C2-phenyl-substituted cyclic ketoenols

FIELD: organic chemistry.

SUBSTANCE: invention describes C2-phenyl-substituted cyclic ketoenols of the general formula: wherein W means hydrogen atom, alkyl with 1-6 carbon atoms; X means alkyl with 1-6 carbon atoms, alkenyl with 2-6 carbon atoms; Y means hydrogen atom, methyl, ethyl, isopropyl, alkenyl with 2-6 carbon atoms, ethynyl; Z means hydrogen atom, alkyl with 1-6 carbon atoms under condition that at least one of residues W, X, Y or Z means a chain with at least 2 carbon atoms but only one of residues X and Y can mean alkenyl with 2-6 carbon atoms; CKE means one of the following groups: , , and wherein A means hydrogen atom, alkyl with 1-6 carbon atoms; B means hydrogen atom, alkyl with 1-6 carbon atoms; A and B in common with carbon atom to which they are bound mean cycloalkyl with 5-6 carbon atoms wherein the ring carbon atom can be substituted with oxygen atom and can be substituted with alkyl with 1-6 carbon atoms or alkoxyl with 1-6 carbon atoms; A and B in common mean group of the formula: D means hydrogen atom or phenyl substituted with fluorine atom if CKE means group of the formula (4); G means hydrogen atom (a) or one of groups of the formula: or wherein R1 means alkyl with 1-6 carbon atoms, alkoxymethyl with 1-2 carbon atoms; R2 means alkyl with 1-4 carbon atoms; A and Q1 in common mean alkanediyl with 3-4 carbon atoms; Q2 means hydrogen atom. Invention provides preparing compound of the formula (I) possessing with insecticide, acaricide and herbicide activity.

EFFECT: valuable properties of compounds.

2 cl, 8 tbl, 32 ex

 

The invention concerns of ketoenols, more precisely With2-phenylsilane cyclic ketoenols.

Described pharmaceutical properties of 3-acyl-pyrrolidine-2,4-diones (S. Suzuki et al. Chem. Pharm. Bull. 15 1120 (1967)). Next R. Schmierer and H.Mildenberger synthesized N-phenylpyrrolidine-2,4-dione (Liebigs Ann. Chem. 1985, 1095). The biological activity of these compounds is not described.

In European patent application EP AND 0262399 and in the patent application in the UK of GB And 2266888 specified structural analogs of compounds (3-aryl-pyrrolidin-2,4-diones), herbicide, insecticide or acaricide action is not described. Known herbicides, insecticides or acaricides are unsubstituted bicyclic derivatives of 3-aryl-pyrrolidin-2,4-dione (European patent application EP AND 355599 and EP AND 415211)and substituted monocyclic derivatives of 3-aryl-pyrrolidin-2,4-dione (European patent application EP AND 377893 and EP AND 442077).

Known polycyclic derivatives of 3-arylpyrimidine-2,4-dione (European patent application EP AND 442073), and derived 1H-arylpyrimidine-dione (European patent application EP AND 456063, EP AND 521334, EP AND 596298, EP AND 613884, EP AND 613885, EP AND 0668267, international application WO 94/01 997, WO 95/26 954, WO 95/20572, WO 96/25395, WO 96/35664, WO 97/01 535, WO 97/02243, WO 97/36868, WO 97/43275, WO 98/05638, WO 98/06721, WO 98/25928, WO 99/16748 WO 99/24437, WO 99/43649, WO 99/48869 and WO 99/55673).

It is known that certain substituted derivatives of Δ3-hydrofuran-2-it have a weed-killing properties (see German patent application DE A 4014420). The synthesis used as starting compounds of tetronic acid derivatives (for example, 3-(2-methyl-phenyl)-4-hydroxy-5-(4-forfinal-Δ3dihydrofurane-(2)) is also described in German patent application DE AND 4014420. Structural analogs of compounds without specifying their insecticidal and/or acaricidal activity described in Campbell et al., J. Chem. Soc., Perkin Trans I, in 1985, (8), 1567-76. From European patent applications EP AND 528156, EP AND 0647637 and international patent applications WO 95/26 345, WO 96/20 196, WO 96/25 395, WO 96/35 664, WO 97/01 535, WO 97/02 243, WO 97/36 868, WO 98/05638, WO 98/25928, WO 99/16748, WO 99/43649, WO 99/48869 and WO 99/55673 known derivatives of 3-aryl-Δ3dihydrofurane with herbicide, acaricide and insecticide properties. Also known derivatives of 3-aryl-Δ3dihydrothebainone (international application WO 95/26345, 96/25395, WO 97/01535, WO 97/02243, WO 97/36868, WO 98/05638, WO 98/25928, WO 99/16748, WO 99/43649, WO 99/48869, WO 99/55673).

Known unsubstituted phenyl ring derivatives phenylpyrrole (see ..Chirazi, Torre und E.Ziegler, Arch. Pharm. 309, 558 (1976) and K.-N. Boltze und K. Heidenbluth, Chem. Ber. 91, 2849), and their possible use as pesticides are not specified. Substituted on the phenyl ring derivatives Panalpina with herbicide, acaricidal and insecticidal properties are described in European patent application EP AND 588137, in international patent applications WO 96 725 395, WO 96/35 664, WO 97/01 535, WO 97/02 243, WO 97/16 436, WO 97/19 941, WO 97/36 868, WO 98/0563, WO 99/43649, WO 99/48869 and WO 99/55673.

Also known unsubstituted on the phenyl ring derivatives of 5-phenyl-1,3-thiazine (see E.Ziegler und E.Steiner, Monatsh. 95, 147 (1964), R.Ketcham, T.Kappe und E.Ziegler, J.Heterocycl. Chem. 10, 223 (1973)), and the possible use of these compounds as pesticides are not specified. In the international patent applications WO 94/14 785, WO 96/02539, WO 96/35664, WO 97/01535, WO 97/02243, WO 97/02243, WO 97/36868, WO 99/05638, WO 99/43649, WO 99/48869 and WO 99/55673 described substituted on the phenyl ring derivatives of 5-phenyl-1,3-thiazine with herbicide, acaricide and insecticide activity.

It is known that certain substituted 2-arylcyclohexylamine have herbicide and acaricidal properties (see, for example, U.S. patent US-4283348; 4338122; 4436666; 4526723; 4551547; 4632698; international application WO 96/01798; WO 96/03366, WO 97/14667 and WO 98/39281, WO 99/43649, WO 99/48869, WO 99/55673). In addition, well-known close substituted derivatives: 3-hydroxy-5,5-dimethyl-2-vinylcyclopentane-2-EN-1-he from the publication Micklefield et al., Tetrahedron, (1992), 7519-26 and natural substance involution (-)-CIS-5-(3,4-dihydroxyphenyl)-3,4-dihydroxy-2-(4-hydroxyphenyl)-cyclopent-2-EN-he from the publication of Edwards et al., J. Chem. Soc. S, (1967), 405-9. Their insecticidal or acaricidal action are not described. In addition, from J. Economic Entomology, 66, (1973), 584 and is lined with application DE-a 2361084 known 2-(2,4,6-trimetilfenil)-1,3-indandione with indication of its herbicide and acaricidal action.

It is known that some of nesennye 2-arylcyclohexylamine have herbicide and acaricidal properties (U.S. patent US-4175135, 4209432, 4256657, 4256658, 4256659, 4257858, 4283348, 4303669, 4351666, 4409153, 4436666, 4526723, 4613617, 4659372, German patent application DE-a 2813341, and Wheeler, T.N., J. Org. Chem. 44,4906 (1979)), the international application WO 99/43649, WO 99/48869, WO 99/55673).

However, the effectiveness and breadth of action of these compounds is not always completely satisfactory, particularly at low concentrations and flow rates. In addition, the compatibility of plants with these compounds is not always sufficient.

The objective of the invention is to expand the range of compounds which possess insecticidal, acaricidal and herbicide activity.

The objective of the invention is solved by a C2-phenylselenenyl cyclic ketoenols General formula (I)

in which

W is hydrogen, alkyl with 1-6 carbon atoms,

X is alkyl with 1-6 carbon atoms, alkenyl with 2-6 carbon atoms,

Y is hydrogen, methyl, ethyl, isopropyl, alkenyl with 2-6 carbon atoms, ethinyl,

Z is hydrogen, alkyl with 1-6 carbon atoms,

provided that at least one of the residues W, X, Y or Z means a chain of at least 2 carbon atoms, and only one of the residues X and Y can mean alkenyl with 2-6 carbon atoms,

The NEC means one of the groups

where a is the waters of the genus, alkyl with 1-6 carbon atoms,

In hydrogen, alkyl with 1-6 carbon atoms,

A and b together with the carbon atom to which they are connected, means cycloalkyl with 5-6 carbon atoms in which the carbon atom of the ring may be replaced by oxygen, and which may be substituted by alkyl with 1-6 carbon atoms or alkoxyl with 1-6 carbon atoms,

A and b together mean a group

D is hydrogen or substituted by fluorine, phenyl, if the NEC shall mean a group of the formula (3),

G is hydrogen (a) or one of the groups

where

R1means alkyl with 1-6 carbon atoms, alkoxymethyl with 1-2 carbon atoms,

R2means alkyl with 1-4 carbon atoms,

And Q1together mean alcander with 3-4 carbon atoms and

Q2means hydrogen.

The compounds of formula (I) can also, depending on the type of substituents exist as geometric and/or optical isomers or mixtures of isomers of different composition, which can be separated, if necessary, in the usual way. The object of the present invention are as pure isomers and mixtures of isomers, their preparation and use, as well as the containing means. In the future, always speaks simply of the compounds of formula (I), but nevertheless, it refers to how the Chi is the train of connections, so, if necessary, and mixed with different proportions of isomeric compounds.

When the NEC group has a value from(1), (2) (3) (4), obtain the following main structures (I-1) to (I-7):

where

A, B, D, G, Q1, Q2, W, X, Y and Z have the above values.

When the NEC defines a group (1), for different values of (a), (b) and (C) of a group G are obtained the following main structures (I-1-a) to (I-1):

where

A, b, D, W, X, Y, Z, R1and R2have the above values.

When the NEC defines a group (2), for different values of (a), (b) and (C) of a group G are obtained the following main structures (I-2-a) to (I-2-c)

where

A, b, W, X, Y, Z, R1and R2have the above values.

The compounds of formula (I-3) depending on the position of the substituent G can exist in two isomeric forms (I-3-a) and (I-3-C).

what is expressed by a dotted line in the formula (I-3).

Compounds of formula (I-3-a) and (I-3) can exist in the form of a mixture, and in four the e pure isomers. A mixture of compounds of formula (I-3-a) and (I-3) can be divided in a known manner by physical methods, for example chromatographic methods.

For reasons of better clarity in the future are presented, respectively, only one of the possible isomers. This does not exclude the fact that the compounds can be optionally in the form of mixtures of isomers or in the respective other isomeric form.

When the NEC defines a group (3), for different values of (a), (b) and (C) of a group G are obtained the following main structures (I-3-a) to (I-3-C)

where

A, D, W, X, Y, Z, R1and R2have 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-a) and (I-4)

what is expressed by a dotted line in the formula (I-4).

Compounds of formula (I-4-a) and (I-4) can exist in the form of mixtures and in the form of pure isomers. A mixture of compounds of formula (I-4-a) and (I-4-b) can, if necessary, be divided in a known manner by physical methods, for example chromatographic methods.

For reasons of better clarity in the future are presented, respectively, only one prob is the author of isomers. This does not exclude the fact that the compounds can exist, if necessary, in the form of mixtures of isomers or in the respective other isomeric form.

The different values of (a), (b) and (C) of a group G are obtained the following main structures (I-4-a) to (I-4-C):

where

A, b, Q1, Q2, W, X, Y, Z, R1and R2have the above values.

The compounds of formula (I) is obtained by carrying out the following reactions:

(A) Substituted 3-phenylpyrrolidine-2,4-diones or their enols of the formula (I-1-a)

in which

A, b, D, W, X, Y and Z have the above values,

are obtained by the intramolecular condensation of ether N-acylamino-acid of the formula (II)

in which

A, b, D, W, X, Y and Z have the above meanings, and

R8means alkyl (preferably alkyl with 1-6 carbon atoms),

in the presence of a solvent and base.

(C) Substituted derivative 3-phenyl-4-hydroxy-Δ3dihydrofurane formula (I-2-a)

in which

A, b, W, X, Y and Z have the above values,

are obtained by the intramolecular condensation of ether carboxylic acids of the formula (III)

inwhich

A, b, W, X, Y, Z, and R8have the above values,

in the presence of a solvent and base.

(C) New substituted derivatives of 3-phenylpyrrole formula (I-3-a)

in which

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

receive by reacting carbonyl compounds of the formula (V)

in which

A and D have the above values,

or similaralcohol ether of the formula (Va)

in which

A, D and R8have the above values,

with halogenerator Kamenovo acid of formula (VI)

in which

W, X, Y and Z have the above meanings and

Hal means halogen (mainly chlorine or bromine),

if necessary, in the presence of a solvent and optionally in the presence of acid binding tools.

(D) Compounds of the formula (I-4-a)

in which

A, b, Q1, Q2, W, X, Y and Z have the above values,

obtained by intramolecular cyclization of the ester ketocarboxylic acids of the formula (VIII)

in which

A, b, Q1, Q2, W, X, Y and Z have the above meanings, and

R8means alkyl (in particular, Akil with 1-8 carbon atoms),

p is necessary, in the presence of a solvent and in the presence of a base.

(E) Compounds of the above formulas from (I-1(a-C)) to (I-4(a-C))where a, b, D, G, Q1, Q2, W, X, Y and Z have the above values,

and X or Y mean

R22means hydrogen or alkyl with 1-4 carbon atoms, preferably hydrogen or alkyl with 1-2 carbon atoms, and especially preferably hydrogen, or Y means ethinyl,

produced by interaction of the compounds of formulas (I-1') to (I-4')

in which

A, b, D, G, Q1, Q2, W, X' and Z have the above values, Y' represents chlorine, bromine, iodine, preferably bromine,

with silylation formula (X-a)

or, by the interaction of the compounds of formulas (I-1') to (1-4'),

in which

A, b, D, G, Q1, Q2, W and Z have the above meanings, and one of the residues X' or Y' have the above meanings, in addition to alkenyl, and other means chlorine, bromine, iodine, preferably bromine,

with vinylstyrene formula (X-b)

where

Alk preferably denotes alkyl with 1-4 carbon atoms,

R21preferably denotes alkyl with 1-4 carbon atoms or phenyl,

R22who appoints hydrogen or alkyl with 1-4 carbon atoms, especially preferably hydrogen or alkyl with 1-2 carbon atoms and very particularly preferably hydrogen,

in the presence of a solvent, if necessary, in the presence of base and catalyst, and the catalyst used, in particular, complexes of palladium.

(F) Compounds of the above formulas (I-1-b) to (I-4-b)in which a, b, D, Q1, Q2, R1, W, X, Y and Z have the above meanings, is produced by interaction of the compounds of the above formulas (I-1-a) to (I-4-a)in which a, b, D, Q1, Q2, W, X, Y and Z have the above values,

(α) halogenerator acid of formula (XI)

in which

R1have the above values and

Hal means halogen (in particular chlorine or bromine)

or

(β) with anhydrides of carboxylic acids of the formula (XII)

in which

R1have the above values,

if necessary, in the presence of a solvent and optionally in the presence of acid binding means;

(G) compounds of formulas (I-1) to (I-4-c), where a, b, D, Q1, Q2, R2, W, X, Y and Z have the above values,

produced by interaction of the compounds of formulas (I-1-a) to (I-4-a)in which a, b, D, Q1, Q2, W, X, Y and Z have the above values,

since ether is Harbourview acid or tieferen Harborview acid of the formula (XIII)

in which

R2has the above value,

if necessary, in the presence of a solvent and optionally in the presence of acid binding tools.

The above General or preferred definitions and the corresponding values of residues can arbitrarily be mutually combined. This applies accordingly to the final products, semi-finished and intermediate products.

Saturated or unsaturated hydrocarbon residues such as alkyl or alkenyl, also United with heteroatoms, such as in alkoxy, can be under the circumstances with a straight chain or branched.

Substituted residues may be single - or multi-substituted, unless otherwise specified, and during the repeated substitution, the substituents may be the same or different.

In particular, apart from those mentioned in the examples produce compounds shall contain the following compounds of formula (I-1-a):

Table 2:
A, b and D as stated in table 1
W stands for CH3, X is CH3, Y represents CH=CH2Z means N.
Table 3:
A, b and D as stated in table 1
W stands for CH3X means2H5, Y represents CH3Z means N.
Table 4:
A, b and D as stated in table 1
W stands for CH3, X is CH3, Y means With2H5Z means N.
Table 5:
A, b and D as stated in table 1
W means2H5X means2H5, Y represents CH3Z means N.

Table 6:

A, b and D as stated in table 1
W stands for C2H5, X is C2H5, Y means With2H5Z means N.
Table 7:

A, b and D as stated in table 1
W stands for CH3X means C=CH2, Y represents CH3Z means N.
Table 8:

A, b and D as stated in table 1
W stands for CH3X means2H5, Y means With2H5, Z OSN which includes N.
Table 9:

A, b and D as stated in table 1
W is N, X is CH3, Y means With≡SN, Z means N.
Table 10:

A, b and D as stated in table 1
W is N, X is CH3Y means C=CH2Z means N.
Table 11:

A, b and D as stated in table 1
W is N, X is C2H5, Y represents CH3Z means N.
Table 12:

A, b and D as stated in table 1
W is N, X is CH3, Y means With2H5Z means N.
Table 13:

A, b and D as stated in table 1
W is N, X is CH3, Y represents N, Z means With2H5.
Table 14:

A, b and D as stated in table 1
W is N, X is CH3, Y represents CH3Z means With2H5.

In particular, apart from those mentioned in the examples produce compounds shall contain the following compounds of formula (I-2-a):

Table 16:

A and b as indicated in table 15
W stands for CH3, X is CH3Y means C=CH2Z means N.
Table 17:

A and b as indicated in table 15
W stands for CH3X means2H5, Y represents CH3Z means N.
Table 18:

A and b as indicated in table 15
W stands for CH3, X is CH3, Y represents C2H5Z means N.
Table 19:

A and b as indicated in table 15
W stands for C2H5X means2H5, Y represents CH3Z means N.
Table 20:

A and b as indicated in table 15
W means2H5X means2H5, Y means With2H5Z means N.
Table 21:

A and b as indicated in table 15
W stands for CH3X means≡CH, Y represents CH3Z means N.
Table 22:

A and b as indicated in table 15
W stands for CH3X means C=CH2, Y represents CH3Z means N.
Table 23:

A and b as indicated in table 15
W stands for CH3X means2H5, Y represents C2H5Z means N.
Table 24:

A and b as indicated in table 15
W is N, X is CH3, Y means With≡SN, Z means N.

Table 25:

A and b as indicated in table 15
W is N, X is CH3Y means C=CH2Z means N.
Table 26:

A and b as indicated in table 15
W is N, X is C2H5, Y represents CH3Z means N.
Table 27:

A and b as indicated in table 15
W is N, X is CH3, Y represents C2H5Z means N.
Table 28:

A and b as indicated in table 15
W is N, X is CH3, Y represents N, Z means With2H5.
Table 29:

A and b as specified in the table is itzá 15
W is N, X is CH3, Y represents CH3Z means With2H5.

If according to the method (A) as the original product using ethyl ester of N-(2-methyl-4-ethinyl-phenylacetyl)-1-aminocyclohexanecarboxylic acid, the process can be represented by the following reaction scheme:

If according to the method (C) using ethyl ester O-(2,4,6-tietilperazin)-2-hydroxyisovaleric acid, the process can be represented by the following reaction scheme:

If, for example, according to method (C) as a source of products used (chlorocarbonyl)-2-(2-ethyl-4,6-dimethyl)-phenyl)-ketene and acetone, the process can be represented by the following reaction scheme:

If according to process (D) use the ethyl ester of 5-(2,4-diethyl-6-were)-2,3-tetramethylene 4-oxo-valerianic acid, the process can be represented by the following reaction scheme:

If according to process (E) using 3-[(2,6-dimethyl-4-bromo)-phenyl]-4,4-(pentamethylene)-pyrrolidin-2,4-dione as starting product, the process can be represented by the following reaction scheme:

If according to the method (Fα ) using 3-(2,6-dimethyl-4-ethynylphenyl)-5,5-dimethylpyrimidin-2,4-dione and pivaloyloxy as the original products, the process can be represented by the following reaction scheme:

Required for process (A) as starting compounds, the compounds of formula (II)

in which

A, b, D, W, X, Y, Z, and R8have the above values,

are new connections.

Esters of acylaminoacyl formula (II) are obtained, for example, by acylation of the derived amino acid of formula (XXI)

in which

A, b, R8and D have the above values,

replaced by halogenide phenylacetic acid of the formula (XXII)

in which

W, X, Y and Z have the above meanings, and

Hal means chlorine or bromine

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

or tarifitsirovannyim of acylaminoacyl formula (XXIII)

in which

A, b, D, W, X, Y and Z have the above values (Chem. Ind. (London) 1568 (1968)).

The compounds of formula (XXIII)

in which

A, b, D, W, X, Y and Z have the above values,

are new.

The compounds of formula formula (XXIII) are obtained, for example, by acylation according to the SCHOTT-Broumana and is of inoculat formula (XXIV)

in which a, b and D have the above values,

replaced by halogenide phenylacetic acid of the formula (XXII)

in which

W, X, Y and Z have the above meanings, and

Hal means chlorine or bromine (Organikum, VEB Deutschler Verlag der Wissenschaften, Berlin 1977, S.505).

The compounds of formula (XXII) are new. They are obtained by known methods (for example, Napesco, Houben-Weyl, Methods der Organischen Chemie, Bd. 8, S.467-469 (1952)).

The compounds of formula (XXII) are obtained, for example, the interaction of substituted phenylacetic acids of the formula (XXV)

in which

W, X, Y and Z have the above values,

with calodromini means (for example, thionyl chloride, tierbroker, oxalicacid, phosgene, phosphorus trichloride, tribromide phosphorus or pentachloride phosphorus), if necessary, in the presence of a diluent (for example optionally chlorinated aliphatic or aromatic hydrocarbon, such as toluene or methylene chloride) at a temperature of from -20°to 150°C, preferably from -10°to 100°C.

The compounds of formula (XXI) and (XXIV) partially known and/or can be obtained by known methods (see, for example, Compagnon, Miocque Ann. Chim. (Paris) [14] 5, S.11-22, 23-27 (1970)).

Substituted cyclic aminocarbonyl acid Faure the uly (XXIV), in which a and b form a ring, get, in General, the methods available through the reaction of Bucherer-Berg or method Striker in respective different isomeric forms. So under the reaction conditions of Bucherer-Berg receive predominantly the isomers (hereinafter for simplicity as specified β-isomers), in which the residues R and the carboxyl group are Equatorial, while the synthesis conditions on Striker receive predominantly the isomers (hereinafter for simplicity as specified α-isomers)in which the amino group and the residues R are Equatorial

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

Hereinafter, used in the above process (A) of starting compound of the formula (II)

in which

A, b, D, W, X, Y, Z, and R8have the above values,

produced by interaction of aminonitriles formula (XXVI)

in which

A, b and D have the above values,

with substituted halogenide phenylacetic acid of the formula (XXII)

in which

W, X, Y, Z and Hal have the above values,

obtaining compounds of formula (XXVII)

in which a, b, D, W, X, Y, and Z they who have the above values,

and subsequent acidic alcoholysis.

The compounds of formula (XXVII) are also new.

Used in process (C) of starting compound of the formula (III)

in which

A, b, W, X, Y, Z, and R8have the above values,

also are new.

Get them known methods.

So obtaining compounds of formula (III) is carried out, for example, by acylation of ester 2-hydroxycarbonic acid of the formula (XXVIII)

in which a, b and R8have the above values,

replaced by halogenide phenylacetic acid of the formula (XXII)

in which

W, X, Y, Z and Hal have the above values (Chem. Reviews 52, 237-416 (1953)).

Further, the compounds of formula (III) is obtained by alkylation of substituted phenylacetic acids of the formula (XXV)

in which

W, X, Y and Z have the above values,

esters α-haloalkaliphilic acids of the formula (XXIX)

in which a, b and R8have the above values and

Hal represents chlorine or bromine.

The compounds of formula (XXV) are also new.

The compounds of formula (XXIX) are commercially available.

The compounds of formula (XXV)

in which

W, X, Y and Z have the above the data values

and Y, can also mean

can be obtained by saponification of esters of phenylacetic acid of formula (XXX)

in which W, X, Y, Z, and R8have the above values,

in the presence of acid or base, in the presence of solvent in the usual well-known standard conditions.

The compounds of formula (XXX) are new.

The compounds of formula (XXX)

in which W, X, Y, Z, and R8have the above values,

and Y also can mean

get, for example, by the interaction of the ester of phenylacetic acid of the formula (XXX-a)

in which R8, W, X and Z have the above meanings and Y represents chlorine, bromine or iodine, in particular bromine,

with silylation formula (X-a)

or interaction of the ester of phenylacetic acid of the formula (XXX-a)

in which R8, W and Z have the above meanings, and one of the residues X and Y have the above meanings, in addition to alkenyl, and other means chlorine, bromine, iodine, preferably bromine,

with vinylstyrene formula (X-b)

in which Alk is preferably denotes alkyl with 1-4 carbon atoms,

R21preferably means alkyl is of 1-4 carbon atoms or phenyl,

R22have the above values,

in the presence of a solvent, if necessary, in the presence of a base and a catalyst (preferably palladium complexes).

Esters of phenylacetic acid of the formula (XXX-a) partially known from international application WO 96/35664, WO 97/02243, WO 97/01535, WO 97/36868 or WO 98/05638 or they can be produced is described there ways.

Obtaining esters of phenylacetic acid of formula (XXX) can be done in following ways (H) and (I).

Used in the above process (C) as starting compounds galoidirovaniya formula (VI) are new compounds. Get them known methods (see, for example, Org. Prep. Proced. Int, 7, (4), 155-158, 1975, and German patent application DE 1 945 703). Thus, the compounds of formula (VI)

in which W, X, Y and Z have the above meanings and

Hal signifies chlorine or bromine,

produced by interaction of substituted phenylmalonic acids of the formula (XXXII)

in which W, X, Y and Z have the above values,

with halogenide acids, such as, for example, thionyl chloride, phosphorus (V) chloride, phosphorus(III)chloride, oxalicacid, phosgene or tierbroker if necessary, in the presence of catalysts, as for example, dimethylformamide, methyl-steelframed or triphenylphosphine, and if not what bademosi, in the presence of bases, such as pyridine or triethylamine.

Substituted phenylmalonamide acid of the formula (XXXII) are new compounds. It can be obtained in a simple manner by known methods (see, for example, Organikum, VEB Deutschler Verlag der Wissenschaften, Berlin 1977, S.517, European patent application EP AND 528156, international application WO 96/35664, WO 97/02243, WO 97/01535, WO 97/36868 and WO 98/05638).

So, phenylmalonamide acid of the formula (XXXII)

in which W, X, Y and Z have the above values,

produced by saponification of esters phenylmalonate acid of the formula (XXXIII)

in which

W, X, Y, Z, and R8have the above values,

first, in the presence of base and solvent, followed by careful acidification (European application EP-528156, international application WO 96/35664, WO 97/02243).

Esters of malonic acids of formula (XXXIII)

in which

W, X, Y, Z, and R8have the above values are partly known compounds.

You can get them in the usual well-known organic chemistry methods (see Tetrahedron Lett. 27, 2763 (1986), Organikum, VEB Deutschler Verlag der Wissenschaften, Berlin 1977, S.587 ff, international application WO 96/35664, WO 97/02243, WO 97/01535, WO 97/36868, WO 98/05638 and WO 99/47525).

Required for process (C) as a source of carbonyl compounds the major derivatives of the formula (V)

in which

A and D have the above values,

or killenaule esters of the formula (Va)

in which

A, D and R8have the above values,

are known commercially available compounds or can be obtained by known methods.

Necessary for carrying out the above process (D) as starting compounds, the compounds of formula (VIII)

in which

A, b, Q1, Q2, W, X, Y, Z, and R8have the abovementioned meanings, are new compounds.

They can be obtained by known methods.

Esters of 5-aryl-4-ketocarboxylic acids of the formula (VIII), for example, obtained by esterification (see, for example, Organikum, 15th. Auflag, Berlin, 1977, page 499) or alkylation (see example receipt) 5-aryl-4-ketocarboxylic acids of the formula (XXXIV)

in which

W, X, Y, Z, A, B, Q1and Q2have the above values.

5-Aryl-4-ketocarboxylic acids of the formula (XXXIV)

in which

A, b, Q1, Q2, W, X, Y and Z have the abovementioned meanings, are new compounds. However, they can be obtained by known methods (see example receipt).

5-Aryl-4-ketocarboxylic acids of the formula (XXXIV) the floor shall be given, for example, decarboxylation of the ester 2-phenyl-3-oxo-adipic acid of the formula (XXXV)

in which

A, b, Q1, Q2, W, X, Y and Z have the above meanings and

R8and R8'mean alkyl (in particular, alkyl with 1-8 carbon atoms), and

when using compounds of formula (XXXVII) R8means hydrogen, optionally in the presence of a diluent and optionally in the presence of a base or acid (see, for example, Organikum, 15th. Auflag, Berlin, 1977, page 519-521).

The compounds of formula (XXXV)

in which

A, b, Q1, Q2, W, X, Y, Z, R8, R8'have the above values and

when using compounds of formula (XXXVII) R8means hydrogen,

are new connections.

The compounds of formula (XXXV) are obtained, for example, by acylation of the acid chloride of Palmyra carboxylic acid of the formula (XXXVI)

in which

A, b, Q1, Q2and R8have the above values and

Hal signifies chlorine or bromine,

or carboxylic acid anhydride of the formula (XXXVII)

in which

A, b, Q1and Q2have the above values,

ester of phenylacetic acid of formula (XXX)

in which W, X, Y, Z and R 8'have the above values,

in the presence of a diluent and base (see MS. Chambers, E.J.Thomas, D.J.Williams, J. Chem. Soc. Chem. Commun., (1987), 1228, as well as examples of receipt).

Compounds of formula (XXXVI) and (XXXVII) partially known from organic chemistry and/or can be obtained well-known simple methods.

The compounds of formula (XXX) is already described in the first stages of the process (B) or described as examples in the following processes (H) and (I).

(H) Compounds of the formula (XXX)

in which

W, X, Y, Z, and R8'have the above values,

get recovery esters atsilfyenilalanil acid of the formula (XLII)

in which

W, X, Y, and R8'have the above meanings and Z' represents an alkyl,

if necessary, in the presence of a solvent appropriate reagents (e.g., Zn/HCL, hydrogen/catalyst, hydrazine/base).

The compounds of formula (XLII) are new.

The compounds of formula (XLII)

in which

W, X, Y, Z' and R8'have the above values,

obtained by acylation according to the Friedel-Crafts esters of phenylacetic acid of the formula (XXX-b)

in which W, X, Y, and R8'have the above meanings and Z denotes hydrogen,

if necessary, in the presence of p is storytale anhydride or acid chloride of the carboxylic acid in the presence of an acid or Lewis acid (for example, aluminofluoride, bromide iron (III)).

Compound (XXX-b) are known or can be obtained is described in the cited literature methods.

(I) Esters of phenylacetic acid of formula (XXX)

in which

X is alkyl,

W, Y and Z denotes hydrogen or alkyl and

R8'means alkyl,

get dihalogenoalkane esters of phenylacetic acid of the formula (XXX-s)

in which

X is alkyl,

R8'means alkyl and at least one of the substituents W, Y, and Z, along with hydrogen and alkyl denotes chlorine or bromine,

in the presence of a solvent and a reducing agent (e.g. hydrogen in the presence of a catalyst of a noble metal such as palladium or platinum).

The compounds of formula (XXX) is known from the above patent applications, or you can get them described in methods.

Required for the above process (E) as starting compounds, the compounds of formulas from (I-1 a) to (I-4'-(a)in which a, b, D, Q1, Q2, W', X', Y' and Z' have the above meanings, partially known (international patent application WO 96/35664, WO 97/02243, WO 97/01535, WO 97/36868, WO 98/05638) or can be obtained by the methods described there.

Compounds of formula (X-a), and (X-b)

in which Alk, R21and R22have the above values,

partially sold or can be made simple by known methods.

In addition, necessary for carrying out process (F), (G) as starting compounds galodamadruga acids of the formula (XI) anhydrides of carboxylic acids of the formula (XII), esters of glamourising acid of the formula (XIII) are known organic and accordingly inorganic chemistry connections.

Compounds of formula (V), (XI), (XII), (XIII), (XXI), (XXIV), (XXVI), (XXVIII), (XXIX), (XXXVI) and (XXXVII) is known from the above references to the prior art and/or can be obtained by the methods described there.

Method (A) is characterized by the fact that the compounds of formula (II)in which a, b, D, W, X, Y, Z, and R8have the above meanings, is subjected to intramolecular condensation in the presence of a base.

As diluents in method (A) can be used all inert organic solvents. Mostly use hydrocarbons, such as toluene and xylene, then 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, and also alcohols, such as methanol, ethanol, propanol, isopropanol, butanol, and butanol and tert-butanol.

When carrying out process (A) as a basis (deprotonation funds) can be used with all common acceptors of protons. Mostly use the oxides of alkali and alkaline earth metals, hydroxides and carbonates, such as sodium hydroxide, potassium hydroxide, magnesium oxide, calcium oxide, sodium carbonate, potassium carbonate and calcium carbonate, in the presence of phase transfer catalysts, such as triethylmethylammonium, tetrabutylammonium, Adogen 464 (metyltrebutyl(C8-C10)ammoniacal) or TDA 1 (Tris-(methoxyethoxymethyl)-Amin). Used alkaline metals such as sodium or potassium. Used, amides and hydrides of alkali and alkaline earth metals, such as sodium amide, sodium hydride and calcium hydride, and additionally also the alcoholate of an alkali metal such as sodium methylate, sodium ethylate and tert-butyl potassium.

When carrying out process (A) the reaction temperature can vary within a wide range. Primarily operate at temperatures from 0°, 250°With, mainly between 50°150°C.

Process (A) is carried out primarily at normal pressure.

When carrying out process (A), the reaction components of the formula (II) and deprotonation reasons, mainly take approximately double equimolar quantities However, it is also possible to use one or the other component in excess (up to 3 mol).

Process (C) is characterized by the fact that the compounds of the formula (III)in which a, b, W, X, Y, Z, and R8have the above meanings, is subjected to intramolecular condensation in the presence of a diluent and base.

As diluents in method (C) can be used all inert organic solvents. Mostly use hydrocarbons, such as toluene and xylene, then 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, and also alcohols, such as methanol, ethanol, propanol, isopropanol, butanol, Isobutanol and tert-butanol.

When carrying out process (C) as a basis (deprotonation funds) can be used with all common acceptors of protons. Mostly use the oxides of alkali and alkaline earth metals, hydroxides and carbonates, such as sodium hydroxide, potassium hydroxide, magnesium oxide, calcium oxide, sodium carbonate, potassium carbonate and calcium carbonate, in the presence of phase transfer catalysts, such as triethylmethylammonium, tetrabutylammonium, Adogen 464 (metyltrebutyl(C8 -C10)ammoniacal) or TDA 1 (Tris-(methoxyethoxymethyl) amine). Used alkaline metals such as sodium or potassium. Used, amides and hydrides of alkali and alkaline earth metals, such as sodium amide, sodium hydride and calcium hydride, and additionally also the alcoholate of an alkali metal such as sodium methylate, sodium ethylate and tert-butyl potassium.

When carrying out process (C), the reaction temperature can vary within a wide range. Primarily operate at temperatures from 0°, 250°With, mainly between 50°150°C.

Process (C) is conducted mainly at normal pressure.

When carrying out process (C), the reaction components of the formula (III) and deprotonation reasons, mostly taken in approximately equimolar amounts. However, it is also possible to use one or the other component in excess (up to 3 mol).

Process (C) is characterized by the fact that carbonyl compounds of the formula (V) or their enologia esters of the formula (V-a) is subjected to interaction with halogenide of ketokislot formula (VI) in the presence of a diluent and optionally in the presence of acid binding tools.

As diluents in method (C) can be used all inert organic solvents. Mostly use hydrocarbons, such as the Wal and xylene, next esters, such as disutility ether, dimethyl ether glycol and the dimethyl ether of diglycol, moreover polar solvents, such as dimethylsulfoxide, sulfolane, dimethylformamide and N-organic.

As acid binding means can be used when carrying out the process variant (C) all ordinary acid acceptors.

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

When carrying out process (C), the reaction temperature can vary within a wide range. Primarily operate at temperatures from 0°, 250°With, mainly between 50°and 220°C.

Process (C) is conducted mainly at normal pressure.

When carrying out process (C), the reaction components of the formulae (V) and (VI)in which A, D, W, X, Y and Z have the above meanings and Hal denotes halogen, and, if appropriate, the acid acceptors mostly taken in equimolar amounts. However, it is also possible to use one or the other component in excess (up to 5 mol).

Process (D) is characterized by the fact that the compounds of the formula (VIII)in which a, b, Q1, Q2, W, X, Y, Z, and R8have the above meanings, is subjected to intramolecular condensation in the presence the AI base.

As diluents in method (D) can be used all inert towards the reagents organic solvents. Mostly use hydrocarbons, such as toluene and xylene, then 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, and also alcohols, such as methanol, ethanol, propanol, isopropanol, butanol, Isobutanol and tert-butanol.

When carrying out process (D) as a basis (deprotonation funds) can be used with all common acceptors of protons. Mainly 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, and in the presence of phase transfer catalysts, such as triethylmethylammonium, tetrabutylammonium, Adogen 464 (metyltrebutyl(C8-C10) ammoniacal) or TDA 1 (Tris-(methoxyethoxymethyl)-Amin). Used alkaline metals such as sodium or potassium. Used, amides and hydrides of alkali and alkaline earth metals, such as sodium amide, sodium hydride and calcium hydride, and furthermore, the alcoholate of an alkali metal such as sodium methylate, sodium ethylate and tert-butyl potassium.

When carrying out process (D) the reaction temperature can vary within a wide range. Primarily operate at temperatures from -75°, 250°mainly between -50°150°C.

Process (D) is conducted mainly at normal pressure.

When carrying out process (D), the reaction components of the formula (VIII) and deprotonation reasons, mostly taken in approximately equimolar amounts. However, it is also possible to use one or the other component in excess (up to 3 mol).

When carrying out process (E) as the catalyst used complexes of palladium (0). Preferred are, for example, tetrakis-(triphenylphosphine)palladium or bis-(triphenyl-phosphine)-palladium-dichloride/triphenylphosphine.

As the acid acceptor, for carrying out process (E) are inorganic or organic bases. They belong mainly hydroxides, acetates, carbonates or bicarbonates of alkali or alkaline earth metals, such as hydroxides of sodium, potassium, barium or ammonium acetates of sodium, potassium, calcium or ammonium carbonates of sodium, potassium or ammonium, sodium bicarbonate or potassium, alkaline fluorides such as cesium fluoride, as well as tertiary and the ins, such as trimethylamine, triethylamine, tributylamine, N,N-dimethylaniline, N,N-dimethylbenzylamine, pyridine, N-methylpiperidine, N-methylmorpholine, N,N-dimethylaminopyridine, diazabicyclo (DABCO), diazabicyclo (DBN) or databaseconnect (DBU).

As diluents for carrying out process (E) use water, organic solvents and any mixtures thereof. As examples can be mentioned: aliphatic, alicyclic or aromatic hydrocarbons, such as petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin; halogenated hydrocarbons, such as chlorobenzene, dichlorobenzene, methylene chloride, chloroform, carbon tetrachloride, dichloro-, trichloroethane or tetrachloroethylene; ethers, such as diethyl ether, diisopropyl ether, methyl tert-butyl ether, methyl-dreamily ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane, dimethyl ether of diethylene glycol or anisole; alcohols, such as methanol, ethanol, n - or ISO-propanol, n-, ISO-, sec - or tert-butanol, ethanediol, propane-1,2-diol, ethoxyethanol, methoxyethanol, onomatology ether of diethylene glycol, manometrically ether of diethylene glycol; water.

The reaction temperature in the method (E) can vary within wide limits. Mainly work at temperatures between 0°C and +140°C, preferably is between 50° C and +100°C.

When carrying out process (E), the reaction components of the formula (X) or (X-b) and compounds of formula (I-1'-a) to (I-4'), mainly taken in a molar ratio of from 1:1 to 5:1, mainly from 1:1 to 2:1. The catalyst is used mainly in the amount of 0.005 to 0.5 mol, mostly from 0.01 mol to 0.1 mol per mol of compound of formula (I-1'-a) to (I-8'-a). The base is mostly used in excess.

The process (F-α) is characterized by the fact that the compounds of the formulae (I-1-a) to (I-4-a), respectively, is subjected to interaction with halogenide carboxylic acids of the formula (XI), optionally in the presence of a diluent and optionally in the presence of acid binding tools.

As diluents for carrying out process (F-α) inert with respect to galodamadruga acids solvents. Mainly use hydrocarbons, such as benzine, benzene, toluene, xylene or tetralin, galoidovodorodami, as for example, 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, beyond that, esters of carboxylic acids, such as ethyl acetate, and also strongly polar solvents, such as dimethylsulfoxide and sulfolane. If hydroly the practical stability of golodnikov xilu allows it, the interaction can also be carried out in the presence of water.

As acid binding means in method (F-α) use conventional acid acceptors. Mainly tertiary amines, such as triethylamine, pyridine, diazabicyclo (DABCO), diazabicyclo (DBU), diazabicyclo (DBN), the base Hunga and N,N-dimethylaniline, and the oxides of alkaline earth metals, such as magnesium oxide and calcium oxide, carbonates of alkaline or alkaline earth metals, such as sodium carbonate, potassium carbonate and calcium carbonate and also alkali hydroxides such as sodium hydroxide and potassium hydroxide.

The reaction temperature in the method (F-α) can vary within wide limits. Primarily operate at temperatures between -20°C and +150°C, preferably between 0°and 100°C.

When carrying out process (F-α) educt of the formula (I-1-a) to (I-4-a) and galodamadruga carboxylic acids of the formula (XI), mainly taken in equimolar ratio. You can also use galoyanized carboxylic acid in excess (up to 5 mol). The processing carried out by conventional methods.

The process (F-β) is characterized by the fact that the compounds of the formulae (I-1-a) to (I-4-a), respectively, is subjected to interaction with halogenide carboxylic acids of the formula (XII), if necessary, in the presence of rabbanites and, if necessary, in the presence of acid binding tools.

As a diluent in method (F-β) can be used primarily those diluents that are mainly used when applying golodnikov acids. However, used in excess of the anhydride of the carboxylic acid can also act simultaneously as the diluent.

As acid binding means in method (F-β) mostly use the linking acid funds, which are primarily used when applying golodnikov acids.

The reaction temperature in the method (F-β) can vary within wide limits. Primarily operate at temperatures between -20°C and +150°mainly between 0°and 100°C.

When carrying out process (F-β) of starting compound of formulas (I-1-a) to (I-4-a) and the carboxylic anhydride of the acid of formula (XII) are mainly used in equivalent quantities. You can also use the anhydride of carboxylic acid in excess (up to 5 mol). The processing carried out by conventional methods.

Mostly thinner and is 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 (G) is characterized by the interaction the compounds of formulas (I-1-a) to (I-4-a) with a complex ether of Harborview acid or tieferen Harborview acid of the formula (XIII), if necessary, in the presence of a diluent and optionally in the presence of acid binding tools.

When carrying out process (G) as the acid binding means use all customary acid acceptors. Mostly use of tertiary amines as triethylamine, pyridine, DABCO, DBU, DBA, based Hunga and N,N-dimethylaniline, and the oxides of alkaline earth metals, such as magnesium oxide and calcium oxide, carbonates of alkali and alkaline earth metals, such as sodium carbonate, potassium carbonate and calcium carbonate and also alkali hydroxides such as sodium hydroxide and potassium hydroxide.

As diluents for carrying out process (G) is an inert towards esters Harborview acid solvents. Mostly use hydrocarbons, such as benzine, benzene, toluene, xylene or tetralin, galoidovodorodami, as for example, 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, in addition, esters of carboxylic acids, such as ethyl acetate, and also strongly polar solvents, such as dimethylsulfoxide and sulfolane.

The reaction temperature when carrying out process (G) may, at reroutes in a wide limit. If you are in the presence of a diluent and an acid binding means, the temperature of the reaction support in General between -20°C and +100°mainly between 0°s and 50°C.

The process (G) is carried out generally under normal pressure.

When carrying out process (G) of starting compound of formulas (I-1-a) to (I-4-a) and the corresponding ester Harborview acid of the formula (XIII) are mainly used in equivalent quantities. You can also use one or another component in excess (up to 2 moles). The processing carried out by conventional methods. Basically separate drop-down salt and the remaining reaction mixture is concentrated by evaporation of the diluent.

It has been found that the compounds of formula (I) show a very good performance as the active substance in the means of pest control, mainly such as insecticides, acaricides and herbicides.

The compounds of formula (I) (hereinafter: the active substances according to the invention are suitable, with good compatibility with plants and low toxicity to warm-blooded animals, for combating animal pests, in particular insects, spiders and nematodes in agriculture, in forestry, to protect stocks and materials, as well as in the field of sanitation. Mainly they can be used as plant protection products. They are effective against the right of sensitive and tolerant species, and on all or individual stages of development. To the abovementioned pests include:

The compounds of formula (I) can be used as herbicides and bactericides, in certain concentrations and expenditure amounts, for example as fungicides, antifungal agents and bactericides. They can also be used as intermediate products or intermediate products for the synthesis of further active substances.

The active substances according to the invention can be converted to conventional preparative forms such as solutions, emulsions, wettable powders, suspensions, powders, spray, pastes, soluble powders, granules, suspesion-emulsion concentrates, impregnated with active ingredient of natural and synthetic materials, as well as nonconception in polymeric materials form.

These preparative forms produced by known methods, for example by mixing the active substances with extenders, such as liquid solvents and/or solid carriers, using, if necessary, surface active substances such as emulsifiers and/or dispersing agents and/or foaming agents.

In the case of using water as a filler, for example, use the AMB organic solvents as auxiliary solvents. As liquid solvents can be used: aromatic compounds such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzene, chlorethylene or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example, oils, 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, clay, talc, chalk, quartz, attapulgite, montmorillonite or hard-shelled land and synthetic stone flour as highly dispersed silicic acid, alumina and silicates, as solid carriers in the granulates are used: for example, crushed and fractionated Estestvennye rocks as calcite, marble, pumice, thick, dolomite, and also synthetic granules of inorganic and organic flour and granules of organic material such as sawdust, peel a coconut, corn cobs and stalks of tobacco; as emulsifiers and/or foam the formers are used: for example, non-ionic and anionic emulsifiers, such as esters polyoxyethylenic acids, esters polyoxyethylene alcohols, for example alkylarylsulphonates ether, alkylsulfonate, alkylsulfate, arylsulfonate and their hydrolysates; as dispersant use: for example, the alkaline sulfite liquor lignin and methylcellulose.

In the formulation may be used for adhesion, such as carboxymethylcellulose, natural and synthetic, powder, granular or latexbased polymers, such as gum Arabic, polyvinyl alcohol, polyvinyl acetate, and also natural phospholipids, such as cephalin and lecithins, and synthetic phospholipids. The following additives can be mineral and vegetable oils.

As the coloring matter can be used as inorganic pigments, for example iron oxide, titanium oxide, Prussian blue, and organic dyestuffs, such as alizarin, azo and metallophthalocyanine dyes and micronutrients, such as iron salts, manganese, boron, copper, cobalt, molybdenum and zinc.

Preparative form mostly contain 0.1 to 95 wt.% active substances, mostly 0.5 to 90%.

The active substance according to the invention can be contained in the standard formulation, and in the prepared from this the x forms application forms in a mixture with other active substances, such as insecticides, rippers, sterilizers, bactericides, acaricides, nematicides, fungicides, growth regulators or herbicides. Insecticides are considered, for example, esters of phosphoric acid, carbamates, esters of carboxylic acids, chlorinated hydrocarbons, prilocaine, substances produced by microorganisms.

Particularly favorable mixed partners are, for example, the following:

Fungicides

Aldemar, Aspropirgos, Lampropeltis-potassium, Andapril, Anilazine, Azaconazole, AZOXYSTROBIN,

Benalaxyl, Benadryl, Benomyl, Benzamycin, Benzamycin-isobutyl, Bialaphos, Binapacryl, Biphenyl, Bitertanol, Blasticidin-S, Bromuconazole, Bupirimate, Bitobit,

The calcium polysulfide, Capsaicin, Captafol, Captan, Carbendazim, Carboxin, carvon,

Chinomethionat (Quinomethionate), Chlormethiazole, Chlorbenzol, Chloroneb, Chloropicrin, CHLOROTHALONIL, Koholint, Hasilkan, Kurane, Cymoxanil, Cyproconazole, Cyprodinil, Capreform,

Debaker, Dichlorophen, Diclobutrazol, Dichlofluanid, Declomycin, Dekoron, Dietphenterm, Difenoconazol, Dimethirimol, Dimethomorph, Diniconazole, Diniconazole-M, Dinakar, Diphenylamine, Dipyrithione, Datalists, Dithianon, Dodemont, Didin, Drazoxolon,

Edifenphos, Epoxiconazol, Itaconate, Ethirimol, Etridiazole,

Famoxadone, Verapamil, Fenarimol, Genbukan is angry Fanforum, Penetapan,

Fenpiclonil, Fenpropidin, Fenpropimorph, Fentiazac, Fistinginaction, Ferbam, Verison, Fluazinam, Flamethower, Fluorone, Fluquinconazole, Flurried, Flusilazol, Flutolanil, Flutolanil, Flutriafol, Folpet, Fosetyl-Aluminum, Fosetyl-sodium, Phtalic, Fuberidazole, Parallaxis, Parameter, Percarbonic, Forconsumer-CIS, Pharmacyclics,

Goitein,

Hexachlorobenzene, Hexaconazole, Hymexazol,

Imazalil, Kabekona, Iminoctadine, Iminoctadine,

Iminoctadine, Iodosorb, Arkanasa, Iprobenfos (IBP), Iprodion, Arunamarin, Isoprothiolane, Isovaleryl,

Kasugamycin, Kresoxim-methyl, preparations of copper such as copper Hydroxide, copper Naphthenate, copper Oxychloride, copper Sulphate, copper Oxide, Oxin-copper and Bordeaux mixture,

Marcopper, MANCOZEB, MANEB, Severinson, Mepanipyrim, Mepronil, Metalaxyl, Metconazole, Metasurfaces, Mefenoxam, Metiram, Memelas, Masulovic, Millionizer, Myclobutanil, Mickleton,

Nickel dimethyldithiocarbamate, Nitrates-isopropyl, Nuarimol,

Furac, Oxadixyl, Oxamate, Oxolinic, Oxycarboxin, Oxidation, Paclobutrazol, Peyratout, Penconazole, Pencycuron, Forgiven, Pimaricin, Piperalin, Polyoxin, Palikari, Provenzal, Prochloraz, Procymidone, Propamocarb, Propanoic-sodium, Propiconazol, Propineb, P is risofos, Pirivenas, Pyrimethanil, Pyroquilon, Proxyfor,

Quinceanos, Quintozene (PCNB),

Sulfur and sulfur drugs,

The tebuconazole, Telital, Tecnazene, Tetcyclacis, Tetraconazole, Mebendazol, Tilian, Leflunomid, Thiophanate-methyl, Thiram, Dioxime, Tolclofos-methyl, tolylfluanid, Triadimefon, Triadimenol, Triazolyl, Triazoxide, Trihemic, Tricyclazole, Tridemorph, Triflumizole, Triforine, Triticonazole,

Uniconazole,

Validamycin And, Vinclozolin, Viceconsul,

Suriname, Zineb, Zir, and

Dagger G,

OK-8705,

OK-8801,

α-(1,1-dimetilfenil)β-(2-phenoxyethyl)-1H-1,2,4-triazole-1-ethanol,

α-(2,4-dichlobenil)-β-fluoro-b-propyl-1H-1,2,4-triazole-1-ethanol,

α-(2,4-dichlobenil)-β-methoxy-a-methyl-1H-1,2,4-triazole-1-ethanol,

α-(5-methyl-1,3-dioxane-5-yl)-β-[[4-(trifluoromethyl)-phenyl]-methylene]-1H-1,2,4-triazole-1-ethanol,

(5RS,6RS)-6-hydroxy-2,2,7,7-tetramethyl-5-(1H-1,2,4-triazole-1-yl)-3-octanone,

(E)-a-(methoxyimino)-N-methyl-2-phenoxy-phenylacetamide,

1-isopropyl ether {2-methyl-1-[[[1-(4-were)-ethyl]-amino]-carbonyl]-propyl}-carbamino acid,

1-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazole-1-yl)-alanon-O-(phenylmethyl)-oxime,

1-(2-methyl-1-naphthalenyl)-1H-pyrrole-2,5-dione,

1-(3,5-dichlorophenyl)-3-(2-propenyl)-2,5-pyrrolidinedione,

1-[(diiodomethyl)-sulfonyl]-4-methyl-benzene,

1-[[2-(2,4-dichlorophenyl)-1,3-dioxolane-2-yl]-methyl]-1H-imidazo is,

1-[[2-(4-chlorophenyl)-3-phenyloxirane]-methyl]-1H-1,2,4-triazole,

1-[1-[2-[(2,4-dichlorophenyl)-methoxy]-phenyl]-ethynyl]-1H-imidazole,

1-methyl-5-nonyl-2-(phenylmethyl)-3-pyrrolidino,

2',6'-dibromo-2-methyl-4'-triptoreline-4'-trifluoromethyl-1,3-thiazole-5-carboxanilide,

2,2-dichloro-N-[1-(4-chlorophenyl)-ethyl]-1-ethyl-3-methyl-cyclopropanecarbonyl-amide,

2,6-dichloro-5-(methylthio)-4-pyrimidinyl-thiocyanate,

2,6-dichloro-N-(4-trifloromethyl)-benzamid,

2,6-dichloro-N-[[4-(trifluoromethyl)-phenyl]-methyl]-benzamide,

2-(2,3,3-tried-2-propenyl)-2H-tetrazol,

2-[(1-methylethyl)-sulfonyl]-5-(trichloromethyl)-1,3,4-thiadiazole,

2-[[6-deoxy-4-O-(4-O-methyl-β-D-glycopyranosyl)-a-D-glyukopiranozil]-amino]-4-methoxy-1H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile,

2 aminobutane,

2-bromo-2-(methyl bromide)-pentanedinitrile,

2-chloro-N-(2,3-dihydro-1,1,3-trimethyl-1H-inden-4-yl)-3-pyridinecarboxamide,

2-chloro-N-(2,6-dimetilfenil)-N-(isothiocyanates)-ndimethylacetamide,

2-phenylphenol (ORR),

3,4-dichloro-1-[4-(deformedarse)-phenyl]-1H-pyrrol-1,2,5-dione,

3,5-dichloro-N-[cyan[(1-methyl-2-PROPYNYL)-oxy]-methyl]-benzamide,

3-(1,1-dimethylpropyl-1-oxo-1H-inden-2-carbonitril,

3-[2-(4-chlorophenyl)-5-ethoxy-3-isoxazolidine]-pyridine,

4-chloro-2-cyan-N,N-dimethyl-5-(4-were)-1H-imidazole-1-sulfonamide,

4-methyl-tetrazole [1,5-a]hinzelin-5(4H)-he,

8-(1,1-dimethylethyl)-N-ethyl-N-propyl-1,4-dioxaspiro[4.5]decane-2-methanamine,

8-GI is oxyhemocyanin,

2-[(phenylamino)-carbonyl]-hydrazide-N-xanthene-9-carboxylic acid,

bis-(1-methylethyl)-3-methyl-4-[(3-methylbenzoyl)-oxy]-2,5-thiophencarboxylic,

CIS-1-(4-chlorophenyl)-2-(1H-1,2,4-triazole-1-yl)-cycloheptanol,

CIS-4-[3-[4-(1,1-dimethylpropyl)-phenyl-2-methylpropyl]-2,6-dimethyl-morpholine hydrochloride

ethyl-[(4-chlorophenyl)-azo]-cyanoacetate,

hydrogen potassium

sodium salt of metanarrative,

methyl-1-(2,3-dihydro-2,2-dimethyl-1H-inden-1-yl)-1H-imidazole-5-carboxylate,

methyl-N-(2,6-dimetilfenil)-N-(5-isoxazolidinone)-DL-alaninate,

methyl-N-(chloroacetyl)-N-(2,dimethylphenyl)-DL-alaninate,

N-(2,3-dichloro-4-hydroxyphenyl)-1-methyl-cyclohexanecarboxylic,

N-(2,6-dimetilfenil)-2-methoxy-N-(tetrahydro-2-oxo-3-furanyl)-ndimethylacetamide,

N-(2,6-dimetilfenil)-2-methoxy-N-(tetrahydro-2-oxo-3-thienyl)-ndimethylacetamide,

N-(2-chloro-4-nitrophenyl)-4-methyl-3-nitro-benzosulfimide,

N-(4-cyclohexylphenol)-1,4,5,6-tetrahydro-2-pyrimidinamine,

N-(4-hexylphenyl)-1,4,5,6-tetrahydro-2-pyrimidinamine,

N-(5-chloro-2-were)-2-methoxy-N-(2-oxo-3-oxazolidinyl)-ndimethylacetamide,

N-(6-methoxy)-3-pyridinyl)-cyclopropanecarboxamide,

N-[2,2,2-trichloro-1-[(chloroacetyl)-amino]-ethyl]-benzamide,

N-[3-chloro-4,5-bis-(2-propenyloxy)-phenyl]-N'-methoxy-methanimidamide,

sodium salt of N-formyl-N-hydroxy-DL-alanine,

O,O-diethyl-[2-(dipropylamino)-2-o-alaninate]-ethylphosphonate,

p> O-methyl-S-phenyl-phenylpropionamide,

S-methyl-1,2,3-benzothiadiazole-7-carbothioic,

Spiro[2H]-1-benzopyran-2,1'(3 N)-isobenzofuran]-3'-he,

Bactericides

Bronopol, dichlorophen, nitrapyrin, Nickel dimethyldithiocarbamate, kasugamycin, Actelion, francebuy acid, oxytetracycline, provenzal, streptomycin, telital, copper sulphate and other drugs of copper.

Insecticides/acaricides/nematicides

The abamectin, Arafat, Acetamiprid, Acrinathrin, Alankar, Aldicarb, Aldoxycarb, alpha-cypermethrin, alpha-methrin, Amitraz, Avermectin, AZ 60 541, Azadirachtin, Azamethiphos, Azinphos And, Azinphos M, Azocyclotin,

Bacillus popilliae, Bacillus sphaericus, Bacillus subtilis, Bacillus thuringiensis, Baculovirus, Beauveria bassiana, Beauveria tenella, Bendiocarb, Benfuracarb, Bensultap, Benoxinate, Betacyfluthrin, Bifenazate, Bifenthrin, Bioeconomical, Bioprotein, VRMS, Bromophos And, Bofenkamp, Buprofezin, Butamifos, Butocarboxim, Butylparaben,

Cadusafos, Carbaryl, Carbofuran, Carbophenothion, Carbosulfan, Cartap, Cloethocarb, Chlorethoxyfos, Chlorfenapyr, chlorfenvinfos, Chlorfluazuron, Chlormephos, chlorpyrifos, chlorpyrifos M, Javaparty, CIS-Resmethrin, CIS-Permethrin, Claritin, Cloethocarb, Clofentezine, Cyanophos, Ciclope, Cicloprofen, Cyfluthrin, Cigalotrin, Cyhexatin, Cypermethrin, Cyromazine, Deltamethrin, Demeton M, Demeton S, Demeton-S-methyl, Defent the damage Diazinon, Dichlorvos, Diflubenzuron, Dimethoate, Dimethylene, Giovanola, Disulfoton, Docusinate-sodium, Dienen,

Fluient, Emamectin, Empenthrin, Endosulfan, Entomopfthora spp., Esfenvalerate, Ethiofencarb, Ation, Ethoprophos, Etofenprox, Etoxazole, Etrimfos, Fenamiphos, Fenazaquin, fenbutatin oxide, Fenitrothion, Fanatical, Tenoxicam, Fenoxycarb, Fenpropathrin, Feneral, Generatin, Fenpyroximate, Fenvalerate, Fipronil, Fluazinam, Fluazuron, Lubricant, Flucycloxuron, Flucythrinate, Flufenoxuron, Lotensin, Fluvalinate, Fonofos, Tomatlan, Fosthiazate, Tupfenrock, Furathiocarb,

Halogenated, HCH, Heptenophos, Hexaflumuron, Hexythiazox, Hydroprene, Imidacloprid, Isazofos, Isofenphos, Isoxathion, Ivermectin,

Lambda cigalotrin, Lufenuron,

Malathion, Mecarbam, Metaldehyde, Metamidophos, Metharhizium anisopliae, Metharhizium flavoviride, Mitigation, Methiocarb, Methomyl, Methoxyfenozide, Metolcarb, Methoxamine, Mevinphos, Milbemectin, Monocrotophos,

Naled, Nitenpyram, Nithiazine, Novaluron

Omethoate, Oxamyl, Oxydemeton M

Paecilomyces fumosoroseus, Parathion And Parathion M, Permethrin, Pentat, Fort, Fozalon, Phosmet, Phosphamidon, Phoxim, Pirimicarb, Pirimiphos And, Pirimiphos M, Profenofos, Promecarb, Propoxur, Prothiofos, Procoat, Pymetrozine, Pyraclofos, Prismatron, Feverfew, Pyridaben, Predation, Pyrimidifen, Periproct the Hairdryer,

Quinalphos,

Ribavirin

Coalition, Sabots, Selflove, Spinosad, Sulfotep, Sulprofos,

Tau-fluvalinate, Tebufenozide, Tebufenpyrad, Tebupirimfos, Teflubenzuron, Tefluthrin, Temephos, Timelines, Terbufos, Tetrachlorvinphos, Tealpirate, Thiamethoxam, Tiopronin, Tiatives, Thiocyclam hydrocalc, Thiodicarb, Thiofanox, Thuringiensis, Telocity, Tralomethrin, Triuralin, Triazamate, Triazophos, Treasure, Trichloride, Trichlorfon, Triflumuron, Trimeter,

Validation, Unilibro, Verticillium lecanii

YI5302

Zeta-cypermethrin, Sulprofos

(1R-CIS)-[5-(phenylmethyl)-3-furanyl]-methyl-3-[(dihydro-2-oxo-3(2H)-furylidene)-methyl]-2,2-dimethylcyclopropanecarboxylate,

(3-phenoxyphenyl)-methyl-2,2,3,3-tetramethylcyclopropanecarboxylate,

1-[(2-chloro-5-thiazolyl)methyl]tetrahydro-3,5-dimethyl-N-nitro-1,3,5-triazine-2(1H)-Imin,

2-(2-chloro-6-forfinal)-4-[4-(1,1-dimethylethyl)phenyl]-4,5-dihydrooxazolo,

2-(atomic charges)-3-dodecyl-1,4-naphthalenedione,

2-chloro-N-[[[4-(1-phenylethane)-phenyl]-amino]-carbonyl]-benzamid,

2-chloro-N-[[[4-(2,2-dichloro-1,1-diflorasone)-phenyl]-amino]-carbonyl]-benzamid,

3-were-propylgallate,

4-[4-(4-ethoxyphenyl)-4-were]-1-fluoro-2-phenoxy-benzene,

4-chloro-2-(1,1-dimethylethyl)-5-[[2-(2,6-dimethyl-4-phenoxyphenoxy)ethyl]thio]-3(2H)-pyridazinone,

4-chloro-2-(2-chloro-2-methylpropyl)-5-[(6-iodine-3-pyridinyl)methoxy]-3(2H)-pyridazino is,

4-chloro-5-[(6-chloro-3-pyridinyl)methoxy]-2-(3,4-dichlorophenyl)-3(2H)-pyridazinone,

Bacillus thuringiensis strain EG-2348,

hydrazide [2-benzoyl-1-(1,1-dimethylethyl)-benzoic acid,

2,2-dimethyl-3-(2,4-dichlorophenyl)-2-oxo-1-oxaspiro[4.5]Dec-3-EN-4-silt ether butane acid,

[3-[(6-chloro-3-pyridinyl) methyl]-2-thiazolidinone]-cyanamide,

dihydro-2-(nitromethylene)-2H-1,3-thiazin-3(4H)-carboxaldehyde,

ethyl-[2-[[1,6-dihydro-6-oxo-1-(phenylmethyl)-4-pyridazinyl]oxy]ethyl]-carbamate,

N-(3,4,4-Cryptor-1-oxo-3-butenyl)-glycine,

N-(4-chlorophenyl)-3-[4-(deformedarse)phenyl]-4,5-dihydro-4-phenyl-1H-pyrazole-1-carboxamide,

N-[(2-chloro-5-thiazolyl)methyl]-N'-methyl-N ' -nitro-guanidine,

N-methyl-N'-(1-methyl-2-propenyl)-1,2-hydrazinecarbothioamide,

N-methyl-N'-2-propenyl-1,2-hydrazinecarbothioamide,

O,O-diethyl-[2-(dipropylamino)-2-oxoethyl]-ethylphosphonate.

There may also be a mixture with other known active substances, such as herbicides, or fertilizers and growth regulators.

The active substances according to the invention can be used as insecticides in the standard formulation, and in the prepared from these forms application forms in a mixture with synergists. Synergists are compounds which increase the action of the active substances, the added synergist should not be effectively active.

The content of the asset is wow substances according to the invention prepared from the standard preparative forms application forms can be varied within wide limits. The concentration of the active substances according to the invention in the application forms can be from 0.0000001 to 95 wt.%, mainly between 0,0001 and 1 wt.%.

Prepared application form apply in the usual way.

When used against pests in sanitation and storage of stocks of active substances according to the invention exhibit high residual effectiveness on wood and clay as well as a good alkaline stability on Izvestkovaya substrates and bases.

The active substances according to the invention act not only against plant pests, sanitation and storage of inventory, but also effective in veterinary medicine against external parasites of animals (ectoparasites), such as casaitalia mites, skin mites, cestocide pliers, running pliers, flies (stinging and licking), parasitic larvae of flies, lice, hair, feather and fleas. These parasites are:

The active substances according to the invention are also suitable for combating arthropods which attack agricultural useful animals, such as cattle, sheep, goats, horses, pigs, donkeys, camels, Buffalo, rabbits, chickens, turkeys, ducks, geese, honeybees, other domestic animals, such as dogs, is Osek, birds, aquarium fish room, as well as the so-called experimental animals, such as hamsters, Guinea pigs, rats and mice. When applying the active substances according to the invention are reduced deaths and decreased productivity (for meat, milk, wool, leather, eggs, honey and so on) at the expense of combating these arthropods, which makes the animal more economical and simple.

The active substances according to the invention is used in veterinary medicine by known methods by enteral introducing them in the form of, for example, tablets, capsules, liquor, jelly, granules, pastes, boluses, through nutrition, suppositories, Peterlee introduction, such as injections (intramuscularly, subcutaneously, intravenously, intraperitoneally, etc.), implants, nasal, transdermal, for example, by diving or bathing (dipping in liquid), spraying (spray), tinctures (with cold water and applying patches), washing, dusting, and by containing the active substance molded bodies, such as necklaces, ear and tail brands, chains or bands for limbs, halters, marking devices and so on.

When applied to livestock, poultry, Pets and so on active substances according to the invention in the form of preparative forms (for example, powders, emulsions, tools, localdatasource), contains the active substance in an amount of from 1 to 80 wt.%, they can be used directly or after 100 to 10 000-fold dilution, or use them in the form of chemical baths.

In addition, it was found that the compounds according to the invention possess high insecticidal action against destructive technical materials insects.

As preferred examples, you can specify the following insects:

Beetles, such as

Hylotrupes bajulus, Chlorophorus pilosis, Anobium punctatum, Xestobium rufovillosum, Ptilinus pecticomis, Dendrobium pertinex, Ernobius mollis, Priobium carpini, Lyctus brunneus, Lyctus africanus, Lyctus planicollis, Lyctus linearis, Lyctus pubescens, Trogoxylon aequale, Minthes rugicollis, Xyleborus spec., Tryptodendron spec., Apate monachus, Bostrychus capucins, Heterobostrychus brunneus, Sinoxylon spec., 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, Reficulitermes lucifugus, Mastotermes darwiniensis, Zootermopsis nevadensis, Coptotermes formosanus.

Seinajoki, such as Lepisma saccharina.

Under the technical material should be understood primarily of synthetic materials, adhesives, glues, paper and cardboard, leather, wood, wood products and paints.

When protecting materials from damage by insects very particularly preferably it is about the protection of wood and wood products.

Under the wood and wood products is the processing, you can protect the active substances according to the invention and, respectively, containing mixtures, you need to understand about the following:

timber, wooden beams, railway sleepers, bridge parts, marinas, boats, wooden vehicles, boxes, palettes, containers, telephone poles, wood paneling, wooden Windows and wooden doors, wooden fences, tiled chips, joinery or wooden products which finds universal application, the construction of a home or construction carpentry workshop.

The active substances according to the invention can be applied as such by themselves, in the form of concentrates or in the usual formulation, such as powders, granulates, solutions, suspensions, emulsions or pastes.

These shapes can be produced by known methods, for example by mixing the active substances according to the invention, at least one solvent and, accordingly, diluent, emulsifier, dispersant and/or binder or fixing agent, water repellent, if necessary, drying and UV stabilizers and, if necessary, coloring agents and pigments, as well as further auxiliary means.

When used for protection of wood and wood materials insecticide the means or containing concentrates, the concentration of the active substance according to the invention is from 0.0001 to 95 wt.%, in particular 0.001 to 60 wt.%.

The number of appointed means and respectively concentrates depends on the type and availability of insects, and the environment. The optimal number can be set near the relevant tests. However, it is often enough from 0.0001 to 20 wt.%, mainly from 0.001 to 10 wt.%, the active substances according to the invention in relation to the protected material.

As solvents and/or diluents used organic chemical solvent or solvent mixture and/or oily or nizkosernistye hard for volatile organic chemical solvent or solvent mixture and/or a polar organic chemical solvent or solvent mixture and/or water and, if necessary, an emulsifier and/or wetting agent.

As organic chemical solvents use oily or nizkosernistye solvents with the number of evaporation over 35 and a flash point mostly above 30°With, mainly over 45°C. as such tielaechi, water-insoluble, oily and nizkosernistyh solvent use appropriate mineral oils or fractions of aromatic compounds or mineral oil solvent mixture, predominantly white spirit, petroleum and/or alkylbenzene.

Advantageously COI is lesofat mineral oil with a boiling point of from 170 to 220° With, white spirit with a boiling point of from 170 to 220°, spun the oil with a boiling point of 250 to 350°, kerosene and accordingly aromatic compounds with a boiling point of from 160 to 280°With turpentine, and others.

In a preferred form of execution used liquid aliphatic hydrocarbons with a boiling temperature from 180 to 210°or high-boiling mixtures of aromatic and aliphatic hydrocarbons with a boiling temperature of 180 to 220°and/or spun oil, and/or monochromator, mainly α-monochromation.

Organic tielaechi oily or nizkosernistye solvents with the number of evaporation over 35 and a flashpoint above 30°C, mostly above 45°partly can be replaced easily or crenelation chemical organic solvent provided that the solvent mixture has a number of evaporation more than 35 and a flashpoint above 30°C, mostly above 45°and that insecticide-fungicide mixture is capable of dissolving or emulgirovanija in this solvent mixture.

In a preferred execution of the portion of the organic chemical solvent or mixture of solvents, aliphatic or polar organic chemical solvent or solvent mixture is replaced. Mainly used alifatic the ski chemical organic solvents, containing hydroxy-and/or ester and/or ether groups, such as glycol ether, ester, and others.

As organic chemical binders used vodorastvorimye, and/or soluble or dispersible and therefore emulsifiable in these organic chemical solvents, synthetic resins and/or binding drying oils, in particular a binder consisting of or containing acrylate resins, vinyl resins, such as polyvinylacetate, polyester resin, polycondensation or stepped polymerized resin, polyurethane resin, alkyd resin and correspondingly modified alkyd resin, phenolic resin, hydrocarbon resin, such as inden-coumarone resin, silicone resin, drying vegetable and/or drying of solid oils and/or physically drying binder based on natural and/or synthetic resin.

Used as a binder of synthetic resin can be used in the form of an emulsion, dispersion or solution. As a binder can also be used bitumen or up to 10 wt.% bituminous substance. You can also use well-known dyes, pigments, water repellent products, korrigentami smell, inhibitors, corrosion-resistant tools, and others.

Preferably the tool or cancer the t as chemical organic binder contains at least one alkyd resin or modified alkyd resin and/or a drying vegetable oil. Preferably according to the invention using an alkyd resin with an oil content of more than 45 wt.%, mostly from 50 to 68 wt.%.

Mentioned binder may be replaced in whole or in part fixing agent (mixture) or a plasticizer (mixture). These additives shall prevent the volatilization of the active substances according to the invention, and accordingly their crystallization. Mostly they refund from 0.01 to 30% binder (relative to 100% assigned binder).

The plasticizers are selected from chemical compounds: esters of phthalic acid, such as dibutil, dioctyl or benzylbutylphthalate, esters of phosphoric acid such as tributyl phosphate, esters of adipic acid, such as di(2-ethylhexyl)-adipate, stearates, as butilstearat or amistart, oleates, as butylurea, ethers of glycerol or vykolochenny glycol ethers, esters of glycerol and esters of p-toluenesulfonic acid.

Fixing means based on the chemical polyvinylalcohol esters, as for example, polivinilbutilovy ether, or ketones, as benzophenone, atelevision.

As solvent or diluent use water, when the need is and in a mixture with one or more of the above-mentioned chemical organic solvents and, accordingly, diluents, emulsifiers and dispersants.

Particularly effective protection of wood is achieved by high-tech methods of impregnation, for example, under vacuum, double vacuum or pressure.

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

As additional components are taken into account mainly described in the international application WO 94/29268 insecticides and fungicides. Referred to in this document connections are an integral part of this application.

A particularly preferred additional components include insecticides like chlorpyrifos, Phoxim, Selfloathing, Alphamethrin, Cyfluthrin, Cypermethrin, Deltamethrin, Permethrin, Imidacloprid, NI-25, Flufenoxuron, Hexaflumuron, Transfluthrin, Thiacloprid, Methoxyfenozide and Triflumuron, and fungicides, as Epoxiconazol, Hexaconazole, Azaconazole, Propiconazole, Tebuconazole, Tsyprokonazolu, Metconazole, Imazalil, Dichlofluanid, tolylfluanid, 3-Iodine-2-propyl-BUTYLCARBAMATE, N-Octyl-isothiazolin-3-one and 4,5-dichloro-N-acterization-3-one.

At the same time the compounds according to the invention can use the change for the protection of vegetation cover items in particular, ship hulls, sieves and filters, nets, buildings, waterfront structures and signaling devices that are in contact with sea or hard water.

The spread of sedentary multiseta worms, such as calcareous tube worms, and by shells and species group Ledamorpha (barnacles), such as various Lepas and Scalpellum species, or by species group Balanomorpha (barnacles), such as Balanus or Pollicipes species, increases the friction resistance of ships and leads, resulting in increased energy consumption and, hence, frequent stay in dry dock and increase production costs.

Along with overgrowing algae, for example Ectocarpus sp. and Ceramium sp., of great importance is the obliteration, in particular, sedentary group Entomostraken, which are combined under the name of Cirripedia) (Cirripedia) (Cirripedia).

Unexpectedly found that the compounds of formula (I) possess by themselves or in combination with other active substances remarkable anti-fouling effect.

Introduction compounds of formula (I) alone or in combination with other active substances allows to refuse from the use of heavy metal compounds, such as bis-(triamcinolone)-sulfide, laurate tri-n-butyanova, chloride, tri-n-butyanova, copper oxide (I), triethylborane, tri-n-butyl(2-phenyl-4-chloro what enocsi)tin, oxide anti, molybdenum disulphide, antimony oxide, polymer butylmalonate, phenyl-(bispyridine)-bismuth chloride, fluoride, tri-n-butyanova, ethylenebisdithiocarbamate manganese, zincdependent, cinqueterreliguria, zinc and copper salts of 2-pyridinethiol-1-oxide, biodimethylether-carbamoyltransferase, zinc oxide, ethylene-bidity-carbamate of copper (I), copper thiocyanate, copper naphthenate and tributylphosphine, or snachitelno to reduce their concentration.

Ready-to-use dyes with antifouling action, if necessary, may contain other active substances, mainly algaecides (against overgrowth of algae), fungicides, herbicides, molluscicides, and accordingly other active substances with anti-fouling effect.

As partners in the media with anti-fouling effect predominantly come:

Algaecides, such as

2-tert-butylamino-4-cyclopropylamino-6-methylthio-1,3,5-triazine, diclofen, Diuron, Endothal, Fentiazac, Isoproturon, Methabenzthiazuron, Oxyfluorfen, Hinkleman and Terbutryn;

Fungicides, such as

Cyclohexylamino-S,S-dioxides[b]thiophencarboxylic acid,

Dichlofluanid, Floortype, 3-iodine-2-PROPYNYL-BUTYLCARBAMATE, tolylfluanid and azoles such as Azaconazole, Tsyprokonazolu, Epoxiconazol, Hexaconazole, Metconazole,Propiconazole and Tebuconazole;

The molluscicides, such as

Fentiazac, Metaldehyde, Methiocarb, Niclosamide, Thiodicarb and Trimeters;

Or conventional active substances with anti-fouling effect, such as 4,5-dichloro-2-octyl-4-isothiazolin-3-one, Iodmethylenetrialkyl, 2-(N,N-dimethylthiocarbamate)-5-nitrothiazole, potassium, copper, sodium and zinc salts of 2-pyridinethiol-1-oxide, pyridine-triphenylborane, tetramethyldisiloxane, 2,3,5,6-tetrachloro-4-(methylsulphonyl)-pyridine, 2,4,5,6-tetrachloroisophthalonitrile, tetramethylthiuramdisulphide and 2,4,6-trichlorotoluene.

Funds from antifouling effect can contain the active substances according to the invention in a concentration of from 0.001 to 50 wt.%, in particular, from 0.01 to 20 wt.%.

Funds from antifouling effect can contain further conventional components, as for example described in Ungerer, Chem. Ind. 1985, 37, 730-732, and Williams, Antifouling Marine Coatings, Noyes, Park Ridge, 1973.

Painting means with antifouling action contain along with algaecides, fungicides, molluscicides, and insecticidal active substances according to the invention, in particular a binder.

Examples of recognized binders are polyvinyl chloride in a solvent system, chlorinated rubber in a solvent system, acrylic resins in a solvent system, in particular in an aqueous system, copolymer system vinyl chloride/in nilacef in the form of aqueous dispersions or in the form of organic solvents, phenylbutazone/styrene/Acrylonitrile rubbers, drying oils such as linseed oil, essential oils or modified hard resins in combination with tar or bitumen, asphalt, and amoxiline connections, minor amounts of chlorinated rubber, chlorinated polypropylene and vinyl resins.

If necessary, coloring tools also contain inorganic pigments, organic pigments or dyes, which are predominantly insoluble in sea water. Further, coloring tools may contain materials, such as rosin, providing modified release of active substances. Next, the ink may contain a plasticizer, modifying means of influencing the rheological quality, as well as other conventional components. The compounds of formula (I) or the above-mentioned mixture can be entered in self polishing system with anti-fouling effect.

The active substances according to the invention are also suitable for combating animal pests, in particular insects, arachnids and mites, which, among other things, live in enclosed spaces, such as apartments, factory halls, offices, vehicle cabs. They can be used to control these pests by themselves or in combination with other active ingredients and auxiliary materials. About the and is effective against sensitive and resistant species and against all stages of their development. These pests include:

From the order Blattaria, for example, Blatta orientalies, Blattella germanica, Blattella asahinai, Leucophaea maderae, Panchlora spp., Parcoblatta spp., Periplaneta australasiae, Periplaneta americana, Periplaneta brunnea, Periplaneta fuliginosa, Supella longipalpa.

Detachment of Saltatoria, for example, Acheta domesticus

From the order Dermaptera, for example Forficula auricularia

From the order Isoptera, for example, Kalotermes spp., Reticulitermes spp.

From the order Psocoptera, for example, Lepinatus spp., Liposcelis spp.

From the order Coleoptera, for example, Anthrenus spp., Attagenus spp., Dermestes spp., Latheticus oryzae, Necrobia spp., Ptinus spp., Rhizopertha dominica, Sitophilus granarius, Sitophilus oryzae, Sitophilus zeamais, Stegobium paniceum.

From the order Diptera, for example Aedes aegypti, Aedes albopictus, Aedes taeniorhynchus, Anopheles spp., Calliphora erythrocephala, Chrysozona pluvialis, Culex quinquefasciatus, Culex pipiens, Culex tarsalis, Drosophila spp., Fannia canicularis, Musca domestica, Phlebotomus spp., Sarcophaga carnaria, Simulium spp., Stomoxys calcitrans, Tipula paludosa

From the order Lepidoptera, for example, Achroia grisella, Galleria mellonella, Plodia interpunctella, Tinea cloacella, Tinea pellionella, Tineola bisselliella

In the household insecticides used by themselves or in combination with other active substances such as esters of phosphoric acids, carbamates, PYRETHROID, growth regulators or active substances from other known classes of insecticides.

The use of exercise in the form of an aerosol spray atomized spraying without pressure, for example spraying with a pump and PU is everystore, automatic mist, mists, foams, gels, evaporation using an evaporation plates of cellulose or plastic, liquid evaporators, gel and membrane evaporators, propeller evaporators, unspirited, for example, passive systems evaporation, paper for moles, pouches for moths and gels for moles, in the form of granules or dust in luring the litter or luring stations.

The active substances according to the invention can be used as defoliants, dessicant destroying grass tools and, in particular, destroying weeds funds. Under the weeds in the broadest sense must be understood all plants which grow in locations where they are undesired. Are there substances according to the invention as total or selective herbicides depends essentially on the applied amounts.

The active substances according to the invention can be used, for example, for the following plants:

However, the use of active substances according to the invention are in any case not restricted to these species, and extends an equal manner to other plants.

The active substances according to the invention are suitable, depending on concentration for the total combating of weeds, for example, in industrial plants is the third and rail routes on the roads and squares with or without tree vegetation. Also the active substances according to the invention can be used for combating weeds in perennial crops, such as forest, ornamental and fruit trees, vineyards, citrus crops, nuts, bananas, coffee, tea, rubber, oil palm, cocoa, berries and hops, decorative and sports lawns and pastures, and for the selective combating of weeds in annual crops.

The compounds of formula (I) exhibit high herbicide efficacy and broad spectrum of action when applied to the soil and aboveground parts of plants. To a certain extent they are also suitable for the selective combating of monocotyledonous and dicotyledonous weeds in monocotyledonous and dicotyledonous crops for both pre-emergence and post-harvest processing.

The active substances according to the invention can be used in certain concentrations and related expenditure amounts for combating animal pests and fungal or bacterial plant diseases. You can process the whole plant or parts of plants. Under the plant refers to all plants and plant populations, as desired and undesired wild plants or crop plants (including, of course, random cultivated plants). Cultivated plants can be the ü obtained by conventional methods of breeding and optimization or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the protected or not protected plant varieties. Under the plant parts must be understood all above-ground and below-ground parts and organs of plants, such as twigs, leaves, inflorescences and roots, such as leaves, needles, stems, trunks, flowers, fruit bodies, fruits and seeds and also roots, tubers and rhizomes. The plant parts also owns the harvest, as well as vegetative and generative material reproduction, for example cuttings, tubers, roots, branches and seeds.

Treatment of plants and plant parts with the active compounds according to the invention is carried out directly or by the impact on their living environment, living space or storage space after the usual processing methods, for example by immersion, spraying, evaporation, dispersion, dissipation, lubrication, and in the case of breeding material, in particular seed, a single-layer or multilayer wrapping or wrap.

As mentioned above, in accordance with the invention, it is possible to process the whole plant and its parts. In a preferred embodiment, spend processing received or conventional biological methods of cultivation, such as crossing or hybridization, or obtained by fusion of protoplasts of species and varieties of plants and their parts. In the future ol doctitle form of exercise is treated transgenic plants and plant varieties, who received genetic engineering methods, if necessary, in combination with conventional methods (Genetic Modified Organisms), and parts thereof. The notion of "part" and "parts of plants" or "plant parts" have been explained above.

Depending on plant species and consequently varieties of plants, location and growth conditions (soils, climate, vegetation period, diet) when processing the active substances according to the invention can be achieved sverhsummarny (synergistic) effect. It is thus possible to achieve, for example, reduction of material consumption quantities and/or expansion of the range of actions and/or enhance the effect of materials and products containing the compounds of formula (I) according to the invention, better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or moisture and salt content in the soil, increased flowering, light harvesting, accelerated maturation, increase yields, improve quality and/or food value of food crops, increase persistence and/or machinability harvest products that exceed the actual the expected effects.

The workpiece to be transgenic (genetically engineered) plants and plant varieties belong to the sun the plants, received with use of genetically engineered modification of genetic material, giving these plants is particularly advantageous assets ("signs"). Examples of such qualities are improved plant growth, increased tolerance to high or low temperatures, increased tolerance (resistance) in relation to drought or moisture and salt content in the soil, increased flowering, light harvesting, accelerated maturation, higher yields, improved quality and/or food value of food crops, increasing the persistence and/or machinability harvest products. Further and particularly emphasized examples of such qualities are the increased defense of the plants against animal and microbial pests, such as insects, mites, phytopathogenic fungi, bacteria and/or viruses, and also increased tolerance of plants against certain substances with herbicide activity. As examples of transgenic plants especially highlights the important cultivated plants such as cereals (wheat, rice), maize, soybeans, potatoes, cotton, rape and also fruit plants (fruit - apples, pears, citrus fruits and grapes), with corn, soybeans, potatoes, cotton and oilseed rape. As a valuable quality ("signs") particularly emphasizes increased for the ITA plants from toxins, occur in plants against insects, in particular those produced in the plant genetic material (such as are produced by the genes CryIA(a), CryIA(b)CryIA(c), CryIIA, CryIIIA, CryIIIB2, Cry9c Cry2Ab, r3b and CryIF and their combination) (hereinafter "Bt plants"). As a valuable quality ("signs") particularly emphasizes further increased tolerance of plants in relation to certain substances with herbicide activity, such as imidazolinone, sulfonylurea, glyphosate or phosphinotricin (for example, "RAT gene). Accordingly transmitted the desired properties ("traits") genes can also occur in combinations with each other in transgenic plants. As examples of "Bt plants" are specified varieties of corn, cotton varieties, soybean varieties and potato varieties which are sold under the trade names YIELD GARD®(for example, corn, cotton, soybeans), KnockOut®(for example maize), StarLink®(for example maize), Bollgard®(cotton), Nucotn®(cotton) and NewLeaf®(potatoes). Examples tolerant to herbicides plants are corn varieties, cotton varieties and soybean varieties sold under the trade names Roundup Ready®(tolerance to glyphosate, for example corn, cotton, soybeans), Liberty Link®(tolerance to phosphinotricin, for example, RA is C), IMI®(tolerance to imidazolinones) and STS®(tolerance to sulfonylurea, for example maize). As resisteth in relation to herbicide (usually cultivated on herbicide tolerance) plants are mentioned also sold under the name Clearfield®varieties (e.g., corn). All of the above of course also applies to plant varieties with genetic qualities ("signs")that will be developed in the future and, accordingly, will be available in the future on the market.

Presents plants particularly preferably be treated with compounds of formula (I). The preferred scope of the above active substances is processing plants. Particular emphasis is placed on the processing plant is specially presented in this text blends.

The active substances according to the invention can be translated in the usual preparative forms such as solutions, emulsions, wettable powders, suspensions, powders, powdered drugs, pastes, soluble powders, granules, suspension-emulsion concentrates, impregnated with active ingredient of natural and synthetic materials, as well as nonconception in polymeric materials form.

These preparative forms produced by known methods, e.g. the mixing of the active substances with extenders, such as liquid solvents and/or solid carriers, using, if necessary, surface active substances such as emulsifiers and/or dispersing agents and/or foaming agents.

In the case of using water as a filler, for example, to use organic solvents as auxiliary solvents. As liquid solvents can be used: aromatic compounds such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzene, chlorethylene or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example oils, mineral and vegetable oils, alcohols, such as butanol or glycol and also their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutylketone 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, clay, talc, chalk, quartz, attapulgite, montmorillonite or hard-shelled land and synthetic stone flour as highly dispersed silicic acid, alumina and silicates, as solid carriers in the granulates are used: for example, the R, crushed and fractionated Estestvennye rocks as calcite, marble, pumice, thick, dolomite, and also synthetic granules of inorganic and organic flour and granules of organic material such as sawdust, peel, coconut, corn cobs and stalks of tobacco; as emulsifiers and/or foaming agents are used: for example nonionic and anionic emulsifiers, such as esters polyoxyethylenic acids, esters polyoxyethylene alcohols, for example alkylarylsulphonates ether, alkylsulfonate, alkylsulfate, arylsulfonate and their hydrolysates; as dispersant use: for example, the alkaline sulfite liquor lignin and methylcellulose.

In the formulation may be used for adhesion, such as carboxymethylcellulose, natural and synthetic, powder, granular or latexbased polymers, such as gum Arabic, polyvinyl alcohol, polyvinyl acetate, and also natural phospholipids, such as cephalin and lecithins, and synthetic phospholipids. The following additives can be mineral and vegetable oils.

As the coloring matter can be used as inorganic pigments, for example iron oxide, titanium oxide, Prussian blue, and organic dyestuffs, such as she is new, azo - and metallophthalocyanine dyes and micronutrients, such as iron salts, manganese, boron, copper, cobalt, molybdenum and zinc.

Preparative form mostly contain 0.1 to 95 wt.% the active substances according to the invention, mainly 0.5 to 90%.

The active substances according to the invention can be used as such or in their formulation, as well as in mixtures with known herbicides and/or additives, which improve the compatibility of cultivated plants ("protection") for combating weeds, and you can use the finished formulation or cooked mixture. It is also possible mixture with a herbicide means that contain one or more known herbicides and fuse.

Examples used for the mixtures are known herbicides are:

Acetochlor, Acifluorfen (-sodium), Klonipin, Alachlor, Aloxide (-sodium), ametrine is high, Nicarbazin, Amithlon, Amidosulfuron, Anilofos, Azul, Atrazine, Azafenidin, Azimsulfuron, BAS-662H, Beflubutamid, Benazolin (-ethyl), Benferhat, Encultured (-methyl), Bentazon, Bestindian, Benzamycin, Benzefoam, Benzoylperoxy (-ethyl), Bialaphos, Bifenox, Bispyribac (-sodium), Bromobutyl, Bromophenoxy, Bromoxynil, Butachlor, Butoverall (-allyl), Butoxide, Butyl, Cafestol, Galaxidi, Carbetamide, Carfentrazone (-ethyl), X is amoxifen, Chloramben, ozone chloride, Chlorimuron (-ethyl), Chlornitrofen, Chlorsulfuron, Chlortoluron, Cinidon (-ethyl), Cinmetacin, Chinaculture, Clefoxydim, clethodim, Modinfop (-propargyl), Clomazone, Clomipram, Clopyralid, Cloperastine (-methyl), Karasulu (-methyl), Cumyluron, Cyanazine, Cybotron, Cycloate, Cycloaliphatic, Cycloxydim, Cyhalofop (-butyl), 2,4-D, 2,4-DB, Desmedipham, Diallate, Dicamba, Dichlorprop (-R), Diclofop (-methyl), Dicloflam, Detail (-ethyl), Difenzoquat, Diflufenican, Diflubenzuron, Dimefuron, Timepart, Dimethachlor, Deltamethrin, Dimethenamid, Dimexidum, Dinitramine, Diphenamid, Diquat, Dithiopyr, Diuron, Aprobada, ARTS, Asbroker, Ethalfluralin, Atomiculture (-methyl), Ethofumesate, Idoxifene, Ethoxysulfuron, Etamesonic, Fenoxaprop (-P-ethyl), Phentramin, Planrep (-isopropyl-isopropyl-L-methyl), Flazasulfuron, Florasulam, Fluazifop (-P-butyl), FlatOut, Flucarbazone (-sodium), Flufenacet, Flumetsulam, Flumiclorac (pencil), Flumioxazin, Flubiprofen, Flumetsulam, Flumeturon, Fluorochloridone, Fluoroglycofen (-ethyl), Floratam, Flourophenyl, Fluspirilene (-methyl-sodium), Flurenol (-butyl), Fluridone, Fluroxypyr (-butoxypropyl, -meptyl), Flurried, Flurtamone, Fluthiacet (-methyl), Flutamide, Fomesafen, Foramsulfuron, Glufosinate (-ammonium), Glyphosate (-isopropylammonium), Galasoft, Haloxyfop (etaxi the Tyl, -R-methyl), Hexazinone, Imazamethabenz (-methyl), Imazamethabenz, Imazamox, Imazapic, Imazapyr, Imazaquin, Imazethapyr, Imazosulfuron, Iodosulfuron (-methyl-sodium), Ioxynil, Isopropylene, Isoproturon, Sauron, Isoxaben, Isoxaflutole, Isoxaflutole, Isocaporate, Lactofen, Lenacil, Linuron, MSRA, Mecoprop, Mefenacet, Mesotrione, Metamitron, Metazachlor, Methabenzthiazuron, Metaventure, Metobromuron, (alpha) Metolachlor, Metosulam, Metoxuron, Metribuzin, Metsulfuron (-methyl), Molinet, Monolinuron, Nitroanilide, Napropamide, Neburon, Nicosulfuron, Norflurazon, Arrancar, Oryzalin, Oxadiargyl, Oxadiazon, Oxasulfuron, Oxacyclobutane, Oxyfluorfen, Paraquat, Pelargonia acid, Pendimethalin, Pentalyn, Phenoxazone, Phenmedipham, Picolinafen, Piperophos, Pretilachlor, Primisulfuron (-methyl), Proplusr, Prometryn, Propachlor, Propanil, Propaquizafop, Propisochlor, Propoxycarbazone (-sodium), Propyzamide, Prosulfocarb, Prosulfuron, Pyraflufen (-ethyl), Pyrazolyl, Pyrazolate, Pyrazosulfuron (-ethyl), Paradoxien, Perbenzoic, Perimutter, Peridot, Perinatal, Piritramid, Perminova (-methyl), Pyrithiobac (-sodium), Quinchlorac, Quinmerac, Quinoclamine, Quizalofop (-P-ethyl, P-tefuryl), Rimsulfuron, Sethoxydim, Simazine, Simetryn, Sulcotrione, Sulfentrazone, Sulfometuron (-methyl), Soulfood, Sulfosulfuron, TABATA is, Tebuthiuron, Tepraloxydim, Terbutylazine, Terbutryn, Tanishlar, Tefloned, Thiazopyr, Thidiazuron, Thifensulfuron (-methyl), Thiobencarb, Thiocarbonyl, Tralkoxydim, Triallate, Triasulfuron, Tribenuron (-methyl), Triclopyr, Tridiphane, Trifluralin, Trifloxysulfuron, triflusulfuron (-methyl), Tritosulfuron.

It is also possible mixture with other known active substances, as fungicides, insecticides, acaricides, nematicides, substances that protect from birds, nutrients for plants, substances and means of improving the soil structure.

The active substance can be used as such, in the form of their formulations or forms prepared from them further breeding and applied forms, such as ready to use solutions, suspensions, emulsions, powders, pastes and granulates. Application takes place in the usual manner, for example by pouring, spraying, spray, atomized spraying, spreading.

The active substances according to the invention can be applied both before and after germination of the plants. They can also be injected into the soil before sowing.

Consumable amount of the active substance according to the invention may vary within a wide range. It depends essentially on the type of desired effect. Basically expendable amount is from 1 g to 10 kg of the active substance per hectare of land area, mostly between 5 g and 5 kg per hectare.

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

Examples retrieve

Example I-1-a-1

To 6.5 g of potassium tert-butylate in 25 ml of anhydrous dimethylformamide (DFA) was added dropwise at 60°From 7.4 g of compound according to example II-1, dissolved in 1 ml of dehydrated DFA and further stirred for controlling the course of the reaction using thin layer chromatography. After the reaction, add 170 ml of ice water, acidified with concentrated hydrochloric acid at temperatures between 0°to 10°to pH 2, and then is sucked off and washed with water with ice. The residue is cleaned using chromatography on silica gel with methylene chloride/methanol 9:1 as the solvent.

Output: 3,90 g (≅58,00% of theory), TPL 199°

By analogy with example (I-1-a-1) and in accordance with the General instructions for the method of obtaining get the following compounds of formula (I-a-1).

Example I-1-b-1

2.5 g of compound I-1-a-10 in 50 ml of anhydrous ethyl ether acetic acid heats with 1.7 ml of triethylamine with stirring under reflux was added dropwise and under stirring to 1.3 ml of the acid chloride is somaclonal acid in 5 ml of dehydrated ethyl ester acetic acid, controlling the course of the reaction using thin layer chromatography. The solvent is distilled off, the residue is absorbed with methylene chloride, washed with 50 ml of 0.5 N NaOH, dried and treated on a rotary evaporator. Then the residue is recrystallized from a system of methyl-tert.-butyl ether (MTB-ether/n-hexane.

Yield: 2 g (≅65% of theory), TPL 209°

By analogy with example (I-1-b-1) and in accordance with the General instructions for the method of obtaining get the following compounds of formula (I-1-b)

Example I-1-C-1

Take of 2.51 g of compound of formula I-1-a-10 and 1.2 ml of triethylamine. At a temperature of from 0 to 10°added dropwise With 0.8 ml of ethyl ether of Harborview acid in 5 ml of dehydrated dichloromethane and stirred at room temperature, controlling the course of the reaction using thin layer chromatography. Washed 0,5N NaOH, dried and the solvent is distilled off. The residue is recrystallized from a system of methyl-tert.-butyl ether/n-hexane.

Yield: 1.1 g (≅30% of theory), TPL 178°

By analogy with example (I-1-s-1) and in accordance with the General instructions for the method of obtaining get the following compounds of formula (I-1-C)

Example II-1

7.5 g of 2,4-dimethyl-6-methyl-what analysisnew acid and 92 ml of thionyl chloride are stirred at 80° With as long as you do not stop the formation of gas. Excess thionyl chloride is distilled off and the residue is dissolved in 30 ml of dry THF. This solution was added dropwise at from 0 to 10°to 12.3 g of methyl ester of 2-amino-2-methylpropanoic acid in 320 ml of dry THF, which was added to 24.6 ml of triethylamine, and 1 hour and stirred at room temperature. This solution is treated on a rotary evaporator, diluted in methylene chloride and 1 N HCI, extracted, dried and treated on a rotary evaporator. The residue is recrystallized from MTB ether/n-hexane.

Output: 8,07 g (≅66% of theory), TPL 120-122°

Example II-11

It was 16.9 g of concentrated sulfuric acid added 10.3 g of the compound according to example XXVII-1 in suspension in 110 ml of methylene chloride at an internal temperature of 30 to 40°C and stirred for 2 hours. Was added dropwise 23 ml of dry methanol and stirred at a temperature of from 40 to 70°6 hours. The solution was poured 0.18 kg of ice, extracted with methylene chloride and washed with a solution of NaHCO3. Dry, rotate in a rotary evaporator and the residue crystallized from MTB ether/n-hexane.

Yield: 8.7 g (76% of theory), TPL 137°

By analogy with example (II-1) and in accordance with the General instructions for the method of obtaining get the following compounds of formula (II)

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Example XXVII-1

of 7.68 g of 2,4-diethyl-6-methyl-phenylacetic acid mixed with 9.1 ml of thionyl chloride at 80°until then, until all the formation of gas. Extra thionylchloride distilled off and the residue is dissolved in 40 ml of dry toluene. This solution was added dropwise at a temperature of from 0 to 10°With 9 g of 4-amino-4-cyano-of tetrahydrofuran and 80 ml of dry THF, which was added 6.2 ml of triethylamine, and 1 hour and stirred at room temperature. This solution is treated on a rotary evaporator, dissolved in 1 N HCL and methylene chloride, dried and treated on a rotary evaporator. The residue is recrystallized from MTB ether/n-hexane.

Yield: 10.3 g (≅85% of theory), TPL 155°

By analogy with example XXVII-1 receive connection example XXVII-2 TPL 142°C.

Example I-2-a-1

To 8,4 g of tert.-the butyl potassium in 50 ml of dehydrated DFA at a temperature of from 0 to 10°added dropwise With 16.6 g of the compound according to example III-1, dissolved in 50 ml of dehydrated DFA and stirred for 8 hours at room temperature. After the reaction was added dropwise under ice cooling to 1000 ml of 1 N HCI and stirred for 30 minutes, Dropped the precipitate is filtered off, washed and dried in vacuum.

Output: 11.5g (≅80% of theory), TPL 135°

By analogy with example (I-2-a-1) is according to the General instructions for the method of obtaining get the following compounds of formula (I-2-a)

Example I-2-b-1

To 2.86 g of the compound according to example I-2-a-1, dissolved in 40 ml of dry methylene chloride (CH2Cl2) add 2,08 ml of triethylamine. At 0-10°add 1.5 g of pualeilani in 10 ml of CH2Cl2and stirred for 20 h at room temperature.

The reaction solution washed first with 10%citric acid and then 1 N NaOH, dried, rotate on a rotary evaporator and the residue is stirred with petroleum ether.

Yield: 2.2 g (≅60% of theory), TPL 110-112°C.

Example I-2-b-2

1.2 g (was 2.76 mmol) of the compound according to example I-2-b-2 of WO 97/02243 diluted in 20 ml of toluene, add 3.5 g (11 mmol) tributyltinhydride, 133 mg (0.11 mmol) of Pd (PPh3)4and 2 crystal of 2,6-di-tert.-butyl-4-methylchrysene, the mixture is boiled overnight under reflux and then dried.

The crude mixture is purified by chromatographic method is not silica gel, initially using cyclohexane elute excess compounds of tin, and then, replacing the solvent to cyclohexane/uxury ether (2:1), elute in this solvent the product. Further purification is performed by rubbing with petroleum ether.

Output: 0,46 g (44% of theory)of colourless crystals with TPL 152-155°C.

By analogy with what reamers (I-2-b-1) and (I-2-b-2) and in accordance with the General instructions for the method of obtaining get the following compounds of formula (I-2-b)

Example III-1

of 8.9 g of 2-ethyl-4-methyl-phenylacetic acid in 50 ml of dry toluene and 7.3 ml of thionyl chloride are stirred at 80°until then, until all the formation of gas. Extra thionylchloride distilled off and the residue is dissolved in 30 ml of dry toluene. This solution was added dropwise at a temperature of from 0 to 10°to 8.6 g of ethyl ester 1-hydroxycyclohexanecarboxylate acid in 50 ml of dry toluene and stirred for 8 hours under reflux. Then this solution is treated on a rotary evaporator. Yield: 16.6 g (≅99% of theory)

The residue without further purification used in the condensation reaction in example I-2-a-1

Example I-4-a-1

2.4 g of 2-ethyl-4,6-dimethyl-2-phenylcarbonylamino diluted in 30 ml of abs. xylene and added dropwise to 1.5 g of 4-forpromotion in 20 ml of abs. xylene. Heated for 8 hours under reflux. Washed with xylene solution of water, dried over sodium sulfate and evaporated in vacuum.

Carry out the chromatographic purification on silica gel with toluene/ethanol 20:1 as additionally separated by.

Yield: 1 g (≅28% of theory) TPL 161-162°C.

Example I-6-a-1

to 5.3 g of compound according to example VIII-1 diluted in 50 ml of dry DFA add 2,95 g tre is.-the butyl potassium and heated 1 hour at 60° C.

The reaction solution is mixed with 100 ml of 1 N HCl, extracted with CH2Cl2, the organic phase is dried and concentrated. The residue is purified by column chromatography (cyclohexane : ethyl ester of acetic acid 5:1). Yield: 2.35 g (49% of theory), TPL 148°C.

Example I-6-b-1

1 g of compound according to example I-6-a-1 diluted in 20 ml of dry methylene chloride, add of 0.77 ml of triethylamine. Was added dropwise under ice cooling to 0.68 ml pualeilani dissolved in 1 ml of methylene chloride, and stirred for 2 hours at room temperature.

The reaction solution is twice extracted with 10% citric acid solution, the organic phase is twice washed with 1 N NaOH, dried and concentrated.

Yield: 1.2 g (92% of theory) of oil.

1H-NMR (500 MHz, CDCl3): δ=1,1 (s, 9H, -C(CH3),

2,31 (s, 3H, Ar-CH3); at 2.45 (q, 2H, Ar-CH2CH3) ppm

Example VIII-1

of 22.8 g of the raw product from example XXXIV-1, dissolved in 200 ml of dry acetone, mixed with 10.9 g of potassium carbonate and added dropwise to 33.6 g (14,75 ml) under the conditions. Stirred for 16 hours under reflux.

The solvent is distilled off and the residue is purified through column chromatography (methylene chloride/petroleum ether: 8:1).

Yield: 3.5 g (30% of theory), oil

The product is used directly in the cyclization at approx the ru I-6-a-1

Example XXXIV-1

11.2 g nanometrology ether cyclohexanedicarboxylic acid is heated with 5.3 ml of thionyl chloride was added dropwise and DFA in 50 ml of dry toluene by heating to 100°until then, until all the formation of gas. Concentrate from the solvent.

To a solution of 50 ml of LDA in 100 ml of dry THF was added dropwise at -15°With a solution of 17.3 g of methyl ester of 2-ethyl-4-methyl-phenylacetic acid in 20 ml of dry THF and stirred for 30 min at this temperature.

Then added dropwise at -15°With the solution of the above freshly prepared acid chloride acid in 15 ml of dry THF.

The original mixture is stirred for one hour at room temperature, then add 150 ml of water and 40 g of ammonium chloride. The intermediate product is extracted with ether, the solution is concentrated. The residue is boiled with 100 g of KOH and 330 ml of water for 2 days under reflux.

Output: 23,70 g (91% of theory), oil

Example XXV-1

To 26 g of compound according to example XXX-1 in 120 ml of THF at room temperature was added dropwise 4.7 g of lithium hydroxide dissolved in 120 ml of water and stirred for 8 hours at room temperature.

The reaction solution rotate on a rotary evaporator, water is added and extracted with methyl tert-butyl ether.

The aqueous phase was adjusted with concentrated hydrochloric acid the th to pH 2 and the drop-down sludge is pumped out and dried.

Yield: 14 g (59% of theory), MP: 156, 3mm°

Example XXX-1

The solution to 7.32 g of compound methyl ester of 2,6-dimethyl-4-bromo-phenylacetic acid (according to example XXVI-1 of WO 97/02243) in 70 ml of triethylamine with stirring in an argon atmosphere at room temperature is added 0.27 g of copper iodide (I), 0,745 g of triphenylphosphine, 1 g of bis(triphenylphosphine)palladium dichloride and then added dropwise to 19.7 ml trimethylsilylacetamide.

For the conversion is monitored by gas chromatography.

Cleanup leading to a chromatographic column with silica gel using petroleum ether/ethyl ester acetic acid, 20:1 as additionally separated by.

Yield: 6 g (73% of theory)

Example XXII-1

39 g of compound according to example XXV-2 is stirred with 300 ml of thionyl chloride at 50°before the termination of the generation of gas.

Excess thionyl chloride is distilled off, the residue is dissolved in 30 ml of dry toluene and distilled.

Yield: 37 g (87% of theory), BP.: 90-92° (0,05 mbar)

Example XXV-2

To 50 g of compound according to example XXX-2 add 60 ml ethanol, 30 ml of water, 25 g of sodium hydroxide and heated for 5 hours under reflux.

After the reaction the solvent is distilled off, the residue is dissolved in water, install an acidic pH using concentri vannoy hydrochloric acid. The precipitation is pumped, washed and dried. Yield: 41 g (93% of theory)

Example XXX-2 ((N))

60 g of compound according to example XLII-1 dissolved in 600 ml of ethanol, mixed with 50 ml of concentrated hydrochloric acid and add 5 g of 10% Pd/C.

At 120°C and 150 bar in the reaction mixture is poured hydrogen.

Upon completion the reaction was filtered, the solvent is distilled off, the residue is dissolved in 300 ml methylenechloride and washed with 300 ml of water, dried and concentrated.

Output: 51 g (91% of theory)

Example XLII-1 ((N))

Mix 200 g ml of carbon disulphide and to 86.7 g of aluminum chloride. When 0°With added dropwise 50 g of methyl ester of 2-methylphenylacetic acid and 28.2 g of acid chloride of propionic acid. The solution is stirred for 4 hours under reflux.

Then the solution serves on 1 kg of ice water and extracted with 500 ml of methylene chloride.

The organic phase is washed with 10% hydrochloric acid, then with soda solution, dried and concentrated.

Yield: 60 g (91% of theory)

Example XXV-3

To 30 g of compound according to example XXX-3 in 32 ml of methanol and 16 ml of water is added 12.2 g of potassium hydroxide and stirred for 5 hours under reflux.

The solution is concentrated and the residue is dissolved in water, washed with ethyl ether acetic acid is set pH of the aqueous phase with concentrated hydrochloric acid to 1. Drop-down sludge is pumped out, washed and dried.

Yield: 25 g (99% of theory), TPL 55-56°

Example XXX-3 (Method I)

of 20.8 g of compound methyl ester of 2,6-dimethyl-4-bromo-phenylacetic acid (according to example XXVI-6 of WO 97/02243) dissolved in 100 ml of methanol. Added 7.2 g of sodium acetate and 2 g of palladium hydroxide. Then hydronaut hydrogen under pressure.

After the reaction solution is filtered and concentrated. The residue is diluted in methylene chloride, washed with water, dried and concentrated.

Yield: 12 g (77% of theory)

Biological examples

Example

Test Myzus

Solvent:7 mass parts of dimethylformamide
Emulsifier:1 mass part alkylsilanes ether polyglycol

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

Cabbage leaves (Brassica oleracea), which was subjected to heavy attack pericolanti vosi (Myzus persicae), is treated by immersion in the mixture of the active substance is desired concentration.

After a certain amount of the belts define a loss in %. 100% means that all personalitie lice were killed; 0% means that none persinality lice were killed.

In this test, the compounds of examples obtain I-2-a-4, I-2-b-5, I-2-b-6, I-1-a-6, I-1-C-4, I-4-and-1 at the approximate concentration of the active substance from 1000 ppm showed 100% mortality after 6 days.

The example In

Test Nephotettix

Solvent:7 mass parts of dimethylformamide
Emulsifier:1 mass part alkylsilanes ether polyglycol

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

Embryos of rice (Oryza sativa) are treated by dipping in the mixture of the active substance of the desired concentration and plant green rice Cicada up until the leaves are still moist.

After a certain period of time to determine the loss in %. 100% means that all cicadas were killed; 0% means that none of the Cicada was not killed.

In this test, the compounds of examples obtain I-2-a-4, I-2-b-9, I-1-a-9, I-1-a-8, I-1-a-2, I-1-a-1, I-1-a-3, I-4-a-1 and the approximate concentration of the active substance from 1000 ppm showed 100% mortality after 6 days.

When the EP With

Test on larvae of Phaedon

Solvent:7 mass parts of dimethylformamide
Emulsifier:1 mass part alkylsilanes ether polyglycol

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

Cabbage leaves (Brassica oleracea) are treated by dipping in the mixture of the active substance of the desired concentration and infect larval sea beetles (Phaedon cochleariae) up until the leaves are still moist.

After a certain period of time to determine the loss in %. 100% means that all beetle larvae have been killed; 0% means that no larvae of the beetle were killed.

In this test, the compounds of examples obtain I-2-a-3, I-2-b-8, I-2-b-6, I-1-a-2, I-1-a-3, I-1-a-21, I-4-a-1 and the approximate concentration of the active substance from 1000 ppm showed 100% mortality after 7 days.

Example D

Test Plutella

Solvent:7 mass parts of dimethylformamide
Emulsifier:1 mass part alkylsilanes ether polyglycol

To obtain optimalnoe drug active substances 1 mass part of the active substance is mixed with the stated amounts of solvent and emulsifier and dilute the concentrate containing emulsifier with water to the desired concentration.

Cabbage leaves (Brassica oleracea) are treated by dipping in the mixture of the active substance of the desired concentration and plant the caterpillars of the cabbage cockroach (Plutella xylostella) up until the leaves are still moist.

After a certain period of time to determine the loss in %. 100% means that all caterpillars have been killed; 0% means that none of the caterpillars were killed.

In this test, the compounds of examples obtain I-1-a-8, I-4-a-1 and the approximate concentration of the active substance from 1000 ppm showed 100% mortality after 7 days.

Example F

Test Spodoptera frugiperda

Solvent:7 mass parts of dimethylformamide
Emulsifier:1 mass part alkylsilanes ether polyglycol

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

Cabbage leaves (Brassica oleracea) are treated by dipping in the mixture of the active substance of the desired concentration and plant caterpillars Heerwurms (Spodoptera rrugiperda) up until the leaves are still moist.

After a certain period of time to determine the loss in %. 100% means that all of the se is enizy died; 0% means that none of the caterpillars were killed.

In this test, the compounds of examples obtain I-2-a-3 and the approximate concentration of the active substance from 1000 ppm showed 100% mortality after 7 days.

Example F

The Tetranychus test (OP-resistant/treatment by immersion)

Solvent:7 mass parts of dimethylformamide
Emulsifier:1 mass part alkylsilanes ether polyglycol

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

Bean plants (Phaseolus vulgaris)were strongly attacked by spider Clasica ordinary (Tetranychus urticae), immersed in the mixture of the active substance is desired concentration.

After a certain period of time to determine the loss in %. 100% means that all spider mites have been killed; 0% means that none of the spider clasic were killed.

In this test, the compounds of examples obtain I-2-a-4, I-2-b-10, I-2-b-11, I-2-b-8, I-2-b-2, I-1-a-3, I-1-a-21, I-1-C-4, I-4-a-1 and the approximate concentration of the active substance from 1000 ppm showed 100% mortality after 7 days.

Example G

Test Bemiia

Solvent:7 mass parts of dimethylformamide
Emulsifier:1 mass part alkylsilanes ether polyglycol

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

Of the cotton plant (Gossypium hirsutum), subjected to severe attack eggs, larvae and puparia (false cocoon) white fly Bemisia tabaci, is dipped in the mixture of the active substance is desired concentration.

After a certain period of time to determine the loss in %. 100% means that all animals were killed; 0% means that no animal was killed.

In this test, the compounds of examples obtain I-2-b-9, I-2-a-4, I-2-b-10 and the approximate concentration of the active substance from 1000 ppm showed 100% mortality after 10 days.

Example N

Post-harvest test

Solvent:5 mass parts of acetone
Emulsifier:1 mass part alkylsilanes ether polyglycol

For optimal preparation of the active substance 1 moscoweast the active substance is mixed with the stated amounts of solvent and emulsifier and dilute the concentrate containing emulsifier with water to the desired concentration.

Test plants which have a height of from 5 to 15 cm are sprayed with the best preparations of the active substance so that per square unit area was desired consumable amount of the active substance. The concentration of the solution for spraying are selected so that with 1000 l of water/ha fell corresponding to the desired amount of the active substance.

After 3 weeks evaluated the degree of plant damage in % damage in comparison with the development are not subjected to the processing of the control.

This means:

0% = no action (as it is not exposed to processing control)

100% = total destruction

Example I

Pre-emergence test

Solvent:5 mass parts of acetone
Emulsifier:1 mass part alkylsilanes ether polyglycol

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

Seeds of the test plants contribute in normal soil. After about 24 hours, the soil is sprayed optimal preparations of the active substance in such a way that the RMS is tnou unit area was desired consumable amount of the active substance. The concentration of the solution for spraying is selected so that with 1000 l of water/ha fell corresponding to the desired amount of the active substance.

After 3 weeks evaluated the degree of plant damage in % damage in comparison with the development are not subjected to the processing of the control.

This means:

0% = no action (as it is not exposed to processing control)

100% = total destruction

Test Myzus

This test was conducted as described in the example As follows.

The compounds, their concentration in ppm and the degree of killing insects in 6 days summarized in table I.

Test Nephotettix

This test was carried out as described in example follows.

The compounds, their concentration in ppm and the degree of killing insects in 6 days summarized in table II.

Test on larvae of Phaedon

This test was carried out as described in example follows.

The compounds, their concentration in ppm and the degree of killing larvae after 6 days summarized in table III.

Test Spodoptera frugiperda

This test was carried out as described in example D.

The compounds, their concentration in ppm and the degree of killing of larvae after 6 days summarized in table IV.

Those who t on herbicide activity

Post-harvest processing

This test was carried out as described in example E.

The investigated compounds, the rate of consumption in g/ha and the degree of damage to the plants is summarized in table V.

Test for herbicide activity

Pre-emergence treatment

This test was carried out as described in example I by the way.

The investigated compounds, the rate of consumption in g/ha and the degree of damage to the plants is summarized in table VI.

The comparison is summarized in tables I-VI data for known compounds and compounds of the formula (I) and clearly shows the presence of compounds of the formula (I) are unknown for this group of properties in qualitative and quantitative terms.

With2-Phenylsilane circular ketoenol General formula

in which W is hydrogen, alkyl with 1-6 carbon atoms,

X is alkyl with 1-6 carbon atoms, alkenyl with 2-6 carbon atoms,

Y is hydrogen, methyl, ethyl, isopropyl, alkenyl with 2-6 carbon atoms, ethinyl,

Z is hydrogen, alkyl with 1 to 6 carbon atoms,

provided that at least one of the residues W, X, Y or Z means a chain with at least 2 carbon atoms, and only one of the residues X and Y can mean alkenyl with 2-6 carbon atoms,

The NEC means one of the groups

where a is hydrogen, alkyl with 1-6 carbon atoms,

In hydrogen, alkyl with 1-6 carbon atoms,

A and b together with the carbon atom to which they are connected, means cycloalkyl with 5-6 carbon atoms in which the carbon atom of the ring may be replaced by oxygen and which may be substituted by alkyl with 1-6 carbon atoms or alkoxyl with 1-6 carbon atoms,

And who In together mean a group

D is hydrogen or substituted by fluorine, phenyl, if the NEC shall mean a group of the formula (4),

G is hydrogen (a) or one of the groups

where R1means alkyl with 1-6 carbon atoms, alkoxymethyl with 1-2 carbon atoms,

R2means alkyl with 1-4 carbon atoms,

And Q1together mean alcander with 3-4 carbon atoms and

Q2means hydrogen.



 

Same patents:

FIELD: organic chemistry, medicine, pharmacy.

SUBSTANCE: invention proposes derivative of 3,4-dihydroisoquinoline of the formula (I) or its nontoxic salt and a pharmaceutical agent comprising its as an active component (wherein all symbols have the same values as given in description). Compound of the formula (I) possesses agonistic effect on CB2-receptors and, therefore, it can be used for prophylaxis and/or treatment of different diseases, for example, asthma, nasal allergy, atopic dermatitis, autoimmune diseases, rheumatic arthritis, immune dysfunction, postoperative pain and carcinomatous pain.

EFFECT: valuable medicinal properties of derivatives.

14 cl, 33 tbl, 561 ex

FIELD: pharmaceutical chemistry, in particular pharmaceutical compositions.

SUBSTANCE: new spyro(2H-1-benzopyrane-2,4'-piperidine) derivatives of general formula I

and pharmaceutically acceptable salts thereof are disclosed. In formula dotted line is optional bond; Y is 1-4 substituents independently selected from hydrogen, halogen, C1-C4-alkyl, optionally substituted with one or more halogen, C1-C6-alkyloxy, optionally substituted with halogen or C3-C6-cycloalkyl, C2-C6-alkenyloxy, C2-C6-alkinyloxy, C3-C6-cycloalkyloxy, C6-C12-aryloxy, arylalkyloxy, pyridilmethoxy, SR3, NR3R4, OSO2R5, and NR3SO2R4; or two Y together may form O-(CH2)n-O or O-(CF2)n-O, wherein n is 1 or 2: or Y is condensed C5-C6-aryl group; X is 1-3 substituents independently selected from hydrogen, halogen, hydroxyl, C1-C6-alkoxy, and C1-C4-alkyl; R1 is hydrogen, C1-C4-alkyl, or C6-C12-aryl; R2, R3, and R4 are independently hydrogen or C1-C4-alkyl; R5 is C6-C12-aryl. Also disclosed are pharmaceutical compositions including said derivatives and having activity in relation to CNS.

EFFECT: new compounds with valuable pharmacological action.

9 cl, 1 tbl, 83 ex

The invention relates to new derivatives of galantamine General formula I:

where R1-R5, G1-G3and W have the meanings indicated in the claims, and the invention relates to a method for producing these compounds, medicinal product and the method of its production

The invention relates to a derivative phthalazine General formula (I) or their pharmaceutically acceptable salts, or hydrates, where R1and R2are the same or different from each other and each represents a halogen atom, a C1-C4alkyl group which may be substituted by a halogen atom, a hydroxyl group or a C1-C4alkoxygroup, which may be substituted by a halogen atom, or cyano; X represents a cyano, a halogen atom, hydroxyimino, optional O-substituted C1-C4alkyl group, or a heteroaryl group selected from thiazoline, thienyl, pyrazolidine, triazolinones and tetrazolyl groups that may be substituted WITH1-C4alkyl group; Y represents a cyclic amino group (i) - (v) described in paragraph 1 of the claims; (vi) etinilnoy or ethyl group substituted WITH1-C4alkyl group, which, in turn, replaced by a number of deputies referred to in paragraph 1 of the claims; (vii) optionally substituted phenyl group; (viii) pyridyloxy or thiazolidine group

The invention relates to new derivatives of pyrrolidinone possessing biological activity, in particular derivatives of 1H-3-aryl-pyrrolidin-2,4-dione

The invention relates to new derivatives of 2-phenyl-4-it formula I

where R1- alkyl or - NR4R5the group, in which each of R4and R5independently from each other represents a hydrogen atom or akilou group;

R2- alkyl, C3-C7cycloalkyl, naphthyl, tetrahydronaphthyl or indanyl or phenyl group which may be unsubstituted or substituted by one or more halogen atoms or alkyl groups, or trifluoromethyl, or alkoxy;

R3the group of methyl, hydroxymethyl, alkoxymethyl, hydroxycarbonyl, nitrile, trifluoromethyl or deformity or the group CH2-R6in which R6is an alkyl group, and

X is a simple bond, an oxygen atom or a methylene group,

or their pharmaceutically acceptable salts, and pharmaceutical compositions based on them, inhibiting the activity of cyclooxygenase-2, and method of treatment

The invention relates to new heterocyclic compounds with biological activity, and more particularly to derivatives of 5,6-dihydropyrone and pharmaceutical compositions based on them

The invention relates to new heterocyclic compounds with biological activity, in particular pyrone derivatives having antibacterial and antiviral activity

The invention relates to new Paramonova compounds useful for the inhibition of retrovirus in human cells infected with the indicated retroviruses

The invention relates to new derivatives of galantamine General formula I:

where R1-R5, G1-G3and W have the meanings indicated in the claims, and the invention relates to a method for producing these compounds, medicinal product and the method of its production

The invention relates to new compounds used in the pharmaceutical industry for the manufacture of medicines

FIELD: organic chemistry, herbicides.

SUBSTANCE: invention describes phenyl-substituted heterocyclic 1,3-ketoenols of the formula (I): wherein R1 and R3 mean independently of one another ethyl or (C1-C2)-alkoxy-group; Q means the group of the formula (Q1): or (Q2): wherein R4 and R5 in common with atoms to which they are joined form 5-7-membered cycle that can comprise additionally anellated alkylene chain consisting of 2-6 carbon atoms that, in turn, can comprise two heteroatoms taken among oxygen atom, and indicated cycle can be substituted with halogen atom, hydroxy-group, (C1-C6)-alkoxy-group, (C1-C6)-alkoxy-(C1-C6)-alkoxy-group, (C1-C4)-alkylcarbonyloxy-group, hydroxy-(C1-C4)-alkoxy-group, hydroxycarbonyl-(C1-C2)-alkoxy-group, methoxycarbonyl-(C1-C2)-alkoxy-group, methoxyimino-, methoxyethoxyethoxy-group; R6 and R7 means (C1-C10)-alkyl; R8 means hydrogen atom; X means oxygen atom; R20 means (C1-C10)-alkyl, and also agronomically acceptable salts and isomers of these compounds. Also, invention describes a method for preparing compounds of the formula (I), herbicide agent and a method for control of weed growth based on compounds of the formula (I). Invention provides preparing compounds possessing the herbicide activity.

EFFECT: improved preparing method, valuable properties of compounds and agents.

5 cl, 28 tbl, 5 ex

FIELD: organic chemistry, medicine.

SUBSTANCE: invention relates to new compound, 1-(3-aminopropyl)-3-hydroxy-5-(4-fluorophenyl)-4-(4-chlorobenzoyl)-3-pyrroline-2-one hydrochloride of the formula:

that elicits an anti-inflammatory activity that allows its using in medicine. Invention describes a method for its preparing.

EFFECT: valuable medicinal properties of compound.

2 tbl, 1 ex

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)

The invention relates to new biologically active compounds 2-pyrrolone, namely 4-acetyl-5-p-itfeel-1-carboxymethyl-3-hydroxy-2,5-dihydropyrrol-2-ONU formula

< / BR>
possessing analgesic activity, suggesting the possibility of its use in medicine as an anaesthetic
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