Derivatives of amide n-sulfonylamino acids, including n-containing 6-membered aromatic ring, fungicide and herbicide compositions and methods of weed control and plant pathogenic fungi

 

(57) Abstract:

Derivatives of amide N-sulfonylamino acids, including N-containing 6-membered aromatic ring, formulas

< / BR>
where R1- C1-C10the alkyl may contain one or two substituent selected from halogen, C3-C5-cycloalkyl, C1-C3-alkylthio, C1-C4-alkylsulfonyl, C1-C4-alkoxycarbonyl, C2-C4-alkylsulphonyl, or R1- C2-C6alkenyl, C2-C6-quinil, cyclo-C5-C6-alkyl, pyrrolidinyl and other R2is hydrogen, (lower) alkoxy (lower) alkyl, R3and R4- independently represent halogen, C1-C4-alkyl, and other Compounds are recommended to create a fungicide and herbicide compositions that are used to control weeds and plant pathogenic fungi. 5 S. and 2 C.p. f-crystals, 12 tab.

The invention relates to the derivatives of amides of N-sulfonylamino acid containing 6-membered aromatic N-containing ring, and also to compositions fungicide and herbicide containing such compounds as active ingredient, and methods of weed control and plant pathogenic fungi.

In the agricultural production of plant diseases caused by pathogenic fungi belonging to Comycetes, such as downy mildew, late blight, or similar, are found in many plants and are among the diseases with which the most difficult to fight. For this reason desirable to develop improved means of struggle.

The inventors have synthesized various derivatives of N-sulfonamides, including N-containing 6-membered aromatic rings, and has completed extensive studies of their influence on the activity of the fungus. As a result, found that derivatives of N-sulfonamide corresponding to the present invention, exhibit antifungal activity. Compounds that, in accordance with the present invention are active ingredients of the composition are new and useful in the fight against various weeds in rice and plowed fields.

The present invention offers a biocide containing the derived N-sulfonamida, including N-containing 6-membered aromatic with one or two substituent, selected from the group comprising: halogen, C3-C5-cycloalkyl, C1-C3-alkylthio, C1-C4-alkylsulfonyl, C1-C4-alkoxycarbonyl, C2-C4-alkylsulphonyl; or R1- C2-C6alkenyl, optionally containing one or two substituent selected from a halogen, or R1- C2-C6-quinil; or R1- cyclo C5-C6-alkyl which can be substituted by oxopropoxy; or R1- 1-pyrrolidinyl, 2-methyl-1-piperidinyl, 1-aziridinyl, the group-NR5R6;

R2is hydrogen, (lower)alkoxy(lower)alkyl;

R3and R4- independently of one another represent halogen, C1-C4-alkyl, lower alkoxy, di(lower)alkylamino;

R5and R6- independently from each other represent hydrogen, C1-C5-alkyl, a lower alkoxy group, lower alkenyl, cyclo(lower)alkyl, lower quinil, C1-C4-alkoxy-C1-C4-alkyl.

More preferred is derived amide N-sulfonylamino acids, including N-containing 6-membered aromatic ring in which R1- C1-C10-alkyl, optionally containing one or two Deputy, select the>alkylsulfonyl, C1-C6-alkoxycarbonyl, C2-C4-alkylsulphonyl; or C2-C6alkenyl, optionally containing one or two substituent selected from a halogen; C2-C6-quinil; or cyclo-C5-C6-alkyl which can be substituted by oxopropoxy; or 1-pyrrolidinyl; 2-methyl-1-piperidinyl; 1-aziridinyl, or the group-NR5R6;

R2is hydrogen, methoxy-C1-C3-alkyl;

R3and R4- independently of one another represent halogen, C1-C3-alkyl, C1-C3-alkoxy, di(C1-C3)alkylamino;

R5is hydrogen, C1-C5-alkyl, C1-C3-alkoxy;

R6- C1-C5-alkyl, C2-C5alkenyl, cyclo-C3-C5-alkyl, C2-C5-quinil.

Even more preferred is derived amide N-sulfonylamino acids, including N-containing 6-membered aromatic ring in which R1represents a C2-C6alkenyl, optionally containing one or two substituent selected from a halogen;

R2is hydrogen, methoxymethyl group;

R3and R4- independently of one another represent halogen, who with the active ingredient - derived amide pyrimidinecarbonitrile acid and the target additives, characterized in that as the amide derivative pyrimidinecarbonitrile acid it contains a compound of the formula:

< / BR>
where

R1represents a C1-C6-alkyl, optionally containing one or two substituent selected from the group comprising halogen, C3-C5-cycloalkyl; C1-C4-alkylthio and oxiranyl group; or (C2-C6alkenyl, optionally containing 1 or 2 halogen or the group-NR5R6in which R5represents hydrogen, C1-C4-alkyl, R6represents a C1-C4-alkyl, C2-C5-quinil, C3-C5-cycloalkyl; R2represents hydrogen, C1-C4-alkoxy-C1-C4-alkyl; R3represents halogen, C1-C4-alkyl, C1-C4-alkoxy; R4represents a C1-C4-alkoxy, di(C1-C4)alkylamino, in an effective amount.

The next object of the invention is a herbicide composition comprising an active ingredient, a derivative of sulfonated amide pyrimidinecarbonitrile acid and targeted supplements, featuring the group of formula:

< / BR>
where

R1represents a C1-C6-alkyl, optionally containing one or two substituent selected from the group comprising: halogen, C3-C5-cycloalkyl, C1-C4-alkylthio, C1-C4-alkylsulfonyl, C1-C4-alkoxycarbonyl, C2-C4-alkylsulphonyl; C2-C6-alkenylphenol group, optionally containing one or two substituent selected from a halogen; C2-C6-quinil; C5-C6-cycloalkyl, which can be substituted by oxopropoxy; 1-pyrrolidinyl; 2-methyl-1-piperidinyl; 1-aziridinyl or the group-NR5R6in which R5represents a hydrogen atom, a C1-C4-alkyl, C1-C4-alkoxy; R6represents a C1-C4-alkyl, C2-C5alkenyl, C1-C4-alkoxy-C1-C4-alkyl; R2represents a hydrogen atom, a C1-C4-alkoxy-C1-C4-alkyl; R3represents halogen, C1-C4-alkyl,

C1-C4-alkoxy; R4represents a C1-C4-alkyl, C1-C4-alkoxy, di(C1-C4)alkylamino in an effective amount.

The present invention, the de as a fungicidal composition using the composition described above, when the application dose of 500 ppm of active ingredient.

Also, a method of weed control by tillage and/or plants herbicide composition, where the composition using the above-described composition at a rate of consumption of the active ingredient, 1,6 - 400 g/10 ar.

Derivatives of N-sulfonamida, including N-containing 6-membered aromatic ring represented by formula /1/, can exist as geometric isomers of E configuration and Z configuration. The present invention includes each geometric isomer and a mixture thereof in an arbitrary ratio. In connection formula /1/ the alkyl group may mean, for example, alkyl group containing from 1 to 10 carbon atoms; Alchemilla group can be represented alkenylphenol group containing 2 to 8 carbon atoms, Alchemilla group can be alkenylphenol group containing from 2 to 8 carbon atoms; cycloalkyl group can be cycloalkyl group containing from 3 to 8 carbon atoms; alkoxygroup can be alkoxygroup containing from 1 to 6 carbon atoms; and a halogen atom may be chlorine, bromine, fluorine or IO the corresponding description of the connection will be referred to under the number given in table. 1 and 2.

Compounds corresponding to the present invention can be obtained by preparative methods A-E.

Preparative method A

/1/

< / BR>
In this scheme, R1, R3, R4X and Y have the foregoing significance.

The compound represented by the formula [I-1] , can be obtained by the interaction of the compounds represented by the formula [II] with 1 to 1.5 equivalents of the compound represented by the formula [III] in a solvent in the presence of a condensing agent.

As the condensing agent, there can be mentioned diethylthiophosphate, N, N'-carbonyldiimidazole, thionyl chloride, N,N'-dicyclohexylcarbodiimide, or etc.

As solvent there may be mentioned benzene, toluene, xylene, dichloromethane, chloroform, diethyl ether, tetrahydrofuran, dioxane, acetonitrile, N,N-dimethylformamide, N,N-dimethylacetamide, dimethylsulfoxide, or the like.

The reaction, if necessary, can be carried out in the presence of a base, such as triethylamine, sodium hydride, pyridine, etc.

The reaction can be carried out at a suitable temperature, which ranges from -20oC to +50oC, during the time from the gene, R1, R3, R4X and Y are set higher than the value R11represents an alkyl group (optionally substituted by alkoxygroup or alkoxycarbonyl group), a benzyl group or alkenylphenol group.

The compound represented by the formula [I-2] can be obtained by the interaction of the compounds represented by the formula [I-1], with 1 to 1.5 equivalents of the compound represented by formula [IV], in a solvent in the presence of a base.

As bases there may be mentioned triethylamine, sodium hydride, pyridine or etc.

As solvent there may be mentioned benzene, toluene, xylene, diethyl ether, tetrahydrofuran, dioxane, acetonitrile, N,N-dimethylformamide, N,N-dimethylacetamide, dimethylsulfoxide, or etc.

This reaction can be carried out at a suitable temperature from -20oC to +50oC for a time from 30 minutes to 20 hours

Preparative method C

/Figure 3/

< / BR>
Here M+represents an alkali metal ion, alkaline earth metal, ammonium, ammoniagenesis ion or transition metal ion, and R1, R3, R4X and Y have the foregoing significance.

Seed], from 0.5 to 1 equivalent of a base in a solvent.

As bases there may be mentioned alkali metals such as sodium, potassium or etc., a hydride of an alkali metal or hydride alkaline earth metal, such as sodium hydride, potassium hydride, calcium hydride or similar , hydroxide of alkali metal or alkali earth metal hydroxide such as sodium hydroxide, potassium hydroxide, calcium hydroxide, or etc., alkali metal alkoxide such as sodium methoxide, tert-piperonyl or potassium, etc., organic amine, such as ammonia, Isopropylamine, or etc.

As solvent there may be mentioned benzene, toluene, xylene, diethyl ether, tetrahydrofuran, dioxane, acetonitrile, methanol, ethanol, N,N-dimethylacetamide, dimethylsulfoxide, water, or etc.

This reaction can be carried out at a suitable temperature from -20oC to +50oC for a time from 30 minutes to 20 hours

Preparative method D

/Figure 4/

< / BR>
Here R1, R3, R4X and Y have the meanings specified above.

The compound represented by the formula [I-1] , can be obtained by the interaction of the compounds represented by formula [VI], with 0.5 to 1 equivalent of the compounds is s benzene, toluene, xylene, dichloromethane, chloroform, diethyl ether, tetrahydrofuran, dioxane, acetonitrile, N,N-dimethylformamide, N,N-dimethylacetamide, dimethylsulfoxide, or etc.

The reaction can be carried out in the presence of a base, such as triethylamine, sodium hydride, pyridine, or so on, if needed.

This reaction can be carried out at a suitable temperature from -20oC to +50oC for a time from 30 minutes to 20 hours

Preparative method E

/5/

< / BR>
Here R3, R4, R5, R6X and Y have the foregoing significance.

The compound represented by the formula [I-4] , can be obtained by the interaction of the compounds represented by formula [VII] with a compound represented by formula [VIII], in a solvent.

The reaction, if necessary, can be carried out in the presence of a base, such as triethylamine, sodium hydride, pyridine, or etc.

The compound represented by formula [VII] can be obtained by the interaction of the compounds represented by formula [III], with 1 to 1.5 equivalents chlorosulfonylisocyanate in solvent.

For each of the above reactions as solvents can be ethical, dimethyl sulfoxide, or so on, This reaction can be carried out at a suitable temperature from -20oC to +50oC for a time from 30 minutes to 20 hours

Methods for obtaining compounds of the present invention, will be discussed further in the following examples.

Example 1. Synthesis of N-isobutylphenyl-4,4-dimethoxypyrimidine-2 - carboxyamide (compound 8)

To a solution containing 2.0 g (11 mmol) of 4,6-dimethoxypyrimidine-2-carboxylic acid, dissolved in 20 ml of N,N-dimethylformamide, add 1.8 g (11 mmol) of N,N-carbonyldiimidazole, and the mixture is then stirred for 1 h at room temperature to prepare a solution containing 4,6-dimethoxypyrimidine-2-carbonyldiimidazole in N,N-dimethylformamide. Next, to a solution containing 1.5 g (11 mol) of Isobutyraldehyde dissolved in 20 ml of N, N-dimethylformamide, add 0.5 g (12 mmol) of 60% sodium hydride. After stirring the mixture for 1 h at room temperature thereto at room temperature is added dropwise a solution containing 4,6-dimethoxypyrimidine-2-carbonyldiimidazole in N,N-dimethylformamide. After stirring the reaction mixture for 3 h at room temperature the mixture was poured into cold water with l who have twice 200 ml of ethyl acetate. The extract is washed with water, the organic layer is dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure and programs 3.1 g of a viscous fluid. A viscous clear liquid column chromatography on silica gel (mixture of ethyl acetate with hexane in a ratio of 1:1), thus obtaining 2.7 g of the desired product (yield 82,0%). White crystalline granules, melting point 128 - 130oC.

Example 2. Synthesis of N-(2-chloro-2-propylsulfonyl)-4,6 - dimethoxypyrimidine-2-carboxyamide (compound N 23)

Dissolve 2.4 g (13 mmol) of 4,6-dimethoxypyrimidine-2-carboxylic acid, 2.0 g (13 mmol) of 2-chloro-2-propanesulfinamide and 3.9 g (39 mmol) of triethylamine in 50 ml of dichloromethane, and the mixture is then stirred for 30 min at room temperature. Then added to the mixture of 3.0 g (13 mmol) of 70% diethylthiophosphate, and the whole mixture was stirred at room temperature overnight. The reaction mixture is washed with diluted hydrochloric acid to remove excess triethylamine, after which the product is extracted with 50 ml saturated aqueous sodium bicarbonate solution. The extract is acidified with diluted hydrochloric acid to achieve a pH of 2 to 3. The organic layer is extracted with twice 200 ml of ethyl acetate. The extract is washed in the receive 1.8 g of a viscous fluid. A viscous clear liquid column chromatography on silica gel (ethyl acetate : hexane = 1:1), thus obtaining 1.4 g of the desired product (yield 33.7 percent). The yellow powder, melting point 125 -130oC.

Example 3. Synthesis of 4,6-dimethoxy-N-methoxymethyl-N - propylsulfonyl-2-carboxyamide (compound No. 48)

To a solution containing 2.0 g (6.8 mmol) of 4,6-dimethoxy-N-propylsulfonyl-2-carboxylic acid, dissolved in 100 ml of N,N-dimethylformamide, added 0.32 g (8.0 mmol) of sodium hydride in small portions and the mixture is then stirred for 1 h at room temperature. Then to the mixture of 0.54 g (6.8 mmol) of methoxymethane, and the whole mixture was stirred at room temperature for 1 h, the Reaction mixture was poured into water. The organic layer is extracted with toluene and dried over anhydrous magnesium sulfate and then concentrated under reduced pressure to get crude product, containing 4,6-dimethoxy-N-methoxymethyl-N-propylsulfonyl-2 - carboxamide. The crude product is purified column chromatography on silica gel (ethyl acetate : hexane = 1:1), thus obtaining 0.5 g of the desired product (yield 22.1 per cent). White powder, melting point 59 - 62oC.

Example 5. Synthesis of 4,6-dimethoxy-N-butylsulfonyl-2 - carboxyamide (compound No. 6)

Dissolve 3.0 g (16 mmol) of 4,6-dimethoxypyrimidine-2-carboxylic acid, 2.6 g (16 mmol) butylmethacrylate and 1.8 g (16 mmol) of triethylamine in 200 ml of chloroform, and the mixture is then stirred for 6 h at room temperature. Then the reaction mixture was washed with 10% hydrochloric acid and water, the organic layer is dried over anhydrous magnesium sulfate and then concentrated under reduced pressure to get crude product, containing 4,6-dimethoxy-N-butylsulfonyl-2-carboxamide. The crude product is purified column chromatography on silica gel (ethyl acetate : hexane = 1:1), and thus, 1.5 g of the desired product (vicoprofen.another)pyrimidine-2-carboxamide (compound N 118)

To a solution containing 3.0 g (16 mmol) of 4,6-dimethoxypyrimidine - 2-carboxylic acid, dissolved in 100 ml of dichloromethane, add small portions of 2.8 g (20 mmol) chlorosulfonylisocyanate, and the mixture is then stirred for 1 h at room temperature. Then to the reaction mixture at room temperature is added dropwise 3.0 g (50 mmol) of Isopropylamine, and the mixture is stirred at room temperature for 3 hours, the Reaction mixture was washed with 10% hydrochloric acid and water. The organic layer is dried over anhydrous magnesium sulfate and then concentrated under reduced pressure to get crude product, containing 4,6-dimethoxy-N-(isopropylaminocarbonyl)pyrimidine-2-carboxamide. The crude product is purified column chromatography on silica gel (ethyl acetate : hexane = 1:3), and thus, 0.8 g of the desired product (yield of 16.0%). White powder, melting point 167 - 169oC.

Biocide corresponding to the present invention is a composition containing as an active ingredient derived N-sulfonamida (-N sulfadimethoxine), including N-containing 6-membered aromatic ring represented by the formula [I]. When the connection strevent, can be entered in appropriate formulations, depending on the purpose of use. The active ingredient is usually diluted with an inert liquid or solid carrier and, if necessary, add a surfactant, a dispersant, adjuvant, etc., the Mixture was then formulated into a thin powder, wettable powder, emulsifiable concentrate, granules, etc.

As a suitable carrier used in the formulation, there may be mentioned, for example, such solid carriers, as talc, bentonite, clay, diatomaceous earth, white carbon, vermiculite, kaolin, hydrated lime, ammonium sulfate, urea, or so forth; and such liquid carriers as isopropyl alcohol, xylene, cyclohexanone, methylnaphthalene, etc., Illustrative examples of surfactants and dispersing agents include the salts dinaftiletilena acid, alkarylsulphonate acid and lignosulfonic acid, Solfatara alcohol, ethers of polyoxyethyleneglycol, ethers of polyoxyethyleneglycol, monoalkylated of polyoxyethylenesorbitan, etc., Suitable examples of auxiliary substances are carboxymethylcellulose, etc., These drugs may be used directly or after dilution to prisciani stems and foliage, the introduction of water for irrigation or soil. The amount of active ingredient is selected depending on requirements. When the formulation is prepared in the form of fine powder or granules, preferably the content of the active ingredient from 0.1 to 20 wt.%. For emulsifiable concentrate or wettable powder is adequate amount of the active ingredient from 5 to 80 wt.%.

The dose of biocide corresponding to the present invention may vary depending on the type of active compound, the type of pest or disease that is the struggle, the nature of the manifestations of the pest or disease, the degree of damage to the environment, the form in which the preparation is used, etc. When the biocide of the present invention is used directly in the form of fine powder or granules, the recommended dose of the active ingredient in the range of from 0.1 g to 5 kg per 10 ar /0.1 ha/, preferably in the range from 1 g to 1 kg per 10 ar. When the biocide of the present invention is in a liquid form such as emulsifiable concentrate or wettable powder, the recommended dose of the active ingredient in the range of from 0.1 to 10 in the structure described above formulations can be used to combat plant diseases, caused by the fungus belonging to Oomycetes. This fungus include, but are not limited to, Pseudoperonospora, such as the causative agent of downy mildew on cucumber (Pseudoperonospora cubensis), Plasmopara, such as the causative agent of downy mildew of grape (Plasmopara Vibicola), and Phytophtora, such as the causative agent of late blight of tomato (Phytophtora intestans).

Biocide corresponding to the present invention, if necessary, can be used in combination with fungicides, insecticides, herbicides, modifiers plant growth, fertilizers, or etc.

Next, typical formulations are illustrated in the following further examples of compositions in which all the mean percent mass percent.

Example composition 1

Fine powder

Mix until smooth 2% of compound (93), 5% of diatomaceous earth and 93% of clay and crushed into fine powder.

Example composition 2

Wettable powder

Mix until smooth 50% of compound (95), 45% of diatomaceous earth, 2% dinaftiletilena sodium and 3% of sodium lignosulphonate and grind in a wettable powder.

Example of part 3

Emulsifiable concentrate

Prepare a homogeneous solution of 30% concentration (80), 20% Catalina, thus obtaining the emulsifiable concentrate.

Example of part 4

Granules

Mix until smooth 5% of compound (98), 2% laurylsulphate sodium, 5% sodium lignosulphonate, 2% carboxymethylcellulose and 86% of clay and grind. To the milled mixture is added 20% water. The resulting mixture is stirred and molded into pellets of size 14 to 32 mesh using an extrusion granulator, and then dried, obtaining the desired granules.

Biocide corresponding to the present invention, can be used as a herbicide for the control of noxious weeds. In this case, with regard to the application and other formulations, preferably, the biocide used in the States, best for use as a herbicide. However, even in the conditions described for biocide above, biocide, corresponding to the present invention can carry out the tasks of the herbicide.

The effect of the invention

Derivatives of N-sulfadimethoxine, including N-containing 6-membered aromatic ring corresponding to the present invention detects not only excellent ability to prevent infection by the fungus, it also detects superb spoila disease of plants, especially for diseases such as downy mildew and late blight, at low concentrations compared with the known compounds described in the patent application of Japan, the first publication N Hei 2-282371. In addition, biocides, corresponding to the present invention have excellent performance by properties such as residual activity and resistance to precipitation.

In addition, the compounds corresponding to the present invention may also deal with weeds found in rice fields and plowed fields. Compounds superb work against various weeds in a plowed fields, including broad-leaved weeds, such as duck-leaved, slender amaranth, pigweed ordinary white, blue morning glory, common Cucklebur, etc. as well as against annual and perennial weeds type site, such as purple nutsedge, yellow nutsedge, himekugu (cyperus brevifolius), sedge, rice syt weerasena, etc. and grass weeds, such as millet plushie, sorghum Halep, Alopecurus myservername, etc. starting from the stage of germination and growth stage. In addition, the compounds can also be used to fight with annual weeds in rice fields, such as early mustard field, smallflower, duckweed (utility (water nutgrass), water chestnuts, Japanese bulrush, narrow-leaved arrowhead, etc.

As suitable crops here we can mention the rice plants, conventional field crops, fruit trees, etc.

The effect of the biocides of the present invention will now be illustrated by the following further testing examples.

Test example 1

Efficacy trials prevent infection of cucumber downy mildew (Pseudoperonospora cubensis).

Seeds of cucumber (variety Sagaminanjiro) are sown in polyvinylchloride (PVC) pots, with the length of each side 9 cm, 12 seeds in each pot. Seeds to grow in the greenhouse for 7 days prior to the stage of emergence of the cotyledons. Wettable powder obtained in example composition 2, dilute with water to a concentration of 500 ppm of active ingredient, and the resulting aqueous preparation is applied in an amount of 10 ml per pot of seedlings at the stage cotyledons. After drying in air plants inoculant spores of the fungus, calling on cucumber downy mildew (Pseudoperonospora cubensis), and then placed in a moist chamber at 22oC for 24 h, and then placed in the greenhouse. On the seventh day after inoculation to assess the prevalence of damages is dinani, relevant to the present invention, the test Results are given in table. 3.

For comparison, use the following compounds disclosed in the patent application of Japan N Hei 2-282371:

Connection for comparison A: N-(2-chlorophenylsulfonyl)-4,6 - dimethoxypyrimidine-2-carboxamide;

Connection for comparison B: N-(2,6-dichlorobenzenesulfonyl)-4,6 - dimethoxypyrimidine-2-carboxamide.

Standards assessments:

Group A: damage does not occur.

Group B: size distribution of less than 25%.

Group C: size distribution of 25% or more but less than 50%.

Group D: the extent of 50% or more (table. 3).

Test example 2

Testing the effectiveness of treatment when infection of cucumber downy mildew (Pseudoperonospora cubensis).

Seeds of cucumber (variety Sagami hanjiro) were seeded in polyvinylchloride (PVC) pots with a side of 9 cm, 12 seeds in each pot. Seeds allow to germinate in a greenhouse for 7 days prior to the stage cotyledons. Seedlings inoculant by spraying a suspension of the zoosporangium inside host fungus that causes downy mildew of cucumber (Pseudoperonospora cubensis) and then placed in a moist chamber at 22oC for 24 h After drying in air the ka, manufactured in example composition 2, up to a concentration of 500 ppm, at a dose of 10 ml per pot. The seedlings are then placed in the greenhouse. On the seventh day after inoculation to assess the degree of the damage in accordance with standards, assessments, data in test example 1 to evaluate the effect of treatment with the compounds disclosed in this invention, the infected plants. The test results are given in table. 4.

Test example 3

Tests of herbicide effectiveness in treating soil of rice fields

In plastic growing pot (100 cm2) filled with soil from the rice field, sown early mustard field (abbreviated as Eo), duckweed (duck tongue) (abbreviated Mo) and Japanese lake reeds (abbreviated Sc) and pour water layer in 3 see the next day wettable powder obtained in accordance with example formulations 2, diluted with water and treated soil from the rice field with water at a dose of 100 g of active ingredient per 10 ar, and after that leave for growing in the greenhouse. Herbicide evaluation carried out on day 21 after treatment. The results were evaluated in accordance with standards specified in the table. 5, and present them in table. 6 under the appropriate numeric indexes.

Test example 4

Test herbicide effectiveness in treating soil plowed fields

In plastic growing pot (120 cm2) filled with soil from plowed fields, sewout plushie millet (abbreviated as Ec), duck-leared (abbreviated as Po), slender aramant (abbreviated Am), common pigweed white (abbreviated Ch) and riceflatsedge (abbreviated Ci) and sprinkled soil. Wettable powder obtained in accordance with example formulations 2, diluted with water and uniformly sprayed on the soil surface with plowed fields, using the compact spray at a dose of 100 l wettable powder per 100 ar, so that the amount of active ingredient was 400 g / 10 ar, and subsequently placed for growth in the greenhouse. Herbicide evaluation carried out on day 21 after treatment. The results were evaluated in accordance with the standards shown in the table. 5, and present them in table. 7 under the corresponding digital codes.

As substances for comparison use the same connection that in test example 1.

Test example 5

Tests of herbicide effectiveness in treating stems and foliage

In plastic vegetation Saxena Po), slender amaranth (abbreviated Am), common pigweed white (abbreviated Ch) and rice flatsedge (abbreviated Ci) and then placed for growing in the greenhouse for 2 weeks. Wettable powder obtained in accordance with example formulations 2, dilute with water and spray the stems and leaves of plants, treating the whole plant, starting from the top, using a compact spray at a dose of 100 l wettable powder 10 ar, so that the amount of active ingredient was 400 g / 10 ar, and subsequently placed in a greenhouse. Herbicide evaluation is performed on day 14 after treatment. The results were evaluated in accordance with the standards shown in the table. 5, and bring them under the appropriate numeric indexes in the table. 8.

As substances for comparison using the same compounds, which are mentioned in test example 1.

Test example 6

Test the selectivity of action in the treatment of soil with plowed fields

In plastic growing pot (600 cm2) filled with soil from plowed fields, sow seeds of cultivated soybean (abbreviated as Gl), ipomea blue (abbreviated as Ip) and common cucklebur (abbreviated Xa) and sprinkled soil. On sleduushego in accordance with example formulations 1, dilute with water, sprinkle evenly over the soil surface with plowed fields, using the compact spray at a dose of 100 l wettable powder 10 ar, and then placed in a greenhouse. Herbicide evaluation carried out on day 21 after treatment. The results were evaluated in accordance with the standards shown in the table. 5, and present them in table. 9 under the corresponding digital codes.

Test example 7

Test the selectivity of the steps in the processing of stems and foliage plants

In plastic growing pot (600 cm2) filled with soil from plowed fields, sow seeds of cultivated soybean (abbreviated as Gl), ipomea blue (abbreviated as Ip) and common cucklebur (abbreviated Xa) and sprinkled soil, and subsequently placed in a greenhouse for growing for 2 weeks. A predetermined effective amount of (act. ingr., g/10 ar) wettable powder obtained in accordance with example formulations 1, diluted with water and sprinkle evenly on the stems and leaves of the plants throughout the plant, starting from the top, using a compact spray at a dose of 100 l wettable powder 10 ar, and placed in the greenhouse. Herbicide evaluation is performed on ablaut in table. 10 under the corresponding digital codes.

Test example 8

Test herbicide effectiveness in treating soil of flooded rice fields

In a plastic pot (100 cm2) filled with soil from the rice fields were sown the seeds of early batoshevo millet (used abbreviation Eo), green hellebore (used abbreviation Mo) and bulrush Japanese (used abbreviation Sc), after which the soil was flooded with water to a depth of 3 see the next day wettable powder obtained in accordance with example composition 2, was diluted with water and dropwise introduced into the soil of flooded rice fields with water at the rate of 100 g of active ingredient per 10 ar, after which the seeds were germinated in the greenhouse. Herbicide evaluation was made on the 21st day after the treatment. The results were determined in accordance with the standards as specified in the table. 11 and illustrated by means of the indexes in the table. 12.

1. Derivatives of amide N-sulfonylamino acids, including N-containing 6-membered aromatic ring, the General formula

< / BR>
where R1- C1- C10-alkyl, optionally containing one or two substituent selected from the group including halogen, C3- C5of IMT, WITH2- C4-alkylsulphonyl, or R1- C2- C6alkenyl, optionally containing one or two substituent selected from a halogen, or R1- C2- C6-quinil, or R1- cyclo-C5- C6-alkyl which can be substituted by exography, or R1- 1-pyrrolidinyl, 2-methyl-1-piperidinyl, 1-aziridinyl, R5R6N-;

R2is hydrogen, (lower)alkoxy(lower)alkyl;

R3and R4independently from each other halogen, C1- C4-alkyl, lower alkoxy, di(lower)alkylamino;

R5and R6independently from each other hydrogen, C1- C5-alkyl, lower alkoxygroup, lower alkenyl, cyclo(lower)alkyl, lower quinil,1- C4-alkoxy-C1- C4-alkyl.

2. Derivatives of amide-N-sulfonylamino acids, including N-containing 6-membered aromatic ring, p. 1, in which R1- C1- C10-alkyl, optionally containing one or two substituent selected from the group comprising halogen, C3- C5-cycloalkyl,1- C3-alkylthio,1- C3-alkylsulfonyl,1- C6-alkoxycarbonyl,2- C4-alkylsulphonyl or SUB> - C6-quinil or cyclo-C5- C6-alkyl which can be substituted by exography, or 1-pyrrolidinyl, 2-methyl-1-piperidinyl, 1-aziridinyl, or the group-NR5R6, R2is hydrogen, methoxy-C1- C3-alkyl, R3and R4independently from each other halogen, C1- C3-alkyl, C1- C3-alkoxy, di(C1- C3)alkylamino, R5is hydrogen, C1- C5-alkyl, C1- C3-alkoxy, R6- C1- C5-alkyl, C2- C5alkenyl, cyclo-C3- C5-alkyl, C2- C5-quinil.

3. Derived amide-N-sulfonylamino acids, including N-containing 6-membered aromatic ring, p. 1, where R1WITH2- C6alkenyl, optionally containing one or two substituent selected from halogen, R2is hydrogen, methoxymethyl group, R3and R4independently from each other halogen, methyl, methoxy, dimethylamino.

4. Fungicidal composition comprising active ingredient - derived amide pyrimidinecarbonitrile acid and the target additives, characterized in that as the amide derivative pyrimidinecarbonitrile acid it contains a compound of General formula
from the group including halogen, C3- C5-cycloalkyl,1- C4-alkylthio and oxiranyl group; or (C2- C6alkenyl, optionally containing 1 or 2 halogen or the group-NR5R6in which R5is hydrogen, C1- C4-alkyl, R6- C1- C4-alkyl, C2- C5-quinil,3- C5-cycloalkyl, R2is hydrogen, C1- C4-alkoxy-C1- C4-alkyl, R3- halogen, C1- C4-alkyl, C1- C4-alkoxy, R4- C1- C4-alkoxy, di(C1- C4)-alkylamino, in an effective amount.

5. Herbicide composition comprising an active ingredient, a derivative of sulfonated amide pyrimidinecarbonitrile acid and the target additives, characterized in that as a derivative of sulfonated amide pyrimidinecarbonitrile acid it contains a compound of General formula

< / BR>
where R1- C1- C6-alkyl, optionally containing one or two substituent selected from the group comprising halogen, C3- C5-cycloalkyl,1- C4-alkylthio,1- C4-alkylsulfonyl,1- C4-alkoxycarbonyl,2- C4-alkylic from halogen, WITH2- C6-quinil,5- C6-cycloalkyl, which can be substituted by exography, 1-pyrrolidinyl, 2-methyl-1-piperidinyl, 1-aziridinyl or the group-NR5R6in which R5is hydrogen, C1- C4-alkyl, C1- C4-alkoxy, R6- C1- C4-alkyl, C2- C5alkenyl,1- C4-alkoxy-C1- C4-alkyl;

R2is hydrogen, C1- C4-alkoxy-C1- C4-alkyl;

R3- halogen, C1- C4-alkyl, C1- C4-alkoxy;

R4- C1- C4-alkyl, C1- C4-alkoxy, di(C1- C4)-alkylamino,

in an effective amount.

6. A method of combating phytopathogenic fungi by treating the plant a fungicidal composition, characterized in that the fungicidal composition use composition on p. 4 when the ava 500 million-1the active ingredient.

7. Method of weed control by tillage and/or plants herbicide composition, characterized in that the composition use composition under item 5 the rate of application of active ingredient 1,6 - 400.0Hz in units of g/10 ar.

 

Same patents:

The invention relates to a new method of obtaining 2-substituted 4,6-dialkoxybenzene General formula I

< / BR>
in which

R1and R2may be the same or different and mean (C1-C4)-alkyl, and R3means R4-O-, R4-S - or R4R5N-, where R4equal to C1-C4-alkyl, R5means a hydrogen atom, a C1-C4-alkyl or phenyl; 2-N-alkylamino-4,6-dimethoxypyrimidine and method for producing a halogen-substituted pyrimidine

Ammonium salts // 2106346

The invention relates to an improved process for the preparation of substituted N-(1,3,5-triazine-2-yl)aminocarbonyl-arylsulfonamides General formula

< / BR>
where R1= Cl, COOCH3;

R2= OCH3N(CH3)2;

R3= CH3, ON=C(CH3)2, ON=C(CH3)C2H5;

R4= H, CH3,

used in agriculture as herbicides and plant growth regulators

The invention relates to new derivatives of catechol and their pharmaceutically acceptable salts and esters which are useful as medicaments, antioxidants

The invention relates to new derivatives of sulfamethoxypyrazine and herbicides containing them as active ingredients

The invention relates to a derivative of propionic acid, useful as fungicides, to fungicidal compositions containing them and to methods used to combat fungi, especially fungal infections of plants

The invention relates to organic synthesis and concerns a method for obtaining substituted falicov and heterocyclic falicov General formula

(I) where ring a is selected from the group comprising residues:

a) phenyl,

b) pyridyl,

b) five-membered heteroaromatic ring containing oxygen, sulfur or nitrogen as a heteroatom;

R cyano, formyl, ketonuria group, carboxyl group, which may be in the form of the free acid, ester or salt, carnemolla group or mono - or disubstituted carnemolla group or ring

Z

Y1, Y2and Y3attached to carbon atoms and are independently hydrogen, halogen, hydroxyl, C1-8-alkyl, C2-8-alkenyl,2-8-quinil,1-8-alkoxy, C2-8-alkenylamine,2-8-alkyloxy,1-8-alkylsulfonate, each of which may be substituted by 1 to 6 halogen atoms and conjugated WITH1-8-alkoxyl,2-8-acyl, phenyl WITH1-8-alkoxyl, phenylthio, each of which can be substituted one or three halogen atoms;

Y1and Y2>W3, W4and W5independently is CH, CR3or N;

Z is a bridge consisting of elements selected from the group of methylene, substituted methylene, -C(O)-;

R1and R2each independently hydrogen, halogen, C1-8-alkyl, C1-8-alkoxy, C2-8-alkenylamine,2-8-alkyloxy, each of which may be substituted by 1 to 6 halogen atoms, 5 - or 6-membered heterocycle-C1-8-alkoxy, phenyloxy or phenyl-C1-8-alkoxy, each of which may be substituted by 1-3 substituents selected from halogen or1-8-alkyl; R2WITH1-8-alkyl, phenyl-C1-8-alkoxy or phenyl;

X and Y each independently hydrogen, hydroxyl, halogen, cyano, C1-8-alkyl, C1-8-alkoxy, C1-8-alkoxycarbonyl,2-8-acyloxy, carbamoylated,1-8-alkylthio, phenyloxy, phenyl S, each of which may be substituted by 1-3 halogen atoms, or together they predstavljaet,S,NH,NOR12илиCR13R14;

or X and R together may form a bridge having the formula-C(O)-O - or-C(O)-NR2where the carbonyl is attached to A; with the proviso that when R carboxyl in free ether or salt and X and Y together javlautsa, one of the rings a and b contains a heteroatom

The invention relates to a method for obtaining new pyrimidine derivatives possessing valuable fungicidal properties, which can find application in agriculture

Ammonium salts // 2106346

The invention relates to fungicidal compositions and methods of using the compositions for controlling fungal infections of plants

The invention relates to a new derived pikolinos acid, useful as components of the herbicide compositions, herbicide compositions containing it, which can be used in rice fields, cultivated fields and non-agricultural land

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

The invention relates to new biologically active compounds derived amide alanovoy acid, three different methods for their preparation, herbicide composition and method for killing weeds that may find application in agriculture

FIELD: organic chemistry, herbicides, agriculture.

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

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

wherein values n, A, R3, R4 and Z are given above. These compounds represent the parent substances used for preparing compound of the formula (I). Compounds of the formula (I) elicit high and selective herbicide activity.

EFFECT: valuable properties of compounds.

7 cl, 8 tbl, 7 ex

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