• 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:
    Novel ???-(1-triazolyl)-keto-derivatives, possessing high fungicidal activity, have the general formula:… …<IMAGE>… in which:… R represents an optionally substituted alkyl, alkenyl or phenyl, R'' represents an alkoxycarbonyl, alkylcarbonyl, arylcarbonyl, aminocarbonyl or cyano group, and… R' represents any one of the groups defined in R and R''. …<??>The novel compounds are prepared by reacting 1,2,4-triazole with a novel intermediate of the formula:… …<IMAGE>… in an inert solvent, in the presence of a catalytic amount of an organic base at the reflux temperature of the reaction mixture.
    公开号:SU1209028A3
    申请号:SU833605553
    申请日:1983-06-02
    公开日:1986-01-30
    发明作者:Цецере Мирелла；Гоццо Франко；Маландра Антонио；Миренна Луиджи
    申请人:Монтэдисон С.П.А. (Фирма)；
    IPC主号:
    专利说明:

    The invention relates to a process for the preparation of new triazo-lilketone derivatives, which have valuable fungicidal properties and find application in agriculture,
    The purpose of the invention is a method for the synthesis of new triazolyl ketones, which are characterized by a higher fungicidal activity.
    Example 1. Preparation of 2-benzoyl-3- (1,2,4-triazolyl) -3- (4-chlorobenzoyl) propionic acid ethyl ester.
    A solution of ITl1 g of ethyl 2-benzoyl-3- (4-chlorobenzoyl) acrylic acid and 3.45 g of 15284-triazole in 150 ml of toluene is refluxed for 12 hours in the presence of a catalytic amount of triethyl per (0.5 ml) ,
    The solution is cooled to room temperature, washed with water and dried with sodium sulfate.
    After distilling off the solvent under reduced pressure, an impure product J is obtained which, upon dilution with a small amount of cold ethyl ether, gives 14.6 g of a white solid (m, mp, 135–13 s).
     I-NMR (HVG1, GC), M.D .:
    l, 0 (3Fs t, SNg-C1C); 3.95 (2H, KB, CHj-CHg); (IH, d, CR, 3 11 Hz); 6.9 (IH, d, CH „3 11 Hz); 7.2-8.2 (YUN, m, aromatic protons + CH of triazole); 8.4 (GN, s, CH, triazole),
    Example 2, Preparation of 4-chlorophenyl-o6-l (19 2,4-triazolyl) 1 zoyl-p-phenylethylketone.
    A mixture of 4.2 g of 1,2,4-triazole5 14 g of 4-chlorophenyl-p-benzoyl-phenylvinyl-ketone, 0.5 ml of triethylamine and 120 ml of toluene is heated under reflux for 32 hours. After cooling to a mixture
    The mixture was washed with water and dried over anhydrous sodium sulfate at the same temperature. After the solvent was distilled off under reduced pressure, the crude product was chromatographed on silica gel (eluant: n-hexane-ethyl acetate 8: 1). white solid), mp, 95 197 С (after crystallization from ethyl acetate and petroleum ether),
    IR spectrum, cm (),
    -one
    1690 1655
    S

    YU
    15 30
    i-dahr (GSS ,, TT C) J, MD: 5.70 (1H, d, CH,: 10 Hz); 6.65 (IR, d, CH. 3 10 H); 7.10-8.25 (UH, m., Aromatic and triazole protons),
    Example 3 / Compounds of formula Sra are given in Table. 1, was prepared as described in the examples and 2j using the appropriate starting materials and 1,254-triazole.
    L
    t
    -C-CH CH-tf I I
    about 1SI
    G01
    (I)
    Example 4. Determination of funktivnosti against oidium cucumbers (Sphaerotheca fuliginea (Schlech) Salmon).
    Prophylactic activity
    Marker variety cucumber plants grown in pots under conditions of a controlled environment are sprayed from the underside of the leaf with the test compound in a water-acetone solution containing 20% acetone (v / v). Then the plants are placed in a controlled environment for 6 days and on the seventh day they sprayed from the upper side of the leaf with an aqueous suspension of conidia Sphaerotheca fuligenea (200 thousand conidia per 1) o Plants in a controlled environment.
    At the end of the incubation period of the fungi, on the eighth day, the degree of infection is estimated, which is given on a scale from 00 (healthy plant) to O (fully affected plant),
    Therapeutic activity.
    Marketer variety cucumber plants grown in pots in a controlled environment are sprayed on the upper side with an aqueous suspension of conidia Sphaerotheca + fulipenea (200 thousand, 1 ml conidia), 24 hours after infection, the plants are treated with test 1 with a compound in an aqueous acetone solution, containing 20% acetone (v / v), pu-. spraying on both sides of the leaf.
    At the end of the incubation period of the fungi (8 days), during which the plants are kept in contact 120428 4
    Rolled environment
    on a scale of 100 (healthy cucumber plants for compounds of the formula
    ) to O (completely Affected by comparing with the known compound) .5 are given in Table 2.
    sh
    vD
    40
    H)
    00 chO
    ft S
    e- m
    X
    “And
    R Oh O. b U) C
    En) h
    ABOUT)
    P)
    Em
    in I)
    TO
    CJ

    - o:
    I u
    o o o i
    Irs
    T
    tSJ
    ABOUT
    about
    ABOUT
    about
    Jk
    Y
    and
    1209028
    12
    table 2
    13
    1209028
    Continuation of table 2
    0.06
    0.5 0.25
    0.125
    0.06
    0.5
    0.25
    0.125
    0.06
    0.5 0.25 0.125 0.06
    0.5
    0.25 0.125
    0.5
    0.25
    0.125
    0.5 0.25 0.125 0.06
    0.5
    0.25
    0.125







    . 100
    100
    100
    100 100 100 100 100 100
    100 100
    ioo
    100 100
    100
    100
    100 100
    100 100 100
    100 100 100
    15
    0.5
    0.25
    0.125
    0.5 0.25
    0.125 0.06
    0.5 0.25 0.125 0.06
    0.5 o, 25
    0.5 0.25
    Known
    dynamic
    2- (1,2,4-tri-
    azol-1-yl) -1, 4-di- (4-
    chlorophenyl)
    butane-1,4-
    Dion
    Compiled by A.Orlov Editor M.Tsitkina Tehred A.Nabinets
    Order 308/61 Circulation 379Subscription
    VNIIPI USSR State Committee
    for inventions and discoveries 113035, Moscow, Zh-35, Raushsk nab., 4/5
    Branch PPP Patent, Uzhgorod, st. Project, 4
    120902816
    Continuation of table 2




    100 100 100
    100 100
    100 100
    100 100 100 100
    100 100
    100
    100
    100
    85
    76
    about
    Proofreader T. Kolb
    权利要求:
    Claims (1)
    [1]
    METHOD FOR PRODUCING << - (1 ~ TRIAZOLYL) KETO DERIVATIVES OF GENERAL FORMULA
    About rc-ch-chr 2 r 3 where R 1 is unsubstituted phenyl or substituted with one substituent from among C ( - C4 alkyl or alkoxyl, halogen } g or C ( - C & alkyl;
    An R-alkylcarbonyl or alkoxycarbonyl group, wherein C, -C 4 -alkyl, unsubstituted phenylcarbonyl group, unsubstituted phenyl or substituted with halogen or C, -C 6 -alkyl;
    R 3 is an alkylcarbonyl or alkoxycarbonyl group, where a C $ -C4 ~ alkyl, an unsubstituted phenylcarbonyl group or one substituted with one substituent from a C 1 -C4 ~ alkyl or alkoxy, or halogen, characterized in that the compound of the general formula
    About rc-ch = cr 2 r 3 where R ( , R z h R '- have the indicated meanings, are reacted with 1,2,4triazole in an inert solvent when boiled in the presence of catalytic amounts of an organic base.
    Priority by signs:
    03.06.82 at P * - C, - C alkyl; R is an alkylcarbonyl or alkoxy carbonyl group, where C ( is C4 alkyl, an unsubstituted phenylcarbonyl group, where C is -C 6 -alkyl;
    R is an alkylcarbonyl or alkoxycarbonyl group, where C ( - C4 alkyl;
    12/30/82 for all other values of R ', R *, R 5 .
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    GB1553907A|1976-07-29|1979-10-10|Ici Ltd|Substituted ketones and their use as fungicidal compounds|
    US4181518A|1976-12-24|1980-01-01|Imperial Chemical Industries Limited|Method of regulating plant growth using triazole and imidazole compounds|
    GB1554490A|1977-12-05|1979-10-24|Ici Ltd|Method of regulating plant growth using triazole and imidazole compounds and some of the compounds themselves|
    DE2831235A1|1978-07-15|1980-01-31|Basf Ag|1-Azolyl-2,2-di:carbonyl substd. ethane derivs. - useful as soil nematocides|
    DE2836945A1|1978-08-24|1980-03-13|Hoechst Ag|DERIVATIVES OF 1,2,4-TRIAZOLE|
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    DE3104311A1|1981-02-07|1982-08-19|Bayer Ag, 5090 Leverkusen|2-AZOLYLMETHYL-1,3-DIOXOLANE AND -DIOXANE DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS FUNGICIDES|IT1170080B|1983-12-30|1987-06-03|Montedison Spa|TRIAZOLYL-KETO-DERIVATIVES HAVING FUNGICIDE ACTIVITIES|
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    法律状态:
    优先权:
    申请号 | 申请日 | 专利标题
    IT21665/82A|IT1157947B|1982-06-03|1982-06-03|ALPHA--KETO-FUNGICIDAL DERIVATIVES|
    IT2504882A|IT1155094B|1982-12-30|1982-12-30|Alpha-triazolyl substd. ketone derivs.|
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