SU1422997A3 - Способ получени производных N-фенилпиразола - Google Patents
Способ получени производных N-фенилпиразола Download PDFInfo
- Publication number
- SU1422997A3 SU1422997A3 SU843814606A SU3814606A SU1422997A3 SU 1422997 A3 SU1422997 A3 SU 1422997A3 SU 843814606 A SU843814606 A SU 843814606A SU 3814606 A SU3814606 A SU 3814606A SU 1422997 A3 SU1422997 A3 SU 1422997A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- hydrogen
- chlorine
- fluorine
- leaves
- compounds
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 6
- 230000012010 growth Effects 0.000 claims abstract description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 12
- 239000001257 hydrogen Substances 0.000 claims abstract description 12
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 11
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 9
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 7
- 239000011737 fluorine Substances 0.000 claims abstract description 6
- WITMXBRCQWOZPX-UHFFFAOYSA-N 1-phenylpyrazole Chemical class C1=CC=NN1C1=CC=CC=C1 WITMXBRCQWOZPX-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract 4
- 150000001875 compounds Chemical class 0.000 claims description 30
- 239000000460 chlorine Substances 0.000 claims description 7
- -1 alkali metal acetate Chemical class 0.000 claims description 5
- 235000007320 Avena fatua Nutrition 0.000 claims description 4
- 241000209764 Avena fatua Species 0.000 claims description 4
- 244000058871 Echinochloa crus-galli Species 0.000 claims description 3
- 235000011999 Panicum crusgalli Nutrition 0.000 claims description 3
- 240000006694 Stellaria media Species 0.000 claims description 3
- 241000990144 Veronica persica Species 0.000 claims description 2
- 238000009835 boiling Methods 0.000 claims description 2
- 239000011541 reaction mixture Substances 0.000 claims description 2
- 238000010992 reflux Methods 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims 2
- 241000219144 Abutilon Species 0.000 claims 1
- 241001621841 Alopecurus myosuroides Species 0.000 claims 1
- 244000025254 Cannabis sativa Species 0.000 claims 1
- 241000205407 Polygonum Species 0.000 claims 1
- 241000405217 Viola <butterfly> Species 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 239000000654 additive Substances 0.000 claims 1
- 230000000996 additive effect Effects 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 238000007363 ring formation reaction Methods 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 241000196324 Embryophyta Species 0.000 abstract description 25
- 230000002363 herbicidal effect Effects 0.000 abstract description 8
- 239000000203 mixture Substances 0.000 abstract description 8
- 238000002360 preparation method Methods 0.000 abstract description 2
- 239000000543 intermediate Substances 0.000 abstract 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 20
- 239000000243 solution Substances 0.000 description 20
- 238000012360 testing method Methods 0.000 description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 238000002474 experimental method Methods 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
- 229960000583 acetic acid Drugs 0.000 description 5
- 238000012545 processing Methods 0.000 description 5
- 238000005507 spraying Methods 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
- 241000209140 Triticum Species 0.000 description 4
- 235000021307 Triticum Nutrition 0.000 description 4
- 229940125904 compound 1 Drugs 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 239000000377 silicon dioxide Substances 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 240000005702 Galium aparine Species 0.000 description 3
- 235000014820 Galium aparine Nutrition 0.000 description 3
- 239000010426 asphalt Substances 0.000 description 3
- 239000002361 compost Substances 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 230000008635 plant growth Effects 0.000 description 3
- 230000026267 regulation of growth Effects 0.000 description 3
- LWEAHXKXKDCSIE-UHFFFAOYSA-M 2,3-di(propan-2-yl)naphthalene-1-sulfonate Chemical compound C1=CC=C2C(S([O-])(=O)=O)=C(C(C)C)C(C(C)C)=CC2=C1 LWEAHXKXKDCSIE-UHFFFAOYSA-M 0.000 description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 229940126062 Compound A Drugs 0.000 description 2
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 2
- 241000220261 Sinapis Species 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WNAGVMRWPDSQKD-UHFFFAOYSA-N [2,3,6-trichloro-4-(trifluoromethyl)phenyl]hydrazine Chemical compound NNC1=C(Cl)C=C(C(F)(F)F)C(Cl)=C1Cl WNAGVMRWPDSQKD-UHFFFAOYSA-N 0.000 description 2
- 230000033228 biological regulation Effects 0.000 description 2
- 229940125782 compound 2 Drugs 0.000 description 2
- 229940126214 compound 3 Drugs 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000004009 herbicide Substances 0.000 description 2
- 238000005580 one pot reaction Methods 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- 239000004576 sand Substances 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- RSICFPWUVXKGAA-UHFFFAOYSA-N 1-[2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl]pyrazole-3-carbonitrile Chemical compound C(#N)C1=NN(C=C1)C1=C(C(=C(C(=C1F)F)C(F)(F)F)F)F RSICFPWUVXKGAA-UHFFFAOYSA-N 0.000 description 1
- OFOAHTJXJLENGQ-UHFFFAOYSA-N 2,3,6-trichloro-4-(trifluoromethyl)aniline Chemical compound NC1=C(Cl)C=C(C(F)(F)F)C(Cl)=C1Cl OFOAHTJXJLENGQ-UHFFFAOYSA-N 0.000 description 1
- KGIWPGKKIFFMKP-UHFFFAOYSA-N 2-(ethoxymethylidene)-3-hydroxybutanedinitrile Chemical compound CCOC=C(C#N)C(O)C#N KGIWPGKKIFFMKP-UHFFFAOYSA-N 0.000 description 1
- OEICGMPRFOJHKO-UHFFFAOYSA-N 2-(ethoxymethylidene)propanedinitrile Chemical compound CCOC=C(C#N)C#N OEICGMPRFOJHKO-UHFFFAOYSA-N 0.000 description 1
- MBBUTABXEITVNY-UHFFFAOYSA-N 2-chloro-4-(trifluoromethyl)aniline Chemical compound NC1=CC=C(C(F)(F)F)C=C1Cl MBBUTABXEITVNY-UHFFFAOYSA-N 0.000 description 1
- QOTPAJSOTBKLAP-UHFFFAOYSA-N 3-aminoheptan-4-one Chemical compound CCCC(=O)C(N)CC QOTPAJSOTBKLAP-UHFFFAOYSA-N 0.000 description 1
- KZAMRRANXJVDCD-UHFFFAOYSA-N 3-chloro-4-(trifluoromethyl)aniline Chemical compound NC1=CC=C(C(F)(F)F)C(Cl)=C1 KZAMRRANXJVDCD-UHFFFAOYSA-N 0.000 description 1
- WUBKSRNCHJHRCD-UHFFFAOYSA-N 5-amino-1-[2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl]pyrazole-4-carbonitrile Chemical compound NC1=C(C#N)C=NN1C1=C(F)C(F)=C(C(F)(F)F)C(F)=C1F WUBKSRNCHJHRCD-UHFFFAOYSA-N 0.000 description 1
- VUUJEGLTTLCWLF-UHFFFAOYSA-N 5-amino-1-[2,3,6-trichloro-4-(trifluoromethyl)phenyl]pyrazole-4-carbonitrile Chemical compound NC1=C(C#N)C=NN1C1=C(Cl)C=C(C(F)(F)F)C(Cl)=C1Cl VUUJEGLTTLCWLF-UHFFFAOYSA-N 0.000 description 1
- NASYGBVRGNBDOD-UHFFFAOYSA-N 5-amino-1-[2-chloro-4-(trifluoromethyl)phenyl]pyrazole-4-carbonitrile Chemical compound NC1=C(C#N)C=NN1C1=CC=C(C(F)(F)F)C=C1Cl NASYGBVRGNBDOD-UHFFFAOYSA-N 0.000 description 1
- MAKQREKUUHPPIS-UHFFFAOYSA-N 5-amino-1-phenyl-1H-pyrazole-4-carbonitrile Chemical compound NC1=C(C#N)C=NN1C1=CC=CC=C1 MAKQREKUUHPPIS-UHFFFAOYSA-N 0.000 description 1
- FVALFZYSHWCLMS-UHFFFAOYSA-N 5-amino-3-methyl-1-(2,3,4-trichlorophenyl)pyrazole-4-carbonitrile Chemical compound NC1=C(C#N)C(C)=NN1C1=CC=C(Cl)C(Cl)=C1Cl FVALFZYSHWCLMS-UHFFFAOYSA-N 0.000 description 1
- 240000006995 Abutilon theophrasti Species 0.000 description 1
- 241000743985 Alopecurus Species 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- UDHXJZHVNHGCEC-UHFFFAOYSA-N Chlorophacinone Chemical compound C1=CC(Cl)=CC=C1C(C=1C=CC=CC=1)C(=O)C1C(=O)C2=CC=CC=C2C1=O UDHXJZHVNHGCEC-UHFFFAOYSA-N 0.000 description 1
- 244000018716 Impatiens biflora Species 0.000 description 1
- 101100005318 Mus musculus Ctsr gene Proteins 0.000 description 1
- 235000019502 Orange oil Nutrition 0.000 description 1
- 240000006928 Persicaria lapathifolia Species 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- 241000394440 Viola arvensis Species 0.000 description 1
- 241001148683 Zostera marina Species 0.000 description 1
- TVSDZBUZBHRNBV-UHFFFAOYSA-N [2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl]hydrazine Chemical compound NNC1=C(F)C(F)=C(C(F)(F)F)C(F)=C1F TVSDZBUZBHRNBV-UHFFFAOYSA-N 0.000 description 1
- FYOWOHMZNWQLFG-UHFFFAOYSA-N [2,6-dichloro-4-(trifluoromethyl)phenyl]hydrazine Chemical compound NNC1=C(Cl)C=C(C(F)(F)F)C=C1Cl FYOWOHMZNWQLFG-UHFFFAOYSA-N 0.000 description 1
- KSESZRGARIEOFC-UHFFFAOYSA-N [2-chloro-4-(trifluoromethyl)phenyl]hydrazine Chemical compound NNC1=CC=C(C(F)(F)F)C=C1Cl KSESZRGARIEOFC-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 229940040526 anhydrous sodium acetate Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000035784 germination Effects 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 239000003415 peat Substances 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 230000035040 seed growth Effects 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/38—Nitrogen atoms
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8122142 | 1981-07-17 | ||
| GB8203369 | 1982-02-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU1422997A3 true SU1422997A3 (ru) | 1988-09-07 |
Family
ID=26280166
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU843814606A SU1422997A3 (ru) | 1981-07-17 | 1984-11-23 | Способ получени производных N-фенилпиразола |
Country Status (28)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2136665C1 (ru) * | 1994-02-22 | 1999-09-10 | Рон-Пуленк Агрошими | Способ сульфинилирования гетероциклических соединений, способ получения 4- сульфинилпиразолов и сульфинамидные соединения |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3420985A1 (de) * | 1983-10-15 | 1985-04-25 | Bayer Ag, 5090 Leverkusen | Substituierte 5-acylamino-1-phenylpyrazole |
| DE3575130D1 (de) * | 1984-05-12 | 1990-02-08 | Fisons Plc | Antiinflammatorische 1,n-diarylpyrazol-3-amine, deren zusammensetzungen und verfahren zu deren herstellung. |
| DE3423582A1 (de) * | 1984-06-27 | 1986-01-09 | Bayer Ag, 5090 Leverkusen | Substituierte 5-acylamino-1-phenylpyrazole |
| DE3539844A1 (de) | 1985-11-09 | 1987-05-14 | Bayer Ag | Substituierte 5-amino-1-aryl-pyrazole |
| DE3706993A1 (de) * | 1987-03-05 | 1988-09-15 | Bayer Ag | 5-amino-3-halogenalkyl-1-aryl-pyrazole |
| DE3737986A1 (de) * | 1987-11-09 | 1989-05-18 | Bayer Ag | Fluor und/oder chlor enthaltende trifluormethylaminobenzole und deren herstellung |
| DE10219435A1 (de) * | 2002-05-02 | 2003-11-13 | Bayer Cropscience Ag | Substituierte Pyrazolo-pyrimidin-4-one |
| CN106074278B (zh) | 2010-09-09 | 2020-11-27 | 玫琳凯有限公司 | 包含植物提取物的局部护肤制剂 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3760084A (en) * | 1972-05-01 | 1973-09-18 | American Cyanamid Co | Method of using 5-amino-1-phenyl or substituted phenyl-4-pyrazolecarbonitriles or carbox-amides |
| EP0026034B1 (en) * | 1979-08-23 | 1983-03-23 | Fbc Limited | 5-amino-4-cyano-1-(2,4,6-trichlorophenyl)pyrazole, process for its preparation, herbicidal compositions containing it and their use |
| BG35741A1 (en) * | 1980-02-26 | 1984-06-15 | May & Baker Ltd | Herbicide composition and method for protection from weeds |
| EP0053699B1 (de) * | 1980-12-05 | 1983-09-21 | BASF Aktiengesellschaft | 2'-Phenylhydrazino-2-cyanacrylsäureester und diese enthaltende Herbizide |
-
1982
- 1982-07-14 MA MA19747A patent/MA19539A1/fr unknown
- 1982-07-15 CA CA000407320A patent/CA1228859A/en not_active Expired
- 1982-07-15 IE IE1699/82A patent/IE53427B1/en unknown
- 1982-07-15 PT PT75255A patent/PT75255B/pt unknown
- 1982-07-15 US US06/398,336 patent/US4505740A/en not_active Expired - Fee Related
- 1982-07-15 BR BR8204107A patent/BR8204107A/pt unknown
- 1982-07-15 NL NL8202864A patent/NL8202864A/nl not_active Application Discontinuation
- 1982-07-15 PL PL1982237490A patent/PL133283B1/pl unknown
- 1982-07-15 CH CH1562/83A patent/CH657360A5/fr not_active IP Right Cessation
- 1982-07-15 BG BG057419A patent/BG37672A3/xx unknown
- 1982-07-15 HU HU822304A patent/HU188583B/hu unknown
- 1982-07-15 GB GB08220498A patent/GB2105324B/en not_active Expired
- 1982-07-15 GR GR68774A patent/GR77224B/el unknown
- 1982-07-15 AT AT0276982A patent/AT383253B/de not_active IP Right Cessation
- 1982-07-15 DK DK318482A patent/DK318482A/da not_active Application Discontinuation
- 1982-07-15 AU AU86029/82A patent/AU563147B2/en not_active Ceased
- 1982-07-15 IT IT48823/82A patent/IT1157220B/it active
- 1982-07-15 WO PCT/GB1982/000212 patent/WO1983000331A1/en active IP Right Grant
- 1982-07-15 PH PH27573A patent/PH17961A/en unknown
- 1982-07-15 DD DD82241681A patent/DD202611A5/de unknown
- 1982-07-15 TR TR21486A patent/TR21486A/xx unknown
- 1982-07-15 SE SE8204348A patent/SE8204348L/xx not_active Application Discontinuation
- 1982-07-15 DE DE19823226496 patent/DE3226496A1/de not_active Withdrawn
- 1982-07-15 IL IL66321A patent/IL66321A/xx unknown
- 1982-07-15 NZ NZ201281A patent/NZ201281A/en unknown
- 1982-07-15 EP EP82902079A patent/EP0084033B1/en not_active Expired
-
1983
- 1983-03-17 OA OA57937A patent/OA08220A/xx unknown
-
1984
- 1984-11-14 US US06/671,243 patent/US4541963A/en not_active Expired - Fee Related
- 1984-11-23 SU SU843814606A patent/SU1422997A3/ru active
-
1985
- 1985-04-15 GB GB08509601A patent/GB2155932B/en not_active Expired
-
1987
- 1987-09-30 AU AU79224/87A patent/AU7922487A/en not_active Abandoned
Non-Patent Citations (1)
| Title |
|---|
| Peet N.R., Sunder S., Barbuch R.I. I.Heteroc. Chem., 1983, V. 20, p.511. * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2136665C1 (ru) * | 1994-02-22 | 1999-09-10 | Рон-Пуленк Агрошими | Способ сульфинилирования гетероциклических соединений, способ получения 4- сульфинилпиразолов и сульфинамидные соединения |
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