Derivatives of pyrimidine exhibiting herbicide activity
(57) Abstract:Purpose: in agriculture. The essence of the invention: pyrimidine derivatives f-crystals 1 where R1-H, lower alkyl, R2-OR3where R3-(C1-C4) -acylcarnitine group, ar- (C1-C4) -alkyl group or phenylcarbonylamino group, where the phenyl ring may be substituted by lower alkoxy (4), lower alkyl (2 or 4), halogen (2 or 4), or two halogen (2 and 6), or R2group f-crystals 2, where n=0 or 1, talimena, dioxyalkylene group, a and b may be the same or different and are alkoxy, haloalkyl, di - C1-C4-alkylamino, ceanography or halogen, exhibiting herbicide activity. Reagent 1: 2,6-bis [(4,6-dimethoxypyrimidine-2-yl)oxy]benzoate. Reagent 2: 1-chlorethylene. The process is carried out in dimethylformamide in the presence of 60%=tion NaH at 100° for 1 h under these conditions obtained all proposed connections, except connections, where R2- , n=1, the latter is obtained by the oxidation of compounds f-ly 1, where R2- table.7. The invention relates to new biologically active compounds - derivatives of pyrimidine exhibiting herbicide activity, which can be found at the activity.However, these compounds are dangerous for crops such as rice, wheat.Found that compounds, which in itself esterified to complex ester benzoic acid, are excellent herbicide action against perennial weeds, as well as against annual weeds, and at the same time they are highly safe for crops, particularly rice and wheat.This invention relates to pyrimidine derivative of the General formula I:
Owhere R1is a hydrogen atom, lower alkyl;
R2group of the formula OR3where R3- (C1-C4)-acylcarnitine group, ar - (C1-C4)-alkyl group, phenylcarbonylamino group in which the phenyl ring may be substituted in position: 4-lower alkoxy, 2 - or 4-lower-alkyl, 2 - and 6 - two halides or R2 group:
S(O) where n is 0 or 1, talimena group or dioxyalkylene group;
A and b may be the same or different and are alkoxy-, haloalkyl-, di- (C1-C4)-alkylamino-, cyano - or halogen atom, with a weed-killing activity.Process A.The compound of formula (1) corresponding to a given hard is it than an equivalent amount of base in a solvent at a temperature ranging from room temperature to the boiling point of the solvent for 0.5-48 hours As a basis it is possible to use alkali metal such as metallic sodium, metallic potassium, and so on; a hydride of an alkali metal and hydride alkaline earth metal, such as sodium hydride, potassium hydride, calcium hydride and so on; a carbonate of an alkali metal such as sodium carbonate, potassium carbonate and so on; and an organic amine, such as triethylamine, pyridine, etc.The solvent may be used carbon solvent, such as benzene, toluene, xylene and so on; halogenated hydrocarbon solvent such as methylene chloride, chloroform and so on; an alcohol solvent such as methanol, ethanol, 2-propanol and so on; a simple ether such as diisopropyl ether, tetrahydrofuran, dioxin, and so forth; ketone solvent such as acetone, methyl ethyl ketone and so on; esters such as methyl acetate, ethyl acetate and so on; aprotic polar solvent such as dimethylformamide, dimethylacetamide, dimethyl sulfoxide and so on; and other solvents such as acetonitrile; or a combination of both.The process Century.The compound of formula (I) in which R2represents - S(O) may be obtained by oxidation of compounds of formula (IV) oxidizing reagent R is]benzoate (compound No. 5)
1.7 g (4.0 mmole) of 2,6-bis-(4,6-dimethoxypyrimidine-2-yl)oxy benzoic acid and 0.2 g of 60% sodium hydride was dissolved in N,N-dimethylformamide. After cessation of hydrogen in solution is injected to 0.68 g (4.4 mmole) of 1-chloramination, and the resulting mixture chemically reacts with the 100aboutC for 1 h After termination of the reaction, the reaction mixture is introduced into ice water and extracted with ethyl acetate. An ethyl acetate layer is dried with anhydrous sodium sulfate, and the ethyl acetate Argonauts.The residual product is purified in a chromatography column with silicagel, it is introduced a mixture of ethanol-hexane to precipitate a solid substance, which is then filtered, and the result is 1.4 g of white crystalline substance with a melting point of from 97aboutWith up to 100aboutC.P R I m m e R 2. Getting 2,2-dimethylpropanolamine-2-(4-chloro-6-methoxypyridine-2-yl)- hydroxy-6-(4,6-dimethoxypyrimidine-2-)oxybenzoates (compound No. 28).0.9 g (2.1 mmole) of 2-(4-chloro-6-methoxypyridine-2-yl)oxy 6-(4,6-dimethoxypyrimidine-2-yl)oksibenzoynoy acid, 0.1 g of 60% sodium hydride and 0.39 g (2.5 mmole) climaterealists chemically interact in N,N-dimethylformamide, treated and cleaned the Nol/hexane to precipitate solids, which is filtered, and the result is 0.6 g of a white crystalline substance with a melting point 83-85aboutC.P R I m e R 3. Getting phenylthiomethyl-2,6-bis[4,6-dimethoxypyrimidine-2-yl)-oxy]benzoate (compound No. 1).1.7 g (4.0 mmole) of 2,6-bis-[(4,6-dimethoxypyrimidine-2-yl)-oxy]benzoate (compound No. 1).1.7 g (4.0 mmole) of 2,6-bis-[(4,6-dimethoxypyrimidine-2-yl)oxy]benzoic acid, 0.2 g of 60% sodium hydride and 0.72 g (4.4 mmole) of chloromethylated chemically interact in N,N-dimethylformamide, treated and purified in the same manner as in example 1, and the result is 1.4 g of a white crystalline substance with a melting point 89-93aboutC.P R I m e R 4. Getting phenylsulfanyl-2,6-bis [(4,6-dimethoxypyrimidine-2-yl)oxy]-benzoate (compound No. 2)
0.7 g (1.3 mmole) phenylthiomethyl-2,6-bis [(4,6-dimethoxypyrimidine-2-yl)oxy] benzoate was dissolved in chloroform and then chloroform solution in which the dissolved 0.25 g of meta-chlormadinone acid, injected dropwise into the above chloroform solution at a temperature of 5-10aboutC in an ice bath. After the chemical reaction of the mixture at the same temperature for one hour, it is introduced an aqueous solution with the W aqueous solution of sodium bicarbonate, dried and concentrated, the result is a light brown viscous liquid. Thus obtained product is purified in a chromatography column, the result is 0.6 g milk-white greasy substance. The compounds obtained in the examples 1-4 are shown in table. 7.Herbicide composition, corresponding to this invention, comprises herbicide-effective amount of a compound corresponding to this invention, and suitable for agricultural use Supplement.The herbicide that meets the present invention may be used as such or can be prepared in the form of various drugs, such as wettable powder, granules, emulsion concentrate or powdered drug by mixing it in the quantity of 0.5 to 95 wt.h., preferably 1-80 wt.h. with media, surface-active agent, dispersing agent or adjuvant additive which is commonly used in the formulations of chemicals for agricultural purposes, in an amount up to the total balance to 100 wt.h.As the carrier that should be used in the formulation of the composition, can be called solid media, such as anasac, ammonium sulfate or urea, or a liquid carrier such as isopropyl alcohol, xylene, cyclohexane or methylnaphthalene. As a surfactant and dispersing agent include, for example, ester alcohol - sulfuric acid, alkylarylsulfonate, ligninsulfonate, polyoxyethyleneglycol simple ether, polyoxyethylenesorbitan simple ether or polyoxyethylenesorbitan-mono-alkylate. As an additive include, for example, carboxymethylcellulose, polyethylene glycol or the Arabian gum.The content of compounds conforming to the present invention, in the formulation of the composition may vary depending on the type of composition, method of application, place of application, time mode, etc. Therefore, it is impossible to give a General definition. Typically, however, the content thereof is 5 to 90 wt.% in wettable powder, 5-80 wt.% in the emulsion concentrate, 1-60 wt.% in running the drug, 0.5 to 20 wt.% in granular drug, 5-40 wt. % in the liquid composition, 0.5 to 10 wt.% in pulverulent preparation and 5-90 wt.% in a dry granular product.The liquid composition may be prepared either by the use of the active ingredient in the salt form, either by typing basically the implement such herbicide may be diluted to the desired concentration prior to its application, or may be added directly as such.The herbicide that meets the present invention is able to suppress a variety of weeds in agricultural fields, for example in the fields of mining areas or orchards or forest lawn and the lawns, or other places for non-agricultural purposes, by processing the leaves.In addition, this herbicide is able to suppress a variety of weeds in rice fields by irrigation, tillage before or after germination of weeds or by processing the leaves.For tillage herbicide that meets the present invention, is deposited dose from 0.12 to 1 kg, preferably 0.5 to 500 g, more preferably 1-100 g of active ingredient per 10 ar. For processing of the foliage it is diluted to a concentration of 1-10 000 h/min to make. A more preferred dose it make is 1-10 g of active ingredient per 10 ar for rice fields, 5-50 g / 10 ar for fruit gardens or lawns and lawns, and 10-100 g for the forest or fields for non-agricultural purposes.If desired, the connection that meets the present invention may be used in combination with insecticides, sterilizing agents, other insecticides, agents regulating the growth of plants, fertilizers and so on,Example formulation 1 (wettable powder).10 o'clock compounds N 1, 0.5 hours of Emulgen 810 (trade mark, the company Kao Corporation) 0.5 hours of Demola (trade mark, company Kao Corporation), 20 hours Canelita 201 (trademark of Kao Corporation) and 69 h Ilita SA (trade mark, firm Kunimine Kogy K. K.) are uniformly mixed and dispersed, resulting wettable powder.Example formulation 2 (wettable powder). 10 o'clock compounds N 2, 0.5 h of Emulgen 810, 0.5 h of Demol N, 20 hours Canelita 201, 5 hours of Complexa 80 and 64 h Ilita SA uniformly mixed and dispersed, the result is a wettable powder.Example formulation 3 (emulsion concentrate).30 hours of compounds No. 5, 60 including an equivalent amount of a mixture of xylene with isoform and 10 o'clock surfactants of Sarpola 800 (trade mark, company Toho Kaguku K. K.) are uniformly mixed, and the resulting emulsion concentrate.Example of formulation 4 (granules). 10 o'clock compounds N 7, 80 hours of filler consisting of a mixture of talc with bentonite in the ratio of 1:3, 5 H. white uperaetsa pasty material. This paste-like material is then extruded through the mesh opening diameter of 0.7 mm, the extruded product is dried and cut into pieces of 0.5-1 mm, resulting granules.Data connection and herbicide composition, corresponding to this invention can effectively suppress annual weeds, such as millet Pucelle (Eskinochloa crusgalli), weed blood (Digitaria Sanguinalis), Elefsina Indian (Eleusine indila), spickle green (Setaria viriclis), Alopecurus water (Alopenirus aegualis), annual bluegrass (Poa annua), Alopecurus makehostkey (Alopecurus myosuroides), wild oat (Avena Fatua), cocklebur multifloral (Lolium Polygonum), Highlander pepper (Polygonum lapathifolium), amaranth (Amaranthus Viridis), pigweed white (hanopodium album), lilioceris (Abutilon theophrasti), breast prickly Sida Spinosa), wall-cress canadian (Cassia tora), starwort (Stellaria media), morning glory (Ipomola spp.), cocklebur (Xanthium Strumarium), Cyperus (Cyperus iria), the broad-fetanka (Brachiaria platyphylla), witchgrass (Rottoboelia exaltata), costner roofing (Bromus tectorum), Highlander vjunkovye (Polygonum convolvulus), mustard field (Brussica arvensis) and branched chain (Bidens frondasa), and perennial weeds such as Cyperus round (Cyperus rotundus), the Johnson grass (Sorghum halepeuse), Bermuda grass (Cyndon dactylon) and quackgrass (Agropyron repens), which grow in the fields of mining locally is.In addition, they are able to effectively suppress annual weeds such as millet plushie (Echinochloa crusgalli), Cyperus melkotsvetnye (yperus difforum), Monochoria (Monochoria vaginalis), and perennial weeds such as bulrushes (Scirpus hotarni), Alisma canaliculatum, Cyperus serotinus, saggittaria pygmala and Eleochoris Kuroguwai, growing in rice fields.On the other hand, herbicides, meets the present invention is highly safe for crops, particularly rice, wheat, barley, maize and others.These effects of these compounds and herbicides that meets the present invention, equivalent to the effects of normal derivatives userinilocation acid and herbicides containing these derivatives as the active ingredients, but they are superior in their effect in making them on the water surface of rice fields these normal compounds and herbicides.Compounds corresponding to this invention, with hardly move in the soil compared with the conventional connection type userimagesettings acid and, therefore, this compound has a smaller effect on environmental pollution than conventional connection.Further herbicide action data with theThe test example 1. (Test for herbicide action in the fields of mining places with the processing of the leaves).In a plastic pot filled with soil in the mountainous area (the surface area of 120 cm2) sow seeds of millet batoshevo (EU), mountain pepper (Ro), amaranth (Am) and Mary white (CH) at a depth of 0.5 to 1 cm, and the cultivation is carried out in a greenhouse for 2 weeks. The specified number of wettable powder prepared according to example 1 formulation, diluted with water and is applied through a small spray on the foliage dose of 100 l/10 ar so that the dose of the active ingredient was 400 g/10 ar. Plants are grown in greenhouses, evaluation is performed on the 14th day after the treatment according to the standard, as defined in the table. 1. The test results are presented in table. 3.The test example 2. (Test for herbicide action by tillage mountainous terrain).In a plastic pot filled with soil in the mountainous area (the surface area of 120 cm2) sow the weed blood (Di), amaranth (Am), white pigweed (CH) and Highlander pepper (Ro) at a depth of 0.5 to 1 cm and covered with soil. The next day specified number of wettable powder preparation, gabaritos atomizer in the amount of 100 l/10 ar so to the dose of the active ingredient was 400 g/ar. Then the plants are grown in greenhouses, evaluation is made on the 21st day after the treatment according to the standard, as defined in the table. 1. The test results are shown in table. 4.The test example 3. (Test on a selective action on the grain plant by processing the leaves on the field mountainous terrain).In a plastic pot (surface area of 600 cm2) filled with field soil in the mountainous areas, sow rice (Og), wheat (Tg), corn (te), millet plushie (It), Johnson grass (So), Alopecurus makehostkey (Al), Highlander pepper (Ro), amaranth (Am) and cocklebur (Ha) to a depth of 0.5-1 cm, growing plants is carried out in a greenhouse for 2 weeks. The specified number of wettable powder (active ingredient, g/10 ar), prepared according to example 1 (formulation), diluted with water and applied to the foliage by a small-sized sprayer in an amount of 100 l/10 ar.Then the plants are grown in a greenhouse evaluation of herbicide effect and phytotoxicity occurs on the 14th day after the treatment according to the standard (table. 1 and 2). The test results are given in table. 5.The test example 4 In a plastic pot (surface area 1/10000 Ara) filled with soil of rice fields, sow millet plushie (EU), Monochoria (Mo) and bulrush at a depth of 0.5 cm after irrigation, soil compaction and leveling of the soil. In this pot transplanted two samples of rice paddy (DG) under 2.5 list for transplanting depth 2 cm, exercise submergence to a depth of 3 see the next day specified quantity (active ingredient, g/10 ar) wettable powder prepared according to example 1 (formulation), diluted with water and bring dropwise on the surface of the water. Then the plants are grown in a greenhouse evaluation of herbicide effect and phytotoxicity is performed on the 28th day after the treatment according to the standards as defined in the table. 1 and 2. The results are summarised in the following table. 6.The following compound is obtained as comparative herbicide.Comparative connection:
2,6-bis-(4,6-dimethoxypyrimidine-2-yl) oxy benzoic acid.The tests showed that the compounds according to the invention have a high herbicide activity and is not harmful to crops. Derivatives of pyrimidine General formula
< / BR>where R1is hydrogen, n group, ar-(C1-C4)-alkyl group or phenylcarbonylamino group in which the phenyl ring may be substituted in position: 4 - lower alkoxy, 2-or 4 - lower alkyl -, 2-and 6 - two halides, or R2group
< / BR>where n = 0 or 1, talimena group, DIOXOLANYL group;
A and b, identical or different, - alkoxy, haloalkyl, di(C1-C4)-alkylamino, ceanography or halogen,
showing herbicide activity.
where R1- alkyl-(C1-C4), O-alkyl-(C1-C4), halogen;
R2- alkyl-(C1-C4), O-alkyl-(C1-C4);
n = 3-5;
Z = COOH, COO-alkyl-(C1-C4), CONHSO2C6H5with herbicide activity, and to a method of controlling undesirable vegetation by processing them in the locus, namely, that the treatment is carried out pyrimidine derivatives of General formula I:
where R1- alkyl-(C1-C4), O-alkyl-(C1-C4), halogen;
R2- alkyl-(C1-C4), O-alkyl(C1-C4);
n = 3-5;
Z = COOH, COO-alkyl-(C1-C4), CONHSO2C6H5in the amount of 1-10 kg/ha
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
FIELD: agriculture, in particular herbicide compositions.
SUBSTANCE: invention relates to weed controlling method for tolerant cotton crops using (A) road spectrum herbicides selected from group (A1) glufosinate (salt) and related compounds; (A2) glyphosate (salt) and related compounds; and (B) herbicides selected from group containing diurone, trifluraeline, linuron, and pendimethalin; lactofen, oxyfluoren, bispiribac and salts thereof, pyrithiobac and salts thereof; setoxydim, cyclosidim, and cletodim; wherein components (A) and (B) are used in synergistically effective ratio. Also are described herbicide compositions containing compound from group (A1) or (A2) and herbicide from group (B).
EFFECT: effective controlling of weeds in cotton crops.
9 cl, 12 tbl, 3 ex
FIELD: organic chemistry, agriculture.
SUBSTANCE: method involves carrying out a seasonal single treatment of plant leaves with asymmetrical derivative of 4,6-bis-(aryloxy)pyrimidine of the formula: wherein X means chlorine atom (Cl), nitro- or cyano-group. Invention provides enhancing the long-term time of plants protection.
EFFECT: enhanced effectiveness and valuable properties of compounds.
6 cl, 6 tbl
FIELD: organic chemistry, herbicides, agriculture.
SUBSTANCE: invention relates to new derivatives of uracil of the formula [I] eliciting the herbicide effect, herbicide composition based on thereof and a method for suppression of weed growth. In the formula [I] W means oxygen (O), sulfur (S) atom or imino-group; Y means oxygen atom (O) or sulfur atom (S); R1 means (C1-C3)-alkyl or (C1-C3)-halogenalkyl; R2 means (C1-C3)-alkyl; R4 means hydrogen atom (H) or methyl; R5 means (C1-C6)-alkyl, (C1-C6)-halogenalkyl, (C3-C6)-alkenyl, (C3-C6)-halogenalkenyl, (C3-C6)-alkynyl or (C3-C6)-halogenalkynyl; X1 means halogen atom, cyano- or nitro-group; X2 means hydrogen atom (H) or halogen atom; each among X3 and X4 means independently hydrogen atom (H), halogen atom, (C1-C6)-alkyl, (C1-C6)-halogenalkyl, (C3-C6)-alkenyl, (C3-C6)-halogenalkenyl, (C3-C6)-alkynyl, (C3-C6)-halogenalkynyl, (C1-C6)-alkoxy-(C1-C6)-alkyl, (C1-C6)-alkoxy-, (C1-C6)-halogenalkoxy-, (C1-C6)-alkoxycarbonyl-(C1-C6)-alkoxy- or cyano-group. Also, invention relates to new intermediate substances used for preparing compounds of the formula [I] corresponding to formulae [VII] , [XXXIV] and [XXXIII] wherein in compound of the formula [VII] W means oxygen (O), sulfur (S) atom or imino-group; Y means oxygen (O) or sulfur atom (S); in compounds of formulae [XXXIV] and [XXXIII] W means oxygen atom (O); R17 means oxygen atom (O); R4 means hydrogen atom (H) or methyl. Also, invention relates to methyl- or ethyl-[2-(5-amino-2-chloro-4-fluorophenoxy)phenoxy]acetate not early described in the literature.
EFFECT: valuable herbicide properties of compounds.
23 cl, 17 sch, 9 tbl, 11 ex
FIELD: organic chemistry, agriculture.
SUBSTANCE: invention relates to selective herbicidal compositions, containing customary auxiliary substances, as well as: a) herbicidal effective amount of compound of formula I or agriculture acceptable salt thereof wherein R are independently C1-C6-alkyl, C1-C6-haloalkyl, C1-C4-alcoxy-C1-C4-alkyl, or C1-C4-alcoxy-C1-C4-alcoxy-C1-C4-alkyl; m = 2; Q is group of formula wherein R23 is hydroxyl and Y is C1-C4-alkylen bridge; and b) synergetically effective amount of one or more herbicides; and methods for controlling of undesired plants in tame cultures using the said composition. Also disclosed is composition containing customary auxiliary substances, as well as herbicidal and synergetically effective amount of 4-hydroxy-3-(2-methyl-6-trifluoromethylpyridine-3-carbonyl)bicyclo[3.2.1]octo-3-ene-2-one of formula 2.2 and herbicidal antagonistically effective amount of antidote of formula 3.1. Compositions based on 4-hydroxy-3-(2-methyl-6-trifluoromethylpyridine-3-carbonyl)bicyclo[3.2.1]octo-3-ene-2-one and herbicidal antagonistically effective amount of antidote, as well as methods for controlling of weeds and cereal grasses in tame cultures also are described.
EFFECT: compositions useful in effective controlling of many weeds both in pre-spring and post-spring phases.
5 cl, 63 tbl, 12 ex
FIELD: organic chemistry, herbicides, agriculture.
SUBSTANCE: invention elates to novel derivatives of uracil of the formula [I] possessing herbicide activity, a herbicide composition based on thereof and to a method for control of weeds. In derivatives of uracil of the formula [I] the group Q-R3 represents a substituted group taken among:
wherein a heterocyclic ring can be substituted with at least a substitute of a single species taken among the group involving halogen atom, (C1-C6)-alkyl-(C1-C6)-alkoxy; Y represents oxygen, sulfur atom, imino-group or (C1-C3)-alkylimino-group; R1 represents (C1-C3)-halogenalkyl; R2 represents (C1-C3)-alkyl; R3 represents OR7, SR8 or N(R9)R10; X1 represents halogen atom, cyano-group, thiocarbamoyl or nitro-group; X2 represents hydrogen or halogen atom wherein each among R7, R8 and R10 represents independently carboxy-(C1-C6)-alkyl and other substitutes given in the invention claim; R9 represents hydrogen atom or (C1-C6)-alkyl. Also, invention relates to intermediate compounds used in preparing uracil derivatives.
EFFECT: improved preparing method, valuable properties of compounds.
40 cl, 16 sch, 12 tbl, 65 ex
FIELD: organic chemistry, chemical technology, herbicides, agriculture.
SUBSTANCE: invention relates to new sulfonamides of the formula (I):
and their salt wherein A represents substituted or unsubstituted benzene ring or 5-membered, or 6-membered substituted or unsubstituted heteroaromatic ring taken among the group comprising thienyl, pyrazolyl, imidazolyl, pyridyl wherein optional substitutes are taken among the group consisting of halogen atom, substituted or unsubstituted (C1-C4)-alkyl, unsubstituted or substituted (C1-C4)-alkoxy-group, nitro-group, phenyl, phenoxy-group, benzoyl and (C1-C4)-alkylcarboxylate when any alkyl fragment in the latter indicated substituted is substituted with one or some halogen atoms, (C1-C4)-alkoxy-groups, cyano-group and phenyl; Q represents -O-, -S- or group of the formula: -CXX' wherein X and X' can be similar or different and each represents hydrogen atom, halogen atom, cyano-group, alkyl comprising 1-8 carbon atoms, or the group -ORa, -SRa; or one of X and X' represents hydroxy-group and another has values determine above; Ra means (C1-C8)-alkyl, phenyl; Rb means (C1-C8)-alkyl, phenyl; Y means nitrogen atom or the group CR9; R1 means unsubstituted (C1-C8)-alkyl or that substituted with halogen atom, cyano-group, phenyl or (C1-C4)-alkoxycarbonylamino-group, or it represents phenyl; R2 means hydrogen atom (H), (C1-C4)-alkyl; R3 and R4 can be similar or different and each represents (C1-C4)-alkyl, (C1-C4)-alkoxy-group, halogen atom; R9 means hydrogen atom (H) under condition that when Q represents oxygen atom (O) or -S- then ring A represents 5-membered substituted or unsubstituted heteroaromatic ring and determined above. Compounds of the formula (I) possess the herbicide activity that allows their using for eradication of weeds. Also, invention describes a method for preparing compounds of the formula (I).
EFFECT: improved preparing method, valuable properties of compounds.
9 cl, 5 tbl, 18 ex
FIELD: organic chemistry, agriculture.
SUBSTANCE: invention relates to pest controlling agents containing compound of formula I in mixture with active fungicidal material selected from azoxystrobin, tebuconazol, prothioconazol etc., in mass ratio of formula I/active fungicidal material providing marked synergic action.
EFFECT: enhanced assortment of pest controlling agents based on nitromethylene derivatives.
2 cl, 15 tbl, 9 ex
FIELD: agriculture, fungicides.
SUBSTANCE: claimed method includes treatment of contaminated cultural plants or cultivation area thereof with effective amount of composition, containing A) N-sulfonylvaline amide of formula I 1, wherein R1 represents hydrogen or haloprenyl; and R1 represents C1-C4-alkyl, in combination with B) methalaxyl, or fluozinam, or mancoceb, or chlorithalonyl, or strobyluzine, or pyraclostrobine, or acibenzolar-S-methyl, or dimethoform, or fludioxonyl, or cimoxanyl, or imazalyl in synergistically effective amounts. Fungicide composition containing effective combination of A and B in synergistically effective amounts in combination with agriculturally acceptable carrier and optionally with surfactant.
EFFECT: composition of increased fungicidal action due to synergic effect.
8 cl, 12 ex
FIELD: organic chemistry, agriculture, herbicides.
SUBSTANCE: invention relates to herbicidal agent containing compound of general formula I wherein X represents residue X1 or X2 and Z, R1 and R2 are as defined in claim of invention, and additional active substance selected from group containing bromoxynil, dicamba, flufenacete, metolachlor, atrazine, pendimethaline, imazetapir, iodosulfuron, nicosulfuron, 2-amino-4-(1-fluoro-1-methyl)-6-(3-phenyl-1-cyclobuthyl-1-propylamino)-1,3,5-triazine and N-[(4,6-dimethoxy-pyrimidine-2-yl)-aminocarbonyl]-2-dimethylamino-carbonyl-5-formyl-benzenesulfonamide. Compound of formula I and additional active substance are taken in mass ratio of 1:20-10:1, respectively.
EFFECT: agent of high herbicidal activity.
6 cl, 15 ex
FIELD: organic chemistry, chemical technology.
SUBSTANCE: invention relates to novel methods (variants) for synthesis of 2-(N-methyl-N-methanesulfonylamino)-pyrimidine of the formula (3) and aminopyrimidine compound of the formula (8) that can be used in synthesis of the known medicinal preparation - rosuvastatin. In compounds of formulae (3) and (8) R represents lower alkyl; each of R1 and R2 represents independently hydrogen atom, alkyl group, alkylsulfonyl group or arylsulfonyl group. Method for synthesis of compound of the formula (3) involves the following steps: (I) isobutyrylacetate ester of compound of the formula (5): wherein R represents lower alkyl is subjected for interaction with 4-fluorobenzaldehyde and urea in the presence of proton compound and metal salt; (II) compound synthesized in reaction at step (I) is oxidized; (III) obtained product after oxidation from stage (II) is subjected for interaction with organic sulfonyl halide of the formula (2): R'-SO2-X wherein R' represents lower alkyl substituted possibly with halogen atoms, phenyl substituted possibly with 1-3 groups chosen from nitro-group, halogen atoms, branched or direct lower alkyl, lower alkoxy-group; X represents halogen atom or organic sulfonic anhydride of the formula (2a): (R'-SO2)-O wherein R' has a value given above in the presence of a base; (IV) product of reaction at step (III) is subjected for interaction with N-methyl-N-methanesulfonamide in the presence of a base. Method for synthesis of compound of the formula (8) involves a step for interaction of corresponding 2-halide- or 2-substituted sulfonylpyrimidine with corresponding amino-compound. Also, invention relates to novel intermediate compounds and methods for their synthesis. Proposed methods provide avoiding toxic compounds and to obtain compounds of high purity and with the high yield.
EFFECT: improved methods of synthesis.
35 cl, 27 ex
SUBSTANCE: invention relates to new pyrimidine of the general formula (I), which possess properties of the inhibitor of CDK-kinase. In the general formula (I) R1 designates hydrogen, halogen, C1-C6alkyl, R2 designates C1-C10alkyl, C1-C10alkenyl, or C3-C10cycloalkyl which can be mono-, bi- or tricyclic or denotes one- or polysubstituted by identical or different substitutes from the number of hydroxy-group, halogen, C1-C6alkoxygroup, C1-C6kalkylthiogroup, -NH-(CH2)n-C3-C10cycloalkyl, C3-C10 cycloalkyl, C1-C6hydroxyalkyl, C1-C6alkoxy-C1-C6alkyl, C1-C6alkoxy-C1-C6alkoxy-C1-C6alkyl, -NHC1-C6alkyl, -N(C1-C6alkyl)2, C1-C6alkanoil, -CONR3R4, -COR5, C1-C6alkylOAc, where Ac indicates C1-C4alkylCO-group, carboxygroups, phenyl, 5-6-member heteroaryl, containing 1-2-heteroatom in the ring, selected from nitrogen, -(CH2)n- phenyl, -(CH2)n-5-6-member heteroaryl containing 1-2-heteroatom in a ring, selected from nitrogen, phenyl-(CH2)n-R5, -(CH2)nPO3(R5)2 and -R6 and -NR3R4C1-C10alkyl, or C3-C10cycloalkyl, in this case phenyl, C3-C10 cycloalkyl, heteroaryl, -(CH2)n-phenyl and -(CH2)n heteroaryl can be one or polysubstituted by identical or different substitutes from halogens, hydroxygroup, C1-C6alkyl, C1-C6alkoxygroup, benzoxy-group and -CF3 groups, and ring of C3-C10 cycloalkyl and C1-C10alkyl can be separated by one or several nitrogen atoms, oxygen and/or sulfur and/or the said ring can be interrupted by one or two groups of =C=O or R2 designates the group X designates oxygen or group-NH-, and one of A and B independently indicates hydrogen, and the other indicates hydrogen, hydroxygroup, C1-C3alkyl, C1-C6alkyoxy,group SR7, SO2R7, CO(OH)R7, CR7(OH)R7, C1-C6alkyl-P(O)OR3OR4, COR7 or A and B together form C3-6-cycloalkyl ring which does not necessarily have to be interrupted by 1-3 atoms of nitrogen, oxygen and/or sulfur and/or can be interrupted by =C=O or =SO2 groups, and/or does not necessarily have to contain one or several double bonds, X designates oxygen or group-NH-, either one from A and B independently indicates hydrogen, and the other indicates hydrogen, hydroxygroup, C1-C3alkyl, C1-C6alkyoxy,group SR7, SO2R7, CO(OH)R7, CR7(OH)R7, C1-C6alkyl-P(O)OR3OR4, COR7 or A and B together form C3-6-cycloalkyl ring which does not necessarily have to be interrupted by 1-3 atoms of nitrogen, oxygen and/or sulfur and/or can be interrupted by =C=O or =SO2 groups, and/or does not necessarily have to contain one or several double bonds, values of R3 -R10 are specified in the formula of the invention.
EFFECT: connections can be used for the treatment of cancer, autoimmune diseases caused by chemotherapeutic means of alopecia and inflammations of mucous membrane, cardiovascular diseases, infectious diseases, chronic neurodegenerative and viral infections.
13 cl, 1 tbl, 540 ex
SUBSTANCE: there is disclosed compounds of formula II , where each R2 independently stands for H, halogen, cyano, NO2, OR5, NR6R7, alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, heterocyclo, substituted heterocyclo, arylalkyl, substituted arylalkyl, heterocycloalkyl or substituted heterocycloalkyl; B represents O, S, SO or SO2; each W and X independently represents C or N; n is within 0 to 4 if both W and X represent C, 0 to 3, if either X or W represent N, and 0 to 2 if both X and W represent N; R3, R5, R6, R7 are independently chosen from H, alkyl, substituted alkyl, alkenyl, alkinyl, substituted alkinyl, cycloalkyl, substituted cycloalkyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, heterocyclo, substituted heterocyclo; R4 represents optionally substituted 5-6-merous heteroaryl containing nitrogen atom provided (a) if R4 stands for pyridyl, R4 is not substituted with both hydroxy and methoxy groups; and (b) R4 stands for pyrimidinyl, it is n-substituted =O; A is chosen from following compounds of formula: , where D stands for S or O; m is within 0 to 6; R16, R17, R18, R19, R20, R21, R22, R23, R24, R25, R26 and R27 are independently chosen from H, halogen, NR30R31, OR32, CO2R33, SO2R36, alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, alkenyl, substituted alkenyl, alkinyl, substituted alkinyl, -CN, aryl, substituted aryl, heteroaryl, substituted heteroaryl, heterocycloalkyl or substituted heterocycloalkyl; R28 and R29 are independently chosen from H, alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, aryl, substituted aryl or together they form carbocyclic or heterocyclic ring consisting of 3 to 8 atoms; and R30, R31, R32, R33 and R36 are independently chosen from H, alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkinyl, substituted alkinyl, cycloalkyl, substituted cycloalkyl, alkoxycarbonyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, heterocyclo, substituted heterocyclo, heterocycloalkyl or substituted heterocycloalkyl as pharmaceutical composition for cancer treatment containing compound of formula II.
EFFECT: production of new compounds and based pharmaceutical composition applied for cancer treatment.
18 cl, 147 ex
FIELD: chemistry, medicine.
SUBSTANCE: invention refers to the method for modulation of the CRTh2-receptor activity with usage of the compounds of formula (I) or their pharmaceutically acceptable salts where: W is O, S(O)n (where n is equal 0, 1 or 2), NR15, CR1OR2 or CR1R2; X is hydrogen, halogen or C1-6 alkyl which can be substituted with one or more halogen atom; Y is hydrogen, halogen; Z is phenyl, pyridyl, pyrimidyl or quinolyl possibly substituted with one or more substituting group independently selected from following groups: halogen, CN, nitro, SO2R9, SO2NR10R11, CONR10R11, NHSO2R9 or C1-3 alkyl substituted with one or more halogen atom; R1 and R2 are independently hydrogen atom or C1-6 alkyl; R9 is C1-6 alkyl; R10 and R11 are independently hydrogen atom or C1-6 alkyl; R15 is hydrogen atom or C1-6 alkyl.
EFFECT: improvement of the method.
19 cl, 68 ex