DE2913975A1 - N-(2-propinyl)-carbanilsaeure-(3-alkoxy- und alkylthiocarbonylamino-phenyl)-ester, verfahren zur herstellung dieser verbindungen sowie diese enthaltende selektive herbizide mittel - Google Patents
N-(2-propinyl)-carbanilsaeure-(3-alkoxy- und alkylthiocarbonylamino-phenyl)-ester, verfahren zur herstellung dieser verbindungen sowie diese enthaltende selektive herbizide mittelInfo
- Publication number
- DE2913975A1 DE2913975A1 DE19792913975 DE2913975A DE2913975A1 DE 2913975 A1 DE2913975 A1 DE 2913975A1 DE 19792913975 DE19792913975 DE 19792913975 DE 2913975 A DE2913975 A DE 2913975A DE 2913975 A1 DE2913975 A1 DE 2913975A1
- Authority
- DE
- Germany
- Prior art keywords
- berlin
- account
- propynyl
- bank
- phenyl
- 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- Withdrawn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 22
- 239000004009 herbicide Substances 0.000 title claims description 8
- 238000004519 manufacturing process Methods 0.000 title description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 63
- -1 xsobutyl Chemical group 0.000 claims description 21
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 16
- 150000002148 esters Chemical class 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 8
- 230000002363 herbicidal effect Effects 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- 235000015244 frankfurter Nutrition 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- FPCVKACKGOHVAO-UHFFFAOYSA-N phenyl(prop-2-ynyl)carbamic acid Chemical compound C(C#C)N(C(O)=O)C1=CC=CC=C1 FPCVKACKGOHVAO-UHFFFAOYSA-N 0.000 claims description 6
- 239000000969 carrier Substances 0.000 claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 239000011593 sulfur Substances 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- IZKIWEYIOKPHLF-UHFFFAOYSA-N n-prop-2-ynylaniline Chemical compound C#CCNC1=CC=CC=C1 IZKIWEYIOKPHLF-UHFFFAOYSA-N 0.000 claims description 3
- 150000007530 organic bases Chemical group 0.000 claims description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- MGQLXUDTBLZEFT-UHFFFAOYSA-N N-phenyl-N-prop-2-ynylcarbamoyl chloride Chemical compound C1(=CC=CC=C1)N(C(=O)Cl)CC#C MGQLXUDTBLZEFT-UHFFFAOYSA-N 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 claims description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- MNBOFGKALCNRMG-UHFFFAOYSA-N [3-(ethoxycarbonylamino)phenyl] N-phenyl-N-prop-2-ynylcarbamate Chemical compound C(C)OC(=O)NC=1C=C(C=CC1)OC(N(C1=CC=CC=C1)CC#C)=O MNBOFGKALCNRMG-UHFFFAOYSA-N 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 241000196324 Embryophyta Species 0.000 description 12
- 239000004480 active ingredient Substances 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-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
- 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 230000006378 damage Effects 0.000 description 4
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 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
- 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
- 239000000654 additive Substances 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 235000002634 Solanum Nutrition 0.000 description 2
- 241000207763 Solanum Species 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- GIRGFOHZHDGCJA-UHFFFAOYSA-N 2-[(2,3,6-trichlorophenyl)methoxy]propan-2-ol Chemical compound CC(C)(O)OCC1=C(Cl)C=CC(Cl)=C1Cl GIRGFOHZHDGCJA-UHFFFAOYSA-N 0.000 description 1
- JSIAIROWMJGMQZ-UHFFFAOYSA-N 2h-triazol-4-amine Chemical class NC1=CNN=N1 JSIAIROWMJGMQZ-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 241000335053 Beta vulgaris Species 0.000 description 1
- 235000011331 Brassica Nutrition 0.000 description 1
- 241000219198 Brassica Species 0.000 description 1
- 240000004385 Centaurea cyanus Species 0.000 description 1
- 235000005940 Centaurea cyanus Nutrition 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 244000299507 Gossypium hirsutum Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 241000207890 Ipomoea purpurea Species 0.000 description 1
- 235000019738 Limestone Nutrition 0.000 description 1
- 244000042664 Matricaria chamomilla Species 0.000 description 1
- 235000007232 Matricaria chamomilla Nutrition 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 240000005498 Setaria italica Species 0.000 description 1
- 235000007226 Setaria italica Nutrition 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 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
- 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
- QJUUGNSQLMIUAJ-UHFFFAOYSA-N [3-(methoxycarbonylamino)phenyl] N-phenyl-N-prop-2-ynylcarbamate Chemical compound COC(=O)NC=1C=C(C=CC1)OC(N(C1=CC=CC=C1)CC#C)=O QJUUGNSQLMIUAJ-UHFFFAOYSA-N 0.000 description 1
- DNWKZHXTBHCPFN-UHFFFAOYSA-N [3-(methoxycarbonylamino)phenyl] carbonochloridate Chemical compound COC(=O)NC1=CC=CC(OC(Cl)=O)=C1 DNWKZHXTBHCPFN-UHFFFAOYSA-N 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229940051881 anilide analgesics and antipyretics Drugs 0.000 description 1
- 150000003931 anilides Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 150000008107 benzenesulfonic acids Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- RYAGRZNBULDMBW-UHFFFAOYSA-L calcium;3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Ca+2].COC1=CC=CC(CC(CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O RYAGRZNBULDMBW-UHFFFAOYSA-L 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000004891 diazines Chemical class 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 241001233957 eudicotyledons Species 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 235000008216 herbs Nutrition 0.000 description 1
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000006028 limestone Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 235000009973 maize Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 210000002741 palatine tonsil Anatomy 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- PWXJULSLLONQHY-UHFFFAOYSA-N phenylcarbamic acid Chemical compound OC(=O)NC1=CC=CC=C1 PWXJULSLLONQHY-UHFFFAOYSA-N 0.000 description 1
- 231100000208 phytotoxic Toxicity 0.000 description 1
- 230000000885 phytotoxic effect Effects 0.000 description 1
- 239000004476 plant protection product Substances 0.000 description 1
- 235000012015 potatoes Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 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
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007921 spray 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
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 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
- 150000003672 ureas Chemical class 0.000 description 1
- 244000045561 useful plants Species 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
- A01N47/22—O-Aryl or S-Aryl esters 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)
Priority Applications (35)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19792913975 DE2913975A1 (de) | 1979-04-05 | 1979-04-05 | N-(2-propinyl)-carbanilsaeure-(3-alkoxy- und alkylthiocarbonylamino-phenyl)-ester, verfahren zur herstellung dieser verbindungen sowie diese enthaltende selektive herbizide mittel |
| FI800832A FI800832A7 (sv) | 1979-04-05 | 1980-03-18 | N-(2- propinyl)-karbanilsyra-(3- metoxikarbonylamino-fenyl)-estrar, förfarande för framställning av desföreningar samt dessa innehållande selektiva herbicida ämnen. |
| NL8001638A NL8001638A (nl) | 1979-04-05 | 1980-03-19 | Carbanilzuur-(3-alkoxycarbonylaminofenyl)-esters, werkwijze voor het bereiden daarvan, alsmede selectieve herbiciden op basis van deze verbindingen. |
| YU00761/80A YU76180A (en) | 1979-04-05 | 1980-03-19 | Process for obtaining phenyl esters of n-(2-propinyl)-carbonylic acid |
| SE8002183A SE8002183L (sv) | 1979-04-05 | 1980-03-20 | N-(2-propinyl)-karbanilsyra-(3-metoxikarbonylaminofenyl)-estrar, sett att framstella dessa samt selektiva herbicida medel, innehallande dessa foreningar |
| IN217/DEL/80A IN154011B (sv) | 1979-04-05 | 1980-03-25 | |
| CH238480A CH645344A5 (de) | 1979-04-05 | 1980-03-26 | N-(2-propinyl)-carbanilsaeure-(3-methoxycarbonylaminophenyl)-ester, verfahren zur herstellung dieser verbindungen sowie diese enthaltende selektive herbizide mittel. |
| CS802160A CS209949B2 (en) | 1979-04-05 | 1980-03-27 | Herbicide means and method of making the active substance |
| SU802901453A SU925248A3 (ru) | 1979-04-05 | 1980-03-28 | Способ получени 3-замещенных карбониламинофениловых эфиров N-(2-пропинил)-карбаниловой кислоты |
| PT71032A PT71032A (de) | 1979-04-05 | 1980-03-28 | N-(2-propinyl)-carbanilsaure-(3-methoxycarbonylaminophenyl)-ester verfahren zur herstellung dieser verbindungen sowie dieese enthaltende selektive herbizide mittel |
| MX808729U MX6017E (es) | 1979-04-05 | 1980-03-31 | Procedimiento para preparar(3-hidrocarbon-oxi-o-tio-carbonilaminofenil)-esteres alifaticos de acido n-(2-propinil)-carbanilico |
| IL59736A IL59736A (en) | 1979-04-05 | 1980-03-31 | Aliphatic esters of 3-(n-propynyl-n-phenylcarbamoyloxy(thio)-carbanilic acid),process for their preparation and herbicidal compositions containing the same |
| GB8010810A GB2049672B (en) | 1979-04-05 | 1980-03-31 | Herbicidally active n-(2-propynyl)-carbanilic acid-(3-aliphatic hydrocarbon-oxy-or-thiocarbonylaminophenyl) esters and their manufacture and use |
| CA348,942A CA1125301A (en) | 1979-04-05 | 1980-04-01 | Herbicidally active n-(2-propynyl)-carbanilic acid (3-aliphatic hydrocarbon-oxy- or - thio- carbonylaminophenyl) esters and their manufacture and use |
| BR8002009A BR8002009A (pt) | 1979-04-05 | 1980-04-01 | Processo para a producao de esteres (3-metoxicarbonilaminofenilicos) de acido n-(2-propinil)-carbanilico e composicoes herbicidas seletivas contendo os mesmos |
| AT0180680A AT365896B (de) | 1979-04-05 | 1980-04-02 | Selektive herbizide mittel |
| BG047214A BG34897A3 (bg) | 1979-04-05 | 1980-04-02 | Селективно хербицидно средство |
| ES490256A ES8107172A1 (es) | 1979-04-05 | 1980-04-02 | Procedimiento para la preparacion de esteres (3-(alcoxi y alcohiltio) carbonilaminofenilicos) de acido n-(2-propinil)-carbanilico |
| AR280534A AR224521A1 (es) | 1979-04-05 | 1980-04-02 | Esteres 3-(alquiltio-carbonilamino)-fenilicos del acido n-(2-propinil)-carbanilico,procedimientos para producir estos compuestos y composiciones herbicidas selectivas que los contienen |
| GR61616A GR67206B (sv) | 1979-04-05 | 1980-04-02 | |
| AU57150/80A AU535374B2 (en) | 1979-04-05 | 1980-04-03 | New compounds |
| BE0/200112A BE882627A (fr) | 1979-04-05 | 1980-04-03 | N-(2-propynyl)-carbanilates de (3-alcoxy-et-alkylthio-carbonylaminophenyle) et leur procede de preparation |
| PL1980223231A PL123694B1 (en) | 1979-04-05 | 1980-04-03 | Selective herbicide |
| DD80220215A DD149996A5 (de) | 1979-04-05 | 1980-04-03 | Selektive herbizide mittel |
| HU80818A HU181764B (en) | 1979-04-05 | 1980-04-03 | Selective herbicide compositions containing n-/2-propinyl/-carbanilic acid /3-methoxycarbonyl-aminophenyl/-esters |
| ZA00802032A ZA802032B (en) | 1979-04-05 | 1980-04-03 | Herbicidally active n-(2-propynyl)-carbanilic acid (3-aliphatic hydrocarbon-ocy-or-thiocarbonylaminophenyl)esters and their manufacture and use |
| ZW79/80A ZW7980A1 (en) | 1979-04-05 | 1980-04-03 | Herbicidally active n-(2-propynl)-carbanilic acid (3-aliphatic hydro-carbon-oxy-or-thiocarbony lamnophenyl) esters and their manufacture and use |
| IT21168/80A IT1148780B (it) | 1979-04-05 | 1980-04-03 | Esteri (3-metossicarbonilamminopenicili) dell'acido n-(2-propinil)-carbanilico, procedimento per preparare tali composti nonche' mezzi erbicidi selettivi contenenti gli stessi |
| TR20575A TR20575A (tr) | 1979-04-05 | 1980-04-03 | N-(2-propinil)-karbanilik asit(3-metoksi karbonilaminofenil)esterler,bu bilesimlerin imaline mahsus usul,ve bu bilesimleri ihtiva eden selektif herbisit maddeler |
| JP55043644A JPS5819672B2 (ja) | 1979-04-05 | 1980-04-04 | Ｎ−（２−プロピニル）−カルバニル酸−（３−メトキシカルボニルアミノフエニル）−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 |
| FR8007670A FR2453142A1 (fr) | 1979-04-05 | 1980-04-04 | N-(propyne-2 yl)-carbanilates de phenyles substitues en 3, procedes pour les preparer, et produits herbicides selectifs qui en contiennent |
| MA18998A MA18803A1 (fr) | 1979-04-05 | 1980-04-04 | N-(propyne-2yl)-carbanilates de phenyles substitues en 3,procedes pour les preparer,et produits herbicides selectifs qui en contiennent |
| RO80100727A RO79220A (ro) | 1979-04-05 | 1980-04-04 | Procedeu pentru prepararea unor esteri alcoxicarbonilaminofenilici aiacidului carbanilic |
| EG207/80A EG14317A (en) | 1979-04-05 | 1980-04-05 | Herbicidally active n-(2-propynyl)-carbanilic acid (3-aliphatic hydrocarbon-oxy-or-thio carbonylaminophenyl)esters and their manufacture and use |
| PH23863A PH17275A (en) | 1979-04-05 | 1980-04-07 | Herbicidally active n-(2-propinyl)-carbanilic acid(3-methoxy-carbonylaminophenyl)esters |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19792913975 DE2913975A1 (de) | 1979-04-05 | 1979-04-05 | N-(2-propinyl)-carbanilsaeure-(3-alkoxy- und alkylthiocarbonylamino-phenyl)-ester, verfahren zur herstellung dieser verbindungen sowie diese enthaltende selektive herbizide mittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2913975A1 true DE2913975A1 (de) | 1980-10-23 |
Family
ID=6067686
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19792913975 Withdrawn DE2913975A1 (de) | 1979-04-05 | 1979-04-05 | N-(2-propinyl)-carbanilsaeure-(3-alkoxy- und alkylthiocarbonylamino-phenyl)-ester, verfahren zur herstellung dieser verbindungen sowie diese enthaltende selektive herbizide mittel |
Country Status (35)
| Country | Link |
|---|---|
| JP (1) | JPS5819672B2 (sv) |
| AR (1) | AR224521A1 (sv) |
| AT (1) | AT365896B (sv) |
| AU (1) | AU535374B2 (sv) |
| BE (1) | BE882627A (sv) |
| BG (1) | BG34897A3 (sv) |
| BR (1) | BR8002009A (sv) |
| CA (1) | CA1125301A (sv) |
| CH (1) | CH645344A5 (sv) |
| CS (1) | CS209949B2 (sv) |
| DD (1) | DD149996A5 (sv) |
| DE (1) | DE2913975A1 (sv) |
| EG (1) | EG14317A (sv) |
| ES (1) | ES8107172A1 (sv) |
| FI (1) | FI800832A7 (sv) |
| FR (1) | FR2453142A1 (sv) |
| GB (1) | GB2049672B (sv) |
| GR (1) | GR67206B (sv) |
| HU (1) | HU181764B (sv) |
| IL (1) | IL59736A (sv) |
| IN (1) | IN154011B (sv) |
| IT (1) | IT1148780B (sv) |
| MA (1) | MA18803A1 (sv) |
| MX (1) | MX6017E (sv) |
| NL (1) | NL8001638A (sv) |
| PH (1) | PH17275A (sv) |
| PL (1) | PL123694B1 (sv) |
| PT (1) | PT71032A (sv) |
| RO (1) | RO79220A (sv) |
| SE (1) | SE8002183L (sv) |
| SU (1) | SU925248A3 (sv) |
| TR (1) | TR20575A (sv) |
| YU (1) | YU76180A (sv) |
| ZA (1) | ZA802032B (sv) |
| ZW (1) | ZW7980A1 (sv) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6014760U (ja) * | 1983-07-09 | 1985-01-31 | フランスベッド株式会社 | マツトレス装置 |
| JPS6074668U (ja) * | 1983-10-28 | 1985-05-25 | フランスベッド株式会社 | マツトレス |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2413933A1 (de) * | 1974-03-20 | 1975-09-25 | Schering Ag | Diurethane mit selektiver herbizider wirkung |
| DE2557552C2 (de) * | 1975-12-18 | 1984-12-20 | Schering AG, 1000 Berlin und 4709 Bergkamen | Diurethane und herbizide Mittel, enthaltend diese Verbindungen als Wirkstoffe |
| DE2650796A1 (de) * | 1976-11-03 | 1978-05-11 | Schering Ag | Diurethane, verfahren zur herstellung dieser verbindungen sowie diese enthaltendes selektives herbizides mittel |
| DE2651526A1 (de) * | 1976-11-09 | 1978-05-18 | Schering Ag | Diurethane, verfahren zur herstellung dieser verbindungen sowie diese enthaltendes selektives herbizides mittel |
-
1979
- 1979-04-05 DE DE19792913975 patent/DE2913975A1/de not_active Withdrawn
-
1980
- 1980-03-18 FI FI800832A patent/FI800832A7/sv not_active Application Discontinuation
- 1980-03-19 YU YU00761/80A patent/YU76180A/xx unknown
- 1980-03-19 NL NL8001638A patent/NL8001638A/nl not_active Application Discontinuation
- 1980-03-20 SE SE8002183A patent/SE8002183L/sv not_active Application Discontinuation
- 1980-03-25 IN IN217/DEL/80A patent/IN154011B/en unknown
- 1980-03-26 CH CH238480A patent/CH645344A5/de not_active IP Right Cessation
- 1980-03-27 CS CS802160A patent/CS209949B2/cs unknown
- 1980-03-28 SU SU802901453A patent/SU925248A3/ru active
- 1980-03-28 PT PT71032A patent/PT71032A/pt unknown
- 1980-03-31 GB GB8010810A patent/GB2049672B/en not_active Expired
- 1980-03-31 IL IL59736A patent/IL59736A/xx unknown
- 1980-03-31 MX MX808729U patent/MX6017E/es unknown
- 1980-04-01 CA CA348,942A patent/CA1125301A/en not_active Expired
- 1980-04-01 BR BR8002009A patent/BR8002009A/pt unknown
- 1980-04-02 BG BG047214A patent/BG34897A3/xx unknown
- 1980-04-02 AT AT0180680A patent/AT365896B/de not_active IP Right Cessation
- 1980-04-02 AR AR280534A patent/AR224521A1/es active
- 1980-04-02 GR GR61616A patent/GR67206B/el unknown
- 1980-04-02 ES ES490256A patent/ES8107172A1/es not_active Expired
- 1980-04-03 BE BE0/200112A patent/BE882627A/fr not_active IP Right Cessation
- 1980-04-03 HU HU80818A patent/HU181764B/hu unknown
- 1980-04-03 ZW ZW79/80A patent/ZW7980A1/xx unknown
- 1980-04-03 TR TR20575A patent/TR20575A/xx unknown
- 1980-04-03 IT IT21168/80A patent/IT1148780B/it active
- 1980-04-03 PL PL1980223231A patent/PL123694B1/pl unknown
- 1980-04-03 AU AU57150/80A patent/AU535374B2/en not_active Ceased
- 1980-04-03 DD DD80220215A patent/DD149996A5/de unknown
- 1980-04-03 ZA ZA00802032A patent/ZA802032B/xx unknown
- 1980-04-04 RO RO80100727A patent/RO79220A/ro unknown
- 1980-04-04 MA MA18998A patent/MA18803A1/fr unknown
- 1980-04-04 JP JP55043644A patent/JPS5819672B2/ja not_active Expired
- 1980-04-04 FR FR8007670A patent/FR2453142A1/fr active Granted
- 1980-04-05 EG EG207/80A patent/EG14317A/xx active
- 1980-04-07 PH PH23863A patent/PH17275A/en unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2812622C2 (de) | (2,3-Dihydro-2,2-dimethyl-benzofuran-7-yl-oxy-N-methyl-carbamoyl)-(N'-alkyl-carbamoyl)-sulfide, Verfahren zu deren Herstellung und diese Verbindungen enthaltende insektizide Mittel | |
| EP0036390B1 (de) | Diphenyläther-Harnstoffe mit herbizider Wirkung | |
| DE2108975C3 (de) | N-Acyl-Diurethane sowie diese enthaltendes herbizides Mittel | |
| EP0028829A1 (de) | Harnstoffe mit cyclischen Substituenten, ihre Herstellung und Verwendung als Herbizide | |
| DE2151766B2 (de) | N-Thiazolinyl-Phenoxycarbonsäureanüde | |
| DE2913975A1 (de) | N-(2-propinyl)-carbanilsaeure-(3-alkoxy- und alkylthiocarbonylamino-phenyl)-ester, verfahren zur herstellung dieser verbindungen sowie diese enthaltende selektive herbizide mittel | |
| DE2210540C2 (de) | Cyanphenylcarbonate, Verfahren zu deren Herstellung sowie diese enthaltende herbizide Mittel | |
| DE1928059A1 (de) | Herbizide Mittel mit einem Gehalt an 4-Nitrophenolverbindungen neue %-Nitrophenolverbindungen und Verfahren zu ihrer Herstellung | |
| DE1944525C3 (de) | Anilinoalkanohydroxamsäureverbindungen, Verfahren zu ihrer Herstellung und ihre Verwendung als herbicide Mittel | |
| DE2121957A1 (de) | Herbizide Methylphenylcarbamate | |
| DE2302029C2 (de) | N,N-disubstituierte &alpha;-Aminothiopropionsäureester, Verfahren zu ihrer Herstellung und ihre Verwendung | |
| DE2320362A1 (de) | Dichlorthiazolylharnstoffe, verfahren zu ihrer herstellung sowie ihre verwendung als herbizide | |
| DE2310649C3 (de) | Diurethane sowie diese enthaltende selektive herbizide Mittel | |
| DE2163381A1 (de) | Herbizide Komposition | |
| DE2310648C3 (de) | Diurethane, Verfahren zur Herstellung dieser Verbindungen sowie diese enthaltende selektive herbizide Mittel | |
| DE2856651C2 (sv) | ||
| DE2036968C3 (de) | 3-Chlor-4-n und i-Propoxyphenylharnstoffe, ihre Herstellung und diese enthaltende Schädlingsbekämpfungsmittel | |
| DE1912294C (de) | Oximcarbamate und ihre Verwendung als Akaricide | |
| DE2819748C2 (de) | N-Äthylcarbanilsäure-(3-methoxycarbonylamino)-phenylester, Verfahren zur Herstellung dieser Verbindung sowie diese enthaltendes selektives herbizides Mittel | |
| EP0024016A1 (de) | Tetrachlorphthalamidsäuren, Verfahren zu ihrer Herstellung und ihre bakterizide Verwendung | |
| DD146540A5 (de) | Herbizides mittel | |
| LU82325A1 (de) | Substituierte carbanilsaeureester,verfahren zur herstellung dieser verbindungen sowie diese enthaltende selektive herbizide mittel | |
| DE2163380A1 (de) | Herbizides Mittel | |
| CH616653A5 (en) | Herbicidal composition containing aniline derivatives | |
| DE2029191A1 (en) | Fluoroacetamide tickicides -n-(2,2,2-trichloro-1-phenylthioethyl) - fluoroacetamides and their prepn |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8139 | Disposal/non-payment of the annual fee |