Derivatives of hydrogenated n-substituted pyridines, the retrieval method, herbicide composition and method of weed control

 

(57) Abstract:

Usage: agriculture as a herbicide. The inventive products: hydrogenated derivatives of N-substituted pyridines f-ly I listed in the description, where A is NH, R1- halogen, R2halogen or cyano, R3is hydrogen, C2-C5alkenyl, C2-C5-quinil, halogen, nitro, R4- hydroxycarbonyl or C1-C5-allyloxycarbonyl, or A and R4form a group - N-C(O). Reagent 1: isocyanate f-crystals II listed in the description. Reagent 2: hydrogenated pyridine f-ly III listed in the description. Reaction conditions: in an aqueous medium in the presence of a base at 0 - 20oC. 4 C. p. F.-ly, 5 PL.

The present invention relates to new derivatives of hydrogenated N-substituted pyridines, the way they are received, as well as to new herbicide compositions and method of weed control.

Known derivatives of N-substituted pyridines, in particular 2-(4-chloro-2-fluoro-5-isopropoxyphenyl)-5,6,7,8-tetrahydroimidazo [1,5-a] pyridine-1,3-(2H, 8A H)-dione (patent EP-A 40389) with high herbicide activity.

The present invention is the creation of new derivatives of hydrogenated N-Zam is the second.

This object is achieved with new derivatives of hydrogenated N-substituted pyridines of General formula I

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in which a is the group NH;

R1halogen;

R2halogen or cyano;

R3hydrogen, C2-C5alkenyl, C2-C5-quinil halogen, nitro, cyano, C1-C5alkylsulfonate, cycloamylose, C1-C5-alkylsulfonyl, C1-C5-alkylthio, C1-C5-allyloxycarbonyl, C1-C5-allyloxycarbonyl, C1-C5-allyloxycarbonyl, C2-C5-alkenylamine, C2-C5-quinil or-O-(C1-C5)alkylene-R5group, in which R5is hydrogen, C1-C5alkyl, C2-C5alkenyl or C2-C5quinil, and a hydrocarbon residue, if necessary, may be substituted with halogen or cyano, or R2and R3together with the phenyl ring form a radical of the formula:

< / BR>
R4hydroxycarbonyl or C1-C5- allyloxycarbonyl or A and R4form a group-N-C(O)-, oriented in such a way that the nitrogen atom is linked to C-O groups of the compound (I).

The compounds of formula I are obtained by vzaimode is 1-R4have the meanings stated above, with subsequent isolation of the target product or a translation of it in the connection in which A and R4form a-N-C(O)- by condensation of amide and ester groups of the compounds of formula I.

The above reaction can be carried out in various solvents under different conditions. One of the options the reaction is carried out in the presence of a base in aqueous medium. The preferred bases are the hydroxides of alkali metals such as sodium hydroxide or potassium. The reaction in this case is carried out at low temperature, namely at a temperature below room temperature, preferably at 0 -20oC. the Target compound can be isolated by known methods, for example by acidification, filtration and extraction.

The reaction is carried out in an inert solvent, for example toluene, diethyl ether or methylene chloride, at a temperature of 0 -100oC, preferably at room or near the temperature. The target connection and in this case produce by known methods, for example by removal of the solvent, chromatography or extraction.

The source compounds are known and can be obtained izvestnyh urea of formula (I). For this purpose, carry out the condensation reaction between Amida and ether group derived urea of formula (I). The reaction is facilitated in the presence of acid or nucleophilic agent. One of the options the reaction is carried out in an environment of alcohol, for example ethanol, in the presence of acid, for example HCl. The reaction can be conducted at a temperature from room temperature up to the boiling point. It is preferable to carry it out at the boiling point. Target product produce by known methods, for example by evaporation or crystallization.

Alternatively the reaction is carried out in an environment of alcohol, for example methanol, in the presence of a nucleophilic agent, such as K2CO3. The reaction can be conducted at temperature close to the room temperature to 60oC, preferably at about 50oC. To obtain the target product of the resulting compound is treated with ammonium chloride. The target product can then be selected by known methods, for example by extraction or crystallization.

The compounds of formula (I) are valuable products, because they can be used effectively to control plant growth. Under plants mean germinated seeds, seedlings and rooted races herbicides, since, as shown by the results of standardized tests, they have a harmful effect on monocotyledonous and dicotyledonous plants. Their herbicide effect is as if predsjedava and post-harvest treatments plants. This herbicide action means that the compounds of formula (I) are of interest, in particular, for combating weeds (undesirable vegetation).

The compounds of formula (I) are more active against dicots than monocots plants. They are less toxic to plants than to the weeds. Therefore, in particular, they are of interest as selective herbicides for controlling weeds of cultivated plants, such as sugar beet, sunflower, cotton, soybean, maize and wheat.

The object of the present invention is also a method of combating weeds in cultivated areas, including management of weeds or their habitat is effective herbicide against a number of the claimed compounds. To ensure selective action number used to handle the connection should be sufficient for the destruction of weeds and at the same time, so that it is not p the present invention as herbicides General or selective effect their consumption may vary depending on a number of factors, such as the nature of the used compounds and plants growing in the treated area, the processing method and form of the drug, the conditions in which processing is carried out, such as the nature of the soil, the weather, etc., As a rule, however, satisfactory results when weed control is achieved when the flow rate of the compounds in accordance with the present invention is 0.01 to 5, preferably 0.01 to 1, most preferably 0.01 to 0.5 kg/ha, If necessary, can be repeated processing. When processing the claimed compounds of cultivated plants consumption, they usually should not exceed about 1 kg/ha As a rule, it is in the range from 0.01 to 1 kg/ha

For practical use as herbicides, the compounds of formula (I) may preferably used in the form of compositions comprising effective from the point of view of herbicide activity amount of the compounds of formula (I) and an inert carrier that is acceptable from an agricultural point of view. Under agricultural acceptability mean that his presence in the composition should not cause poisoning of the surrounding agricultural environment, including the soil on arable land, the plants, or ocasionalmente, 0 to 20 wt. acceptable from the point of view of their use in agriculture surfactant and 1 to 99.99 wt. inert carrier. In some cases it is advisable to use a composition with a higher ratio of surface-active substance and the active ingredient. Ready for use form of the inventive compositions typically contain 0.01 to 25 wt. the active component. Its content, however, may be larger or smaller and depends on the purpose of the composition and physical properties of compounds. Concentrated form of compositions, which are diluted before use, usually contain 2 to 90, preferably 10 to 80% of the active component.

The composition of compounds in accordance with the present invention include dusty, granulates, tablets, concentrates, suspensions, wettable powders, concentrates, emulsions, etc. All these are the usual ways, for example by mixing the compounds in accordance with the present invention with an inert carrier. In particular, the liquid composition obtained by mixing components of fine particulate compositions by mixing and, as a rule, grinding, slurry, wet grinding, granulates and tabletirovannye media or glomerulone.

For example, dusty can be obtained by grinding and mixing the active ingredient with a solid inert carrier such as talc, clay, silica, etc., the Granules can be obtained by applying the compound, usually dissolved in a suitable solvent, or impregnating it with a solution of granular media, such as attapulgite or vermiculite, with the size of the particles is typically in the range from about 0.3 to 1.5 mm Wettable powders which can be dispersed in water or oil to any desired concentration of the active component can be obtained by incorporating wetting in concentrates Farrukh Dustov.

Compounds in accordance with the present invention can also be used in microencapsulated form.

To improve the characteristics of the active component, reduce foam, caking and corrosion activity in herbicide compositions can be introduced acceptable from the point of view of their use in agriculture supplements.

Under surfactants in this case we have in mind is acceptable from the point of view of their use in agriculture materials is the modification of the surface properties. Examples of surfactants are ligninsulfonate and sodium lauryl sulfate.

Under the media in this case refers to liquid or solid material used to dilute the concentrate to usable or desired concentration. In the case of Farrukh Dustov or granules may be, for example, talc, kaolin or diatomaceous earth; in the case of liquid concentrates hydrocarbons, for example xylene or alcohols, particularly isopropanol, and in the case of liquid forms for processing, for example, water or diesel fuel.

Compositions in accordance with the present application may include and other compounds having biological activity, e.g. compounds having similar or complementary herbicide activity, or connection-antidotes or possessing fungicidal or insecticidal activity.

Typical herbicide compositions in accordance with the present invention are illustrated below by examples A, B and C, in which the content of components, expressed in mass units.

If this is not specified, the given temperature expressed in degrees Celsius.

Example A.

1[[(4-chloro-2-fluoro-5-isopropoxyphenyl)and hydrochloride 1,2,3,6-tetrahydro-2-pyridineboronic acid in 40 ml of 1 n NaOH solution is added in stages of 4.6 g (0,02 mol) of solid finely chopped 4-chloro-2-fluoro-5-isopropoxyaniline. In the process of adding using ice baths maintain the temperature of the 5oC. After the addition the solution was stirred at room temperature for 4.5 h, then filtered, sucking away the sediment.

The filtrate is carefully acidified with 15% hydrochloric acid.

The precipitate is sucked off, washed with water and dissolved in 150 ml of methylene chloride.

Dry (Na2SO4) the solution is evaporated to obtain a viscous liquid and triturated with 200 ml of a mixture of diethyl ether and hexane (5:1), resulting in the pure target compound in the form of almost colorless crystals. The pace. plvl. 115 -116oC.

Example Century.

Methyl ether (I) [[(4-chloro-2-fluoro-5-isopropoxyphenyl)amino]-carbonyl]-1,2,3,6-tetrahydro-2-pyridineboronic acid (compound 1.2).

To mix the solution 5,65 g (0,04 mole) methyl ester 1,2,3,6-tetrahydro-2-pyridineboronic acid in 75 ml of dry toluene is added dropwise without cooling of 9.2 g (of 0.04 mole) 4-chloro-2-fluoro-5-isopropoxyaniline dissolved in 200 ml of dry toluene.

After attenuation exothermic reaction (29o) the reaction mixture is stirred for 5 h at ambient temperature and then evaporated the DOS is the Xan and diethyl ether (3:2) leads to the production of target compounds first, in the form of a yellow syrup, which, however, then hardens. The pace. plvl. 88 89o.

In the same manner as described in examples A and B, the resulting connection in accordance with the table. 1.

Example C.

2-(4-chloro-2-fluoro-5-isopropoxyphenyl)-8,8-dihydroimidazo [1,5-a] -pyridine-1,3-(2H,5H)-dione (compound 2.3).

A solution of 1.43 g (0,004 mol) 1-[[(4-chloro-2-fluoro-5-isopropoxyphenyl)amino] carbonyl] -1,2,3,6-tetrahydro-2-pyridineboronic acid in 20 ml ethanol and 20 ml of 2 n HCl is refluxed for 4 hours After concentrating the reaction solution in a rotary evaporator apparatus receives the target compound as a pale yellow syrupy liquid, which represent according to thin-layer chromatography (Rf0,35, stationary phase silica gel, mobile phase mixture ethyl acetate and hexane in a ratio of 1:1, the manifestation of using a 10% aqueous solution KMnO4) individual connection.

When cooled overnight at -15ocomes complete solidification with the formation of the crystalline mass (rubbing with hexane). The pace. plvl. 90 -92oC.

Example D.

2-(2,4-dichloro-5-isopropoxyphenyl)-8,8 a-dihydroimidazo [1,5-a]-pyridine-1,3-(2H,5H is but] carbonyl]-1,2,3,6-tetrahydro-2-pyridineboronic acid in 18 ml of ethanol and 18 ml of 2 n hydrochloric acid is boiled for 4 hours under reflux, then evaporated in vacuum.

The residue is dissolved in methylene chloride, washed with 75 ml of water, dried (Na2SO4) and filtered.

Remaining after evaporation of the filtrate syrup was dissolved in 20 ml of diethyl ether.

Cooling overnight at -18oleads to the formation of the target compound as colorless crystals. The pace. plvl. 125 126o.

Example E.

2(4-chloro-2-fluoro-5 oksifenil)-8,8 a-dihydroimidazo [1,5-a] -pyridine-1,3-(2H,5H)-dione (compound 2.2).

Stirred for 2 h at 50oa mixture of 8.4 g (0,0217 mole) of methyl ester 1-[[(4-chloro-2-fluoro-5-methoxycarbonylaminophenyl)-amino] carbonyl]-2-pyridineboronic acid, 3 g (0,0217 mol) K2CO3and 175 ml of methanol.

The resulting reaction mixture is yellow then evaporated in vacuo and the residue treated with 200 ml of a saturated solution of NH4Cl.

The resulting target compound is extracted with three portions 120 ml of diethyl ether and the ether extracts dried over anhydrous Na2SO4.

Crystalline mass remaining after evaporation of the solvent in a rotary evaporator apparatus, triturated with a mixture of hexane and diethyl everflow-2-fluoro-5-isopropoxyphenyl)-8,8 a-dihydroimidazo [1,5-a] pyridine-1,3-(2H,5H)-dione (compound 2.3).

To mix the solution 2,82 g (0,02 mol) methyl ester 1,2,3,6-tetrahydro-2-pyridineboronic acid in 40 ml of dry toluene containing 0.8 ml of triethylamine add without cooling of 4.6 g (0,02 mol) 4-chloro-2-fluoro-5-isopropoxyaniline in 100 ml of toluene. After adding the total amount of isocyanate, the reaction mixture was stirred at room temperature for 18 h and then evaporated in vacuum.

Remaining after evaporation of viscous liquid is dissolved in 50 ml of a mixture of hexane and diethyl ether (1:1) and filtered.

The filtrate was incubated overnight at -15o, resulting in the formation of colorless crystals. The pace. plvl. 90 -92oC.

In the same manner as described in example F, by reacting methyl ester 1,2,3,6-tetrahydro-2-pyridineboronic acid with the appropriate arylisocyanate or arylisocyanates get the target compounds in accordance with the table. 2.

Reduction.

(1) a mixture of 4 - and 5-substituted isomers,

(2) Ar 2-R2-4-R3-5-R4-phenyl,

(3) Ar12,4-dihydrobenzo[b]-1,4-Bessin-3-one-6-Il,

(4) Ar23,4-dihydro-2H-cinoxacin-2-one-7-Il,

(5) Ar31H-cinoxacin-2-one-7-Il,

(6) Ar4benzo[d]- parts of the compounds of formula (I) and 90 parts of powdered talc are mixed in a mechanical mill-mixer and pulverized to obtain a homogeneous bulk dust with the desired particle size. The resulting dust can be used for treatment of areas affected by weeds.

Example Century.

Obtain wettable powder.

Mixed and pulverized 25 parts of the compound of formula (I), 25 parts of synthetic fine silica, 2 parts of laurilsulfate sodium, 3 parts ligninsulfonate sodium and 45 parts of finely ground kaolin to obtain particles with an average size of about 5 microns. Obtained wettable powder is diluted before use with water to the desired concentration, resulting in the liquid for spraying.

Example C.

Obtaining emulsion concentrate (EC).

Mix in a glass of 13 parts of the compounds of formula (I) with 7 parts tokimura 360A (a mixture of anionic and nonionic surfactants with a predominant content of nonionic surfactants), 24 parts of dimethylformamide and 56 parts tanico 500-100 (mainly a mixture of alkyl aromatic compounds such as xylene and ethylbenzene) to obtain a solution. Thus obtained EU diluted with water before use.

Biological tests

Herbicide activity connect Eshtemoa and post-harvest treatments. The tests were carried out on the following weeds: Abutilon theophrasti, Amoranthus retrofleax, Sinapis alba, Solanum nigrus, Bromus teetorum, Setaria viridis, avena fatua and Echinochloa crus-galli.

In experiments on predsjedava processing small plastic pots filled with dry earth, sowed the seeds of various weeds. In 24 hours or less after seeding the pots were sprayed with water to moisten the soil, and then produced spraying the soil surface compounds or compositions of the tested compounds in the form of aqueous emulsions or acetone solutions with the determination of the content of the emulsifier. After spraying, the pots were placed in a greenhouse, where they were heated in accordance with the need and watered once a day or more often. The plants were kept in these conditions, 14 and 21 days, after which assessed their condition and the damage he had done.

In experiments on post-harvest processing of the compounds or compositions of the tested compounds in the form of aqueous emulsions were sprayed leaves of various weeds at a certain stage of development. After treatment, plants were placed in a greenhouse, where they were watered once a day or more so that water falling on leaves. After 21 days after treatment was assessed caused to plants damage.

Otch analogues conduct, to determine the effect of structural differences on herbicide activity.

Compound A (known): 2-(4-chloro-2-fluoro-5-isopropoxyphenyl)-5,6,7,8-tetrahydroimidazo [1,5-a] pyridine-1,3-(2H, in)-dione (described in EP-A 70389, example 1, table. 1, connection # 7)

< / BR>
Connection 2.3: 2-(4-chloro-2-fluoro-5-isopropoxyphenyl)-5,8-dihydroimidazo [1,5-a] pyridine-1,3-(2H,in)-dione

< / BR>
Method.

A. Prevschatuyu herbicide test.

Prevschatuyu the test is carried out in greenhouse pots filled with sandy soil-inopinata type and sowing the seeds of weeds: Abutilon theophrasti, Capsella bursa-pastoris, Chenopodium album, Datura stramonium, Ipomoea purpurea, Portulaca Oleracea, Sida spinosa, Solanum nigrum, Stellaria media, Digitaria sanguinalis and Panicum dichotoniflorum and seeds of cotton, soybean, sugar beet, sunflower, maize, wheat and sorghum ordinary.

The seeds are covered with soil, and then the pots are sprayed with 100 g of the asset. ing./ha and 330 g act.ing./ha volume spraying 600 l/ha

Pots moisturize if needed and kept in the greenhouse under standard conditions. Herbicide activity is assessed visually (0 to 100% inhibition compared to untreated control) 25 days after application.

C. post-harvest herbicide test.

Polished the priori grass: Abutilon theophrasti, Capsella bursa-pastoris, Chenopodium album, Datura stramonium, Ipomoea purpurea, Portulaca oleracea, Sida spinosa, Solanum nigrum, Stellaria media, Digitaria sanguinalis and Panicum dichotoniflorum and seeds of cotton, soybean, sugar beet, maize, wheat and sorghum ordinary. The pots are cultivated in a greenhouse under standard conditions. When the plants have two leaves, they are sprayed three rules 110, 330 and 1000 g act.ing. /ha, with a volume of 600 l/ha Pots moisturize if needed and kept in the greenhouse under standard conditions.

Herbicide activity is assessed visually after 25 days after application. The results are given in table. 3 and 4.

In both tests, as predsjedava and post-harvest, compound, and 2.3 have a very high herbicide activity against the tested weeds.

In tested plants both compounds tolerant cotton and sunflower predsjedava test and the corn in the post-harvest test.

Suddenly the connection 2.3 also tolerant soybeans, corn and wheat in prevschatuyu period and soybeans and sunflower in the post-harvest period. In very low concentrations connection 2.3 also tolerant to wheat and sorghum.

Similarly, test herbicide activity other representatives of the compounds the Results are summarized in table. 5.

Indicate in the table. 5:

1 0% inhibition,

2 10% suppression,

9 90% suppression.

1. Derivatives of hydrogenated N-substituted pyridines of General formula I

< / BR>
where a group NH;

R1halogen;

R2halogen or cyano;

R3hydrogen, C2WITH5alkenyl,2- C5-quinil, halogen, nitro, cyano, C1- C5-alkylsulfonate, cycloamylose,1- C5-alkylsulfonyl, C1WITH5- alkylthio,1- C5-allyloxycarbonyl,1WITH5-allyloxycarbonyl,2WITH5-quinil or-O-(C1WITH5-alkylen; R5the group, in which R5hydrogen, C1- C5-alkyl, C1WITH5alkenyl or2- C5-quinil, and a hydrocarbon residue, if necessary, may be substituted with halogen or cyano, or R2and R3together with the phenyl ring form a radical of the formula

< / BR>
< / BR>
< / BR>
< / BR>
< / BR>
< / BR>
R4-hydroxycarbonyl or1WITH5allyloxycarbonyl or a and R4form a group-N-C(O)-, oriented in such a way that the nitrogen atom is linked to the C=O groups of the compounds I.

2. The way formula fields

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subjected to interaction with gidrirovanny pyridine of General formula

< / BR>
where R1R4have the values listed in paragraph 1,

with subsequent isolation of the target product or a translation of it in the connection in which a and R4form a group-N-C(O)- by condensation of amide and ester groups of the compounds of formula I.

3. Herbicide composition comprising an active ingredient derived hydrogenated N-substituted pyridine and the target additives, characterized in that as a hydrogenated derivative of N-substituted pyridine she contains a compound of formula I under item 1 in an effective amount.

4. Method of weed control by handling the places of their growth herbicide composition comprising an active ingredient derived hydrogenated N-substituted pyridine and the target additives, characterized in that as a herbicide composition use composition under item 3 in the effective amount of active ingredient/ha

 

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< / BR>
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