• 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:
    The invention concerns novel compounds of the formula I <CHEM> The compounds are herbicides and in further embodiments the invention provides processes for the preparation of compounds of formula I, intermediates useful in the preparation of compounds of formula I, herbicidal composition containing as active ingredient a compound of formula I, and processes for severely damaging or killing unwanted plants by applying to the plants or to the growth medium of the plants an effective amount of a compound of formula I.
    公开号:SU1205766A3
    申请号:SU802969267
    申请日:1980-08-29
    公开日:1986-01-15
    发明作者:Сербан Александр；Джон Фаркухарсон Грэм；Лайдейт Джек
    申请人:Ай-Си-Ай Аустралиа Лимитед (Фирма)；
    IPC主号:
    专利说明:

    one
    The invention relates to a method for producing new 1,2,4-benzotriazine derivatives having herbicidal properties and which can be used in agriculture.
    The reaction of o-alkylation of phenols with alkyl halides is known, preferably in the presence of a base, in particular in the presence of hydroxides or carbonates of a regular or alkaline type.
    Lands
    T.l from 6b1g: - a method of obtaining new 1,2,4-benzotri derivatives
    Iaiya, with a selection of herbicidal acid.
     The goal is achieved based on the method of obtaining 1,2,4-benzotriazine derivatives of the general formula
    A is hydrogen, halogen, kil, C (-C, -alkoxy or C -Cf, -haloalkyl; B is hydrogen or halogen; and Rj is independently hydrogen or C4-C; -alkyl; G - C - Sat-alkoxy; n is O or 1.
    The method is that, 4-benzotriazine of the general formula
    (0) n

    . lnc f 0
    -N I /.
    (Ii)
    (Iii)
    Where A, B, p and R, have the indicated meanings,
    subjected to interaction with the compound of the General formula
    RO o i II Hal-SI-C-G
    where Hal is chlorine, bromine or iodine;
    G has the indicated meanings, followed by allocation of the desired product.
    The reaction is usually carried out in an organic solvent.
    057662
    Suitable as solvents are ketones, eg acetone, methyl ethyl ketone, methyl isobutyl ketone, dipolar aprotic solvents, for example
    5 dimethylformamide, dimethylacetamide, dimethyl sulfoxide, N-methylpyrrolidone, hexamethylphosphoric triamide, sulpholane.
    As a rule, the reaction contributes
    10 heating and usually the reaction temperature is 40-150 ° C, the reaction time is 0.5-20 hours. However, they can be used with higher or lower
    temperatures and / or long or more than 15 short reaction times.
    The compounds of formula 1 possess herbicidal activity. Some of them have selective activity towards monocotyledonous
    ;) 0 plants, with two-share plants sufficiently resistant to the quantities used to significantly damage or destroy other plant varieties.
    In addition, some compounds of formula 1 have selective activity with respect to a group of monocotyledonous plants and can be used with a consumption rate sufficient to destroy or significantly damage monocotyledons weed growing together with monocotyledonous cereals.
    The compounds of formula 1 can be directly applied to the plant (in the period after germination) or on the soil before the germination of the plant (pre-emergence application). However, it is usually more effective to use after germination.
    The compounds of formula 1 can be used to inhibit the growth, significant damage or destruction of plants, but it is preferable to use them as a composition containing the compound in admixture with a carrier, which is a solid or liquid diluent.
    5- Compositions based on compounds
    according to the invention include both diluted compositions, ready for immediate use, and concentrated, which must be diluted
    5 before use (usually water). Preferably, such compositions contain from 0.01 to 90% by weight of the active ingredient, Diluted compositions,
    40
    45
    Products for use preferably contain 0.01-2% of the active ingredient, while the concentrated may contain 20-90% of the active ingredient, preferably 20-70%.
    The solid compositions may be in the form of granules or dusts in which the active ingredient is mixed with a finely divided solid diluent, for example kaolin, bentonite, diatomaceous earth, dolomite, calcium carbonate, talcum, powdered magnesium, fuller earth and gypsum. They may also be in the form of dispersible powders or granules containing a mixing agent in order to facilitate the formation of a dispersion of powder or grains in a liquid. Solid powder formulations can be used as foliar dusts.
    Liquid compositions may contain a solution or dispersion of the active ingredient in water, sometimes containing a surface-active agent, a solution or dispersion of the active ingredient in a water-immiscible organic liquid, which is dispersed in the form of droplets in water.
    Example 1. Methyl-2- 4-N-methyl-H- (7-chloro-1-oxide-1,2,4-benzotriazin-3-yl) amino phenoxy} propionate (1).
    A. A mixture of 3, 7-DICHLOR-1, 2,4-benz.-triazin-1-oxide (3.5 g), (N-methylamino) phenolsulfate (5.6 g) and aqueous ethanol (50 ml) is refluxed for 18 hours. The solvent is partially removed by evaporation, and the red solid (3.0 g) is separated by filtration. Chromatography on silica gel (80 g) using chloroform as eluant gives 4-methyl-M- (7-chloro-1-oxide-1,2,4-benzotriazin-3-yl) amino phenol (2) , 1 g) as a red solid.
    Mass spectrum: M (molecular ion) was found at m / e 302; C, 4H, CIN
    B. A mixture of 4-N-methyl-L- (7-chloro-oxide-1,2,4-benzotriazin-3-Sh1) amy-HoJ phenol (2.1 g), methyl 2-bromopropionate ( 1.9 g), anhydrous calcium carbonate (1.6 g) and methyl ethyl ketone (30 ml) are refluxed for 20 hours. The reaction mixture is filtered and the solvent is distilled off under reduced pressure.


    ten
    05766
    pressure, an orange solid (3.0 g) is obtained. As a result of chromatographic separation on a silica gel column (70 g) using chloroform / methanol system, -methyl-K- (7-chloro-1-oxide-1,2,4-benzotriazin-3-yl) amine phenoxy is obtained as eluent. propionate (2.7 g) as an orange solid.
    Mass spectrum: M (molecular ion) found at m / e 386; C, d N 1 386.
    Example 2. Methyl-2- 4-M-methyl-15-N- (7-chloro-1-oxide-1,2,4-benzotriazin-3-yl) amino phenoxy propionate (1).
    A. A mixture of 3,7-dichloropropane-1,2,4-benzo-tripiasin-1-oxides (30.0 g), 4- (N-methylamino) phenolsulfate (48.0 g), water (400 ml) and acetonitrile (400 ml) are boiled under reflux with stirring for 24 hours. The resulting solution is concentrated, cooled, red crystals are formed, which are recrystallized from acetonitrile-water, to give 4-s-methyl-M- (7 -chloro-1-oxide-1,2,4-benzotriazin-3-yl) amino phenol (36.5 g) as red crystals, m.p. 228-230 ° C.
    A mixture of 4-N-methyl-N- (7-chloro-1-oxy-1, 2,4-benzotriazin-3-yl) amine-HoJ phenol (20.8 g), methyl 2-bromopropionate ( 13.8 g), anhydrous potassium carbonate (11.4 g) and anhydrous dimethylformamide (100 ml) are heated with stirring at 100 ° C for 2 hours. Dichloromethane is added to the cooled solution and the mixture is washed several times with water. The organic phase is dried with anhydrous magnesium sulphate and the solvent is removed by distillation under reduced pressure. The reaction product is recrystallized from metonol, get the specified product (16.8 g) in VI25
    thirty
    35
    40
    45
    yes orange crystals, mp.132 C.
    The structures were confirmed by PMR spectroscopy and mass spectrometry.
    Example 3: Compounds 7-13, 16 and 39 listed in Table. 1 is prepared from the corresponding 1,2,4-triazine 4- (K-methylamine) phenolsulfate and
    corresponding alkyl-2-gaJ ppropyonate using a procedure similar to example 1 or 2,
    The proposed structure for each of the compounds was confirmed by PMR spectroscopy and mass spectrometry, the corresponding physicochemical data are presented in Table 2.
    Example 4. Methyl-2- (7- -chloro-1-oxide-1,2,4-benzotriazin-3 aMHHoJ phenoxy propionate (2).
    A. A mixture of 3,7-dichloro-1,2,4-benzo-tripiaen-1-oxides (3j5 g), 4-a. Aminophenol (3.5 g) and aqueous ethanol (30 ml) is boiled with reflux for 18 hours. The solvent is removed by distillation under reduced pressure to give (-7-chloro-1-oxide-1,2,4-benzotriazin-3-yl) amino phenol (4.0 g)
    B. A mixture of (7-chloro-1-oxide-1, 2,4-benzotriazin-3-yl) amino phenol (4.0 g), methyl 2-bromopropionate
    (3.7 g), anhydrous potassium carbonate (3.0 g) and methyl ethyl ketone (40 ml) are refluxed for 18 hours. The solvent is removed by distillation under reduced pressure and the residue is partitioned between water and chloroform. The chloroform layer is dried; the chloroform is evaporated; a solid is formed. (3.0 g), which is washed with a boiling methanol, give 2- (7-chloro-1-oxide-1, 2,4-benzotriazin-3-yl) amino phenoxy | propionate (2.0 g) as a red solid.
    Mass spectrum: M (molecular ion) found at m / e 374; C | H, CIN, 04 374.
    Example 5. Compounds 6.33, 35.41.41, and 52 are listed in Table I. 1 is prepared from the corresponding 1,2,4 ™ benzotriazine, 4-aminophenol and the corresponding 2-halopropionate, according to the procedure of Example 4.
    The proposed structure dp; Each of the compounds was confirmed by cdn by the methods of PMR spectroscopy and mass spectrometry, the corresponding physicochemical data are presented in Table 2.
    Example 6. Methyl-2- 4-N-methyl-N- (7-chloro-1,2,4-benz otraazin-3-yl) amine J phenoxy propionate (3).
    A. 4-, n-methyl-K- (7-chloro-1-oxide-1,2,4-benzotriazin-3-yl) amino J phenol (10.0 g) and powdered zinc (4.3 g) was added to a mixture of acetic acid (100 ml) and water (10 ml). The resulting mixture is heated under stirring vigorously for 30 minutes. Zinc powder (4.3) is added, heating and stirring
    continue for another 30 min. The cooled mixture is filtered, the filtrate is added to a solution of hydrogen peroxide 5 ml of a 30% solution (volume / volume) in water (100 ml), the aqueous mixture is stirred at room temperature for 1 hour. The solid is collected by filtration, washed with water and dried. 4-c-methyl-L- (7-chloro-1,2,4-benzotriazin-3-yl) aminoZ fnol (8.2 g) is obtained as a red crystalline substance, mp, 225 - -226 ° С .
    B. 4-K-methyl-Y- (7-chloro-1,2,4-benzotriazin-3-yl) amino phenol is reacted with methyl 2-bromopropionate according to the procedure of Example 1 to obtain the product, m.p. .
    The proposed structure is confirmed by PMR spectroscopy and mass spectrometry.
    Example 7. Compounds 14, 15, 17, 21, 23, 32, and 40 are listed in Table. 1, is obtained by reducing the corresponding 4-N-methyl-N- (1-oxide-1,2,4-benzotriazin-3-yl) amino phenol and then reacting 4-N-methyl-N- (1,2,4- benzotriazin-3-yl) amino phenol with an appropriate 2-halopropionate according to the procedure of Example 6.
    The proposed structure for each of the compounds is confirmed by PMR spectroscopy and mass spectrometry, the relevant physicochemical data are presented in Table. 2,
    Example 8. Ethyl-2- 4-N-methyl-M - (- 6-chloro-1,2,4-benzotriazin-3-yl) amino-phenoxy -2-methylpropionate (53).
    A mixture of 4-N-methyl-N- (7-chloro-1,2, 4-benzotriazin-3-yl) amino-phenol (1, 5 g) ethyl 2-bromo-2-methylpropionate (1, 23 g), anhydrous potassium carbonate (0.87 g) and dimethylformamide (15 ml) are heated with stirring at 100 ° C for 3 days. The cooled solution is poured into dichloromethane and the mixture is washed with water. The aqueous phase is dried with anhydrous magnesium sulphate and the solvent is removed by distillation under reduced pressure to give an oil. The crude product is purified by chromatography on silica gel (eluent dichloromethane) to give
    compound (0.9) as a red oil.
    The proposed structure is confirmed by the methods of PMR spectroscopy and mass spectrometry, PMR spectrum (ppm of CDCl,): 1.30; t, 3H; 1.70; S, 6H; 3.65; s, NN; 4.30; g, 2H; 7.20, t, 4H; 7.60; s, 2H; 8.20; s, 1H.
    Example 9. Compounds 47.48, 50.51 and 54 are prepared from the corresponding 4-C-methyl-H- (1,2,4-benzotriazin-3-yl) aMHHoJ phenol and the corresponding alkyl-2-haloalkanecarboxyl - that, following the method of example 8.
    The structure assumed for each of the compounds was confirmed by PMR spectroscopy and mass spectrometry. The corresponding physico-chemical data are presented in table. 2
    A number of compounds listed in table. are solids and can be identified by their melting points. Most of the compounds are oily products, they are characterized and can be identified by their PNR spectra.
    Example 10. Concentrated formulations of the compounds obtained as follows.
    A. In the case of oily and waxy solids, they are dissolved in toluene containing 7% (v / v) Terik 13 (Terik is a commercial name, Terik 13 is a nonylphenol ethoxylation product supplied by ICI Australia Zimited) and 3% ( v / v) Kemmat C-15B (Kemmat Trade Name, Kemmat C15B — composition based on calcium dodecyl benzosulphonate); in the case of crystalline solids 5 wt. including such a compound and 1 wt. The PT range (Trade name Diapol, Diapol PT is an anionic suspending agent) is added to 94 wt. h, an aqueous solution containing 0.25% (v / v) Terric 8 (nonylphenol ethoxylation product), the mixture is ground in a ball mill to form a stable suspension. Then, emulsifiable concentrates and suspensions are diluted with water to obtain an aqueous composition of the required concentration required to assess the pre-emergence and post-emergence herbicidal activity of the compounds prepared according to the invention.
    Example 1. Pre-emergence germicidal activity of the compounds in the form of the indicated compositions obtained according to Example 10 is assessed according to the following procedure.
    The seeds of the test plants are immersed to a depth of 2 cm in the soil in the landing boxes. Monocotyledonous and dicotyledonous plants are immersed in separate boxes, and after planting, these boxes are sprayed with the required number of compositions of one of the compounds. Two control boxes are prepared similarly, but not sprayed, they are used for comparison. All boxes are placed in a greenhouse, slightly moistened by spraying from above to initiate germination, and then sub-irrigated, which is required for optimal plant growth. After three weeks, the boxes were removed from the greenhouse and the treatment effect was visually assessed. The results obtained are presented in Table. 3 (plant damage is rated on a scale of 0-3, where O is 0-23% damage, 3 is 75-99% destruction, and 3+ means 100% destruction, an (-) sign indicates that no experiments were performed).
    The abbreviations of the names of the tested plants are as follows: Wh - wheat; Ot - wild oat; Rg - chaff; 1t — Japanese blackberry; P - peas; 1p - ipome MS - mustard; Sf - sunflower.
    PRI me R 12. The post-emergence herbicidal activity of compounds 1 in the form of the formulations described in example 10 is assessed according to the following procedure.
    Seeds of the tested plant varieties are sown in rows at a depth of 2 cm into the soil in seedlings. Monocotyledonous and dvukhdolennye plants are placed in separate boxes with duplication. These four seed pots are placed in a greenhouse, lightly sprayed on top with water spray to initiate PI treatment and then sub-irrigated for optimal plant growth. After plants grow to a height of 10 to 12.5 cm, one box of each of the monocotyledonous and doped plants is removed from the greenhouse and sprayed with the required amount of Compound 1 composition. After the sprayers, the boxes are returned to the greenhouse and the composition
    They are poured for another 3 weeks, and then the effect of the treatment is evaluated visually in comparison with the machined boxes. The results are presented in Table. 4, plant damage is rated on a scale of 0-3, where O is 0-25% damage, 3 is 75-99% damage, and 3+ means 100% destruction, an (-) sign indicates that the experiment was not conducted (reduction the names of the tested plants are the same as in Table 3).
    The abbreviation in the table. 5 and 6
    the following: Sb sugar beets
    RP Canola
    5 Ct Cotton
    Sy Co
    Mz Corn
     Mw Winter wheat RC wheat Rice Sn Senecio vulgaris
    IP Ipomea purpurea 10 Am Amaranthus retroflexus
    Pi Polygonum aviculare
    Ca Chenopodium album po Portulaca oleracea
    15 XaXanthiuni pensylvanicum
    AbAbutilon theophrasti
    CvConvolvulus arvensis
    CoCassia obtusifolia
    Avavena fatua
    20 Dg Digitaria sanguinalis Al Alopecurus myosuroides
    StSetaria viridis
    25 ShSorghum halepense
    AgAgropyronrepens
    CnCyperug rotundas
    ten
    0576610
    P p and M e p 13, Compounds are compounded for testing by mixing the appropriate amount with 5 ml of emulsion-HHj obtained by diluting 160 ml
    5 solution containing 21.8 g / l of Spas 80 and 78.2 g / l of Tween 20 in methyl cyclohexanone 600 ml of water. (Span 80 is the trade name of a surfactant based on sorbate monolaurate), Tween 20 is the trade name of a surfactant consisting of a condensate of sorbitan monolaurate with 20 mol. H, ethylene oxide. Then every 5 ml of the emulsion,
    5 containing the compound to be tested, working, drinking 40 lp of water and spraying young plants (post-emergence test) related to those listed in Table. 5 species m. Defeat
    20 test plants are assessed after 14 days on a scale of 0-5, in which O means a lesion of 0-20%, and 5 means complete destruction, In tests of pre-emergence herbicidal activity
    35 seeds of test plants are sown in small holes formed on the surface of the soil in plastic plates. Then the soil surface is leveled and sprayed, and a thin layer of fresh soil is applied to the surface of the treated soil. Evaluation of a herbicidal lesion was carried out after 1 day using the same scale on a scale of 0-5 as in the post-emergence testing experiments. In both cases, the degree of herbicidal lesion is assessed in comparison with untreated control plants. The results are presented in Table. 5, The (-) sign indicates that the experiment was not performed. Abbreviations of the names of the test plants, see below.
    Example 14, Selective germicidal activity of compounds in their field use.
    Test compounds are used in compositions prepared according to the procedure of Example 10,
    50 Seeds of test plants are sown on flat areas of elevations that are 1 m apart from each other. Two types are sown at each elevation, 55 Flat areas of elevations are grouped into sub-sites according to the normal application of test compound 1, Plant Species
    35
    40
    11120576612
    are sown at different times, 14, 28, and 56 days after spraying, so that they can reach approximately. The results obtained, expressed from one age stage to one in percent destruction, are presented in Table. 7
    5 The abbreviations of the test plants are as follows:
    of time.
    Each flat area of the surface to be pollinated with the test compound is marked in the center of a circle with a diameter of 1.25 m with a peg and sprayed to a width of 1 m with a spray .10
    In the pre-emergence test, flat areas of the hill are sprayed with the test compound after sowing the seeds, and damage to the test plants is visually assessed after 15, 14, 21, 35 and 63 days after spraying. The results, expressed as a percentage of destruction, are presented in Table. 6
    In the post-emergence test, 20 flat areas of elevations are sprayed with the test compound after the test plants reach stage 2-3 leaves, and the lesion is individually assessed at 7, 25
    Syco
    EtCotton
    PpDrahis
    Mz Corn
    (Bethal) (Delta Pine 16) (Red Spinish) (XL 45)
    SS Setaria anseps
    Dg Digitaria Sanguinalis Es Echinochloa cres-galli
    Sg Sorghum (Goldrush) Sh Sorghum Halepense
    Table 1 i
    7-clj
    7-f
    7-CHjO
    7-br
    7-cl
    7-CFj
    7-F 7-Cl
    6-Cl 6-Cl
    0 0
    one
    0
    With
    Cotton
    Drachis
    Corn
    (Bethal) (Delta Pine 16) (Red Spinish) (XL 45)
    Setaria anseps
    Digitaria Sanguinalis Echinochloa cres-galli
    Sorghum (Goldrush) Sorghum Halepense
    Table 1 i
    CH,
    c.
    CH,
    CH,
    C.
    CH,
    SLO
    CH,
    C, H, 0
    CH,
    C, H, 0

    II II
    C, H, 0 C.
    CH,
    C, H, 0
    CH:
    C, H, 0
    Continuation of table 1
    17
    120576618
    Continued table. 3
    nineteen
    1205766
    20 Continuation of table 3
    Table 7


    0.5 0.5
    28
    56
    7
    14 28 56
    3 o
    About About 5 5
    About About About About
     DAT is the number of days after treatment when the evaluation was performed and C is the untreated control plants.
    Compiled by Editor 0. Tehred Kolesnikova 3.Paly Proofreader G. Reshetnik
    Order 202 Circulation 379 Subscription
    VNIIPI USSR State Committee
    for inventions and discoveries 113035, Moscow, Zh-35, Raushsk nab., 4/5.
    Branch PGS Patent, Uzhgorod, ul, Proektnl, h
    100
    100 I
    oo
    oo
    oo
    oo
    90100
    93100
    OO
    oo
    oo
    oo
    100 100
    100
    oh oh oh
    100
    oh oh oh
    100 100
    Ltd
    about
    权利要求:
    Claims (3)
    [1]
    * 1. METHOD FOR PRODUCING 1,2,4-BENZOTRIAZINE DERIVATIVES of the general formula (0) n where A is hydrogen, halogen, C ( -C 6 -alkyl, C ( -C 6 -alkoxyl or C ( -C 6 -haloalkine;
    B is hydrogen or halogen;
    Ry hRj is independently hydrogen or C <-C 6 alkyl;
    G - C (- C 6 alkoxide;
    η - 0 or 1, characterized in that, 1,2,4-benzotriazine of the general formula where A, B, η and R <have the indicated meanings, are reacted with the compound q of the general formula
    Ro O G II Hat-CH-C-G where Hal is chlorine, bromine or iodine;
    G has the indicated meanings, followed by highlighting the target προ-ι duct.
    [2]
    2. The method of pop. ^ characterized in that the process is carried out in the presence of a base.
    [3]
    3. The method according to p. 2, characterized in that, as the base use hydroxides or carbonates of alkali or alkaline earth metals.
    >
    类似技术:
    公开号 | 公开日 | 专利标题
    US4213773A|1980-07-22|Herbicidal substituted bicyclic triazoles
    HU188525B|1986-04-28|Herbicidal preparations containing tetrahydrophthalimide derivatives and process for the production of the active substance
    HU185882B|1985-04-28|Herbicides containing 4h-3,1-benzoxazine derivatives and process for preparing 4h-3,1-benzoxyzine derivatives
    CH631711A5|1982-08-31|COMPOUNDS AND COMPOSITIONS WITH HERBICIDE PROPERTIES AND THEIR PREPARATION METHOD.
    US4749403A|1988-06-07|Herbicidal derivatives of imidazolidinone and imidazolidine thione
    JP2015518841A|2015-07-06|1,5-dimethyl-6-thioxo-3- | -3,4-dihydro-2H-benzo [b] [1 , 4] Oxazin-6-yl) -1,3,5-triazinan-2,4-dione crystal form B
    EP0374839A1|1990-06-27|2-|benzaldoximes, preparation processes thereof, herbicides containing the same, and herbicidal compositions containing the same along with other active ingredients
    US4032326A|1977-06-28|Herbicidal 2-substituted aryl-4,5,6,7-tetrahydro-2h-isoindole-1,3-diones
    CA1182452A|1985-02-12|5-amino-1-phenyl-pyrazole-4-carboxylic acidderivatives and their use for controlling undesirable plant growth
    CS207776B2|1981-08-31|Herbicide means
    SU1205766A3|1986-01-15|Method of producing derivatives of 1,2,4-benzotriazine
    HU204667B|1992-02-28|Herbicidal compositions comprising n-aryl tetrahydrophthalimides as active ingredient and process for producing the active ingredient
    US4124373A|1978-11-07|Tetrahydroindazole herbicides
    HU214217B|1998-01-28|Herbicidal composition containing salicylether derivatives, process for the preparation of salicylether derivatives and method for weed control
    HU208226B|1993-09-28|Herbicidal compositions comprising pyrrolidine-2,5-dione or 4,5,6,7-tetrahydroisoindole-1,3-dione derivatives as active ingredient and process for producing the active ingredient
    US4804400A|1989-02-14|N-phenyl-maleimides and herbicidal and plant growth regulating methods of use thereof
    HU189217B|1986-06-30|Herbicide compositions containing 4,5-dimethoxy-pyridazone derivatives and process for producing the active agents
    EP0891336B1|2002-06-05|Substituted 1-methyl-3-benzyluracils
    HU214645B|1998-04-28|1-amino-3-phenyluracil derivatives, preparation thereof, using thereof as herbicides, desiccants and defoliants, such compositions and process for the production of the latters
    CS242883B2|1986-05-15|Herbicide and method of its efficient component production
    DE3724395A1|1989-02-02|3-phenylpropionic acid derivatives
    US4120693A|1978-10-17|Substituted isoindoles
    US4451284A|1984-05-29|Derivatives of 2-nitro-4- or -5-pyridyloxyphenylphosphonic acid, the preparation thereof, the use thereof as herbicides and/or plant growth regulators
    EP1034166B1|2003-05-02|Substituted 2-phenyl-3|-pyridazinones
    EP0387869B1|1993-07-21|4-ethyl-3-|-1-|-2-pyrrolidinone derivatives, processes for the preparation and use thereof, herbicidal compositions containing them
    同族专利:
    公开号 | 公开日
    HU186743B|1985-09-30|
    DK366880A|1981-03-01|
    ES8106508A1|1981-08-16|
    CS222188B2|1983-05-27|
    MY8700525A|1987-12-31|
    BR8005527A|1981-03-17|
    CA1145336A|1983-04-26|
    IE801763L|1981-02-28|
    PH16262A|1983-08-19|
    ZA804924B|1981-08-26|
    DK157192B|1989-11-20|
    ES494594A0|1981-08-16|
    DE3069461D1|1984-11-22|
    PT71754B|1981-06-08|
    EP0024931A3|1981-06-03|
    IL60831A|1985-04-30|
    DK157192C|1990-04-23|
    EP0024931A2|1981-03-11|
    IE50112B1|1986-02-19|
    IL60831D0|1980-10-26|
    NZ194612A|1982-12-21|
    PT71754A|1980-09-01|
    US4310347A|1982-01-12|
    EP0024931B1|1984-10-17|
    引用文献:
    公开号 | 申请日 | 公开日 | 申请人 | 专利标题
    US2489355A|1947-01-10|1949-11-29|Merck & Co Inc|Benzotriazines|
    US2966487A|1958-07-01|1960-12-27|Searle & Co|3-aminoalkylaminobenzotriazine-1-oxides|
    DE2223894C3|1972-05-17|1981-07-23|Hoechst Ag, 6000 Frankfurt|Herbicidal agents based on phenoxycarboxylic acid derivatives|
    DE2255947A1|1972-11-15|1974-05-22|Bayer Ag|SUBSTITUTED 3-AMINO-BENZO-1,2,4TRIAZINE-DI-N-OXIDES , METHOD FOR MANUFACTURING AND USING THEM AS ANTIMICROBIAL AGENTS|
    IE38778B1|1973-02-02|1978-05-24|Ciba Geigy|New 1,2,4-benzotriazine derivatives|
    US4105435A|1975-10-29|1978-08-08|Ishihara Sangyo Kaisha Ltd.|Herbicidal compound, herbicidal composition containing the same, and method of use thereof|
    DE2640730C2|1976-09-10|1983-08-25|Hoechst Ag, 6230 Frankfurt|Benzoxazolyloxy and benzothiazolyloxyphenoxy compounds and herbicidal agents containing them|
    CA1247625A|1977-07-22|1988-12-28|Howard Johnston|Trifluoromethyl pyridinyloxyphenoxy propanoic acidsand propanols and derivatives thereof and methods ofherbicidal use|
    ZA796645B|1978-12-22|1980-12-31|Ici Australia Ltd|Herbicidally active compounds and compositions|NZ197421A|1980-07-01|1984-08-24|Ici Australia Ltd|Isoquinoline derivatives and herbicidal compositions|
    NZ200031A|1981-04-02|1984-11-09|Ici Australia Ltd|Quinoline derivatives and herbicidal compositions containing such|
    GB9003553D0|1990-02-16|1990-04-11|Ici Plc|Herbicidal compositions|
    EP1502918A1|2003-07-31|2005-02-02|Bayer CropScience GmbH|The use of fused ring-1,2,4-benzotriazine derivatives as herbicides or plant growth regulators for the control of undesired plants or vegetation, compounds and compositions thereof, and processes for their preparation|
    法律状态:
    优先权:
    申请号 | 申请日 | 专利标题
    AUPE029979|1979-08-31|
    AUPE305380|1980-04-08|
    [返回顶部]