Substituted 1-phenyl-or 1-pyridinyl-benzotriazole, herbicide composition, the method of controlling undesirable plants

 

(57) Abstract:

Describes the new substituted 1-phenyl - or 1-pyridinyl-benzotriazole General formula (I), where the values of R1- R7specified in paragraph 1 of the claims. The compounds exhibit herbicide activity. Also describes herbicide composition based on compounds of the formula (I) and a method of controlling undesirable plants. 3 S. and 21 C.p. f-crystals, 3 tables.

This invention relates to substituted benzotriazoles formula

< / BR>
in which

R1, R2and R3can independently represent hydrogen; halogen; nitro; hydroxy; cyano; alkyl; amino; alkoxyalkyl; cianelli; carboxyethyl; carboalkoxylation; cyano (carbalkoxy)alkyl; hydroxyalkyl; alkoxyalkyl; alkylsulfonamides; haloalkylthiol; (alkyl)naminoalkyl; (alkylcarboxylic)zalkyl; haloalkyl; formyl; alkylsulphonyl; carboxy or its salts; Coolkill; carboxamido; mono - or di-substituted, carboxamido, where the nitrogen substituents can be selected from hydrogen, alkyl, haloalkylthio and alkylsulfonyl; sulphonamido, where the nitrogen substituents can be selected from hydrogen and alkyl; (alkylsulfonyl)zamino; (aceti is t -(R10)m-COR11; -(R10)m-SO2R11;

< / BR>
alkyl; haloalkyl; hydroxyalkyl; aralkyl; cianelli; acetoxyethyl; alkoxyalkyl; hikkoshi; alkenyl or quinil;

R9represents hydrogen; alkyl; quinil; alkenyl or alkylaryl;

R10is alkylene;

R11is alkyl; haloalkyl; hydrogen; hydroxy; alkoxy; haloalkoxy; alkoxyalkyl; alkoxyalkane; alkoxyalkyl; dialkoxybenzene; aryloxy; aralkyl; alkoxycarbonyl; hydroxycarbonyl; alkoxycarbonylmethyl; hydroxyarylalkyl; (alkyl)namino, (alkyl)nhydrazino; alkoxycarbonylmethyl; hydroxyethylamino; (alkyl)n- aminoethylamino; (alkyl)naminocarbonylmethyl; hydroxycarbonylmethyl; alkylsulfonyl; arylsulfonyl; acetylaminofluorene; N-alkoxy-N-(alkyl)mamino; N-hydroxy-N-(alkyl)mamino; cyanoaniline; (alkenyl)n- amino; alkoxyalkyl; (quinil)namino; alkenylamine; alkyloxy or semicarbazide;

or R2and R3taken together with the carbon atom to which they are attached, form a optionally substituted saturated or unsaturated heterocycle, sod of alkyl, alkoxy, halogen, haloalkyl, cyano, carboxy, formyl, oxo, carbalkoxy;

or R3represents -(CH2)qR14in which R14denotes a 5-, 6 - or 7-membered saturated or unsaturated optionally substituted heterocycle, where the ring members selected from the group consisting of nitrogen, carbon, oxygen and sulfur, and where the substituents are selected from the group consisting of alkyl, alkoxy, halogen, haloalkyl, cyano, carboxy, formyl, oxo, carbalkoxy;

or R3is YR8in which R8or R11can be a 5-, 6 - or 7-membered saturated or unsaturated optionally substituted heterocycle, in which the members of the cycle are selected from nitrogen, carbon, oxygen, and sulfur, and the substituents are selected from alkyl, alkoxy, halogen, haloalkyl, cyano, carboxy, formyl, oxo, carbalkoxy;

m is 0 or 1;

n is 0, 1 or 2;

z is 1 or 2;

q is 0 or 1;

M and Q independently represent alkoxy; alkyl; (alkyl)namino; hydroxy; hydrogen; alkenylamine; (alkenyl)namino; alkyloxy or (quinil)namino;

L represents oxygen or sulfur;

P represents phosphorus;

R4represents hydrogen, halogen, alkyl or nitro;

R
R6represents hydrogen; halogen; haloalkyl; haloalkoxy; cyano or SOyR12and R12denotes alkyl or haloalkyl and y is 0, 1 or 2;

R7represents hydrogen or halogen;

X represents N or CR13where

R13denotes hydrogen; halogen; haloalkyl; cyano; nitro; alkylthio; alkylsulfonyl; alkylsulfonyl or alkoxy; and their agricultural acceptable salts.

Description of the invention

Specific preferred variant embodiments within the scope of the above formula are the following:

R1represents hydrogen; halogen; cyano; alkyl and haloalkyl. More preferably hydrogen, halogen and cyano.

R2is hydrogen; nitro; alkyl; halogen; alkoxy; carbonyloxy; haloalkyl; haloalkoxy; Coolkill; SO3H and YR8where Y represents O, NR9and S(O)n.

R3represents hydrogen; alkyl; halogen; hydroxy; haloalkyl; amino; a 5-, 6 - or 7-membered heterocycle, in which the heterocyclic ring is connected with the ring benzotriazole through N-atom or YR8where Y represents O, NR9or S(O)nand R8is (-R10)mCORAny and R11denotes alkoxy, alkyl, alkyloxy.

R4represents hydrogen and alkyl.

R5represents a hydrogen or halogen.

R6is haloalkyl, halogen and SOyR12.

More preferably haloalkyl.

R7represents hydrogen.

R1represents-CH2-, -CH2CH2- or-CH(CH3)-.

X represents N or CR13in which R13denotes hydrogen, halogen or haloalkyl. More preferably N or C-chlor.

The preferred embodiment includes: R1is hydrogen, alkyl, cyano, halogen, haloalkyl or alkoxy;

R2is hydrogen, halogen, alkyl, nitro, alkoxy, haloalkyl, Coolkill or or8; R3is hydrogen, alkyl, halogen, hydroxy or YR8; R4is hydrogen; R5is halogen or hydrogen; R6- haloalkyl or SOyR12;

R7is hydrogen and X Is N or C-chlor.

Another preferred embodiment of the invention includes: R1is hydrogen, alkyl or halogen; R2is hydrogen or halogen; R3- 5-, 6 - or 7-membered saturated or unsaturated optionally substituted heterocycle, in which the members of the cycle and choose the mA; R4is hydrogen; R5is hydrogen or halogen, R6- haloalkyl; R7is hydrogen and X Is N or C-halogen.

Another preferred embodiment includes: R1is hydrogen, halogen, alkyl or haloalkyl; R2is hydrogen, alkyl or halogen; R3- YR8; R4is hydrogen, R5is hydrogen or halogen; R6- haloalkyl; R7is hydrogen; X Is N, C-halogen or C is hydrogen.

Further, the preferred embodiment includes:

R1is hydrogen; R2is chlorine or fluorine; R3- YR8in which Y represents O, NR9or S(O)n; R4is hydrogen; R5- chlorine; R6- haloalkyl; R7is hydrogen and X is N.

The above embodiments illustrate the invention and are not intended to limit the invention in General.

Have in mind that the term "alkyl" and all groups containing alkyl fragments include linear, branched and cyclic groups. Examples include: methyl, ethyl, n-propyl, isopropyl, cyclopropyl, n-butyl and t-butyl. Each alkyl group can contain from one to six carbon atoms. For example, (C1-C6) alkoxy(C1-C6)alkoxy; amino-(C1-C6)alkylsulphonyl. Similarly, the terms Ala.

In the above definitions, the term "halogen" includes fluorine, chlorine, bromine and iodine group. The term "haloalkyl" refers to an alkyl group substituted by one or more halogen atoms.

Under the heterocyclic mean cycle saturated or unsaturated, containing at least one nitrogen atom, oxygen or sulfur. Examples include azole, furan, imidazole, isopropyl, morpholine, oxazole, piperazine, piperidine, pyridine, pyrimidine, thiazole, thiophene, and triazole.

The invention also includes stereo and optical isomers of the compounds described in the claims, and mixtures of these compounds in all relationships.

Used herein, the terms "herbicide" and "herbicide" refers to an inhibitory regulation and modification of the growth of undesirable plants. Inhibitory control and modification include all deviations from natural development, such as, for example, the complete destruction, growth retardation, leaf removal, desiccation, regulation, stunting, tillering, stimulation, burning leaves, and the delay in development and the like. Used herein, the term "herbicide effective amount" means any amount that allows such regulation and plants. It is implied that the term "plant" includes sprouted seeds, sprouted seedlings and rooted vegetation, including roots and aboveground parts.

Used herein, the term "selskohozjajstvenno-acceptable salt" means a salt or salts, which are easily ionized in the aquatic environment, and includes salts of sodium, potassium, calcium, ammonium, magnesium and acid salts such as hydrochloride, sulfate and nitrate.

Found that the compounds of the present invention are active herbicides, having useful properties as herbicides used prior to germination (before germination) and after germination (after germination), and is useful against a wide range of plant species, including deciduous and herbaceous species. Some compounds have a selective suppression of plant species in some crops, such as rice, corn and soybeans.

Further, this invention relates also to a method for control of unwanted vegetation, comprising applying to areas that require regulation of such vegetation, either before or after emergence of such vegetation herbicide effective amount of a compound as described herein, together with inert RA is and the present invention can be obtained by the following common methods, described below.

Here (see the General scheme of the interactions at the end of the description) ortho-nitroaniline obtained by nitration of the corresponding anilide, easy allroute appropriate helgaleena in the presence of a base such as sodium hydride or potassium carbonate in an inert solvent, such as N,N-dimethylformamide (DMF) or dimethylsulfoxide, at temperatures between 0oC and 100oC. Tsepliaeva the halide group can be represented by a fluorine, chlorine or bromine. Antonito intermediate compound is then easily restore the iron in a mixture of alcohol/water, or chloride of tin or other reducing metal salts on the same methodology. The obtained 1,2-phenylendiamine easily cyclists to the final product with a source of nitrite or inorganic nitrite salts of metals in the presence of acid, or organic nitrites such as isoamylase, in the presence or absence of an acid catalyst.

These examples are provided to illustrate and not limit the scope of the invention and the attached items.

Example 1

Getting 6-hydroxy-1-[2'-(3'-chloro-5'-trifluoromethyl) pyridyl]1[H]-benzotriazole

(compound 15)

a) M-residentura environment 30 minutes. The mixture cool and add 50 ml (0.8 M) of concentrated nitric acid. The mixture is diluted with water, obtaining 35 g of 2-nitro-5-methoxy acetanilide.

(b) the Product of stage (a) is mixed with 50 ml of water, 100 ml of concentrated hydrochloric acid and heated to the boiling temperature under reflux. The mixture was poured into water, getting 5.5 g of 2-nitro-5-methoxy aniline.

(c) the Product of stage (b) (5.5 g, 33 mmol) are mixed in a nitrogen atmosphere with 2,3-dichloro-5-trifluoromethyl (7,1 g , 33 mmol) and 75 ml of N,N-dimethylformamide (DMF). Slowly add sodium hydride (1.7 g, 71 mmol) and the mixture is left to mix for a 2.0 hours at ambient temperature. The mixture is slowly poured into diluted hydrochloric acid on the ice, getting 10.0 g of solid 2-nitro-5-methoxy-N-[2'-(3'-chloro-5'-trifluoromethyl)pyridyl]aniline.

(d) a Mixture of 31.6 ml of ethanol, iron (4.4 g, 70 mmol), restored electrolytic, 26,3 ml of water and 0.34 ml of concentrated hydrochloric acid is heated to the boiling temperature under reflux. To the above mixture add the product of stage (c) (9,1 g of 26.3 mmol) maintaining the temperature of reflexa. The resulting mixture was boiled for an additional 30 minutes, then cooled down to 60 - 65oC, neutralized with 50% sodium hydroxide (0.34 in the tea and 7.7 g of 4-methoxy-2-[2'-(3'-chloro-5'-trifluoromethyl) pyridyl]1,2-phenylenediamine.

(e) the Product of stage (d) (3,18 g, 10 mmol) is mixed with 30 ml of dichloromethane and cooled to -78oC. and Then added dropwise to tribromide boron (3.8 ml, 40 mmol) dissolved in 6 ml dichloromethane. The reaction mixture is allowed to warm to ambient temperature, then cooled to -30oC adding 60 ml of methanol. The mixture is dispersed in a vacuum. The residue is treated with an aqueous sodium bicarbonate and extracted with dichloromethane, dried over magnesium sulfate (MgSO4and dispersed in a vacuum. The remainder of dichlormethane solutions extracted with 200 ml of methanol, separating light fractions in vacuo and suspended in water, to which add sodium bicarbonate until the aqueous solution is neutral, obtain 3.0 g of 4-hydroxy-2-[2'-(3'-chloro-5'-trifluoromethyl)pyridyl]1,2-phenylenediamine.

(f) the Product of stage (e) (2.0 g, 59 mmol) is mixed with 20 ml DMF, isoamylamine (0,97 ml, 7,26 mmol), a few drops of methansulfonate and stirred at ambient temperature overnight. To complete the reaction to impose an additional 0.1 ml isoamyl nitrite and a drop of methansulfonate. The mixture is dispersed in vacuum, obtaining a solid product. Then the solid product is washed with water, filtered and dried, obtaining the claimed connection 6-GI-1-[2'-(3-chloro-5'-trifluoromethyl)pyridyl]1[H]benzotriazole

(compound 16)

(a) 4-methoxy-2-[2'(3'-chloro-5'-trifluoromethyl) pyridyl]-1,2-phenylene diamine (8.7 g, a 27.4 mmol) is mixed with 82 ml of dichloromethane, cooled to -70oC isopropanolate bath with dry ice and added dropwise to 10.4 ml (110 mmol) of boron tribromide in 20 ml of dichloromethane. The mixture is heated to ambient temperature, and then cooled to -30oC and added dropwise 160 ml of methanol. The mixture is dispersed in vacuo, neutralized with sodium bicarbonate, extracted with dichloromethane and filtered. The solid product is extracted with methanol and distilled volatile fraction, obtaining 4.0 g of 4-hydroxy-2-[2'-(3'-chloro-5'-trifluoromethyl)pyridyl]-1,2-phenylenediamine.

(b) the Product of stage (a) (4.0 g, 13,2 mmol) is mixed with 40 ml DMF) 1,95 g (14.5 mmol) of isoamylamine and 3 drops of methansulfonate (catalyst) and stirred over night at ambient temperature. The mixture is dispersed in a vacuum, then extracted with dichloromethane and treated with water. The organic phase is dried over magnesium sulfate and distilled in vacuum, obtaining 3.1 g of 6-hydroxy-2-[2'-(3'-chloro-5'-trifluoromethyl)pyridyl-1-H-benzotriazole.

(c) the Product of stage (b) (1.9 g, 6 mmol) is mixed with 20 ml of acetonitrile, 0,83 g (6 mmol) of powdered potassium carbonate and bromoacetonitrile is the Aquum. The obtained solid products are extracted with dichloromethane, treated with water, dried over magnesium sulfate, filtered and the solution in dichloromethane is distilled in vacuum.

Then solid foods clean extragere a mixture of hot hexane/25% benzene and the solid product is filtered, obtaining 0.9 g of the named compound, 6-(cyano)methoxy-1-[2'-(3'-chloro-5'-trifluoromethyl)pyridyl] 1[H]-benzotriazole. Solution in a mixture of hexane/benzene is distilled in vacuum, Astrovirus diethyl ether and the ether is distilled off in vacuum, obtaining additional 0.4 g of product after trituration.

Example 3

Getting 5-methyl-6-methoxy-1-[2'-(3'-chloro-5'-trifluoromethyl)pyridyl]1[H] -benzotriazole

(compound 21)

(a) 4-methyl-3-methoxy aniline (7.6 g, 50 mmol), 6 ml of acetic acid and 6 ml of acetic anhydride are mixed, causing an exothermic reaction. The mixture is cooled to ambient temperature. Add cooled in an ice bath, concentrated nitric acid (15 ml). The mixture is crystallized and abundantly watered, receiving of 7.8 g of 2-nitro-4-methyl-5-methoxy acetanilide in the form of a solid substance.

(b) the Product of stage (a) (7,8 g, to 34.7 mmol) is mixed with 100 ml of concentrated hydrochloric acid and heated at boiling temperature with-4-methyl-5-methoxy aniline.

(c) the Product of stage (b) (5,2 g, 28 mmol) are mixed in a nitrogen atmosphere with 75 ml of DMF and 6.5 g (0.30 mmol) of 2,3-dichloro-5-trifluoromethyl pyridine. Sodium hydride (1.5 g, 62.5 mmol) is added slowly to the mixture in portions. Mixture is allowed to mix for 2.5 hours at ambient temperature and then slowly poured into a mixture of dilute hydrochloric acid/ice, then collect 9.5 g of 2-nitro-4-methyl-5-methoxy-N-[2'-(3'-chloro-5'-trifluoromethyl)pyridyl] aniline in the form of a solid product.

(d) Iron (4.3 g, 77,1 mmol), restored electrolytic, 80 ml of ethanol, and 67.2 ml of water and of 0.333 ml of concentrated hydrochloric acid are mixed and heated to the boiling temperature under reflux. To this mixture is added in portions at a rate that permits to maintain boiling, the product of stage (c) (9.3 g, of 25.7 mmol). The mixture is boiled for 45 minutes, cooled to 60 - 65oC, neutralize of 0.333 g of 50% sodium hydroxide, filtered through diatomaceous earth, distilled volatile compounds in vacuo, suspended in water and filtered, obtaining of 7.1 g of 4-methoxy-5-methyl-2-[2'-(3'-chloro-5'-trifluoromethyl)pyridyl]-1,2-phenylenediamine in the form of a solid substance.

(e) the Product of stage (d) (2.0 g, 6.0 mmol) is mixed with 20 ml DMF, to 0.89 ml (6.6 mmol) isoamyl nitrite and 3 drops (catalyst) methanesulfonamide solid product is treated with water, filtered and dried, obtaining 1.7 g of 5-methyl-6-methoxy-1-[2'-(3'-chloro-5'-trifluoromethyl)pyridyl]-1[H]-benzotriazole in the form of a solid substance.

Example 4

Getting 5-fluoro-5-[2'-(3'-chloro-5'-trifluoromethyl)pyridyl]-1[H]-benzotriazole

(compound 25)

(a) 2-nitro-4-ftoranila (6 g, a 38.5 mmol) are mixed in a nitrogen atmosphere with 75 ml of DMF and 8.3 g (38.4 mmol) of 2,3-dichloro-5-trifluoromethyl pyridine. To the mixture slowly and portions add sodium hydride 1,9 g a (80.0 mmol). The mixture is stirred overnight at ambient temperature and then slowly poured into a mixture of dilute hydrochloric acid/ice, then collect 11.1 g of 2-nitro-4-fluoro-N-[2'-(3'-chloro-5'-trifluoromethyl)pyridyl] aniline in the form of a solid substance.

(b) Iron (reduced electrolytic) (5.5 g, to 98.4 mmol), 100 ml of ethanol, 85 ml of water and 0.42 ml (catalyst) of concentrated hydrochloric acid are mixed and heated to the boiling point, to this mixture add portions of the product of stage (a) (11 g, is 32.8 mmol) with speed, providing boiling throughout this time. The mixture is boiled for 40 minutes, cooled to 60-65oC, then neutralized 0,42 g 50% sodium hydroxide, filtered through diatomaceous earth, is distilled in vacuo, suspended in water and filtered, poluchat stage (b) (2 g, 6,55 mmol) is mixed with 20 ml DMF, to 0.97 ml (7.2 mmol) isoamyl nitrite and 3 drops (catalyst) methanesulfonate and stirred at ambient temperature over night.

The mixture is distilled in vacuum, obtaining a solid product, which is treated with water, filtered and dried, obtaining 2.0 g of 5-fluoro-[2'-(3'-chloro-5'-trifluoromethyl)pyridyl]1[H]-benzotriazole in the form of a solid substance.

Example 5

Getting 6-methylthio-1-[2'-(3'-chloro-5'-trifluoromethyl)1[H]-benzotriazole

(compound 29)

(a) 2-nitro-5-Chloroaniline (12.9 g, 75 mmol) is mixed with 125 ml of DMF and 16.2 g (75,0 mmol) of 2,3-dichloro-5-trifluoromethyl pyridine in a nitrogen atmosphere. Sodium hydride (3.0 g, 130 mmol) is added in portions, and slowly to provide stirring at ambient temperature. The next morning, add sodium hydride (0.8 g, 35 mmol) and the mixture is stirred for 1.5 hours at ambient temperature and then slowly poured into a mixture of dilute hydrochloric acid/ice, resulting in a gain of 23.9 g of 2-nitro-5-chloro-N-[2'-(3'-chloro-5-trifluoromethyl)pyridyl]analena in the form of a solid product.

(b) the Product of stage (a) (3.5 g, 10 mmol) is mixed with 30 ml DMF and 0.8 g (11 mmol) of sodium methanoate and heated to 70oC for one minute, then mix the 2'-(3'-chloro-5-trifluoromethyl)pyridyl]aniline in the form of a solid substance.

(c) Iron (electrolytic restored) (1,62 g, 29 mmol), 50 ml of ethanol, to 42.5 ml of water and 0.12 ml of concentrated hydrochloric acid are mixed and heated to the boiling point. To this mixture is added in portions 3.5 g (9,63 mmol) of 4-methylthio-2-nitro-N-[2'-(3'-chloro-5-trifluoromethyl)pyridyl]aniline at a speed that allows you to maintain boiling. The mixture is heated at boiling point for one hour, cooled down to 60 - 65oC, after which it is neutralized 0.12 g of 50% sodium hydroxide, filtered through diatomaceous earth, is distilled in vacuo, suspended in water and filtered, obtaining 3.0 g of 4-methylthio-2-[2'-(3'-chloro-5-tripometer)pyridyl]-1,2-phenylenediamine in the form of a solid substance.

(d) the Product of stage (c) (3.0 g, 9 mmol) is mixed with 30 ml of dimethylformamide, to 1.33 ml (9.9 mmol) of isoamylamine and 4 drops of methansulfonate and stirred for one hour at ambient temperature. The mixture is distilled in vacuo, then extracted with diethyl ether, treated with water. Organic products are dried over magnesium sulfate and distilled in vacuum, obtaining 2.5 g of 6-methyl-thio-1-[2'-(3'-chloro-5'-trifluoromethyl)pyridyl] 1[H] -benzotriazole in the form of a solid substance.

Example 6

Getting 6-dimethylamino-1-[2'-(3'-chloro-5'- trifluoromethyl)pyridyl]1[H]-benzo is more with 30 ml DMF, 5 g (44 mmol) of dimethylaniline (40% in water), heated at boiling temperature for 4 hours, cooled to ambient temperature, then poured into water, and then collect and 3.3 g of 5-methylamino-2-nitro-N-[2'-(3'-chloro-5'-trifluoromethyl)pyridyl] aniline in the form of a solid substance.

(b) Iron (electrolytic restored) (1,62 g, 29 mmol), 50 ml of ethanol, to 42.5 ml of water and 0.12 ml of concentrated hydrochloric acid are mixed and heated to the boiling point. The product of stage (a) (3,3 g, 9.2 mmol) is added by portions at speeds that support the boil. The mixture is boiled for 0.5 hour, cooled to 60-65oC, neutralize 0.12 g of 50% sodium hydroxide, filtered through diatomaceous earth, is distilled in vacuo, suspended in water and filtered, obtaining 2.7 g of 5-dimethylamino-2-[2'-(3'-chloro-5'-trifluoromethyl)pyridyl]-1,2-phenylenediamine in the form of a solid substance.

(c) the Product of stage (b) (2.7 g, 8.2 mmol) is mixed with 20 ml DMF, to 1.33 ml (9.9 mmol) of isoamylamine and 3 drops (catalyst) methansulfonate and stirred at ambient temperature for one hour. The mixture is distilled in vacuo, extracted with diethyl ether, treated with water, the organic portion is dried over magnesium sulfate, and suspended in vacuum, obtaining 2.5 g of 6-dimethylamino-is giving 5-carboxymethoxy-6-methoxy-1-[2'-(3'-chloro-5'-trifluoromethyl)pyridyl][1[H]- benzotriazole

(compound 44)

(a) 4-Aminosalicylic acid (30,6 g, 200 mmol), 300 ml of acetone and 24 g of potassium hydroxide (KOH) are mixed and allowed to mix at ambient temperature overnight. To a mixture of quick drops add dimethylsulfate (57 g, 450 mmol) and stirred for one hour at ambient temperature. After gas-liquid chromatography shows that the reaction is complete, add an additional 5 g of KOH and the mixture is stirred for another hour, distilled under vacuum, mixed with 150 ml of water, extracted a large number of dichloromethane. The solution is dried over magnesium sulfate, and then distilled in vacuum, obtaining 50 g crude product, which was triturated with diethyl ether, giving to 15.8 g of 4-carboxymethoxy-5-methoxyaniline in the form of a solid product.

(b) the Product of stage (a) (15,8 g, 87 mmol), 15 ml of acetic anhydride (100 mmol) and 15 ml of acetic acid are mixed, which is accompanied by evolution of heat, stirred at ambient temperature and distilled in vacuum. The residue is added to a solution of 20 ml (320 mmol) of concentrated nitric acid, cooled in an ice bath, stirred for several hours and then poured into water. The obtained solid foods rinsed with water, carrying omeganaut. To the resulting precipitate add methanol (100 ml). The mixture is boiled for 2 hours and distilled in vacuum. To the flask was added sodium hydroxide (50 ml, 1 M), followed by stirring, and then extracted with a large number of dichloromethane, the organic portion is dried over magnesium sulfate and distilled in vacuum, obtaining 2.2 g of pure product.

(c) the Product of stage (b) is mixed with 25 ml of DMF and 2.1 g (10.0 mmol) of 2,3-dichloro-5-trifluoromethyl pyridine in a nitrogen atmosphere. Slowly portions add sodium hydride (5 g, 21,0 mmol) and the mixture is left to mix overnight at ambient temperature. The mixture is slowly poured into ice water, then collect 3.5 g of 4-carbomethoxy-5-carboxy-2-nitro-N-[2'-(3'-chloro-5'-trifluoromethyl)pyridyl] aniline in the form of a solid substance.

(d) Iron (reduced electrolytic) (4 g, 70 mmol), 80 ml of ethanol, 50 ml of water and 0.2 ml of catalyst are mixed and heated to the boiling point. To this mixture add portions 3 g (7.5 mmol) of 4-carbomethoxy-5-carboxy-2-nitro-N-[2'-(3'-chloro-5-trifluoromethyl) pyridyl] aniline at a speed that allows you to maintain the boiling point. The mixture is heated at boiling point for 6 hours and cooled to 60-65oC. the Mixture is neutralized with 0.2 g of 50% N2OH, distilled, is, obtaining 0.8 g of 4-carboxymethyl-5-carboxy-2-[2'-(3'-chloro-5'-trifluoromethyl)pyridyl-1,2-phenylendiamine balance.

(e) All products stage (d) is mixed with 10 ml of DMF, a small amount of isoamylamine and a few drops of methansulfonate and left to mix overnight at ambient temperature. The mixture is distilled, extracted with diethyl ether, treated with water and then with 5% potassium carbonate. The organic phase is dried over magnesium sulfate and distilled, obtaining a solid substance, which is treated with a mixture of diethyl ether and pentane, receiving 0.15 g 5-carbomethoxy-6-methoxy-1-[2'-(3'-chloro-5'-trifluoromethyl)pyridyl]1[H] -benzotriazole in the form of a solid substance.

Example 8

Getting 5-chloro-6-(pentamethylene)amino-1-[2'-(3'-chloro-5'-trifluoromethyl)pyridyl]1[H]- benzotriazole

(compound 48)

(a) 4,5-dichloro-2-nitroaniline (15 g, from 72.5 mmol), 315 ml of DMF and 15,66 g (72,5 mmol) of 2,3-dichloro-5-trifluoromethyl pyridine are mixed in a nitrogen atmosphere. Portions and slowly add sodium hydride 3.8 g (159 mmol). The mixture is left to mix overnight at ambient temperature and then slowly poured into a mixture of dilute hydrochloric acid/ice, resulting in the gathering of 26.1 g of 2-nitro-4,5-dichloro-N-2'-(3'-PI the (excess) of pyridine gently mixed, heat just to boiling point. To the mixture of diluted hydrochloric acid and the product is filtered, obtaining 3.2 g of 2-nitro-4-chloro-5-(pentamethylene)amino-N-[2'(3'-chloro-5'-trifluoromethyl)pyridyl] aniline in the form of a solid product.

(c) Iron (reduced electrolytic) (1.3 g, of 22.8 mmol), 40 ml of ethanol, 35 ml of water and 0.1 ml (catalyst) of concentrated hydrochloric acid are mixed and brought to a boil. The product of stage (b) is added in portions to this mixture (3.2 g, 7.4 mmol) at a rate that permits to maintain the boil. The mixture is boiled for 1.5 hours, cooled down to 60 - 65oC, then neutralized with 0.1 g of 50% sodium hydroxide, filtered through diatomaceous earth, is distilled in vacuo, suspended in water and filtered, obtaining 2.5 g of 4-chloro-5-(pentamethylene)amino-1-[2'-(3'-chloro-5'-trifluoromethyl)pyridyl] -1,2-phenylenediamine in the form of a solid substance.

(d) Mixing the product of stage (c) (2.5 g, 6.2 mmol), 25 ml of DMF, to 0.92 ml (6.8 mmol) of isoamylamine a few drops (catalyst) methansulfonate and allowed to mix at ambient temperature over night. The mixture is distilled with the purpose of drying in vacuum, extracted with diethyl ether, treated with water and separated. The organic phase is dried over sulfate is Ola in the form of a solid substance.

Example 9

Getting 5-chloro-6-(N-methyl-N-carboxymethyl)amino-1-[2'-(3'-chloro-5'-trifluoromethyl)pyridyl] 1[H]-benzotriazole

(compound 49)

(a) 2-Nitro-4,5-dichloro-N-[2'-(3'-chloro-5'-trifluoromethyl)pyridyl] aniline (3.0 g, 7,76 mmol), 20 ml of 1-methyl-2-pyrrolidinone, 0.8 g (9.0 mmol) of sarcosine and 2 g (0.019 mmol) of triethylamine are mixed and heated at 85-100oC 2.5 days. The mixture is cooled to ambient temperature. Add dilute caustic and the mixture is treated with diethyl ether and separated phases. The caustic solution is acidified, gaining 1.4 g 2-nitro-4-chloro-(N'-methyl-N'-carboxymethyl)amino-N-[2"-(3"-chloro-5 ' - trifluoromethyl) pyridyl] aniline in the form of a solid substance.

(b) Iron (reduced electrolytic) (2.3 g 40 mmol), 40 ml of ethanol, 10 ml of water and 0.2 ml of concentrated hydrochloric acid are mixed and heated to the boiling point. The product of stage (a) (2.7 g, 6 mmol) is added in portions at a rate that permits to maintain the boil. The mixture is boiled for 3 hours, cooled down to 60 - 65oC, neutralized with 0.2 ml of 50% NaOH and filtered through diatomaceous earth. After that, the mixture is distilled in vacuo, extracted with a large number of dichloromethane, the organic phase is washed with diluted hydrochloric acid and separated. The organic part is rmutil) pyridyl]-1,2-phenylendiamine product.

(c) the Product of stage (b) (1.2 g, 3.0 mmol) is mixed with 10 ml of DMF, 0.4 g (3.4 mmol) of isoamylamine and one drop (catalyst) methansulfonate and allowed to mix at room temperature over night. The mixture is distilled, extracted with diethyl ether and treated with water. The organic phase is dried over magnesium sulfate and distilled, obtaining 1.2 g of pure product.

Pure product was dissolved in diethyl ether and extracted with dilute sodium hydroxide. The caustic layer is acidified and extracted with dichloromethane, dried over magnesium sulfate and distilled in vacuum, obtaining 0.5 g of 5-chloro-6-(N-methyl-N-carboxymethyl)amino-1-[2'-(3'-chloro-5'-trifluoromethyl)pyridyl]1[H]-benzotriazole in the form of a solid product.

Example 10

5-fluoro-6-(1'-carboxymethoxy)ethoxy-1-[2"-(3"-chloro-5-trifluoromethyl) pyridyl] 1[H]-benzotriazole

(compound 51)

(a) 2.5-diferena (20 g, to 15.4 mmol) was dissolved in 50 ml of methylene chloride under stirring. 11 ml (176,0 mmol) concentrated nitric acid is added dropwise and the mixture is cooled in an ice bath. The mixture is divided into phases. The organic phase is dried over magnesium sulfate and distilled, receiving 27 g of product which is triturated with 10% benzene in hexane, giving of 14.4 g of 2,5-is,3 g of potassium carbonate and 3 g of allylbromide mix, heated at boiling temperature for one hour and distilled. The mixture is extracted with dichloromethane, treated with water and separated. The organic phase is dried over magnesium sulfate and distilled, obtaining of 1.9 g of 4-allyloxy-2,5-deformirovannoe.

(c) the Product of stage (b) (1,9 g, 9.3 mmol), 20 ml of DMF and 1.8 g (9.0 mmol) of 2-amino-3-chloro-5-trifluoromethyl pyridine are mixed in a nitrogen atmosphere. To the mixture slowly and portions add sodium hydride (0.5 g, 21,0 mmol). The mixture is left to mix overnight at ambient temperature. Add water to the mixture, giving 2.5 g of the solid product is treated with a solution of 50: 50 diethyl ether:pentane, receiving 4-fluoro-5-allyloxy-2-nitro-1[2'-(3'-chloro-5'-trifluoromethyl)pyridyl] -aniline in the form of a solid substance.

(d) iron Powder (reduced electrolytic) (2 g, 33.0 mmol), 25 ml of ethanol, 7 ml of water and 0.2 ml (catalyst) of concentrated hydrochloric acid are mixed and heated to the boiling point. The product of stage (c) (1.4 g, 3.6 mmol) is added in portions to the above mixture at a rate that permits to maintain the boil. After complete addition, the mixture is boiled for 3 hours, then cooled down to 60 - 65oC, then neutralized with 0.2 g of 50% sodium hydroxide. Mixture and divide. The organic layer is dried over magnesium sulfate and distilled in vacuum, obtaining 1.3 g of 4-fluoro-5-allyloxy-1-[2'-(3'-chloro-5'-trifluoromethyl) pyridyl]-1,2-phenylendiamine product.

(e) the Product of stage (d) (1.3 g, 3.6 mmol), 10 ml of DMF, 0.5 g (4.0 mmol) of isoamylamine and 2 drop (catalyst) methansulfonate mixed and stirred over night at ambient temperature. The mixture is distilled, extracted with diethyl ether, treated with water and separated. The organic layer is dried over magnesium sulfate and distilled, obtaining 1 g of 5-fluoro-6-allyloxy-1-[2'-(3'-chloro-5'-trifluoromethyl)pyridyl]1[H]-benzotriazole.

(f) the Product of stage (e) (1 g, 2.7 mmol), 10 ml of tetrahydrofuran, and 0.3 g (3.0 mmol) of triethylamine and a catalytic amount of palladium acetate are mixed and heated to boiling. Formic acid (0.2 g, 4.0 mmol) is added to the mixture, which is heated at the boiling temperature for 1.5 hours. The mixture is distilled, extracted with diethyl ether, treated with water and separated. The organic layer is dried over magnesium sulfate and distilled, gaining 0.7 g of 5-fluoro-6-hydroxy-1-[2'-(3'-chloro-5'-trifluoromethyl)pyridyl]1[H]-benzotriazole.

(g) the Product of stage (f) (0.7 g, 2.1 mmol), 10 ml of acetonitrile, 0.4 g (2.4 mmol) of methyl 2-bromopropionate and 0.4 g (2.8 mm the Ute, extracted with dichloromethane, treated with water and separated. The organic layer is dried over magnesium sulfate and distilled, obtaining 0.8 g of 5-fluoro-6-(1'-carbomethoxy)ethoxy-1-[2"-(3"-chloro-5"-trifluoromethyl)predil] 1 [H]-benzotriazole in the form of a semi-solid product.

The structure of the final product for each stage of each sample set using infrared spectroscopy, mass spectroscopy and nuclear magnetic resonance.

Table I gives typical compounds of this invention obtained by the above method.

Test for herbicide selection

Connections shown earlier in the table, tested on herbicide activity in different ways and at different rates of application. The results of some of these tests are given below. As is known to every expert in the relevant field of technology, the results obtained in the test for herbicide selection, dependent on a number of factors, which are difficult to control. Examples of such factors are environmental conditions, such as amount of sunlight and rainfall, soil type, soil pH, temperature, and humidity. Other factors that can affect the results of the test is to vary the transition from culture to culture and within varieties of culture.

Herbicide screening test prior to germination (pre-emergence)

On the day prior to the test, seeds of several different kinds of weed grasses are sown in the soil of clay and sand with humus to a depth of 0.5 inch (1.3 cm) of individual rows using one species per row across the width of the flat surface (box). The soil fertilized with ograblenie 17-17-17 (K-P2O5-K2O) on the basis of weight and pasteurized. Sown seeds: spickle green (Setaria viridis), oats empty (Avena fatua), barnyard millet (Echinochloa crusgalli), wild mustard (Sinapsis azvensis), canetic Theophrastus (Abutilon theophrastic), annual morning glory (Ipomoea haderaces) and yellow nut sedge (Cyperus esculentus).

Depending on the size of the plants planting density ranges from 3 to 25 plants per row.

Solutions of test compounds are prepared by weighing 74,7 or 18.8 milligram (mg) of the test compound into a 60 ml wide-mouthed flask and then dissolving the compound in a 7.0 ml of acetone containing 1% tween-20(polyoxyethylene sorbitan monolaurate-emulsifier), and then adding 7 ml of deionized water to obtain a final volume of 14 ml Contents tween-200.5% V/V of the final spray volume. If necessary to dissolve the soy is sprayed within the linear table for spraying. Surface spray aerosol solution, calibrated to submit 748 l/ha Rate of application is 4.0 or 1.0 kg/ha

The boxes are placed in a greenhouse at 21-29oC and sprayed with water daily. The degree of control of weed grasses assessed visually and recorded on 17-21 days after treatment as a percentage of control compared to the growth of the same species of the same age in untreated control boxes.

Herbicide evaluation after germination (post-harvest)

The soil is prepared and seeded with the same species and in the same way as described for the test to germinate. The boxes are placed in a greenhouse at 21 - 29oC and water spraying. The seeds of species of weeds are sown for 10-12 days before processing. Usually herbs are sprayed with erusalem 2-3 deciduous stage and broadleaf - 1-2 deciduous stage. When spraying the height of yellow nut sedge reaches 5-7 see the Water treated plants restricted to water only the soil surface, but not foliage sprouted plants. The degree of control of weed grasses assessed visually and recorded on 17 - 21 days after treatment, as a percent of control compared to the growth of the same species of the same age in the raw whom all factors including the suppression of germination, the destruction of plant tissue after emergence, stunting, malformation, chlorosis, and other types of damage. Rating regulation varies from 0 to 100%, where 0 means no impact on development, equal to the untreated control, and 100 indicates complete destruction: the dash indicates that the test was not conducted at this level spraying.

The results are shown in table II, Express the average regulation three grasses (GR)(oats empty wild, chicken millet and spickle green), three of deciduous Saanich plants (BL) (annual morning glory, wild mustard and canetic of Efrata) and yellow nut sedge (NS) at the rate of deposition of 4.0 kg/ha of test compound. Table III shows the average control value of the same species of weeds that are obtained from the normal application of 1.0 kg/ha of the tested compounds.

In practice, a pure compound can be used as a herbicide. However, usually, the connection before use, pre-mixed with one or more inert carriers or diluents suitable for herbicide use.

Compositions or formulations comprising compounds as opisanie to the formation of emulsion concentrates, fluid form and paste. Such compositions may contain, in addition to the active compound or compounds, different carriers and solvents; surfactants (wetting means dispersing means and/or emulsifying means); solvents (water or organic solvents, such as aromatic solvents or chlorinated aliphatic solvents); adhesives; thickening agents; binding agents; antifoaming agents and other substances, as mentioned above. Solid carriers or diluents, which are included in such compositions or formulations may include, for example, basic natural materials, such as kaolin, alumina, calcium carbonate, silica, diatomaceous earth, clay and so on; the main synthetic minerals, such as various silicates and aluminosilicates, and the basic vegetable products, such as Hina, corn flour, sawdust, powdered cellulose, and the like.

For the industrial production of solid compositions, the active substances are mixed with solid carriers or diluents, such as those mentioned above, and the mixture is ground to the appropriate dimensions. Granules can be obtained by dissolving the active compound in an organic ( as silicon dioxide. In order to facilitate binding of the compounds with solid particles can also be used adhesives. Tablets or granules can be manufactured by extrusion with appropriate carriers and binders.

Wettable powders, flowable formulations and paste obtained by mixing and grinding the active compound with one or more dispersing means and/or solid carriers or diluents. May also include moisturizers and/or dispersing means, such as lignins, methyl cellulose, derivatives naphthalenesulfonate, sulfates of fatty alcohols and different types of salts of alkaline and alkaline-earth metals and fatty acids.

Forming emulsion concentrates are usually obtained by dissolving the active compound in an organic solvent, for example butanol, cyclohexanol, xylenes or high-boiling aromatic hydrocarbons. For producing suspensions or emulsions in water usually add moisturizers.

The composition can also be used in the form of microcapsules. Microcapsules consist of a fully enclosed or contained in the capsule drops or granules containing the active compound, mounted inside an inert porous membrane is ansto with controlled velocity.

Useful for encapsulation materials include natural and synthetic rubber or latex materials from cellulose, styrene-butadiene copolymers, polyacrylonitrile, polyacrylates, polyesters, polyamides, polyurethanes and starch xanthates.

You can use highly concentrated liquid compositions containing up to 95% by weight of active compound or even pure active compounds for those compounds which are liquid at application connection in the form of finely sprayed liquid, by using a variety of spray devices, for example using methods of crop dusting aircraft. However, for other purposes various types of compositions that can be used for these compounds will include different numbers of compounds in accordance with the type of composition and the intended use.

Typically, the compositions may contain from 0.1 to 95% active compound, more preferably from 0.5 to 90%. Some typical compositions contain the following number of active connections: wettable powders, flowable formulations and paste - 20 - 90% active compound; oil suspensions, emulsions, solutions, emulsifiable the mouth) and powders - 1 - 25% active compound; granules and tablets - 1 - 20% of the active compounds.

The rate of application of active compound on areas that require regulation, depends on the activity of the compounds and/or compositions and regulated nature of seeds and plants and varies from about 0.01 to 50 pounds per acre (approximately 0.06% to 56 kg/ha).

Compositions containing one or more of the described active compounds, herbicide effective amount can be applied to plants or areas that require regulation, any normal way. So, powders and a variety of liquid compositions containing the active compound can be applied by using a powerful vacuum cleaners, mechanical and hand sprayers and spray device or by spraying from planes as mists and aerosols. When applied the latter method, they can be effective in very low doses. To modify or control growth of germinating seeds or emerging seedlings liquid compositions can be applied to the ground by conventional means and may be introduced into the soil to a depth of 1/2 inch (1.25 cm) from the soil surface. The composition need not be mixed with soil particles, and can be applied proctologist by mixing with irrigation water, applied to fields that require processing. This method of application promotes the penetration of compounds into the soil, because it absorbs water.

Examples of typical compositions are given in the end of the description.

Compositions of the invention may include, in addition to one or more compounds of the invention, one or more compounds that are not included in the invention, but showing biological activity. Connections that are not included in the present invention, there may be other pesticide means, such as herbicides, fungicides, insecticides, acaricides, nematicides, bactericides and plant growth regulators. Such compositions may also contain solid disinfectants or means for fumigation and, in addition, may include fertilizers, thus making it possible to obtain multi-purpose compositions containing one or more compounds described herein, as well as, optionally, other pesticides, and fertilizers, all designed and made for use on the same plots. Thus, in the following embodiment of the invention provides a herbicide composition comprising a mixture of at least one herbicide compound of formula (I) defined corresponding to the formula (I). It is usually a herbicide, providing additional impact in this application.

Examples of useful additional herbicides include:

A. benzo-2,1,3-thiadiazin-4-one-2,2-dioxides such as bentazon;

B. hormone herbicides, in particular phenoxy alcamovia acid, such as MSRA (2-methyl-4-chlorophenoxyacetate acid), MSRA-thioethyl, dichlorprop, 2,4,5-T(2,4,5-trichlorophenoxyacetic acid), SRV (4-(2-methyl-4-chlorophenoxy)butyric acid), 2,4-D (2,4-dichlorophenoxyacetic acid), 2,4-DB, mecoprop, triclopyr, fluroxypyr, clopyralid and their derivatives (e.g. salts, esters and amides);

C. derivatives of 1,3-dimethylpyrazole, such as paradoxien, pyrazolate, benzefoam;

D. dinitrophenol and their derivatives (for example, acetates such as DNOC (dinitrocresol), dinoterb, dinoseb and its esters, dinoseb acetate);

E. dinitroaniline herbicides, such as dinitramine, trifluralin, ethalfluralin, pendimethalin and oryzalin;

F. arylcarbamoyl herbicides, such as Diuron, fluometuron, metoxuron, neburon, Isoproturon, chlortoluron, chloroxuron, linuron, monolinuron, chlorbromuron, Diuron and methabenzthiazuron;

G. phenylcarbamoyloxyphenylcarbamate, such as phenmedipham desmedipham, bromacil and terbacil;

J. triazine herbicides, such as atrazine, Simazine, isoprotein, cyanazine, prometryn, deltamethrin, simetryn and terbutryn;

K. phosphorotioate herbicides, such as piperophos, bensulide and butamifos;

L. thiolcarbamate herbicides, such as cycloate, vernolate, molinet, thiobencarb, butyl*, EPTC*triallate, diallate, ethyl asbroker, thiocarbonyl, peridot and timepart;

M. 1,2,4-triazine-5/he herbicides, such as metamitron, metribuzin;

N. benzoic acid herbicides such as 2,3,6-TBA, dicamba and chloramben;

O. anilide herbicides, such as pretilachlor, butachlor corresponding alachlor, the corresponding connection of propachlor, propanil, metazachlor, metolachlor, acetochlor and dimethachlor;

P. dihalomethane herbicides, such as dichlobenil, bromoxynil and ioxynil;

Q. haloalkane herbicides such as dalapon, TCA (trichloroacetic acid) and its salts;

R. simple diphenyl ether herbicides such as lactofen, fluoroglycofen or its salts or esters, nitrogen, bifenox, acifluorfen and its salts and esters, oxyfluorfen and fomesafen, chlornitrofen and chlorotoxin;

S. phenoxybenzamine herbicides, such as diclofop and his kostelany ether;

T. cyclohexanedione herbicides, such as aloxide and its salts, sethoxydim, cycloxydim, tralkoxydim, clethodim;

U. herbicides sulfonyl urea, such as chlorsulfuron, sulfometuron, metsulfuron and its esters; beskulture and its esters such as methyl ester, DPX-M6313, chlorimuron and esters such as ethyl ether, primisulfuron and esters, such as methyl ether, DPX-LS 300 and pyrazosulfuron;

V. Imidazolidinone herbicides, such as imagin, imazamethabenz, imazapyr and his isopropylammonium salt, imazethapyr;

W. aryanised herbicides, such as femprep and its esters, benzoylperoxy-ethyl, diflufenican;

X. herbicides amino acids, such as glyphosate and glufosinate and its salts and esters, sulfosate and milanapos;

Y. ergonomically herbicides such as MSMA;

Z. herbicide amide derivatives, such as napropamide; propyzamide, carbetamide, tabulam, bromated, isoxaben, nitroanilide, diphenamid and naptalam;

AA. mixed herbicides, including ethofumesate, cinmetacin, difenzoquat and its salts, such as salt methyl sulfate, clomazone, oxadiazon, bromophenoxy, Barban, tridiphane, (in the ratio 3:1) flurochloridone, csinhl is that active structural unit is paraquat, and those in which the active structural unit is Diquat.

*These compounds are preferably used in combination with compounds providing safety, such as 2,2-dichloro-N,N-di-2-propylacetamide (dichlormid).

1. Substituted 1-phenyl - or 1-pyridinyl-benzotriazole General formula I

< / BR>
where R1represents hydrogen or halogen(C1-C6)alkyl;

R2represents C1-C6-alkyl, halogen, hydrogen, halogen (C1-C6)alkyl, C1-C6-alkoxycarbonyl or-SO3H;

R3represents hydrogen, halogen, hydroxy, C1-C6-alkyl, halogen(C1-C6)alkyl, cyano(Carbo-C1-C6-alkoxy)C1-C6the alkyl group of the formula YR8where Y represents O, NR9or S(O)n, R8represents C1-C6-alkyl, halogen(C1-C6)alkyl, cyano(C1-C6)alkyl, C2-C6alkenyl, C2-C6-quinil or a group of the formula -(R10)m-COR11or -(R10)mSO2R11where R9represents hydrogen, C1-C6-alkyl or C1-C6-alkylsulphonyl, R10represents C1-C6alkylene, R11predstavljaet 5, 6 or 7-membered saturated or unsaturated heterocycle, where the ring members selected from the group including nitrogen, carbon, oxygen, which may be substituted C1-C6-alkyl, formyl or carboxy;

R4represents hydrogen;

R5represents halogen;

R6represents halogen (C1-C6)alkyl;

R7represents hydrogen;

X represents N or C-R13where R13represents halogen,

or agricultural acceptable salt.

2. Connection on p. 1, in which R1represents hydrogen or halogen (C1-C6)alkyl, R2represents hydrogen, halogen (C1-C6)alkyl, halogen or (C1-C6)alkyl, R3represents hydrogen, halogen, or Y, R8, R4is hydrogen, R5represents halogen, R6represents halogen (C1-C6)alkyl, R7is hydrogen and X is N, C-halogen.

3. Connection on p. 2, in which R1is hydrogen, R2represents hydrogen, halogen (C1-C6)alkyl or halogen, R6represents halogen (C1-C6)alkyl and X represents N or C-halogen.

4. Connection on p. 2, where R1-C6) alkyl, R7denotes hydrogen and X is N.

5. Connection on p. 2, in which R1is hydrogen, R2is hydrogen, halogen or (C1-C6)alkyl, R3indicates OR8in which R8is (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6) quinil, cyano(C1-C6)alkyl and halogen(C1-C6)alkyl, R4is hydrogen, R5- halogen, R6- halogen(C1-C6)alkyl, R7is hydrogen and X represents C-halogen.

6. Connection on p. 1, in which R1is hydrogen, R2hydrogen, halogen (C1-C6)alkyl, (C1-C6)alkyl or halogen and R3- YR8.

7. Connection on p. 6, in which R3- YR8, R4is hydrogen, R5- halogen, R6- halogen(C1-C6)alkyl, R7is hydrogen and X Is N or C-halogen.

8. Connection on p. 1, in which R1represents hydrogen or halogen(C1-C6)alkyl, R2is hydrogen, (C1-C6)alkyl, halogen (C1-C6)alkyl or halogen, R3represents a 5, 6 or 7-membered saturated or unsaturated heterocycle, in which the members of the cycle are selected from the group consisting of nitrogen, carbon, kishtawal N, C-halogen.

9. Connection on p. 8, in which the heterocycle is associated with benzotriazole through the nitrogen atom.

10. Connection on p. 9, in which the heterocycle contains one nitrogen atom and one other heteroatom selected from nitrogen and/or oxygen.

11. Connection on p. 8, in which the heterocyclic atom substituted (C1-C6)alkyl.

12. Connection on p. 1, in which R1is hydrogen, R2- chlorine, fluorine or triptorelin, R3is hydrogen, R4is hydrogen, R5- halogen, R6- halogen(C1-C6)alkyl, R7is hydrogen and X Is N or C-halogen.

13. Connection on p. 1, in which R1is hydrogen, R3is hydrogen, R4is hydrogen, R5is chlorine, R6- CF3, R7is hydrogen and X is C-Cl.

14. Connection on p. 1, in which R1- H, R2- H or fluorine,

R4- H, R5is chlorine, R6- CF3, R7- H and H - n

15. Connection on p. 1, in which R1is hydrogen, R2- fluorine, R3- OC2H5, R4is hydrogen, R5chlorine, R6- CF3, R7is hydrogen and X is N.

16. Connection on p. 1, in which R1is hydrogen, R2is chlorine, R3- N (CH3)2, R4is hydrogen, R5is chlorine, R6is R or chlorine, R4is hydrogen, R5is chlorine, R6- CF3, R7is hydrogen and X is N.

18. Connection on p. 1, in which R1is hydrogen, R2- chlorine,

R4is hydrogen, R5is chlorine, R6- CF3, R7is hydrogen and X is N.

19. Connection on p. 1, in which R1is hydrogen, R2is chlorine, R4is hydrogen, R5is chlorine, R6- CF3, R7is hydrogen and X is N.

20. Herbicide composition, characterized in that it contains herbicide-effective amount of compounds of formula I

< / BR>
in which R1is hydrogen, C1-C6-alkyl, halogen(C1-C6)alkyl,

R2is hydrogen, nitro, C1-C6-alkyl, halogen, C1-C6-alkoxycarbonyl, halogen(C1-C6)alkyl, SO3H;

R3is hydrogen, C1-C6-alkyl, halogen, hydroxy, halogen - C1-C6-alkyl, cyano (Carbo-C1-C6-alkoxy) C1-C6-alkyl, (C1-C6-alkyl)n-amino-C1-C6-alkyl,

YR8where Y represents O, NR9or S(O)nand R8represents - (R10)m- COR11C1-C6-alkyl, halogen(C1-C6)alkyl, cyano-C1-C6-alkyl, C2-C6alkenyl is UP>11
represents hydroxy, C1-C6-alkoxy, or R3represents a 5,6 or 7-membered saturated or unsaturated optionally substituted heterocycle, where the ring members selected from the group consisting of nitrogen, carbon, oxygen and sulfur, and where the substituents are selected from the group consisting of C1-C6-alkyl, carboxy, formyl, m is 1, n is 0, 1 or 2, R4is hydrogen, R5represents halogen, R6represents halogen(C1-C6)alkyl, R7represents hydrogen, X represents N or CR13where R13denotes halogen, his agricultural-acceptable salts and agricultural-acceptable diluents or carriers.

21. Herbicide composition according to p. 20, in which R1is hydrogen, C1-C6-alkyl, halogen (C1-C6)alkyl, R2represents hydrogen, C1-C6-alkyl, nitro, halogen(C1-C6)alkyl or halogen, R3is hydrogen, halogen or YR8, R4is hydrogen, R5- halogen, R6- halogen(C1-C6)alkyl, R7is hydrogen and X Is N or CR13in which R13- halogen.

22. The composition according to p. 20, in which R1is hydrogen, R2is hydrogen, C1-C6-alkyl or halogen, R6 the economic crops, characterized in that it comprises applying to such vegetation or its habitat herbicide effective amount of a compound having the formula

in which R1represents hydrogen, C1-C6-alkyl, halogen(C1-C6)alkyl;

R2represents hydrogen, nitro, C1-C6-alkyl, halogen, C1-C6-alkoxycarbonyl, halogen(C1-C6)-alkyl, SO3H;

R3represents hydrogen, C1-C6-alkyl, halogen, hydroxy, halogen(C1-C6)alkyl, cyano(Carbo-C1-C6-alkoxy)C1-C6-alkyl, (C1-C6-alkyl)namino-C1-C6-alkyl, YR8where Y represents O, NR9or S(O)nand R8represents -(R10)m-COR11C1-C6alkyl, halogen(C1-C6)alkyl, cyano(C1-C6)-alkyl, C2-C6alkenyl or C2-C6-quinil, R9represents C1-C6-alkyl, R10is alkylene, R11represents hydroxy, C1-C6-alkoxy,

or R3represents a 5, 6 or 7-membered saturated or unsaturated optionally substituted heterocycle, where the ring members selected from the group consisting of nitrogen, is rmil, m is 1, n is 0, 1 or 2;

R4represents hydrogen;

R5represents halogen;

R6represents halogen(C1-C6)alkyl;

R7represents hydrogen;

X is N or CR13where R13denotes halogen, and its agricultural acceptable salts and agricultural acceptable diluents or carriers.

24. The method according to p. 23, in which R1is hydrogen, R2is hydrogen, (C1-C6)alkyl or halogen, R3is hydrogen or YR8, R4is hydrogen, R5- halogen, R6- CF3, R7is hydrogen and X is N.

 

Same patents:

The invention relates to new derivatives of erythromycin, method of production thereof, to pharmaceutical compositions based on them and to intermediate compounds

The invention relates to new aryl-substituted derivatives of piperidine, which has antagonistic activity to the receptor NK3person, to a method for their production and to their use in pharmaceutical compositions

The invention relates to a new group of imidazole compounds, method of their production and use for the treatment of diseases, mediasound cytokines, as well as to pharmaceutical compositions used for such therapy

The invention relates to 4-amino-1-piperidinecarbonitrile formula (I):

< / BR>
where R1and R2each independently of one another denote H, A, Ph, Ph-ALK, CO-A, CO-Het, or known of the chemistry of protective peptides for amino group;

R1and R2together also denote alkylene with 4-5 C atoms, and one or two CH2- groups may be replaced by-O-, -S-, -CO-, -NH-, -NA - and/or N-CH2-Ph and, if necessary, the benzene ring may be precondensation so that the formed dihydroindole, tetrahydropyrimidines, tetrahydroisoquinolinium or dehydrobenzperidol the rest;

R3and R4each independently of one another denote H, A, Gal, -X-R5, CN, NO2, CF3CH2-CF3, SOn-R7or SO2-NR5R6;

R5denotes H, A, CF3CH2-CF3Ph, Ph-alk, C5-C7- cycloalkyl or C5-C7-cycloalkyl-alk;

R6denotes H or A, or

R5and R6together also denote alkylene with 4-5 C atoms, and one CH2group can be replaced by-O-, -S-, -NH-or-N-CH2-Ph;

R7denotes A or Romani;

Gal denotes F, Cl, Br or I;

Ph denotes unsubstituted or one-or two-, or three times substituted by A, OA, Gal, CF3, NH2, NHA or NA2phenyl;

Het denotes a saturated or unsaturated five - or six-membered heterocyclic residue with 1 to 4 atoms of nitrogen, oxygen and/or sulfur; and

"n" represents 1 or 2;

and their physiologically acceptable salts

The invention relates to a derivative of a simple ester, application and intermediate compounds used for their production

The invention relates to ether compounds and their use

FIELD: chemistry.

SUBSTANCE: invention describes novel potassium or hydrazinium salts of 4-dinitromethyl-1,2,3-triazoles of general formulae V-VIII: V, VI VII, VIII, where Kat+ =K+ (V,VII), NH2NH3+ (VI;VIII).

EFFECT: higher herbicidal activity.

1 cl, 2 tbl, 4 ex

FIELD: chemistry.

SUBSTANCE: invention describes N-cycloalkylbenzylamide derivatives of formula

, where A denotes a saturated 5-member heterocyclic group, Z1 denotes a substituted C3-C7-cycloalkyl; Z2 and Z3, which can be identical or different from each other, denote a hydrogen atom; C1-C8-alkyl; cyano; C1-C8-alkoxycarbonyl; a method of producing said compounds, use thereof as fungicidal active substances, particularly in form of fungicidal compositions, and method of controlling phytopathogenic fungi, mainly in plants, using said compounds or compositions.

EFFECT: higher activity, low amount of active substance while maintaining efficiency at least equivalent to that of existing compounds.

11 cl, 5 ex

FIELD: agriculture.

SUBSTANCE: invention relates to agriculture. Presowing treatment of seeds of winter wheat is carried out with a mixture of aqueous solution "PMAG" polymethacrylateguanidine with a molecular mass of 500 thousand specific units, with a concentration of 0.2% with protectant Kinto Duo® (BASF) at a dose of 1.5 l/t at an operating flow of 15 litres per 1 ton of seeds.

EFFECT: invention enables to reduce labor intensity of seeds treatment and to provide enhanced properties of seeds sown, to increase yield and quality of winter wheat grain.

7 tbl, 4 ex

FIELD: chemistry.

SUBSTANCE: invention relates to agriculture. In order to protect vegetative sunflower plants from the damaging effect of 2,4-dichlorophenoxy acetic acid, said plants are treated with benzyl ether (4,6-dimethyltriazolo-[1,5-a]pyrimidyl-2-sulphanyl)-acetic acid of formula I: in amount of 200 g/ha, three days after applying the herbicide.

EFFECT: invention increases sunflower yield.

1 tbl

FIELD: chemistry.

SUBSTANCE: invention relates to agriculture. As active, composition contains combination of florasulam with 2,4-dihlorphenoxyacetic acid ether, necessary for obtaining its preparative form target additives and, at least, 0.1 wt % of 2,4- dichlorophenoxyacetic acid. As ether of 2,4-dihlorphenoxyacetic acid, composition contains 2-ethylhexyl or isooctyl ether of 2,4-dihlorphenoxyacetic acid, and as target additives - SAS, solvent, defoamer, antifreeze, thickener, biocide and acidity regulator. Weed plants and place of their vegetation are treated with effective quantity of herbicidal composition.

EFFECT: invention makes it possible to obtain stable and safe in application preparative forms of herbicidal compositions, stable in prolonged storage and able to suppress weed plants in grain crops and maize.

6 cl, 3 tbl, 6 ex

FIELD: chemistry.

SUBSTANCE: described are preparations, which possess fungicidal activity, containing hydrazones of nitro-1,2,3-tiazol-4-yl-carbaldehyde of formula

Ia-c,

in concentration 30 mg/l in acetone, which can be applied in agriculture for fight against fungal diseases of plants.

EFFECT: improved qualities of claimed preparations.

1 tbl, 4 ex

FIELD: chemistry.

SUBSTANCE: invention relates to agriculture, in particular to means for fighting undesirable vegetation. A herbicidal composition is created on the base of a sinergically effective combination of sulphonylureas (I) and triazolopyrimidines (II). The ratio of active substances (I) and (II) changes in the range from 1:5 to 5:1. A mixture of agriculturally acceptable adjuvants from the group of ethoxylated fatty alcohols and organosilicon compounds from the class of silixane is added to the said composition. The ratio of ethoxylated fatty alcohols and siloxanes in the mixture changes in the range from 1:10 to 10:1 respectively. A mixture of isodecyl alcohol ethoxylate with an organosilicon compound as an adjuvant is applied. In order to fight undesirable vegetation in crops of cultivated plants an effective quantity of the herbicidal composition is applied on it.

EFFECT: obtaining the means for fighting undesirable vegetation.

13 cl, 4 tbl, 2 ex

FIELD: agriculture.

SUBSTANCE: composition is intended for germination and growth of cucumbers. Retardant growth has molecular formula C9H18Cu2N14O10 and consists of active substance, 4H-1,2,4-triazol-4-yl([4H-1,2,4-triazol-4-yl [(4H-1,2,4-triazol-4-yl-amino)methyl]amino]methyl] amino)methanol coordinated with ions of copper(II). To obtain retardants reacting copper(II) nitrate with 4H-1,2,4-triazol-4-yl([4H-1,2,4-triazol-4-yl[(4H-1,2,4-triazol-4-yl-amino)methyl]amino]methyl] amino)methanol (L):

2Cu(NO3)2+3H2O+L→(CuOH)2L(NO3)2·H2O↓+2HNO3, obtained by reaction of condensation of 4-amino-1,2,4-triazole with formaldehyde in aqueous medium at temperature 60 °C for 45 minutes

.

EFFECT: higher efficiency of growth of cucumbers.

2 cl, 2 dwg, 1 tbl

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