DE2133867A1 - N-arylharnstoffe, verfahren zu ihrer herstellung und ihre verwendung als herbizide - Google Patents
N-arylharnstoffe, verfahren zu ihrer herstellung und ihre verwendung als herbizideInfo
- Publication number
- DE2133867A1 DE2133867A1 DE2133867A DE2133867A DE2133867A1 DE 2133867 A1 DE2133867 A1 DE 2133867A1 DE 2133867 A DE2133867 A DE 2133867A DE 2133867 A DE2133867 A DE 2133867A DE 2133867 A1 DE2133867 A1 DE 2133867A1
- Authority
- DE
- Germany
- Prior art keywords
- ureas
- hydrogen
- aryl
- carbon atoms
- difluorochloromethylsulfinyl
- 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
- 238000000034 method Methods 0.000 title claims description 9
- 239000004009 herbicide Substances 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title claims 2
- 239000004202 carbamide Substances 0.000 title description 2
- 241000196324 Embryophyta Species 0.000 claims description 12
- 235000013877 carbamide Nutrition 0.000 claims description 12
- -1 difluorochloromethylsulfinyl Chemical group 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 150000003672 ureas Chemical class 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 6
- 239000007800 oxidant agent Substances 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 239000004606 Fillers/Extenders Substances 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- BATXDAOYKMKRSG-UHFFFAOYSA-N FCl(CCl)(F)S Chemical compound FCl(CCl)(F)S BATXDAOYKMKRSG-UHFFFAOYSA-N 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 239000004094 surface-active agent Substances 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 description 17
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- 239000003995 emulsifying agent Substances 0.000 description 5
- 230000002363 herbicidal effect Effects 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 241000219146 Gossypium Species 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-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
- 241000209140 Triticum Species 0.000 description 3
- 235000021307 Triticum Nutrition 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 244000075850 Avena orientalis Species 0.000 description 2
- 241000209200 Bromus Species 0.000 description 2
- 241000723377 Coffea Species 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 235000007351 Eleusine Nutrition 0.000 description 2
- 241000209215 Eleusine Species 0.000 description 2
- 244000042664 Matricaria chamomilla Species 0.000 description 2
- 235000007232 Matricaria chamomilla Nutrition 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 241000209094 Oryza Species 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 240000006694 Stellaria media Species 0.000 description 2
- 241000219422 Urtica Species 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 125000002877 alkyl aryl group Chemical group 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000006072 paste Substances 0.000 description 2
- 229920000151 polyglycol Polymers 0.000 description 2
- 239000010695 polyglycol Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 240000002245 Acer pensylvanicum Species 0.000 description 1
- 235000006760 Acer pensylvanicum Nutrition 0.000 description 1
- 240000005528 Arctium lappa Species 0.000 description 1
- 235000003130 Arctium lappa Nutrition 0.000 description 1
- 235000008078 Arctium minus Nutrition 0.000 description 1
- 235000005781 Avena Nutrition 0.000 description 1
- 235000007319 Avena orientalis Nutrition 0.000 description 1
- 235000016068 Berberis vulgaris Nutrition 0.000 description 1
- 241000335053 Beta vulgaris Species 0.000 description 1
- 244000056139 Brassica cretica Species 0.000 description 1
- 235000003351 Brassica cretica Nutrition 0.000 description 1
- 235000003343 Brassica rupestris Nutrition 0.000 description 1
- 235000007866 Chamaemelum nobile Nutrition 0.000 description 1
- 241000251730 Chondrichthyes Species 0.000 description 1
- 244000000626 Daucus carota Species 0.000 description 1
- 235000002767 Daucus carota Nutrition 0.000 description 1
- 244000239348 Echinochloa crus galli var. praticola Species 0.000 description 1
- 241000234642 Festuca Species 0.000 description 1
- 241000748465 Galinsoga Species 0.000 description 1
- 241001101998 Galium Species 0.000 description 1
- 235000009438 Gossypium Nutrition 0.000 description 1
- 241000209219 Hordeum Species 0.000 description 1
- 240000005979 Hordeum vulgare Species 0.000 description 1
- 235000007340 Hordeum vulgare Nutrition 0.000 description 1
- 241000801118 Lepidium Species 0.000 description 1
- 244000211187 Lepidium sativum Species 0.000 description 1
- 235000007849 Lepidium sativum Nutrition 0.000 description 1
- 241000209510 Liliopsida Species 0.000 description 1
- 241000209082 Lolium Species 0.000 description 1
- 235000017945 Matricaria Nutrition 0.000 description 1
- MGJKQDOBUOMPEZ-UHFFFAOYSA-N N,N'-dimethylurea Chemical compound CNC(=O)NC MGJKQDOBUOMPEZ-UHFFFAOYSA-N 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 241000209117 Panicum Species 0.000 description 1
- 235000006443 Panicum miliaceum subsp. miliaceum Nutrition 0.000 description 1
- 235000009037 Panicum miliaceum subsp. ruderale Nutrition 0.000 description 1
- 241000219833 Phaseolus Species 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- 241000746981 Phleum Species 0.000 description 1
- 241000746983 Phleum pratense Species 0.000 description 1
- 241001310793 Podium Species 0.000 description 1
- 240000000111 Saccharum officinarum Species 0.000 description 1
- 235000007201 Saccharum officinarum Nutrition 0.000 description 1
- 241000780602 Senecio Species 0.000 description 1
- 240000003705 Senecio vulgaris Species 0.000 description 1
- 235000005775 Setaria Nutrition 0.000 description 1
- 241000232088 Setaria <nematode> Species 0.000 description 1
- 241000220261 Sinapis Species 0.000 description 1
- 235000002634 Solanum Nutrition 0.000 description 1
- 241000207763 Solanum Species 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 244000062793 Sorghum vulgare Species 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 244000274883 Urtica dioica Species 0.000 description 1
- 235000009108 Urtica dioica Nutrition 0.000 description 1
- 241000209149 Zea Species 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 150000008422 chlorobenzenes Chemical class 0.000 description 1
- KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 241001233957 eudicotyledons Species 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 244000230030 foxtail bristlegrass Species 0.000 description 1
- AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 235000009973 maize Nutrition 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 235000019713 millet Nutrition 0.000 description 1
- 235000010460 mustard Nutrition 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 235000012015 potatoes Nutrition 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 239000011435 rock Substances 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/26—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C317/32—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C317/34—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having sulfone or sulfoxide groups and amino groups bound to carbon atoms of six-membered aromatic rings being part of the same non-condensed ring or of a condensed ring system containing that ring
- C07C317/38—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having sulfone or sulfoxide groups and amino groups bound to carbon atoms of six-membered aromatic rings being part of the same non-condensed ring or of a condensed ring system containing that ring with the nitrogen atom of at least one amino group being part of any of the groups, X being a hetero atom, Y being any atom, e.g. N-acylaminosulfones
- C07C317/42—Y being a hetero atom
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 (12)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE785930D BE785930A (fr) | 1971-07-07 | Nouvelles arylurees, leur procede de preparation et leur application comme herbicides | |
| DE2133867A DE2133867A1 (de) | 1971-07-07 | 1971-07-07 | N-arylharnstoffe, verfahren zu ihrer herstellung und ihre verwendung als herbizide |
| OA54633A OA04253A (fr) | 1971-07-07 | 1972-07-03 | Nouvelles arylurées, leur procédé de préparation et leur application comme herbicides. |
| IL39825A IL39825A (en) | 1971-07-07 | 1972-07-04 | N-chlorodifluoromethylsulphinyl phenyl ureas,processes for their manufacture and herbicidal compositions containing them |
| BG020894A BG19074A3 (bg) | 1971-07-07 | 1972-07-05 | Хербецидно средство |
| IT26677/72A IT962470B (it) | 1971-07-07 | 1972-07-05 | N ariluree procedimento per la loro preparazione e loro impiego come erbicidi |
| CH1009972A CH586669A5 (enrdf_load_stackoverflow) | 1971-07-07 | 1972-07-05 | |
| GB3171872A GB1331217A (en) | 1971-07-07 | 1972-07-06 | N-arylureas processes for their manufacture and their use as herbicides |
| DD164231A DD101268A5 (enrdf_load_stackoverflow) | 1971-07-07 | 1972-07-06 | |
| NL7209439A NL7209439A (enrdf_load_stackoverflow) | 1971-07-07 | 1972-07-06 | |
| FR7224687A FR2145319A5 (enrdf_load_stackoverflow) | 1971-07-07 | 1972-07-07 | |
| BR4498/72A BR7204498D0 (pt) | 1971-07-07 | 1972-07-07 | Processo de preparacao de novas n-aril-ureias composicoes herbicidas a base das mesmas processo para combater plantas daninhas com emprego das mesmas e processo para preparacao das ditas composicoes |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2133867A DE2133867A1 (de) | 1971-07-07 | 1971-07-07 | N-arylharnstoffe, verfahren zu ihrer herstellung und ihre verwendung als herbizide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2133867A1 true DE2133867A1 (de) | 1973-01-25 |
Family
ID=5812972
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2133867A Pending DE2133867A1 (de) | 1971-07-07 | 1971-07-07 | N-arylharnstoffe, verfahren zu ihrer herstellung und ihre verwendung als herbizide |
Country Status (12)
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5995281A (ja) * | 1982-11-19 | 1984-06-01 | Kotobuki Seiyaku Kk | チアゾ−ル誘導体及びその製造方法 |
-
0
- BE BE785930D patent/BE785930A/xx unknown
-
1971
- 1971-07-07 DE DE2133867A patent/DE2133867A1/de active Pending
-
1972
- 1972-07-03 OA OA54633A patent/OA04253A/xx unknown
- 1972-07-04 IL IL39825A patent/IL39825A/xx unknown
- 1972-07-05 CH CH1009972A patent/CH586669A5/xx not_active IP Right Cessation
- 1972-07-05 BG BG020894A patent/BG19074A3/xx unknown
- 1972-07-05 IT IT26677/72A patent/IT962470B/it active
- 1972-07-06 GB GB3171872A patent/GB1331217A/en not_active Expired
- 1972-07-06 DD DD164231A patent/DD101268A5/xx unknown
- 1972-07-06 NL NL7209439A patent/NL7209439A/xx unknown
- 1972-07-07 BR BR4498/72A patent/BR7204498D0/pt unknown
- 1972-07-07 FR FR7224687A patent/FR2145319A5/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB1331217A (en) | 1973-09-26 |
| BE785930A (fr) | 1973-01-08 |
| IT962470B (it) | 1973-12-20 |
| DD101268A5 (enrdf_load_stackoverflow) | 1973-11-05 |
| IL39825A0 (en) | 1972-09-28 |
| IL39825A (en) | 1975-04-25 |
| NL7209439A (enrdf_load_stackoverflow) | 1973-01-09 |
| BG19074A3 (bg) | 1975-04-30 |
| BR7204498D0 (pt) | 1973-05-03 |
| CH586669A5 (enrdf_load_stackoverflow) | 1977-04-15 |
| OA04253A (fr) | 1979-12-31 |
| FR2145319A5 (enrdf_load_stackoverflow) | 1973-02-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHN | Withdrawal |