CA1125301A - Herbicidally active n-(2-propynyl)-carbanilic acid (3-aliphatic hydrocarbon-oxy- or - thio- carbonylaminophenyl) esters and their manufacture and use - Google Patents
Herbicidally active n-(2-propynyl)-carbanilic acid (3-aliphatic hydrocarbon-oxy- or - thio- carbonylaminophenyl) esters and their manufacture and useInfo
- Publication number
- CA1125301A CA1125301A CA348,942A CA348942A CA1125301A CA 1125301 A CA1125301 A CA 1125301A CA 348942 A CA348942 A CA 348942A CA 1125301 A CA1125301 A CA 1125301A
- Authority
- CA
- Canada
- Prior art keywords
- compound
- propynyl
- ester
- general formula
- 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.)
- Expired
Links
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 5
- 150000002148 esters Chemical class 0.000 title claims description 11
- 150000001875 compounds Chemical class 0.000 claims abstract description 54
- 241000196324 Embryophyta Species 0.000 claims abstract description 36
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 5
- 238000000034 method Methods 0.000 claims description 20
- -1 N-(2-Propynyl)-carbanilic acid (3-ethoxycarbonyl-aminophenyl) ester Chemical compound 0.000 claims description 10
- 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 9
- 238000011282 treatment Methods 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 claims description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- 229920000742 Cotton Polymers 0.000 claims description 2
- 241000219146 Gossypium Species 0.000 claims description 2
- 240000007594 Oryza sativa Species 0.000 claims description 2
- 235000007164 Oryza sativa Nutrition 0.000 claims description 2
- 244000061456 Solanum tuberosum Species 0.000 claims description 2
- 235000002595 Solanum tuberosum Nutrition 0.000 claims description 2
- 235000021307 Triticum Nutrition 0.000 claims description 2
- 240000008042 Zea mays Species 0.000 claims description 2
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 claims description 2
- 235000002017 Zea mays subsp mays Nutrition 0.000 claims description 2
- UKDDOPTXFLHHDI-UHFFFAOYSA-N [3-(2-methylpropoxycarbonylamino)phenyl] N-phenyl-N-prop-2-ynylcarbamate Chemical compound CC(COC(=O)NC=1C=C(C=CC1)OC(N(C1=CC=CC=C1)CC#C)=O)C UKDDOPTXFLHHDI-UHFFFAOYSA-N 0.000 claims description 2
- HBPZNRCEZMZLPW-UHFFFAOYSA-N [3-(prop-2-ynoxycarbonylamino)phenyl] N-phenyl-N-prop-2-ynylcarbamate Chemical compound C(C#C)OC(=O)NC=1C=C(C=CC1)OC(N(C1=CC=CC=C1)CC#C)=O HBPZNRCEZMZLPW-UHFFFAOYSA-N 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 235000009973 maize Nutrition 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 150000007530 organic bases Chemical group 0.000 claims description 2
- 235000009566 rice Nutrition 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 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 1
- 241000209140 Triticum Species 0.000 claims 1
- OSVIHDQVYCBTAL-UHFFFAOYSA-N [3-(but-3-en-2-yloxycarbonylamino)phenyl] N-phenyl-N-prop-2-ynylcarbamate Chemical compound CC(C=C)OC(=O)NC=1C=C(C=CC1)OC(N(C1=CC=CC=C1)CC#C)=O OSVIHDQVYCBTAL-UHFFFAOYSA-N 0.000 claims 1
- SZINGGZTFSFGPI-UHFFFAOYSA-N [3-(ethanethioylamino)phenyl] N-phenyl-N-prop-2-ynylcarbamate Chemical compound CC(=S)NC=1C=C(C=CC1)OC(N(C1=CC=CC=C1)CC#C)=O SZINGGZTFSFGPI-UHFFFAOYSA-N 0.000 claims 1
- RKTRPIMFQHMEQF-UHFFFAOYSA-N [3-(propan-2-yloxycarbonylamino)phenyl] N-phenyl-N-prop-2-ynylcarbamate Chemical compound CC(C)OC(=O)NC=1C=C(C=CC1)OC(N(C1=CC=CC=C1)CC#C)=O RKTRPIMFQHMEQF-UHFFFAOYSA-N 0.000 claims 1
- 150000001447 alkali salts Chemical class 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 230000002363 herbicidal effect Effects 0.000 abstract description 10
- 238000002360 preparation method Methods 0.000 abstract description 8
- 239000000969 carrier Substances 0.000 abstract description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 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
- 239000013543 active substance Substances 0.000 description 6
- 239000004009 herbicide Substances 0.000 description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-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
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 235000002634 Solanum Nutrition 0.000 description 2
- 241000207763 Solanum Species 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- PWXJULSLLONQHY-UHFFFAOYSA-N phenylcarbamic acid Chemical compound OC(=O)NC1=CC=CC=C1 PWXJULSLLONQHY-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 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
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 240000004385 Centaurea cyanus Species 0.000 description 1
- 235000005940 Centaurea cyanus Nutrition 0.000 description 1
- 241000905957 Channa melasoma Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 101100536354 Drosophila melanogaster tant gene Proteins 0.000 description 1
- 235000021506 Ipomoea Nutrition 0.000 description 1
- 241000207783 Ipomoea Species 0.000 description 1
- 244000303225 Lamium amplexicaule Species 0.000 description 1
- 235000009198 Lamium amplexicaule Nutrition 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
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 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
- 241000212342 Sium Species 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 239000005864 Sulphur Chemical group 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 1
- 244000098338 Triticum aestivum Species 0.000 description 1
- 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 description 1
- 229940022682 acetone Drugs 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
- 239000003513 alkali Substances 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
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 1
- 150000008107 benzenesulfonic acids Chemical class 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 229940112021 centrally acting muscle relaxants carbamic acid ester Drugs 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- XTEGARKTQYYJKE-UHFFFAOYSA-N chloric acid Chemical compound OCl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-N 0.000 description 1
- 229940005991 chloric acid Drugs 0.000 description 1
- AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical compound OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 150000004891 diazines Chemical class 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 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
- 229920005610 lignin Polymers 0.000 description 1
- 239000006028 limestone Substances 0.000 description 1
- 235000012054 meals Nutrition 0.000 description 1
- 239000011707 mineral Substances 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
- 231100001184 nonphytotoxic Toxicity 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
- 235000012015 potatoes Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000003223 protective agent Substances 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
- 239000002904 solvent Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 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
- 235000012222 talc Nutrition 0.000 description 1
- 150000003560 thiocarbamic acids Chemical class 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- JFALSRSLKYAFGM-UHFFFAOYSA-N uranium(0) Chemical compound [U] JFALSRSLKYAFGM-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 238000009736 wetting Methods 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)
Applications Claiming Priority (2)
| 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 |
| DEP2913975.1 | 1979-04-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1125301A true CA1125301A (en) | 1982-06-08 |
Family
ID=6067686
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA348,942A Expired 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 |
Country Status (35)
| Country | Link |
|---|---|
| JP (1) | JPS5819672B2 (cs) |
| AR (1) | AR224521A1 (cs) |
| AT (1) | AT365896B (cs) |
| AU (1) | AU535374B2 (cs) |
| BE (1) | BE882627A (cs) |
| BG (1) | BG34897A3 (cs) |
| BR (1) | BR8002009A (cs) |
| CA (1) | CA1125301A (cs) |
| CH (1) | CH645344A5 (cs) |
| CS (1) | CS209949B2 (cs) |
| DD (1) | DD149996A5 (cs) |
| DE (1) | DE2913975A1 (cs) |
| EG (1) | EG14317A (cs) |
| ES (1) | ES490256A0 (cs) |
| FI (1) | FI800832A7 (cs) |
| FR (1) | FR2453142A1 (cs) |
| GB (1) | GB2049672B (cs) |
| GR (1) | GR67206B (cs) |
| HU (1) | HU181764B (cs) |
| IL (1) | IL59736A (cs) |
| IN (1) | IN154011B (cs) |
| IT (1) | IT1148780B (cs) |
| MA (1) | MA18803A1 (cs) |
| MX (1) | MX6017E (cs) |
| NL (1) | NL8001638A (cs) |
| PH (1) | PH17275A (cs) |
| PL (1) | PL123694B1 (cs) |
| PT (1) | PT71032A (cs) |
| RO (1) | RO79220A (cs) |
| SE (1) | SE8002183L (cs) |
| SU (1) | SU925248A3 (cs) |
| TR (1) | TR20575A (cs) |
| YU (1) | YU76180A (cs) |
| ZA (1) | ZA802032B (cs) |
| ZW (1) | ZW7980A1 (cs) |
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/fi 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/ 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 MX MX808729U patent/MX6017E/es unknown
- 1980-03-31 IL IL59736A patent/IL59736A/xx unknown
- 1980-03-31 GB GB8010810A patent/GB2049672B/en not_active Expired
- 1980-04-01 BR BR8002009A patent/BR8002009A/pt unknown
- 1980-04-01 CA CA348,942A patent/CA1125301A/en not_active Expired
- 1980-04-02 BG BG047214A patent/BG34897A3/xx unknown
- 1980-04-02 ES ES490256A patent/ES490256A0/es active Granted
- 1980-04-02 AR AR280534A patent/AR224521A1/es active
- 1980-04-02 AT AT0180680A patent/AT365896B/de not_active IP Right Cessation
- 1980-04-02 GR GR61616A patent/GR67206B/el unknown
- 1980-04-03 ZA ZA00802032A patent/ZA802032B/xx unknown
- 1980-04-03 PL PL1980223231A patent/PL123694B1/pl unknown
- 1980-04-03 IT IT21168/80A patent/IT1148780B/it active
- 1980-04-03 BE BE0/200112A patent/BE882627A/fr not_active IP Right Cessation
- 1980-04-03 ZW ZW79/80A patent/ZW7980A1/xx unknown
- 1980-04-03 TR TR20575A patent/TR20575A/xx unknown
- 1980-04-03 HU HU80818A patent/HU181764B/hu unknown
- 1980-04-03 AU AU57150/80A patent/AU535374B2/en not_active Ceased
- 1980-04-03 DD DD80220215A patent/DD149996A5/de unknown
- 1980-04-04 MA MA18998A patent/MA18803A1/fr unknown
- 1980-04-04 JP JP55043644A patent/JPS5819672B2/ja not_active Expired
- 1980-04-04 RO RO80100727A patent/RO79220A/ro unknown
- 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 |
|---|---|---|
| RU2056415C1 (ru) | Производные сульфонилмочевины или их соли, способ их получения, фенилсульфонамиды, сульфонилкарбаматы, фенилсульфохлориды, гербицидное и подавляющее рост растений средство, способ борьбы с нежелательным ростом растений и способ подавления роста растений | |
| US4921525A (en) | Thiodiazolylurea-containing agent for defoliating plants | |
| EP0459949B1 (de) | Sulfonylharnstoffe mit herbizider und pflanzenwuchsregulierender Wirkung | |
| EP0165003A2 (en) | Herbicidal sulfonamides | |
| US4559079A (en) | Substituted phenylsulfonyl guanidine herbicides and intermeditates therefor | |
| CA1125301A (en) | Herbicidally active n-(2-propynyl)-carbanilic acid (3-aliphatic hydrocarbon-oxy- or - thio- carbonylaminophenyl) esters and their manufacture and use | |
| US3989710A (en) | Certain 2-mercapto-4,5-dichloro-thiazole compounds | |
| US4626273A (en) | Herbicidal novel 2-alkoxyaminosulfonyl-benzene-sulfonylureas | |
| CA1051925A (en) | Substituted phenylureas, their preparation and their use as herbicides | |
| PL120535B1 (en) | Pesticide or plant growth regulator and process for manufacturing sulfonanilidesenijj i sposob poluchenija sul'fonanilidov | |
| US4619688A (en) | Herbicidal sulfonylguanidine derivatives | |
| GB2034697A (en) | Herbicidally active carbamic acid phenyl esters and their manufacture and use | |
| EP0626958A1 (en) | Sulfonylureas as herbicides | |
| KR840000572B1 (ko) | N-(-2-프로피닐)-카바닐산(3-지방족탄화수소-옥시-또는-티오-카보닐아미노페닐)에스테르의 제조방법 | |
| US4239524A (en) | Thiadiazolyl ureas with herbicidal effect | |
| US4855478A (en) | N,N'-diaryl-N-alkylureas and method of use | |
| US3954785A (en) | Acylated urea compounds and herbicidal compositions | |
| US4119432A (en) | Herbicidal N-(dialkylcarbamyl)-N-trifluoromethyl-phenylcarbamyl alkyl disulfides | |
| US4075235A (en) | N-Aryl-urea compounds and herbicidal compositions | |
| US3931312A (en) | Novel N(-difluoromethylmercaptophenyl) urea compounds and herbicidal compositions | |
| KR820001256B1 (ko) | 제초제인 디우레탄의 제조방법 | |
| CA1100987A (en) | Herbicidally active carbanilic acid esters | |
| KR790001913B1 (ko) | 메타-디우레탄의 제조방법 | |
| EP0342456A2 (en) | Sultamsulfonamide derivatives and herbicides | |
| US4137068A (en) | Novel ureas |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |