• 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 relates to novel heterocyclically substituted azoles and azines of the formula I <IMAGE> in which R1, X, Y and Z are as defined in the description, their preparation, and their use as agents with herbicidal activity.
    公开号:SU1722204A3
    申请号:SU884356592
    申请日:1988-10-06
    公开日:1992-03-23
    发明作者:Ганцер Михаель；Франке Вильфрид；Дорфмайстер Габриеле；Йоханн Герхард；Арндт Фридрих；Рис Ричард
    申请人:Шеринг Аг (Фирма)；
    IPC主号:
    专利说明:

    This invention relates to chemical means of controlling weeds and undesirable vegetation.
    The purpose of the invention is to increase the herbicidal activity of an agent containing
    as active substance is a heterocyclic nitrogen-containing compound.
    EXAMPLE 1. Preparation of 6- (6,6-dimethyl-3,5,6,7-tetrahydropyrrolo 2, 2, diazol-3-ylenimino) -4- (2-propynyl) -2H-1 ;
    317222044
    4-benzoxazin-3 (4H) -one (compound up to -20 ° С is slowly instilled solution
    1.01) .2.3 g of bromine in 10 ml of methylene chloride and re-2, 6 g of 2-amino-4,4-dimethylpyrrolidine are stirred for an additional 1 hour, and the hydrochloride is suspended in 20 ml of methyperature rises to 10 ° C. Thereafter
    at 5 ° C, a solution of 0.75 g of hydrochloricity, 30 ml of water, 30 ml of 5% sodium hydroxide solution in 5 ml of water and sodium hydroxide stirrer, and 30 ml are added in drops at 5 ° C. water. Phase
    30 min, and the reaction mixture of methylene dichloride is dried over anhydrous
    becomes transparent. Thereafter, sodium sulfate is then filtered, and the solution of 6-isothiocyanate-4- {2-10 schut is bubbled. The residue is purified by the chromato chromatopropinyl) -2H-1,4-benzoxazin-3 (4H) -one method on a column of silica gel.
    100 ml of methylene dichloride so as not to pre-yield 1.5 g (25% of theory), mp. 65 ° C.
    leave the temperature at 5 ° C; additionally, the mixture is obtained in the same way for 3 hours, and the temperature of the compounds:
    extend to 20 ° C. After that, when cooled-15
    Compound ns Compound mp, ° C
    1.026- (6,6-Dimethyl-3,5,6,7-tetrahydro-pyrrolo-2, 2.4 thiadiazol-3-or-denimino) -4-methyl-2H-1.4 benzoxazin-3 (4H) -on133
    1.036- (6,6-Dimethyl-3,5,6,7-tetrahydropyrrol-2,1-c 1,2,4 thiadiazol-3-ylidenimino) -7-fluoro-4- (2-propynyl) -2H1, 4-benzoxazin-3 (4H) -on62
    1.044- (2,3-Dibrom-2-propenyl) -6- (6,6-dimethyl-Z.b.-tetrahydropyrrolo-L-c3-thiadiazol-3-ylidenimino) -7-fluoro-2H- 1,4-benzoxazin-3 (4H) -on65
    1.055- (6,6-Dimethyl-5,6-dihydro-3H-thiazolo 2,3-c 1,2,4 thiadiazol-3-ylenimino) -6-fluoro-3- (2-propynyl) -2 (3N ) -benzthiazolone195
    1.065- (6,6-Dimethyl-3,5,6,7-tetrahydropyrrolo 2,1-11,2,4 thiadiazol-3-ylidenimino) -6-fluoro-3- (2-propynyl) -2 (3N) -benzthiazolone190
    1.076- (6,6-Dimethyl-5,6-dihydro-ZN-thiazolo 2,3-c 1,2,4 thiadiazol-3-ylenimino) -4- (2-propynyl) -2H-1,4 -benzoxazin-3 (-4H) -on124-26
    1.086 (6,6-Dimethyl-3,5,6,7-tetrahydropyrrolo 2,1-with 1,2,4 thiadiazol-3-ylidenimino) -4- (2-propynyl) -2H-1,4besoxazine- 3 (4H) -on110
    1.096- (6,6-Dimethyl-5,6-dihydro-ZN-thiazolo 2,3-c 1,2,4 thiadiazol-3-ylenimino) 4- (2-propynyl-2H-1,4-benzoxazine -3 (4H) -on93
    1.106- (6,6-Dimethyl-5,6-dihydro-ZN-thiazolo 2,3-c 1,2,4 thiadiazol-3-ylenimino) -4-propyl-2H-1,4-benzoxazin-3 (4H ) -one53
    1.116- (6,6-Dimethyl-3,5,6,7-tetrahydropyrrolo 2,1-c 1,2,4, thiadiazol-3-ylenimino) -4-propyl-2H1, 4-benzoxazin-3 (4H) —on41: 1.6068
    1.127- (6,6-Dimethyl-3,5,7-tetrahydropyrrolo 2,1-c 1,2,4 thiadiazol-3-ylidenimino) -1- (2-propynyl) -2- (1H) -quinoxalinon163
    1.137- (6,6-Dimethyl-5,6-dihydro-ZN-thiazolo 2,3-c 1,2,4 thiadiazol-3-ylenimino) -1- (2-propinyl) -2- (1H) quinoxalinon174
    1.146- (6,6-Dimethyl-3,5,6,7-tetrahydropyrrolo 2,1-с11,2,4 thiadiazol-3-ylenimino) -4- (2-propinyl) -2H-1,4-benzthiazine- 3 (4H) -one65
    517222046
    1.156- (6,6-Dimethyl-5, b-dihydro-ZN-thiazol-2 ,, 2.4 thiadiazol-3-yldenium N o} -7-fluto-p-4- (2-prop and n and l) -2 H-1,4-benzoxazin-3 (4H) -on135-140
    1.166- (6,6-Dimethyl-3,5,6,7-tetrahydropyrrolo
    2,1-cJI, 2,41giadiazol-3-ylidenimino) -7-fluoro-4-propyl-2H-1,4-benzoxazin-3 (4H) -on 161
    1.176- {6,6-Dimethyl-5,6-dihydro-ZN-thiazolo
    2,3-с11,2,4 thiadiazol-3-ylideneimino) -7-fluoro-4-propyl-2H-1,4-benzoxazin 3 (4H) -on 156
    1.184-Cyanomethyl-6- (6,6-dimethyl-3,5,6,7-tetrahydropyrrolo 2 ,, 2,4 thiadiazol-3-ylidenimino H-M-benzoxazin-3 (4H) -on170-171
    1.196- (6,6-Methyl-3,5,6,7-tetrahydropyrrolo
    2,1-с11,2,4 thiadiazol-3-ylidenimino) - 4- (2-propinyl) -2H-1,4-benzoxazin3 (4H) -one-171-172
    1.207-Fluoro-6- (6-methyl-3,5,6,7-tetrahydropyrrolo 2, 2.4 thiadiazol-3-ylidenimino) - 4- (2-propinyl) -2H-1,4-benzoxazin3 (4H he is 161-162
    1.215- (6,6-Dimethyl-3,5,6,7-tetrahydropyrrolo 2, 1-с11,2,4 thiadiazol-3-ylmenimino-3-propyl-2 (ZN) -benzoxazolone 113
    1.225- (6,6-Dimethyl-5,6-dihydro-ZN-thiazolo 2,3-s
    1,2,4 thiadiazol-2-ylidenimino) -3-pr-opil-2 (ZN) -benzoxazolone113
    1.235- (6,6-Dimethyl-3,5,6,7-tetrahydropyrrolo
    2,1-с11,2,4 thiadiazol-3-ylidenimino) -6-fluoro-3-propyl-2 (ZN) -benzoxazol124-127
    1.245- (6,6-Dimethyl-5,6-dihydro-ZN-thiazolo
    2,3-s11,2,4 thiadiazol-3-ylidenimino) -6-fluoro-3-propyl-2 (3N) -benzoxazolone 141-142
    1.255- (6,6-Dimethyl-3,5,6,7-tetrahydropyrrolo
    2,1-с11,2,4 thiadiazol-3-ylidene-imino) -3- (2-propinyl) -2 (ZN) -benzoxazolone 158
    1.265- (6,6-Dimethyl-5,6-dihydro-ZN-thiazole
    2,3-cJI, 2,4 thiadiazol-3-ylidenimino) -3- (2-propinyl) -2 (ZN) -benzoxazolone 137
    1.275 (6,6-Dimethyl-3,5,6,7-tetrahydropyrrolo
    2,1-с11,2,4 thiadiazol-3-ylidenimino) -6-fluoro-3- (2-propynyl) -2 (ZN) -benzoxazolone 169-173
    1.285- (6,6-Dimethyl-5,6-dihydro-ZN-thiazolo
    2,3-с11,2,4 thiadiazol-3-ylidenimino) -6-fluoro-3- (2-propynyl) -2 (ZN) benzoxazolone 138-142
    EXAMPLE 2. Preparation of 1-6-fluoro-2-oxogts, stirred for 8 hours at 80 ° C, cooled 3- (2-propynyl) -2,3-dihydrobenzoxazole-5-th reaction mixture was poured into 500 ml
    , 4-dimethyl-3-pyrrolin-2.5 (1H) -dioned water, precipitated Cree (compound 2.01) are sucked off and washed with ice water. Dried
    To a solution of 4 g of 5-amino-6-fluoro-3- (2-pro-20 in vacuum at 50 ° C.
    pinyl) -2 (ZN) -benzoxazolone in 50 ml of ice -Exit 2.3 g (38% of theory), so pl. 165 ° C. 2.8 g are added in acetic acid in the same way. 2,3-dimethylmaleic acid compounds are obtained following the anhydride.
    717222048
    Ms of compound Compound: mp, ° C
    2.021-6-Fluoro-2-oxo-3- (2-propynyl) -2,3 dihydro-benzthiazol-5-yl-3, 4-dimethyl-3-pyrrolin-2.5 (1H)) -dione 229
    2.031- 3-oxo-4- (2-Propinyl) -3,4-dihydro2H-1, 4-benzthiazin-6-yl-3,4-dimethyl-3-pyrrolin-2.5 (1H) -dione279
    2.041-2-oxo-2,3-dihydro-1H-benzimidazol-5-yl-3, 4-dimethyl-3-pyrrolin2, 5 (1H) -dione280
    2.051- 2-oxo-1- (2-Propynyl) -1H-quinoxalin-7-yl-3, 4-dimethyl-3-pyrrolin2, 5 (H) -dione265
    2.06 1- 2-oxo-3- (2-Propinyl) -2,3-dihydrobenzoxazol-5-yl-3, 4-dimethyl-3-pyrrolin-2, 5 (1H) -dione 189
    2.07H2-oxo-3-Propyl -2,3-dihydrobenzoxazol-5-yl-3, 4-dimethyl-3-pyrrolin2, 5 (1H) -dione110
    2.081-3-Methyl-2-oxo-1-propyl-1,3-dihydro2H-indole-6-yl-3, 4-dimethyl-3-pyrrolin-2, 5 (1H dion180
    2.091-3-methyl-2-oxo-1- (1-methylethyl) -1,3-dihydro-2H-indole-6-yn-3, 4-dimethyl-3-pyrrolin-2.5 (1H) -dione142-144
    Example 3. Preparation of 2- 7-fluoro-3-oxo-noic acid. Boil t 10 h at boiling.
    4- (2-propynyl) -3,4-dihydro-2H-1,4benzox-After cooling, the solvent is distilled off into
    azin-6-yl - perhydroimidazo 1,5-a under a pyri-vacuum and the residue is separated on a column with
    din-1,3-dione (compound 3.01). silica gel using acetic ester 5p / hexane.
    6.4 g of 7-fluoro-4- (2-propynyl) -Exit 4.8 g (52% of theory) are dissolved, m.p. 2021, 4-beoxoxin-3- (4H) -on-6-yl-isocyanate B 204 ° C.
    50 ml of tetrahydrofuran and the following are added in an analogous manner: 4 ml of piperidine-2-carboxylic ester:
    Compound ns Compound mp. ° C
    3.022-3-oxo-4- (2-propinyl) -3,4-dihydro-2H-1, 4-benzoxazin-6-yl -perhydroimidazo 1,5-a-pyridine-1,3-dione 180-185
    3.032-3-oxo-4- (2-Propinyl) -3,4-dihydro2H-1, 4-benzoxazin-6-yl -perhydroimidazo 1, 5-a-pyridine-1,3 Dion157-158
    3.042-7-Fluoro-3-oxo-4- (2-propynyl) -3,4 dihydro-2H-1, 4-benzoxazin-6-yl J-3-thioxoperhydroimidazo 1,5-a pyridin-1-one 151
    3.052-6-Fluoro-2-oxo-3- (2-propynyl) -2,3-dihydro-benzoxazol-5-yl-3-thioxoper hydroimidazo 1,5-a pyrimidin-1-one 189-195
    3.062- (2-oxo-1- (2-Propinyl) -1H-quinoxalin-7yl-perhydroimidazo 1, 5-a pyridine1, 3-dione199-200
    3.072-2-oxo-3- (2-P roles, 3-di hydrobene nzoxazol-5-and -perhydroimidazo 1, 5-a pyridine-1,3-dione179
    EXAMPLE 4: Preparation of 3- (3-oxo-4-propyl-3,4-dihydro-2H-1,4-benzoxazin-6-yl) -5,6,7,8 tetrahydroquinazoline 2.4 (1H, 3N) - dione (compound 4.01).
    2.0 g of sodium metal is dissolved in 100 ml of ethanol, 4.4 g of ethyl ester (3-oxo-4-propyl-3,4-dihydro - {2H) -1,4-benzoxazin-6- or ) -ureic acid to -1-cyclohexenecarboxylic acid, dissolved in 50 ml of ethanol, and the reaction mixture is heated to boiling for 1 hour. After completion of the reaction, the solution is concentrated, the residue is mixed with 300 ml of water, the precipitate is filtered off and the filtrate is acidified with hydrochloric acid. The precipitated product is filtered off with suction, washed with water and recrystallized from ethyl acetate / diisopropyl ether.
    Output: 3.56 g (56% of theory), so pl. 250 ° C.
    Preparation of 1-methyl-3- (4-propyl-3,4-di-hydro-2H-1,4-benzoxazin-6-yl) -5,6,7,8-tetrahydroquinazolin-2.4 (1 H, ZN) -dione (compound 4.02).
    2.0 g of 3- (4-propyl-1,5-benzoxazin-3- (4H) -on-6-yl) -5,6,7,8-tetrahydroquinazoline -2.4 (1 H, 3N) - dione is dissolved in 20 ml of dimethylformamide, 0.17 g of 80% sodium hydride suspension is added and stirred
    1 hour at 60 ° C. The mixture is cooled to room temperature, 0.77 g of iodomethane is added, the mixture is heated to 60 ° C for 2 hours. After cooling, the precipitated crystals are filtered off with suction and recrystallized from diisopropyl ether / ethyl acetate.
    Output 1.3 g (65% of theory), 218 ° C. PRI mme R 5. Getting 2- 6-fluoro-2-oxy-so-3- (2-propinyl) -2,3-dihydrobenzthiazol-5yl -2,3,5,6,7,8-hexahydro -1,2,4-triazolo 4,3-a pyridin-3-one (compound 5.01).
    3.6 g of 5-hydrazino-6-fluoro-3- (2-propynyl) -benzthiazolone are dissolved in 40 ml of xylene, 2.8 g of 1-ethoxycarbonyl2-piperidone and 1 g of half-thioxyphosphorus and bale are added t t mixture for 2 h at boiling. After cooling, the reaction mixture is added to 100 ml of water and the organic phase is separated. The organic phase is washed with 40 ml.
    potassium bicarbonate solution, dried over magnesium sulphate and concentrated. The residue is chromatographed on silica gel with ethyl acetate / hexane mixtures as a solvent.
    Exit 380 mg (6.7% of theory), so pl.
    154-160 ° C.
    The following compounds are prepared in a similar manner:
    unity


    Compound
    2- 2-oxo-3- (2-propynyl) -2,3-dihydrobenzoxazol-5-yl -2,3,5, 6,7,8-hexagidro-1,2,4-triazolo 4 , 3-pyridine-3-one
    2- 7-Fluoro-3-oxo-4- (2-pop in and l) 3,4-dihydro-2H-1,4-benzoxazin-6-yl - 2,3,5,6,7,8 -hexahydro-1,2,4-tria, 3-a pyridin-3-one 2- 6-fluoro-2-oxo-1- (2-propynyl) -3,4-di-hydro-1H-hinoxanine 7-yl -2,3,5,6,7,8-hexahydro-1,2,4-triazolo 4,3-a pyridine-3-one
    2-6-Fluoro-2-oxo-1- (2-propinyl-1H-chinoxalin-7-yl -2,3,5,6,7,8, -hexahydro-1,2,4-triazolo- 4.3 Pyridin-3-one 2-6-Fluoro-2-oxo-3,4-dihydro-1H-quinoxaline-7-yl -2,3,5,6,7,8-hexahydro-1, 2,4-triazolo-4,3-a pyridin-3-one
    Example Preparation of 2- 7-fluoro-3-ox-so-4- (2-propynyl) -3,4-dihydro-2H-1,4-benz oxazin-6, 5,6,7-tetrahydro-2H-1, 2,3-triazolo 3,4-a pyridin-8-y-3-olata (compound 6.01).
    5.0 g 6-amino-7-fluoro-4- (2-propynyl) -2H-1,4-benzoxazin-3 (-4H) -one is suspended in a mixture of 12.2 ml of concentrated salt T. Mp. ° WITH
    190 194-196
    226-230 210-211 190-192
    Acidic acid and 52 ml of water and cooled to -10 ° C and -5 ° C. A solution of 1.74 g of sodium nitrite in 6 ml of water is added dropwise so that the temperature of the reaction mixture does not exceed -5 ° C. At the end of the addition, the mixture is stirred at -5 ° C for 1 hour and the excess nitrous acid is decomposed with urea, until the test becomes negative with
    using the reaction with iodine starch paper. The solution thus obtained is heated to 0 ° C. and 2.9 g of pipecolic acid and 10.5 ml of triethylamine are poured into an ice-cooled solution in 38 ml of water. At the end of the addition, the mixture is stirred at 0 ° C for 1 h and the reaction mixture is extracted several times with methylene chloride. The combined organic phases are dried over magnesium sulfate and the solvent is evaporated. The residue is dissolved in 60 ml of ether and mixed with 5.2 ml of anhydrous compound 6.02.
    6.03
    ConnectionT.pl., ° C
    2- 6-Fluoro-2-oxo-3- (2-propynyl) -2,3 dihydro-benzoxazol-5-yl 4, 5,6,7-tetrahydro-2H-1, 2,3-triazolo 3,4- and pyridine-8th-olat203
    2- 6-Fluoro-2-oxo-3- (2-propynyl) -2,3-di-hydro-benzthiazol-5-ylp1,5,6,7-tetrahydro-2H-1,2,3- triazolo 3,4-a-pyridin-8th-olat 210
    Example. Preparation of 3- (3-methyl-2-ox-1-propyl-1,3-dihydro-2H-indole-6-yl-5 - (1,1-dimethyl-ethyl) -1,3,4- oxadiazol-2 (ZN) -one (compound 7.01).
    2.6 g of 3-methyl-6-M - (2,2-dimethylpropanoyl) -hydrazino -1-propyl-1H- -indole-2 (3N) -one is dissolved in 15 ml of a 20% phosgene solution in toluene and then boil for 4 hours. Stir overnight at room temperature, then carefully add
    unity

    Compound
    3- 2-oxo-3- (2-Propinyl) -2,3-dihydrobenzoxazol-5-yl-5- (1,1-dimethylethyl) 1,3,4-oxadiazol-2 (ZN) -one 3 - 7-Fluoro-3-oxo-4- (2-propinyl) -3,4-di-hydro-2H-1,4-benzoxazin-6-yl} -5- (1,1-dimethylethyl) - 1,3,4-oxadiazol-2 (ZN) -one 3-6-Fluoro-2-oxo-1- (2-propynyl) -3,4-di-hydro-1H-hinoxan-7-yl 5- ( 1,1-dimethylethyl) 1,3,4-oxadiazol-2 (3N) -one 3 6-Fluoro-2-oxo-1 - (2-propynyl) -1 H-quinoxaline-7-yl - 5- (1,1-dimethylethyl) 1, 3,4-oxadiazol-2 (ZN) -one 3- {7-Fluoro-3-oxo-3,4-dihydro-2H-1,4 benzoxazin-6- IL-5- (1,1-dimethylethyl) -1,3,4-oxadiazol-2 (3N) -one 3-6-Fluoro-2-oxo-3,4-dihydro-2H-quinoxaline-7- IL-5- (1,1-dimethylethyl) -1,3,4-oxadiazol-2 (3H) -one
    0
    Read acetic acid and 2.6 ml of pyridine. The mixture is stirred overnight at room temperature and then poured onto 150 ml of ice-cold water, extracted with ethyl acetate, dried with magnesium sulfate and the solvent is evaporated. The residue is chromatographed on silica gel with a solvent of ethyl acetate / methanol 95: 5.
    Output 1.0 g (13% of theory), so pl. 202-203 ° C.
    The following compounds are prepared in a similar manner:
    20 ml of methanol and distilled off the solution in vacuo. The residue is chromatographed on silica gel with a solvent of hexane / ethyl acetate 7: 3.
    Output 1.7 g (61% of theory),, 5366.
    The following compounds are prepared in a similar manner:
    Mp ° C
    127-130 143-144 66-68 152-153 171-172 248
    ExampleB Preparation of 3-chloro-2-2-oxy-3-3- (2-propynyl) -2,3-dihydrobenzoxazole-5-yl-4 5,6,7-tetrahydro-2H-indazole (compound 8.01).
    4.5 g of 2- 2-oxo-3- (2-propynyl) -2,3-dihydrobenzoxazol-5-yl 1,3,4,5,6, 7-hexahydro-2H-indazol-3- are mixed It is filled with 20 ml of rxalil chloride and boiled for 4 hours. After cooling, the reaction mixture is poured into 100 ml of ice water, extracted with methylene chloride, the organic compound 8.02 is combined.
    8.03
    ConnectionT.pl., ° C
    3-Chloro-2-7-fluoro-3-oxo-4-2-propynyl) -3,4-dihydro-2H-1,4-benzoxazin-6-yl -4,5,6,7-tetra hydro2H- indazol 150
    3-Chloro-2- 6-fluoro-3-oxo-1 - (2-p ropinyl) -3,4-dihydro-1 H-quinoxalin-7-yl 4, 5,6,6-tetrahydro-2H-iodazole 195
    Preparative forms of herbicide means:
    A. Wettable powder, wt.%: Active substance 20; bentonite 35; silicon acid 35; calcium salt of ligninsulfonic acid 8; sodium salt of N-methyl-M-oleyl taurine 2,
    B. Emulsifiable concentrate, wt.%: Active substance 20; isophorone 75; dodecyl benzene sulphoxy acid 2 calcium salt; nonylphenylpolyoxyethylene 3.
    PRI me R 9. Post-harvest processing of plants.
    Experimental plants are grown in greenhouses up to a certain stage of development and treated with a suspension of a wettable powder at the rate of 0.1 kg of active substance per hectare and water consumption of 500 l / ha.
    Evaluation of herbicidal activity was carried out three weeks after treatment on a scale from 0 to 4 points: 0 - no damage; 1 - up to 24 damage; 2 - 25-74% damage; 3 - 75-89% damage; 4 - 90-100% damage.
    For comparison, a known herbicide is used.
    The results of the experiments are presented in table.1.
    0
    The phases are extracted by shaking with a saturated solution of sodium bicarbonate and with water, dried over magnesium sulfate. The solvents are distilled off in vacuo. The residue is chromatographed on silica gel with hexane / ethyl acetate mixtures as solvents.
    Output 3.9 g (82% of theory), so pl. 143-146 ° C.
    The following compounds are prepared in a similar manner:
    five
    0
    50
    five
    0
    Under the conditions of Example 9, other experiments were carried out, the results of which are presented in Tables 2-5. In this case, a germicidal agent in the form of an emulsifying concentrate is used.
    An example. Pre-emergence treatment of plants. The seeds of the experimental plants are sown in special vessels under greenhouse conditions and then the soil is treated with active substances in the form of a suspension of a wettable powder at a rate of 0.1 kg / ha of active substance with a water consumption of 500 l / ha.
    Evaluation of herbicidal activity was carried out weeks after treatment according to the rating scale presented in Example 9.
    The results of the experiments are presented in table 6 and 7.
    权利要求:
    Claims (1)
    [1]
    Invention Formula
    A herbicidal agent containing an active substance - a heterocyclic nitrogen-containing compound, a carrier and a surfactant, characterized in that, in order to increase the herbicidal activity, it contains as an active substance a heterocyclic nitrogen-containing compound of the general formula
    five
    I
    where Ri is hydrogen, methyl, cyanomethyl, propyl, isopropyl, allyl, 2,3-dibromollyl, propinyl;
    X - CH (CH3), CH2NH, CHrN. CH20, CH2S, NH. O, S;
    Y is hydrogen, fluorine;
    Z is a heterocyclic fragment of Zi-Ze,
    about „-snz
    -VV 4 / J. K.
    . - (22) - (Z3)
    : ° з «о va
    Wus)
     J.
    n vi
    H, MV
    -N-VI
    W (z,)
    a is hydrogen or methyl; Нз - hydrogen or methyl; U is oxygen or sulfur;
    (2,}
    0
    five
    T-CH2 or S;
    provided that if Z is Zi, then X does not mean CH20; if Z means 7.2 or Z4, then X does not mean S; as a carrier, a mixture of bentonite and silicic acid at a mass ratio of 35:35 or isophorone; and as a surfactant - a mixture of calcium salt of ligninsulfonic acid and sodium salt of M-methyl-M-oleyl taurine at a mass ratio of 8: 2 or a mixture of potassium salt of dodecylbenzenesulfonic acid and nonylphenyl polyoxyethylene at a mass ratio of 2: 3 with the following content of ingredients of the herbicidal agent, wt. %:
    Active substance20
    Carrier70-75 Surface-active
    substance5-10
    Table 1
    O 1 1 1 O 2
    k k k k k 2
    Table 2
    Tablez
    Table
    3
    four
    3
    four
    four
    four
    3 4 3 4 4 2
    nineteen
    1722204
    20
    Table3
    类似技术:
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    SU1722204A3|1992-03-23|Herbicide agent
    AU605304B2|1991-01-10|Benzo-fused cyclic compounds
    EP0105721B1|1987-11-11|2-substituted phenyl-4,5,6,7-tetrahydro-2h-indazoles, and their production and use
    DK164503B|1992-07-06|AZOLYLOXYCARBOXYLIC ACID AMIDES, THEIR PREPARATION AND THEIR USE AS HERBICIDE AGENTS
    EP0328001B1|1993-08-11|Benzoxazinone compounds and herbicidal composition containing the same
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    AU609512B2|1991-05-02|Tetrahydroindazolyl-benzoxazines, their production and use
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    GB2119252A|1983-11-16|Use of thiadiazolylimidazolidinones to control aquatic vegetation
    JPH07304759A|1995-11-21|Iminothiazolone derivative and use thereof
    KR19990036324A|1999-05-25|Pyrimidin-4-one derivatives, their use as herbicides, intermediates for their preparation, and methods of preparing these compounds
    JP2762505B2|1998-06-04|Condensed heterocyclic derivative, production method and herbicide
    US4824465A|1989-04-25|Benzothiazolones, and their production and use
    JPH06321941A|1994-11-22|Dihydrobenzofuran derivative and herbicide containing the same as active ingredient
    EP0705829A1|1996-04-10|Epoxyphenol derivatives and herbicides containing them as active ingredients
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    JPH09221483A|1997-08-26|Arylthiadiazolone compound having herbicidal activity
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    同族专利:
    公开号 | 公开日
    JPH01157977A|1989-06-21|
    PH27146A|1993-04-02|
    FI884625A|1989-04-10|
    IL87887D0|1989-03-31|
    FI92585B|1994-08-31|
    HU207330B|1993-03-29|
    BR8805182A|1989-05-23|
    AU614775B2|1991-09-12|
    AR244235A1|1993-10-29|
    ES2058206T3|1994-11-01|
    AU2356888A|1989-04-13|
    DE3881468D1|1993-07-08|
    EP0311135B1|1993-06-02|
    AT90091T|1993-06-15|
    KR890006615A|1989-06-14|
    FI92585C|1994-12-12|
    EP0311135A3|1989-09-06|
    IL87887A|1993-04-04|
    EP0311135A2|1989-04-12|
    DE3734745A1|1989-04-20|
    CN1032479A|1989-04-26|
    DK563488D0|1988-10-07|
    HUT49356A|1989-09-28|
    FI884625A0|1988-10-07|
    JP2765873B2|1998-06-18|
    DK563488A|1989-04-10|
    ZA887559B|1989-06-28|
    DD282847A5|1990-09-26|
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    法律状态:
    优先权:
    申请号 | 申请日 | 专利标题
    DE19873734745|DE3734745A1|1987-10-09|1987-10-09|TETRAHYDROPYRROLO -THIADIAZOL-3-YLIDENIMINOBENZOXAZINONE AND OTHER HETEROCYCLICALLY SUBSTITUTED AZOLES AND AZINES, METHODS FOR THE PRODUCTION THEREOF AND THEIR USE AS AGENTS WITH HERBICIDES|
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