Derivatives dihydrobenzofuran, herbicide composition and method for killing weeds

 

(57) Abstract:

Discover new dihydrobenzofuran formula I

< / BR>
where a is hydrogen, fluorine or chlorine;

X is fluorine, chlorine or bromine;

Y is methyl substituted by one or more halogen atoms;

Z - methyl;

R1- hydrogen and C1-C6-alkyl;

R2- C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-hydroxyalkyl, C1-C6alkoxy(C1-C6)alkyl, C1-C6-alkoxy(C1-C6)alkoxy-(C1-C6)alkyl, C1-C7-acyloxy(C1-C6)alkyl, carboxyl,1-C6-alkoxycarbonyl, C1-C6-gloucestershi,3-C6-cycloalkylcarbonyl, C2-C6-alkylalkoxysilane, as well as intermediate compounds of formulas II and IV. Also disclosed herbicide composition containing servicenotification amount of compound (I) as active ingredient and method of destruction of unfavorable weeds application servicenotification amount of compound (I) in the square, where grow or will grow unfavorable weeds.

< / BR>
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5C and 4 C.p. f-crystals, 9 PL.

The present invention otnositeljno.

It is well known that certain types of substituted dihydrobenzofuran derivatives can be used as active ingredients of herbicides (see, for example, U.S. patent N 4881967).

These compounds, however, have little herbicide activity and poor selectivity to cultivated plants and weeds and it is not always possible to say that they are satisfactory ingredients of herbicides.

Under these circumstances, the authors of the present invention intensively studied various compounds. As a result, they have found that certain types dihydrobenzofuran derivatives have an excellent herbicide activity and show excellent selectivity with respect to cultivated plants and weeds, thereby making full the present invention.

Thus, the present invention offers new dihydrobenzofuran derivatives of the formula I

< / BR>
where A is hydrogen, fluorine or chlorine;

X is hydrogen, fluorine, chlorine or bromine;

Y is methyl, optionally substituted by one or more halogen atoms;

Z is methyl or amino;

R1is hydrogen or C1- C6-alkyl;

R2- C1- C6-UB>)alkyl, C1- C6-alkoxy(C1- C6)alkoxy(C1- C6)alkyl, C1- C7-acyloxy(C1- C6)alkyl, carboxyl, C1- C6-alkoxycarbonyl, C1- C6-haloalkoxy, C3- C6-cycloalkylcarbonyl, C2- C6-alkyloxyaryl, aminocarbonyl, C1- C6-alkylaminocarbonyl or phenylenecarbonyl containing phenyl group, optionally substituted C1- C6-alkyl, C1- C6-alkoxy, C1- C6-Galaxia, C1- C6-haloalkoxy, halogen, nitro, cyano or C1- C6-alkylthio.

In formula I, above, examples of acyl groups are C1- C6-alkylsulphonyl, C1- C6-haloalkylthio, C3- C6-cycloalkylcarbonyl or benzoyl, and examples of the halogen atom are fluorine, chlorine and bromine.

The present invention also offers a herbicide composition comprising herbicide effective amount of the compound (I) as an active ingredient, and a method for killing unwanted weeds by applying herbicide effective amount of compound (I) on the area where you are growing or will grow nenia (a).

The compound (I), where R2- C1- C6-alkyl, can be obtained by the intramolecular cyclization reaction of the compounds of formula II

< / BR>
where R4and R3the same or different, is hydrogen or C1- C6-alkyl, provided that the total number of carbon atoms in R3and R4not more than 6;

A, X, Y, Z, and R1everyone has values, as defined above.

The reaction is usually carried out without any solvent or in a solvent in the presence or in the absence of catalyst at 0 - 250oC, preferably 20 to 200oC, within 1/2 - 24,0 hours the Catalyst is used in amount of 0.01 - 0.5 mol per 1 mol of compound (II).

Examples of solvents are aliphatic hydrocarbons such as petroleum ether and hexane; aromatic hydrocarbons such as toluene and xylene; halogenated hydrocarbons such as chloroform, 1.2 - dichloroethane, chlorobenzene and o-dichlorobenzene; ethers, such as diethyl ether, diisopropyl ether, 1.4 - dioxane, tetrahydrofuran, and dimethyl ether of ethylene glycol; ketones, such as acetone, methyl isobutyl ketone and cyclohexanone; fatty acids, such as formic acid and acetic acid; alcohols such as methanol, ethano taronites; amides of acids, such as formamide, N,N-dimethylformamide and ndimethylacetamide; sulfur-containing compounds such as dimethylsulfoxide and sulfolan; and water. These solvents may be used alone or in combination.

Examples of catalysts are sulfonic acids such as p-toluensulfonate acid and methanesulfonamide acid; sulfonates, such as pyridi-p-toluensulfonate; and mineral acids such as sulfuric acid and hydrochloric acid.

After the reaction, the reaction mixture is subjected to ordinary post-processing. For example, the reaction mixture was poured into water and the precipitated catalyst is separated by filtration or, on the contrary, the reaction mixture is extracted with an organic solvent and concentrated. If you spend any purification, such as chromatography was carried out, distillation or recrystallization, thus obtaining the desired compound.

The compound (II) can be obtained by reaction of compounds of formula III

< / BR>
where A, X, Y, Z, R1, R3, R4each has the meaning as defined above,

without any solvent or in a solvent at 20 to 300oC, preferably 100 to 250oC, within 1/2 - haxan; aromatic hydrocarbons, such as toluene, xylene and m-isobutylene; halogenated hydrocarbons such as chloroform, 1.2-dichloroethane, chlorobenzene and o-dichlorobenzene; ethers, such as diethyl ether, diisopropyl ether, 1.4-dioxane, tetrahydrofuran, and dimethyl ether of ethylene glycol; ketones, such as acetone, methyl isobutyl ketone and cyclohexanone; fatty acids, such as formic acid and acetic acid; alcohols such as methanol, ethanol and ethylene glycol; esters such as ethyl acetate and diethylcarbamyl nitro compounds such as nitroethane and nitrobenzene; NITRILES, such as acetonitrile isobutyronitrile; tertiary amines such as pyridine, triethylamine, N,N-dimethylaniline; acid amides, such as formamide, N,N-dimethylformamide and ndimethylacetamide; sulfur-containing compounds such as dimethylsulfoxide and sulfolan; and water. These solvents may be used alone or in combination.

After the reaction, the reaction mixture is subjected to ordinary post-processing. For example, the reaction mixture was poured into water and the precipitated catalyst is separated by filtration or, on the contrary, the reaction mixture is extracted with an organic solvent and concentrated. If neophocaena the desired connection.

The compound (III) can be obtained according to the method described in patent JP-A63-41466 and EP-517181-A.

(Method get (b)).

The compound (I), where R2- C1- C6-hydroxyalkyl can be obtained by the interaction of the compounds (II), which is the starting compound of method of obtaining (a), with amoxicillim agent (first stage) and then the subsequent cyclization reaction product in the presence of a catalyst (second stage), if necessary, as shown in the following diagram:

< / BR>
where

N,N - diethylaniline and N - methylmorpholine;

A, X, Y, Z, R1, R3, R4"each has the meaning as defined above.

The first stage is usually carried out in a solvent at a temperature of from -20 to 150oC., preferably 0 to 80oC for 0.5 - 24 hours Epoxygenase agent is used in quantities of 1 to 5 mol per 1 mol of compound (II).

Examples of solvents that can be used in the first stage, are aliphatic hydrocarbons such as petroleum ether and hexane; fatty acids, such as formic acid and acetic acid; and halogenated hydrocarbons such as methylene chloride, chloroform and 1,2 - dichloroethane. Examples epoxydiols the lot and cryptocercus acid.

After the reaction, the reaction mixture is treated regenerating agent such as aqueous sodium thiosulfate and water hydrosulfite sodium, and subjected to conventional post-processing, such as extraction with an organic solvent and concentration, after which apply any treatment, if necessary, such as chromatography was carried out or recrystallization, thus obtaining the compound (IV) or the desired compound (I - I), which is prepared from the compound (IV) direct cyclization.

The second stage is usually carried out in a solvent in the presence or absence of a catalyst at a temperature of from -20 to 250oC, preferably from 0 to 200oC during the period of time from moment to 24 hours. The catalyst is used in quantities of from a catalytic amount to 5 mol per 1 mol of compound (IV).

Examples of solvents that can be used in the second stage, represent aliphatic hydrocarbons such as petroleum ether and hexane; aromatic hydrocarbons such as toluene and xylene; halogenated hydrocarbons such as chloroform, 1.2 - dichloroethane, chlorobenzene and o-dichlorobenzene; ethers such as diethyl ether, diisopropyl Eton and cyclohexanone; fatty acids, such as formic acid and acetic acid; alcohols such as methanol, ethanol and ethylene glycol, esters such as ethyl acetate and diethylmalonate; nitro compounds such as nitroethane and nitrobenzene; NITRILES such as acetonitrile and isobutyronitrile; tertiary amines such as pyridine, triethylamine, N,N-dimethylaniline, N,N-diethylaniline and N-methylmorpholine; acid amides, such as formamide, N,N-dimethylformamide and ndimethylacetamide; sulfur-containing compounds such as dimethylsulfoxide and sulfolan; and water. These solvents may be used alone or in combination.

Depending on the type of the used solvent can be used in a variety of catalysts, examples of which include sulfonic acids such as p-toluensulfonate acid and methanesulfonamide acid; sulfonates, such as pyridi-p-toluensulfonate; mineral acids such as sulfuric acid, hydrochloric acid; a Lewis acid such as boron TRIFLUORIDE, diethylether and zinc chloride; inorganic bases such as potassium carbonate, sodium hydroxide and potassium hydroxide; and metal hydrides such as sodium hydride and potassium hydride.

After the reaction, R is lly separated by filtration, or, on the contrary, the reaction mixture is extracted with an organic solvent and concentrated. If necessary, apply any purification, such as chromatography was carried out, distillation or recrystallization, thus obtaining the desired compound.

(Method of obtaining a (c)).

The compound (I), where R2represents C1- C6-alkoxy(C1- C6)-alkyl or C1- C6-alkoxy(C1- C6)alkoxy( C1- C6)alkyl can be obtained by interaction of the compound (I - I), which is obtained by the method of obtaining (b), as described above, with the compound of the formula V

R5J,

where R5- C1- C6-alkyl or C1- C6-alkoxy(C1- C6)alkyl;

J is halogen, methanesulfonate or p-toluensulfonate.

The reaction is usually conducted in a solvent in the presence of a base at a temperature of -20oC to temperature phlegmy solvent, if used, during the time from moment to 24 hours. The compound (V) and the base is used in an appropriate amount of 1 to 10 mol per 1 mol of compound (I - I).

Examples of solvents are aliphatic hydrocarbons such as petroleum ether and Arm, 1.2-dichloroethane, chlorobenzene and o-dichlorobenzene: ethers, such as diethyl ether, diisopropyl ether, 1.4-dioxane, tetrahydrofuran, and dimethyl ether of ethylene glycol; ketones, such as acetone, methyl isobutyl ketone and cyclohexanone; ethers complex, such as ethyl acetate and diethylmalonate; nitro compounds such as nitroethane and nitrobenzene; NITRILES such as acetonitrile and isobutyronitrile; tertiary amines such as pyridine, triethylamine, N-dimethylaniline, N, N-diethylaniline and N-methylmorpholine; acid amides, such as formamide, N,N-dimethylformamide and ndimethylacetamide; and sulfur-containing compounds such as dimethylsulfoxide and sulfolan. These solvents may be used alone or in combination.

Examples of bases are inorganic bases such as potassium carbonate, sodium hydroxide, potassium hydroxide; metal hydrides such as sodium hydride and potassium hydride; and organic bases such as triethylamine, diisopropylethylamine, pyridine and 4-dimethylaminopyridine.

After the reaction, the reaction mixture is subjected to ordinary post-processing. For example, the reaction mixture was poured into water and the precipitated crystals are separated by filtration or, on the contrary, reaction akuu as the chromatography was carried out, distillation or recrystallization, thus obtaining the desired compound.

(Method of obtaining a (d)).

The compound (I), where R2represents C1-C7-aryloxyalkyl, can be obtained by interaction of the compound (I - I), which is obtained by the method of obtaining (b), as described above, with the compound of the formula VI

R6G,

where R6- C1- C7-acyl; G is chlorine or bromine,

or the compound of formula VII

(R6)2O,

where R6has the meaning as defined above.

The reaction is usually carried out without any solvent or in a solvent in the presence of a base at temperatures between -20oC to 200oC, preferably from 0oC to temperature phlegmy, the solvent, if used, during the period of time from moment to 24 hours. The compound (VI) or (VII) and the base is used in an appropriate amount from 1 mol to a large excess per 1 mole of compound (I - I).

Examples of solvents are aliphatic hydrocarbons such as petroleum ether and hexane; aromatic hydrocarbons such as toluene and xylene; halogenated hydrocarbons such as chloroform, 1.2-dichloroethane, chlorobenzene and o-dichlor the initial ether of ethylene glycol; ketones, such as acetone, methyl isobutyl ketone, and cyclohexanone; esters such as ethyl acetate and diethylmalonate; nitro compounds such as nitroethane and nitrobenzene; NITRILES such as acetonitrile and isobutyronitrile; tertiary amines such as pyridine, triethylamine, N,N-dimethylaniline, N, N-diethylaniline, and N-methylmorpholine; acid amides, such as formamide, N, N-dimethylformamide and ndimethylacetamide; sulfur-containing compounds such as dimethylsulfoxide and sulfolan. These solvents may be used alone or in combination.

Examples of bases are inorganic bases such as potassium carbonate, sodium hydroxide and potassium hydroxide; metal hydrides such as sodium hydride and potassium hydride; and organic bases such as triethylamine, diisopropylethylamine, pyridine and 4-dimethylaminopyridine.

After the reaction, the reaction mixture is subjected to ordinary post-processing. For example, the reaction mixture was concentrated; the reaction mixture is poured into water and the precipitated crystals are separated by filtration; or the reaction mixture is extracted with an organic solvent and concentrated. If necessary, perform any cleanup, such as chromatographicaliy predstavljaet aryloxyalkyl, can be obtained by interaction of the compound (I - I), which is obtained by the method of obtaining (b) with the compound of the formula VII-2

R6-OH,

where R6has the meaning as defined above.

The reaction is usually carried out without any solvent or in a solvent in the presence of acid or condensing agent at a temperature of from 0 to 200oC, preferably between 10oC to temperature phlegmy solvent, if used, or preferably from 10 to 100oC if you do not use a solvent during the period of time from moment to 24 hours. Compound (VII-2) is used in an amount of from 1 mol to a large excess per 1 mole of compound (I-I). The acid is used in a catalytic amount or up to a maximum amount of 1 mol per 1 mol of compound (I - I). The condensing agent is used in quantities of 1 to 5 mol per 1 mol of compound (I - I)

Examples of solvents are aliphatic hydrocarbons such as petroleum ether and hexane; aromatic hydrocarbons such as toluene and xylene; halogenated hydrocarbons such as chloroform, 1.2-dichloroethane, chlorobenzene and o-dichlorobenzene: ethers, such as diethyl ether, diisopropyl ether, 1.4-dioxane, tetrahydrofuran and the, such as ethyl acetate diethylcarbamyl; nitro compounds such as nitroethane, nitrobenzene; NITRILES, such as acetonitrile, and isobutyronitrile; tertiary amines such as pyridine, triethylamine and N,N-diethylaniline, N-methylmorpholine; acid amides, such as formamide and N,N-dimethylformamide and ndimethylacetamide; sulfur-containing compounds such as dimethylsulfoxide and sulfolan. These solvents may be used alone or in combination.

Examples of acids are sulfonic acids such as p-toluensulfonate acid; sulfonates, such as pyridi-p-toluensulfonate; and mineral acids such as sulfuric acid and hydrochloric acid.

Examples of condensing agents are N,N'-disubstituted of carbodiimide such as N, N'-dicyclohexylcarbodiimide; 2,4,6-trimethylbenzenesulfonamide and N,N'-carbonyldiimidazole.

After the reaction, the reaction mixture is subjected to ordinary post-processing. For example, the reaction mixture is concentrated, the reaction mixture was poured into water and the precipitated crystals are removed by filtration; or the reaction mixture is extracted with an organic solvent and concentrated. If necessary, perform any cleanup, such as Holocene (e).

The compound (I), where R2is carboxyl, can be obtained by oxidation of compound (I - I)

where R3and R4are both hydrogen, and an oxidizing agent.

The reaction is usually carried out in a solvent at a temperature of from -80 to 100oC, preferably 0 to 50oC, for a time of 0.5 - 12 hours. Oxidizing agent is used in an amount of from 1 mol to a large excess per 1 mole of compound (I - I).

Examples of the oxidizing agent are permanganates such as potassium permanganate; chromic acid, such as chromium trioxide(sulphuric acid, potassium bichromate and pyridineboronic; and gaseous oxygen.

Depending on the used type of oxidizing agent, can be used in a variety of solvents, examples of which include aliphatic hydrocarbons such as petroleum ether and hexane; aromatic hydrocarbons such as toluene and xylene; halogenated hydrocarbons such as chloroform, 1.2-dichloroethane, chlorobenzene and o-dichlorobenzene: ketones, such as acetone, methyl isobutyl ketone and cyclohexanone; fatty acids, such as formic acid and acetic acid; ethers, such as ethyl acetate and diethylmalonate; amides of acids,sulfolan; and the water. These solvents may be used alone or in combination.

After the reaction, the reaction mixture is subjected to ordinary post-processing. For example, the reaction mixture was poured into water and the precipitated crystals are separated by filtration or, on the contrary, the reaction mixture is extracted with an organic solvent and concentrated. If you spend any purification, such as chromatography was carried out distillation or recrystallization, thus obtaining the desired compound.

(Method of obtaining a (f)).

The compound (I), where R2represents C1- C6-alkoxycarbonyl, C1- C6-haloalkoxy, C3- C6-cycloalkylcarbonyl or C2- C6-alkyloxyaryl can be obtained by reaction of the compound (I), where R2is carboxyl, which is obtained by the method of obtaining (e), with the compound of the formula VIII

R7-OH,

where R7- C1- C6-alkyl, C1- C6-haloalkyl, C3- C6-cycloalkyl or C2- C6-quinil.

The reaction is usually carried out databases of any solvent or in a solvent in the presence of acids at temperatures of from 20 to 200o2is carboxyl.

Examples of acids are mineral acids such as sulfuric acid and hydrochloric acid; and sulfonic acids such as p-toluensulfonate acid.

Examples of solvents are aliphatic hydrocarbons such as petroleum ether and hexane; aromatic hydrocarbons such as toluene and xylene; halogenated hydrocarbons such as chloroform, 1.2-dichloroethane, chlorobenzene or o-dichlorobenzene; ethers, such as diethyl ether, diisopropyl ether, 1.4-dioxane, tetrahydrofuran, and dimethyl ether of ethylene glycol; amides of acids, such as formamide and N,N-dimethylformamide and ndimethylacetamide; and sulfur-containing compounds such as dimethylsulfoxide and sulfolan. These solvents may be used alone or in combination.

After the reaction, the reaction mixture is subjected to ordinary post-processing. For example, the reaction mixture was poured into water and the precipitated crystals are separated by filtration or, on the contrary, the reaction mixture is extracted with an organic solvent and concentrated. If you spend any purification, such as chromatography was carried out, justify or precrystallization, haloalkoxy, cycloalkylcarbonyl or lineaccessori, can be obtained by interaction of the compound (I), where R2is carboxyl, which is obtained by the method of obtaining (e), in its activated reactive derivative in accordance with chemically acceptable way and then the interaction of this derivative with the compound (VIII).

To activate can be used in a variety of ways, such as those where the use of phosgene, oxalicacid, thionyl chloride. the phosphorus oxychloride, N, N'-carbonyldiimidazole, N, N'-dicyclohexylcarbodiimide, or 2,4,6-trimethylbenzenesulfonamide.

The reaction of the reactive derivative with the compound (VIII) is usually conducted in a solvent in the presence of a base or in the absence of a base at a temperature of from -20 to 100oC, during the period of time from moment to 24 hours. The compound (VIII) is used in an amount of from 1 mol to a large excess per 1 mole of compound (I), where R2is carboxyl. The base is used in amounts of 1 to 5 mol per 1 mol of compound (I), where R2is carboxyl.

Examples of solvents are aliphatic hydrocarbons such as petroleum ether and Gorm, 1.2-dichloroethane, chlorobenzene and o-dichlorobenzene: ethers, such as diethyl ether, diisopropyl ether, 1.4-dioxane, tetrahydrofuran, and dimethyl ether of ethylene glycol; ketones, such as acetone, methyl isobutyl ketone, and cyclohexanone; nitro compounds such as nitroethane and nitrobenzene; NITRILES such as acetonitrile and isobutyronitrile; tertiary amines such as pyridine, triethylamine, N, N-dimethylaniline, N,N-diethylaniline and N-methylmorpholine; acid amides, such as formamide, N, N-dimethylformamide and ndimethylacetamide; sulfur-containing compounds such as dimethylsulfoxide and sulfolan. These solvents may be used alone or in combination.

Examples of bases are inorganic bases such as potassium carbonate, sodium hydroxide and potassium hydroxide; tertiary amines such as pyridine and triethylamine.

After the reaction, the reaction mixture is subjected to ordinary post-processing. For example, the reaction mixture was poured into water and the precipitated crystals are separated by filtration or, on the contrary, the reaction mixture is extracted with an organic solvent and concentrated. If you spend any purification, such as chromatography was carried out, justify or perakis the s (I), where R2- aminocarbonyl, C1- C6-alkylaminocarbonyl or phenylenecarbonyl containing a phenyl group optionally substituted C1- C6-alkyl, C1- C6-alkoxy, C1- C6-haloalkoxy, C1- C6-haloalkyl, halogen, nitro, cyano or C1- C6-tilkian, can be obtained by converting compound (I), where R2is carboxyl, which is obtained by the method of obtaining (e), its reactive derivative according to the method of obtaining (f), as described above, and then the interaction of this derivative with the compound of the formula IX

R8R9NH,

where R8and R9are the same or different and independently represent hydrogen, C1- C6-alkyl, or phenyl, optionally substituted C1- C6-alkyl, C1- C6-alkoxy, C1- C6-haloalkyl, C1- C6-haloalkoxy, halogen, nitro, cyano or C1- C6-thioalkyl.

The reaction is usually carried out in a solvent at a temperature from 0 to 100oC, preferably from 5 to 80oC, during the period of time from moment to 24 hours. The compound (IX) is used in an amount of from 1 mol to the large of the amount of aliphatic Uglevodorody, such as petroleum ether and hexane; aromatic hydrocarbons, such as chloroform, 1,2-dichloroethane, chlorobenzene and o-dichlorobenzene; ethers, such as diethyl ether, Diisopropylamine ether, 1,4-dioxane, tetrahydrofuran, and dimethyl ether of ethylene glycol; ketones, such as acetone, methyl isobutyl ketone, and cyclohexanone; esters such as ethyl acetate, and diethylmalonate; nitro compounds such as nitroethane and nitrobenzene; NITRILES such as acetonitrile and isobutyronitrile; tertiary amines such as pyridine, triethylamine, N, N-dimethylaniline; N,N-diethylaniline, and N-methylmorpholine; acid amides, such as formamide, N,N-dimethylformamide and ndimethylacetamide; sulfur-containing compounds such as dimethylsulfoxide and sulfolan. These solvents may be used alone or in combination.

After the reaction, the reaction mixture is subjected to ordinary post-processing. For example, the reaction mixture was poured into water and the precipitated crystals are separated by filtration or, on the contrary, the reaction mixture is extracted with an organic solvent and concentrated. If you spend any purification such as chromatography was carried out, distillation or recrystallization, thus obtaining the desired soy is SUB>-haloalkyl, can be obtained by gorodilova the compound (I - I), which is obtained by the method of obtaining (b), palodiruyut agent.

The reaction is usually carried out without any solvent or in a solvent at a temperature of from -20 to 200oC, preferably from 0 - 150oC for from 0.5 to 24 hours. Gaodirelwe agent is used in quantities of 1 to 10 mol per 1 mol of compound (I - I).

Examples of the solvent are halogenated hydrocarbons such as dichloromethane and chloroform; methylene chloride; aromatic hydrocarbons such as toluene and xylene; ethers such as diethyl ether and tetrahydrofuran.

Examples Ganoderma agents are fluorinating agents, such as diethylaminosulfur; gloriouse agents, such as tetrachloride/triphenylphosphine; and brainwashee agents, such as tetrabromide/triphenylphosphine.

After the reaction, the reaction mixture is subjected to ordinary post-processing. For example, the reaction mixture was poured into water and the precipitated crystals are separated by filtration or, on the contrary, the reaction mixture is extracted with an organic solvent and concentrated. If necessary, carry out any cleaning such as x According to any of the above methods of obtaining (a) - (h), compounds (I) are obtained, as shown in table 1, where the symbols (n) and (c) note normal alkyl chain and cycloalkyl groups, respectively.

The compound (I) of the present invention have excellent herbicide activity and some of them show excellent selectivity with respect to cultivated plants and weeds. Thus, compound (I) of the present invention have a weed-killing activity against a variety of adverse weeds, such as the following when handling the leaves, or soil treatment on upland fields.

Polygonaceae:

Highlander Curling (Polygonum convolvulus), pale knotweed pepper (Polygonum lapathifolium), Pennsylvania Highlander pepper (Polygonum pensylvanicum), sorrel curly (Rumex crispus), sorrel bubble (Rumex obtusifolius).

Portulacaceae: garden purslane (Portulaca oleracea)

Caryophyllaceae: sigcatch average (Stellaria media)

Chenopodiaceae: white pigweed common (Chenopodium album), kochia (Kochia scoparia)

Amaranthaceae:

amaranth spiked (Ameranthus retroflexus, Amaranthus hybrid (Amaranthus hybridus)

Crusiferae:

radish wild (field) (Raphanus raphanistrum), mustard field (Brassica kaber), shepherd's-purse common (Capsella bursa-pastoris)

Leguminosae:

hemp sesbania (Sesbania exaltata), wall-cress canadian (Cassia obtusifolia), Florida
Violaceae: violet field (Viola arvensis), wild Pansy (Viola tricolor)

Rubiaceae:

cleaver (cleavers (Galium aparine)

Convolvulaceae:

morning glory plusline (Ipomoea hederacea), morning glory high (Ipomoea purpurea), morning glory plusline (Ipomoea hederacea var.integriuscula), morning glory celesta (Ipomoea lacunosa), field bindweed (Convolvulus arvensis)

Labiatae:

the red dead-nettle (Lamium purpureum), dead-nettle (Lamium amplexicaule)

Solanaceae:

jimson weed (Datura stramonium), black nightshade (Solanum nigrum)

Scrophulariaceae:

Veronica Persian (Veronica persica), Veronica plusline (Veronica hederaefolia)

Compositae:

cocklebur (Xanthium pensylvanicum), annual sunflower (Helianthus annuus), chamomile (matricaria inodora), slative (Chrysanthemum segetum), pineappleweed (Matricaria matricarioides), abrosia (Ambrosia artemisiifolia), ragweed trenatacna (Ambrosia trifida), melkosopochnik canadian (Erigeron canadensis)

Spread over:

the field forget-me-not (Myosotis arvensis)

Asclepiadaceae:

walochnik Syrian (Asclepias syriaca)

Euphorbiaceae:

milkweed cancelled (Euphorbia helioscopia), spotted spurge (Euphorbia maculata)

Gramineae:

chicken millet (Echinochloa crus-galli), spickle green (Setaria viridis), sainik (Setaria faberi), weed blood (Digitaria sanguinalis), Elefsina Indian (Eleusine indica), annual bluegrass (Poa annua), Alopecurus myservername (Alopecurus myosuroides), wild oat (Avena fatua), sorghum Halep (Sorgh is some (Panicum texanum), (Sorghum vulgare)

Commelinaceae:

commelina (Commelina communis)

Equisetaceae:

horsetail (Eguisetum arvense)

Cyperaceae:

syt weerasena (Cyperus iria), (Cyperus rotundus) and yellow nutsedge (Cyperus esculensus).

In addition, some compounds (I) of the present invention have no phytotoxicity against major cultivated plants such as maize (Zea mays), wheat (Triticum aestivum), barley (Hordeum vulgare), rice (Oryza sativa), sorghum (Sorghum bicolor), soybean (Glycine max), cotton (Gossypium spp), beet (Beta vulgarius), groundnut (Arachis hypogaea(, sunflower (Haliantnus annuus) and canola (Brassica napus) and orchard crops, such as flowers, ornamental plants, and vegetables. In particular, compound (I), where R2is carboxyla, or alkoxycarbonyl have excellent selectivity to soybean and weeds such as morning glory high, chicken millet and Rogovik unioloides soil on uplands.

In addition, compound (I) of the present invention can be very effective against weeds in cultivated areas. In addition, some of them have no phytotoxicity relative to cultivated plants, such as soybean, corn and wheat.

The compound (I) of this izaberete the processing during the irrigation of the rice fields.

Gramineae:

chicken millet (Echinochloa oryzicola)

Scropulariaceae:

common falsepimpernel (Lindernia procumbens)

Lythraceae:

Rotala indica, Ammannia multiflora

Elatinaceae:

Elatine trianda

Cyperaceae:

smallflower umbellaplant (Cyperus difformis), hardstem bulrush (Scirpus juncoides), needle spikerush (Eleocharis acicularis), Cyperus serotinus, Eleocharis kuroguwai

Pontederiaceae:

Monochoria vaginalis

Alismataceae:

Sagittaria pygmaea, Sagittaria trifolia, Alisma canaliculatum

Potamogetonaceae:

roundleaf pondweed (Potamogeton distinctus).

In addition, some compounds (I) of the present invention have no phytotoxicity compared to transplanted rice or rice sown directly.

In addition, some compounds (I) of the present invention may not be very effective against a variety of adverse weeds in orchards, vineyards, plantations, pastures or forests, slopes or other uncultivated lands.

If the compound (I) of the present invention are used as active ingredient of the herbicide, it is usually administered in a composition with a solid or liquid carriers or diluents, and surfactants and other auxiliary agents in conventional compositions, granules, concentrated emulsions, water-dispersible granules and process is and when its content in the range 0.003 - 80 wt.%, preferably 0.01 - 70 wt.%. on the total weight of each composition.

Examples of the solid carrier or diluent are fine powders or granules of minerals such as kaolin clay, attapulgite clay, bentonite, terra alba, pyrophyllites, talc, diatomaceous earth or calcite; organic substances such as powder, walnut shell; a water-soluble organic substances such as urea; inorganic salts such as ammonium sulfate; and synthetic water-silicate. As the liquid carrier or diluent there may be examples of aromatic hydrocarbons, such as alkyl benzenes (e.g., xylene, methylnaphthalene, phenylxylylethane; alcohols, such as isopropanol, ethylene glycol and 2-ethoxyethanol; esters, such as dialkyl ethers phthalic acid; ketones, such as acetone, cyclohexanone and isophorone; mineral oils such as machine oil; vegetable oils such as soybean oil and cottonseed oil; dimethylsulfoxide, N, N-dimethylformamide, acetonitrile, N-an organic, water and the like.

Examples of surface-active agents used for emulsification, dispersion or spray form, zinati phosphates and polyoxyethylene alkylsilanes ether, and the connection of non-ionic type, such as alkalemia esters of polyoxyethylene polyoxypropylene, esters arbetarnas fatty acids, and esters polyoxyethylenesorbitan fatty acids.

Examples of the auxiliary agent used for the composition are lignosulfonates, alginates, polyvinyl alcohol, gum Arabic of Arabicas, carboxymethylcellulose (CMC) and acidic isopropyl phosphate (PAP).

The compound (I) of the present invention is usually used in the composition of any appropriate composition and use for preschoolage or post-harvest monitoring of adverse weeds on the high fields and paddy (paddy) fields. Tillage includes processing the soil surface and sealing in the soil. The processing of the leaves includes the processing of all plants and is directly applied to the weeds in order to protect the leaves of cultivated plants from any chemical compounds.

In addition, compound (I) of the present invention can be used together with another herbicide to enhance its herbicide activity. In addition, it can be used in mixture with insecticides, acaricides, nematicides, fungicides, plant growth regulators, udobreniy is as an active ingredient of herbicides, the doses are usually in the range from 0.1 to 8000 g, preferably from 1 to 2000 g / ha, although the dose may largely depend on the prevailing weather conditions, the composition, timing of application, type of application, the treated soil, crop and type of weeds and the like. Noted the amount of compound (I) is prepared in the form of emulsifiable concentrate, wettable powder, flowable composition, concentrated emulsions, water-dispersible granules, a solution or the like, can usually be applied by diluting it with water to a volume of about 10 to 1000 liters per 1 ha, if necessary, with the addition of adjuvants, such as spraying agent. The compound (I), included in the form of granules or some kind of fluid compositions or solutions can usually be used without any dilution.

Examples of adjuvants include, in addition to surface-active agents described above, the resin polyoxyethylene resin acids (esters), lignosulfonates, abietate, dinaftiletilena, oil concentrates of cultivated plants and vegetable oils such as soybean oil, corn oil, cottonseed oil and sunflower oil.

The compound (I harvest, such as defoliants and drying agents for cotton and drying agents for potato (Solanum tuberosum). In this case, the compound (I) is usually prepared in the same manner as in the case when it is used as an active ingredient of herbicides, and use the connection itself or in a mixture with other additives that increase the harvest.

The present invention will be further illustrated by the following examples of the preparation, examples of compositions and examples of tests, which should not be construed as limited within their volume. Compounds of the present invention are marked with corresponding numbers as shown in the table. 1.

Example of getting 1. Obtaining the compounds (1).

In 5 ml of xylene was dissolved 0.5 g of 1-/4-chloro-6-fluoro-3-hydroxy-2- /2-methyl-2-propenyl/phenyl/-3-methyl-4-trifluoromethyl-1,2,3,6 - tetrahydropyrimidin-2,6-dione and 50 mg of the monohydrate of p-toluensulfonate acid and the solution is refluxed for 5 hours. After the reaction, the reaction solution was poured into water and the mixture extracted with 100 ml diethyl ether. The extract is washed with water, dried and concentrated. The residue is cleaned chromatography on a column of silica gel (eluent; hexane : ethyl is 3.61 /3H, with/, 6.42 /1H/, 7.18 /1H, d, j = 10 Hz/.

Example of getting a 2. Obtaining compound (4).

In 5 ml of chloroform was dissolved 0.4 g of 1-/4-chloro-6-fluoro-3-hydroxy - 2-/2-methyl-2-propenyl/phenyl/-3-methyl-4-trifluoromethyl-1,2,3,6 - tetrahydropyrimidin-2,6-dione and the solution added dropwise a suspension containing 0.26 g m-chloroperbenzoic acid in 5 ml of chloroform at room temperature and the reaction is carried out under conditions of boiling under reflux for 3 hours. After the reaction, the reaction mixture was cooled to room temperature and add saturated aqueous sodium thiosulfate solution and the mixture is stirred and extracted with chloroform. The extract was washed with aqueous sodium hydrogen carbonate solution, dried and concentrated. The residue is cleaned chromatography on silica gel (eluent; hexane : ethyl acetate = 2 : 1), which give 0.17 g of compound (4).

1H-NMR /M. D./ /60 MHz, CDCl3/ : 1.47 /3H/, 2.3 - 2.6 /2H, Shir./, 2.8 - 3.3 /2H, m/ 3.56 /3H/, 3.64 /2H,/, 6.39 /1H/, 7.11 /1H, d, j = 10 Hz/.

Example of getting a 3. Obtaining the compounds (11).

In 5 ml of pyridine was dissolved 0.5 g of compound /4/ and to the solution was added 50 mg of 4-dimethylaminopyridine. While cooling the mixture with ice add 0.2 g of acetic anhydride and the reaction providam ether. The extract was washed with diluted hydrochloric acid, dried and concentrated. The residue is cleaned chromatography on silica gel (eluent; hexane : ethyl acetate = 2 : 1), which gives 0.2 g of compound (11).

1H-NMR /M. D./ /60 MHz, CDCl3/ : 1.29 /3H/, 1.89 /3H/, 2.7 - 2.9 /2H, m/ 3.33 /3H/, 4.00 /2H,/, 6.12 /1H/, 6.88 /1H, d, j = 10 Hz/.

Example 4. Obtaining the compounds (15).

In the same manner as described in example receiving 3, except that the use of 0.17 g of propionic anhydride instead of acetic anhydride, to obtain 0.19 g of compound /15/.

1H-NMR /M. D./ /60 MHz, CDCl3/ : 1.03 /3H, t/, j = 8 Hz/, 1.51 /3H/, 2.30 /2H, q/, j = 8 Hz/, 2.9 - 3.1 /2H, m/ 3.52 /3H/, 4.19 /2H,/, 6.30 /1H/, 7.03 /1H, d, j = 10 Hz/.

Example of getting a 5. Obtaining compounds (23).

In 5 ml of acetone was dissolved 0.5 g of compound (4) and to the solution is slowly added dropwise 2 mg regenerate Jones, cooling this reaction mixture with ice, followed by stirring for 4 hours. After the reaction, the reaction mixture was poured into water and the mixture extracted with ethyl acetate. The extract is washed with water, dried and concentrated and obtain 0.45 g of compound (23).

1H-NMR /M. D./ /60 MHz, CDCl3/ : 1.75 /3H/, 2.9 - 3.3 /2H, m/ 3.53 /3H/, 6.29 /1H,/, 7 0.45 g of compound (23) and to the solution was added 50 mg of the monohydrate of p-toluensulfonate acid and the reaction is carried out under conditions of boiling under reflux for 3 hours. After the reaction, the reaction mixture was extracted with diethyl ether. The extract is washed with water, dried and concentrated. The residue is cleaned chromatography on silica gel /eluent; hexane : ethyl acetate = 4 : 1/, which gives 0.18 g of compound (24).

1H-NMR /M. D./ /60 MHz, CDCl3/ : 1.74 /3H/, 3.1 - 3.5 /2H, m/ 3.53 /3H/, 3.76 /3H/, 6.27 /1H/, 7.03 /1H, d, j = 10 Hz/.

Example of getting a 7. Obtaining compounds (25).

In the same manner as described in example receiving 6, except that the use of 0.5 g of compound (23) and 5 ml of ethanol, to obtain 0.26 g of compound (25).

1H-NMR /M. D./ /60 MHz, CDCl3/ : 1.24 /3H, t/j = 7 Hz/, 1.70 /3H/, 3.1 - 3.5 /2H, m/ 3.52 /3H/, 4.22 /2H, q/, j = 7 Hz/, 6.31 /1H/, 7.09 /1H, d, j = 10 Hz/.

Example of getting 8. Obtaining compounds (32).

In the same manner as described in example receiving 6, except that the use of 0.5 g of compound (23) and 5 ml of 1-butanol, obtain 0.13 g of compound (32).

1H-NMR /M. D./ /60 MHz, CDCl3/ : 0.91 /3H, t, j = 6 Hz/, 1.1 - 1.9 /4H, m/ 1.73 /3H/, 3.1 - 3.5 /2H, m/ 3.55 /3H/, 4.17 /2H, t/, j = 6 Hz/, 6.31 /1H/, 7.09 /1H, d, j = 10 Hz/.

Example of getting a 9. Obtaining compounds (38).

In the same manner as described in example receiving 6, except that ispolkoms, CDCl3/ : 1.74 /3H/, 2.49 /1H, t, j = 2 Hz/, 3.1 - 3.5 /2H, m/ 3.50 /3H/, 4.71 /2H, d, j = 2 Hz/, 6.26 /1H/, 7.04 /1H, d, j = 10 Hz/.

Example 10. Obtaining compounds (39).

In the same manner as described in example receiving 6, except that the use of 0.5 g of compound (4) and 0.17 g of benzoyl chloride, to obtain 0.18 g of compound (39), so pl. 157 - 158oC.

1H-NMR /M. D./ /60 MHz, CDCl3/ : 1.64 /3H/, 3.1 - 3.3 /2H, m/ 3.54 /3H/, 4.3 - 4.5 /2H, m/ 6.35 /1H/, 7.10 /1H, d, j = 10 Hz/, 7.4 - 7.7 /3H, m/, 7.8 - 8.1 /2H, m/

Example of getting 11. Obtaining compounds (49).

In chloroform was dissolved 6.0 g of 1-/4-chloro-3-hydroxy-2- /2-methyl-propyl/phenyl/-3-methyl-4-trifluoromethyl-1,2,3,6 - tetrahydropyrimidin-2,6-dione, and to the solution was added 7.1 g of m-chloroperbenzoic acid and refluxed for 2 hours. After the reaction, the reaction mixture was cooled to room temperature and add it to the water Hydrosulphite solution of sodium and the mixture is extracted with chloroform. The organic layer was washed with aqueous potassium carbonate solution and water, dried and concentrated, giving 5.6 g of compound (49).

1H-NMR /M. D./ /60 MHz, CDCl3/ : 1.48 /3H/, 2.05 - 2.49 /1H, Shir./, 2.87 /1H, s, Shir./, 3.06 /1H, s, Shir./, 3.54 /3H/, 3.64 /2H, with, W/, 6.29 /1H/, 6.59 /1H, d, j = 8 Hz/, 7.22 /1H, s, j the Ute 0.3 g of compound (49), to the solution add 0.5 ml under the conditions and 0.05 g of sodium hydride (60% in oil) in 5oC and the mixture is heated to room temperature and stirred for 6 hours. After the reaction, the reaction mixture was poured into water and the mixture extracted with ethyl acetate. The extract is washed with water, dried and concentrated. The residue is cleaned preparative thin-layer chromatography that give 0.12 g of compound (50).

1H-NMR /M. D./ 300 MHz, CDCl3/ : 1.52 /3x1/2H,/, 1.53 /3x1/2H,/, 2.78 /I/2H, d, j = 16 Hz/, 2.80 /I/2H, d, j = 16 Hz/, 3.10 /I/2H, d, j = 16 Hz/, 3.13 /I/2H, d, j = 16 Hz/, 3.40 /3x1/2H,/, 3.41 /3x1/2H,/, 3.49 /2H, m/ 3.55 /3H/, 6.33 /I/2H,/, 6.64 /I/2H, d, j = 8,5 Hz/, 7.24 /1H, d, j = 8.5 Hz/.

Example of receipt 13. Obtaining compounds (53).

In 10 ml of chloform dissolve 0.3 g of compound (49), to the solution add 0.5 ml of diisopropylethylamine and 0.15 g chloromethylmethylether ether and the mixture is stirred at room temperature for 17 hours. After the reaction, the reaction mixture was poured into water and the mixture extracted with ethyl acetate. The organic layer is dried and concentrated. The residue is cleaned preparative thin-layer chromatography, giving 0.23 g of compound (53).

1H-NMR /M. D./ /300 MHz, CDCl3/ : 1.54 /3H/, 2.82 /I/2H, d/, j = 16 Hz/, 2.83 /I/2H, d/, j = 16 Hz/, 3.15 /I/2H, d, j = 16 Hz/, 3.16 //P> Example of getting a 14. Obtaining connection (56).

To 0.2 g of compound (49) add 1.5 ml of pyridine and 1.5 ml of acetic anhydride and stirred at room temperature for 15 hours. After the reaction, the reaction mixture was concentrated. The residue is cleaned preparative thin-layer chromatography, giving 0.18 g of compound (56).

1H-NMR /M. D. / 250 MHz, CDCl3/ : 1.58 /3H/, 2.07 /3H/, 2.92 /I/2H, d/, j = 16 Hz/, 2.93 /I/2H, d/, j = 16 Hz/, 3.12 /1H, d, j = 16 Hz/, 3.59 /3H/, 4.22 /1H, d, j = 12 Hz/, 4.30 /I/2H, d, j = 12 Hz/,4.31 /I/2H, d, j = 12 Hz/, 6.38 /1H, s, 6.69 /1H, d, j = 8,5 Hz/, 7.30 /1H, d, j = 8.5 Hz/.

Example of receipt 15. Obtaining the compound (69).

To 40 ml of acetone was dissolved 3.0 g of compound (49), to which is added Jones reagent at room temperature until, until there is no longer the original substance. After the reaction is added 2-propanol to the reaction mixture, which is stirred for 1 hour. The reaction mixture was poured into water and the mixture extracted with diethyl ether. The organic layer is washed with water, dried and concentrated, giving 2.72 g of compound (69).

1H-NMR /M. D./ 60 MHz, CDCl3/ : 1.70 /3H/, 3.11 /1H, s, Shir./, 3.38 /1H, s, Shir. /, 3.49 /1H, s, Shir./, 6.26 /1H/, 6.61 /1H, d, j = 8 Hz/, 7.19 /1H, d, j = 8 Hz

Example of 16. Obtaining connection is mesh refluxed for 3 hours.

After the reaction, the reaction mixture was poured into water and the mixture extracted with diethyl ether. The extract is washed with water, dried and concentrated. The residue is cleaned preparative thin-layer chromatography, giving 0.24 g of compound (70).

1H-NMR /M. D./ /60 MHz, CDCl3/ : 1.74 /3H/, 3.15 /1H, s, Shir./, 3.42 /1H, s, Shir./, 3.52 /3H/, 3.77 /3H/, 6.29 /1H/, 6.64 /1H, d,/, j = 8 Hz/, 7.23 /1H, d, j = 8.5 Hz/.

Example of receipt 17. Obtaining compound (72).

In the same manner as described in example 16, except that use 30 ml of 1-propanol instead of methanol, to obtain 0.3 g of compound (72).

1H-NMR /M. D./ /60 MHz, CDCl3/ : 0.90 /3H, t, j = 7 Hz/, 1.39 - 1.85 /2H, m/ 1.74 /3H/, 3.41 /1H/, 3.52 /3H, s, 4.11 /2H, t, j = 7 Hz/, 6.31 /1H/, 6.64 /1H, d, j = 8 Hz/, 7.24 /1H, d, j = 8 Hz/.

Example obtain 18. Obtaining compound (73).

In the same manner as described in example 16, except that use 30 ml of 1-butanol instead of methanol, to obtain 0.2 g of compound (73).

1H-NMR /M. D./ /60 MHz, CDCl3/ : 0.90 /3H, t, j = 7 Hz/, 1.12 - 1.92 /4H, m/ 1.72 /3H/, 3.14 /1H/, 3.40 /1H/, 3.51 /3H/, 4.14 /2H, t, j = 7 Hz/, 6.29 /1H/, 6.63 /1H, d, j = 8 Hz/, 7.72 /1H, d,/, j = 8 Hz/.

Example obtain 19. Obtaining compound (75).

The same is and, obtain 0.3 g of compound(75).

1H-NMR /M. D./ /60 MHz, CDCl3/ : 1.37 /6H, d, j = 7 Hz/, 1.73 /3H/, 3.14 /1H/, 3.39 /1H/, 3.52 /3H/, 5.02 /1H, t, j = 7 Hz/, 6.31 /1H, s, 6.63 /1H, d, j = 8 Hz/, 7.24 /1H, d,/, j = 8 Hz.

An example of obtaining 20. Obtaining connection (104).

In 600 ml of chloroform was dissolved 58 g of 1-/2-allyl/-4-chloro - 6-fluoro-3-hydroxyphenyl/-3-methyl-4-trifluoromethyl-1,2,3,6 - tetrahydropyrimidin-2,6-dione, to the solution was added a suspension containing 38 g of m-chloroperbenzoic acid in 300 ml of chloroform dropwise at room temperature and the mixture is heated to boiling under reflux. After 6 hours the reaction mixture is cooled to room temperature and to it was added a saturated aqueous sodium thiosulfate solution and the mixture is stirred. After the reaction the organic layer was washed with aqueous sodium hydrogen carbonate solution, dried and concentrated. The residue is cleaned chromatography on silica gel /eluent; hexane : ethyl acetate = 3 : 1/ that give 43.2 g of compound (104) in the form of colorless crystals. so pl. 104.1oC.

1H-NMR /M. D./ /60 MHz, CDCl3/ : 3.10 /2H, d, j = 6 Hz/, 3.56 /3H/, 3.65 - 3.85 /2H, m, 5.0 - 5.2 /1H, m, 6.33 /1H/, 7.05 /1H, d, j = 10 Hz/.

Example of getting a 21. Obtaining compound (105).

In 15 ml of methylene chloride Rast is NML 0.22 g TRIFLUORIDE diethylaminobenzoic acid /DAST/ and stirred for 2 hours. After the reaction, the reaction mixture is extracted with methylene chloride. The extract is washed with sodium hydrogen carbonate solution, dried and concentrated. The residue is cleaned chromatography on silica gel /eluent; hexane : ethyl acetate = 4 : 1/ that give 0.26 g of compound (105).

1H-NMR /M. D./ /60 MHz, CDCl3/ : 3.13 /1H, d, j = 8 Hz/, 3.16 /1H, d, j = 9 Hz/, 3.54 /3H/, 4.59 /2H, DD, j = 4.47 Hz/, 4.48 - 5.4 /1H, m, 6.33 /1H/, 7.10 /1H, d, j = 10 Hz/.

Example of getting a 22. Obtaining compound (107).

In 15 ml of dichloromethane is dissolved 1.30 g of compound (104) and 1.3 g of carbon tetrachloride, to the solution was added 1.2 g of triphenylphosphine in 5oC and the mixture is stirred at room temperature for 24 hours. After the reaction, the reaction mixture was concentrated. The residue is cleaned chromatography on silica gel /eluent; hexane : ethyl acetate = 3 : 1/ that give 1.43 g of compound /107/.

1H-NMR /M. D./ /60 MHz, CDCl3/ : 3.0 - 3.3 /2H, m, 3.45 - 3.55 /2H, m/ 3.50 /3H/, 4.9 - 5.3 /1H, m, 6.22 /1H/, 6.96 /1H, d, j = 10 Hz/.

An example of retrieving 23. Obtaining compounds (111).

In 10 ml of pyridine was dissolved 0.5 g of compound (104) and 50 g of 4-dimethylaminopyridine, to the solution was added 0.15 g of acetic anhydride, the mixture is stirred at room temperature during the new ether. The extract was washed with diluted hydrochloric acid, dried and concentrated. The residue is cleaned chromatography on silica gel /eluent; hexane : ethyl acetate = 3 : 1/ that give 0.39 g of the compound (111).

1H-NMR /M. D./ /60 MHz, CDCl3/ : 2.03 /3H/, 2.99 /1H, d, j = 7 Hz/, 3.12 /1H, d, j = 9 Hz/, 3.50 /3H/, 4.24 /2H, d, j = 5 Hz/, 4.9 - 5.2 /1H, m/ 6.25 /1H/, 6.97 /1H, d, j = 6 Hz/.

Example of getting 24. Obtaining connection (112).

In the same manner as described in example receiving 23, except that the use of 0.5 g of compound (104) and 0.26 g of monochloracetic anhydride as starting compounds, obtain 0.35 g of the compound (112).

1H-NMR /M. D./ /60 MHz, CDCl3/ : 3.00 /1H, d, j = 7 Hz/, 3.11 /1H, d,/, j = 10 Hz/, 3.50 /3H/, 4.01 /2H,/, 4.36 /2H, d, j = 4 Hz/, 4.9 - 5.3 /1H, m, 6.24 /1H/, 6.98 /1H, d, j = 10 Hz/

An example of obtaining 25. Obtaining connection (114).

In the same manner as described in example receiving 23, except that the use of 0.5 g of compound (104) and 0.277 g trichloroacetamide as starting compounds, receive 0.3 g of compound (114).

1H-NMR /M. D./ /60 MHz, CDCl3/ : 3.15 /1H, d, j = 7 Hz/, 3.28 /1H, d,/, j = 9 Hz/, 3.56 /3H/, 4.59 /2H, d, j = 4 Hz/, 5.05 - 5.40 /1H, m, 6.54 /1H, s, 7.09 /1H, d, j = 10 Hz/.

Example of receipt 26. Obtaining connection (115).

1H-NMR /M. D./ /60 MHz, CDCl3/ : 1.08 /3H, t, j = 7 Hz/, 2.32 /2H, q/, j = 7 Hz/, 2.98 /1H, d,/, j = 7 Hz/, 3.11 /1H, d,/, j = 8 Hz/, 3.49 /3H/, 4.26 /2H, d, j = 4 Hz/, 5.0 - 5.1 /1H, m, 6.22 /1H/, 6.94 /1H, t, j = 10 Hz/.

Example of getting 27. Obtaining connection (116).

In the same manner as described in example receiving 23, except that the use of 0.5 g of compound (104) and 0.24 g of butyl anhydride as starting compounds, obtain 0.37 g of the compound (116).

1H-NMR /M. D./ /60 MHz, CDCl3/ : 0.90 /3H, t, j = 6 Hz/, 1.61 /2H, sq j = 6.6 Hz/, 2.30 /2H, t, j = 6 Hz/, 3.02 /1H, d, j = 7 Hz/, 3.15 /1H, d, j = 9 Hz/, 3.51 /3H/, 4.28 /2H, d, j = 4 Hz/, 4.95 - 5.25 /1H, m, 6.28 /1H/, 7.00 /1H, d, j = 10 Hz/.

Example of getting 28. Obtaining compounds (117).

In the same manner as described in example receiving 23, except that the use of 0.5 g of compound (104) and 0.24 g isobutyramide anhydride as starting compounds, obtain 0.31 g of compound (117).

1H-NMR /M. D./ /60 MHz, CDCl3/ : 1.12 /6H, d, j = 7 Hz/, 2.3 - 2.9 /3H, m/, 3.0 - 3.3 /2H, m/ 3.50 /3H/, 4.26 /2H, d, j = 4 Hz/, 4.9 - 5.3 /1H, m/ 6.25 /1H/, 7.07 /1H, d, j = 10 Hz/.

Example get 29. Obtaining connection (120).

In the same manner as described in example receiving 23, except that the COI is, the.sq. 145oC.

1H-NMR /M. D./ /60 MHz, CDCl3/ : 1.14 /9H, s, 2.8 - 3.0 /2H, m/ 3.56 /3H/, 4.20 - 4.40 /2H, m, 5.1 - 5.3 /1H, m, 6.31 /1H/, 7.15 /1H, d, j = 10 Hz/.

Example 30. Obtaining connection (121).

In the same manner as described in example receiving 23, except that the use of 0.5 g of compound (104) and 0.2 g cyclopentanecarbonyl chloride as starting compounds, obtain 0.42 g of compound (121).

1H-NMR /M. D./ /60 MHz, CDCl3/ : 1.5 - 1.9 /8H, m/, 2.6 - 2.8 /1H, m/ 3.04 /1H, d, j = 7 Hz/, 3.17 /1H, d, j = 9 Hz/, 3.53 /3H/, 4.31 /2H, d, j = 4 Hz/, 4.95 - 5.30 /1H, m, 6.37 /1H/, 7.11 /1H, d, j = 10 Hz/.

Example of getting 31. Obtaining connection (122).

In the same manner as described in example receiving 23, except that the use of 0.5 g of compound (104) and 0.22 g cyclohexanecarbonyl chloride as starting compounds, obtain 0.41 g of compound (122).

1H-NMR /M. D./ /60 MHz, CDCl3/ : 1.15 - 1.95 /10H, m/, 2.2 - 2.4 /1H, m/ 3.05 /1H, d, j = 8 Hz/, 3.18 /1H, d, j = 9 Hz/, 3.58 /3H/, 4.32 /2H, d, j = 4 Hz/, 5.0 - 5.3 /1H, m, 6.37 /1H/, 7.08 /1H, d, j = 10 Hz/.

Example get 32. Obtaining connection (123).

In 150 ml of acetone was dissolved 20 g of compound (104) and to the solution is slowly added dropwise 40 ml of Jones reagent under ice cooling and the mixture re the camping mix. The reaction mixture was poured into water and the mixture extracted with ethyl acetate. The extract was washed with water, dried and concentrated, giving 15.3 g of compound (123).

1H-NMR /M. D./ /60 MHz, CDCl3/ : 3.2 - 3.4 /2H, m/ 3.51 /3H/, 5.1 - 5.4 /1H, m/ 6.30 /1H/, 7.02 /1H, d, j = 10 Hz/.

An example of obtaining 33. Obtaining connection (124).

In 15 ml of methanol was dissolved 0.7 g of compound (123) to the solution add 0.05 g of p-toluensulfonate acid and the mixture is heated to boiling under reflux for 2 hours. After the reaction, the reaction mixture was poured into water and the mixture extracted with diethyl ether. The extract is washed with water, dried and concentrated. The residue is cleaned chromatography on silica gel /eluent; hexane : ethyl acetate = 3 : 1/ that gives 0.4 g of compound (124).

1H-NMR /M. D./ /60 MHz, CDCl3/ : 3.37 /2H, d, j = 9 Hz/, 3.48 /3H/, 3.72 /3H/, 5.28 /1H, t, j = 9 Hz/, 6.23 /1H/, 7.01 /1H, d, j = 10 Hz/.

An example of retrieving 34. Obtaining connection (125).

In the same manner as described in example obtain 33, except that they use 15 g of ethanol, receive and 0.38 g of compound (125).

1H-NMR /M. D./ /60 MHz, CDCl3/ : 1.26 /3H, t, j = 7 Hz/, 3.33 /2H, d, j = 7 Hz/, 3.47 /3H/, 4.18 /2H, q, j = 7 Hz/, 5.24 /1H, t, j = 7 Hz/, 6.20 /1H/, 7.01 /1H, d, confident of obtaining 33, except that they use 15 ml of 2-ftramadol instead of methanol, to obtain 0.28 g of compound (126).

1H-NMR /M. D. / /60 MHz, CDCl3/ : 3.25 - 3.45 /2H, m/ 3.50 /3H/, 4.15 /2H,/, 4.79 /2H, dt, j = 21.4 Hz/, 5.33 /1H, DD, j = 7.9 Hz/, 6.28 /1H/, 7.06 /1H, d, j = 10 Hz/.

Example obtain 36. Obtaining compounds (127).

In the same manner as described in example obtain 33, except that they use 15 ml of 2-chlorethane instead of methanol, to obtain 0.32 g of compound (127).

1H-NMR /M. D./ /60 MHz, CDCl3/ : 3.37 /1H, d, j = 7 Hz/, 3.39 /1H, d, j = 8 Hz/, 3.50 /3H/, 3.66 /2H, t, j = 6 Hz/, 4.40 /2H, t, j = 6 Hz/, 5.31 /1H, DD, j = 7.8 Hz/, 6.26 /1H/, 7.04 /1H, d, j = 10 Hz/.

Example of getting 37. Obtaining connection (128).

In the same manner as described in example obtain 33, except that they use 15 ml of n-propyl alcohol instead of methanol, to obtain 0.44 g of compound (128).

1H-NMR /M. D./ /60 MHz, CDCl3/ : 1.41 /3H, t, j = 7 Hz/, 1.16 /2H, m, j = 7 Hz/, 3.36 /2H, d/, j = 8 Hz/, 3.49 /3H/, 4.11 /2H, t, j = 7 Hz/, 5.29 /1H, t, j = 8 Hz/, 6.26 /1H/, 7.03 /1H, d, j = 10 Hz/.

Example of getting 38. Obtaining connection (129).

In the same manner as described in example obtain 33, except that they use 15 ml of isopropyl alcohol instead of methanol, poluchaut/, 3.46 /3H/, 4.98 /1H, m, 5.19 /1H, DD, j = 6.8 Hz/, 6.20 /1H/, 6.97 /1H, d, j = 10 Hz/.

An example of retrieving 39. Obtaining connection (131).

In the same manner as described in example obtain 33, except that they use 15 ml of 3-chloropropanol instead of methanol, to obtain 0.45 g of compound (131).

1H-NMR /M. D./ /60 MHz, CDCl3/ : 1.8 - 2.2 /4H, m/, 3.25 - 3.45 /2H, m/ 3.50 /3H/, 3.70 /2H, t, j = 6 Hz/, 4.28 //2H, t, j = 6 Hz/, 5.25 /1H, DD, j = 8.9 Hz/, 6.23 /1H/, 7.00 /1H, d, j = 10 Hz/.

Example of getting 40. Obtaining connection (132).

In the same manner as described in example obtain 33, except that they use 15 ml of 3-chloro-2-propanol instead of methanol, to obtain 0.31 g of compound (132).

1H-NMR /M. D./ /60 MHz, CDCl3/ : 1.39 /3H, d, j = 6 Hz/, 3.35 - 3.60 /2H, m/ 3.60 /3H/, 3.65 /2H, d, j = 6 Hz/, 5.15 - 5.45 /1H, m/ 5.45 /1H, DD, j = 8.9 Hz/, 6.44 /1H/, 7.23 /1H, d, j = 10 Hz/.

An example of retrieving 41. Obtaining connection (133).

In the same manner as described in example obtain 33, except that they use 15 ml of 1,3-debtor-2-propanol instead of methanol, to obtain 0.27 g of compound (133).

1H-NMR /M. D./ /60 MHz, CDCl3/ : 3.25 - 3.45 /2H, m/ 3.51 /3H/, 4.0 - 4.3 /1H, m/ 4.57 /4H, m/ 5.1 - 5.5 /1H, m/ 6.29 /1H/, 7.05 /1H, d, j = 10 Hz/.

Example get 42. Getting sued 15 ml of cyclohexanone instead of methanol, obtain 0.3 g of compound (138).

1H-NMR /M. D./ /60 MHz, CDCl3/ : 1.1 - 2.0 /10H, m/ 3.34 /1H, d, j = 7 Hz/, 3.40 /1H, d, j = 9 Hz/, 3.53 /3H/, 4.7 - 5.1 /1H, m, 5.27 /1H, DD, j = 7.9 Hz/, 6.31 //1H,/, 7.07 /1H, d, j = 10 Hz/.

An example of retrieving 43. Obtaining compound (139).

In 5 ml of xylene was dissolved 0.20 g of 1-/2-allyl/-4,6-debtor - 3-hydroxyphenyl/-3-methyl-4-trifluoromethyl-1,2,3,6 - tetrahydropyrimidin-2,6-dione and 10 mg monohydride p-toluensulfonate acid and the solution refluxed for 7 hours. After the reaction, the reaction mixture was poured into water and the mixture extracted with 100 ml diethyl ether. The organic layer is washed with water, dried and concentrated. The residue is cleaned chromatography on silica gel /eluent; hexane : ethyl acetate = 3 : 1/ that give 0.13 g of compound (139).

1H-NMR /M. D./ /60 MHz, CDCl3/ : 1.47 /3H, d, j = 6 Hz/, 2.8 - 3.2 /2H, m/ 3.49 /3H/, 4.9 - 5.2 /1H, m, 6.22 /1H/, 6.73 /1H, d, j = 10 Hz/.

An example of retrieving 44. Obtaining connection (142).

In 42 ml of methylene chloride was dissolved 1.0 g of 1-/2-allyl/-4,6-debtor - 3-hydroxyphenyl/-3-methyl-4-trifluoromethyl-1,2,3,6 - tetrahydropyrimidin-2,6-dione, to which are added dropwise, the suspension containing 0.71 g of m-chloroperbenzoic acid in 12 ml methylenchloride at room temperature and left the mixture is cooled to room temperature and add sodium thiosulfate and the mixture is stirred and extracted with chloroform. The extract was washed with aqueous sodium hydrogen carbonate solution, dried and concentrated to remove solvent. The residue is cleaned chromatography on silica gel /eluent; hexane : ethyl acetate = 7 : 3/, which gives 1.1 g of compound (142) in the form of yellowish-white crystals, so pl. 57.6oC.

1H-NMR /M. D./ /60 MHz, CDCl3/ : 3.0 /2H, d, j = 6 Hz/, 3.5 /3H/, 3.65 - 3.86 /2H, m, 4.81 - 5.25 /1H, m, 6.27 /1H/, 6.77 /1H, t, j = 11 Hz/.

An example of retrieving 45. Obtaining compound (147).

In 3 ml of dimethylformamide are suspended 0.05 g of sodium hydride and the suspension is added a solution containing 0.5 g of compound (142) in 1 ml of dimethylformamide and the mixture is stirred for 10 minutes. Then there is added 0.4 g under the conditions and the mixture is stirred at room temperature for 6 hours. After the reaction, the reaction mixture was extracted with ethyl acetate. The extract is washed with water, dried and concentrated. The residue is cleaned chromatography on silica gel /eluent; hexane : ethyl acetate = 3 : 1/ that gives 0.25 g of compound (147).

1H-NMR /M. D./ /60 MHz, CDCl3/ : 2.9 - 3.2 /2H, m/ 3.40 /3H/ 3.55 /3H/, 3.60 /2H, d/, j = 5 Hz/, 4.9 - 5.3 /1H, m, 6.31 /1H/, 6.83 /1H, t, j = 10 Hz/.

An example of a receipt 46. Obtaining connection (150).

In 5 ml of pyridine was dissolved 0.3 g sondigo anhydride and the reaction is carried out at room temperature for 3 hours. After the reaction, the reaction mixture was extracted with diethyl ether. The extract was washed with diluted hydrochloric acid, dried and evaporated to remove solvent. The residue is cleaned chromatography on silica gel /eluent; hexane : ethyl acetate = 3 : 1/ that gives 0.25 g of compound (150) in the form of white crystals, so pl. 47.2oC.

1H-NMR /M. D./ /60 MHz, CDCl3/ : 2.11 /3H/, 3.16 /2H, t, j = 10 Hz/, 3.62 /3H/, 4.43 /2H, d/, j = 4 Hz/, 4.92 - 5.41 /1H, m, 6.44 /1H/, 6.92 /1H, t, j = 10 Hz/.

An example of retrieving 47. Obtaining compound (152).

In 1.1 ml of pyridine is dissolved 0.5 connection (142) and 50 g of 4-dimethylaminopyridine and to the solution was added with ice cooling 0.20 g dichloroacetylene and the reaction is carried out at room temperature for 6 hours. After the reaction, the reaction mixture was extracted with ethyl acetate. The extract was washed with diluted hydrochloric acid, dried and evaporated to remove solvent. The residue is cleaned chromatography on silica gel /eluent; hexane : ethyl acetate = 7 : 3/ that give 0.23 g of compound (152).

1H-NMR /M. D./ /60 MHz, CDCl3/ : 2.93 - 3.34 /2H, m/ 3.51 /3H/, 4.42 /2H, d, j = 5 Hz/, 4.92 - 5.37 //2H, m/ 5.91 /1H/, 6.23 /1H/, 6.77 /1H, t, j = 10 Hz/.

Example get 48. Obtaining compound (153).

is soedinenii 0.5 g of compound (142) and 0.24 g of trichloroacetaldehyde, obtain 0.3 g of compound (153).

1H-NMR /M. D. / /60 MHz, CDCl3/ : 3.07 - 3.43 /2H, m, 3.67 /3H/, 4.67 /2H, d, j = 5 Hz/, 5.13 - 5.56 /1H, m, 6.48 /1H/, 7.01 /1H, t, j = 10 Hz/.

Example get 49. Obtaining compound (154).

In 16 ml of tetrahydrofuran, was dissolved 0.5 g of compound (142) and 0.19 mg 4-dimethylaminopyridine and to the solution while cooling add 0.57 g triperoxonane anhydride and the reaction is carried out at room temperature for 3 hours. After the reaction, the reaction mixture was extracted with diethyl ether. The extract is washed with water, dried and evaporated to remove solvent. The residue is cleaned chromatography on silica gel /eluent; hexane : ethyl acetate = 7 : 3/, which gives 0.3 g of compound (154).

1H-NMR /M. D. / /60 MHz, CDCl3/ : 2.68 - 3.01 /2H, m/ 3.81 /3H/, 4.85 /2H, d, j = 5 Hz/, 5.3 - 5.85 /1H, m, 6.70 /1H/, 7.25 /1H, t, j = 10 Hz/.

Example of getting 50. Obtaining connection (155).

In the same manner as described in example receiving 49, except that the use of 0.5 g of compound (142) and 0.17 g of propionic anhydride as starting compounds, obtain 0.48 g of compound (155).

1H-NMR /M. D./ /60 MHz, CDCl3/ : 1.05 /3H, t, j = 7 Hz/, 2.31 /2H, q/, j = 7 Hz/, 3.0 /2H, t/, j = 7 Hz/, 3.50 /3H/, 4.40 /2H, d, j = 6 Hz/, 4.84 - 5.27 as described in example receiving 49, except that used as starting compounds 0.5 g of compound (142) and 0.21 g of butyl anhydride, obtain 0.6 g of compound (157).

1H-NMR /M. D./ /60 MHz, CDCl3/ : 0.92 /3H, t/, j = 7 Hz/, 1.42 - 2.05 /2H, m/ 2.35 /2H, t, j = 8 Hz/, 3.10 /2H, t, j = 8 Hz/, 3.58 /3H/, 4.35 /2H, d, j = 5 Hz/, 5.00 - 5.52 /1H, m, 6.42 /1H/, 6.98 /1H, t, j = 11 Hz/.

An example of retrieving 52. Obtaining compound (158).

In the same manner as described in example receiving 47, except that the use of 0.5 g of compound (142) and 0.17 g of Isobutyraldehyde as starting compounds, receive 0.21 g of compound (158).

1H-NMR /M. D./ /60 MHz, CDCl3/ : 1.08 /3H/, 1.19 /3H, s, 2.24 - 2.81 /1H, m/ 3.09 /2H, t, j = 8 Hz/, 3.57 /3H/, 4.30 /2H, d, j = 4 Hz/, 4.94 - 5.37 /1H, m, 6.32 /1H/, 6.87 /1H, t, j = 10 Hz/.

Example get 53. Obtaining compound (165).

In the same manner as described in example receiving 47, except that the use of 0.5 g of compound (142) and 0.19 g of benzoyl chloride as starting compounds, obtain 0.28 g of compound (165).

1H-NMR /M. D. / /60 MHz, CDCl3/ : 3.09 - 3.30 /2H, m/ 3.98 /3H/, 4.41 - 4.54 /2H, m, 5.02 - 5.43 /1H, m, 6.38 /1H/, 6.81 /1H, t, j = 10 Hz/, 7.21 - 8.10 /5H, m/.

Example of getting 54. Obtaining compound (166).

In 30 ml of acetone was dissolved 4 g're asked for 2 hours. After the reaction, there is added dropwise at about 5 ml of isopropyl alcohol and the mixture is stirred. The reaction mixture was poured into water and the mixture extracted with ethyl acetate. The extract is washed with water, dried and evaporated to remove the solvent, giving 3.95 g of compound (166).

1H-NMR /M. D./ /60 MHz, CDCl3/ : 2.9 - 3.1 /2H, m/ 3.49 /3H/, 4.7 - 5.2 /1H, m, 6.23 /1H/, 6.73 /1H, t, j = 10 Hz/.

Example of getting 55. Obtaining compound (167).

In 0.42 g of methanol was dissolved 0.5 g of compound (166) and to the solution add 50 ml of monohydride p-toluensulfonate acid, the reaction is carried out by boiling under reflux for 4 hours. After the reaction, the reaction mixture was extracted with diethyl ether. The extract is washed with water, dried and evaporated to remove solvent. The residue is cleaned chromatography on silica gel /eluent; hexane : ethyl acetate = 4 : 1/ that give 0.24 g of compound (167).

1H-NMR /M. D. / /60 MHz, CDCl3/ : 3.29 - 3.47 /2H, m/ 3.52 /3H/, 3.75 /3H/, 5.30 /1H, t, j = 9 Hz/, 6.25 /1H/, 6.82 /1H, t, j = 10 Hz/.

An example of receiving 56. Obtaining connection (168).

In the same manner as described in example receiving 55, except that the use of 0.61 g of ethanol instead of methanol, receive kV, j = 7 Hz/, 5.28 /1H, t, j = 9 Hz/, 6.26 /1H/, 6.85 /1H, t, j = 10 Hz/.

An example of retrieving 57. Obtaining compound (171).

In the same manner as described in example receiving 55, except that the use of 0.79 g of 1-propanol instead of methanol, to obtain 0.29 g of compound (171).

1H-NMR /M. D./ /60 MHz, CDCl3/ : 0.94 /3H, t/, j = 8 Hz/, 1.25 - 1.85 /2H, m, 3.37 - 3.43 /2H, m/ 2.53 /3H/, 4.23 /2H, t, j = 7 Hz/, 5.28 /1H, t, j = 9 Hz/, 6.27 /1H/, 6.85 /1H, t, j = 10 Hz/.

An example of retrieving 58. Obtaining compound (172).

In the same manner as described in example receiving 55, except that the use of 0.79 g of 2-propanol instead of methanol, to obtain 0.12 g of compound (172).

1H-NMR /M. D./ /60 MHz, CDCl3/ : 1.28 /6H, d/, j = 6 Hz/, 3.27 - 3.44 /2H, m/ 3.53 /3H/, 4.90 - 5.50 /2H, m/ 6.30 /1H/, 6.86 /1H, t, j = 10 Hz/.

Example retrieve 59. Obtaining compound (173).

In the same manner as described in example receiving 55, except that the use of 0.62 g of 3-chloro-1-propanol instead of methanol, to obtain 0.31 g of compound (173).

1H-NMR /M. D./ /60 MHz, CDCl3/ : 2.13 /2H, t/, j = 6 Hz/, 3.30 - 3.46 /2H, m, 3.55 /3H, c/, 3.67 - 3.85 /2H, m/, 4.35 /2H, t, j = 6 Hz/, 5.27 /1H, t, j = 8 Hz/, 6.26 /1H/, 6.84 /1H, t, j = 10 Hz/.

Example of getting 60. Obtaining compound (175).

The same about the are square-0.09 g of compound (175).

1H-NMR /M. D./ /60 MHz, CDCl3/ : 0.81 - 1.72 /7H, m/, 3.27 - 3.43 /2H, m/ 3.52 /3H/, 4.17 /2H, t, j = 7 Hz/, 5.24 /1H, t, j = 9 Hz/, 6.24 /1H/, 6.82 /1H, t, j = 10 Hz/.

An example of a receipt 61. Obtaining compound (181).

In 5 ml of xylene was dissolved 0.3 g of 1-/2-allyl/-4-chloro-3 - hydroxyphenyl/-3-methyl-4-trifluoromethyl-1,2,3,6 - tetrahydropyrimidin-2,6-dione, and to the solution was added a catalytic amount of monohydrate p-toluensulfonate acid and the mixture is refluxed for 3 hours. After the reaction, the reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with aqueous sodium hydrogen carbonate solution, dried and concentrated. The residue is cleaned preparative thin-layer chromatography, giving 0.3 g of compound (181).

1H-NMR /M. D./ /250 MHz, CDCl3/ : 1.52 /3H, d, j = 6.2 Hz/, 2.73 /I/2H, DD, j = 4.1, 13 Hz/, 2.77 /1/2H, DD/, j = 3.9, 13 Hz/, 3.20 /I/2H, DD, j = 3.1, 13 Hz/, 3.23 /I/2H, DD, j = 3.1, 13 Hz/, 3.55 /3H/, 5.08 /1H, m, 6.35 /1H/, 6.63 /1H, d, j = 8.9 Hz/, 7.24 /1H, d, j = 8.9 Hz/.

An example of retrieving 62. Obtaining compound (194).

In 600 ml of chloroform was dissolved 4.0 g of 1-/2-allyl/-4-chloro-3 - hydroxyphenyl/-3-methyl-4-trifluoromethyl-1,2,3,6 - tetrahydropyrimidin-2,6-dione, and to the solution was added 3.6 g of m-chloroperbenzoic acid in 5oC and the reaction pursuing the target of hydrosulfite sodium and the mixture is extracted with ethyl acetate. The organic layer was washed with aqueous solution of sodium carbonate and then water, dried and concentrated. The residue is cleaned chromatography on silica gel, giving 3.8 g of compound (194).

1H-NMR /M. D./ /250 MHz, CDCl3/ : 1.90 /1H, Shir./, 2.93 - 3.12 /2H, m, 3.55 /1H/, 3.76 /I/2H, DD, j = 5.4, 12 Hz/, 3.77 /I/2H, DD, j = 5.7, J = 12 Hz/, 3.88 /I/2H, DD, j = 7.7, 12 Hz/, 3.89 /I/2H, DD, j = 7.5, 12 Hz/, 5.0 /1H, m, 6.34 /I/2H,/, 6.35 /I/2H, d/, j = 8.5 Hz/, 7.25 /1H, d, j = 8.5 Hz/.

An example of retrieving 63. Obtaining connection (195).

In 5 ml of N, N-dimethylformamide is dissolved 0.3 g of compound (194) and to the solution add 0.2 ml under the conditions and 0.1 g of sodium hydride /60% in oil and the mixture is stirred at room temperature for 20 hours. After the reaction, the reaction mixture was poured into water and the mixture extracted with diethyl ether. The extract is dried and concentrated. The residue is cleaned preparative thin-layer chromatography, giving 0.19 g of compound (195).

1H-NMR /M. D./ /250 MHz, CDCl3/ : 3.0 /1H, m, 3.18 /1H, m, 3.41 /3H/, 3.55 /3H/, 3.57 - 3.71 /2H, m, 5.07 /1H, m, 6.35 /1H/, 6.65 /1H, d, j = 8.5/, 7.23 /1H, d, j = 8.5 Hz/.

Example obtain the 64. Obtaining compound (198).

In 5 ml of chloroform was dissolved 0.3 g of compound (194) and to the solution add 0.5 ml of diisopropylethylamine and 0.15 g chloromethylation mixture was poured into water and the mixture extracted with ethyl acetate. The organic layer is dried and concentrated. The residue is cleaned preparative thin-layer chromatography, giving 3.8 g of compound (198).

1H-NMR /M. D./ /300 MHz, CDCl3/ : 2.96 /I/2H, DD, j = 4.6, 16 Hz/, 2.98 /I/2H, DD, j = 4.6, 16 Hz/, 3.17 /I/2H, DD, j = 4.9, 15 Hz/, 3.20 /I/2H, DD, j = 4.8, 15 Hz/, 3.37 /3H, s, 3.55 /3H/, 3.71 - 3.83 /2H, m/ 4.67 /2H,/, 5.10 /1H, m/ 6.35 /1H, d,/, j = 8.5 Hz/, 7.25 /1H, d, j = 8.5 Hz/.

Example obtain 65. Obtaining connection (201).

To 0.4 g of compound (194) add 5 ml of pyridine and 3 ml of acetic anhydride and the mixture is stirred at room temperature for 3 hours. After the reaction, the reaction mixture was concentrated. The residue is cleaned preparative thin-layer chromatography that give 0.37 g of compound (201).

1H-NMR /M. D./ 250 MHz, CDCl3/ : 2.08 /3H/, 2.92 /1H, DD/, j = 6.7, 15 Hz/, 3.21 /I/2H, DD/, j = 9.5, 15 Hz/, 3.23 /I/2H, DD/, j = 9.5, 15 Hz/, 3.55 /3H/, 4.33 /2H, d, j = 4.60 Hz/, 5.12 /1H, m, 6.35 /1H/, 6.67 /1H, d, j = 8.1 Hz/, 7.27 /1H, d, j = 8.1 Hz/.

An example of retrieving 66. Obtaining compounds (214).

To 20 ml of acetone was dissolved 1.8 g of compound (194), to which is added 3.0 jones reagent and the mixture is stirred at room temperature for 4 hours. After the reaction, the reaction mixture was filtered and the filtrate poured into water. The mixture is extracted with etilize is C, CDCl3/ : 3.30 - 3.55 /2H, m, 3.58 /3H/, 5.38 /1H, m/ 6.40 /1H/, 6.76 /1H, d,/, j = 8.5 Hz/, 7.34 /1H, d, j = 8.5 Hz/.

An example of retrieving 67. Obtaining compounds (215).

In 5 ml of methanol is dissolved 0.3 g of compound (214) and to it add a catalytic amount of monohydride p-toluensulfonate acid and the mixture is heated to boiling under reflux for 4 hours. After the reaction, the reaction mixture was poured into a saturated aqueous solution of sodium bicarbonate and the mixture extracted with ethyl acetate. The organic layer is washed with water, dried and concentrated. The residue is cleaned preparative thin-layer chromatography that give 0.21 g of compound (215).

1H-NMR /M. D./ /250 MHz, CDCl3/ : 3.30 /1H, m/ 3.48 /1H, m/ 3.55 /1H/, 3.81 /1H/, 5.34 /1H, DD/, j = 7.2, 10.5 Hz/, 6.34 /1H/, 6.71 /1H, d,/, j = 8.6 Hz/, 7.29 /1H, d, j = 8.6 Hz/.

Example of getting 68. Obtaining compounds (218).

In the same manner as described in example getting 67, except that using 5 ml of 1-butanol instead of methanol, to obtain 0.2 g of compound (218).

1H-NMR /M. D./ /250 MHz, CDCl3/ : 0.93 /3H, t, j = 7.5 Hz/, 1.35 /2H, m/ 1.65 /2H, m/ 3.27 /1H, m/ 3.45 /1H, m/ 3.55 /3H/, 4.21 /2H, t, j = 6.6 Hz/, 5.31 /1H, DD, j = 8.3, 10.5 Hz/, 6.35 /1H/, 6.70 /1H, DD, j = 8.5 Hz/, 7.51 /1H, d/, j = 8.5 Hz/.

Removing a 1-/2-allyl/-4-chloro-6-fluoro - 3-hydroxyphenyl/-3-methyl-4-trifluoromethyl-1,2,3,6 - tetrahydropyrimidin-2,6-dione.

In 30 ml of N,N-diethylaniline dissolve 10.0 g of 1-/5-allyloxy - 4-chloro-2-forfinal/-3-methyl-4-trifluoromethyl-1,2,3,6 - tetrahydropyrimidin-2,6-dione and the solution is refluxed for 3.5 hours. After the reaction, the reaction mixture was poured into water and the mixture is extracted with 300 ml of ethyl acetate. The extract is washed with three times 100 ml of 100% hydrochloric acid, dried and concentrated. The residue is cleaned chromatography on silica gel /eluent; hexane : ethyl acetate = 2 : 1/, which gives 7.9 g of the desired compound, so pl. 148.0oC.

1H-NMR /M. D./ /60 MHz, CDCl3/ : 3.30 /2H, d, j = 6 Hz/, 3.54 /3H/, 4.75 - 4.90 /1H, m, 5.0 - 5.1 /1H, m, 5.5 - 5.9 /2H, m, 6.34 /1H/, 7.12 /1H, d, j = 10 Hz/.

Example of getting 70. Getting 1-/2-allyl/-4,6-debtor-3 - hydroxyphenyl/-3-methyl-4-trifluoromethyl-1,2,3,6 - tetrahydropyrimidin-2,6-dione.

In 10 ml of m-Diisobutylene dissolve 2.0 g 1-/5-allyloxy - 2,4-differenl/-3-methyl-4-trifluoromethyl-1,2,3,6 - tetrahydropyrimidin-2,6-dione and the solution is refluxed for 4 hours. After the reaction, the reaction mixture was cooled to room temperature and directly clean chromatography on silica gel /eluent; hexane : ethyl acetate = 2 : 1/ that give 1.52 g of the desired compound, so pl. 142.9oC.

<0 Hz/.

Example of getting 71. Getting 1-/4-chloro-6-fluoro-3 - hydroxy-2-/2-methyl-2-propenyl/phenyl/-3-methyl-4-trifluoromethyl - 1,2,3,6-tetrahydropyrimidin-2,6-dione.

In 50 ml of N,N-diethylaniline dissolve 21.6 g of 1-/4-chloro-2-fluoro-5/-2-methyl-2-propenyloxy/phenyl/-3-methyl-4 - trifluoromethyl-1,2,3,6, -tetrahydropyrimidin-2,6-dione and the solution is refluxed for 4 hours. After the reaction, the reaction mixture was cooled to room temperature and extracted with diethyl ether. The extract was washed with diluted hydrochloric acid, dried and concentrated. The residue is cleaned chromatography on silica gel /eluent; hexane : ethyl acetate = 2 : 1/ that give 19.5 g of the desired compound.

1H-NMR /M. D./ /60 MHz, CDCl3/ : 1.60 /3H/, 3.28 /2H,/, 3.48 /3H/, 4.4 - 4.6 /1H, m, 4.6 - 4.8 /1H, m/ 5.76 /1H/, 6.36 /1H/, 7.09 /1H, d, j = 10 Hz/.

Example of getting 72. Getting 1-/2-allyl/-4-chloro-3 - hydroxyphenyl/-3-methyl-4-trifluoromethyl-1,2,3,6 - tetrahydropyrimidin-2,6-dione.

In 100 ml of N, N-diethylaniline dissolve 8.0 g of 1-/3-allyloxy-4-chlorophenyl/-3-methyl-4-trifluoromethyl-1,2,3,6 - tetrahydropyrimidin-2,6-dione and the solution stirred at 180oC for 3 hours. After the reaction, the reaction mixture was cooled to room temperature and poured into will centerour. The residue is cleaned chromatography on silica gel, giving 6.3 g of the desired compound.

1H-NMR /M. D./ /60 MHz, CDCl3/ : 3.15 /1H, s, 3.25 /1H/, 3.42 /3H/, 4.65 - 5.05 /2H, m/ 5.65 /1H, m, 5.80 /1H/, 6.25 /1H/, 5.57 /1H, d, j = 8 Hz/, 7.25 /1H, d, j = 8 Hz/.

Example of getting 73. Getting 1-/4-chloro-3-hydroxy-2- /2-methyl-2-propenyl/phenyl/-3-methyl-4-trifluoromethyl-1,2,3,6 - tetrahydropyrimidin-2,6-dione.

In 150 ml of N, N-diethylaniline dissolving 7.4 g of 1-/4-chloro-3-/2-methyl-2-propenyloxy/phenyl/-3-methyl-4 - trifluoromethyl-1,2,3,6-tetrahydropyrimidin-2,6-dione and the solution stirred at 160oC for 3 hours. After the reaction, the reaction mixture was cooled to room temperature and poured into water. The mixture is extracted with diethyl ether. The organic layer was washed with diluted hydrochloric acid, dried and concentrated, giving 6.2 g of the desired compound.

1H-NMR /M. D./ /60 MHz, CDCl3/ : 1.58 /3H/, 3.28 /2H,/, 3.46 /3H, s, 4.45 /1H/, 4.58 /1H/, 6,14 /1H, c/, 6.26 /1H, s, 6.60 /1H, d,/, j = 8 Hz/, 7.26 /1H, d, j = 8 Hz/.

Next will be described an example of obtaining the compound (IV).

Example of getting 74. In 500 ml of chloroform was dissolved 50 g of 1-/4-chloro-6-fluoro-3-hydroxy-2-/2-methyl-2-propenyl/phenyl/-3-methyl - 4-trifluoromethyl-1,2,3,6-tetrahydropyrimidin-2,6-dione, to coromuel the end of the reaction, the reaction mixture was cooled to room temperature and subjected to fractionation to separate the funnel, using chloroform and an aqueous solution of sodium sulfite. The organic layer was washed with saturated aqueous sodium hydrogen carbonate and then water, dried and concentrated. The residue is subjected to recrystallization, which gives 46 g 1/4-chloro-6-fluoro-3-hydroxy-2-/2,3-epoxy-2 - methylpropyl/phenyl/-3-methyl-4-trifluoromethyl-1,2,3,6 - tetrahydropyrimidin-2,6-dione.

1H-NMR /M. D./ /60 MHz, CDCl3/ : 1.29 /I/2x3H,/, 1.31 /I/2x3H,/, 2.75 /3H, m/ 3.10 /1H, m, 3.58 /3H/, 6.31 /1H/, 7.20 /1H, d,/, j = 8 Hz/. 7.45 /1H, s/.

Next will be described examples of compositions, where part of the weight. Compounds of the present invention indicate the corresponding numbers as shown in the table. 1.

Example composition 1.

50 parts of any of the compounds(1), (4), (11), (13) - (17), (23) - (25), (28), (29), (32), (33), (36), (38), (39), (44), (49), (50), (53), (56), (70), (72), (73), (75), (101), (104), (105), (107), (108), (111) - (117), (120) - (129), (131) - (134), (138), (139), (142), (143), (147), (150), (152) - (155), (157) - (158), (162), (163), (165) - (169), (171) - (175), (178), (180), (194), (195), (198), (201), 3 part ligninsulfonate calcium, 2 parts laurylsulphate sodium and 45 parts of synthetic aqueous silicate mix well until then, until you get horoscopesfemale powder.

Example composition 2.

10 parts of any one of the compounds(1), (4), (11), (13) - (17), (23) - (25), (28), (29), (32), (352) - (155), (157) - (158), (162), (163), (165) - (169), (171) - (175), (178), (180), (194), (195), (198), (201), 14 parts polyoxyethyleneglycol ether, 6 parts of dodecylbenzenesulfonate sodium, 35 parts of xylene and 35 parts of cyclohexanone are well mixed to produce a well-emulsifiable concentrate.

Example of composition 3.

2 part of any of the compounds(1), (4), (11), (13) - (17), (23) - (25), (28), (29), (32), (33), (36), (38), (39), (44), (49), (50), (53), (56), (70), (72), (73), (75), (101), (104), (105), (107), (108), (111) - (117), (120) - (129), (131) - (134), (138), (139), (142), (143), (147), (150), (152) - (155), (157) - (158), (162), (163), (165) - (169), (171) - (175), (178), (180), (194), (195), (198), (201), 2 part synthetic aqueous silicate, 2 parts ligninsulfonate calcium, 30 parts of bentonite and 64 parts of kaolin clay are well mixed to obtain a powder product. The mixture is then kneaded with water, granularit and dried to obtain granules.

Example of composition 4.

25 parts of any of the compounds(1), (4), (11), (13), (14), (16), (17), (23), (24), (25), (28), (29), (32), (33), (38), (39), (49), (70), (101), (104), (105), (107), (108), (111), (112), (113), (114), (120), (121), (123), (124), (126), (127), (132), (133), (139), (150), (152), (153), (158), (162), (163), (166), (167), (168), (172), (173),(194), (201), 50 parts of 10% solution of polyvinyl alcohol and 25 parts of water are well mixed and the mixture pulverized to particle size not exceeding 5 microns to achieve tecosystems rooms as shown in the table. 1, and the compounds used for comparison are designated by numbers, as shown in table. 2.

Herbicide activity against the weeds and the phytotoxicity with respect to cultural plants was determined by visual observation as the degree of germination and growth of test plants /ie weeds and cultivated plants and the rate of occurrence of plants with index 0, 1, 2, 3, 4 or 5, the number "0" indicates that there is a slight or no differences occur, as compared with untreated plants and the number "5" indicates the total loss of the tested plants or complete inhibition of germination or growth.

Example test 1. Cylindrical plastic vessels /with a diameter of 10 cm and a height of 10 cm was filled with earth altitudes and the seeds of wild oats and ipomea were sown in them and covered with soil. The test compound in the form of an emulsion concentrate according to example composition 2 was diluted with water and the diluted solution was sprayed on the soil surface automatic sprayer, applying a quantity of calculate 1000 l per 1 hectare Subjects plants were placed in the greenhouse for 19 days and studied herbicide activity. The results are shown in table. 3 the Yali earth altitudes and were sown in them the seeds of wild oats and placed in the greenhouse for 7 days. After that the test compound in the form of an emulsion concentrate according to example composition 2 was diluted with water containing the spray agent, and the diluted solution was respectively on the leaves of the test plants automatic sprinkler using the number of calculation 1000 l per 1 hectare After treatment, subjects plants were then placed in a greenhouse for 19 days and studied herbicide activity. The results are shown in table. 4

Example of test 3. Plastic containers (25 x 18 x 7 cm) were filled with earth altitudes and they were sown the seeds of soybean, ipomea and barnyard millet and Rakovica unloving and covered with earth. The test compound in the form of an emulsion concentrate according to example composition 2, was diluted with water and the solution was sprayed on the soil surface automatic sprinkler using the number from the calculation of 1000 liters per hectare. Subjects plants were placed in a greenhouse at 18 days and was determined herbicide activity and phytotoxicity. The results are shown in table. 5.

Example test 4.

Plastic vessels /25 x 18 x 7 cm were filled with earth altitudes and they were sown the seeds of wheat, cleaver, Veronica Asherah and violet treemenu composition 2 was diluted with water and sprayed on the leaves of the test plants automatic sprinkler using the number from the calculation of 1000 liters per hectare. The subjects of the plants were then placed in a greenhouse for 25 days and was determined herbicide activity and phytotoxicity with respect to the crop. At this time, the subjects of the plants were in stages 1 - 4 leaf 3 - 25 cm in height, although the growth stage of trial plants varies depending on their type. The results are shown in table. 6.

Example test 5.

Plastic vessels /19 x 29 x 8 cm/ filled the earth altitudes and they were sown the seeds of cotton and placed in the greenhouse for 3 months. The test compound in the form of an emulsion concentrate according to example composition 2 was diluted with water containing the spray agent, and the diluted solution was sprayed on the leaves of the test plants spray device using the number of calculation 1000 l ha After treatment, the test plants were then placed in a greenhouse for 9 days and determined the effect drying of cotton leaves. During treatment, subjects plants were 50 cm in height and began to collect seed pods. The effect of drying of cotton leaves was determined 0 - 100%, a value of "0" indicates that there is no difference compared with the untreated plant and a value of 100 indicates complete stykovye vessels (20 x 30 x 8 cm deep), filled the earth altitudes and they were sown the seeds of ipomea ploscolistny, lapusnik and Siennica. Each test compound in the form of an emulsion concentrate according to example composition 2, was diluted with water and each diluted solution used for spraying the soil surface in the vessels of the spraying device. The dose of each test compound was 250 g per 1 hectare and the number was calculated for 1,000 l per 1 hectare

After treatment, the test plants were placed in the greenhouse for 25 days and have control over every weed determine the effect of drying leaves of cotton.

The results are shown in table. 8.

Example test 7.

Plastic vessels /20 30 8 cm deep/ were filled with earth altitudes and they were sown the seeds of ipomea ploscolistny, mountaineer pepper pale, limnocharis, barnyard millet and wild oats and placed in the greenhouse for 31 days. Each test compound in the form of an emulsion concentrate according to example composition 2, was diluted with water containing the spray agent and each diluted solution used for spraying the leaves of test plants spray device. Doses who ha At this time, the subjects of the plants were approximately 5 - 20 cm in height. After treatment, the test plants were placed in a greenhouse at 25 days and monitored for each weed.

The results are shown in table. 9.

As described above, the compounds (I) of the present invention have an excellent herbicide activity against various unfavorable weeds when the soil or the leaves on the high fields and processing during the irrigation of the rice fields and some of them find excellent selectivity with respect to cultivated plants and weeds, so they can be useful as active ingredients of herbicides.

1. Derivatives dihydrobenzofuran formula I

< / BR>
where A is hydrogen, fluorine or chlorine;

X is fluorine, chlorine or bromine;

Y is methyl substituted by one or more halogen atoms;

Z - methyl;

R1is hydrogen or C1- C6-alkyl; R2- C1- C6-alkyl, C1- C6-hydroxyalkyl, C1- C6-alkoxy(C1- C6)-alkyl, C1- C6-alkoxy(C1- C6)alkoxy-(C1- C6)alkyl, C1- C7-acyloxy (C1- C6)alkyl, carboxyl, C1- C6- C6-alkyloxyaryl.

2. Connection on p. 1, in which R1- C1- C3-alkyl.

3. Connection on p. 1, in which R1is methyl.

4. Connection on p. 1, in which A is hydrogen.

5. Connection on p. 1 with herbicide activity.

6. The compound of formula II

< / BR>
where A is hydrogen, fluorine or chlorine;

X is fluorine, chlorine or bromine;

Y is methyl substituted by one or more halogen atoms;

Z - methyl;

R1is hydrogen or C1- C6)-alkyl;

R3and R4the same or different, hydrogen or C1- C6-alkyl provided that the total number of carbon atoms in R3and R4does not exceed 6.

7. The compound of formula IY

< / BR>
where A is hydrogen, fluorine or chlorine;

X is fluorine, chlorine or bromine;

Y is methyl substituted by one or more halogen atoms;

Z - methyl;

R1is hydrogen or C1- C6)-alkyl;

R3and R4same and different, hydrogen or C1- C6-alkyl provided that the total number of carbon atoms in R3and R4does not exceed 6.

8. Herbicide composition containing the active ingredient is a derivative of tetrahydropyrimidine-2.4 and inert RIT compound of formula I under item 1 in herbicide effective amount.

9. Way to destroy unfavorable weeds, including processing areas, where growing or will grow unfavorable weeds, derived tetrahydropyrimidine-2,4, characterized in that as a derivative of tetrahydropyrimidine-2,4 used as a compound of formula I under item 1 in herbicide effective amount.

 

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< / BR>
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< / BR>
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