2-[n-(2'-iodophenyl)carboxamido]-3-amino-4,6-dimethylthieno[2,3-b]pyridine as stimulator of sunflower seed germination

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

 

The invention relates to chemistry and agriculture, particularly to substituted the pyridinethiones as plant growth regulators.

It is known the use of sodium HUMATE V.R., which is used as a growth stimulant plants, as well as for the stimulation of seed germination by soaking in an aqueous solution for 1 h [see the List of pesticides and agrochemicals permitted for use on the territory of the Russian Federation; Supplement to the journal "Protection and quarantine of plants", 2003, № 6]. The disadvantages of the use of sodium HUMATE V.R. are relatively high cost (240 thousand rubles per ton on 10.12.02), a narrow range recommended for seed treatment and relatively low stimulatory activity (it is weakly stimulates the development of the hypocotyl and root of seedlings).

Also known 2-R-3-amino-4,6-dimethyl-5-X-thieno[2,3-b]pyridine structure

which are used as an effective antidote herbicide hormonal action type [see U.S. Pat. Of the Russian Federation No. 2232762. / Iagaiganognia, Vukasin, Waitingin, Nieko, Gdescription, Lviagra, Lieskove, Vdistrict. Trialkylamine and thieno[2,3-b]pyridine - antidotes herbicides hormonal action of 2,4-dichlorophenoxyacetic acid. BI No. 20, 2004]. Use it as poststimulatory - unknown.

Technical resenje task Ki is expanding Arsenal of biologically active substances, obtained synthetically, for their application in agriculture as postregulation.

The task is achieved by using well-known derived series of thienopyridine (Catalog Name: Interchim Intermediates, CAS Registry No. 698993-58-7, 17.09.2004), namely 2-[N-(2'-itfeel)carboxamido]-3-amino-4,6-dimethylthieno[2,3-b]pyridine structure:

which can be used as an effective stimulator prorostania seeds that can increase the length of hypocotyl and root of seedlings of sunflower and sunflower harvest.

The novelty of the claimed proposal is seen that offered a certain substance 2-[N-(2'-itfeel)carboxamido]-3-amino-4,6-dimethylthieno[2,3-b]pyridine as a means of stimulating the germination and increases the yield of sunflower. Astragaloside properties discovered for the first time. The connection has a high growth stimulating activity, even at high (1·10-4-1·10-5wt.%) the dilutions that dramatically reduces consumption by DV and improves the environment; it is synthesized in a relatively simple and cheap source of food, which reduces its value.

Thus stated thienopyridine get known two-stage method the interaction of the corresponding 3-cyano-4,6-dimethyl-1(N)pyridine-2-thiones with aquamarine is the amount of KOH and 2-idfamilia Chloroacetic acid at a temperature of 20-25° With subsequent cyclization [see Synthesis of substituted 2-alkyl(aryl)thio-3-cyanopyridines and 3-aminothieno-[2,3-b]pyridines / Iagaiganognia, Ludkovsky, Snehalata. Vukasin, Vggallglkewyc // -CHC, 1996, No. 10, s-1437]. The original 3-cyano-4,6-dimethyl-1(N)-peridinin-2 and N-(2-itfeel)amide Chloroacetic acid get and purified by a known method [see Weigand-Hilgetag. Methods experiment in organic chemistry. - M.: Chemistry, 1969, s-582].

Dimethylformamide (DMF) immediately before use are cleaned and dried by a known method [see Agordon, Rford. Satellite chemist. M.: Mir, 1976. - 541 S.], and CON used in the medication qualification of analytical grade.

For comparison astragalina activity using known postregulatory - HUMATE potassium V.R., which is recommended for sunflower in a dose of 250 ml/ha in phase 2-3 true leaves [see the List of pesticides and agrochemicals permitted for use on the territory of the Russian Federation; Supplement to the journal "Protection and quarantine of plants", 2003, № 4, s]. This is the prototype for the application.

Examples of performance stated suggestions are presented below.

Example 1. 2-[N-(2'-itfeel)carboxamido]-3-amino-4,6-dimethylthieno[2,3-b]pyridine (FCTP)

To the suspension to 0.72 g (4.4 mmol) of 3-cyano-4,6-dimethyl-1(N)-pyridinone-2 in 12 ml of purified DMF under stirring at a temperature of 20±1°C was added dropwise a solution of 0.25 g (4.4 mm is l) of KOH in 4 ml of water, stir to dissolve the precipitate and was added dropwise a solution of 1.3 g (4.4 mmol) of N-(2-itfinal)amide Chloroacetic acid in 2 ml of DMF. Stirring is continued at the same temperature for another 1 h, the reaction mixture is make a solution of 0.25 g (4.4 mmol) of KOH in 4 ml of water and stirred for further 40 minutes, the Reaction mixture is diluted with 50 ml water, the precipitate is filtered off, washed with water and dried. After recrystallization from DMF obtain 1.2 g (67%) of the desired product as white crystalline powder with MP 242-244°C.

Found, %: C 45,66; N 3,51; N 9,80. C16H14IN3OS. Calculated, %: 45,40; N 3,34; N To 9.93.

X νcm-1(group): 3425, 3390 USSR. (NH); 1720 cf. (C=O); 1610, 1580, 1545 cf. (C=C, C=N - comp.).

TMR, δ, ppm (group): 8.99 (1H, S., N-H); 7.30-7.91 (4H, m, HAr); 7.09 (1H, m, 5-H PY); 6.88 (2H, S., NH2); 2.75 (3H D., 4-CH3PN), J=0,3; 2.52 (3H D., 6-CH3Ru) J=0,3.

Mol. ion (mass spectrometrically) 423.

Experimental evaluation of growth-stimulating activity FCTP on seedlings and plants of sunflower conducted on an experimental basis of VNIIBT and is illustrated by the following examples.

Example 2. Assessment astragalina activity claimed FCTP on seedlings of sunflower

Sunflower seeds were placed for 1 h in a solution of the claimed compounds. Seeds of control variant were soaked in water. 1 the seeds evenly laid out on a strip of filter paper, it was rolled up into rolls and put in glasses of water, then in a thermostat at 28°C. After 3 days was measured by the length of the stem and root. As similar properties used HUMATE sodium V.R.

Growth-stimulating activity was determined by increasing the length of hypocotyl and root of seedlings treated with a solution of the analyte, compared to control.

Experiment was repeated five times. In each replication were used for 25 seeds.

The measurement results were subjected to statistical analysis using t-student test at P or=0.90 and P=0,95. The data obtained are shown in table 1.

Example 3. Assessment astragalina activity claimed FCTP in field experience

Growth-stimulating activity of the claimed compounds FCPT also studied in small-plot field experience according to the standard technique of TIN. For this plant sunflower varieties VNIIMK-8883 in the phase of 2-3 leaves were treated with a solution FCPT at a dose of 200 g/ha and a solution of sodium HUMATE (prototype) at a dose of 250 ml/ha at the rate of fluid flow 300 l/ha Area of the experimental plots 5 m2when the fivefold repetition of experiments. Cleaning and evaluation of the harvest was carried out in the period of full maturity of the seeds. Growth-stimulating activity was determined by the increase in seed yield of sunflower processed Appl is subject to joint or prototype in comparison with the control (treatment with water only, 300 l/ha). Statistical processing of experimental data was performed using t-student test at P=0,95. The data obtained are shown in table 2.

As can be seen from these tables, the use of the proposed pyridinethione as postregulatory sunflower leads to the following results.

If PKT its use as poststimulatory in laboratory experiences in a concentration of 0.01 to within 0.00001 wt.% increases the length of the hypocotyl in comparison with the control 18-34% (105-120 instead of 89 mm), while the application of known poststimulatory of sodium HUMATE increases this ratio in comparison with control only 7-12% (95-100 instead of 89 mm). At the same time root length increased by 16-33% (71-81 instead of 61 mm), while the use of sodium HUMATE increases this rate by only 8-11% (66-68 instead of 61 mm).

If PKT its use as poststimulatory in field experiments at a dose of 200 g/ha increases the seed yield of sunflower 2.4 t/ha or 16%, while the application of known poststimulatory of sodium HUMATE increases this ratio in comparison with control only 1.4 kg/ha or by 9.3% (17,4 instead of 16.4 kg/ha).

Thus, the application of the proposed pyridinethione as a growth regulator can increase the length to which the hypocotyl of seedlings of sunflower, and to increase the yield and to expand the range of known poststimulation.

Table 1

Growth stimulating properties FCPT in relation to seeds and seedlings of sunflower
ConnectionControl (water) And mmThe concentration, wt.%
1·10-21·10-31·10-41·10-5
AndB**AndB*AndB*AndB*
HUMATE sodium V.R.
(PKT)
And is the average length of hypocotyl (the numerator) and the root (the denominator), mm; B - with respect to the control (hypocotyl/root)%;

The difference is significant: *) when P=0,95; **) if R=0,90
Table 2

Growth stimulating properties FCPT relative to the seed yield of sunflower
ConnectionDose, g(ml)/haYield, kg/haGain control
kg/ha%
HUMATE sodium25016,41,49,3
PKT20017,42,41
Control-15,0--

The use of 2-[N-(2'-itfeel)carboxamido]-3-amino-4,6-dimethylthieno[2,3-b]pyridine structure

as a growth stimulator sunflower.



 

Same patents:

FIELD: organic chemistry of heterocyclic compounds, pharmacy.

SUBSTANCE: invention relates to new bicyclic heteroaromatic compounds of the general formula (I): wherein R1 represents phenyl optionally substituted with NHR5 or OR5; R2 represents (C1-C4)-alkyl or phenyl; R5 represents phenylcarbonyl, (C4-C6)-heterocycloalkylcarbonyl, (C2-C8)-alkenylsulfonyl and others; Y represents nitrogen atom (N); Z represents -NH2 or -OH. A represents sulfur atom (S) or a bond; B represents -N(H) or oxygen atom (O); X1-X2 represent C=C, -NH-C(O), C=N and others; Proposed compounds show agonistic activity with respect to LH receptor and can be used in medicine.

EFFECT: valuable medicinal properties of compounds.

10 cl, 34 ex

FIELD: organic chemistry, biochemistry, pharmacy.

SUBSTANCE: invention relates to new derivatives of β-carboline of the general formula (I)

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EFFECT: improved preparing method, valuable medicinal and biochemical properties of compounds and composition.

14 cl, 11 sch, 7 tbl, 13 ex

FIELD: biochemistry, medicine, in particular new bioactive compounds having peptide hormone vasopressin agonistic activity.

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41 cl, 19 tbl, 193 ex

FIELD: organic chemistry, medicine, hematology.

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EFFECT: valuable medicinal properties of compounds.

13 cl, 1 tbl, 195 ex

FIELD: organic chemistry, medicine, pharmacy.

SUBSTANCE: invention relates to new nitrogen-containing aromatic derivatives of the general formula:

wherein Ag represents (1) group of the formula:

; (2) group represented by the formula:

or ; (3) group represented by the formula:

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

40 cl, 51 tbl, 741 ex

FIELD: organic chemistry, medicine, pharmacy.

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EFFECT: valuable medicinal properties of medicinal substances and compositions.

7 cl, 8 tbl, 32 ex

FIELD: organic chemistry, medicine, biochemistry, pharmacy.

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

6 cl, 1 tbl, 16 ex

FIELD: pharmaceutical chemistry, medicine.

SUBSTANCE: invention relates to substituted pyridines and pyridazines with angiogenesis inhibition activity of general formula I

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26 cl, 6 tbl, 114 ex

FIELD: organic chemistry, medicine, pharmacy.

SUBSTANCE: invention relates to new compounds of the general formula (1)

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EFFECT: valuable medicinal properties of compounds, improved method for treatment.

26 cl, 1 tbl, 119 ex

FIELD: organic chemistry, medicine, pharmacy.

SUBSTANCE: invention describes derivatives of piperazine of the general formula (I): wherein Y represents lower alkylene; R1 represents phenyl substituted with one or two similar or different substitutes taken among a group including lower alkoxy-group, mono- (or di-, or tri-)-halogen-lower)-alkyl, nitro-, amino-, lower alkylamino-, di-(lower)-alkylamino-, lower alkylthio-group,alkylsulfonyl, lower alkylaminosulfonyl, di-(lower)-alkylaminosulfonyl, and pyrrolyl; R2 means phenyl substituted with hydroxy-group at position 3 and with lower alkyl and halogen atom additionally; R3 means hydrogen atom; R4 represents (2,6-dimethylmorpholino)-(lower)-alkyl, (2-methoxymethylmorpholino)-(lower)-alkyl, (3-methoxymethylmorpholino)-(lower)-alkyl. Also, invention relates to their pharmaceutically acceptable salts, to method for their preparing, pharmaceutical composition and a method for vomiting inhibition. Proposed compounds are antagonists of tachykinin and can be used for vomiting inhibition.

EFFECT: improved preparing method, valuable medicinal properties of compounds.

9 cl, 47 ex

FIELD: agriculture, in particular, means for killing of mice and rats.

SUBSTANCE: rodenticide composition contains active substance - anticoagulant, attractant, food base, and sodium citrate, said components being used in the following ratio, wt%: anticoagulant 0.005-0.02; sodium citrate 3-5; attractant 2-5; food base the balance. Warfarin, difenacin, ethylfenacin, isoindan may be used as anticoagulant. Sugar, non-refined vegetable oil, and dried milk may be used as attractant. Cereal grain and groats, and combined feed may be used as food base. Rodenticide may further contain food colorant used in an amount of 0.02-0.05 wt%, with methylene blue or brilliant green or indigo carmine being used as colorant.

EFFECT: increased activity of rodenticide composition.

6 cl, 22 ex

FIELD: organic chemistry, chemical technology, medicine, veterinary science.

SUBSTANCE: invention describes the compound R-(-)-1-[2-(7-chlorobenzo[b]thiophene-3-ylmethoxy)-2-(2,4-dichlorophenyl)ethyl]-1H-imidazole of the formula (I) and its salts, in particular, its mononitrate. Also, invention relates to a method for preparing compound of the formula (I) possessing antifungal effect based on compound of the formula (I), and using compound of the formula (I) as an active component of the antifungal composition. Compound of the formula (I) can be used in compositions for treatment of fungal infections in humans or animals and against diseases of agricultural crops.

EFFECT: improved preparing method, valuable properties of compound and composition.

15 cl, 1 tbl, 10 ex

FIELD: agriculture.

SUBSTANCE: plant growth promoter comprises the following components used in the ratio, wt%: potassium humate 0.7-1.5; polyethylene oxide-400 15.0-40.0; polyethylene oxide 1500 30.0-60.0; water the balance.

EFFECT: increased activity of plant growth promoter, provision for regulation of sugar content in cellular water and increased cryoprotective and adaptogenic properties.

4 dwg, 29 ex

FIELD: chemistry of metalloorganic compounds, agriculture.

SUBSTANCE: invention describes derivatives of mepiquate borate of the general formula (I): wherein DMP means N,N-dimethylpiperidinium (mepiquate); M means metal cation acceptable for agriculture and chosen from a series comprising sodium, potassium, magnesium, calcium, zinc, manganese or copper, hydrogen atom or NH4+; O means oxygen atom; A means chelate of complex-forming fragment bound with one boron atom and representing (lower)-alkylglycols or sugars; n and m mean similar whole numbers in the range from 1 to 6; x means a whole or fraction number in the range from 0 to 10; y means a whole or fraction number in the range from 1 to 48; z means a whole or fraction number in the range from 0 to 48; v means a whole or fraction number in the range from 0 to 24, and w means a whole or fraction number in the range from 0 to 24. Also, invention describes methods for preparing compound of the formula (I) by interaction of N,N-dimethylpiperidinium hydroxide with boric acid and/or boron-containing oxides and optionally with metal hydroxides acceptable for agriculture indicated above or electrochemical method involving interaction of N,N-dimethylpiperidinium halide in the presence of water and boric acid and in the presence metal hydroxides acceptable for agriculture by bipolar electrodialysis. Invention describes electrochemical method for preparing N,N-dimethylpiperidinium hydroxide and a suspension concentrate possessing the plant growth-regulating effect prepared by mixing N,N-dimethylpiperidinium hydroxide, boron-containing compound chosen from boric acid and borate salt with a thickening agent and water, or by mixing compound of the formula (I) with Na2B8O13 x 4 H2O, a thickening agent and water. Prepared derivatives of mepiquate borate possess the improved indices of hygroscopicity and corrosion activity.

EFFECT: improved preparing methods, valuable properties of derivatives.

22 cl, 7 tbl, 16 ex

FIELD: agriculture.

SUBSTANCE: invention proposes using the plant roof avens (Geum urbanum L.) preparations that are prepared by pharmacopoeia method. Rood avens preparations in form of powder or extract are used for treatment of fresh-water mollusks inhabitation sites on the pasture or on the lowered pond bed that provides practically total eradication of mollusks and their egg mass for 3-6 days. Invention allows expanding assortment of agents and to realize the indicated designation.

EFFECT: valuable properties of agent.

6 ex

FIELD: agriculture.

SUBSTANCE: invention proposes using the plant water avens (Geum rivale L.) preparations prepared by pharmacopoeia method. Water avens preparations in form of powder or extract are used for treatment of fresh-water mollusks inhabitation sites on pasture or on the lowered pond bed that provides practically total eradication of mollusks and their egg mass for 3-6 days. Invention allows expanding assortment of agents and to realize the indicated designation.

EFFECT: valuable properties of agent.

6 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

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