Pyrimidine derivatives

 

(57) Abstract:

Usage: as compounds with herbicide activity. The inventive product of General formula (I) in which R is hydrogen, -N=C(R1)2where R1- lower alkyl,-chloro, methoxy; D and E may be the same or different, represent a hydrogen atom, halogen, lower alkyl group, lower CNS group, lower alojamiento lower CNS group, or salts of alkaline metal, alkaline earth metal, ammonium, organic ammonium salts. Formula I is: 9 the table.

The aim of the invention are new pyrimidine derivatives or their salts.

In the U.S. patents NN 4248619 and 4427437 indicates that 2-phenoxypyridine derivatives possess herbicide activity.

However, the connection represented in these contrasted materials have the disadvantage, which is reflected in the fact that their herbicide activity does not meet the necessary requirements.

Have conducted extensive studies of pyrimidine derivatives with the aim of creating a connection with a higher herbicide activity, and as a result discovered that connected xipamide derivatives, characterized by excellent weed-killing activity against perennial weeds and annual weeds, and at the same time they provide a high level of safety for crops, particularly rice and wheat.

When comparing compounds presented in U.S. patent N 4248619, with the compounds according to the invention is that the last connection surpass the indicated compounds on herbicide activity, in particular on herbicide activity during post-harvest processing. In addition, the compounds according to the invention are characterized by a broad spectrum herbicide action and can destroy at a relatively low dose of the weeds as Xanthium strumarium L. (Xantium strumarium), morning glory (Jpomola spp) and chufa (Cyperus rotunrus), the control of which usually causes great difficulties. In addition, the compounds according to the invention provide a high level of safety for rice due to the low dose required for effective weed control.

The invention provides pyrimidine derivatives of the formula

in which R represents a hydrogen atom or-N=C(R1)2where each element of R is a lower alkyl group, a represents a chlorine atom or Afleet a hydrogen atom, halogen atom, a lower alkyl group, lower CNS group or alojamiento lower CNS group, or a salt of an alkali metal, alkaline earth metal, ammonium, organic ammonium salts.

In table. 1 presents typical examples of compounds according to the invention. Rooms compounds listed in this table will be listed in the description.

P R I m e R 1. Getting isopropylammonium-2,6-bis[4,6-dimethoxypyrimidine-2-yl)oxy]benzoic acid (compound 1).

2.0 g (3.8 mmole) benzyl-2,6-bis/(4,6-dimethoxypyrimidine-2-yl)oxy/ benzoate (so pl. 130-132aboutC) was dissolved in methanol. This solution was added to 0.3 g of 10% palladium charcoal, pre-moistened with acetic acid and methanol. For the implementation of the catalytic reduction was introduced hydrogen at atmospheric pressure. After cessation of hydrogen absorption, the reaction was considered complete, the reaction solution was subjected to filtration. The filtrate was concentrated under reduced pressure. To the residue was then added ethyl acetate and water with the aim of separating liquid. The ethyl acetate layer was washed with water, dried and concentrated. Thus obtained crystals were washed with hexane, which poses eremein-2-yl)oxy] benzoic acid (compound 1).

When using 5.5 g (10 mmol) 4-methoxybenzyl-2,6-bis[(4,6-dimethoxy - ridin-2-yl)oxy]benzoate (so pl. 82-83aboutC) performed the same procedure as in example 1, which allowed us to obtain 3.0 g of the target compound in the form of a white powder with so pl. 148-150aboutC.

P R I m e R 3. Obtaining 2-(4-chloro-6-methoxypyridine-2-yl)-hydroxy-6-(4,6-DiMeo - xinitimage-2-yl) oksibenzoynoy acid (compound 2).

Getting trimethylsilylmethyl-2-(4-chloro-6-methoxypyridine-2-yl)oxy-6-(4,6 - dimethoxypyrimidine-2-yl)oxybenzoic NaH (0.4 g, purity, 60%) was suspended in 50 ml of tetrahydrofuran. To this suspension was added trimethylsilylmethyl-6-(4,6-dimethoxypyrimidine-2-yl)oxicillin (3.0 g) and then the mixture was stirred at room temperature for 30 minutes To this mixture was added 4-chloromethoxy-2-methylsulfonylamino (1.8 g), then the mixture was stirred at room temperature for 12 hours After the reaction to this mixture was added water, after which it was extracted with ethyl simple ether. A simple layer of ethyl ether was dried over anhydrous magnesium sulfate. The solvent is kept at reduced pressure. Thus obtained crude extract was purified using chromatography on columns of the increase of 2-(4-chloro-6-methoxypyridine-2-yl)oxy-6-(4,6-dimethoxypyrimidine - n-2-yl)oksibenzoynoy acid.

Trimethylsilylmethyl-2-(4-chloro-6-methods - xipamide-2-yl) oxy-6-(4,6-dimethoxypyrimidine-2-yl)oxybenzoic (4.0 g) was dissolved in 80 ml of dimethylformamide. To this solution was added trihydrate tetrabutylammonium fluoride (5.9 g), after which the mixture was stirred at room temperature for 15 minutes After the reaction in the mixture were added water and a small amount of an aqueous solution of potassium bisulfate, and then the mixture was extracted with ethyl acetate. The organic layer was washed saturated aqueous sodium chloride and dried over anhydrous magnesium sulfate. The solvent is kept under reduced pressure and the thus obtained crystals were washed with a mixture of hexane and isopropylene (IPE), which allowed to obtain the specified compound in the form of white crystals (3.2 g). So pl. 150-152aboutC.

P R I m e R 4. Getting isopropylamino-2,6-bis[(4,6-dimethoxypyrimidine-2-yl)oxy]benzoate (compound 13).

2,6-bis[(4,6-Dimethoxypyrimidine-2-yl) oxy]benzoic acid (2.0 g) and Isopropylamine (1.0 g) was dissolved in 30 ml of tetrahydrofuran, then the mixture was stirred at room temperature for 12 hours, the Reaction solution was concentrated and precipitated as a result, the crystals flushing the>P R I m e R 5. Getting isopropylidenebis of aminoether 2,6-bis[(4,6-dimethoxypyrimidine-2-yl)oxy]benzoic acid (compound 19).

2,6-bis[(4,6-Dimethoxypyrimidine-2-yl) oxy]benzoic acid (3.0 g) and N, N-carbonyldiimidazole (1.2 g) was dissolved in 50 ml of tetrahydrofuran, after which the solution was heated under reflux for 15 minutes To this reaction solution was added acetone oxime (0.6 g), and then the mixture was heated under reflux for 16 hours

After the reaction to this mixture was added water and the mixture was extracted with ethyl acetate. The organic layer was washed saturated aqueous sodium chloride and dried over anhydrous magnesium sulfate. The solvent is then drove away under reduced pressure. Thus obtained crude extract was purified using chromatography on columns of silica gel, which allowed us to obtain the above compound in the form of white crystals (2.1 g), (so pl. 114-117aboutC).

P R I m e R 6. Obtaining 2,6-bis[(4,6-dimethoxypyrimidine-2-yl)oxy] benzoate Tris (2-oxyethyl)ammonium (compound No. 15) of 2,6-bis[(4,6-dimethoxypyrimidine-2-yl)oxy] benzoic acid (2.0 g) and triethanolamine (0.7 g) was dissolved in 30 ml of tetrahydrofuran, after which it is listed and precipitated as a result, the crystals were washed with hexane, allowing for the connection specified in the form of white crystals (2.4 g). (So pl. pp. 103 -- 110aboutC).

P R I m e R 7. 2,6-bis[(4,6-Dimethoxypyrimidine-2-yl)oxy]benzoate ammonium (compound 18).

2,6-bis[(4,6-dimethoxypyrimidine-2-yl) oxy]benzoic acid (5.1 g) and 28% aqueous ammonia solution (1.7 g) was mixed with a mixture solvent consisting of tetrahydrofuran and ethanol. The precipitated crystals were washed with acetone with the formation of the above compound in the form of white crystals (3.7 g).

(So pl. 135-140aboutC).

P R I m e R 9. Obtaining 2,6-bis[(4,6-dimethoxypyrimidine-2-yl)oxy]-benzoic acid (compound 1). 60% sodium hydride (1.4 g) suspended in tetrahydrofuran. To this suspension was added benzyl-2,6-deoxybenzoin (8.0 g), and then the mixture was stirred at room temperature for 15 minutes Then to this mixture was added 4,6-dimethoxy-2-methylsulfonylamino (7,8 g), after which the mixture was subjected to interaction within 8 h under reflux.

After cooling, the reaction solution was poured into water and was extracted with ethyl simple ether. The organic layer was washed saturated aqueous sodium chloride and dried over anhydrous is and columns of silica gel with the formation of benzyl-6-(4,6-dimethoxypyrimidine-2-yl) oxicarinata (2.0 g) as white crystals. (Melting point: 63-65aboutC).

Thus obtained benzyl-6-(4,6-dimethoxypyrimidine-2-yl) oxicillin were subjected to interaction with 4,6-dimethoxy-2-methylsulfonylamino-DIN the same way as in example 4, the result of which was obtained benzyl-2,6-bis[(4,6-dimethoxypyrimidine-2-yl)-oxy] benzoate. So pl. 130-132aboutWith in the form of white needle crystals.

Thus obtained benzyl-2,6-bis[(4,6-dimethoxypyrimidine-2-yl-oxy] benzoate was subjected to hydrolysis in the same way as in example 1, which allowed us to obtain 2,6-bis[(4,6-dimethoxypyrimidine-2-yl)oxy] benzoic acid as a white powder (melting point: 148-150aboutC).

P R I m e R 10. Obtaining 2,6-bis[(4-chloro-6-methoxy - (pyrimidine-2-yl)-oxy]benzoic acid (compound 8).

60% sodium hydride (1.6 g) suspended in tetrahydrofuran. To this suspension was added 2,6-deoxybenzoin acid (2.0 g), after which the mixture was stirred at room temperature for 30 minutes Then to this mixture was added 4-chloro-6-methoxy-2-methylsulfonylamino (5.8 g), after which the mixture was subjected to interaction at room temperature for two days.

After the interaction, the reaction mixture was poured into water and isusually over anhydrous sodium sulfate. The solvent is kept at reduced pressure. The residue was purified using chromatography on columns with the formation of the indicated compound (1.6 g) as light yellow crystals (so pl. 149-150aboutC).

The herbicide according to the invention is capable of destroying a variety of weeds on such agricultural land, as the land or of the fruit of the garden or in the woods, on lawns or other non-agricultural land by tillage before or after emergence of the weeds or by spraying the leaves. In addition, this herbicide can destroy various weeds in a rice field by processing the irrigated soil before or after emergence of the weeds or by spraying the leaves.

For soil, the herbicide according to the invention is used in a dose of from 1 g to 10 kg, preferably 5-5000 g and most preferably 10-1000 g of active ingredient per 1 ha For leaf spraying the herbicide is diluted to a concentration equal to 1-10000 hours/million Most preferred option is its application in a dose of from 10 to 100 g of active ingredient per 1 ha for rice fields, in a dose of from 50 to 500 g per 1 ha for fruit garden or lawn and at a dose of from 100 to 1000 g for forest or agricultural lands.

P Corporation"), 0.5% Demol N (trade name of the company "Kao Corporation), 20% of menilite 202 (trade name of the firm "Cunmin Kogyo K. K.), and 69% of galita SA (trade name of the company, "Gilit company LMT) were uniformly mixed and sprayed with the formation of a wettable powder.

Further herbicide activity of the herbicides according to the invention will be described with reference to test examples.

The following abbreviations denote the following subjects plants:

Or:Tr: wheat, EU: plushie millet, Se: spickle green, Ro: Highlander pepper, Am: sirica thin, Ip: morning glory, Ha: Xanthium strumarium L., S.G.: chufa, Si: weed blood, Ch: white pigweed, Ci: syt rice, CD: raw materials weerasena, IU: Monochoria, Sc: reed, Se", AI: listowel smooth and AB: canetic Theophrastus.

Test example 1. (spraying the leaves in the dry valleys).

In a pot filled with soil (surface area: 100 cm2), were sown the seeds batoshevo millet (RS), Rosicky blood (Si), mountain pepper (Ro), chirici thin (Am), Marie white (Ch) and Siti rice (Ci) and covered by a soil layer of thickness from 0.5 to 1 see the Pot was kept in a greenhouse at a temperature of from 20 to 25aboutC for 2 weeks, after which a predetermined amount of the wettable powder is 10 ar (dose of active ingredient: 4 g (1 ha). The evaluation was made on the 14th day after spraying in accordance with the standard shown in the table. 2.

The results denoted by the index numbers in table. 3.

Test example 2 (tillage in dry areas).

In a pot filled with soil (surface area 100 cm2), were sown the seeds batoshevo millet (EU), Rosicky blood (Si), mountain pepper (Ro), chirici thin (Am), Marie white (Ch) and Siti rice (CI), and then covered by soil layer thickness of 0.5-1 see Through day after sowing, a predetermined amount of wettable powder obtained in accordance with example 1, was diluted with water and applied on the soil surface at the rate of 1000 liters per 1 ha), the dose of the active ingredient, 4 kg (1 ha). The evaluation was made on the 20th day after the treatment in accordance with the standard specified in the table. 2. The results shown by the index numbers in the table. 4.

Test example 3 (test for weed control in rice field).

In a pot filled with rice field soil (surface area: 100 cm2), were sown the seeds batoshevo millet (EU), site veeravalli (CD), Monochoria (Mo) and bulrush (Sc), after which the soil was watered with water to a depth of 3 see two on the composition of 1, was diluted with water and dropwise introduced on the surface of the water at a dose equivalent to 1000 g (1 kg) of active ingredient per 1 hectare Assessment was made on the 21st day after the treatment in accordance with the standard specified in table. 2. The results are expressed as index numbers in the table. 5.

Test example 4 (selective herbicide test).

In a pot filled with soil (surface area: 600 cm2), were sown the seeds of rice (Or), wheat (Tr), batoshevo millet (EU), the results of the analysis of green (Se), mountain pepper (Ro), chirici thin (Am), ipomea (Ip) and Xanthium strumarium L. (Ha), planted chufa tubers (Cr) and covered with a soil layer of thickness 0.5-1 see This pot was placed in a greenhouse at 20-25aboutWith two weeks, after which a predetermined amount of the wettable powder prepared in accordance with example 1, was diluted with water and this mixture was sprayed leaves at the rate of 1000 liters per 1 ha

The evaluation was made on the 30th day after spraying in accordance with the standard specified in table. 2. The results are shown in the form of index numbers in the table. 6.

Test example 5 (leaf spray - herbicide test).

In a pot filled with soil (surface area of 600 cmwow (Ro), serizy thin (Am), cantica Theophrastus (Ah), ipomea (Ip) and Xanthium strumarium L. (Ha), after which the seeds were covered with a soil layer of thickness 0.5-1 see This pot was placed in a greenhouse at 20-30aboutWith ten days, and then a predetermined amount of the wettable powder obtained in accordance with example 1, was diluted with water containing an inhibitor, and this composition was sprayed leaves at the rate of 1000 liters per 1 hectare Assessment was made on the 21st day after spraying in accordance with the standard specified in table. 2. The results are indicated by the index numbers in the table. 7.

Below are comparative compounds 1,2,3,4 and 5 (U.S. patent N 4248619).

Comparative compound I:

1,3-bis[(4,6-dimethyl-2-pyrimidinyl - C]benzene.

Comparative compound 2:

1,1-bis[5-chloro-2-pyrimidinone]-2-methylbenzo.

Comparative compound 3:

1,3-bis[5-chloro-2-pyrimidinedione]2-nitrobenzene.

Comparative compound 4:

5-chloro-2-(3)-4,6-dimethyl-2-pyrimidine - lexi(phenoxy)pyrimidine.

Comparative compound 5:

1,2-bis(5-chloro-2-pyrimidinone)be Sol.

Test example 6 (leaf spray - test for phytotoxicity in unassert: Labella), and then they were covered with a soil layer of thickness 0.5 see This pot was placed in a greenhouse at 20-30aboutTo achieve phase blooming 2,5 leaves, after which a predetermined amount of the wettable powder obtained in accordance with example 1, was diluted with water containing an inhibitor of growth with this composition was sprayed leaves at the rate of 1000 liters per 1 ha dose of the active ingredient; 6.3 and 1.6 g of 10 ar. Phytotoxicity was determined on the 30th day after spraying in accordance with the standard specified in table. 2. As a result of these trials found no phytotoxicity at any dose in the case of compounds 1, 6, 13, 14, 15, 16, 17, 18 according to the present invention.

Test example 7 (tillage - herbicide test).

In a pot filled with soil (surface area: 600 cm2), were sown the seeds batoshevo millet (EU), the results of the analysis of green (Se), Guma (So) and Alopecurus smooth (AI), and then they were covered with a soil layer of thickness 0.5-1 see Through day after sowing, a predetermined amount of wettable powder obtained in accordance with example 1, was diluted with water and applied on the soil surface at the rate of 1000 liters per 1 hectare After processing this pot was placed in Teplice. 2. The results are shown in the form of index numbers in the table. 8.

Test example 8 (herbicide test against tigernuts used as a perennial weed).

In a pot filled with soil (surface area 100 cm2), and the planting chufa tubers (Cr) and covered them with soil layer thickness of 1 see This pot was placed in a greenhouse at 20-30aboutTo achieve the blooming phase of the fourth sheet, after which a predetermined amount of the wettable powder obtained in accordance with example 1, was diluted with water containing an inhibitor, and this composition was sprayed leaves. The evaluation was made on the 20th day after the spraying in accordance with the standard specified in table. 2. The results are indicated in the form of index numbers in the table. 9.

PYRIMIDINE DERIVATIVES of General formula

< / BR>
where R is hydrogen or-N=C(R1)2;

R1is lower alkyl;

A - chlorine, methoxy;

D and E are the same or different, is hydrogen, halogen, lower alkyl group, lower CNS group or galizana lower CNS group, or salts of alkaline metal, alkaline earth metal, ammonium, organic ammonium salts.

 

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SUBSTANCE: invention describes substituted benzoylcyclohexanediones of the general formula (I):

wherein m = 0 or 1; n = 0 or 1; A means a single bond or alkanediyl (alkylene) with 1-4 carbon atoms; R1 means hydrogen atom or unsubstituted alkyl with from 1 to 6 carbon atoms; R2 means methyl; R3 means hydrogen atom, nitro-, cyano-group, halogen atom, alkyl with from 1 to 4 carbon atoms substituted with halogen atom, alkoxy-group with from 1 to 4 carbon atoms or alkyl sulfonyl with from 1 to 4 carbon atoms; R4 means nitro-group, halogen atom, unsubstituted alkyl with from 1 to 4 carbon atoms of that substituted with halogen atom; Z means heterocycle, and herbicide agent based on thereof. Also, invention describes substituted derivatives of benzoic acid of the general formula (III):

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EFFECT: enhanced effectiveness and valuable properties of compounds.

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SUBSTANCE: invention relates to new derivatives of uracil of the formula [I] eliciting the herbicide effect, herbicide composition based on thereof and a method for suppression of weed growth. In the formula [I] W means oxygen (O), sulfur (S) atom or imino-group; Y means oxygen atom (O) or sulfur atom (S); R1 means (C1-C3)-alkyl or (C1-C3)-halogenalkyl; R2 means (C1-C3)-alkyl; R4 means hydrogen atom (H) or methyl; R5 means (C1-C6)-alkyl, (C1-C6)-halogenalkyl, (C3-C6)-alkenyl, (C3-C6)-halogenalkenyl, (C3-C6)-alkynyl or (C3-C6)-halogenalkynyl; X1 means halogen atom, cyano- or nitro-group; X2 means hydrogen atom (H) or halogen atom; each among X3 and X4 means independently hydrogen atom (H), halogen atom, (C1-C6)-alkyl, (C1-C6)-halogenalkyl, (C3-C6)-alkenyl, (C3-C6)-halogenalkenyl, (C3-C6)-alkynyl, (C3-C6)-halogenalkynyl, (C1-C6)-alkoxy-(C1-C6)-alkyl, (C1-C6)-alkoxy-, (C1-C6)-halogenalkoxy-, (C1-C6)-alkoxycarbonyl-(C1-C6)-alkoxy- or cyano-group. Also, invention relates to new intermediate substances used for preparing compounds of the formula [I] corresponding to formulae [VII] , [XXXIV] and [XXXIII] wherein in compound of the formula [VII] W means oxygen (O), sulfur (S) atom or imino-group; Y means oxygen (O) or sulfur atom (S); in compounds of formulae [XXXIV] and [XXXIII] W means oxygen atom (O); R17 means oxygen atom (O); R4 means hydrogen atom (H) or methyl. Also, invention relates to methyl- or ethyl-[2-(5-amino-2-chloro-4-fluorophenoxy)phenoxy]acetate not early described in the literature.

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