DE2913976A1 - Substituierte carbanilsaeureester, verfahren zur herstellung dieser verbindungen sowie diese enthaltende selektive herbizide mittel - Google Patents
Substituierte carbanilsaeureester, verfahren zur herstellung dieser verbindungen sowie diese enthaltende selektive herbizide mittelInfo
- Publication number
- DE2913976A1 DE2913976A1 DE19792913976 DE2913976A DE2913976A1 DE 2913976 A1 DE2913976 A1 DE 2913976A1 DE 19792913976 DE19792913976 DE 19792913976 DE 2913976 A DE2913976 A DE 2913976A DE 2913976 A1 DE2913976 A1 DE 2913976A1
- Authority
- DE
- Germany
- Prior art keywords
- deep
- chloro
- carbanilic acid
- ester
- dichloro
- 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.)
- Withdrawn
Links
- 150000001875 compounds Chemical class 0.000 title claims description 28
- PWXJULSLLONQHY-UHFFFAOYSA-N phenylcarbamic acid Chemical class OC(=O)NC1=CC=CC=C1 PWXJULSLLONQHY-UHFFFAOYSA-N 0.000 title claims description 7
- 239000004009 herbicide Substances 0.000 title claims description 5
- 238000004519 manufacturing process Methods 0.000 title 1
- -1 carbanilic acid ester Chemical class 0.000 claims description 32
- 239000001257 hydrogen Substances 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 9
- 239000000460 chlorine Substances 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 230000002363 herbicidal effect Effects 0.000 claims description 6
- 239000000969 carrier Substances 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- 125000006022 2-methyl-2-propenyl group Chemical group 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 3
- 239000012948 isocyanate Substances 0.000 claims description 3
- 150000002513 isocyanates Chemical class 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- USUFULRODJKQDU-UHFFFAOYSA-N methyl n-[3-chloro-4-[(2,2-dichlorocyclopropyl)methoxy]phenyl]carbamate Chemical compound ClC1=CC(NC(=O)OC)=CC=C1OCC1C(Cl)(Cl)C1 USUFULRODJKQDU-UHFFFAOYSA-N 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- XCSLTHLBXFNJOJ-UHFFFAOYSA-N propyl n-[3-chloro-4-[(2,2-dichlorocyclopropyl)methoxy]phenyl]carbamate Chemical compound ClC1=CC(NC(=O)OCCC)=CC=C1OCC1C(Cl)(Cl)C1 XCSLTHLBXFNJOJ-UHFFFAOYSA-N 0.000 claims description 3
- RUECMRAGWYGREK-UHFFFAOYSA-N [3-chloro-4-[(2,2-dichloro-1-methylcyclopropyl)methoxy]phenyl]carbamic acid Chemical compound ClC=1C=C(NC(O)=O)C=CC=1OCC1(C(C1)(Cl)Cl)C RUECMRAGWYGREK-UHFFFAOYSA-N 0.000 claims 2
- SKQABCHLXUUCGX-UHFFFAOYSA-N 2-methylprop-2-enyl N-[3-chloro-4-[(2,2-dichloro-1-methylcyclopropyl)methoxy]phenyl]carbamate Chemical compound CC(COC(NC1=CC(=C(C=C1)OCC1(C(C1)(Cl)Cl)C)Cl)=O)=C SKQABCHLXUUCGX-UHFFFAOYSA-N 0.000 claims 1
- JKYHCGGKRNEEQC-UHFFFAOYSA-N 2-methylprop-2-enyl N-[3-chloro-4-[(2,2-dichlorocyclopropyl)methoxy]phenyl]carbamate Chemical compound CC(COC(NC1=CC(=C(C=C1)OCC1C(C1)(Cl)Cl)Cl)=O)=C JKYHCGGKRNEEQC-UHFFFAOYSA-N 0.000 claims 1
- UZFIBINUOLGTNH-UHFFFAOYSA-N ethyl N-[3-chloro-4-[(2,2-dichloro-3-methylcyclopropyl)methoxy]phenyl]carbamate Chemical compound C(C)OC(NC1=CC(=C(C=C1)OCC1C(C1C)(Cl)Cl)Cl)=O UZFIBINUOLGTNH-UHFFFAOYSA-N 0.000 claims 1
- DIDDJBKATVHPFB-UHFFFAOYSA-N ethyl N-[3-chloro-4-[(2,2-dichlorocyclopropyl)methoxy]phenyl]carbamate Chemical compound CCOC(=O)NC1=CC=C(OCC2CC2(Cl)Cl)C(Cl)=C1 DIDDJBKATVHPFB-UHFFFAOYSA-N 0.000 claims 1
- WRUSQFIDTLILST-UHFFFAOYSA-N methyl N-[3,5-dichloro-4-[(2,2-dichlorocyclopropyl)methoxy]phenyl]carbamate Chemical compound COC(NC1=CC(=C(C(=C1)Cl)OCC1C(C1)(Cl)Cl)Cl)=O WRUSQFIDTLILST-UHFFFAOYSA-N 0.000 claims 1
- MBAMTFAKEIUZDL-UHFFFAOYSA-N methyl N-[3-chloro-4-[(2,2-dichloro-3-methylcyclopropyl)methoxy]phenyl]carbamate Chemical compound COC(NC1=CC(=C(C=C1)OCC1C(C1C)(Cl)Cl)Cl)=O MBAMTFAKEIUZDL-UHFFFAOYSA-N 0.000 claims 1
- QBLUCPUAZISDIX-UHFFFAOYSA-N methyl n-[3-chloro-4-[(2,2-dichloro-1-methylcyclopropyl)methoxy]phenyl]carbamate Chemical compound ClC1=CC(NC(=O)OC)=CC=C1OCC1(C)C(Cl)(Cl)C1 QBLUCPUAZISDIX-UHFFFAOYSA-N 0.000 claims 1
- QLROQXPJUOCNOJ-UHFFFAOYSA-N propan-2-yl N-[3-chloro-4-[(2,2-dichloro-3-methylcyclopropyl)methoxy]phenyl]carbamate Chemical compound C(C)(C)OC(NC1=CC(=C(C=C1)OCC1C(C1C)(Cl)Cl)Cl)=O QLROQXPJUOCNOJ-UHFFFAOYSA-N 0.000 claims 1
- KVZXQACEZSMKSG-UHFFFAOYSA-N propan-2-yl N-[3-chloro-4-[(2,2-dichlorocyclopropyl)methoxy]phenyl]carbamate Chemical compound C(C)(C)OC(NC1=CC(=C(C=C1)OCC1C(C1)(Cl)Cl)Cl)=O KVZXQACEZSMKSG-UHFFFAOYSA-N 0.000 claims 1
- XPFMSKHUTCNOAX-UHFFFAOYSA-N propyl N-[3-chloro-4-[(2,2-dichloro-1-methylcyclopropyl)methoxy]phenyl]carbamate Chemical compound C(CC)OC(NC1=CC(=C(C=C1)OCC1(C(C1)(Cl)Cl)C)Cl)=O XPFMSKHUTCNOAX-UHFFFAOYSA-N 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000004480 active ingredient Substances 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 241000196324 Embryophyta Species 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000000243 solution Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- 240000005979 Hordeum vulgare Species 0.000 description 4
- 235000007340 Hordeum vulgare Nutrition 0.000 description 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 244000038559 crop plants Species 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- CNKAIOFSBLLUHC-UHFFFAOYSA-N 2-chloro-1-[(2,2-dichlorocyclopropyl)methoxy]-4-nitrobenzene Chemical compound ClC1=CC([N+](=O)[O-])=CC=C1OCC1C(Cl)(Cl)C1 CNKAIOFSBLLUHC-UHFFFAOYSA-N 0.000 description 3
- MGSOUTVJDSBNCH-UHFFFAOYSA-N 3-chloro-4-[(2,2-dichlorocyclopropyl)methoxy]aniline Chemical compound ClC1=CC(N)=CC=C1OCC1C(Cl)(Cl)C1 MGSOUTVJDSBNCH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000006378 damage Effects 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- 239000000395 magnesium oxide Substances 0.000 description 3
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 3
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- KONKYDDIDBAUNP-UHFFFAOYSA-N 2-chloro-1-[(2,2-dichlorocyclopropyl)methoxy]-4-isocyanatobenzene Chemical compound ClC1=CC(N=C=O)=CC=C1OCC1C(Cl)(Cl)C1 KONKYDDIDBAUNP-UHFFFAOYSA-N 0.000 description 2
- 235000007319 Avena orientalis Nutrition 0.000 description 2
- 244000075850 Avena orientalis Species 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 240000007594 Oryza sativa Species 0.000 description 2
- 235000007164 Oryza sativa Nutrition 0.000 description 2
- 239000007868 Raney catalyst Substances 0.000 description 2
- 229910000564 Raney nickel Inorganic materials 0.000 description 2
- WOZQBERUBLYCEG-UHFFFAOYSA-N SWEP Chemical compound COC(=O)NC1=CC=C(Cl)C(Cl)=C1 WOZQBERUBLYCEG-UHFFFAOYSA-N 0.000 description 2
- 244000082988 Secale cereale Species 0.000 description 2
- 235000007238 Secale cereale Nutrition 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
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- 235000021307 Triticum Nutrition 0.000 description 2
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- 238000001816 cooling Methods 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
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- 239000012071 phase Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
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- KEZQSZUPYPHPKE-UHFFFAOYSA-N 2-(bromomethyl)-1,1-dichlorocyclopropane Chemical compound ClC1(Cl)CC1CBr KEZQSZUPYPHPKE-UHFFFAOYSA-N 0.000 description 1
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- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 150000003560 thiocarbamic acids Chemical class 0.000 description 1
- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000008096 xylene 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
- A01N47/20—N-Aryl derivatives thereof
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)
- Indole Compounds (AREA)
Priority Applications (40)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19792913976 DE2913976A1 (de) | 1979-04-05 | 1979-04-05 | Substituierte carbanilsaeureester, verfahren zur herstellung dieser verbindungen sowie diese enthaltende selektive herbizide mittel |
| NL8001747A NL8001747A (nl) | 1979-04-05 | 1980-03-25 | Gesubstitueerde carbanilzuuresters, werkwijze voor het bereiden daarvan, alsmede selectieve herbiciden op basis van deze verbindingen. |
| CH238380A CH646142A5 (de) | 1979-04-05 | 1980-03-26 | Substituierte carbanilsaeureester, verfahren zur herstellung dieser verbindungen sowie diese enthaltende selektive herbizide mittel. |
| NZ193299A NZ193299A (en) | 1979-04-05 | 1980-03-28 | Substituted carbanilic acid esters herbicidal compositions |
| IL59738A IL59738A (en) | 1979-04-05 | 1980-03-31 | Substituted carbanilic acid esters,processes for the manufacture of these compounds and herbicidal preparations containing them |
| SE8002506A SE8002506L (sv) | 1979-04-05 | 1980-04-01 | Substituerade karbanilsyraestrar, sett att framstella dessa samt selektiva herbicida medel, innehallande dessa foreningar |
| BR8002002A BR8002002A (pt) | 1979-04-05 | 1980-04-01 | Processo para a producao de esteres de acido carbanilico substituidos e composicoes herbicidas seletivas contendo os mesmos |
| NO800945A NO151284C (no) | 1979-04-05 | 1980-04-01 | Substituerte carbanilsyreestere og herbicide midler inneholdende disse |
| SU802901455A SU1048983A3 (ru) | 1979-04-05 | 1980-04-01 | Способ получени замещенных сложных эфиров карбаниловой кислоты |
| DD80220133A DD151041A5 (de) | 1979-04-05 | 1980-04-01 | Selektive herbizide mittel |
| IT21093/80A IT1148777B (it) | 1979-04-05 | 1980-04-01 | Esteri sostitiuiti dell'acido carbanilico, procedimento di preparazione di tali composti e mezzi erbicidi selettivi contenenti gli stessi |
| SU802900896A SU1210650A3 (ru) | 1979-04-05 | 1980-04-01 | Гербицидное средство (его варианты) |
| GR61613A GR66674B (enExample) | 1979-04-05 | 1980-04-02 | |
| DK146580A DK146580A (da) | 1979-04-05 | 1980-04-02 | Substituerede carbanilsyreestere fremgangsmaade til fremstilling af disse forbindelser og selektive herbicide midler indeholdende dem |
| YU00908/80A YU90880A (en) | 1979-04-05 | 1980-04-02 | Process for obtaining substituted esters of carbonylic acid |
| ES490257A ES490257A0 (es) | 1979-04-05 | 1980-04-02 | Procedimiento para la preparacion de esteres de acidos car- banilicos sustituidos |
| AT0180880A AT379289B (de) | 1979-04-05 | 1980-04-02 | Selektive herbizide mittel |
| BG047215A BG31474A3 (en) | 1979-04-05 | 1980-04-02 | Herbicide means |
| MX808737U MX6140E (es) | 1979-04-05 | 1980-04-02 | Procedimiento para preparar esteres de acido carbanilico substituidos |
| TR20607A TR20607A (tr) | 1979-04-05 | 1980-04-03 | Ikame edilmis karbanilik asit esterleri,bu bilesimlerin imaline mahsus usuller ve bunlari ihtiva eden selektif herbisit maddeler |
| PL1980223232A PL121299B1 (en) | 1979-04-05 | 1980-04-03 | Selective herbicide and method of manufacture of novel substituted esters of carbanilic acidhhennykh ehfirov karbanilovojj kisloty |
| PT71059A PT71059A (de) | 1979-04-05 | 1980-04-03 | Substituierte carbanilsaureester verfahren zur herstellungdieser verbindungen sowie diese enthaltende selektive |
| LU82325A LU82325A1 (de) | 1979-04-05 | 1980-04-03 | Substituierte carbanilsaeureester,verfahren zur herstellung dieser verbindungen sowie diese enthaltende selektive herbizide mittel |
| GB8011331A GB2049674B (en) | 1979-04-05 | 1980-04-03 | Substituted carbanilic acid esters processes for the manufacture of these compounds and herbicidal preparations containing them |
| AU57154/80A AU531347B2 (en) | 1979-04-05 | 1980-04-03 | Substituted carbanilic acid estors |
| IE679/80A IE49660B1 (en) | 1979-04-05 | 1980-04-03 | Substituted carbanilic acid esters processes for the manufacture of these compounds and herbicidal preparations containing them |
| HU80820A HU182605B (en) | 1979-04-05 | 1980-04-03 | Selective herbicide compositions containing substituted esters of carbanilic acid |
| BE0/200116A BE882631A (fr) | 1979-04-05 | 1980-04-03 | Esters d'acide carbanilique substitues leur procede de preparation et leur utilisation |
| ZA00802034A ZA802034B (en) | 1979-04-05 | 1980-04-03 | Substituted carbanilic acid esters,processes for the manufacture of these compounds and herbicidal preparations containing them |
| IN244/DEL/80A IN154063B (enExample) | 1979-04-05 | 1980-04-03 | |
| CA000349209A CA1142535A (en) | 1979-04-05 | 1980-04-03 | Substituted carbanilic acid esters, processes for the manufacture of these compounds and herbicidal preparations containing them |
| CS807124A CS214828B2 (en) | 1979-04-05 | 1980-04-04 | Method of making the carbanilic acid esters |
| FR8007672A FR2453141A1 (fr) | 1979-04-05 | 1980-04-04 | Esters carbaniliques substitues, procedes pour les preparer, et produits herbicides selectifs qui en contiennent |
| MA18999A MA18804A1 (fr) | 1979-04-05 | 1980-04-04 | Esters carbaniliques substitues,procede pour les preparer,et produits herbicides qui en contiennent |
| CS802363A CS214827B2 (en) | 1979-04-05 | 1980-04-04 | Selective herbicide means and method of making the active substance |
| RO80100725A RO79224A (ro) | 1979-04-05 | 1980-04-04 | Procedeu pentru prepararea unor esteri substituiti ai acidului carbanilic |
| JP55043645A JPS5825659B2 (ja) | 1979-04-05 | 1980-04-04 | 置換カルバニル酸エステル、その製造法及び該化合物を含有する選択的除草剤 |
| EG208/80A EG14377A (en) | 1979-04-05 | 1980-04-05 | Substituted carbonilic acid esters,process for the manufacture of these compounds and herbicidal preparations containing them |
| PH23862A PH15714A (en) | 1979-04-05 | 1980-04-07 | Substituted carbonilic acid esters,herbicidal compositions and method of use thereof |
| US06/406,897 US4479822A (en) | 1979-04-05 | 1982-08-10 | Substituted carbanilic acid esters and herbicidal composition containing same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19792913976 DE2913976A1 (de) | 1979-04-05 | 1979-04-05 | Substituierte carbanilsaeureester, verfahren zur herstellung dieser verbindungen sowie diese enthaltende selektive herbizide mittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2913976A1 true DE2913976A1 (de) | 1980-10-23 |
Family
ID=6067687
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19792913976 Withdrawn DE2913976A1 (de) | 1979-04-05 | 1979-04-05 | Substituierte carbanilsaeureester, verfahren zur herstellung dieser verbindungen sowie diese enthaltende selektive herbizide mittel |
Country Status (38)
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6070775U (ja) * | 1983-10-21 | 1985-05-18 | ヤンマーディーゼル株式会社 | 横形内燃機関の燃料浄化装置 |
| FR2662159B1 (fr) * | 1990-05-15 | 1994-03-11 | Matieres Nucleaires Cie Gle | Nouveaux ligands thio-ethers et leur utilisation pour separer le palladium de solutions aqueuses, en particulier de soludtions nitriques de dissolution d'elements combustibles nucleaires irradies. |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1195549B (de) | 1961-01-25 | 1965-06-24 | Fmc Corp | Selektive herbicide Mittel |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4093447A (en) * | 1971-06-23 | 1978-06-06 | Bayer Aktiengesellschaft | N-Arylcarbamic acid esters and plant growth regulant compositions and methods |
| DE2417487C2 (de) * | 1974-04-10 | 1983-01-20 | Hoechst Ag, 6000 Frankfurt | Benzyl-phenoxyalkancarbonsäuren, deren Derivate und Verfahren zu ihrer Herstellung |
| US4149874A (en) * | 1977-06-21 | 1979-04-17 | Stauffer Chemical Company | Substituted cyclopropylmethoxy anilides and their use as herbicides |
| US4230483A (en) * | 1977-06-21 | 1980-10-28 | Stauffer Chemical Company | Substituted cyclopropylmethoxy phenyl carbamates and thiocarbamates and their use as herbicides |
| DE2804739A1 (de) * | 1978-02-02 | 1979-08-09 | Schering Ag | Phenylharnstoff-derivate, verfahren zur herstellung dieser verbindungen sowie diese enthaltendes selektives herbizides mittel |
-
1979
- 1979-04-05 DE DE19792913976 patent/DE2913976A1/de not_active Withdrawn
-
1980
- 1980-03-25 NL NL8001747A patent/NL8001747A/nl not_active Application Discontinuation
- 1980-03-26 CH CH238380A patent/CH646142A5/de not_active IP Right Cessation
- 1980-03-28 NZ NZ193299A patent/NZ193299A/xx unknown
- 1980-03-31 IL IL59738A patent/IL59738A/xx unknown
- 1980-04-01 SU SU802900896A patent/SU1210650A3/ru active
- 1980-04-01 BR BR8002002A patent/BR8002002A/pt unknown
- 1980-04-01 IT IT21093/80A patent/IT1148777B/it active
- 1980-04-01 DD DD80220133A patent/DD151041A5/de unknown
- 1980-04-01 SE SE8002506A patent/SE8002506L/ not_active Application Discontinuation
- 1980-04-01 NO NO800945A patent/NO151284C/no unknown
- 1980-04-01 SU SU802901455A patent/SU1048983A3/ru active
- 1980-04-02 DK DK146580A patent/DK146580A/da not_active IP Right Cessation
- 1980-04-02 YU YU00908/80A patent/YU90880A/xx unknown
- 1980-04-02 MX MX808737U patent/MX6140E/es unknown
- 1980-04-02 AT AT0180880A patent/AT379289B/de not_active IP Right Cessation
- 1980-04-02 BG BG047215A patent/BG31474A3/xx unknown
- 1980-04-02 GR GR61613A patent/GR66674B/el unknown
- 1980-04-02 ES ES490257A patent/ES490257A0/es active Granted
- 1980-04-03 CA CA000349209A patent/CA1142535A/en not_active Expired
- 1980-04-03 AU AU57154/80A patent/AU531347B2/en not_active Ceased
- 1980-04-03 HU HU80820A patent/HU182605B/hu unknown
- 1980-04-03 LU LU82325A patent/LU82325A1/de unknown
- 1980-04-03 GB GB8011331A patent/GB2049674B/en not_active Expired
- 1980-04-03 IE IE679/80A patent/IE49660B1/en unknown
- 1980-04-03 ZA ZA00802034A patent/ZA802034B/xx unknown
- 1980-04-03 TR TR20607A patent/TR20607A/xx unknown
- 1980-04-03 PL PL1980223232A patent/PL121299B1/pl unknown
- 1980-04-03 PT PT71059A patent/PT71059A/pt unknown
- 1980-04-03 BE BE0/200116A patent/BE882631A/fr not_active IP Right Cessation
- 1980-04-03 IN IN244/DEL/80A patent/IN154063B/en unknown
- 1980-04-04 JP JP55043645A patent/JPS5825659B2/ja not_active Expired
- 1980-04-04 CS CS807124A patent/CS214828B2/cs unknown
- 1980-04-04 FR FR8007672A patent/FR2453141A1/fr active Granted
- 1980-04-04 MA MA18999A patent/MA18804A1/fr unknown
- 1980-04-04 CS CS802363A patent/CS214827B2/cs unknown
- 1980-04-04 RO RO80100725A patent/RO79224A/ro unknown
- 1980-04-05 EG EG208/80A patent/EG14377A/xx active
- 1980-04-07 PH PH23862A patent/PH15714A/en unknown
-
1982
- 1982-08-10 US US06/406,897 patent/US4479822A/en not_active Expired - Fee Related
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1195549B (de) | 1961-01-25 | 1965-06-24 | Fmc Corp | Selektive herbicide Mittel |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8141 | Disposal/no request for examination |