• 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:
    METHOD OF OBTAINING ACYLANILINES of the general formula 4cClvt Z x-1 ng) KI: S and R have the same or different values and represent hydrogen, methyl, ethyl and propyl, CH, - CH CH - CH R have the same or different values and represent H, alkyl C — C or R and R together may represent a (CH 2) group. X -C-OCH -CO-Cj Hj or CHCOfej-tg ОО Re - methyl, n 0.1 (- (.-С, -, СНз 2- - Oti-Hj, i СО ЧНг-С-ОйНз о -CHft -C-CHoiil, iH2-C-iH5 IIH oo. Distinguished by the fact that the anigline of the general formula is -B 3. (I XCCHg), NH Where X, R, R, - have the indicated meanings, are reacted with a compound of the formula Cl -tZ where Z - has the indicated value, in an inert solvent in the presence of a base.
    公开号:SU1128832A3
    申请号:SU802997902
    申请日:1980-10-30
    公开日:1984-12-07
    发明作者:Бозоне Энрико；Камагги Джованни；Де Вриес Ламбертус；Гаравалья Карло；Гарласкелли Луиджи；Гоццо Франко；Корнелис Овереем Ян；Лоруссо Симоне
    申请人:Монтэдисон С.П.А. (Фирма)；
    IPC主号:
    专利说明:

    Priority on the signs: 02.02.78 лри g CHj-СО-ОН. ,, CH2-CO-CHJJC1, C% -CO-CHj.
    04.07.78 npHZ - the rest of the meanings listed in the claims.
    : The invention relates to the synthesis of new acipiaiilines, koHKpeTHO, to compounds of the total X- (CH2) l, where R and RA have the same or individual values and represent hydrogen methyl, ethyl, and SlNu, CHg, Kl and Rji and the same or different values and p are hydrogen alkyl, or R and together can represent a (CH) group. x -c-o-; ns, - "lo-UzHs or YSHOIB, RC - methyl, n 0.1,, -CHj-0, (-CH20-OCH5-0 ° - (ii, - Sn - (} n , (1H2 (10- (H2C1, (iO (Hs, having a fungicidal action. These compounds can be used in agriculture. Acylanilines ij are known, showing fungicidal properties of Sises CH3 / (iH-COOCHj where Z.H, methyl Zj-methyl, acetyl, bn-alkyl. However, these compounds are phytotoxic. The purpose of the invention is to develop a method that allows the synthesis of new acylanilines having a fungicidal effect with less phytotoxicity. but the method for the preparation of acylaniline. In 1 by the reaction of anilines of the general formula XidHjIrt-NH de X, R. - RX the indicated values, by compounds of the formula di- (-Z II where Z has the specified value. In an inert solvent in the presence of a base. Method It is based on the known reaction of reacting nitrogen-containing compounds with acid halides in an inert solvent medium in the presence of compounds, linking the etched hydrogen halide 2j. Example 1, Preparation of N (2,6-dimethylphenyl) -H-acetoacetyl-o (, -amine methyl propionate (compound 18, TABLE 5). 7.06 g of freshly distilled di-ketene is added to 14.5 g of methyl ester - N- (2,6-dimethylphenyl -2-aminopropionic acid in 25 ml of toluene. The reaction mixture is heated under reflux for 24 hours. After cooling and evaporation of the solvent, the residue is purified by chromatography on a column of silica gel. Chloroform is obtained as eluent. Get 20 g of the desired product in the form of oil, with a yield of 98% relative to the theoretical The structure of the product was confirmed by NMR spectroscopy. Example 2. Preparation of N- (2,6-diallylphenyl) -N-acetoacetyl-oC-aminomethylpropionate (compound 26, Table 1),, 0.02 mol of N- methyl ester With 2,6-diallylphenyl) -o6-aminopropionic acid, toluene (10 ml) is dissolved in 0.025 mol of just the first diketene that is added to the solution and the whole mixture is heated at reflux temperature for 24 hours. After cooling and evaporation the solvent residue is purified by silica gel column chromatography using a mixture of hexane and ethyl acetate (4: 1) as ve eluent. 3 g of the expected product are obtained in the form of an oil. Example 3. Production of a- (2-al lsh1phenyl) -H-acetoacetyl - () 6-aminomers of pro-pionate (compound 30, table 5). O, 02 and mol of methyl N- (2-allylphenyl) - -aminopropionic acid are dissolved in 20 mp of benzogl. To the solution was added 0.5 mol of pyridine and 0.25 mol of freshly transferred. beaten diketena. The reaction mixture is heated under reflux for 10 hours. After cooling, it is diluted with benzene, washed with a solution of hydrogen chloride (1% concentration) and water. The organic phase is separated, acidified with Na2 SO4 and the solvent is evaporated. The residue is purified by chromatography on a column of silica gel using hexane-ethyl acetate (4: 1) as eluent. 3 g of the expected product are obtained (oil). Example 4. In Examples 1, 2 or 3, compounds 19, 27, 28,. 29, 31, 33 and 34 (Table 5). Example 5. Preparation of N- (2-methyl-6-allylphenyl) -Y- (carboxymethyl-acetyl) -c-aminomethyl propionate (compound 20, Table 5). 5 g (0.021 mol) of N- (2-methyl-6-allyl-phenyl) -oi-aminopropionic acid methyl ester is dissolved in toluene (120 ml). To the solution is added dropwise with stirring for 15 minutes at room temperature 3.5 g (0.027 mol) of the one-chloro-substituted methyl malonic acid tilic ester (C1CO-CHL-COOCH). The reaction mixture is then moved at room temperature for 1 hour, then heated under reflux for 5 hours. After cooling, the solution is filtered and the solvent is evaporated. The oily residue is purified by chromatography on a silica gel column using hexane-ethyl acetate (3: 1) as eluent. 4.6 g of the expected product are obtained in the form of a red oil. Example 6. Preparation of N- (2,6-dimethylphenyl) -N- (2,2-dimethoxyatst) -car. Bomethocryacetamide (compound 32, Table 5). To a solution of N- (2,2-dimethoxyethyl) 2, 6-dimethylaniline (4.45 g, 0.02 mol), riethylamine (2.76 ml, 0.02 mol) in ethyl acetate (25 ml) is added o drops for 15 minutes while stirring at 0-5 ° C. monochlorine methyl ester of malonic acid (2.1 ml, 0.02 mol). The reaction mixture is then stirred for 1 hour at and 10 minutes at room temperature, then it is filtered, washed twice with 10 ml of hydrogen chloride (5%), then with water until neutral pH (3 x 10 ml). 5 The organic phase is acidified with anhydrous and the solvent is evaporated. The residue (yellow oil) is purified by chromatography on a silica gel column using hexane-ethyl acetate (7: 3) as eluent. Obtain 2.1 g of the target product (oil). Example 7: In Examples 5 or 6, compounds 21-25 are prepared. Example 8. Preparation of N- (2,6-dimethylphenyl) -H- (1-carbomethoxyethyl-phenylacetamide (compound 4, table 5) 17 g (0.11 mol) of phenylacetyl chloride is added dropwise over 30 minutes and at room temperature temperature to a solution of N- (1-carboxymethyl) -2, 6-dimethylaniline; (21.2 g at 95% purity, 0.1 mol) in toluene (150 ml and dimethylfloamide (.1 ml). The reaction mixture is stirred for 1 at room temperature and 3 hours at reflux temperature, then it is cooled to room temperature and washed with 5% aqueous NaHCO solution, and then the organic phase is separated off with water and acidified anhydrous Na.SO. The solvent is evaporated and the resulting crude product is recrystallized from ligroin (75-120 ° C., thereby obtaining 26 g of the expected product (white solid, mp 78-80 ° C). 9. In Example 8 nony Example Compounds 1, 2, 3, 7–10, 12–17, and 34 (Table 5); however, compounds 10,., 13, and 34 (oils at room temperature) are purified by silica gel column chromatography (eluant hexane-ethyl acetate ( 3: 1) instead of recrystallization. Example 10. Preparation of N- (2,2.-Dimethoxyethyl) -N- (2,6-dimethylphenyl) -benzamide (Compound 6, Table 5). 2.81 g (0.02 mol) of benzoyl chloride is added dropwise over the course of 20 minutes and at the solution of N- (2,2-dimethoxyethyl) -2,6-dimethylaniline (4.45 g, 0.02 mol) in ethyl ether (20 MP) containing triethylamine (2.76 MP, 0.02 mol). The reaction mixture was stirred at room temperature for 15 minutes. The resulting salt is filtered and the solution is washed with 8 ml of an aqueous solution of hydrochloric acid at 5% and then with water until neutral pH. The organic phase is acidified with anhydrous CalZole and the solvent is evaporated, thus obtaining 5.2 g of a white solid, which upon crystallization From petroleum ether (25 ml) gives 4.5 g of product (91% by thin layer chromatography) in 65 , 5% (white substance, t, pl. 58-59c). Example 11. Acting according to Example 10 and starting from N- (1-methyl-2,2-dimethoxyethyl) -2,6-dimethyl-aniline and from benzoyl chloride, is obtained as a clear oil N- (1-methyl-2,2 -dimethoxyethyl) -N- (2, 6-dimethylphenyl) -benzamide (compound 5, Table 5). Example 12. Getting N- (methylme. Toxycarbonylmethylene) -2,6-di-. methylaniline. To a solution of 2.6 dimethylaniline (37.2 MP, O, 3 mol) in benzene (200 m), add 0.5 g of ZnCl2 at room temperature, and then 33.2 ml, (0.33 mol) of methyl ether pyruvic acid. The reaction mixture is heated under reflux for 7 hours with simultaneous azeotropic distillation of water formed during the reaction, then the solvent is evaporated to obtain 65 g of substance in the form of oil, which is distilled, fractions boiling at 87–8.8 ° C are collected under pressure 0 , 07 mm Hg Thus, 42.5 g of product are obtained having a purity of 92% by thin layer chromatography (yield | b3, 5%). Example 13. Preparation of N- (2,6-dimethylphenyl) -N- (1-carbomethoxyvinyl) phenylacetamide (Compound T1, Table 5). 4.35 MP of phenylacetyl chloride (0.033 mol) is added dropwise and at room temperature to a solution of 6.7 g (0.03 mol) of H- (methylmethoxycarbonylmethylene) -2,6-dimethylaniline (prepared as described in Example 12, with a frequency of 92%) in toluene (100 mp). ; 71 The reaction mixture is heated under reflux and held in a stream of nitrogen for 3 hours, until the solvent is evaporated, yielding 10.8 g of a light yellow oil, which solidifies on friction. The resulting crude product is recrystallized from petroleum ether to give 2 g of product (more solid, pure by TLC), the yield is 21%. In Table. 1 shows curative activity, at a dose of 0.01% against P. viticola on grapes, expressed as a percentage reduction in infection. Table. 2 shows the activity at a dose of 0.01% against P. tabacina H. N2, 6-dimethylphenyl-N- (1 carbomethoxyethyl) -2-furoyl amide. (2,6-dimethylphenyl) -N- (1-carbomethoxyethyl) methoxyacetamide. 32.8 per cent of tobacco plants. reduce infection. In tab. Figure 3 shows prophylactic activity at a dose of 0.01% against P. viticola, on grapes, expressed as a percentage of infection inhibition. In tab. 4 shows the phytotoxicity index at a dose of 0.3% on grapes, shown in a scale of values from O (absence of phytotoxicity, healthy plant) to tOO (complete phytotoxicity, the plant is completely damaged or destroyed).
    T
    Activity,%
    Compound
    90 100 100 100 TOO 80 IQO. 100 100 100 100
    too
    100
    100
    100
    100
    100
    100
    100
    100
    100
    90
    100
    table 2
    Activity%
    Compound
    100
    18 22 23 25 26
    100
    100
    100
    100
    100 27 31 32 33 35
    100
    100
    100
    100
    uralaxyl
    100 . idomyl
    100
    100
    Table 3
    100 100 100 100
    , 90. 100 100 100 100 100
    100
    100
    100
    95
    100
    100
    100
    100
    jj
    Zineb is zinc ethylene bis dithiocarbamate.
    25
    ABOUT
    five
    ten
    40
    36
    thirty
    eight
    18
    ten
    29
    6
    100
    95
    100
    100
    100
    thirty
    Table 4
    2
    25
    38
    29
    ;
    38
    thirty
    25
    15
    laxyl
    100
    myl
    100
    c-deHs
    , nI 0
    2 - ((1НзНн-0-С- (
    OI o
    YU)
    97-100 74.31 7.42 4.13 74.45 7.77 4.25
    B
    3,
    CH, o-j-da / (
    ABOUT
    114-115 Н5 Н, й-0-е- 1Г е-ЙН ,, “:: / о H, ((H3
    1Нз
     f -M
    about
    6. M-Own-YNg / - (JgHs
    Нз6-о / VH dHjv I iH
    73.37 7.70 4.18 75.4 8.4 4.3
    58-59 72.81 7.40 4.47 73.14 7.66 4.69; "7.12 4.30, 75.34 7.47 4.67 l
    15
    Connection Formula

    Hjii-o-t-CH, (, H5
    W II O I o
    (1H2 (1H (1H2
    (iHj
    -about
    "N, (, -" - СН Д- "н, 8 .ОI О
    CH. . , - CFL / OI
     / -V
    , 0 (tH3) i - ((Ht- {e} СНз
    n
    ft
    H3e-o- | -c t-CH, -0
    11. a - f, Hz 12. H5 (1-0-е- Н / - (И2- (о) 51-52 О ТО
    sixteen
    1128832
    Continued table. five
    74.28 6.54 4.33 73.6 6.6 4.6
    63-64 65.23 6.39 4.23 66.53 6.74 4.54
    Mas74, 76 7.70 3.96 73.84 7.91 3.09 Lo
    56-57
    07 -; -, ..,;,:. : - / L) (; H ° 70.36 6.79 4.10 70.5 6.9 4.0 O 74.31 7.424.13 74.037.524,
    Connection Formula
    dHs
    3-H5 (i, 0-j4il - (lH2- {o)
    About CH5
    (iH.
    yng
    14
    5 iN II W
    Elemental analysis, Z
    t 1g ---- j
    CHN I SI I N
    Oil74, 31 7,424,13 72,967,164,34
    69-70 73.82 .7.12 4.30 73.41 7.28 4.31

    n, Co-e (1n S "
    0,
    Hgri
    97-10065.99 5.83 4.06 67.0 5.9 3.7.
    f HS
    16. Nd (1-0 - ({- (H, C - (} Hn
    II 1J / 1I
    0.0
    (Jhj
    Hxd
    60-64 72.47 8.82 4.22 71.75 9.12 3.81 Hid-oC-dH (J-lH2- / oVo H, II u / "Xl / 0 70 90-93 70.96 7.09 3.94 70.59 7.28 3.70
    dHs
    18.
    Hjd-o-d-KlH / d-dHgII -N / ll 00
    Hch ,
    about
    Butter
    nineteen
    fHs. n.ygO th SN / fdHjdciHs
    And 1 / ii and
    about 1 about o., L. (n,
    (n
    20.I, Hjd-ci-CH "idHotioOHs
    II ll / U 11
    oh i oh oh
    n jd ,, Л, (1Н2 - н (1н 2
    dHs I
    ii-du / -Cu2-C-o (iH5
    II N
    oh i oh oh
    oh oh yn
    HS
    23.
    -li-4,
    oh i oh hsc
    CH-t
    I.
    NZS-o - {- (n / ongoyne,
    and 5i .. 5
    II
    Q o o
    CH2CH,
    20
    1128832 Continuation of the table. five
    64.85 6.95 4.20 64.84 7.24 4.51
    66.83 7.01 3.90 67.93 7.72 4.67
    Butter
    21
    1H5 25I
     NTYO-S-yn. (I ((li
     II F and and
    about 1 0 o
    HsCo-C-dH / -dHo-diiHs II -H / tt II o 1 o o (.xCH2CHH CH2
    22
    1128832 Continuation, tab. .five
    105-110 lo 69.95 7.34 4.08 68.60 7.30 4.32
    (iHs 27.I.H5 ((iH. (iiiHodtHa II N / 11 and
    I 1 J o M -, (iH (iHCH5, 28.I Mas CHjIaCH-O-d-XlH i-iiHgtiOls lo H / -JJcH / HjC-J-CH C-dHg-jjdUg lo 68,12 OI Oo (lH2
    - --- J-liH, II / ii
    oh oh
    ABOUT
    (1Ig- (
    68.12 7.30 4.41 65.85 7.49 4.35
    4.62 66.2 6.90 4.90 67.69 7.89 4.38 67.718.324.40 7.30 4.41 67.707.334.36
    权利要求:
    Claims (1)
    [1]
    METHOD FOR PRODUCING Acylanilines of general formula have the same or different meanings and are hydrogen, methyl, ethyl and propyl, -CHg-CH = CH ,,
    - СН = СН - С1Ц,
    R and R ^ have the same or different meanings and are H, alkyl C {-Cj or R and Bd together can represent five, (= CH g ) a group,
    111 IHMLII "·" .ί and, "
    X = -C-OCH , -С-О-С, Н s or snСбк.к
    II 3 And. g '' 2
    About 0
    R. - methyl, n = 0.1
    - С-ОСНз II 0 -Си 2 - С -Си 2 <11, € and 2 -с- € and 8
    0 o. Characterized in that the anilines of the general formula where X, R <, R |, - have the indicated meanings, are reacted with a compound of the formula
    Cl-c-z
    II about
    where Z - has the indicated meaning, in an inert solvent in the presence of a base.
    IS ω
    1128832 A priority on the grounds of; . 07/04/78 at £ - the rest of the 02.02.78 ions Z = СН 2 - СО-ОСН-р, the values listed in the formula
    CHj-CO-CHgC1, CH ^ -CO-CHj. inventions.
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    同族专利:
    公开号 | 公开日
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    HU182903B|1984-03-28|
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    DE2903612C2|1988-12-22|
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    RO76487A|1981-04-30|
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    PT69153A|1979-02-01|
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    引用文献:
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    法律状态:
    优先权:
    申请号 | 申请日 | 专利标题
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    IT2529578A|IT1101052B|1978-07-04|1978-07-04|N-Substd. N-acyl-aniline derivs. - useful as systemic fungicides|
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