2,4,5-triple-substituted phenylethanol, intermediate compounds for their preparation and method and means for controlling insects and arachnids on their basis

 

(57) Abstract:

The invention relates to 2,4,5-triple-substituted phenylethanol formula I, in which HET denotes one of the groups(1), (2), (3), (4), (5). Described as intermediates for producing compounds of formula I, means for controlling insects and arachnids and used this method of struggle. The compounds possess a broad spectrum of activity and compatibility with respect to cultural plants. 11 c. and 2 C.p. f-ly, 33 PL.

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The invention relates to new phenylselenenyl cyclic ketoenols, in particular to 2,4,5-triple-substituted phenylethanol, to intermediate compounds for their production, to a method and means for controlling insects and arachnids on the basis of them.

It is already known that certain phenylsilane circular ketoenol active as insecticides, acaricides and/or herbicides.

Already described pharmaceutical properties of 3-acylpyrrole-2,4-diones (S. Suzuki and others, Chem. Pharm. Bull., 15, 1120 (1967)). Hereinafter, R. Schmierer and N. Mildenberger (Liebigs Ann. Chem. 1985, 1095) was synthesized N-phenylpyrrolidine-2,4-diones. The biological activity of these compounds is not described.

In the application for the European patent Ene-2,4-diones), however, there are no data about their herbicide, insecticide or acaricide action. Aware of herbicide, insecticide or acaricide action unsubstituted bicyclic derivatives of 3-arylpyrimidine-2,4-dione (applications for European patents EP-A 355 599 and EP-415 211) and substituted monocyclic derivatives of 3-arylpyrimidine-2,4-dione (applications for European patents EP-377 893 and EP-442 077).

Also known polycyclic derivatives of 3-arylpyrimidine-2,4-dione (application for European patent EP-442 073) and derivatives of 1H-arylpyrimidine (applications for European patents EP-A 456 063, EP-521 334, EP-A 596 298, EP-613 884, EP-613 885, patent Germany 4 440 594, international application WO 94/01 997 and WO 95/01 358).

It is known that certain substituted derivatives 3-dihydrofuran-2-it have a weed-killing properties (see patent application Germany 4 014 420). The synthesis of the tetronic acid derivatives (such as 3-(2-were)-4-hydroxy-5-(4-forfinal)-3-dihydrofurane-(2)) used as starting compounds, are also described in the patent application Germany 4 014 420. Compounds of similar structure without insecticidal and/or acaricidal activity is known from the publication Campbell and others, J. Chem. soc., Perkin Trans. 1, 1985 isthmi known from a European patent application EP-A 528 156, of a European patent application EP-A 0 647 637, and international application WO 95/26345.

Already known for certain, unsubstituted phenyl ring derivatives phenylpyrrole (see A. M. Chirazi, So the Carr and E. Ziegler, Arch. Pharm. 309, 558 (1976) and K. - N. Boltze and K. Heidenbluth, Chem. Ber. 91, 2849), although these compounds do not specify the possibility of their use as pesticides. Substituted in the phenyl ring derivatives Panalpina with herbicide, acaricidal and insecticidal properties are described in the application for the European patent EP-588 137.

Also known for certain, unsubstituted phenyl ring derivatives of 5-phenyl-1,3-thiazine (see E. Ziegler, and E. Steiner, Monatsh. 95, 147 (1964), R. Ketcham, So the Carr and E. Ziegler, J. Heterocycl. Chem., 10, 223 (1973)), moreover, these compounds do not specify the possibility of their use as pesticides. Substituted in the phenyl ring derivatives of 5-phenyl-1,3-thiazine with herbicide, acaricidal and insecticidal properties are described in international application WO 94/14 785.

In addition, known and derivatives of phenylmethanol possessing insecticidal, acaricidal and herbicide activity, in which the phenyl residue substituted in position 2, 4 and 6 (EP 0596298, C 07 D 11.05.94, EP 0613885, C 07 D 07.09.94, EP 0647637, C 07 D 12.04.95.)

However, acaricidal and insecticidal AK is Yu to cultivated plants, is not always sufficient.

The objective of the invention is the expansion of the range of the derivative of phenylmethanol having insecticidal and acaricidal activity.

The problem is solved in 2,4,5-triple-substituted-phenylethanol General formula (I)

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where X means halogen, alkyl with 1-6 carbon atoms, alkenyl with 2-6 carbon atoms, quinil with 2-6 carbon atoms, alkoxy with 1-6 carbon atoms, halogenated with 1-4 carbon atoms, halogenoalkanes with 1-4 carbon atoms, a cyano or a nitro-group;

Y represents halogen, alkyl with 1-6 carbon atoms, alkoxy with 1-6 carbon atoms, halogenated with 1-4 carbon atoms, halogenoalkanes with 1-4 carbon atoms, a cyano or a nitro-group;

Z denotes halogen, alkyl with 1-6 carbon atoms, alkoxy with 1-6 carbon atoms, halogenated with 1-4 carbon atoms, halogenoalkanes with 1-4 carbon atoms, hydroxyl, cyano, a nitro-group, or fenoxaprop, phenylthiourea, thiazoleacetate, pyridyloxy, primidealhalbgrouppen, personalantispy, phenylalkylamine with 1-4 carbon atoms in the alkyl part or phenylalkylamine with 1-4 carbon atoms in the alkyl part, each of which can be settled by alkyl with 1-4 carbon atoms, halogenation with 1-4 carbon atoms, a nitro-group, or cyano; or

Y and Z together denote unsubstituted or substituted with halogen, alkyl with 1-6 carbon atoms, alkoxyl with 1-6 carbon atoms or halogenation with 1-4 carbon atoms alcander with 3-4 carbon atoms or alkerdeel with 3-4 carbon atoms, where independently from each other from one to three links can be replaced by oxygen, sulfur, nitrogen or carbonyl group, and X is any one of the above values;

Het denotes one of the groups:

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where a represents hydrogen, unsubstituted or substituted with halogen alkyl with 1-12 carbon atoms, alkenyl with 2-8 carbon atoms, alkyl with 1-8 carbon atoms, substituted alkoxygroup with 1-10 carbon atoms, polyalkoxyalkyl with 1-8 carbon atoms in all alkyl groups or alkyl with 1-6 carbon atoms, substituted alkylthiol with 1-10 carbon atoms, unsubstituted or substituted with halogen, alkyl with 1-6 carbon atoms or alkoxygroup with 1-6 carbon atoms cycloalkyl with 3-8 carbon atoms, in which one or two methylene groups may be replaced by oxygen atom and/or sulfur atom, either unsubstituted or substituted with halogen, alkyl with 1-6 at the of POI with 1-6 carbon atoms, the cyano or nitro-group is phenyl, naphthyl, phenyl substituted by alkyl with 1-6 carbon atoms, naphthyl, substituted alkyl with 1-6 carbon atoms, or heteroaryl with 5 or 6 atoms in the cycle and from one to three heteroatoms from the series oxygen, sulphur and nitrogen,

In denotes hydrogen, alkyl with 1-12 carbon atoms or alkyl with 1-6 carbon atoms, substituted alkoxygroup with 1-8 carbon atoms, or

A, b and the carbon atom to which they are linked, represent cycloalkyl with 3-10 carbon atoms or cycloalkenyl with 5-10 carbon atoms in which one methylene group may be replaced by oxygen atom or sulfur atom and which is not substituted or substituted by alkyl with 1-8 carbon atoms, cycloalkyl with 3-10 carbon atoms, halogenation with 1-8 carbon atoms, alkoxygroup with 1-8 carbon atoms, alkylthiol with 1-8 carbon atoms, halogen or phenyl,

or

A, b and the carbon atom to which they are linked, represent cycloalkyl with 5-6 carbon atoms which may be substituted with one or two oxygen atom and/or sulfur alkylenediamine group, or alkylenediamines or alkylenediamine group, which with the carbon atom to which they are attached, form an additional 5-8-commi carbon or cycloalkenyl with 5-8 carbon atoms, where two Deputy together with the carbon atoms to which they are linked, represent unsubstituted or substituted by alkyl with 1-6 carbon atoms, alkoxygroup with 1-6 carbon atoms or halogen alcander with 3-6 carbon atoms, alkerdeel with 3-6 carbon atoms or alkadienes with 4-6 carbon atoms in which one methylene group may be replaced by oxygen atom or a sulfur atom,

D is hydrogen, unsubstituted or substituted with halogen alkyl with 1-12 carbon atoms, alkenyl with 3-8 carbon atoms, quinil with 3-8 carbon atoms, alkyl of 2-8 carbon atoms, substituted alkoxygroup with 1-10 carbon atoms, alkyl of 2-8 carbon atoms, polyamidine alkoxygroup with 1-8 carbon atoms each, or alkyl of 2-8 carbon atoms, substituted alkylthiol with 1-10 carbon atoms; unsubstituted or substituted with halogen, alkyl with 1-4 carbon atoms, alkoxygroup with 1-4 carbon atoms or halogenation with 1-4 carbon atoms, cycloalkyl with 3-8 carbon atoms, in which one or two non-directly adjacent methylene groups may be replaced by oxygen atom and/or sulfur atom; or an unsubstituted or substituted with halogen, alkyl with 1-6 carbon atoms, halogen is a, the cyano or nitro-group is phenyl, heteroaryl with 5-6 atoms in the cycle, and one or two heteroatoms from the series oxygen, sulphur and nitrogen, phenyl substituted by alkyl with 1-6 carbon atoms, or heteroaryl with 5-6 atoms in the cycle, and one or two heteroatoms from the series oxygen, sulfur and nitrogen substituted by alkyl with 1-6 carbon atoms, or

A and D together denote a group: alcander with 3-6 carbon atoms, alkerdeel with 3-6 carbon atoms or alkadienes with 4-6 carbon atoms in which one methylene group may be replaced by oxygen atom or sulfur atom and which is unsubstituted or substituted with halogen, or unsubstituted or substituted by halogen, alkyl with 1-10 carbon atoms, alkoxygroup with 1-6 carbon atoms, alkylthiol with 1-6 carbon atoms, cycloalkene with 3-7 carbon atoms, phenyl or benzyloxycarbonyl or the other, forming secondinstance ring alkadienes group with 3-6 carbon atoms, allendales group with 3-6 carbon atoms or acadieville group with 4-6 carbon atoms in which one methylene group in each case may be replaced by oxygen atom or sulfur atom and which is unsubstituted or substituted by alkyl with 1-6 atoms operad group with 3-6 carbon atoms, which may contain one of the following groups:

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or

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G means hydrogen (a) or one of the groups:

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E (E) or

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where E is the equivalent of a metal ion or ammonium ion,

L is an oxygen atom or a sulfur atom,

M is an oxygen atom or a sulfur atom,

R1means unsubstituted or substituted with halogen alkyl with 1-20 carbon atoms, alkenyl with 2-20 carbon atoms, alkoxyalkyl with 1-8 carbon atoms in both alkyl groups, alkylthiols with 1-8 carbon atoms in both alkyl groups, or polyalkoxyalkyl with 1-8 carbon atoms in all alkyl groups, or unsubstituted or substituted by halogen, alkyl with 1-6 carbon atoms or alkoxygroup with 1-6 carbon atoms cycloalkyl with 3-8 carbon atoms, in which one or two methylene groups may be replaced by oxygen atom and/or sulfur atom;

unsubstituted or substituted with halogen, a cyano, a nitro-group, alkyl with 1-6 carbon atoms, alkoxygroup with 1-6 carbon atoms, halogenation with 1-6 carbon atoms, halogenlampe with 1-6 carbon atoms, alkylthiol with 1-6 carbon atoms or alkylsulphonyl with 1-6 carbon atoms is, what alkoxygroup with 1-6 carbon atoms, halogenation with 1-6 carbon atoms or halogenlampe with 1-6 carbon atoms phenylalkyl with 1-6 carbon atoms in the alkyl part;

unsubstituted or substituted by halogen or alkyl with 1-6 carbon atoms 5 - or 6-membered heteroaryl with one or two heteroatoms from the series oxygen,sulphur and nitrogen;

unsubstituted or substituted by halogen or alkyl with 1-6 carbon atoms peroxyacyl with 1-6 carbon atoms in the alkyl part;

unsubstituted or substituted with halogen, amino or alkyl with 1-6 carbon atoms 5 - or 6-membered heteroepitaxial with 1-6 carbon atoms in the alkyl portion with one or two heteroatoms from the series oxygen, sulphur and nitrogen,

R2means unsubstituted or substituted with halogen alkyl with 1-20 carbon atoms, alkenyl with 2-20 carbon atoms, alkyl of 2-8 carbon atoms, substituted alkoxygroup with 1-8 carbon atoms, or alkyl of 2-8 carbon atoms, polyamidine alkoxygroup with 1-8 carbon atoms in each alkyl group;

unsubstituted or substituted with halogen, alkyl with 1-6 carbon atoms or alkoxygroup with 1-6 carbon atoms cycloalkyl with 3-8 carbon atoms, or

unsubstituted or substituted what loginaction with 1-6 carbon atoms or halogenlampe with 1-6 carbon atoms, phenyl or benzyl;

R3means unsubstituted or substituted with halogen alkyl with 1-8 carbon atoms or an unsubstituted or substituted with halogen, alkyl with 1-6 carbon atoms, alkoxygroup with 1-6 carbon atoms, halogenation with 1-4 carbon atoms, halogenlampe with 1-4 carbon atoms, cyano or nitro-group is phenyl or benzyl;

R4and R5independently from each other, each represent unsubstituted or substituted with halogen alkyl with 1-8 carbon atoms, alkoxy with 1-8 carbon atoms, alkylamino with 1-8 carbon atoms, dialkylamino with 1-8 carbon atoms in each alkyl group, alkylthio with 1-8 carbon atoms or alkanity with 3-8 carbon atoms, or an unsubstituted or substituted with halogen, a nitro-group, cyano, alkoxygroup with 1-4 carbon atoms, halogenlampe with 1-4 carbon atoms, alkylthiol with 1-4 carbon atoms, halogeenilamppu with 1-4 carbon atoms, alkyl with 1-4 carbon atoms or halogenation with 1-4 carbon atoms, phenyl, phenoxy or phenylthio;

R6and R7independently from each other, each denote hydrogen, unsubstituted or substituted with halogen alkyl with 1-8 carbon atoms, cycloalkyl with 3-8 carbon atoms, alkoxy with 1-8 atoms gullerud; unsubstituted or substituted with halogen, alkyl with 1-8 carbon atoms, halogenation with 1-8 carbon atoms or alkoxygroup with 1-8 carbon atoms, phenyl or benzyl, or together denote unsubstituted or substituted by alkyl with 1-6 carbon atoms alkalinity balance with 3-6 carbon atoms in which one methylene group may be replaced by oxygen atom or a sulfur atom;

R13means hydrogen or unsubstituted or substituted by halogen alkyl with 1-8 carbon atoms or alkoxy with 1-8 carbon atoms, unsubstituted or substituted with halogen, alkyl with 1-4 carbon atoms or alkoxygroup with 1-4 carbon atoms, cycloalkyl with 3-8 carbon atoms in which one methylene group may be replaced by oxygen atom or a sulfur atom, or unsubstituted or substituted by halogen, alkyl with 1-6 carbon atoms, alkoxygroup with 1-6 carbon atoms, halogenation with 1-4 carbon atoms, halogenlampe with 1-4 carbon atoms, a nitro-group or a cyano phenyl, phenylalkyl with 1-4 carbon atoms in the alkyl part or phenylalkyl with 1-4 carbon atoms in the CNS;

R14means hydrogen or alkyl with 1-8 carbon atoms or

R13and R14together oznacujuci with 1-6 carbon atoms or

R15and R16together mean ascandilwy residue with 2 to 4 carbon atoms which may be substituted by alkyl with 1-6 carbon atoms or phenyl, unsubstituted or substituted with halogen, alkyl with 1-4 carbon atoms, halogenation with 1-4 carbon atoms, alkoxygroup with 1-4 carbon atoms, halogenlampe with 1-4 carbon atoms, a nitro-group, or cyano;

R17and R18independently from each other, each denote hydrogen, unsubstituted or substituted with halogen alkyl with 1-8 carbon atoms, either unsubstituted or substituted with halogen, alkyl with 1-6 carbon atoms, alkoxygroup with 1-6 carbon atoms, halogenation with 1-4 carbon atoms, halogenlampe with 1-4 carbon atoms, a nitro-group or a cyano phenyl, or

R17and R18together with the carbon atom to which they are linked, represent a carbonyl group, unsubstituted or substituted by alkyl with 1-4 carbon atoms or alkoxygroup with 1-4 carbon atoms, cycloalkyl with 5-7 carbon atoms in which one methylene group may be replaced by oxygen atom or a sulfur atom;

R19and R20independently from each other, each represent alkyl with 1-10 carbon atoms, alkenyl themselves carbon dialkylamino with 1-10 carbon atoms in each alkyl group or dialkylamino with 3-10 carbon atoms in each alkenylphenol group.

The compounds of formula (I) depending on the nature of the substituents may exist as geometric and/or optical isomers or mixtures of isomers in various proportions, which if necessary can be separated by conventional means. The object of the present invention are as pure isomers and mixtures of isomers, as well as the method and means of combating insects and arachnids are based on them. However, in the future, for the sake of simplicity, always speaks of the compounds of formula (I), although meant as a pure compound, if necessary, and mixed with different ratios of isomeric compounds.

With the introduction of Het-groups of the formulas from (1) to (5) given the following main structures (I-1) to (I-5):

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where a, b, D, G, X, Y and Z have the above values.

If Het represents the group of formula (1), when the group G with values: (a) (b), (C), (d), (d), (e) and (f) receive the following main structures (I-1-a) to (I-1-W):

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where A, B, D, E, L, M, X, Y, Z, R1, R2, R3, R4 is the formula (2), when the group G with values: (a) (b), (C), (d), (e), (f) and (g) are formed following main structures (I-2-a) to (I-2-g):

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where a, b, E, L, M, X, Y, Z, R1, R2, R3, R4R5, R6and R7have the above values.

If Het represents the group of formula (3), when different values of G (a), (b), (C), (d), (d), (e) and (f) receive the following main structures (I-3-a) to (I-3-g):

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where

A, B, E, L, M, X, Y, Z, R1, R2, R3R4R5R6and R7have the above values.

The compounds of formula (I-4) depending on the position of the substituent G can exist in two isomeric forms: (I-4)andand (I-4)b:

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in the formula (I-4) should be reflected by a dotted line.

Compounds of formula (I-4)andand (I-4)bcan exist in the form of mixtures and in the form of pure isomers. A mixture of compounds of formula (I-4)andand (I-4)bif necessary, you can split itself in a known manner by means of physical methods, such as chromatography.

Further clarity in each case the unity can exist as mixtures of isomers or accordingly, in another isomeric form.

If Het represents the group of formula ( 4 ), then, with the introduction of different values Deputy G (a), (b), (C), (d), (d), (e) and (f) receive the following main structures (I-4-a) to (I-4-g):

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where A, D, E, L, M, X, Y, Z, R1, R2, R3R4R5, R6and R7have the above values.

If Het represents a group of formula (5) then, with the introduction of different values of the Deputy group G (a), (b), (C), (d), (e), (f) and (g) given the following critical structures (I-5-a) to (I-5-g):

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where A, D, E, L, M, X, Y, Z, R1, R2, R3R4R5, R6and R7have the above values.

The proposed compounds of formula (I) receive one of the following describes the methods:

(A) the compounds of formula (I-1)

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where a, b, X, Y and Z have the above values,

get the intramolecular condensation of compounds of the formula (II)

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where a, b, X, Y and Z have the above values, and

R8means alkyl (preferably alkyl with 1-6 carbon atoms), in the presence of a diluent and base;

(B) in addition, the nuclear biological chemical (NBC condensation of the compounds of the formula (III)

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where a, b, X, Y, Z, and R8have the above meanings, in the presence of a diluent and base;

(C) further, the compounds of formula (I-3)

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where a, b, X, Y and Z have the above values,

get intramolecular cyclization of compounds of formula (IV)

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where a, b, X, Y, Z, and R8have the above values;

W stands for hydrogen, halogen, alkyl (preferably 1-6 carbon atoms) or alkoxy (preferably 1-8 carbon atoms);

optionally, in the presence of a diluent and in the presence of an acid;

(G) next, the compounds of formula (I-4-a)

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where A, D, X, Y and Z have the above values,

get when the compounds of formula (V)

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where a and D have the above values;

or Millenaire esters of the formula (Va)

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where a and D have the above values,

R8'means alkyl (preferably methyl),

subjected to interaction with compounds of the formula (VI)

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where X, Y and Z have the above values,

Gal means a halogen (preferably chlorine or bromine), and optionally in the presence of a diluent and optionally in the presence of an acid acceptor;

(D) further, the compounds of formula (I-5-a)

A has the above meaning,

subjected to interaction with compounds of the formula (VI)

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where Gal, X, Y and Z have the abovementioned meaning, optionally in the presence of a diluent and optionally in the presence of an acid acceptor.

In addition,

(E) compounds of the above formulas from (I-1-b) to (I-5-b) in which a, b, D, R1X, Y and Z have the values above get when compounds of the above formulas from (I-1-a) to (I-5-a) in which a, b, D, X, Y and Z have the above meanings, is subjected to interaction

with halogenide acids of the formula (VIII)

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where R1has the above meaning and Gal means halogen (in particular chlorine or bromine), or

with anhydrides of carboxylic acids of the formula (IX)

R1-CO-O-CO-R1(IX)

where R1has the above mentioned meaning, optionally in the presence of a diluent and optionally in the presence of means linking acid;

(G) compounds of the above formulas from (I-1) to (I-5) in which a, b, D, R2, M, X, Y and Z have the abovementioned meanings and L is oxygen, receive, when each of the compounds of the above formulas from (I-1-a) to (I-5-a) in which a, b, D, X, Y and Z have the above values,

subject of co is-CO-Cl-(X),

where R2and M have the above values,

optionally, in the presence of a diluent and optionally in the presence of means linking acid;

(C) compounds of the above formulas from (I-1) to (I-5) in which a, b, D, R2, M, X, Y and Z have the abovementioned meanings and L is a sulfur atom, when each of the compounds of the above formulas from (I-1-a) to (I-5-a) in which a, b, D, X, Y and Z have the above meanings, is subjected to interaction

) with esters of hormonestimulated acid or esters of chartitemevent acid of formula (XI)

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where M and R2have the above values,

optionally, in the presence of a diluent and optionally in the presence of means connecting the acid; or

) with carbon disulphide and then with compounds of the formula (XII)

R2-Gal (XII),

where R2has the above value and

Gal means chlorine, bromine or iodine, optionally in the presence of a diluent and optionally in the presence of a base;

(I) compounds of the above formulas from (I-1-g) to (I-5-g) in which a, b, D, R3X, Y and Z have the above values, when each of the compounds above Fotini sulphonic acids of the formula (XIII)

R3-SO2-Cl (XIII),

where R3has the above value, and optionally in the presence of a diluent and optionally in the presence of means linking acid;

(K) compounds of the above formulas from (I-1-d) to (I-5-d) in which a, b, D, L, R4, R5X, Y and Z have the above values, when each of the compounds of the above formulas from (I-1-a) to (I-4-a) in which a, b, D, X, Y and Z have the above meanings, is subjected to the interaction with phosphorus compounds of the formula (XIV)

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where L, R4and R5have the above values and

Gal means halogen (in particular chlorine or bromine), if necessary, in the presence of a diluent and optionally in the presence of means linking acid;

(L) compounds of the above formulas from (I-1-e) to (I-5-e) in which a, b, D, E, X, Y and Z have the above values, when each of the compounds of formulas from (I-1-a) to (I-5-a) in which a, b, D, X, Y and Z have the above meanings, is subjected to the interaction with metal compounds or amines of the formulae (XV) or (XVI)< / BR>
Me(OR10)t(XV),

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where Me means a monovalent or divalent metal (preferably the alkaline and 2 and

R10, R11, R12independently of one another, each represent hydrogen or alkyl (preferably alkyl with 1-8 carbon atoms), optionally in the presence of a diluent;

(M) compounds of the above formulas from (I-1-g) to (I-5-g) in which a, b, D, L, R6, R7X, Y and Z have the above values, when each of the compounds of the above formulas from (I-1-a) to (I-5-a) in which a, b, D, X, Y and Z have the above meanings, is subjected to interaction

) with isocyanates or isothioscyanates formula (XVII)

R6-N=C=L (XVII),

in which R6and L have the abovementioned meaning, optionally in the presence of a diluent and optionally in the presence of a catalyst; or

with anhydrides karbinovykh or thiocarbamide acids of the formula (XVIII)

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where L, R6and R7have the above values, if necessary in the presence of a diluent and optionally in the presence of means connecting the acid.

Further, it is found that the new compounds of formula (I) show a very good activity as pesticides, preferably as insecticides and acaricides, and, moreover, they are very well compatible with plants, EDINENIE formula (I),

where X is fluorine, chlorine, bromine, alkyl with 1-4 carbon atoms, alkoxy with 1-4 carbon atoms, halogenated with 1-2 carbon atoms, halogenoalkanes with 1-2 carbon atoms, cyano or nitro-group;

Y represents fluorine, chlorine, bromine, alkyl with 1-4 carbon atoms, alkoxy with 1-4 carbon atoms, halogenated with 1-2 carbon atoms, halogenoalkanes with 1-2 carbon atoms, cyano or nitro-group;

Z means fluorine, chlorine, bromine, alkyl with 1-4 carbon atoms, alkoxy with 1-4 carbon atoms, halogenated with 1-2 carbon atoms, halogenoalkanes with 1-2 carbon atoms, a cyano, a nitro-group or phenoxy or benzyloxy, each of which is not substituted or substituted by fluorine, chlorine, bromine, alkyl with 1-4 carbon atoms, alkoxyl with 1-4 carbon atoms, halogenation with 1-2 carbon atoms, halogenation with 1-2 carbon atoms, a nitro-group, or cyano; or

Y and Z together denote unsubstituted or substituted by fluorine, chlorine, bromine, alkyl with 1-4 carbon atoms, alkoxyl with 1-4 carbon atoms or halogenation with 1-2 carbon atoms alcander with 3-4 carbon atoms or alkerdeel with 3-4 carbon atoms, where one or two non-directly adjacent link independently will dragonache one of the groups:

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A represents hydrogen, unsubstituted or substituted by fluorine or chlorine, alkyl with 1-10 carbon atoms, alkenyl with 2-6 carbon atoms, alkyl with 1-6 carbon atoms, substituted alkoxygroup with 1-8 carbon atoms, alkyl with 1-6 carbon atoms, polyamidine alkoxygroup with 1-6 carbon atoms each, or alkyl with 1-6 carbon atoms, substituted alkylthiol with 1-8 carbon atoms, either unsubstituted or substituted by fluorine, chlorine, alkyl with 1-4 carbon atoms or alkoxygroup with 1-4 carbon atoms, cycloalkyl with 3-7 carbon atoms, in which one or two methylene groups may be replaced by oxygen atom and/or sulfur atom, or unsubstituted or substituted by fluorine, chlorine, bromine, alkyl with 1-4 carbon atoms, halogenation with 1-4 carbon atoms, alkoxygroup with 1-4 carbon atoms, halogenlampe with 1-4 carbon atoms, cyano or nitro-group is phenyl, furanyl, pyridyl, imidazolyl, triazolyl, pyrazolyl, indolyl, thiazolyl, thienyl, or phenylalkyl with 1-4 carbon atoms in the alkyl part;

In denotes hydrogen, alkyl with 1-10 carbon atoms or alkyl with 1-4 carbon atoms, substituted alkoxygroup with 1-6 carbon atoms, or

A, b and the carbon atom,kind, in each of which one methylene group may be replaced by oxygen atom or sulfur atom and which may be substituted by alkyl with 1-6 carbon atoms, cycloalkyl with 3-8 carbon atoms, halogenation with 1-3 carbon atoms, alkoxygroup with 1-6 carbon atoms, alkylthiol with 1-6 carbon atoms, fluorine, chlorine or phenyl, or

A, b and the carbon atom to which they are linked, represent cycloalkyl with 5-6 carbon atoms, which is substituted by not containing or containing one or two oxygen atom or sulfur alkylenediamines or alkylenediamines or alkylenediamine group, which with the carbon atom to which it is linked, forms an additional five - semiline ring, or

A, b and the carbon atom to which they are linked, represent cycloalkyl with 3-6 carbon atoms or cycloalkenyl with 5-6 carbon atoms, where two Deputy together with the carbon atoms to which they are linked, represent unsubstituted or substituted by alkyl with 1-4 carbon atoms, alkoxygroup with 1-4 carbon atoms, fluorine, chlorine or bromine alcander with 3-5 carbon atoms, alkerdeel with 3-5 carbon atoms or butadienyl, in each of which one methylene group may be replaced by al with 1-10 carbon atoms, alkenyl with 3-6 carbon atoms, quinil with 3-6 carbon atoms, alkyl with 2-6 carbon atoms, substituted alkoxygroup with 1-8 carbon atoms, alkyl with 2-6 carbon atoms, polyamidine alkoxygroup with 1-6 carbon atoms each, or alkyl with 2-6 carbon atoms, substituted alkylthiol with 1-8 carbon atoms, unsubstituted or substituted by fluorine, chlorine, alkyl with 1-4 carbon atoms, alkoxygroup with 1-4 carbon atoms or halogenlampe with 1-2 carbon atoms, cycloalkyl with 3-7 carbon atoms, in which one or two non-directly adjacent methylene groups may be replaced by oxygen atom and/or sulfur atom, or unsubstituted or substituted by fluorine, chlorine, bromine, alkyl with 1-4 carbon atoms, halogenation with 1-4 carbon atoms, alkoxygroup with 1-4 carbon atoms, halogenlampe with 1-4 carbon atoms, cyano or nitro-group is phenyl, furanyl, imidazolyl, pyridyl, thiazolyl, pyrazolyl, pyrimidyl, pyrrolyl, thienyl, triazolyl or phenylalkyl with 1-4 carbon atoms in the alkyl part, or

A and D together represent landiolol group having 3-5 carbon atoms or alkantiolsul group having 3-5 carbon atoms, in each of which one atom pleaaseee or substituted by fluorine or chlorine alkyl with 1-6 carbon atoms, alkoxygroup with 1-4 carbon atoms, alkylthiol with 1-4 carbon atoms, cycloalkyl with 3-6 carbon atoms, phenyl or benzyloxycarbonyl or where in each case optionally contains one of the following groups:

< / BR>
< / BR>
< / BR>
< / BR>
or

< / BR>
G means hydrogen (a) or one of the groups:

< / BR>
< / BR>
< / BR>
< / BR>
E (E) or

< / BR>
where E is the equivalent of a metal ion or ammonium ion,

L is an oxygen atom or a sulfur atom,

M is an oxygen atom or a sulfur atom,

R1means unsubstituted or substituted by fluorine or chlorine, alkyl with 1-16 carbon atoms, alkenyl from 2-16 carbon atoms, alkoxyalkyl with 1-6 carbon atoms in the alkyl and parts of the CNS, alkylthiols with 1-6 carbon atoms in the alkyl and alkylthiolated or polyalkoxyalkyl with 1-6 carbon atoms in the alkyl and in all alkoxygroup, either unsubstituted or substituted by fluorine, chlorine, alkyl with 1-5 carbon atoms or alkoxygroup with 1-5 carbon atoms cycloalkyl with 3-7 carbon atoms in which one or two methylene groups may be replaced by oxygen atom or a sulfur atom;

unsubstituted or substituted by fluorine, chlorine, bromine, cyano, a nitro-group, alkyl with 1-4 carbon atoms, alkoxy alkylthiophene with 1-4 carbon atoms or alkylsulphonyl with 1-4 carbon atoms, phenyl;

unsubstituted or substituted by fluorine, chlorine, bromine, alkyl with 1-4 carbon atoms, alkoxygroup with 1-4 carbon atoms, halogenation with 1-3 carbon atoms or halogenlampe with 1-3 carbon atoms, phenylalkyl with 1-4 carbon atoms in the alkyl part;

unsubstituted or substituted by fluorine, chlorine, bromine or alkyl with 1-4 carbon atoms pyrazolyl, thiazolyl, pyridyl, pyrimidyl, furanyl or thienyl;

unsubstituted or substituted by fluorine, chlorine, bromine or alkyl with 1-4 carbon atoms, phenoxyethyl with 1-5 carbon atoms in the alkyl part, or

unsubstituted or substituted by fluorine, chlorine, bromine, amino or alkyl with 1-4 carbon atoms, peridiocally with 1-5 carbon atoms in the alkyl part, pyrimidinemethanol with 1-5 carbon atoms in the alkyl part or thiazoleacetate with 1-5 carbon atoms in the alkyl part;

R2means unsubstituted or substituted by fluorine or chlorine, alkyl with 1-16 carbon atoms, alkenyl from 2-16 carbon atoms, alkyl with 2-6 carbon atoms, substituted alkoxygroup with 1-6 carbon atoms, or alkyl with 2-6 carbon atoms, polyamidine alkoxygroup with 1-6 carbon atoms in each;

unsubstituted or substituted by fluorine, chlorine, alkylidene or substituted by fluorine, chlorine, bromine, cyano, a nitro-group, alkyl with 1-4 carbon atoms, alkoxygroup with 1-3 carbon atoms, halogenation with 1-3 carbon atoms or halogenlampe with 1-3 carbon atoms, phenyl or benzyl;

R3means unsubstituted or substituted by fluorine or chlorine, alkyl with 1-6 carbon atoms, either unsubstituted or substituted by fluorine, chlorine, bromine, alkyl with 1-4 carbon atoms, alkoxygroup with 1-4 carbon atoms, halogenation with 1-2 carbon atoms, halogenlampe with 1-2 carbon atoms, cyano or nitro-group is phenyl or benzyl;

R4and R5independently from each other, each represent unsubstituted or substituted by fluorine or chlorine, alkyl with 1-6 carbon atoms, alkoxy with 1-6 carbon atoms, alkylamino with 1-6 carbon atoms, dialkylamino with 1-6 carbon atoms in each alkyl group, alkylthio with 1-6 carbon atoms or alkanity with 3-4 carbon atoms, either unsubstituted or substituted by fluorine, chlorine, bromine, nitro-group, cyano, alkoxygroup with 1-3 carbon atoms, halogenlampe with 1-3 carbon atoms, alkylthiol with 1-3 carbon atoms, halogeenilamppu with 1-3 carbon atoms, by alkyl with 1-3 carbon atoms or halogen is jdy, mean hydrogen, unsubstituted or substituted by fluorine or chlorine, alkyl with 1-6 carbon atoms, cycloalkyl with 3-6 carbon atoms, alkoxy with 1-6 carbon atoms, alkenyl with 3-6 carbon atoms or alkyl with 2-6 carbon atoms, substituted alkoxygroup with 1-6 carbon atoms, unsubstituted or substituted by fluorine, chlorine, bromine, halogenation with 1-5 carbon atoms, alkyl with 1-5 carbon atoms or alkoxygroup 1-5 carbon atoms, phenyl or benzyl or together represent an unsubstituted or substituted by alkyl with 1-4 carbon atoms alkalinity balance with 3-6 carbon atoms, in which one methylene group may be replaced by oxygen atom or a sulfur atom;

R13means hydrogen or unsubstituted or substituted by fluorine or chlorine, alkyl with 1-6 carbon atoms or alkoxy with 1-6 carbon atoms, unsubstituted or substituted by fluorine, alkyl with 1-2 carbon atoms or alkoxygroup with 1-2 carbon atoms, cycloalkyl with 3-7 carbon atoms in which one methylene group may be replaced by oxygen atom or a sulfur atom, or unsubstituted or substituted by fluorine, chlorine, bromine, alkyl with 1-5 carbon atoms, alkoxygroup with 1-5 carbon atoms, halogenation with 1-2 carbon atoms is of glared in the alkyl part or phenylalkyl with 1-2 carbon atoms in the CNS;< / BR>
R14means hydrogen or alkyl with 1-6 carbon atoms, or

R13and R14together represent alcander with 4-6 carbon atoms;

R15and R16are the same or different and represent alkyl with 1-4 carbon atoms or

R15and R16together represent ascandilwy residue with 2 to 3 carbon atoms which may be substituted by alkyl with 1-4 carbon atoms or unsubstituted or substituted by fluorine, chlorine, bromine, alkyl with 1-2 carbon atoms, halogenation with 1-2 carbon atoms, alkoxygroup with 1-2 carbon atoms, halogenlampe with 1-2 carbon atoms, a nitro-group or cyano-phenyl.

Most preferred are phenylethanol General formula (I), where

X is fluorine, chlorine, bromine, methyl, ethyl, propyl, butyl, isobutyl, isopropyl, tert-butyl, methoxy group, ethoxypropan, propoxylate, isopropoxy, trifluoromethyl, cryptometer, dipterocarp, cyano or nitro-group;

Y represents fluorine, chlorine, bromine, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, methoxy group, ethoxypropan, propoxylate, isopropoxy, trifluoromethyl, cryptometer, diformal, isopropyl, tert-butyl, methoxy group, ethoxypropan, propoxylate, isopropoxy, trifluoromethyl, cryptometer, dipterocarp, cyano or nitro-group; or

Y and Z together denote unsubstituted or substituted by fluorine, chlorine, stands, ethyl, propylene, isopropyl, methoxy group, ethoxypropane, propoxyphene, isopropoxycarbonyl or trifluoromethyl alcander with 3-4 carbon atoms, in which two not directly adjacent link can be replaced by oxygen, and X is any one of the above values;

Het represents one of the groups:

< / BR>
< / BR>
< / BR>
< / BR>
< / BR>
A represents hydrogen, unsubstituted or substituted by fluorine or chlorine, alkyl with 1-8 carbon atoms, alkenyl with 2-4 carbon atoms, alkyl with 1-4 carbon atoms, substituted alkoxygroup with 1-6 carbon atoms, polyalkoxyalkyl with 1-4 carbon atoms in the alkyl part and in all CNS groups, or alkyl with 1-4 carbon atoms, substituted alkylthiol with 1-6 carbon atoms, either unsubstituted or substituted by fluorine, chlorine, stands or a methoxy group cycloalkyl with 3-6 carbon atoms, in which one or two methylene groups may be replaced by oxygen atom and/or autobigraphy, ethoxypropane, trifluoromethyl, cryptomaterial, cyano or nitro-group is phenyl, pyridyl or benzyl;

In denotes hydrogen, alkyl with 1-8 carbon atoms or alkyl with 1-2 carbon atoms, substituted alkoxygroup with 1-4 carbon atoms, or

A, b and the carbon atom to which they are linked, represent cycloalkyl with 3-8 carbon atoms or cycloalkenyl with 5-8 carbon atoms in which one methylene group may be replaced by oxygen atom or sulfur atom and which is not substituted or substituted by stands, ethyl, n-propylene, isopropyl, bootrom, isobutyl, second-bootrom, tert-bootrom, cyclohexyl, trifluoromethyl, methoxy group, ethoxypropane, n-propoxyphene, isopropoxycarbonyl, butoxypropyl, isobutoxy, second-butoxypropyl, tert-butoxypropyl, methylthiourea, ethylthiourea, fluorine, chlorine or phenyl, or

A, b and the carbon atom to which they are linked, represent cycloalkyl with 5-6 carbon atoms, which is not substituted or substituted alkylenediamine group may contain an oxygen atom or a sulfur atom, or alkylenedioxy group, which with the carbon atom to which it is linked, forms an additional five - or six-membered ring, or
lceil with 5-6 carbon atoms, in which two Deputy together with the carbon atoms to which they are linked, represent alcander with 3-4 carbon atoms, alkerdeel with 3-4 carbon atoms or butadienyl in which one methylene group may be replaced by oxygen atom or a sulfur atom;

D is hydrogen, unsubstituted or substituted by fluorine or chlorine, alkyl with 1-8 carbon atoms, alkenyl with 3-4 carbon atoms, quinil with 3-4 carbon atoms, alkyl with 2 to 4 carbon atoms, substituted alkoxygroup with 1-6 carbon atoms, alkyl with 2 to 4 carbon atoms, polyamidine alkoxygroup with 1-4 carbon atoms in each group, alkyl with 2 to 4 carbon atoms, substituted alkylthiol with 1-4 carbon atoms, or cycloalkyl with 3-6 carbon atoms, in which one or two non-directly adjacent methylene groups may be replaced by oxygen atoms and/or sulfur, either unsubstituted or substituted by fluorine, chlorine, bromine, stands, ethyl, n-propylene, isopropyl, methoxy group, ethoxypropane, trifluoromethyl, cryptomaterial, cyano or nitro-group is phenyl, furanyl, pyridyl, thienyl or benzyl, or

A and D together represent landiolol group having 3-5 carbon atoms or alkantiolsul group the market and which may be substituted by fluorine, chlorine or not substituted or substituted by fluorine or chlorine alkyl with 1-6 carbon atoms, alkoxygroup with 1-4 carbon atoms, alkylthiol with 1-4 carbon atoms, cycloalkyl with 3-6 carbon atoms, phenyl or benzyloxycarbonyl, or

G means hydrogen (a) or one of the groups:

< / BR>
< / BR>
< / BR>
< / BR>
E (E) or

< / BR>
where E is the equivalent of a metal ion or ammonium ion,

L is an oxygen atom or a sulfur atom,

M is an oxygen atom or a sulfur atom;

R1means unsubstituted or substituted by fluorine or chlorine, alkyl with 1 to 14 carbon atoms, alkenyl with 2-14 carbon atoms, alkyl with 1-6 carbon atoms, substituted alkoxygroup with 1-4 carbon atoms, alkyl with 1-6 carbon atoms, substituted alkylthiol with 1-4 carbon atoms, alkyl with 1-4 carbon atoms, polyamidine arcoxia with 1-4 carbon atoms or unsubstituted or substituted by fluorine, chlorine, stands, ethyl, n-propylene, isopropyl, n-bootrom, isobutyl, tert-bootrom, a methoxy group, ethoxypropane, n-propoxyphene or isopropoxycarbonyl cycloalkyl with 3-6 carbon atoms, in which one or two methylene groups may be replaced by oxygen atom and/or sulfur atom;

unsubstituted or substituted by fluorine, chlorine, bromine, qi the sludge, cryptomaterial, methylthiourea, ethylthiourea, methylsulfonyl or ethylsulfonyl phenyl;

unsubstituted or substituted by fluorine, chlorine, bromine, stands, ethyl, n-propylene, isopropyl, methoxy group, ethoxypropane, trifluoromethyl, cryptomaterial benzyl;

unsubstituted or substituted by fluorine, chlorine, bromine, stands or ethyl furanyl, thienyl or pyridyl;

unsubstituted or substituted by fluorine, chlorine, stands or ethyl peroxyacyl with 1-4 carbon atoms in the alkyl part, or unsubstituted or substituted by fluorine, chlorine, amino group, stands or ethyl peridiocally with 1-4 carbon atoms in the alkyl part, pyrimidinemethanol with 1-4 carbon atoms in the alkyl part or thiazoleacetate with 1-4 carbon atoms in the alkyl part.

R2means unsubstituted or substituted by fluorine or chlorine, alkyl with 1 to 14 carbon atoms, alkenyl with 2-14 carbon atoms, alkyl with 2-6 carbon atoms, substituted alkoxygroup with 1-4 carbon atoms or alkyl with 2-6 carbon atoms, polyamidine alkoxygroup with 1-4 carbon atoms in each group;

unsubstituted or substituted by fluorine, chlorine, stands, ethyl, n-propylene, isopropyl or methoxy group, cyclo, what etiam, ethyl, n-propylene, isopropyl, methoxy group, ethoxypropane, trifluoromethyl or cryptomaterial phenyl or benzyl;

R3means unsubstituted or substituted by fluorine or chlorine, methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, either unsubstituted or substituted by fluorine, chlorine, bromine, stands, ethyl, isopropyl, tert-bootrom, a methoxy group, ethoxypropane, isopropoxy, trifluoromethyl, cryptomaterial, cyano or nitro-group is phenyl or benzyl;

R4and R5independently from each other, each represent unsubstituted or substituted by fluorine or chlorine, alkyl with 1-4 carbon atoms, alkoxy with 1-4 carbon atoms, alkylamino with 1-4 carbon atoms, dialkylamino with 1-4 carbon atoms in each alkyl group or alkylthio with 1-4 carbon atoms, either unsubstituted or substituted by fluorine, chlorine, bromine, nitro-group, cyano, stands, a methoxy group, a trifluoromethyl or cryptomaterial phenyl, phenoxy or phenylthio;

R6and R7independently from each other, each denote hydrogen, unsubstituted or substituted by fluorine or chlorine, alkyl with 1-4 carbon atoms, cycloalkyl with 3-6 carbon atoms, alkoxy with 1-4 carbon atoms, alkene tamaseni or substituted by fluorine, chlorine, bromine, stands, a methoxy group or a trifluoromethyl phenyl or benzyl, or together denote unsubstituted or substituted by stands or ethyl alkalinity balance with 5-6 carbon atoms in which one methylene group may be replaced by oxygen atom or a sulfur atom.

Saturated or unsaturated hydrocarbon residues such as alkyl or alkenyl, also in combination with heteroatoms, such as, for example, in alkoxygroup, can be linear or branched.

Optionally substituted residues may be substituted one or more times, and in the case of multiple substitution, the substituents may be the same or different.

If according to the method (A) as the initial substance use ethyl ester of N-[(4,5-dichloro-2-methyl)-phenylacetyl]-1-amino-4-ethylcyclohexylamine acid, the process can be represented by reaction scheme 1 (see the end of the description).

If according to process (B) use the ethyl ester of O-[(2,5-dichloro-4-methyl)phenylacetyl] hydroxyoctanoic acid, the process can be represented by reaction scheme 2 (see the end of the description).

If according to the method (C) using ethyl ester 2-[(2-chloro-4,5-dimethyl)FeNi is scheme 3 (see at the end of the description).

If, for example, according to process (G) as starting substances used (chlorocarbonyl)-2-[(4,5-dichloro-2-methyl)phenyl ] ketene and acetone, the process can be represented by reaction scheme 4 (see end of description)

If, for example, according to method (D) as a source of substances used (chlorocarbonyl)-2-[(2,4,5-trimethyl)phenyl] ketene and thiobenzamide, the process can be represented by reaction scheme 5 (see the end of the description).

If according to process (E) as the original substances using 3-[(2,5-dichloro-4-methyl)phenyl]-5,5-dimethylpyrimidin-2,4-dione and pivaloyloxy, the process can be represented by reaction scheme 6 (see the end of the description).

If according to process (E) (option ) as the original substances using 3-[(2,4,5-trichloro)phenyl]-4-hydroxy-5-phenyl-3-dihydrofuran-2-he and acetic anhydride, the process can be represented by reaction scheme 7 (see the end of the description).

If according to process (G) as starting compounds using 8-[(2,4-dichloro-5-methyl)phenyl] -5,5-pentamethylpiperidin-2,4-dione and ethoxyethyl ether of Harborview acid, the process can be represented by reaction scheme 8 (see end of description).

If according to the way tilby ether of hormonestimulated acid, the flowing reaction can be depicted in scheme 9 (see at the end of the description).

If according to process (H) (option ) as the original substances using 5-[(5-chloro-2-fluoro-4-methyl)phenyl]-6-hydroxy-2-(4-chlorophenyl)-thiazin-4-one, carbon disulfide and methyliodide, then flowing the reaction can be depicted in scheme 10 (see the end of the description).

If according to the method (S) as the original substances using 2-[(2,4,5-trimethyl)phenyl] -5,5-(3-methyl)pentamethylpiperidin-2,4-dione and methansulfonate, then flowing the reaction can be represented by reaction scheme 11 (see the end of the description).

If according to process (K) as the original substances using 2-[(2-chloro-4,5-dimethyl)phenyl] -4-hydroxy-5-methyl-6-(2-pyridyl)-pyrone and 2,2,2-triptoreline ester acid chloride of metalliferous acid, then flowing the reaction can be represented by reaction scheme 12 (see the end of the description).

If according to process (L) as components using 3-[(2,4,5-trichloro)phenyl] -5-cyclopropyl-5-methylpyrrolidine-2,4-dione and the sodium hydroxide, the process flow can be represented by reaction scheme 13 (see the end of the description).

If according to the method (M) (option ) as starting substances espolla reaction can be represented by reaction scheme 14 (see at the end of the description).

If according to the method (M) (option ) as the original substances using 3-[(2-chloro-4,5-dimethyl)phenyl]-5-methylpyrrolidine-2,4-dione and the acid chloride dimethylcarbinol acid, then flowing the reaction can be represented by reaction scheme 15 (see the end of the description).

The compounds of formula ( II)

< / BR>
where a, b, X, Y, Z, and R8have the above values, required as starting materials in the method (a) is a further object of the present invention.

Esters of acylaminoacyl formula (II) are obtained, for example, if the derived amino acid of formula (XIX)

< / BR>
where a, b, R8have the above values, acelerou replaced by halogenide phenylacetic acid of the formula (XX)

< / BR>
where X, Y and Z have the above values and

Gal means chlorine or bromine

(Chem. Reviews 52, 237-416 (1953); Bhattacharrya, Indian J. Chem. 6, 341-5, (1968));

or if atrificial acylaminoalkyl formula (XXI)

< / BR>
where a, b, X, Y and Z have the values indicated above (Chem. Ind. (London) 1568 (1968)).

The compounds of formula (XXI)

< / BR>
where a, b, X, Y and Z have the abovementioned meanings, are also an object of the present invention.

The compounds of formula (XXI) are obtained, mu substituted halogenide phenylacetic acid of the formula (XX)

< / BR>
where X, Y and Z have the above values and

Gal means chlorine or bromine

(Organikum, Ed. VEB Deutscher Verlag der Wissenschaften, Berlin 1977, S. 505).

The compounds of formula (XX) are partly new, and they can be obtained by known methods.

The compounds of formula (XX) are obtained, for example, the fact that the substituted phenylacetic acids of the formula (XXIII)

< / BR>
where X, Y and Z have the above values,

subjected to interaction with halogenation agents (for example thionyl chloride, tierbroker, oxalicacid, phosgene, phosphorus trichloride, tribromide phosphorus or with phosphorus pentachloride), if necessary in the presence of a diluent (for example, chlorinated aliphatic or aromatic hydrocarbons, such as toluene or methylene chloride) at temperatures from -20 to 150oC, preferably from -10 to 100oC.

The compounds of formula (XXIII) are partly new, you can get them known from the literature (Organikum, 15th edition, S. 533, VEB Deutscher Verlag der Wissenschaften, Berlin, 1977).

The compounds of formula (XXV) are obtained, for example, by hydrolysis of the substituted esters of phenylacetic acid of the formula (XXIV)

< / BR>
where X, Y, Z, and R8have the above value is R, the alkali metal hydroxide, such as sodium hydroxide or potassium hydroxide) and, if necessary, in the presence of a diluent (for example an aqueous alcohol, such as methanol or ethanol) at temperatures between 0 and 150oC, preferably between 20 and 100oC.

The compounds of formula (XXIV) are partly new, you can get them on the principle of the known methods.

The compounds of formula (XXIV) are obtained, for example, the fact that substituted 1,1,1-trichloro-2-phenylethane formula (XXV)

< / BR>
where X, Y and Z have the above values,

are engaging first alcoholate (for example, with alkali metal alcoholate such as sodium methylate or sodium ethylate) in the presence of a diluent (for example, alcohol, from which is formed the alcoholate at temperatures between 0 and 150oC, preferably between 20 and 120oWith, and then with an acid (preferably an inorganic acid, such as, for example, sulphuric acid) at temperatures between -20 and 150oC, preferably between 0 and 100o(See patent Germany 33 14 249).

The compounds of formula (XXV) are partly new, you can get them on the principle of the known methods.

The compounds of formula (XXV) are obtained, for example, when the first vinylidenechloride (CH2= CCl2in the presence of Alternaria formula (XXVII)

R21-ONO (XXVII),

where R21means alkyl, preferably alkyl with 1-6 carbon atoms;

in the presence of copper chloride (II), and optionally in the presence of a diluent (for example, aliphatic nitrile such as acetonitrile) at a temperature of from -20 to 80oC, preferably from 0 to 60o(See J. Org. Chem. 53 (1988), 3637).

Compounds of formula (XXVI) and (XXVII) are known in organic chemistry compounds. Chloride copper (II) and vinylidenechloride long been known and are commercial products.

Compounds of formula (XIX) and (XXII) are partly known and/or can be obtained by known methods (see, for example, Compagnon, Miocque Ann. Chim. (Paris) [14] 5, pages 11-22, 23-27 (1970)).

Substituted cyclic aminocarbonyl acid of the formula (HHA) in which a and b form a ring, in General, can be synthesized by Bucherer-Bergs or Striker and in each case are formed in different isomeric forms. Thus, in the synthesis conditions on Bucherer-Bergs mostly get isomers (hereinafter, for simplicity, called isomers), in which the residues R and the carboxyl group are Equatorial position, while in Erami), we are in the Equatorial position are the amino group and the remains of the R.

< / BR>
< / BR>
(L. Munday, J. Chem. Soc. 4372 (1961); J. T. Eward, S. Jitrangeri, Can. J. Chem. 53,3339(1975).

Used in the above method of the parent substance of the formula (II)

< / BR>
where a, b, X, Y, Z, and R8have the above values, is obtained if aminonitriles formula (XXVIII)

< / BR>
where a and b have the above meanings, is subjected to the interaction with substituted halogenide phenylacetic acid of the formula (XX)

< / BR>
where X, Y, Z and Gal have the above values, with the formation of compounds of formula (XXIX)

< / BR>
where a, b, X, Y and Z have the above meanings, followed by acidic alcoholysis of these compounds.

The compounds of formula (XXIX) are also the object of the present invention.

The compounds of formula (III)

< / BR>
where a, b, X, Y, Z, and R8have the above values, required as starting materials in the method (B) according to the invention, a further object of the present invention.

It can be obtained in a simple way, in principle, the known methods.

The compounds of formula (III) receive, if, for example, esters of 2-hydroxycarbonic acids of the formula (XXX)

< / BR> the acid of formula (XX)

< / BR>
where X, Y, Z and Gal have the above values

(Chem. Reviews 52, 237-416 (1953)),

Further, the compounds of formula (III) are obtained when substituted phenylacetic acids of the formula (XXIII)

< / BR>
where X, Y, and Z have the above values, alkylate esters-halogencarbonic acids of the formula (XXXI)

< / BR>
where a, b and R8have the above values and

Gal means chlorine or bromine.

The compounds of formula (XXXI) are trademarks.

The compounds of formula (IV)

< / BR>
where a, b, W, X, Y, Z, and R8have the above values, required as starting materials in the method (B) is a further object of the present invention.

They can be obtained in principle by known methods. For example, the compounds of formula (IV) are obtained when substituted esters of phenylacetic acid of the formula (XXIV)

< / BR>
where X, Y, R8and Z have the above values, acelerou halogenide 2-benzelstierna acids of the formula (XXXII)

< / BR>
where a, b and W have the above values and

Gal means halogen (in particular chlorine or bromine);

in the presence of strong bases (see , for example, M. S. Chambers, E. J. Thomas, D. J. Williams, J. Chem. Soc. Chem. Commun, (1987), 1228).

Galodamadruga S="ptx2">

Halogenecarbonate formula (VI) required as starting materials in the method (G), are also the object of the present invention. Get them in principle by known methods in a simple way (see, for example, Org. Prep. Proced. Int., 7, (4), 155-158, 1975 and the Federal Republic of Germany patent 1945703).

The compounds of formula (VI)

< / BR>
where X, Y and Z have the above values and

Gal means chlorine or bromine, get that replaced phenylmalonamide acid of the formula (XXXIII)

< / BR>
where X, Y and Z have the above values,

subjected to interaction with halogenide acids, such as, for example, thionyl chloride, Piatigorsky phosphorus, phosphorus trichloride, oxalicacid, phosgene or thienylboronic, optionally in the presence of catalysts, such as, for example, diethylformamide, metalstroyforum or triphenylphosphine, and optionally in the presence of bases, such as, for example, pyridine or triethylamine, at temperatures between -20 and 200oC, preferably between 0 and 150oC.

Substituted phenylmalonamide acid of the formula (XXXIII) is a further object of the present invention. However, you can get a simple manner by known methods (see , for example, Organikim, Ed. VEB Deutscher Verlag der Wissenschaften, Berlin is UP>8
have the above meaning, by saponification.

Required as starting compounds for the method (D) carbonyl compounds of the formula (V) or their simple Millenaire esters of the formula (Va)

< / BR>
< / BR>
where A, D and R8have the above values are trademarks, well-known or can be obtained by known methods.

Getting anhydrides ketonovyh acids of the formula (VI) required as starting substances for implementing the method (D), has already been described in method (D). Thioamides of the formula (VII)

< / BR>
where a has the above meaning, are necessary to implement the method (D) are well known in organic chemistry compounds.

The esters of malonic acids of formula (XXXIV)

< / BR>
where R8X, Y and Z have the abovementioned meanings, are a further object of the present invention and can also be well-known in organic chemistry methods (see, for example, Tetrahedron Lett. 27, 2763 (1986) and Organikim, Ed. VEB Deutscher Verlag der Wissenschaften, Berlin 1977, S. 587 et seq).

Furthermore required as starting substances for the implementation of the methods (E), (G), (H), (I), (K), (L) and (M) galodamadruga acids of the formula (VIII), anhydrides of carboxylic acids formultidisciplinary acid of formula (XI), alkylhalogenide formula (XII), the anhydrides of sulfonic acids of the formula (XIII), phosphorus-containing compounds of the formula (XIV) and metal hydroxides, metal alcoholate, or amines of the formulae (XV) and (XVI) and isocyanates of the formula (XVII) and anhydrides karbinovykh acids of the formula (XVIII) are known compounds of organic or inorganic chemistry.

In addition, the compounds of formula (V), (VII) to (XVIII), (XIX), (XXII), (XXVIII), (XXX), (XXXI), (XXXII), (XXXIII) and (XXXIV) are known from the first patent applications and/or can be obtained listed there ways.

Method (A) differs in that the compounds of formula (I) in which a, b, X, Y, Z, and R8have the above values, are subjected to intramolecular condensation in the presence of a diluent and base.

As diluents in method (A) can be used all organic solvents which are inert to the substances participating in the reaction. Preferably used solvents are hydrocarbons, such as toluene and xylene, ethers such as disutility ether, tetrahydrofuran, dioxane, dimethyl ether glycol and the dimethyl ether of diglycol, moreover polar solvents, such as dimethylsulfoxide, sulfolane, dimethylformamide and butanol.

As reason (deproteinised agents) in the process (A) you can use all the usual acceptors of protons. Preferably used oxides, hydroxides and carbonates of alkali and alkaline earth metals such as sodium hydroxide, potassium hydroxide, magnesium oxide, calcium oxide, sodium carbonate, potassium carbonate and calcium carbonate, which can also be used in the presence of phase transfer catalysts such as, for example, triethylmethylammonium, tetrabutylammonium, Adogen 464 (=methyltrioctylammonium with 8-10 carbon atoms in each alkyl part) or TDA 1 (=Tris-(methoxyethoxymethyl)amine). It is also possible to use alkali metals such as sodium or potassium. In addition, you can use amides and hydrides of alkali and alkaline earth metals, such as sodium amide, sodium hydride and calcium hydride, and alkali metal alcoholate such as sodium methylate, sodium ethylate and tert-butyl potassium.

The reaction temperature in the process (A) may vary within wide limits. Typically operate at temperatures between 0 and 250oC, preferably between 50 and 150oC.

Method (A) is usually carried out at normal pressure.

Method (B) is characterized in that compounds of the formula (III) in which a, b, X, Y, Z, and R8have the above values, are subjected to intramolecular condensation in the presence of a diluent and base.

As diluents in method (B) you can use all organic solvents which are inert with respect to participating in the reaction substances. Preferably used solvents are hydrocarbons, such as toluene and xylene, furthermore, ethers, such as disutility ether, tetrahydrofuran, dioxane, dimethyl ether glycol and the dimethyl ether of diglycol, moreover polar solvents, such as dimethylsulfoxide, sulfolane, dimethylformamide and N-organic. You can also use alcohols, such as methanol, ethanol, propanol, isopropanol, butanol, Isobutanol and tert-butanol.

As reason (deproteinised agents) in the process (B) you can use all the usual acceptors of protons. It is preferable to use oxides, hydroxides and carbonates of alkali and alkaline earth metals such as sodium hydroxide, potassium hydroxide, oxide MAGN the tvii interphase catalysts, such as triethylmethylammonium, tetrabutylammonium, Adogen 464 or TDA 1. It is also possible to use alkali metals such as sodium or potassium. In addition, you can use amides and hydrides of alkali and alkaline earth metals, such as sodium amide, sodium hydride and calcium hydride, and alkali metal alcoholate such as sodium methylate, sodium ethylate and tert-butyl potassium.

The reaction temperature in the process (B) can vary within wide limits. Typically operate at temperatures between 0 and 250oC, preferably between 50 and 150oC.

Method (B) is usually carried out at normal pressure.

In the process (B) components of the reaction formula (III) and deprotonized base is used usually in approximately equimolar amounts. However, you can also use one component in a larger excess (up to 3 mol).

Method (C) characterized in that compounds of the formula (IV) in which a, b, W, X, Y, Z, and R8have the above values, are subjected to intramolecular cyclization in the presence of an acid and optionally in the presence of a diluent.

As diluents in the way () you can use the used solvents are hydrocarbons, such as toluene and xylene, halogenated hydrocarbons such as dichloromethane, chloroform, telengard, chlorobenzene, dichlorobenzene, moreover polar solvents, such as dimethylsulfoxide, sulfolane, dimethylformamide and N-organic. It is also possible to use alcohols such as methanol, ethanol, propanol, isopropanol, butanol, Isobutanol, tert-butanol.

If necessary, a diluent may also be used acid.

As the acids in the method (C) it is possible to use all customary inorganic and organic acids, such as, for example, kaleidostone acid, sulfuric acid, alkyl-, aryl - and halogenated.sulphonated, especially halogenated alkalicarbonate acid, such as, for example, triperoxonane acid.

The reaction temperature in the process (B) may vary within wide limits. Typically operate at temperatures between 0 and 250oC, preferably between 50 and 150oC.

Method (C) is usually carried out at normal pressure.

In the process (In) components of the reaction formula (IV) and acid, for example, are used in equimolar amounts. However, if necessary you can use is of formula (V) or their Millenaire esters of the formula (Va) is subjected to interaction with halogenide ketonovyh acids of the formula (VI), optionally in the presence of a diluent and optionally in the presence of an acid acceptor.

As diluents in the method (G) can be used all organic solvents which are inert with respect to participating in the reaction substances. Preferably used solvents are hydrocarbons, such as o-dichlorobenzene, tetralin, toluene and xylene, furthermore, ethers, such as disutility ether, dimethyl ether glycol and the dimethyl ether of diglycol, moreover polar solvents, such as dimethylsulfoxide, sulfolane, dimethylformamide or N-organic.

As acid acceptors in the process (G), it is possible to use all customary acid acceptors.

Preferably use tertiary amines, such as triethylamine, pyridine, diazabicyclo (DABCO), diazabicyclo (DBU), diazabicyclo (DBN), the base Hunga or N,N-dimethylaniline.

The reaction temperature in the process (G) may vary within wide limits. It is advisable to operate at temperatures between 0 and 250oC, preferably between 50 and 220oC.

Method (D) is preferably carried out at normal pressure.

When carrying out process (G) use the components of the reaction formulas (V) and (VI) and the necessity to the aqueous component in a larger excess (up to 5 mol).

Method (D) is characterized by the fact that the thioamides of the formula (VII) is subjected to interaction with halogenide ketonovyh acid optionally in the presence of a diluent and necessary in the presence of an acid acceptor.

As diluents in method (D) can be used all inert organic solvents. Preferably used solvents are hydrocarbons, such as o-dichlorobenzene, tetralin, toluene and xylene, furthermore, ethers, such as disutility ether, dimethyl ether glycol and the dimethyl ether of diglycol, moreover polar solvents, such as dimethylsulfoxide, sulfolane, dimethylformamide or N-organic.

As acid acceptors in the process (D) it is possible to use all customary acid acceptors.

Preferably use tertiary amines, such as triethylamine, pyridine, DABCO, DBU, DBN, the base Hunga and N,N-dimethylaniline.

The reaction temperature in the process (D) may vary within wide limits. It is advisable to operate at temperatures between 0 and 250oC, preferably between 20 and 220oC.

Method (D) it is better to perform under normal davle acid is used usually in approximately equimolar amounts. However, it is also possible to use one component in a larger excess (up to 5 mol).

Method (E) is characterized by the fact that each of the compounds of formulas from (I-1-a)was added dropwise(I-5-a) is subjected to interaction with halogenide carboxylic acids of the formula (VIII) optionally in the presence of a diluent and optionally in the presence of means connecting the acid.

As diluents in method (E) can be applied all inert towards the acid chlorides of the acids and solvents. Preferably used solvents are hydrocarbons, such as benzine, benzene, toluene, xylene, tetralin, further, halogen-substituted hydrocarbons, such as methylene chloride, chloroform, carbon tetrachloride, chlorobenzene and o-dichlorobenzene, additionally ketones, such as acetone and methylisobutylketone, then, ethers, such as diethyl ether, tetrahydrofuran and dioxane, esters of carboxylic acids, such as ethyl acetate, and also strongly polar solvents, such as dimethylformamide, dimethylsulfoxide and sulfolane. If the resistance to hydrolysis of galodamadruga acid, the interaction can also be carried out in the presence of water.

As Crestline used tertiary amines, such as triethylamine, pyridine, DABCO, DBU, DBN, the base Hunga and N,N-dimethylaniline, furthermore, the oxides of alkaline earth metals, such as magnesium oxide and calcium oxide, moreover, carbonates of alkali and alkaline earth metals such as sodium carbonate, potassium carbonate and calcium carbonate, and hydroxides of alkali metals such as sodium hydroxide and potassium hydroxide.

The reaction temperature in the process (E) may vary within wide limits. In General, operate at temperatures between -20 and +150oC, preferably between 0 and 100oC.

When performing the method (S) of the parent substance of the formulas from (I-1-a)was added dropwise(I-5-a) and galoyanized carboxylic acid of the formula (VIII) used in each case, in General, approximately equimolar amounts. However, you can also use galodamadruga carboxylic acid in a larger excess (up to 5 mol). The treatment is carried out by conventional methods.

Method (E) is characterized in that compounds of the formulas from (I-1-a)was added dropwise(I-5-a) in each case is subjected to interaction with anhydrides of carboxylic acids of the formula (IX) optionally in the presence of a diluent and optionally in the presence of means connecting sour is also respectful when using acid chlorides of the acids. However used in excess of the anhydride of carboxylic acids also can serve as a diluent.

As an added means for binding the acid in the method (E) is preferably used the same ciclofosfamida means, which preferably is also used when applying golodnikov acids.

The reaction temperature in the process (E) may vary within wide limits. In General, operate at temperatures between -20 and +150oC, preferably between 0 and 100oC.

When performing the method (S) of the parent substance of the formulas from (I-1-a) to (I-5-a) and the carboxylic anhydride of the acid of formula (IX) in each case apply, in total, approximately equimolar amounts. However, you can also use the carboxylic acid anhydride in a larger excess (up to 5 mol). The treatment is carried out in the usual way.

In General, the diluent present in excess of the anhydride of carboxylic acid, and the resulting carboxylic acid is removed by distillation or by washing with an organic solvent or water.

Method (F) is characterized by the fact that each of the compounds of formulas from (I-1-a) to (I-5-a) is subjected to interaction with esters of Harborview keys is necessary in the presence of funds linking acid.

As a means of binding acid, in the method (G) use all customary acid acceptors. Mainly used tertiary amines such as triethylamine, pyridine, DABCO, DBU, DBN, the base Hunga and calcium oxide, carbonates of alkali and alkaline earth metals such as sodium carbonate, potassium carbonate and calcium carbonate, and hydroxides of alkali metals such as sodium hydroxide and potassium hydroxide.

As diluents in the way (W), it is possible to use all solvents which are inert towards the esters Harborview acid or esters thiols and Harborview acid. Preferably used solvents are hydrocarbons, such as benzine, benzene, toluene, xylene or tetralin, halogen-substituted hydrocarbons, such as methylene chloride, chloroform, carbon tetrachloride, chlorobenzene and o-chlorobenzene, ketones, such as acetone and methylisobutylketone, ethers, such as diethyl ether, tetrahydrofuran and dioxane, NITRILES, such as acetonitrile, esters of carboxylic acids, such as ethyl acetate, and also strongly polar solvents, such as dimethylformamide, dimethylsulfoxide and sulfolane.

Temperature reactsoC, preferably between 0 and 50oC.

Method (F) is usually carried out at normal pressure.

When carrying out process (G) of the parent substance of the formulas from (I-1-a) to (I-5-a) and the corresponding ether of Harborview acid or the ester thiol and Harborview acid of formula (X), in General, in each case used in approximately equimolar quantities. However, you can also use one component in a larger excess (up to 2 mol). The treatment is carried out in the usual ways. In General, the precipitated salts are removed and the remaining reaction mixture is concentrated by removal of the diluent.

Method (C) is characterized by the fact that each of the compounds of formulas from (I-1-a) to (I-5-a) is subjected to interaction with compounds of the formula (XI) in the presence of a diluent and optionally in the presence of means linking acid (method (C)), or with carbon disulphide and then with alkylhalogenide formula (XII) optionally in the presence of a diluent and optionally in the presence of a base (method (C)).

In the production method of (C) per mole of the parent substance of the formulas from (I-1-a) to (I-5-a) is injected into the reaction of about 1 mole of the ether hormonestimulated acid or ether of chartitemevent Kovalainen optionally diluents used all inert polar organic solvents, such as ethers, amides, sulfones, sulfoxidov and halogenoalkane.

It is preferable to use dimethyl sulfoxide, tetrahydrofuran, dimethylformamide or methylene chloride.

If in the preferred embodiment, by adding a strong deproteinised means, such as, for example, sodium hydride or tert-butyl get potassium enolate compounds of formulas from (I-1-a) to (I-5-a), it is possible to waive additional additives means connecting the acid. If you use the linking acid, they are customary inorganic or organic base, examples of which include sodium hydroxide, sodium carbonate, potassium carbonate, pyridine and triethylamine.

The reaction may be carried out at normal or at elevated pressure, preferably working under normal pressure. The treatment is carried out in the usual way.

In the production method of (C) per mole of each of the starting substances of the formulae (I-1-a) to (I-5-a) add an equimolar amount or an excess of carbon disulphide. While it is preferable to work at temperatures from 0 to 50oAnd especially from 20 to 30oC.

It is often advisable at first and sodium hydride to obtain the corresponding salt. Compounds of formulas (1-1) to (I-5-a), respectively, are subjected to interaction with carbon disulphide until then, until the formation of intermediate compounds, for example, after several hours of stirring at room temperature.

As grounds in method (C) use all the usual acceptors of protons. Preferably used bases are hydrides of alkali metals, alcoholate, alkali metal carbonates or bicarbonates of alkali and alkaline earth metals or nitrogenous bases. It should be called, for example, sodium hydride, sodium methylate, sodium hydroxide, calcium hydroxide, potassium carbonate, sodium bicarbonate, triethylamine, dibenzylamine, Diisopropylamine, pyridine, quinoline, DABCO, DBN and DBU.

As diluents in this way you can use all the usual solvents.

Preferably used solvents are aromatic hydrocarbons, such as benzene or toluene, alcohols, such as methanol, ethanol, isopropanol or ethylene glycol, NITRILES, such as acetonitrile, ethers, such as tetrahydrofuran or dioxane, amides, such as dimethylformamide, or other polar solvents, such as dimethyldodecylamine at a temperature from 0 to 70oAnd especially from 20 to 50oC. While introducing the reaction of at least equimolar amount of alkylhalogenide.

The process is carried out at normal or at elevated pressure, preferably under normal pressure.

The treatment is carried out in the usual way.

Method (S) characterized in that each of the compounds of formulas from (I-1-a) to (I-5-a) is subjected to interaction with anhydrides of sulfonic acids of the formula (XIII) optionally in the presence of a diluent and optionally in the presence of means connecting the acid.

In the production method of (I) per mole of each of the source materials of formulas from (I-1-a) to (I-5-a) is injected into the reaction of about 1 mole of sulfonic acid chloride of formula (XIII) at a temperature of from -20 to 150oC, preferably from 20 to 70oC.

Method (S) carried out preferably in the presence of a diluent.

As diluents used all inert polar organic solvents, such as ethers, amides, ketones, esters, carboxylic acids, NITRILES, sulfones, sulfoxidov or halogen-substituted hydrocarbons, such as methylene chloride.

It is preferable to use dimethyl sulfoxide, tetrahydrofuran, Ÿ strong deproteinised tools (such as, for example, sodium hydride or tert-butyl potassium) get enolate compounds of formulas from (I-1-a) to (I-5-a), it is possible to waive additional additives means connecting the acid.

If you use the linking acid, they are customary inorganic or organic bases; for example, include sodium hydroxide, sodium carbonate, potassium carbonate, pyridine and triethylamine.

The reaction may be carried out at normal or at elevated pressure, preferably working under normal pressure. The treatment is carried out in the usual way.

Method (C) is characterized by the fact that each of the compounds of formulas from (I-1-a) to (I-5-a) is subjected to interaction with phosphorus compounds of the formula (XIV) optionally in the presence of a diluent and optionally in the presence of means connecting the acid.

For the synthesis of compounds of formulas from (I-1-a) to (I-5-a) according to the method of (K) 1 mol of these compounds is introduced into the reaction from 1 to 2, preferably from 1 to 1.3 mol of the phosphorus-containing compound of the formula (XIV) at temperatures between -40 and 150oWith, preferably between -10 and 110oC.

Method (C) is preferably carried out in the presence of a diluent.

Preferably use acetonitrile, dimethyl sulfoxide, tetrahydrofuran, dimethylformamide, methylene chloride.

As added if necessary, means for binding the acid is used usual inorganic or organic bases, such as hydroxides, carbonates or amines. For example, include sodium hydroxide, sodium carbonate, potassium carbonate, pyridine and triethylamine.

The interaction can be carried out at normal or at elevated pressure, preferably working under normal pressure. The treatment is carried out by conventional methods customary in organic chemistry. The end products are preferably purified by crystallization, chromatographic methods or by the so-called "distillation", that is, by removing the volatile components in vacuo.

Method (L) is characterized by the fact that each of the compounds of formulas from (I-1-a) to (I-5-a) is subjected to interaction with metal hydroxides or alkoxides of the metals of the formula (XV) or amines of the formula (XVI), if necessary in the presence of a diluent.

As diluents in spacebirdy, such as methanol, ethanol, isopropanol, and water. Method (L) is in General carried out at normal pressure. The reaction temperature is, in General, is between -20 and 100oC, preferably between 0 and 50oC.

Method (M) is characterized by the fact that each of the compounds of formulas from (I-1-a) to (I-5-a) is subjected to interaction with compounds of the formula (XVII), if necessary in the presence of a diluent and optionally in the presence of a catalyst (method M) or with compounds of the formula (XVIII) if necessary in the presence of a diluent and optionally in the presence of means linking acid (method M).

In the method of obtaining (M) for each mol of the parent substance of the formulas from (I-1-a) to (I-5-a) is injected into the reaction, about 1 mol of isocyanate of the formula (XVII) at a temperature of from 0 to 100oC, preferably from 20 to 50oC.

Method (M) is preferably carried out in the presence of a diluent.

As diluents used all inert organic solvents, such as aromatic hydrocarbons, halogenated hydrocarbons, ethers, amides, NITRILES, sulfones or sulfoxidov.

To accelerate the reaction if necessary, you can add catalysts. As a researcher who tilelander.

The method is preferably carried out at normal pressure.

In the method of obtaining (M) per mole of starting compound of formulas (I-1-a) to (I-5-a) is injected into the reaction of about 1 mole of acid chloride of carbamino acid of formula (XVIII) at a temperature of from 0 to 150oC, preferably from 20 to 70oC.

As an added optionally diluents used all inert polar organic solvents, such as ethers, esters, carboxylic acids, NITRILES, ketones, amides, sulfones, sulfoxidov or halogen-substituted hydrocarbons.

It is preferable to use dimethyl sulfoxide, tetrahydrofuran, dimethylformamide or methylene chloride.

If in the preferred embodiment, by adding a strong deproteinised tools (such as sodium hydride or tert-butyl potassium) get enolate compounds of formulas from (I-1-a) to (I-5-a), it is possible to waive additional additives means connecting the acid.

If you use the linking acid, they are customary inorganic or organic bases, of which examples include sodium hydroxide, sodium carbonate, potassium carbonate, preferably operate at normal pressure. The treatment is carried out in the usual way.

Biologically active substances are suitable for combating animal pests, preferably insects and arachnids, encountered in agriculture, in forests, in the storage of inventory and raw materials.

They are effective against species with normal sensitivity and against resistant species and against all or individual stages of development. The abovementioned pests include:

From a number of the Isopoda, for example Oniscus asellus, Armadillidium vulgare, Porcellio scaber.

From a number of the Diplopoda, for example Blaniulus guttulatus.

From a number of the Chilopoda, for example, Geophillus carpophagus, type Scutigera.

From a number of the Symphyla, for example, Scutigirella immaculata.

From a number of the Thysanura, for example Lepisma saccharina.

From a number of Collembola, for example Onychiurus armatus.

From a number of Orthoptera, for example Blatta orientalis, Periplaneta americana, Leucophaea maderae, Blattella germanica, Acheta domesticus, views Gryllotalpa, Locusta migratoria, migratorioides, Melanoplus differentialis, Schistocerca gregaria.

From a number of the Dermaptera, for example Forficula auricularia.

From a number of the Isoptera, for example Reticulitermes species.

From a number of the Anoplura, for example Phylloxera vastatrix, type Pemphigus, Pediculus hymanus corporis, species: Haematopinus, Linognathus.

From a number of Mallophaga, for example, species: Trichodectes, Damalinea.

From a number of the Homoptera, for example, Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Doralis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Macrosiphum avenae, species Myzus, Phorodon humuli, Rhopalosiphum padi, type Empoasca, Euscelis bilobatus, Nethotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, species: Pseudococcus, Psylla.

Of a number of Lepidoptera, for example, Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletis blancardella, Hyponomeuta padella, Plutella maculipennis, Malacosuma neustria, Euproctis chrysorrhoea, type Lymantria, Bucculatrix thurberiella, Phyllocnistis citrella, species: Agrotis, Euxoa, Feltia; Earias insolana, type Heliothis, Spodoptera exigua, Mamestra brassicae, Panolis flammea, Prodenia litura, Spodoptera species, Trichuplusia ni, Caprocapsa pomonella, Pieris species, Chilo; Pyrausta nobilalis, Ephestia kuehniella, Galleria mellonella, Tineola bisselliella, Tinea pellionella, Hofmannophila pseudospretella, Cacoecia podana, Capua reticulana, Choristoneura fumiferana, Clysia ambiguella, Homona magnanima, Tortrix veridana.

From a number of Coleoptera, for example, Anobium punctatum, Rhizopertha dominica, Acanthoscelides obtectus, Hylotrupes bajulus, Aelastica ani, Leptinotarsa decemlineata, Phaedon cochleariae, Diabrotica species, Psylliodes chrysocephala, Epilachna varivestis, type Atomaria, Oryzaephilus surinamensis, species: Anthonomus sitophilus; Otiorrhynchus sulcatus, Cosmopolites sordidus, Ceuthorrhynchus assimilis, Hypera postica, species: Dermestes, Trogoderma, Anthrenus, Attagenus, Lyctus; Meligethes aeneus, type Ptinus, Niptus hololeucus, Gibbium psylloides, Tribolium species, Tenebrio molitor, a species, Agriotes, Cono derus; Melolontha melolontha, Amphimallon solsti tialis, Costelytra zealandica.

From a number of Hymenoptera, for example, in the water: Musca, Fannia; Calliphora erithrocephala, species: Lucilia, Chrysomyia, Cuterebra, Gastrophilus, Hyppobosca, Stomoxys, Oestrus, Hypoderma, Tabanus, Tannea; Bibio hortulanus, Oscinella frit, type Phorbea, Pegomyia hyoscyami, Ceratites capitata, Dacus oleae, Tipula paludosa.

From a number of the Siphonaptera, for example Xenopsylla cheopis, type Ceratophyllus.

From a number of the Arachnida, for example Scorpio maurus, Latrodectus mactans.

From a number of Acarina, for example Acarus siro, species: Argas, Ornithodoros; Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, species: Boophilus, Rhipicephalus, Amblyomma, Hyalomma, Ixodes, Psoroptes, Chorioptes, Sarcoptes, Tarsonemus; Bryobia praetiosa, species: Panonychus, Tetranychus.

Biologically active substances according to the invention have a high insecticidal and acaricidal activity.

Particularly successful they can be used to control insect pests of plants, such as, for example, against the larvae of the beetle pest of leaves horseradish (Phaedon cochleariae) or against the larvae of the green rice cicadas (Nephotettix cincticeps) or against the larvae of cabbage cockroach (Plutella maculipennis).

Biologically active substances can be included in the conventional compositions, such as solutions, emulsions, wettable powders, suspensions, powders, pulverized tools, pastes, soluble powders, granules, suspension-emulsion concentrates, impregnated with biologically active substances of natural and synthetic materials, and takrima by mixing the biologically active substances, fillers, therefore, liquid solvents and/or solid carriers, optionally with the use of surface-active substances, therefore, emulsifiers and/or dispersants and/or foam.

When used as filler water as an auxiliary for dissolving means can for example also be used organic solvents. As liquid solvents are used, in the main, aromatic hydrocarbons, such as xylene, toluene or alkylnaphthalenes, chlorine substituted aromatic and chlorine substituted aliphatic hydrocarbons, such as chlorobenzene, chloroethylene or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example petroleum fractions, mineral and vegetable oils, alcohols, such as butanol or glycol and also their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethylformamide and dimethylsulfoxide, and water.

As solid carriers used, for example, ammonium salts and natural stone flour as kaolin, alumina, talc, chalk, quartz, attapulgite, montmorillonite or duty; as solid carriers for granules are used, for example, crushed and fractionated natural rocks such as calcite, marble, pumice, thick, dolomite, and also synthetic granules of inorganic and organic powder, and granules of organic material such as sawdust, coconut shell, corn cobs and stalks of tobacco; as emulsifiers and/or foaming agents are used, for example, nonionic and anionic emulsifiers, such as esters of polyoxyethylene and fatty acids, ethers of polyoxyethylene and fatty alcohols, for example alkylarylsulphonate ethers, alkyl sulphonates, the alkyl sulphates, arylsulfonate, and also protein hydrolysates; as dispersing agents are used, for example, ligninsulfonate waste liquors and methylcellulose.

The compositions can be used substances to enhance the adhesion, such as carboxymethylcellulose, natural and synthetic powdered, granular, or Latecoere polymers, such as gum Arabic, polyvinyl alcohol, polyvinyl acetate, and also natural phospholipids, such as Catalina and lecithins, and synthetic phospholipids. To copulate dyes, such as inorganic pigments, for example iron oxide, titanium dioxide, ferrocyanide blue, and organic dyestuffs, such as alizarin dyes, azo dyes, metal-containing phthalocyanine dyes, and trace elements such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.

Typically, the compositions contain a biologically active substance in amounts of between 0.1 and 95 wt. %, preferably between 0.5 and 90 wt. %.

The biologically active substance according to the invention in their trademark songs, and in the prepared from these compositions forms of application can be mixed with other biologically active substances such as insecticides, baits, sterilizing agents, acaricides, nematicides, fungicides, nutrients, growth regulators or herbicides. The insecticides include, for example, phosphoric esters, carbamates, esters of carboxylic acids, chlorine substituted hydrocarbons, prilocaine, substances produced by microorganisms, and others.

Especially beneficial components in mixtures are, for example, the following:

Insecticides/Acaricides:

the abamectin, AC 303 630, Arafat, acrinathrin, alankar, aldicarb, alphamethrin, the b, bensultap, betacellulin, bifenthrin, VRMS, papenbrock, bromophos And, bofenkamp, buprofezin, butocarboxim, butylparaben, cadusafos, carbaryl, carbofuran, carbophenothion, carbosulfan, cartap, CGA 157419, CGA 184699, caretakers, chlorethoxyfos, Chlorfenvinphos, chlorfluazuron, chlormephos, chlorpyrifos, chlorpyrifos M, CIS-resmethrin, claritin, clofentezine, cyanophos, cicloprofen, cyfluthrin, cyhalothrin, cyhexatin, cypermethrin, cyromazine, deltamethrin, demeton M, demeton S, demeton-S-methyl, diafenthiuron, diazinon, dichlofenthion, dichlorvos, declivous, dicrotophos, diation, diflubenzuron, dimethoate, dimethylene, dioxathion, disulfoton, edifenphos, emamectin, esfenvalerate, ethiofencarb, ation, etofenprox, ethoprophos, etrimfos, fenamiphos, fenazaquin, fenbutatin, fenitrothion, fenobucarb, fanatical, fenoxycarb, fenpropathrin, feneral, fenpyroximate, fenthion, fenvalerate, fipronil, fluazinam, flucycloxuron, flucythrinate, flufenoxuron, flavandiols, fluvalinate, fonofos, formation, fosthiazate, tupfenrock, furathiocarb, HCH, heptenophos, hexaflumuron, hexythiazox, Imidacloprid, iprobenfos, isazofos, isofenphos, isoprocarb, isoxathion, ivemectin, Lamda-cyhalothrin, lufenuron, Malathion, mecarbam, mevinphos, mesotopos, moxidectin, naled, NC 184, NI 25, nitenpyram, omethoate, oxamyl, oxydemeton M, oxidation, parathion And parathion M, permethrin, pentat, Fort, fosalan, phosmet, phosphamidon, phoxim, pirimicarb, pirimiphos M, primiphos And, profenofos, promecarb, propafol, propoxur, prothiofos, procoat, pymetrozine, pyraclofos, peradventure, prismatron, feverfew, pyridaben, pyrimidifen, pyriproxifen, finalpos, RH 5992, salicion, sabots, selflove, sulfotep, sulprofos, tebufenozide, tebufenpyrad, tebupirimfos, teflubenzuron, tefluthrin, temephos, terram, terbufos, tetrachlorvinphos, titanox, thiodicarb, thiofanox, thiometon, thionazin, thuringiensis, tralomethrin, triuralin, triazophos, treasure, trichlorfon, triflumuron, trimeter, validation, CMS, killchar, YI 5301/5302, catameran.

In addition, the biologically active substance in his trademark songs, and in the prepared from these compositions forms of application may be in a mixture with synergists. The synergists are compounds that enhance the effectiveness of biologically active substances, thus he added synergist may not be biologically active.

The content of biologically active substances in the forms of application of the active substances in application forms can be from 0.0000001 to 95 wt. %, preferably from 0.0001 to 1 wt. %.

Application carried out in the usual way, adapted to the application forms.

When applied against household pests, and storage pests biologically active substance has an excellent residual effect on wood and clay, as well as high stability against alkali Izvestkovaya grounds.

Biologically active substances according to the invention act not only against plant pests, household pests, and storage pests, but also in the field of veterinary medicine against animal parasites (ectoparasites), such as pasture mites, argasid, cestocide mites, krasnoselka, flies (stinging and licking), parasitic larvae of flies, lice, ect., hematophagous biting and fleas. These parasites include:

From a number Anoplurida, for example, species: Haematopinus, Linognathus, Pediculus, Phtirus, Solenopotes.

From a number Mallophagida and contracts Amblycerina and Ischnocerina, for example, species: Trimenopon, Menopon, Trinoton, Bovicola, Werneckiella, Lepikentron, Damalina, Trichodectes, Felicola.

From a number of Diptera and contracts Nematocerina and Brachycerina, for example, species: Aedes, Anopheles, Culex, Simulium, Eusimulium, Phlebotomus, Lutzomyia, Culicoides, Chrysops, H., Atylotus, Tabanus, Haematopota, Philipomyia, Braula, Musca, Hydrotaea, Stomoxys, Haematobia, Morellia, Fannia, G is er, species: Pulex, Ctenocephalides, Xenopsylla, Ceratophyllus.

From a number Heteropterida, for example, species: Cimex, Triatoma, Rhodnius, Panstrongylus.

From a number Blattarida, for example, Blatta orientalis, Periplaneta americana, Blattela germanica, type Supella.

From the subclass of the Acaria (Acarida) and from the ranks of the Meta-and Mesostigmata, for example, species: Argas, Ornithodorus, Otabius, Ixodes, Amblyomma, Boophilus, Dermacentor, Haemaphysalis, Hyalomma, Rhipicephalus, Dermanyssus, Raillietia, Pneumonyssus, Sternostoma, Varroa.

From a number of the Actinedida (Prostigmata) and Acaridida (Astigmata), for example, species: Acarapis, Cheyletiella, Ornithocheyletia, Myobia, Psorergates, Demodex, Trombicula, Listrophorus, Acarus, Tyrophagus, Caloglyphus, Hypodectes, Pterolichus, Psoroptes, Chorioptes, Otodectes, Sarcoptes, Notoedres, Knemidocoptes, Cytodites, Laminosioptes.

For example, they exhibit a high activity against Boophilus microplus and Lucilia cuprina.

Biologically active substances of the formula (I) according to the invention are also suitable for combating arthropods that affect farm animals, such as cattle, sheep, goats, horses, pigs, donkeys, camels, Buffalo, rabbits, chickens, turkeys, ducks, geese, bees, other domestic animals such as dogs, cats, pet birds, aquarium fish and so-called experimental animals such as hamsters, Guinea pigs, rats and mice. By destroying these arthropods can contribute to, the food and so on), so thanks to the use of biologically active substances is possible more economical and simpler animal keeping.

The use of biologically active substances according to the invention in veterinary medicine is carried out in a known manner by enteral administration in the form of, for example, tablets, capsules, medicines, injections, granules, pastes, boluses, through food, in the form of suppositories, by parentline introduction, as, for example, by injections (intramuscularly, subcutaneously, intravenously, intraperitoneally, etc.), vaccinations, by entering through the nose, exposure through the skin, for example, by dipping or bathing (makanya), spraying (spray), pouring, washing, audriana, and by containing the biologically active substance of shaped articles such as collars, ear marks, tail marks, bandages on the legs, clamps, fixtures for marking and so on.

For livestock, poultry, Pets and so on biologically active substances of the formula (I) can be applied as formulations (for example powders, emulsions, liquid funds) containing these substances in quantities of from 1 to 80 wt. % directly or after 100-10000 times Rabaul the organisations of the formula (I) exhibit high insecticidal activity against insects, destructive technical materials.

As an example, and preferably, but without limitation, the following list should include the following insects:

Beetles, such as Hylotrupes bajulus, Chlorophorus pilosis, Anobium punctatum, Xestobium rufovillosum, Ptilinus pecticornis, Dendrobium pertinex, Ernobius mollis, Priobium carpini, Lyctus brunneus, Lyctus africanus, Lyctus planicollis, Lyctus linearis, Lyctus pubescens, Trogoxylon aequale, Minthes rugicollis, Xyleborus, type Tryptodendron, type Apate monachus, Bostrychus capucins, Heterobostrychus brunneus, Sinoxylon, type Dinoderus minutus.

Hymenopterans, such as

Sirex juvencus, Urocerus gigas, Urocerus gigas taignus, Urocerus augur.

Termites, such as

Kalotermes flavicollis, Cryptotermes brevis, Heterotermes indicola, Reticulitermes flavipes, Reticulitermes santonensis, Reticulitermes lucifugus, Mastotermes darwiniensis, Zootermopsis nevadensis, Coptotermes formosanus.

Seinajoki, such as

Lepisma saccharina.

In this context, the technical materials should be understood primarily plastics, adhesives, glues, paper and cardboard, leather, wood and products of its processing and coating materials.

Highly preferably, when in the case protected from damage by insects of the material we are talking about wood and its processing products.

Under the wood and its processing products, which can be protected by using sledstvennye beams, railway sleepers, parts of bridges, quay bridges, wooden vehicles, boxes, racks, containers, telephone poles, wood paneling, wooden Windows and doors, plywood, chipboard, joinery products or wood products, which, in General, are used in the construction of houses or in the carpentry business.

Biologically active substances can be applied as such, in the form of concentrates or generally known conventional compositions, such as powders, granulates, solutions, suspensions, emulsions or pastes.

These compositions can be obtained by themselves, in a known manner, for example by mixing the biologically active substances, at least one solvent or diluent, emulsifier, dispersant and/or binder or fixing agent, water repellent, if necessary, with siccatives and UV stabilizers and, if necessary, dyes and pigments, as well as other subsidiary in the preparation of substances.

Insecticidal preparations or concentrates used to protect wood and wood-based materials, contain biologically active substance according yamago funds or concentrate depends on the type and availability of insects and the environment. Optimal the amount used in each case can be established using a number of tests. In General, however, it is enough to apply the biologically active substance in amounts of from 0.0001 to 20 wt. %, preferably from 0.001 to 10 wt. % (based on the protected material.

Solvent and/or diluent is an organic solvent or mixture of solvents, and/or oily or oily volatile ingredients organic solvent or mixture of solvents, and/or a polar organic solvent or mixture of solvents and/or water and, if necessary, an emulsifier and/or wetting.

As organic solvents mainly use oily or oily solvents factor volatility over 35 and a flash point above 45oC. as such volatile ingredients of water-insoluble oily and oily solvents use appropriate mineral oils or their fractions of aromatic hydrocarbons, or solvent mixtures containing mineral oils, preferably BitSpirit, kerosene and/or alkylbenzene.

Successfully used mineral oil, boiling in the range of from 170 to 220othe, erosin or aromatic hydrocarbons, boiling in the range from 160 to 280oWith, turpentine and the like.

Preferably use a liquid aliphatic hydrocarbon boiling in the range from 180 to 210oWith, or high-boiling mixtures of aromatic and aliphatic hydrocarbons, boiling in the range from 180 to 220oWith, and/or spun oil and/or monochromator, preferably monochromation.

Organic volatile ingredients oily or oily solvents factor volatility over 35 and a flash point above 30oC, preferably above 45oWith, can be partially replaced easily or srednekamsky organic solvents provided that the solvent mixture also will have a coefficient of volatility over 35 and a flash point above 30oC, preferably above 45oWith, and that insecticide-fungicide mixture will dissolve or emulgirovanija in this solvent mixture.

In a preferred embodiment, the portion of the organic solvent or solvent mixture is replaced by an aliphatic polar organic solvent or mixture of solvents. Preferably used as Rostova ether, such as, for example, a simple glycol ethers, esters and the like.

As organic binders in this invention use themselves known, diluted with water and/or soluble or dispersible or emulsifiable in the applicable organic solvents, synthetic resins and/or binding drying oils, in particular binders composed of or containing acrylic resin, vinyl resin such as polyvinyl acetate, resin-based complex polyester obtained by polycondensation or polyaddition resin, polyurethane resin, alkyd resin or modified alkyd resin, phenolic resin, hydrocarbon resin, as inden-coumarone resin, silicone resin, drying vegetable and/or drying oils and/or physically drying binders based on natural and/or synthetic resin.

Used as a binder resin may be in the form of an emulsion, dispersion or solution. As binders can also be used bitumen or bituminous substances in an amount up to 10 wt. %. Additionally, you can use themselves known classication tools and the like.

According to the invention is preferably in the tool or in the concentrate as the organic binder contains at least one alkyd resin or modified alkyd resin and/or one-drying vegetable oil. According to the invention preferably use an alkyd resin with an oil content of more than 45 wt. %, preferably from 50 to 68 wt. %.

Mentioned binder may be completely or partially replaced by a fixative (mixture) or a plasticizer (mixture). These additives shall prevent the volatilization of biologically active substances, as well as crystallization or precipitation. It is preferable to replace from 0.01 to 30% binder (considering 100% of the used binder).

Plasticizers belong to the chemical classes of esters of phthalic acid such as dibutyl phthalate, dioctylphthalate or benzylbutylphthalate, phosphoric esters such as tributyl phosphate, esters of adipic acid, such as di(2-ethylhexyl)adipate, stearates, such as butilstearat or amistart, oleates, such as butylurea, ethers of glycerol or macromolecular simple glycol ethers, esters of glycerol and esters of p-naprimer, as polivinilbutilovy ether, or ketones, such as benzophenone, atelevision.

As solvents or diluents in particular use water, if necessary, in a mixture with one or more of the abovementioned organic solvents or diluents, emulsifiers and dispersants.

Especially effective wood protection is achieved through the application of industrial methods of impregnation, for example vacuum, double vacuum or under pressure.

Ready-to-use tools, if necessary, may contain additional insecticides and, if necessary, one or more fungicides.

As a further addition to the mixtures preferably used insecticides and fungicides mentioned in the international application WO 94/29-268. Compounds named in this document are part of this application.

In highly preferred additives to the mixtures can be insecticides, such as chlorpyrifos, phoxim, selfloathing, alphamethrin, cyfluthrin, cypermethrin, deltamethrin, permethrin, Imidacloprid, NI-25, flufenoxuron and triflumuron, and also fungicides, such as epoxyconazole, gleaned, 3-iodine-2-propynylbutylcarbamate, n-octyl-isothiazolin-3-one and 4,5-dichloro-M-acterization-3-one.

Preparation and application of biologically active substances according to the invention is shown in the following examples that use the following abbreviations:

i = ISO-structure

s = vtorichnyi

t = tertiary

dec = decomposition

C = cyclo

Examples of making

Example I-1-a-1

< / BR>
To a solution of 18.5 g (0,165 mol) of potassium tert-butylate in 57 ml of anhydrous tetrahydrofuran at the boiling under reflux was added dropwise a solution of 25.0 g (0,072 mol) of the compound according to example (II-2) in 150 ml of anhydrous toluene and stirred for one and a half hours while boiling under reflux. To handle add 220 ml of water, separating the aqueous phase is extracted with toluene phase with 110 ml of water, the aqueous phase is combined, washed them toluene and at a temperature of from 10 to 20oWith acidified with approximately 26 ml of concentrated hydrochloric acid. The product is filtered under vacuum, washed, dried and washed by stirring in a mixture of methyl tert-butyl ether n-hexane.

Yield: 18.0 g (79% of theoretically calculated amount); the temperature has been melted down is given the following compounds of formula (I-1-a) (see table. 1).

Example I-1-b-1

< / BR>
4.5 g (0.015 mol) of the compound according to example I-1-a-1 and 2.1 ml (15 mmol) of triethylamine in 70 ml of absolute methylene chloride at a temperature of from 0 to 10oWith mixed with 1.13 ml (0.015 mol) of acetylchloride in 5 ml of absolute methylene chloride. Stirred at room temperature until such time as according to the control by means of thin layer chromatography, the reaction is completed. To process washed twice with 50 ml of 0.5 n sodium hydroxide solution, dried over magnesium sulfate and evaporated. The crude product is recrystallized from a mixture of methyl tert-butyl ether n-hexane.

Yield: 3.4 g (66% of theoretically calculated amount); melting point: 209oC.

Similarly, respectively, according to the above General data synthesis given the following compounds of formula (I-1-b) (see tab. 2).

Example (I-1-b-1)

< / BR>
To 4.5 g (0.015 mol) of the compound according to example I-1-a-1 and 2.1 ml of triethylamine in 70 ml of absolute methylene chloride at a temperature of from 0 to 10oWith added dropwise a solution of 1.5 ml (15 mmol) of the ethyl ether of Harborview acid in 5 ml of absolute methylene chloride and stirred at room temperature until such time as compliance by using 50 ml of 0.5 N. the sodium hydroxide solution, dried over magnesium sulfate and evaporated.

Output: 3,3 g (59% of theoretically calculated amount); melting point: 193oC.

Similarly, respectively, according to the above General data synthesis given the following compounds of formula (I-1) (see tab. 3).

Example I-1-g-1

< / BR>
1.2 ml of triethylamine are added to a solution of 2.0 g (6.3 mmol) of the compound according to example I-1-a-2, dissolved in 40 ml of methylene chloride. of 0.53 ml methanesulfonanilide, dissolved in a small amount of methylene chloride, is added to the reaction mixture, cooled in an ice bath. Then the reaction mixture allowed to warm, stirred at room temperature for 2 hours, then add 0.1 ml of methanesulfonanilide. The reaction mixture was stirred at room temperature overnight and further at a temperature of 40oWith in an hour. The reaction mixture is processed by washing with 10% by weight citric acid solution and the aqueous phase is extracted with methylene chloride. The combined organic phase is twice washed with 1 N. solution of sodium hydroxide. The resulting aqueous phase is extracted with methylene chloride and all get CLASS="ptx2">

1H-NMR(400 MHz. MCOd6):

=1,45-2,05 (m, 8H, cyclohexyl-H)

2.09 (s, 3H, aryl-CH3)

to 2.18(s, 3H, aryl-CH3)

2.20(s, 3H, aryl-CH3)

2.86 (s, 3H, O2N-CH3)

< / BR>
of 3.27 (s, 3H, och3)

6.89 (s, 1H, aryl-H)

7.03 (s, 1H, aryl-H)

9.08 (s, 1H, N-H)

Example II-1

< / BR>
To 30,3 g (0,308 mol) of concentrated sulfuric acid at a temperature of from 30 to 40oWith carefully added dropwise a solution of 17.5 g of compound according to example II-66 approximately 100 ml of methylene chloride and stirred for two hours at this temperature. Then added dropwise 41 ml of absolute methanol so that the internal temperature was maintained approximately 40oC, and stirred for 6 hours at a temperature of from 40 to 70oC.

The reaction mixture is processed due to the fact that poured 0.29 kg of ice, extracted with methylene chloride, washed with aqueous sodium hydrogen carbonate solution, dried and evaporated. The crude product is purified by column chromatography on silica gel using a mixture of methylene chloride with ethyl acetate in the ratio of 2:1 as additionally separated by.

Yield: 13.1 g (67% of theoretically calculated amount); melting point: 147oC.

Example II-2
is their thirty minutes at room temperature and then at a temperature of 50oWith until the cessation of gas evolution. Excess thionyl chloride is removed under vacuum at a temperature of 50oWith, then add 50 ml of absolute toluene and again evaporated. The residue is dissolved in 100 ml of absolute tetrahydrofuran (solution 1).

To a solution of 47.9 g of methyl ester of CIS-4-methylcyclohexylamine-1-carboxylic acid and a 64.6 ml (0,460 mol) of triethylamine in 600 ml of absolute tetrahydrofuran at a temperature of from 0 to 10oWith added dropwise a solution of 1, and then stirred for one hour at room temperature. Then filtered under vacuum, washed with absolute tetrahydrofuran and evaporated. The residue is dissolved in methylene chloride, washed with a 0.5 N. hydrochloric acid, dried and evaporated. The crude product is purified by column chromatography on silica gel using a mixture of methylene chloride with ethyl acetate in the ratio of 7:1.

Yield: 25 g (32% of theoretically calculated amount); melting point: 158oC.

Analogously to examples II-1 and II-2 and according to the above General data synthesis given the following compounds of formula (II) (see tab. 4).

< / BR>
Example II-77

< / BR>
On the basis of 17.8 g of 2,4,5-trimethylpentane acid according to met the slots (70%) and 16.8 ml (0.12 mol) of triethylamine in 150 ml of absolute tetrahydrofuran at a temperature of from 0 to 10oWith added dropwise a solution of 1 and stirred for one hour at room temperature. Then the reaction mixture is evaporated and the residue is dissolved in methylene chloride, washed with a 0.5 N. hydrochloric acid, dried and evaporated. The crude product is recrystallized from a mixture of methyl tert-butyl ether n-hexane.

Yield: 17.5 g (61% of theoretically calculated amount); melting point: 156oC.

Example I-2-a-1

< / BR>
8,42 g (75 mmol) of potassium tert-butylate bring in 50 ml of dimethylformamide, at a temperature of from 0 to 10oWith added dropwise a solution of 16.6 g (50 mmol) 1-ethoxycarbonylmethyl ester 2,4,5-trimethylpentane acid obtained according to example III-1, in 50 ml of dimethylformamide and stirred overnight at room temperature.

For processing the reaction mixture was added dropwise to 500 ml ice 1 N. hydrochloric acid, precipitated precipitated product is filtered under vacuum, washed with water and dried in a vacuum drying Cabinet. For further purification the crude product is boiled in a mixture of n-hexane with acetone.

Yield: 9.2 grams (64% of theoretically calculated amount); melting point: from 209 to 212oC.

table. 5).

Example I-2-b-1

< / BR>
2.86 g (10 mmol) of the compound according to example 1-2-a-1 contribute in 40 ml of methylene chloride, added 1.52 g (15 mmol) of triethylamine under ice cooling was added dropwise a solution of 1.57 g (13 mmol) of pualeilani in 40 ml of dichloromethane and additionally stirred for one to two hours at room temperature.

For processing sequentially washed with 10% citric acid, 1 n sodium hydroxide solution and sodium chloride solution, the organic phase is dried over magnesium sulfate and evaporated. The crude product to further purification mix even with a small amount of petroleum ether.

Yield: 3.0 g (81% of theoretically calculated amount); melting point: from 128 to 132oC.

Similarly, respectively, according to the above General data synthesis given the following compounds of formula (I-2-b) (see tab. 6).

Example I-2-in-1

< / BR>
0.55 g (5.5 mmol) of triethylamine are added to a solution 1,58 g (5 mmol) of the compound according to example I-2-a-3 in 30 ml of methylene chloride. At a temperature of 0 to 10oTo add to 0.78 g (5 mmol) of phenylcarbamate. The resulting reaction mixture is stirred over night at room those who authorized the pressure. Get 1,60 g (73% of theory) of the desired product in the form of butter.

1H-NMR (CDCl3): or =1.5-2-3 (m, 17H), 3,25/a 3.6 (m, 1H), 3,3/3,4 (s, 3H), 6,95-7,05 (m, 2H), and 7.3 (m, 5H).

Analogously to example 1-2-in-1 or above shared data on the synthesis got more compounds of formula 1-2, are given in table. 7.

Example I-2-g-1

< / BR>
0.55 g (5.5 mmol) of triethylamine are added to a solution 1,58 g (5 mmol) of the compound according to example I-2-a-3 in 30 ml of methylene chloride. At a temperature of 0 to 10oTo add 0,57 g (5 mmol) of methanesulfonamide. The resulting reaction mixture is stirred over night at room temperature, washed with 1 N. aqueous hydrochloric acid and 1 N. solution of sodium hydroxide, dried and concentrated under reduced pressure. Obtain 1.50 g (76% of theory) of the desired product in the form of butter.

1H-NMR(CDCl3): or =1.5 to 2.3 (m, 17 H); 2,55/to 2.65 (s, 3H); 3,25/a 3.6 (m, 1H); 3,3/3,4 (s, 3H); 6,95-7,05 (m, 2H).

Similarly, the example I-2-g-1 or above shared data on the synthesis receive the compounds of formula (I-2-g), given in the table. 8.

Analogously to example I-2-b-1 or above shared data on the synthesis receive the compounds of formula I-2-d, are given in table. 9.

Similarly to the above General data on the synthesis recip is on and spatula databaseconnect added to a solution of 0.47 g (1.48 mmol) of the compound according to example I-2-a-3 in 30 ml of methylene chloride. At a temperature of 0 to 10oTo add drops to 0.23 g (1.48 mmol) of N-(chlorocarbonyl)of the research. Then the reaction mixture was stirred at room temperature overnight, then partitioned between water and methylene chloride, the organic layer is separated, dried and concentrated under reduced pressure. The resulting crude product is mixed with petroleum ether, sucked off and dried. Obtain 0.24 g (38% of theory) of the target product with so pl. 143oC.

Example III-1

< / BR>
of 8.9 g (50 mmol) of 2,4,5-trimethylpentane acids contribute in 50 ml of toluene, added 11.9 g (100 mmol) of thionyl chloride, stirred at a temperature of 80oWith up to stop shedding chloride and evaporated. The crude acid chloride acid together with 8.6 g (50 mmol) of ethyl ester 1-hydroxycyclohexanecarboxylate acid in 50 ml of toluene is boiled overnight and then evaporated.

Yield: 18.6 g (quantitative) 1-ethoxycarbonylmethylene ether 2,4,6-trimethylpentane acid as a colourless oil.

Similarly, respectively, according to the above General data on the synthesis receive the compounds of formula (III), are given in table. 11.

Example I-3-a-1

< / BR>
26,0 g (60,7 mmol) of the compound soglasno. Excessive triperoxonane acid is removed in vacuo, the residue is mixed with 400 ml of water and 120 ml of methyl tert-butyl ether using sodium hydroxide establish a pH value equal to 14. Extracted twice with methyl tert-butyl ether, the aqueous phase is acidified with concentrated hydrochloric acid and extracted three times with methyl tert-butyl ether. The organic phase is dried and concentrated.

Yield: 8.8 g (52% of theoretically calculated amount); melting point: 160 to 162oC.

Similarly receive connection I-3-a-2 the following formula

< / BR>
So pl. 180-183oWITH

Example I-3-b-1

< / BR>
Receive:

1.0 g (3.6 mmol) of the compound according to example I-3-a-1 contribute in 15 ml of absolute methylene chloride and mixed with 0.75 ml of triethylamine. Under ice cooling was added dropwise a solution of 0.82 g (to 4.68 mmol) of acid chloride of 6-chloronicotinic acid in 3 ml of absolute methylene chloride. The reaction mixture is stirred for two hours at room temperature, then washed twice with 10% citric acid and the combined aqueous phase is extracted with methylene chloride. The combined organic phases are washed twice with 1 N. ruskie phase is dried, concentrated and the residue is stirred with petroleum ether.

Output: 1,37 g (91% of theoretically calculated amount); melting point: from 123 to 126oC.

Similarly to the method of example I-3-b-1, respectively, according to the above General data on the synthesis get listed in table. 12 the compounds of formula (I-3-b):

Example I-3-in-1

< / BR>
Receive:

1.0 g (3.6 mmol) of the compound according to example 1-3-a-1 contribute in 15 ml of absolute methylene chloride and mixed with 0.75 ml (1.5 equivalents) of triethylamine. Under ice cooling was added dropwise a solution of 0.61 ml (0.64 g; and 4.68 mmol) isobutyl ether 6-Harbourview acid in 3 ml of absolute methylene chloride. The reaction mixture is stirred for two hours at room temperature, then washed twice with 10% citric acid and the combined aqueous phase is extracted with methylene chloride. The combined organic phases are washed twice with 1 n sodium hydroxide solution, aqueous alkaline phase is extracted with methylene chloride. Finally the combined organic phases are dried and concentrated.

Output: 1,32 g (97% of theoretically calculated amount); oil.

1H-NMR spectrum (400 MHz, dimetilan I-3-in-1 are the compounds of formula (I-3), summarized in table. 13

Example IV-1

< / BR>
A: 25 g (98 mmol) of the compound of formula (HGH-1):

< / BR>
and 1 drop of dimethylformamide together with 17.5 g (147 mmol) of thionyl chloride in 100 ml of toluene is stirred for five minutes at room temperature and then at 100 ° oTo stop gassing. Volatile components are removed under high vacuum.

B: To a solution of 18 ml (130 mmol) of Diisopropylamine in 100 ml of tetrahydrofuran under ice cooling was added dropwise 72 ml (118 mmol) of utility (1.6 M) and stirred for fifteen minutes at this temperature. Then at a temperature of 0oWith added dropwise a solution of 18.8 g (108 mmol) of the compound obtained according to example (XXIV-3, in 40 ml of tetrahydrofuran and stirred for thirty minutes at this temperature. After this, at a temperature of 0oWith added dropwise to the solution obtained in stage a, the carboxylic acid in 40 ml of tetrahydrofuran, stirred for one hour at room temperature. Then add 350 ml of methyl tert-butyl ether and a few drops of water, extracted twice with 10% aqueous solution of ammonium chloride, the organic phase is dried and concentrated. The crude product in an amount of 40 g purified by column ptx2">

Output: 27,0 g (64% of theoretically calculated amount); oil.

1H-NMR spectrum (400 MHz, deuterochloroform):

< / BR>
< / BR>
< / BR>
< / BR>
< / BR>
< / BR>
< / BR>
Example 1-4-a-1

< / BR>
6.7 g (30 mmol) of 2-(2,4,5-trimetilfenil)chlorocarbonate with 4.3 g (30 mmol) of 4,5-dihydro-of 2.2.5.5-tetramethyl-3-(2H)-furanone for four hours is heated at a temperature of 200oC. After purification by column chromatography on silica gel using a mixture of toluene with ethanol in a ratio of 20:1 as the eluting means obtain 4.6 g (46% of theoretically calculated amount) of target compound; melting point: 182 to 184oC.

Similarly, respectively, according to the above General data on the synthesis receive the compounds of formula (1-4-a), are given in table. 14.

Example I-4-b-1

< / BR>
2.5 g (7.5 mmol) of the compound obtained according to example I-4-a-1, bring in 25 ml of ethyl acetate, mixed with 0.75 g of triethylamine and at a temperature of 0oWith added dropwise a solution of 0.6 g of acetylchloride in 20 ml of ethyl acetate. Is stirred for twenty hours at room temperature, the precipitate is separated, the organic phase is washed twice with 50 ml of concentrated solution of chloride Netanya mixture of toluene with acetone in the ratio of 50:1.

Yield: 0.8 g (29% of theoretically calculated amount); melting point: from 143 to 144oC.

Similarly to the method of example I-4-b-1, respectively, according to the above General data on the synthesis receive the compounds of formula (I-4-b) are given in table. 15.

Example 1-4-in-1

< / BR>
1.7 g (5 mmol) of the compound according to example I-4-a-3 make in 20 ml of ethyl acetate, mixed with 0.5 g (5 mmol) of triethylamine and at a temperature of 0oWith added dropwise a solution of 0.5 g (5 mmol) of methyl ether of Harborview acid in 5 ml of ethyl acetate. Is stirred for twenty hours at room temperature, the precipitate was separated, the organic phase is washed twice with 50 ml policecontributing solution of sodium chloride, dried over sodium sulfate and evaporated in vacuum. The remainder chromatographic on silica gel using a mixture of toluene with acetone in the ratio of 30:1.

Yield: 1.0 g (51% of theoretically calculated amount); melting point: from 144 to 146oC.

Similarly, respectively, according to the above General data on the synthesis receive the compounds of formula (I-4-C), are given in table. 16.

Example I-5-a-1

< / BR>
2.2 g (10 mmol) of 2-(2,4,5-trimetilfenil)chlorocarbon the re 50oC. the Precipitate was separated, washed with cyclohexane and dried. Obtain 2.8 g of product (82% of theoretically calculated amount); the melting point of 215 to 216oC.

Example XXIII-1

< / BR>
To a mixture of 100 g (1,785 mol) of potassium hydroxide in 130 ml of water and 260 ml of methanol at room temperature was added dropwise 247 g (1,162 mol) of the compound according to example (XXIV-1 (75%) and refluxed for five hours. After cooling, diluted with 300 ml of water and extracted with ethyl acetate. The aqueous phase is acidified using policecontributing hydrochloric acid, the precipitate is filtered under vacuum and dried.

Output: 77 g (45% of theoretically calculated amount); melting point: from 119 to 121oC.

Example XXIII-2

< / BR>
Similarly to the method of example XXIII-1 receive 2,4,5-trichlorophenoxy acid. Melting point: from 112 to 115oC.

Getting 2,4,5-trimethylpentane acid (see scheme 16 in the end of the description).

Example XXIII-3

286 g (1.4 mol) 66% 1,2,4,5-tetramethylbenzene dissolved in 563 ml tetrachlorophenol and at room temperature consistently contribute 27.5 g (0.15 mol) of N-bromosuccinimide and 0.4 g of benzoyl chloride. Naked is within thirty minutes at a temperature of 80oC and then cooled down to room temperature. The solid is filtered off under vacuum and the solvent is removed at a pressure of 20 mbar. Then the residue is distilled in high vacuum and get 226 g (66% of theoretically calculated amount) of 2,4,5-trimethylbenzaldehyde with a boiling point 95oC at a pressure of 0.05 mbar and a purity of 86%.

To a solution of 57 g (of 1.16 mol) of sodium cyanide in 63 ml of water and 0.6 g of Aliquat 336 at a temperature of from 60 to 80oWith added dropwise a solution of 226 g (of 0.91 mol) of 2,4,5-trimethylbenzaldehyde (86%) 94 ml of toluene and then additionally stirred for four hours at a temperature of 80oC. After cooling to room temperature, the phases are separated and the organic phase is washed twice with water and twice with saturated sodium chloride solution, dried and concentrated. After distillation 103 g (70% of theoretically calculated amount) of 2,4,5-trimethylbenzaldehyde with a purity of 99% and a boiling point of 120oC at a pressure of 0.2 mbar.

To 2662 ml of water at room temperature was added dropwise 2118 ml of concentrated sulfuric acid and the solution heated to 90oC. At this temperature, add 355 g (2,23 mol) of 2,4,5-trimethylbenzaldehyde the 100oC. After cooling the reaction mixture with vigorous stirring make iced water and the precipitate is filtered off under vacuum. The solid is washed repeatedly with water and then with petroleum ether and dried. Receive 358 g (90% of theoretically calculated amount) of 2,4,5-trimethylpentane acid; melting point: from 123 to 125oC.

Similar to the methods of examples XXIII-1 and HH-3 get listed in table. 17 new phenylacetic acid of the formula (XXIII)

The compounds of formula (XXIII) are novel with the exception of compounds in which X, Y, Z denote methyl and in which X, Y, Z denote chlorine.

Example XXIV-1

< / BR>
To a solution of 347 g (0,948 mol) of the compound according to example XXV-1 (73%) in 410 ml of methanol at room temperature was added dropwise to 700 ml of 30% methanolic solution of sodium methylate, is refluxed for five hours, cooled to room temperature and added dropwise 110 ml of concentrated sulfuric acid. Refluxed for one hour, the methanol is distilled off and the solid residue is treated with water. The organic phase is separated and the aqueous phase is extracted twice with 1.5 l of methylene chloride. United organicheski the calculated amount) with the contents of the product 75% (gas chromatography).

Example XXIV-2

< / BR>
Similarly to the method of example XXIV-1 are methyl ester 2,4,5-trichlorophenoxy acid in the form of a dark oil with a yield of 95% of theoretically calculated amount and purity of 80% (gas chromatography).

Example XXIV-3

< / BR>
35 g (0,143 mol) methyl ester 2-chloro-4-bromo-5-methylphenylacetic acid and 31 g of copper cyanide in 350 ml of dimethylformamide is refluxed for one day. Then the reaction mixture was concentrated in vacuo, the residue partitioned between water and methyl tert-butyl ether, the organic phase is dried and concentrated.

Output: 18,

By analogy with the procedure of example XXIV-1 are listed in table. 18 new esters of phenylacetic acid of the formula (XXIV).

Example XXV-1

< / BR>
To a well-cooled mixture 229,7 g (2,272 mol) tert-butylnitrite and 254,8 g (1,775 mol) of anhydrous ferrous chloride copper in 990 ml of anhydrous acetonitrile was added dropwise 2205 g (22.7 mol) 1,1-dichloroethane, and the mixture support at a temperature below 30oC. and Then at a temperature below 30oWith added dropwise a mixture of 232 g (1,49 mol) 4-chloro-2,5-dimethylaniline and 1500 ml of anhydrous acetonitrile. At room temperature and stirred until the pre is using 6 l, extracted with methyl tert-butyl ether. The combined organic phases are washed with 20% hydrochloric acid and concentrated. Obtained as residue oil is subjected to fractional distillation.

Output: 347 g of a dark oil (approximately 63% of theoretically calculated amount) with the contents of the product 74% (gas chromatography).

Example XXV-2

Similarly to the method of example XXV-1 get 2-(2,4,5-trichlorophenyl)-1,1,1-trichloroethane in the form of a dark oil with a yield of 81% of theoretically calculated amount and content of 78%.

By analogy with the procedure of example XXV-1 are still listed in the table. 19 1,1,1-trichloro-2-phenylethane formula (XXV)

Oil without further purification can be used to obtain compounds of formula XXIV. The compounds of formula XXV are new with the exception of compounds in which X, Y, Z denote chlorine.

Synthesis of 2,4,5-trimethylenetrinitramine

Methyl ester 2,4,5-trimethylpentane acid

< / BR>
100 g (of 0.56 mol) of 2,4,5-trimethylpentane acid are dissolved in 230 ml of methanol, mixed with 6 ml of concentrated sulfuric acid for ten hours, refluxed. Then cooled to room temperature and metanarratives with 200 ml of toluene. The organic phase is separated, dried, concentrated and distilled. Get to 48.6 g of methyl ester of 2,4,5-trimethylpentane acid with a boiling point of 86oC at a pressure of 0.2 mbar.

Dimethyl 2-(2, 4, 5-trimetilfenil)malonic acid

< / BR>
18.6 g (of 0.62 mol, 80%) of sodium hydride contribute in 384 ml dimethylcarbonate and heated to approximately 80oC. Then was added dropwise a solution of 48 g (0.25 mol) of methyl ester of 2,4,5-trimethylpentane acid in 100 ml of dimethylcarbonate and within four hours refluxed. The mixture is cooled to room temperature, the excess sodium hydride is decomposed with ethanol and then the reaction mixture is poured into 1500 ml of ice water. Using 6 N. hydrochloric acid set pH 4 to 5, and the organic phase is treated with toluene. The organic phase is separated, dried, concentrated and without further purification used in the nearest stage. Get to 51.6 g of dimethyl 2-(2,4,5-trimetilfenil) of malonic acid in the form of butter.

1H-NMR-spectrum (deuterochloroform), (M. D.): 7,12 (S., 1H); 6,98 (S., 1H); 4,84 (s, 1H); 3.75 to (C, 6N); and 2.27 (s, 3H); of 2.23 (s, 3H); of 2.21 (s, 3H).

Similarly receive connections, are given in table. 20.

The residue is mixed with ice water and washed with a small amount of toluene. The aqueous solution while cooling with ice, acidified with concentrated hydrochloric acid to pH 1, the precipitate is filtered under vacuum and dried. Get to 30.3 g of 2-(2,4,5-trimetilfenil)malonic acid.

1H-NMR-spectrum (fully deuterated dimethyl sulfoxide), (M. D.): 7,03 (s, 1H); to 6.95 (s, 1H); of 4.66 (s, 1H); 2,17 (s, 3H); 2,16 (C, 6N).

Similarly receive more compounds are given in table. 21.

2,4,5-Trimethylchlorosilane

< / BR>
30 g of 2-(2,4,5-trimetilfenil)of malonic acid at a temperature of from 50 to 60oWith suspended in 60 ml of toluene dropwise and mixed with 62.5 ml of thionyl chloride. The mixture was then heated for fifteen hours at a temperature of from 90 to 100oC. After cooling, the volatile components are removed by Stripping with protective gas and the excess thionyl chloride is distilled off. As allocate the remainder of 30.6 g of 2,4,5-trimethylchlorosilane.

1H-NMR spectrum (deuterochloroform), (M. D.): 7,07 (s, 2H); and 2.27 (s, 3H); 2,22 (emery

An example of a

Test Phaedon

1 wt. hours specified in the table. And the active substance is mixed with 7 wt. hours of dimethylformamide as solvent and 1 wt. including simple alkylarylsulphonates ether as an emulsifier, and the resulting concentrate is diluted with water to a concentration of the active substance, equal to 0.1%.

Cabbage leaves (Brassica oleracea) are treated by dipping into the active drug substance, and while the leaves are still moist, they put the larvae of leaf shitty (Phaedon cochleariae).

After 7 days to determine the degree of killing of larvae in %. 100% means that all dead larvae of the beetle; 0% means that no died no one larva of the beetle.

The active substance and the results of the experiment are given in table. A.

Example B

Test Plutella

1 wt. hours specified in the table. B active substances are mixed with 7 wt. hours of dimethylformamide as solvent and 1 wt. including simple alkylarylsulphonates ether as an emulsifier, and the resulting concentrate is diluted with water to a concentration of the active substance, equal to 0.1%.

Cabbage leaves (Brassica oleracea) are treated by dipping into the active drug substance, and while the leaves are still moist, they put caterpillars mo is 00% mean that killed all caterpillars; 0% means that no died no one caterpillar.

The active substance and the results of the experiment are given in table. B.

The example IN

Test Spodoptera

1 wt. hours specified in the table. The active substance is mixed with 7 wt. hours of dimethylformamide as solvent and 1 wt. including simple alkylarylsulphonates ether as an emulsifier, and the resulting concentrate is diluted with water to a concentration of the active substance, equal to 0.1%.

Cabbage leaves (Brassica oleracea) are treated by dipping into the active drug substance, and while the leaves are still moist, they put caterpillars scoop (Spodoptera frugiperda).

After 7 days to determine the degree of killing of larvae in %. 100% means that all dead caterpillars; 0% means that no died no one caterpillar.

The active substance and the results of the experiment are given in table. Century

Example D

Test Nephotettix

1 wt. hours specified in the table. G 1 and G 2 of the active substance is mixed with 7 wt. hours of dimethylformamide as solvent and 1 wt. including simple alkylarylsulphonates ether as an emulsifier, and the resulting concentrate is diluted with water to the concentrations indicated in the table. G 1 and G 2.

Sprouts rest green rice cicadas (Nephotettix cincticeps).

After 6 days determine the degree of killing cicadas in %. 100% means that all dead cicadas; 0% means that no died no Cicada.

Active substances, their concentrations and the results of the experiment are given in table. G 1 and G 2.

Example D

Test Myzus

1 wt. hours specified in the table. D 1 and D 2 of the active substance is mixed with 7 wt. hours of dimethylformamide as solvent and 1 wt. including simple alkylarylsulphonates ether as an emulsifier, and the resulting concentrate is diluted with water to a concentration of the active substances listed in table. D 1 and D 2.

Cabbage leaves (Brassica oleracea), strongly affected peach aphid (Myzus persicae), treated by dipping into the active drug substance.

After 6 days determine the degree of killing aphids in %. 100% means that all dead aphids; 0% means that no died no aphids.

Active substances, their concentrations and the results of the experiment are given in table. D 1 and D 2.

Example E

The Tetranychus test (resistant derivatives of phosphoric acid/processing dipping)

1 wt. hours specified in the table. E. the active substance is mixed with 7 wt. hours of dimethylformamide as solvent and 1 mdeu to the concentration of the active substance, equal to 0.1 or 0.01%.

Plant kidney beans (Phaseolus vulgaris), heavily infected spider mite (Tetranychus urticae) in all stages of development, dip in the preparation of the active substance.

After respectively 5, 7, 13 and 14 days to determine the degree of killing mites in %. 100% means that all dead spider mites; 0% means that no died no spider mite.

Active substances, their concentrations and the results of the experiment are given in table. E.

Example G

Predsjedava test

1 wt. including the active substance example (I-4-a-3 mixed with 5 wt. including acetone as solvent and 1 wt. including simple alkylarylsulphonates ether as an emulsifier, and the resulting concentrate is diluted with water to the desired concentration.

Seeds of the test plants are sown in normal soil and, after 24 hours, watered with the preparation of the active substance. It is reasonable to maintain a constant amount of water per unit area. The concentration of active substance in the preparation is of no importance, crucial only the consumption rate per unit area of the active substance.

Three weeks later assess the degree of damage to the plants in percentage compared the actions (as untreated control plants)

100% means complete destruction of the plants.

In this test, the above compound with a consumption rate of 500 g/ha and good tolerability of Beta vulgaris damage by 90% in the case of Alopecurus myosuroides, 96% in the case of Avena fatua and 95% in the case of Setaria viridis.

Example C

Test with larvae of flies/the vast development of action

Test animals: all larval stages of Lucilia cuprina (- resistant derivatives of phosphoric acid) [pupae and adults (without contact with the biologically active substance)]

3 wt. including the active substance example (I-1-a-1 mixed with 7 wt. o'clock, consisting of 50 wt. % simple etilenpropilendienovogo ether and 50 wt.% simple nonylphenolethoxylate ether as solvent, and the thus obtained emulsion concentrate is diluted with water corresponding to the desired concentration.

From 30 to 50 larvae per concentration put on in the tubes of horse meat (1 cm3), on which a pipette put 500 ál of the test diluted formulation. The tubes are placed in plastic cups, the bottom of which is covered with sand, and kept in a climate chamber (temperature 261,5oC; relative humidity 7010%). Control C is igrali larvae (approximately seventy-two hours) the tubes were removed and the glasses served perforated plastic lids. After polutorakratnomu duration of development (hatching control flies) count the number of hatched flies, and the number of pupae/shells pupae.

As a criterion of validity accept the occurrence of death in the case of the treated larvae after forty-eight hours (larvicide effect), respectively, the inhibition of hatching of adults from pupae, respectively suppression of the formation of pupae. As a criterion of validity in vitro substances are taken suppressing development of fleas, accordingly, the termination of the development to the adult stage. This constitutes 100% of larvicide effect means that after forty-eight hours, all larvae died. Of 100% of the vast development of the action means that none of the adult flies are not hatched.

In this test, the above compound at a concentration of 1000 parts per million has 100% effect.

Example

Test with resistant Boophilus microplus/resistant derivatives of phosphoric acid type ticks

Test animals: adult suckling females

Solvent: dimethylsulfoxide

20 mg below the active substance is dissolved in 1 ml of dimethyl sulfoxide, smaller konkretnom definition. 1 μl of the solution is administered by injection into the abdomen, animals are moved into cups and incubated in a climate chamber. The action is determined by the suppression of oviposition. 100% means that no ticks no.

In this test, the compounds according to examples I-4-a-1 and I-4-b-1 at a concentration of about 20 µg per animal have 100% effect.

The following experiments to determine the phytotoxicity suggests that the proposed 2,4,5-triple-substituted phenylethanol to the General formula (I) are substantially less phytotoxicity than the well-known phenylethanol.

Example TO

Test Cucumis sativus

1 wt. hours specified in the table. The active substance is mixed with 7 wt. hours of dimethylformamide as solvent and 1 wt. including simple alkylarylsulphonates ether as an emulsifier, and the resulting concentrate is diluted with water to the concentrations indicated in the table. K.

On the shoots of cucumber (Cucumis sativus) napraschivaet solution containing the active substance, and then rustici transferred to the greenhouse.

After 7 or 14 days to determine the degree of damage to plants in %. 100% means full damage and 0% means that the plants are not damaged.

Active BR>
1 wt. hours specified in the table. The active substance is mixed with 7 wt. hours of dimethylformamide as solvent and 1 wt. including simple alkylarylsulphonates ether as an emulsifier, and the resulting concentrate is diluted with water to the concentrations indicated in the table. L.

On the shoots of tomato (Lycopersicon lycopersicum) napraschivaet solution containing the active substance, and then rustici transferred to the greenhouse.

After 7 or 14 days to determine the degree of damage to plants in %. 100% means full damage and 0% means that the plants are not damaged.

Active substances, their concentrations and the results of the experiment are given in table. L.

Example M

Test Malus sylvestris

1 wt. hours specified in the table. The active substance is mixed with 7 wt. hours of dimethylformamide as solvent and 1 wt. including simple alkylarylsulphonates ether as an emulsifier, and the resulting concentrate is diluted with water to the concentrations indicated in the table. M

On the shoots of Apple (Malus sylvestris) napraschivaet solution containing the active substance, and then rustici transferred to the greenhouse.

After 21 days, determine the degree of damage to the plants in %. 100% means full pareapet summarized in table. M

1. 2,4,5-triple-substituted phenylethanol General formula (I)

< / BR>
where X means halogen, alkyl with 1-6 carbon atoms, alkenyl with 2-6 carbon atoms, quinil with 2-6 carbon atoms, alkoxy with 1-6 carbon atoms, halogenated with 1-4 carbon atoms, halogenoalkanes with 1-4 carbon atoms, a cyano or a nitro-group;

Y represents halogen, alkyl with 1-6 carbon atoms, alkoxy with 1-6 carbon atoms, halogenated with 1-4 carbon atoms, halogenoalkanes with 1-4 carbon atoms, a cyano or a nitro-group;

Z denotes halogen, alkyl with 1-6 carbon atoms, alkoxy with 1-6 carbon atoms, halogenated with 1-4 carbon atoms, halogenoalkanes with 1-4 carbon atoms, hydroxyl, cyano, a nitro-group or fenoxaprop, phenylthiourea, thiazoleacetate, pyridyloxy, primidealhalbgrouppen, personalantispy, phenylalkylamine with 1-4 carbon atoms in the alkyl part or phenylalkylamine with 1-4 carbon atoms in the alkyl part, each of which may be unsubstituted or substituted with halogen, alkyl with 1-4 carbon atoms, alkoxyl with 1-4 carbon atoms, halogenation with 1-4 carbon atoms, halogenation with 1-4 carbon atoms, the nitro-group, or cyano; or

Het denotes one of the groups

< / BR>
< / BR>
< / BR>
< / BR>
< / BR>
where a represents hydrogen, unsubstituted or substituted with halogen alkyl with 1-12 carbon atoms, alkenyl with 2-8 carbon atoms, alkyl with 1-8 carbon atoms, substituted alkoxygroup with 1-10 carbon atoms, polyalkoxyalkyl with 1-8 carbon atoms in all alkyl groups or alkyl with 1-6 carbon atoms, substituted alkylthiol with 1-10 carbon atoms, unsubstituted or substituted with halogen, alkyl with 1-6 carbon atoms or alkoxygroup with 1-6 carbon atoms cycloalkyl with 3-8 carbon atoms, in which one or two methylene groups may be replaced by oxygen atom and/or sulfur atom, either unsubstituted or substituted with halogen, alkyl with 1-6 carbon atoms, halogenation with 1-6 carbon atoms, alkoxygroup with 1-6 carbon atoms, halogenlampe with 1-6 carbon atoms, cyano or nitro-group is phenyl, naphthyl, phenyl substituted by alkyl with 1-6 carbon atoms, naphthyl, substituted alkyl with 1-6 carbon atoms, or heteroaryl with 5 or 6 atoms in the CEC is of geroda or alkyl with 1-6 carbon atoms, replaced by alkoxygroup with 1-8 carbon atoms, or

A, b and the carbon atom to which they are linked, represent cycloalkyl with 3-10 carbon atoms or cycloalkenyl with 5-10 carbon atoms in which one methylene group may be replaced by oxygen atom or sulfur atom and which is unsubstituted or substituted by alkyl with 1-8 carbon atoms, cycloalkyl with 3-10 carbon atoms, halogenation with 1-8 carbon atoms, alkoxygroup with 1-8 carbon atoms, alkylthiol with 1-8 carbon atoms, halogen or phenyl; or

A, b and the carbon atom to which they are linked, represent cycloalkyl with 5-6 carbon atoms which may be substituted with one or two oxygen atom and/or sulfur alkylenediamine group, or alkylenediamines or alkylenediamine group, which with the carbon atom to which they are attached, form an additional 5-8-membered ring; or

A, b and the carbon atom to which they are linked, represent cycloalkyl with 3-8 carbon atoms or cycloalkenyl with 5-8 carbon atoms, where two Deputy together with the carbon atoms to which they are linked, represent unsubstituted or substituted by alkyl with 1-6 carbon atoms, alkoxygroup with 1-6 atomapi carbon atoms, in which one methylene group may be replaced by oxygen atom or a sulfur atom;

D is hydrogen, unsubstituted or substituted with halogen alkyl with 1-12 carbon atoms, alkenyl with 3-8 carbon atoms, quinil with 3-8 carbon atoms, alkyl of 2-8 carbon atoms, substituted alkoxygroup with 1-10 carbon atoms, alkyl of 2-8 carbon atoms, polyamidine alkoxygroup with 1-8 carbon atoms each, or alkyl of 2-8 carbon atoms, substituted alkylthiol with 1-10 carbon atoms; unsubstituted or substituted with halogen, alkyl with 1-4 carbon atoms, alkoxygroup with 1-4 carbon atoms or halogenation with 1-4 carbon atoms, cycloalkyl with 3-8 carbon atoms, in which one or two non-directly adjacent methylene groups may be replaced by oxygen atom and/or sulfur atom; or an unsubstituted or substituted with halogen, alkyl with 1-6 carbon atoms, halogenation with 1-6 carbon atoms, alkoxygroup with 1-6 carbon atoms, halogenlampe with 1-6 carbon atoms, cyano or nitro-group is phenyl, heteroaryl with 5-6 atoms in the cycle, and one or two heteroatoms from the series oxygen, sulphur and nitrogen, phenyl substituted by alkyl with 1-6 carbon atoms, or heteroaromatic carbon; or

A and D together denote a group: alcander with 3-6 carbon atoms, alkerdeel with 3-6 carbon atoms or alkadienes with 4-6 carbon atoms in which one methylene group may be replaced by oxygen atom or sulfur atom and which is unsubstituted or substituted with halogen, or unsubstituted or substituted by halogen, alkyl with 1-10 carbon atoms, Alcock-syrupy with 1-6 carbon atoms, alkylthiol with 1-6 carbon atoms, cycloalkene with 3-7 carbon atoms, phenyl or benzyloxycarbonyl or the other, forming secondinstance ring alkadienes group with 3-6 carbon atoms, allendales group with 3-6 carbon atoms or acadieville group with 4-6 carbon atoms in which one methylene group in each case may be replaced by oxygen atom or sulfur atom and which is unsubstituted or substituted by alkyl with 1-6 carbon atoms; or

A and D together represent landiolol group with 3-6 carbon atoms or alkantiolsul group with 3-6 carbon atoms, which may contain one of the following groups:

< / BR>
< / BR>
< / BR>
< / BR>
< / BR>
< / BR>
< / BR>
< / BR>
or

< / BR>
G means hydrogen (a) or one of the groups

< / BR>
< / BR>
< / BR>
< / BR>BR>
M is an oxygen atom or a sulfur atom,

R1means unsubstituted or substituted with halogen alkyl with 1-20 carbon atoms, alkenyl with 2-20 carbon atoms, alkoxyalkyl with 1-8 carbon atoms in both alkyl groups, alkylthiols with 1-8 carbon atoms in both alkyl groups, or polyalkoxyalkyl with 1-8 carbon atoms in all alkyl groups, or unsubstituted or substituted by halogen, alkyl with 1-6 carbon atoms or alkoxygroup with 1-6 carbon atoms cycloalkyl with 3-8 carbon atoms, in which one or two methylene groups may be replaced by oxygen atom and/or sulfur atom; unsubstituted or substituted with halogen, a cyano, a nitro-group, by alkyl with 1-6 carbon atoms, alkoxygroup with 1-6 carbon atoms, halogenation with 1-6 carbon atoms, halogenlampe with 1-6 carbon atoms, alkylthiol with 1-6 carbon atoms or alkylsulphonyl with 1-6 carbon atoms phenyl; unsubstituted or substituted with halogen, a nitro-group, cyano, alkyl with 1-6 carbon atoms, alkoxygroup with 1-6 carbon atoms, halogenation with 1-6 carbon atoms or halogenlampe with 1-6 carbon atoms phenylalkyl with 1-6 carbon atoms in the alkyl part; unsubstituted or Sames range: oxygen, sulfur and nitrogen; unsubstituted or substituted by halogen or alkyl with 1-6 carbon atoms peroxyacyl with 1-6 carbon atoms in the alkyl part; unsubstituted or substituted with halogen, amino or alkyl with 1-6 carbon atoms 5 - or 6-membered heteroepitaxial with 1-6 carbon atoms in the alkyl portion with one or two heteroatoms from the series oxygen, sulphur and nitrogen,

R2means unsubstituted or substituted with halogen alkyl with 1-20 carbon atoms, alkenyl with 2-20 carbon atoms, alkyl of 2-8 carbon atoms, substituted alkoxygroup with 1-8 carbon atoms, or alkyl of 2-8 carbon atoms, polyamidine alkoxygroup with 1-8 carbon atoms in each alkyl group; unsubstituted or substituted with halogen, alkyl with 1-6 carbon atoms or alkoxygroup with 1-6 carbon atoms cycloalkyl with 3-8 carbon atoms or an unsubstituted or substituted with halogen, a cyano, a nitro-group, alkyl with 1-6 carbon atoms, alkoxygroup with 1-6 carbon atoms, halogenation with 1-6 carbon atoms or halogenlampe with 1-6 carbon atoms, phenyl or benzyl;

R3means unsubstituted or substituted with halogen alkyl with 1-8 carbon atoms or an unsubstituted or substituted with halogen, alkyl what syruppy with 1-4 carbon atoms, the cyano or nitro-group is phenyl or benzyl;

R4and R5independently from each other, each represent unsubstituted or substituted with halogen alkyl with 1-8 carbon atoms, alkoxy with 1-8 carbon atoms, alkylamino with 1-8 carbon atoms, dialkylamino with 1-8 carbon atoms in each alkyl group, alkylthio with 1-8 carbon atoms or alkanity with 3-8 carbon atoms, or an unsubstituted or substituted with halogen, a nitro-group, cyano, alkoxygroup with 1-4 carbon atoms, halogenlampe with 1-4 carbon atoms, alkylthiol with 1-4 carbon atoms, halogeenilamppu with 1-4 carbon atoms, alkyl with 1-4 carbon atoms or halogenation with 1-4 carbon atoms, phenyl, phenoxy or phenylthio;

R6and R7independently from each other, each denote hydrogen, unsubstituted or substituted with halogen alkyl with 1-8 carbon atoms, cycloalkyl with 3-8 carbon atoms, alkoxy with 1-8 carbon atoms, alkenyl with 3-8 carbon atoms or alkyl of 2-8 carbon atoms, substituted alkoxygroup with 1-8 carbon atoms; unsubstituted or substituted with halogen, alkyl with 1-8 carbon atoms, halogenation with 1-8 carbon atoms or alkoxygroup with 1-8 carbon atoms, phenyl or benzyl, the mi of carbon, in which one methylene group may be replaced by oxygen atom or a sulfur atom;

R13means hydrogen or unsubstituted or substituted by halogen alkyl with 1-8 carbon atoms, or alkoxy with 1-8 carbon atoms, unsubstituted or substituted with halogen, alkyl with 1-4 carbon atoms or alkoxygroup with 1-4 carbon atoms, cycloalkyl with 3-8 carbon atoms in which one methylene group may be replaced by oxygen atom or a sulfur atom, or unsubstituted or substituted by halogen, alkyl with 1-6 carbon atoms, alkoxygroup with 1-6 carbon atoms, halogenation with 1-4 carbon atoms, halogenlampe with 1-4 carbon atoms, a nitro-group or a cyano phenyl, phenylalkyl with 1-4 carbon atoms in the alkyl part or phenylalkyl with 1-4 carbon atoms in the CNS;

R14means hydrogen or alkyl with 1-8 carbon atoms; or

R13and R14together mean alcander with 4-6 carbon atoms;

R15and R16are identical or different and denote alkyl with 1-6 carbon atoms; or

R15and R16together mean ascandilwy residue with 2 to 4 carbon atoms which may be substituted by alkyl with 1-6 carbon atoms of Hillerod, alkoxygroup with 1-4 carbon atoms, halogenlampe with 1-4 carbon atoms, a nitro-group, or cyano;

R17and R18independently from each other, each denote hydrogen, unsubstituted or substituted with halogen alkyl with 1-8 carbon atoms, either unsubstituted or substituted with halogen, alkyl with 1-6 carbon atoms, alkoxygroup with 1-6 carbon atoms, halogenation with 1-4 carbon atoms, halogenlampe with 1-4 carbon atoms, a nitro-group or a cyano phenyl; or

R17and R18together with the carbon atom to which they are linked, represent a carbonyl group, unsubstituted or substituted by alkyl with 1-4 carbon atoms or alkoxygroup with 1-4 carbon atoms, cycloalkyl with 5-7 carbon atoms in which one methylene group may be replaced by oxygen atom or a sulfur atom;

R19and R20independently from each other, each represent alkyl with 1-10 carbon atoms, alkenyl with 2-10 carbon atoms, alkoxy with 1-10 carbon atoms, alkylamino with 1-10 carbon atoms, alkenylamine with 3-10 carbon atoms, dialkylamino with 1-10 carbon atoms in each alkyl group or dialkylamino with 3-10 carbon atoms in each alkenylphenol group.3. 2,4,5-triple-substituted phenylethanol General formula (I) under item 1 or 2, where X denotes fluorine, chlorine, bromine, methyl, ethyl, propyl, butyl, isobutyl, isopropyl, tert. -butyl, methoxy group, ethoxypropan, propoxylate, isopropoxy, trifluoromethyl, cryptometer, dipterocarp, cyano or nitro-group; Y represents fluorine, chlorine, bromine, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert. -butyl, methoxy group, ethoxypropan, propoxylate, isopropoxy, trifluoromethyl, cryptometer, dipterocarp, citil, a methoxy group, ethoxypropan, propoxylate, isopropoxy, trifluoromethyl, cryptometer, dipterocarp, cyano or nitro-group; or Y and Z together denote unsubstituted or substituted by fluorine, chlorine, stands, ethyl, propylene, isopropyl, methoxy group, ethoxypropane, propoxyphene, isopropoxycarbonyl or trifluoromethyl alcander with 3-4 carbon atoms, in which two not directly adjacent link can be replaced by oxygen, and X is any one of the above values; Het represents one of the groups

< / BR>
< / BR>
< / BR>
< / BR>
< / BR>
where a represents hydrogen, unsubstituted or substituted by fluorine or chlorine, alkyl with 1-8 carbon atoms, alkenyl with 2-4 carbon atoms, alkyl with 1-4 carbon atoms, a substituted alkoxy group with 1-6 carbon atoms, polyalkoxyalkyl with 1-4 carbon atoms in the alkyl part and in all CNS groups, or alkyl with 1-4 carbon atoms, substituted alkylthiol with 1-6 carbon atoms, either unsubstituted or substituted by fluorine, chlorine, stands or a methoxy group cycloalkyl with 3-6 carbon atoms, in which one or two methylene groups may be replaced by oxygen atom and/or sulfur atom, or unsubstituted and trifluoromethyl, cryptomaterial, cyano or nitro-group is phenyl, pyridyl or benzyl;

In denotes hydrogen, alkyl with 1-8 carbon atoms or alkyl with 1-2 carbon atoms, zalesny alkoxygroup with 1-4 carbon atoms, or

A, b and the carbon atom to which they are linked, represent cycloalkyl with 3-8 carbon atoms or cycloalkenyl with 5-8 carbon atoms in which one methylene group may be replaced by oxygen atom or sulfur atom and which is unsubstituted or substituted stands, ethyl, n-propylene, isopropyl, bootrom, isobutyl, Deut. -bootrom, tert-bootrom, cyclohexyl, trifluoromethyl, methoxy group, ethoxypropane, n-propoxyphene, isopropoxycarbonyl, butoxypropyl, isobutoxy, starbucksyou, tert. -butoxypropyl, methylthiourea, ethylthiourea, fluorine, chlorine or phenyl; or

A, b and the carbon atom to which they are linked, represent cycloalkyl with 5-6 carbon atoms, which is unsubstituted or substituted alkylenediamine group may contain an oxygen atom or a sulfur atom, or alkylenedioxy group, which with the carbon atom to which it is linked, forms an additional five - or six-membered ring; or

A, b and the carbon atom, to the which two Deputy together with the carbon atoms, to which they are linked, represent alcander with 3-4 carbon atoms, alkerdeel with 3-4 carbon atoms or butadienyl in which one methylene group may be replaced by oxygen atom or a sulfur atom;

D is hydrogen, unsubstituted or substituted by fluorine or chlorine, alkyl with 1-8 carbon atoms, alkenyl with 3-4 carbon atoms, quinil with 3-4 carbon atoms, alkyl with 2 to 4 carbon atoms, substituted alkoxygroup with 1-6 carbon atoms, alkyl with 2 to 4 carbon atoms, polyamidine alkoxygroup with 1-4 carbon atoms in each group, alkyl with 2 to 4 carbon atoms, substituted alkylthiol with 1-4 carbon atoms, or cycloalkyl with 3-6 carbon atoms, in which one or two non-directly adjacent methylene groups may be replaced by oxygen atoms and/or sulfur, either unsubstituted or substituted by fluorine, chlorine, bromine, stands, ethyl, n-propylene, isopropyl, methoxy group, ethoxypropane, trifluoromethyl, cryptomaterial, cyano or nitro-group is phenyl, furanyl, pyridyl, thienyl or benzyl; or

A and D together represent landiolol group having 3-5 carbon atoms or alkantiolsul group having 3-5 carbon atoms in which one methylene hesameddini or substituted by fluorine or chlorine, by alkyl with 1-6 carbon atoms, alkoxygroup with 1-4 carbon atoms, alkylthiol with 1-4 carbon atoms, cycloalkyl with 3-6 carbon atoms, phenyl or benzyloxycarbonyl; or

G means hydrogen (a) or one of the groups

< / BR>
< / BR>
< / BR>
< / BR>
E (E) or

< / BR>
where E is the equivalent of a metal ion or ammonium ion;

L is an oxygen atom or a sulfur atom;

M is an oxygen atom or a sulfur atom;

R1means unsubstituted or substituted by fluorine or chlorine, alkyl with 1 to 14 carbon atoms, alkenyl with 2-14 carbon atoms, alkyl with 1-6 carbon atoms, substituted alkoxygroup with 1-4 carbon atoms, alkyl with 1-6 carbon atoms, substituted alkylthiol with 1-4 carbon atoms, alkyl with 1-4 carbon atoms, polyamidine arcoxia with 1-4 carbon atoms or unsubstituted or substituted by fluorine, chlorine, stands, ethyl, n-propylene, isopropyl, n-bootrom, isobutyl, tert. -bootrom, a methoxy group, ethoxypropane, n-propoxyphene or isopropoxycarbonyl cycloalkyl with 3-6 carbon atoms, in which one or two methylene groups may be replaced by oxygen atom and/or sulfur atom; unsubstituted or substituted by fluorine, chlorine, bromine, cyano, a nitro-group, stands, ethyl, n-propylene, isopro, methylsulfonium or ethylsulfonyl phenyl; unsubstituted or substituted by fluorine, chlorine, bromine, stands, ethyl, n-propylene, isopropyl, methoxy group, ethoxypropane, trifluoromethyl, cryptomaterial benzyl; unsubstituted or substituted by fluorine, chlorine, bromine, stands or ethyl furanyl, thienyl or pyridyl; unsubstituted or substituted by fluorine, chlorine, stands or ethyl peroxyacyl with 1-4 carbon atoms in the alkyl part, or unsubstituted or substituted by fluorine, chlorine, amino group, stands or ethyl peridiocally with 1-4 carbon atoms in the alkyl part, pyrimidinemethanol with 1-4 carbon atoms in the alkyl part or thiazoleacetate with 1-4 carbon atoms in the alkyl part;

R2means unsubstituted or substituted by fluorine or chlorine, alkyl with 1 to 14 carbon atoms, alkenyl with 2-14 carbon atoms, alkyl with 2-6 carbon atoms, substituted alkoxygroup with 1-4 carbon atoms or alkyl with 2-6 carbon atoms, polyamidine alkoxygroup with 1-4 carbon atoms in each group; unsubstituted or substituted by fluorine, chlorine, stands, ethyl, n-propylene, isopropyl or methoxy group cycloalkyl with 3-6 carbon atoms, or unsubstituted or substituted by fluorine, chlorine, cinegroupe what reformatorskomu phenyl or benzyl;

R3means unsubstituted or substituted by fluorine or chlorine, methyl, ethyl, propyl, isopropyl, butyl, tert. -butyl, either unsubstituted or substituted by fluorine, chlorine, bromine, stands, ethyl, isopropyl, tert. -bootrom, a methoxy group, ethoxypropane, isopropoxy-sing, trifluoromethyl, cryptomaterial, cyano or nitro-group is phenyl or benzyl;

R4and R5independently from each other, each represent unsubstituted or substituted by fluorine or chlorine, alkyl with 1-4 carbon atoms, alkoxy with 1-4 carbon atoms, alkylamino with 1-4 carbon atoms, dialkylamino with 1-4 carbon atoms in each alkyl group or alkylthio with 1-4 carbon atoms, either unsubstituted or substituted by fluorine, chlorine, bromine, nitro-group, cyano, stands, a methoxy group, a trifluoromethyl or cryptomaterial phenyl, phenoxy or phenylthio;

R6and R7independently from each other, each denote hydrogen, unsubstituted or substituted by fluorine or chlorine, alkyl with 1-4 carbon atoms, cycloalkyl with 3-6 carbon atoms, alkoxy with 1-4 carbon atoms, alkenyl with 3-4 carbon atoms or alkyl with 2 to 4 carbon atoms, substituted alkoxygroup with 1-4 carbon atoms, either unsubstituted or somewut unsubstituted or substituted by stands or ethyl alkalinity balance with 5-6 carbon atoms, in which one methylene group may be replaced by oxygen atom or a sulfur atom.

4. Compounds of General formula (II)

< / BR>
where a, b, X, Y and Z are specified in paragraph 1 values, and

R8means alkyl,

representing intermediate compounds to obtain 2,4,5-triple-substituted of fenilcetonuria formula (I) under item 1.

5. The compounds of formula (III)

< / BR>
where a, b, X, Y and Z are specified in paragraph 1 values

R8means alkyl,

representing intermediate compounds to obtain 2,4,5-triple-substituted of fenilcetonuria formula (I) under item 1.

6. The compounds of formula (XXI)

< / BR>
where a, b, X, Y and Z are specified in paragraph 1 values representing intermediate compounds to obtain 2,4,5-triple-substituted of fenilcetonuria formula (I) under item 1.

7. The compounds of formula (XXIX)

< / BR>
where a, b, X, Y and Z are specified in paragraph 1 values representing intermediate compounds to obtain 2,4,5-triple-substituted of fenilcetonuria formula (I) under item 1.

8. The compounds of formula (IV)

< / BR>
where a, b, X, Y and Z have the above meanings;

R8means alkyl;

W stands for hydrogen, halogen, alkyl or alkoxyl,

representing the FDS is soedineniya formula (VI)

< / BR>
where X, Y and Z are specified in paragraph 1 values;

Gal means chlorine or bromine,

representing intermediate compounds to obtain 2,4,5-triple-substituted of fenilcetonuria formula (I) under item 1.

10. The compounds of formula (XXXIII)

< / BR>
where X, Y and Z are specified in paragraph 1 values representing intermediate compounds to obtain 2,4,5-triple-substituted of fenilcetonuria formula (I) under item 1.

11. The compounds of formula (XXXIV)

< / BR>
where X, Y and Z have the above meanings;

R8means alkyl,

representing intermediate compounds to obtain 2,4,5-triple-substituted of fenilcetonuria formula (I) under item 1.

12. Means for controlling insects and arachnids that contains the active substance on the basis of substituted phenylethanol, characterized in that substituted phenylethanol it contains compounds of General formula (I)

< / BR>
where X means halogen, alkyl with 1-6 carbon atoms, alkenyl with 2-6 carbon atoms, quinil with 2-6 carbon atoms, alkoxy with 1-6 carbon atoms, halogenated with 1-4 carbon atoms, halogenoalkanes with 1-4 carbon atoms, a cyano or a nitro-group;

Y represents halogen, alkyl with 1-6 carbon atoms, al is the group or the nitro-group;

Z denotes halogen, alkyl with 1-6 carbon atoms, alkoxy with 1-6 carbon atoms, halogenated with 1-4 carbon atoms, halogenoalkanes with 1-4 carbon atoms, hydroxyl, cyano, a nitro-group or fenoxaprop, phenylthiourea, thiazoleacetate, pyridyloxy, primidealhalbgrouppen, personalantispy, phenylalkylamine with 1-4 carbon atoms in the alkyl part or phenylalkylamine with 1-4 carbon atoms in the alkyl part, each of which may be unsubstituted or substituted with halogen, alkyl with 1-4 carbon atoms, alkoxyl with 1-4 carbon atoms, halogenation with 1-4 carbon atoms, halogenation with 1-4 carbon atoms, the nitro-group, or cyano; or

Y and Z together denote unsubstituted or substituted with halogen, alkyl with 1-6 carbon atoms, alkoxyl with 1-6 carbon atoms or halogenation with 1-4 carbon atoms alcander with 3-4 carbon atoms or alkerdeel with 3-4 carbon atoms, where independently from each other from one to three links can be replaced by oxygen, sulfur, nitrogen or carbonyl group, and X is any one of the above values;

Het denotes one of the groups

< / BR>
< / BR>
< / BR>
< / BR>
< / BR>
where a represents hydrogen, unsubstituted or smeshannyi alkoxygroup with 1-10 carbon atoms, polyalkoxyalkyl with 1-8 carbon atoms in all alkyl groups or alkyl with 1-6 carbon atoms, substituted alkylthiol with 1-10 carbon atoms, unsubstituted or substituted with halogen, alkyl with 1-6 carbon atoms or alkoxygroup with 1-6 carbon atoms cycloalkyl with 3-8 carbon atoms, in which one or two methylene groups may be replaced by oxygen atom and/or sulfur atom, or unsubstituted or substituted by halogen, alkyl with 1-6 carbon atoms, halogenation with 1-6 carbon atoms, alkoxygroup with 1-6 carbon atoms, halogenlampe with 1-6 carbon atoms, cyano or nitro-group is phenyl, naphthyl, phenyl substituted by alkyl with 1-6 carbon atoms, naphthyl, substituted alkyl with 1-6 carbon atoms, or heteroaryl with 5 or 6 atoms in the cycle and from one to three heteroatoms from the series oxygen, sulphur and nitrogen;

In denotes hydrogen, alkyl with 1-12 carbon atoms or alkyl with 1-6 carbon atoms, substituted alkoxygroup with 1-8 carbon atoms; or

A, b and the carbon atom to which they are linked, represent cycloalkyl with 3-10 carbon atoms or cycloalkenyl with 5-10 carbon atoms in which one methylene group may be replaced by oxygen atom or sulfur atom and which is with 1-8 carbon atoms, alkoxygroup with 1-8 carbon atoms, alkylthiol with 1-8 carbon atoms, halogen or phenyl; or

A, b and the carbon atom to which they are linked, represent cycloalkyl with 5-6 carbon atoms which may be substituted with one or two oxygen atom and/or sulfur alkylenediamine group, or alkylenediamines or alkylenediamine group, which with the carbon atom to which they are attached, form an additional 5-8-membered ring; or

A, b and the carbon atom to which they are linked, represent cycloalkyl with 3-8 carbon atoms or cycloalkenyl with 5-8 carbon atoms, where two Deputy together with the carbon atoms to which they are linked, represent unsubstituted or substituted by alkyl with 1-6 carbon atoms, alkoxygroup with 1-6 carbon atoms or halogen alcander with 3-6 carbon atoms, alkerdeel with 3-6 carbon atoms or alkadienes with 4-6 carbon atoms in which one methylene group may be replaced by oxygen atom or a sulfur atom;

D is hydrogen, unsubstituted or substituted with halogen alkyl with 1-12 carbon atoms, alkenyl with 3-8 carbon atoms, quinil with 3-8 carbon atoms, alkyl of 2-8 carbon atoms, substituted alkoxygroup each, or alkyl of 2-8 carbon atoms, substituted alkylthiol with 1-10 carbon atoms; unsubstituted or substituted with halogen, alkyl with 1-4 carbon atoms, alkoxygroup with 1-4 carbon atoms or halogenation with 1-4 carbon atoms, cycloalkyl with 3-8 carbon atoms, in which one or two non-directly adjacent methylene groups may be replaced by oxygen atom and/or sulfur atom; or an unsubstituted or substituted with halogen, alkyl with 1-6 carbon atoms, halogenation with 1-6 carbon atoms, alkoxygroup with 1-6 carbon atoms, halogenlampe with 1-6 carbon atoms, cyano or nitro-group is phenyl, heteroaryl with 5-6 atoms in the cycle, and one or two heteroatoms from the series oxygen, sulphur and nitrogen, phenyl substituted by alkyl with 1-6 carbon atoms, or heteroaryl with 5-6 atoms in the cycle, and one or two heteroatoms from the series oxygen, sulfur and nitrogen substituted by alkyl with 1-6 carbon atoms; or

A and D together denote a group: alcander with 3-6 carbon atoms, alkerdeel with 3-6 carbon atoms or alkadienes with 4-6 carbon atoms in which one methylene group may be replaced by oxygen atom or sulfur atom and which is unsubstituted or substituted halog the carbon alkylthiophene with 1-6 carbon atoms, cycloalkene with 3-7 carbon atoms, phenyl or benzyloxycarbonyl or the other, forming secondinstance ring alkadienes group with 3-6 carbon atoms, arkendale group with 3-6 carbon atoms or acadieville group with 4-6 carbon atoms in which one methylene group in each case may be replaced by oxygen atom or sulfur atom and which is unsubstituted or substituted by alkyl with 1-6 carbon atoms; or

A and D together represent landiolol group with 3-6 carbon atoms or alkantiolsul group with 3-6 carbon atoms, which may contain one of the following groups:

< / BR>
< / BR>
< / BR>
< / BR>
< / BR>
< / BR>
< / BR>
< / BR>
or

< / BR>
G means hydrogen (a) or one of the groups

< / BR>
< / BR>
< / BR>
< / BR>
E (E) or

< / BR>
where E is the equivalent of a metal ion or ammonium ion;

L is an oxygen atom or a sulfur atom;

M is an oxygen atom or a sulfur atom,

R1means unsubstituted or substituted with halogen alkyl with 1-20 carbon atoms, alkenyl with 2-20 carbon atoms, alkoxyalkyl with 1-8 carbon atoms in both alkyl groups, alkylthiols with 1-8 carbon atoms in both alkyl groups, or Poliak the m with 1-6 carbon atoms or alkoxygroup with 1-6 carbon atoms cycloalkyl with 3-8 carbon atoms, in which one or two methylene groups may be replaced by oxygen atom and/or sulfur atom; unsubstituted or substituted with halogen, a cyano, a nitro-group, alkyl with 1-6 carbon atoms, alkoxygroup with 1-6 carbon atoms, halogenation with 1-6 carbon atoms, halogenoalkane group with 1-6 carbon atoms, alkylthiol with 1-6 carbon atoms or alkylsulphonyl with 1-6 carbon atoms phenyl; unsubstituted or substituted with halogen, a nitro-group, cyano, alkyl with 1-6 carbon atoms, alkoxygroup with 1-6 carbon atoms, halogenation with 1-6 carbon atoms or halogenoalkane group with 1-6 carbon atoms phenylalkyl with 1-6 carbon atoms in the alkyl part; unsubstituted or substituted by halogen or alkyl with 1-6 carbon atoms 5 - or 6-membered heteroaryl with one or two heteroatoms from the series oxygen, sulphur and nitrogen; unsubstituted or substituted by halogen or alkyl with 1-6 carbon atoms peroxyacyl with 1-6 carbon atoms in the alkyl part; unsubstituted or substituted with halogen, the amino group or alkyl with 1-6 carbon atoms 5 - or 6-membered heteroepitaxial with 1-6 carbon atoms in the alkyl portion with one or two heteroatoms from the series oxygen, sulphur and nitrogen;

R2
R3means unsubstituted or substituted with halogen alkyl with 1-8 carbon atoms or an unsubstituted or substituted with halogen, alkyl with 1-6 carbon atoms, alkoxygroup with 1-6 carbon atoms, halogenation with 1-4 carbon atoms, halogenlampe with 1-4 carbon atoms, cyano or nitro-group is phenyl or benzyl;

R4and R5independently from each other, each represent unsubstituted or substituted with halogen alkyl with 1-8 carbon atoms, alkoxy with 1-8 carbon atoms, alkylamino with 1-8 carbon atoms, dialkylamino with 1-8 carbon atoms in each alkyl group, alkylthio with 1-8 carbon atoms by alkoxygroup with 1-4 carbon atoms, halogenlampe with 1-4 carbon atoms, alkylthiol with 1-4 carbon atoms, halogeenilamppu with 1-4 carbon atoms, alkyl with 1-4 carbon atoms or halogenation with 1-4 carbon atoms, phenyl, phenoxy or phenylthio;

R6and R7independently from each other, each denote hydrogen, unsubstituted or substituted with halogen alkyl with 1-8 carbon atoms, cycloalkyl with 3-8 carbon atoms, alkoxy with 1-8 carbon atoms, alkenyl with 3-8 carbon atoms or alkyl of 2-8 carbon atoms, substituted alkoxygroup with 1-8 carbon atoms; unsubstituted or substituted with halogen, alkyl with 1-8 carbon atoms, halogenation with 1-8 carbon atoms or alkoxygroup with 1-8 carbon atoms, phenyl or benzyl, or together denote unsubstituted or substituted by alkyl with 1-6 carbon atoms alkalinity balance with 3-6 carbon atoms, in which one methylene group may be replaced by oxygen atom or a sulfur atom;

R13means hydrogen or unsubstituted or substituted by halogen alkyl with 1-8 carbon atoms or alkoxy with 1-8 carbon atoms, unsubstituted or substituted with halogen, alkyl with 1-4 carbon atoms or alkoxygroup with 1-4 carbon atoms, cycloalkyl with 3-8 atoms angle is s or substituted with halogen, by alkyl with 1-6 carbon atoms, alkoxygroup with 1-6 carbon atoms, halogenation with 1-4 carbon atoms, halogenlampe with 1-4 carbon atoms, a nitro-group or a cyano phenyl, phenylalkyl with 1-4 carbon atoms in the alkyl part or phenylalkyl with 1-4 carbon atoms in the CNS;

R14means hydrogen or alkyl with 1-8 carbon atoms; or

R13and R14together mean alcander with 4-6 carbon atoms;

R15and R16are identical or different and denote alkyl with 1-6 carbon atoms; or

R15and R16together mean ascandilwy residue with 2 to 4 carbon atoms which may be substituted by alkyl with 1-6 carbon atoms or phenyl, unsubstituted or substituted with halogen, alkyl with 1-4 carbon atoms, halogenation with 1-4 carbon atoms, alkoxygroup with 1-4 carbon atoms, halogenlampe with 1-4 carbon atoms, a nitro-group, or cyano;

R17and R18independently from each other, each denote hydrogen, unsubstituted or substituted with halogen alkyl with 1-8 carbon atoms, either unsubstituted or substituted with halogen, alkyl with 1-6 carbon atoms, alkoxygroup with 1-6 carbon atoms, halogenoalkane the

R17and R18together with the carbon atom to which they are linked, represent a carbonyl group, unsubstituted or substituted by alkyl with 1-4 carbon atoms or alkoxygroup with 1-4 carbon atoms, cycloalkyl with 5-7 carbon atoms in which one methylene group may be replaced by oxygen atom or a sulfur atom;

R19and R20independently from each other, each represent alkyl with 1-10 carbon atoms, alkenyl with 2-10 carbon atoms, alkoxy with 1-10 carbon atoms, alkylamino with 1-10 carbon atoms, alkenylamine with 3-10 carbon atoms, dialkylamino with 1-10 carbon atoms in each alkyl group or dialkylamino with 3-10 carbon atoms in each alkenylphenol group.

13. A method of combating insects and arachnids by affecting them and/or their habitat substituted phenylethanol, characterized in that as substituted phenylethanol used as a compound of General formula (I)

< / BR>
where X means halogen, alkyl with 1-6 carbon atoms, alkenyl with 2-6 carbon atoms, quinil with 2-6 carbon atoms, alkoxy with 1-6 carbon atoms, halogenated with 1-4 carbon atoms, halogenoalkanes with 1-4 carbon atoms, a cyano or a nitro-group;

Y angelegenheit with 1-4 carbon atoms, the cyano or nitro-group;

Z denotes halogen, alkyl with 1-6 carbon atoms, alkoxy with 1-6 carbon atoms, halogenated with 1-4 carbon atoms, halogenoalkanes with 1-4 carbon atoms, hydroxyl, cyano, a nitro-group or fenoxaprop, phenylthiourea, thiazoleacetate, pyridyloxy, primidealhalbgrouppen, personalantispy, phenylalkylamine with 1-4 carbon atoms in the alkyl part or phenylalkylamine with 1-4 carbon atoms in the alkyl part, each of which may be unsubstituted or substituted with halogen, alkyl with 1-4 carbon atoms, alkoxyl with 1-4 carbon atoms, halogenation with 1-4 carbon atoms, halogenation with 1-4 carbon atoms, the nitro-group, or cyano; or

Y and Z together denote unsubstituted or substituted with halogen, alkyl with 1-6 carbon atoms, alkoxyl with 1-6 carbon atoms or halogenation with 1-4 carbon atoms alcander with 3-4 carbon atoms or alkerdeel with 3-4 carbon atoms, where independently from each other from one to three links can be replaced by oxygen, sulfur, nitrogen or carbonyl group, and X is any one of the above values;

Het denotes one of the groups

< / BR>
< / BR>
< / BR>
< / BR>
< / BR>
where And aznaa, alkyl with 1-8 carbon atoms, substituted alkoxygroup with 1-10 carbon atoms, polyalkoxyalkyl with 1-8 carbon atoms in all alkyl groups or alkyl with 1-6 carbon atoms, substituted alkylthiol with 1-10 carbon atoms, unsubstituted or substituted with halogen, alkyl with 1-6 carbon atoms or alkoxygroup with 1-6 carbon atoms cycloalkyl with 3-8 carbon atoms, in which one or two methylene groups may be replaced by oxygen atom and/or sulfur atom, or unsubstituted or substituted by halogen, alkyl with 1-6 carbon atoms, halogenation with 1-6 carbon atoms, alkoxygroup with 1-6 carbon atoms, halogenlampe with 1-6 carbon atoms, cyano or nitro-group is phenyl, naphthyl, phenyl substituted by alkyl with 1-6 carbon atoms, naphthyl, substituted alkyl with 1-6 carbon atoms, or heteroaryl with 5 or 6 atoms in the cycle and from one to three heteroatoms from the series oxygen, sulphur and nitrogen;

In denotes hydrogen, alkyl with 1-12 carbon atoms or alkyl with 1-6 carbon atoms, substituted alkoxygroup with 1-8 carbon atoms; or

A, b and the carbon atom to which they are linked, represent cycloalkyl with 3-10 carbon atoms or cycloalkenyl with 5-10 carbon atoms, in which one m the sludge with 1-8 carbon atoms, cycloalkyl with 3-10 carbon atoms, halogenation with 1-8 carbon atoms, alkoxygroup with 1-8 carbon atoms, alkylthiol with 1-8 carbon atoms, halogen or phenyl; or

A, b and the carbon atom to which they are linked, represent cycloalkyl with 5-6 carbon atoms which may be substituted with one or two oxygen atom and/or sulfur alkylenediamine group, or alkylenediamines or alkylenediamine group, which with the carbon atom to which they are attached, form an additional 5-8-membered ring; or

A, b and the carbon atom to which they are linked, represent cycloalkyl with 3-8 carbon atoms or cycloalkenyl with 5-8 carbon atoms, where two Deputy together with the carbon atoms to which they are linked, represent unsubstituted or substituted by alkyl with 1-6 carbon atoms, alkoxygroup with 1-6 carbon atoms or halogen alcander with 3-6 carbon atoms, alkerdeel with 3-6 carbon atoms or alkadienes with 4-6 carbon atoms in which one methylene group may be replaced by oxygen atom or a sulfur atom;

D is hydrogen, unsubstituted or substituted with halogen alkyl with 1-12 carbon atoms, alkenyl with 3-8 carbon atoms, alkene is 8 carbon atoms, politeley alkoxygroup with 1-8 carbon atoms each, or alkyl of 2-8 carbon atoms, substituted alkylthiol with 1-10 carbon atoms; unsubstituted or substituted with halogen, alkyl with 1-4 carbon atoms, alkoxygroup with 1-4 carbon atoms or halogenation with 1-4 carbon atoms, cycloalkyl with 3-8 carbon atoms, in which one or two non-directly adjacent methylene groups may be replaced by oxygen atom and/or sulfur atom; or an unsubstituted or substituted with halogen, alkyl with 1-6 carbon atoms, halogenation with 1-6 carbon atoms, alkoxygroup with 1-6 carbon atoms, halogenlampe with 1-6 carbon atoms, cyano or nitro-group is phenyl, heteroaryl with 5-6 atoms in the cycle, and one or two heteroatoms from the series oxygen, sulphur and nitrogen, phenyl substituted by alkyl with 1-6 carbon atoms, or heteroaryl with 5-6 atoms in the cycle, and one or two heteroatoms from the series oxygen, sulfur and nitrogen substituted by alkyl with 1-6 carbon atoms; or

A and D together denote a group: alcander with 3-6 carbon atoms, alkerdeel with 3-6 carbon atoms or alkadienes with 4-6 carbon atoms in which one methylene group may be replaced by oxygen atom or TomTom, by alkyl with 1-10 carbon atoms, alkoxygroup with 1-6 carbon atoms, alkylthiol with 1-6 carbon atoms, cycloalkene with 3-7 carbon atoms, phenyl or benzyloxycarbonyl or the other, forming secondinstance ring alkadienes group with 3-6 carbon atoms, arkendale group with 3-6 carbon atoms or acadieville group with 4-6 carbon atoms in which one methylene group in each case may be replaced by oxygen atom or sulfur atom and which is unsubstituted or substituted by alkyl with 1-6 carbon atoms; or

A and D together represent landiolol group with 3-6 carbon atoms or alkantiolsul group with 3-6 carbon atoms, which may contain one of the following groups:

< / BR>
< / BR>
< / BR>
< / BR>
< / BR>
< / BR>
< / BR>
< / BR>
or

< / BR>
G means hydrogen (a) or one of the groups

< / BR>
< / BR>
< / BR>
< / BR>
E (E) or

< / BR>
where E is the equivalent of a metal ion or ammonium ion;

L is an oxygen atom or a sulfur atom;

M is an oxygen atom or a sulfur atom;

R1means unsubstituted or substituted with halogen alkyl with 1-20 carbon atoms, alkenyl with 2-20 carbon atoms, alkoxyalkyl with 1-8 carbon atoms in both alkyl groups, alkylic groups, either unsubstituted or substituted with halogen, alkyl with 1-6 carbon atoms or alkoxygroup with 1-6 carbon atoms cycloalkyl with 3-8 carbon atoms, in which one or two methylene groups may be replaced by oxygen atom and/or sulfur atom; unsubstituted or substituted with halogen, a cyano, a nitro-group, alkyl with 1-6 carbon atoms, alkoxygroup with 1-6 carbon atoms, halogenation with 1-6 carbon atoms, halogenlampe with 1-6 carbon atoms, alkylthiol with 1-6 carbon atoms or alkylsulphonyl with 1-6 carbon atoms phenyl; unsubstituted or substituted with halogen, a nitro-group, cyano, by alkyl with 1-6 carbon atoms, alkoxygroup with 1-6 carbon atoms, halogenation with 1-6 carbon atoms or halogenlampe with 1-6 carbon atoms phenylalkyl with 1-6 carbon atoms in the alkyl part; unsubstituted or substituted by halogen or alkyl with 1-6 carbon atoms 5 - or 6-membered heteroaryl with one or two heteroatoms from the series oxygen, sulphur and nitrogen; unsubstituted or substituted by halogen or alkyl with 1-6 carbon atoms peroxyacyl with 1-6 carbon atoms in the alkyl part; unsubstituted or substituted with halogen, amino or alkyl with 1-6 carbon atoms of the 5-series: oxygen, sulfur and nitrogen,

R2means unsubstituted or substituted with halogen alkyl with 1-20 carbon atoms, alkenyl with 2-20 carbon atoms, alkyl of 2-8 carbon atoms, substituted alkoxygroup with 1-8 carbon atoms, or alkyl of 2-8 carbon atoms, polyamidine alkoxygroup with 1-8 carbon atoms in each alkyl group; unsubstituted or substituted with halogen, alkyl with 1-6 carbon atoms or alkoxygroup with 1-6 carbon atoms cycloalkyl with 3-8 carbon atoms; or an unsubstituted or substituted with halogen, a cyano, a nitro-group, alkyl with 1-6 carbon atoms, alkoxygroup with 1-6 carbon atoms, halogenation with 1-6 carbon atoms or halogenlampe with 1-6 carbon atoms, phenyl or benzyl;

R3means unsubstituted or substituted with halogen alkyl with 1-8 carbon atoms or an unsubstituted or substituted with halogen, alkyl with 1-6 carbon atoms, alkoxygroup with 1-6 carbon atoms, halogenation with 1-4 carbon atoms, halogenlampe with 1-4 carbon atoms, cyano or nitro-group is phenyl or benzyl;

R4and R5independently from each other, each represent unsubstituted or substituted with halogen alkyl with 1-8 carbon atoms, alkoxy from 1 to 8 atoms in the tio with 1-8 carbon atoms or alkanity with 3-8 carbon atoms, or unsubstituted or substituted with halogen, a nitro-group, cyano, alkoxygroup with 1-4 carbon atoms, halogenlampe with 1-4 carbon atoms, alkylthiol with 1-4 carbon atoms, halogeenilamppu with 1-4 carbon atoms, alkyl with 1-4 carbon atoms or halogenation with 1-4 carbon atoms, phenyl, phenoxy or phenylthio;

R6and R7independently from each other, each denote hydrogen, unsubstituted or substituted with halogen alkyl with 1-8 carbon atoms, cycloalkyl with 3-8 carbon atoms, alkoxy with 1-8 carbon atoms, alkenyl with 3-8 carbon atoms or alkyl of 2-8 carbon atoms, substituted alkoxygroup with 1-8 carbon atoms; unsubstituted or substituted with halogen, alkyl with 1-8 carbon atoms, halogenation with 1-8 carbon atoms or alkoxygroup with 1-8 carbon atoms, phenyl or benzyl, or together denote unsubstituted or substituted by alkyl with 1-6 carbon atoms alkalinity balance with 3-6 carbon atoms, in which one methylene group may be replaced by oxygen atom or a sulfur atom;

R13means hydrogen or unsubstituted or substituted by halogen alkyl with 1-8 carbon atoms or alkoxy with 1-8 carbon atoms, unsubstituted or substituted kind, in which one methylene group may be replaced by oxygen atom or a sulfur atom, or unsubstituted or substituted by halogen, alkyl with 1-6 carbon atoms, alkoxygroup with 1-6 carbon atoms, halogenation with 1-4 carbon atoms, halogenlampe with 1-4 carbon atoms, a nitro-group or a cyano phenyl, phenylalkyl with 1-4 carbon atoms in the alkyl part or phenylalkyl with 1-4 carbon atoms in the CNS;

R14means hydrogen or alkyl with 1-8 carbon atoms; or

R13and R14together mean alcander with 4-6 carbon atoms;

R15and R16are identical or different and denote alkyl with 1-6 carbon atoms; or

R15and R16together mean ascandilwy residue with 2 to 4 carbon atoms which may be substituted by alkyl with 1-6 carbon atoms or phenyl, unsubstituted or substituted with halogen, alkyl with 1-4 carbon atoms, halogenation with 1-4 carbon atoms, alkoxygroup with 1-4 carbon atoms, halogenlampe with 1-4 carbon atoms, a nitro-group, or cyano;

R17and R18independently from each other, each denote hydrogen, unsubstituted or substituted with halogen alkyl with 1-8 atoms upggrade, halogenation with 1-4 carbon atoms, halogenlampe with 1-4 carbon atoms, a nitro-group or a cyano phenyl; or

R17and R18together with the carbon atom to which they are linked, represent a carbonyl group, unsubstituted or substituted by alkyl with 1-4 carbon atoms or alkoxygroup with 1-4 carbon atoms, cycloalkyl with 5-7 carbon atoms in which one methylene group may be replaced by oxygen atom or a sulfur atom;

R19and R20independently from each other, each represent alkyl with 1-10 carbon atoms, alkenyl with 2-10 carbon atoms, alkoxy with 1-10 carbon atoms, alkylamino with 1-10 carbon atoms, alkenylamine with 3-10 carbon atoms, dialkylamino with 1-10 carbon atoms in each alkyl group or dialkylamino with 3-10 carbon atoms in each alkenylphenol group.

Priority points and features:

28.06.19951 by 1-13 to the following values radicals: X is halogen, alkyl with 1-6 carbon atoms, alkoxy with 1-6 carbon atoms, halogenated with 1-4 carbon atoms, halogenoalkanes with 1-4 carbon atoms, a cyano or a nitro-group; Z means a halogen, alkyl with 1-6 carbon atoms, alkoxy with 1-6 carbon atoms, halogenated with 1-4 atoms wgnych radicals Y, Gets, a, b, D, G, E, L, M, R'-R8, R13- R20and Gal;

25.01.1996 on PP. 1-13 - for the following values radicals: X alkenyl with 2-6 carbon atoms, quinil with 2-6 carbon atoms; Z is hydroxyl, or fenoxaprop, phenylthiourea, thiazoleacetate, pyridyloxy, primidealhalbgrouppen, personalantispy, phenylalkylamine with 1-4 carbon atoms in the alkyl part or phenylalkylamine with 1-4 carbon atoms in the alkyl part, each of which may be unsubstituted or substituted with halogen, alkyl with 1-4 carbon atoms, alkoxyl with 1-4 carbon atoms, halogenation with 1-4 carbon atoms, halogenation with 1-4 carbon atoms, a nitro-group, or cyano; and for all these values of the remaining radicals Y, Gets, a, b, D, G, E, L, M, R1-R8, R13-R20and Gal.

 

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< / BR>
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< / BR>
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< / BR>
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< / BR>
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