DE2530908B2 - Von Phenylhydroxylamin abgeleitete Carbaminsäureester, Verfahren zu ihrer Herstellung und herbizide Mittel, die diese Verbindungen als Wirkstoffe enthalten - Google Patents
Von Phenylhydroxylamin abgeleitete Carbaminsäureester, Verfahren zu ihrer Herstellung und herbizide Mittel, die diese Verbindungen als Wirkstoffe enthaltenInfo
- Publication number
- DE2530908B2 DE2530908B2 DE2530908A DE2530908A DE2530908B2 DE 2530908 B2 DE2530908 B2 DE 2530908B2 DE 2530908 A DE2530908 A DE 2530908A DE 2530908 A DE2530908 A DE 2530908A DE 2530908 B2 DE2530908 B2 DE 2530908B2
- Authority
- DE
- Germany
- Prior art keywords
- carbo
- preparation
- phenylhydroxylamine
- phenoxy
- compounds
- 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.)
- Granted
Links
- 238000002360 preparation method Methods 0.000 title claims description 31
- 150000001875 compounds Chemical class 0.000 title claims description 12
- CKRZKMFTZCFYGB-UHFFFAOYSA-N N-phenylhydroxylamine Chemical compound ONC1=CC=CC=C1 CKRZKMFTZCFYGB-UHFFFAOYSA-N 0.000 title claims description 7
- 229940112021 centrally acting muscle relaxants carbamic acid ester Drugs 0.000 title claims description 3
- 238000000034 method Methods 0.000 title claims description 3
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 title claims description 3
- 230000002363 herbicidal effect Effects 0.000 title description 12
- 239000004480 active ingredient Substances 0.000 title description 5
- 239000000203 mixture Substances 0.000 title description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 229910052801 chlorine Chemical group 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 241000196324 Embryophyta Species 0.000 description 21
- 239000000460 chlorine Substances 0.000 description 14
- 238000002844 melting Methods 0.000 description 13
- 230000008018 melting Effects 0.000 description 13
- -1 aryl chlorocarbonate Chemical compound 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 239000004009 herbicide Substances 0.000 description 8
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 8
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 7
- 235000021536 Sugar beet Nutrition 0.000 description 7
- 239000000839 emulsion Substances 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 240000008415 Lactuca sativa Species 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
- 238000009331 sowing Methods 0.000 description 6
- 244000300264 Spinacia oleracea Species 0.000 description 5
- 235000009337 Spinacia oleracea Nutrition 0.000 description 5
- 239000013543 active substance Substances 0.000 description 5
- AOGYCOYQMAVAFD-UHFFFAOYSA-M carbonochloridate Chemical compound [O-]C(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-M 0.000 description 5
- 239000012141 concentrate Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical compound NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 description 4
- 235000016068 Berberis vulgaris Nutrition 0.000 description 4
- 241000335053 Beta vulgaris Species 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 244000062793 Sorghum vulgare Species 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 235000019713 millet Nutrition 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 240000001592 Amaranthus caudatus Species 0.000 description 3
- 235000009328 Amaranthus caudatus Nutrition 0.000 description 3
- 244000036975 Ambrosia artemisiifolia Species 0.000 description 3
- 235000003129 Ambrosia artemisiifolia var elatior Nutrition 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 240000008100 Brassica rapa Species 0.000 description 3
- 240000006122 Chenopodium album Species 0.000 description 3
- 241000192043 Echinochloa Species 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 244000042664 Matricaria chamomilla Species 0.000 description 3
- 235000007232 Matricaria chamomilla Nutrition 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 235000003484 annual ragweed Nutrition 0.000 description 3
- 235000006263 bur ragweed Nutrition 0.000 description 3
- 235000003488 common ragweed Nutrition 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- AKSIQQBEDAZPLD-UHFFFAOYSA-N n-(3,4-dichlorophenyl)hydroxylamine Chemical compound ONC1=CC=C(Cl)C(Cl)=C1 AKSIQQBEDAZPLD-UHFFFAOYSA-N 0.000 description 3
- QITLDCYUPWIQCI-UHFFFAOYSA-N n-(3-methylphenyl)hydroxylamine Chemical compound CC1=CC=CC(NO)=C1 QITLDCYUPWIQCI-UHFFFAOYSA-N 0.000 description 3
- RWSLVCOQGBADFY-UHFFFAOYSA-N n-phenoxy-n-phenylhydroxylamine Chemical compound C=1C=CC=CC=1N(O)OC1=CC=CC=C1 RWSLVCOQGBADFY-UHFFFAOYSA-N 0.000 description 3
- 235000009736 ragweed Nutrition 0.000 description 3
- 235000012045 salad Nutrition 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- 229940018563 3-aminophenol Drugs 0.000 description 2
- 235000011293 Brassica napus Nutrition 0.000 description 2
- 235000000540 Brassica rapa subsp rapa Nutrition 0.000 description 2
- 235000007866 Chamaemelum nobile Nutrition 0.000 description 2
- 241000965754 Chenopodium acuminatum subsp. virgatum Species 0.000 description 2
- 235000011498 Chenopodium album var missouriense Nutrition 0.000 description 2
- 235000013328 Chenopodium album var. album Nutrition 0.000 description 2
- 235000014052 Chenopodium album var. microphyllum Nutrition 0.000 description 2
- 235000014050 Chenopodium album var. stevensii Nutrition 0.000 description 2
- 235000013012 Chenopodium album var. striatum Nutrition 0.000 description 2
- 206010053759 Growth retardation Diseases 0.000 description 2
- 235000003228 Lactuca sativa Nutrition 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- JWNBSBVOTFTCBO-UHFFFAOYSA-N N-(3-chlorophenyl)-N-phenoxyhydroxylamine Chemical compound ON(OC1=CC=CC=C1)C1=CC(Cl)=CC=C1 JWNBSBVOTFTCBO-UHFFFAOYSA-N 0.000 description 2
- AYDPYVVPZRNZKC-UHFFFAOYSA-N N-(3-methylphenyl)-N-phenoxyhydroxylamine Chemical compound O(C1=CC=CC=C1)N(O)C=1C=C(C=CC=1)C AYDPYVVPZRNZKC-UHFFFAOYSA-N 0.000 description 2
- 244000046052 Phaseolus vulgaris Species 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 150000001346 alkyl aryl ethers Chemical class 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 235000021374 legumes Nutrition 0.000 description 2
- CTTWLAMAVFBFAR-UHFFFAOYSA-N n-(3-chlorophenyl)hydroxylamine Chemical compound ONC1=CC=CC(Cl)=C1 CTTWLAMAVFBFAR-UHFFFAOYSA-N 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 125000001273 sulfonato group Chemical class [O-]S(*)(=O)=O 0.000 description 2
- 241000219305 Atriplex Species 0.000 description 1
- 241000219198 Brassica Species 0.000 description 1
- 235000005637 Brassica campestris Nutrition 0.000 description 1
- 235000003351 Brassica cretica Nutrition 0.000 description 1
- 235000014750 Brassica kaber Nutrition 0.000 description 1
- 235000010149 Brassica rapa subsp chinensis Nutrition 0.000 description 1
- 235000010570 Brassica rapa var. rapa Nutrition 0.000 description 1
- 235000003343 Brassica rupestris Nutrition 0.000 description 1
- 235000009344 Chenopodium album Nutrition 0.000 description 1
- 240000008620 Fagopyrum esculentum Species 0.000 description 1
- 235000009419 Fagopyrum esculentum Nutrition 0.000 description 1
- 241000748465 Galinsoga Species 0.000 description 1
- 241000287828 Gallus gallus Species 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- 235000010702 Insulata Nutrition 0.000 description 1
- 235000017945 Matricaria Nutrition 0.000 description 1
- FLBGHPBLEGXANR-UHFFFAOYSA-N N-(4-chlorophenyl)-N-phenoxyhydroxylamine Chemical compound O(C1=CC=CC=C1)N(C1=CC=C(C=C1)Cl)O FLBGHPBLEGXANR-UHFFFAOYSA-N 0.000 description 1
- RHAFSVJQOHTAIA-UHFFFAOYSA-N OC(=O)NC1(C)CC=CC=C1 Chemical compound OC(=O)NC1(C)CC=CC=C1 RHAFSVJQOHTAIA-UHFFFAOYSA-N 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- 231100000674 Phytotoxicity Toxicity 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 240000005578 Rivina humilis Species 0.000 description 1
- 241000862969 Stella Species 0.000 description 1
- 240000006694 Stellaria media Species 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 244000098338 Triticum aestivum Species 0.000 description 1
- 235000002096 Vicia faba var. equina Nutrition 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- DDKMFOUTRRODRE-UHFFFAOYSA-N chloromethanone Chemical compound Cl[C]=O DDKMFOUTRRODRE-UHFFFAOYSA-N 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 235000005489 dwarf bean Nutrition 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000010413 gardening Methods 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 235000010460 mustard Nutrition 0.000 description 1
- AGJOAIMUXIQLCN-UHFFFAOYSA-N n-(4-methylphenyl)hydroxylamine Chemical compound CC1=CC=C(NO)C=C1 AGJOAIMUXIQLCN-UHFFFAOYSA-N 0.000 description 1
- CPQCSJYYDADLCZ-UHFFFAOYSA-N n-methylhydroxylamine Chemical compound CNO CPQCSJYYDADLCZ-UHFFFAOYSA-N 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 210000003296 saliva Anatomy 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000009333 weeding Methods 0.000 description 1
- 239000012224 working solution Substances 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
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/24—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing the groups, or; Thio analogues thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Hydrogenated Pyridines (AREA)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE158121A BE831163A (fr) | 1975-07-09 | 1975-07-09 | N-carboaryloxy-n-arylhydroxylamines, leur procede de preparation et leurs utilisations |
| DE2530908A DE2530908B2 (de) | 1975-07-09 | 1975-07-10 | Von Phenylhydroxylamin abgeleitete Carbaminsäureester, Verfahren zu ihrer Herstellung und herbizide Mittel, die diese Verbindungen als Wirkstoffe enthalten |
| FR7522581A FR2318150A1 (fr) | 1975-07-09 | 1975-07-18 | N-carboaryloxy-n-arylhydroxylamines, leur procede de preparation et applications a titre d'herbicides |
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE158121A BE831163A (fr) | 1975-07-09 | 1975-07-09 | N-carboaryloxy-n-arylhydroxylamines, leur procede de preparation et leurs utilisations |
| BE831163 | 1975-07-09 | ||
| DE2530908A DE2530908B2 (de) | 1975-07-09 | 1975-07-10 | Von Phenylhydroxylamin abgeleitete Carbaminsäureester, Verfahren zu ihrer Herstellung und herbizide Mittel, die diese Verbindungen als Wirkstoffe enthalten |
| FR7522581A FR2318150A1 (fr) | 1975-07-09 | 1975-07-18 | N-carboaryloxy-n-arylhydroxylamines, leur procede de preparation et applications a titre d'herbicides |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2530908A1 DE2530908A1 (de) | 1977-01-13 |
| DE2530908B2 true DE2530908B2 (de) | 1978-07-06 |
| DE2530908C3 DE2530908C3 (enrdf_load_stackoverflow) | 1979-03-01 |
Family
ID=27424641
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2530908A Granted DE2530908B2 (de) | 1975-07-09 | 1975-07-10 | Von Phenylhydroxylamin abgeleitete Carbaminsäureester, Verfahren zu ihrer Herstellung und herbizide Mittel, die diese Verbindungen als Wirkstoffe enthalten |
Country Status (3)
| Country | Link |
|---|---|
| BE (1) | BE831163A (enrdf_load_stackoverflow) |
| DE (1) | DE2530908B2 (enrdf_load_stackoverflow) |
| FR (1) | FR2318150A1 (enrdf_load_stackoverflow) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5109011A (en) * | 1990-07-30 | 1992-04-28 | Hoechst-Roussel Pharmaceuticals Incorporated | P-acylaminophenoxycarbamates and derivatives |
-
1975
- 1975-07-09 BE BE158121A patent/BE831163A/xx not_active IP Right Cessation
- 1975-07-10 DE DE2530908A patent/DE2530908B2/de active Granted
- 1975-07-18 FR FR7522581A patent/FR2318150A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| FR2318150A1 (fr) | 1977-02-11 |
| DE2530908C3 (enrdf_load_stackoverflow) | 1979-03-01 |
| FR2318150B1 (enrdf_load_stackoverflow) | 1977-12-16 |
| BE831163A (fr) | 1976-01-09 |
| DE2530908A1 (de) | 1977-01-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |