• 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:
    Compounds of the formula: where: A is oxygen or sulphur: R' is aryl: R2 is 1-imidazolyl or 1,2,4-triazol-1-yl: and R3, R4, R5 and R6, which may be the same or different, are each hydrogen, halo, alkyl or alkoxy, have fungicidal and plant growth regulant activity.
    公开号:SU1402262A3
    申请号:SU853984288
    申请日:1985-11-22
    公开日:1988-06-07
    发明作者:Эрик Грин Дэвид；Персивал Альберт
    申请人:Фбс Лимитед (Фирма)；
    IPC主号:
    专利说明:

    ISD IsD
    about: to
     cm
    The invention relates to a process for the preparation of a novel chemical compound, namely 3- (2,4-dichlorophenyl; -2 -2 (1,2,4-triazol-1-yl) -quinazolin-4 (3N) -one
    It has fungicidal activity and can be used in agriculture.
    The aim of the invention is a process for the preparation of a compound having 1,2,4-triazole. and having fungicidal activity, surpassing the fungicidal activity of other compounds containing 1,2,4-triazole.
    Example. 3- (2,4-Dichlorophenyl) -2- (1,2,4-triazol-1-yl) quinazo; lin-4 (3N) -one.
    a) 3- (2,4-Dichlorophenyl) -1,2-dihydro-2-thioquinazolin-4 (3N) -one.
    2,4-Dichlorophenyl isothiadianate (13.0 g) ext: is in anthranilic acid (8.7 g) in absolute alcohol (80 ml) and the resulting mixture is heated under reflux for 18 hours. This mixture is further cooled to at room temperature, the solid product is filtered and 12.8 g of product are obtained, mp. 248-251 ° C.
    b) 2-Chloro-3- (2,4-dichlorophenyl) -hin zin-4 (3N) -one.
    Sulfuryl chloride in an amount of 5.4 m is added dropwise at room temperature to a suspension of the thioquinazolin-4 (3H) -one obtained (21.6 g) in chloroform (150 ml). The resulting mixture was heated under reflux for 4 hours, then extracted into water (1 l), filtered off, the solid washed with dichloromethane (100 ml). The organic layer is separated from the filtrate, concentrated in vacuo. The residue obtained is extracted with boiling cyclohexane (200 ml). The organic extract is subjected to condensation in vacuo and chromatographed on silica using a silica gel.
    five
    0
    five
    0
    five
    0
    five
    0
    five
    eluent dichloromethane. Obtain 7.3 g of the product, so pl. 14-6-148 ° C.
    c) 3- (2,4-Dichlorophenyl-2- (1,2,4-trizolol-l -yl) -quinazolin-4 (3N) -one.
    A mixture of 2-chloroquinazolin-4 (3N) -one (3.25 g), triazole (0.76 g) and potassium carbonate (1.38 g) in adetonitrile (60 ml) is refluxed for 8 hours. The mixture cooled to room temperature and concentrated in vacuo. The residue is boiled with diclohexane (30 ml), the solid is filtered off after cooling. By recrystallization from absolute alcohol, 1.6 g of product are obtained, m.p. 163-165 ° C.
    The compound is subjected to tests to determine activity against the following types of mold: Puccinia hepodidae, brown leafy rust of wheat (PR) Erysiphe graminis, false host disease (EG),
    The compound was prepared in an aqueous solution of acetone using a Tween-20 moisturizing agent to give a co-concentration equal to 500 mAh. per 1 million compounds (125 parts by weight per 1 million wetting agents), 20,000 mas. hours. per million of acetone; for cereals, Plyronic L 61, which is a block copolymer of ethylene oxide and propylene oxide, is used as an additional wetting agent. This wetting agent is added in an amount corresponding to a concentration of 1000 mash. per million. Plants are then treated with diluted suspensions and inoculated (grafted) 24 hours after treatment with the compound by spraying mold spores. Then they are grown in a humid atmosphere at a relative humidity in excess of 98%.
    The environmental conditions for growing are given in table. one.
    After an appropriate period of time under incubation conditions, the extent of infestation of the leaf surface is visually suited.
    In tab. 2 presents the test results.
    Prochloraz-1-GN-propyl-H- 2 (2,4,6-trichlorophenoxy) ethyl carbamoyl imidazole, propiconazole-2- (2,4-dichloro-nyl) -4-propyl-2- (1H- I, 2,4-triazolyl3U
    -1-methyl) -, 3-dioxolane, triadimefon-3,3-dimethyl-1 - (1H-1,2,4-triazolyl-1) -1- (4-chlorophenoxy) butanone-2.
    Thus, the proposed compound surpasses the known 1,2,4-triazole fragment in its composition for fungicidal activity and can be used in rural areas.
    host
    权利要求:
    Claims (1)
    [1]
    Invention Formula
    The method of obtaining 3- (2,4-dichlorophenyl) -2- (1,2,4-triazol-1-yl) -quinazolin-4 (3N) -one
    Table I
    Pathogen Period Temperature, C Conditions of illumination of the chanting-out-singing, daytime of the night is harmful.
    high humidity, days
    P.recondita 12 18 14, One day in the dark, 1
    16 h in the light / 8 h in the dark every day
    E. graminis 9 18 14 .. 16 h in the light / 8 h at 11
    darkness every day
    Table2 Compound Application rate, g / ha (% mortality)
    False-Mu-: Brown Oats Cucumbers
    nista ro-leafy
    Sa, mold, rust, whetstone
    In the example 20 (83%) 40 (90%) 20 (72%) 50 (64%) Prochloraz 20 (28%) 40 (31%)
    N
    characterized in that the 2-chloro-3- (2,4-dichlorophenyl) -quinazoline-4 (3N) -one is reacted with 1,2,4-triazole in the presence of a base.
    类似技术:
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    引用文献:
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    DE1249281B|1963-05-18|
    FR4721M|1964-06-03|
    FR7865M|1968-10-22|1970-04-27|
    CH612432A5|1975-05-12|1979-07-31|Sandoz Ag|
    GB2002746A|1977-06-17|1979-02-28|Gist Brocades Nv|Copper complexes|
    US4377581A|1980-03-03|1983-03-22|Pfizer Inc.|Chloro- and alkoxy-substituted-2,4-diaminoquinazolines|
    US4419357A|1982-01-18|1983-12-06|The Dow Chemical Company|3--4-quinazolinones|
    DE3412080A1|1984-03-31|1985-10-03|Bayer Ag, 5090 Leverkusen|MICROBICIDES CONTAINING 2- -4- -QUINAZOLINONE|GB8612796D0|1986-05-27|1986-07-02|Fbc Ltd|Fungicides|
    DE3825867A1|1988-03-04|1989-09-14|Bayer Ag|HETEROCYCLICALLY SUBSTITUTED SULFONYLAMINOAZOLES AND THEIR USE AS HERBICIDES|
    US5084457A|1990-07-23|1992-01-28|American Cyanamid Company|Benzoylaminoquinazolinones|
    US5276038A|1992-06-01|1994-01-04|American Cyanamid Company|1-aryl-3-urea fungicidal agents|
    DE4339209A1|1993-11-17|1995-05-18|Hoechst Ag|Process for the preparation of substituted quinazoline-2,4-diones|
    DE4428535A1|1994-08-12|1996-02-15|Bayer Ag|Process for the selective production of fluorinated aromatic amines and fluorinated aromatic amines with particularly low levels of defluorinated components|
    DE4429978A1|1994-08-24|1996-02-29|Bayer Ag|Process for the preparation of quinazoline-2,4-diones|
    US5804686A|1996-01-19|1998-09-08|Neurogen Corporation|fused pyrrolecarboxamides; a new class of GABA brain receptor ligands|
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    US5723462A|1996-04-26|1998-03-03|Neurogen Corporation|Certain fused pyrrolecarboxamides a new class of GABA brain receptor ligands|
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    法律状态:
    优先权:
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    GB848429739A|GB8429739D0|1984-11-24|1984-11-24|Fungicides|
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