IL28241A - Difluorochloromethylaryl ureas,their preparation and use as herbicides - Google Patents
Difluorochloromethylaryl ureas,their preparation and use as herbicidesInfo
- Publication number
- IL28241A IL28241A IL28241A IL2824167A IL28241A IL 28241 A IL28241 A IL 28241A IL 28241 A IL28241 A IL 28241A IL 2824167 A IL2824167 A IL 2824167A IL 28241 A IL28241 A IL 28241A
- Authority
- IL
- Israel
- Prior art keywords
- compound
- stands
- difluorochloromethylphenyl
- radical
- compounds
- Prior art date
Links
- 235000013877 carbamide Nutrition 0.000 title claims description 14
- 150000003672 ureas Chemical class 0.000 title claims description 14
- 238000002360 preparation method Methods 0.000 title claims description 9
- 239000004009 herbicide Substances 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims description 33
- 241000196324 Embryophyta Species 0.000 claims description 19
- -1 alkoxy radical Chemical class 0.000 claims description 17
- 239000012948 isocyanate Substances 0.000 claims description 15
- 150000002513 isocyanates Chemical class 0.000 claims description 11
- 239000004480 active ingredient Substances 0.000 claims description 9
- 230000029936 alkylation Effects 0.000 claims description 8
- 238000005804 alkylation reaction Methods 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 230000002363 herbicidal effect Effects 0.000 claims description 8
- 239000007795 chemical reaction product Substances 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 239000002270 dispersing agent Substances 0.000 claims description 5
- 239000007787 solid Substances 0.000 claims description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 4
- 239000000853 adhesive Substances 0.000 claims description 4
- 230000001070 adhesive effect Effects 0.000 claims description 4
- 150000003973 alkyl amines Chemical class 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 4
- 239000000080 wetting agent Substances 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 238000000227 grinding Methods 0.000 claims description 3
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims description 2
- 238000000034 method Methods 0.000 claims 3
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical group [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims 3
- 230000003115 biocidal effect Effects 0.000 claims 2
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims 2
- JJCFRYNCJDLXIK-UHFFFAOYSA-N cyproheptadine Chemical compound C1CN(C)CCC1=C1C2=CC=CC=C2C=CC2=CC=CC=C21 JJCFRYNCJDLXIK-UHFFFAOYSA-N 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000003208 petroleum Substances 0.000 description 6
- 230000006378 damage Effects 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 239000005533 Fluometuron Substances 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- RZILCCPWPBTYDO-UHFFFAOYSA-N fluometuron Chemical compound CN(C)C(=O)NC1=CC=CC(C(F)(F)F)=C1 RZILCCPWPBTYDO-UHFFFAOYSA-N 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 244000046052 Phaseolus vulgaris Species 0.000 description 3
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 244000075850 Avena orientalis Species 0.000 description 2
- 240000006122 Chenopodium album Species 0.000 description 2
- 235000009344 Chenopodium album Nutrition 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 2
- 240000004713 Pisum sativum Species 0.000 description 2
- 240000006694 Stellaria media Species 0.000 description 2
- 241000209140 Triticum Species 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000003337 fertilizer Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000009331 sowing Methods 0.000 description 2
- XINQFOMFQFGGCQ-UHFFFAOYSA-L (2-dodecoxy-2-oxoethyl)-[6-[(2-dodecoxy-2-oxoethyl)-dimethylazaniumyl]hexyl]-dimethylazanium;dichloride Chemical compound [Cl-].[Cl-].CCCCCCCCCCCCOC(=O)C[N+](C)(C)CCCCCC[N+](C)(C)CC(=O)OCCCCCCCCCCCC XINQFOMFQFGGCQ-UHFFFAOYSA-L 0.000 description 1
- XEMRAKSQROQPBR-UHFFFAOYSA-N (trichloromethyl)benzene Chemical compound ClC(Cl)(Cl)C1=CC=CC=C1 XEMRAKSQROQPBR-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- OVUKQQRPTLPXTD-UHFFFAOYSA-N 1-(chloromethyl)-2,3-difluorobenzene Chemical compound FC1=CC=CC(CCl)=C1F OVUKQQRPTLPXTD-UHFFFAOYSA-N 0.000 description 1
- 244000291564 Allium cepa Species 0.000 description 1
- 235000005255 Allium cepa Nutrition 0.000 description 1
- 241001500843 Allium parvum Species 0.000 description 1
- 235000007319 Avena orientalis Nutrition 0.000 description 1
- 235000008427 Brassica arvensis Nutrition 0.000 description 1
- 244000024671 Brassica kaber Species 0.000 description 1
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 1
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical compound NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 241000220485 Fabaceae Species 0.000 description 1
- 241001289540 Fallopia convolvulus Species 0.000 description 1
- 244000214240 Galinsoga parviflora Species 0.000 description 1
- 235000018914 Galinsoga parviflora Nutrition 0.000 description 1
- 240000000697 Pinguicula vulgaris Species 0.000 description 1
- 235000010582 Pisum sativum Nutrition 0.000 description 1
- 244000110797 Polygonum persicaria Species 0.000 description 1
- 235000004442 Polygonum persicaria Nutrition 0.000 description 1
- 241000780602 Senecio Species 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 239000003139 biocide Substances 0.000 description 1
- PVXRCPDNJSFYBV-UHFFFAOYSA-N carbamoyl fluoride Chemical compound NC(F)=O PVXRCPDNJSFYBV-UHFFFAOYSA-N 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 150000008050 dialkyl sulfates Chemical class 0.000 description 1
- 125000005265 dialkylamine group Chemical group 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000003682 fluorination reaction Methods 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000003864 humus Substances 0.000 description 1
- 150000002443 hydroxylamines Chemical class 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 231100001184 nonphytotoxic Toxicity 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 230000000885 phytotoxic effect Effects 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 244000045561 useful plants Species 0.000 description 1
- 239000002699 waste material 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
- C07C275/28—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
-
- 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)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF49761A DE1300106B (de) | 1966-07-22 | 1966-07-22 | Verfahren zur Herstellung von Difluorchlormethylphenylharnstoffen |
| DEF0049762 | 1966-07-22 | ||
| US6853970A | 1970-08-31 | 1970-08-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| IL28241A true IL28241A (en) | 1971-06-23 |
Family
ID=27210493
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL28241A IL28241A (en) | 1966-07-22 | 1967-07-03 | Difluorochloromethylaryl ureas,their preparation and use as herbicides |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US3681422A (de) |
| BE (1) | BE701718A (de) |
| CH (1) | CH487587A (de) |
| DE (2) | DE1300106B (de) |
| DK (1) | DK115692B (de) |
| ES (1) | ES343018A1 (de) |
| GB (1) | GB1183737A (de) |
| IL (1) | IL28241A (de) |
| LU (1) | LU54124A1 (de) |
| NL (1) | NL6709902A (de) |
| SE (1) | SE317965B (de) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2234586A1 (de) * | 1972-07-14 | 1974-01-31 | Bayer Ag | N-arylharnstoffe, verfahren zu ihrer herstellung und ihre verwendung als herbizide |
| US3937627A (en) * | 1973-07-23 | 1976-02-10 | Shell Oil Company | Perchlorylphenylurea herbicide |
| JPS5636171B2 (de) * | 1973-10-30 | 1981-08-22 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3079244A (en) * | 1957-06-14 | 1963-02-26 | Hoechst Ag | Herbicidal method |
| NL128363C (de) * | 1959-08-21 | |||
| FR1310269A (de) * | 1961-01-19 | 1963-03-06 | ||
| DE1187605B (de) * | 1963-03-16 | 1965-02-25 | Bayer Ag | Verfahren zur Herstellung von acylierten Alkansulfensaeureamiden |
| US3520929A (en) * | 1966-10-19 | 1970-07-21 | Exxon Research Engineering Co | Hexafluoro-2-propanol-2-amines |
-
1966
- 1966-07-22 DE DEF49761A patent/DE1300106B/de active Pending
- 1966-07-22 DE DE19661542882 patent/DE1542882A1/de active Pending
-
1967
- 1967-07-03 IL IL28241A patent/IL28241A/en unknown
- 1967-07-14 ES ES343018A patent/ES343018A1/es not_active Expired
- 1967-07-14 DK DK366867AA patent/DK115692B/da unknown
- 1967-07-17 NL NL6709902A patent/NL6709902A/xx unknown
- 1967-07-18 LU LU54124D patent/LU54124A1/xx unknown
- 1967-07-19 CH CH1033967A patent/CH487587A/de not_active IP Right Cessation
- 1967-07-20 GB GB33418/67A patent/GB1183737A/en not_active Expired
- 1967-07-21 SE SE10740/67*A patent/SE317965B/xx unknown
- 1967-07-24 BE BE701718D patent/BE701718A/xx unknown
-
1970
- 1970-08-31 US US68539A patent/US3681422A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| SE317965B (de) | 1969-12-01 |
| DE1542882A1 (de) | 1970-06-04 |
| GB1183737A (en) | 1970-03-11 |
| ES343018A1 (es) | 1968-10-16 |
| US3681422A (en) | 1972-08-01 |
| BE701718A (de) | 1968-01-24 |
| DK115692B (da) | 1969-11-03 |
| DE1300106B (de) | 1969-07-31 |
| CH487587A (de) | 1970-03-31 |
| NL6709902A (de) | 1968-01-23 |
| LU54124A1 (de) | 1969-05-21 |
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