DE1226569B - Verfahren zur Herstellung von Harnstoffderivaten - Google Patents
Verfahren zur Herstellung von HarnstoffderivatenInfo
- Publication number
- DE1226569B DE1226569B DEB82033A DEB0082033A DE1226569B DE 1226569 B DE1226569 B DE 1226569B DE B82033 A DEB82033 A DE B82033A DE B0082033 A DEB0082033 A DE B0082033A DE 1226569 B DE1226569 B DE 1226569B
- Authority
- DE
- Germany
- Prior art keywords
- methyl
- bicyclo
- octyl
- urea
- carbamic acid
- 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 8
- 150000003672 ureas Chemical class 0.000 title claims description 7
- 238000004519 manufacturing process Methods 0.000 title description 2
- 239000004202 carbamide Substances 0.000 claims description 10
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 9
- -1 2-bicyclo- [3,2,1] -octyl Chemical group 0.000 claims description 7
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical class NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 claims description 3
- 239000012948 isocyanate Substances 0.000 claims description 3
- 150000002513 isocyanates Chemical class 0.000 claims description 3
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 2
- 229940112021 centrally acting muscle relaxants carbamic acid ester Drugs 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- SEDYEJKMKNWLGX-UHFFFAOYSA-N n-methylbut-3-yn-2-amine Chemical compound CNC(C)C#C SEDYEJKMKNWLGX-UHFFFAOYSA-N 0.000 claims description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 2
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims 1
- 240000006122 Chenopodium album Species 0.000 description 10
- 241000196324 Embryophyta Species 0.000 description 10
- 244000292693 Poa annua Species 0.000 description 10
- 235000013877 carbamide Nutrition 0.000 description 9
- 240000006694 Stellaria media Species 0.000 description 8
- 244000042664 Matricaria chamomilla Species 0.000 description 7
- 235000007232 Matricaria chamomilla Nutrition 0.000 description 7
- 235000009108 Urtica dioica Nutrition 0.000 description 7
- 244000024671 Brassica kaber Species 0.000 description 6
- 235000011498 Chenopodium album var missouriense Nutrition 0.000 description 6
- 235000013328 Chenopodium album var. album Nutrition 0.000 description 6
- 235000014052 Chenopodium album var. microphyllum Nutrition 0.000 description 6
- 235000014050 Chenopodium album var. stevensii Nutrition 0.000 description 6
- 235000013012 Chenopodium album var. striatum Nutrition 0.000 description 6
- 244000000626 Daucus carota Species 0.000 description 6
- 235000002767 Daucus carota Nutrition 0.000 description 6
- 240000005979 Hordeum vulgare Species 0.000 description 6
- 235000007340 Hordeum vulgare Nutrition 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 241000209140 Triticum Species 0.000 description 6
- 235000021307 Triticum Nutrition 0.000 description 6
- 240000008042 Zea mays Species 0.000 description 6
- 239000004480 active ingredient Substances 0.000 description 6
- 230000002363 herbicidal effect Effects 0.000 description 5
- BMLIZLVNXIYGCK-UHFFFAOYSA-N monuron Chemical compound CN(C)C(=O)NC1=CC=C(Cl)C=C1 BMLIZLVNXIYGCK-UHFFFAOYSA-N 0.000 description 5
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 241000219198 Brassica Species 0.000 description 4
- 235000008427 Brassica arvensis Nutrition 0.000 description 4
- 235000003351 Brassica cretica Nutrition 0.000 description 4
- 235000003343 Brassica rupestris Nutrition 0.000 description 4
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 4
- 235000007866 Chamaemelum nobile Nutrition 0.000 description 4
- 235000009344 Chenopodium album Nutrition 0.000 description 4
- 240000004153 Hibiscus sabdariffa Species 0.000 description 4
- 235000001018 Hibiscus sabdariffa Nutrition 0.000 description 4
- 235000005291 Rumex acetosa Nutrition 0.000 description 4
- 244000274883 Urtica dioica Species 0.000 description 4
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 4
- 241001148683 Zostera marina Species 0.000 description 4
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 235000010460 mustard Nutrition 0.000 description 4
- 235000003513 sheep sorrel Nutrition 0.000 description 4
- 241001456088 Hesperocnide Species 0.000 description 3
- 240000004713 Pisum sativum Species 0.000 description 3
- 235000010582 Pisum sativum Nutrition 0.000 description 3
- 241000219053 Rumex Species 0.000 description 3
- 244000061456 Solanum tuberosum Species 0.000 description 3
- 235000002595 Solanum tuberosum Nutrition 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 240000001592 Amaranthus caudatus Species 0.000 description 2
- 235000009328 Amaranthus caudatus Nutrition 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 235000005637 Brassica campestris Nutrition 0.000 description 2
- 235000014750 Brassica kaber Nutrition 0.000 description 2
- 235000010149 Brassica rapa subsp chinensis Nutrition 0.000 description 2
- 235000010570 Brassica rapa var. rapa Nutrition 0.000 description 2
- YIIMEMSDCNDGTB-UHFFFAOYSA-N Dimethylcarbamoyl chloride Chemical compound CN(C)C(Cl)=O YIIMEMSDCNDGTB-UHFFFAOYSA-N 0.000 description 2
- 244000214240 Galinsoga parviflora Species 0.000 description 2
- 235000018914 Galinsoga parviflora Nutrition 0.000 description 2
- MGJKQDOBUOMPEZ-UHFFFAOYSA-N N,N'-dimethylurea Chemical compound CNC(=O)NC MGJKQDOBUOMPEZ-UHFFFAOYSA-N 0.000 description 2
- 235000007244 Zea mays Nutrition 0.000 description 2
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 2
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 235000005822 corn Nutrition 0.000 description 2
- 244000038559 crop plants Species 0.000 description 2
- 210000003734 kidney Anatomy 0.000 description 2
- 235000009973 maize Nutrition 0.000 description 2
- 235000012015 potatoes Nutrition 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- OXIQWCQQDYUWRW-UHFFFAOYSA-N 3-(2-bicyclo[3.2.1]octanyl)-1,1-dimethylurea Chemical compound C12C(CCC(CC1)C2)NC(=O)N(C)C OXIQWCQQDYUWRW-UHFFFAOYSA-N 0.000 description 1
- QGCXJGIWFPLTGG-UHFFFAOYSA-N 3-(2-bicyclo[3.2.1]octanyl)-1-methoxy-1-methylurea Chemical compound C12C(CCC(CC1)C2)NC(=O)N(OC)C QGCXJGIWFPLTGG-UHFFFAOYSA-N 0.000 description 1
- 241000743985 Alopecurus Species 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- DQZCVNGCTZLGAQ-UHFFFAOYSA-N Cycluron Chemical compound CN(C)C(=O)NC1CCCCCCC1 DQZCVNGCTZLGAQ-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical group 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 210000003298 dental enamel Anatomy 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- SHQJHXLWZDMQEJ-UHFFFAOYSA-N n-methoxy-n-methylcarbamoyl chloride Chemical compound CON(C)C(Cl)=O SHQJHXLWZDMQEJ-UHFFFAOYSA-N 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/32—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing >N—CO—N< or >N—CS—N< groups directly attached to a cycloaliphatic ring
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB82033A DE1226569B (de) | 1965-05-20 | 1965-05-20 | Verfahren zur Herstellung von Harnstoffderivaten |
| FR61512A FR1479858A (fr) | 1965-05-20 | 1966-05-13 | Dérivés de l'urée et mélanges herbicides les contenant |
| BE681090D BE681090A (en:Method) | 1965-05-20 | 1966-05-16 | |
| GB2161566A GB1139919A (en) | 1965-05-20 | 1966-05-16 | Urea derivatives and herbicidal compositions containing same |
| NL6606862A NL6606862A (en:Method) | 1965-05-20 | 1966-05-18 | |
| AT479266A AT260615B (de) | 1965-05-20 | 1966-05-20 | Herbizide Mischung |
| ES0326953A ES326953A1 (es) | 1965-05-20 | 1966-05-20 | Procedimiento para preparar una composicion. |
| DK258266A DK112908B (da) | 1965-05-20 | 1966-05-20 | Herbicid. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB82033A DE1226569B (de) | 1965-05-20 | 1965-05-20 | Verfahren zur Herstellung von Harnstoffderivaten |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1226569B true DE1226569B (de) | 1966-10-13 |
Family
ID=6981349
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEB82033A Pending DE1226569B (de) | 1965-05-20 | 1965-05-20 | Verfahren zur Herstellung von Harnstoffderivaten |
Country Status (7)
| Country | Link |
|---|---|
| AT (1) | AT260615B (en:Method) |
| BE (1) | BE681090A (en:Method) |
| DE (1) | DE1226569B (en:Method) |
| DK (1) | DK112908B (en:Method) |
| ES (1) | ES326953A1 (en:Method) |
| GB (1) | GB1139919A (en:Method) |
| NL (1) | NL6606862A (en:Method) |
-
1965
- 1965-05-20 DE DEB82033A patent/DE1226569B/de active Pending
-
1966
- 1966-05-16 GB GB2161566A patent/GB1139919A/en not_active Expired
- 1966-05-16 BE BE681090D patent/BE681090A/xx unknown
- 1966-05-18 NL NL6606862A patent/NL6606862A/xx unknown
- 1966-05-20 DK DK258266A patent/DK112908B/da unknown
- 1966-05-20 ES ES0326953A patent/ES326953A1/es not_active Expired
- 1966-05-20 AT AT479266A patent/AT260615B/de active
Also Published As
| Publication number | Publication date |
|---|---|
| GB1139919A (en) | 1969-01-15 |
| NL6606862A (en:Method) | 1966-11-21 |
| AT260615B (de) | 1968-03-11 |
| BE681090A (en:Method) | 1966-11-16 |
| ES326953A1 (es) | 1967-08-01 |
| DK112908B (da) | 1969-01-27 |
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