• 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:
    Diphenyl ether cyclic imine derivatives having the general formula I: <CHEM> wherein R1 represents a halogen atom or a haloalkyl group; R2 and R3, which may be the same or different. each independently represents a hydrogen or halogen atom or a nitro, cyano or haloalkyl group; A represents a cyano, alkyl, aryl, alkoxy, aryloxy, alkylthio or arylthio or their S-oxygenated derivatives, acyl, acyloxy or alkoxycarbonyl group; and B represents a hydrogen atom or one of the meanings given for A. The preparation of such compounds; compositions containing them; and their use as herbicides.
    公开号:SU1412595A3
    申请号:SU853951200
    申请日:1985-09-12
    公开日:1988-07-23
    发明作者:Мунро Давид；Антонио Бит Рино
    申请人:Шелл Интернэшнл Рисерч Маатсхаппий Б.В. (Фирма)；
    IPC主号:
    专利说明:

    tc ate
    coke

    s
    This invention relates to chemical methods for controlling weeds and unwanted vegetation.
    The purpose of the invention is to increase the germicidal action of the method of controlling undesirable vegetation based on the use of diphenyl ether derivatives.
    Example 1. Method for preparing 4- (2-chloro-4-trifluoromethylphenoxy) 2- - (5-methoxycarbonylisoxazol-3-yl) -nitrobenzene (compound 1). 2-nitro-5- (2-chloro-4-trifluorometh-1 phenoxy) -o-chlorobenzene oxime (2 g) is dissolved in diethyl ether (10 ml) with methyl acrylate (0.55 g) and added dropwise a solution of triztilamine (0.7 g) in ether (5 ml) under nitrogen atmosphere with stirring at ambient temperature. The precipitated triethylamine hydrochloride is filtered off, the solvent is removed under reduced pressure, the remaining oil is purified by the chromatographic method and the final substance is obtained as a colorless oil.
    NMR spectrum, S 3.55 (d, I 9H, 2H); 3.9 (s, 3N); 5.25 (t, I 9H ,, 1H), 7.0-8.3 (t, 6H).
    Found,%: C 47.7; H 2.7; N 5.9.
    C, H, N, C1F, 0 ,.
    Calculated,%: C 48.6; H 2.7; N 6, Under the conditions of Example 1, other compounds are prepared using other unsaturated substances instead of methyl acrylate. The list of synthesized compounds is presented in table. one.
    Example 2. 3- (2-Chloro-4-trifluorometh-1 phenoxy) -6-nitro (| 4-chlorobenzaldoxime (2 g) is dissolved in diethyl ether (20 ml), added Dimethyl fumarate (1 g) dissolved in dry tetrahydrofuran (5 ml) and triethyl amine (1 g) are added dropwise with vigorous stirring over a period of more than one minute at ambient temperature. A precipitate of hydrochloric triethylamine is immediately formed. ether / water mixture (50/50; 200 ml), the organic layer is separated, washed and dried. An orange oil is obtained. Chromatographic Single followed by recrystallisation yielded a crystalline solid article. mp. 125 C, a compound of formula (I), wherein A and B represent Me- toksikatebonil.
    0 5
    0
    five
    0
    five
    0
    five
    The structure has the hran configuration and is confirmed by NMR.
    Calculated,%; C, 47.75; H 2.8; N 5.55. .
    Found,%: C 47.75; H 2.8; N 5.55 (compound 11A).
    The cis form of the same compound was also obtained as a crystalline solid with mp. 1 22 C. The analysis gave the following: C 47.9; H 2.7; N 5.5 (compound 11B).
    Example 3. Herbicidal action. To evaluate the herbicidal effect, compounds are tested on specific plants: maize, rice, coarse millet, oats, flax seed, mustard, sugar beet, soybeans.
    The trials are divided into two categories: pre-emergence and post-emergence emergence. Tests of the category up to seedlings include spraying with liquid forms a compound of the soil on which plant seeds have recently been sown. The post-emergence test categories include two types of tests, namely, watering the soil and spraying the leaves. In tests involving irrigation of the soil, the soil in which the seeds of the plants were sown is watered with liquid forms containing the indicated compound, and in tests involving spraying the leaves, the planted plants are sprayed with these forms.
    In tests, soil prepared in the form of a garden loam is used.
    The formulations used in the tests are prepared from solutions of the test compounds in acetone containing 0.4% by weight alkylphenol / ethylene oxide condensate. These acetone solutions are diluted with water and the resulting formulations are applied at dose levels corresponding to 5 kg or 1 kg of active substance per hectare, in volume equivalent to 600 liters per hectare, in tests involving spraying the soil and spraying the leaves, and dose levels of 10 kg of active substance per hectare, in volume equivalent to approximately 3000 liters per hectare, in tests involving irrigation of the soil.
    The control groups use untreated sown soil in the test category before germination and untreated soil with plant sprouts in the test category after the emergence of seedlings.
    The herbicidal effects of the test compounds are assessed visually twelve days after spraying the leaves and soil and thirteen days after watering the soil. Data recorded in accordance with the scale of 0-9. The O mark indicates growth, the same as that of the untreated control groups, the 9 mark means the death of plants.
    For comparison, a known herbicidal active compound is used.
    01 CHj
    If / "G, 0, CPa-Ooh) - 0-CH-s - N
    CHs
    权利要求:
    Claims (2)
    [1]
    The test results are shown in Table.
    [2]
    2. The formula of the invention
    A way to combat unwanted plant 1 by treating it or
    soil on which it grows, derivatives of diphenyl ether, which is characterized by the fact that, in order to increase the herbicidal effect, a compound of the formula is used as a derivative of diphenyl ether.
    ten
    .Ci
    CF340VO-4Q
    N02
    15
    20

    25
    where a is methoxy, cyano, methoxycar; bonyl, acetyl, acetyloxy, phenyl, phenylthiophenylsulfonyl, carbamoyl or diethylphosphoryl
    B is hydrogen;
    or A and B both mean methoxycarbonl in the amount of 1-10 kg / ha.
    Table 1
    f sold plg CC - saek1ta sugar a, NE - soya bean.
    Table 2
    类似技术:
    公开号 | 公开日 | 专利标题
    US4314069A|1982-02-02|Herbicidal compound, herbicidal composition containing the same, and method of use thereof
    SU1428196A3|1988-09-30|Method of producing 2-substituted phenyl-4,5,6,7-tetrahydro-2h-isoindole-1,3-dions
    CA1048498A|1979-02-13|2-sulfonyloxyethyl-phosphonic or thionophosphonic acid derivatives as plant growth regulators
    SU1412595A3|1988-07-23|Method of controlling unwanted growth
    IE54555B1|1989-11-22|A fungicidal indanylbenzamide
    GB1577485A|1980-10-22|Substitued isoxazolyl benzoates and their use as herbicides and plant growth regulants
    KR840000891B1|1984-06-26|Unsymmetrical thiophosphonate insecticides and mematocides
    US4229204A|1980-10-21|Trifluoromethylphenyl isoxazolyl benzoates
    US3427146A|1969-02-11|Phenoxypyridazines as herbicides
    US4551171A|1985-11-05|2-Nitro-5-| phenylalkanone oxime and imine derivatives as herbicides
    US4166732A|1979-09-04|Oxadiazol-5-yl-benzoates
    HU184675B|1984-09-28|Herbicides containing substituted cyclopropyl-methoxy-anilide and process for preparing such compounds
    US4273769A|1981-06-16|O-Ethyl S-alkyl S-isopropyl phosphoro-dithiolate, and their use as nematocide
    US4039635A|1977-08-02|Soil fungicidal phosphorothioate
    CA1091686A|1980-12-16|Thiophosphorylguanidines for combating pests
    US4209629A|1980-06-24|3&#39;-|-spiro[isobenzofuran-1|,5&#39;|-isoxazol]-3-ones
    US4203979A|1980-05-20|Insecticidal 1-sec. and tert.-alkyl-2-disubstituted-phosphoryl hydrazines
    US4334909A|1982-06-15|N-|-2&#39;-nitro-6&#39;-substituted-2-haloacetanilides and their use as herbicides and plant growth regulants
    US4095970A|1978-06-20|2,6-Dichlorothiolbenzoates and use thereof as plant growth regulators
    US4134752A|1979-01-16|Plant growth regulators
    US3927062A|1975-12-16|Plant growth regulators
    US3949023A|1976-04-06|Novel oximino -phosphorothiolate derivatives
    KR800001571B1|1980-12-28|Oxazolidines &amp; thiazolidines-herbi cidal antidotes
    KR830001655B1|1983-08-22|Method for preparing 3 &#39;-| -spiro [isobenzofuran-1 |, 5&#39; | -isoxazol] -3-one
    US4401457A|1983-08-30|3&#39;-|-spiro[isobenzofuran-1|,5&#39;|-isoxazol]-3-ones and their use as herbicides
    同族专利:
    公开号 | 公开日
    PH22372A|1988-08-12|
    CS264121B2|1989-06-13|
    EG17662A|1990-08-30|
    PT81119A|1985-10-01|
    FI853161A0|1985-08-16|
    IL76371D0|1986-01-31|
    EP0174685A3|1987-02-25|
    HU198168B|1989-08-28|
    AU4739285A|1986-03-20|
    ES8702380A1|1986-12-16|
    CS651385A2|1988-09-16|
    DK415985A|1986-03-15|
    PT81119B|1987-10-20|
    ZA856983B|1986-04-30|
    BR8504413A|1986-07-15|
    JPS6172769A|1986-04-14|
    GB8423252D0|1984-10-17|
    IL76371A|1989-10-31|
    MA20526A1|1986-04-01|
    NZ213453A|1989-01-27|
    ES546914A0|1986-12-16|
    KR860002482A|1986-04-26|
    GR852221B|1986-01-14|
    HUT40602A|1987-01-28|
    CA1250588A|1989-02-28|
    FI853161L|1986-03-13|
    AU588251B2|1989-09-14|
    DK415985D0|1985-09-12|
    EP0174685A2|1986-03-19|
    引用文献:
    公开号 | 申请日 | 公开日 | 申请人 | 专利标题
    US4283403A|1976-06-14|1981-08-11|Eli Lilly And Company|Substituted isoxazolines for control of plant phytopathogens|
    US4139366A|1977-05-12|1979-02-13|Monsanto Company|2-[5-aryl-2-isoxazolin-3-yl]benzoates and use as herbicides|
    US4129568A|1977-05-12|1978-12-12|Monsanto Company|2-[3-Aryl-2-isoxazolin-5-yl]benzoates|
    AU6651581A|1980-02-01|1981-08-06|Rhone-Poulenc, Inc.|2-nitro- benzoyl derivatives as herbicides|DE3736113A1|1987-10-26|1989-05-03|Hoechst Ag|DRUGS, PHOSPHORUS-BASED 2-ISOXAZOLINES AND ISOXAZOLES CONTAINING THEREOF, AND METHOD OF PREPARING THESE HETEROCYCLIC COMPOUNDS|
    GB9110858D0|1991-05-20|1991-07-10|Shell Int Research|Herbicidal compounds|
    DE10114597A1|2001-03-23|2002-10-02|Bayer Cropscience Gmbh|Arylisoxazoline derivatives, process for their preparation and their use as pesticides|
    US9084277B2|2007-05-04|2015-07-14|Qualcomm Incorporated|Method and apparatus for UL ACK allocation|
    US8687652B2|2008-03-27|2014-04-01|Qualcomm Incorporated|Uplink ACK/NAK resource allocation|
    PL2900644T3|2012-09-25|2017-03-31|Bayer Cropscience Ag|Herbicidal and fungicidal 5-oxy-substituted 3-phenylisoxazolin-5-carboxamides and 5-oxy-substituted 3-phenylisoxazolin-5-thioamides|
    US9585392B2|2012-09-25|2017-03-07|Bayer Cropscience Ag|3-phenylisoxazolin derivatives with herbicidal action|
    法律状态:
    优先权:
    申请号 | 申请日 | 专利标题
    GB848423252A|GB8423252D0|1984-09-14|1984-09-14|Ether herbicides|
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