Derivatives of 1-pyridinemethanol and insecticidal composition
(57) Abstract:Usage: in agriculture, in particular as insecticidal agents. The inventive product - derivatives of 1-pyridinemethanol f-ly 1, where R1- H, C1-C3-alkyl, R2- C1-C4- haloalkyl; R3is halogen or trifluoromethyl. R4- C1-C3- haloalkyl. Insecticidal composition contains the active ingredients in an amount of 0.1 to 95% and the rest of the target additives. 2 S. p. f-crystals, 8 PL. The structure of f-crystals, 1: The invention relates to new derivatives of pyridinemethanol of the formula I where RN R1represents a hydrogen atom, a C1-C3-alkyl; R2is1-C4-haloalkyl; R3represents a halogen atom, trifluoromethyl; R4is1-C3-haloalkyl, the method of obtaining these compounds and insecticides containing these compounds as active ingredients.In U.S. patent N 3868458, U.S. patent N 3940484 and U.S. patent N 3996366 indicated that certain imidazole derivatives used as active ingredients of insecticides.As a result of intensive studies of compounds with excellent insecticide cidney activity.According to the invention are derivatives of pyridinemethanol formula I
RN , where R1is a hydrogen atom, a C1-C3-alkyl, C1-C3-allylthiourea or2-C3-alkoxyalkyl; R2is a hydrogen atom or a C1-C4-haloalkyl; R3is a halogen atom, a nitro-group or trifluoromethyl; R4- C1-C3-haloalkyl or1-C3-haloalkoxy, given the method of obtaining these compounds are insecticides containing these compounds as active ingredients.In the formula I, examples of the halogen atom are the same as for the Deputy, and include a fluorine atom, a chlorine atom or a bromine atom.Among the derivatives of pyridinemethanol recommended derivatives, in which R1is a hydrogen atom or a C1-C3-alkyl; R2- C1-C3-haloalkyl, including at least a fluorine atom, a chlorine atom or a bromine atom as the halogen atom; R3a fluorine atom, a chlorine atom or trifluoromethyl; R4- C1-C3-haloalkyl, including as a halogen atom at least a fluorine atom. More preferably, if R1is a hydrogen atom or methyl; R2- C2-haloalkyl, including as atom - trifluoromethyl.But it is particularly preferred if R1is a hydrogen atom or methyl; R2- haloalkyl formula-CF2CF2X, where X is a hydrogen atom, a fluorine atom, a chlorine atom or a bromine atom; R3- chlorine atom; R4- trifluoromethyl; most recommended option when R1is methyl; R2- haloalkyl formula-CF2CF2X, in which X represents a hydrogen atom, a fluorine atom, a chlorine atom or a bromine atom; R3- chlorine atom; R4- trifluoromethyl.Compounds according to the invention can be synthesized according to the following reaction scheme:
R+H where R1, R2, R3and R4everyone takes these values and a represents a halogen atom.The connection according to the invention can be obtained by the reaction of salidroside formula III with imidazole derivatives of the formula II at the 5-150aboutC for 1-24 h in a solvent and in the presence of removing hydrohalic reagent.Used in the reaction, the amounts of reactants are 1-2 equivalent salidrosides formula III and 1-4 equivalent of removing hydrohalic reagent per one equivalent of imidazole derivative of the formula II.Examples of solvents used in both the above reactions include,cities, such as benzene, toluene, xylene and so on; halogenated hydrocarbons such as chloroform, carbon tetrachloride, dichloroethane, chlorobenzene, dichlorobenzene and so on; ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran, dimethyl ether of ethylene glycol and so on; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, isophorone, cyclohexanone, and so on; esters such as ethyl acetate, butyl acetate and so on; nitro compounds such as nitroethane, nitrobenzene, and so on; tertiary amines, such as pyridine, triethylamine, N, N-diethylaniline, tributylamine, N-methylmorpholine and so on; NITRILES, such as acetonitrile, isobutyronitrile and so on; amides of acids, such as formamide, N,N-dimethylformamide, N, N-dimethylacetamide, etc.; sulfur compounds such as dimethylsulfoxide, sulfolan etc. or mixtures thereof.Examples remove hydrohalic reagents include organic bases such as pyridine, triethylamine, N,N-diethylaniline and so forth; inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, calcium carbonate, sodium hydride, etc. ; alkali metal alkoxides such as sodium methoxide, ethoxide sodium, etc.may be subjected to additional purification by chromatography, distillation, recrystallization, etc.Imidazole derivatives of the formula II and salidroside formula III used as starting products in the synthesis of compounds of the invention may be obtained by methods described in J. org. Chem., 47 2867 (1982), the Japan patent, U.S. patent N 3888932, U.S. patent N 3928416, European patent 23100, European patent 34402, the United Kingdom patent N 1121211 or similar ways.Examples of compounds of the present invention are shown in table. 1.Examples of harmful insects, against which the compounds of the invention show remarkable activity include.Harmful insects belonging to miptera:
vegetable fleas, such as small brown plant Bloch (Laodelpha striatellus), brown herbal flea (Nilaparvata lugens), white-backed rice Bloch (Sogatella furcifera); cycatki, such as green rice Cicada (Nephotettix cinticeps), (Nephotettix virescens) and so on; aphids, bugs, whiteflies, scale insects, bugs-lace, listblock etc.Lepidoptera:
Moth-the liquidation, such as hillock (hilo suppressalis), rice trubkovich (naphalocrocis medinalis), mol Indian flour (Plodia mterpunctella) and so on; butterflies, such as: scoop tobacco (Spodoptera litura), a scoop of rice (Pseudaletia separata), softky, such as: type of Adoxophyes spp.), view Grapholita spp. and so on; Carposinidae, lyonetiidae moths (Lyonetiidae), wananchi (Lymantriidae), propagandize beet (Autographa nigrisigna); harmful insects belonging to the mind Agrothis spp, such as: Vovka turnesa (Agrothis segetum), scoop-Upsilon (Agrotlus ipsilon); harmful insects belonging to the mind Hiliothis spp.; the cabbage moth (Plutella xylostella), a moth (Tineidae), mol transparent (Tpea translucens), mol a spider (Tineola bisselliella), and so on Harmful insects belonging to Diptera:
Mosquitoes, such as mosquito ordinary (ulex pipiens pallens), Culex tritaeniorhynchus, and so on; species Aedes spp., such as Aedes aeggpti, Aedes albopictus, and so on; species Anopheles spp., such as Anopheles sinensia, and so on ; Midge (Chironomidae), Muscidae, such as the fly room (Musea domestica, house fly (Muscina stabulans) and so on; Calliphoridae; Sarcophagida) and so on ; lliphoridae; Sarcophagida; fly small room (Fannia canicularis); Anthomyiidae or anthomyidae flies, such as the larvae of flies germ (Delia platura), larvae of the onion fly (Delia antigua), and so on; fruit flies (Tephritidae); Drosophila (Drosophilidae); baboonery (Psychodidae); simuliid (Simuliidae); Tabanidae; jagalchi autumn (Stomoxyidae), etc.: Harmful insects belonging to leoptera:
Flea dlinnoyu, such as Western blaska Donousa (Diabrotiea virgifera), southern blaska Donousa (Diabrotiea undceimpunctata) and so on: the scarabs (Searabaeidae), such as: x orgonotic rice water (Lissorhoptrus oryzophilus), weevil Chinese (allosobruchys chineneis) and so on: chernotsky, (Tenebrionidae) such as flour large garden chafer (Tenebrio melitor), garden chafer chestnut (Tribolium castancum) and so on, leaf beetles (Chrysomelidae) such as leaf pumpkin (Aulacophora femoralis) blaska striped (Phyllotreta striolata), and so on, Anobiidae species of Epilachna such as twenty societatii Ladybird (Epilachna vigintiootopunctata and so on; dravograd (Lyctidae); pseudodemocracy (ostrychidae), Cerambycidae, Kapuscinski (Palderus fusipes) and so onHarmful insects belonging to Dictyoptora
the Prussians (Blattella germanica), American cockroach (Periplaneta americana), cockroach smoky-brown (Periplaneta fuliginosa), brown cockroach (Periplaneta brunnea), cockroach black (latta orientalis), etc.Harmful insects belonging to Thysanoptera:
Thrips palmi, flower thrips (Thrips hawaiiensis), etc.Harmful insects belonging to Hymenoptera.ants (Formicidae), hornets (Vespidae), wasps bestility (thylidae), these sawflies (Tenthredinidae), such as cabbage Sawfly (Athalia rosae ruficornis), etc.Harmful insects belonging to Orthoptera:
the mole crickets (Gryllotalpidae): locusts (Acrididae), and so on:
Harmful insects belonging to Aphaniptera:
Parex irritans, etc.Harmful insects belonging to Anaplura:
Pediculus humanus capitis, Phthirus pubis, etc.Additionally, the compounds according to the invention is very effective to insects have developed resistance to conventional insecticides.In the case of using compounds of the invention as active ingredients of insecticidal compositions, these compounds can be used in pure form without adding any other components, but usually the connection is mixed with a solid carrier, liquid carrier, gaseous carrier, food, etc. and, if necessary and desired, in the mixture add additional surfactant and other adjuvants used to produce insecticidal preparations to receive them in the form of oil sprays, emulsifiable concentrates, wettable powders, granular components, granules, Farrukh Dustov, aerosols, fumigants (forming fog), poisoned baits, etc.Such compositions typically contain from 0.01 to 95 wt.%, compounds according to the invention as an active ingredient.Examples of solid carriers used for obtaining compositions include fine powders or granules of clays (Kali, diatomaceous earth, synthetic gidratirovannuyu silicon dioxide, bentonite, white clay fubasami and so on), talc, ceramics, neorganic so on), mineral fertilizers (ammonium sulfate, ammonium phosphate, ammonium nitrate, urea, ammonium chloride, and so on).Examples of liquid carriers include water, alcohols (methanol, ethanol etc ), ketones (acetone, methyl ethyl ketone, and so on), aromatic hydrocarbons (benzene, toluene, xylene, ethylbenzene, methylnaphthalene, and so on), aliphatic hydrocarbons (hexane, cyclohexane, kerosene, gasoil, and so on), esters (ethyl acetate, butyl acetate, and so on), NITRILES (acetonitrile, isobutyronitrile and so on ), ethers (diisopropyl ether, dioxane and so on), acid amides (N, N-dimethylformamide, N,N-dimethylacetamide, and so on), halogenated hydrocarbons (dichloromethane, trichloroethane, carbon tetrachloride and so on), dimethyl sulfoxide; vegetable oils such as soybean oil, cottonseed oil, etc. are Examples of gaseous carriers, i.e., propellants include freon, butane, LPG (liquefied petroleum gas), dimethyl ether, carbon dioxide, etc.Examples of surfactants include alkyl sulphates, salts alkylsulfonyl, salt alkylarylsulfonates, alkylsilane ethers and their polyoxyethylene derivatives, ethers of polyethylene glycol, esters of polyhydric alcohols, derivatives of alcohols, sahraie tools and so on, include gelatin, casein, polysaccharides (starch powders, gumarabic, cellulose derivatives, alginic acid and so on), lignin derivatives, bentonite, sugars, synthetic water-soluble high-molecular substance (polyvinyl alcohol, polyvinylpyrrolidone, polyacrylic acid, and so on). Examples of stabilizers include PAP (acidic isopropylacetate), BHT (2,6-di-tert-butyl-4-METHYLPHENOL), BHA (mixture of 2-tert-butyl-4-methoxyphenol and 3-tert-butyl-4-methoxyphenol), vegetable oils, mineral oils, surfactants, fatty acids or their esters, etc.As the basis of poisoned baits are used, for example, components of food, such as grain flour, essential oil, sugar, crystalline cellulose, etc.: antioxidants, such as dibutylaminoethanol, nordihydroguaiaretic acid and so on; preservatives such as dehydroacetic acid, etc., food seasonings such as paprika powders and so forth, stimulating fragrances such as cheese flavor, onion flavor, etc.The resulting compositions can be used as such or after dilution with water, etc. Or compounds may be used in the plants, synergistic agents, fertilizers, Povolotskaya, food, animals, etc. or can be used in conjunction with them without adding to them.When using the compounds according to the invention as insecticides in agriculture, their dosage is 0.1-100 g on ar: when using emulsified concentrates, wettable powders, flowable concentrates, and so on , after dilution with water the concentration is 0.1-500 h/million Granules, dusty, etc. can be used as such without dilution. In the household or for the purposes of public hygiene emulsifiable concentrates, wettable powders, flowable concentrates, etc. is diluted with water to a concentration of 0.1-500 ppm, oils, aerosols, fumigants, poison baits, etc. can be used as such.See dosage and concentration can vary depending on species composition, time of use, place of use, method of application, type of insect, damage, etc., and can be increased or decreased regardless of the given intervals.P R I m e R synthesis 1 (synthesis of compound 3). To a solution of 0.37 g (2 mmole) 4(5)-pentafluorothiophenol. In 5 ml of N,N-dimethylformamide at emperature 10 minutes Upon completion of the reaction, to the reaction mixture are added dropwise 0,43 g (2 mmole) of 2,3-dichloro-5-triptoreline, followed by stirring at room temperature for 8 hours After completion of the reaction, the reaction mixture is transferred into water and extracted with ethyl acetate. Then the extract was washed with brine, dried over magnesium sulfate and concentrate under reduced pressure. Chromatography of the residue on silica gel obtain 0.24 g of 1-(3-chloro-5-triptorelin-2-yl)-4-pentafluorothiophenol, so pl. 52aboutC.P R I m e R synthesis 2 (synthesis of compound (II). The solution is 0.22 g (1 mmol) of 2-methyl-4(5)-(2-chloro-1,1,2,2-tetraborate) of imidazole in 5 ml of N,N-dimethylformamide simultaneously added 0.21 g (1.5 mmole) of anhydrous potassium carbonate and 0.22 g (1 mmol) of 2,3-dichloro-5-triptoreline, followed by stirring for 7 h at 80-85aboutC. Upon completion of the reaction, the reaction mixture is transferred into water, extracted with ethyl acetate, the extract washed with brine, dried over magnesium sulfate and concentrate under reduced pressure. Chromatography of the resulting residue on silica gel obtain 0.27 g of 1-(3-chloro-5-triptorelin-2-yl)-2 methyl-4-(2-chloro-1,1,2,2-tetraborate)imidazole, T. pl. 137,5aboutC.Examples of compounds according to the invention, the synthetic parts are given by weight, and compounds of the present invention is marked with the numbers listed in table. 2.P R I m e R of structure 1. Emulsifiable concentrate.After dissolving 10 o'clock each of compounds (1) to(27) of the invention in 35 hours of xylene and 35 hours of dimethylformamide, to the solution was added 14 PM steelfinish ether of polyoxyethylene and 6 o'clock dodecylsulfonate calcium. The resulting mixture is thoroughly mixed and the result is a 10% emulsifiable concentrate.P R I m e R of part 2. Wettable powder.After adding 20 hours of compounds (1) to(27) of the invention to a mixture of 4 hours lauryl sodium, 2 hours ligninsulfonate calcium, 20 hours a fine powder of synthetic hydrated silicon dioxide and 54 including diatomaceous earth, the mixture is stirred in a mixer for juice and receive a 20% wettable powder.P R I m e R of part 3. Granules.After adding 5 o'clock a fine powder of synthetic hydrated silicon dioxide, 5 hours of dodecylbenzenesulfonate, 30 hours of bentonite and 55 including clay to 5 hours of compounds (1) to(27) of the invention the mixture is thoroughly stirred. After stirring to the mixture add the required amount of water. The mixture granularit using the pellet mill and after drying in the air recip is placed in an appropriate amount of acetone to the solution add 5 hours a fine powder of synthetic hydrated silicon dioxide, 0,3 including RAR and 93,7 including clay. The mixture is stirred in a mixer for juice and after evaporation of the acetone receive 1% dust.P R I m e R of part 5. Bulk concentrate.After mixing 20 hours of connection 23 of the invention and 1.5 hours of trioleate sorbitol from 28.5 hours of an aqueous solution containing 2 hours of polyvinyl alcohol, a mixture of finely crushed (to particles with a diameter less than 3 Ám) using a sand eraser. Then to the powder add 40 hours of an aqueous solution containing 0.05 tsp xanthan gum and 0.1 PM alumomagnesium silicate, also add 10 hours of propylene glycol. The mixture was thoroughly stirred and receive a 20% bulk concentrate for aqueous suspensions.P R I m e R of part 6. Oil spray.After dissolving the compounds (1) to(27) of the invention (or 0.1 hours) 5 hours of xylene and 5 o'clock trichloroethane solution is mixed with 89,9 including deodorized kerosene and receive a 0.1% oil spray.P R I m e R of part 7. Oil spray.Mix and dissolve 0,1 h compounds (1) to(27) of the invention, 0,2 hours of tetramethrin, 0,1 o'clock o' phenothrin, 10 am, trichloroethane and 59.6 hours deodorized kerosene and the resulting solution is filled aerosol is tyano gas) and get oil spray.P R I m e R of part 8. Water aerosol.Mixed together and dissolved in 0.2 parts of the compound (24) of the present invention, 0,2 o'clock o' allethrin, 0,2 o'clock o' phenothrin, 5 hours xylene, 3,4 including deodorized kerosene and 1 tsp emulsifier /ATMOS 300 (registered mark, Atlas chemical Co., Ltd.)/ and the resulting solution with 50 hours of distilled water is filled aerosol container. After the establishment of the container valve through it under pressure from the pump 40 hours of propellant (liquefied petroleum gas) with a water spray.P R I m e R of part 9. Mosquito spiral.After addition of 0.3 hours o' -allethrin to 0.3 g of compound (20) of the present invention, the mixture was dissolved in 20 ml of acetone. Then the solution is evenly mixed with with 99.4 g of a carrier for mosquito coil (tobacco crumbs:salesny powder: wood flour 4:3:3) under stirring, and then added to the mixture of 120 ml of water. The mixture is thoroughly kneaded, molded and after drying receive mosquito spiral.P R I m e R composition 10. Electric mosquito Mat.A mixture of 0.4 g of the compound (19) of the present invention, 0.4 g' -allethrin and 0.4 g of piperonylbutoxide dissolved in acetone to volume in mossy, cured plate) electric Mat size 2.5 SMH,5 cm and a thickness of 0.3 cm with obtaining electric mosquito Mat.P R I m e R of part 11. The fumigant.After dissolving 100 mg of compound 16 according to the invention in the required amount of acetone, the resulting solution is impregnated with a porous ceramic plate size 4x4 cm and a thickness of 1.2 cm with the receipt of fumigant.P R I m e R composition 12. Poisoned bait.After dissolving 10 mg of the compound (1) to(27) according to the invention in 0.5 ml of acetone, the resulting solution was applied to 5 g of dry powder animal feed. After drying of the powder is 5% poisoned bait.Further, the effectiveness of the compounds according to the invention as active ingredients of insecticidal compositions is described with reference to examples of trials where the compounds of the invention identified under the numbers given in the table. 2, and the compounds used for comparison and control, marked with the numbers given in the table. 3.P R I m e R test 1. (Insecticidal test on the Nymphs of the brown plant of a flea).Emulsifiable concentrate of the test compound, prepared in accordance with primerano submerged shoots of rice plants (approximately 12 cm). After drying in air shoots of rice plants are placed in a test tube for testing, which also put about 30 nymphs brown herbal flea beetle (Nilaparvata lugens). Six days later reveal the presence of living and dead nymphs. Assessment tests indicate the following way. and the lack of live insects, live insects 5 or less, with living insects 6 or more.The results are shown in table. 4.P R I m e R test 2. (Insecticidal test on blaske dinosau South).At the bottom of a polyethylene Cup with a diameter of 5.5 cm is placed filter paper of the same size, which is dotted 1 ml water diluted (500 or 50 ppm) of the emulsifiable concentrate of the test compound, prepared in accordance with example 1, and on which is placed in the quality of the food one germ of corn. In a bowl put about 30 eggs a flea dinosau South (Diabrotica undecimpunctata). Eight days after covering cups reveal the presence of living or dead hatched larvae. Criterion test results indicate the following.and the lack of live insects
in - living insects 5 or less
with living insects 6 or more
Obtained).Emulsifiable concentrate of the test compound obtained according to example 1, diluted with water and the diluted solution (0.7 ml) is added to 100 ml of deionized water (concentration of the active component of 3.5 ppm). In the mixture out 20 larvae of ordinary mosquito (Culex pipiens pallens) in the last mask stage. A day after the release of reveal mortality among larvae. Evaluation criteria indicate as follows.a - 90% or higher
in not less than 10% but less than 90%
with less than 10%
The results are shown in table. 6.P R I m e R test 4. (Insecticidal test on the beetles).At the bottom of a polyethylene Cup with a diameter of 5.5 cm is placed filter paper of the same size, which is dotted 0.7 ml water diluted (500 ppm) of the emulsifiable concentrate of the test compound, prepared in accordance with example 1. As food for filter paper evenly distribute 30 mg of sucrose. In the Cup run 10 adult male German cockroach (Prusak) (Blattella germanica). Six days after covering the Cup determines the number of dead or live insects to calculate mortality.The results ol polietileno Cup with a diameter of 5.5 cm is placed filter paper of the same size, which dotted 0.7 ml water diluted (500 ppm) of the emulsifiable concentrate of the test compound, prepared in accordance with example 1. As food for filter paper evenly distribute 30 mg of sucrose. In the Cup run 10 adult females home (Musea domestica). After 48 h after covering the Cup determines the number of dead or living insects with detection of mortality (2 repeat). The results are shown in table. 8 DERIVATIVES OF 1-PYRIDINEMETHANOL AND INSECTICIDAL COMPOSITION.1. Derivatives of 1-pyridinemethanol General formula
< / BR>where R1is hydrogen, C1- C3-alkyl;
R2- C1- C4-haloalkyl;
R3- halogen, trifluoromethyl;
R4- C1- C3-haloalkyl.2. Insecticidal composition comprising an active ingredient is a derivative of imidazole and target additives, characterized in that, to increase insecticidal activity, it as a derivative of imidazole contains a compound of General formula
< / BR>where R1is hydrogen, C1- C3-alkyl;
R2- C1- C4-haloalkyl;
wny ingredient - 0,1 - 95,0
Targeted supplements - the Rest
< / BR>Compound I has astragalina activity and can be used to stimulate growth of wheat
FIELD: organic chemistry, herbicides, agriculture.
SUBSTANCE: invention relates to new substituted benzoylketones of the general formula (I): , all possible tautomeric forms and possible salts that can represent active substance as a component of herbicide agent. In the formula (I) A means (C1-C4)-alkyl; R1 means cyclo-(C3-C6)-alkyl; R2 means hydrogen atom (H), cyano-group (CN); R3 means hydrogen atom (H), halogen atom, CF3, (C1-C4)-alkylsulfonyl; R4 means halogen atom; X means groups: or wherein R5 means (C1-C4)-alkyl, (C1-C4)-alkoxy-group, (C1-C4)-alkylthio-group, di-(C1-C6-alkyl)-amino-group; R6 means (C1-C4)-alkyl, (C1-C4)-alkoxy-group, cyclo-(C3-C6)-alkyl; n = 0 or 1 including all possible tautomeric forms and possible salts. Compounds of the formula (I) elicit herbicide activity and can be used in herbicide composition.
EFFECT: valuable properties of compounds.
3 cl, 1 sch, 3 tbl, 13 ex
FIELD: organic chemistry, herbicides, agriculture.
SUBSTANCE: invention describes a synergistic composition of herbicides comprising components (A) and (B) wherein (A) represents herbicide taken among the group of the formula (I):
wherein R1 means (C1-C4)-alkyl; R2 means (C1-C4)-alkyl; R3 means hydrogen atom; X and Y mean (C1-C4)-alkoxy-group; (B) represents one or two herbicides taken among the group of compounds or their acceptable forms: alachlor, metolachlor, acetochlor, dimetenamide, atrazine, cyanasin, metribusin, fluthiamide, nicosulfuron, rimsulfuron, primisulfuron, pendimetalin, sulcotrion, dicamba, mesotrion, isoxachlortol, metosulam, anilofos, fenoxaprop-ethyl, setoxydim, diclofop-methyl, MCPA, bromoxynil, pyridat, clopyralid, iodosulfuron-methyl, ethoxysulfuron, amidosulfuron, gluphosinat-amminium, isopropylammonium-glyphosate, imasetapir wherein components (A) and (B) are taken in the effective doses. Also, invention describes a method for control of weeds by using above indicated herbicide composition. Invention provides the development of the synergistic herbicide composition eliciting high activity.
EFFECT: improved method for control, valuable properties of composition.
6 cl, 26 tbl, 3 ex
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: 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: 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, 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: organic chemistry, insecticides.
SUBSTANCE: invention relates to an insecticide-acaricide agent comprising a mixture of compound of the formula (I): wherein X means halogen atom, (C1-C4)-alkyl, (C1-C4)-alkoxyl; W, Y and Z mean independently of one another hydrogen atom (H), halogen atom, (C1-C4)-alkyl, (C1-C4)-alkoxyl; A means H, (C1-C6)-alkyl; B means H, methyl or ethyl; A and B in common with carbon atom to which they are bound form saturated unsubstituted (C3-C6)-ring or substituted with (C1-C4)-alkoxy-group; D means H, (C1-C6)-alkyl; G means H or one of the following groups: (b) or (c) wherein L means oxygen atom (O); M means O; R1 means (C1-C10)-alkyl, (C3-C6)-cycloalkyl that if necessary can comprise one nitrogen atom (N) or O; R2 means (C1-C10)-alkyl and agonist, respectively, antagonist of nicotine acetylcholine receptors chosen from the group comprising compounds of formulas: (IIa) (IIe) (IIg) (IIh) (IIi) (IIk) (IIl) and (IIm) taken in synergetically effective ratio.
EFFECT: valuable biological properties of substances.
6 cl, 22 tbl, 6 ex
SUBSTANCE: synergetic herbicide composition contains active substances such as chlorimuron-ethyl (I) and imazetapir (II) and salts thereof, used in the ratio of (I):(II)-10:1, and also contains fillers, diluents, surfactants and other functional additives needed for producing of preparation forms. Method for controlling of weed plants in sown farm crops involves using effective doses of preparations adapted for suppressing weed plants without affecting leguminous crops such as soya, feed beans, pea etc.
EFFECT: wider range of weed plant controlling means and processes.
5 cl, 2 dwg, 7 tbl, 13 ex
FIELD: organic chemistry, fungicides.
SUBSTANCE: invention describes substituted 1-(pyridinyl-2)-2-azolylethanols of the general formula (I): wherein R means hydrogen atom, direct or branched alkyl with 1 to 8 carbon atoms, cycloalkyl with from 3 to 8 carbon atoms; X means nitrogen atom or CH-group. Also, invention relates to a method for synthesis of these compounds and a fungicide composition that contains compound of the formula (I). Invention provides expanding assortment of fungicides for carrying out the effective control of harmful fungi.
EFFECT: valuable fungicide properties of compounds and composition.
5 cl, 1 tbl, 7 ex
FIELD: organic chemistry, medicine, pharmacy.
SUBSTANCE: invention relates to using phenylethenyl- or phenylethynyl-derivatives as antagonists of glutamates receptors. Invention describes using compound of the general formula (I):
wherein each among R1, R2, R3, R4 and R5 means independently of one another hydrogen atom, (C1-C6)-alkyl, -(CH2)n-halogen, (C1-C6)-alkoxy-group, -(CH2)n-NRR', -(CH2)n-N(R)-C(O)-C1-C6)-alkyl, phenyl or pyrrolyl that can be unsubstituted or substituted with one or more (C1-C6)-alkyl; each among R, R' and R'' means independently of one another hydrogen atom or (C1-C6)-alkyl; A means -CH=CH- or C≡C; B means ,, , , or wherein R6 means hydrogen atom, (C1-C)-alkyl, -(CH2)n-C(O)OR, or halogen atom; R7 means hydrogen atom, (C1-C6)-alkyl, -(CH2)n-C(O)OR', halogen atom, nitro-group or oxodiazolyl group that can be unsubstituted or substituted with (C1-C6)-alkyl or cycloalkyl; R8 means hydrogen atom, (C1-C6)-alkyl, -(CH2)n-OH, -(CH2)n-C(O)OR'' or phenyl; R9 means (C1-C6)-alkyl; R10 and R11 mean hydrogen atom; R12 means -(CH2)n-N(R)-C(O)-(C1-C6)-alkyl; R13 means hydrogen atom; each R14, R15, R16 and R17 independently of one another means hydrogen atom or (C1-C6)-alkoxy-group; each R18, R19 and R20 independently of one another means hydrogen atom; R21 means hydrogen atom or (C1-C6)-alkyl; R22 means hydrogen atom, (C1-C6)-alkyl or (C1-C6)-alkyl comprising one or more substitutes chosen from groups hydroxy- or halogen atom; R23 means hydrogen atom, (C1-C6)-alkanoyl or nitro-group; each among R24, R25 and R26 independently of one another means hydrogen atom or (C1-C6)-alkyl; n = 0, 1, 2, 3, 4, 5 or 6; X means -O- or -S-; Y means -CH= or -N=, and its pharmaceutically acceptable salts used in preparing medicinal agents designates for treatment or prophylaxis of disorders mediated by mGluR5-receptors. Also, invention describes compounds of the formula (I-A), compound of the formula (I-B-1) given in the invention description, and a medicinal agent used in treatment or prophylaxis of disorders mediated by mGluR5-receptors.
EFFECT: valuable medicinal properties of compounds.
44 cl, 1 tbl, 44 ex
FIELD: organic chemistry, medicine.
SUBSTANCE: invention describes derivatives of 1H-imidazole-4-carboxamide of the formula (I): wherein R represents phenyl, 2-pyridinyl, 3-pyridinyl that can be substituted; R1 means phenyl, 5-membered aromatic heterocyclic ring comprising one nitrogen atom (N) as a heteroatom that can be substituted; R2 means hydrogen atom (H), (C1-C8)-alkyl; R3 represents (C2-C8)-alkyl, (C1-C8)-alkoxy-group, (C3-C8)-cycloalkyl, benzyl group, aromatic ring that can be substituted; R4 means hydrogen or halogen atom, cyano-group, sulfamoyl, methanesulfonyl, methylsulfanyl or (C1-C4)-alkyl. Also, invention describes methods for synthesis of these compounds and pharmaceutical compositions. Derivatives of 1H-imidazole-4-carboxamide are effective agonists, partial agonists or antagonists of cannabinoid CB1-receptors that can be useful in treatment of psychic and neurological diseases and other diseases with involving cannabinoid neurotransmission.
EFFECT: valuable biological and medicinal properties of compounds and pharmaceutical compositions.
11 cl, 1 tbl, 113 ex
SUBSTANCE: in novel compounds of formula (I) X stands for C, N; R1 stands for H or (lower) alkyl, R2 stands for 9(lower) alkyl, -(CH2)n-R2a; R2a stands for C3-C8cycloalkyl, optionally and independently mono-, di-, tri- or tetrasubstituted with the following groups: OH, (lower)alkyl, (lower)alkoxy, 5- or 6-member single-valent saturated heterocyclic ring, containing from one to two heteroatoms, independently selected from nitrogen, oxygen and sulfur, said heterocyclic ring being optionally and independently mono-, di- or tri-substituted with the following groups: OH, (lower)alkyl, (lower)alkoxy, 5- or 6-member single-valent heteroaromatic ring, containing from one to two heteroatoms, independently selected from nitrogen, oxygen and sulfur, said heteroaromatic ring being optionally and independently mono-, di- or tri-substituted with the following groups: OH, (lower) alkyl, (lower)alkoxy, C3-C6cycloalkyl; R3 stands for C3-C6cycloalkyl, being optionally and independently mono-, di- or tri- or tetra-substituted with groups: OH, (lower) alkyl, (lower)alkoxy, phenyl, which optionally and independently is mono-, di- or tri- or tetra-substituted with groups: OH, (lower)alkyl, (lower)alkoxy, halogen, (lower)alkylamino, halogenated (lower)alkyl, halogenated (lower)alkoxy, nitro; R4 stands for 5- or 6-member single-valent heteroaromatic ring, containing from one to two nitrogen heteroatoms, said heteroaromatic ring being optionally and independently mono-, di- or tri- substituted with the following groups: OH, (lower) alkyl, (lower)alkoxy, halogen; naphtyl, which optionally and independently is mono-, di- or tri- substituted with groups: OH, (lower)alkyl, (lower)alkoxy, halogen, (lower)alkylamino, halogenated (lower)alkyl, halogenated (lower)alkoxy, nitro; or phenyl, which optionally and independently is mono-, di- or tri- substituted with groups: OH, (lower)alkyl, (lower)alkoxy, halogen, nitro, halogenated (lower)alkyl, halogenated (lower)alkoxy, cyano, (lower)alkylsulfonyl, -NR7R8; or two neighbouring substituents in said phenyl residue together represent -O-(CH2)p-O-, -(CH2)2-C(O)NH-; R5 and R6 each independently represent H, (lower)alkyl; R7 and R8 each independently represent hydrogen, (lower)alkyl, or R7 and R8 together with nitrogen atom, to which they are bound, form 5- or 6- member saturated or aromatic heterocyclic ring, which optionally contain nitrogen as additional heteroatom; said saturated or aromatic heterocyclic ring, being optionally substituted with the following groups: OH, (lower)alkyl, (lower)alkoxy; m equals 1 or 2, n equals 0 or 1, p equals 1, 2 or 3; or their pharmaceutically acceptable salts.
EFFECT: increased antagonistic activity of compounds.
SUBSTANCE: invention refers to 1,2,4,5-tetrasubstituted imidazole derivatives of general formula (I) , where R1 represents chlorine, bromine, fluorine or hydrogen atom, R2 represents chlorine or bromine atom, A represents nitrogen atom or group CH, X represents sulphur atom or sulphoxide (S=O) group, or sulphonic (SO2) group, Y represents hydrogen atom or methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl group, Z represents CH group, n represents number 1,2 or 3, and pharmacologically acceptable salts of compounds. Besides, the invention concerns a pharmaceutical composition based on the compound of general formula (I), to the compounds of general formulas and and to application of compounds of general formula (I).
EFFECT: new imidazole derivatives being selective modulators of cannabinoid receptors CB1 with high selectivity.
12 cl, 1 tbl, 4 ex
SUBSTANCE: invention refers to imidazoline derivatives having CB1-antagonist activity of general formula where: R1 and R2 independently stand for phenyl which can be substituted with 1-2 substitutes Y being identical and represent chlorine, bromine, fluorine, iodine, X stands for one subgroup or , where: R3 stands for hydrogen atom or linear C1-3 alkyl group, R4 stands for C3-8 cycloalkyl or C5-10, and said groups can contain one atom N, R7 represents benzyl or phenyl group, and specified groups can be substituted in aromatic ring by 1 substitute Y, where Y is evaluated as specified above being either identical, or different, or R7 stands for C1-8dialkylaminogroup, R8 represents hydrogen atom, R9 represents hydrogen atom and their salt. Additionally, the invention concerns a pharmaceutical composition based on compound of formula I, and to its application for therapy of diseases caused by canabiod neurotransmission.
EFFECT: new compounds possess useful biological activity.
9 cl, 1 tbl, 3 ex
SUBSTANCE: present invention relates to new imidazole derivatives of general formula I , where R1 is C1-C10alkyl or C3-C10cycloalkyl, each possibly and independently substituted with 1 substitute selected from C3-C10cycloalkyl or aryl or a heteroaryl group, possibly substituted with one or two halogens; aryl or heteroaryl; R2 is C1-C10alkoxy or C1-C10thioalkyl; R3 is C1-C10alkoxy, possibly substituted with one C1-C10alkoxy or nitrile, where the said alkoxy group can be cyclic or can contain one O heteroatom; R4 is C1-C10alkyl; C2-C10alkenyl; C1-C10alkoxy or C3-C10cycloalkyl, each possibly and independently substituted with 1 or 2 substitutes selected from C1-C10alkoxy, C3-C10cycloalkyl, carboxylic ester, or with one or two aryl or heteroaryl groups, possibly substituted with one substitute selected from C1-C10alkyl, C3-C10cycloalkyl, nitro or halogen; aryl or heteroaryl, each possibly and independently substituted with 1-3 substitutes selected from C1-C10alkyl, C3-C10cycloalkyl, C1-C10alkoxy, phenoxy, thiophenyl, halogen, nitro, nitrile or aryl group, possibly substituted with one halogen; where up to three hydrogen atoms of the alkyl group can be substituted with fluorine atoms; where the said cycloalkyl can independently have one or two carbon atoms substituted with O or N; where the said aryl denotes an aromatic ring having 6 to 10 carbon atoms, including mono- and bicyclic compounds; and where the said heteroaryl denotes an aromatic ring having 3 to 10 carbon atoms, including mono- and bicyclic compounds in which one to three ring atoms are oxygen, nitrogen or sulphur atoms; except compounds given in paragraph 1. The invention also pertains to use of the said compounds for making a medicinal agent, a treatment and prevention method, a compound of formula II (values of radicals are given in the formula of invention).
EFFECT: new imidazole derivatives having positive allosteric modulator effect on GABAB receptor are obtained.
30 cl, 6 ex
FIELD: medicine, pharmaceutics.
SUBSTANCE: there is described a compound of formula I: or its pharmaceutically acceptable salt, where R2 represents (CR3R4)n-NR5R6 and m, p, q, Ar, R1, R3, R4, R5 and R6 are those as specified in the patent claim and defined as selective 5-NT6 and/or 5-NT2A antagonists. There is also described a pharmaceutical composition containing this compound, and application thereof in preparing drugs for treating diseased conditions of central nervous system chosen from psychoses, schizophrenia, manic depressions, neural disorders, memory impairment, attention deficient syndrome, Parkinson's disease, amyotrophic lateral sclerosis, Alzheimer's disease, malnutrition and Huntington's disease.
EFFECT: preparation of the compounds which can find application in treatment of a diseased condition of central nervous system.
27 cl, 1 tbl, 29 ex
FIELD: medicine, pharmaceutics.
SUBSTANCE: claimed invention relates to novel derivatives of 1H-imidazole of formula I, in which R1 represents hydrogen, halogen atom, C1-3-alkyl group, and said C1-3-alkyl groupcan include 1-3 fluorine atoms or R1 represents cyclopropyl, piano, or methylsulfanyl group, R2 represents phenyl group, which can be substituted with 1 substituent Y, selected from methoxy, chlorine, fluorine, trifluoromethyl and cyano, or R2 represents pyridyl group, on condition that R2 is not 6-methyl-2-pyridyl group, or R2 represents fully saturated 6-7-member monocyclic, condensed bicyclic ring system or benzothiazolyl, benzodioxane or thiazole group, and said groups can be substituted by 1 fluorine atom, or R2 represents group of general formula CH2-R5, in which R5 represents phenyl group or fully saturated 7-member condensed bicyclic carbocyclic ring system, or R5 represents piperidine or tetrahydrofuran ring system, which can be substituted by methyl, or R2 represents methylsulfonylamino(C3)alkyl group, R3 represents hydrogen, halogen atom, C1-6-alkylsulfonyl, cyanogroup, or R3 represents C1-8-alkyl group, and said C1-8-alkyl group can be substituted by 1-3 fluorine atoms, or R3 represents phenyl group, which is substituted by substituent Y, where Y has value, specified above, or R3 represents furanyl group, R4 represents one of subgroups (i) or (ii), where R6 represents C4-8-branched or linear alkyl group or naphtyl group, R7 represents hydrogen atom, linear C1-6-alkyl group, R8 represents C2-6-alkyl group, substituted by 1-3 fluorine atoms, or R8 represents C3-8-cycloalkyl group, piperidine group, C3-8-cycloalkyl- C1-2-alkyl group, tetrahydrofuranyl- C1-2-alkyl group, C5-10-bicycloalkyl group, C5-10-bicycloalkyl-C1-2-alkyl group, C6-10-tricycloalkyl group, C6-10-tricycloalkyl-C1-2-alkyl group, and said groups can be substituted by 1-3 substituents, selected from methyl or hydroxyl, or R8 represents phenyl group, substituted by 1-2 substituents Y, specified above, or R8 represents naphtyl, 1,2,3,4-tetrahydronaphtyl or indanyl group, and said groups can be substituted by 1 substituent Y, or R8 represents phenyl- C1-3-alkyl group, diphenyl- C1-3-alkyl group, and said groups can be substituted ob their phenyl ring by 1 substituent Y, where Y has value specified above, or R8 represents benzyl group, substituted by 2 substituents Y, or R8 represents quinilinyl, pyridinyl, benzimidazole or naphtylmethyl group which can be substituted by substituent Y, where Y has value, specified above, or R8 represents asabicyclo[3,3,0]octanyl group, on condition that R8 is neither 6-methoxybenzothiazole-2-yl group, nor [3-chlor-5-(trifluoromethyl)pyrid-2-yl]methyl group, or R7 and R8 together with nitrogen atom, to which they are bound, form saturated, non-aromatic, monocyclic or bicyclic heterocyclic group, including only one nitrogen atom, having 7-10 ring atoms, which can be subslituted by 3 C1-3-alkyl groups, or R7 and R8 together with nitrogen atom, to which they are bound, form saturated, monocyclic heterocyclic group, optionally including another N atom, having 6 ring atoms, and said heterocyclic group is substituted by C1-3-alkyl groups, on condition that R7 and R8 together with nitrogen atom, to which they are bound, do not form trimethylsubstituted asabicyclo[3,3,0]octanyl group, as well as their stereoisomers and pharmacologically acceptable salts of said formula (I) compounds and their stereoisomers Invention also relates to intermediate compounds of formula XIV, pharmaceutical composition based on formula I compound, method of obtaining such pharmaceutical composition and application of formula T compound.
EFFECT: obtained are novel derivatives of IH-imidazole, which are modulators of cannabinoid CB2-receptors.
8 cl, 1 tbl, 3 ex