HU188583B - Herbicides containing n-phenyl-pyrazole derivatives and process for preparing the active substances - Google Patents
Herbicides containing n-phenyl-pyrazole derivatives and process for preparing the active substances Download PDFInfo
- Publication number
- HU188583B HU188583B HU822304A HU230482A HU188583B HU 188583 B HU188583 B HU 188583B HU 822304 A HU822304 A HU 822304A HU 230482 A HU230482 A HU 230482A HU 188583 B HU188583 B HU 188583B
- Authority
- HU
- Hungary
- Prior art keywords
- formula
- phenyl
- pyrazole
- amino
- cyano
- Prior art date
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- WITMXBRCQWOZPX-UHFFFAOYSA-N 1-phenylpyrazole Chemical class C1=CC=NN1C1=CC=CC=C1 WITMXBRCQWOZPX-UHFFFAOYSA-N 0.000 title claims abstract description 26
- 239000004009 herbicide Substances 0.000 title claims description 42
- 239000013543 active substance Substances 0.000 title abstract description 17
- 238000004519 manufacturing process Methods 0.000 title 1
- 230000002363 herbicidal effect Effects 0.000 claims abstract description 31
- 239000001257 hydrogen Substances 0.000 claims abstract description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 18
- 238000000034 method Methods 0.000 claims abstract description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 11
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 11
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 10
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims abstract description 7
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 78
- 239000004480 active ingredient Substances 0.000 claims description 62
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 28
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 23
- 239000007787 solid Substances 0.000 claims description 21
- 239000004094 surface-active agent Substances 0.000 claims description 21
- 239000003085 diluting agent Substances 0.000 claims description 20
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 18
- -1 trimethylbenzene aromatic hydrocarbon Chemical class 0.000 claims description 18
- 239000007788 liquid Substances 0.000 claims description 16
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 12
- 239000000843 powder Substances 0.000 claims description 12
- 239000000654 additive Substances 0.000 claims description 11
- 239000004563 wettable powder Substances 0.000 claims description 11
- 239000012141 concentrate Substances 0.000 claims description 10
- 235000008504 concentrate Nutrition 0.000 claims description 10
- 239000008187 granular material Substances 0.000 claims description 10
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
- YJHMXFBILMSTSZ-UHFFFAOYSA-N 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]pyrazole-4-carbonitrile Chemical group NC1=C(C#N)C=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl YJHMXFBILMSTSZ-UHFFFAOYSA-N 0.000 claims description 9
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 claims description 9
- 239000007900 aqueous suspension Substances 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- 239000002562 thickening agent Substances 0.000 claims description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- 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 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 6
- 239000000377 silicon dioxide Substances 0.000 claims description 6
- 229910052708 sodium Inorganic materials 0.000 claims description 6
- 239000004546 suspension concentrate Substances 0.000 claims description 6
- FYGHSUNMUKGBRK-UHFFFAOYSA-N 1,2,3-trimethylbenzene Chemical compound CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-UHFFFAOYSA-N 0.000 claims description 5
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 claims description 5
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- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 239000011734 sodium Substances 0.000 claims description 5
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 4
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- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 3
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- 239000000080 wetting agent Substances 0.000 claims description 3
- TVFWYUWNQVRQRG-UHFFFAOYSA-N 2,3,4-tris(2-phenylethenyl)phenol Chemical compound C=1C=CC=CC=1C=CC1=C(C=CC=2C=CC=CC=2)C(O)=CC=C1C=CC1=CC=CC=C1 TVFWYUWNQVRQRG-UHFFFAOYSA-N 0.000 claims description 2
- VUUJEGLTTLCWLF-UHFFFAOYSA-N 5-amino-1-[2,3,6-trichloro-4-(trifluoromethyl)phenyl]pyrazole-4-carbonitrile Chemical group NC1=C(C#N)C=NN1C1=C(Cl)C=C(C(F)(F)F)C(Cl)=C1Cl VUUJEGLTTLCWLF-UHFFFAOYSA-N 0.000 claims description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 2
- 239000011575 calcium Substances 0.000 claims description 2
- 229910052791 calcium Inorganic materials 0.000 claims description 2
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 claims description 2
- GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 claims description 2
- 150000004676 glycans Chemical class 0.000 claims description 2
- XCOBTUNSZUJCDH-UHFFFAOYSA-B lithium magnesium sodium silicate Chemical compound [Li+].[Li+].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Na+].[Na+].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3 XCOBTUNSZUJCDH-UHFFFAOYSA-B 0.000 claims description 2
- 235000010446 mineral oil Nutrition 0.000 claims description 2
- 229910052901 montmorillonite Inorganic materials 0.000 claims description 2
- 229920001282 polysaccharide Polymers 0.000 claims description 2
- 239000005017 polysaccharide Substances 0.000 claims description 2
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 claims description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 2
- 229920001285 xanthan gum Polymers 0.000 claims description 2
- SCWWKKUJPHRBRV-JEDNCBNOSA-N (2s)-2,6-diaminohexanoic acid;sodium Chemical compound [Na].NCCCC[C@H](N)C(O)=O SCWWKKUJPHRBRV-JEDNCBNOSA-N 0.000 claims 1
- CJYPDGRCXRPJLB-UHFFFAOYSA-N 5-phenyl-1h-pyrazole-4-carbonitrile Chemical compound N#CC1=CNN=C1C1=CC=CC=C1 CJYPDGRCXRPJLB-UHFFFAOYSA-N 0.000 claims 1
- GJCOSYZMQJWQCA-UHFFFAOYSA-N 9H-xanthene Chemical compound C1=CC=C2CC3=CC=CC=C3OC2=C1 GJCOSYZMQJWQCA-UHFFFAOYSA-N 0.000 claims 1
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- YRIUSKIDOIARQF-UHFFFAOYSA-N dodecyl benzenesulfonate Chemical compound CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 YRIUSKIDOIARQF-UHFFFAOYSA-N 0.000 claims 1
- 229940071161 dodecylbenzenesulfonate Drugs 0.000 claims 1
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- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract description 6
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Classifications
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- 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 |
|---|---|
| HU188583B true HU188583B (en) | 1986-04-28 |
Family
ID=26280166
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU822304A HU188583B (en) | 1981-07-17 | 1982-07-15 | Herbicides containing n-phenyl-pyrazole derivatives and process for preparing the active substances |
Country Status (28)
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2716453B1 (fr) * | 1994-02-22 | 1996-03-29 | Rhone Poulenc Agrochimie | Procédé de sulfinylation de composés hétérocycliques. |
| DE3420985A1 (de) * | 1983-10-15 | 1985-04-25 | Bayer Ag, 5090 Leverkusen | Substituierte 5-acylamino-1-phenylpyrazole |
| EP0178035B1 (en) * | 1984-05-12 | 1990-01-03 | FISONS plc | Anti-inflammatory 1,n-diarylpyrazol-3-amines, compositions containing them and processes for their preparation |
| 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 |
| WO2012033634A2 (en) | 2010-09-09 | 2012-03-15 | Mary Kay Inc. | Topical skin care formulations comprising plant extracts |
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 |
| RO86895B (ro) * | 1980-02-26 | 1985-05-31 | May & Baker Limited | Procedeu pentru prepararea unor derivati de n-fenilpirazol |
| EP0053698B1 (de) * | 1980-12-05 | 1985-01-09 | BASF Aktiengesellschaft | 5-Amino-1-phenylpyrazol-4-carbonsäureester, Verfahren zu ihrer Herstellung, diese enthaltende Herbizide und ihre Anwendung als Herbizide |
-
1982
- 1982-07-14 MA MA19747A patent/MA19539A1/fr unknown
- 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 EP EP82902079A patent/EP0084033B1/en not_active Expired
- 1982-07-15 IL IL66321A patent/IL66321A/xx unknown
- 1982-07-15 BG BG057419A patent/BG37672A3/xx unknown
- 1982-07-15 PL PL1982237490A patent/PL133283B1/pl unknown
- 1982-07-15 DE DE19823226496 patent/DE3226496A1/de not_active Withdrawn
- 1982-07-15 WO PCT/GB1982/000212 patent/WO1983000331A1/en active IP Right Grant
- 1982-07-15 CH CH1562/83A patent/CH657360A5/fr not_active IP Right Cessation
- 1982-07-15 GB GB08220498A patent/GB2105324B/en not_active Expired
- 1982-07-15 US US06/398,336 patent/US4505740A/en not_active Expired - Fee Related
- 1982-07-15 PH PH27573A patent/PH17961A/en unknown
- 1982-07-15 NL NL8202864A patent/NL8202864A/nl not_active Application Discontinuation
- 1982-07-15 CA CA000407320A patent/CA1228859A/en not_active Expired
- 1982-07-15 NZ NZ201281A patent/NZ201281A/en unknown
- 1982-07-15 SE SE8204348A patent/SE8204348L/xx not_active Application Discontinuation
- 1982-07-15 IE IE1699/82A patent/IE53427B1/en unknown
- 1982-07-15 AU AU86029/82A patent/AU563147B2/en not_active Ceased
- 1982-07-15 TR TR21486A patent/TR21486A/xx unknown
- 1982-07-15 IT IT48823/82A patent/IT1157220B/it active
- 1982-07-15 DK DK318482A patent/DK318482A/da not_active Application Discontinuation
- 1982-07-15 HU HU822304A patent/HU188583B/hu unknown
- 1982-07-15 PT PT75255A patent/PT75255B/pt unknown
- 1982-07-15 BR BR8204107A patent/BR8204107A/pt unknown
- 1982-07-15 DD DD82241681A patent/DD202611A5/de unknown
-
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
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