• 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:
    A tetrahydro-1,3,5-thiadiazin-4-one represented by the general formula, <IMAGE> (I) wherein R1, R2 and R3, which may be the same or different, represent each an alkyl group, allyl group, cycloalkyl group, alkoxyalkyl group, benzyl group, phenyl group or substituted phenyl group having as substituents alkyl groups, nitro group, halogen atoms, alkoxy groups, or trifluoromethyl group and R2 and R3 may also represent hydrogen atoms, is a new compound and useful for controlling insects and mites.
    公开号:SU1454235A3
    申请号:SU782625202
    申请日:1978-06-07
    公开日:1989-01-23
    发明作者:Икеда Кенити；Канно Хидео；Ясуи Митихиро；Харада Тацуо
    申请人:Нихон Нохияку Ко, Лтд (Фирма)；
    IPC主号:
    专利说明:

    The invention relates to chemical plant protection products, namely, an insecticidal composition in the form of variants based on a tetrahydrodiazinone derivative,
    The purpose of the invention is to increase insecticidal activity.
    Examples of obtaining active substance
    EXAMPLE 1 2-Ethylimino-3-phen-NSh1-5- (0-chlorophene br) tetrahydro-1,3,5-thiadiazin-4-it (compound 1)
    In 50 ml of benzene, 2.4 g (0.01 mol) of N-chloromethyl-N- (0-chlorophenyl) carbamoyl chloride and g (0.01 mol of 1-EtH1 3-phenylthiourea) are dissolved. After adding 8 ml of 10% - sodium hydroxide solution, the mixture is reacted with heating from 40 to 50 ° C and under stirring for 4 hours. After the completion of the reaction, the benzene layer is washed with water, dried and concentrated to obtain a viscous oily substance which is recrystallized from isopropyl alcohol - n-hexane (1; 1). Obtain 0.8 g (14%) of white crystals, melting at 77-79 C.
    EXAMPLE 2. 2 Tert-butsh1mino-3-isopropyl-5- (p-tolyl) -tetrahydro-1J3,5-thiadiazin-4-one (compound 2). 1.0 g (0.0028 mol) of 1,3,5-tris-1p-tolyl) hexahydro-sim-triazine is suspended in 10 ml of tetrahydrofuran. The resulting suspension is added dropwise with stirring to 5 ml of ice-cold benzene, which contains 0.9 h (0.0042 mol) of trichloromethyl chloroformate. After completion of the dropwise addition, the mixture is stirred for t hours at room temperature. About 20 ml of benzene containing 1.4 g (0.0083 mol) of 1-isopropyl-3-tert-butyl thiourea are added to the mixture. After adding 7 ml of a 1b% solution of sodium hydroxide, the mixture was stirred for 4-6 hours at 40-50 seconds. The reaction mixture is washed with water, dried and benzene is distilled off by distillation. The crude product thus obtained is recrystallized from isopropyl alcohol to give 1.2 g (yield 45%) of white crystals, melting at 118-120 C 5 Br (CBC1) 6: 4.75 (S, 2 H); 4.70 (ha, 1H); 2.35 (s, 3H); 1.47 (d, 6H); 1.33 (s, 9H).

    Q d
    0
    The compounds obtained are listed in Table. one.
    Examples of the preparation of compositions. Examples Zi4. A wettable powder is obtained by thoroughly mixing the following ingredients, may including: Example 3 4
    Compound 2 45 70 A mixture of powdered clay and highly dispersed silicic acid 55 25
    (54: 1) (22.9:
    : 2.1)
    A mixture of nonylphenyl ether polypolyoxyethylene and calcium alkanolbenzenesulfonate 10 10 Examples 5-7 An emulsifiable concentrate is obtained by homogeneous mixing of the following ingredients, wt.h.
    Example5 67
    Connection 1 1 25 50
    Xylene 96 70 42
    Nonylphenyl Simple Mixture
    polyoxyethylene ether and alkyl benzene sulfonate
    calcium 3 58
    (2.4: (4: (6.4:: 0.6): 1): 1.6)
    PRI me R 8. The granulated composition is obtained by homogeneous mixing of the following ingredients, wt.h .: Compound 33
    A mixture of powdered bentonite tO clay82
    Calcium ligninsulfonate 3 Polyvinyl alcohol 2 The resulting composition is thoroughly mixed with the right amount of water, granulated and dried.
    Examples 9-11. Wettable powder is obtained by homogeneous mixing of the following ingredients, wt.h .:

    Example 9 Compound 3 20 A mixture of powdered
    ten
    45
    11 70
    clay and synthetic highly dispersed silicic acid
    A mixture of nonylphenyl polyoxyethylene ether and calcium alkyl benzene sulfonate
    75
    (74.4:
    : 0.6)
    55
    (54:
    :one)
    25
    (22.9:
    : 2.1)
    ten
    ten
    (8: 2) (8: 2)
    10 (8: 2)
    Examples 12-14. Emulsified concentrate is obtained by homogeneous mixing of the following ingredients, and ach:
    Example
    Connection 3
    Xylene
    Nonylphenyl Blend
    simple
    polyoxyethylene ester
    and calcium alkyl benzene sulphonate
    12
    one
    96
    13 25 70
    14 50 42
    five
    (four:
    :one)
    3
    (
    : 0,6)
    Examples 15-17 The composition is obtained by homogeneous mixing of the following ingredients, ma.h
    Dustovoy
    eight
    (6.4:: 1.6)
    Example Compound 4 Powder Clay Powdered Kieselguhr Examples
    15 1
    84 15
    16 5
    80 15
    17 10
    75 15
    18-20. Dustovs
    the compositions are prepared by mixing the following ingredients, wt. example: Example 18 19 20 Compound 3 1 5 10 Powdered clay 84 80 75 Powdered kieselguhr 15 15 15 Example 21. Wettable powder is prepared by homogeneous mixing of the following ingredients, wt..h .: Compound 2 20 A mixture of powdered clay and synthetic highly dispersed silicic acid
    75 (74.4:: 0.6)
    9:
    10 (8: 2)
    ten
    )

    15
    20
    Nonylphenyl ether mixture
    polyoxyethylene and
    calcium alkylbenzenesulfonate
    PRI me R 22 (test). . Rice plants are grown in water in pots (18 h 18 cm), which corresponds to 1/4000 ares. When the plants reach the stage of 7-8 leaves, the water depth in the pods is set to 5 cm and the compounds are added to it, respectively. according to examples 3-21, each in an amount of 20 g / 10 are. After that, eight appropriate insect pests are introduced into the pots. After 5 days, the test is performed and mortality is calculated.
    The results are presented in table 2.
    权利要求:
    Claims (3)
    [1]
    25 claims
    : 6)
    1. An insecticide composition in the form of a wettable powder, comprising an active substance derived from tetrahydrodiazinone, a surface active agent and carrier, characterized in that, in order to increase the insecticidal activity, it contains a compound of the general formula
    ABOUT
    thirty
    35
    Rj-n
    40
    .N-Rj S N-R3
    L J.
    45
    in which R, is phenyl, 4-methylphenyl; isopropyl; tert-butyl, as a surface-active agent, a mixture of nonylphenyl ether of polyoxyethylene and alkanolbenzenesulfonate calcium at a mass ratio of 8: 2, as a carrier — a mixture of powdered clay and highly dispersed silicic acid at a mass ratio of 74.4: 0, 6, 54: 1 and 22.9: 2.1 with the following content, ma.ch .:
    Active substance 20-70 Surface-active agent10 Carrier 25-65
    2. The insecticidal composition in the form of an emulsifiable concentrate / comprising the active substance - a derivative of tetrahydrodiazinone, the thinner Ht is a surface-active agent, and in order to increase the insecticidal activity tlH, it is derived tetrahydrodiazinone contains: pc compound of general formula
    [2]
    ABOUT
    } |
     :
    five
    1-10 75-84 15
    gur with the following compotent content, wt.%:
    Active substance
    Powdered /
    clay
    Powdery
    diatomaceous earth
    4. The insecticidal composition in the form of granules, comprising the active substance - a tetrahydrodiazinone derivative, a carrier and a surface-active agent, characterized in that, in order to increase the insecticidal activity, it contains a compound of the general formula as tetrahydrodiazinone derivative
     R is phenyl, 3-chlorophenyl; Rj is isopropyl, phenyl; RJ - ethyl, tert-butyl. As a diluent - xylene, as a surface-active agent fa - a mixture of nonylphenyl polyoxyethylene fiber and alkylbenzene-calcium sulfate apc; mass ratio (2.4-6.4) :( O, 6-1.6) with the following content of components, mAh. Active substance 1-50 Thinner42-96
    Surface active agent3-8
    [3]
    3. Insecticidal composition in the fordust, including the active substance derived from tetrahydrodiazinone and carrier, characterized by teM, which, in order to increase the insecticidal activity, it contains a compound of the general formula as an active derivative of tetrahydrodiazinone
    ABOUT
    R -N -K-R / S N - R3
    Where R is tert-butyl, phenyl;
    R. - n-butyl, isopropyl;
    R - n-butyl, t-butyl, as a carrier - powdered clay and powdered kizel-
    ABOUT
    RI-N-N-R
    where R is phenyl;
    R is isopropyl; R is tert-butyl,
    as a carrier - a mixture of bentonite and clay at a mass ratio of 10:82, as a surface-active agent - a mixture of calcium ligninsulfonate and polyvinyl alcohol at a mass ratio of 3: 2 with the following content of components, wt.: Active substance 3 Carrier92
    Surface active agent5
    Priority signs: 09.06.77 with R - phenyl; Rj is isopropyl, n-butylphenyl; Rg is ethyl, n-butyl, t-butyl;
    06.29.77 when R is t-butyl;
    02.28.78 when R is 4-methylphenyl, 2-chlorophenyl.
    Table (
    - 2-Methyl-4- (3,4-dichlorophenyl) perhydro-1,2, A-oxadnazin-3-one, which was. introduced in the formulation similar to examples 8-17. Formulations are tested by applying each: of them at a concentration of 20 g / 10 are.
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    同族专利:
    公开号 | 公开日
    US4159328A|1979-06-26|
    PH18213A|1985-04-30|
    引用文献:
    公开号 | 申请日 | 公开日 | 申请人 | 专利标题
    DE1912225U|1964-12-21|1965-03-18|Bader Soehne G M B H D|EXTENSION FRAME.|
    US3741964A|1971-06-01|1973-06-26|Monsanto Co|Method for producing amino-3,4-dihydro-2h-1,3,5-thiadiazin-2-ones|US4452795A|1981-09-03|1984-06-05|Ciba-Geigy Corporation|5-Phenoxyphenyl-tetrahydro-1,3,5-thiadiazin-4-ones|
    US4443445A|1981-09-10|1984-04-17|Ciba-Geigy Corporation|Imidazo- and pyrimido-1,3,5-thiadiazin-4-ones|
    US5021412A|1987-09-25|1991-06-04|Mitsui Toatsu Chemicals, Inc.|Thiadiazines, and insecticidal and acaricidal preparations|
    JPH0541632B2|1990-11-15|1993-06-24|Kogyo Gijutsuin|
    DE19953775A1|1999-11-09|2001-05-10|Bayer Ag|Active ingredient combinations with insecticidal and acaricidal properties|
    DE102006031976A1|2006-07-11|2008-01-17|Bayer Cropscience Ag|Drug combinations with insecticidal and acaricidal properties|
    EP2039248A1|2007-09-21|2009-03-25|Bayer CropScience AG|Active agent combinations with insecticide and acaricide properties|
    DE102007045922A1|2007-09-26|2009-04-02|Bayer Cropscience Ag|Drug combinations with insecticidal and acaricidal properties|
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    法律状态:
    优先权:
    申请号 | 申请日 | 专利标题
    JP6813877A|JPS5539547B2|1977-06-09|1977-06-09|
    JP7759477A|JPS6121954B2|1977-06-29|1977-06-29|
    JP2255078A|JPS5539550B2|1978-02-28|1978-02-28|
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