Using 3-[(substituted phenyl)carboxamido]-1,4,6-trimethyl-5-r-pyrazolo[4,5-b]pyridines as antidote of 2,4-d

FIELD: organic chemistry, agriculture.

SUBSTANCE: invention describes using 3-[(substituted phenyl)carboxamido]-1,4,6-trimethyl-5-R-pyrazolo[4,5-b]pyridines of the formula (1-4): wherein in (1) R means hydrogen atom (H); in (2) R means H; X means 2-methoxyphenyl; in (3) R means chlorine atom (Cl); X means 2-methoxyphenyl; in (4) R means Cl; X means ethyl as an antidote against 2,4-dichlorophenoxyacetic acid (2,4-D) in sunflower. Invention provides expanding assortment of biologically active substances prepared by synthetic method for their using in agriculture as an antidote of herbicide 2,4-D. Method involves treatment of sunflower seedlings damaged with herbicide by proposed 3-[(substituted phenyl)carboxamido]-1,4,6-trimethyl-5-R-pyrazolo[4,5-b]pyridines.

EFFECT: valuable biological properties of antidotes.

1 tbl, 6 ex

 

The invention relates to a synthetic, biologically active chemical substances of some heterocyclic compounds of formula 1-4:

1 - R=H, X=4-were;

2 - R=H, X=2-methoxyphenyl;

3 - R=Cl, X=2-methoxyphenyl;

4 - R=Cl, X=ethyl,

as a means of protection of plants from fetotoksicheskoe action of the herbicide 2,4-dichlorophenoxyacetic acid (antidotes). The claimed compounds previously known (Catalog of Chemical Blok Stok Library, Cas Registry No. 728887-44-3, 10.08.2004; No. 728888-08-2, 10.08.2004; No. 727667-16-5, 10.08.2004 and No. 728887-48-7, 10.08.2004 compounds 1-4, respectively),but their antidote properties identified for the first time.

As you know, the sunflower is extremely sensitive culture herbicide group, 2,4-D, and in cases of unintentional contact of herbicide on his crop losses can be depending on the dose up to 100% [Diganto, Mesocolon. Herbicide effect of 2,4-D and other halogenosilanes. M.: Nauka, 1973].

Still protecting vegetative plants of sunflower from the damaging effects of 2,4-D remains unresolved.

To the closest analogs in the structure of the claimed compounds can be classified as 3-amino-4,6-dimethyl-1H-pyrazolo[4,5-b]-pyridine 5 [M Lacan, Tabakovic K. Syntesis of pirazolo-, and tetrazolopyridines. /Croat. cem. Acta/ 1975, 47, No. 2, s.127-133].

As similar properties is known Sulfalen ["Antidote herbicide hormonal action of 2,4-dichlorophenoxyacetic acid and 4-amino-3,5,6-trichloro-Kalinovo acids" U.S. Pat. Of the Russian Federation No. 2043021 from 10.09.95,application No. 5042089 from 14.05.92] 6

Sulfalen formula 6 is used as a means of reducing the negative effects of the herbicide 2,4-D, he dose of 200 g/ha applied on damaged vegetating plants. At the same time Sulfalen widely used as antibacterial agents in clinical practice, its synthesis is described in the literature [Wegelius. Pharmaceutical chemistry. - M.: Higher school. 1985. p.383, 768.] However antidote activity Sulfalena is not high enough.

The present invention is to expand the Arsenal of biologically active substances obtained synthetically, for their application in agriculture as antidotes.

This is achieved by using 3-[(substituted phenyl)-carboxamido]-1,4,6-trimethyl-5-R-pyrazolo[4,5-b]pyridines 1-4 on seedlings of sunflower.

While the claimed compounds get known method - acylation of 3-amino-1,4,6-trimethyl-5-R-pyrazolo[4,5-b]pyridines anhydrides of aromatic and aliphatic carboxylic acids at a temperature of 10-12°in the medium of anhydrous benzene in the presence of triethylamine as an acceptor of hydrogen chloride [see Weigand Hilgefort experiment in organic chemistry. - M.: Chemistry. 1969. s.431].

The original 3-amino-1,4,6-trimethyl-5-pyrazolo[4,5-b]pyridine also on ucaut known method [see Shabica, Mbonabucya, Waiter, Glauber. Some reactions of nucleophilic substitution in the range of 2-chloro-3-cyanopyridines. - CHC, 1976, No. 8, s-1088].

Used benzene and acetone absolutetruth known method [smailagic, Proskauer, Griddim, Etopia solvents. M: Foreign literature, 1958, s].

The invention is illustrated by the following examples:

Example 1. 3[-(4-were)-carboxamido]-1,4,6-trimethyl-pyrazolo[4,5-b]pyridine (compound 1)

To a suspension of 0.7 g (0,00370 mol) 3-amino-1,4,6-trimethylpyrazole[4,5-b]-pyridine and 0.38 (0,00370 mol) of triethylamine in 20 ml of absolute benzene was added dropwise over a 40-50 minute solution 0,69 g(0,00440 mol) of 4-methylbenzylamine in 10 ml of absolute benzene, maintaining the temperature of the reaction mixture in the range of 10-12°C. Upon completion of addition, stirred at the same temperature for another 10-20 minutes, then at room temperature for 3 hours. From the reaction mixture the precipitate was separated by filtration, washed it with warm water (3×20 ml), dried. The mother liquor is evaporated to dryness, the residue is treated with 15 ml of sulphuric ether, and dried. Both sediment unite, recrystallized from ethanol, to obtain 1.1 g (72%) of the target product 1 in the form of white crystals with TPL 236-237°C.

Found, %: C To 69.61; H 6,27; N 18,54. C17H18N4O

Calculated, %: C 69,35; N 6,18; N18,36.

TMR, δ, ppm(group is: to 2.35 (3H, with a, CH3Ph); to 2.55 (3H, s, 4-CH3Ru); to 2.65 (3H, s, 6-CH3Ru); 3,98 (3H, s, N-CH3); to 6.88 (1H, s, 5-H PY); 7,35...to 7.93 (4H, m, CH-Ph); 10,45 (1H, c, N-H).

The mass spectrum; m/z (relative. intensity): 294 M+(28); 134(3); 119(100); 104(5); 91(30); 65(12).

Example 2. 3-[(2-methoxyphenyl)-carboxamido]-1,4,6-trimethyl-pyrazolo [4,5-b]pyridine (compound 2)

To a suspension of 0.6 g (0,00320 mol) 3-amino-1,4,6-trimethylpyrazole[4,5-b]-pyridine and 0.32 (0,00320 mol) of triethylamine in 18 ml of absolute benzene was added dropwise over 40 minutes a solution of 0.52 g (0,00380 mol) of 2-methoxybenzylamine in 10 ml of absolute benzene, maintaining the temperature of the reaction mixture in the range of 10-12°C. Upon completion of addition, stirred at the same temperature for another 10-20 minutes, then at room temperature for 2 hours.

The reaction mass is separated from the precipitate (triethylamine hydrochloride), evaporated to dryness, the residue is treated with 10 ml of Et2O. After recrystallization from ethyl acetate to obtain 0.66 g (68%) of target compound 2, in the form of white crystals with TPL 158-159°C.

Found %: C 65,51; N 5,72; N 18.28; C17H18N4O;

Calculated, %: C 65,78; N 5,86; N 18,05.

TMR, δ, ppm(group): 2.58 (3H, s, 4-CH3Ru); in 2.68(3H, s, 6-CH3Ru); 3,90 (3H, s, N-CH3); of 4.05 (3H, s, och3); make 6.90 (1H, s, 5H PN); 7,09...a 7.85 (4H, m, CH Ph); 10,12 (1H, c. N-H).

Mass spectrum, m/z (relative. intensity): 310 M+(16); 135(100); 104(4); 92(12); 77(22)

Example 3. 3-[(2-methoxyphenyl-carboxamido]-1,4,6-trimethyl-5-chloropyrazole[4,5-b]pyridine (compound 3).

To a suspension of 0.8 g (0,00380 mol) 3-amino-1,4,6-trimethyl-5-chloropyrazole[4,5-b]-pyridine and 0.38 (0,00380 mol) of triethylamine in 25 ml of absolute benzene was added dropwise over a 40-50 minute solution 0,78 g (0,00456 mol) of 2-methoxybenzylamine in 10 ml of absolute benzene, maintaining the temperature of the reaction mixture in the range of 10-12°C. Upon completion of addition, stirred at the same temperature for another 10-20 minutes, then at room temperature for 3 hours.

The reaction mass is separated from the precipitate (triethylamine hydrochloride), evaporated to dryness, the residue is treated with 10 ml of Et2O. After recrystallization from ethyl acetate to obtain 0.84 g (64%) of target compound 3 in the form of white crystals with TPL 173-174°C.

Found, %: C 59,44; N Rate 4.79; N, 16.41; C17H17ClN4About

Calculated, %: 59,20; N To 4.98; N 16,25.

TMR, δ, ppm (group): 2.58 (3H, s, 4-CH3Ru); in 2.68 (3H, s, 6-CH3Ru); 3,90 (3H, s, N-CH3); 4,00 (3H, s, och3); 7,09...to 7.35 (4H, m, CH Ph); 10,15 (1H, c.N-H).

Mass spectrum, m/z (relative. intensity): 344 M+(7); 135(100); 92(11); 77(24).

Example 4. 3-(ethylcarbodiimide)-1,4,6-trimethyl-5-chloropyrazole [4,5-b] pyridine (compound 4)

To a suspension of 0.8 g (0,00380 mol) 3-amino-1,4,6-trimethyl-5-chloropyrazole[4,5-b]-pyridine and 0.38 (0,00380 mol) of triethylamine in 25 ml of absolute benzene was added dropwise within 40-50 minutes a solution of 0.33 g (0,0043 mol) propionitrile in 10 ml of absolute benzene, supporting t is mperature the reaction mixture in the range of 10-12° C. Upon completion of addition, stirred at the same temperature for another 10-20 minutes, then at room temperature for 3 hours.

The reaction mass is separated from the precipitate (triethylamine hydrochloride), evaporated to dryness, the residue is treated with 10 ml of Et2O. After recrystallization from ethanol to 0.67 g (71%) of target compound 4 in the form of white crystals with TPL 194-195°C.

Found, %: C 54,30; N 5,52; 21.18 N; C12H15ClN4About

Calculated, %: 54,03; N. Of 5.68; N 21,01.

TMR, δ, ppm (group): of 1.12 (3H, t, CH2CH3); 2,35 (2N, K, CH2CH3); to 2.55 (3H, s, 4-CH3Ru); to 2.65 (3H, s, 6-CH3Ru); 3,91 (3H, s, N-CH3); 10,08(1H, s, N-h).

Mass spectrum, m/z (relative. intensity): 266 M+(5); 210(35); 77(6); 44(100).

Example 5. 3-amino-1,4,6-trimethylpyrazole[4,5-b]pyridine (compound 5)

A mixture of 1.0 g (0,0061 mol) of 2-chloro-3-cyano 4,6-dimethylpyridine, 1.22 g (0,0244 mol) of hydrazine hydrate is added and 25 ml of anhydrous ethanol is boiled for 9 hours. After cooling the reaction mixture the precipitate is filtered off, washed on the filter with alcohol and recrystallized from methanol, get to 0.72 g (73%) of target compound 5 in the form of crystals pale yellow with TPL 239-240°

Found %: 59,39; N 6,12; N of 34.40; C8H10N4

Calculated, %: C 59,22; N 6,23; N 34,55.

TMR, δ, ppm (group): 2,40 (3H, s, 4-CH3Ru); to 2.55 (3H, s, 6-CH3Ru); to 5.08 (2H, NH2); to 6.58 (1H, s, NRW); 11,1 (1H, c, N-H).

Mass spectrum, m/z (relative. intensity): 162 M+(100); 133(24); 107(40); 105(32); 92(5); 84(12).

Example 6. Evaluation of compounds 1-6 on antidote activity in seedlings of sunflower

Sprouted sunflower seeds with the length of the embryonic root of 2-4 mm were placed for 1 h in a solution of 2,4-dichlorophenoxyacetic acid (2,4-D) at a concentration of 10-3% get 40-60% inhibition of hypocotyl growth. After herbicide exposure seedlings were rinsed with water and placed in the test solutions on the antidote activity of substances in concentrations of 10-2, 10-3, 10-4, 10-5(a variant of the herbicide + antidote). After 1 h, the seeds were washed with water and spread out on a strip of filter paper (size 10×75 cm) of 20 pieces, which were rolled into rolls and placed in beakers with 50 ml of water. Further germination of seeds was performed in an incubator for 3 days at a temperature of 28°C. the temperature of the solutions and wash water 28°C.

Seeds option "herbicide" (standard) kept for 1 h in a solution of 2,4-D at a concentration of 10-3and 1 h in water.

Seeds of control variant 2 hours stood in the water.

Experiment was repeated three times. In each replication were used for 20 pieces of seeds.

Protective (antidote), the effect was determined by increasing the length of hypocotyl and root in the embodiment, the herbicide + antidote otnositel the named values in the variant "herbicide" (reference).

Statistical processing of experimental data carried out using t-student test at P=0,95.

The research results are summarized in the table.

As can be seen from the table, the application on the background of the impact of herbicide offered as antidotes 3-(substituted phenylcarbonylamino)-1,4,6-trimethyl-1-R-pyrazolo[4,5-b]pyridines 1-4 dramatically reduces the toxic effect of the herbicide.

Compounds 1-4 were reduced negative effect of 2,4-D on the hypocotyl of seedlings, sunflower 28-41% using mainly three or more concentrations, while compound 5 (similar structure) protective effect was not shown, and the amount of antidote effect Sulfalena (prototype) was 12-20%.

Compounds 1-4 were reduced inhibitory effect of 2,4-D on the roots of seedlings on 29-55% when using three or more concentrations, compound 5 did not increase the root length of seedlings and Sulfalen (prototype) showed antidote effect on the level of 18-28%.

Thus, the use of the inventive 3-(substituted phenylcarbonylamino)-1,4,6-trimethyl-1-R-pyrazolo[4,5-b]pyridines as antidotes to effectively protect the sunflower from the effects of 2,4-D, as well as to expand the range of known antidotes.

Table.

EN Iduna activity of compounds 1-6 to 2,4-D on seedlings of sunflower varieties VNIIMK-8883.
MedicationConcentration %The length of the hypocotylRoot length
mmTo 2,4-D, %mmTo 2,4-D, %
Control068119
2,4-D10-33635
2,4-D + connection 110-251141*54153*
10-34312048138*
10-448134*49140*
10-548134*53151*
2,4-D + connection 210-24412246131*
10-349136*48136*
10-446128*41116
10-545124*45129*
2,4-D + with the Association 3 10-248133*50142*
10-349136*50142*
10-44512445129
10-546128*52148*
2.4-D + connection 410-249236*55155*
10-347132*49140*
10-446128*49140*
10-546128*53151*
2,4-D + connection 510-2328939111*
10-338106*3393
10-43710335100
10-538106*3086
2,4-D + Sulfalen(6) (prototype)10-24011245 128*
10-342118*45128*
10-445124*40114
10-543120*41118*
*Differences between the variants are significant at P=0,95.

Application of 3-[(substituted phenyl)carboxamido]-1,4,6-trimethyl-5-R-pyrazolo[4,5-b]pyridines of formula 1-4

1. R=H, X=4-were;

2. R=H, X=2-methoxyphenyl;

3. R=Cl, X=2-methoxyphenyl;

4. R=Cl, X is ethyl,

as an antidote against 2,4-dichlorophenoxyacetic acid in sunflower.



 

Same patents:

FIELD: organic chemistry, agriculture.

SUBSTANCE: invention describes using 3-amino-(substituted amino)-1,4,6-trimethyl-5-R-pyrazolo[4,5-b]pyridines of the formula (1-2): wherein in (1) R means chlorine atom (Cl); in (2) R means hydrogen atom (H); X means 4-methylphenyl as regulators of sunflower growth. Invention provides expanding assortment of some biologically active substances prepared by synthetic method for their using in agriculture as regulators of plants growth.

EFFECT: valuable biological properties of substances.

1 tbl, 4 ex

FIELD: organic chemistry, antidotes, agriculture.

SUBSTANCE: invention describes using N-substituted 3-cyano-4,6-dimethyl-5-chloropyridyl-2-sulfonylamides of the formula (1-2): wherein in (1) R means benzimidozolyl-1; in (2) R means furfurylamino-group as antidotes of herbicide 2,4-dichlorophenoxyacetic acid in sunflower. Invention provides expanding assortment of biologically active substances prepared by synthetic method for their using in agriculture as antidotes against 2,4-D. Method involves treatment of sunflower seedlings damaged with herbicide by proposed N-substituted 3-cyano-4,6-dimethyl-5-chloropyridyl-2-sulfonylamides.

EFFECT: valuable biological properties of antidotes.

1 tbl, 3 ex

FIELD: agriculture, in particular, suppression of weeds with developed triazine resistance resulted from selection stress acting upon weed population and caused by repeated application of triazines.

SUBSTANCE: method involves introducing into said weed locus combination of mesotrione and triazine, selected from the group consisting of atrazine, cyanazine, propazine, terbutilazine, trietazine, simazine and metribuzine. Mesotrione is introduced in an amount of from 20 to 210 g/hectare, triazine in an amount of from 0.1 to 2 kg/hectare.

EFFECT: increased efficiency of said combination as compared to that of mesotrione in case said combination is used with regard to triazine tolerable weeds.

3 cl, 9 tbl, 6 ex

FIELD: organic chemistry, herbicides.

SUBSTANCE: invention relates to a compound of the general formula [I]: wherein R1 and R2 can be similar or different and each represents (C1-C10)-alkyl group; each among R3 and R4 represents hydrogen atom; R5 and R6 can be similar or different and each represents hydrogen atom or (C1-C10)-alkyl group; Y represents 5-6-membered aromatic heterocyclic group or condensed aromatic heterocyclic group comprising one or some heteroatoms chosen from nitrogen atom, oxygen atom and sulfur atom wherein heterocyclic group can be substituted with 0-6 of similar or different groups chosen from the following group of substitutes α, and so on; n means whole values from 0 to 2; [Group of substitutes α]: hydroxyl group, halogen atoms, (C1-C10)-alkyl groups, (C1-C10)-alkyl groups wherein each group is monosubstituted with group chosen from the following group of substitutes β, (C1-C4)-halogenalkyl groups, (C3-C8)-cycloalkyl groups, (C1-C10)-alkoxy-groups, (C1-C10)-alkoxy-groups wherein each group is monosubstituted with group chosen from the following group of substitutes and so on; [Group of substitutes β]: hydroxyl group, (C3-C8)-cycloalkyl groups that can be substituted with halogen atom or alkyl group, (C1-C10)-alkoxy-group, (C1-C10)-alkylthio-groups, (C1-C10)-alkylsulfonyl groups, (C1-C10)-alkoxycarbonyl groups, amino-group, carbamoyl group (wherein its nitrogen atom can be substituted with similar or different (C1-C10)-alkyl groups), (C1-C6)-acyl groups, (C1-C10)-alkoxyimino-groups, cyano-group, optionally substituted phenyl group; [Group of substitutes γ]: optionally substituted phenyl group, optionally substituted aromatic heterocyclic groups, cyano-group. Also, invention relates to herbicide comprising derivative of isoxazoline of the formula [I] as an active component or its pharmaceutically acceptable salt. Invention provides the development of isoxazoline derivative possessing the herbicide activity with respect to resistant weeds, selectivity for cultural crop and weed.

EFFECT: valuable herbicide properties of substances.

18 cl, 24 tbl, 106 ex

FIELD: agriculture, in particular method for increasing of beet yield and sugar content.

SUBSTANCE: seeds are treated by spraying in leaf clamping step with titanium tetrachloride diluted in dimethylsulfoxide (DMSO). Concentration of DMSO is 0.1-2 %; titanium tetrachloride consumption is up to 50 g per 1 hectare of seeds. Ratio of titanium tetrachloride:dimethylsulfoxide is 100-200 l per 1 hectare. Treatment is carried out twice in vegetation period, namely the first treatment is carried out in leaf clamping step and the second one in 15-20 days before harvesting of root crops.

EFFECT: increased beet yield and sugar content.

1 tbl, 1 ex

FIELD: agriculture, organic chemistry.

SUBSTANCE: invention relates to agent for controlling of plant pathogen fungi containing compound of general formula I as active ingredient, wherein X represents =N-; E represents NO2 or CN; R representsthiazolulmethyl or pyridylmethyl substituted with halogen; A represents hydrogen; Z represents C1-C4-alkylamino group; or A and Z together with atoms bonded thereon form thiazolidine, imidazolidine, hexahydro-1,3,5-triazine, N2- and N5-substituted with two C1-C4-alkyl in alkyl group, 6-membered saturated heterocycle fragment including additionally oxygen and N-(C1-C4)alkyl heterogroup; and fungicide compound selected from group containing cyproconazole, triadimenol, methalaxide, azoxistrobin, kresoximmethyl, etc., in weight ratio compound of formula I/fungicidal agent of 1:(0.1-10). Also disclosed is insecticide agent containing compound of formula I and compound selected from group containing cyproconazole, azoxistrobin, kresoximmethyl, biterthanol, tiram, methalaxide, etc. in ratio of 1:(0.1-10).

EFFECT: enhanced assortment of agents for controlling of plant pathogen fungi and agents for insect controlling.

4 cl, 15 tbl, 15 ex

FIELD: agriculture, organic chemistry.

SUBSTANCE: invention relates to agent for controlling of plant pathogen fungi containing compound of general formula I as active ingredient, wherein X represents =N-; E represents NO2 or CN; R representsthiazolulmethyl or pyridylmethyl substituted with halogen; A represents hydrogen; Z represents C1-C4-alkylamino group; or A and Z together with atoms bonded thereon form thiazolidine, imidazolidine, hexahydro-1,3,5-triazine, N2- and N5-substituted with two C1-C4-alkyl in alkyl group, 6-membered saturated heterocycle fragment including additionally oxygen and N-(C1-C4)alkyl heterogroup; and fungicide compound selected from group containing cyproconazole, triadimenol, methalaxide, azoxistrobin, kresoximmethyl, etc., in weight ratio compound of formula I/fungicidal agent of 1:(0.1-10). Also disclosed is insecticide agent containing compound of formula I and compound selected from group containing cyproconazole, azoxistrobin, kresoximmethyl, biterthanol, tiram, methalaxide, etc. in ratio of 1:(0.1-10).

EFFECT: enhanced assortment of agents for controlling of plant pathogen fungi and agents for insect controlling.

4 cl, 15 tbl, 15 ex

FIELD: agricultural chemistry.

SUBSTANCE: invention relates to herbicidal composition containing (A) mesotrion and (B) the second herbicide selected from amicarbazone, metribuzine, flumetsulfam, trifloxysulfuron, pyriphthalide, prosulfocarb or herbicidically active salts thereof in (A):(B) ratio from 32:1 to 1:3. Disclosed is method for controlling of undesired plants which includes application of herbicidically effective amount of said composition into locus with such plants.

EFFECT: composition of high herbicidal activity.

8 cl, 6 tbl

FIELD: method for controlling of arthropod pests.

SUBSTANCE: claimed method includes application in environments of pests of germinal calls thereof effective amount at least one vicinal diol of formula R(OH)2 selected from group containing diols, wherein R represents aliphatic hydrocarbon chain with the proviso that carbon atom in the chain adjacent to diol functional group is not substituted with ethyl and chain skeleton contains 8-20 carbon atoms. Composition for insecticidal and arachnicidal application containing abovementioned diol of formula R(OH)2 also is disclosed. Methods for controlling of sucking lice, flies, mites, cockroaches, and pests from group comprising Pediculus humanus, Dermatophagoides pteronyssinus, and Musca domestica.

EFFECT: death or non-vitality of pests after treatment.

26 cl, 4 tbl, 4 ex

FIELD: method for controlling of arthropod pests.

SUBSTANCE: claimed method includes application in environments of pests of germinal calls thereof effective amount at least one vicinal diol of formula R(OH)2 selected from group containing diols, wherein R represents aliphatic hydrocarbon chain with the proviso that carbon atom in the chain adjacent to diol functional group is not substituted with ethyl and chain skeleton contains 8-20 carbon atoms. Composition for insecticidal and arachnicidal application containing abovementioned diol of formula R(OH)2 also is disclosed. Methods for controlling of sucking lice, flies, mites, cockroaches, and pests from group comprising Pediculus humanus, Dermatophagoides pteronyssinus, and Musca domestica.

EFFECT: death or non-vitality of pests after treatment.

26 cl, 4 tbl, 4 ex

FIELD: agricultural chemistry.

SUBSTANCE: invention relates to herbicidal composition containing (A) mesotrion and (B) the second herbicide selected from amicarbazone, metribuzine, flumetsulfam, trifloxysulfuron, pyriphthalide, prosulfocarb or herbicidically active salts thereof in (A):(B) ratio from 32:1 to 1:3. Disclosed is method for controlling of undesired plants which includes application of herbicidically effective amount of said composition into locus with such plants.

EFFECT: composition of high herbicidal activity.

8 cl, 6 tbl

FIELD: organic chemistry.

SUBSTANCE: invention describes C2-phenyl-substituted cyclic ketoenols of the general formula: wherein W means hydrogen atom, alkyl with 1-6 carbon atoms; X means alkyl with 1-6 carbon atoms, alkenyl with 2-6 carbon atoms; Y means hydrogen atom, methyl, ethyl, isopropyl, alkenyl with 2-6 carbon atoms, ethynyl; Z means hydrogen atom, alkyl with 1-6 carbon atoms under condition that at least one of residues W, X, Y or Z means a chain with at least 2 carbon atoms but only one of residues X and Y can mean alkenyl with 2-6 carbon atoms; CKE means one of the following groups: , , and wherein A means hydrogen atom, alkyl with 1-6 carbon atoms; B means hydrogen atom, alkyl with 1-6 carbon atoms; A and B in common with carbon atom to which they are bound mean cycloalkyl with 5-6 carbon atoms wherein the ring carbon atom can be substituted with oxygen atom and can be substituted with alkyl with 1-6 carbon atoms or alkoxyl with 1-6 carbon atoms; A and B in common mean group of the formula: D means hydrogen atom or phenyl substituted with fluorine atom if CKE means group of the formula (4); G means hydrogen atom (a) or one of groups of the formula: or wherein R1 means alkyl with 1-6 carbon atoms, alkoxymethyl with 1-2 carbon atoms; R2 means alkyl with 1-4 carbon atoms; A and Q1 in common mean alkanediyl with 3-4 carbon atoms; Q2 means hydrogen atom. Invention provides preparing compound of the formula (I) possessing with insecticide, acaricide and herbicide activity.

EFFECT: valuable properties of compounds.

2 cl, 8 tbl, 32 ex

FIELD: biotechnology.

SUBSTANCE: claimed composition contains (mass %): sodium lignogumate 0.5-1; hydropterine 0.5-1; and balance up to 100 %: water.

EFFECT: increased yield per unit; agriculture production of improved quality.

3 ex, 4 tbl

FIELD: agriculture, organic chemistry.

SUBSTANCE: invention relates to application of 2-[N-(2'-iodophenyl)carboxamido]-3-amino-4,6-dimethylthieno[2,3-b]pyridine of formula as stimulator of sunflower growth.

EFFECT: stimulation of sunflower seed germination; increased sunflower productivity.

2 tbl, 3 ex

FIELD: agriculture.

SUBSTANCE: method involves treating plants with 3-amino-2-N-[4-chlorobenzene)carbamido]-4,5,6-trimethylthieno-[2,3-b]-pyridine used in an amount of 200 g/hectare five days after application of herbicide. Method provides for protection of growing sunflower plants from injuring effect of 2,4-D.

EFFECT: increased yield of sun flower as compared to control sun flower plant treated with herbicide.

1 tbl

FIELD: organic chemistry, herbicides.

SUBSTANCE: invention describes a synergetic composition with the effective content of components (A) and (B) wherein (A) means herbicide chosen from the group of compounds of the formula (I): wherein R1, R2, R, X, Y and Z have values given in the invention claim or their salts; (B) means one or some herbicides among the following groups: (B1) selective herbicides with activity in some dicotyledonous cultures against monocotyledonous and dicotyledonous weeds; (B2) selective herbicides with activity in some dicotyledonous cultures against dicotyledonous weeds; (B3) selective herbicides with activity in some dicotyledonous cultures with preferable effect against monocotyledonous weeds. Also, invention describes a method for control against weeds using the proposed composition. Using the combination of proposed herbicides results to the synergetic effect.

EFFECT: valuable herbicide properties of composition.

3 cl, 7 tbl, 2 ex

Herbicide agent // 2273994

FIELD: herbicides, agriculture.

SUBSTANCE: invention describes a herbicide agent comprising fluphenacet and compound from the group comprising butaphenacyl-allyl, cinidon-ethyl, florasulam, flucarbazon-sodium, flupyrsulfuron-methyl-sodium, iodosulfuron-methyl-sodium, mezotrion, procarbazon-sodium chosen in the synergetic effective ratio. Proposed agent is used for selective eradication of weeds in different useful vegetable crops.

EFFECT: valuable properties of agent.

3 cl, 46 tbl, 4 ex

FIELD: organic chemistry, herbicides.

SUBSTANCE: invention describes phenyl-substituted heterocyclic 1,3-ketoenols of the formula (I): wherein R1 and R3 mean independently of one another ethyl or (C1-C2)-alkoxy-group; Q means the group of the formula (Q1): or (Q2): wherein R4 and R5 in common with atoms to which they are joined form 5-7-membered cycle that can comprise additionally anellated alkylene chain consisting of 2-6 carbon atoms that, in turn, can comprise two heteroatoms taken among oxygen atom, and indicated cycle can be substituted with halogen atom, hydroxy-group, (C1-C6)-alkoxy-group, (C1-C6)-alkoxy-(C1-C6)-alkoxy-group, (C1-C4)-alkylcarbonyloxy-group, hydroxy-(C1-C4)-alkoxy-group, hydroxycarbonyl-(C1-C2)-alkoxy-group, methoxycarbonyl-(C1-C2)-alkoxy-group, methoxyimino-, methoxyethoxyethoxy-group; R6 and R7 means (C1-C10)-alkyl; R8 means hydrogen atom; X means oxygen atom; R20 means (C1-C10)-alkyl, and also agronomically acceptable salts and isomers of these compounds. Also, invention describes a method for preparing compounds of the formula (I), herbicide agent and a method for control of weed growth based on compounds of the formula (I). Invention provides preparing compounds possessing the herbicide activity.

EFFECT: improved preparing method, valuable properties of compounds and agents.

5 cl, 28 tbl, 5 ex

FIELD: organic chemistry, agriculture.

SUBSTANCE: invention relates to synergetic herbicidal agent with active content of biologically active compounds including 2-(4-tiocarbamoil-2-fluoro-5-ethylsulfonamino-phenyl)-4-methyl-5-trifluoromethyl-2,4-dihydro-3h-1,2,4-triazol-3-one and sodium methyliodosulfurone or methosulam in ratio of 1:(0.1-2.5). Method for controlling of undesired plants using agent of present invention also is disclosed.

EFFECT: agent of high herbicidal activity and good tolerance in relates to culture plants.

3 cl, 7 tbl, 1 ex

FIELD: organic chemistry, insecticides.

SUBSTANCE: invention describes insecticide composition comprising the active amount of one pyridine compound of the formula (I)

or its salt wherein Y represents halogenalkyl group comprising from 1 to 2 carbon atoms and halogen atoms from 1 to 5; m = 0; Q represents compound of the formula:

wherein X represents oxygen atom; R1 and R2 represent independently hydrogen atom, alkyl group comprising from 1 to 6 carbon atoms and substituted with cyan-group, and one insecticide taken among carbofuran, carbosulfan, cipermethrin, bifentrin, acetamiprid, chlorfauazuron, fluphenoxuron, piriproxiphen, spinosad, emamectine benzoate, avermectin, buprophezin and fipronil taken in the weight ratio of compound of the formula (I) and other insecticide = from 1:2 to 100:1. The composition provides stable and strong effect and eradicates insects.

EFFECT: strong insecticide effect of composition.

4 cl, 11 tbl, 5 ex

FIELD: organic chemistry, antidotes, agriculture.

SUBSTANCE: invention describes using N-substituted 3-cyano-4,6-dimethyl-5-chloropyridyl-2-sulfonylamides of the formula (1-2): wherein in (1) R means benzimidozolyl-1; in (2) R means furfurylamino-group as antidotes of herbicide 2,4-dichlorophenoxyacetic acid in sunflower. Invention provides expanding assortment of biologically active substances prepared by synthetic method for their using in agriculture as antidotes against 2,4-D. Method involves treatment of sunflower seedlings damaged with herbicide by proposed N-substituted 3-cyano-4,6-dimethyl-5-chloropyridyl-2-sulfonylamides.

EFFECT: valuable biological properties of antidotes.

1 tbl, 3 ex

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