DE2223839A1 - 2-Fluor-5-halogenphenylharnstoffe,Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende herbizide Mittel - Google Patents
2-Fluor-5-halogenphenylharnstoffe,Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende herbizide MittelInfo
- Publication number
- DE2223839A1 DE2223839A1 DE19722223839 DE2223839A DE2223839A1 DE 2223839 A1 DE2223839 A1 DE 2223839A1 DE 19722223839 DE19722223839 DE 19722223839 DE 2223839 A DE2223839 A DE 2223839A DE 2223839 A1 DE2223839 A1 DE 2223839A1
- Authority
- DE
- Germany
- Prior art keywords
- compounds
- fluoro
- general formula
- urea
- meaning given
- 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
- 150000001875 compounds Chemical class 0.000 title claims description 44
- 238000000034 method Methods 0.000 title claims description 8
- 230000002363 herbicidal effect Effects 0.000 title description 16
- 239000000203 mixture Substances 0.000 title description 9
- 239000000460 chlorine Substances 0.000 claims description 35
- 239000004009 herbicide Substances 0.000 claims description 17
- 235000013877 carbamide Nutrition 0.000 claims description 12
- 150000003672 ureas Chemical class 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 239000000969 carrier Substances 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 239000012948 isocyanate Substances 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- GRRYSIXDUIAUGY-UHFFFAOYSA-N n-methylcarbamoyl chloride Chemical compound CNC(Cl)=O GRRYSIXDUIAUGY-UHFFFAOYSA-N 0.000 claims description 2
- 239000004094 surface-active agent Substances 0.000 claims description 2
- 239000000654 additive Substances 0.000 claims 1
- 241000196324 Embryophyta Species 0.000 description 25
- XMTQQYYKAHVGBJ-UHFFFAOYSA-N 3-(3,4-DICHLOROPHENYL)-1,1-DIMETHYLUREA Chemical group CN(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 XMTQQYYKAHVGBJ-UHFFFAOYSA-N 0.000 description 10
- 239000005510 Diuron Substances 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 239000004202 carbamide Substances 0.000 description 9
- 230000006378 damage Effects 0.000 description 8
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 235000017587 Medicago sativa ssp. sativa Nutrition 0.000 description 5
- 240000007594 Oryza sativa Species 0.000 description 5
- 235000007164 Oryza sativa Nutrition 0.000 description 5
- 241000209504 Poaceae Species 0.000 description 5
- 235000013339 cereals Nutrition 0.000 description 5
- 235000009566 rice Nutrition 0.000 description 5
- -1 2,5-dichlorophenyl Chemical group 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 241000219823 Medicago Species 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- ORKBTDVDVWNPNL-UHFFFAOYSA-N 1-(2,5-difluorophenyl)-3-methylurea Chemical compound CNC(=O)NC1=CC(F)=CC=C1F ORKBTDVDVWNPNL-UHFFFAOYSA-N 0.000 description 3
- KYVZSMXJIDJHDY-UHFFFAOYSA-N 1-(5-chloro-2-fluorophenyl)-3-methylurea Chemical compound CNC(=O)NC1=C(C=CC(=C1)Cl)F KYVZSMXJIDJHDY-UHFFFAOYSA-N 0.000 description 3
- 239000007900 aqueous suspension Substances 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 239000004495 emulsifiable concentrate Substances 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 125000001207 fluorophenyl group Chemical group 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000009331 sowing Methods 0.000 description 3
- 240000006995 Abutilon theophrasti Species 0.000 description 2
- 244000237956 Amaranthus retroflexus Species 0.000 description 2
- 235000013479 Amaranthus retroflexus Nutrition 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 240000006122 Chenopodium album Species 0.000 description 2
- 235000009344 Chenopodium album Nutrition 0.000 description 2
- 244000025670 Eleusine indica Species 0.000 description 2
- 235000014716 Eleusine indica Nutrition 0.000 description 2
- 240000008620 Fagopyrum esculentum Species 0.000 description 2
- 235000009419 Fagopyrum esculentum Nutrition 0.000 description 2
- 244000020551 Helianthus annuus Species 0.000 description 2
- 235000003222 Helianthus annuus Nutrition 0.000 description 2
- 235000021506 Ipomoea Nutrition 0.000 description 2
- 241000207783 Ipomoea Species 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 210000003608 fece Anatomy 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 244000045561 useful plants Species 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 239000004563 wettable powder Substances 0.000 description 2
- SNHIIFOXCRYGGY-UHFFFAOYSA-N 1,4-difluoro-2-isocyanatobenzene Chemical compound FC1=CC=C(F)C(N=C=O)=C1 SNHIIFOXCRYGGY-UHFFFAOYSA-N 0.000 description 1
- AZPHOESBVUWFJB-UHFFFAOYSA-N 3-(2,4-difluorophenyl)-1,1-dimethylurea Chemical compound CN(C)C(=O)NC1=CC=C(F)C=C1F AZPHOESBVUWFJB-UHFFFAOYSA-N 0.000 description 1
- DOVGZPJULHERQI-UHFFFAOYSA-N 3-(2,5-dichlorophenyl)-1,1-dimethylurea Chemical compound CN(C)C(=O)NC1=CC(Cl)=CC=C1Cl DOVGZPJULHERQI-UHFFFAOYSA-N 0.000 description 1
- IAVUGNQDGAZJAZ-UHFFFAOYSA-N 4-chloro-1-fluoro-2-isocyanatobenzene Chemical compound FC1=CC=C(Cl)C=C1N=C=O IAVUGNQDGAZJAZ-UHFFFAOYSA-N 0.000 description 1
- 241001290610 Abildgaardia Species 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- 240000004658 Medicago sativa Species 0.000 description 1
- 244000088461 Panicum crus-galli Species 0.000 description 1
- 235000011999 Panicum crusgalli Nutrition 0.000 description 1
- 235000005775 Setaria Nutrition 0.000 description 1
- 241000232088 Setaria <nematode> Species 0.000 description 1
- 240000003461 Setaria viridis Species 0.000 description 1
- 235000002248 Setaria viridis Nutrition 0.000 description 1
- 206010047700 Vomiting Diseases 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 125000003963 dichloro group Chemical group Cl* 0.000 description 1
- 125000004188 dichlorophenyl group Chemical group 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 230000012010 growth Effects 0.000 description 1
- 239000003630 growth substance Substances 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000010871 livestock manure Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 231100000208 phytotoxic Toxicity 0.000 description 1
- 230000000885 phytotoxic effect Effects 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 230000008673 vomiting Effects 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
- C07C275/28—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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US14441371A | 1971-05-17 | 1971-05-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2223839A1 true DE2223839A1 (de) | 1972-12-07 |
Family
ID=22508473
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722223839 Pending DE2223839A1 (de) | 1971-05-17 | 1972-05-16 | 2-Fluor-5-halogenphenylharnstoffe,Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende herbizide Mittel |
Country Status (11)
| Country | Link |
|---|---|
| AR (1) | AR192779A1 (enExample) |
| AT (1) | AT313299B (enExample) |
| AU (1) | AU4231372A (enExample) |
| BR (1) | BR7203084D0 (enExample) |
| DE (1) | DE2223839A1 (enExample) |
| FR (1) | FR2139253A5 (enExample) |
| GB (1) | GB1341153A (enExample) |
| IL (1) | IL39453A0 (enExample) |
| IT (1) | IT957899B (enExample) |
| NL (1) | NL7206600A (enExample) |
| ZA (1) | ZA723312B (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0433809A1 (de) * | 1989-12-22 | 1991-06-26 | Bayer Ag | Difluorphenylharnstoffe |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4313755A (en) * | 1980-07-21 | 1982-02-02 | Shell Oil Company | N-Cyclopyopyl-N-(fluorophenyl)-N-acylureas and their herbidical use |
-
1972
- 1972-04-24 FR FR7214404A patent/FR2139253A5/fr not_active Expired
- 1972-05-16 BR BR3084/72A patent/BR7203084D0/pt unknown
- 1972-05-16 AR AR242019A patent/AR192779A1/es active
- 1972-05-16 IL IL39453A patent/IL39453A0/xx unknown
- 1972-05-16 GB GB2293172A patent/GB1341153A/en not_active Expired
- 1972-05-16 NL NL7206600A patent/NL7206600A/xx unknown
- 1972-05-16 DE DE19722223839 patent/DE2223839A1/de active Pending
- 1972-05-16 AT AT423972A patent/AT313299B/de not_active IP Right Cessation
- 1972-05-16 AU AU42313/72A patent/AU4231372A/en not_active Expired
- 1972-05-16 IT IT50286/72A patent/IT957899B/it active
-
1973
- 1973-05-16 ZA ZA723312A patent/ZA723312B/xx unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0433809A1 (de) * | 1989-12-22 | 1991-06-26 | Bayer Ag | Difluorphenylharnstoffe |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2139253A5 (enExample) | 1973-01-05 |
| GB1341153A (en) | 1973-12-19 |
| AR192779A1 (es) | 1973-03-14 |
| BR7203084D0 (pt) | 1973-04-26 |
| IT957899B (it) | 1973-10-20 |
| ZA723312B (en) | 1973-07-25 |
| AT313299B (de) | 1974-02-11 |
| AU4231372A (en) | 1973-11-22 |
| IL39453A0 (en) | 1972-07-26 |
| NL7206600A (enExample) | 1972-11-21 |
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