• 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:
    Use: in agriculture, as a chemical agent for weed control. The essence of the invention: the destruction of weed plants using a herbicidal agent containing targeted additives and the active substance is a derivative of cyclohexenone of the general formula C (R2) CH2C (OH) (RihN-0-A-XC6H4 C (. Where RI is methyl, ethyl, propyl; R2 is ethylthiopropyl, 2-ethyltmo-2-methylpropyl, tetrahydrothiopyran-3-yl, tetrahydropyran-3-yl, tetrahydropmran-4-yl, 3,4-dibromotetrahydro-pyran-3-yl, 4- pyridyl, 3-pyridyl, thyl-cyclohex-3-enyl, 3,4-dioxycycpohexyl, 2,6,6, -trimethylcyclohex-1-enyl, X - hydrogen, 3-chloro, 4-chloro, 4-fluoro , 4-methyl, 4-trifluoromethyl; A - bu. Ylen, but-4-enylene, b t-3-enylene; in an amount of 10 wt% Table 4
    公开号:SU1757439A3
    申请号:SU4742334
    申请日:1989-11-10
    公开日:1992-08-23
    发明作者:Каст Юрген；Коласса Дитер；Майер Норберт；Ширмер Ульрих；Харреус Альбрехт；Вильд Иохен；Вестфален Карл-Отто；Вюрцер Бруно
    申请人:Басф Аг (Фирма)；
    IPC主号:
    专利说明:

    This invention relates to the field of chemical control of weeds, in particular to a herbicidal agent.
    A herbicidal agent containing an active substance based on a cyclohexenone derivative and at least one additive from the group of solid or liquid carriers is known.
    A disadvantage of the known herbicidal agent is that its activity is insufficient.
    The aim of the invention is to increase the activity of the herbicidal agent based on the cyclohexenone derivative.
    The goal is achieved with a temperate herbicidal agent containing the active substance, a derivative of cyclohexenone. carrier and surfactant, contains as manufactured by n9:
    th cyclohexenone compound of the general formula
    OH ..--.l.x
    H

    .NOA- I,
    V
    H

    where RI is methyl, ethyl, propyl;
    R2 is 2-ethylthiopropyl, 2-othylthio-2-methylpropyl, tetrahydrothiopyran-3-yl, tetrahydropyran-3-yl, tetrahydropyran-4-yl, 3,4-dibromotetrahydropyran-3-yl. 4-pyridyl, 3-pyridyl, 4-methylcyclohex-3-enyl, 3,4-dioxycyclohexyl, 2,6,6-trimethyl-cyclohex-1-enyl,
    X is hydrogen, 3-chloro, 4-chloro, 4-fluoro, 4-methyl, 4-trifluoromethyl;
    A - butylene, but-2-enylene, but-3-enylene,

    as the carrier is xylene, as a surfactant is simple nonylphenol polyethylene glycol ether with the following content of ingredients, wt.%:
    Active substance10
    Carrier83,7
    Surfactant 6.3 This remedy is obtained by simple mechanical mixing of the respective ingredients.
    Example 1. Preparation of (4-phenylbut-2-enyloximino) propyl-5- (tetragm-rothiopyranyl) cyclohex-2-en-1-one.
    A. To a solution of 93.1 g (1 mol) of aniline in 340 ml of water and 225 ml of concentrated hydrochloric acid at a temperature of 0 ° C, 69.1 g (1 mol) of sodium nitrite in 100 ml of water are added.
    B. In 840 ml of acetone and 50 ml of water, 67.6 g (1.25 mol) of butadiene are added at -15 ° C, 15.5 g of copper (II) chloride and 22.5 g of calcium oxide are added, then the diazonium salt solution obtained in stage A is added over 2 hours. The resulting reaction mixture is heated to 25 ° C, stirred for 6 hours, then extracted with methyl tert-butyl ether, the organic extract is concentrated and distilled off using a thin-film evaporator at 0 , 2 torr and 80 ° C. The result is a mixture of 1-chloro-4-phenyl-2-ene and 3-chloro-4-phenyl-1-ene in a ratio of 78; 22; yield 55%.
    B. To 480 ml of dry M-methylpyrrolidone, 78.3 g (0.48) of N-hydroxyphthalimide and 44.2 g (0.32 mol) of potassium carbonate are sequentially added. At a temperature of 40 ° C, 88.8 g ( 0.54 mol) of the mixture of chlorides obtained in stage B is heated to 60 ° C and continued to stir for another 6 hours. After cooling, the mixture is poured onto 2 liters of ice water and filtered. Washed and dried, 90% are obtained. From theory (E) -N (4-phenyl-2-butenyloxy) -phthalimide. Mp 70-71 ° C (from isopropanol).
    G, To 55.5 g (0.19 mol) of the phthalimide ester obtained in Step B in 190 ml of ethyl acetate are added with stirring, and at a temperature of 60 ° C 11.6 g (0.19 mol) of ethanolamine are added. After 5 hours, the precipitated M- (hydroxyethyl) -phthalimide is filtered and 18.8 g of oxalic acid in 30 ml of ethyl acetate are added to the filtrate. As a result, 95% of the theory of (E) -4-phenyl-2-butenyloxy-amine is obtained in the form of an oxalic acid salt. M.p. 127-129 ° C.
    D, 4.3 g (0.016 mol) of 2-propionyl-5- {3-tetrahydrothiopyranyl byblogexan-T.Z-dione,
    0
    five
    0
    five
    0
    five
    0
    4.5 g (0.018 mol) of 4-phenyl-but-2-enyloxyammonium oxalate and 3.0 g of sodium bicarbonate are stirred at 100 ° C. for 16 hours in 100 ml of methanol. The solvent is distilled off under reduced pressure, the residue is subjected to chromatography on silica gel using a mixture of toluene and ethyl acetate in a volume ratio of 8: 2 as eluant.
    After removal of the solvent, 2.2 g (34.4% of theory) of (4-phenyl-but-2-enyloximino) -propyl-5- (tetrahydrothiopiranil) cyclohex-2-en-1-one are obtained in the form of a resin, listed in Table 2 as compound 2.1.
    Similarly, the remaining compounds are given in Tables 1 and 2.
    Example 2. The experiments were carried out in a greenhouse. Plastic pots filled with clay sand containing about 3.0% humus as a substrate are used as vessels for growing plants. Seeds of experimental plants are sown separately by species. After reaching a height of 3-15 cm, the experimental plants are treated with a herbicidal agent diluted with water. The consumption of the agent is 0.06, 0.125, 0.25 and 0.5 kg / ha of the active substance, respectively.
    The plants used in the experiments and the results of the experiments carried out in the greenhouse are listed in Tables 3 and 4.
    权利要求:
    Claims (1)
    [1]
    Invention Formula
    The herbicidal agent containing the active substance is cyclohexenone aqueous production, a carrier and a surfactant, characterized in that, in order to increase the herbicidal activity, it contains as an active substance a cyclohexenone derivative of the general formula
    lm about ACHOUh
    R,
    five
    WITH
    about
    one
    five
    0
    where RI is methyl, ethyl, propyl;
    Ra - 2-ethylthiopropyl, 2-ethylthio-2-methylpropyl, tetrahydrothiopyran-3-yl, tetrahydropyran-3-yl, tetrahydropyran-4-yl, 3,4-dibromotetrahydropyran-3-yl, 4-pyri- dil, 3-pyridyl, 4-methylcyclohex-3-enyl, 3,4-dioxycyclohexyl, 2,6,6-trimethyl-cyclohex-1-enyl;
    X is hydrogen, 3-chloro, 4-chloro, 4-fluoro, 4-methyl, 4-trifluoromethyl;
    A - butylene, but-2-enylene, but-3-enylene, xylene as a carrier, nonionylphenol polyethylene g or icyl ether as a surfactant with the following content of ingredients, May.%:
    Active substance10
    Carrier 83.7
    PU supernatural active substance € .3
    f h & l and n a f
    Continuation of table 2
    2- (1-A piloximyio-n-propyl) -5- (; 1-amiophenip) -3-O1ssicicyclohex - -2-en-1-one.
    Table
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    引用文献:
    公开号 | 申请日 | 公开日 | 申请人 | 专利标题
    US3950420A|1973-08-15|1976-04-13|Nippon Soda Company, Ltd.|Cyclohexane derivatives|
    BE897413A|1982-08-09|1983-11-14|Chevron Res|2- [1- -ALKYLIDENE] -5- -CYCLOHEXANE-1,3-DIONES SUBSTITUTED HERBICIDES|
    GB2137200A|1983-03-30|1984-10-03|Ici Australia Ltd|Herbicidal Cyclohexane-1,3-dione Derivatives|
    DE3324707A1|1983-07-08|1985-01-17|Basf Ag, 6700 Ludwigshafen|CYCLOHEXAN-1,3-DIONE DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE FOR COMBATING UNWANTED PLANT GROWTH|
    AU566671B2|1983-07-18|1987-10-29|Ici Australia Limited|Cyclohexene-1,3-dione derivatives|
    AT52769T|1986-04-24|1990-06-15|Ciba Geigy Ag|ACYL-CYCLOHEXANDIONE AND THEIR OXIMAETHER WITH HERBICIDAL AND REGULATING EQUIPMENT REGULATING EFFECT.|
    DE3838309A1|1988-11-11|1990-05-31|Basf Ag|CYCLOHEXENONE OXIMETHER, METHOD FOR THE PRODUCTION THEREOF, AND ITS USE AS HERBICIDE|DE3838309A1|1988-11-11|1990-05-31|Basf Ag|CYCLOHEXENONE OXIMETHER, METHOD FOR THE PRODUCTION THEREOF, AND ITS USE AS HERBICIDE|
    DE4014983A1|1990-05-09|1991-11-14|Basf Ag|CYCLOHEXENONOXIMETHER, METHOD AND INTERMEDIATE PRODUCTS FOR THEIR PREPARATION AND THEIR USE AS HERBICIDES|
    DE4014985A1|1990-05-09|1991-11-14|Basf Ag|HERBICIDES THAT CONTAIN CYCLOHEXENONE DERIVATIVES AS HERBICIDAL ACTIVE SUBSTANCES AND NAPHTHALINE DERIVATIVES AS ANTIDOTS|
    DE4014988A1|1990-05-09|1991-11-14|Basf Ag|CYCLOHEXENONE OXIMETHER, METHOD FOR THE PRODUCTION THEREOF, AND ITS USE AS HERBICIDE|
    DE59102689D1|1990-05-09|1994-10-06|Basf Ag|Cyclohexenone oxime ether, process for their preparation and their use as herbicides.|
    DE4014987A1|1990-05-09|1991-11-14|Basf Ag|CYCLOHEXENONOXIMETHER, METHOD AND INTERMEDIATE PRODUCTS FOR THEIR PREPARATION AND THEIR USE AS HERBICIDES|
    US5364833A|1990-05-09|1994-11-15|Basf Aktiengesellschaft|Cyclohexenone oxime ethers, their preparation and their use as herbicides|
    DE4014984A1|1990-05-09|1991-11-14|Basf Ag|CYCLOHEXENONOXIMETHER, METHOD AND INTERMEDIATE PRODUCTS FOR THEIR PREPARATION AND THEIR USE AS HERBICIDES|
    EP0481354B1|1990-10-19|1994-08-03|BASF Aktiengesellschaft|Unsaturated cyclohexenonoximethers|
    US5604183A|1991-08-09|1997-02-18|Basf Aktiengesellschaft|Cyclohexenone oxime ethers|
    DE4126479A1|1991-08-09|1993-02-11|Basf Ag|CYCLOHEXENONE OXIME ETHERS|
    DE4135265A1|1991-10-25|1993-04-29|Basf Ag|cyclohexenone|
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    DE4204204A1|1992-02-13|1993-08-19|Basf Ag|MIXTURES OF OPTICALLY ACTIVE CYCLOHEXENONE OXIMETHERS, PROCESSES AND INTERMEDIATE PRODUCTS FOR THEIR PREPARATION AND THEIR USE AS HERBICIDES|
    DE4227896A1|1992-08-22|1994-02-24|Basf Ag|Cyclohexenone oxime ethers, their preparation and their use|
    DE19510183A1|1994-03-31|1995-10-05|Basf Ag|New imino:alkyl-aminomethyl-cyclohexenone derivs.|
    DE4415871A1|1994-05-05|1995-11-09|Basf Ag|O-ethyl-cyclohexenone oxime ether and their use as herbicides|
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    UA60295C2|1995-09-20|2003-10-15|Басф Акцієнгезельшафт|Herbicidal mixture containing cyclohexenonoxymic ether, a herbicidal preparation, a method of obtaining thereof and a method of controlling the undesirable vegetation|
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    法律状态:
    2005-05-10| REG| Reference to a code of a succession state|Ref country code: RU Ref legal event code: MM4A Effective date: 20031111 |
    优先权:
    申请号 | 申请日 | 专利标题
    DE3838309A|DE3838309A1|1988-11-11|1988-11-11|CYCLOHEXENONE OXIMETHER, METHOD FOR THE PRODUCTION THEREOF, AND ITS USE AS HERBICIDE|
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