DE1768835C3 - N-Pheny l-K-methy l-NT-alkenoxyharnstoffe und diese enthaltende Herbizide - Google Patents
N-Pheny l-K-methy l-NT-alkenoxyharnstoffe und diese enthaltende HerbizideInfo
- Publication number
- DE1768835C3 DE1768835C3 DE1768835A DE1768835A DE1768835C3 DE 1768835 C3 DE1768835 C3 DE 1768835C3 DE 1768835 A DE1768835 A DE 1768835A DE 1768835 A DE1768835 A DE 1768835A DE 1768835 C3 DE1768835 C3 DE 1768835C3
- Authority
- DE
- Germany
- Prior art keywords
- methyl
- urea
- dichlorophenyl
- alkenoxyureas
- pheny
- 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.)
- Expired
Links
- 239000004009 herbicide Substances 0.000 title description 5
- 235000013877 carbamide Nutrition 0.000 description 33
- 239000004202 carbamide Substances 0.000 description 25
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 21
- 241000196324 Embryophyta Species 0.000 description 16
- 150000003672 ureas Chemical class 0.000 description 11
- 150000001875 compounds Chemical class 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 241000209140 Triticum Species 0.000 description 6
- 235000021307 Triticum Nutrition 0.000 description 6
- -1 alkenyl radicals Chemical class 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 241000209504 Poaceae Species 0.000 description 5
- 239000004480 active ingredient Substances 0.000 description 4
- 230000018109 developmental process Effects 0.000 description 4
- 230000002363 herbicidal effect Effects 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 244000292697 Polygonum aviculare Species 0.000 description 3
- VHPJXYDOOWUMBR-UHFFFAOYSA-N 1,2-dichlorocyclohexa-1,3,5-triene Chemical compound ClC1=C[C]=CC=C1Cl VHPJXYDOOWUMBR-UHFFFAOYSA-N 0.000 description 2
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 2
- 235000007320 Avena fatua Nutrition 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 235000006386 Polygonum aviculare Nutrition 0.000 description 2
- 240000005592 Veronica officinalis Species 0.000 description 2
- 235000013339 cereals Nutrition 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 244000045561 useful plants Species 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- 240000002245 Acer pensylvanicum Species 0.000 description 1
- 235000006760 Acer pensylvanicum Nutrition 0.000 description 1
- 235000001674 Agaricus brunnescens Nutrition 0.000 description 1
- OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 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
- 244000075850 Avena orientalis Species 0.000 description 1
- 235000008427 Brassica arvensis Nutrition 0.000 description 1
- 244000056139 Brassica cretica Species 0.000 description 1
- 235000003351 Brassica cretica Nutrition 0.000 description 1
- 244000024671 Brassica kaber Species 0.000 description 1
- 235000003343 Brassica rupestris Nutrition 0.000 description 1
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 1
- ALJMBSNPELPZSM-UHFFFAOYSA-N CN(C(NC(C=CC=C1Cl)=C1Cl)=O)O Chemical compound CN(C(NC(C=CC=C1Cl)=C1Cl)=O)O ALJMBSNPELPZSM-UHFFFAOYSA-N 0.000 description 1
- 241000217446 Calystegia sepium Species 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 240000004385 Centaurea cyanus Species 0.000 description 1
- 235000005940 Centaurea cyanus Nutrition 0.000 description 1
- 241000219312 Chenopodium Species 0.000 description 1
- 244000033714 Clidemia hirta Species 0.000 description 1
- 235000014277 Clidemia hirta Nutrition 0.000 description 1
- 241001354404 Cyanus Species 0.000 description 1
- 240000003173 Drymaria cordata Species 0.000 description 1
- 241001289540 Fallopia convolvulus Species 0.000 description 1
- 240000005979 Hordeum vulgare Species 0.000 description 1
- 235000007340 Hordeum vulgare Nutrition 0.000 description 1
- VSNHCAURESNICA-UHFFFAOYSA-N Hydroxyurea Chemical compound NC(=O)NO VSNHCAURESNICA-UHFFFAOYSA-N 0.000 description 1
- 244000042664 Matricaria chamomilla Species 0.000 description 1
- 240000001090 Papaver somniferum Species 0.000 description 1
- 235000003898 Papaver sp Nutrition 0.000 description 1
- 244000031615 Papaver sp Species 0.000 description 1
- 244000286177 Raphanus raphanistrum Species 0.000 description 1
- 235000000241 Raphanus raphanistrum Nutrition 0.000 description 1
- 235000005373 Uvularia sessilifolia Nutrition 0.000 description 1
- 235000005545 Veronica americana Nutrition 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- SLUNEGLMXGHOLY-UHFFFAOYSA-N benzene;hexane Chemical compound CCCCCC.C1=CC=CC=C1 SLUNEGLMXGHOLY-UHFFFAOYSA-N 0.000 description 1
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000001066 destructive effect Effects 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000035784 germination Effects 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000003306 harvesting Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 235000010460 mustard Nutrition 0.000 description 1
- CPQCSJYYDADLCZ-UHFFFAOYSA-N n-methylhydroxylamine Chemical compound CNO CPQCSJYYDADLCZ-UHFFFAOYSA-N 0.000 description 1
- 125000005429 oxyalkyl group Chemical group 0.000 description 1
- 244000045947 parasite Species 0.000 description 1
- 239000003415 peat Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 231100000916 relative toxicity Toxicity 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
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 (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR48902A FR1540424A (fr) | 1967-07-11 | 1967-07-11 | Nouvelles urées substituées et leurs applications |
| FR69050523 | 1968-05-30 | ||
| FR50053A FR95412E (fr) | 1967-07-11 | 1968-05-30 | Nouvelles urées substituées et leurs applications. |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1768835A1 DE1768835A1 (de) | 1972-01-05 |
| DE1768835B2 DE1768835B2 (de) | 1973-10-04 |
| DE1768835C3 true DE1768835C3 (de) | 1974-05-09 |
Family
ID=27253630
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1768835A Expired DE1768835C3 (de) | 1967-07-11 | 1968-07-05 | N-Pheny l-K-methy l-NT-alkenoxyharnstoffe und diese enthaltende Herbizide |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3846465A (esLanguage) |
| BE (1) | BE717897A (esLanguage) |
| DE (1) | DE1768835C3 (esLanguage) |
| FR (2) | FR1540424A (esLanguage) |
| GB (1) | GB1217068A (esLanguage) |
| NL (1) | NL6809682A (esLanguage) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1540424A (fr) * | 1967-07-11 | 1968-09-27 | Progil | Nouvelles urées substituées et leurs applications |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2723192A (en) * | 1954-02-23 | 1955-11-08 | Du Pont | Herbicidal process and product |
| US3079244A (en) * | 1957-06-14 | 1963-02-26 | Hoechst Ag | Herbicidal method |
| US3306726A (en) * | 1963-08-06 | 1967-02-28 | Velsicol Chemical Corp | Method for the control of weeds |
| DE1190249B (de) * | 1963-11-27 | 1965-04-01 | Basf Ag | Selektives Herbizid |
| US3352899A (en) * | 1965-06-04 | 1967-11-14 | Nippon Soda Co | Substituted benzohydroxamates |
| FR1540424A (fr) * | 1967-07-11 | 1968-09-27 | Progil | Nouvelles urées substituées et leurs applications |
-
1967
- 1967-07-11 FR FR48902A patent/FR1540424A/fr not_active Expired
-
1968
- 1968-05-30 FR FR50053A patent/FR95412E/fr not_active Expired
- 1968-07-05 DE DE1768835A patent/DE1768835C3/de not_active Expired
- 1968-07-09 NL NL6809682A patent/NL6809682A/xx unknown
- 1968-07-10 BE BE717897D patent/BE717897A/xx unknown
- 1968-07-11 GB GB33197/68A patent/GB1217068A/en not_active Expired
-
1971
- 1971-03-11 US US00123440A patent/US3846465A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| DE1768835B2 (de) | 1973-10-04 |
| FR95412E (fr) | 1970-11-06 |
| DE1768835A1 (de) | 1972-01-05 |
| GB1217068A (en) | 1970-12-23 |
| NL6809682A (esLanguage) | 1969-01-14 |
| FR1540424A (fr) | 1968-09-27 |
| US3846465A (en) | 1974-11-05 |
| BE717897A (esLanguage) | 1968-12-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| EHJ | Ceased/non-payment of the annual fee |