• 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:
    Pesticidal Compositions Compounds of the formula I < IMG > ( I) wherein R1 represents C1-C4 alkyl, C1-C4 alkoxy or halogen, R2 represents hydrogen, C1-C3 alkyl, C1-C4 alkoxy or halogen, R3 represents hydrogen, C1-C3 alkyl or halogen, and R4 represents hydrogen or methyl, with the proviso that the total number of carbon atoms contained by the substituents R1, R2, R3 and R4 does not exceed 8, X represents < IMG > and R5 represents hydrogen or methyl and R6 represents C1-C6 alkyl which is unsubstituted or substituted by halogen or represents C2-C4 alkenyl or C3-C6 cycloalkyl or the group -N(R7)R8, in which R7 represents hydrogen or C1-C4 alkyl and R8 represents C1-C6 alkyl which is unsubstituted or substituted by halogen, which are useful in combatting microorganisms in particular phytopathogenic fungi.
    公开号:SU741772A3
    申请号:SU772524451
    申请日:1977-09-16
    公开日:1980-06-15
    发明作者:Хубеле Адольф；Эккхардт Вольфганг；Кунц Вальтер
    申请人:Циба-Гейги Аг (Фирма)；
    IPC主号:
    专利说明:

    (54) FUNGICIDE MEANS
    one
    This invention relates to a chemical plant protection agent, specifically a fungicidal agent based on acetanilide derivatives.
    It is known that N-methoxymethyl-No - (methylsulfonoxy) -2,6-dimethylanilide has a fungicidal effect, but insufficient fungicidal activity 1.
    It is known that N- (1-methoxycarbonylmethyl) -N- (thiomethyl) -2,6-dimethylanilide also exhibits fungicidal properties 2. However, this compound also has a low activity with an insufficient spectrum of action.
    The aim of the invention is to find a new fungicidal agent with enhanced fungicidal activity.
    This goal is achieved using an agent containing acetanilide derivatives of the formula I as an active substance.
    (J-tHz-O Oz-R, M
    about
    where R. is methyl, methoxy, RJ, is methyl, chlorine, RJ is hydrogen, methyl, chlorine, R is hydrogen, methyl,
    Rg is chloropropyl, alkyl,
    allyl, cyclohexyl or CHj
    m (s; nz) 2, NC ;;,
    NHtHj
    dHjeHzdi
    ten
    fHj

    x-eH-ciooCHj,
    IS
    in an amount of 0.1-95 wt.% and an additive selected from the group of carrier, dispersant, emulsifier.
    Compounds of formula I are prepared by the reaction of exchange decomposition of compounds of formula II
    Cs
    X n
    25
    St.-Ohm
     RE About K with a compound of formula III
    HaesOiRg
    The reactions are carried out at temperatures between -40 and + 180 ° C, preferably between -20 and in the presence of inert solvents.
    Example 1 describes a process for the preparation of N- (1-methoxycarbonylethyl) -N- (methylsulphonoxy) acetyl-2,6-dimethylaniline. . „,,.
    Example 1. In a mixture of 26.5 g
    N- (1-methoxycarbonylethyl) -N-hydroxy-acetyl-2, b-dimethylaniline and 8.7 g of pyridine in 150 ml of acetonitrile are introduced dropwise with stirring at 12.6 g of methanesulfonic chloride in 50 m of acetonitrile. After 18 hours stirring at room temperature
    the reaction mixture is poured into 500 ml of water, then extracted three times with 150 MP of methylene chloride, the combined extracts are dried over sodium sulfate, filtered and the solvent is evaporated. The dense precipitate melts after crystallization from ether (from petroleum ether 40–60 ° C) at 58–61 s.
    The remaining compounds of formula I are prepared analogously. They are listed in Table 1. In compounds 1-13)
    Ccussa, connections 14-25
    1P

    Table
    The compounds of formula I are used together with suitable carriers and / or other fillers. Carriers and fillers can be solid or liquid and are commonly used in industry substances, such as natural and regenerated minerals, solvents, dispersants, wetting agents, adhesives, thickeners, adhesives and fertilizers. The manufacture of these substances is carried out in a known manner by thoroughly mixing and grinding the constituents.
    Compounds of the formula I can be used in both solid and liquid forms of manufacture (the preferred percentages of active substance are indicated in weight percent)
    Solid forms
    dusting agent, soil preparation (up to 10%) in the form of various granules and structures, grain (rgCPets) 1-80%.
    Liquid forms of manufacture
    a) water dispersible concentrates of the active substance: wettable powder, pastes (25-90% in commercial packaging, 0.01-15% in ready-to-use solution), emulsions, solution concentrates 10-50%; 0.01-15% in ready-to-use solution);
    b) solutions: aerosols. Example 2. Action against
    Phytophthora infestans on tomatoes.
    a) therapeutic effect. Red Tomatoes
    after three weeks of growth, they are sprayed with a zoospore suspension of the fungus and incubated in a special cabin at a temperature of 18-20 ° C and air saturated with humidity. Moistening is discontinued after 24 hours. After drying, the plants are sprayed with a composition containing the active substance, formed as a wettable powder, with a concentration of 0.06%. After the drug was dried, the plants were again placed in a humidification cabin for 4 days. The number and size of typical follicle spots for such a disease after this time evaluate the effectiveness of the test substances.
    b) Preventive-systemic action.
    Formed as a wetting powder, an active substance with a concentration of 0.006% (by volume of soil) was introduced into the top layer of the soil, where the red gnome varieties were planted three weeks ago. After three days of exposure, the lower side of the foliage of the plants is sprayed with a zoospore suspension.
    Phytophthorainfestans. The plants are then placed on a bb day in a spray booth and kept at a temperature of 18-20 ° C in saturated air. By the number and size of the typical spots formed on
    The equipment was evaluated for the effectiveness of the test substances.
    c) Residual and prophylactic action.
    Tomatoes varieties of red gnome three weeks after planting are sprayed with a composition containing 0.06% of the active substance, made in the form of a wetted powder: ka. After drying, the plants are infected with a zoospore suspension of Phytophthora infestans. After that, they are kept for 6 days in the chamber at 18–20 ° C with high air humidity created by
    0 artificial small-scale spraying. After this time, the spots formed on the foliage will evaluate the efficacy of the test substance by 1 number and size.
    5 Example 4. Action against the fungus Plasmopara viticola on grapes.
    Shasla grapes are grown in the greenhouse. At the stage of appearance of the tenth leaf, three plants are sprayed with a composition containing 0.06% of the active substance formed as a wettable powder. After drying the liquid
    5, the lower part of the foliage of plants is uniformly infected with a spore suspension of a fungus. The plants are then incubated for 8 days in a humidification chamber. After this time on
    The control plants clearly show symptoms of the disease. The efficacy of the test substances was evaluated by the number and size of lesions on the treated plants.
    Example 5. Action against
    5 Pythlum debarianum fungus on sugar beet.
    The fungus is cultivated on sterile oat grains and introduced into the mixture of soil and sand. The ground contaminated in this way is placed in flower pots and sugar beets are sown in it. Immediately after sowing, a water suspension is poured onto the ground, containing a test preparation formed as a wettable powder (20 ppm of active substance to the soil volume).
    Then pods for 2-3 weeks kept in the greenhouse at 20-24 s-.
    0 Lightly spray the soil in an evenly wet state. When evaluating the test, beet growth is determined, as well as the proportion of healthy and diseased plants. Results are shown in Table. 2
    Otsvyhn about - 0% lesion 1 - 5-20% lesion
    Continuation of table 2
    de R methyl, methoxy,
    l methyl, chlorine, hydrogen, methyl ,, chlorine,
    "Hydrogen, methyl,
    Re chloropropyl, alkyl C, -C ,, allnl, cyclohexyl or
    .} Nz
    KS
    (iHjdHttfi
    at. an amount of 0.1-95 wt.% and an additive selected from the group of carrier, dispersant, emulsifier.
    Priority on the grounds of 17.09.76 with R is methyl, methoxy, R is methyl, chlorine, RJ is hydrogen, methyl, chlorine,
    sn.
    X - CH - COOCH,
    04.08.77 with R - NHCH ,, N {CH,), U1CH3O;
    , Sources of information taken into account in the examination
    1. The patent of Germany 2349256, cl. C 07 C 143/68, off .
    2. For the 2124200,
    cl. And 01 N 9/20, 1975, according to which the decision to grant a patent (prototype).
    权利要求:
    Claims (2)
    [1]
    Claim
    A fungicidal agent containing acetanilide derivatives as an active substance and an additive selected from the group of carrier, dispersant, emulsifier, characterized in that, in order to enhance fungicidal activity, it contains compounds of the general formula l <K / where methyl methoxy
    R 4 is methyl, chlorine, R, is hydrogen, methyl ,, chlorine,
    R ^ - is hydrogen, methyl, R s - chloropropyl, alkyl C, -C ,, allyl, cyclohexyl or 3 nnsn ^ H ,, M (B, ·), '' (Η , βΗ, βι , v% of Λ CM-C00CH 3 , J-0, in an amount of 0.1-95 wt.% And an additive selected from the group of carrier, dispersant, emulsifier.
    Featured Priority
    09/17/76 at R ^ - methyl, methoxy, R t - methyl, chlorine, R - hydrogen, methyl, chlorine,
    hydrogen, methyl, chloropropyl, alkyl C 4 -C t , allyl, cyclohexyl, 5 sn1X - sn - coaxial
    08/04/07 at R 5 - NHCHj,,. 'sn 4 ss g s “, Sources of information taken into account during the examination
    1. The patent of Germany No. 2349256, ° C. C 07 C 143/68, off 19 ^ 5.
    [2]
    2. Application No. 2124200, cl. A 01 N 9/20, 1975, according to which a decision was made to grant a patent (prototype).
    Editor L. Emelyanova Compiled by N. ArmeevaTechred I. Birchak Corrector, V. Butyaga Order 3222/56 Circulation 723 Subscription
    TsNIIIPI of the USSR State Committee for Inventions and Discoveries 113035, Moscow, Zh-35, Raushskaya nab., 4/5
    PPP Branch * ’Patent’ *, Uzhhorod, st. Project, 4
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    引用文献:
    公开号 | 申请日 | 公开日 | 申请人 | 专利标题
    US3536721A|1963-09-13|1970-10-27|Stauffer Chemical Co|Substituted-sulfonyl glycolamide compositions|
    CA975775A|1969-03-12|1975-10-07|Eugene G. Teach|Bromoacetanilides and their utility as biocides|
    US3960919A|1972-11-29|1976-06-01|Badische Anilin- & Soda-Fabrik Aktiengesellschaft|Substituted sulfonylglycolic acid anilides|
    US3954827A|1972-01-13|1976-05-04|Basf Aktiengesellschaft|Substituted o-[aminosulfonyl]-glycolic anilides|
    DE2310757A1|1973-03-03|1974-09-12|Basf Ag|SUBSTITUTED O- GLYCOLIC ANILIDES|
    FR2265726B1|1974-04-01|1978-03-17|Ciba Geigy Ag|
    DE2458972A1|1974-12-13|1976-06-16|Basf Ag|SUBSTITUTED O-ALKYL SULFONYL GLYCOLIC ANILIDES|
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    JPS5297919A|1976-02-13|1977-08-17|Basf Ag|Substituted ooalkylsulfonylglycolic acid anilide|DE2845454A1|1977-11-01|1979-05-10|Chevron Res|3-- GAMMA -BUTYROLACTONE AND - GAMMA -BUTYROTHIOLACTONE AND FUNGICIDE AGENTS|
    CH636093A5|1978-01-28|1983-05-13|Ciba Geigy Ag|MICROBICIDAL AGENTS.|
    CH635580A5|1978-01-28|1983-04-15|Ciba Geigy Ag|MICROBICIDAL AGENTS.|
    CH637368A5|1978-10-27|1983-07-29|Ciba Geigy Ag|ANILINE DERIVATIVES AND Pesticides Manufactured From Them.|
    CH641760A5|1978-11-27|1984-03-15|Ciba Geigy Ag|PEST CONTROL.|
    CH639940A5|1978-12-05|1983-12-15|Ciba Geigy Ag|Substituted N-alkoxycarbonylethyl-N-acylanilines, microbicides containing them, and process for the preparation of the compounds|
    FR2451914B1|1979-03-20|1983-08-26|Ciba Geigy Ag|
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    MA18800A1|1979-04-10|1980-12-31|Ciba Geigy Ag|ACYLATED NAPHTYLAMINES, PROCESS FOR THEIR PREPARATION AND THEIR APPLICATION AS PHYTOFUNGICIDES|
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    US4377587A|1980-07-25|1983-03-22|Ciba-Geigy Corporation|Arylamine derivatives and use thereof as microbicides|
    MA19215A1|1980-07-25|1982-04-01|Ciba Geigy Ag|NOVEL ARYLAMINE DERIVATIVES, PROCESS FOR THEIR MANUFACTURE AND USE AS MICROBICIDES.|
    US4599351A|1981-08-14|1986-07-08|Chevron Research Company|Fungicidal 3- lactones|
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