DE2601987A1 - (5-alkylureido-1,3,4-thiadiazol-2- yl-thio)-essigsaeureester, verfahren zur herstellung dieser verbindungen sowie diese enthaltende herbizide mittel - Google Patents
(5-alkylureido-1,3,4-thiadiazol-2- yl-thio)-essigsaeureester, verfahren zur herstellung dieser verbindungen sowie diese enthaltende herbizide mittelInfo
- Publication number
- DE2601987A1 DE2601987A1 DE19762601987 DE2601987A DE2601987A1 DE 2601987 A1 DE2601987 A1 DE 2601987A1 DE 19762601987 DE19762601987 DE 19762601987 DE 2601987 A DE2601987 A DE 2601987A DE 2601987 A1 DE2601987 A1 DE 2601987A1
- Authority
- DE
- Germany
- Prior art keywords
- thiadiazol
- acetic acid
- general formula
- thio
- agents
- 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- Withdrawn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 17
- 238000002360 preparation method Methods 0.000 title claims description 7
- 239000004009 herbicide Substances 0.000 title claims description 6
- 238000000034 method Methods 0.000 title claims description 6
- 239000003795 chemical substances by application Substances 0.000 title description 14
- 150000002168 ethanoic acid esters Chemical class 0.000 title 1
- 229940112021 centrally acting muscle relaxants carbamic acid ester Drugs 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 4
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- LATBKRVSJOHSJQ-UHFFFAOYSA-N tert-butyl 2-[[5-(methylamino)-1,3,4-thiadiazol-2-yl]sulfanyl]acetate Chemical compound CNC1=NN=C(SCC(=O)OC(C)(C)C)S1 LATBKRVSJOHSJQ-UHFFFAOYSA-N 0.000 claims description 3
- KNIXYQKIWMJXNF-UHFFFAOYSA-N tert-butyl 2-[[5-[dimethylcarbamoyl(methyl)amino]-1,3,4-thiadiazol-2-yl]sulfanyl]acetate Chemical compound CN(C)C(=O)N(C)C1=NN=C(SCC(=O)OC(C)(C)C)S1 KNIXYQKIWMJXNF-UHFFFAOYSA-N 0.000 claims description 3
- LFQFCKMCRZKWDP-UHFFFAOYSA-N tert-butyl 2-[[5-[methyl(methylcarbamoyl)amino]-1,3,4-thiadiazol-2-yl]sulfanyl]acetate Chemical compound CNC(=O)N(C)C1=NN=C(SCC(=O)OC(C)(C)C)S1 LFQFCKMCRZKWDP-UHFFFAOYSA-N 0.000 claims description 3
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical class NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 150000003973 alkyl amines Chemical class 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 239000011230 binding agent Substances 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 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
- 229910052717 sulfur Chemical group 0.000 claims description 2
- 239000011593 sulfur Chemical group 0.000 claims description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- -1 alkyl radical Chemical group 0.000 description 12
- 239000004480 active ingredient Substances 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 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
- 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
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 241000196324 Embryophyta Species 0.000 description 5
- 230000002363 herbicidal effect Effects 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
- 230000000694 effects 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
- 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
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 239000007900 aqueous suspension Substances 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 150000008282 halocarbons Chemical class 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 241000743985 Alopecurus Species 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 241000219318 Amaranthus Species 0.000 description 1
- 244000105624 Arachis hypogaea Species 0.000 description 1
- 241000209761 Avena Species 0.000 description 1
- 241000209764 Avena fatua Species 0.000 description 1
- 235000007320 Avena fatua Nutrition 0.000 description 1
- 235000007319 Avena orientalis Nutrition 0.000 description 1
- 241000132570 Centaurea Species 0.000 description 1
- 235000007516 Chrysanthemum Nutrition 0.000 description 1
- 240000005250 Chrysanthemum indicum Species 0.000 description 1
- 244000192528 Chrysanthemum parthenium Species 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 235000017896 Digitaria Nutrition 0.000 description 1
- 241001303487 Digitaria <clam> Species 0.000 description 1
- 241000192043 Echinochloa Species 0.000 description 1
- 244000025670 Eleusine indica Species 0.000 description 1
- 235000014716 Eleusine indica Nutrition 0.000 description 1
- 241001101998 Galium Species 0.000 description 1
- 240000005979 Hordeum vulgare Species 0.000 description 1
- 235000007340 Hordeum vulgare Nutrition 0.000 description 1
- 241000520028 Lamium Species 0.000 description 1
- 241000209510 Liliopsida Species 0.000 description 1
- 235000019738 Limestone Nutrition 0.000 description 1
- 235000017945 Matricaria Nutrition 0.000 description 1
- 235000007232 Matricaria chamomilla Nutrition 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 240000004713 Pisum sativum Species 0.000 description 1
- 235000010582 Pisum sativum Nutrition 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 241000205407 Polygonum Species 0.000 description 1
- 241000780602 Senecio Species 0.000 description 1
- 235000005775 Setaria Nutrition 0.000 description 1
- 241000232088 Setaria <nematode> Species 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 240000002439 Sorghum halepense Species 0.000 description 1
- 244000062793 Sorghum vulgare 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
- 241001506766 Xanthium Species 0.000 description 1
- 241000607479 Yersinia pestis 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
- 241001148683 Zostera marina Species 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 150000008107 benzenesulfonic acids Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229920005551 calcium lignosulfonate Polymers 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
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000003857 carboxamides Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000002837 defoliant Substances 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- XHFGWHUWQXTGAT-UHFFFAOYSA-N dimethylamine hydrochloride Natural products CNC(C)C XHFGWHUWQXTGAT-UHFFFAOYSA-N 0.000 description 1
- IQDGSYLLQPDQDV-UHFFFAOYSA-N dimethylazanium;chloride Chemical compound Cl.CNC IQDGSYLLQPDQDV-UHFFFAOYSA-N 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- DGDIOLRTMXZVFP-UHFFFAOYSA-N ethyl 2-[[5-[dimethylcarbamoyl(methyl)amino]-1,3,4-thiadiazol-2-yl]sulfanyl]acetate Chemical compound CCOC(=O)CSC1=NN=C(N(C)C(=O)N(C)C)S1 DGDIOLRTMXZVFP-UHFFFAOYSA-N 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 241001233957 eudicotyledons Species 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 150000007529 inorganic bases Chemical class 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
- 150000002576 ketones Chemical class 0.000 description 1
- 239000006028 limestone Substances 0.000 description 1
- 235000009973 maize Nutrition 0.000 description 1
- HKTDABGEKQJVGB-UHFFFAOYSA-N methyl 2-[[5-[methyl(methylcarbamoyl)amino]-1,3,4-thiadiazol-2-yl]sulfanyl]acetate Chemical compound COC(CSC=1SC(=NN1)N(C(=O)NC)C)=O HKTDABGEKQJVGB-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 235000019713 millet 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
- 230000009965 odorless effect Effects 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 210000002741 palatine tonsil Anatomy 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 235000012015 potatoes Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- TXHPAWGOZBSFDR-UHFFFAOYSA-N propan-2-yl 2-[[5-(methylcarbamoylamino)-1,3,4-thiadiazol-2-yl]sulfanyl]acetate Chemical compound C(C)(C)OC(CSC=1SC(=NN1)NC(=O)NC)=O TXHPAWGOZBSFDR-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000011541 reaction mixture Substances 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
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000002689 soil Substances 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
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 1
- 229960000278 theophylline Drugs 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
- C07D285/125—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
- C07D285/135—Nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Plural Heterocyclic Compounds (AREA)
- Lubricants (AREA)
Priority Applications (33)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19762601987 DE2601987A1 (de) | 1976-01-16 | 1976-01-16 | (5-alkylureido-1,3,4-thiadiazol-2- yl-thio)-essigsaeureester, verfahren zur herstellung dieser verbindungen sowie diese enthaltende herbizide mittel |
| IL50982A IL50982A (en) | 1976-01-16 | 1976-11-24 | (5-alkylureido-1,3,4-thiadiazol-2-yl-thio)-acetic acid esters,process for the preparation of said compounds and herbicidal compositions containing the same |
| FI763459A FI57755C (fi) | 1976-01-16 | 1976-12-01 | (5-metylureido-1,3,4-tiadiazol-2-yltio)-aettiksyra-tert -butylestrar foer anvaendning som herbicider |
| PT65947A PT65947A (de) | 1976-01-16 | 1976-12-09 | (5-alkylureido-1,3,4-thiadiazol-2-ylthio)-essigsaeureester,verfahren zur herstellung dieser verbindungen sowie diese enthaltende herbizide mittel |
| IN2182/CAL/76A IN145509B (enExample) | 1976-01-16 | 1976-12-10 | |
| DD196309A DD127484A5 (enExample) | 1976-01-16 | 1976-12-13 | |
| DK563276A DK563276A (da) | 1976-01-16 | 1976-12-15 | (5-alkylureido-1,3,4-thiadiazol-2-yl-thio)-eddikesyreestere, fremgangsmade til fremstilling af disse forbindelser, samt herbicide midler indeholdende dem |
| RO7688802A RO72836A (ro) | 1976-01-16 | 1976-12-21 | Procedeu de preparare a esterilor acidului (5-alchilureido-1,3,4-tiadiazol-2-il-tio)-acetic |
| LU76453A LU76453A1 (enExample) | 1976-01-16 | 1976-12-22 | |
| BG035049A BG27518A3 (bg) | 1976-01-16 | 1976-12-29 | Хербицидно средство |
| AT975776A AT349828B (de) | 1976-01-16 | 1976-12-29 | Herbizide mittel |
| NZ183029A NZ183029A (en) | 1976-01-16 | 1977-01-07 | Tertiary botyl (5-(1,3-dimethylureido-1,3,4-thiadiazol-2-yl-thio)-acetates |
| NL7700130A NL7700130A (nl) | 1976-01-16 | 1977-01-07 | (5-alkylureido-1,3,4,-thiadiazool- -2-yl-thio)-azijnzuuresters, werkwijze voor het bereiden van deze verbindingen, alsmede herbici- de middelen, die deze verbindingen bevatten, en werkwijze voor het bereiden van deze herbicide middelen. |
| TR19437A TR19437A (tr) | 1976-01-16 | 1977-01-10 | (5-alkiluereido-13,4-thiadiazol yl-thio)-sirke asidi esterleri bu bilesimlerin imal usulleri ve bunlari ihtiva eden herbisit maddeler |
| GB707/77A GB1575462A (en) | 1976-01-16 | 1977-01-10 | Herbicidally active (5-alkylureido-1,3,4-thiadiazol-2-yl-thio)-acetic acid esters process for their manufacture and their use |
| BR7700106A BR7700106A (pt) | 1976-01-16 | 1977-01-10 | Esteres de acido (5-alquilureido-1,3,4-tiadiazol-2-il-tio)-cetico,processo para preparacao destes compostos,bem como composicoes herbicidas contendo os mesmos |
| SE7700319A SE7700319L (sv) | 1976-01-16 | 1977-01-13 | (5-alkylureido-1,3,4-tiadiazol-2-yl-tio)-ettikssyraestrar, sett att framstella dessa foreningar och herbicida medel innehallande foreningarna |
| IE66/77A IE44435B1 (en) | 1976-01-16 | 1977-01-14 | Herbicidally active (5-alkylureido-1,3,4-thiadiazol-2-yl-thio)-acetic acid esters, process for their manufacture and their use |
| SU772439811A SU651700A3 (ru) | 1976-01-16 | 1977-01-14 | Способ получени сложных эфиров (5-алкилуреидо-1,3,4-тиадиазол2-ил-тио) уксусной кислоты |
| PH19350A PH13863A (en) | 1976-01-16 | 1977-01-14 | 5 alkylureido-1,3,4,-thiadiazol-yl-thio acetic acid esters,process for their manufacture and use |
| US05/759,560 US4072497A (en) | 1976-01-16 | 1977-01-14 | (5-Alkylureido-1,3,4-thiadiazol-2-yl-thio) acetic acid tert-butyl esters and herbicidal compositions and processes |
| SU772439556A SU646876A3 (ru) | 1976-01-16 | 1977-01-14 | Гербицидное средство |
| PL1977195314A PL101775B1 (pl) | 1976-01-16 | 1977-01-14 | A herbicide |
| ZA00770201A ZA77201B (en) | 1976-01-16 | 1977-01-14 | Herbicidally active(5-alkylureido-1,3,4-thiadiazol-2-yl-thio)-acetic acid esters,process for their manufacture and their use |
| CA279,723A CA1078392A (en) | 1976-01-16 | 1977-01-14 | Herbicidally active (5-alkylureido-1,3,4-thiadiazol-2-yl-thio)-acetic acid esters |
| IT19310/77A IT1079104B (it) | 1976-01-16 | 1977-01-14 | Esteri dell'acido (5-alchilureido-1, 3, 4-tiadiazol-2-il-tio)-acetico,procedimento per la loro preparazione e mezzi erbicidi che li contengono |
| BE174091A BE850394A (fr) | 1976-01-16 | 1977-01-14 | Esters d'acide (5-alkylureido-1,3,4-thiadiazol-2-yl-thio)-acetique |
| GR52582A GR62392B (en) | 1976-01-16 | 1977-01-15 | 5-alkyl ureido-1,3,4-thiadiazol-2-yl-thio)aceticesters,preparation process thereof and medium containing the said herbicides |
| EG25/77A EG12242A (en) | 1976-01-16 | 1977-01-15 | Process for preparing of(5-alkylureido-1,3,4 thiadiazole-2-yl-thio)acid esters,and their use as herbicides |
| CS77282A CS191184B2 (en) | 1976-01-16 | 1977-01-17 | Herbicide means and method for preparation of the active agent |
| JP386177A JPS5289673A (en) | 1976-01-16 | 1977-01-17 | Production of *55 alkylureidoo1*3*44 thiadiazoll22yllthio** acetic acid ester and herbicide containing the same |
| FR7701166A FR2338270A1 (fr) | 1976-01-16 | 1977-01-17 | Esters d'acides (thiadiazolylthio)-acetiques doues de proprietes herbicides |
| AU21382/77A AU2138277A (en) | 1976-01-16 | 1977-01-17 | 1,3,4-thiadiazole derivatives |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19762601987 DE2601987A1 (de) | 1976-01-16 | 1976-01-16 | (5-alkylureido-1,3,4-thiadiazol-2- yl-thio)-essigsaeureester, verfahren zur herstellung dieser verbindungen sowie diese enthaltende herbizide mittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2601987A1 true DE2601987A1 (de) | 1977-07-21 |
Family
ID=5967827
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19762601987 Withdrawn DE2601987A1 (de) | 1976-01-16 | 1976-01-16 | (5-alkylureido-1,3,4-thiadiazol-2- yl-thio)-essigsaeureester, verfahren zur herstellung dieser verbindungen sowie diese enthaltende herbizide mittel |
Country Status (32)
| Country | Link |
|---|---|
| US (1) | US4072497A (enExample) |
| JP (1) | JPS5289673A (enExample) |
| AT (1) | AT349828B (enExample) |
| AU (1) | AU2138277A (enExample) |
| BE (1) | BE850394A (enExample) |
| BG (1) | BG27518A3 (enExample) |
| BR (1) | BR7700106A (enExample) |
| CA (1) | CA1078392A (enExample) |
| CS (1) | CS191184B2 (enExample) |
| DD (1) | DD127484A5 (enExample) |
| DE (1) | DE2601987A1 (enExample) |
| DK (1) | DK563276A (enExample) |
| EG (1) | EG12242A (enExample) |
| FI (1) | FI57755C (enExample) |
| FR (1) | FR2338270A1 (enExample) |
| GB (1) | GB1575462A (enExample) |
| GR (1) | GR62392B (enExample) |
| IE (1) | IE44435B1 (enExample) |
| IL (1) | IL50982A (enExample) |
| IN (1) | IN145509B (enExample) |
| IT (1) | IT1079104B (enExample) |
| LU (1) | LU76453A1 (enExample) |
| NL (1) | NL7700130A (enExample) |
| NZ (1) | NZ183029A (enExample) |
| PH (1) | PH13863A (enExample) |
| PL (1) | PL101775B1 (enExample) |
| PT (1) | PT65947A (enExample) |
| RO (1) | RO72836A (enExample) |
| SE (1) | SE7700319L (enExample) |
| SU (2) | SU646876A3 (enExample) |
| TR (1) | TR19437A (enExample) |
| ZA (1) | ZA77201B (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS626341A (ja) * | 1985-07-02 | 1987-01-13 | Nec Corp | 情報処理装置 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1817949U (de) | 1958-11-12 | 1960-09-08 | John Deerflanz Ag | Dreschmaschine, insbesondere maehdrescher. |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1817949A1 (de) * | 1968-12-23 | 1974-11-07 | Bayer Ag | 1,3,4-thiadiazolyl(5)-harnstoffe, ihre verwendung als herbizide und verfahren zu ihrer herstellung |
| CH521711A (de) * | 1968-12-23 | 1972-04-30 | Bayer Ag | Herbizides Mittel |
-
1976
- 1976-01-16 DE DE19762601987 patent/DE2601987A1/de not_active Withdrawn
- 1976-11-24 IL IL50982A patent/IL50982A/xx unknown
- 1976-12-01 FI FI763459A patent/FI57755C/fi not_active IP Right Cessation
- 1976-12-09 PT PT65947A patent/PT65947A/pt unknown
- 1976-12-10 IN IN2182/CAL/76A patent/IN145509B/en unknown
- 1976-12-13 DD DD196309A patent/DD127484A5/xx unknown
- 1976-12-15 DK DK563276A patent/DK563276A/da unknown
- 1976-12-21 RO RO7688802A patent/RO72836A/ro unknown
- 1976-12-22 LU LU76453A patent/LU76453A1/xx unknown
- 1976-12-29 AT AT975776A patent/AT349828B/de not_active IP Right Cessation
- 1976-12-29 BG BG035049A patent/BG27518A3/xx unknown
-
1977
- 1977-01-07 NZ NZ183029A patent/NZ183029A/xx unknown
- 1977-01-07 NL NL7700130A patent/NL7700130A/xx unknown
- 1977-01-10 BR BR7700106A patent/BR7700106A/pt unknown
- 1977-01-10 GB GB707/77A patent/GB1575462A/en not_active Expired
- 1977-01-10 TR TR19437A patent/TR19437A/xx unknown
- 1977-01-13 SE SE7700319A patent/SE7700319L/xx unknown
- 1977-01-14 PH PH19350A patent/PH13863A/en unknown
- 1977-01-14 PL PL1977195314A patent/PL101775B1/pl unknown
- 1977-01-14 US US05/759,560 patent/US4072497A/en not_active Expired - Lifetime
- 1977-01-14 CA CA279,723A patent/CA1078392A/en not_active Expired
- 1977-01-14 BE BE174091A patent/BE850394A/xx unknown
- 1977-01-14 ZA ZA00770201A patent/ZA77201B/xx unknown
- 1977-01-14 IT IT19310/77A patent/IT1079104B/it active
- 1977-01-14 SU SU772439556A patent/SU646876A3/ru active
- 1977-01-14 IE IE66/77A patent/IE44435B1/en unknown
- 1977-01-14 SU SU772439811A patent/SU651700A3/ru active
- 1977-01-15 GR GR52582A patent/GR62392B/el unknown
- 1977-01-15 EG EG25/77A patent/EG12242A/xx active
- 1977-01-17 FR FR7701166A patent/FR2338270A1/fr not_active Withdrawn
- 1977-01-17 JP JP386177A patent/JPS5289673A/ja active Granted
- 1977-01-17 AU AU21382/77A patent/AU2138277A/en not_active Expired
- 1977-01-17 CS CS77282A patent/CS191184B2/cs unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1817949U (de) | 1958-11-12 | 1960-09-08 | John Deerflanz Ag | Dreschmaschine, insbesondere maehdrescher. |
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| 8139 | Disposal/non-payment of the annual fee |