The way to obtain e-isomer derivatives of acrylic acid
(57) Abstract:Usage: as fungicides in agriculture. The inventive product: E - isomers acrylic acid derivatives of General formula , where W is pyridinyl or pyrimidinyl, substituted with halogen, C1-C4-alkyl, which, in turn, can be substituted by homogena, phenyl; C1-C4-alkoxyl, fenoxaprop, which can be substituted 1-methoxycarbonyl-2-methoxyethanol, halogen, cyano - or nitro-group, amino, formamido-, nitro-, cyano -, or N-oxide group, or W-chinoline or ginasolinspu, possibly substituted with halogen, and associated with one of the carbon atoms of zinc, And oxygen or a group S(O)nwhere n=0 or 1, or 2, provided that when W is 5-cryptomaterial-2, And is not oxygen. Reagent 1: compound of General formula . Reagent 2: W - L, where L is halogen. Process conditions: in the presence of a base in an organic solvent, possibly in the presence of a catalyst from among transition metal or its salts. 9 table. The invention relates to a process for the preparation of new heterocyclic derivatives of acrylic acid, possess valuable fungicidal properties and which is zignago tools.The disadvantage of this known tool is its relatively low efficiency.The purpose of the invention is a method of obtaining new derivatives of acrylic acid with a higher fungicidal activity.The goal achieved by a method of obtaining E-isomers acrylic acid derivatives of General formula I.The following examples illustrate the method according to the invention and fungicidal properties of the obtained compounds.P R I m e R 1. /E/-Methyl-2-/2'-(5"-nitropyridine-2"-yloxy)phenyl/-3-methoxyamine - lat (compound 133, PL.1).2-/Hydroxyphenyl/acetic acid /50 g/ are added to a solution of hydrogen chloride in methanol (prepared from acetylchloride /25 ml/ methanol /250 ml/). The solution was stirred at room temperature for 3 h, and then incubated for 15 h the resulting mixture was concentrated under reduced pressure, the residue is taken up in a simple ether /250 ml and washed with aqueous sodium bicarbonate solution as long as you do not stop the rapid evolution of gas. The ether solution is dried, and then concentrated under reduced pressure. The obtained solid is recrystallized from a mixture of simple ether/petrol; receive methyl-(2-hydroxyphenyl)and the memorial plaques: 3,70 (2H, with in), 3.75 (3H, s), 6,80-to 6.95 (2H, m), 7,05-7,10 (1H, m), 7,15-of 7.25 (1H, m), 7,40 (1H, s).Methyl (2-hydroxyphenyl)acetate (21,0 g) dissolved in dimethylformamide (200 ml), add potassium carbonate (19,35 g) in one portion. To the mixture are added dropwise benzylbromide (23,94 g) in dimethylformamide (50 ml) under stirring at room temperature. After 18 h the mixture was poured into water (500 ml) and extracted with diethyl ether (CH ml). The extracts washed with water (I ml) and brine (100 ml), dried and filtered through silica gel (50 g, Merck 60), then concentrated under reduced pressure to obtain a yellow oil, distillation (160about/0.5 mm RT.CT.) gives methyl-2-benzyloxyaniline in the form of a colorless oil (26,99 g, 83% yield), IR (film): 1730 cm-1;1H NMR (90 MHz), M. D.: of 3.60 (3H, in), 3.75 (2H, s), 4,10 (2H, s), 6,80-7,40 (N, m).A mixture of methyl 2-benzyloxybenzoate (26,99 g) and methylformate (126,62 g) in dry dimethylformamide (300 ml) is added dropwise to a stirred suspension of sodium hydride (50% dispersion in oil, 10,13 g) in DMF (300 ml) at 0aboutC. After stirring at 0aboutC for 2 h the mixture was poured into water (1000 ml) and washed with diethyl ether (CH ml). The aqueous layer was acidified to pH 4 with 6 M hydrochloric acid, then extracted with diatrofi loxitane/-3-hydroxyacrylates in the form of a yellow oil, IR (film) 1720, 1660 cm-1.The crude methyl 2-/2'-benzyloxyphenyl/-3-hydroxyacrylates dissolved in dry dimethylformamide (100 ml) in one portion add potassium carbonate (29.0 g). Then added dropwise dimethylsulfate (16,00 g) in dry DMF (100 ml) under stirring. After 90 min, water is added and the solution extracted with diethyl ether (CH ml). After washing with water (I ml) and saline extracts are dried and concentrated under reduced pressure, the obtained yellow oil solidified upon trituration with a mixture of diethyl ether and gasoline. Recrystallization from dry methanol gives (E)-methyl-2(2'-benzyloxyphenyl)-3-metocean - relat in the form of a white crystalline solid (5,44 g, 17% yield based on methyl-2-benzyloxyphenyl), so pl. 76-77aboutC; IR (nujol): 1710, 1640 cm-1;1H NMR (90 MHz), M. D. : 3,63 (3H, in), 3.75 (3H, s), is 5.06 (2H, s), 6,80-7,40 (N, m) to 7.50 (1H, s).(E)-Methyl 2-(2'-benzyloxyphenyl)-3-me - toxicant (5,44 g) dissolved in ethyl acetate (50 ml) and add 5% palladium on coal (0.25 g). Stir the mixture hydronaut at a pressure of 3 ATM under stirring until cessation of hydrogen absorption, then filtered through celite silica gel (50 g, Merck 60). Concentration of the filtrate of substances (3,76 g, 99% yield), so pl. 125-126aboutC; IR (nujol): 3400, 1670 cm-1;1H NMR (270 MHz), M. D.:of 3.80 (3H, s), 3,90 (3H, s), of 6.20 (1H, s), 6,80-7,00 (2H, m), 7,10-7,30 (2H, m), 7,60 (1H, s).(E)-Methyl 2-(2'-hydroxyphenyl)-3-meth-oxacillin (0,30 g, 1.44 mmole), 2-chloro-5-nitropyridine (0,48 g, 2.88 mmole) and potassium carbonate (0.40 g, 2.88 mmole) is stirred in DMF (20 ml) at room temperature under nitrogen atmosphere. After 18 h, the reaction mixture was poured into water and then extracted twice with diethyl ether. The combined ether layers are washed twice with water and brine, and then dried. The resulting solution was filtered through a layer of silica gel and then concentrated, to obtain a pink solid. Chromatography (eluent: diethyl ether) to give (E)-methyl 2-[2'-(5"-nitropyridine-2"-yloxy)phenyl] -3-ethoxyacrylate (240 mg) as a yellow resin, which crystallizes upon standing, so pl. 107-109aboutC.P R I m m e R 2. (E)-Methyl 2-[2'-(4"-chloropyrimidine-2"-yloxy)phenyl]-3-methoxyamine - lat (compound N 61 table 1).E-Methyl 2-(2'-hydroxyphenyl)-3-ethoxyacrylate (0,63 g), 2,4-dichloropyrimidine (0.75 g) and potassium carbonate (0,69 g) is stirred in DMF at room temperature. After 2 h the reaction mixture was poured into water (50 ml) and extracted twice with diethyl ether. The combined EF is eigendom pressure, get a light oil. Chromatography using as eluent diethyl ether gives (E)-methyl 2-[2'-(4"-chloropyrimidine-2"-yloxy/phenyl] -3-ethoxyacrylate (0.35 g) in the form of an oil which crystallizes after trituration with ether; so pl. 120-121,5about;1H NMR, , M. D.: of 3.60 (3H, s), of 3.80 (3H, s), 6,60 (1H, d, j = 4 Hz), 7,40 (1H, s), 8,40 (1H, d, j = 4 Hz).P R I m e R 3. (E)-methyl-2-[2'-(6"-methylpyridin-3"-yloxy)phenyl]-3-ethoxyacrylate (compound 45, PL.1).6-Methyl-3-hydroxypyridine (9.5 g) is suspended in toluene (30 ml) and treated with an aqueous potassium hydroxide (4.9 g in water, 3 ml). The mixture is vigorously stirred for 15 min, then evaporated under reduced pressure. The last traces of water removed by repeated evaporation in the presence of toluene. The resulting brown semi-solid substance is treated with a mixture of 2-(2-bromophenyl)-1,3-dioxolane (10.0 g), copper chloride (60 mg) and Tris [2-(2-methoxyethoxymethyl] amine (0,194 g) to solubilize the copper salt in dry DMF (25 ml), and the mixture is heated at 155aboutWith under stirring in nitrogen atmosphere for 30 hours. Add additional copper chloride (60 mg) and heating continued for 14 hours.The mixture is cooled, poured into water and extracted with ethyl acetate. EXT the th acid. The acidic aqueous extract is treated with solid potassium carbonate to pH 8 and then extracted with ethyl acetate. The organic extract is dried, and then evaporated under reduced pressure to obtain 2-/6'-methylpyridin-3'-yloxy benzaldehyde (2.2 g) as an oil; IR (film) 1697, 1606, 1480 cm-1;1H NMR, ,M. D.: of 2.58 (3H, s) 6,86 (1H, s), 7,28 (3H, m), 7,55 (1H, t), 7,95 (2H, m), at 8.36 (1H, m), 10,53 (1H, s).2-(6'-Methylpyridin-3'-yloxy)benzal - digid (2,08 g) and methylsulfonylmethane (1,21 g) dissolved in dry THF (15 ml) and Triton B (1.5 ml) is added slowly dropwise with stirring at room temperature. The mixture was incubated over night, diluted with water and extracted with ethyl acetate. The extract is dried, and then evaporated under reduced pressure to obtain an orange-brown oil (3.2 g). The oil is treated with a methanol solution of hydrogen chloride (25 ml, 2.6 standards.) and incubated over night at room temperature. The solution is then diluted with water and adjusted to pH 8 by adding sodium carbonate. The mixture is extracted with ethyl acetate, the extract is dried and evaporated, get a brown oil (2,23 g), which is cleaned by liquid chromatography high resolution (eluent 1: 1 mixture of ethyl acetate: hexane), to obtain methyl[2, memorial plaques: to 2.54 (3H, s), 3,63 (3H, s) to 3.64 (2H, s), at 6.84 (1H, d), from 7.24 (5H, m), and 8.3 (1H, d).A mixture of methyl [2-(6'-methylpyridin-3'-yloxy)phenyl] acetate (1.3 g) and methylformate (1.52 g) in DMF (5 ml) is added dropwise to a suspension of sodium hydride (316 mg, 50% dispersion in oil) in DMF (5 ml) under stirring at 5aboutC. After stirring for 4 h the mixture is diluted with water, do weakly acidic by adding glacial acetic acid (pH 4-5) and extracted with ethyl acetate. The extract after drying and evaporation under reduced pressure to give methyl 2-[(2'-(6"-methylpyridin-3"-yloxy)-phenyl]-3-hydroxyacrylates in the form of a yellow oil (1,15 g),1H NMR, , M. D.: 2,53 (3H, s), 3,63 (3H, s), 6.89 in (1H, s) to 7.2 (5H, m), 8,21 (1H, d).Oil (1,14 g) dissolved in DMF (15 ml) is added potassium carbonate (1.1 g) and the mixture stirred for 15 min Dimethylsulfate (0,53 g) dissolved in DMF (5 ml) and this solution is added to the mixture. The resulting mixture is stirred for 80 min, then diluted with water and the resulting emulsion is extracted with ethyl acetate. The extract is dried and evaporated under reduced pressure to obtain a yellow oil (of 2.06 g), which is purified using chromatography high pressure (eluent:ethyl acetate), get (E)-methyl-2-[2'-(6"-IU - terpyridine-3"-yloxy)phenyl] -3-metocean - relat in the form of BC is? 7.04 baby mortality-to 7.32 (5H, m), 7,51 (1H, s), compared to 8.26 (1H, d).P R I m e R 4. Using the methodology of example 1, have the following connections:
1. (E)-methyl 2-[2'-(5"-chloropyridin-2"-yloxy)phenyl]-3-ethoxyacrylate, so pl. 77-78aboutC; IR 1700, 1625, 1260, 1200 cm-1;1H NMR (CCl3): , M. D.: of 3.57 (3H, s), 3,74 (3H, s), of 6.75 (1H, d), 7,41 (1H, s), 8,10 (1H, Shir.C.), a 7.1 to 7.6 (m).2. (E)-methyl-2-[2'-(5"-cyano-2"-yloxy)phenyl] -3-ethoxyacrylate (connection N127, PL.1), in the form of white crystals so pl. 108,5-109,5aboutS.1H NMR, , M. D.: to 3.58 (3H, in), 3.75 (3H, s). of 6.9 (1H, d), and 7.1 (1H, d), 7,28 to 7.4 (4H, m), 7,45 (1H, s), a 7.85 (1H, HF), to 8.45 (1H, d).3. (E)-methyl-2-2'-(5"-chloropyridin-2"-ylthio/phenyl-3-ethoxyacrylate (compound 14, table.1) in the form of a thick resin, IR 1700, 1630 cm-1;
4. (E)-methyl 2-[2'-(5"-pampered-2"-ylsulphonyl)phenyl-3-ethoxyacrylate resin.5. (E)-methyl 2-[2'-(5"-pampered-2"-ylsulphonyl)phenyl]-3-ethoxyacrylate in the form of an amorphous solid.6. (E)-methyl 2-[2'-(5"-methoxycarbonylmethyl-2"-yloxy)phenyl] 3-ethoxyacrylate (compound 141, PL. 1).1H NMR, , M. D.: 3,47 (3H, s), 3,62 (3H, s), 3,82 (3H, s), 6.75 in with 7.3 (5H, m), 7,32 (1H, s), 8,15 (1H, HF), 8,72 (1H, d).7. (E)-methyl 2-[2'-(5"-benzyloxycarbonylamino-2"-yloxy)phenyl]-3-metocean - relat (compound 184, PL.1), in the form of resin;1H NMR, , M. D.: 3,55 (3H, Logiczne get other connections table.I, II and III, the structure of which is also confirmed by PMR spectra.The following are examples of compositions suitable for agricultural and horticultural applications, which can be converted into ready preparative forms of the compounds of this invention.P R I m e R 5. Emulsifying concentrate is prepared by mixing and stirring the ingredients until dissolved,%: Connection 61, PL.1 10 Benzyl alcohol 30
Dodecylbenzenesulfonate calcium 5
Epileptologist (13 moles ethylene oxide) 10 alkyl benzenes 45
P R I m e R 6. The active ingredient is dissolved in methylenechloride, the resulting liquid spray granules attapulgite clay. The solvent then allow to evaporate, get the composition in the form of pellets,%: Compound 14, table.1 5 Granules attapulgite 95
P R I m e R 7. A composition suitable for seed treatment, is prepared by grinding and mixing the three ingredients,%: Connection 61, PL.1 50 Mineral oil 2 Chinese clay 48
P R I m e R 8. Dostawy powder is prepared by grinding and blending the active ingredient with talc, %: Connection 61, PL.1 5 Talc 95
P R I m e R 9. The suspension concentrate is prepared by grinding in resultant sodium 10 clay bentonite compounds, preventing Water 1 49
This new form can be used in the form of a spray by dilution with water or applied directly to seed treatment.P R I m e R 10. The form of a wettable powder is prepared by mixing and grinding the ingredients up until they are mixed thoroughly,%: Connection 61, PL.1 25 Lauryl sulfate 2 sodium Lignosulphonate 5 Silica 25 China clay 43
P R I m e R 11. Compounds were tested against a number of fungal diseases of foliage plants. The technology used in the tests was as follows.Plants were grown in compost for pots of John Innes (1 or 2) in minihorse 4 diameter see compound was converted into finished form of the drug or grinding balls with water Dispersol T, or in the form of a solution in acetone, or a mixture of acetone and ethanol, which was diluted to the required concentration immediately before use. In the case of diseases of the foliage of the drug (100 PM to 1 million of active ingredient) was sprayed on the leaves, and were introduced to the plant roots in the soil. Sprays were applied to the maximum retention on the surface, and the roots were moist to a final concentration equivalent to approximately 40 hours to obtain a final concentration of 0.05%.In the case of most of the test compound was applied to the soil (roots) and the leaves (spraying) for one or two days before infection of a plant disease. The exception was the test against Erysiphe graminis, in which the plants were inoculators for 24 h before processing. Deciduous pathogens were applied by spraying suspensions of spores on the leaves, used plants. After inoculation the plants were placed in a suitable environment to enable development of the disease, and then were incubated up until inoculation was not ready for evaluation. The period between inoculation and evaluation varied from 4 to 14 days, depending on disease and environmental conditions.The disease was recorded according to the following scale:
4 - the absence of disease;
3 - tracks - 5% of disease on untreated plants;
2 - 6-25% of disease on untreated plants;
1 - 26-59% of disease on untreated plants;
0 - 60-100% of disease on untreated plants.The results are shown in table.4.P R I m e R 12. This example illustrates the properties of compounds 14-16, 22, 61, 132 and 138-140 (PL.1) to regulate the growth of plants.These compounds IDA plants, used in this screening are presented in table.5, indicating leaf stage at which the plants were sprayed.The preparation of each chemical was applied in the amount of 4000 hours/million (4 kg/ha under field volume 1000 l/ha) using a track sprayer and nozzle SS8004E (Teejet). Additional tests were conducted on tomatoes using 2000 and 500 hours/millionAfter spraying, the plants were grown in a greenhouse with day temperatures of 25aboutAnd at night - 22aboutC. with the Exception of this trial was the cereal of temperate climate, wheat and barley were grown at daytime temperatures 13-16aboutWith and the temperatures at night - 11-13aboutC. If necessary, to ensure that the average duration of the photoperiod 16 h (minimum 14 hours) was used for additional lighting.After 2-6 weeks spent in the greenhouse, depending on species and time of year of plants was assessed visually in relation to morphological characteristics in comparison with the control plants, spray form drugs without active substance. The results are presented in table.6.P R I m e p 13. This example illustrates the insecticidal properties of some compounds of formula 1.The test procedure used for each of the pests was basically the same and included the location of a number of pests on the environment, which was usually the host-plant or food that eat pests, and handling or environment, or pests, or both drugs. The mortality of the pests was assessed over periods generally ranging from one to seven days after treatment.The test results are given in table.5 for each of the products that are taken in an amount in parts per million given in the second column, and the rating scale mortality was designated as 9.5 or 0, where 9 indicates 80-100% mortality (70-100% reduction in regrowth of roots compared to untreated plants in the case of Meloidogyne incognita, 5 indicates 50-79% mortality (50-69% reduction in regrowth of roots in the case Meloidogyne the pest organism is denoted by a letter code, and the kinds of pests, the environment or food, and the type and duration of the trials are given in table.7.The fungicidal action of the compounds according to the invention (compound II table.1) was compared with strobilurins And formulas
< / BR>The test was conducted in accordance with the procedure described in example 11, but the compounds were tested at a concentration of 25 h/million Compound 11 was applied by spraying the leaves, and strobilurin And were applied to the foliage and in the soil under the roots. The results (table.9) use of estimates defined in example 16.These results show that compound 11 of table.1 is more active than strobilurin And as a fungicide for plants, even when strobilurin And used by a combination of spraying foliage and impregnation roots, while compound 11 was used only by spraying the foliage.The compounds I belong to the group of low-toxic compounds. The WAY to OBTAIN E-ISOMER ACRYLIC ACID DERIVATIVES of General formula
< / BR>where W is pyridinyl or pyrimidinyl, substituted with halogen, C1- C4-alkyl, which, in turn, can be substituted with halogen, phenyl, C1- C4-alkoxyl, peppol, amino, formamido-, nitro-, cyano -, or N-oxide group, or W - chinoline or ginasolinspu, possibly substituted with halogen, and associated with one of the carbon atoms of the cycle;
And oxygen or a group S(O)nwhere n=0 or 1, or 2, provided that when W is 5-cryptomaterial-2-, a is not oxygen,
characterized in that the compound of General formula
< / BR>where a has the value
subjected to interaction with the compound of General formula
W - L,
where W is the specified value;
L is halogen,
in the presence of a base in an organic solvent, possibly in the presence of a catalyst from among transition metal or its salts.
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, fungicides.
SUBSTANCE: invention describes derivative of benzoylpyridine of the formula (I) or its salt:
wherein X represents halogen atom, (C1-C6)-alkoxy-group optionally substituted with a substitute taken among halogen atom, phenyl, methoxy-, methylthio-, dimethylamino-group, vinyl or ethynyl; phenoxy-group, (C3-C6)-cycloalkoxy-group, hydroxyl group, (C1-C6)-alkyl group, (C2-C6)-alkenyl group, CF3, (C1-C6)-alkylthio-group, (C1-C6)-alkoxycarbonyl group, (C1-C6)-dialkylaminocarbonyl group, (C1-C6)-alkylcarbonyloxy-group, (C1-C6)-alkylcarbonyl group, amino-group, (C1-C4)-alkylamino-group or di-(C1-C4)-alkylamino-group; n represents 1, 2, 3 or 4; R1 represents (C1-C6)-alkyl group; R2 represents (C1-C6)-alkyl group, (C1-C6)-alkoxy-group optionally substituted with phenyl, phenoxy-group, (C3-C10)-cycloalkyloxy-group or hydroxyl group; m = 1, 2 or 3 under condition that if m = 2 then R2 can form ring -OCH2O- (with exception when pyridine ring is substituted with benzoyl group at 2-position; pyridine ring is substituted with (C1-C6)-alkoxy-group, hydroxyl group or benzyloxy-group; n = 1; m = 1 or 2). Also, invention describes fungicide comprising compound of the formula (I) or it salt as an active component, methods for preparing derivatives of benzoylpyridine, phenylpyridylmethanol that is an intermediate compounds used for synthesis of compound of the formula (I). Invention provides fungicide properties of compound of the formula (I) or its salt.
EFFECT: improved method for preparing, valuable properties of compounds.
17 cl, 36 tbl, 4 ex