DE1925196A1 - Harnstoffderivate - Google Patents
HarnstoffderivateInfo
- Publication number
- DE1925196A1 DE1925196A1 DE19691925196 DE1925196A DE1925196A1 DE 1925196 A1 DE1925196 A1 DE 1925196A1 DE 19691925196 DE19691925196 DE 19691925196 DE 1925196 A DE1925196 A DE 1925196A DE 1925196 A1 DE1925196 A1 DE 1925196A1
- Authority
- DE
- Germany
- Prior art keywords
- dimethylurea
- trifluoromethyl
- cyclohexenyl
- phenyl
- active ingredient
- 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.)
- Pending
Links
- 150000003672 ureas Chemical class 0.000 title claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 6
- 230000002363 herbicidal effect Effects 0.000 claims description 6
- 239000004009 herbicide Substances 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 description 21
- 241000209219 Hordeum Species 0.000 description 8
- 241000209140 Triticum Species 0.000 description 8
- 235000021307 Triticum Nutrition 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 240000006122 Chenopodium album Species 0.000 description 7
- 235000009344 Chenopodium album Nutrition 0.000 description 7
- 241000196324 Embryophyta Species 0.000 description 5
- 244000237956 Amaranthus retroflexus Species 0.000 description 4
- 235000013479 Amaranthus retroflexus Nutrition 0.000 description 4
- 235000017896 Digitaria Nutrition 0.000 description 4
- 241001303487 Digitaria <clam> Species 0.000 description 4
- 241000192043 Echinochloa Species 0.000 description 4
- 240000002024 Gossypium herbaceum Species 0.000 description 4
- 240000006597 Poa trivialis Species 0.000 description 4
- 244000234609 Portulaca oleracea Species 0.000 description 4
- 235000001855 Portulaca oleracea Nutrition 0.000 description 4
- 244000137827 Rumex acetosa Species 0.000 description 4
- 235000005291 Rumex acetosa Nutrition 0.000 description 4
- 235000005775 Setaria Nutrition 0.000 description 4
- 241000232088 Setaria <nematode> Species 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 235000004341 Gossypium herbaceum Nutrition 0.000 description 3
- 235000007340 Hordeum vulgare Nutrition 0.000 description 3
- 244000303225 Lamium amplexicaule Species 0.000 description 3
- 235000009198 Lamium amplexicaule Nutrition 0.000 description 3
- 240000004296 Lolium perenne Species 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 235000013877 carbamide Nutrition 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000002689 soil Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 229920000742 Cotton Polymers 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- 241000219146 Gossypium Species 0.000 description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 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
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 241000219312 Chenopodium Species 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 241000520028 Lamium Species 0.000 description 1
- 241000209510 Liliopsida Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 239000002262 Schiff base Substances 0.000 description 1
- 150000004753 Schiff bases Chemical class 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000011280 coal tar Substances 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 238000000354 decomposition reaction Methods 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
- XHFGWHUWQXTGAT-UHFFFAOYSA-N dimethylamine hydrochloride Natural products CNC(C)C XHFGWHUWQXTGAT-UHFFFAOYSA-N 0.000 description 1
- IQDGSYLLQPDQDV-UHFFFAOYSA-N dimethylazanium;chloride Chemical compound Cl.CNC IQDGSYLLQPDQDV-UHFFFAOYSA-N 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 241001233957 eudicotyledons Species 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- -1 m-trifluoromethylphenyl Chemical group 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- JOHLTMWXHJLNDE-UHFFFAOYSA-N methoxyurea Chemical compound CONC(N)=O JOHLTMWXHJLNDE-UHFFFAOYSA-N 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/64—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups singly-bound to oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C275/30—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by halogen atoms, or by nitro or nitroso groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19691925196 DE1925196A1 (de) | 1969-05-17 | 1969-05-17 | Harnstoffderivate |
| CH696370A CH523010A (de) | 1969-05-17 | 1970-05-11 | Herbizides Mittel |
| NL7006940A NL7006940A (enrdf_load_stackoverflow) | 1969-05-17 | 1970-05-13 | |
| BE750468D BE750468A (fr) | 1969-05-17 | 1970-05-15 | Derives d'uree |
| GB2357570A GB1301939A (enrdf_load_stackoverflow) | 1969-05-17 | 1970-05-15 | |
| FR7017829A FR2047832A5 (enrdf_load_stackoverflow) | 1969-05-17 | 1970-05-15 | |
| ZA703306A ZA703306B (en) | 1969-05-17 | 1970-05-15 | Urea derivatives |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19691925196 DE1925196A1 (de) | 1969-05-17 | 1969-05-17 | Harnstoffderivate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1925196A1 true DE1925196A1 (de) | 1970-11-26 |
Family
ID=5734433
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19691925196 Pending DE1925196A1 (de) | 1969-05-17 | 1969-05-17 | Harnstoffderivate |
Country Status (7)
| Country | Link |
|---|---|
| BE (1) | BE750468A (enrdf_load_stackoverflow) |
| CH (1) | CH523010A (enrdf_load_stackoverflow) |
| DE (1) | DE1925196A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2047832A5 (enrdf_load_stackoverflow) |
| GB (1) | GB1301939A (enrdf_load_stackoverflow) |
| NL (1) | NL7006940A (enrdf_load_stackoverflow) |
| ZA (1) | ZA703306B (enrdf_load_stackoverflow) |
-
1969
- 1969-05-17 DE DE19691925196 patent/DE1925196A1/de active Pending
-
1970
- 1970-05-11 CH CH696370A patent/CH523010A/de not_active IP Right Cessation
- 1970-05-13 NL NL7006940A patent/NL7006940A/xx unknown
- 1970-05-15 ZA ZA703306A patent/ZA703306B/xx unknown
- 1970-05-15 FR FR7017829A patent/FR2047832A5/fr not_active Expired
- 1970-05-15 GB GB2357570A patent/GB1301939A/en not_active Expired
- 1970-05-15 BE BE750468D patent/BE750468A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ZA703306B (en) | 1971-01-27 |
| CH523010A (de) | 1972-05-31 |
| NL7006940A (enrdf_load_stackoverflow) | 1970-11-19 |
| BE750468A (fr) | 1970-11-16 |
| GB1301939A (enrdf_load_stackoverflow) | 1973-01-04 |
| FR2047832A5 (enrdf_load_stackoverflow) | 1971-03-12 |
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