Salt triazinetrione acids with astragalina activity against plant and tool based on them
(57) Abstract:Salt triazinetrione acids with astragalina activity against plant and tool based on them. The invention relates to the field of chemistry and agriculture. The obtained water-soluble effective poststimulatory with a wide range of actions - derivatives of s-triazine of the General formula:
< / BR>R - lower alkoxy, di(lower)alkylamino or diphenylamino, R= NH+4, K+, Na+that can be used as postregulation and means for presowing treatment of seeds based on them. The synthesis is performed by the interaction of the corresponding 2-substituted-4,6-bis(4-carboxyphenoxy)-s-triazines with an aqueous solution of the corresponding alkali or ammonia at a molar ratio of 1:2. 2 S. p. f-crystals, 2 tab. The invention relates to the field of chemistry and agriculture, and in particular to substituted SIMM-triazines as postregulation and means for pre-processing based on them.Known application of IAA (indelicacy acid) as a stimulant for germination of seeds of fruit and berry crops, consisting of pre-soaking seeds in 0.001% is, 990, S. 11).Disadvantages of its use are the need of bodrstvovaniya in alcohol (due to poor solubility in water), relatively high cost (1.5 million rubles per kg on 01.12.93), a narrow range recommended for seed treatment and low photoregulatory activity.It is also known application of Symm-triazinetrione acids as curing adhesive compositions (ed. St. USSR N 836068, B. I., 1981, N 21). The use of such acids as poststimulation unknown.The purpose of the invention the receiving water soluble, effective poststimulation with a broad spectrum of activity and relatively inexpensive.This goal is achieved by obtaining new derivatives of s-triazine, namely salts triazinetrione acids (Sebacina-11) General formula:
< / BR>where R= OCH3N(C2H5)2N(C6H5)2; R=NH+4, K+, Na+; which can be used as postregulation and means for presowing treatment of seeds on the basis of them.Source triazinetrione acid synthesized by the interaction of 2,4-dichloro-6-substituted-s-triazines with an aqueous-alkaline solution of 4-oksibenzoynoy kislota when the criterion acidification and acid secretion by a known method (Pogosyan, M. Assadourian I. A. Zaplishny Century. N. AWP. chem. W. 1977, T. 30, N 7, S. 597-601).Synthesis of salts Curaxin-11 were carried out by the interaction of 2-substituted-4,6-bis(4-carboxyphenoxy)-s-triazines with aqueous solutions of the corresponding source of alkali or ammonia at a molar ratio of acid: Osnovnye:2, followed by Visaginas salt, alcohol, or acetone by a known method, at 20oC (E technique. Scientific-technical collection of Materials. M. 1970, vol. 2, S. 76-81).Example 1. 2-Methoxy [4,6-carboxylations(sodium)] -1,3,5-triazine (Curaxin-11a).To a suspension of 3.84 g (0.01 mol) of 2-methoxy-4,6-bis(4-carboxyphenoxy)-1,3,5-triazine in 8 ml of water under stirring at a temperature of 20-25oWith added dropwise 3 ml of an aqueous solution containing 0,78 g (0,0195 mol) sodium hydroxide. The mixture is stirred for 1.5 h and filtered. The filtrate, under stirring, slowly added dropwise at 30 to 35 ml of ethanol, and the precipitated residue was filtered, washed with 2x5 ml of ethanol and dried in vacuum at 50-60oC to constant weight. Get 3,82 g (89%) Sebacina-11a in the form of a pale yellow powder, soluble in water and DMF insoluble in other organic solvents.Analysis for C18H11N3Na2O
Calculated C 53,9; H 3,9; N 12,0;
Found, C Of 53.7; H 3,7; N 12,2.X, n, cm-1(group): 1645-1625 ush.CL. (COO-); 1595, 1560, 1530, 1500 S. and Ms. (C= C and C= N-t. ); 1230, 1200, 1165, 1135, 1065 (COC); 803 SL. (deformats. fluctuations 1,4-disubstituted benzene).Other examples of synthesis, outputs, and properties of the synthesized salts of Covaccine-11 are presented in table. 1.The salts triazinetrione acids (Kovaciny-11) is used as a means for presowing treatment of seeds with different crops, as poststimulatory. When preparing aqueous solutions of salts of the concentration of the p indolyl-acetic acid (IAA) concentration of 0.001 wt. which was prepared previously podesteria IAA in ethanol. As control was used the option of soaking seeds in distilled water.The use of Covaccine-11 as a means for presowing treatment of seeds with different crops, the concentration and properties of the seedlings are illustrated by the examples presented in table. 2. The seeds were germinated in Petri dishes on constantly moist filter paper at 20-21oC for 25 days; corresponding measurements of root length and seedling conducted after 5 and 10 days, and the number of germinated seeds judged germination.From the data table. 2 shows that all the proposed salt are growth-stimulating activity. In the case of seeds of cucumber (examples 10-26) presowing cultivation of seeds Covaccine-11 at concentrations of 0.01 and 0.0001 wt. by the slight improvement in germination compared to the control (100% instead of 97,3% ) provides an increase in the length of 10-day-old seedlings and roots (17,0-33% and 2-11,9% respectively), while poorly soluble in water IAA at concentrations an order of magnitude higher (i.e., at a higher flow rate) stimulates these indicators only at 10.0 and 1.0%, respectively.If samajist in comparison with the control (100% instead of 97,3%) provides an increase in the root length of 10-day-old seedlings 2.2-87% while the IAA germination of seeds of melons do not stimulate.In the case of rice seeds (examples 44-60) pre-treatment with Sebacina in conc. of 0.01 and 0.0001 wt. provides increased germination (80-92% instead of 79%) and an increase in the length of 10-day-old seedlings and roots (3.9-12.9% and 3.3% and 19.4% respectively), while the IAA even at concentrations much higher these parameters does not improve.In the case of oats (examples 61-78) pre-treatment with Sebacina-11 at a concentration of from 0.01 to 0.0001 wt. provides improved germination in comparison with control (11-32% instead of 9%) and increases the length of the 10-day-old seedlings and roots (7.7-78% and 17.7-94.3%), while the IAA even at concentrations much higher on these parameters has no effect.In the case of seeds eggplant (examples 79-95) pre-treatment with Sebacina-11 at a concentration of from 0.01 to 0.0001 wt. provides improved germination in comparison with control (68-76,7% instead of 66%) and increases the length of the 10-day-old seedlings and roots (8.4-37,8% and 4.3 is 25.2%, respectively), while the IAA on the length of the root is generally not affected, and the length of the seedlings at a concentration of 0.001 wt. increases only by 3.7%
In the case of pea seeds (examples 96-110) processing Sebacina-11 at a concentration of from 0.01 to 0.0001 wt. virtually no effect on Park the IAA on this parameter have little influence.Thus, the proposed connection and means for presowing treatment of seeds are more effective than their counterparts on the structure and use and allow you to get available and soluble in water postregulatory, and seed treatment of their aqueous solutions can improve the germination of seeds and to increase the length of shoots and roots of various crops. 1. Salt triazinetrione acids of General formula
< / BR>where R is lower alkoxy, di(lower)alkylamino or diphenylamino;
R' K+, Na+or NH4+,
with astragalina activity against plants.2. Growth stimulating agent for pre-treatment of seeds, comprising the active substance and water, characterized in that the active substance it contains a connection on p. 1, where R is methoxy, diethylamino or diphenylamino, R' K+, Na+, NH4+, in the following ratio, wt.Active substance 0,0001 0,001
Water The Rest
SUBSTANCE: invention relates to application of 2-chloro-4,6-bis[thiophenyl]-1,3,5-triazine as antidote to reduce phytotoxic action of 2,4-dichlorophenoxyacetic acid butyl ester thereof to sunflower germs end vegetating plants.
EFFECT: effective increase of root length and sunflower yield.
2 tbl, 8 ex
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: agricultural industry.
SUBSTANCE: herbicidal compound preparation method includes diethyl ethanol amine salt of N-1,3,5-triazinyl aminocarbonyl arylsulfonamide as an active compound expressed by the general formula: , where R1=Cl or COOCH3; R2=H or CH3; R3=OCH3 or N(CH3)2; R4=CH3, ONC(CH3)2 or ONC(CH3)C2H5, which are used in agricultural industry as herbicides and plant growth-regulating chemicals. Method includes condensation of arylsulphonyl isocyanate with substituted 1,3,5-aminotriazine in the organic solvent medium, treatment of reaction mixture containing N-1,3,5-triazinyl aminocarbonyl arylsulfonamide, and excess arylsulphonyl isocyanate and phosgene used as impurities, with aliphatic alcohol, and then with diethyl ethanol amine, water extraction of salt, cleaning filtration, separation of water layer and mixing of water layer containing the active compound with auxiliary components. Output is 98.3-99.6%.
EFFECT: improving product yield, manufacturing capacity and environmental safety of the process.
2 cl, 1 tbl, 23 ex
SUBSTANCE: proposed is improved method of preparing a herbicide compound which active component is diethylethanolamine salt of N-1,3,5-triazinylaminocarbonylarylsulphonamide with general formula of: , where R1=Cl or COOCH3; R2=H or CH3; R3=OCH3 or N(CH3)2; R4=CH3, ONC(CH3)2 or ONC(CH3)C2H5; this type compounds are used in the sphere of agriculture as herbicides and phytohormones. The method envisages condensation of arylsulphonylizocyanate with replaced 1,3,5-aminotriazine in an organic solvent medium, treatment of the N-1,3,5-triazinylaminocarbonylarylsulphonamide being generated with diethylethanolamine, water extraction of the salt having generated and separation of the water stratum with the water eventually delivered for admixture of additive components. N-1,3,5-triazinylaminocarbonylarylsulphonamide treatment includes two phases: first diethylethanolamine becomes batched to the N-1,3,5-triazinylaminocarbonylarylsulphonamide in an organic solvent medium until the medium pH value in the water stratum is equal to 8.2÷9.4 with the free diethylethanolamine concentration amounting to 0.3÷1.0%; after that after the water stratum separation diethylethanolamine is added to the water until the medium pH value is equal to 9.3÷9.7 with the free diethylethanolamine concentration amounting to 1.2÷2.0%, the water is delivered for admixture of additive components and the organic stratum to have undergone regeneration is returned to the arylsulphonylizocyanate retrieval phase.
EFFECT: increased target product output.
SUBSTANCE: composition preventing plant diseases including components I and II as active ingredients is described. Component I is (RS)-N-[2-(1,3-dimethylbutyl)thiophene-3-yl]-1-methyl-3-trifluoromethyl-1H-pyrazol-4-carboxamides. Component II is selected from tetrakonazol, flutriafol, imibenkonazol, triadimefon, simekonazol, oxpokonazol fumarate, protiokonazol, bupirimate, spyroxamine, metiram, dodine, anilazine, chlozolinate, oxicarboxine, ethaboxam, iprovalikarb, pirazophos, phtorimide, diflumetorim, fenhexamide, famoxadone, fenamidone, ciazofamide, zoxamide, ciflufenamide, boskalid, isopropyl bentyavalikarb, pikoxistrobine, piraklostrobine, fluoxastrobine or dimoxistrobine. Also, the method preventing plant disease is described.
EFFECT: composition has synergistic effect which is not expected for each separate components, is able to significant increase of preventive effect against different phytopathogens with lower quantity of chemicals and do not invoke phytotoxic lesion.
2 cl, 9 tbl, 6 ex
SUBSTANCE: claimed invention relates to benzenesulphonamide derivatives of formula I and to their salts applied in agriculture. In formula I
X1 represents hydrogen or halogen; X2 chlorine; X3 represents hydrogen; Y represents group -C(A)B; A represents oxygen; B represents oxygen; R1 represents C1-C6-alkyl, which can be optionally substituted with C1-C6-alkoxyl, C1-C6-alkylcarbonyl, C3-C7-cycloalkyl, phenyl-C1-C4-alkyl; Q represents residue Q21; A8, A9 represent oxygen; R29 represents C1-C6-alkyl; R30, R31 represent hydrogen, C1-C6-halogenalkyl.
EFFECT: elaboration of method for obtaining benzenesulphonamide derivatives of formula I, herbicidal preparation based on them, method of obtaining herbicidally active preparations, method used to fight undesirable plant growth, application as herbicides and to benzenesulphonylisocyanates of formula II.
8 cl, 4 tbl, 6 ex
SUBSTANCE: invention relates to a synergetic insecticide containing active substances in form of a compound of general formula where E denotes NO2 or CN, R denotes thiazolyl-methyl or pyridyl-methyl, substituted with a halogen, A denotes hydrogen, Z denotes an alkylamino group with 1-4 carbon atoms or A and Z together with atoms with which they are bonded form thiazolidine, imidazolidine, hexahydro-1,3,5-triazine in which nitrogen atoms in positions 3 and 5 are substituted with two alkyl groups with 1-4 carbon atoms in the alkyl group, a 6-member saturated heterocyclic fragment which additionally contains oxygen and a N-alkyl heterogroup, where the alkyl in the N-alkyl group contains 1-4 carbon atoms, and a fungicidal active substance selected from a group comprising difenoconazole, triadimefon, fluquinconazole, fenpropimorph, procymidone, dichlofluanide, captan, anilazine, maneb, mancozeb, benomyl and sulphur.
EFFECT: high efficiency of the insecticide.
3 cl, 5 ex, 3 tbl
SUBSTANCE: method of obtaining microcapsules of triazine series pesticides is characterised by the following: 0.1 g of triazine series pesticide and 0.02 g of E472c preparation as emulsifier are added to 10 g of 5% water solution of polyvinyl alcohol (PVA), and obtained mixture is subjected to mixing. After dissolution of reaction mixture components and formation of transparent solution 15 ml of isopropanol are very slowly drop-by-drop poured in, and obtained suspension of microcapsules is stayed for 1 minute, filtered on filter, washed several times with isopropanol and dried. Method is realised at 25°C without special equipment.
EFFECT: simplification of the process of obtaining microcapsules and increased output by mass.
SUBSTANCE: invention relates to field of microcapsulation of heterocyclic compounds of triazine series. Method of obtaining microcapsules of triazine series pesticides is characterised by the fact that 0.1 g of triazine series pesticide and 0.02 g of E472c preparation as emulsifying agent are added to 10 g of 5% water solution of polyvinyl alcohol (PVA) and obtained mixture is subjected to mixing. Reaction mixture components are dissolved until transparent solution is formed after which 5 ml of carbinol as the first precipitating agent and then 10 ml of isopropanol as the second precipitating agent are added slowly drop-by-drop. After that, obtained suspension of microcapsules is kept for 1 minute, filtered on filter, washed with propanol several times, dried, with method being realised at 25°C without special equipment.
EFFECT: simplification of the process of obtaining microcapsules and increase output by weight.
SUBSTANCE: invention relates to agriculture, in particular to means for fighting undesirable vegetation. A herbicidal composition is created on the base of a sinergically effective combination of sulphonylureas (I) and triazolopyrimidines (II). The ratio of active substances (I) and (II) changes in the range from 1:5 to 5:1. A mixture of agriculturally acceptable adjuvants from the group of ethoxylated fatty alcohols and organosilicon compounds from the class of silixane is added to the said composition. The ratio of ethoxylated fatty alcohols and siloxanes in the mixture changes in the range from 1:10 to 10:1 respectively. A mixture of isodecyl alcohol ethoxylate with an organosilicon compound as an adjuvant is applied. In order to fight undesirable vegetation in crops of cultivated plants an effective quantity of the herbicidal composition is applied on it.
EFFECT: obtaining the means for fighting undesirable vegetation.
13 cl, 4 tbl, 2 ex
FIELD: organic chemistry, fat and oil industry.
SUBSTANCE: invention elates to a new derivative of sym.-triazine - 2-diphenylamino-4,6-bis-(nonyloxycarbonylmethylthio)-1,3,5-triazine that represents active supplement inhibiting oxidation processes in vegetable oils (antioxidant).
EFFECT: valuable properties of compound.
2 cl, 2 ex
FIELD: organic chemistry, herbicides.
SUBSTANCE: invention relates to novel arylsulfonylureas of the formula (I): wherein Q means oxygen atom (O); Y means -CH or nitrogen atom (N); Z means N; R means hydrogen atom (H), (C1-C12)-alkyl, (C2-C10)-alkenyl; R1 means H, (C1-C3)-alkyl; R2 means H, halogen atom, (C1-C3)-alkyl, (C1-C3)-alkoxy-group wherein both latter residues are unsubstituted or mono- or multiple-substituted with halogen atom or (C1-C3)-alkoxy-group; R3 means H, halogen atom, (C1-C3)-alkyl, (C1-C3)-alkoxy-, (C1-C3)-alkylthio-groups wherein indicated alkyl-containing groups are unsubstituted or mono- or multiple-substituted with halogen atom, or mono- or bisubstituted with (C1-C3)-alkoxy- or (C1-C3)-alkylthio-groups, or it means -NR5R6 wherein R5 and R6 mean independently H, (C1-C4)-alkyl. Compounds of the formula (I) elicit herbicide activity and therefore they can be used for the selective control for harmful plants. Also, invention describes intermediate compounds and methods for synthesis of compound of the formula (I).
EFFECT: improved method of synthesis, valuable properties of compounds.
14 cl, 22 tbl, 13 ex
FIELD: medicine, pharmaceutics.
SUBSTANCE: invention relates to compounds of formula (I) and their pharmaceutically acceptable salts, possessing antagonistic activity with respect to P2X3- and/or P2X2/3-receptor. In formula Ra, Rb and Rc represent (a) Ra and Rb, taken together, represent =Z; =Z represents =O; Rc stands for group, represented by R1c; R1c represents hydrogen, substituted or non-substituted C1-8alkyl, C2-8alkenyl, C3-7cycloalkyl; or (b) Rb and Rc together form bond; Ra stands for group, represented by group -Y-R1a; R1a represents substituted or non-substituted C1-12alkyl, benzyl; -Y- represents -O-, -S-, -N(R7)- or -CH2-; R7 represents hydrogen, substituted or non-substituted C1-8alkyl or R7 and R1a together form substituted with oxogroup 5-membered nitrogen-containing non-aromatic heterocyclic group; n represents integer number, equal 1 or 2; R2 represents substituted or non-substituted C3-7cycloalkyl, substituted or non-substituted phenyl or substituted or non-substituted 5-6-membered heteroaryl, containing one heteroatom, selected from N and S; R3 represents group, represented by formula: where A ring represents C3-7cycloalkyl; 6-membered non-aromatic heterocyclic group, containing 1-2 heteroatoms, independently selected from N and O; phenyl; 5-6-membered heteroaryl, containing 1-2 heteroatoms, independently selected from N and O, substituted with oxogroup 9-membered heteroaryl, containing 1-2 heteroatoms, independently selected from N and O; s represents integer number from 0 to 2; values of the remaining radicals are presented in invention formula. Invention also relates to pharmaceutical composition, to application of compounds in obtaining medication for treatment and/or prevention of disease, associated with P2X3- and/or P2X2/3-receptor, and to method of treating and/or prevention of disease, associated with P2X3- and/or P2X2/3-receptor.
EFFECT: obtained are compounds, which can be used in treatment and/or prevention of diseases, associated with P2X3- and/or P2X2/3-receptor.
18 cl, 123 tbl, 29 ex
FIELD: medicine, pharmaceutics.
SUBSTANCE: invention relates to formula (VIII) compounds and their pharmaceutically acceptable salts. Invention compound possess antagonistic effect with respect to P2X3 and/or P2X2/3 receptor. In formula (VIII) Z1 and Z2, each independently represent oxygen atom or sulphur atom; D ring represents benzene ring, pyridine ring, pyrimidine ring, pyrazine ring or pyridazine ring; B ring represents 6-membered aromatic heterocyclic ring with 1-3 nitrogen atoms, 5-membered aromatic heterocyclic ring with one nitrogen atom and one oxygen atom, one sulphur atom, one nitrogen atom and one sulphur atom, one oxygen atom, two nitrogen atoms, one oxygen atom and two nitrogen atoms, one sulphur atom and two nitrogen atoms, four nitrogen atoms or three nitrogen atoms, or non-substituted 9-membered condensed aromatic heterocyclic ring with one nitrogen atom and one oxygen atom or two nitrogen atoms. Values of other radicals are given in invention formula.
EFFECT: invention relates to formula (IX) compounds, formula (VII) compounds, formula (X) compounds, structural formulae and values of radicals of which are given in invention formula, to pharmaceutical composition, possessing antagonistic effect with respect to P2X3 and/or P2X2/3 receptor, to method of treatment and/or prevention of disease, associated with P2X3 and/or P2X2/3 receptor, to pharmaceutical composition, possessing analgesic effect and to method of obtaining formula (VIII) compound.
34 cl, 586 tbl, 107 ex