DE1542702A1 - Selektive Herbizide - Google Patents
Selektive HerbizideInfo
- Publication number
- DE1542702A1 DE1542702A1 DE19651542702 DE1542702A DE1542702A1 DE 1542702 A1 DE1542702 A1 DE 1542702A1 DE 19651542702 DE19651542702 DE 19651542702 DE 1542702 A DE1542702 A DE 1542702A DE 1542702 A1 DE1542702 A1 DE 1542702A1
- Authority
- DE
- Germany
- Prior art keywords
- acid
- butyn
- carbon atoms
- radical
- anilide
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Ceased
Links
- 239000004009 herbicide Substances 0.000 title claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 150000003931 anilides Chemical class 0.000 claims description 6
- 239000000460 chlorine Chemical group 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 229940051881 anilide analgesics and antipyretics Drugs 0.000 claims description 3
- NJYFRQQXXXRJHK-UHFFFAOYSA-N (4-aminophenyl) thiocyanate Chemical group NC1=CC=C(SC#N)C=C1 NJYFRQQXXXRJHK-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Chemical group 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 16
- 239000004480 active ingredient Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
- MFOUDYKPLGXPGO-UHFFFAOYSA-N propachlor Chemical compound ClCC(=O)N(C(C)C)C1=CC=CC=C1 MFOUDYKPLGXPGO-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- 240000001592 Amaranthus caudatus Species 0.000 description 4
- 235000009328 Amaranthus caudatus Nutrition 0.000 description 4
- 244000178937 Brassica oleracea var. capitata Species 0.000 description 4
- 241000196324 Embryophyta Species 0.000 description 4
- 239000013543 active substance Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 244000291564 Allium cepa Species 0.000 description 3
- 235000011301 Brassica oleracea var capitata Nutrition 0.000 description 3
- 241000219146 Gossypium Species 0.000 description 3
- 244000042664 Matricaria chamomilla Species 0.000 description 3
- 235000007232 Matricaria chamomilla Nutrition 0.000 description 3
- 240000004713 Pisum sativum Species 0.000 description 3
- 235000010582 Pisum sativum Nutrition 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 235000009108 Urtica dioica Nutrition 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 230000002363 herbicidal effect Effects 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- CDULGHZNHURECF-UHFFFAOYSA-N 2,3-dimethylaniline 2,4-dimethylaniline 2,5-dimethylaniline 2,6-dimethylaniline 3,4-dimethylaniline 3,5-dimethylaniline Chemical class CC1=CC=C(N)C(C)=C1.CC1=CC=C(C)C(N)=C1.CC1=CC(C)=CC(N)=C1.CC1=CC=C(N)C=C1C.CC1=CC=CC(N)=C1C.CC1=CC=CC(C)=C1N CDULGHZNHURECF-UHFFFAOYSA-N 0.000 description 2
- 235000002732 Allium cepa var. cepa Nutrition 0.000 description 2
- 235000007320 Avena fatua Nutrition 0.000 description 2
- 244000075850 Avena orientalis Species 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- 241001249699 Capitata Species 0.000 description 2
- 235000007866 Chamaemelum nobile Nutrition 0.000 description 2
- 240000006122 Chenopodium album Species 0.000 description 2
- 235000011498 Chenopodium album var missouriense Nutrition 0.000 description 2
- 235000013328 Chenopodium album var. album Nutrition 0.000 description 2
- 235000014052 Chenopodium album var. microphyllum Nutrition 0.000 description 2
- 235000014050 Chenopodium album var. stevensii Nutrition 0.000 description 2
- 235000013012 Chenopodium album var. striatum Nutrition 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- 240000006694 Stellaria media Species 0.000 description 2
- 244000274883 Urtica dioica Species 0.000 description 2
- 235000012735 amaranth Nutrition 0.000 description 2
- 239000004178 amaranth Substances 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 235000008504 concentrate Nutrition 0.000 description 2
- 244000038559 crop plants Species 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 230000008635 plant growth Effects 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- DGMOBVGABMBZSB-UHFFFAOYSA-N 2-methylpropanoyl chloride Chemical compound CC(C)C(Cl)=O DGMOBVGABMBZSB-UHFFFAOYSA-N 0.000 description 1
- XOGYQVITULCUGU-UHFFFAOYSA-N 3,4,5-trichloroaniline Chemical class NC1=CC(Cl)=C(Cl)C(Cl)=C1 XOGYQVITULCUGU-UHFFFAOYSA-N 0.000 description 1
- FVZODFVCIDBDGS-UHFFFAOYSA-N 3-bromo-4-chloroaniline Chemical compound NC1=CC=C(Cl)C(Br)=C1 FVZODFVCIDBDGS-UHFFFAOYSA-N 0.000 description 1
- 235000005255 Allium cepa Nutrition 0.000 description 1
- 241001621841 Alopecurus myosuroides Species 0.000 description 1
- 241001666377 Apera Species 0.000 description 1
- 241000209764 Avena fatua Species 0.000 description 1
- 235000007319 Avena orientalis Nutrition 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 1
- 240000004585 Dactylis glomerata Species 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 244000214240 Galinsoga parviflora Species 0.000 description 1
- 235000018914 Galinsoga parviflora Nutrition 0.000 description 1
- 235000009438 Gossypium Nutrition 0.000 description 1
- 241001456088 Hesperocnide Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- -1 Monochloroacetic acid N-cyanomethyl-3,4-dichloroanilide Chemical compound 0.000 description 1
- 244000292693 Poa annua Species 0.000 description 1
- 244000200882 Setaria barbata Species 0.000 description 1
- 235000001561 Setaria barbata Nutrition 0.000 description 1
- 244000152045 Themeda triandra Species 0.000 description 1
- 235000005373 Uvularia sessilifolia Nutrition 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229960003369 butacaine Drugs 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 229940106681 chloroacetic acid Drugs 0.000 description 1
- 239000011280 coal tar Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 239000002283 diesel fuel Substances 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 150000004994 m-toluidines Chemical class 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 150000004993 o-toluidines Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 150000004995 p-toluidines Chemical class 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- 150000004992 toluidines Chemical class 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US595650A US3535377A (en) | 1965-12-24 | 1966-11-21 | N-butyn-(1)-yl-(3)-anilides as herbicides |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB0085152 | 1965-12-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1542702A1 true DE1542702A1 (de) | 1970-07-02 |
Family
ID=6982777
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19651542702 Ceased DE1542702A1 (de) | 1965-12-24 | 1965-12-24 | Selektive Herbizide |
Country Status (8)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0037019A1 (de) * | 1980-04-01 | 1981-10-07 | Bayer Ag | N-Allenyl-halogenacetanilide, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Wachstumsregulatoren und Herbizide |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2077979A1 (en) * | 1970-02-25 | 1971-11-05 | Jovanovic Dusan | Fluoroacetanilides - with analgesic antiinflammatory, antipyretic tranquillizing and sedative activity |
-
1965
- 1965-12-24 DE DE19651542702 patent/DE1542702A1/de not_active Ceased
-
1966
- 1966-11-25 ES ES0333767A patent/ES333767A1/es not_active Expired
- 1966-12-19 BE BE691424D patent/BE691424A/xx unknown
- 1966-12-21 NL NL6617962A patent/NL141759B/xx unknown
- 1966-12-23 AT AT1183266A patent/AT269549B/de active
- 1966-12-23 FR FR88716A patent/FR1507401A/fr not_active Expired
- 1966-12-23 GB GB5763466A patent/GB1164480A/en not_active Expired
-
1971
- 1971-12-31 MY MY7100101A patent/MY7100101A/xx unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0037019A1 (de) * | 1980-04-01 | 1981-10-07 | Bayer Ag | N-Allenyl-halogenacetanilide, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Wachstumsregulatoren und Herbizide |
Also Published As
| Publication number | Publication date |
|---|---|
| ES333767A1 (es) | 1967-10-16 |
| NL141759B (nl) | 1974-04-16 |
| BE691424A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1967-06-19 |
| GB1164480A (en) | 1969-09-17 |
| FR1507401A (fr) | 1967-12-29 |
| AT269549B (de) | 1969-03-25 |
| NL6617962A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1967-06-26 |
| MY7100101A (en) | 1971-12-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| E77 | Valid patent as to the heymanns-index 1977 | ||
| EHV | Ceased/renunciation |