Derivatives of pyridine or its salt, the retrieval method, herbicide composition and method for killing weeds

 

(57) Abstract:

Essence: new derivatives of pyridine total f-crystals of l and its salts, the method of production thereof and herbicide composition containing them as effective ingredients, and method of controlling weeds. Pyridine derivatives or their salts have a herbicide against annual and perennial weeds growing in paddy fields and upland land at very low doses are safe for rice, wheat, cotton and corn, and may be suitable for use as herbicides on the fields which are cultivated these plants. 4 C. and 6 C.p. f-crystals, 14 PL. Connection structure of f-crystals of l

The invention relates to new derivatives of pyridine and their salts, to a method for their herbicide composition containing a specified derivative as an effective ingredient, and to a method of controlling weeds.

Hitherto known were derived pyridineboronic acid with herbicide activity, derivative 3-(4,6-dimethoxypyrimidine-2-yl) accipitrinus acid (Japanese patent publication has not passed the examination, No. 84/1989), derived pyrimidinetrione to the Katsia N 121 973/1990 and 149 567/1990).

However, these references do not describe the derivatives of nicotinic acid with Deputy containing heterocyclic ring in 2-position, as in the compound of the present invention.

To date we developed many herbicides, and contributions to conservation (savings) energy for agricultural operations and improve production efficiency. However, their practical use of such herbicides have different problems. For example, due to problems related to the environment, the required herbicide, herbicide reaching effect, especially at low dose. In particular, the desired herbicide should be herbicide action to destroy perennial weeds such as sorghum Halep (Sorgum halepense) and sedge purple (Cyperus rotundus), which are widely spread on farmland around the world and difficult to destroy. In addition, in connection with the management and agriculture is particularly desirable herbicide with satisfactory selectivity and safety in relation to cultivated plants.

So far, all known compounds described in the above cited sources, are not always provided udomainname nicotinic acid to develop connections, possessing satisfactory herbicide activity, and as a result have found that pyridine derivatives of the present invention, which are derivatives of nicotinic acid with 2-position Deputy containing heterocyclic ring, have an excellent herbicide activity for the destruction of annual and perennial weeds, including grassy weeds and sedge weeds and broad-leaved weeds, in the processing of water in rice fields and soil treatment or foliage on upland fields, and also have satisfactory security in respect of cultivated plants, including rice, wheat, and similar. The present invention was achieved on the basis of this discovery.

A derivative of pyridine of the present invention is defined by the General formula (I)

(1)

where R represents a hydrogen atom, hydroxyl group, alkoxy group, alkoxyalkyl, aryloxyalkanoic group, benzyloxy group which may be substituted, trimethylsilyloxy group, alkylsulfonyl, alkylthio, phenoxy group which may be substituted, thiophenoxy group which may be substituted, or imidazolidinyl group;

R1and R2ablauts is amino, haloalkoxy or alkyl group;

X represents a halogen atom, halogen-substituted alkyl group, acylamino group, alkyl group, cycloalkyl, haloidalkyls, alkenylamine group, alkyloxy group, alkoxycarbonyl group, alkoxy, alkylamino, dialkylamino group, phenyl group, substituted phenyl group, benzyloxy group which may be substituted, benzylthio group which may be substituted, a benzyl group which may be substituted, phenoxy group which may be substituted, thiophenoxy group which may be substituted, alkoxyalkyl, acyl group, alkylthio group, arylamino group which may be substituted, or a group having the formula

< / BR>
W represents an oxygen atom, a sulfur atom, NH group or a group of the formula > NCOB (where represents a hydrogen atom or alkoxy group);

Z represents a methine group or a nitrogen atom; and

n represents 0 or an integer from 1 to 3, and X may be a combination of different groups, when n is at least 2.

The invention relates to a derivative of pyridine and its salts.

In addition, the invention relates also to a method for producing derivatives of peg, salt, and to a method of controlling weeds.

In the General formula (l) examples of alkoxy groups R include (1-7)-alkoxy group with a straight or branched chain, such as methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy group, isobutoxy group, Deut.-butoxy, tert-butoxy group, n-pentyloxy, isopentylamine, sec-pentyloxy, tert-pentyloxy, n-hexyloxy, 2,2-dimethylpropylene group, 2-methylbutoxy group, 2-ethylbutane, 3,s-Dimethylbutane group and 1,3 .3m-trimethylbutane group.

Examples of the alkoxy group, R1and R2are groups defined in the above alkoxy group R. Examples of the halogen atom include chlorine, bromine, fluorine and iodine. Examples of alkylamino groups include alkylamino group with straight or branched (1-3) With chain, such as methylamino, ethylamino, n-propylamino, isopropylamino group. Examples of dialkylamino groups include (1-3) With dialkylamino group with a straight or branched chain, such as dimethylamino, diethylamino, methylethylamine group, di-n-propylamino, diisopropylamino group. Examples of haloalkoxy groups include (1-7) With haloalkoxy group with a straight or branched chain, having part or all of the alkoxy group substituted by the above-mentioned halogen atoms is the SCP with a straight or branched chain, such as methyl, ethyl, n-sawn, ISO-propyl, n-bucilina, isobutylene group, sec-bucilina, tert-bucilina, n-pencilina, isopentyl, second-pencilina, tert-pencilina group, n-exilda, 2,2-dimethylpropylene group, 2-methylbutyl group, 2-motivationa, 3,3-dimethylbutyl group and 1,3 .3m-trimethylethylene group.

Examples of the halogen atom, alkylamino group, dialkylamino group X are such as defined in the definition of the above-mentioned halogen atoms, alkylamino group, and dialkylamino group, R1and R2. Examples of the halogen-substituted alkyl groups include alojamiento alkyl group having part of a group or the whole (1-3) alkyl group with straight or branched chain, substituted by the above-mentioned halogen atoms such as deformational group, chlormethine and tribromoaniline group. Examples of alkyl groups are as defined in the designation of the above-mentioned alkyl group, R1and R2. Examples of alkoxy groups are as defined in characterizing the above-mentioned alkoxy group, R1and R2.

Examples of haloalkoxy groups are the groups defined above in include (3-7) With cycloalkyl group, such as cyclopropyl group, cyclopentolate and tsiklogeksilnogo group.

Examples of alkenylacyl, alkyloxy groups include (2-8) With alkenylacyl, alkyloxy group.

Examples of substituted phenyl groups include a substituted phenyl group, and some or all of the phenyl group is substituted by the above-mentioned halogen, lower alkyl, lower alkoxy, alkylamino, dialkylamino, halogen-substituted alkyl, haloalkoxy, nitro, hydroxy, alkoxyalkane, alkoxycarbonyl, alkoxycarbonylmethyl, alkylthiols, benzyloxy, cyano, phenoxy, replaced phenoxy, alkylthio, alkoxyalkyl or etinilnoy group, such as p-chloraniline group and 3-taillow group.

Examples of preferred compounds include the compound of General formula (l) in which R represents a hydroxyl group, methoxy, ethoxy, benzyloxy, ethoxyethoxy group, pivaloyloxymethyl or trimethylsilyloxy group; R1and R2are the same or different and represent a hydrogen atom, chlorine atom, methyl, methoxy group, dimethylamino group or a halogen-substituted methoxy group; X represents a hydrogen atom, a chlorine atom, a bromine atom, a methyl group is th phenyl group, methoxy-substituted phenyl group or a mono - or di-methylamino group; W represents an atom of oxygen, sulfur, NH group, or acylamino group; Z represents a methine group or a nitrogen atom; and n is 9 or an integer of 1-3.

The compound of the present invention of General formula (I) can be obtained, for example, using the following methods to obtain, but the present invention is not limited to these methods.

The method of obtaining 1.

Reaction scheme 1

< / BR>
(where L represents a halogen atom, alkylsulfonyl, benzylaniline group which may be substituted, alkylsulfonate group, haloalkylthio group and benzylmalonate group which may be substituted; and W, X, n, R, R1, R2and Z have the meanings defined above).

The compound of General formula (I) can be obtained by reaction of compounds of formula (A) with the compound of the formula (V) in the presence of a base in an amount at least equivalent, in an appropriate solvent, at a temperature ranging from room temperature up to the boiling point of the solvent over a period of 0.5 to 24 hours

Examples of bases include alkali metals such as metal is isopropylated (LDA); hydrogenated alkali metals and hydrogenated alkali-earth metals such as hydrogenated sodium, potassium hydrogenated and hydrogenated calcium; an alkali metal alcoholate such as tert-butyl potassium. carbonates of alkali metals such as sodium carbonate and potassium carbonate; and alkali metal hydroxide such as sodium hydroxide and potassium hydroxide.

Examples of solvents include the solvents of the hydrocarbon type such as hexane, benzene, toluene and xylene; halogenated hydrocarbon solvents such as dichloromethane and chloroform; solvents such ethers such as diethyl ether, tetrahydrofuran and 1,4-dioxane; ester solvents such as methyl acetate and ethyl acetate; solvent type ketones such as acetone and methyl ethyl ketone; aprotic polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide and dimethyl sulfoxide; acetonitrile and so on.

The compound of formula (A) can be obtained in accordance with the methods described in Journal of Medicinal Chemistry" (vol. 6, page 294, 1963; vol 7. page 17, 1964), "Berichte" (V, page I III, 1941), "Liebigs Ann. Chem" (371, 1979) and similar, and can also be obtained using the following methods.

The reaction scheme SUP> are the same or different and represent a hydrogen atom, a lower alkyl group, lower alkoxy group, alkylamino group, dialkylamino group, phenyl group or substituted phenyl group; and R6represents alkyl group).

The compound of formula (IV) can be obtained by heating the compounds of formula (II) and acatalog the compounds of formula (III) in the presence or absence of an inorganic or organic base during the period of time from 0.1 to 10 h in an appropriate solvent, including broken such as methanol and ethanol, ethers such as tetrahydrofuran, aprotic polar solvents such as N, N-dimethylformamide or acetonitrile ("Archix der Pharmazie volume 318, page 481, 1985).

The compound of formula (V) can be obtained by further reaction of the above compounds of formula (IV) at room temperature over a period of from 1 h to 7 days, in acid, such as polyphosphoric acid, water galoidovodorodov, sulfuric acid and acetic acid.

The compound of formula (VI) can also be obtained by the interaction of the compounds of formula (IV) with Hydrobromic or hydrochloric gas in an inert dissolve the deposits of solvent, preferably at a temperature of from 10 to 50oC.

In addition, the compound of formula (VII) can be obtained by using the reaction of the above compounds of formula (VI) with thiourea at 50 120oC for 0.5-10 h, in the presence of water and mineral acids such as hydrochloric acid and sulfuric acid, treatment of the resulting product with an alkaline material such as sodium hydroxide and potassium hydroxide, and then acidification of the resulting product acid such as hydrochloric acid (see not passed the examination of Japanese patent publication N 275 562/1989).

Thus obtained product contains small amounts of sulfide and disulfide in addition to the target toolname connection.

The method of obtaining 2.

Reaction scheme 3

< / BR>
(where L, X, n, R, R1, R2, Z and W have the meanings defined above).

The compound of formula (I) can also be obtained by reaction of compounds of formula (C) with the compound of the formula (D) in the presence of a base, taken in an amount equal to at least the equivalent amount in an appropriate solvent for 0.5-24 hours at a temperature in the range from room temperature to the boiling point rastvor get 3.

Reaction scheme 4

< / BR>
(where R2represents an alkyl group or trimethylsilylethynyl group; X, n, W, Z, R1and R2have the meanings defined above).

The compound of formula (F) can be obtained through reaction of compounds of formula (E) in the presence of a base, in a quantity at least equivalent to the amount), in an appropriate solvent such as water or a solvent containing water for 0.5-24 hours at a temperature of from room temperature to the boiling point of the solvent, and then acidification of the resulting product.

Examples of the base include alkali metal hydroxide such as sodium hydroxide and potassium hydroxide; carbonates of alkali metals such as sodium carbonate and potassium carbonate, and acid carbonates of alkali metals such as sodium bicarbonate and potassium bicarbonate. If trimethylsilylacetamide ether examples of the base include tetrabutylammonium fluoride and potassium fluoride.

Examples of the solvent include hydrocarbon solvents such as hexane; solvent type, halogenated hydrocarbons such as dichloromethane and chloroform; alcohol solvents, such as mean; the type solvents ketones such as acetone and methyl ethyl ketone; aprotic polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide and dimethyl sulfoxide; acetonitrile or similar.

The method of obtaining 4.

Reaction scheme 5

< / BR>
(where M+is 1 equivalent amount of alkali metal, alkaline earth metal, ammonium or organic ammonium ion; and X, n, W, Z, R1and R2have the meanings defined above).

The compound of formula (G) can be obtained by the interaction of the compounds of formula (F) with an equivalent amount of a base in an appropriate solvent for 0.5-24 hours at a temperature in the range from room temperature to the boiling point of the solvent.

Examples of the base include hydrogenated alkali metals, such as sodium hydride and potassium hydride, an alcoholate of an alkali metal such as sodium methylate and sodium ethylate; alkali metal hydroxide and a hydroxide of alkaline-earth metals such as sodium hydroxide, potassium hydroxide and calcium hydroxide; carbonates of alkali metals and carbonates of alkaline-earth metals such as sodium carbonate and calcium carbonate; b is ammonia and Isopropylamine.

Examples of solvents include solvent-type hydrocarbons such as benzene, toluene and xylene, halogenated hydrocarbon solvents such as dichloromethane and chloroform; solvents such as alcohols such as methanol, ethanol and 2-propanol; solvents such ethers such as diethyl ether, tetrahydrofuran and dioxane; aprotic polar solvents such as N,N-dimethylacetamide and dimethyl sulfoxide; acetonitrile, water, or similar.

The method of obtaining 5.

Reaction scheme 6

(where Q represents a halogen atom, cyano group, imidazolidinyl group or substituted, amidines group; and R, R1, R2, X, n, W and Z have the meanings defined above).

The intermediate compound of formula (N) to obtain the compounds of the present invention of formula (I) can be obtained by reaction of compounds of formula (F) with a condensing agent in a quantity at least equivalent to the amount in the appropriate solvent for 0.5-24 hours at a temperature in the range -10oC to the boiling point of the solvent. The intermediate compound thus obtained may be separated or may not be separated, and the compound of formula (I) can valentno number, in an appropriate solvent, for 0.5-24 hours at a temperature in the range -10oC to the boiling point of the solvent.

Examples of the condensing agent include thionyl chloride, dichlorohydrin oxalic acid, ester chlorocarbonate (harpalini) acid, carbonyldiimidazole, ester cyanophosphonate acid, carbodiimide and similar. Examples of the base and solvent used in the process are such as defined in the description of the method of obtaining 1.

The method of obtaining 6.

Reaction scheme 7

< / BR>
(where R8represents an alkyl group, alkoxyalkyl group, aryloxyalkyl group or a benzyl group which may be substituted; R1, R2, L, W, X, n and Z have the meanings defined above).

The compound of formula (I) can be obtained by the interaction of the compounds of formula (F) with the compound of the formula (K) in the presence of a base in at least an equivalent amount, in a suitable solvent, for 0.5-24 hours at a temperature in the range -10oC to the boiling point of the solvent. Examples used the base and the solvent are those defined in the description of the method Poluchenie with examples.

Example of getting 1. Synthesis of methyl 2-(4,6-dimethoxypyrimidine-2-yloxy)-4-phenyldiamine (compound 18).

50.0 g (0,22 mole) of methyl 2-hydroxy-4-phenyldiamine and 200 ml of dichloromethane were weighed and added dropwise to 50.0 g (0,24 mol) triftormetilfullerenov anhydride at a temperature of about -20oC. After adding dropwise the resulting mixture was further mixed at a temperature of from -20 to -10oC for 30 min, and then the temperature was allowed to reach room temperature. The reaction mixture was then poured into water and was extracted with 300 ml-mi dichloromethane, and the organic layer was then washed with water and saturated aqueous sodium chloride. After drying, the solvent was distilled, giving 50.0 g of a yellow viscous liquid methyl-2-methanesulfonyl-4-phenyldiamine (yield 64%).

Then were weighed and heated at 80oC for 30 min 25,0 g (0,16 mol) of 4,6-dimethoxy-2-hydroxypyrimidine, 25,0 g (0,18 mol) of potassium carbonate and 200 ml of dimethylsulfoxide. After cooling the resulting mixture to room temperature, thereto was added 50.0 g (of 0.14 mole) of the above synthesized sulfonate, and the resulting mixture reacted CSOs organic layer was washed with water and saturated aqueous sodium chloride, and dried with anhydrous sodium sulfate. The solvent is then distilled, and the residue was purified using chromatography on silicagel column to obtain 3.6 g of the above product.

Output: 4,5% So pl. 111-115oC.

Example of getting a 2. Synthesis of 2-(4,6-dimethoxypyrimidine-2-yloxy)-4-phenyldiamine acid (compound 7).

2.6 g (of 0.07 mol) of methyl 2-(4,6-dimethoxypyrimidine-2-yloxy)-4-phenyldiamine and 50 ml of dimethyl sulfoxide were weighed and thereto was added dropwise an aqueous solution of 2N sodium hydroxide in the amount of 4.6 ml (0,009 mole) at 60oC. Obtained drip after adding the mixture was further mixed for 30 min at 60oC. the resulting mixture was poured into water and washed twice with ethyl acetate. The aqueous layer was then brought to pH 2 with an aqueous solution of 10% hydrochloric acid and the precipitated crystals were filtered off. Thus obtained crystals were washed with water and then dried. The dried crystals were precrystallization with ethyl acetate, was obtained 1.1 g of white crystals.

Yield: 44% So pl. 165 to 169oC.

Example of getting a 3. Synthesis of methyl 2-(4,6-dimethoxypyrimidine-2-yloxy)-6-methylnicotinate (compound 11).

5.0 g (of 0.003 mol)0 ml of dimethylformamide were weighed, and subjected to reaction at 100oC for 4 h, the Reaction mixture was then poured into water and was extracted with 100 ml of ethyl acetate. The organic layer was then washed with water and saturated aqueous sodium chloride. After drying over anhydrous sodium sulfate, the solvent was distilled, and the residue was purified using chromatography on silicagel column, yielding 0.73 g of the target product.

Output: 8,0% So pl. 99-103oC.

Example 4. Synthesis of 2-(4,6-dimethoxypyrimidine-2-yloxy)-4,6-dimethylaniline potassium (compound 2).

1.5 g (0,005 mol) of 2-(4,6-dimethoxypyrimidine-2-yloxy)-4,6-diethylnicotinamide acid, 0,49 g (0,005 mol) of potassium bicarbonate, 10 ml of acetone and 10 ml of water were weighed and stirred at room temperature for 1 h and then at 50oC for 20 minutes the Solvent was distilled under reduced pressure and to the residue was added 10 ml of ethyl acetate. The crystals precipitated thus precipitated was filtered off and dried, yielding 1.6 g of the target product.

Yield: 95% melting point: 188-195oC.

Example of getting a 5. Synthesis of 4-(4,6-dimethoxypyrimidine-2-yloxy)-2-phenyl-6-methylnicotinic acid (compound 4).

2.0 g (0,004 mol) 2-trimethylsilyltriflate 12 ml of 1 mol of an aqueous solution of tetrabutylammonium fluoride. The resulting mixture was stirred at room temperature for one night. The reaction mixture was then poured into 200 ml of water, and to the mixture was added 1.5 ml of concentrated hydrochloric acid. The resulting reaction mixture was extracted with ethyl acetate, and washed with water. The resulting reaction mixture is then dried by magnesium sulfate, and the solvent was distilled, yielding 0.9 g of the target product.

Output. 60% melting point: 277-284oC.

Example of getting a 6. Synthesis of methyl 4-(4-chlorophenyl)-2-(4,6-dimethoxypyrimidine-2-ylthio) nicotinate (compound 93).

73,9 g (0,24 mol) of 2-bromo-4-(4-chlorophenyl)nicotinic acid and 22.0 g (to 0.29 mol) of thiourea were weighed, and thereto was added 100 ml of 5% HCl aqueous solution and 150 ml of acetic acid. The resulting mixture was stirred at 100oC for 2 h and poured into water. Then to the resulting mixture were added 400 ml of 50% aqueous sodium hydroxide solution, and the mixture is stirred at room temperature for 30 minutes the Mixture was then padillas 20% aqueous HCl solution, and the precipitated crystals thus filtered and rinsed with water. The washed crystals are then dried, yielding crude is i.i.d. crystals, 66,0 g (0,30 mol) of 4,6-dimethoxy-2-methylsulfonylamino and 104,0 g (of 0.75 mol) of potassium carbonate were weighed, and to the mixture was added 500 ml of dimethyl sulfoxide. The resulting mixture was stirred at 80oC for 2 hours After the temperature was allowed to reach room temperature, the reaction mixture was added to 68.0 g (of 0.48 mole) under the conditions, and the resulting reaction mixture was stirred at room temperature for 30 m, the Reaction mixture was then poured into water and was extracted in 1 l of ethyl acetate. After washing with water and saturated aqueous sodium chloride, and the mixture was dried with anhydrous sodium sulfate. After filtration the solvent was distilled, and the residue was purified using chromatography on silicagel column (showing a solvent mixture of ethyl acetate/hexane 1/4), giving 19,0 of white crystals of the target product.

Output: 19,2% melting point: 138-141,5oC.

Example of getting a 7. Synthesis of 4-(4-chlorophenyl)-2-(4,6-dimethoxypyrimidine-2-ylthio)nicotinic acid (compound 94).

Tried to hitch up to 16.8 g (0,040 mol) of methyl 4-(4-chlorophenyl)-2-(4,6-dimethoxypyrimidine-2-ylthio)nicotinate and 150 ml of dimethyl sulfoxide, and to the mixture was added 35 ml (0,070 mole) 2 norms. water restoraoC for 30 minutes. The mixture was then poured into water and washed twice with ethyl acetate. Thus obtained aqueous layer was pagkilala 10% aqueous hydrochloric acid solution and was extracted with 500 ml of ethyl acetate. After washing with water and saturated aqueous sodium chloride it was dried with anhydrous sodium sulfate. After filtration the solvent was distilled, and the remaining crystals were washed with methanol and isopropyl ether, giving of 11.5 g of white crystals of the target product.

Output: 70,8% melting point: 219-223oC.

Example of getting 8. Synthesis pivaloyloxymethyl 4-(4-forfinal)-2-(4,6-dimethoxypyrimidine-ylthio)nicotinate (compound 106).

0,70 g (0,0019 mole) of 4-(4-forfinal)-2-(4,6-dimethoxypyrimidine-2-ylthio)nicotinic acid and 0.50 g (0,0036 mole) of potassium carbonate was otvalivalas, and thereto was added 10 ml of dimethylformamide. The mixture was then stirred at room temperature for 1 h then to the mixture was added 0.34 g (0,0022 mole) chloromethylphosphonate, and the mixture is stirred at room temperature for 2 h the Mixture was then poured into water and was extracted with 50 ml ethyl acetate. After washing with water and saturated aqueous sodium chloride mixture asiasociety chromatography (exhibiting a solvent mixture of ethyl acetate/hexane=1/4), giving 0,81 g yellowish thick syrupy target product.

Output: 88,0% refractive index (n2D0): 1,5615.

Example of getting a 9. Synthesis of methyl-4-(4-isopropoxyphenyl)-2(4,6-dimethylpyrimidin-2-ylthio)nicotinate (compound 180).

20,0 g (0,059 mole) of 2-bromo-4-(4-isopropoxyphenyl)nicotinic acid and 5.5 g (0,072 mole) of thiourea was otvalivalas, and thereto were added 40 ml of 5% aqueous HCl and 60 ml of acetic acid. The resulting mixture was stirred at 100oC for 2 hours After pouring the reaction mixture into water to it was added 200 ml of 50% aqueous sodium hydroxide solution, and the mixture is stirred at room temperature for 30 minutes. The mixture was padillas 20% HCl to precipitate crystals, and loose precipitated crystals were washed with water, then dried. After this was taken the sample synthesized above crude crystals thiosalicylic acid, 11.1 g (to 0.060 mole) of 4,6-dimethyl-2-methylsulfonylamino and 25.0 g (0,18 mol) of potassium carbonate, and to the mixture was added 200 ml of dimethyl sulfoxide, and the resulting mixture was mixed at 80oC within 2 hours After allowing the temperature to reach room temperature in the reaction mixture we use the mixture was then poured into water and was extracted with 500 ml of ethyl acetate. After washing with water and saturated aqueous sodium chloride, and the mixture was dried with anhydrous sodium sulfate. After filtration the solvent was distilled, and the residue was purified using chromatography on silicagel column (showing a solvent mixture of ethyl acetate>hexane 1/2), giving 6.5 g of light yellowish thick syrupy target product.

Output: 26.7% of the refractive index (n2D0):1,5965

Example 10. 4-(4-chlorophenyl)-2-(4,6-dimethylpyrimidin-2-ylthio)sodium nicotinate (compound 307).

0.50 g (0,0012 mole) of 4-(4-chlorophenyl)-2-(4,6-dimethoxypyrimidine-2-ylthio)nicotinic acid and 7 ml of ethanol were weighed, and at room temperature was added to 0.30 g (0,0016 mol) of methanol solution of 28% sodium methylate is added dropwise. After adding dropwise, the mixture is additionally stirred at room temperature for 20 minutes Dropped thus precipitated crystals were filtered off and were washed with ethanol and dried, giving and 0.46 g of white powder of the desired product.

Output: 86,0% melting Point: 244-247oC.

Example of getting 11. Synthesis of 2-(4,6-dimethoxypyrimidine-2-ylthio)nicotinic acid (compound 52).

4.0 g (0,026 mol) of 2-Mer what I weighed, and added 70 ml of dimethylformamide, and the mixture was mixed at 80oC for 2 h the resulting mixture was poured into water, and was filtered 100 ml-mi of ethyl acetate. The aqueous layer was then pagkilala 10% aqueous HCl solution to precipitate crystals. Fallen thus precipitated crystals were filtered off and were washed and dried. The crystals were then precrystallization from methanol, giving of 5.3 g of light yellow crystals of the target product.

Yield: 70.1% of the melting point: 165-168oC.

Example 12. Synthesis of ethoxy methyl 2-(4,6-dimethoxypyrimidine-2-yloxy)-4 - fenilcetonuria (compound 86).

0.50 g (0,0014 mole) of 2-(4,6-dimethoxypyrimidine-2-yloxy)-4-phenyldiamine acid and 0.24 g (0,0017 mole) of potassium carbonate were weighed and thereto was added 10 ml of dimethylformamide, and the mixture is stirred at room temperature for 1 h then to the mixture was added additional 0.14 g (0,0015 mole) of ethoxymethylene, and the mixture is stirred at room temperature for 30 minutes the Mixture was then poured into water and was extracted with 50 ml ethyl acetate. Extracted material was rinsed with water and saturated aqueous sodium chloride, and dried with anhydrous sulfate Noah column (the solvent etelaat/hexane 1/4), giving of 0.54 g of light yellowish thick syrupy target product.

Yield: 93.1% of the refractive index (n2D0): 1,5701.

Example of receipt 13. Synthesis of 4-(3-chlorophenyl)-2-(4,6-dimethoxypyrimidine-2-ylthio-)-N - methylsulfonylmethane (compound 301).

3.0 g (0,0074 mole) of 4-(3-chlorophenyl)-2-(4,6-dimethoxy-pyrimidine-2-ylthio)nicotinic acid were weighed and added to 30 ml of dimethylformamide. Then, to the mixture, with stirring, gradually was added 1.50 g (0,0093 mole) of carbonyldiimidazole, and the mixture is stirred at room temperature for 24 hours of 1.80 g (0,0019 mole) of methanesulfonamide and of 0.60 g (0,0015 mole) of 60% sodium hydride were weighed, and thereto was added 30 ml of dimethylformamide, and the mixture was mixed at 80oC for 2 hours After that, it was added previously prepared dimethylformamide solution carbonyldiimidazole nicotinic acid at room temperature, and the mixture was mixed at 80oC for 2 h, the Reaction mixture was then poured into water and washed with 50 ml of ethyl acetate. Then the aqueous layer was pagkilala 10% aqueous HCl solution and was extracted with 100 ml of ethyl acetate. Extracted material was rinsed with water and saturated aqueous Rast residue was purified using chromatography on silica gel (manifesting solvent: ethyl acetate/hexane 1/1), giving 3.0 g of light yellowish glassy target product.

Yield: 81.3% melting Point: 54-58oC.

Example of getting a 14.

Synthesis of benzyl 2-(4,6-dimethoxypyrimidine-2-ylamino)nicotinate (compound 398).

2.3 g (0,01 mol) of benzyl 2-aminonicotinate, 2.2 g (0,01 mol) of 4,6-dimethoxy-2-methylsulfonylamino and 0.4 g (0,01 mol) of 60% sodium hydride were weighed and thereto was added 10 ml of dimethylformamide, and the mixture is stirred at 100oC for 2 h the Mixture was then poured into water and was extracted with 100 ml of ethyl acetate. Extracted material was then rinsed with water and saturated aqueous sodium chloride, and dried with anhydrous sodium sulfate. After filtration, the solvent was distilled, and the residue was precrystallization with ethanol, giving 1.6 g of a yellow-brownish powder of the desired product.

Output: 43,0% melting Point: 128-131oC.

The following examples of the preparation of the intermediate products of the compounds of the present invention are illustrated as reference examples.

Referential example 1. Synthesis of 1-cyano-1-methoxycarbonyl-4-(N,N-dimethylamino)-2-(4-methoxyphenyl)-1,3-butadiene.

85,0 g (of 0.44 mol) of 1-cyano-1-methoxycarbonyl-2-(4-methodology the offer was heated under reflux for 30 min under stirring. The reaction mixture was cooled with ice water to precipitate crystals which were then filtered off. The crystals thus obtained were washed three times with 100 ml of methanol and dried, giving 103,6 g of greenish-yellow of the target product.

Output: 81,4% melting Point: 175-178oC.

Referential example 2. Synthesis of methyl 2-hydroxy-4-(4-were)nicotinate.

117,0 g (of 0.54 mol) of 1-cyano-1-methoxycarbonyl-4-(N,N-dimethylamino)-2-(4-were)-1,3-butadiene was added to 250 ml of concentrated sulfuric acid at a temperature below 20oC under stirring, and the mixture is stirred at room temperature for 48 hours the Reaction mixture was poured into 1 l of ice water, and precipitated material was filtered off. The filtrate was brought to pH 6 with aqueous solution of sodium hydroxide to precipitate the desired product which was then filtered. Precipitated material was rinsed with water and methanol, and dried, giving a rate of 74.9 g of white crystals of the target product.

Output 60,9% melting point: 222-224oC.

Reference example 3. Synthesis of methyl 2-bromo-4-(4-chlorophenyl)nicotinate.

80,0 g (0,28 mol) of 1-cyano-1-methoxycarbonyl-4-(N,N-dimethylamino)-2-(4-chlorophenyl)-1,3-butadiene weighted is based temperature and under stirring acetic acid solution of 25% HB. After adding dropwise the resulting mixture stirred at room temperature for 3 hours the Reaction mixture was then poured into ice water to precipitate crystals. Precipitated crystals thus filtered and rinsed with water and dried, giving 75,0 g of white crystals of the target product.

Yield: 83.5% of the melting point: 73-76oC.

Reference example 4. Synthesis of 2-bromo-4-(4-chlorophenyl)nicotinic acid.

Took a sample of 50.0 grams (0.15 mole) of methyl 2-bromo-4-(4-chlorophenyl )nicotinate, and thereto was added 300 ml of dimethylsulfoxide and 60 ml of 30% aqueous solution of sodium hydroxide, and the mixture was mixed at 80oC for 3 hours the Mixture was then poured into water and washed with 300 ml of ethyl acetate. Then the aqueous layer was pagkilala 10% aqueous HCl solution to precipitate crystals which were then filtered off. Precipitated crystals thus were washed with water and isopropyl ether and dried, giving 41,0 g of white crystals of the target product.

Output: 85,7% melting point: 204-208oC.

Below in the following description of examples of the compounds of the present invention, thus obtained, are illustrated in table. 1. Legend soutenue compounds, referred to, will show the numbers under which they are given in the table.

Pym is not: 4,6-Dimethoxypyrimidine-2-ilen group.

Tri: 4,6-Dimethoxytrityl-2-ilen group.

Ph: Phenyl group.

(a): 2-(4,6-Dimethylpyrimidin-2-yl)oxy group

(b): 2-(4-Deformedarse-6-methoxypyridine-2-yl)oxy group.

(C): 2-(4-Chloro-6-methoxypyridine-2-yl)oxy group

(d): 2-(4-Methoxy-6-methylpyrimidin-2-yl)oxy group

(e): 2-(4-Dimethylamino-6-methoxypyridine-2-yl)oxy group

(f): 2-(4-Methoxypyridine-2-yl)oxy group

(g): 2-(4,6-Dimethylpyrimidin-2-yl)thio group

(h): 2-(4-Methoxy-6-mailtrain-2-yl)thio group

(i): 2-(4-Methoxy-6-methylpyrimidin-2-yl)thio group

(j): 2-(4,6-Dimethoxypyrimidine-2-yl)amino group

(k): 2-(N-formyl-(4,6-dimethoxypyrimidine-2-yl)amino)group

(l): 2-((N-methoxycarbonyl)-4,6-dimethoxypyrimidine-2-yl)amino group

(m): 2-(4-chloro-6-methoxypyridine-2-yl)thio group.

In tables 2 to 4 are examples of intermediate products obtained as described above.

Herbicide composition of the present invention includes at least one pyridine derivative of General formula (I) and its salt as an effective ingredient.

As the media used in these formulation, can be transferred to solid media such as gilit, talc, bentonite, clay, kaolin, diatomaceous earth, white carbon, vermiculite, calcium carbonate, slaked lime, siliceous sand, ammonium sulfate or urea, or a liquid media such as isopropanol, xylene, cyclohexanone or methylnaphthalene.

As surface-active agent and dispersing agent can be named, for example, a metal salt of alkylbenzenesulfonate, metal salt dinaftiletilena acid, ester alcohol and sulfuric acid, alkylarylsulfonate, ligninsulfonate, polyoxyethyleneglycol ether, polyoxyethylenated-arrowy ether or polyoxyethylenesorbitan-monoalkyl. As adjuvants can be, for example, lists carboxymethylcellulose, polyethylene is with a powdered solid carrier. Wettable powder may be obtained by mixing the active ingredient with a powdered solid carrier, a surface-active agent and dispersing agent. Emulsifiable concentrate can be obtained by mixing the active ingredient with liquid media, surfactants and dispersing agents. The drug is in the form of granules can be obtained by coating a granular solid carrier of the active ingredient together with adjuvant, or by adding water to the solid carrier, the active ingredient and adjuvant and extruding the mixture through the holes. The number or proportion of the active ingredient is selected arbitrarily depending on its use, and it usually ranges from 0.01 to 20% by weight, preferably from 0.1 to 10% by weight, in the cases of growth and preparative forms in the form of granules, and from 0.1 to 80% by weight, preferably from 1 to 50% by weight, in cases emulsifiable concentrate and wettable powder.

In the practical application of the herbicide of the present invention may be diluted to a suitable concentration before applying or can be applied directly. The amount of the herbicide of the present invention can vary arbitrarily in C the environment and the type of formulation. When the herbicide of the present invention can be applied directly, as in the case formulation in the form of powder and granules, it is used in a dose of from 0.1 g to 5 kg, preferably from 1 g to 1 kg of active ingredient per 10 ar. In the case of a liquid such as emulsifiable concentrate and preparative form of a wettable powder of the active ingredient may not be diluted to a concentration of from 0.1 to 10000 ppm, preferably from 10 to 5,000 parts per million, for later use.

The herbicide of the present invention can be applied to foliage, soil or water surface.

If desired, the compound of the present invention can be used in combination with insecticides, sterilizers, other herbicides, agents regulating the growth of plants, fertilizers or similar.

Now will be given typical examples ready preparative forms herbicide compositions of the present invention. The types of compounds and additives and the ratio in the mixtures should not be limited to these, and they can vary arbitrarily within wide limits. In these examples, "part" means "part by weight".

Example 1 preparationincome-naphthalenesulfonate sodium and formalin, 20 parts of diatomaceous earth and 69 parts of clay were mixed and pulverizadores, giving wettable powder.

Example 2 formulation (wettable powder). 10 parts of compound 7, 0.5 parts polyoxyethyleneglycol ether, 0.5 parts of a condensate of formalin with b-naphthalenesulfonate sodium, 20 parts of diatomaceous earth, 5 parts of white carbon black, and 64 parts of clay were mixed and pulverizadores, giving wettable powder.

Example 2 formulation (wettable powder containing calcium carbonate). 10 parts of compound 23, 0.5 parts polyoxyethyleneglycol ether, 0.5 parts sodium naphthalenesulfonate-formalin condensate, 5 parts of white carbon black, and 64 parts of calcium carbonate were mixed with pulverizadores, giving wettable powder.

Example 4 formulation (emulsifiable concentrate). 30 parts of compound 25, 60 parts of an equivalent amount of a mixture of xylene and isophorone and 10 parts of surface active substances: polyoxyethylenesorbitan, polyoxyethyleneglycol polymer and alkylarylsulfonate fully mixed, giving emulsifiable concentrate.

Example 5 formulation (granules). 10 parts of compounds 49, 80 parts of the filling of ieeetransactions, polyoxyethyleneglycol polymer and alkylarylsulfonate and 10 parts of water were thoroughly mixed, giving a pasty material. Pasty material was then abstrogirovalsya through a sieve with holes of diameter 0.7 mm, and the extruded product was dried and cut into pieces of 0.5-1 mm, giving pellets.

The compound having General formula (I), and salts thereof of the present invention are effective in very small doses to destroy a variety of pernicious weeds, causing serious problems growing on upland fields, in a wide interval from the stage of emergence (germination) to the stage of growth, and examples of weeds include broad-leaved weeds such as knotweed pale (Polygonum lapathifolium), amaranth (Amaranthus viridis), quinoa common (Chenopodium album), starwort (Stellaria media), limnocharis (Abutilon theophrasti), prickly SIDA (Sida spinosa), morning glory (Pomoca sp. ), and Xanthium strumarium L. (Xanthum strumarium); perennial and annual juice weeds such as sedge purple (Cyperus rotundus), yellow sedge, Kyllinga brevifolia, umbrella plant (Cyperus microiria) and rice sedge (Cyperus iria); and gramineous weeds such as barnyard grass (Echinochloa crusgalli), weed blood (Digitaria sp.), spickle (Setaria sp.), the annual bluegrass (Poa annua), sorghum allep the different effects on annual weeds such as barnyard grass (Echinochloa crusgalli), sedge small-flowered (Cyperus difforus) and Monochoria (Monochoria vaginalis), and perennial weeds such as Sagittaria pygmaca, Cyperus serotinus, Elecharis Kuroguwai, reed (Seirpus notarui), and Alisma canaliculatum), grown in paddy rice fields. Depending on the type of connection of the present invention does not show phytotoxicity with respect to rice, wheat, cotton and maize, and is therefore suitable as a herbicide under cultivation of these crops.

Now will be described herbicide effects of the compounds of the present invention with reference to the following examples of tests.

Example 1 tests. (Test for herbicide action during cultivation of rice paddy fields).

Plastic powder (surface area of 100 square cm) filled with soil of rice fields, after compaction and levelling of soil were inoculated barnyard grass (EU), Monochoria (Mo) and bulrush (Sc), and the soil is filled with water to a depth of 3 see the next day wettable powder prepared in accordance with example 1 preparative forms was diluted with water and applied drops on the water surface so that was applied to 100 g of active ingredient per 10 ar. Plants were then grown VI, shown in the table. 5. The results are shown in table. 6.

In the example test, the following compounds were used as comparative examples (hereinafter, the same in each trial).

Comparative compound a:

methyl 5-chloro-3-(4,6-dimethoxypyrimidine-2-yl)accipitrinus (see not passed the examination of Japanese Patent application N 84/1989).

Comparative connection:

N-3-(4,6-dimethoxypyrimidine-2-yl)triftormetilfullerenov (see not passed the examination of Japanese Patent application N 149 567/1990).

Example 2 tests. (Test for herbicide effect during cultivation in upland fields).

In a plastic pot (surface area: 120 sq. cm) filled with soil Nagorno field was sown seeds of barnyard grass (EU), Highlander pale (Ro), amaranth (Am), quinoa ordinary (Ch) and site veeravalli (rice) (CI) and closed soil. Wettable powder prepared in accordance with example 1 formulation, it was diluted with water and applied evenly to the soil surface using a sprayer small amount of 100 l / 10 ar so that the flow rate was 100 g of active ingredient per 10 ar. Plants were then grown in the greenhouse, and proizvedenii in table. 5. The results are shown in table. 7.

Example 3 tests. (Test for herbicide effect during the processing of the leaves on the high field.

In a plastic pot (surface area of 120 sq. cm) filled with soil sublime field was sown barnyard grass, knotweed pale, aramant, quinoa ordinary and syt and closed soil and were grown in the greenhouse for 2 weeks. Wettable powder prepared in accordance with example 1 formulation, it was diluted with water and applied to the foliage using a small sprayer in the amount of 100 l/10 ar so that the flow rate of the active ingredient was 100 g / 10 ar. Plants were then grown in the greenhouse and evaluated herbicide effect on the 14th day after the treatment in accordance with the standards shown in the table. 5. The results are shown in table. 8.

Example 4 tests. (Test for weed-killing effect and test for phytotoxicity against rice during the processing of the leaves on the high field.

In a plastic pot (surface area: 600 sq. cm) filled with soil Nagorno field was sown rice (Or), sorghum Halep (So), Alopecurus aequalis (Al), Highlander pale (Ro), amaranth (Am) and quinoa ordinary (Ch) and closed soil and warstwie example 1 preparative forms it was diluted with water in an amount of 100 l of water for 10 AP and was applied to the sheets by means of a small sprayer. Plants were then grown in the greenhouse, and on day 14 after treatment evaluated herbicide effect and phytotoxicity in accordance with the standards, as shown in the table. 5. The results are shown in table. 9. The dose of the active ingredient in the table shows the amount of active ingredient (g) 10 ar.

Example 5 tests. (Test for weed-killing effect and phytotoxicity with respect to rice soil sublime field).

In a plastic pot (surface area of 600 sq. cm) filled with soil Nagorno fields were cultivated and closed ground seeds of rice (Or), sorghum Halep (So), Alopecurus aequalis (Al), Highlander pale (Ro), amaranth (Am) and quinoa ordinary (Ch). After absorbing water from the bottom of the pot a specified number of wettable powder prepared in accordance with example 1 formulation was diluted with water in an amount of 100 l / 10, ar, and was applied to the soil surface using a small sprayer. Plants were then grown again in the greenhouse, and on the 20th day after the treatment has been assessed herbicide effect and Pittock is gradient in the table shows the number of the active ingredient in grams per 10 ar.

Example 6 tests. (Test for herbicide action and test the phytotoxicity with respect to wheat during processing of the leaves on the upper field).

In a plastic pot (surface area of 600 sq. cm) filled with soil elevated or mountainous field was sown wheat (Tr), sorghum Halep (So), Alopecurus aequalis (Al), Highlander pale (Ro), amaranth (Am) and quinoa ordinary (Ch) and closed with soil and cultivated in a greenhouse for 2 weeks. The specified number of wettable powder prepared in accordance with example 1 formulation was diluted to 100 l of water for 10 AP and deposited on the foliage with small opryskivatel. Plants are then grown in the greenhouse, and on the 14th day after the treatment has been assessed herbicide effect and phytotoxicity in accordance with the standard scale, shown in table. 5. The results are shown in the following below table 11. The dose of the active ingredient in the table shows the number of the active ingredient (grams) 10 ar.

Example 7 tests. (Test for herbicide action and test the phytotoxicity against wheat soil Nagorno-field).

In a plastic pot (surface area region (Ro), amaranth (Am) and quinoa ordinary (Ch) and closed with a layer of soil. After absorption of water from the bottom of the pot a specified number of wettable powder prepared in accordance with example 1 formulation was diluted with water in an amount of 100 l / 10, ar, and deposited on the soil surface using a small sprayer. Plants are then grown in the greenhouse, and on the 20th day after the treatment has been assessed herbicide effect and phytotoxicity in accordance with the standard grading scale shown in table. 5. The results are shown in table. 12. The dose of the active ingredient in the table shows the amount of active ingredient (g) 10 ar.

Example 8 testing. (Test for herbicide action and test the phytotoxicity against the cotton in the processing of the leaves on the upper field).

In a plastic pot (surface area of 600 sq. cm) filled with soil Nagorno field was sown cotton (Go), sorghum Halep (So), Alopecurus aequalis (Al), Highlander pale (Ro), amaranth (Am) and quinoa ordinary (Ch) and closed with a layer of soil and were grown in the greenhouse for 2 weeks. The specified number of wettable powder prepared in accordance with Example 1 preparative Faure is El. Plants are then grown in the greenhouse, and on day 14 after treatment evaluated herbicide effect and phytotoxicity in accordance with standard estimates, shown in table. 5 above. The results are shown in table. 13. The dose of the active ingredient in the table shows the amount of active ingredient per 100 ar.

Example 9 testing. (Test for herbicide action and test the phytotoxicity against cotton soil in upland fields).

In a plastic pot (surface area of 600 sq. cm) filled with soil Nagorno field was sown cotton (Go), sorghum Halep (So), Alopecurus aequalis (Al), Highlander pale (Ro), amaranth (Am) and quinoa ordinary (Ch), and closed with a layer of soil. After absorption of water from the bottom of the pot a specified number of wettable powder prepared in accordance with example 1 preparative forms and was diluted to 100 l of water at 10 ar, and was applied to the soil surface using a small sprayer. Plants are then grown in the greenhouse, and on the 20th day after the treatment in accordance with the standards shown in the table. 5, evaluated herbicide effect and phytotoxicity. The results are presented in table. 14. Dose Akti is kzt38

1. Derivatives of pyridine having the following General formula

< / BR>
where R is hydrogen, a hydroxyl group, WITH1-C7-alkoxygroup, alkoxyalkyl having 1-7 carbon atoms in each alkyl part, lower acyloxy(C1-C7-alkoxygroup, benzyloxy, lower alkyloxybenzoic group, trimethylsilyloxy lowest alkylsulfonamides lowest allylthiourea or imidazolidine group,

R1and R2may be the same or different and each represents C1-C7-alkoxygroup, halogen atom or WITH1-C7is an alkyl group;

W is an oxygen atom, a sulfur atom, a group of the formula NC(O)B ( where B is a hydrogen atom or a lower alkoxy group),

Z methine group or a nitrogen atom,

X is a halogen atom, halogen-substituted C1-C3is an alkyl group, a C1-C7is an alkyl group, a C1-C7-alkoxygroup, phenyl group or phenyl group substituted by 1-3 substituents selected from C1-C3-alkyl, halogen, C1-C3-alkoxy, nitro, halogen WITH1-C3-alkyl or CI-C1-C3-alkylamino, or menzilcioglu;

n is 0 or an integer from 1 to 3;

X can be a combination of ream

R is a hydrogen atom, a hydroxyl group, WITH1-C3-alkoxygroup, benzyloxy or trimethylsilyloxy;

X halogen atom, halogen-substituted C1-C3is an alkyl group, a lower alkyl group, lower alkoxygroup, phenyl group or phenyl group substituted by 1-3 substituents selected from C1-C3-alkyl, C1-C3-alkoxy, halogen atom, nitro, halogen (C1-C3)-alkyl, CI-C1-C3-alkylamino;

W is an oxygen atom or a sulfur atom;

Z, R1, R2and n have the specified values.

3. Derivatives under item 1, characterized in that

R is a hydroxyl group, methoxy, ethoxy, benzyloxy, ethoxyethoxy, trimethylsilyloxy;

R1and R2may be the same or different and each represents methyl, methoxy group, chlorine atom;

X halogen atom, methyl, halogen-substituted methyl group, phenyl group, halogen-substituted phenyl group, methyl-substituted phenyl group, a methoxy-substituted phenyl group;

W is an oxygen atom, a sulfur atom;

Z methine group or a nitrogen atom;

n is 0 or an integer cislo from 1 to 3.

4. Derivatives of pyridine or IP7-alkoxy-C1-C7-alkoxygroup, lower acyloxy (C1-C7-alkoxygroup, benzyloxy lowest alkoxybenzenes, trimethylsilyloxy lowest alkylsulfonamides lowest allylthiourea or imidazolidine group;

R1and R2may be the same or different and each represents C1-C7-alkoxygroup,1-C7is an alkyl group or halogen;

W is an oxygen atom, a sulfur atom, a group having the formula NC(O)B, where B is a hydrogen atom or a lower alkoxygroup;

Z methine group or a nitrogen atom;

X phenyl group, phenyl group substituted by 1-3 substituents selected from C1-C3-alkyl, halogen atom, WITH1-C3-alkoxy, nitro, halogen WITH1-C3-alkyl, CI-C1-C3-alkylamino, or menzilcioglu;

n is an integer from 1 to 3, and X may be a combination of different groups, when n is not less than 2.

5. Derivatives of pyridine under item 1, having the following General formula

< / BR>
where R is a hydrogen atom, a hydroxyl group, WITH1-C7-alkoxygroup,1-C7-alkoxy-C1-C7-alkoxygroup, lower acyloxy-C1-C7-alkoxygroup, benzyloxy or tighrope or imidazolidine group;

R1and R2may be the same or different and each represents C1-C7-alkoxygroup, halogen atom or WITH1-C7is an alkyl group;

W is an oxygen atom or a sulfur atom;

Z methine group or a nitrogen atom;

X1halogen atom, a C1-C7is an alkyl group, a C1-C7-alkoxygroup or halogen-substituted C1-C3is an alkyl group;

X2halogen atom, a C1-C7is an alkyl group, halogen-C1-C3is an alkyl group, a C1-C7-alkoxygroup, phenyl group, phenyl group, substituted by 1 or 2 substituents selected from C1-C3-alkyl, C1-C3-alkoxy, halogen atom, nitro, halogen-C1-C3-alkyl or CI-C1-C3-alkylamino;

l is 0 or an integer from 1 to 3 and X1can be a combination of different groups, when l is not less than 2;

m is 0 or an integer Chiloe 1 or 2 and X2can be a combination of different groups, when m is 2, or their salts.

6. Derivatives of pyridine under item 1, having the following General formula

< / BR>
where R is a hydroxyl group, WITH1-C7-alkoxygroup,1-C7-alkoxy-C1-C7-alkoxygroup, lower aciloc the PA, lowest alkylsulfonamides lowest allylthiourea or imidazolidine group;

W is an oxygen atom or a sulfur atom;

Z methine group or a nitrogen atom;

X1halogen atom, a C1-C7is an alkyl group, a C1-C7-alkoxygroup, halogen WITH1-C3is an alkyl group;

l is 0 or an integer of 1-3, and X1can be a combination of different groups, when 1 is not less than 2, or their salts.

7. The method of obtaining pyridine derivatives having the General formula

< / BR>
where R, R1, R2, X, n, W and Z have the meanings given in paragraph 1, and their salts, characterized in that the compound of General formula

< / BR>
where R, X, n and W have the meanings given in paragraph 1, is subjected to reaction with a compound of General formula

< / BR>
where L is a halogen atom, alkylsulfonyl group, benzylaniline group which may be substituted, alkylsulfonate group, aloitusohjeita group or benzylmalonate group which may be substituted;

R1, R2and Z have the meanings given in paragraph 1,

in the presence of a base.

8. The method of obtaining pyridine derivatives having the General formula

< / BR>
where R1, R2, X, n, W and Z have values that determine the health of the group or trimethylsilylethynyl group;

R1, R2, X, n, W and Z have the meanings given in paragraph 1,

subjected to reaction with a base and then acidifying the resulting reaction product.

9. Herbicide composition containing the active agent and a diluent or carrier, wherein the active agent it contains a derivative of pyridine or its salt as defined in any of paragraphs.1 6, in an amount of 0.01-80 wt.

10. Method of controlling weeds using a processing plant or the soil where these plants grow, herbicide, characterized in that as herbicide use pyridine derivative or its salt as defined in any of paragraphs.1 6, in the amount of 0.001 to 50 kg/ha

 

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