• 专利附录
  • 专利说明
  • 权利要求
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    • 专利摘要:
    Maleimide and succinimide derivatives and preparation and use thereof, said derivatives having the general formulae <IMAGE> and <IMAGE> wherein R, R1, R2 and R3 are each hydrogen or various substituents. The compounds may be made by acylation of the corresponding derivative unsubstituted on nitrogen. They may be formulated into herbicidal compositions and used as pre- and post-emergence herbicides. The compounds can also be used as chemical intermediates.
    公开号:SU1282814A3
    申请号:SU782640407
    申请日:1978-07-24
    公开日:1987-01-07
    发明作者:Шереш Ене；Дароци Иштванне；Варконьи Яношне；Хорват Габор；Силадьи Илдико；Радвани Белани
    申请人:Хиноин Дьедьсер Еш Ведьесети Термекек Дьяра Рт (Инопредприятие)；
    IPC主号:
    专利说明:

    11282814
    This invention relates to methods for producing novel malein-imide derivatives and succinimide (common formgo).
    (0 measure 25
    X-Y
    oVo
    WITH
    X - Y is a group
    ,
    R is phenylamino, which can be Substituted by alkyl With-C, methoxy, l
    20
    R is one or two halogen atoms, a cyclohexylamino group, a benzylamino group, a furfurylamino group, a naphthylamino group, an amino group;
    hydrogen, chlorine, phenyl, which can be substituted by methyl, phenylthio, phenylsulfonyl, cyclohexylthio, alkylthio C
    It
    benzoxy
    ,} R, - alkoxy C —C,
    14
    LI X - Y is a group
    thirty
    35
    R. R-C- jH-Ri
    where R is phenyl, hydrogen;
    R is hydrogen, phenyl 1 H 1 ogroup, which can be methyl or chlorine; Rj is alkyl C / -C, hydrogen. The compounds of general formula (1) possess herbicidal activity and can also be used as intermediates for the synthesis of new uracil and dihydrouracilcarboxylic acid derivatives exhibiting valuable pharmacological properties.
    Example 3 3.876 g (0.02 mol) of 3-phenylamino-maleiimide is dissolved in .60 ml of acetic anhydride by heating. The solution is heated for the purpose of the present invention. It is the development of a method for producing new biofuels for 5 hours under reflux and gas-active preparations, which are left overnight. Precipitated
    extending the area of impact on a living organism.
    Example 1, 7.52 g (0.04 mol) of 3-phenylamino-Mapin imide is dissolved 55 with stirring in 280 mp of acetone ,. 6.48 g (0.06 mol) of ethyl chloroformate and 6.06 g of 218-219 Co are added dropwise to this mixture simultaneously.
    the yellow crystals are filtered and washed three times with water using a cat dice for 10 ml of water. The product, if desired, is recrystallized from acetone or dioxane.
    3-Phenylamino-N-acetyl-maleimide is obtained. Yield 4 g (86%), t, pl.
    (0.06 mol) of triethylamine with stirring. During the addition, the temperature of the mixture is maintained at 25-30 ° C. After the addition, the mixture is stirred at room temperature for 1.5 hours and refluxed for 10 minutes. The mixture is left overnight and the precipitated triethylamine hydrochloride is filtered,
    The acetone containing mother liquor is concentrated. The precipitated yellow crystalline substance, if desired, is washed twice with water each time using 15 ml of water and
    filtered,
    After the essence, the resulting 3-phenyl-lmino-gY-carbethoxy-Mapine imide is recrystallized from ethyl acetate or absolute alcohol. Output 7.6 g - (73%), t, pl. 168-172 ° C
    five
    0
    Example 2, 1.88 g (0.01 mol) of 3-phenylamino-maleimide is dissolved while moving in 70 ml of acetone. 1.17 g (0.015 mol) of acetyl chloride and 1.51 g ( 0.015 mol) of triethylamine with stirring. The temperature of the mixture during the addition is maintained at 25-35 ° C. After that, the mixture is stirred for 2.5 hours at room temperature, boiled for 1.5 hours and left overnight at room temperature, 5 The product is precipitated along with trichloroethyl hydrochloride. The crystal mixture is filtered and washed twice with water using 5 MP of water each time.
    After drying, a yellow product is obtained which is recrystallized from acetone and dioxane, 3-phenylamino-N-acetyl-maleimide, Yield 0.85 g (36.9%), t, mp, 217-219 C,
    Example 3 3.876 g (0.02 mol) of 3-phenylamino-maleiimide is dissolved in .60 ml of acetic anhydride by heating. The solution is heated under reflux for 5 hours and left overnight. Precipitated
    218-219 Co
    the yellow crystals are filtered and washed three times with water using a cat dice for 10 ml of water. The product, if desired, is recrystallized from acetone or dioxane.
    3-Phenylamino-N-acetyl-maleimide is obtained. Yield 4 g (86%), t, pl.
    Example 4. 1.88 g (0.01 mol) of 3-phenylamino-maleimide is dissolved under stirring in 70 ml of acetone. To this mixture, 2.1 g (0.015 mol) of benzoyl chloride and 1.51 g (0.015 g) are added dropwise at the same time. mol) triethylamine with stirring. During the addition, the temperature is maintained at 25-30 ° C. After the addition, the mixture is stirred at room temperature for 2.5 hours and boiled for 1.5 hours. The mixture is left overnight. The product is precipitated with triethylamine hydrochloride. The crystal mixture is filtered, washed twice with water using 10 ml of water each time.
    After drying, the resulting 3-phenyl and Ho-N-benzoyl-maleinimide, if desired, are recrystallized from chloroform or acetone. The output of 1.24 g (42.4%), t, pl, 23 | 8-24GS,
    For example, 4.44 g (0.015 mol) of 3-phenylamino-4-phenylthio-maleinimide is dissolved with stirring in 60 ml of acetone, and 1.95 mp (0.025 mol ) methyl e4ir chloroformic acid and 2.25 ml (0.016 mol) of triethylamine. After the addition, stir for another 3 hours while cooling with ice water. The precipitated triethylamine hydrochloride is filtered. The mother liquor containing acetone is concentrated. The orange crystals thus obtained are washed with petroleum ether.
    After drying, the resulting 3-phenyl-amino-4-phenylthio-N-carbmethoxy-maleimide, if desired, is recrystallized from methanol. The output of 4.55 g (85%), t, pl, 156-157 C,
    Example 6, 18.9 g (0.1 mol) of 3-phenyl-3-methyl succinimide is dissolved in 100 ml of acetone with stirring. At the same time, 16.2 g (0.015 mol) of methyl e (chloroformate) and 15.1 g,: (0.15 mol) of triethylamine are added dropwise to the solution while stirring. During the addition, the temperature is maintained at 25-30 ° C, The mixture is then stirred for 2 hours at room temperature and heated under reflux for 10 minutes. The mixture is left overnight and the precipitated triethyl hydrochloride
    amine filter; -Acetone; the mother liquor is concentrated. The oily residue is crystallized upon cooling. The practically white crystals thus obtained are treated with water and filtered.
    After drying, the resulting 3-phenyl-3-methyl-K-carbethoxy-succinimide, if desired, is recrystallized from 96% alcohol. Yield 13.75 g (52%), t, pl,,
    Listed in the table, nor the general formula
    R-, Ri
    o (vo
    1 connection0 C-OS2N5
    is prepared according to the method described in Example 1 from substituted male-imide.
    Example 40, analogously to example 1, receive compound 3-phenyl-amino-4- (iso-butylthio) -Y-carbomethoxy-maleinimide, t, mp, 113-115 ° C,
    Example 41, Analogously to the example, the compound 3-phenyl-amino-4-ethylthio-K-carbomethoxy-maleinimide is obtained, t, mp, 83-86 ° C,
    Example 42, analogously to example 1, receive the compound 3-phenylamino-4-benzylthio-N-carboxometoxy-small. Ein-imide, t, mp,
    Example 43, analogously to example 1, receive the compound 3-phenylamino-4-cyclohexylthio-N-carbomethoxy-maleinimide, t, mp, 131-134 ° C,
    Example 44 Analogously to Example 1, the compound 3-phenyl-amino-4-chloro-N-carbomethoxy-malein-imide is obtained, m, mp, 155-1-57 ° C,
    Example 45-47 Listed in the table, 2 compounds of the general formula
    R
    ots; Vo -N /
    prepared according to example 6 from the corresponding substituted succinimides of the indicated general formula,
    The herbicidal effect of the general formula is confirmed by the following example: Mi,
    Example 48, Germination inhibition test.
    5I2828I4
    Mustard (Synapis alba) and bristle (Setari sp.) Are used as the test plants. The test active principle is used at a dose of 10 mg (Peter's cup), and the inhibition of germination is assessed one week after germination in the dark (%) compared to untreated control plants.
    Example 49. Pre-emergence test.
    The seeds of the studied plants mustard and bristle seed are sown in culture dishes. The active principle is then applied to the soil in an amount of 20 kg / ha and the culture vessel is exposed for one week to the greenhouse. Herbicidal action rate (%) after one week
    an aqueous solution of potassium hydroxide. The reaction mixture is heated to and kept for 2 hours at this temperature. The reaction mixture is evaporated to approximately 15 ml, and the product is precipitated by the addition of 5N hydrochloric acid. The white crystals formed are filtered, dried and recrystallized from aqueous alcohol. Obtain 2.1 g (90.5%) of 1-phenyluracil-6-carboxylic acid, so pl. 254-263 C (decomposition).
    Example 53 2.6 g (0.01 mol) of 3-phenylamino-N-carbztoxy-maleinimide-5 are suspended in 52 ml of a 1 molar aqueous solution of potassium hydroxide. The reaction mixture is heated to 65 ° C and maintained at this temperature for 2 hours. The reaction mixture is ox10
    ny plants
    Example 50. Post-harvest testing.
    Foliage one-week study
    Compared to the un-scrubbed controls, 20 are limped and 30 ml of a cation-exchange resin of the Varion KS type in H-form is added. After 1/2 hour of stirring, the resin is filtered, the mother liquor is evaporated to dryness and the resulting
    The mustard and bristle plants of the spray-crista Jfic product are recrystallized with the composition of the active principle, lysable from aqueous ethanol. With a semi-appropriate dose of the active one, 2.14 g (92.2%) of 1-phenyluracil-6- beginning 20 kg / ha is started. The herbicidal effect of the carboxylic acid without crystalline is evaluated after one week (%) of alcohol, t. Pl. 253-263 С (in comparison with the untreated control - -30 position). mn plants .. Example 54. 2.6 g (0.01 mol)
    The obtained results are shown in 3-phenylamino-N-carbonic acid-small table. 3. imide suspended in 50 ml of 0.5 mo-B table. 4 given the code numbers of the aqueous hydroxide solution
    compounds.-zg sodium. The reaction mixture is heated
    As intermediate products, 35 "is incubated for 2 hours to synthesize new proizvodstven x x uracil; „Temperature and after that
    cool. Add There are 30 mp cation exchange resin of the Varion KS type. The reaction mixture is stirred for 1/2 hour at room temperature, the resin is filtered off and the mother liquor is evaporated to dryness. The resulting crystalline product is recirculated from the water of 45 crystals. 2.12 g (91.3%) of 1-phenyluracil-6-carboxylic acid are obtained, m.p., 253- (decomposition) -,.
    Example 55. 2.6 g (0.01 mol)
    and dihydrouracilcarboxylic acids exhibiting pharmacological activity, use (the following compounds, ..
    Example 51.5.2 g (0.02 mol) of 3-phenylamino-N-carboxethoxy-smallin-imide is dissolved with stirring in 250 ml of alcohol. Mixture is added dropwise 115 ml of a 2.5% aqueous solution of potassium hydroxide. The reaction mixture is heated to boiling for 1 hour and then evaporated to approximately 30 ml. Proz-phenylamino-L-carbethoxy-maleinduct is precipitated with the help of 5 n, salt -. -, about
    imide is suspended in a solution of 7.85 g (0.025 mol) of barium hydroxide and 385 ml of water. The reaction mixture is heated to 65 ° C, drained in acid, filtered and recrystallized from water. The resulting white crystals are melted at. Obtain 4.1 g 2h at this temperature and for- (88.3%) 1-phenyl-uracil-6-carboxylic acid.
    imide is suspended in a solution of 7.85 (0.025 mol) of barium hydroxide and 385 ml of water. The reaction mixture is heated to 65 ° C, held in
    so cool. 30 ml of Varion K-type cation-exchange resin are added and the mixture is stirred for ½ h at a rotate temperature. The resin is removed.
    acids. „, / l, -
    Example 52. 2.6 g (0.01 mol)
    Z-phenylamino-N-carbethoxy-maleinim-, and suspended in 52 ml of 1-molar
    five
    an aqueous solution of potassium hydroxide. The reaction mixture is heated to and kept for 2 hours at this temperature. The reaction mixture is evaporated to approximately 15 ml, and the product is precipitated by the addition of 5N hydrochloric acid. The white crystals formed are filtered, dried and recrystallized from aqueous alcohol. Obtain 2.1 g (90.5%) of 1-phenyluracil-6-carboxylic acid, so pl. 254-263 C (decomposition).
    Example 53 2.6 g (0.01 mol) of 3-phenylamino-N-carbztoxy-maleinimide-5 are suspended in 52 ml of a 1 molar aqueous solution of potassium hydroxide. The reaction mixture is heated to 65 ° C and maintained at this temperature for 2 hours. The reaction mixture is oX0
    s-phenylamino-Y-carbethoxy-malein-. -, about
     2h at this temperature and the order is "..
    imide is suspended in a solution of 7.85 g (0.025 mol) of barium hydroxide and 385 ml of water. The reaction mixture is heated to 65 ° C, held for 2 hours at this temperature and temperature.
    so cool. 30 ml of a cation-exchange resin of the Varion KS type is added, and the mixture is stirred for 1/2 hour at room temperature. The resin is removed.
    by filtration and the mother liquor is evaporated to dryness. The crystalline product obtained is recrystallized from water. 2.26 g (97.4%) of 1-phenyl-uracil-6-carboxylic acid, m.p. 255-264 ° C. (decomposition) are obtained.
    Example 56, 2.6 g (0.01 mol) of 3-phenylamino-K-carbethoxy-maleinimide is dissolved in 235 ml of anhydrous
    alcohol, and the solution is added with stirring to a solution of 1.68 g (0.03 mol) of potassium hydroxide in 110 m of anhydrous alcohol. The reaction mixture is stirred for 1/2 h at
    at room temperature and then heated to boiling for 1 hour. The solution is evaporated to approximately 70 ml and the precipitated product is filtered off. 2.89 g (93.5%) of 1-phenyluracil-6-carboxylic dicalpium salt, m.p., 295-305 ° С (decomposition) are obtained.
    Example 57, 7.86 g (0.03 mol) of 3-phenylamino-N-carbethoxy-succinimide is suspended in 156 mp of a 1-molar aqueous solution of potassium hydroxide. The suspension is stirred at room temperature for 1 hour. A clear solution is formed. Then 90 ml of Varnon KS-type cation-exchange resin in H-form are added. After 1 hour of stirring at room temperature, the mixture is filtered, to a solution
    five
    0
     five
    0 5
    0
    five
     evaporated to dryness. The oily residue is crystallized upon cooling. The crystals are recrystallized from aqueous acetone. Yield 2.31 g (30.6%) of 1-phenyl-dihydrouracil-6-carboxylic acid, t, pl. 206-213 seconds, i. Example 58-73. The compounds of the above formula given in Table 5 are prepared in a manner similar to the method of their respective compounds described in Examples 51-56. .
    The compounds prepared according to examples 63,65,69, 70 and 72 contain 1 mol, water of crystallization, compounds according to example 68-2 mol, water of crystallization, and compounds according to example 73 - 1 mol, crystalline alcohol.
    Examples 74-84, Compounds of this general formula are prepared as in Example 51 using the corresponding starting materials listed in Table 6,
    Analogously to Example 57, from the corresponding compounds, the compounds are obtained in the form of carboxyl monopotassium salts by concentrating the reaction solution and from scavenging the precipitated product.
    Thus, the novel compounds of the proposed general formula possess a herbicidal action and, in addition, are intermediates for the synthesis of pharmacologically active preparations, thereby expanding the means of action on a living organism.
    Table 1
    Hydrogen
    8 9 10
    .11 12
    |


    68.9
    108-112
    -chloro-S carbethoxy-malein-imide
    3- (4-Methoxy-phenylamino) -4-xnop-N-Kap63TOKCH-ManeHH-imide
    1243 3-Amino-4-chloro-N-carbethoxy-maleinimide
    12713- (4-Chloro-phenylamino) -4- -chlorop-N-carboxethoxy-maleimide
    12723- (3,5-Dichloro-phenylamino) -4-chloro-N-carbethoxy-malein-imide
    1473 3-Phenylsulfonic-N-carbethoxy-maineimide
    1524 C-N-Butylamino-N-carbethoxy-maleinimide
    15273-phenylamino-N-carboxethoxy-succinimide
    15283- (3,4-Dimethoxy-phenyl-ethyl-amino) -Y-carbethoximapeinimd
    1532 3- (5eto.-Naphthylamino) -4-chloro-N-carbethoxy-maleinimide
    1539 3- (4-Methyl-phenylamino) -K-Carbethoxy-succinimide
    15413- (4-Chloro-phenylamino. O) -H- -carbethoxy-succinimide
    15423- (I-Hexylamino) -K-carb-ethoxy-maleinimide
    1622 3-Fe NILamino-4-fe nylthio-N-carbethoxy-maleinimide
    1662 3-Phenylamino-4-phenylsulfo-, nyl-K-carbethoxymaleinimide
    1667Z-Phenylamino-4- (i) y-butyltis) -N-carbethoxy-malein MID
    16683-Phenylamino-4- (iso-butyl-tis) .- K-carbethoxy-malein-imide
    1670 3-Fensch1-amino-4-benzylthio-K- -carbatsksi-maleinikid
    1673 3-Feiyl-4-cyclohexyl-tis-K-carbethoxy-maleinimide
    权利要求:
    Claims (1)
    [1]
    METHOD FOR PRODUCING MAPEINIMIDE AND SUCCINIMIDE DERIVATIVES of General Formula
    X — Y s
    where X - Y is a group ’
    R - C = C - R
    II ’’ where R is a phenylamino group which may be substituted with C ^ -Cg alkyl, C, -C Methoxy, one or two halogen atoms, a cyclohexylamino group, a benzylamino group, a FurFurylamino group, a naphthylamino group, an amino group;
    R is hydrogen, chlorine, phenyl, which may be substituted by methyl; phenylthio, phenylsulfonyl, cyclohexylthio, benzylthio, alkylthio C-C, sulfonyl;
    R 3 is alkoxyl C 1 -C, benzoxy or X-Y represents a group
    R-C-CH-Rt
    I G where R is phenyl, hydrogen;
    R g is hydrogen, phenyl amino groups a, which may be substituted with methyl or chlorine;
    R 2 is alkyl ^ -C ^, hydrogen, characterized in that the compound of the general formula
    X — γ where X - Y has the indicated meaning, is reacted with an acylating agent of the general formula
    R is CO - C1, where Rj has the indicated meaning.
    SU „„ 1282814
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