2-alkyl-cycloalk(en)yl-carboxamides

FIELD: chemistry.

SUBSTANCE: described is 2-alkyl-cycloalk(en)yl-carboxamides of formula

, in which X, s, R1 , L, R2 and A assume values given in the formula of invention, a method of producing said compounds, an agent and use of said compounds against unwanted microorganisms.

EFFECT: higher activity compared to existing compounds, low toxicity and high toleration by plants.

6 cl, 8 tbl, 6 ex

 

The present invention relates to new 2-alkyl-cyclol(EN)yl-carboxamide, several processes for their preparation and to their use for controlling undesirable microorganisms.

It is known that various carboxamide have the properties of fungicides (see, for example, international application WO 98/03495, WO 98/03486 and European patent application EP-A 0589313). So, the fame gained some 2-alkyl-cycloalkyl-carboxamide, as, for example, N-(2-Deut-butylcyclohexyl)-2-methyl-4,5-dihydrofuran-3-carboxamide described in international application WO 98/03495, N-[2-(2-ethylbutyl)cyclohexyl]-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide described in international application WO 98/03486, and N-(2-Deut-Butylcyclohexyl)-2-methyl-4-(trifluoromethyl)-1,3-thiazole-5-carboxamide described in European patent application EP-A 0589313. These substances have good efficiency, but in some cases, for example when a small expense, it leaves much to be desired.

Were detected new 2-alkyl-cyclol(EN)yl-carboxamide formula (I),

in which

X is-CR3R4R5or SiR49R50R51

s means 1 or 2,

R1denotes hydrogen, alkyl with 1-8 carbon atoms, alkylsulfonyl with 1-6 carbon atoms, alkylsulfonyl with 1 to 6 carbon atoms, C1-C4-alkoxy-C1-C4-alkyl, the cycle is alkyl with 3 to 8 carbon atoms; halogenated with 1-6 carbon atoms, halogenation with 1-4 carbon atoms, halogenacetylenes with 1-4 carbon atoms, halogen alkylsulfonyl with 1 to 4 carbon atoms, halogen-C1-C4-alkoxy-C1-C4-alkyl, halogenosilanes with 3-8 carbon atoms, in each case with 1-9 atoms of fluorine, chlorine and/or bromine; formyl, formyl-C1-C3-alkyl, (C1-C3-alkyl)carbonyl-C1-C3-alkyl, (C1-C3-alkoxy)carbonyl-C1-C3-alkyl; halogen-(C1-C3-alkyl)carbonyl-C1-C3-alkyl, halogen-(C1-C3-alkylamino)carbonyl-C1-C3-alkyl, in each case 1 to 13 fluorine atoms, chlorine and/or bromine;

(C1-C8-alkyl)carbonyl, (C1-C8-alkoxy)carbonyl, (C1-C4-alkoxy-C1-C4-alkyl)carbonyl, (C3-C8-cycloalkyl)carbonyl; (C1-C6-halogenated)carbonyl, (C1-C6-halogenoalkane)carbonyl, (halo-C1-C4-alkoxy-C1-C4-alkyl)carbonyl, (C3-C8-halogenosilanes)carbonyl, in each case with 1-9 atoms of fluorine, chlorine and/or bromine; or-C(=O)C(=O)R6, -CONR7R8or-CH2NR9R10,

L means L1or L2,

L1means3-C7-cycloalkyl-1,2-ene(C3-C7-cycloalkyl-1,2-diyl), PR is necessary, having from 1 to 4 identical or different substituents from the series comprising fluorine, chlorine, alkyl with 1-4 carbon atoms or haloalkyl with 1-4 carbon atoms,

L2means cyclohexadien (cyclohexanediyl), optionally having from 1 to 4 identical or different substituents from the series comprising fluorine, chlorine, alkyl with 1-4 carbon atoms or haloalkyl with 1-4 carbon atoms,

R2means hydrogen, halogen, alkyl with 1-4 carbon atoms or halogenated with 1-4 carbon atoms, with 1-9 atoms of fluorine, chlorine and/or bromine,

R3means halogen, alkyl with 1-8 carbon atoms or halogenated with 1-6 carbon atoms, with 1 to 13 fluorine atoms, chlorine and/or bromine,

R4means halogen, alkyl with 1-8 carbon atoms or halogenated with 1-6 carbon atoms, with 1 to 13 fluorine atoms, chlorine and/or bromine,

R5means hydrogen, halogen, alkyl with 1-8 carbon atoms or halogenated with 1-6 carbon atoms, with 1 to 13 fluorine atoms, chlorine and/or bromine,

R3and R4in addition, together with the carbon atom to which they are bound, form a 3-6-membered carbocyclic or heterocyclic, saturated or unsaturated ring, optionally, zamienne halogen, alkyl with 1-4 carbon atoms, alkoxygroup with 1-4 carbon atoms, haloalkyl with 1-4 carbon atoms or alkylamino with 1-4 carbon atoms,

R49and R50independently of one another denote hydrogen, al the sludge with 1-8 carbon atoms, alkoxygroup with 1-8 carbon atoms, C1-C4-alkoxy-C1-C4-alkyl, C1-C4-alkylthio-C1-C4is alkyl or halogenated with 1-6 carbon atoms,

R51denotes hydrogen, alkyl with 1-8 carbon atoms, alkoxygroup with 1-8 carbon atoms, C1-C4-alkoxy-C1-C4-alkyl, C1-C4-alkylthio-C1-C4-alkyl, alkenyl with 2-8 carbon atoms, quinil with 2-8 carbon atoms, halogenated with 1-6 carbon atoms, halogenoalkanes with 2-6 carbon atoms, halogenoalkanes with 2-6 carbon atoms, cycloalkyl with 3-6 carbon atoms, or in each case optionally substituted phenyl or phenylalkyl,

R6denotes hydrogen, alkyl with 1-8 carbon atoms, alkoxygroup with 1-8 carbon atoms, C1-C4-alkoxy-C1-C4-alkyl, cycloalkyl with 3-8 carbon atoms, halogenated with 1-6 carbon atoms, halogenated-alkoxygroup with 1-6 carbon atoms, halogen-C1-C4-alkoxy-C1-C4-alkyl, halogenosilanes with 3-8 carbon atoms, in each case with 1-9 atoms of fluorine, chlorine and/or bromine,

R7and R8independently of one another denote hydrogen, alkyl with 1-8 carbon atoms, C1-C4-alkoxy-C1-C4-alkyl, cycloalkyl with 3-8 carbon atoms, halogenated with 1-8 carbon atoms, halogen-C1-C4-alkoxy-C 1-C4-alkyl, halogenosilanes with 3-8 carbon atoms, in each case with 1-9 atoms of fluorine, chlorine and/or bromine,

R7and R8in addition, together with the nitrogen atom to which they are linked, form a saturated a heterocycle with 5 to 8 atoms in the ring, optionally substituted one or more times by halogen or alkyl with 1-4 carbon atoms, with identical or different substituents, and the heterocycle may contain 1 or 2 are not adjacent to each other heteroatoms from the group comprising oxygen, sulfur or NR11,

R9and R10independently of one another denote hydrogen, alkyl with 1-8 carbon atoms, cycloalkyl with 3-8 carbon atoms, halogenated with 1-8 carbon atoms, halogenosilanes with 3-8 carbon atoms, in each case with 1-9 atoms of fluorine, chlorine and/or bromine,

R9and R10in addition, together with the nitrogen atom to which they are linked, form a saturated cycle with 5 to 8 atoms in the ring, optionally substituted one or more times by halogen or alkyl with 1-4 carbon atoms, with identical or different substituents, and the heterocycle may contain 1 or 2 are not adjacent to each other heteroatoms from the group comprising oxygen, sulfur or NR11,

R11means hydrogen or alkyl with 1-6 carbon atoms,

A represents the residue of formula (is 1)

in which

R12means hydrogen, cyano, halogen, the nitro-group, alkyl with 1-4 carbon atoms, alkoxygroup with 1-4 carbon atoms, alkylthiols with 1-4 carbon atoms, cycloalkyl with 3-6 carbon atoms, halogenated with 1-4 carbon atoms, halogenlampe or halogenation, in each case with 1 to 5 halogen atoms, aminocarbonyl group or aminocarbonyl-C1-C4-alkyl,

R13means hydrogen, halogen, cyano, alkyl with 1-4 carbon atoms, alkoxygroup with 1-4 carbon atoms or alkylthiols with 1-4 carbon atoms,

R14denotes hydrogen, alkyl with 1-4 carbon atoms, hydroxyalkyl with 1-4 carbon atoms, alkenyl with 2-6 carbon atoms, cycloalkyl with 3-6 carbon atoms, C1-C4-alkylthio-C1-C4-alkyl, C1-C4-alkoxy-C1-C4-alkyl, halogenated with 1-4 carbon atoms, C1-C4-allogenicity-C1-C4-alkyl, C1-C4-halogen-alkylalkoxy-C1-C4-alkyl, in each case with 1 to 5 halogen atoms, or phenyl,

or

A represents the residue of formula (A2)

in which

R15and R16independently of one another denote hydrogen, halogen, alkyl with 1-4 carbon atoms or halogenated with 1-4 carbon atoms and 1-5 atoms is halogen,

R17means halogen, cyano or alkyl with 1-4 carbon atoms, or halogenated with 1-4 carbon atoms or halogenlampe with 1-4 carbon atoms, in each case with 1 to 5 halogen atoms

or

A represents the residue of formula (A3)

in which

R18and R19independently of one another denote hydrogen, halogen, alkyl with 1-4 carbon atoms or halogenated with 1-4 carbon atoms and 1 to 5 halogen atoms,

R20means hydrogen, halogen, alkyl with 1-4 carbon atoms or halogenated with 1-4 carbon atoms and 1 to 5 halogen atoms,

or

A represents the residue of formula (A4)

in which

R21means hydrogen, halogen, a hydroxy-group, cyano, alkyl with 1-6 carbon atoms, halogenated with 1-4 carbon atoms, halogenlampe with 1-4 carbon atoms or halogenation 1-4 carbon atoms, in each case with 1 to 5 halogen atoms,

or

A represents the residue of formula (A5)

in which

R22means halogen, a hydroxy-group, cyano, alkyl with 1-4 carbon atoms, alkoxygroup with 1-4 carbon atoms, alkylthiols with 1-4 carbon atoms, halogenated with 1-4 carbon atoms, halogenation 1-4 carbon atoms or halogenlampe with 1-4 carbon atoms,in each case with 1 to 5 halogen atoms,

R23means hydrogen, halogen, cyano, alkyl with 1-4 carbon atoms, alkoxygroup with 1-4 carbon atoms, alkylthiols with 1-4 carbon atoms, halogenated with 1-4 carbon atoms, halogenlampe with 1-4 carbon atoms, in each case with 1 to 5 halogen atoms, alkylsulfonyl group with 1-4 carbon atoms or alkylsulphonyl group with 1-4 carbon atoms,

or

A represents the residue of formula (A6)

in which

R24means alkyl with 1-4 carbon atoms or halogenated with 1-4 carbon atoms, with 1 to 5 halogen atoms, R25means alkyl with 1-4 carbon atoms,

Q1means S (sulfur),

O (oxygen), SO, SO2or CH2,

p denotes 0, 1 or 2, and if R represents 2, under R25understand the same or different residues,

or

A represents the residue of formula (A7)

in which

R26means alkyl with 1-4 carbon atoms or halogenated with 1-4 carbon atoms, with 1 to 5 halogen atoms,

or

A represents the residue of formula (A8)

in which

R27means alkyl with 1-4 carbon atoms or halogenated with 1-4 carbon atoms, with 1 to 5 halogen atoms,

or

A represents the residue of formula (A9)

in which

R28and R29 independently of one another denote hydrogen, halogen, amino, alkyl with 1-4 carbon atoms or halogenated with 1-4 carbon atoms, with 1 to 5 halogen atoms,

R30means hydrogen, halogen, alkyl with 1-4 carbon atoms or

halogenated with 1-4 carbon atoms, with 1 to 5 halogen atoms,

or

A represents the residue of formula (a10)

in which

R31and R32independently of one another denote hydrogen, halogen, an amino group, a nitrogroup, alkyl with 1-4 carbon atoms or halogenated with 1-4 carbon atoms, with 1 to 5 halogen atoms,

R33means hydrogen, halogen, alkyl with 1-4 carbon atoms or halogenated with 1-4 carbon atoms, with 1 to 5 halogen atoms,

or

A represents the residue of formula (A11)

in which

R34means hydrogen, halogen, amino, alkylamino with 1-4 carbon atoms, di(C1-C4-alkyl)amino, cyano, alkyl with 1-4 carbon atoms or halogenated with 1-4 carbon atoms, with 1 to 5 halogen atoms,

R35means halogen, alkyl with 1-4 carbon atoms or halogenated with 1-4 carbon atoms, with 1 to 5 halogen atoms,

or

A represents the residue of formula (A12)

in which

R36means hydrogen, halogen, amino, alkylamino from 1-4 at the Mami carbon di(C1-C4-alkyl)amino, cyano, alkyl with 1-4 carbon atoms or halogenated with 1-4 carbon atoms, with 1 to 5 halogen atoms,

R37means halogen, alkyl with 1-4 carbon atoms or halogenated with 1-4 carbon atoms, with 1 to 5 halogen atoms,

or

A represents the residue of formula (A13)

in which

R38means halogen, alkyl with 1-4 carbon atoms or halogenated with 1-4 carbon atoms, with 1 to 5 halogen atoms,

or

A represents the residue of formula (A14)

in which

R39means hydrogen or alkyl with 1-4 carbon atoms,

R40means halogen or alkyl with 1-4 carbon atoms,

or

A represents the residue of formula (A15)

in which

R41means alkyl with 1-4 carbon atoms or halogenated with 1-4 carbon atoms, with 1 to 5 halogen atoms,

or

A represents the residue of formula (A16)

in which

R42means hydrogen, halogen, alkyl with 1-4 carbon atoms or halogenated with 1-4 carbon atoms, with 1 to 5 halogen atoms,

or

A represents the residue of formula (A17)

in which

R43means halogen, a hydroxy-group, alkyl with 1-4 carbon atoms, alkoxygroup with 1-4 carbon atoms,alkylthiols with 1-4 carbon atoms, halogenated with 1-4 carbon atoms, halogenation 1-4 carbon atoms or halogenlampe with 1-4 carbon atoms, in each case with 1 to 5 halogen atoms,

or

A represents the residue of formula (A18)

in which

R44means hydrogen, cyano, alkyl with 1-4 carbon atoms, halogenated with 1-4 carbon atoms, with 1 to 5 halogen atoms, C1-C4-alkoxy-C1-C4-alkyl, hydroxy-C1-C4-alkyl, alkylsulfonyl with 1 to 4 carbon atoms, di(C1-C4-alkyl)-aminosulfonyl, alkylaryl with 1-6 carbon atoms or in each case optionally substituted phenylsulfonyl or benzoyl,

R45means hydrogen, halogen, alkyl with 1-4 carbon atoms or halogenated with 1-4 carbon atoms, with 1 to 5 halogen atoms,

R46means hydrogen, halogen, cyano, alkyl with 1-4 carbon atoms or halogenated with 1-4 carbon atoms, with 1 to 5 halogen atoms,

R47means hydrogen, halogen, alkyl with 1-4 carbon atoms or halogenated with 1-4 carbon atoms, with 1 to 5 halogen atoms,

or

A represents the residue of formula (A19)

in which

R48means alkyl with 1-4 carbon atoms.

In addition, it was found that to obtain a 2-alkyl-cyclol(EN)yl-carboxamido formula (I)

(and derivatives of carboxylic acids of the formula (II)

in which

A has the above meanings, and

X1means halogen or hydroxy-group,

subjected to interaction with aniline derivatives of the formula (III)

in which X, s, R1L and R2have the above values, if necessary, in the presence of a catalyst, optionally in the presence of a condensing agent, if necessary in the presence of an acid binding agent and, if necessary, in the presence of a diluent, or

(b) 2-alkyl-cyclol(EN)yl-carboxamide formula (1-a)

in which X, s, L, R2and a have the above meanings, is subjected to the interaction with halides of the formula (IV)

in which

R1Ameans alkyl with 1-8 carbon atoms, alkylsulfonyl with 1-6 carbon atoms, alkylsulfonyl with 1 to 6 carbon atoms, C1-C4-alkoxy-C1-C4-alkyl, cycloalkyl with 3-8 carbon atoms; halogenated with 1-6 carbon atoms, halogenation with 1-4 carbon atoms, halogenacetylenes with 1-4 carbon atoms, halogenallylacetic with 1-4 carbon atoms, halogen-C1-C4-alkoxy-C1-C4-alkyl, halogenosilanes with 3-8 carbon atoms, in each case with 1-9 atoms of fluorine, chlorine and / or bromine is; formyl, formyl-C1-C3-alkyl, (C1-C3-alkyl)carbonyl-C1-C3-alkyl, (C1-C3-alkoxy)carbonyl-C1-C3-alkyl; halogen-(C1-C3-alkyl)carbonyl-C1-C3-alkyl, halogen-(C1-C3-alkylamino)carbonyl-C1-C3-alkyl, in each case 1 to 13 fluorine atoms, chlorine and/or bromine;

(C1-C8-alkyl)carbonyl, (C1-C3-alkoxy)carbonyl, (C1-C4-alkoxy-C1-C4-alkyl)carbonyl, (C3-C8-cycloalkyl)carbonyl;

(C1-C6-halogenated)carbonyl, (C1-C6-halogenoalkane)carbonyl, (halo-C1-C4-alkoxy-C1-C4-alkyl)carbonyl, (C3-C8-halogen-cycloalkyl)carbonyl, in each case with 1-9 atoms of fluorine, chlorine and/or bromine; or-C(=O)C(=O)R6, -CONR7R8or-CH2NR9R10,

R6, R7, R8, R9and R10have the above values,

X2means chlorine, bromine or iodine,

in the presence of a base and in the presence of a diluent.

In addition, it was found that the new 2-alkyl-cyclol(EN)yl-carboxamide formula (I) have very good microbicidal properties and can be used for controlling undesirable microorganisms for the protection of plants and materials.

Connection is according to the invention can, if necessary, to be presented in the form of various possible isomers, in particular stereoisomers, for example, E - and Z-, Treo and retroporn, as well as optical isomers and, if necessary, also of tautomers. The invention applies to both E-and Z-isomers, as well as to tree and erythrosora, as well as optical isomers, any mixtures of these isomers, and also the possible tautomeric forms.

2-Alkyl-cyclol(EN)yl-carboxamide according to the invention are defined by formula (I) in General. Preferred values of residues in the formulae above and below, are given below. These values apply equally both to the end products of the formula (I), and for all intermediate products.

X is preferably-CR3R4R5.

X means, in addition, preferably SiR49R50R51.

s means preferably 1.

s means, in addition, preferably 2.

s means particularly preferably 1.

R1means is preferably hydrogen, alkyl with 1-6 carbon atoms, alkylsulfonyl with 1-4 carbon atoms, alkylsulfonyl with 1 to 4 carbon atoms, C1-C3-alkoxy-C1-C3-alkyl, cycloalkyl with 3-6 carbon atoms; halogenated with 1-4 carbon atoms, halogenation with 1-4 carbon atoms, halogenacetylenes with 1-4 carbon atoms,halogenallylacetic with 1-4 carbon atoms, halogen-C1-C3-alkoxy-C1-C3-alkyl, halogenosilanes with 3-8 carbon atoms, in each case with 1-9 atoms of fluorine, chlorine and/or bromine; formyl, formyl-C1-C3-alkyl, (C1-C3-alkyl)carbonyl-C1-C3-alkyl, (C1-C3-alkoxy)carbonyl-C1-C3-alkyl; halogen-(C1-C3-alkyl)carbonyl-C1-C3-alkyl, halogen-(C1-C3-alkoxy)carbonyl-C1-C3-alkyl; in each case 1 to 13 fluorine atoms, chlorine and/or bromine;

(C1-C6-alkyl)carbonyl, (C1-C4-alkoxy)carbonyl, (C1-C3-alkoxy-C1-C3-alkyl)carbonyl, (C3-C6-cycloalkyl)carbonyl; (C1-C4-halogen-alkyl)carbonyl, (C1-C4-halogenoalkane)carbonyl, (halo-C1-C3-alkoxy-C1-C3-alkyl)carbonyl, (C3-C6-halogenosilanes)carbonyl; in each case with 1-9 atoms of fluorine, chlorine and/or bromine; or-C(=O)C(=O)R6, -CONR7R8or-CH2NR9R10.

R1means particularly preferably hydrogen, methyl, ethyl, n-propyl or isopropyl, n-butyl, isobutyl, sec-butyl or tert-butyl, pentyl or hexyl, methylsulfinyl, ethylsulfinyl, n-propylsulfonyl or isopropylphenyl, n-butylsulfonyl, isobutylphenyl, second-butylsulfonyl or tert-butylsulfide is, methylsulphonyl, ethylsulfonyl, n-propylsulfonyl or isopropylalcohol, n-butylsulfonyl, isobutylphenyl, second-butylsulfonyl or tert-butylsulfonyl, methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, cyclopropyl, cyclopentyl, cyclohexyl, trifluoromethyl, trichloromethyl, triptorelin, detorioration, triptoreline, triptorelin, trifloromethyl, trifloromethyl; formyl, -CH2-Cho, -(CH2)2-Cho, -CH2-CO-CH3, -CH2-CO-CH2CH3, -CH2-CO-CH(CH3)2, -(CH2)2-CO-CH3, -(CH2)2-CO-CH2CH3, -(CH2)2-CO-CH(CH3)2, -CH2-CO2CH3, -CH2-CO2CH2CH3, -CH2-CO2CH(CH3)2, -(CH2)2-CO2CH3, -(CH2)2-CO2CH2CH3, -(CH2)2-CO2CH(CH3)2, -CH2-CO-CF3, -CH2-CO-CCl3, -CH2-CO-CH2CF3, -CH2-CO-CH2CCl3, -(CH2)2-CO-CH2CF3, -(CH2)2-CO-CH2CCl3, -CH2-CO2CH2CF3, -CH2-CO2CF2CF3, -CH2-CO2CH2CCl3, -CH2-CO2CCl2CCl3, -(CH2)2-CO2CH2CF32)2-CO2CF2CF3, -(CH2)2-CO2CH2CCl3, -(CH2)2-CO2CCl2CCl3; methylcarbamyl, ethylcarbazole, n-propylboronic, isopropylcarbonate, tert-butylcarbamoyl, methoxycarbonyl, etoxycarbonyl, tert-butoxycarbonyl, cyclopropanecarbonyl; triptoreline, trevormarsicano, or-C(=O)C(=O)R6, -CONR7R8or-CH2NR9R10.

R1means very preferably hydrogen, methyl, methoxymethyl, formyl, -CH2-Cho, -(CH2)2-Cho, -CH2-CO-CH3, -CH2-CO-CH2CH3, -CH2-CO-CH(CH3)2-C(=O)Cho, -C(=O)C(=O)CH3-C(=O)C(=O)CH2OCH3-C(=O)CO2CH3-C(=O)CO2CH2CH3.

L means preferably L1.

L1means preferably one of the following groups

in which

m means 0, 1 or 2,

n means 0, 1, 2, 3, or 4,

Y1means fluorine, chlorine, methyl, ethyl, n - or isopropyl, n-butyl, isobutyl, sec-butyl or tert-butyl, trifluoromethyl or deformity, and the remains of the Y1may be the same or different when m or n greater than 1.

L1means particularly before occhialino one of the following groups

in which

m means 0, 1 or 2,

n means 0, 1, 2, 3, or 4,

Y1means fluorine, chlorine, methyl, ethyl, n - or isopropyl, n-butyl, isobutyl, sec-butyl or tert-butyl, trifluoromethyl or deformity, and the remains of the Y1may be the same or different when m or n greater than 1.

L means, in addition, preferably L2.

L2means preferably cyclohexenyl (cyclohexanediyl), optionally substituted (from one to four, same or different substitution) fluorine, chlorine, stands, ethyl, n-propylene or isopropyl, n-bootrom, isobutyl, second-bootrom or tert-bootrom, trifluoromethyl or deformation, and the double bond may be in positions 1,2, 2,3, 3,4, 4,5 or 5,6.

L2means particularly preferably a group

in which

r is 0 or 1,

Y2means fluorine, chlorine or methyl.

R2means preferably hydrogen, fluorine, chlorine, methyl, ethyl, n-propyl or isopropyl, or methyl, ethyl, n-propyl or isopropyl, n-butyl, isobutyl, sec-butyl or tert-butyl, in each case singly or multiply substituted by identical or different substituents from the series comprising fluorine, chlorine or bromine.

R2 is particularly preferably hydrogen, fluorine, chlorine, methyl, ethyl, trifluoromethyl, deformity, vermeil, trichloromethyl, dichloromethyl, chloromethyl, CHLOROFORMATES, fertiliser, diperchlorate, pentafluoroethyl, 1-foretel, 2-foretel, 2,2-dottorati, 2,2,2-triptorelin, 2-chloro-2-foretel, 2-chloro-2,defloratin, 2-chloro-2,2-dottorati, 2-dichloro-2-foretel, 2,2,2-trichloroethyl, 1-chlorobutyl, getattr-n-propyl or heptafluoroisopropyl.

R2means very preferably hydrogen, methyl, ethyl or trifluoromethyl.

R2means very preferably hydrogen or methyl.

R3means preferably fluorine, chlorine, bromine, methyl, ethyl, n-propyl or isopropyl, n-butyl, isobutyl, sec-butyl or tert-butyl, or methyl, ethyl, n-propyl or isopropyl, n-butyl, isobutyl, sec-butyl or tert-butyl, in each case singly or multiply substituted by identical or different substituents from the series comprising fluorine, chlorine or bromine.

R3means particularly preferably fluorine, chlorine, methyl, ethyl, n-propyl or isopropyl, n-butyl, isobutyl, sec-butyl or tert-butyl, trifluoromethyl, deformity, vermeil, trichloromethyl, dichloromethyl, chloromethyl, CHLOROFORMATES, fertiliser, diperchlorate, pentafluoroethyl, 1-foretel, 2-foretel, 2,2-dottorati, 2,2,2-triptorelin, 2-chloro-2-foretel, 2-chloro-2,defloratin, 2-chloro-2,2-dottorati, 2-dichloro-2-foretel, 2,2,2-trichloroethyl, 1-harbu the sludge, getattr-n-propyl or heptafluoroisopropyl.

R3means extremely preferably chlorine, methyl, ethyl, isopropyl or trifluoromethyl.

R4means preferably fluorine, chlorine, bromine, methyl, ethyl, n-propyl or isopropyl, n-butyl, isobutyl, sec-butyl or tert-butyl, or methyl, ethyl, n-propyl or isopropyl, n-butyl, isobutyl, sec-butyl or tert-butyl, in each case singly or multiply substituted by identical or different substituents from the series comprising fluorine, chlorine or bromine.

R4means particularly preferably fluorine, chlorine, methyl, ethyl, n-propyl or isopropyl, n-butyl, isobutyl, sec-butyl or tert-butyl, trifluoromethyl, deformity, vermeil, trichloromethyl, dichloromethyl, chloromethyl, CHLOROFORMATES, fertiliser, diperchlorate, pentafluoroethyl, 1-foretel, 2-foretel, 2,2-dottorati, 2,2,2-triptorelin, 2-chloro-2-foretel, 2-chloro-2,defloratin, 2-chloro-2,2-dottorati, 2-dichloro-2-foretel, 2,2,2-trichloroethyl, 1-chlorobutyl, getattr-n-propyl or heptafluoroisopropyl.

R4means extremely preferably chlorine, methyl, ethyl, isopropyl or trifluoromethyl.

R5means preferably hydrogen, fluorine, chlorine, bromine, methyl, ethyl, n-propyl or isopropyl, n-butyl, isobutyl, sec-butyl or tert-butyl, or methyl, ethyl, n-propyl or isopropyl, n-butyl, isobutyl, sec-butyl or tert-butyl, in each case the e one or more times substituted by identical or different substituents from the series comprising fluorine, chlorine or bromine.

R5means particularly preferably hydrogen, fluorine, chlorine, methyl, ethyl, n-propyl or isopropyl, n-butyl, isobutyl, sec-butyl or tert-butyl, trifluoromethyl, deformity, vermeil, trichloromethyl, dichloromethyl, chloromethyl, CHLOROFORMATES, fertiliser, diferior-methyl, pentafluoroethyl, 1-foretel, 2-foretel, 2,2-dottorati, 2,2,2-triptorelin, 2-chloro-2-foretel, 2-chloro-2,defloratin, 2-chloro-2,2-dottorati, 2-dichloro-2-foretel, 2,2,2-trichloroethyl, 1-chlorobutyl, getattr-n-propyl or heptafluoroisopropyl.

R5means very preferably hydrogen, chlorine, methyl, ethyl, isopropyl or trifluoromethyl.

R3and R4together with the carbon atom to which they are attached, preferably form a 3-6-membered carbocyclic or heterocyclic, saturated or unsaturated ring optionally substituted stands, ethyl or trifluoromethyl,

R3and R4together with the carbon atom to which they are bound, form a particularly preferably a 3-membered, 5-membered or 6-membered saturated carbocyclic ring optionally substituted with stands, ethyl or trifluoromethyl,

R3and R4together with the carbon atom to which they are bound, form an extremely preferably 6-membered unsaturated carbocyclic ring optionally substituted with halogen, IU the sludge, the ethyl, methoxy group, trifluoromethyl or cryptomaterial.

R49and R50independently from each other mean preferably alkyl with 1-6 carbon atoms, alkoxygroup with 1-6 carbon atoms, C1-C3-alkoxy-C1-C3-alkyl or C1-C3-alkylthio-C1-C3-alkyl.

R49and R50independently from each other mean particularly preferably methyl, ethyl, methoxy group, ethoxypropan, methoxymethyl, ethoxymethyl, IU-toxity, ethoxyethyl, methylthiomethyl, ethylthiomethyl, methylthioethyl or ethylthioethyl.

R49and R50independently from each other mean very preferably methyl, a methoxy group, methoxymethyl or methylthiomethyl.

R49and R50in each case, the mean extremely preferably methyl.

R51means are preferably alkyl with 1-6 carbon atoms, alkoxygroup with 1-6 carbon atoms, C1-C3-alkoxy-C1-C3-alkyl, C1-C3-alkylthio-C1-C3-alkyl, cycloalkyl with 3-6 carbon atoms, phenyl or benzyl.

R51means particularly preferably methyl, ethyl, n-propyl or isopropyl, n-butyl, isobutyl, sec-butyl or tert-butyl, methoxy group, ethoxypropan, n-propoxylate or isopropoxy, n-butoxypropyl, isobutoxy, sec-butoxypropyl or tert-butoxypropyl, met kemetyl, ethoxymethyl, methoxyethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, methylthioethyl, ethylthioethyl, cyclopropyl, phenyl or benzyl.

R51means very preferably methyl, ethyl, n-propyl or isopropyl, n-butyl, isobutyl, sec-butyl or tert-butyl, methoxy group, isopropoxy, isobutoxy or tert-butoxypropyl, methoxybutyl, methylthiomethyl, or phenyl.

R51means extremely preferably methyl, ethyl, n-propyl or isopropyl, isobutyl or tert-butyl, methoxy group, isopropoxy, isobutoxy or tert-butoxypropan.

R51- highlights methyl.

R6means is preferably hydrogen, alkyl with 1-6 carbon atoms, alkoxygroup with 1-4 carbon atoms, C1-C3-alkoxy-C1-C3-alkyl, cycloalkyl with 3-6 carbon atoms; halogenated with 1-4 carbon atoms, halogenlampe with 1-4 carbon atoms, halogen-C1-C3-alkoxy-C1-C3-alkyl, halogenosilanes with 3-6 carbon atoms in each case with 1-9 atoms of fluorine, chlorine and / or bromine.

R6means particularly preferably hydrogen, methyl, ethyl, n-propyl or isopropyl, n-butyl, isobutyl, sec-butyl or tert-butyl, methoxy group, ethoxypropan, n-propoxylate or isopropoxy, tert-butoxypropyl, methoxybutyl, cyclopropyl; trifluoromethyl, triptoreline the foam.

R7and R8independently from each other mean preferably hydrogen, alkyl with 1-6 carbon atoms, C1-C3-alkoxy-C1-C3-alkyl, cycloalkyl with 3-6 carbon atoms; halogenated with 1-4 carbon atoms, halogen-C1-C3-alkoxy-C1-C3-alkyl, halogenosilanes with 3-6 carbon atoms, in each case with 1-9 atoms of fluorine, chlorine and/or bromine.

R7and R8in addition, together with the nitrogen atom to which they are attached, preferably form a saturated a heterocycle with 5 or 6 atoms in the ring, if necessary, with identical or different substituents a number from 1 to 4, comprising halogen or alkyl with 1-4 carbon atoms, and the heterocycle may contain 1 or 2 are not adjacent to each other heteroatoms from the group comprising oxygen, sulfur or NR11.

R7and R8independently from each other mean particularly preferably hydrogen, methyl, ethyl, -propyl or isopropyl, n-butyl, isobutyl, sec-butyl or tert-butyl, methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, cyclopropyl, cyclopentyl, cyclohexyl; trifluoromethyl, trichloromethyl, triptorelin, trifloromethyl.

R7and R8in addition, together with the nitrogen atom to which they are bound, form particularly preferably rich heterocycle from the series, including morpholine, trimorph the Lin or piperazine, if necessary, with identical or different substituents a number from 1 to 4, comprising fluorine, chlorine, bromine or methyl, where the piperazine in the position of the second nitrogen atom can be substituted by R11.

R9and R10independently from each other mean preferably hydrogen, alkyl with 1-6 carbon atoms, cycloalkyl with 3-6 carbon atoms; halogenated with 1-4 carbon atoms, halogenosilanes with 3-6 carbon atoms, in each case with 1-9 atoms of fluorine, chlorine and/or bromine.

R9and R10together with the nitrogen atom to which they are attached, preferably form a saturated a heterocycle with 5 or 6 atoms in the ring, optionally with one or more identical or different substituents comprising halogen or alkyl with 1-4 carbon atoms, and the heterocycle may contain 1 or 2 are not adjacent to each other heteroatoms from the group comprising oxygen, sulfur or NR11.

R9and R10independently from each other mean particularly preferably hydrogen, methyl, ethyl, -propyl or isopropyl, n-butyl, isobutyl, sec-butyl or tert-butyl, methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, cyclopropyl, cyclopentyl, cyclohexyl; trifluoromethyl, trichloromethyl, triptorelin, trifloromethyl.

R9and R10in addition, together with the nitrogen atom to which they are bound, form a is particularly preferably a saturated a heterocycle from the series, including morpholine, trimorphodon or piperazine, optionally, with identical or different substituents a number from 1 to 4, comprising fluorine, chlorine, bromine or methyl, where the piperazine in the position of the second nitrogen atom can be substituted by R11.

R11means are preferably hydrogen or alkyl with 1-4 carbon atoms.

R11means particularly preferably hydrogen, methyl, ethyl, -propyl or isopropyl, n-butyl, isobutyl, sec-butyl or tert-butyl.

And means preferably one of the residues A1, A2, A3, A4, A5, A6, A9, a10, A11, A12, A16, A17 or A18.

And means particularly preferably one of the residues

A1, A2, A3, A4, A5, A6, A9, A11, A16, A17, A18.

And means very preferably the residue of A1.

And means, in addition, it is preferably the residue of A2.

And means, in addition, it is preferably the residue A3.

And means, in addition, it is preferably the residue of A4.

And means, in addition, it is preferably the residue A5.

And means, in addition, it is preferably the residue A6.

And means, in addition, it is preferably the residue A9.

And means, in addition, it is preferably the residue A11.

And means, in addition, it is preferable balance A16.

And means, in addition, it is preferably the residue A17.

And means, in addition, it is preferable ostate the A18.

R12means preferably hydrogen, cyano, fluorine, chlorine, bromine, iodine, methyl, ethyl, isopropyl, methoxy group, ethoxypropan, methylthiourea, ethylthiourea, cyclopropyl, halogenated with 1-2 carbon atoms, halogenlampe with 1-2 carbon atoms, in each case with 1-5 fluorine atoms, chlorine and/or bromine, triptoreline, deformationof, aminocarbonyl, aminocarbonylmethyl or aminocarbonylmethyl.

R12means particularly preferably hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, isopropyl, MonitorMaster, monitorate, deformity, trifluoromethyl, diperchlorate, trichloromethyl, dichloromethyl, cyclopropyl, a methoxy group, ethoxypropan, cryptometer, trichlormethiazide, methylthiourea, ethylthiourea, triptoreline or deformationof.

R12means very preferably hydrogen, fluorine, chlorine, bromine, iodine, methyl, isopropyl, MonitorMaster, monitorate, deformity, trifluoromethyl, diperchlorate or trichloromethyl.

R12means extremely preferably methyl, deformity, trifluoromethyl or 1-feratel.

R13means preferably hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, methoxy group, ethoxypropan, metalcorp or ethylthiourea.

R13means particularly preferably hydrogen, fluorine, chlorine, bromine, iodine or methyl.

R means very preferably hydrogen, fluorine, chlorine or methyl.

R14means preferably hydrogen, methyl, ethyl, n-propyl, isopropyl, halogenated with 1-2 carbon atoms, with 1-5 fluorine atoms, chlorine and/or bromine, hydroxymethyl, hydroxyethyl, cyclopropyl, cyclopentyl, cyclohexyl or phenyl.

R14means particularly preferably hydrogen, methyl, ethyl, isopropyl, trifluoromethyl, deformity, hydroxymethyl, hydroxyethyl or phenyl.

R14means very preferably hydrogen, methyl, trifluoromethyl or phenyl.

R14means extremely preferably methyl.

R15and R16mean independently from each other preferably hydrogen, fluorine, chlorine, bromine, methyl, ethyl or halogenated with 1-2 carbon atoms, with 1-5 fluorine atoms, chlorine and/or bromine.

R15and R16means independently of one another particularly preferably hydrogen, fluorine, chlorine, bromine, methyl, ethyl, deformity, trifluoromethyl, di-perchloromethyl or trichloromethyl.

R15and R16mean independently from each other very preferably hydrogen, fluorine, chlorine, bromine, methyl, ethyl, deformity, trifluoromethyl or trichloromethyl.

R15and R16means in each case, very preferably hydrogen,

R17means preferably fluorine, chlorine, bromine, cyano, methyl, ethyl, halogenated with 1-2 atom is mi carbon halogenlampe with 1-2 carbon atoms, in each case with 1-5 fluorine atoms, chlorine and/or bromine.

R17means particularly preferably fluorine, chlorine, bromine, cyano, methyl, trifluoromethyl, cryptometer, dipterocarp, diperchlorate or trichlormethiazide.

R17means very preferably a fluorine, chlorine, bromine, iodine, methyl, trifluoromethyl or cryptometer.

R17means extremely preferably methyl.

R18and R19independently from each other mean preferably hydrogen, fluorine, chlorine, bromine, methyl, ethyl or halogenated with 1-2 carbon atoms, with 1-5 fluorine atoms, chlorine and/or bromine.

R18and R19independently from each other mean particularly preferably hydrogen, fluorine, chlorine, bromine, methyl, ethyl, deformity, trifluoromethyl, diperchlorate or trichloromethyl.

R18and R19mean independently from each other very preferably hydrogen, fluorine, chlorine, bromine, methyl, ethyl, deformity, trifluoromethyl or trichloromethyl.

R18and R19means in each case, very preferably hydrogen.

R20means preferably hydrogen, fluorine, chlorine, bromine, methyl, ethyl or halogenated with 1-2 carbon atoms, with 1-5 fluorine atoms, chlorine and/or bromine.

R20means particularly preferably hydrogen, fluorine, chlorine, bromine, th is d, methyl or trifluoromethyl.

R20means very preferably methyl.

R21means preferably hydrogen, fluorine, chlorine, bromine, iodine, hydroxy-group, cyano, alkyl with 1-4 carbon atoms, halogenated with 1-2 carbon atoms, halogenlampe with 1-2 carbon atoms or halogenation with 1-2 carbon atoms, in each case with 1 to 5 fluorine atoms, chlorine and/or bromine.

R21means particularly preferably hydrogen, fluorine, chlorine, bromine, iodine, hydroxy-group, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl or tert-butyl, deformity, trifluoromethyl, diperchlorate, trichloromethyl, cryptometer, dipterocarp, diperchlorate, trichlormethiazide, triptoreline, deformationof, detorioration or trichloromethylmercapto.

R21means very preferably hydrogen, fluorine, chlorine, bromine, iodine, methyl, deformity, trifluoromethyl or trichloromethyl.

R21means extremely preferably iodine, methyl, deformity or trifluoromethyl.

R22means preferably fluorine, chlorine, bromine, iodine, hydroxy-group, a hydroxy-group, cyano, alkyl with 1-4 carbon atoms, a methoxy group, ethoxypropan, methylthiourea, ethylthiourea, deformationof, triptoreline, halogenated with 1-2 atoms is carbon or halogenlampe with 1-2 carbon atoms, in each case, with 1-5 fluorine atoms, chlorine and/or bromine.

R22means particularly preferably fluorine, chlorine, bromine, iodine, hydroxy-group, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl or tert-butyl, trifluoromethyl, deformity, di-perchloromethyl, trichloromethyl, a methoxy group, ethoxypropan, methylthiourea, ethylthiourea, deformationof, triptoreline, cryptometer, dipterocarp, diperchlorate or trichlormethiazide.

R22means very preferably a fluorine, chlorine, bromine, iodine, methyl, trifluoromethyl, deformity or trichloromethyl.

R23means preferably hydrogen, fluorine, chlorine, bromine, iodine, cyano, alkyl with 1-4 carbon atoms, a methoxy group, ethoxypropan, methylthiourea, ethylthiourea, halogenated with 1-2 carbon atoms or halogenation with 1-2 carbon atoms in each case 1 to 5 fluorine atoms, chlorine and/or bromine, alkylsulfonyl with 1-2 carbon atoms, or alkylsulfonyl with 1 to 2 carbon atoms.

R23means particularly preferably hydrogen, fluorine, chlorine, bromine, iodine, cyano, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl or tert-butyl, trifluoromethyl, deformity, diperchlorate, three-chloromethyl, a methoxy group, ethoxypropan, methylthiourea, ethylthiourea, cryptometer, diplomatarium is, diperchlorate, trichlormethiazide, methylsulfinyl or methylsulphonyl.

R23means very preferably hydrogen, fluorine, chlorine, bromine, iodine, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl or tert-butyl, trifluoromethyl, deformity, trichloromethyl, methylsulfinyl or methylsulphonyl.

R23means extremely preferably hydrogen.

R24means preferably methyl, ethyl or halogenated with 1-2 carbon atoms, with 1-5 fluorine atoms, chlorine and/or bromine.

R24means particularly preferably methyl, ethyl, trifluoromethyl, deformity, diperchlorate or trichloromethyl.

R25means preferably methyl or ethyl.

R25means particularly preferably methyl.

Q1means preferably S (sulphur), SO2or CH2.

Q1means particularly preferably S (sulfur) or CH2.

Q1means extremely preferably S (sulfur).

R means preferably 0 or 1.

R means particularly preferably 0.

R26means preferably methyl, ethyl or halogenated with 1-2 carbon atoms, with 1-5 fluorine atoms, chlorine and/or bromine.

R26means particularly preferably methyl, ethyl, trifluoromethyl, deformity, diperchlorate or trichloromethyl.

R26means very preferably methyl, trifluoromethyl, debtor ethyl or trichloromethyl.

R27means preferably methyl, ethyl or halogenated with 1-2 carbon atoms, with 1-5 fluorine atoms, chlorine and/or bromine.

R27means particularly preferably methyl, ethyl, trifluoromethyl, deformity, diperchlorate or trichloromethyl.

R27means very preferably methyl, trifluoromethyl, deformity or trichloromethyl.

R28and R29mean independently from each other preferably hydrogen, fluorine, chlorine, bromine, amino, methyl, ethyl or halogenated with 1-2 carbon atoms, with 1 to 5 fluorine atoms, chlorine and/or bromine.

R28and R29means independently of one another particularly preferably hydrogen, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, deformity, diperchlorate or trichloromethyl.

R28and R29mean independently from each other very preferably hydrogen, fluorine, chlorine, bromine, methyl, trifluoromethyl, deformity or trichloromethyl.

R28and R29means in each case, very preferably hydrogen.

R30means preferably hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl or halogenated with 1-2 carbon atoms, with 1-5 fluorine atoms, chlorine and/or bromine.

R30means particularly preferably hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, trifluoromethyl, deformity, diperchlorate or trichloromethyl.

R30means Carniola is preferably hydrogen, fluorine, chlorine, bromine, methyl, trifluoromethyl, deformity or trichloromethyl.

R30means extremely preferably methyl.

R31and R32mean independently from each other preferably hydrogen, fluorine, chlorine, bromine, an amino group, a nitrogroup, methyl, ethyl or halogenated with 1-2 carbon atoms, with 1-5 fluorine atoms, chlorine and/or bromine.

R31and R32means independently of one another particularly preferably hydrogen, fluorine, chlorine, bromine, a nitro-group, methyl, ethyl, trifluoromethyl, deformity, diperchlorate or trichloromethyl.

R31and R32mean independently from each other very preferably hydrogen, fluorine, chlorine, bromine, methyl, trifluoromethyl, deformity or trichloromethyl.

R31and R32means in each case, very preferably hydrogen.

R33means preferably hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl or halogenated with 1-2 carbon atoms, with 1-5 fluorine atoms, chlorine and/or bromine.

R33means particularly preferably hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, trifluoromethyl, deformity, diperchlorate or trichloromethyl.

R33means very preferably hydrogen, fluorine, chlorine, bromine, methyl, trifluoromethyl, deformity or trichloromethyl.

R33means extremely preferably methyl.

R34means preferably is hydrogen, fluorine, chlorine, bromine, amino group, alkylamino with 1-4 carbon atoms, di(C1-C4-alkyl)-amino group, cyano, methyl, ethyl or halogenated with 1-2 carbon atoms, with 1-5 fluorine atoms, chlorine and/or bromine.

R34means particularly preferably hydrogen, fluorine, chlorine, bromine, amino group, methylaminopropyl, methylaminopropyl, dimethylaminopropyl, cyano, methyl, ethyl, trifluoromethyl, deformity, diperchlorate or trichloromethyl.

R34means very preferably hydrogen, fluorine, chlorine, bromine, amino group, methylaminopropyl, dimethylaminopropyl, methyl, trifluoromethyl, deformity or trichloromethyl.

R34means extremely preferably an amino group, methylaminopropyl, dimethylaminopropyl, methyl or trifluoromethyl.

R35means preferably fluorine, chlorine, bromine, methyl, ethyl or halogenated with 1-2 carbon atoms, with 1-5 fluorine atoms, chlorine and/or bromine.

R35means particularly preferably fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, deformity, diperchlorate or trichloromethyl.

R35means very preferably a fluorine, chlorine, bromine, methyl, trifluoromethyl, deformity or trichloromethyl.

R35means extremely preferably methyl, trifluoromethyl or deformity.

R36means preferably hydrogen, fluorine, chlorine, bromine, amino group, ALK is luminograph with 1-4 carbon atoms, di(C1-C4-alkyl)-amino group, cyano, methyl, ethyl or halogenated with 1-2 carbon atoms, with 1-5 fluorine atoms, chlorine and/or bromine.

R36means particularly preferably hydrogen, fluorine, chlorine, bromine, amino group, methylaminopropyl, dimethylaminopropyl, cyano, methyl, ethyl, trifluoromethyl, deformity, diperchlorate or trichloromethyl.

R36means very preferably hydrogen, fluorine, chlorine, bromine, amino group, methylaminopropyl, dimethylaminopropyl, methyl, trifluoromethyl, deformity or trichloromethyl.

R36means extremely preferably an amino group, methylaminopropyl, dimethylaminopropyl, methyl or trifluoromethyl.

R37means preferably fluorine, chlorine, bromine, methyl, ethyl or halogenated with 1-2 carbon atoms, with 1-5 fluorine atoms, chlorine and/or bromine.

R37means particularly preferably fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, deformity, diperchlorate or trichloromethyl.

R37means very preferably a fluorine, chlorine, bromine, methyl, trifluoromethyl, deformity or trichloromethyl.

R37means extremely preferably methyl, trifluoromethyl or deformity.

R38means preferably fluorine, chlorine, bromine, methyl, ethyl or halogenated with 1-2 carbon atoms, with 1-5 fluorine atoms, chlorine and/or bromine.

R38means the OS is Bo preferably fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, deformity, diperchlorate or trichloromethyl.

R38means very preferably a fluorine, chlorine, bromine, methyl, trifluoromethyl, deformity or trichloromethyl.

R39means preferably hydrogen, methyl or ethyl.

R39means particularly preferably methyl.

R40means preferably fluorine, chlorine, bromine, methyl or ethyl.

R40means particularly preferably fluorine, chlorine or methyl.

R41means preferably methyl, ethyl or halogenated with 1-2 carbon atoms, with 1-5 fluorine atoms, chlorine and/or bromine.

R41means particularly preferably methyl, ethyl, trifluoromethyl, deformity, diperchlorate or trichloromethyl.

R41means very preferably methyl, trifluoromethyl, deformity or trichloromethyl.

R41means extremely preferably methyl or trifluoromethyl.

R42means preferably hydrogen, fluorine, chlorine, bromine, methyl, ethyl or halogenated with 1-2 carbon atoms, with 1-5 fluorine atoms, chlorine and/or bromine.

R42means particularly preferably hydrogen, fluorine, chlorine, bromine, methyl or trifluoromethyl.

R43means preferably fluorine, chlorine, bromine, iodine, hydroxy-group, alkyl with 1-4 carbon atoms, a methoxy group, ethoxypropan, methylthiourea, ethylthiourea, deformationof is, triptoreline, halogenated with 1-2 carbon atoms or halogenlampe with 1-2 carbon atoms, in each case with 1-5 fluorine atoms, chlorine and/or bromine.

R43means particularly preferably fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl, butyl, isobutyl, sec-butyl or tert-butyl, trifluoromethyl, deformity, diperchlorate or trichloromethyl.

R43means very preferably a fluorine, chlorine, bromine, iodine, methyl, trifluoromethyl, deformity or trichloromethyl.

R44means preferably hydrogen, methyl, ethyl, or halogenated with 1-2 carbon atoms, with 1-5 fluorine atoms, chlorine and / or bromine, With1-C2-alkoxy-C1-C2-alkyl, hydroxymethyl, hydroxyethyl, methylsulphonyl or dimethylaminomethyl.

R44means particularly preferably hydrogen, methyl, ethyl, trifluoromethyl, methoxymethyl, ethoxymethyl, hydroxymethyl or hydroxyethyl,

R44means very preferably methyl or methoxymethyl.

R45means preferably hydrogen, fluorine, chlorine, bromine, methyl, ethyl or halogenated with 1-2 carbon atoms, with 1-5 fluorine atoms, chlorine and/or bromine.

R45means particularly preferably hydrogen, fluorine, chlorine, bromine, methyl, ethyl trifluoromethyl, deformity or trichloromethyl.

R45means very preferably hydrogen or methyl.

R4 means preferably hydrogen, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, isopropyl or halogenated with 1-2 carbon atoms, with 1-5 fluorine atoms, chlorine and/or bromine.

R46means particularly preferably hydrogen, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, isopropyl, trifluoromethyl, deformity, diperchlorate or trichloromethyl.

R46means very preferably hydrogen, methyl, deformity or trifluoromethyl.

R47means preferably hydrogen, fluorine, chlorine, bromine, methyl, ethyl or halogenated with 1-2 carbon atoms, with 1-5 fluorine atoms, chlorine and/or bromine.

R47means particularly preferably hydrogen, fluorine, chlorine, bromine, iodine, methyl or trifluoromethyl.

R47means very preferably hydrogen.

R48means preferably methyl, ethyl, n-propyl or isopropyl.

R48means particularly preferably methyl or ethyl.

Preferred such compounds of formula (I), in which all residues are in each case above, the preferred values. Particularly preferred such compounds of formula (I), in which all residues are in each case above, particularly preferred values.

Highly preferred are such compounds of formula (I), in which all residues are in each case above, highly preferred value is expression.

In each case should be considered the preferred and which part of the above compounds (I) of the following groups of new carboxamido:

Group 1: 2-alkyl-cyclol(EN)yl-carboxamide formula (I-g)

where s, L, R2, R3, R4, R5and a have the above values.

Group 2: 2-alkyl-cyclol(EN)yl-carboxamide formula (I-b)

in which s, R1A, L, R2, R3, R4, R5and a have the above values.

R1Ameans are preferably alkyl with 1-6 carbon atoms, alkylsulfonyl with 1-4 carbon atoms, alkylsulfonyl with 1 to 4 carbon atoms, C1-C3-alkoxy-C1-C3-alkyl, cycloalkyl with 3-6 carbon atoms; halogenated with 1-4 carbon atoms, halogenation with 1-4 carbon atoms, halogenacetylenes with 1-4 carbon atoms, halogenallylacetic with 1-4 carbon atoms, halogen-C1-C3-alkoxy-C1-C3-alkyl, halogenosilanes with 3-8 carbon atoms, in each case with 1-9 atoms of fluorine, chlorine and / or bromine; formyl, formyl-C1-C3-alkyl, (C1-C3-alkyl)carbonyl-C1-C3-alkyl, (C1-C3-alkoxy)carbonyl-C1-C3-alkyl; halogen-(C1-C3-alkyl)carbonyl-C1-C3-alkyl, halogen-(C1/sub> -C3-alkoxy)carbonyl-C1-C3-alkyl, in each case 1 to 13 fluorine atoms, chlorine and/or bromine; (C1-C6-alkyl)carbonyl, (C1-C4-alkoxy)carbonyl, (C1-C3-alkoxy-C1-C3-alkyl)carbonyl, (C3-C6-cycloalkyl)carbonyl; (C1-C4-halogenated)-carbonyl, (C1-C4-halogenoalkane)carbonyl, (halo-C1-C3-alkoxy-C1-C3-alkyl)carbonyl, (C3-C6-halogenosilanes)carbonyl, in each case with 1-9 atoms of fluorine, chlorine and/or bromine; or-C(=O)C(=O)R6, -CONR7R8or-CH2NR9R10.

R1Ameans particularly preferably methyl, ethyl, n-propyl or isopropyl, n-butyl, isobutyl, sec-butyl or tert-butyl, pentyl or hexyl, methylsulfinyl, ethylsulfinyl, n-propylsulfonyl or isopropylphenyl, n-butylsulfonyl, isobutylphenyl, second-butylsulfonyl or tert-butylsulfonyl, methylsulphonyl, ethyl sulfonyl, n-propylsulfonyl or isopropylalcohol, n-butylsulfonyl, isobutylphenyl, second-butylsulfonyl or tert-butylsulfonyl, methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, cyclopropyl, cyclopentyl, cyclohexyl, trifluoromethyl, trichloromethyl, triptorelin deformationof, detorioration, triptoreline, triptorelin, triformis honil, trifloromethyl; formyl, -CH2-Cho, -(CH2)2-Cho, -CH2-CO-CH3, -CH2-CO-CH2CH3, -CH2-CO-CH(CH3)2, -(CH2)2-CO-CH3, -(CH2)2-CO-CH2CH3, -(CH2)2-CO-CH(CH3)2, -CH2-CO2CH3, -CH2-CO2CH2CH3, -CH2-CO2CH(CH3)2, -(CH2)2-CO2CH3, -(CH2)2-CO2CH2CH3, -(CH2)2-CO2CH(CH3)2, -CH2-CO-CF3, -CH2-CO-CCl3, -CH2-CO-CH2CF3, -CH2-CO-CH2CCl3, -(CH2)2-CO-CH2CF3, -(CH2)2-CO-CH2CCl3, -CH2-CO2CH2CF3, -CH2-CO2CF2CF3, -CH2-CO2CH2CCl3, -CH2-CO2CCl2CCl3, -(CH2)2-CO2CH2CF3, -(CH2)2-CO2CF2CF3, -(CH2)2-CO2CH2CCl3, -(CH2)2-CO2CCl2CCl3; methylcarbamyl, ethylcarbazole, n-propylboronic, isopropylcarbonate, tert-butylcarbamoyl, methoxycarbonyl, etoxycarbonyl, tert-butoxycarbonyl, cyclopropanecarbonyl; triptoreline, trevormarsicano, or-C(=O)C(=O)R6, -CONR7R8 or-CH 2NR9R10.

R1Ameans very preferably methyl, methoxymethyl, formyl, -CH2-Cho, -(CH2)2-Cho, -CH2-CO-CH3, -CH2-CO-CH2CH3, -CH2-CO-CH(CH3)2-C(=O)Cho, -C(=O)C(=O)CH3-C(=O)C(=O)CH2OCH3-C(=O)CO2CH3-C(=O)CO2CH2CH3.

Group 3: 2-alkyl-cyclol(EN)yl-carboxamide formula (I-c)

in which s, R1, R2, R3, R4, R5, A, Y1and n have the above values.

Particularly important compounds with formula (I-c), in which n is 0.

Particularly important compounds with formula (I-c), in which R1means hydrogen.

Particularly important compounds with formula (I-c), in which s means 1.

Group 4: 2-alkyl-cyclol(EN)yl-carboxamide formula (I-d)

in which s, R1, R2, R3, R4, R5, A, Y1and n have the above values.

Particularly important compounds with formula (I-c), in which n is 0.

Particularly important compounds with formula (I-c), in which R1means hydrogen.

Particularly important compounds with formula (I-c), in which s means 1.

Group 5: 2-alkyl-cyclol(EN)yl-carboxamide with the formula (1-e)

in which s, R1, R2, R3, R4, R5, A, Ysup> 1and m have the above values.

Particularly important compounds with formula (I-c), in which m is 0.

Particularly important compounds with formula (I-c), in which R1means hydrogen.

Particularly important compounds with formula (I-c), in which s means 1.

Group 6: 2-alkyl-cyclol(EN)yl-carboxamide formula (I-f)

in which s, R1, R2, R3, R4, R5, A, Y2and g have the above values.

Particularly important compounds with formula (I-c), in which g is 0.

Particularly important compounds with formula (I-c), in which R1means hydrogen.

Particularly important compounds with formula (I-c), in which s means 1.

Group 7: 2-alkyl-cyclol(EN)yl-carboxamide formula (I-h)

where s, L, R2, R49, R50, R51and a have the above values.

Group 8: 2-alkyl-cyclol(EN)yl-carboxamide formula (I-i)

in which s, R1A, L, R2, R49, R50, R51and a have the above values.

Group 9: 2-alkyl-cyclol(EN)yl-carboxamide formula (I-k)

in which s, R1, R2, R49, R50, R51, A, Y1and n have the above values.

Particularly important compounds with formula (I-c), in which n is 0.

Persons is important compounds with formula (I-c), in which R1means hydrogen.

Particularly important compounds with formula (I-c), in which s means 1.

Group 10: 2-alkyl-cyclol(EN)yl-carboxamide formula (I-I)

in which s, R1, R2, R49, R50, R51And, Y1and n have the above values.

Particularly important compounds with formula (I-c), in which n is 0.

Particularly important compounds with formula (I-c), in which R1means hydrogen.

Particularly important compounds with formula (I-c), in which s means 1.

Group 11: 2-alkyl-cyclol(EN)yl-carboxamide formula (I-m)

in which s, R1, R2, R49, R50, R51, A, Y1and m have the above values.

Particularly important compounds with formula (I-c), in which m is 0.

Particularly important compounds with formula (I-c), in which R1means hydrogen.

Particularly important compounds with formula (I-c), in which s means 1.

Group 12: 2-alkyl-cyclol(EN)yl-carboxamide formula (I-n)

in which s, R1, R2, R49, R50, R51, A, Y2and r have the above values.

Particularly important compounds with formula (I-c), in which r is 0.

Particularly important compounds with formula (I-c), in which R1means hydrogen.

Particularly important compounds with formula (I-c), to the Torah's meaning 1.

Particularly important compounds of the formula (I) (and also belong to groups 2-6 and 8-12), in which R1or R1Amean formyl.

In addition, a particularly important compounds of the formula (I) (and also belong to groups 2-6 and 8-12), in which R1or R1Ameans-C(=O)C(=O)R6and R6has the above values.

Saturated or unsaturated hydrocarbons, for example, alkyl and alkenyl, including those associated with heteroatoms, such as, for example, alkoxy groups may in each case, to the extent possible, be promocao Laundry or branched.

Substituted, if necessary, the residues can be substituted once or many times, whereby the multiple substitution, the substituents may be the same or different. Thus, the value of dialkylamino" includes the amino group with an asymmetric substitution alkilani, for example, methylaminopropyl.

Residues substituted with halogen, such as, for example, halogenated, galogenirovannyie one or more times. When multiple halogenization the halogen atoms may be the same or different. Halogen means fluorine, chlorine, bromine and iodine, in particular fluorine, chlorine and bromine.

Any combination of residues, as defined above in General and described with refinements in preferred cases. This applies to both the target products and intermediate and primary products, respectively. In particular, the compounds included in groups 1-6, can be combined with the substances mentioned as preferred, particularly preferred, etc. and also in each case, all possible combinations between the preferred cases.

Description of the method according to the invention to obtain a 2-alkyl-cyclol(EN)yl-carboxamido formula (I) and intermediates.

Method (a)

If the original substances using 5-fluoro-1,3-dimethyl-1H-pyrazole-4-carbonylchloride and 2-(1,3-dimethylbutyl)cyclohexanes, the method (a) according to the invention can be schematically represent the following chemical scheme:

Derivatives of carboxylic acids required as starting substances for the implementation of the method (a) according to the invention are defined in General formula (II). In the formula (II) is preferred, particularly preferred or very preferred are those values that were specified as preferred, particularly preferred or very preferred for that rest above, in the description of compounds of formula (I) according to the invention. X1means preferably chlorine, bromine or hydroxy-group.

Derivatives of carboxylic acids of the formula (II) are known and/or can be synthesized by known methods (cf. international application WO 03/066609, WO 03/066610, European patent application EP-A 0545099, EP-A 0589301, EP-A 0589313 and U.S. patent US 3547917).

Derivatives of aniline, also required as starting substances for the implementation of the method (a) according to the invention are defined in General formula (III). In the formula (III) X, s, R1L and R2have the preferred, particularly preferred or very preferred are those values that were specified as preferred, particularly preferred or very preferred for these residues and notation above, in the description of compounds of formula (I) according to the invention.

Derivatives of aniline of the formula (111) partially known or can be synthesized by known methods (cf. for example European patent application EP-A 0589313).

It is also possible first to synthesize derivatives of aniline of formula (III-a)

in which X, s, L, and R2have the above values, then, if necessary, to conduct the reaction with halides of the formula (IV)

,

in which R3Aand X4have the above meanings, in the presence of a base and in the presence of a diluent [respectively, the actual reaction conditions (b) according to the invention].

Derivatives of aniline of formula (III) can also be obtained, if (C) cyclic ket is of the formula (V)

in which

L1ameans alkylen (alcander) with 2-6 carbon atoms, optionally having from 1 to 4 identical or different substituents from the series comprising fluorine, chlorine, alkyl with 1-4 carbon atoms or haloalkyl with 1-4 carbon atoms, is first subjected to interaction with carbonyl compounds of the formula (VI)

where X, s and R2have the above meanings, in the presence of a base, to obtain the compounds of the formulas (VIIa) and (VIIb)

in which

X, s and R2have the above values and

L1bmeans alkylen (alcander) with 1-5 carbon atoms, optionally having from 1 to 4 identical or different substituents from the series comprising fluorine, chlorine, alkyl with 1-4 carbon atoms or haloalkyl with 1-4 carbon atoms, after which the latter is subjected to reductive aminating the usual way.

Cyclic ketones required as starting substances for the implementation of the method (s) according to the invention are defined in General formula (V). In the formula (V) L1ameans preferably -(CH2)2-if necessary, m-fold substituted Y1or -(CH2)3- -(CH2)4-, -(CH2)5- or -(CH2)6in to the each case, if necessary, the n-fold substituted Y1where m, n and Y1have the above values. L1ameans particularly preferably -(CH2)2-if necessary, m-fold substituted Y1or -(CH2)4- or -(CH2)5in each case, if necessary, the n-fold substituted Y1where m, n and Y1have the above values.

Carbonyl compounds, are also required as starting substances for the implementation of the method (s) according to the invention are defined in General formula (VI). In the formula (VI) X, s and R2have the preferred, particularly preferred or very preferred are those values that were specified as preferred, particularly preferred or very preferred for these residues and notation above, in the description of compounds of formula (I) according to the invention.

Compounds formed as intermediates during the implementation of method (C) according to the invention are defined in General formulae (VIIa) and (VIIb). In formulas (VIIa) and (VIIb) L1bmeans preferably -(CH2)2-if necessary, m-fold substituted Y1or -(CH2)3- -(CH2)4-, -(CH2)5- or -(CH2)6-in each case optionally n-times substituted Y1where m, n and Y1have given is installed above values. L1bif necessary, the m-fold substituted Y1or -(CH2)3- or -(CH2)4-in each case optionally n-times substituted Y1where m, n and Y1have the above values of X, s and R2have the preferred, particularly preferred or very preferred are those values that were specified as preferred, particularly preferred or very preferred for these residues and notation above, in the description of compounds of formula (I) according to the invention.

Cyclic ketones of the formula (V) and carbonyl compounds (VI) are known or can be synthesized by known literature methods (Organic Letters 2001, Vol.3, 573; Tetrahedron Letters 42 (2001) 4257).

Method (b)

If the original substances using N-[2-(1,3-dimethylbutyl)cyclohexyl]-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide and acetylchloride, the method (b) according to the invention can be represented the following chemical scheme:

2-Alkyl-cyclol(EN)yl-carboxamide required as starting substances for the implementation of the method (b), defined in General formula (I-a). In the formula (I-a) X, s, L, R2and have the preferred, particularly preferred or very preferred are those values that were specified as preferred, particularly preferred or edge is e preferred for these residues and notation above, when describing the compounds of formula (I) according to the invention.

The compounds of formula (I-a) connection according to the invention, they can be obtained by method (a).

The halides, are also required as starting substances for the implementation of the method (b), defined in General formula (IV). In the formula (IV) R1Ahave the preferred, particularly preferred or very preferred are those values that were specified as preferred, particularly preferred or very preferred for that rest above, in the description of compounds of formula (I-b). X4means chlorine, bromine or iodine.

The halides of the formula (IV) are known.

Conditions reactions

As diluents for the implementation of the method (a) according to the invention can be used all inert organic solvents. It is advisable to use aliphatic, acyclic or aromatic hydrocarbons, such as petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin; halogenated hydrocarbons, such as chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloroethane or trichloroethane; ethers, for example diethyl ether, diisopropyl ether, methyl tert-butyl ether, methyl tert-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane Il is the anisole; ketones, such as acetone, butanone, methyl isobutyl ketone or cyclohexanone; NITRILES, such as acetonitrile, propionitrile, n-butyronitrile or isobutyronitrile or Ben-sonitrol; amides such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylformamide, N is an organic or triamide HEXAMETHYL-phosphoric acid; mixtures thereof with water or pure water.

Method (a) according to the invention, if necessary, is carried out in the presence of a suitable proton acceptor [Säureakzeptor]. As such, you can use all common inorganic and organic bases. It is advisable to apply the hydrides, hydroxides, amides, alcoholate, acetates, carbonates or bicarbonates of alkali or alkaline earth metals, for example, sodium hydride, sodium amide, diisopropylamide lithium, sodium methylate, sodium ethylate, tert-butyl potassium, sodium hydroxide, potassium hydroxide, sodium acetate, sodium carbonate, potassium carbonate, potassium bicarbonate, sodium bicarbonate or ammonium carbonate, and also tertiary amines, such as trimethylamine, triethylamine, tributylamine, N,N-dimethylaniline, N,N-dimethyl-benzylamine, pyridine, N-methylpiperidine, N-methylmorpholine, N,N-dimethylaminopyridine, diazabicyclo (DABCO), diazabicyclo (DBN) or databaseconnect (DBU).

Method (a) according to the invention, if necessary, carried the t in the presence of a suitable condensing agent. As such, you can apply all of the condensing agents commonly used in such amidation reactions. As an example, you should call the agents forming the acid halides, such as phosgene, postertime, phosphorotrithioite, gospocentric, phosphoroxychloride or thionyl chloride; agents which form anhydrides, for example, ethyl ether of Harborview acid, methyl ether of Harborview acid, propyl ether of Harborview acid, butyl ether of Harborview acid or methansulfonate; carbodiimide, for example, N,N'-dicyclohexylcarbodiimide (DCC) or other conventional condensing agents, for example, factorinduced, polyphosphoric acid, N,N'-carbonyldiimidazole, 2-ethoxy-N-etoxycarbonyl-1,2-dihydroquinoline (EEDQ), triphenylphosphine/tetrachlorophenol or bromine-triprolidine-phosphonium-hexaphosphate.

Method (a) according to the invention, if necessary, is carried out in the presence of a catalyst. As examples should be called 4-dimethylaminopyridine, 1-hydroxybenzotriazole or dimethylformamide.

The reaction temperature in the process (a) according to the invention can be varied within wide limits. As a rule, operate in temperatures from 0°C to 150°C, preferably at temperatures from 0°C to 80°C.

For implementing the method (a) according to izobreteny is to obtain the compounds of formula (I) per mole carboxylic acid derivative of the formula (II) in General spend from 0.8 to 15 mol, preferably 0.8 to 8 mol aniline derivative of the formula (III).

As diluents for implementing the method (b) according to the invention can be used all inert organic solvents. It is advisable to use aliphatic, acyclic or aromatic hydrocarbons, such as petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin; halogenated hydrocarbons, such as chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloroethane or trichloroethane; ethers, for example diethyl ether, diisopropyl ether, methyl tert-butyl ether, methyl tert-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole; or amides such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylformamide, N is an organic or triamide hexamethylphosphoric acid.

Method (b) according to the invention is carried out in the presence of a base. As such, you can use all common inorganic and organic bases. It is advisable to apply the hydrides, hydroxides, amides, alcoholate, acetates, carbonates or bicarbonates of alkali or alkaline earth metals, for example, sodium hydride, sodium amide, sodium methylate, sodium ethylate, tert-butyl potassium hydroxide sodium hydroxide is Aliya, the ammonium hydroxide, sodium acetate, potassium acetate, calcium acetate, ammonium acetate, sodium carbonate, potassium carbonate, potassium bicarbonate, sodium bicarbonate or cesium carbonate, and also tertiary amines, such as trimethylamine, triethylamine, tributylamine, N,N-di-methylaniline, N,N-dimethyl-benzylamine, pyridine, N-methylpiperidine, N-methylmorpholine, N,N-dimethylaminopyridine, diazabicyclo (DABCO), diazabicyclo (DBN) or databaseconnect (DBU).

The reaction temperature in the process (b) according to the invention can be varied within wide limits. As a rule, operate in temperatures from 0°C to 150°C, preferably at temperatures from 20°C to 110°C.

To implement the process (b) according to the invention for preparing compounds of formula (I) per mole of 2-alkyl-cyclol(EN)yl-carboxamide of the formula (I-a) in General spend from 0.2 to 5 mol, preferably 0.5 to 2 mol of the halide of formula (IV).

Unless otherwise stated, all methods according to the invention is carried out in General under atmospheric pressure. It is possible, however, to work at elevated or reduced pressure, typically between 0.1 bar and 10 bar.

As diluents for implementing the method (s) according to the invention can be used all inert organic solvents. It is advisable to use aliphatic, acyclic or aromatic the ski hydrocarbons, as, for example, petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin; halogenated hydrocarbons, such as chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloroethane or trichloroethane; ethers, such as diethyl ether, diisopropyl ether, methyl tert-butyl ether, methyl tert-amyl ether, dioxane, tetrahydrofuran, 1,2 - dimethoxyethane, 1,2-diethoxyethane or anisole; or amides such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylformamide, N is an organic or triamide hexamethylphosphoric acids, alcohols, e.g. methanol, ethanol, isopropanol, n-butanol, sec-butanol or tert-butanol, and mixtures thereof with water or pure water.

Method (C) according to the invention is carried out in the presence of a base. As such, you can use all common inorganic and organic bases. It is advisable to apply the hydrides, hydroxides, amides, alcoholate, acetates, carbonates or bicarbonates of alkali or alkaline earth metals, for example, sodium hydride, sodium amide, sodium methylate, sodium ethylate, tert-butyl potassium, sodium hydroxide, potassium hydroxide, ammonium hydroxide, sodium acetate, potassium acetate, calcium acetate, ammonium acetate, sodium carbonate, potassium carbonate, potassium bicarbonate, sodium bicarbonate or Carbo is at cesium, and also tertiary amines, such as trimethylamine, triethylamine, tributylamine, N,N-di-methylaniline, N,N-dimethyl-benzylamine, pyridine, N-methylpiperidine, N-methylmorpholine, N,N-dimethylaminopyridine, diazabicyclo (DABCO), diazabicyclo (DBN) or databaseconnect (DBU).

The reaction temperature in the process (C) according to the invention can be varied within wide limits. As a rule, operate in temperatures from -20°C to 150°C, preferably at temperatures from 0°C to 110°C.

For implementing the method (s) according to the invention for preparing compounds of the formula (III) per mole of cyclic ketone of formula (V) in General spend from 0.2 to 5 mol, preferably 0.5 to 2 mol of the carbonyl compounds of formula (VI).

Unless otherwise stated, all methods according to the invention is carried out in General under atmospheric pressure. It is possible, however, to work at elevated or reduced pressure, typically between 0.1 bar and 10 bar.

Way-2 - reductive amination

As diluents for implementing the method (2) according to the invention can be used all inert organic solvents. It is advisable to use aliphatic, acyclic or aromatic hydrocarbons, such as petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or deck is in; halogenated hydrocarbons, such as chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloroethane or trichloroethane; ethers, such as diethyl ether, diisopropyl ether, methyl tert-butyl ether, methyl tert-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole; or amides such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylformamide, N is an organic or triamide hexamethylphosphoric acids, alcohols, e.g. methanol, ethanol, isopropanol, n-butanol, sec-butanol or tert-butanol, and mixtures thereof with water or pure water.

Reductive amination in method (C) according to the invention is carried out in the presence of an amine and a reducing agent. As the amine component, you can use ammonia, salts of ammonia, such as ammonium formate, but also ammonia with a simple substitution, for example, methylamine, ethylamine, Propylamine, cyclopropylamine etc. as reductants can be used with all common inorganic and organic reducing agents. It is advisable to apply hydrides and hydroxides of alkaline or alkaline earth metals or boron hydrides, for example sodium hydride, cyanoborohydride sodium, sodium borohydride, or hydrogen donors, such as elemental hydrogen, hydrazine, cyclohexadien or formate and formate matched with the appropriate amine components.

Reductive amination in method (C) according to the invention is carried out, if necessary, in the presence of a catalyst. As catalysts it is possible to apply conventional, for example, hydrogenation catalysts, for example, metal palladium, Nickel (Raney Nickel), platinum, iron, ruthenium, osmium or their salts. These catalysts can also be applied to the media, for example, coal, silicon, zeolites, etc. or stable ligands.

The reaction temperature in the implementation of restorative amination in method (C) according to the invention can be varied within wide limits. As a rule, operate in temperatures from 0°C to 150°C, preferably at temperatures from 20°C to 110°C.

In the implementation of restorative amination in method (C) according to the invention for preparing compounds of the formula (III) per mole of cyclic ketones of the formula (V) in General spend from 0.2 to 50 mol, preferably 1 to 20 mol amine and a reducing agent, and 0.01 to 10 mol % of catalyst.

Unless otherwise stated, all methods according to the invention is carried out in General under atmospheric pressure. It is possible, however, to work at elevated or reduced pressure, typically between 0.1 bar and 10 bar.

The substances according to the invention possess strong antimicrobial activity and can be applied to DL the fight against harmful microorganisms, for example, fungi and bacteria, in the field of protection of plants and materials.

Fungicides can be used in plant protection for combating Plasmodio-phoromycetes, Oomycetes, Chytridiomycota, Zygomycetes, Ascomycetes, Basi-diomycetes and Deuteromycetes.

Microbicides can be used in plant protection for combating Pseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae and Streptomycetaceae.

As examples, non-misleading, however, restrictions should be called some pathogens of fungal and bacterial diseases that fall under the above General definition:

Diseases caused by pathogens true powdery mildew, for example,

By Blumeria species, as, for example, Blumeria graminis;

By Podosphaera species, such as Podosphaera leucotricha;

By Sphaerotheca species, such as, for example, Sphaerotheca fuliginea;

Types of Uncinula-Arten, as, for example, Uncinula necator;

Diseases caused by rust pathogens of plants, for example, Gymnosporangium Species, such as, for example, Gymnosporangium sabinae Hemileia Species, such as, for example, Hemileia vastatrix;

By Phakopsora species, such as, for example, Phakopsora pachyrhizi and Phakopsora meibomiae;

By Puccinia species, such as Puccinia recondita;

By Uromyces species, such as Uromyces appendiculatus;

Diseases caused by pathogens group oomycete, for example,

By Bremia species, such as Bremia lactucae;

Species of Peronospora., as, for example, Peronospora. pisi or P. brassicae;

Species of Phytophthora, as, for example, Phytophthora infestans;

By Plasmopara species, such as, in the example, Plasmopara viticola;

Pseudoperonospora species, such as Pseudoperonospora humuli or Pseudoperonospora Species cubensis;

The Pythium species, such as Pythium ultimum;

Spotting and wilting of leaves, caused by, for example,

Species of Alternaria, such as Alternaria solani;

The Cercospora species, such as, for example, Cercospora beticola;

Species Cladiosporum, as, for example, Cladiosporium cucumerinum;

By Cochliobolus species, such as Cochliobolus sativus

(Forms conidia: Cereals, synonym: Helminthosporium);

Species of Colletotrichum, as, for example, Colletotrichum lindemuthanium;

Cycloconium species, such as, for example, cyclomatic oleaginum;

By Diaporthe species, such as dirth citri;

By Elsinoe species, such as, for example, Elsinoe fawcettii;

By Gloeosporium species, such as, for example, Gloeosporium laeticolor;

By Glomerella species, such as, for example, Glomerella cingulata;

By Guignardia species, such as, for example, Guignardia bidwelli;

By Leptosphaeria species, such as, for example, Leptosphaeria maculans;

By Magnaporthe species, such as, for example, Magnaporthe grisea;

Species of Mycosphaerella, as, for example, Mycosphaerelle graminicl;

By Phaeosphaeria species, such as, for example, Phaeosphaeria nodorum;

By Pyrenophora species, such as Pyrenophora teres;

By Ramularia species, such as, for example, Ramularia collo-cygni;

By Rhynchosporium species, such as, for example, Rhynchosporium secalis;

The Septoria species, such as, for example, Septoria apii;

The Typhula species, such as, for example, Typhula incarnata;

By Venturia species, such as Venturia inaequalis;

Diseases of the stem and root, caused by, for example,

Corticium, as, for example, Corticium frost;

The Fusarium species such as, for example, Fusarium oxysporum;

By Gaeumannomyces species, such as, for example, Gaeumannomyces graminis;

By Rhizoctonia species, such as, for example, Rhizoctonia solani;

Tapesia species, such as, for example, Tapesia acuformis;

By Thielaviopsis species, such as, for example, Thielaviopsis basicola;

Disease stalks and panicles (including corn cobs), caused by,

for example,

Species of Alternaria, such as Alternaria spp.;

Species of Aspergillus, such as Aspergillus flavus;

Species of Cladosporium, as, for example, Cladosporium spp.;

The Claviceps species, such as, for example, Claviceps purpurea;

The Fusarium species such as, for example, Fusarium culmorum;

By Gibberella species, such as, for example, Gibberella zeae;

Monographella species, such as, for example, Monographella nivalis;

Diseases caused by Golovneva mushrooms, for example,

By Sphacelotheca species, such as, for example, Sphacelotheca reiliana;

By Tilletia species, such as Tilletia caries;

By Urocystis species, such as, for example, Urocystis occulta;

By Ustilago species, such as Ustilago nuda;

Fruit rot caused, for example,

Species of Aspergillus, such as Aspergillus flavus;

The Botrytis species, such as Botrytis cinerea;

Species of Penicillium, such as Penicillium expansum;

By Sclerotinia species, such as, for example, Sclerotinia sclerotiorum;

By Verticilium species, such as, for example, Verticilium alboatrum;

Seed and soil types of rot and decay, and also diseases of seedlings,

caused, for example,

The Fusarium species such as, for example, Fusarium culmorum;

Species of Phytophthora Arten, wie beispielsweise Phytophthora cactorum;

The Pythium species, such as Pythium ultimum;

By Rhizoctonia species, such as, for example, Rhizoctonia solani;

The Sclerotium species, such as, for example, Sclerotium rolfsii;

Cancerous diseases, galls and witches broom caused, for example,

Types of Agent, as Agent galligena;

Volostye diseases caused by, for example, by Monilinia Species, such as, for example, Monilinia laxa;

Deformations of leaves, flowers and fruits caused, for example,

By Taphrina species, such as, for example, Taphrina deformans;

Degeneration of woody plants caused, for example,

By Esca species, such as Phaemoniella clamydospora;

Blüten - and Samenerkrankungen, hervorgerufen durch z.B.

The Botrytis species, such as Botrytis cinerea;

Diseases of tubers of plants caused, for example, by Rhizoctonia Species, such as, for example, Rhizoctonia solani;

Diseases caused by bacterial pathogens, such as

The Xanthomonas species, such as Xanthomonas campestris pv. oryzae;

Species of Pseudomonas, such as Pseudomonas syringae pv. lachrymans;

By Erwinia species, such as, for example, Erwinia amylovora;

Suitable struggle with the following diseases of soya beans:

Fungal diseases of leaves, stems, pods and seeds caused, for example,

Alternaria leaf spot (Alternaria spec. atrans tenuissima), Anthracnose (Colletotrichum gloeosporoides dematium var. truncatum), Brown spot (Septoria glycines), Cercospora leaf spot and blight (Cercospora kikuchii), Choanephora leaf blight (Choanephora infundibulifera trispora (Syn.)), Dactuliophora leaf spot (Dactuliophora glycines), Downy Mildew (Peronospora. manshurica), Cereals blight (Cereals glycini), Frogeye Leaf spot (Cercospora sojina), Leptosphaerulina Leaf Spot (Leptosphaerulina trifolii), Phyllostica Leaf Spot (Phyllosticta sojaecola), PowderyMildew (Microsphaera diffusa), Pyrenochaeta Leaf Spot (Pyrenochaeta glycines), Rhizoctonia Aerial, Foliage, and Web Blight (Rhizoctonia solani), Rust (Phakopsora pachyrhizi), Scab (Sphaceloma glycines), Stemphylium Leaf Blight (Stemphylium botryosum), Target Spot (Corynespora cassiicola)

Fungal diseases of roots and the stem base caused, for example,

Black Root Rot (Calonectria crotalariae), Charcoal Rot (Macrophomina phaseolina), Fusarium Blight or Wilt, Root Rot, and Pod and Collar Rot (Fusarium oxysporum, Fusarium orthoceras, Fusarium semitectum, Fusarium equiseti), Mycoleptodiscus Root Rot (Mycoleptodiscus terrestris), Neocosmospora (Neocosmopspora vasinfecta), Pod and Stem Blight (Diaporthe phaseolorum), Stem Canker (Diaporthe phaseolorum var. caulivora), Phytophthora Rot (Phytophthora megasperma), Brown Stem Rot (Phialophora gregata), Pythium Rot (Pythium aphanidermatum, Pythium irregulare, Pythium debaryanum, Pythium myriotylum, Pythium ultimum), Rhizoctonia Root Rot, Stem Decay and Damping-Off (Rhizoctonia solani), Sclerotinia Stem Decay (Sclerotinia sclerotiorum), Sclerotinia Southern Blight (Sclerotinia rolfsii), Thielaviopsis Root Rot (Thielaviopsis basicola).

The active substances according to the invention also have a pronounced strengthening effect in plants. For this reason, they are suitable for mobilizing their own immunity of plants to protect against destruction of harmful microorganisms.

Under restorative (increasing resistance) substances in the current context involve substances that can stimulate the defense system of plants in such a way that the treated plants were able to demonstrate a high resistance to subsequent inoculation of undesirable microorganisms.

Under unwanted organisms in this case it is necessary to understand the phytopathogenic fungi, bacteria and viruses. The substances according to the invention can thus be used to protect plants within a certain period after treatment against the destruction of the mentioned pests. The period for which protection applies generally for 1 to 10 days, preferably for 1 to 7 days after treatment of the plants active ingredients.

Good tolerance of the plants active ingredients in the concentrations required for combating plant diseases, permits to handle the aerial parts of plants, planting and seed and soil.

When this active substances according to the invention with particular success can be applied to diseases of cereals, for example, Puccinia species and diseases in viticulture, horticulture and vegetable growing, for example, against species of Botrytis, Venturia or Alternaria.

The active substances according to the invention is also suitable for increasing the yield. In addition, they have low toxicity, and plants demonstrate their good tolerability.

Compounds according to the invention can, if necessary, in certain concentrations, or when a certain flow rate be used as herbicides, for influencing plant growth and for combating animal pests. Also, if necessary, their possible use is as an intermediate or starting products for the synthesis of other active ingredients.

According to the invention it is possible to treat all plants and plant parts. Under the plants in this case refers to all plants and plant populations such as desired and undesired wild and cultivated plants (including cultivated plants found in the wild). Cultivated plants can be removed by conventional methods of breeding and optimization or by biotechnological and genetic engineering methods or combinations of such methods, including genetically modified plants and plant varieties protected or not protected breeding law. Under parts of plants should understand all above-ground and below-ground parts and organs of plants, such as shoot, leaf, flower and root, and as an example leaves, needles, stems, trunks, flowers, fruit bodies, fruits and seeds and also roots, tubers and rhizomes. The plant parts also include the harvest and the material for the vegetative and generative reproduction, for example cuttings, tubers, rhizomes, cuttings and seeds.

The process according to the invention of the plants and parts of plants active substances produced directly or by action on their surroundings, habitat or storage by conventional means, for example by immersion, spraying, treatment pairs, dispersion, dissipation, lubrication is, and in the case of breeding material, in particular seed, also by coating a single layer or a multilayer shell.

In the protection of materials the substances according to the invention can be used for the protection of technical materials from damage and destruction by unwanted microorganisms.

Under the technical materials under this text should be understood inanimate materials, prepared for use in the technique. Examples of technical materials, protected active substances according to the invention from modification and destruction of microbes can be adhesives, glues, paper and cardboard, textiles, leather, wood, paints and plastic articles, lubricant-coolants and other materials, affected, or biodegradable. Among the protected materials should also be called part of the production equipment, such as cooling circuits which can damage the growth of microorganisms. In the framework of the present invention may be called as technical materials, adhesives, glues, paper and cardboard, leather, wood, paints, cooling lubricants and liquid fluids, the most suitable tree.

As microorganisms capable of causing destruction or the application of technical materials should be called, for example, bacteria, fungi, yeast, algae and slimy organisms [Schleimorganismen]. The active substances according to the invention are preferably fungi, in particular mould, coloring and destructive tree mushrooms (Basidiomycota), as well as on the mucous membranes of the organisms and algae.

As examples include microorganisms of the following genera:

Alternaria, for example, Alternaria tenuis,

Aspergillus, for example, Aspergillus niger,

Chaetomium, for example, Chaetomium globosum,

Coniophora, for example, Coniophora puetana,

Lentinus, for example, Lentinus tigrinus,

Penicillium, for example, Penicillium glaucum,

Polyporus, for example, Polyporus versicolor,

Aureobasidium, for example, Aureobasidium pullulans,

Sclerophoma, such as, Sclerophoma pityophila,

Trichoderma, for example, Tpichoderma viride,

Escherichia, such as Escherichia coli,

Pseudomonas, for example, Pseudomonas aeruginosa,

Staphylococcus, for example, Staphylococcus aureus,

Active substances, depending on their physical and/or chemical properties, in each case, can be introduced into the usual formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, small polymer capsules and weight for shells, seed, and formulations for hot and cold spray aerosols with minimal volume drops (ULV-Kalt - and Warmnebel-Formulierungen).

These formulations are produced in a known manner, for example by mixing the active substances with extenders, i.e. the LM is Kimi solvents, liquefied gases under pressure and/or solid carriers, optionally using surfactants, i.e. emulsifiers or dispersing agents and/or foaming agents. If the filler used water, an additional solvent may be, for example, an organic solvent. The main liquid solvents: aromatics such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzene, chloroethylene or methylene chloride, aliphatic hydrocarbons, e.g. cyclohexane or paraffins, for example, oils of mineral or vegetable oils, alcohols, such as butanol or glycol and also their ethers and esters, ketones, such as acetone, methyl ethylketone, methyl-isobutylketone or cyclohexanone, solvents with high polarity, for example, dimethylsulfoxide, and water. Under liquefied gaseous extenders and media mean fluid at normal temperature and atmospheric pressure are in the gaseous state, for example, aerosol engine gases, such as kalogeropoulou, as well as butane, propane, nitrogen and carbon dioxide. Solid carriers can be mineral powders such as kaolin, alumina, talc, chalk, quartz, and Capulet, montmorillonite or hard-shelled land and synthetic stone flour, for example, highly dispersed silicic acid, alumina and silicates. Solid carriers for granules can be, for example, crushed and fractionated minerals, such as calcite, pumice, marble, thick, dolomite, and also synthetic granules of inorganic and organic powders and granules of organic material such as sawdust, coconut shells, corn cobs and stalks of tobacco; emulsifiers and/or foaming agents may be, for example, nonionic and anionic emulsifiers, as esters of polyoxyethylene and fatty acids, ethers of polyoxyethylene and fatty alcohols, for example, alkylaryl-polyglycolide ethers, alkyl sulphonates, alkyl sulphates, arylsulfonate, as well as protein hydrolysates. As dispersing agents it is possible to apply, for example, the spent sulfite liquor with lignin and methylcellulose.

In recipes you can use additives to improve adhesion, for example, carboxymethyl cellulose, natural or synthetic polymers in powdered, granular or latexotica condition, such as gum Arabic, polyvinyl alcohol, polyvinyl acetate, and also natural phospholipids, as Catalina or lecithins, and synthetic phospholipids. You can also add mineral and races who sustained fashion oils.

It is possible to use colorants such as inorganic pigments, for example iron oxide, titanium, sankalia (Ferrocyanblau), and organic dyestuffs, such as alizarin, softlotion and metallophthalocyanine dyes, and trace elements such as iron, manganese, boron, copper, cobalt, molybdenum and zinc.

As a rule, the content of active substance in the formulation is from 0.01 to 95 wt.%, preferably from 0.5 to 90%.

Active substances as such or in formulations can be applied in a mixture with known fungicides, bactericides, acaricides, nematicides or insecticides, for example, to expand thus the spectrum of action or to prevent the development of resistance. In many cases, the observed synergistic effects, i.e. the effectiveness of the mixture is higher than that of the individual components.

For use in the blends of the most convenient, for example, the following connections:

Fungicides.

Inhibitors of nucleic acid synthesis: for example benalaxyl, benalaxyl-M, bupirimate, hirasaki, clothingon, dimethirimol, ethirimol, parallaxis, hymexazol, mefenoxam, metalaxyl, metalaxyl-M, operas, oxadixyl, oxolinic acid;

2) Inhibitors of mitosis and cell division: for example, benomyl, carbendazim, dietphenterm, ethaboxam, fuberidazole, pencycuron, thiabendazole, TIF netmeter, zoxamide;

3) Respiratory inhibitors (inhibitors of the respiratory chain):

3.1) Inhibitors I complex of the respiratory chain: for example, diplomatarium;

3.2) Inhibitors II complex of the respiratory chain: for example, boscalid/nicobifen, carboxin, fanforum, flutolanil, parameter, pharmacyclics, mepronil, oxycarboxin, pentopia, leflunomid;

3.3) Inhibitors III complex in the respiratory chain: for example amisulbrom, AZOXYSTROBIN, cyazofamid, dimoxystrobin, anestrous, famoxadone, fenamidone, fluoxastrobin, kresoximmethyl, metamyosyn, orysastrobin, picoxystrobin, pyraclostrobin, Trifloxystrobin;

4) Pulpers communication: for example dinocap, fluazinam, mathildenhohe;

5) Inhibitors of ATP production: for example, fentiazac, findingaid, fistinginaction, silthiofam;

6) Inhibitors of the biosynthesis of amino acids and proteins: such as andapril, blasticidin-S, cyprodinil, kasugamycin, Casamicciola hydrate, mepanipyrim, Pyrimethanil;

7) Inhibitors of the signal: for example, fenpiclonil, fludyoksonil of quinoxyfen;

8) Inhibitors of fat synthesis and membrane synthesis: for example, biphenyl, chlozolinate, edifenphos, iodosorb, iprobenfos, iprodion, isoprothiolane, procymidon, propamocarb, propamocarb hydrochloride, pyrazophos, cyclophosphates, vinclozolin;

9) Inhibitors of ergosterol biosynthesis: for example aldim the RF, azaconazole, bitertanol, bromuconazole, tsyprokonazolu, diclobutrazol, difenoconazole, diniconazole, diniconazole-M, dodemont, dudemanpeace, epoxiconazol, itaconate, fenarimol, fenbuconazole, fenhexamid, fenpropidin, fenpropimorph, fluiconnecto, Floridita, flusilazol, flotrol, vorconizole, vorconizole, hexokinase, imazalil, maslishat, kabekona, ipconazole, metconazole, myclobutanil, naftifine, nuarimol, Expocentr, paclobutrazol, peyratout, penconazole, prochloraz, propiconazole, prothioconazole, perimutter, pirivenas, simionato, spiroxamine, tebuconazole, terbinafine, terconazole, triadimefon, triadimenol, tridemorph, triflumizole, triforine, triticonazole, uniconazole, viceconsul, voriconazole;

10) Inhibitors of cell wall synthesis: for example benthiavalicarb, dimethomorph, floorf, iprovalicarb, polyoxins, palikari, validamycin;

11) melanin biosynthesis Inhibitors: for example napropamide, diclocil, phenoxyl, phtalic, pyroquilon, tricyclazole;

12) Inducers of resistance: for example, acibenzolar-8-methyl, provenzal, tudinal;

13) Connect multiple actions: for example Bordeaux mixture, captafol, Captan, CHLOROTHALONIL, copper naphthenate, copper oxide, copper oxychloride, preparations of copper, such as copper hydroxide, copper sulfate, dichlofluanid, dithianon, dodine, is one of the free base, ferbam, feriole guazatine, guazatine, iminoctadine, iminoctadine, iminoctadine, man-copper, MANCOZEB, MANEB, metiram, metiram zinc, oxin-copper, propineb, sulfur and sulfur drugs, including calcium polysulfide, thiram, tolyfluanid, zineb, Zir;

14) One of the compounds from the following list: (2E)-2-(2-{[6-(3-chloro-2-methylphenoxy)-5-ftorpirimidinu-4-yl]oxy}phenyl)-2-(methoxyimino)-N-methyl-ndimethylacetamide, (2E)-2-{2-[({[(1E)-1-(3-{[(E)-1-fluoro-2-phenyl]oxy}phenyl)ethylidene]amino}oxy)methyl]phenyl}-2-(methoxyimino)-N-methylacetamide, 1-(4-chlorophenyl)-2-(1H-1,2,4-triazole-1-yl)cycloheptanol, 1-[(4-methoxyphenoxy)-methyl]-2,2-dimethylpropyl-1H-imidazole-1-carboxylate, 2-(4-chlorophenyl)-N-{2-[3-methoxy-4-(prop-2-in-1 yloxy)phenyl]ethyl}-2-(prop-2-in-1 yloxy)ndimethylacetamide, 2,3,5,6-tetrachloro-4-(methylsulphonyl)pyridine, 2-butoxy-6-iodine-3-propyl-4H-chromen-4-one, 2-chloro-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)nicotinamide, 2-phenylphenol and its salts, 3,4,5-trichloropyridine-2,6-dicarbonitrile, 3,4-dichloro-N-(2-cyanophenyl)isothiazol-5-carboxamide, 3-[5-(4-chlorophenyl)-2,3-dimethylisoxazole-3-yl]pyridine, 5-chloro-6-(2,4,6-tri-forfinal)-N-[(1R)-1,2,2-trimethylpropyl][1,2,4]triazolo[1,5-a]pyrimidine-7-amine, 5-chloro-7-(4-methylpiperidin-1-yl)-6-(2,4,6-tryptophanyl)[1,2,4]triazolo[1,5-a]pyrimidine, 5-chloro-N-[(1 R)-1,2-dimethylpropyl]-6-(2,4,6-Cryptor-phenyl)[1,2,4] triazolo[1,5-a]pyrimidine-7-amine, 8-hydroxyquinolinato, bentazon, bentaxel, capsaicin, arvon, chinomethionat, kurane, cyflufenamid, having cymoxanil, dazomet, dibakar, dichlorophen, declomycin, dicloran, difenzoquat, difenzoquat the methyl sulfate, diphenylamine, verison, flamethower, torpille, foromic, glucolipid, fosetyl-aluminum, fosetyl-calcium, fosetyl-sodium, hexachlorobenzene, arunamarin, metasurfaces, methyl (2-chloro-5-{(1E)-N-[(6-methylpyridin-2-yl)-methoxy]ethanamide}benzyl)carbamate, methyl (2E)-2-{2-[({cyclopropyl[(4-methoxyphenyl)imino]methyl}thio)methyl]phenyl}-3-ethoxyacrylate, methyl 1-(2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)-1H-imidazole-5-carboxylate, methyl 3-(4-chlorophenyl)-3-{[N-(isopropoxycarbonyl)valil]amino}propanoate, methyl isothiocyanate, metrafenone, millionizer, N-(3',4'-dichloro-5-forbiden-2-yl)-3-(deformity)-1-methyl-1H-pyrazole-4-carboxamide, N-(3-ethyl-3,5,5-tri-methylcyclohexyl)-3-(formylamino)-2-hydroxybenzamide, N-(4-chloro-2-nitro-phenyl)-M-ethyl-4-methylbenzenesulfonamide, N-[(5-bromo-3-chloropyridin-2-yl)methyl]-2,4-dichloronicotinic, N-[1-(5-bromo-3-chloropyridin-2-yl)ethyl]-2,4-dichloronicotinic, N-[1-(5-bromo-3-chloropyridin-2-yl)ethyl]-2-fluoro-4-Jody-codenamed, N-[2-(4-{[3-(4-chlorophenyl)prop-2-in-1-yl]oxy}-3-methoxyphenyl)-ethyl]-N2-(methylsulphonyl)valinamide, N-{(2)-[(cyclopropylmethoxy)-imino]-[6-(deformedarse)-2,3-differenl]methyl}-2-phenylacetamide, N-{2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]ethyl}-2-(trifluoromethyl)benzamid, natamycin, dimethylthiocarbamate Nickel, neath hotel-isopropyl, O-{1-[(4-methoxy-phenoxy)methyl]-2,2-dimethylpropyl} 1H-imidazol-1-carbothioate, Actelion, oxamate, oxidation, pentachlorophenol and its salts, phosphoric acid and its salts, piperalin, propanecarboxylate, propanoic-sodium, proquinazid, pyrrolnitrin, quintozene, telital, tecnazene, triazoxide, trihemic, Suriname.

Microbicides.

Bronopol, dichlorophen, nitrapyrin, dimethylthiocarbamate Nickel, kasugamycin, Actelion, francebuy acid, oxytetracycline, provenzal, streptomycin, telital, copper sulphate and other formulations of copper-based.

Insecticides/acaricides/nematicides.

1. Inhibitors of acetylcholinesterase (AChE)

1.1. Carbamates (for example, alankar, aldicarb, aldoxycarb, allistar, aminocarb, azamethiphos, bendiocarb, benfuracarb, bofenkamp, betacar, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, cloethocarb, coumaphos, cyanofenphos, cyanophos, dimetilan, ethiofencarb, fenobucarb, fanatical, fomentant, furathiocarb, isoprocarb, METAM-sodium, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, promecarb, propoxur, thiodicarb, thiofanox, triazamate, trimeter, CMS, killchar)

1.2. Organophosphates (e.g., acetat, azamethiphos, azinphos (methyl, ethyl) bromoacetyl, pumpevents (methyl), butamifos, cadusafos, carbophenothion, chlorethoxyfos, chlorfenson the OS, chlormephos, chlorpyrifos methyl, ethyl), coumaphos, cyanofenphos, cyanophos, chlorfenvinfos, demeton-8-methyl, demeton-8-methylsulfone, dialifos, diazinon, dichlofenthion, dichlorvos (DDVP), dicrotophos, dimethoate, dimethylene, dioxybenzone, disulfoton, EPN, ethion, ethoprophos, etrimfos, famphur, fenamiphos, fenitrothion, fensulfothion, fenthion, flupirtine, fonofos, formation, tomatlan, fosthiazate, heptenophos, iodofenphos, iprobenfos, isazofos, isofenphos, isopropyl O-salicylate, isoxathion, Malathion, mecarbam, methacrifos methamidophos, methidathion, mevinphos, monocrotophos, naled, omethoate, oxydemeton-methyl, parathion (methyl, ethyl), pentat, Fort, fosalan, phosmet, phosphamidon, fastcars, phoxim, pirimiphos (methyl, ethyl), profenofos, propafol, propetamphos, prothiofos, procoat, pyraclofos, predatation, predation, quinalphos, sabots, sulfotep, sulprofos, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, trichlorfon, validation)

2. Modulators of sodium channels (potential-dependent blockers of sodium channels)

2.1. Pyrethroids (for example, acrinathrin, allethrin (d-CIS-TRANS, d-TRANS), beta-cyfluthrin, bifenthrin, bioallethrin, bioallethrin-6-cyclopentyl-isomer, bioeconomical, bioprotein, bioresmethrin, lowprotein, CIS-cypermethrin, CIS-resmethrin, CIS-permethrin, claritin, cicloprofen, cyfluthrin, zihal the trine, cypermethrin (alpha-, beta-, theta-, Zeta), cyphenothrin, DDT, deltamethrin, empenthrin (IR-isomer), esfenvalerate, etofenprox, fenfluthrin, fenpropathrin, generatin, fenvalerate, lubricant, flucythrinate, flavandiols, flumethrin, fluvalinate, tupfenrock, gamma cyhalothrin, imiprothrin, kadethrin, lambda cyhalothrin, metofluthrin, permethrin (CIS-, TRANS-), phenothrin (IR-TRANS-isomer), prallethrin, perflutren, protrudent, prismatron, resmethrin, RU 15525, selflove, Tau fluvalinate, tefluthrin, tarletan, tetramethrin (1R-isomer), tralomethrin, transfluthrin, ZXI 8901, pyrethrins (feverfew))

2.2. Oxadiazine (for example, indoxacarb)

3. Agonists and antagonists of acetylcholine receptors

3.1. Chloronicotinyl/neonicotinoids (e.g., acetamiprid, clothianidin, dinotefuran, Imidacloprid, nitenpyram, nithiazine, thiacloprid, thiamethoxam)

3.2. Nicotine, bensultap, cartap

4. Modulators of acetylcholine receptors

4.1. Spinosyn (for example, spinosad)

5. Antagonists, chloride channel, managed GABA

5.1. Cyclodiene organochlorine (for example, camphechlor, chlordane, endosulfan, gamma-HCH, HCH, heptachlor, lindane, Methoxychlor

5.2. Pipoly (for example, acetarsol, ethiprole, fipronil, unilibro)

6. Activators chloride channels

6.1. Machine (e.g., abamectin, avermectin, emamectin, emamectin-benzoate, ivermectin is, milbemectin, milbemycin)

7. The juvenile hormone mimetics

(for example, giovanola, epitonin, fenoxycarb, hydroprene, CANopen, methoprene, pyriproxyfen, triplen)

8. Antagonists and disintegrator ecdysone

8.1. Diacylhydrazines have (for example, chromafenozide, halogenated, methoxyfenozide, tebufenozide)

9. Inhibitors of chitin biosynthesis

9.1. Benzoylacetone (for example, bistriflate, chlorfluazuron, diflubenzuron, fluazuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, notimplemented, enflurane, teflubenzuron, triflumuron)

9.2. Buprofezin

9.3. Cipromycin

10. Inhibitors of oxidative phosphorylation, disintegrator ATP

10.1. Diafenthiuron

10.2. ORGANOTIN (for example, azocyclotin, cyhexatin, fenbutatin-oxide)

11. Uncouplers of oxidative phosphorylation by interruption of the proton gradient

11.1. The pyrrole (for example, chlorfenapyr)

11.2. Dinitrophenol (for example, binapacryl, dinobuton, dinocap, DNOC)

12. Inhibitors of electron transport in position 1

12.1. Inhibitors of mitochondrial electron transport (for example, fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad, elfenberg)

12.2. Hydramethylnon

12.3. Dicofol

13. Inhibitors of electron transport in position 2

13.1. Rotenon

14. Inhibitors of the electronic the electronic transport in position 3

14.1. Acequinocyl, flociprin

15. Microbial disruptors of the intestinal membrane insect Strains of Bacillus thuringiensis

16. Inhibitors of fat synthesis

16.1. Tetronic acid (for example, spirodiclofen, spiromesifen)

16.2. Tetralogie acid [e.g., 33-(2,5-dimetilfenil)-8-methoxy-2-oxo-1-azaspiro[4.5]Dec-3-EN-4-yl ethyl carbonate (aka: carboxylic acid, 3-(2,5-dimetilfenil)-8-methoxy-2-oxo-1-azaspiro[4.5]Dec-3-EN-4-yl ester, (CAS.: 382608-10-8) and carboxylic acid, dimetilfenil)-8-methoxy-2-oxo-1-azaspiro[4.5]Dec-3-EN-4-yl ethyl ester (CAS.: 203313-25-1)]

17. Carboxamide

(for example, flonicamid)

18. Agonists octopamine

(for example, amitraz)

19. Inhibitors of magnesium-stimulated ATPase (for example, propargyl)

20. Phthalic amides

(for example, N2-[1,1-Dimethyl-2-(methylsulphonyl)ethyl]-3-iodine-N1-[2-methyl-4-[1,2,2,2-titrator-1-(trifluoromethyl)ethyl]phenyl]-1,2-benzenedicarboxamide (CAS: 272451-65-7), flubendiamide)

21. Analogues of toxins nymphs

(for example, thiocyclam-hydrocalc, thiosulfat-sodium)

22. Biologicals, hormones or pheromones

(for example, azadirachtin, Bacillus spec., Beauveria spec., Coleman, Metarrhizium spec., Paecilomyces spec., thuringiensis, Verticillium spec.)

23. Active ingredients with unknown or non-specific mechanism of action

23.1. The fumigants (e.g., aluminum phosphide, methyl bromide, Sulfuryl-fluoride)

23.2. izbiratelnye suppression of appetite (for example, cryolite, flonicamid, pymetrozine)

23.3. The mite growth inhibitors (e.g., kafentzis, etoxazole, hexythiazox)

23.4. Midflame, banknotes, benoxinate, bifenazate, bromopropylate, buprofezin, chinomethionat, Chlordimeform, Chlorobenzilate, chlorine picrin, clotiazepam, ciclope, titlemedium, dicyclanil, tenoxicam, pentaphenyl, flibanserin, lufenuron, lotensin, gossiper, hydramethylnon, japonicus, methoxamine, petroleum, piperonyl piperonyl, sodium oleate, perflubron, pyridalyl, periphral, sulfluramid, tetradifon, tetrasul, triuralin, verboten, as well as the compounds 3-methyl-phenyl-propylgallate (somacid Z), the compound 3-(5-chloro-3-pyridinyl)-8-(2,2,2-triptorelin)-8-azabicyclo[3.2.1]Octan-3-carbonitrile (CAS 185982-80-3) and the corresponding 3-endosomes (CAS 185984-60-5) (see international application WO 96/37494, WO 98/25923), as well as preparations containing plant extracts, nematodes, fungi or viruses with insecticidal action.

It is also possible mixing with other known active substances, such as herbicides, or with fertilizers and growth regulators, protective equipment or semiochemicals (Semiochemicals).

In addition, the compounds according to the invention of the formula (I) possess very good antifungal activity. Spectrum of antifungal activity is very wide, especially the impact on dermatophyte and yeast, moulds and diphasic fungi (for example, species of Candida, such as Candida albicans, Candida glabrata), and Epidermophyton floccosum, Aspergillus species such as Aspergillus niger and Aspergillus fumigatus, Trichophyton species such as Trichophyton mentagrophytes, Microsporon species such as Microsporon canis and audouinii. The enumeration of these fungi in any case does not represent a limitation of the spectrum, and is only the nature of the notes.

The active substances can be applied as such, in the form of recipes or prepared from them ready-to-use forms, such as ready-to-use solutions, suspensions, wettable powders, pastes, soluble powders, spray means and granulates. Application carried out in the usual manner, for example by watering, spraying, sprinkling, scattering, dispersion, lubrication, etc. in Addition, you can create suspensions of active substances by way of Ultra-Low-Volume" or to be injected formulation of the active substance or active substance itself into the soil. You can also handle seed plants.

When using the active compounds as fungicides their consumption, depending on the processing method, can be varied within a wide range. When processing parts of plants, the consumption of active ingredient is usually from 0.1 to 10,000 g/ha, preferably from 10 to 1,000 g/ha When processing the seed of the plant is the first consumption of the active substance is usually, from 0.001 to 50 g per kilogram of seed, preferably from 0.01 to 10 g per kilogram of seed. Soil consumption of active ingredient is usually from 0.1 to 10,000 g/ha, preferably from 1 to 5,000 g/ha

As described above, according to the invention it is possible to treat all plants and their parts. In a preferred form of execution of the process plant species and varieties found in the wild or bred conventional biological methods, for example, by crossing or by fusion of protoplasts and their parts. In another preferred form of execution of process plants and varieties, obtained by genetic engineering methods, if necessary in combination with conventional methods (Genetic Modified Organisms), and parts thereof. The terms "parts" and "parts of plants" were explained above.

The most appropriate process according to the invention plants are common on the market or used varieties. Under the plant varieties understand plants with new properties ("Traits"traits), obtained as conventional breeding or by mutagenesis or by using recombinant DNA technology. This can be varieties, biotypes or strains.

Depending on the species or plant variety, growing location and growth conditions (soils, climate, vegetation period, diet), the treatment according to image meniu can cause "sverhzapominaniya" ("synergistic") effects. This can be, for example, reducing consumption and/or expansion of the range of exposure and/or gain exposure to the chemicals and agents used according to the invention, better plant growth, improved root development, improving the sustainability of the species or varieties of plants, increased shoot growth, increased vitality of plants, increase resistance to high or low temperatures, drought or salt content in the water or soil, the increase in the intensity of flowering, easier harvesting, accelerated maturation, growth yields, bigger fruits, plants, improvement of green colour of foliage ([grünere Blattfarbe])earlier flowering, higher quality and/or nutritional value of the harvested crop, the increase in the concentration of sugar in fruit, increased persistence and/or facilitating a processing of the harvest in excess of the expected effects.

To transgenic (received genetic engineering methods) plants or plant varieties that are suitable to process according to the invention include all plants which, thanks to genetic engineering modification, received genetic material which provides these plants are particularly valuable useful properties ("Traits"traits). Examples of such properties are better plant growth, increased resistance to high or low temperatures, drought is or contents of salts in water or soil, the increase in the intensity of flowering, easier harvesting, accelerated maturation, increasing productivity, improving quality and/or nutritional value of the crop, increasing its persistence and/or ease of processing. Additional particularly useful examples of such properties are increasing the ability of plants to defend themselves against animal and microbial pests, such as against insects, mites, pathogens of plants, fungi, bacteria and/or viruses, and also increased plant resistance to certain herbicides. As examples of transgenic plants should mention the most important cultivated plants such as cereals (wheat, rice), maize, soybeans, potatoes, sugar beets, tobacco, rape and also fruit plants (with the fruits apples, pears, citrus fruits and grapes), with corn, soybeans, potatoes, cotton, tobacco and oilseed rape should highlight. Among the properties ("Traits", signs) of particular note is the increasing resistance of plants to insects, arachnids, worms and snails caused by toxins produced by plants, particularly those which plants produce due to the genetic material (for example by the genes CryIA(a), CryIA(b)CryIA(c), CryIIA, CryIIIA, CryIIIB2, Cry9c Cry2Ab, Cry3Bb and CryIF and also combinations) from Bacillus Thuringiensis ("Bt plants"). Among the properties ("Traits"signs) should taqreeb to mention the increased resistance of plants to fungi, bacteria and viruses due to systemic acquired resistance (SAR), sisteminin, phytoalexins, elicitors and resistance genes and correspondingly eksponirovanie proteins and toxins. Among the properties ("Traits"signs) should, in addition, to emphasize the increased resistance of plants to certain herbicides, such as imidazolinones, sulfonylureas, glyphosate or phosphinotricin (for example, gene "PAT"), and Genes, forming the desired properties ("Traits", attributes) may be present in the transgenic plants also in combinations with each other. Examples of "Bt plants" are varieties of corn, cotton, soybeans and potatoes, distributed under the trade names YIELD GARD® (for example maize, cotton, soybeans), KnockOut® (for example maize), StarLink® (for example maize), Bollgard® (cotton), Nucoton® (cotton) and NewLeaf® (potato). Examples of herbicide-tolerant plants are maize, cotton and soya, distributed under the trade names Roundup Ready® (tolerance to glyphosate, for example, corn, cotton, soybeans), Liberty Link® (tolerance to phosphinotricin, for example, rape), IMI® (tolerance to imidazolinones) and STS® (tolerance to sulfonylureas, for example, corn). Among herbicide-resistant plants (inferred conventional breeding for resistance to herbicides) with whom eduit also mention varieties, distributed under the name Clearfield® (for example maize). These statements relate to, of course, also the future of plant varieties with these genetic properties ("Traits", signs) or those that will be newly developed, which will be listed or will in future appear on the market.

Particularly suitable to handle these plant compounds of General formula (I) according to the invention or mixtures of active substances according to the invention. In preferred cases described above for the active substances or mixtures, it is also relevant to the treatment of these plants. Noteworthy plant treatment compounds or mixtures that are specifically listed in the present text.

Preparation and application of active substances according to the invention is illustrated by the following examples.

Examples retrieve

Example 1

Getting 2-(1,3-dimethylbutyl)cyclohexanamine

In a solution consisting of 20,0 g (0,113 mol) of 2-(1,3-dimethylbutyl)aniline in 300 ml of tetrahydrofuran, add 5 g of Ru/C 5% and hydronaut 24 hours at 120°With hydrogen under a pressure of 100 bar. After cooling to room temperature, the catalyst is filtered off through Celite 545 and concentrated product in a vacuum. Gain of 19.1 g (92.4% of theory) of 2-(1,3-dimethylbutyl)cyclohexanamine content 100% agreement is but HPLC and logP(pH 2.3), equal 4,07.

Getting amide 4-(deformity)-N-[2-(1,3-dimethylbutyl)-cyclo-hexyl]-2-methyl-1,3-thiazole-5-carboxylic acid

In a solution consisting of 0.16 g (0.82 mmol) of 4-(deformity)-2-methyl-1,3-thiazole-5-carboxylic acid and one drop of DMF) in 15 ml dichloromethane added at room temperature dropwise in 0.104 g (0.82 mmol) of oxalic acid dichloride and stirred at room temperature for 1 hour.

To a solution consisting of 0.15 g (0.82 mmol) of 2-(1,3-dimethylbutyl)cyclohexanamine and 0.25 g (0,0025 mol) of triethylamine in 5 ml of dichloromethane, is added dropwise the above solution of the acid chloride at room temperature and stirred the reaction mixture for 12 hours at room temperature.

Washed twice with 10 ml of water in each case, dried over sodium sulfate and concentrated in vacuum. The remainder chromatographic on silica gel with n-hexane/methyl tert-butyl ether (3:1). Obtain 0.12 g (38.9% of theoretical) of amide 4-(deformity)-N-[2-(1,3-dimethylbutyl)cyclohexyl]-2-methyl-1,3-thiazole-5-carboxylic acid as a mixture of diastereoisomers with a content of 95% according to HPLC and logP (pH 2.3), equal 4,45/4,53.

Table 2
For all compounds are shown in table 2, n=0.
* LogP values given for the main diastereoisomer of Stereolab in the case when they can be detected:
Nr.sR1R2R3R4R5ALog P*/flash (F), (°C)
I-d-11HHCH3CH3H4,22/a 4.53
Table 3
For all compounds are shown in table 3, n=0.
* LogP values given for the main diastereoisomer of Stereolab in the case when they can be detected:
Nr.sR1R2R49R50R51ALog P*/flash (F), (°C)
I-k-11HHCH3CH3CH34,15

Nr.sR1R2R49R50R51ALog P*/flash (F), (°C)
I-k-21H CH3CH3CH3CH34,51
I-k-31HHCH3CH3CH35,13
I-k-41HCH3CH3CH3CH35,44
I-k-51HHCH3CH3CH34,25/4,54
I-k-61HCH3CH3 CH3CH34,56
I-k-71HHCH3CH3CH34,82/5,06
I-k-81HCH3CH3CH3CH35,13

The determination of the logP values given in the table, was performed according EEC Directive 79/831 Annex V.A8 by HPLC (high performance liquid chromatography) column C18 reversed-phase. Temperature 43°C.

The determination is carried out in an acidic region at pH 2.3 with 0.1% aqueous solution of phosphoric acid and acetonitrile as eluents; linear gradient from 10% acetonitrile to 90% acetonitrile.

Determination using LC-MS in the neutral region is carried out at pH 7.8 with 0.001 to molar aqueous solution of ammonium bicarbonate and acetonitrile as eluents; a linear gradient from 10% acetonitrile to 95% acetonitrile.

Calibration was carried out unbranched Alkan-2-areas (having 3 to 16 carbon atoms), whose logP values are known (Determination of the logP values by the retention time using linear interpolation between the two following each other by alkenone).

Values of lambda max was received, based on the UV spectra in the range of 200-400 nm on the maxima of the chromatographic signals.

Examples of the application

Example

The test collection Podosphaera/protective (apples)

Solvent:24,5 mass parts of acetone
24,5 mass parts of dimethylacetamide
Emulsifier:1 mass part of the alkyl-aryl-polyglycolic ether

For the preparation of ready-to-use product containing the active substance, 1 mass part of the active substance is mixed with the stated amounts of solvent and emulsifier and dilute concentrate with water to the desired concentration.

To test the effectiveness of the protection of young plants are sprayed with a mixture containing the active substance, with the specified application rates. After drying sediments spraying RA the plants inoculant aqueous spore suspension Podosphaera leucotricha. Then the plants are placed in a greenhouse where the temperature is about 23°C and a relative humidity of around 70%.

Within 10 days after inoculation evaluate the results. 0% mean efficiency corresponding to the control and efficiency of 100% means that the infection was not observed.

Table a
The test collection Podosphaera/protective (apples)
The active substance according to the inventionThe flow rate of the active substance in g/haEfficiency in %
(I-c-4)100100
(I-c-5)100100
(I-c-7)100100
(I-c-1)10088

The example In

The test collection Ventuia/protective (apples)

Solvent:24,5 mass parts of acetone
24,5 mass parts of dimethylacetamide
Emulsifier:1 mass part of the alkyl-aryl-polyglycolic ether

For the preparation of ready-to-use product containing the active substance, 1 mass part of the active substance is mixed with the stated amounts of solvent and emulsifier and dilute concentrate with water to the desired concentration.

To test the effectiveness of the protection of young plants are sprayed with a mixture containing the active substance, with the specified application rates. After drying sediments spraying plants inoculant with an aqueous suspension of conidia of the pathogen scab Apple Venturia inaequalis and leave for days at a temperature of about 20°C and 100% relative humidity in the incubation chamber. Then the plants are placed in a greenhouse with a temperature of around 21°C and a relative humidity of around 90%. Within 10 days after inoculation evaluate the results. 0% mean efficiency corresponding to the control and efficiency of 100% means that the infection was not observed.

Table
The test collection Venturia/protective (apples)
The active substance according to the inventionThe flow rate of the active substance in g/haEfficiency in %
(I-c-4)10098
(I-c-5)100100
(I-c-6)10099

Table
The test collection Venturia/protective (apples)
The active substance according to the inventionThe flow rate of the active substance in g/haEfficiency in %
(I-c-7)100100
(I-c-11) 10090
(I-c-1)100100

The example

The test collection Botrytis/protective (bean)

Solvent:24,5 mass parts of acetone
24,5 mass parts of dimethylacetamide
Emulsifier:1 mass part of the alkyl-aryl-polyglycolic ether

For the preparation of ready-to-use product containing the active substance, 1 mass part of the active substance is mixed with the stated amounts of solvent and emulsifier and dilute concentrate with water to the desired concentration.

To test the effectiveness of the protection of young plants are sprayed with a mixture containing the active substance, with the specified application rates. After drying sediments spraying on each sheet put two small pieces of agar covered with Botrytis cinerea. Inoculated plants are placed in a dark chamber with a temperature of 20°C and a relative humidity of 100%.

2 days after inocula the AI determine the size of the stain of defeat. 0% mean efficiency corresponding to the control and efficiency of 100% means that the infection was not observed.

Table
The test collection Botrytis/protective (beans)
The active substance according to the inventionThe flow rate of the active substance in g/haEfficiency in %
(I-c-4)50095
(I-c-5)50099
(I-c-6)50090
(I-c-7)50094

Table
The test collection Botrytis/protective (beans)
The active substance according to the inventionThe flow rate of the active substance in g/haEfficiency in %
(I-c-11)50096

Example D

The test collection Puccinia/protective (wheat)

Solvent: 50 mass parts of N,N-dimethylacetamide

Emulsifier: 1 mass part of the alkyl-aryl-polyglycolic ether

For the preparation of ready-to-use product containing the active substance, 1 mass part of the active substance is mixed with the stated amounts of solvent and emulsifier and dilute concentrate with water to the desired concentration.

To test the effectiveness of the protection of young plants are sprayed with a mixture containing the active substance, with the specified application rates. After drying sediments plants are sprayed with an aqueous suspension of conidia of Puccinia recondita. Plants left for 48 hours at a temperature of about 20°C and 100% relative humidity in the incubation chamber. Then the plants are placed in a greenhouse with a temperature of around 20°C and a relative humidity of around 80%.

Within 10 days after inoculation evaluate the results. 0% mean efficiency, appropriate control, effektivnosti 100% means, that infection was not observed.

Table D
The test collection Puccinia/protective (wheat)
The active substance according to the inventionThe flow rate of the active substance in g/haEfficiency in %
(I-c-3)500100
(I-c-4)500100
(I-c-14)500100
(I-c-5)500100
(I-c-6)500100
(I-c-7)500100

Table D
The test collection Puccinia/protective (wheat)
The active substance according to the inventionThe flow rate of the active substance in g/haEfficiency in %
(I-c-9)500100
(I-c-10)500100
(I-c-12)500100
(I-c-1)500100

Example F

The test collection Alternaria/protective (tomatoes)

Solvent: 49 mass parts of N,N-dimethylformamide

Emulsifier: 1 mass part of the alkyl-aryl-polyglycolic ether

For the preparation of ready-to-use product containing the active substance, 1 mass part of the active substance is mixed with the stated amounts of solvent and emulsifier and dilute concentrate with water to the desired concentration.

To test the effectiveness of the protection of young tomato plants are sprayed with a mixture containing the active substance, with the specified application rates. One day after treatment the plants inoculant with an aqueous suspension of spores Alternaria solani and then left for 24 hours at 100% relative humidity and 20°C. Then the plants are at 96% relative humidity and 20°C.

In 7 days after inoculation evaluate the results. 0% mean efficiency corresponding to the control and efficiency of 100% means that the infection was not observed.

Table E
The test collection Alternaria/protective (tomatoes)
The active substance according to the inventionThe flow rate of the active substance in g/haEfficiency in %
(I-c-4)750100
(I-c-14)750100
(I-c-5) 750100
(I-c-7)750100

Table E
The test collection Alternaria/protective (tomatoes)
The active substance according to the inventionThe flow rate of the active substance in g/haEfficiency in %
(I-c-10)750100

1. 2-Alkyl-cyclol(EN)yl-carboxamide formula (I)

in which X represents-CR3R4R5,
s means 1 or 2,
R1means hydrogen,
L means cyclohexyl,
R2denotes hydrogen, alkyl with 1-4 carbon atoms,
R3means alkyl with 1-8 carbon atoms,
R4means alkyl with 1-8 carbon atoms,
R5denotes hydrogen, alkyl with 1-8 carbon atoms,
A represents the residue of formula (A1)

in which R12means halogen, alkyl with 1-4 carbon atoms, Galaga is alkyl with 1-4 carbon atoms and 1 to 5 halogen atoms,
R13means hydrogen, halogen,
R14means alkyl with 1-4 carbon atoms,
or
A represents the residue of formula (A2)

in which R15and R16mean hydrogen,
R17means halogen, alkyl with 1-4 carbon atoms or halogenated with 1-4 carbon atoms and 1 to 5 halogen atoms,
or
A represents the residue of formula (A3)

in which R18and R19mean hydrogen,
R20means halogen or halogenated with 1-4 carbon atoms and 1 to 5 halogen atoms,
or
A represents the residue of formula (A4)

in which R21means halogen, alkyl with 1-6 carbon atoms, halogenated with 1-4 carbon atoms and 1 to 5 halogen atoms,
or
A represents the residue of formula (A5)

in which R22means halogen,
R23means hydrogen,
or
A represents the residue of formula (A6)

in which R24means alkyl with 1-4 carbon atoms or halogenated with 1-4 carbon atoms and 1 to 5 halogen atoms,
Q1means S(sulfur),
p denotes 0,
or
A represents the residue of formula (A9)

in which R28and R29mean hydrogen,
R30means alkyl with 1-4 carbon atoms,
or
A represents the residue of formula (A11)

in which R34means alkyl with 1-4 carbon atoms,
R35means halogenated with 1-4 carbon atoms and 1 to 5 halogen atoms,
or
A represents the residue of formula (A16)

in which R42means halogen,
or
A represents the residue of formula (A18)

in which R44means alkyl with 1-4 carbon atoms,
R45means hydrogen,
R46means hydrogen or halogenated with 1-4 carbon atoms and 1 to 5 halogen atoms,
R47means hydrogen,

2. The method of obtaining 2-alkyl-cyclol(EN)yl-carboxamido formula (I) according to claim 1, characterized in that
derivatives of carboxylic acids of the formula (II)

in which a has the meanings given in claim 1, and
X1means halogen or hydroxy-group, is subjected to the interaction with aniline derivatives of the formula (III)

in which R1, L, R2, R3, R4and R5have the meanings given in claim 1, optionally in the presence of a catalyst, optionally in the presence of a condensing agent, optionally in the presence of an acid binding agent and optionally in the presence of a diluent.

3. Means of combating undesirable microorganisms, characterized in that the but contains at least one 2-alkyl-cyclol-(EN)yl-carboxamide formula (I) according to claim 1 and a solvent and/or surfactant.

4. The use of 2-alkyl-cyclol(EN)yl-carboxamido formula (I) according to claim 1 for controlling undesirable microorganisms.

5. The method of controlling undesirable microorganisms, wherein the microorganisms and/or their habitat are treated with 2-alkyl-cyclol(EN)yl-carboxamide formula (I) according to claim 1.

6. A way of raising funds for unwanted microorganisms, characterized in that 2-alkyl-cyclol(EN)yl-carboxamide formula (I) according to claim 1 are mixed with extenders and/or surfactants.



 

Same patents:

FIELD: chemistry.

SUBSTANCE: present invention relates to hot or sweet flavourants in form of a synthetic amide compound or edible salt thereof in amount ranging from approximately 0.001 parts per million to approximately 100 parts per million. The amide compound has formula

where A is a phenyl or a 5- or 6-member heteroaryl ring selected from a group comprising pyridine, pyrazine, pyrazole, thiazole, furan, thiophene, benzofuran and benzothiophene; m equals 1, 2 or 3, each R1 is independently selected from hydroxyl, fluorine, chlorine, SEt, SCH3, methyl, ethyl, isopropyl, vinyl, trifluoromethyl, methoxy, ethoxy and isopropoxy, or alternatively two R1 are bonded to form a saturated C1-C3 alkylenedioxy ring on the phenyl; and R2 is a C3-C10 branched alkyl. The amide compound also has formula

in which substitutes A, B, R50, R60, R70, R80, n and m assume values given in the formula of invention. The amide compound is also a specific chemical compound.

EFFECT: obtaining hot and sweet taste modifiers and boosters for food and medicinal products.

39 cl, 7 tbl, 180 ex

FIELD: chemistry.

SUBSTANCE: invention relates to a compound of formula (1) or salts thereof, (1), where R1 denotes a hydrogen atom or a C1-6alkyl group; R2 denotes a hydrogen atom, R3 denotes a hydrogen atom or a C1-6alkyl group when R4 and R5 denote hydrogen atoms, R6 denotes a hydrogen atom or a cyano group, or in >C(R6) C(R5)(R4) - denotes a double bond, R4 and R6 are absent, and R5 denotes a hydrogen atom; or R4 denotes a hydrogen atom and R5 denotes a hydroxy group or a halogen atom, R6 denotes a hydrogen atom or a cyano group, R7 denotes one or two substitutes selected from a group comprising a hydrogen atom, a halogen atom, a nitro group and C1-6alkoxy group, A denotes a 5-member or a 6-member non-aromatic heterocyclic ring which contains one sulphur atom (the sulphur atom can form an oxide), W denotes an oxo group, two hydrogen atoms, two fluorine atoms or a combination of a hydrogen atom and a hydroxy group, and X denotes an oxygen atom or a sulphur atom.

EFFECT: medicinal agent based on these compounds have inhibitory action on production of prostaglandin E2 and can be used in medicine to treat urological diseases.

5 cl, 7 tbl, 69 ex

FIELD: chemistry.

SUBSTANCE: invention relates to a method of producing dimethyl ether of 2,5-thiophene dicarboxylic acid by reacting thiophene with carbon tetrachloride in the presence of methanol and a tris(2,4-pentanedionato)iron catalyst Fe(acac)3 which is activated by a nitrogen-containing ligand - quinoline or pyridine, at temperature 150°C for 6 hours in molar ratio 0.04:0.4:4:45:30. Dimethyl ether of 2,5-thiophene dicarboxylic acid is used in production of electroconductive polymers, electrodes, sensors, capacitors, displays, optical brighteners, gel electrolytes and ion-exchange membranes.

EFFECT: high output of product.

1 tbl

FIELD: chemistry.

SUBSTANCE: invention relates to a method of producing dimethyl ether of 2,5-thiophene dicarboxylic acid, , which involves reaction of 2-thiophene carboxylic acid with methanol and CCl4 in the presence of a catalyst tris(2,4-pentanedionato)iron Fe(acac)3, activated with a nitrogen-containing ligand - pyridine with molar ratio [Fe(acac)3] : [C5H5N] : [2-thiophene carboxylic acid] : [methanol] : [CCl4]=0.01:0.05-0.1:1:45-135:30, at temperature of 140-160°C for 3-6 hours.

EFFECT: high output of dimethyl ether of 2,5-thiophene dicarboxylic acid which is the base material for production of electroconductive polymers, electrodes, sensors, capacitors, displays, gel electrolytes, ion-exchange membranes and optical bleaching agents.

1 cl, 1 tbl, 1 ex

FIELD: chemistry.

SUBSTANCE: invention relates to novel biologically active compounds of formula , where substitutes R, R1, R2 and R3 are defined in the formula of invention, and can be obtained using a method which involves reaction of corresponding chloroacetamides with a prepared solution of elementary sulphur with morpholine or piperidine, passing the obtained solution of monothiooxamides through a layer of sorbent and then reaction of monothiooxamides with hydrazine-hydrate, reaction of the obtained compound with aldehydes in dimethyl formamide at room temperature and precipitation with methanol which gives good output of the end product.

EFFECT: obtained compounds are highly effective against pathogenic bacteria, are characterised by selectivity and can be used to inhibit type III secretion in pathogenic bacteria.

3 cl, 8 dwg, 1 tbl, 21 ex

FIELD: chemistry.

SUBSTANCE: invention relates to N-substituted derivatives of oxamic acid thiohydrazides of general formula: , where R and R1 denote H, unsubstituted or substituted Het, phenyl, Alk, wherein substitutes can be Alk, Hal, CF3, COOR3, SR3, or R+R1=C2H4OC2H4; R2 denotes H, Alk, OR3, Hal, where R3=Alk; Het denotes a 5- or 6-member ring which contains one or two heteroatoms selected from N and S. The invention also relates to a method for synthesis of said compounds.

EFFECT: obtaining novel compounds which exhibit antibacterial activity and can be used as antibacterial agents for inhibiting pathogenic bacteria, including Chlamydia.

4 cl, 21 ex

FIELD: chemistry.

SUBSTANCE: invention relates to new biologically active substances and specifically to 4-(methylphenyl)-4-oxo-2-[3-ethoxycarbonyl-4,5-R2,R1-thiophen-2-ylamino]but-2-enoic acid of general formula: R1,R2=CH3 R1+R2=(CH2)3.

EFFECT: obtaining new compounds having anti-inflammatory and analgesic activity, as well as low toxicity, which can be used as medicinal agents.

1 cl, 1 tbl, 4 ex

FIELD: chemistry; biochemistry.

SUBSTANCE: invention relates to compounds of general formula (II) and pharmaceutically acceptable salts thereof, and to use and a pharmaceutical composition based on the said compounds. In formula (II) compounds, A is a heteroaromatic 5-member cyclic system containing one group X selected from a group consisting of S and O; Z1 and Z2 independently represent O; R2 is OR6; R6 is H; R8 is hydrogen or (C1-C6)alkyl; E is phenyl which is optionally substituted with 1-4 substitutes in form of halogen; Y is phenyl which is optionally substituted with 1-2 substitutes selected from halogen, (C1-C6)alkoxy or halogen((C1-C6))alkyloxy; m equals 0; n equals 0; q equals 0; t equals 0; or pharmaceutically acceptable salts thereof.

EFFECT: obtaining aromatic compounds of formula (II) for inhibiting dehydroorotate dehydrogenase.

6 cl, 22 ex

FIELD: chemistry.

SUBSTANCE: invention is related to the field of organic chemistry, in particular, to method for production of methyl ethers of 2-thiophen carbonic acid intended for use in synthesis of optical whiteners, dyes for cotton, wool, artificial fibers, medical preparations, and also as additive to oils or hydraulic liquids. Substance of the method consists in thiophen interaction with methanol in presence of carbon tetrachloride under action of catalysts - oxo-bis-(2,4-pentanodionato)vanadium VO(acac)2 or tris (2,4-pentanodionato)iron Fe(acac)3, or molybdenum hexacarbonyl Mo(CO)6 at the temperature of 130-170°C for 3-6 hours at the following mole ratio - catalyst:thiophen:CCl4:methanol equal to 1:100:200-300:200-300.

EFFECT: suggested method makes it possible to produce target product with yield of 63-85%, using simplified technology.

1 tbl, 14 ex

FIELD: chemistry.

SUBSTANCE: invention concerns enantiomers of thiophene hydroxami acid derivatives of general formula I and their pharmaceutically acceptable salts. , where Ar is aryl or heteroaryl group selected out of thiophene, morpholine, which can be non-substituted or mono-, di- or trisubstituted by halogen, phenyl, alkyl, -O-alkyl, -OH; R1 is hydrogen, phenyl or alkyl; together with Ar-group R1 forms tetrahydronaphthaline or indane cycle; R2 is hydrogen or alkyl; and their pharmaceutically acceptable salts.

EFFECT: application as histondesacetylase inhibitors in obtaining medicine for neoplasm treatment in hemopoietic and lymphatic system.

29 cl, 10 ex

The invention relates to new compounds for combating pests, in particular derivatives carbanilide and fungicide-insecticidal tool based on them

The invention relates to the field of organic chemistry

The invention relates to a method of stereoselective obtain enantiomer heterobicyclic alcohol

The invention relates to new heterocyclic condensed to benzoylpyridine General formula I, where R1and R2denote independently from each other H or A; X denotes CR4R5; C=Z or O, Y represents CR6R7Z denotes O or CH2, R4, R5, R6or R7denote independently from each other H, A, HE or OA, or R5and R6or R7and R8indicate link together, with each molecule may receive a maximum of only one such bond, or R4and R5indicate together O-(CH2)2-O or O-(CH2)3-O, or R8and R9denote independently from each other H or A; And denotes alkyl with 1 to 6 C-atoms; n represents 0 or 1, and their physiologically acceptable salts

FIELD: chemistry.

SUBSTANCE: invention relates to compounds of general formula (I) and to their pharmaceutically acceptable salts, optical isomers or their mixture as glucokinase activators. In general formula (I) where R1 is C3-8-cycloalkyl, C3-8-cycloalkenyl, a 6-member heterocyclyl with 1 nitrogen atom, condensed phenyl-C3-8-cycloalkyl, each of which is possibly substituted with one or two substitutes R3, R4, R5 and R6; R2 is C3-8-cycloalkyl, a 5-6-member heterocyclyl with 1-2 heteroatoms selected from N, O, or S, each of which can be substituted with one or two substitutes R30, R31, R32 and R33, and R3, R4, R5, R6, R30, R31, R32 and R33 are independently selected from a group consisting of halogen, hydroxy, oxo, -CF3; or -NR10R12; or C1-6-alkyl, phenyl, C1-6-alkoxy, C1-6-alkyl-C(O)-O-C1-6-alkyl, each of which is possibly substituted with one substitute independently selected from R12; or -C(O)-R27, -S(O)2-R27; or two substitutes selected from R3, R4, R5 and R6 or R30, R31, R32 and R33, bonded to the same atom or to neighbouring atoms, together form a -O-(CH2)2-O- radical; R10 and R11 independently represent hydrogen, C1-6-alkyl, -C(O)-C1-6-alkyl, -C(O)-O- C1-6-alkyl, -S(O)2- C1-6-alkyl; R27 is C1-6-alkyl, C1-6-alkoxy, C3-8-cycloalkyl, C3-8-cycloalkyl-C1-6-alkyl, phenyl, phenyl-C1-6-alkyl, a 5-6-member heteroaryl with 1-2 heteroatoms selected from N or S, a 6-member heteroaryl-C1-6-alkyl with 1 nitrogen atom, a 6-member heterocyclyl-C1-6-alkyl with 1-2 heteroatoms selected from N or O, R10R11-N- C1-6-alkyl, each of which is possibly substituted with one substitute independently selected from R12; R12 is a halogen, CF3, C1-6-alkoxy, -NR10R11; A is a 5-9-member heteroaryl with 1-3 heteroatoms selected from N, O or S, which is possibly substituted with one or two substitutes independently selected from R7, R8 and R9; R7, R8 and R9 are independently selected from halogen, cyano, -CF3; or C1-6-alkyl, C2-6-alkenyl, C1-6-alkoxy, C1-6-alkylthio, -C(O)-O-C1-6-alkyl, formyl, - C1-6-alkyl-C(O)-O-C1-6-alkyl, -C1-6-alkyl-O-C(O)-C1-6-alkyl or hydroxy-C1-6-alkyl, each of which is possibly substituted with a substitute independently selected from R16; or phenyl, 5-member heteroaryl-C1-6-alkylthio with 2-4 nitrogen atoms, phenylthio, 5-6-member heteroarylthio with 1-2 nitrogen atoms, each of which is possibly substituted on the aryl or heteroaryl part with one or two substitutes independently selected from R17; or C3-8-cycloalkyl; or a 6-member heterocyclyl with 2 nitrogen atoms, 5-7-member heterocyclyl-C1-6-alkylthio with 1-2 heteroatoms selected from N or O, each of which is possibly substituted with one substitute independently selected from R16; or C1-6-alkyl-NR19R20, -S(O)2-R21 or -S(O)2-NR19R20; or -C(O)NR22R23; R16, R17 and R18 independently represent C1-6-alkyl, carboxy, -C(O)-O-C1-6-alkyl, -NR19R20, -C(O)NR19R20; R19 and R20 independently represent hydrogen, C1-6-alkyl, phenyl, 5-member heteroaryl with 2 heteroatoms selected from N or S, 6-member heterocyclyl with 1 nitrogen atom, -C(O)-O-C1-6-alkyl or -S(O)2-C1-6-alkyl, each of which is possibly substituted with one substitute independently selected from R24; or R19 and R20 together with a nitrogen atom to which they are bonded form a 5-7-member heterocyclic ring with the said nitrogen atom, where this heterocyclic ring possibly contains one additional heteroatom selected from nitrogen, oxygen and sulphur, where this heterocyclic ring is possibly substituted with one substitute independently selected from R24; R21 is selected from C2-6-alkenyl; or R22 and R23 are independently selected from hydrogen, -C1-6-alkyl-C(O)-O-C1-6-alkyl, -C1-6-alkyl-S(O)2-C1-6-alkyl, C3-8-cycloalkyl; or R22 and R23 together with a nitrogen atom to which they are bonded form a 6-member heterocyclic ring with the said nitrogen atom, where this heterocyclic ring is possibly substituted with one substitute independently selected from R24; R24 is oxo, C1-6-alkyl, carboxy- C1-6-alkyl, a 6-member heterocyclyl with 1 nitrogen atom, -NH-S(O)2R28 or -S(O)2R28, where each cyclic group is possibly substituted with one substitute independently selected from R29; R28 is C1-6-alkyl, -C1-6-alkyl-C(O)-O- C1-6-alkyl or -N(CH3)2; R29 is C1-6-alkyl.

EFFECT: obtaining compounds which can be used for treating and preventing diseases mediated by low glucokinase activity.

21 cl, 1 dwg, 608 ex, 1 tbl

FIELD: chemistry.

SUBSTANCE: invention relates to new compounds of formula (I) , in which Ar is furanyl, thiophenyl, thiazolyl, pyridinyl; R1 is independently chosen from a group consisting of hydrogen, lower alkyl, lower alkoxy, halogen and nitro; R2 is independently chosen from a group consisting of hydrogen and halogen; R4 is hydroxyl or residue of pyrrolidine-2-carboxylic acid, piperidine-2-carboxylic acid or 1-aminocyclopentane carboxylic acid, bonded through a nitrogen atom of an amino acid residue; n is 0, 1, 2, 3, 4 or 5; m is 0, 1, 2, 3 or 4; p is 0, and s is 0, or to their pharmaceutically acceptable salts, under the condition that, the compound is not S-1- [5-(biphenyl-4-yloxymethyl)furan-2-carbonyl]pyrrolidin-2-carboxylic acid, 5-(biphenyl-4-yloxymethyl)furan-2-carboxylic acid, 3-(biphenyl-4-yloxymethyl)benzoic acid, 2-(biphenyl-3-yloxymethyl)benzoic acid, 4-(biphenyl-3-yloxymethyl)benzoic acid, 4-(biphenyl-4-yloxymethyl)benzoic acid, 5-(biphenyl-4-yloxymethyl)thiophene-2-carboxylic acid. Invention also relates to a pharmaceutical composition based on formula (I) compounds, which stimulates glycogen synthase activity.

EFFECT: wider range of use of the compounds.

27 cl, 34 ex, 8 dwg

FIELD: chemistry.

SUBSTANCE: invented compounds have inhibitory activity towards protein kinase. In formula 1a m lies between 0 and 1, R1 is chosen from a group which includes hydrogen, methyl, isopropyl, imidazolylpropyl, piperazinylpropyl, pyridinyl, diethylaminopropyl, hydroxyethyl, pyrimidinyl, morpholinopropyl, phenyl, cyclopropyl, morpholinoethyl, benzyl and morpholino, where any of pyridinyl, imidazolyl, piperazinyl or pyrimidinyl in R1 are optionally substituted with 1-3 radicals, independently chosen from a group, which includes methyl, methylamine, dimethylaminomethyl, cycloproylamine, hydroxyethylamine, diethylaminopropylamine, pyrrolydinylmethyl, morpholino, morpholinomethyl, piperazinylmethyl and piperazinyl, where any of morpholino and piperazinyl in R1 are optionally further substituted with a radical, chosen from a group which includes methyl, hydroxyethyl and ethyl, R2, R3 and R5 each represents hydrogen, R4 represents methyl, L is chosen from a group which includes -NR5C(O)- and -C(O)NR5-, R10 represents trifluoromethyl, and R11 is chosen from a group which includes halogen, morpholinomethyl, piperazinyl, optionally substituted with a methyl, ethyl or hydroxyethyl group; piperazinylmethyl, optionally substituted with a methyl or ethyl group, imidazolyl, optionally substituted with methyl, pyrrolidinylmethoxy and piperidinyl, optionally substituted with a hydroxy group.

EFFECT: more effective treatment.

4 cl, 1 tbl, 3 ex

FIELD: chemistry.

SUBSTANCE: invented compounds have antagonist properties towards CB1 receptors. In formula (I) , R1 is a lower alkoxy, (lower alkyl amino)-(lower alkoxy) or -N(Ra)Rb; Ra is hydrogen, lower alkyl, carbamoyl-(lower alkyl), hydroxy-(lower alkyl), dihydroxy-(lower alkyl), lower alkynyl, lower alkoxy, (lower alkoxy)-(lower alkyl), di-(lower alkylamino)-(lower alkyl), C3-6cycloalkyl; or Ra is a phenyl-(lower alkyl) group, where the phenyl fragment can be optionally mono-substituted, independently, by lower alkyl, lower alkoxy or halogen; or Ra is a 5- or 6-member heteroaromatic ring system, containing one or two nitrogen atoms in the ring, where the said heteroaromatic ring system is bonded to the remaining part of the molecule by lower alkylene; or Ra is a 5-, 6- or 7-member saturated heterocyclic ring system, containing one nitrogen heteroatom, where the said heterocyclic ring system is optionally mono-substituted by lower alkyl; Rb is hydrogen, lower alkyl or (lower alkoxy)-(lower alkyl); or Ra and Rb together with a nitrogen atom to which they are bonded, for a 4-, 5- or 6-member saturated or partially unsaturated heterocyclic ring system, optionally containing an extra heteroatom, which is chosen from nitrogen, oxygen or sulphur, where the said heterocyclic ring system is optionally mono- or disubstituted, independently, by lower alkyl, hydroxy group, hydroxy-(lower alkyl), lower alkoxy, (lower alkoxy)-(lower alkyl) group, cyano group, halogen, phenyl and/or benzyl; R2 is hydrogen or lower alkyl; R3 is phenyl, mono- or disubstituted, independently, by lower alkoxy, halogen, or perfluoro-(low alkoxy) group; and R4 is phenyl, which is mono- or disubstituted with a halogen.

EFFECT: new compounds have useful biological properties.

18 cl, 195 ex

FIELD: chemistry.

SUBSTANCE: invention concerns new compounds of the formula (I) and pharmaceutically acceptable salts. Claimed compounds have modulation effect on CB cannabinoid receptor. In the general formula (I) , R and R1 are the same or different and are phenyl optionally substituted by 1-3 substitutes Y, where Y is substitute selected out of group including chlorine, iodine, bromine, fluorine, on condition that X is not a sub-group (ii); or one of R and R1 radicals is phenyl group, while the other radical is formed or linear C2-8-alkyl group or benzyl group; X is one of the sub-groups (i) or (ii). Also invention concerns application of the compounds in obtaining pharmaceutical composition, pharmaceutical composition with modulation effect on CB cannabinoid receptor, and compound of the general formula (IV) with radical values as indicated in the claim.

EFFECT: enhanced efficiency of composition and treatment method.

5 cl, 1 tbl, 25 ex

FIELD: chemistry.

SUBSTANCE: in novel compounds of formula I R1 represents phenyl, possibly substituted with phenyl or heterocyclic group, or heterocyclic group, possibly substituted with phenyl, where said heterocyclic group represents mono- or bicyclic ring, containing 4-12 atoms, of which at least one atom is selected from nitrogen, sulfur or oxygen, each phenyl or heterocyclic group possibly being substituted with one or more than one of the following groups: C1-6alkyl group; phenylC1-6alkyl, alkyl, phenyl or alkylphenyl group is possibly substituted with one or more than one from Rb; halogen; -ORa; -OSO2Rd; -SO2Rd; -SORd; -SO2ORa; where Ra represents H, C1-6alkyl group, phenyl or phenylC1-6alkyl group; where R represents halogeno, -OH, -OC1-4alkyl, Ophenyl, -OC1-4alkylphenyl, and Rd represents C1-4alkyl; group -(CH2)m-T-(CH2)n-U-(CH2)p- is bound either in third, or in fourth position in phenyl ring, as shown with figures in formula I, and represents group selected from one or more than one of the following: O(CH2)2, O(CH2)3, NC(O)NR4(CH2)2, CH2S(O2)NR5(CH2)2, CH2N(R6)C(O)CH2, (CH2)2N(R6)C(O)(CH2)2, C(O)NR7CH2, C(O)NR7(CH2)2 and CH2N(R6)C(O)CH2O; V represents O, NR8 or single bond; q represents 1, 2 or 3; W represents O, S or single bond; R2 represents halogeno or C1-4alkoxyl group; r represents 0, 1, 2 or 3; s represents 0; and R6 independently represent H or C1-10alkyl group; R4, R5, R7 and R8 represent hydrogen atom; and to their pharmaceutically acceptable salts.

EFFECT: increase of composition efficiency.

12 cl, 31 ex

FIELD: chemistry, pharmacology.

SUBSTANCE: invention relates to novel compounds -acidified arylcycloalkylamins of formula I in any of their stereoisomeric forms or in form of their mixture in any ratio, or their pharmaceutically acceptable salts, where in formula I : R1 represents aryl, not obligatory substituted with one or two similar or different substitutes, selected from group that includes C1-C6-alkyl and halogen; R2 represents aryl or heteroaryl, which represents residue of 5-6-member aromatic monocyclic heterocycle, containing 1-2 nitrogen atoms as heteroatom and/or 1 sulfur atom or oxygen atom, or residue of 9-10-member aromatic bicyclic heterocycle, containing 1-2 nitrogen atoms as heteroatom, each of which is unsubstituted or contains 1-3 similar or different substitutes, selected from group, consisting of halogens, NH2, unsubstituted C1-C10-alkyl, C1-C10 -alcoxy, C1-C10-alkylamino and di(C1-C10-alkyl)amino, and at least monosubstituted C1-C10-alkyl, etc., n represents 1, 2, 3 or 4. Invention relates to pharmaceutical composition, stimulating expression of endothelial NO synthase, based on said compounds, as well as application of compounds of formula I for production of medication for stimulating expression of endothelial NO-synthase and for treatment of such cardiovascular diseases as atherosclerosis, thrombosis, coronary artery disease, hypertension and impaired cardiac function.

EFFECT: invention ensures enhancing composition and treatment method efficiency.

9 cl, 2 tbl, 41 ex

Up!