• 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:
    Disclosed are compounds such as 3-[5-(1,1-dimethylethyl)-3-isoxazolyl]-1-methyl-4-hydroxy-2-imidazolid inone; their control of weeds such as johnsongrass; the process of making them; and intermediates for making them, the compounds being represented by a Formula I: <IMAGE> (I) wherein A is <IMAGE> where R is an alkyl of up to six carbon atoms; an alkenyl of up to five carbon atoms; an alkynyl of up to five carbon atoms; a cycloalkyl selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl; a haloalkyl of up to six carbon atoms; -R4-O-R5, or -R4-S-R5, where R4 is an alkylene of up to six carbon atoms and R5 is an alkyl of up to six carbon atoms; <IMAGE> where Z is nitro (NO2), chloro (Cl), bromo (Br), fluoro (F), or R5, and n is 0, 1, 2, or 3; R1 is an alkyl of up to three carbon atoms, or allyl; R2 is hydroxy (OH), chloro (Cl) or bromo (Br); and R3 is hydrogen (H), an alkyl of up to four carbon atoms, allyl, or hydroxy (OH).
    公开号:SU1306465A3
    申请号:SU813248101
    申请日:1981-02-16
    公开日:1987-04-23
    发明作者:Майкл Лаваниш Джером
    申请人:Ппг Индастриз Инк (Фирма)；
    IPC主号:
    专利说明:

    The invention relates to agriculture and the mole (it can be used in the control of weeds when cultivating useful plants.
    The purpose of the invention is to increase the efficiency of the method of weed control using the imidazolidinone-3-5- (1,1-dimethyl-N) -3-isoxazolyl -1-methyl-4-hydroxy-2-imidazolide derivative as a herbicide. - nona
    Example 1, Synthesis of (1, - -dimethylethyl) -3-isoxazlyl-1-methyl-4-hydroxy-2-imidazolidinone.
    fO
    holding (1,1-dimethylether1) -3- -isoxazolyl -1 -methyl-1- (2, 2-dimethoxyethyl) urea. The oil crystallizes on cooling; crystals; p; recrystallized from a solution of ethyl ether / hexane during cooling. The crystals are excipient by suction filtration and air dried, resulting in the formation of 5.2 g of white crystals (1,1-dimethylethyl) -3-isoxazolyl -1-methyl-1- (2,2-dimethoxistil) urea, m.p. 80-, JK-spectrum (paste) bands in 3260, 1670, 1600 and 1530 cm, ion
    A. Formation of 5 - (, 1-dimethylethyl) MS in m / e 285. -isoxazol-3-yl isocyanate. (NMR spectrum (CDClj), (Singh 3-necked flask equipped with a magnetic stirrer, thermometer and cooler with a dry ice (draining
    20
    years, 1H); 6.61 (singlet, W); 4.52 (triplet, 1H); 3.42 (singlet, 8H); 3.50 (doublet, 8H); 3.13. (Singlet.
    thirty
    tube with a capacity of 300 ml), pour 100 ml of a solution of ethyl acetate containing 4.8 g (0.034 mol) and 3-ag-n-5- (1,1-dimethylethyl) isoxazole. Through a solution of sparging from dehydrated hydrogen chloride (10 g) and then 20 g of phosgene is bubbled through the solution, while this solution is cooled in an ice bath. The solution is kept at ambient temperature for 17 hours, and then the flask is rinsed with argon. until the SOCE is completely removed, the solution is filtered under a nitrogen atmosphere, and then the precipitate is washed with benzene, resulting in a precipitate containing approximately 0.034 mol (3.6 g) of 5- (1,1- -dimethylethyl) isoxazol-3-yl isocyanate.
    E ;. The formation of (1, 1-dimethyl- ethyl) -3-isoxazolyl -1-methyl-1 - (2,2-, -dimethoxyethyl) urea.
    At an ambient temperature of 4.2 g (0.035 mol), methylaminoacetaldehyde dimethyl acetate I in 15 ml of benzene is fast 45 - (multiplet); 4.92
    ZN); 1.30 (singlet, 9H).
    C. Synthesis of (1,1-dimethylethyl) -3-isoxazolyl -1-methyl-4-hydroxy-2-imidazolidinone.
    In a round bottom flask, 2.6 g (1,1-dimethylethyl) -3-iso-xazolyl-α-metst- (2,2-dimethoxy-ethyl) urea, 150 ml of water and 1.5 ml of concentrated hydrochloric acid are loaded. (HC1). The resulting mixture is heated to form a single phase, crystals form on the walls of the flask, an O5 mixture is drawn, the crystals are scraped off, and the solution is filtered. The crystalline precipitate is washed. 35 in two separate portions of water, and then air dried, resulting in 1.9 g of white crystals of 3- (5- (151-dimethylethyl) -3-isoxa). 3olyl -1-methyl-4-hydroxy-2-imidazolidinone. TP ≈ 173-177 s, IR spectrum (paste) of the band at 3400, 3140, 1700 and 1590 cm-.
    40
    NM
    -spectrum (CDC1), /: 6.64 (sing-.
    (broad singlet, 1H); 3.83-3.17 (multiplet ,, 2H); 2.89 (singlet, ZN); 1.30 (singlet, 9H).
    The ro is added to 50 ml of benzene solution containing 0.034 mol (5.6 g) of 5- (1,1-dimethylethyl) isoxazo-LIL-3-IL isocyanate precipitate. The resulting slurry is heated to reflux temperature, which is held for 2 minutes, filtered, cooled and 20 ml of hexane is added, but no crystals are formed during holding and cooling in the refrigerator. The slurry is then subjected to distillation to obtain light fractions using vacuum at 70 ° C, resulting in the formation of 5.7 g of a viscous oil, with
    holding (1,1-dimethylether1) -3- -isoxazolyl -1 -methyl-1- (2, 2-dimethoxyethyl) urea. The oil crystallizes on cooling; crystals; p; recrystallized from a solution of ethyl ether / hexane during cooling. The crystals are excipient by suction filtration and air dried, resulting in the formation of 5.2 g of white crystals (1,1-dimethylethyl) -3-isoxazolyl -1-methyl-1- (2,2-dimethoxistil) urea, m.p. 80-, JK-spectrum (paste) bands in 3260, 1670, 1600 and 1530 cm, ion
    MS in m / e 285. NMR spectrum (CDCl1), (sing5 MS in m / e 285. NMR spectrum (CDCli), (sing0
    years, 1H); 6.61 (singlet, W); 4.52 (triplet, 1H); 3.42 (singlet, 8H); 3.50 (doublet, 8H); 3.13. (Singlet.
    0
    ZN); 1.30 (singlet, 9H).
    C. Synthesis of (1,1-dimethylethyl) -3-isoxazolyl -1-methyl-4-hydroxy-2-imidazolidinone.
    In a round bottom flask, 2.6 g (1,1-dimethylethyl) -3-iso-xazolyl-α-metst- (2,2-dimethoxy-ethyl) urea, 150 ml of water and 1.5 ml of concentrated hydrochloric acid are loaded. (HC1). The resulting mixture is heated to form a single phase, crystals form on the walls of the flask, an O5 mixture is drawn, the crystals are scraped off, and the solution is filtered. The crystalline precipitate is washed. 5 in two separate portions of water, and then air dried, resulting in 1.9 g of white crystals of 3- (151-dimethylethyl) -3-isox-. 3olyl -1-methyl-4-hydroxy-2-imidazolidinone. TP ≈ 173-177 s, IR spectrum (paste) of the band at 3400, 3140, 1700 and 1590 cm-.
    0
       - (multiplet); 4.92
    NM
    -spectrum (CDC1), /: 6.64 (sing-.
       - (multiplet); 4.92
    (broad singlet, 1H); 3.83-3.17 (multiplet ,, 2H); 2.89 (singlet, ZN); 1.30 (singlet, 9H).
    Data on the herbicidal activity of the compound but Example 1 are presented in Table. 1 (post-emergence application) and 2 (pre-emergence application).
    The herbicidal activity of this compound in relation to various types of weed plants is evaluated visually, periodically after application, the determination of the numerical degree of pores, all over, is carried out. The magnitude of the numerical extent of the lesion is measured on a scale of 0-10, where O is no lesion, and 10 is total lesion.
    This parameter is a quantitative measure, expressed as a percentage for damage to various types of weeds.
    In the event that the magnitude of the numerical extent of the lesion exceeds 0, one or more characteristics of the degree of physiological effect are determined by visual assessment.
    The degree of physiological effect is a qualitative characteristic and determines the nature of the lesion, i.e. necrosis, slower growth, reduced germination, etc.
    The compounds are used by spraying a solution of this compound in a solvent. As
    the solvent uses a mixture consisting of acetone: methanol: dimethylformamide in a ratio of 90: 8: 2 v / v of the mixture.
    The proposed method allows to reduce the consumption of herbicide per unit of the treated surface and thereby increase its efficiency.
    权利要求:
    Claims (1)
    [1]
    Invention Formula
    The method of killing weeds by treating them or the soil on which they grow, derivatives of w-shdazolidinone, characterized in that, in order to increase the efficiency of the method, 3- -L5- (1,1-dimethylethyl) is used as an imidazolidinone derivative -3-isoxazole1 - - -metsch1-4-oxy-2-imidazolidinone in the amount of 0.56-11.2 kg / ha.
    e
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    five
    - m in,.
    "G 01 about c 0)
    and-1 and C; a and

    2 &
    about and
    I
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    同族专利:
    公开号 | 公开日
    US4268679A|1981-05-19|
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    KR830005210A|1983-08-03|
    CS235512B2|1985-05-15|
    ES509900A0|1983-02-16|
    JPS6330913B2|1988-06-21|
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    引用文献:
    公开号 | 申请日 | 公开日 | 申请人 | 专利标题
    US3544582A|1965-04-06|1970-12-01|Hoffmann La Roche|Process for preparing aminoisoxazoles|
    US3773780A|1971-03-10|1973-11-20|Bayer Ag|1--imidazolidinone-compounds|
    US3847935A|1972-04-12|1974-11-12|Upjohn Co|5-substituted 1--2-imidazolidinones|
    JPS5163170A|1974-11-27|1976-06-01|Shionogi Seiyaku Kk| 33 isookisazorirunyosoruino seizoho|
    DE2727586A1|1977-06-20|1979-01-04|Bayer Ag|Beta lactam antibacterials - with 2-oxo-imidazolidine type substit. in the side chain, are useful e.g. for increasing growth rate of animals|
    NZ197589A|1980-07-07|1984-11-09|Lilly Co Eli|3--4 hydroxyimidazolidin-2-ones and corresponding imidazolin-2-ones|US4507145A|1980-02-19|1985-03-26|Ppg Industries, Inc.|Herbicidal 3-[substituted 3- or 5-isoxazolyl]-1-4-, or 5-substituted-2-imidazolidinones|
    NZ197589A|1980-07-07|1984-11-09|Lilly Co Eli|3--4 hydroxyimidazolidin-2-ones and corresponding imidazolin-2-ones|
    US4354030A|1981-12-24|1982-10-12|Eli Lilly And Company|Isoxazolylimidazolidinone herbicides|
    US4421546A|1981-12-24|1983-12-20|Eli Lilly And Company|Aquatic method|
    US4857099A|1982-02-12|1989-08-15|American Cyanamid Company|Terrestrial and aquatic herbicidal methods|
    US4426527A|1982-02-12|1984-01-17|Ppg Industries, Inc.|3-[5- Or 3-substituted-1,2,4-oxadiazol-3- or -5-yl]-1-substituted-4-substituted-5-substituted or unsubstituted-2-imidazolidinones|
    US4581458A|1984-02-02|1986-04-08|Warner-Lambert Company|5-substituted-3-aminoisoxazole compounds|
    US4471123A|1983-04-29|1984-09-11|Eli Lilly And Company|Synthesis of isoxazolyl imidazolidinones|
    US4689071A|1983-05-05|1987-08-25|Ppg Industries, Inc.|Herbicidally active 3-isoxazolyl-2-imidazolidinone derivatives|
    GR82037B|1983-05-27|1984-12-12|Lilly Co Eli|
    US4604127A|1984-07-17|1986-08-05|Eli Lilly And Company|Herbicidal pyridazinylimidazolidinone compounds|
    US4600430A|1985-02-22|1986-07-15|Eli Lilly And Company|Pyridinylimidazolidinone compounds|
    JPH0482149B2|1985-10-23|1992-12-25|Shionogi Seiyaku Kk|
    JPH0437500B2|1987-01-29|1992-06-19|Fujitsu Ltd|
    US4770668A|1988-01-19|1988-09-13|National Starch And Chemical Corporation|Ethylene urea compositions useful as permanent press promoting chemicals|
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    US7649007B2|2006-08-15|2010-01-19|Wyeth Llc|Oxazolidine derivatives as PR modulators|
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    CN109790150A|2016-08-11|2019-05-21|拜耳作物科学股份公司|Substituted pyrazolinyl derivative, preparation method and its purposes as herbicide and/or plant growth regulator|
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    法律状态:
    优先权:
    申请号 | 申请日 | 专利标题
    US06/122,633|US4268679A|1980-02-19|1980-02-19|3-[5- or 3-Substituted-5- or 3-isoxazolyl]-1-allyl or alkyl-4-substituted-5-substituted or unsubstituted-2-imidazolidinones|
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