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    • 专利摘要:
    1. METHOD OF OBTAINING PRO} 13 WATER ANILINE General formula 1 l -HH-CO-Q where X is halogen; C is alkyl; C - alcock si; C-alkenyl, trifluoromethyl, cyano; n is an integer from O to 3 and if n is more than 1; substituents X may be the same or different; a is the radical A or B of the formulas H HH. rtTT-g GLT1 NzS "SNz SNz n, with H A in - cyano group or SOF - in which R where R 2 is lower alkoxy, from the exclusion that the anilide of the general formula UknsosngSosnz (and) WrK - where the values X and n are given above , is reacted with an aminoethylene derivative 1m of the general form H2H-CCH-Ri. (L. RZ, where the values of R ;, and Rj are given above, and formaldehyde, and the resulting target product is isolated, in which Q is the above radical L, or is subjected to dehydrogenation of its solution in acetic acid with sodium nitrite, and the target product, in which Q means the above-mentioned radical B, you 4 are divided. 00 2. The method according to Claim 1, which is based on the fact that the reaction of the mutual action of anilide of the general formula II and a. Amino-ethylene derivative of the general Formula III and formaldehyde is carried out in an organic solvent solution at 15-100 ° C.
    公开号:SU1064866A3
    申请号:SU813366254
    申请日:1981-12-23
    公开日:1983-12-30
    发明作者:Де Рейнах Хиртцбах Франсуа；Амброси Доминик
    申请人:Рон-Пуленк Агрошими (Фирма)；
    IPC主号:
    专利说明:

    This invention relates to a process for the preparation of novel derivatives of aniline of the general formula I f nH-CQ-a, where X is a halogen atom / C-j-alkyl; alkoxy; (alkenyl, trifluoromethyl, cyan p means an integer from O to 3 and, if n is more than 1, the substituents X may be identical or different, Q is the radical A or B of the formulas H and C, in which RJ - - cyano group or CORj ,, where Rg is lower alkoxy having herbicidal properties. These compounds can be used in agriculture. A method is known for producing dihydropyridine derivatives by reacting 3-ketocarbonyl compounds with amino-ethylene derivatives and aldehydes, usually a reaction inert organic solution It is also known that dehydrogenation is carried out under the action of an oxidizing agent, for example, nitrous acid C21. 1,4-Dihydro-3-p-phenylcarbamoylpyridine derivatives are known, their herbicidal activity is not known 33The purpose of the invention is the development, on the basis of a well-known method for the preparation of new amine derivatives with herbicidal activity. The aim is achieved by a method for the preparation of anilic derivatives based on the general formula 1, that NHCOCHgCOCHs general formula: wherein X and / vshe 7 shows reacted with aminoethyl ene derivative of general formula Hzl-C CH-Ri (-. where is the value of Well and Hj. above, both formaldehyde and P9-irradiated target product, in which Q is the above-mentioned radical A, or is isolated or dehydrogenated with its solution in acetic acid nit nitride with sodium, and the final product, in which Q is the above-mentioned radical B, is isolated. Preferably, the reaction of an anklide of general formula III with an aminoethyl derivative of general formula III and formaldehyde is carried out in an organic solvent at 15-100 ° C. The reaction of reacting the compound of general formulas II and III and formaldehyde is exothermic. It is carried out at room temperature as well as at a higher temperature to avoid destruction of the initial reagents. As an organic solvent, protic and aprotic organic solvents are used, such as aromatic carbons, aliphatic hydrocarbons, or cycloaliphatic hydrocarbons, halogenated hydrocarbons; lower alkanols, such as methanol, ethanol, isopropanol, tert-butyl alcohol; ethers, for example, diethyl ether, nitriles, such as acetonitrile, amides, for example, dimethylformamide. Preferably, the reaction is carried out at the boiling point of the solvent used. If necessary, the reaction can be carried out in an atmosphere of an inert gas, for example nitrogen. The structure of these compounds was confirmed by NK spectrometry and / or NMR spectrometry, and the spectra were taken at 60 MHz in DMSO with hexamethyldisiloxane. as an internal standard. Example. Preparation of 1,4-di-hydro-H1- (2, 6-diethyl-phenyl) -3-carbamoyl-5-ethoxycarbonyl-lutidine-2, 6 (compound No. 1) frrg: ula (a J. In a three-neck flask With a capacity of 250 ml, equipped with a refrigerator, a thermometer and a mechanical stirrer, 23.3 g {0.1 mol / 2,5-diethyl-acetoacetanilide, 12.9 g (0.1 mol J of ethyl / 3-aminocrotonate, 50 ml) are charged. ethanol. The mixture is stirred, then heated from room temperature until the reactants are completely dissolved. After cooling: 10 ml of aqueous 30% (by weight of formaldehyde solution) (or about 0.1 mol.) The reaction is exothermic and the temperature rises spontaneously from 20 to about 55 ° C. Then the reaction mixture is then refluxed for 60 minutes. After cooling to room temperature, filtration, washing the precipitate with water, 14.5 g of the mixture are obtained including, on the one hand, the target product (compound No. 1) and, on the other hand, 1,4-dihydro-3, 5-di- (ethoxycarbonyl) lutuidin-2,6-, which is formed as a by-product, Result: the condensation of two moles of ethyl-J3-aminocoronate with one mole of formaldehyde. By recrystallization from 250 ml of ethanol, 9 g of compound No. 1 is obtained. The yield of the starting acetoacetanilide is 25%, m.p. 209 C. Gross formulas Ca / Hj Oj. The starting 2,6-diethyl acetoacetate lead is obtained by the interaction, 2,6-diethylaniline and diketene, according to a known method, Example 2: Preparation of compounds No. 2-22. . Following the procedure of Example 1, compounds 2-22 are prepared from the corresponding starting materials. The formulas and physico-chemical characteristics of these compounds are listed in Table A. PRI me R 3. -Getting compounds. B23. Following the procedure of Example 1, 1,4-dihydro-K- (2,6-diethylphenyl-3-carbamoyl-5-cyano-lutidine-2,6 Tpl.) is obtained from the corresponding starting materials. Gross formula C “Na) H O. —Pr and m e. P 4 Preparation of N- (2,6. Diethyl-fevil) -3-carbamoyl-5-ethoxy-carbonyl-lutidine-2, b / compound No. 2 or ego equivalent under the name 2,6-methyl-K- (2,6-diethyl-phenyl-3-carbamoyl-5-ethoxycarbonyl-pyridine. The starting material used is 1, 4-dihydro-K- (2,6-diethylphenyl) - 3-carbamryl-5-ethoxycarbonyl-lu tidine-2,6 (the preparation is described in Example B: a three-neck flask with a capacity of 250 m; with a fridge, thermometer and mechanical stirrer, 5.5 g of 1,4-dihydro-H- (2,6-diethylphenyl) -3-carbamoyl-5-ethoxycar6onyl-lutilin-2, 6 and 5.5 ml of acetic acid are charged. the mixture is cooled to 16 ° C and then 1.2 g of sodium nitrite is added in small portions.The exothermic reaction is controlled by cooling with an ice bath so that the temperature of the reaction mixture does not exceed 25 After stirring for 30 minutes at a temperature of about 20-25 C, the reaction mixture is poured on ice and neutralized with 75 ml of concentrated ammonia . The precipitate obtained is filtered and washed with water. After filtration through 120 g of silica, eluting with a mixture of methylene chloride and ether (8/2), 4.2 g of the title compound are obtained (compound No. 24). M.p. 216 ° C. Exit (from dehydrolutidine) 77%. Gross formula Cj / Hj NgOj. P & M 5. - Preparation of compounds No. 25-53. Following the procedure of the previous example, the compounds # 25-531 formulated from the corresponding substances. The formulas and physicochemical characteristics of these compounds are presented in Table. A. The yields indicated in this table are calculated with respect to the starting acetoacetanilide. Example 6. Preparation of N- {2,6-dimethyl-phenyl) -3-carbamoyl-5-cyano-lutidine-2, 6 (compound No. 54) This compound, melted at 243 ° C, is obtained using the method of example 4 / using 1,4-dihydro-I- (2,6-dimethyl-phenyl) -3-carbamoyl-5-cyano-lutidine-2, 6 as the starting material, which is obtained by the method described in example 3.
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    СООСгНв C2iH2ffH203 P p and m e p 7. Herbicidal activity in the greenhouse before germination of plant species. In pots 9x9x9 cm in size, filled with light agricultural land, the amount of grains sown is determined depending on the plant species and on the grain size. Moreover, the grains are covered with a layer of earth about 3 mm thick. After the soil is moistened, the pots are worked by spraying with the amount of broth per pot, corresponding to a volume of 500 l / ha and containing the active principle in the dose in question. The broth is obtained by diluting it with a certain amount of water so that the desired concentration of the wettable powder is obtained as follows. Composition, wt.% Active test beginning 20 Solid inert base-kaolinite 69 Surface-active agent Sdefflocula nt) Calcium lignosulfonate 5 Surface active-. wetting agent: sodium isopropyl naphthalene sulfonate 1 Preventing the clumping of silica 5 This powder is obtained by smearing and grinding the ingredients in a micronizer so that a particle size of less than 49 microns is obtained; Depending on the concentration of the active principle in the broth, the dose of applied active agent is .2–8 kg / ha. The treated pots are then placed in floor tanks.
    -Table continuation
    188
    20
    21
    178
    70
    50 water by sprinkling, E as a subirrigation, and incubated for 35 days at room temperature with a relative humidity of 70%. After 35 days, the number of live plants in pots treated with the test active broth is counted, and the number of live plants in the control pot treated under the same conditions but using broth containing no active principle. In this way, the percent destruction of the treated plants with respect to the untreated control is determined. The percentage of destruction, equal to 100%, shows that there is a complete destruction of the plant species under consideration, and a percentage of 0% indicates that the number of living plants in the treated pot is identical to that in the control pot. For this experience, the plant species used were as follows: Used Wild-growing symbol Oats wild Rosicka Chicken millet Multiflorous RAY Bristles SET Fox-field VUL MarSNE Nightshade MY Hazitz field MOV Starfish medium STE cultural Cotton. COT Sunflower ROY The results obtained are presented in Table B. And show a good herbicidal activity of the compounds on a variety of treated wild plants, both monocots (cereals / and dicotyledons, as well as their selectivity with respect to the cultivated plants.
    For use in practice, the proposed compounds are rarely used. They are used individually, and most often they are used in the form of compositions, which usually contain, besides the active principle, a solid or liquid base, PLV, etc.
    Example Reproduce Example 7 using the same compounds as the active principle, but having tested the broth obtained from the wettable powder of the following composition, wt%:
    Active start80
    Alkylnaphthalene sulfonate sodium. . 2
    Lignosulfonate
    on three . 2
    Silicon dioxide
    kaolinite13
    When used on plants, the same results are obtained as in Example 7.
    Example 9: Reproduction of Example 7, using the compound as the active principle, but testing the broth obtained and the wettable powder of the following composition, wt.%:
    Active start 50
    Sodium alkyl naphthyl sulfonate 2
    Methyl cellulose 2
    Diatomaceous earth 46
    When used on plants, the same results are obtained as in Example 7.
    Example 10: Reproduction of Example 7, using the same compounds as an active principle, but testing the broth obtained from the wetting powder of the following composition, wt.%:
    Active principle 90 Dioctyl sodium sulfosuccinate 0.2
    Synthetic dioxide
    silicon, 9.8
    When used on plants, the same results are obtained as in Example 7.
    Example 11 Reproduction of measure 7, using the same compounds as the active, but testing the broth obtained from the wetting powder of the following mass, wt.%:
    Active start 25
    Isoactylphenoxypolyoxyethylene ethanol 2,5
    Equilibrium mixture of chalk
    from Champagne and hydroxyethylcelluloseIF
    Sodium aluminosilicate 54.3
    Kieselguhr16,5
    When used on plants, the same results are obtained as in Example 7.
    Example12. Reproduce Example 7 using the same compounds as the active principle, but testing the broth obtained from the wettable powder of the following composition, wt.% :.
    Active start10
    A mixture of sodium salts of saturated fatty bisulfate3
    The condensation product of formaldehyde and naphthalene sulfonic acid 5 Kaolin82
    When used on plants, the same results are obtained as in Example 7.
    Example 13: Reproduction of Example 7, using the same compounds as the active ingredient, but testing the broth obtained from an aqueous suspension of the following composition, wt.%:
    Active principle 22.7 Complex Zfir of phosphoric acid and polyoxyethylated alcohols. Soprophor FL5
    Ethyl Tributyl Phenol and Ethylene Oxide Compozy. nat t0801
    . Propyl glycol5
    Anti-igniter A 0; 3 Zoda66
    When used on plants, the same results are obtained as in Example 7.
    PRI me R 14 (comparative) Comparison of the proposed compounds for herbicidal activity with the used strong herbicide-oxadiazon.
    Oxydiazon or 5-tert-butyl-3- (2, i-dichloro-5-isopropoxyphenyl) -1, 3,4-oxydiazole-3-one, a herbicide used mainly for processing rice, as well as cotton. The technology and plant species used are described in Example 7. On the basis of the percentage of destruction, the following is determined: for crops, the limiting dose of selectivity, i.e. the highest dose in kg / ha, which causes less than 15% of crop destruction (DL15), for weeds - the maximum dose of efficiency, i.e. the weakest dose in vg / ha, providing at least 90% of weed control (DL90). Gjkextzzst htpekmnfns d. The results, in kg / ha. Compound 1 Oxydiazon
    Cotton (DL15) 82
    Sunflower (DL15) 8 2 Wild Oat (DL90) 82 Thimble Nka (DL90) 0,50,7 Panisse (DL90) 10,5 Ryegrass (DL90) 20,7 Bristle (1) 1.90) 0,59,6 1,21 Foxtail (DL90) Quinoa (DL90) 0,50,5 0,74 Nightshade {PL90) Mustard (DL90) 84 Star Sprockets (DL90) 0,54 From a comparison of the data it can be seen that Compound No. 1 has a herbicidal effect on weeds, almost equivalent to oxadiazon , but it is significantly less toxic for cotton and sunflower crops. Therefore, its use for selective treatment is much safer than oxadiazone, since there is no risk of crop destruction.
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    about . о о о о о пЧ ооооо voorom in tN о о о о о о OOOOOOO.O gNgNgCH gCh inOOO fN, 4CN OORO ininroLn OOOOOOL ooocrit4mCN tCh oo 00 oo 00rit t oo N rOin VO G (
    权利要求:
    Claims (2)
    [1]
    , 54) 1. METHOD FOR PRODUCING ANILINE DERIVATIVES of the general formula ''
    UH-C0-Q ’where X is halogen;
    C is alkyl;
    C * - Alcock si, '
    CL is alkenyl, trifluoromethyl, cyano; η is an integer from 0 to 3 and, if η is more than 1; substituents X may be the same or different;
    B is the radical A or B of the formulas
    N g Ή N G H 3 C ^ sun 3H 3 s N sun 3 and BUT AT in which R 1 - cyano group or SOI 7 where R 2- lower alkoxy about t l and -
    that is, an anilide of the general formula. ()
    NHCOCH 2 COCH3 where the values of X and η are given above, are reacted with an aminoethylene derivative of the general form H 2 H ~ C = CH-R 1 .
    R 2 where the values of and ( 2 2 are given above, and formaldehyde and the obtained target product are isolated in which Q is the radical A above, or they are dehydrogenated in acetic acid with sodium nitrite, and the target product in which Q is indicated above radical B, is isolated.
    [2]
    2. The method according to claim 1, characterized in that the reaction of the anilide of the general formula II with an a. Aminoethylene derivative of the general formula III and formaldehyde is carried out in an organic solvent at 15-100 ° C.
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    引用文献:
    公开号 | 申请日 | 公开日 | 申请人 | 专利标题
    BE492229A|1948-11-17|
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    EP2103990B1|2006-12-21|2017-08-16|Hitachi Chemical Company, Ltd.|Light control film and light control glass|FR2508446B1|1981-06-25|1986-05-02|Rhone Poulenc Agrochimie|HERBICIDES WITH AMIDE AND ESTER FUNCTIONS DERIVED FROM PYRIDINE AND THEIR PREPARATION AND APPLICATION PROCESS|
    DE3239273A1|1982-10-23|1984-04-26|Bayer Ag, 5090 Leverkusen|TETRAHYDROPYRIDINE, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE IN MEDICINAL PRODUCTS|
    FR2537580B1|1982-12-13|1985-09-20|Rhone Poulenc Agrochimie|NOVEL BENZYLCARBAMOYLPYRIDINE DERIVATIVES, PROCESSES FOR THEIR PREPARATION AND THEIR USE AS HERBICIDES FOR WEEDING CROPS|
    ES535014A0|1983-08-11|1985-08-01|Monsanto Co|A PROCEDURE FOR PREPARING SUBSTITUTED PIRIDINE DERIVATIVES IN POSITIONS 2 AND 6|
    US4618679A|1983-08-11|1986-10-21|Monsanto Company|3,5-dicarboxylic acid esters of 2,6-bis-2,6-bis piperidines|
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    法律状态:
    优先权:
    申请号 | 申请日 | 专利标题
    FR8015994A|FR2486939B2|1980-07-16|1980-07-16|
    FR8015993A|FR2486938B1|1980-07-16|1980-07-16|
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