• 专利附录
  • 专利说明
  • 权利要求
  • 类似技术
  • 同族专利
  • 引用文献
  • 法律状态
  • 优先权
    • 专利摘要:
    1. A substituted sulfonic acid anilide of the formula (I) see diagramm : EP0013742,P14,F1 where R**1 is alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkenyl (each of up to 12 carbon atoms) or arylalkyl (of 7 to 14 carbon atoms), each of which may be unsubstituted or substituted by halogen, cyano, thiocyanato, azido, nitro, C1-4 -alkoxy, C6-10 -aryloxy, C1-4 -alkylthio, C6-8 -arylthio, C1-4 -alkylsulfinyl, C1-4 -alkylsulfonyl, arylsulfinyl, arylsulfonyl, C1-5 -alkanoyl, C1-5 -alkoxycarbonyl, C1-5 -alkylcarbamyl, di-(C1-5 -alkyl)-carbamyl, C1-4 -alkanoylamino, C1-4 -haloalkanoylamino, C1-6 -alkanoyloxy, C1-4 -alkanoylthio, C1-4 -alkoxycarbonyl-amino, C7-13 -aroyloxy, C1-6 -alkylamino, di-(C1-6 -alkyl)-amino, C6-12 -arylamino, C1-6 -alkylcarbamyl-amino, di-(C1-6 -alkyl)-carbamylamino, C1-6 -alkyl-carbamyloxy, di-(C1-6 -alkyl)-carbamyloxy, C1-4 -alkylaminosulfonyloxy or di-(C1-4 -alkyl)-amino-sulfonyloxy or combinations of these groups, or is cyano, thiocyanato, unsubstituted or C1-4 -alkyl-substituted amino, aminosulfonyl, guanyl, N2 -hydroxyguanyl, hydroximoyl or C1-5 -alkoxy-imidoyl, or is unsubstituted or halogen-substituted C1-4 -alkylsulfenyl or C1-4 -alkylsulfinyl, or is unsubstituted or halogen- and/or C1-4 -alkyl-substituted arylsulfinyl or arylsulfonyl, where aryl is of up to 10 carbon atoms, R**2 and R**3 are identical or different and each is halogen, cyano, thiocyanato, nitro or unsubstituted or halogen-substituted C1-4 -alkyl, C1-4 -alkoxy, C1-4 -alkylthio, C1-4 -alkylsulfinyl, C1-4 -alkylsulfonyl or C1-4 -alkanoyl.
    公开号:SU932965A3
    申请号:SU802863202
    申请日:1980-01-04
    公开日:1982-05-30
    发明作者:Штубенраух Герд；Хампрехт Герхард；Эйккен Карл；Юнг Иоганн
    申请人:Басф Аг(Фирма)；
    IPC主号:
    专利说明:

    where R has the abovementioned banners and L denotes a nucleophilic displaced detachable group, in particular, halogen, hydrogen sulfate, halogen sulfate, 4 or more substituted or substituted alkyl, sulfonyloxy, arylsulfonyloxy, alkyl sulfate residues, oxonyls, sulfonates, oxonols, oxonics, sulfonyls, aromas, oxonyls, sulfonylsulfate, oxonyls, oxalons, oxalons, oxalons, halogen, hydroxylsulphates the presence of a diluent and / or acid acceptor and / or accelerator of the reaction at temperatures between 0 and 170 ° C or
    b) compound of general formula
    NH-Oo-dHj
    (Iv)
    to
    1H, H
    where R has the above meanings is reacted with sulphonating agents of the formula
    CP3 - S02- Z, (V) where Z denotes a leaving group, in particular halogen or anhydride residue CF S020-, in appropriate cases in the presence of a diluent or organic or inorganic
    jsTHe - bnz
    H.d
    CH N
    base at temperatures between -60 and + 120C.
    Instead of the free hydrogen compounds of the formula II or IV, the corresponding salts can also be used, which are obtained by known methods in a preliminary reaction or, in the appropriate case, by adding an equivalent amount of an organic or inorganic base, for example, alkali or alkaline earth metal salts or, in the corresponding case, alkyl-substituted ammonium salts.
    The derivative thus obtained, where K is alkylthioalkyl or arylthioalkyl, can be suitably oxidized to the corresponding sulfynyl or sulfonyl compound.
    Derivatives in which R is a cyano group can be converted to the corresponding guanyl or alkoxy imidoyl compounds with amines, alcohols or hydroxylamines. If anilide 5 acetamido-2, + - dimethyl trifluoromethanesulfonic acid and methyl bromide are used as starting materials, the reaction according to variant d proceeds according to the scheme
    NHd - ciHs If the starting material used is sodium salt of anilide 5 acetamido-2, (α-dimethyl trifluoromethane iTHci-ciHs N- $ OzClF3 + ciid JH a) If you use 5 acetamido-2-methylphenyl cyanamide and chloramine, as a starting material, 5 acetamido-2-methylphenyl-cyanamide and the hydrochloride sodium chloride are used as starting materials. ) ... CF3 SNEN of sulfonic acid and as a reaction accelerator sodium iodide, the reaction according to variant O follows the NHC-c1H3 scheme (iF5 yrql -NaCl f-tormethanesulfonic acid, the reaction according to the version follows the scheme ivMdoCHj dl dH. N For both options For example, the following solvents and diluents may be used: water, formamides , such as dimethyl ormamide formamide, dimethyl acetamide; anisole, dimethoxyethane, n-butylethyl ether, dioxane nitroalkanes, for example nitromethane; nitrobenzene; alcohols, such as methanol, ethanol, isopropanol, n-butanol, 3 methylbutanol; ureas such as tetramethyl urea; ether alcohols, for example ethylene glycol monomethyl ether; sulfones, for example sulfolane; esters such as acetic acid ester, propionic acid methyl ester, formic acid methyl ester; halogenated hydrocarbons, in particular chlorinated hydrocarbons, for example, methylene chloride, chloroform, 1, 2-dichloroethane, 1,1, 2,2- or 1,1, 1,2-tetrachloroethane, dichloropropane, trichloroethylene, chlorobenzene, o, M, p- dichlorobenzene, fluorobenzene, o, / and p-chlorotoluene, dichloro-naphthalene, carbon tetrachloride; aliphatic or cycloaliphatic hydrocarbons such tcaK heptane, o, M, P-kimol, gasoline fractions in the boiling point range of 70-190 ° C, cyclohexane, methylcyclohexane, decalin, petroleum ether, ligroin, 2,2,4-trimethylpentane, octane; aromatic hydrocarbons, such as benzene, toluene, o, m, p-xylene, tetralin; and the corresponding mixtures. It is advisable to use a solvent in an amount of 100-2000 wt. 4, preferably 100-1000 wt.% In the calculation of the starting compounds II and IV. Options o and b are preferably in the presence of an organic or inorganic base. In particular, basic oxides, basic oxides, tertiary amines, alcohols, carbonates or hydrides such as potassium hydroxide, sodium, potassium carbonate, calcium oxide, oxide are used. barium, magnesium hydroxide, magnesium oxide, barium hydroxide, calcium carbonate, magnesium carbonate, magnesium bicarbonate, zinc hydroxide, zinc oxide, zinc carbonate, zinc bicarbonate, sodium methyl acetate, magnesium t methyl, potassium methoxide, sodium propyl, isopropyl t aluminum, sodium butyl, lithium methylate, calcium cyclohexinolate, sodium isopropylate, potassium t-butoxide, trimethylamine, triethylamine, tripropylamine, triisopropylamine, tributylamine, triisobutylamine, tri-sec. , trihexylamine, N, N-dimetilaiilin, N, N-dietilanilin, N, N-diisopropylaniline, N, N-dimetiltoluidin, N, N-dietiltoluidin, M, M-dipropiltoluidin, N, N-dimethyl-n-aminopiridin, M , N-diethyl-P-aminopyridine, N-methylpiperidine, N-ethylpiperidine, N-methylpyrrolidine, N-ethylpyrrolidine , N-methylpyrrole, N-methylmorpholine, N-ethylmorpholine, N-metilgeksametilenimin, pyridine, quinoline, O6, 1, y-picoline, N, N, N, N-tetramethylethylenediamine, N-ethyldiisopropylamine, N, N-dimethylcyclohexylamine, hydride sodium, lithium hydride, calcium hydride. However, it is also possible to use commonly used base materials. Preferably, iodides and metal bromides are used as a reaction accelerator, for example, sodium iodide, potassium bromide, calcium iodide; Crown ether quaternary ammonium compounds, such as iodide or tetrabutylammonium bromide; or combinations of these substances. Option a is carried out mainly at 0-170 ° C, preferably at, for 30 minutes and 100 hours, preferably for 1 hour and 2 hours, without pressure or with pressure, continuously or discontinuously. In embodiment a, in general, 1 mol of compound II and the corresponding salt of 0.5-2 mol, preferably 0.9-1.5 mol, of compound 111 are used, in the corresponding case 0.5-2 mol of base, and 0.01-0.1 mol of the reaction accelerator. To isolate the desired products of the formula I, the reaction solution or the residue remaining after removal of the solvent and diluent is added, in the case of using water-miscible solvents or diluents, to a dilute aqueous alkaline solution. If an oil separates, it is extracted or the solution above is decanted; the resulting precipitate is sucked off; With water-immiscible diluents, the orpanic phase is extracted with a dilute aqueous solution of caustic alkali, dried and concentrated. If during the reaction the desired product directly precipitates, it can be isolated by simple suction. The desired products can, if appropriate, be purified in the usual manner, for example by recrystallization or chromatography. Variant S is carried out at -60 and + 120 ° C, preferably at and + 80 ° C for 1 hour to 100 hours, without pressure or with pressure, continuously. At 1 mol of compound of formula IV, in general, 0 , 8-1.3 mol, preferably 0,, 1 mol of sulfonating agent, as well as 0.8-2 mol of base. Isolation of the desired product of formula I is carried out according to variant o. 1. To a suspension of 19.2 h. Bromine in 80 parts of water is added dropwise with stirring for about 10 minutes at 0-10 ° C. A solution of 5.9 parts of sodium cyanide in 0 hours of water. After bleaching the mixture, a solution of kh sodium hydroxide and 31 anilide 5 acetamido-2,4-dimethyl trifluoromethanesulfonic acid in 50 hours water is added and further stirred at 5 ° C at 50 ° C. After cooling, the mixture is alkalinized with a small amount of an aqueous solution of caustic in the mixture and the precipitate is sucked off. After drying, 29.5 parts (88 from theory) of anilide 5 of acetamido-H-cyano-2, 4-dimethyl trifluoromethanesulfonic acid, m.p. 110-111 C. According to the method described above, other compounds of general formula I are obtained. The new compounds have a strong biological effect on plants, i.e. they act on the growth of plants either by inhibiting growth in height, or by changing the concentration of substances contained in the plants, or by destroying unwanted plants while simultaneously preserving beneficial uranium. The proposed compounds are used, for example, in the form of directly sprayed solutions, powders, suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, soil application agents, granules during spraying, spraying, spraying, scattering or watering. The form of the substance depends entirely on the intended use. For the preparation of directly sprayed solutions, emulsions, pastes and oil dispersions, fractions of medium to high boiling point oils, such as kerosene or diesel oil, coal tar oils, etc., are used, and such oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, for example benzene, toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, for example methanol, ethanol, propanol, butanol, chloroform, tetrachloromethane an, cyclohexanol, cyclohexanone, chlorobenzene, isophorone, etc. To, highly polar solvents, for example, dimethylformamide, dimethyl sulfoxide, N-methylpyrilidone, water, etc. Aqueous use forms can be obtained from emulsion concentrates, pastes or wettable powders, oil dispersions by the addition of water. To prepare emulsions, pastes or oil dispersions, substances can be homogenized as such or dissolved in oil or in solvent by means of adhesives, wetting agents, dispersants or emulsifiers in water. Concentrates may also be prepared consisting of an active principle, a wetting agent, an adhesive, a dispersant or an emulsifier and, if appropriate, a solvent or oil, which are suitable for dilution with water. I as surfactants should indicate salts with alkali or alkaline-earth metals or ammonium of lignosulfonic acid, naphthalenesulfonic acid, phenyl sulphonic acid, alkylarylsulfonates, alkyl sulfates, alkylsulfonates, salts with alkali and alkaline earth metals dibutylnaphthalenesulfonic acid, lauryl ether sulfate, fatty alcohol sulfates, fatty acid salts of alkali and alkaline earth metals9, salts of sulfated hexadec nols, heptadecanols, octadecanols, and sulphate alcohols. , isotridecyl alcohol, condensates of fatty alcohols with ethylene oxide, ethoxylated castor e oil, polyoxyethylene alkyl ethers, ethoxylated lioxypropylene, lauryl alcohol polyglycol ether acetal, sorbitol ester, lignin, spent sulfite liquors and methylcellulose. Powders for soil application and dusts can be obtained by mixing or co-grinding the active principles with a solid carrier. Granules, for example, coated, impregnated and homogeneous, can be obtained by binding the active principles to solid carriers. Solid carriers are, for example, mineral earths, for example silica gel, cream nevy acids, silica gels, talc silicates, kaolin, attacli, limestone, chalk, talc, bolus, loess, clay, dolmoMMj, diatomaceous earth, calcium sulfate and magnesium. , magnesia, ground plastics, fertilizers, such as superphosphate, sulfate, phosphate, ammonium nitrate, ureas, and vegetable products, such as different types of bread meal, wood bark flour, wood flour and peanut flour, cellulose powder and other solid carriers . The compositions contain 0.1-95% by weight of active ingredient, preferably 0% by weight. In various cases, the combination or mixture of the proposed substances with other plant growth regulators, such as ethylene-forming substances of different chemical structures (for example, phosphonic acid derivatives, silanes, ethyl hydrazines), onium compounds (for example, trimethylammonium salts, hyDrazoni and sulfonium, morpholine derivatives 5 piperidinium and pyrazine compounds) may be beneficial. Interesting are other growth-regulating substances, for example, from the group of maleic hydrazides, derivatives of abscissic acid, chlorinated phenoxy; (caustic-like common acids, as well as polyhydric alcohols and esters of fatty acids with a specific effect on meristematic tissues. Offered remedies can be varied an amount that depends mainly on the desired effect. The consumption rate is 0.115 or more, preferably 0.2-6 kg of active ingredient per hectare. The beginnings affect the growth of above-ground and underground parts of plants in different ways and have only minor toxicity to warm-blooded plants in ordinary working concentrations. The new tools interfere with ({the biological processes of plant development and can be used for various purposes. The various effects of these active principles depends mainly on the time of application, based on the stage of development of the seeds or plants, as well as on the applied concentrations. New agents affect vegetative and generative growth of plants, as well as at the appropriate concentration and ability to germinate. The effect on vegetative development consists mainly in reducing the height of growth, as a result of which in many plants, in particular in cereals, the resistance is increased and the tendency towards so-called lodging is reduced. At the same time, tillering improves, leading to the development of a larger number of stem-bearing stems per unit area. In grasses, a reduced height is reflected in the formation of a denser, more stable grass cover, and above all in the fact that it does not need to be mowed frequently. The latter is advantageous for decorative turf, however, for grass areas along the streets of public gardens it has an advantage in ore capacity. Moreover, parallel to a smaller height of growth, an increase in chlorophyll content occurs, as a result of which treated grass and other vegetation cover takes on a dark green color. The effect on vegetative growth contributes to numerous plants, such as cotton and soybean, to the increased formation of flowers and fruits. Especially it should be emphasized that the treatment of the proposed substances promotes the growth of the root. This leads to a more rational use of water and nutrients from treated plants; Not only does drought resistance increase, but frost resistance is versatile and extensive is also possible in fruit growing and ornamental plant growing, as well as in creating artificial landscapes, including a suitable vegetative influence on parks, as well as on airfields and training floor x. The proposed substances can also be successfully used to influence the processes of flowering and maturation, as well as within the framework of special growing methods. New tayuha agents can positively affect the concentration of important substances found in plants. The size and type of action depends on various factors, in particular on the time of application, depending on the stage of development of the plant and the consumption rate. However, these factors in turn depend on the plant species and the desired effect. For example, lawns are treated throughout the growing season; ornamental plants, which should increase the intensity of bloom and the number of flowers, are treated before the formation of flowers; Plants whose fruits are used should be processed in an appropriate period of time before harvest. Various derivatives of the above class of compounds have herbicidal properties. Therefore, they are suitable for eliminating and inhibiting unwanted plant growth. Example .20 weight.h. The compounds of Example 1 were carefully rehecting the floor of the 3rd conglomerate. sodium salts of diisobutylnaphthalene-o6-sulfonic acid, 17 parts by weight sodium salts of ligninsulfonic acid from spent sulfite liquor and 60 parts by weight. powdered 512 different gels of silicic acid and ground in a hammer mill. By finely distributing the mixture to 20,000 parts by weight. water, a spray solution is obtained which contains 0.1% by weight of active ingredient. Example 5. 3 weight.h. The compounds of Example 2 were thoroughly mixed with 97 parts by weight. highly dispersed kaolin. So get powdered drug, which contains 3 wt. acting start. Example 6. 30 weight.h. The compounds of Example 3 were thoroughly mixed with a mixture of 92 parts by weight. powdered silica gel and 8 weight.h. paraffin oil, which is sprayed onto the surface of the silica gel. Thus, an active agent with good adhesion is obtained. Example 7. 0 pbw of the compound is thoroughly mixed with 10 parts of the sodium salt of the condensate phenolsulfonic acid-urea-formaldehyde, 2 hours, silica gel and 48 parts of water. A stable aqueous dispersion is obtained. By adding 100,000 parts by weight. WATER receive an aqueous dispersion containing Q, weight. acting start. Example 8. 20 parts of the compound are thoroughly mixed with 2 parts of the calcium salt of dodecylbenzenesulfinic acid, 8 parts of polyglycolic ester of fatty alcohol, 2 parts of the sodium salt of the condensate phenolsulfonic acid-urea-formaldehyde and 68 parts of paraffin mineral oil. A stable oily dispersion is obtained. Example 9. Mix 90 parts by weight. Compounds of example 1 with 10 v.ch. To -methyl- (L-pyrrolidone and get a solution suitable for use in the form of tiny droplets. Example 10. Dissolve 20 parts by weight of the compound of example 2 in a mixture consisting of 80 weight h, xylene, .10 parts by weight of an addition product 8-10 mol of ethylene oxide to 1 mol of oleic acid N-monoethanolamide, 5 parts by weight of dodecylbenzosulfonic acid calcium salt and 5 parts of an addition product of lO mol of ethylene oxide to 1 mole of castor oil. By pouring and finely distributing the solution in 100,000 parts by weight of water.
    13
    an aqueous dispersion is obtained containing 0.02 wt D of the active principle.
    Example 11. 20 weight.h. The compounds of Example 3 are dissolved in a mixture consisting of 0 pbw. cyclohexanone, 30 weight.h. Isobutanol, 20 weight.h. product of the addition of 7 mol of ethylene oxide to 1 mol of isooctylphenol and 10 weight.h. when the compound is 0 mol of ethylene oxide to 1 mol of castor oil. By infusing and finely distributing the solution in 100,000 parts by weight. water receive an aqueous dispersion containing 0.02 weight. acting start.
    Example. 12. 20 weight.h. The compounds of Example 3 are dissolved in a mixture consisting of 25 wt. hours. cyclohexanol, b5 weight ,, h. fractions of mineral oil so kip. 210-28 ° C and 10 weight.h. an addition product of 0 mol of ethylene oxide to 1 mol of castor oil. By infusing and finely distributing the solution in 100,000 parts by weight. water get an aqueous dispersion containing 0.02 weight; acting start.
    The proposed agents can also be used together with other active principles, for example, herbicides, insecticides, plant growth regulators and fungicides, or they can be mixed with fertilizers. When mixed with fungicides, in many cases, an expansion of the spectrum of action and an increase in productivity (synergism) are obtained. Fungicides can be combined with the proposed compounds. For example , ammonia complex (N, N-ethylene-bis-dithiocarbaiat) zinc, and M, M-polyethylene-bis- (thiocarbamoyl) disulfide, (M, M-propylene-bis-dithioKarbag1ata) zinc, ammonium complex (M, M-propylene bis-dithiocarbamate) -tin and M, N-polypropylene-bis- (thiocarbamoyl) -disulfide. NITROPHENOL derivatives, such as dinitro (1-methylheptyl) -phenylcrotonate; 2-sec. Butyl-4,6-dinitophenyl-3,3-dimethylacrylate; 2-sec, butyl-, 6-dinitrophenyl-i-propylcarbonate;
    329651
    heterocyclic structures such as N-trichloromethylthio-tetrahydrophthalimide; N-trichloromethylthio-phthalimide; 2-heptadecyl-2-imidazole-ace5 tat; 2, 4-dichloro-b- (O-chloroanilino) -S-S-triazine; O, 0-diethyl-phthalimidofonionate; 5-amino-1 (dimethylamino) -phosphinyl -Z-phenyl-1, 2,4-triazole; 5-ethoxy-3-trichloromethyl-1,2, -tri0 adiazole; 2,3-dicyano-1, -dithiaanraquinone; 2-TIO-1,3-Dithio - {, 5-6) -quinoxaline; 1-butylcarbamoyl-2-benzimidazole-carbamic acid methyl ester; 2-methoxycarbonylamino-benzimidazole;
     2-rhodanmethylthiobenzthiazole; - (2-chlorophenylhydrazono) -3-methyl-5-isoxazolone; pyridin-2-thiol-1-oxide; 8-hydroquinoline or its copper salt; 2,3-dihydro-5-carboxanilido-6-methyl20-1, A-oxathiin-4, 4-dioxide; 2,3-dihydro-5-carboxanilido-6-methyl-1, α-oxathiine; 2- (furyl- 2)) - benzimidazole; piperazin-1, -diyl-bis-1 - {2, 2,2-trichloro-ethyl) -formamide; 2-thiazolyl- (k)
     benzimidazole; 5 butyl-2-dimethylamino-4-hydroxy-6-methy-l-pyrimidine; bis- (p-chlorophenyl) -3-pyridine methanol; 1,2-bis- (3-ethoxycarbonyl-2-thioureido) benzene; 1,2-bis- (3-methoxycarbonyl 30 -2-thioureido) benzene; and various
    fungicides such as dodecylguanidine acetate; 3- (2- (3, 5-Dimethyl-2-hydroxycyclohexyl) -2-hydroxyethyl) glutarimide; hexachlorobenzene; N-dichloro35 fluoromethylthio-N, M-dimethyl-M-phenyl-sulfuric acid diamide; D, 1-methyl-Y- (2,6-dimethyl-phenyl) -N-furyl (2) -alaninate; D, L-N- (2,6-dimethyl-phenyl) -N- (2-methoxy-acetyl) -alanine methyl ester; 5-nitro-isophthalic acid di-isopropyl ester; 2,5-dimethyl-furan-3-carboxylic anilide; 2, 5-dimethyl-furan-3-carboxylic acid cyclohexylamide; 2-methylbenzoic acid anilide; 1- (3, -dichloroanilino) -1-Oormiamino-2,2,2-trichloroethane; 2,6-dimethyl-M-tridecyl-morpholine and its salts; 2,6-dimethyl-M-cyclododecyl morpholine and its salts;
    ° 2,3Dichloro-1, + - naphthoquinone; 1, dichloro-2, 5-dimethoxybenzene; p -dimethylaminobenzene-diazine sodium sulfate; 1-chloro-2-nitro-propane; polychloronitrobenols, such as pentachloronite, robenzene, methyl isocyanate, fungicidal antibiotics, such as griseofulvin or kasugamycin, tetrafluorodichlorI acetone, 1-phenylthiosemicarbicide, borosc mixture, nickel-containing compounds or sulfur. The effect of substances on cereals (in the amount of the comparative substance is fluoroamide and mellidid), see s table. 1-3. In the greenhouse, they are sown in plastic pots with a diameter of 11.5 cm in a peat culture substrate, sufficiently supplied with nutrients — 10, cereals - Kolibri wheat and barley from Union variety. The operating principles are mowed down in the usual way by spraying at various rates of expenditure on the leaves. The application of 15 is carried out at a plant height of 10 cm. During the vegetation period of 18 days, untreated plants show a significantly smaller measure of length compared to control plants, 20 which could be proved by final length measurements. A measure is taken from each treated row of 100 plants. The results of the action of substances on the hummingbird wheat are listed in Table. one.
    Table 1 93296
    100
    The results of the action of substances on the rotary barley Union are given in Table. 2
    table 2
    26.0 100 20.0, 76.9
    Fluoroamide 1,3
    The effect of substances on the grass and turf (see Table A).
    In the vegetative experiment, they sow in the vessels of Micherlich on the clay sand of the sod of the following standard mixture. %: AgrastJs tenuis 10, Cunosurus cristatus 10, oats nnitsa red 15, pasture ryegrass 35, m meadow meadow 30. 30. Sodium 1.5 is removed as ammonium nitrate and 1 g as secondary potassium phosphate. After the two preceding cuttings, the active principles are normal the method is sprayed with different consumption rates at height of height k cm. 20 days after treatment, height of growth is determined; after the first mowing, re-growth is observed for 4 weeks before the second mowing and that the formula of the invention is a way to regulate the growth of cereal. plants, including the treatment of plants with an active substance, characterized in that.
    where R - CN, - CH OOSN.,
    R - And, - CH3, in the amount of 0.25-6.0 kg / ha.
    Sources of information taken into account in the examination of NH1. US patent number 3894078, cl. 260-501.19, 1975.
    2. US Patent N, cl. 260-556, 1972. 5 to roll the aftereffect length measurements are taken. Compared with the control, plants from the treated rows have greatly reduced growth. As the table shows. It is better to determine the aftereffect than the known substances given for comparison. Table A, in order to reduce the growth of plants, the treatment of plants is carried out by spraying, and a compound of the general formula CO-CH, K-OGSS E is used as an active substance.
    权利要求:
    Claims (1)
    [1]
    Claim
    The way to regulate the growth of cereals. of plants, including the treatment of plants with an active substance, characterized in that 30 , in order to reduce the growth of plants, the plants are treated by spraying, and as an active substance, a compound of the general formula is used where R <- CN, - CH 2 0С0СН h , R 2 - N, - CH 3 , in an amount of 0.25-6.0 kg / ha.
    类似技术:
    公开号 | 公开日 | 专利标题
    IE53269B1|1988-09-28|7-aminoazolo|pyrimidines and fungicides containing these compounds
    CS248724B2|1987-02-12|Fungicide agent
    CS214681B2|1982-05-28|Fungicide means
    SU932965A3|1982-05-30|Cereal plant growth control method
    EP0081141B1|1985-07-31|Urea derivatives, process for their preparation and their use in combating undesired plant growth
    CS215143B2|1982-07-30|Fungicide means
    EP0254866A1|1988-02-03|Quinolin derivatives, method for their preparation, microbizides containing them and their use in combating bacteria and fungi
    EP0135838B1|1990-04-18|3-phenyl-4-methoxycarbonyl pyrazoles, process for their preparation and their use against plant growth
    CZ466989A3|1998-02-18|Oximether derivative, fungicidal agent containing thereof and method of fighting fungi
    PT89845B|1994-05-31|PROCESS FOR THE PREPARATION OF PESTICIDE COMPOSITION CONTAINING SUBSTITUTED ACRYLATES AND INTERMEDIATE PRODUCTS
    EP0232724B1|1989-08-02|Cyclohexenone derivatives, process for their preparation and their use as herbicides and plant growth regulating agents
    CS264282B2|1989-06-13|Fungicide agent and preparation method for actives compounds
    US6642179B2|2003-11-04|Inhibition of vegetative growth
    EP0001271B1|1982-10-27|Heterocyclic norbornane derivatives, plant-growth regulating compositions containing these compounds and process for the preparation of these compositions
    CS224622B2|1984-01-16|Microbicide
    EP0282792B1|1990-05-30|Substituted 2,3-epoxy-5-cyclohexenone derivatives and fungicides and herbicides containing them
    EP0107123B1|1987-07-01|Aniline derivatives, process for their preparation and their use in combating undesired plant growth
    EP0010691B1|1982-12-22|Derivatives of 1,2,4-triazole, method for their preparation, their use in the preparation of plant protecting compositions, method for the production of fungicides, method for combating fungi and fungicidal compositions
    US5163992A|1992-11-17|Oxalic acid derivatives and plant growth regulators containing them
    JP2522807B2|1996-08-07|Cyclohexenone derivative and plant growth regulator containing the compound
    EP0008731B1|1981-05-13|N-sulfenyl formanilides, their preparation and their use as fungicides
    US6451741B1|2002-09-17|Inhibition of vegetative growth
    CN1185149A|1998-06-17|2-2[-| phenyl]-crotonates used as pesticides and fungicides
    US5199968A|1993-04-06|Plant growth regulators containing oxalic acid derivatives
    EP0114299A2|1984-08-01|Derivatives of phenylglyoxylic acid, process for their preparation and their use to fight undesirable plant growth
    同族专利:
    公开号 | 公开日
    DD148581A1|1981-06-03|
    IL59051D0|1980-03-31|
    EP0013742A1|1980-08-06|
    FI800013A|1980-07-11|
    CS212334B2|1982-03-26|
    DK9680A|1980-07-11|
    PL119195B2|1981-12-31|
    DE2900685A1|1980-07-24|
    CA1144560A|1983-04-12|
    DE2964393D1|1983-01-27|
    EP0013742B1|1982-12-22|
    BR8000095A|1980-10-07|
    AT2067T|1983-01-15|
    JPS5594355A|1980-07-17|
    PL221261A2|1980-12-15|
    引用文献:
    公开号 | 申请日 | 公开日 | 申请人 | 专利标题
    US3639474A|1969-06-12|1972-02-01|Minnesota Mining & Mfg|N-substituted perfluoroalkane-sulfonamides|
    US3725451A|1970-04-13|1973-04-03|Riker Laboratories Inc|Substituted benzoylhaloalkanesulfonanilides|
    NL174644C|1970-04-13|1984-07-16|Minnesota Mining & Mfg|METHOD FOR PREPARING A HERBICIDE COMPOUND; ALSO METHOD FOR PREPARING A PREPARATION WITH HERBICIDE ACTION.|
    US3793372A|1971-07-28|1974-02-19|Minnesota Mining & Mfg|N-cyanohaloalkanesulfonanilides|
    US3981914A|1971-08-03|1976-09-21|Minnesota Mining And Manufacturing Company|N-alkylsulfonylperfluoroalkanesulfonanilides|
    US3894078A|1973-02-12|1975-07-08|Minnesota Mining & Mfg|5-Acetamido-2,4-dimethyltrifluoromethanesulfonanilide|
    JPS49125337A|1973-03-16|1974-11-30|EP0049042B1|1980-09-18|1984-03-21|Minnesota Mining And Manufacturing Company|Acyclicacylaminoperfluoroalkanesulfonanilides and derivatives thereof|
    US4312663A|1980-09-18|1982-01-26|Minnesota Mining And Manufacturing Company|Cyclicacylaminoperfluoroalkanesulfonanilides and derivatives thereof|
    US4405359A|1980-09-18|1983-09-20|Minnesota Mining And Manufacturing Company|Acyclicacylaminoperfluoroalkanesulfonanilides and derivatives thereof|
    EP0048551B1|1980-09-18|1985-04-10|Minnesota Mining And Manufacturing Company|N,n-diacylaminoperfluoroalkanesulfonanilides and derivatives thereof|
    法律状态:
    优先权:
    申请号 | 申请日 | 专利标题
    DE19792900685|DE2900685A1|1979-01-10|1979-01-10|SUBSTITUTED SULPHONIC ACID ANILIDES, THEIR PRODUCTION AND USE|
    [返回顶部]