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    • 专利摘要:
    Nouveaux dérivés de l'acide (pyridyl-3)-2 phénylamino-2 acétique répondant à la formule: avec: Ro: -CN, -COOH, CONH2, COOR4, R1: H, alkyle inférieur, cycloalkyle, phényle, éventuellement substitué, aralkyle éventuellement substitué, R2: H, alkyle inférieur, éventuellement substitué, Ar: phényle éventuellement substitué, Z: halogène, alkyle inférieur, alkoxy inférieur, alkylthio inférieur. Ils sont utilisables en agriculture pour la lutte contre les champignons phytopathogènes tels que les sclérotiniacées.
    公开号:SU1316557A3
    申请号:SU843818300
    申请日:1984-11-23
    公开日:1987-06-07
    发明作者:Бюло Жан-Поль
    申请人:Рон-Пуленк Агрошими (Фирма)；
    IPC主号:
    专利说明:

    The invention relates to a process for the preparation of novel 2- (3-pyridyl) -3-phenylamino acetic acid derivatives which can be used to protect plants against phytopathogenic fungi.
    The purpose of the invention is to obtain new derivatives of 2- (3-pyridsh1) -2-phenylaminoacetic acid, which have antifungal properties relative to Botrytis, in contrast to the structural analogue, which has the same type of activity.
    Example 1. Preparation of 2-phenyl Thus, 11.3 g of (4-phenylphenyl-1-imino) -3-ethylpyridine of the formula
    W
    3.9 g of potassium cyanide was added to 11.3 g of (4-phenylphenyl-1-imino) -3-ethylpyridine in 50 ml of acetic acid. The mixture is stirred for 24 hours
    amino-2- (3-pyridyl) -propanenitrile (at room temperature. By filter. In this way, 11.3 g of (4-phenylphenyl-1-imino) -3-ethylpyridine of the formula
    3.9 g of potassium cyanide was added to 11.3 g of (4-phenylphenyl-1-imino) -3-ethylpyridine in 50 ml of acetic acid. The mixture is stirred for 24 hours at
    room temperature. By taming 1).
    A flask equipped with a stirrer, a thermometer and a rising cooler is used. The flask is sequentially charged with 40 ml of acetic acid, 12.1 g of 3-acetylpyridine and 9.3 g of aniline and holding the mixture with stirring for 30 minutes at ambient temperature. Then add 20
    25
    Radium of the reaction medium is separated by a white solid, which is subsequently washed with 300 ml of water, 300 ml of 10% potassium bicarbonate solution and 300 ml of water. After drying the product under reduced pressure, 7.8 g of (4-phenylphenyl) -2-amino-2- (3-pyridyl) -propanenitrile are obtained in the form of a white solid, melting
    thirty
    8.5 g of potassium cyanide, B 20 ml of water.
    The mixture is kept for 20 hours at room temperature and the precipitate formed is separated by filtration.
    The solid thus obtained is washed successively with water (200 ml), an aqueous solution (100 ml) of 10% KHCOj, water (200 ml) and then pentane.
    The resulting crude solid-35 is recrystallized in 30 g of ethanol in reflux. This gives 14 g (0.063 mol) of 2-phenylamino-2- (3-pyridyl) -propanenitized at 189 C, yield (calculated on
    3-acetylpyridine) 48%.
    Note 3. In the same way as Example 1, the following is obtained:
    2- (methyl) - (4-chlorophenyl) -amino - (Z-pyridyl) -acetonitrile (compound 3);
    - (4-chlorophenyl) -2-amino-2- (3-pyr dile) -propanenitrile (compound 4);
    - (4-fluorophenyl) -2-amino-2- (3-pyr dil) -propanenitrile (compound 5);
    - (2-fluorophenyl) -2-amino-2- (3-pyr dyl) -propanenitrile (compound 6);
    - (2-fluorophenyl) -2-amino-2- (3-pyridyl) -propanenitrile (compound 6);
    - (4-bromophenyl) -2-amino-2- (3-pyriryl as a white solid,
    melting at 156 ° C. The release of (propagated) -propannitrsh1 (compound 7).
    read on acetylpyridin) 63%. Analogously to example 2 receive:
    EXAMPLE 2. Preparation of (4-phenylphenyl) -2-amino-2- (3-pyridyl) propanenitrile (compound 2).
    The product is obtained in two stages, similar to Example 1,
    6 g of 3-acetylpyridine, 9.3 g of 4-aminobiphenyl and 0.9 g of p-toluenesulfonic acid are dissolved in 100 ml of toluene. The solution is heated to a temperature of 50–2- (3-pyrid) -acetonitrile (the solvent compound is for 4
    - (3,4-dichlorophenyl) -2-amino- (3-pyridyl) -propanenitrile (compound 8);
    - (3-chlorophenyl) -2-amino-2- (3-pyrid-d1) -propanenitrile (compound 9);
    - (2,4-dichlorophenyl) -2-amino-2- (3-pyridyl) -propanenitrile (compound 10);
    - (4-fluorophenyl) -2-amino-2-phenyl, and
    the resulting water is collected in a Dean-Stark collection.
    After cooling, the solution is washed with water (3-100 ml), dried on sodium sulfate in the presence of coal, then filtered and evaporated at reduced pressure.
    11);
    -2-phenylamino-2-phenyl-2- (3-pyridyl) -acetonitrile (compound 12);
    - (2,4-difluorophenyl) -2-amicho-2- (3-pyridyl) -propanenitrile (compound 13);
    - (3-fluorophenyl) -2-amino-2- (3-pyridyl) -propanenitrile (compound 14);
    Radium of the reaction medium is separated by a white solid, which is successively washed with 300 ml of water, 300 ml of 10% potassium bicarbonate solution and 300 ml of water. After drying the product under reduced pressure, 7.8 g of (4-phenylphenyl) -2-amino-2- (3-pyridyl) -propanenitrile are obtained in the form of a white solid, melting
    at 189 C, the output (calculated on
    thirty
    35
    3-acetylpyridine) 48%.
    Example 3. Analogously to example 1, receive:
    2- (methyl) - (4-chlorophenyl) -amino 2 - (3-pyridyl) -acetonitrile (compound 3);
    - (4-chlorophenyl) -2-amino-2- (3-pyridyl) -propanenitrile (compound 4);
    - (4-fluorophenyl) -2-amino-2- (3-pyridyl) -propanenitrile (compound 5);
    - (2-fluorophenyl) -2-amino-2- (3-pyridyl) -propanenitrile (compound 6);
    - (4-bromophenyl) -2-amino-2- (3-pyr dyl) -propannitr1 (compound 7).
    -2- (3-pyridium) - acetonitrile (compound
    - (3,4-dichlorophenyl) -2-amino- (3-pyridyl) -propanenitrile (compound 8);
    - (3-chlorophenyl) -2-amino-2- (3-pyrid-d1) -propanenitrile (compound 9);
    - (2,4-dichlorophenyl) -2-amino-2- (3-pyridyl) -propanenitrile (compound 10);
    - (4-fluorophenyl) -2-amino-2-phenyl. 50 -2- (3-pyridium) - acetonitrile (compound
    11);
    -2-phenylamino-2-phenyl-2- (3-pyridyl) -acetonitrile (compound 12);
    - (2,4-difluorophenyl) -2-amicho-2- (3-pyridyl) -propanenitrile (compound 13);
    - (3-fluorophenyl) -2-amino-2- (3-pyridyl) -propanenitrile (compound 14);
    - (3-chloro-4-fluorophenyl) -2-amino-2- (3-pyridyl) -propanenitrile (compound 15);
    - (3-cyanophenyl) -2-amino-2- (3-pyrile dil) -propanenitrsh (compound 16);
     - (3-bromophenyl) -2-amino-2- (3-pyri-dSh1) -propanenitrile (compound 17);
    - (3-methylphenyl) -2-amino-2 -. (3-pyr dyl) -propanenitrile (compound 18);
    - (4-chlorophenyl) -2-amino-2- (3-pyridyl) -pentanenitrile (compound 19);
    - (3-bromo-4-chlorophenyl) -2-amino-2- (3-pyridyl-propanenitrile (compound 20);
    - (3,4-dichlorophenyl) -2-amino-2- (3-pyridyl) -pentanenitryl (compound 21);
    - (3,4,5-trichlorophenyl) -2-amine-2- (3-pyridyl) -propanenitrile (compound 22);
    - (3-chloro-4-fluorophenyl) -2-amino-2- (3-pyridyl) -pentanenitrile (compound 23);
    - (3,4, -dichlorophenyl) -2-amino-2- (3-pyridyl) -2-phenylacetonitrile (compound 24);
    - (4-chlorophenyl) -2-amino-2- (3-pyridyl) -4-methylpentanenitrile (compound 25);
    - (3,4-dichlorophenyl) -2-amino-2- (3-pyridyl) -4-methylpentanenitrile (compound 26);
    - (3-bromo-4-chlorophenyl) -2-amino-2- (3-pyridam1-2-phenylacetonitrile (compound 27);
    - (3-chloro-4-fluorophenyl) -2-amino) -2- - (3-pyridyl) -4-fetylpentanenitrile (compound 28);
    - (4-methoxycarbonylphenyl-2-amino--2- (3-pyridyl) -propanenitrile (compound 29);
    - (4-fluorophenyl) -2-amino-2- (3-pyridyl) -pentanenitrile (compound 30);
    - (3-methylthiophenyl) -2-amino-2- (3-pridyl-3) -propanenitrile (compound 31)
    -. (4-Chlornifel) -2-amino-2- (3-pyridyl) -butanenitrile (compound 32);
    - (3-chloro-4-fluorofensh1-2-amino-2- (3-pyridyl) -butanenitrile (compound 33)
    - (4-chlorophenyl) -2-amino-2- (3-pyridyl) -hexanenitrile (compound 34);
    - (3,4-dichlrrphenyl) -2-amino-2- (3-pyridyl) -butanenitrile (compound 35
    - (3-bromophenyl) -2-amino-2- (3-pyridyl) -butanenitrile (compound 36);
    - (4 Chlorophenyl) -2-amino-2- (3-pyridyl) -3-methylbutanenitrile (compound 37);
    - (4-fluorophenyl) -2-amino-2- (3-pyridyl) -3-methylbutanenitrile. (Compound. 38);
    - (4-fluorophenyl) -2-amino-2- (3-pyridyl) -butanenitrile (compound 39);
    - (3-chloro-4-fluorophenyl) -2-amino-2- (3-pyridsh1) -3-phenylpropanenitrile (compound 40);
    - (4-trifluoromethylphenyl) -2-amino-2- (3-pyridyl) -butanenitrile (compound 41);
    - (3,4-difluorophenyl) -2-amino-2- (3- -pyridsh1) -butanenitrile (compound 42)
    -2-phenylamino-2- (3-pyridyl) -butane nitrile (compound 43);
    - (3-chloro-4-fluorofensh1) -2-amino-2- (3-pyridsh1) -3-methylthiopropanenitrile (compound 44);
    - (4-bromophenyl) -2-amino-2- (3-pyridyl) -pen tannitrile (compound 45);
    - (4-bromophenyl) -2-amino-2- (3-pyri-d1) -butanenitrile (compound 46);
    - (4-chlorophenyl) -2-amino-2- (3-pyridyl) -2-cycloamile tannitrile (compound 47);
    - (3,4-difluorophenyl) -2-amino-2- (3-pyridyl) -pentanenitrile (compound 48); - (3,4-difluorophenyl) -2-amino-2- (3-pyridyl) -3 -methylbutanenitrile (compound 49);
    -4- (trifluoromersh1phenyl) -2-amino-.2- - (3-pyridyl) -3-methylbutanenitrile (compound 50);
    - (4-chlorophenyl) -2-amino-2- (5-methyl-3-pyridyl) -butanenitrile (compound 51);
    - (4-chlorofensh1) -2-amino-2- (4-methyl-3-pyridyl) -butanenitrile (compound 52);
    - (3-chloro-4-fluorophenyl) -2-amino-2- (4-metsh-3-pyridyl) -butanenitrile (compound 53);
    - (4-chlorophenyl) -2-amino-2- (4,5-dimethyl-3-pyridyl) -butanenitrile (compound 54);
    - (3-chloro-4-fluorophenyl) -2-amino-2- (4-ethyl-3-pyridyl) -butanenitrile (compound 55);
    - (4-fluorophenyl) -2-amino-2- (4-ethyl-3-pyridyl) -butanenitrile (compound 56);
    - (3,4-dichlorophenyl) -2-amino-2- (4-thyl-3-pyridyl) -propanenitrile (compound 57);
    - (4-chlorophenyl) -2-amino-2- (4-methyl-3-pyridyl) -propanenitrile (compound 58);
    - (4-chlorophenyl) -2-amino-2- (4-methoxy-3-pyridyl) -butanenitrile (compound 59);
    - (4-chloro4) enyl) -2-amino-2- (4-methoxy-3-pyridyl) -propanenitrile (compound 60);
    - (3,4-dichlorophenyl) -2-amino-2- (4- -methoxy-3-pyridyl) -propanenitrile (compound 61);
    - (3,4-difluorofensh1) -2-amino-2- (4-methyl-3-pyridyl) -butanenitrile (compound 62);
    - (4-bromophenyl) -2-amino-2 (4-methyl-3-pyridyl) -butanenitrile (compound 63);
    - (4-fluoroferyl) -2-amino-2- (4-i-eopropyl-3-pyridyl) -butanenitrile (compound 72).
    Data on the compounds obtained are given in table. 1 and 2.,
    Example 4 Preparation of the chlorohydrate of compound 4.
    To 5 g of a solution of (4-chlorophenyl) -2-amino- (3-pyridyl) -propanenitrile in 2.5 liters of anhydrous ether is added 18 ml of a solution of HCl. 1.08 N, filtered, dried, and thus receive 5.5 g hydrochloride of compound 4, melted at 120 ° C,
    Example 5 “Preparation of (3,4-dichlorophenyl) -2-amino-2- (3-pyridyl) propane amide (compound 64)
    The flask is charged with 20 g of (3,4-dichlorfensh1) -2-amino-2- (3-pyridyl-propannitrile (compound 8) and 170 ml of anhydrous methanol
    After cooling the suspension to 0.5 ° C, the gas stream of hydrochloric acid is slowly stirred until saturated, after going to ambient temperature it is stirred for 16 hours. Then the reaction mixture is diluted with 150 ml of anhydrous ether. The obtained solid is quickly dried, washed with 300 ml of anhydrous ether, then placed in an aqueous solution with 10% KHCOj. After filtration, washing with distilled water, ethanol, and drying in vacuo, 19.6 g (3,4-dichloro-nSH1) -2-aminopropanamide are obtained in the form of a white solid, melting at 175 ° C. (yield 92%).
    Example 6. Preparation of (3,4-dichlorophenyl) -2-amino-2- (3-pyridyl) -pro-panovoic acid (compound 65).
    19.2 g of (3,4-di-; chlorophenyl) -2-amino-2- (3-pyridyl) -propanamide (compound 64) and 190 ml of hydrochloric acid 6N are charged to the flask, then heated in reflux for 7 hours. In this case, a precipitate forms, which is filtered and treated with 800 m of water and 25 ml of concentrated ammonium hydroxide. Then the ammonium selenate heated to ammonium is filtered and treated with 25 ml of glacial acetic acid. After filtration, the solid is washed with water and then dried under vacuum.
    13.2 g of (3,4-dichlorophenyl--2-amino-2- (3-pyridyl) propanoic acid) are obtained in the form of a solid, melting at 190 s.
    EXAMPLE 7 Preparation of (3,4-dichlorophenyl) -2-amino-2- (3-pyridyl) methylpropionate (compound 66).
    A flask is charged with 4.8 g of (3,4-diclorophenyl) -2-amino-2- (3-pyridyl) propanoic acid (compound 64) in 25 ml of anhydrous methanol. After cooling to minus, 1.3 ml of sulfinyl chloride are added simultaneously, then slowly brought to reflux.
    After 3 hours, cool again to minus 10 ° C, then 1.3 ml of sulphinyl chloride is added.
    After 5 hours of heating in reflux, the reaction mixture is evaporated under reduced pressure, then the initial product is treated in succession with 50 m of ether, 50 ml of distilled water, 5 g of potassium bicarbonate.
    After decantation, the organic phase is dried on sodium sulphate and evaporated. The oily residue is purified by chromatography on a silica column (eluent ether).
    3.5 g of (3,4-dichlorophenyl) -2-amino-2- (3-pyridyl) -methylpropion and pale yellow color are obtained, yield 72%.
    PRI m e. R 8. Analogously to example 7, from the corresponding initial substances receive:
    (4-chlorofensh1) -2-amino-2- (3-pyridyl) methyl propionate, melting at (compound 67);
    (4-chlorophenyl) -2-amino-2- (3-pyridyl) methyl butyrate, melting at 154 s (compound 68); : (3,4-dichlorophenyl) -2-amino-2- (3-pyridyl) methyl butyrate, melting at
    at 112 ° C (compound 69);
    (3-bromo-4 Chlorophenyl) -2-amino-2- - (3-pyridyl) methyl butyrate, melting at (compound 70);
    11316557
    (3, A-dichlorophenyl) -2-amino-2- (3-pius with
    ridyl) -methylbentirate as a yellow oil (compound 71).
    PRI me R 9. Testimony in the test at the omenium barley .5
    Prepare a thin aqueous suspension of the active substance to be tested. The following composition: active substance to be tested 40 mg; tween-80 (surfactant in the form of sorbitan polyoxyethylene monolaurate) 0.4 ml; water 40 ml.
    The aqueous suspension is then diluted with water to obtain the desired concentration. five
    Barley seedlings of Hordeum vulgare Beras are diluted in cups. After 5 days, they are infected by dyeing through the spores of oidium barley Erysiphe graminis, then kept in a greenhouse 20 at 22 + 2 C with a relative humidity of 70-80%.
    2 days after infection, when the foliage is covered with oidium, the seedlings are sprayed onto each seedling with 8 ml suspension of the active substance in distilled water containing 0.02 mass%, tween-80% of a given concentration .. Process
    After 24 hours, the leaves are cut and put into two Petri dishes (diameter 11 cm, the bottom of which is pre-equipped with a disk in the form of a wet paper filter (5 leaves per cup).
    The inoculation is then carried out using a syringe by applying a spore suspension (three drops per leaf) to the suspension. This suspension of Botryt cinerea spores is obtained from a culture of 15 days old, which is then placed in a nutrient solution (80000 units / cm.) 4 days after infection, the wire is checked by comparison with an intact control sample.
    Under these conditions, at a concentration of 1000 mg / l, the protection is respectively 95% for compounds 4,5,7-9, 14,15,19,23,29,30,32-35,37,42-45,48 49.55-59.61-63.66; 80% (not less than 95 for compounds 17,25,28,51,60; 50% (but less than 80%) for compounds 16,18 20,36,38,39,41,46,50,52,65; 20 % (but it is 50%) for compounds 24,26,40, 53 and 54.
    Example 11. Antifungal effect on beet germ disease (Ce cospora Beticola).
    Sugar beet (Beta vulgaris
    substance in three doses. Monostar is grown in the greenhouse in the same way.
    control samples of seedlings are processed at once, but without the active substance .-,
    Then the treated seedlings are again placed in a greenhouse with the specified temperature and humidity conditions.
    10 days after treatment of the seedlings with a suspension of the active substance, the percentage of growth inhibition of the fungus is calculated as compared to the untreated control sample.
    Under these conditions, at a concentration of 500 mg / l, the deceleration of the development of the fungus is respectively 90% for compounds 4,10,15,17,19,20,21,25-28, 45 30,32-39,42,43; 70% (but less than 90%) for compounds 1-9, 11-14, 18,23,29,40, 44,51,56; 20% (but less than 70%) for At compounds, 47.48.
    50
    PRI me R 10. Antifungal effects on tomato Botrytis cinerea.
    Tomatoes grown in a greenhouse (Marmande variety), 60-75 days old, have treated plastic cups with a mixture of river sand and 12 days when grown at the stage of two sheets of 7 cm, they are treated with aqueous suspensions as in Example 10 with different active substances. A dose of about 5 ml corresponds to a dose of 1000 l / substance of each concentration in three cups.
    Then inoculate the veterinarian so that approximately 5 ml of this
    After this, the incubation la is infected for 2 days in a sparse atmosphere and in the dark for 12 days in normal tones (20 + 2 s and 60-80
    The check carried out after infection and vychas protection compared to
    They are melted by spraying an aqueous suspension control sample.
    The composition of Example 9 with different concentrations of active substance (the experiments are repeated two times).
    eight
    After 24 hours, the leaves are cut and placed in two Petri dishes (diameter 11 cm), the bottom of which is pre-equipped with a disk in the form of a wet paper filter (5 leaves per cup).
    The inoculation is then carried out using a syringe by applying a spore suspension (three drops per leaf) to the suspension. This spore suspension of Botrytis cinerea is obtained from a 15-day culture, which is then placed in a nutrient solution (80000 units / cm). Four days after infection, the test is performed by comparison with an untreated control sample.
    Under these conditions, at a concentration of 1000 mg / l, the protection is respectively 95% for compounds 4,5,7-9, 14,15,19,23,29,30,32-35,37,42-45,48, 49.55-59.61-63.66; 80% (at least 95%) for compounds 17,25,28,51,60; 50% (but less than 80%) for compounds 16.18, 20.36.38,39,41,46,50,52,65; 20% (but not its 50%) for compounds 24,26,40, 53 and 54.
    Example 11. Antifungal effect on beet germ disease (Seg-cospora Beticola).
    Sugar beet (Beta vulgaris)
    Monostar cultivar grown in the greenhouse
    in plastic cups containing a mixture of river sand and peat (1/1), after 12 days, when the sprouts are at the stage of two sheets, 5–7 cm high, they are sprayed with aqueous suspensions of the composition of example 10 with different concentrations of active substances. Each cup receives about 5 ml of the composition, which corresponds to a dose of 1000 l / ha. The active substance of each concentration is introduced into three cups of
    Then inoculate with an atomizer so that each cup receives about 5 ml of this suspension.
    After that, the infected plants undergo an incubation period first for 2 days at 26 ° C in a humid atmosphere and in the dark, then about 12 days in normal greenhouse conditions (20 + 2 s and 60-80% humidity).
    The test is carried out 14 days after infection and the percentage of protection compared to the untreated
    control sample.
    Under these conditions, at a concentration of 1000 mg / l, the protection is respectively 95% for compounds 19,2.1,23,
    913
    25,26,28,30,32,33,37,42; 80% (but less than 95%) for compounds 35.36.46; 50% (but less than 80%) for compounds 20.29.
    These results show a good antifungal activity of the proposed compounds.
    The proposed compounds are of great interest from the point of view of their activity with respect to sclerotinicide, in particular to Botrytis, and as a result, can be used for such crops as cereals (e.g. barley), rice, grapes, sugar

    crops (peanuts. and banana), in vegetable growing, floriculture and in cultivation of trees (fruit). Among the compounds according to the invention, compounds 4,7,8,19,21,23,32, 33,35,37,42,44,55 are particularly preferred.
    The results of the experiments are given in table. 1 and 2.
    权利要求:
    Claims (2)
    [1]
    1. A method for the production of single 2- (3-pyridyl) -2-phenylaminoacetic acid of the general formula
    7, RS
    N RI
    (I)
    de
    R, -CN, COOH,
    t
    CONH, COOR .;
    l .4
    lower alkyl, hydrogen, phenyl lower apyl, substituted by phenyl, thio; lower alkyl, lower alkoxy; hydrogen atom; d
    lower alkyl; 0,1,2,3;
    phenyl or phenyl substituted by halogen, alkylthio group esterified by carboxyl group,
    similar to the pyridine derivatives of the general formula
    Z - R, m Ar 35
    g
    (zv € jr °
    N
    (Ii)
    Where
    Rj. Z
    and m have the specified sign
    cheny
    subjected to interaction with an aniline derivative of the general formula
    - five
    ten
    R,
    Hn-ar
    (Iii)
    five
    ABOUT
    five
    0
    five
    where Ar has the indicated meanings, in the presence of hydrocyanic acid, possibly obtained in situ in situ, to give the desired product, where R (-CN, or the resulting compound, where R, is CN, is hydrated to give a compound of the general formula (I), where RI-CONH, or by hydrolysis of a compound of the general formula (1), where R, CONHj, in an acidic medium, followed by neutralization to obtain a compound of the general formula (I), where R is COOH, or by esterifying the resulting compound, where R / 1-COOH, or by esterifying the resulting compound, where R, is —COOH, the alcohol R.OH, and the allocation of the target product. ukta
    [2]
    2. A process for the preparation of 2- (3-pyridyl) -2-phenylaminoacetic acid derivatives of general formula
    2 Kg
    ). N RI.
    (I)
    where R,, R ,, R ,, Z, m
    and Ar have the indicated meanings, characterized in that the reaction is carried out in the presence of a dehydrating agent with an azeotropic distillation of water of the pyridine derivative of the general formula
    .
    ()
    N
    (Iv)
    and m have the indicated values R, Z
    neither
    with an aniline derivative of general formula
    Hjn
    - Ar,
    (V)
    where Ar has the indicated meanings to give a compound of the general formula
    50
    (
    (Vi)
    N
    55 where Z, t, R and Ar have indicated
    values that are reacted with hydrocyanic acid, possibly formed locally, and
    11 1316557.12
    the obtained compound of the general formula followed by neutralization to obtain (I), where R, -CN, or is prepared, or the compound of the general formula (I), is hydrated to obtain the compound where R, -COOH, or by esterification of the semi-general formula (I), where R .-CONH, of the designated compound, where R, -COOH, alcohol-hydrolysis of the compound of general formula 5. t and isolation of the desired pro (I), where R, -CONH, in an acidic medium of the compound.
    RiBi f C-N-Ar
    U:
    Table 1
    13
    1316557
    14 Continued table. one
    Cyclopenyl
    - (CH) CH, H
    - (CH) (CH,) 2 N
    -CH (CH,) ,, H
    p-C1-CjH,
    m ,, t, pg ,, p-CF, -C, H
    ) CN
    sn.
    tV
    -N
    -c, n
    156
    57 28 19
    table 2
    pd-C H
    14750
    52
    WITH
    N
    -0, H p-C1-CjH
    14637
    sn
    SNC
     N CH.
    1SI
    N С2Н5
    0 ".
    Lg
    TO
    .
    -s, n
    -СН5
    sn.
    m-CI-p-Fp-d-C H
    m-Cl-p-F-C .jHyP-F-CgH
    m.p-Clj C
    m-CI-p-FCfiHj
    15544
    pd-C H
    12322
    m-Cl-p-FC H,
    14847
    11714
    m.p-Clj C H, .15641
    3 60 / L (G er-C1-CnH417125
    O-Shz
    61H CHt, p-C12-SbN, 14521
    N SNS
    62 JT-С Nute.r-Rg-C Ne13842
    Yu,
    cV
    631 -C Kfp-Br-CgH 15543
    N
    72l; Jj-cjhyp-f-cjh 172
    N.
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    同族专利:
    公开号 | 公开日
    PT79546B|1986-12-15|
    AU3575484A|1985-05-30|
    ES537893A0|1985-10-16|
    FR2555579B1|1987-11-20|
    OA07872A|1986-11-20|
    EP0145620A3|1986-01-08|
    DK557184A|1985-07-02|
    US4743603A|1988-05-10|
    PT79546A|1984-12-01|
    PL143772B1|1988-03-31|
    PL250497A1|1985-09-10|
    FI844610L|1985-05-25|
    HU194690B|1988-03-28|
    KR850003714A|1985-06-26|
    IL73478A|1988-06-30|
    EP0145620A2|1985-06-19|
    IL73478D0|1985-02-28|
    BG44534A3|1988-12-15|
    FR2555579A1|1985-05-31|
    ES8601137A1|1985-10-16|
    BR8405975A|1985-08-27|
    RO89783A|1986-07-30|
    FI844610A0|1984-11-23|
    MA20274A1|1985-07-01|
    DD234603A5|1986-04-09|
    ZA849123B|1985-07-31|
    GR80994B|1985-03-08|
    PH21141A|1987-07-27|
    TR22096A|1986-04-03|
    AU586613B2|1989-07-20|
    DK557184D0|1984-11-23|
    JPS60136559A|1985-07-20|
    NZ210286A|1988-10-28|
    CS247091B2|1986-11-13|
    HUT37333A|1985-12-28|
    引用文献:
    公开号 | 申请日 | 公开日 | 申请人 | 专利标题
    DE1026318B|1954-07-09|1958-03-20|Thomae Gmbh Dr K|Process for the production of ª ‡ -tert. -Amino-acetonitriles|
    US3313683A|1963-04-22|1967-04-11|Lilly Co Eli|Nematocidal and fungicidal methods|
    CA1132567A|1978-08-08|1982-09-28|Pieter T. Haken|Phenyliminomethylpyridinederivatives|US5180827A|1988-03-29|1993-01-19|Rhone-Poulenc Agrochimie|2- propanenitrile derivatives|
    FR2629455B1|1988-03-29|1991-09-27|Rhone Poulenc Agrochimie|DERIVATIVES OF 2-3-PROPANENITRILE|
    WO1997036870A1|1996-04-02|1997-10-09|Uniroyal Chemical Company, Inc.|Pyridylmethyl nitriles, amides and thioamides useful as fungicides|
    US9334232B2|2009-06-05|2016-05-10|Akzo Nobel Chemicals International B.V.|Process to prepare a chelating agent or precursor thereof using a cyanide salt|
    JP5801799B2|2009-06-05|2015-10-28|アクゾ ノーベル ケミカルズ インターナショナル ベスローテン フエンノートシャップＡｋｚｏ Ｎｏｂｅｌ Ｃｈｅｍｉｃａｌｓ Ｉｎｔｅｒｎａｔｉｏｎａｌ Ｂ．Ｖ．|Electrochemical method for preparing chemicals using cyanide salts|
    法律状态:
    优先权:
    申请号 | 申请日 | 专利标题
    FR838318976A|FR2555579B1|1983-11-24|1983-11-24|NOVEL PYRIDYLACETONITRIL DERIVATIVES, THEIR PREPARATION AND THEIR USE AS ANTIFUNGALS IN THE AGRICULTURAL FIELD|
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