between the rows or method of application. Preferably the range of effective norms of the active compounds is atriplicifolia 10 g/ha to about 400 g/ha, more preferably from about 50 g/ha to about 200 g/ha When the pest is passed through the soil, active compound, usually in the prepared compositions, distribute evenly on the area to be processed (that is, for example, randomly making or tape making) by any suitable means and is applied when the norms of from about 10 g/ha to about 400 g/ha of active ingredient, more preferably from about 50 g/ha to about 200 g/ha of active ingredient. When applied in the form dip the roots of seedlings or drip irrigation for plants a liquid solution or suspension contains from about 0,075 to about 1000 mg of active ingredient/l, preferably from about 25 to about 200 mg of active ingredient/l Application may be made, if desired, on the field or the area of cultivation of agricultural crops in whole or in close proximity to the seeds or plants to be protected from the attack of pests. The connection according to this invention can leach into the soil by spraying with water in this area or can be left to the natural action of rainfall. During or after application prepared as a composition of a compound can be, if desired, divided mechanically into the soil, e.g. the R, plow tillage, disking or by use of the chain loop. Application can be made before planting, at planting, after planting, but before will happen germination or after germination.

The connection according to this invention and methods of pest control with its use are very important in the protection of field, forage crops, crops on plantations, greenhouses, fruit and vegetable crops and vineyards, ornamental plants or trees on plantations or in forestry, for example: cereals (such as wheat and rice), cotton, vegetables (such as peppers), field crops (such as sugar beet, soybean or oilseed rape), crops, grassland or forage crops (such as maize or sorghum), crops of fruit and vegetable farms or gardens (such as with stone or one-seeded fruit crops or citrus crops), ornamental plants, flowers or vegetables or shrubs in greenhouses or gardens or parks, or forest trees (both deciduous garden trees, and evergreen trees in forests, plantations or nurseries.

The compounds of this invention are also valuable in the protection of timber (standing timber, felled timber, lumber stored timber or construction timber from attack, for example,sawflies or beetles pests or termites.

They have application in the protection of stored products such as grains, fruits, nuts, spices or tobacco, either in General form or blended or compounded in the products, from the attacks of moths, beetles, mites or weevil. They also protect stored animal products, such as skin, hair or feathers in natural or processed form (e.g., in the form of carpets or fabrics), from attack by moths or beetles pests and stored meat, fish or grain from attack by beetles, mites or flies.

The composition described below for application to growing crops or pockets of cultivation of agricultural crops or for use as seed treatment, can generally be used an alternative for the protection of stored products, household goods, property, or, in General, the areas of the environment. Suitable methods of applying the compounds of this invention include: for the growing of crops in the form of sprays of leaves (e.g., in the form of sprays for inclusion in the grooves), Farrukh Dustov, granules, fogs or pins or also as suspensions of finely divided or encapsulated compositions in the form of soil or roots of liquid impregnation, powders, granules, okurivanie or pen; for seeds of crops through application in the form of protravlivanie seed liquid particles or powder is mi;

for the environment in General or to specific locations where pests lurk, including stored products, timber, household goods and household or industrial buildings, in the form of sprays, mists, powders, fumes, wax putties, varnishes, granules, or baits, or in the form of drip feed in water courses, wells, reservoirs or other running or standing water.

The compounds of formula (I) can be used for pest control in crops of known genetically engineered plants or genetically engineered plants that have yet to be developed. As a rule, the transgenic plants are characterized by particularly advantageous properties, for example, resistance to a specific protection agents inoculation, resistance to plant diseases or pathogens of plant diseases, such as particular insects or microorganisms such as fungi, bacteria or viruses. Other important properties include, for example, collected material concerning the quantity, quality, and ability to persist during storage of the composition and specific components. For example, the famous transgenic plants, in which the starch content is increased, or the quality of the starch is changed, or in which the collected material has a different composition of fatty the acid.

Use in economically important transgenic crops of useful plants and ornamental plants is preferred, for example of cereals such as wheat, barley, rye, oats, millet, rice, cassava (manioc), and corn, or for crops of sugar beet, cotton, soya, oilseed rape, potato, tomato, peas and other types of vegetables.

When used in transgenic crops, particularly crops that are resistant to insects often see the effects, in addition to action against harmful organisms, which should be observed in other crops, which are specific for application in the present transgenic crops, for example a modified or specifically widened scope of pests that can be destroyed, or modified standards apply, which can be used for drawing.

Thus, this invention relates also to the use of compounds of formula (I) for pest control in crops of transgenic plants.

According to the next object of the present invention proposed pesticide composition comprising one or more compounds of the present invention, as defined above, together, and preferably homogeneous dispersed in them, with one or more pesticide-acceptable diluents or carriers and/and is also a surface-active agents [i.e. diluents or carriers and/or surface-active agents of the type usually recognized in this area as suitable for use in pesticide compositions that are compatible with the compounds of the present invention].

In practice, the compounds according to this invention most often are the components of the compositions. These compositions can be used for combating arthropod (Arthropoda), especially insects, or plant nematodes or mites. These compositions can be compositions of any type known in the field, suitable for application to the desired pest in any premises or located indoors or outdoors area. These compositions contain at least one compound of the present 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, adjuvants, surface-active agents or the like, for the intended application and which are acceptable in the field of agriculture or medicine. These compositions can be prepared by any known in this field by the way, also form part of this invention.

Compounds according to this invention, commercially available compositions and forms of application of preparation the data from these compositions, may be present in mixtures with other active substances such as insecticides, attractants, sterilant, acaricides, nematicides, fungicides, growth regulators or herbicides.

These pesticides include, for example, phosphoric esters, carbamates, esters of carboxylic acids, formamidines, tin compounds and substances produced by microorganisms.

Preferred components in mixtures are the components:

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, famphur, fenamiphos, fenitrothion, fensulfothion, fenthion, flupirtine, fonofos, formation, fosthiazate, heptenophos, isazofos, isocial, isoxathion, Malathion, methacrifos methamidophos, methidathion, salicion, mevinphos, monocrotophos, naled, omethoate, oxydemeton-methyl, parathion, parathion-methyl, pentat, Fort, fosalan, phosfolan, fastcars (BAS-301), phosmet, phosphamidon, phoxim, pirimiphos, pirimiphos-ethyl, pirimiphos-methyl, profenofos, propafol, propetamphos, prothiofos, pyraclofos, peridinin, finalpos, sulprofos, temephos, terbufos, tebupirimfos, tetrachlorobis the OS, 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-m-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-furylmethyl(E)-(1R)-CIS-2,2-dimethyl-3-(2-oxathiolan-3-ylidenemethyl)cyclopropanecarboxylate, beta calotren, alpha-cypermethrin, beta-cypermethrin, bioallethrin, bioallethrin ((S)-cyclopentolate), bioresmethrin, bifenthrin, (RS)-1-cyano-1-(6-phenoxy-2-pyridyl)methyl(1RS)-TRANS-3-(4-tert-butylphenyl)-2,2-dimethylcyclopropanecarboxylate (NCI 85193), cicloprofen, cyfluthrin, cigalotrin, Caitrin, cypermethrin, cyphenothrin, deltamethrin, empenthrin, esfenvalerate, fenfluthrin, fenpropathrin, fenvalerate, flucythrinate, flumethrin, fluvalinate (D-isomer), imiprothrin (S-41311), lambda cigalotrin, permethrin, phenothrin (®-isomer), prallethrin, pyrethrin (natural products), resmethrin, tefluthrin, tetramethrin, theta-cypermethrin, tralomethrin, transfluthrin, Zeta-cypermethrin (F-56701);

4. from the group amidino

amitraz, Chlordimeform;

5. the group is joining tin

cyhexatin, fenbutatin oxide;

6. other

the abamectin, ABG-9008, acetamiprid, achiezer, 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, chlormadinone, 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, benzoate emamectin, endosulfan, ethiprole (sulfation), etofenprox, etoxazole, fenazaquin, fenoxycarb, fipronil, fluazuron, flumet (Florentin, SZI-121), 2-fluoro-5-(4-(4-ethoxyphenyl)-4-methyl-1-pentyl)diphenyl ether (MTI 800), viruses granules and nuclear polyhedrosis, 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-00, 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, 12thEdition, British Crop Protection Council, Farnham 2000.

Dose the effective application of the compounds used in this invention can vary within wide limits, in particular, depending on the nature of the subject of the destruction of the pest or the degree of contamination, for example, crops of these pests. In General, the compositions of this invention usually contain about 0.05 to about 95 wt.% one or more active ingredients in accordance with this invention, it is not necessarily approximately 1 - approximately 95% of one or more solid or liquid carriers, approximately 0.1 to approximately 50% of one or more other compatible components, such as surface-active agents or the like, In this case, 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. Thus, this media is generally inert and it must be acceptable (for example, agronomically acceptable, in particular for the processing plant).

The carrier may be solid, for example, clays, natural or synthetic silicates, silica, resins, waxes, solid fertilizers (e.g. ammonium salts), ground natural minerals such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite, bentonite or diatomaceous earth, or crushed synthetic minerals, such as silica, alumina (aluminum oxide) or silicates, in particular, silicates of aluminum or magnesium. As solid carriers for granules suitable are 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 which, such as sawdust, coconut shell, rods corn cobs, sheet wrapper of corn or tobacco stems; kieselguhr, tricalcium phosphate, powdered cork or activated carbon; water-soluble polymers, resins, waxes; and solid fertilizers. Such solid compositions may, if desired, contain one or more compatible moisturizing, dispersing, emulsifying or coloring agents, which, when they are solids, can also serve as a diluent.

The media may also be liquid, for example water, alcohols, in particular butanol or glycol and also their simple or esters, in particular the acetate methylglycol; ketones, in particular acetone, cyclohexanone, methyl ethyl ketone, methyl isobutyl ketone or isophorone; oils, such as paraffinic or aromatic hydrocarbons, in particular, xylene 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, dimethyl sulfoxide or N-organic; liquefied gases; or the like, or their mixture.

Surface-active agent may be an emulsifying agent, disperging the second agent or wetting agent of ionic or nonionic type, or a mixture of such surface-active agents. Among them are, for example, salts of polyacrylic acids, salts of lignosulphonic acids, salts of Phenolsulphonic or naphthalenesulphonic 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), phosphoric esters of alcohols or of polycondensates 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 generally essential when the active ingredient and/or the inert carrier are only slightly soluble in water or are water-based and agent-carrier composition for the application is water.

The compositions of this invention can optionally contain other additives, such as adhesives and dyes. In these compositions can be used such adhesives as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or grids, such as the Arabian gum, polyvinyl alcohol or polyvinyl acetate, natural phospholipids, such as capalini or lecithin, or synthetic is practical phospholipids. Can be used 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.

Thus, for agricultural use of the compounds of this invention are usually in the form of compositions, which are in various solid or liquid forms. Solid forms of compositions which can be used are apadravya powders (with a content of compounds of this invention in the range of up to 80%), wettable powders or granules (including water dispersible granules), in particular, the pellets obtained by extrusion, compacting, impregnation of a granular carrier, or granulation using as a source material powder (the content of compounds of this invention in these wettable powders or granules is between approximately 0.5 and approximately 80%). Solid homogeneous or heterogeneous compositions containing one or more compounds of the present invention, for example, granules, beads, pellets or capsules, can be used for the treatment of flowing water n the for some period of time. A similar effect can be achieved with the use of drip or intermittent feed dispersible in water concentrates, as described here.

Liquid compositions include, for example, aqueous or non-aqueous solutions or suspensions (such as emulsifiable concentrates, emulsions, flowable materials, dispersions or solutions or aerosols. Liquid compositions include, in particular, emulsifiable concentrates, dispersions, emulsions, flowable materials, aerosols, wettable powders (or powders for spraying), dry flowable materials or pasta as a form of compositions which are liquid or are intended for formation of liquid compositions when applied, for example, in the form of water sprays (including low or ultra-low volume) or in the form of mists or aerosols.

Liquid compositions, for example, in the form of emulsifiable or soluble concentrates, contain the most often about 5 to about 80 wt.% the active ingredient, whereas emulsions or solutions which are ready for application contain, in this case, approximately 0.01 to approximately 20% active ingredient. In addition to the solvent, the emulsifiable or soluble concentrates can contain, when required, approximately 2 to approximately 50% of suitable additives, such as stabilizers, over OSTO-active agents, wetting agents, corrosion inhibitors, dyes or adhesives. Emulsions of any desired concentration, which are particularly 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 emulsions of the type water-in-oil type or oil-in-water and they can have a thick consistency.

Liquid compositions according to this invention can be used, in addition to the normal agricultural applications, for example, for processing substrates or places, or infected with the risk of infecting arthropods (or other pests, destroying compounds of the present invention), including spaces, storage areas or processing outdoors or indoors, containers or equipment or stagnant or flowing water.

All these water dispersion or emulsion, or a mixture of spray can be applied, for example, to crops by any appropriate means, mainly by spraying, with norms that usually are of the order of about 100 - about 1200 litres of the mixture for spraying per hectare, but can be higher or lower (e.g., low or ultra-low volume) depending on the mu is the necessity or the method of application. The compound or composition of this invention is conveniently applied to the vegetation and, in particular, on the roots or leaves that have pests that need to be resolved. Another method of applying the compounds and compositions of this invention is the application of chemicalization, i.e. making the compositions containing the active ingredient in irrigation (irrigation) water. This irrigation may be irrigation of the sprinkler apparatus for deciduous pesticides or it may be the soil by irrigation or subsurface irrigation for soil or for systemic pesticides.

Concentrated suspensions, which can be applied by spraying, are prepared so as to obtain a stable fluid product which does not settle (fine grinding) and usually contains about 10 to about 75 wt.% the active ingredient, about 0.5 to about 30% surface-active agents, about 0.1 to about 10% of thixotropic agents, from approximately 0 to approximately 30% of suitable additives, such as protivovspenivayushchie agents (defoamers, corrosion inhibitors, stabilizers, wetting agents (penetrants), adhesives, and as carrier, water or an organic liquid in which the active ingredient is slightly soluble or insoluble. Some organic the solid substances or inorganic salts can be dissolved in the carrier to prevent settling or act as antifreeze agents for water.

Wettable powders (or powder for spraying) are usually prepared so that they contain about 10 to about 80 wt.% the active ingredient, about 20 to about 90% solid carrier, approximately 0 to approximately 5% wetting agent, about 3 to about 10% dispersing agent and, if necessary, approximately 0 to approximately 80% of one or more stabilizers and/or other additives, such as wetting agents (penetrants), 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 ground using a mill or other suitable machine for grinding. This gives wettable powders, which are preferred wettability and suspenderbelt. They can be suspended in water to obtain any desired concentration and these suspensions can be used very advantageous way, in particular, for application to the foliage of plants. These "water-dispersible granules (WG)" (granules, which are easily dispersible in water) have compositions that are essentially similar to the composition of wettable powders. Animagus to be prepared by granulating compositions described for wettable powders or wet granulation (contacts micronized active ingredient with an inert filler and a small amount of water, for example, 1-20 wt.% or with an aqueous solution of a dispersing agent or a binding agent, followed by drying and sieving), or dry (pressing with subsequent grinding and sieving).

Norms and concentration of the prepared compositions can vary depending on the method of application or the nature of the compositions or their use. In General, compositions for application to the destruction of arthropod or nematode plant pests usually contain approximately 0,00001 approximately 95 wt.%, more preferably approximately 0,0005 - 50 wt.%, one or more compounds of this invention or of all active ingredients (i.e. compounds of this invention together with other toxic substances in relation to arthropod or plant nematodes, synergists, trace elements or stabilizers). The actual compositions used and their rate of application will be selected to achieve the desired action (action) farmer, breeder, medical practitioner or veterinarian, technician (operator) for the destruction of pests or other person with qualifications what s in this field.

Solid or liquid compositions for topical application to animals, timber, stored products or household economy usually contain approximately 0,00005 is approximately 90 wt.%, more preferably about 0.001 to about 10 wt.%, one or more compounds of the present invention. For oral or parenteral administration, including percutaneous introduction, animal solid or liquid compositions, these compositions typically contain about 0.1 to about 90 wt.%, one or more compounds of the present invention.

Containing medicinal product feeds usually contain about 0.001 to about 3 wt.%, one or more compounds of the present invention. Concentrates or additives for mixing with feeds usually contain about 5 to about 90 wt.%, preferably about 5 to about 50 wt.%, one or more compounds of the present invention. Mineral salt lisence usually contain about 0.1 to about 10 wt.%, one or more compounds of the formula (I) or their pesticide-acceptable salts.

Dusty or liquid compositions for application to cattle, things, premises or outdoor areas may contain approximately 0.0001 of approximately 15 wt.%, more than an hour is about 0.005 to about 2.0 wt.%, one or more compounds of the present invention.

Suitable concentrations in treated waters are approximately of 0.0001 ppm, about 20 ppm, more preferably approximately 0,001 ppm is approximately 5,0 ppm of one or more compounds of the present invention, and they can be used therapeutically in fish farming with appropriate processing periods. Edible baits may contain about 0.01 to about 5 wt.%, preferably about 0.01 to about 1.0 wt.%, one or more compounds of the present invention.

With the introduction of vertebrate parenteral, oral or percutaneous method or other methods, the dose of the compounds of the present invention will depend on the age or health of the spine and on the nature and the extent of its actual or potential contamination of arthropod pests or worms. For oral or parenteral administration is generally suitable dose for a single injection of about 0.1 to about 100 mg, preferably about 2.0 to about 20.0 mg per kg animal body weight, or a dose of about 0.01 to 20.0 mg, preferably about 0.1 to about 5.0 mg per kg of animal body weight per day for drugs prelungirea the aqueous release. Through the use of compositions or devices for extended release doses are required over a period of months, can be combined and fed to the animals once.

The following EXAMPLES 2A-2M illustrate compositions for use against arthropods, especially mites and insects, or against nematodes of plants, which contain as active ingredient the compounds of this invention, such as described in the preparative examples. Each of the compositions described in EXAMPLES 2A-2M, can be diluted with getting the spray compositions in concentrations suitable for use in the field. General chemical description ingredients (for which all of the following percentages are given in weight percent)used in the examples of compositions 2A-2M below, are as follows:

Trade nameChemical 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 media silicate of magnesium
Apropos T36Sodium salts of polycarboxylic acids
Redigel 23Polysaccharide xanthan gum
Benton 38Organic derivative of magnesium montmorillonite
AerosilMicroecology silicon dioxide

EXAMPLE 2A

Water-soluble concentrate is prepared with the following 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 to dissolve. The resulting solution is brought to volume with the remainder of the solvent.

EXAMPLE 2B

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

The active ingredient25% (max)
Suprior BSU10%
Arylan CA 5%
N-organic50%
Solvesso 15010%

The first three components are dissolved in N-organic and then to the solution was added Solvesso 150 to obtain the final volume.

EXAMPLE 2C

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

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

These ingredients are mixed and milled in a hammer mill to a powder with a particle size less than 50 microns.

EXAMPLE 2D

Water-flowing form is prepared with the following composition:

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

These ingredients are homogeneously mixed and ground in a bead mill to obtain an average particle size of smaller than 3 micron.

EXAMPLE 2E

Concentrate emulsifiable suspension is prepared with the following the respective composition:

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

These ingredients are homogeneously mixed and ground in a bead mill to obtain an average particle size of smaller than 3 micron.

EXAMPLE 2F

Dispersible granule in water is prepared with the following composition:

The active ingredient30%
Darvan NO215%
Arylan S8%
Celite PF47%

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

EXAMPLE 2G

The powder dust is prepared with the following composition:

The active ingredient1-10%
A fine powder of talc99-90%

These ingredients are homogeneously mixed and then pulverized as necessary to obtain a fine powder. This paragraph shall rosok can be applied to the source of infection arthropods, for example, waste dumps, stored products or household economy, or animals that are infected or at risk getting infected arthropods, for the destruction of arthropods by swallowing their powder. Suitable methods for distribution of dust-forming powder in an infectious arthropods include mechanical blowers, hand shaking the device or devices for Samoobrona cattle.

EXAMPLE 2H

Edible bait prepared with the following composition:

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

These ingredients are homogeneously mixed and molded, as appropriate, in the form of bait. This edible bait can be distributed in the focus of infection, for example, in domestic or industrial premises, for example, in kitchens, hospitals or shops, or in outdoor areas, infected arthropods, such as ants, grasshoppers, cockroaches or fleas, for the destruction of these arthropods by swallowing them this lure.

EXAMPLE 2I

The form of the solution prepared with the following composition:

Active is ngredient 15%
The sulfoxide85%

The active ingredient is dissolved in dimethyl sulfoxide with stirring or heating as necessary. This solution may be injected or percutaneous application by pouring on domestic animals infected arthropods, or, after sterilization by filtration through a PTFE membrane (pore size 0.22 μm), parenteral injection, at a rate of application of from 1.2 to 12 ml per 100 kg of animal body weight.

EXAMPLE 2J

Wettable powder is prepared with the following composition:

The active ingredient50%
Atilan HRV5%
Aerosil5%
Celite PF40%

Atilan HRV absorb the Aerosol, which is then mixed with other ingredients and crushed in a hammer mill to obtain wettable powder, which may be diluted with water to a concentration of 0.001-2 wt.% active compounds and deposited on the hearth of infected arthropods, for example, the larvae of flies or nematodes of plants, spraying or domestic animals, or infected with the risk of infecting arthropods, spraying or dipping is whether by oral administration in drinking water for the destruction of arthropods.

EXAMPLE 2K

Bolus composition slow release form of pellets, containing the following components in varying percentage amounts (similar to that described for the previous songs), depending on the needs:

The active ingredient

Agent density

Agent slow release

Binder

Uniformly mixed ingredients formed into pellets, which are pressed into a ball (bolus) with a specific gravity of 2 or more. It can be administered orally ruminants pet for retention in the grid-scar (the second and first stomach of ruminants) to obtain a continuous slow release of the active compound over a prolonged period of time to destroy the infection of ruminants with Arthropoda.

EXAMPLE 2L

The slow release composition in the form of granules, beads, pellets or the like can be prepared with the following composition:

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

These components are mixed and then formed into a suitable shape by extrusion from the melt or by molding. This composition is applicable, n is the sample, to add in standing water or for the manufacture of collars or tags to attach to the pet to kill pests by slow release of the active ingredient.

EXAMPLE 2M

Dispersible granule in water is prepared with the following composition:

The active ingredient85% (max)
Polyvinylpyrrolidone5%
Clay attapulgite6%
Sodium lauryl sulfate2%
Glycerin2%

These ingredients are mixed in the form of a 45% suspension (slurry) with water, pulverized using a mill wet grinding until the particle size of 4 μm and then dried by spray drying to remove the water.

METHODS of APPLICATION of PESTICIDES

The following are typical test procedure using the compounds of this invention was carried out to determine parasiticides and pesticidal activity of the compounds of this invention.

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

The test container was filled with 10 adult Ctenocephalides felis. Glass cylinder closed at one end by parafilm and placed on top of the test container. Then the solution testseite has pietravalle in bovine blood and added to the glass cylinder. Processed Ctenocephalides felis kept in artificial dog test (blood 37°C, relative humidity of 40-60%; Ctenocephalides felis 20-22°C, relative humidity 40-60%) and the evaluation was performed at 24 and 48 hours after application. Rooms compounds 1-2, 1-8, 1-9, 1-10, 1-14, 1-15, 1-16, 1-17, 1-19, 1-34, 1-35, 1-36, 1-37, 1-38, 1-39, 1-40, 2-2, 2-8, 2-9, 2-10, 2-14, 2-16, 2-17, 2-19, 2-35, 2-36, 3-19 gave at least 90% destruction of Ctenocephalides felis at the test concentration of 5 ppm or less.

METHOD: Screening Diabrotica undecimpunctata (South blascoe dinosau)

Two days before applying corn seeds were soaked in water in a warm environment for the rapid induction of germination. One day before application, eggs Diabrotica undecimpunctata were transferred to one half of the Japanese filter paper, placed in a plastic Petri dish. After that sprouted seed corn was placed on a moistened pad next to this filter paper. At the egg gently pietravalle three drops of 200 microlitres solution of the test compound. The remaining solution was placed on the corn and then the Petri dish was closed. Processed eggs in Petri dishes kept in climatic chambers for 6 days. The transfer efficiency (the percentage of dead eggs and/or larvae compared to untreated control) was assessed after 6 days after application using a binocular microscope.

Non connect the deposits 1-17, 1-19, 1-35, 1-36, 1-38, 1-39, 2-9, 2-19, 2-35 and 2-36 gave at least 90% destruction of Diabrotica undecimpunctata at test concentrations of 10 ppm

METHOD: Screening Nephotettix cinciceps (rice leafhopper)

The sheets 12 in rice plants with long stems to 8 cm was immersed for 5 seconds in an aqueous solution prepared in the form of ready-made forms of the test compounds. After draining of the solution of the rice plants, thus treated, was placed in a Petri dish and was inhabited by approximately 20 larvae (L3 stage) Nephotettix cinciceps. The Petri dish was closed and then kept in a climate chamber (16 hours of light per day, 25°C, relative humidity 40-60%). After 6 days of incubation was determined mortality percentage of larvae cicadas.

Rooms compounds 1-8, 1-9, 1-19, 1-35, 1-37, 2-2, 2-8, 2-19 and 2-36 gave at least 98% mortality of larvae Nephotettix cinciceps at the test concentration of 100 ppm

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

Solutions of test compounds were placed dropwise on filter paper, dried and the filter paper were placed in test tubes and used to infect 10 adult Ctenocephalides felis. Processed Ctenocephalides felis kept in a climatic chamber (26°C, relative humidity 80%) and percentage efficacy was evaluated after 24 hours and 48 hours after application compared to untreated control.

Rooms with the of dinani 1-2, 8-2 8-10 gave at least 70% contact destruction Ctenocephalides felis at the test concentration of 1000 ppm

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

Solutions of test compounds were placed dropwise on filter paper, dried and the filter paper were placed in test tubes and were infected 20-30 larvae (L1) Rhipicephalus sanguineus and these tubes were closed with a clip. Processed Rhipicephalus sanguineus was kept in a climatic chamber (25°C, relative humidity 90%) and percentage efficacy was evaluated after 24 hours after application compared to untreated control.

Rooms compounds 1-2, 3-3, 8-8, 8-10 and 8-22 gave at least 70% contact destruction of Rhipicephalus sanguineus at the test concentration of 100 ppm

1. Way to destroy parasites in the animal body or on the body of the animal, providing for the introduction of this animal effective to kill parasites amount derivative of 5-substituted acylaminopyrazoles formula (I):

where

R1denotes CN;

W represents C-halogen;

R2denotes halogen;

R3means (C1-C3-halogenated, (C1-C3)-halogenoalkane;

R4denotes hydrogen, (C2-C 6)-alkenyl, (C2-C6)-quinil, (C3-C7-cycloalkyl, COR8, CO-(CH2)q-R9- - (C1-C4)-alkyl-(C1-C6)-alkoxy, -CO2-(CH2)q-R7, CO2R8, -CH2R7, OR8; or (C1-C6)-alkyl, substituted by one radical selected from the group consisting of halogen, (C1-C6)-alkoxy, (C3-C7)-cycloalkyl;

And means (C1-C12-alkylen;

R5denotes H, (C3-C6)-alkenyl, -(CH2)qR7or NR10R11provided that the last-mentioned radical m is 2; or denotes (C1-C6)-alkyl, unsubstituted; or, when a represents (C1-C12-alkylene and R5means (C1-C6)-alkyl, unsubstituted or substituted by one or more radicals halogen, one or more of the carbon atoms of R5may, together with S(O)mand one or more carbon atoms And form tetrahydrothieno;

R6means (C1-C6-halogenated;

R7denotes phenyl, unsubstituted or substituted (C1-C6)-alkoxy;

R8means (C1-C6)-alkyl;

R9denotes an unsubstituted tetrahydrofuranyl;

R 10means (C1-C6)-alkyl;

and R11means (C1-C6)-alkyl;

m, n and p each independently 0, 1 or 2;

q is 0 or 1; and

or pesticide acceptable salt.

2. The method according to claim 1, where the symbols and indices in formula (I) have the following meanings:

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 radical selected from the group consisting of halogen and (C1-C3)-alkoxy;

And means (C1-C4-alkylen;

R5represents -(CH2)qR7, (C1-C6)-alkyl or (C1-C6-halogenated; or, when R5means (C1-C6)-alkyl, one or more of the carbon atoms of the group R5may, together with a group S(O)mand one or more carbon atoms And form tetrahydrothieno;

R6means CF3, CF2Cl, CFCl2, CBrF2or CHF2;

R7denotes phenyl;

m and n are each independently 0, 1 or 2; and

q is 0 or 1.

3. The method according to claim 1, where the symbols and indices in the formula (a) have the following meanings:

R1denotes CN;

W denotes C-Cl;

R2denotes Cl;

R3means CF3or OCF3;

R4denotes hydrogen, (C2-C6)-alkenyl, (C2-C6)-quinil, (C3-C7-cycloalkyl, COR8, CO-(CH2)q-R9- - (C1-C4)-alkyl-(C1-C6)-alkoxy, -CO2-(CH2)q-R7, CO2R8, -CH2R7, OR8; or (C1-C6)-alkyl, substituted by one radical selected from the group consisting of halogen, (C1-C6)-alkoxy, (C3-C7)-cycloalkyl;

And means (C1-C6-alkylen;

R5means (C3-C6)-alkenyl, -(CH2)qR7or NR10R11provided that the last-mentioned radical m is 2; or denotes a (C1-C6)-alkyl or (C1-C6-halogenated;

R6means CF3, CF2Cl, CFCl2, CBrF2, CHF2;

R7denotes phenyl, unsubstituted or substituted (C1-C6)-alkoxy;

R8means (C1-C6)-alkyl;

R10means (C1-C6)-alkyl;

R11means (C1-C6)-alkyl;

m and n are each independently 0, 1 or 2;

< num="727"> q is 0 or 1.

4. Derivatives of 5-substituted alkalinisation formula (I):

where

R1denotes CN;

W represents C-halogen;

R2denotes halogen;

R3means (C1-C3-halogenated, (C1-C3)-halogenoalkane;

R4denotes hydrogen, (C2-C6)-alkenyl, (C2-C6)-quinil, (C3-C7-cycloalkyl, COR8, CO-(CH2)q-R9- - (C1-C4)-alkyl-(C1-C6)-alkoxy, -CO2-(CH2)q-R7, CO2R8, -CH2R7, OR8; or (C1-C6)-alkyl, substituted by one radical selected from the group consisting of halogen, (C1-C6)-alkoxy, (C3-C7)-cycloalkyl;

And means (C1-C12-alkylen;

R5denotes H, (C3-C6)-alkenyl, -(CH2)qR7or NR10R11provided that the last-mentioned radical m is 2; or denotes a (C1-C6)-alkyl, unsubstituted; or, when a represents (C1-C12-alkylene and R5means (C1-C6)-alkyl, unsubstituted or substituted by one or more radicals halogen, one or more of the carbon atoms of R5could the t, together with S(O)mand one or more carbon atoms And form tetrahydrothieno;

R6means (C1-C6-halogenated;

R7denotes phenyl, unsubstituted or substituted (C1-C6)-alkoxy;

R8means (C1-C6)-alkyl;

R9denotes an unsubstituted tetrahydrofuranyl;

R10means (C1-C6)-alkyl;

R11means (C1-C6)-alkyl;

m, n and p each independently 0, 1 or 2;

q is 0 or 1;

or pesticide acceptable salt.

5. Derivatives of 5-substituted alkalinisation formula (I) according to claim 4, where

R1denotes CN;

W represents C-halogen;

R2denotes halogen;

R3means (C1-C3-halogenated, (C1-C3)-halogenoalkane;

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

And means (C1-C12-alkylen;

R5denotes H, (C3-C6)-alkenyl, -(CH2)qR7or NR10R11provided that the last-mentioned radical S(O)mmeans SO2; or denotes (C1-C6)-alkyl, unsubstituted; or, when a represents C1-C12)-alkyl is n and R 5means (C1-C6)-alkyl, substituted by one or more radicals halogen, one or more of the carbon atoms of R5may, together with S(O)mand one or more carbon atoms And form tetrahydrothieno;

R6means (C1-C6-halogenated;

R7denotes phenyl, unsubstituted or substituted (C1-C6)-alkoxy;

R8means (C1-C6)-alkyl;

R9denotes an unsubstituted tetrahydrofuranyl;

R10means (C1-C6)-alkyl;

R11means (C1-C6)-alkyl;

m and n are each independently 0, 1 or 2;

q is 0 or 1.

6. Derivatives of 5-substituted alkalinisation formula (I) according to claim 4, where

R1denotes CN; R2denotes chlorine; R3means CF3or OCF3; W denotes C-Cl; R4denotes hydrogen or (C1-C6)-alkyl; R5means (C1-C6)-alkyl; R6means CF3; And means (C2-C3-alkylene and m and n each, independently, 0, 1, or 2,

or pesticide acceptable salt.

7. The use of compounds of formula (I) and their pesticide acceptable salts according to any one of claims 4 to 6 for the destruction of parasites in the animal body and on the body of the animal.

8. The use of compounds of formula (I) and their pesticide acceptable salts according to any one of claims 4 to 6 for the preparation of veterinary medicines.

9. Pesticide composition for use against arthropods, containing the compound of formula (I) or its pesticide acceptable salt as defined in any of claims 4-6, together with pesticide acceptable diluent or carrier and/or surface-active agent.



 

Same patents:

FIELD: organic chemistry.

SUBSTANCE: invention relates to new amide-type carboxamide derivatives of formula [1] , wherein X represents -N= or -CH= group; R1 represents halogen atom, lower alkyl and a like; R1 represents -CO-R21-R22 (meanings of R21 and R22 are as defined in claim 1); Y1 and Y2 are independently halogen atom, lower alkyl, lower alcoxy group, and a like; ring A represents phenyl and a like; or pharmaceutically acceptable salts thereof. Said derivatives are useful as FXa inhibitors. Also disclosed are pharmaceutical composition based on abovementioned compounds and uses thereof.

EFFECT: new amide-type carboxamide derivatives.

7 cl, 105 ex

FIELD: synthesis of biologically active compounds.

SUBSTANCE: invention relates to hydroxamate derivatives described by general formula I: , in which R1 represents H or linear C1-C6-alkyl; R2 hydrogen, С110-alkyl optionally substituted by 1-5 constituents selected from hydroxy, amino, hydroxyalkyl; C4-C9-cycloalkyl; aryl; C4-C9-heterocycloalkyl, C4-C9-heterocycloalkylalkyl containing 2 heteroatoms (nitrogen and/or oxygen); C4-C9-cycloalkylalkyl; arylalkyl; heteroarylalkyl containing 1-4 nitrogen atoms as heteroatoms; -(CH2)nC(O)R6, -(CH2)nOC(O)R6, -N(R12)C(O)-W; HONH-C(O)-CH=C(R1)arylalkyl, and (CH2)nR7; R3 and R4, identical or different, independently denote hydrogen, optionally OH-substituted C1-C6-alkyl; C(O)-O-W, or -N(R12)C(O)W; or R3 and R4 together with carbon atom, to which they are linked, represent C=O; or R2 together with carbon atom, to which it is linked, and R3 together with carbon atom, to which it is linked, can form C4-C9-heterocycloalkyl containing 2 nitrogen atoms as heteroatoms; or mixed aryl or non-aryl polyheterocyclic ring; R5 is selected from hydrogen; C1-C6-alkyl; C4-C9-cycloalkyl; C(O)-W; aryl optionally substituted by 1-2 constituents selected from halogen and hydroxyalkyl; heteroaryl containing nitrogen as heteroatom; arylalkyl; aromatic polycycle; polyheteroaryl containing 1-2 nitrogen atoms as heteroatoms and optionally substituted by 1-2 substituents selected from hydroxyalkyl, halogen, alkyl, and aryl; mixed aryl-nonaryl polyheterocycle containing nitrogen or oxygen atom as heteroatom and optionally substituted by groups -N-OH, =N-OH; n, n1, n2, and n3, identical or different, are independently selected from within a range of 0-6; X and Y, identical or different, are independently selected from hydrogen, halogen, and nitro group; or pharmaceutically acceptable salt thereof. Invention also relates to a pharmaceutical composition showing inhibitory activity toward hydroxamate derivative of general formula I in combination with one or several pharmaceutically acceptable carriers. Hydroxamate derivative of general formula I are also appropriate for treating proliferative disease and regulating p21 promoter.

EFFECT: enabled use of hydroxamate derivatives as deacetylase inhibitors.

42 cl, 6 tbl, 272 ex

FIELD: organic chemistry, medicine, pharmacy.

SUBSTANCE: invention describes novel compounds of the general formula (I) wherein p, R1, R2, R3 and A are determined in the invention description, their individual isomers and their pharmaceutically acceptable salts. Proposed compounds possess antagonistic effect with respect to muscarinic receptors that allows their using in treatment and prophylaxis of diseases yielding to treatment with muscarinic receptor antagonist. Also, invention describes a pharmaceutical composition containing these compounds.

EFFECT: valuable medicinal properties of compounds and pharmaceutical composition.

23 cl, 22 ex

FIELD: organic chemistry, medicine, pharmacy.

SUBSTANCE: invention relates to novel substituted derivatives of 4-phenyltetrahydroisoquinoline of the general formula (I): wherein R1, R2, R3 and R4 mean independently of one another hydrogen (H), fluorine (F), chloride (Cl), bromine (Br) atoms, CaH2a+1 wherein one or more atoms H are substituted with F, -NR11R12 or -SOj-R15 wherein a = 1-8; R11 and R12 mean independently of one another H, CeH2e+1 or CrrH2rr-1 wherein e = 1-4; rr = 3, 4, or in common with nitrogen atom to which they are bound form a cycle chosen from group consisting of pyrrolidinyl, piperidinyl, N-methylpiperazinyl, piperazinyl or morpholine; j = 1 or 2; R15 means CkH2k+1 wherein k = 1-8; R5 means CpH2p+1 or CssH2ss-1; p = 1-8; ss = 3-8; R6 means H; R7, R8 and R9 mean independently of one another mean -SOwR23, -NR32COR30, NR32CSR30, -NR32SObbR30, H, F, Cl, Br, -OH, -NH2, CeeH2ee+1, -NR40R41, -CONR40R41 or -COOR42 wherein w = 0, 1 or 2; bb = 2 or 3; R23 means NR25R26 wherein R25 and R26 mean independently of one another H or CzH2z+1, CzzH2zz-1 wherein z = 1-8; zz = 3-8 wherein in CzH2z+1 and CzzH2zz-1 one or more H atoms are substituted with fluorine atom and one or more CH2-groups are substituted with -C(=O) or NR27 wherein R27 means H or CaaH2aa+1 wherein aa = 1-4; or R25 and R26 in common with nitrogen atom to which they are bound form 5-, 6- or 7-membered cycle; R30 means H, CccH2cc+1, CyyH2yy-1, pyrrolydinyl, piperidinyl wherein in their cycles CH2-group can be substituted with oxygen atom (O) or -NR33; R32 and R33 mean independently of one another H or ChH2h+1 wherein cc = 1-8; yy = 3-8; h = 1-8 wherein in the group ChH2h+1 one or more hydrogen atoms are substituted with fluorine atom, and in the groups CccH2cc+1 and CyyH2yy-1 one or more hydrogen atoms can be substituted with fluorine atom, and CH2-group can be substituted with O or -NR31 wherein NR31 means H, methyl, ethyl, acetyl or -SO2CH3; or R30 means 6-membered heteroaryl with 1-4 nitrogen atoms, 0 or 1, S-atoms or 0, or 1 O-atom that represents unsubstituted or substituted with up to three substitutes chosen from group consisting of F, Cl, Br, J, CooH2oo+1 wherein one or more hydrogen atoms can be substituted with fluorine atom, -NO2 or -NR70R71 wherein oo = 1-8; R70 and R71 mean independently of one another H, CuuH2uu+1 or -COR72 wherein uu = 1-8; R72 means H, CvvH2vv+1 wherein vv = 1-8; ee = 1-8; R40 and R41 mean independently of one another H, CttH2tt+1 or -C(NH)NH2 wherein tt = 1-8 and wherein in the group CttH2tt+1 one or more CH2-groups can be substituted with NR44 wherein R44 means CggH2gg+1 wherein gg = 1-8; R42 means H or ChhH2hh+1 wherein hh = 1-8 being, however, two substitutes from group R7, R8 and R9 can't mean -OH simultaneously, and at least one residue from R7, R8 and R9 must be chosen from group consisting of -CONR40R41, -OvSOwR23, -NR32COR30, -NR32CSR30 and -NR32SObbR30. Also, invention relates to using above given compounds for preparing a medicinal agent. Also, invention considers a medicinal agent representing inhibitor of sodium-proton exchange of subtype III (NHE3) based on proposed compounds. Invention provides synthesis of novel compounds, a medicinal agent based on thereof for aims of treatment of such diseases as nervous system ischemia, insult and brain edema, in treatment of snore, shock, impaired respiratory impulse, as purgative agents, as agents against extoparasites, for prophylaxis of gall stones formation, as anti-atherosclerotic agents, agents against diabetes mellitus later complications, cancer diseases, fibrous diseases, endothelial dysfunction, hypertrophies and hyperplasia of organs and others.

EFFECT: valuable medicinal properties of compounds and medicinal agents.

21 cl, 15 tbl, 221 ex

FIELD: organic chemistry, medicine, pharmacy.

SUBSTANCE: invention describes derivatives of quinoline of the formula (I): wherein R1 and R2 are chosen independently from hydrogen atom, alkyl, cycloalkyl, cycloalkylalkyl, alkylcarbonyl, cycloalkylcarbonyl, phenyl, unsubstituted benzyl or benzyl substituted with halogen atom, cyano-group, trifluoromethyl, alkyl, alkoxy-group, benzylcarbonyl, pyridinyl, furyl, thiophenyl, indanyl, phenyl-SO2-, pyridinyl-SO2-, thiophenyl-SO2; or R1 and R2 in common with atom N to which they are added form piperidino-group, pyrrolidinyl, morpholinyl, azepanyl, 3,4-dihydro-1H-isoquinolinyl, and wherein heterocyclic ring is optionally substituted with one or some substitutes chosen independently from alkyl and alkoxy-group; R3 represents hydrogen atom, alkyl; R4 represents hydrogen atom; A in common with nitrogen atom that is added to quinoline ring represents pyrrolidinyl, azepanyl, and ring A is optionally substituted with one-three substitutes chosen independently from alkoxy-group, hydroxyalkyl, alkoxyalkyl. Also, invention describes methods of synthesis of quinoline derivatives of the formula (I). Proposed compounds can be used as components of pharmaceutical formulations in treatment or prophylaxis of arthritis, cardiovascular diseases, diabetes mellitus, renal insufficiency, disorders in food eating and obesity.

EFFECT: valuable medicinal properties of compounds and pharmaceutical composition.

20 cl, 122 ex

FIELD: organic chemistry, medicine, pharmacy.

SUBSTANCE: invention relates to derivatives of piperidine of the general formula (I): or their pharmaceutically acceptable salts wherein rings A and B represent optionally substituted benzene rings; R1 represents alkyl, hydroxyl, thiol, carbonyl, sulfinyl, unsubstituted or substituted sulfonyl group and others; R2 represents hydrogen atom, hydroxyl, amino-group, alkyl, unsubstituted or substituted carbonyl group or halogen atom; Z represents oxygen atom or group -N(R3)- wherein R3 and R4 represent hydrogen atom or alkyl group under condition that N-acetyl-1-benzyloxycarbonyl-2-phenyl-4-piperidineamine is excluded. Compounds of the formula (I) or their salts possess antagonistic activity with respect to tachykinin NK1-receptors and can be used in medicine in treatment and prophylaxis of inflammatory, allergic diseases, pain, migraine, diseases of central nervous system, digestive organs and others.

EFFECT: valuable medicinal properties of compounds and pharmaceutical composition, improved method of treatment.

18 cl, 138 tbl, 527 ex

FIELD: organic chemistry, agriculture.

SUBSTANCE: invention relates to novel pyrrole carboxylic acid amides or pyrrole thiocarboxylic acid amides of the formula (I): wherein X represents oxygen atom (O), sulfur atom (S); R1 represents -CF3- or -CF2H-group; R2 represents (C1-C3)-alkyl or (C1-C3)-alkoxy-(C1-C3)-alkyl; R3 represents hydrogen (H) or fluorine (F) atom; Q represents compounds of the formulas wherein R4 represents (C6-C14)-bicycloalkyl, (C6-C14)-bicycloalkenyl, (C6-C14)-bicycloalkadienyl, group of the formula: wherein R7, R8 and R9 represent independently of one another (C1-C3)-alkyl or (C1-C3)-halogenalkyl or group of the formula: wherein R10 and R11 represent H; R5 and R6 represent H. Compounds of the formula (I) can be used for protection of plants against infection with phytopathogenic fungi. Also, invention describes a method for synthesis of these compounds.

EFFECT: valuable properties of compounds.

20 cl, 4 sch, 8 tbl, 17 ex

FIELD: organic chemistry, medicine, pharmacy.

SUBSTANCE: invention relates to novel derivatives of benzimidazole of the general formula (I): wherein A represents -CH2- or -C(O)-; Y represents -S- or -NH-; R1 and R2 represent independently hydrogen atom, (C1-C8)-alkyl, (C5-C9)-bicycloalkyl optionally substituted with one or some similar or different (C1-C6)-alkyl radicals, or radical of the formula -(CH2)n-X wherein X represents amino-group, (C3-C7)-cycloalkyl and other values of radicals also given in the invention claim; R3 represents -(CH2)p-W-(CH2)p'-Z3 wherein W3 represents a covalent bond, -CH(O)- or -C(O)-; Z3 represents (C1-C6)-alkyl, aryl radical, heteroaryl and other values of radical also; V3 represents -O-, -S-, -C(O)-, -C(O)-O-, -SO2- or a covalent bond; Y3 represents (C1-C6)-alkyl radical optionally substituted with one or some halogen-radicals, amino-group, di-((C1-C6)-alkyl)-amino-group, phenylcarbonylmethyl, heterocycloalkyl or aryl radicals; p, p' and p'' represent independently a whole number from 0 to 4; R4 represents radical of the formula: -(CH2)s-R''4 wherein R''4 represents heterocycle comprising at least one nitrogen atom and optionally substituted with (C1-C6)-alkyl or aralkyl, and other values of radicals given in the invention claim also. Also, invention relates to a pharmaceutical composition showing antagonistic property with respect to GnRH and based on these compounds. Also, using above proposed compounds for preparing a medicament is considered. Invention provides synthesis of novel compounds, preparing pharmaceutical composition and medicament based on thereof in aims for treatment of such diseases as endometriosis, fibroma, polycystic ovary, breast, ovary and endometrium cancer, gonadotropic hypophysis desensitization in medicinal stimulation of ovary in fertility treatment in females.

EFFECT: valuable medicinal properties of compounds and pharmaceutical composition.

18 cl, 2 tbl, 538 ex

FIELD: organic chemistry, medicine, pharmacy.

SUBSTANCE: invention relates to novel derivatives of sulfonamide of the general formula (I): wherein A means a substitute chosen from 5- or 6-membered heteroaromatic ring comprising 1 or 2 heteroatoms chosen from oxygen (O), nitrogen (N) or sulfur (S) optionally substituted with 1 or 2 halogen atoms, (C1-C4)-alkyl or phenyl radical, or 5- or 6-membered heteroaryl radical comprising 1 or 2 atoms of O, N or S; bicyclic heteroaromatic ring comprising from 1 to 3 heteroatoms chosen from O, N or S and optionally substituted with 1 or 2 halogen atoms or (C1-C4)-alkyl; R1 means hydrogen atom (H), (C1-C4)-alkyl, benzyl; n means 0, 1, 2, 3 or 4; R2 means -NRR5 or the group of the formula: wherein a dotted line means optional chemical bond; R, R4 and R5 mean independently H or (C1-C4)-alkyl; or one of its physiologically acceptable salts. Compounds of the formula (1) possess antagonistic activity with respect to serotonin HT6-receptors that allows their using in pharmaceutical composition and for preparing a medicament.

EFFECT: valuable medicinal properties of derivatives and pharmaceutical composition.

10 cl, 2 tbl, 7 ex

FIELD: organic chemistry, chemical technology.

SUBSTANCE: invention describes a method for synthesis of novel R-methyl-derivatives of 3,5-diamino-1,2,4-triazole of the general formula (I):

wherein R means benzene ring possibly substituted with one or some substitutes, such as branched or linear (C1-C4)-alkyl, -O-(C1-C4)-alkyl, -N-[(C1-C4)-alkyl]2, halogen atom, nitro-group; or R means naphthalene or heterocycle of the order: thiophene, furan substituted possibly with methyl group. Method is carried out by successive interaction of 1-acetyl-3,5-diamino-1,2,4-triazole (II) with sodium hydroxide, acetic acid and aldehyde of the formula: R-C(=O)H (III) and sodium boron hydride in the mole ratio of reagents (II) : sodium hydroxide : (III) : sodium boron hydride = 1:(1.0-1.2):(0.9-1.0):(1.2-2.0), respectively. Method provides decreasing the cost of compounds of the formula (I) and enhancing safety of process in their synthesis. Synthesized compounds can be used in manufacture of medicaments and biologically active substances.

EFFECT: improved method of synthesis, valuable properties of compounds.

2 cl, 13 ex

FIELD: organic chemistry, medicine, pharmacy.

SUBSTANCE: invention describes novel compounds of the general formula (I) wherein p, R1, R2, R3 and A are determined in the invention description, their individual isomers and their pharmaceutically acceptable salts. Proposed compounds possess antagonistic effect with respect to muscarinic receptors that allows their using in treatment and prophylaxis of diseases yielding to treatment with muscarinic receptor antagonist. Also, invention describes a pharmaceutical composition containing these compounds.

EFFECT: valuable medicinal properties of compounds and pharmaceutical composition.

23 cl, 22 ex

FIELD: organic chemistry, pharmacy.

SUBSTANCE: invention relates to anthranylamidepyridine amides of selective effect as inhibitors of VEGFR-2 and VEGFR-3. Invention describes compounds of the general formula (I): wherein A, B and D represent independently of one another nitrogen atom or carbon atom wherein at least one nitrogen atom is in a ring; E represents aryl comprising 6-12 ring carbon atoms or heteroaryl comprising 5 or 6 ring atoms and comprising in ring instead carbon atom similar or different heteroatoms chosen from nitrogen or sulfur atoms, or represents group -COOR8, -CONR2R3 or -C≡C-R9; G represents nitrogen atom or group -C-X; L represents nitrogen atom or group -C-X; M represents nitrogen atom or group -C-X; Q represents nitrogen atom or group -C-X and wherein a ring comprises maximally one nitrogen atom; X represents hydrogen atom; W represents hydrogen or halogen atom; R1 represents aryl similarly or differently optionally mono- or multi-substituted with halogen atom, hydroxy-, (C1-C6)-alkoxy-group, (C1-C6)-alkyl or group =O and wherein aryl comprises 6-12 ring carbon atoms, or heteroaryl comprising from 3 to 16 ring atoms and comprising in ring instead carbon one or more similar or different heteroatoms, such as oxygen, nitrogen or sulfur and it can be mono-, bi- or tricyclic and condensed additionally condensed with benzene ring; R2 and R3 represent independently of one another hydrogen atom or aryl similarly or differently mono- or multi-substituted with halogen atom, cyano-group, (C1-C6)-alkyl, phenyl, hydroxy-(C1-C6)-alkyl, halogen-(C1-C6)-alkyl or group -NR6R7, -OR5, (C1-C6)-alkyl-OR5-(C1-C6)-alkyl, (C3-C6)-cycloalkyl, (C3-C6)-cycloalkenyl wherein aryl comprises 6-12 ring carbon atoms, or heteroaryl comprising from 3 to 6 ring atoms and comprising in ring instead carbon one or more heteroatoms, such as nitrogen or sulfur; or R2 and R3 in common with nitrogen atom form (C3-C8)-ring that can comprise optionally one more nitrogen or oxygen atom or it can comprise group -N(R10); R5 represents hydrogen atom; R6 and R7 represent independently of one another hydrogen atom or (C1-C6)-alkyl; R8 represents (C1-C6)-alkyl mono- or multi-substituted optionally with halogen atom or benzyl; R9 represents hydrogen atom or tri-(C1-C6)-alkylsilyl; R10 represents hydrogen atom or (C1-C6)-alkyl, and their isomers, enantiomers and salts also. Also, invention describes a medicinal agent based on compounds of the formula (I). Invention provides synthesis of novel compounds possessing valuable biological properties.

EFFECT: valuable medicinal properties of compounds.

8 cl, 2 tbl, 162 ex

FIELD: organic chemistry, medicine, pharmacy.

SUBSTANCE: invention relates to novel derivatives of pyrimidine of the general formula (I): or its pharmaceutically acceptable salts or esters hydrolyzed in vivo and possessing properties of selective inhibitor of cyclin-dependent kinases, such as CDK-2, and inhibiting proliferation of cells. Compounds can be used in preparing medicinal agents used in treatment of cancer diseases. In compounds of the formula (I) R1 represents halogen atom; p = 0 or 1; R2 represents sulfamoyl or group B-E-; q = 0 or 1 wherein p + q = 1; R3 represents hydrogen atom, (C1-C6)-alkyl wherein R3can be substituted optionally at carbon atom with one or some M; R4 represents (C1-C6)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (C3-C8)-cycloalkyl wherein R4 can be substituted optionally with one or some M; or R3 and R4 taken with nitrogen atom to which they are bound form heterocyclic ring substituted optionally at carbon atom with one or some M wherein if indicated heterocyclic ring comprises group -NH then nitrogen atom can be substituted optionally with group chosen from Q; B is chosen from (C1-C6)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (C3-C8)-cycloalkyl, (C3-C8)-cycloalkyl-(C1-C6)-alkyl, phenyl-(C1-C6)-alkyl or (heterocyclic group)-(C1-C6)-alkyl wherein B can be substituted optionally at carbon atom with one or some D and wherein indicated heterocyclic group comprises group -NH- then nitrogen atom can be substituted optionally with group chosen from G; E represents -S(O)r- or -N(Ra)SO2- wherein Ra represents hydrogen atom or (C1-C6)-alkyl and r = 2; D is chosen independently from halogen atom, nitro-, cyano-, hydroxy-, amino-group, (C1-C6)-alkyl, (C1-C6)-alkoxy-, N-(C1-C6)-alkylamino-, N,N-((-C1-C6)-alkyl)2-amino-, (C1-C6)-alkanoylamino-group, (C1-C6)-alkyl-S(O)a wherein a = 0-2, wherein D can be substituted optionally at carbon atom with one or some V; M is chosen independently from halogen atom, nitro-, cyano-, hydroxy-group, (C1-C6)-alkyl, (C1-C6)-alkoxy-, N,N-((C1-C6)-alkyl)2-amino-group, (C1-C6)-alkoxycarbonyl, (C3-C8)-cycloalkyl or heterocyclic group wherein M can be substituted optionally at carbon atom with one or some P; P, X and Y are chosen independently from hydroxy-group, methyl, methoxy-, dimethylamino-group; G and Q are chosen independently from (C1-C4)-alkyl, (C1-C4)-alkylsulfonyl, (C1-C4)-alkoxycarbonyl wherein Q can be substituted optionally at carbon atom with one or some X. Also, invention relates to methods for synthesis of compounds, preparing pharmaceutical compositions based on thereof and to a method for inhibition of proliferation of cells.

EFFECT: valuable medicinal properties of compounds and pharmaceutical compositions, improved method of inhibition, improved method of synthesis of compounds.

15 cl, 2 sch, 133 ex

FIELD: organic chemistry, medicine, oncology, pharmacy.

SUBSTANCE: invention relates to novel C-2'-methylated derivatives of paclitaxel of the formula (I): wherein R represents trifluoromethyl group, phenyl, 2-furyl, 2-thienyl; R1 represents tert.-butoxycarbonyl or benzoyl group; R2 represents hydroxy-group; R3 means hydrogen atom or in common with R2 forms residue of cyclic carbonate of the formula: under condition that when R3 means hydrogen atom then R is not phenyl. Also, invention relates to a pharmaceutical composition based on thereof and using for preparing medicinal agents possessing an antitumor activity. Invention provides preparing novel derivatives of paclitaxel that possess antitumor activity.

EFFECT: valuable medicinal property of derivatives and pharmaceutical composition.

4 cl, 1 tbl, 6 ex

FIELD: organic chemistry of natural compounds, medicine, oncology.

SUBSTANCE: invention relates to new compounds - C7-ester-substituted taxanes of the general structural formula:

wherein R2 represents benzoyloxy-group; R7 represents R7aCOO-; R10 represents hydroxy-group; X3 represents (C1-C8)-alkyl, (C2-C8)-alkenyl, (C2-C8)-alkynyl or 5- or 6-membered heteroaryl group comprising heteroatom taken among oxygen (O), nitrogen (N) and sulfur (S) atoms; X5 represents -COX10 wherein X10 represents (C1-C8)-alkyl, (C2-C8)-alkenyl, phenyl or 5- or 6-membered heteroaryl group comprising heteroatom taken among O, N and S; or it (X5) represents -COOX10 wherein X10 represents (C1-C8)-alkyl or (C2-C8)-alkenyl; R7a represents (C1-C20)-alkyl or (C2-C20)-alkenyl; Ac represents acetyl group. These compounds possess an anti-tumor activity. Also, invention relates to a method for inhibition of tumor growth in mammals and to a pharmaceutical composition based on synthesized compounds. Invention provides preparing new derivatives of taxanes possessing the enhanced anti-tumor activity and reduced toxicity as compared with taxol and taxoter.

EFFECT: improved and valuable medicinal properties of compounds.

39 cl, 4 tbl, 10 ex

FIELD: pharmaceutical chemistry, medicine.

SUBSTANCE: present invention relates to new heterocyclic derivatives having calpain inhibition activity or oxygen reactive form recovering entrapping activity of formula I

1, wherein Het represent monocyclic 5-6-membered hetericyclic radical containing 1-2 heteroatoms selected from O or N; A represents A1

2, A'1 3, A2 4, A3 5 and A4 6; X represent -(CH2)n-, -(CH2)n-CO-, -N(R45)-CO-(CH2)n-CO, -CO-N(R45)-D-CO-, -N(R45)-(CH2)n-CO-, -N(R45)-CO-C(R46R47)-CO-, -O-(CH2)n-CO-, -N(R45)-CO-NH-C(R46R47)-CO-, -CO-N(R45)-C(R46R47)-CO- or -Z-CO Y represents -(CH2)p-, C(R53R54)-(CH2)p-, C(R53R54)-CO-; R1 represents hydrogen, group CR3 or oxo; R3 represents hydrogen, monocyclic saturated 6-membered heterocycloalkylcarbonyl, wherein heterocycle contains two heteroatoms selected from nitrogen or oxygen, C1-C6-alkylcarbonyl, phenylcarbonyl or phenyl(C1-C6)-alkylcarbonyl optionally substituted with NR4R5, or R4 and R5 independently represent C1-C6-alkyl; R2 represents hydrogen, and pharmaceutical compositions containing the same.

EFFECT: new heterocyclic drugs.

18 cl, 37 ex

FIELD: organic chemistry, herbicides, agriculture.

SUBSTANCE: invention describes derivatives of 2-amino-1,3,5-triaziene of the formula (I): wherein R1 means phenyl or alkyl with from 1 to 6 carbon atoms that can be substituted with one or some radicals taken among halogen atom and cyano-group; R2 means unsubstituted cyclopropyl, cyclobutyl or cyclopentyl groups or substituted that with radical taken among halogen atom and alkyl with from 1 to 4 carbon atoms, or furyl, or tetrahydrofuryl; R3 means radical of the formula -N(B1-D1)(B2-D2); R4 means radical of the formula -B3-D3; A1 means direct alkylene with 1-5 carbon atoms or direct alkenylene with 2-5 carbon atoms; A2 means a direct bond or direct alkylene with 1-4 carbon atoms; B1, B2 and B3 mean a direct bond; D1, D2 and D3 mean hydrogen atom; (X)n means a number of X substitutes wherein X means independently halogen atom, nitro-group or unsubstituted alkyl with 1-6 carbon atoms or substituted that with one or some radicals taken among halogen atom and alkoxy-group with 1-6 carbon atoms; n = 0, 1 or 2 and wherein the total sum of carbon atoms in radicals A1 and A2-R2 is at least 6 carbon atoms. Also, invention describes the herbicide agent containing compound of the formula (I) and additives used usually for plants protection and a method for control of hazard plants and using the effective dose of compound of the formula (I) for treatment of plants or planting surface. Invention provides preparing effective herbicides.

EFFECT: valuable properties of compounds.

7 cl, 45 tbl, 4 ex

FIELD: organic chemistry, pharmaceutical industry, medicine.

SUBSTANCE: invention relates to new derivatives of S-substituted N-1-[(hetero)aryl]alkyl-N'-1-[(hetero)aryl]alkylisothioureas of general formula I

in form of free base and salts with pharmaceutically accepted acids, as well as racemate, individual optical isomers or mixture thereof. In formula R1, R2, R3, R4, Y and Z are as described in specification. Compounds of present invention are capable to potentiate (positively modulate) AMPA/KA glutamate receptors and simultaneously to block transmembrane currents induced by activation of NMDA glutamate receptors. Also disclosed are method for production of said compounds, including optical isomers; pharmaceutical composition; method for investigation of glutamatergic system, and method for Alzheimer's disease, treatment; as well as method for extreme retentiveness of memory by administering of effective amount of claimed compounds.

EFFECT: new pharmaceutically active compounds for Alzheimer's disease treatment.

23 cl, 1 tbl, 11 ex

FIELD: organic chemistry, chemical technology, medicine, biochemistry, pharmacy.

SUBSTANCE: invention relates to new derivatives of sulfonamides of the formula (I) or their pharmaceutically acceptable salts wherein R1 means -OH or -NHOH; R2 means hydrogen atom; R3 means alkyl, alkoxyalkyl, arylalkyl, pyridylalkyl or morpholinylalkyl; A means piperidyl or tetrahydrofuranyl; n = 0; E means a covalent bond; (C1-C4)-alkylene, -C(=O)-, -C(=O)O- or -SO2-; X means hydrogen atom, alkyl, aryl, arylalkyl, alkoxyalkyl, morpholinyl or tetrahydropyranyl; each among G and G' means -C(R5)=C(R5') wherein R5 and R5' mean hydrogen atom; M means the group -CH-; z means the group -(CR7R7')a-L-R8 wherein a = 0 and each among R7 and R7' means hydrogen atom; L means a covalent bond; R8 means halogen atom or alkoxy-group. Compounds of the formula (I) are inhibitors of metalloproteases and can be used for treatment of arthritis, cancer tumors and other diseases.

EFFECT: valuable medicinal properties of compounds.

15 cl, 7 tbl, 56 ex

The invention relates to new chemical compounds of the heterocyclic series, with pronounced anticalcium activity, which may find application in medical practice in the treatment and prevention of cardiovascular diseases and represent derivatives of 2-N-1-benzopyran-2-it General formula I

where R and R1have the meanings indicated in the claims

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

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