DE2621647A1 - 2-(dimethylcarbamoylimino)-1,3,4- thiadiazolin-3-carbonsaeure-ester, verfahren zur herstellung dieser verbindungen sowie diese enthaltende herbizide mittel - Google Patents
2-(dimethylcarbamoylimino)-1,3,4- thiadiazolin-3-carbonsaeure-ester, verfahren zur herstellung dieser verbindungen sowie diese enthaltende herbizide mittelInfo
- Publication number
- DE2621647A1 DE2621647A1 DE19762621647 DE2621647A DE2621647A1 DE 2621647 A1 DE2621647 A1 DE 2621647A1 DE 19762621647 DE19762621647 DE 19762621647 DE 2621647 A DE2621647 A DE 2621647A DE 2621647 A1 DE2621647 A1 DE 2621647A1
- Authority
- DE
- Germany
- Prior art keywords
- thiadiazoline
- dimethylcarbamoylimino
- carboxylic acid
- ester
- carboxylate
- 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- Withdrawn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 45
- 238000000034 method Methods 0.000 title claims description 12
- 239000004009 herbicide Substances 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title claims description 7
- -1 DIMETHYLCARBAMOYLIMINO Chemical class 0.000 title description 22
- 150000002148 esters Chemical class 0.000 claims description 73
- 239000002253 acid Substances 0.000 claims description 51
- 150000002736 metal compounds Chemical class 0.000 claims description 8
- 239000011230 binding agent Substances 0.000 claims description 6
- 239000007800 oxidant agent Substances 0.000 claims description 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- PQHUNICQRBELNW-UHFFFAOYSA-N ethyl 2-(dimethylcarbamoylimino)-5-methylsulfanyl-1,3,4-thiadiazole-3-carboxylate Chemical compound CCOC(=O)N1N=C(SC)SC1=NC(=O)N(C)C PQHUNICQRBELNW-UHFFFAOYSA-N 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- PNWXIVHAFKHCRF-UHFFFAOYSA-N 2-(dimethylcarbamoylimino)-1,3,4-thiadiazole-3-carboxylic acid Chemical class CN(C(=O)N=C1SC=NN1C(=O)O)C PNWXIVHAFKHCRF-UHFFFAOYSA-N 0.000 claims 2
- PMRUKVCRVFJRCV-UHFFFAOYSA-N 2-methylpropyl 2-(dimethylcarbamoylimino)-5-hexylsulfanyl-1,3,4-thiadiazole-3-carboxylate Chemical compound C(C(C)C)OC(=O)N1C(SC(=N1)SCCCCCC)=NC(N(C)C)=O PMRUKVCRVFJRCV-UHFFFAOYSA-N 0.000 claims 1
- PHGPCARYJWOZOV-UHFFFAOYSA-N 2-methylpropyl 2-(dimethylcarbamoylimino)-5-methylsulfanyl-1,3,4-thiadiazole-3-carboxylate Chemical compound CSC1=NN(C(=O)OCC(C)C)C(=NC(=O)N(C)C)S1 PHGPCARYJWOZOV-UHFFFAOYSA-N 0.000 claims 1
- AYLWYVAKWIUMPJ-UHFFFAOYSA-N 2-methylpropyl 2-(dimethylcarbamoylimino)-5-methylsulfonyl-1,3,4-thiadiazole-3-carboxylate Chemical compound CC(C)COC(=O)N1N=C(S(C)(=O)=O)SC1=NC(=O)N(C)C AYLWYVAKWIUMPJ-UHFFFAOYSA-N 0.000 claims 1
- LNGORYLUJOKKDE-UHFFFAOYSA-N 3-chloropropyl 2-(dimethylcarbamoylimino)-5-propylsulfanyl-1,3,4-thiadiazole-3-carboxylate Chemical compound CCCSC1=NN(C(=O)OCCCCl)C(=NC(=O)N(C)C)S1 LNGORYLUJOKKDE-UHFFFAOYSA-N 0.000 claims 1
- PNODJTGTJSJWET-UHFFFAOYSA-N butyl 2-(dimethylcarbamoylimino)-5-(2-methylpropylsulfanyl)-1,3,4-thiadiazole-3-carboxylate Chemical compound C(CCC)OC(=O)N1C(SC(=N1)SCC(C)C)=NC(N(C)C)=O PNODJTGTJSJWET-UHFFFAOYSA-N 0.000 claims 1
- VXHCZOQTDNVASO-UHFFFAOYSA-N butyl 2-(dimethylcarbamoylimino)-5-(2-methylpropylsulfonyl)-1,3,4-thiadiazole-3-carboxylate Chemical compound C(CCC)OC(=O)N1C(SC(=N1)S(=O)(=O)CC(C)C)=NC(N(C)C)=O VXHCZOQTDNVASO-UHFFFAOYSA-N 0.000 claims 1
- ATVSVKZZVQKCJU-UHFFFAOYSA-N butyl 2-(dimethylcarbamoylimino)-5-hexylsulfanyl-1,3,4-thiadiazole-3-carboxylate Chemical compound C(CCC)OC(=O)N1C(SC(=N1)SCCCCCC)=NC(N(C)C)=O ATVSVKZZVQKCJU-UHFFFAOYSA-N 0.000 claims 1
- YFXPCVAXBXYKPG-UHFFFAOYSA-N butyl 2-(dimethylcarbamoylimino)-5-hexylsulfonyl-1,3,4-thiadiazole-3-carboxylate Chemical compound C(CCC)OC(=O)N1C(SC(=N1)S(=O)(=O)CCCCCC)=NC(N(C)C)=O YFXPCVAXBXYKPG-UHFFFAOYSA-N 0.000 claims 1
- PVYCSOHHHZDPKF-UHFFFAOYSA-N butyl 2-(dimethylcarbamoylimino)-5-methylsulfanyl-1,3,4-thiadiazole-3-carboxylate Chemical compound C(CCC)OC(=O)N1C(SC(=N1)SC)=NC(N(C)C)=O PVYCSOHHHZDPKF-UHFFFAOYSA-N 0.000 claims 1
- ZSVHBDFRUWPVKA-UHFFFAOYSA-N butyl 2-(dimethylcarbamoylimino)-5-methylsulfonyl-1,3,4-thiadiazole-3-carboxylate Chemical compound C(CCC)OC(=O)N1C(SC(=N1)S(=O)(=O)C)=NC(N(C)C)=O ZSVHBDFRUWPVKA-UHFFFAOYSA-N 0.000 claims 1
- WOUZLXVBMOTPNP-UHFFFAOYSA-N butyl 2-(dimethylcarbamoylimino)-5-prop-2-enylsulfanyl-1,3,4-thiadiazole-3-carboxylate Chemical compound C(CCC)OC(=O)N1C(SC(=N1)SCC=C)=NC(N(C)C)=O WOUZLXVBMOTPNP-UHFFFAOYSA-N 0.000 claims 1
- HYCPJJSOQOUYMK-UHFFFAOYSA-N butyl 2-(dimethylcarbamoylimino)-5-propan-2-ylsulfanyl-1,3,4-thiadiazole-3-carboxylate Chemical compound C(CCC)OC(=O)N1C(SC(=N1)SC(C)C)=NC(N(C)C)=O HYCPJJSOQOUYMK-UHFFFAOYSA-N 0.000 claims 1
- FFYAKFBZVMKTCP-UHFFFAOYSA-N butyl 2-(dimethylcarbamoylimino)-5-propan-2-ylsulfonyl-1,3,4-thiadiazole-3-carboxylate Chemical compound C(CCC)OC(=O)N1C(SC(=N1)S(=O)(=O)C(C)C)=NC(N(C)C)=O FFYAKFBZVMKTCP-UHFFFAOYSA-N 0.000 claims 1
- UOWTZMMMUSXJQB-UHFFFAOYSA-N butyl 5-but-2-enylsulfanyl-2-(dimethylcarbamoylimino)-1,3,4-thiadiazole-3-carboxylate Chemical compound C(CCC)OC(=O)N1C(SC(=N1)SCC=CC)=NC(N(C)C)=O UOWTZMMMUSXJQB-UHFFFAOYSA-N 0.000 claims 1
- OVFGZYLIJLMMOS-UHFFFAOYSA-N ethyl 2-(dimethylcarbamoylimino)-5-ethylsulfanyl-1,3,4-thiadiazole-3-carboxylate Chemical compound C(C)OC(=O)N1C(SC(=N1)SCC)=NC(N(C)C)=O OVFGZYLIJLMMOS-UHFFFAOYSA-N 0.000 claims 1
- GFVQHFDOPMKUFO-UHFFFAOYSA-N ethyl 2-(dimethylcarbamoylimino)-5-ethylsulfonyl-1,3,4-thiadiazole-3-carboxylate Chemical compound CCOC(=O)N1N=C(S(=O)(=O)CC)SC1=NC(=O)N(C)C GFVQHFDOPMKUFO-UHFFFAOYSA-N 0.000 claims 1
- RGKYKNZRPPLJCY-UHFFFAOYSA-N ethyl 2-(dimethylcarbamoylimino)-5-hexylsulfanyl-1,3,4-thiadiazole-3-carboxylate Chemical compound C(C)OC(=O)N1C(SC(=N1)SCCCCCC)=NC(N(C)C)=O RGKYKNZRPPLJCY-UHFFFAOYSA-N 0.000 claims 1
- KWIPOCASRDNEKH-UHFFFAOYSA-N ethyl 2-(dimethylcarbamoylimino)-5-methylsulfonyl-1,3,4-thiadiazole-3-carboxylate Chemical compound C(C)OC(=O)N1C(SC(=N1)S(=O)(=O)C)=NC(N(C)C)=O KWIPOCASRDNEKH-UHFFFAOYSA-N 0.000 claims 1
- NRVLKXMRJGTGJC-UHFFFAOYSA-N methyl 2-(dimethylcarbamoylimino)-5-ethylsulfanyl-1,3,4-thiadiazole-3-carboxylate Chemical compound CCSC1=NN(C(=O)OC)C(=NC(=O)N(C)C)S1 NRVLKXMRJGTGJC-UHFFFAOYSA-N 0.000 claims 1
- MKIZCXBFBRAUHT-UHFFFAOYSA-N methyl 2-(dimethylcarbamoylimino)-5-ethylsulfonyl-1,3,4-thiadiazole-3-carboxylate Chemical compound CCS(=O)(=O)C1=NN(C(=O)OC)C(=NC(=O)N(C)C)S1 MKIZCXBFBRAUHT-UHFFFAOYSA-N 0.000 claims 1
- YLCGVEMJQIIEGX-UHFFFAOYSA-N methyl 2-(dimethylcarbamoylimino)-5-hexylsulfanyl-1,3,4-thiadiazole-3-carboxylate Chemical compound CCCCCCSC1=NN(C(=O)OC)C(=NC(=O)N(C)C)S1 YLCGVEMJQIIEGX-UHFFFAOYSA-N 0.000 claims 1
- CPFFMIWOJNRVDE-UHFFFAOYSA-N methyl 2-(dimethylcarbamoylimino)-5-methylsulfanyl-1,3,4-thiadiazole-3-carboxylate Chemical compound COC(=O)N1N=C(SC)SC1=NC(=O)N(C)C CPFFMIWOJNRVDE-UHFFFAOYSA-N 0.000 claims 1
- HOTXYOPRCDCSOP-UHFFFAOYSA-N methyl 2-(dimethylcarbamoylimino)-5-methylsulfonyl-1,3,4-thiadiazole-3-carboxylate Chemical compound COC(=O)N1N=C(S(C)(=O)=O)SC1=NC(=O)N(C)C HOTXYOPRCDCSOP-UHFFFAOYSA-N 0.000 claims 1
- LDDLXRPGDPSEFH-UHFFFAOYSA-N methyl 2-(dimethylcarbamoylimino)-5-pentylsulfanyl-1,3,4-thiadiazole-3-carboxylate Chemical compound CCCCCSC1=NN(C(=O)OC)C(=NC(=O)N(C)C)S1 LDDLXRPGDPSEFH-UHFFFAOYSA-N 0.000 claims 1
- LZJZKPWZKHFBTC-UHFFFAOYSA-N methyl 2-(dimethylcarbamoylimino)-5-prop-2-enylsulfanyl-1,3,4-thiadiazole-3-carboxylate Chemical compound COC(=O)N1N=C(SCC=C)SC1=NC(=O)N(C)C LZJZKPWZKHFBTC-UHFFFAOYSA-N 0.000 claims 1
- SPEDCIDJBOQOLU-UHFFFAOYSA-N methyl 2-(dimethylcarbamoylimino)-5-propylsulfanyl-1,3,4-thiadiazole-3-carboxylate Chemical compound CCCSC1=NN(C(=O)OC)C(=NC(=O)N(C)C)S1 SPEDCIDJBOQOLU-UHFFFAOYSA-N 0.000 claims 1
- YCHYQWHDEFAUDW-UHFFFAOYSA-N methyl 5-but-2-enylsulfanyl-2-(dimethylcarbamoylimino)-1,3,4-thiadiazole-3-carboxylate Chemical compound COC(=O)N1N=C(SCC=CC)SC1=NC(=O)N(C)C YCHYQWHDEFAUDW-UHFFFAOYSA-N 0.000 claims 1
- UIOKUCVRQRCTOG-UHFFFAOYSA-N pentyl 2-(dimethylcarbamoylimino)-5-ethylsulfanyl-1,3,4-thiadiazole-3-carboxylate Chemical compound C(CCCC)OC(=O)N1C(SC(=N1)SCC)=NC(N(C)C)=O UIOKUCVRQRCTOG-UHFFFAOYSA-N 0.000 claims 1
- RDEGPHUKFCYVRH-UHFFFAOYSA-N pentyl 2-(dimethylcarbamoylimino)-5-methylsulfanyl-1,3,4-thiadiazole-3-carboxylate Chemical compound C(CCCC)OC(=O)N1C(SC(=N1)SC)=NC(N(C)C)=O RDEGPHUKFCYVRH-UHFFFAOYSA-N 0.000 claims 1
- GCHJRLPOSBCUSO-UHFFFAOYSA-N pentyl 2-(dimethylcarbamoylimino)-5-methylsulfonyl-1,3,4-thiadiazole-3-carboxylate Chemical compound C(CCCC)OC(=O)N1C(SC(=N1)S(=O)(=O)C)=NC(N(C)C)=O GCHJRLPOSBCUSO-UHFFFAOYSA-N 0.000 claims 1
- WNRIXTZCYAFSJO-UHFFFAOYSA-N pentyl 2-(dimethylcarbamoylimino)-5-propan-2-ylsulfanyl-1,3,4-thiadiazole-3-carboxylate Chemical compound C(CCCC)OC(=O)N1C(SC(=N1)SC(C)C)=NC(N(C)C)=O WNRIXTZCYAFSJO-UHFFFAOYSA-N 0.000 claims 1
- PRQHFEVGGQJMSK-UHFFFAOYSA-N pentyl 2-(dimethylcarbamoylimino)-5-propan-2-ylsulfonyl-1,3,4-thiadiazole-3-carboxylate Chemical compound C(CCCC)OC(=O)N1C(SC(=N1)S(=O)(=O)C(C)C)=NC(N(C)C)=O PRQHFEVGGQJMSK-UHFFFAOYSA-N 0.000 claims 1
- NTVVQODQIKFJKZ-UHFFFAOYSA-N pentyl 2-(dimethylcarbamoylimino)-5-propylsulfanyl-1,3,4-thiadiazole-3-carboxylate Chemical compound C(CCCC)OC(=O)N1C(SC(=N1)SCCC)=NC(N(C)C)=O NTVVQODQIKFJKZ-UHFFFAOYSA-N 0.000 claims 1
- LTQMKJDPXAGXDG-UHFFFAOYSA-N pentyl 2-(dimethylcarbamoylimino)-5-propylsulfonyl-1,3,4-thiadiazole-3-carboxylate Chemical compound C(CCCC)OC(=O)N1C(SC(=N1)S(=O)(=O)CCC)=NC(N(C)C)=O LTQMKJDPXAGXDG-UHFFFAOYSA-N 0.000 claims 1
- QOADHLLGMURUNG-UHFFFAOYSA-N prop-2-enyl 2-(dimethylcarbamoylimino)-5-(2-methylpropylsulfanyl)-1,3,4-thiadiazole-3-carboxylate Chemical compound CC(C)CSC1=NN(C(=O)OCC=C)C(=NC(=O)N(C)C)S1 QOADHLLGMURUNG-UHFFFAOYSA-N 0.000 claims 1
- QZMRVRCBMZXZME-UHFFFAOYSA-N prop-2-enyl 2-(dimethylcarbamoylimino)-5-methylsulfanyl-1,3,4-thiadiazole-3-carboxylate Chemical compound CSC1=NN(C(=O)OCC=C)C(=NC(=O)N(C)C)S1 QZMRVRCBMZXZME-UHFFFAOYSA-N 0.000 claims 1
- ABZMLLKVVODUGL-UHFFFAOYSA-N prop-2-enyl 2-(dimethylcarbamoylimino)-5-methylsulfonyl-1,3,4-thiadiazole-3-carboxylate Chemical compound CN(C)C(=O)N=C1SC(S(C)(=O)=O)=NN1C(=O)OCC=C ABZMLLKVVODUGL-UHFFFAOYSA-N 0.000 claims 1
- IAGBXQSMFXXOLQ-UHFFFAOYSA-N prop-2-enyl 2-(dimethylcarbamoylimino)-5-propan-2-ylsulfanyl-1,3,4-thiadiazole-3-carboxylate Chemical compound CC(C)SC1=NN(C(=O)OCC=C)C(=NC(=O)N(C)C)S1 IAGBXQSMFXXOLQ-UHFFFAOYSA-N 0.000 claims 1
- FILXGDSYXYDAMN-UHFFFAOYSA-N prop-2-enyl 2-(dimethylcarbamoylimino)-5-propan-2-ylsulfonyl-1,3,4-thiadiazole-3-carboxylate Chemical compound CC(C)S(=O)(=O)C1=NN(C(=O)OCC=C)C(=NC(=O)N(C)C)S1 FILXGDSYXYDAMN-UHFFFAOYSA-N 0.000 claims 1
- HACNBSYTQOAGBM-UHFFFAOYSA-N prop-2-enyl 5-but-2-enylsulfanyl-2-(dimethylcarbamoylimino)-1,3,4-thiadiazole-3-carboxylate Chemical compound CC=CCSC1=NN(C(=O)OCC=C)C(=NC(=O)N(C)C)S1 HACNBSYTQOAGBM-UHFFFAOYSA-N 0.000 claims 1
- AFLGLGACODWYCU-UHFFFAOYSA-N propan-2-yl 2-(dimethylcarbamoylimino)-5-ethylsulfanyl-1,3,4-thiadiazole-3-carboxylate Chemical compound CCSC1=NN(C(=O)OC(C)C)C(=NC(=O)N(C)C)S1 AFLGLGACODWYCU-UHFFFAOYSA-N 0.000 claims 1
- MYBPZHYVNADFDS-UHFFFAOYSA-N propan-2-yl 2-(dimethylcarbamoylimino)-5-ethylsulfonyl-1,3,4-thiadiazole-3-carboxylate Chemical compound CCS(=O)(=O)C1=NN(C(=O)OC(C)C)C(=NC(=O)N(C)C)S1 MYBPZHYVNADFDS-UHFFFAOYSA-N 0.000 claims 1
- XBTWBXMPMWTXQH-UHFFFAOYSA-N propan-2-yl 2-(dimethylcarbamoylimino)-5-hexylsulfanyl-1,3,4-thiadiazole-3-carboxylate Chemical compound CCCCCCSC1=NN(C(=O)OC(C)C)C(=NC(=O)N(C)C)S1 XBTWBXMPMWTXQH-UHFFFAOYSA-N 0.000 claims 1
- RBHHFXJGDOQCQC-UHFFFAOYSA-N propan-2-yl 2-(dimethylcarbamoylimino)-5-methylsulfanyl-1,3,4-thiadiazole-3-carboxylate Chemical compound CSC1=NN(C(=O)OC(C)C)C(=NC(=O)N(C)C)S1 RBHHFXJGDOQCQC-UHFFFAOYSA-N 0.000 claims 1
- MPGDMWCVIWYLSI-UHFFFAOYSA-N propan-2-yl 2-(dimethylcarbamoylimino)-5-methylsulfonyl-1,3,4-thiadiazole-3-carboxylate Chemical compound C(C)(C)OC(=O)N1C(SC(=N1)S(=O)(=O)C)=NC(N(C)C)=O MPGDMWCVIWYLSI-UHFFFAOYSA-N 0.000 claims 1
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- PVEOYINWKBTPIZ-UHFFFAOYSA-M but-3-enoate Chemical compound [O-]C(=O)CC=C PVEOYINWKBTPIZ-UHFFFAOYSA-M 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 230000002363 herbicidal effect Effects 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 239000007900 aqueous suspension Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 244000038559 crop plants Species 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 239000003495 polar organic solvent Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000375 suspending agent Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- IDAFAPNAZCWRKV-UHFFFAOYSA-N 1,1-dimethyl-3-(1,3,4-thiadiazol-2-yl)urea Chemical class CN(C)C(=O)NC1=NN=CS1 IDAFAPNAZCWRKV-UHFFFAOYSA-N 0.000 description 1
- QUKGLNCXGVWCJX-UHFFFAOYSA-N 1,3,4-thiadiazol-2-amine Chemical class NC1=NN=CS1 QUKGLNCXGVWCJX-UHFFFAOYSA-N 0.000 description 1
- CMQJDYXIZIONAP-UHFFFAOYSA-N 1,3,4-thiadiazol-2-ylurea Chemical class NC(=O)NC1=NN=CS1 CMQJDYXIZIONAP-UHFFFAOYSA-N 0.000 description 1
- AKUNSTOMHUXJOZ-UHFFFAOYSA-N 1-hydroperoxybutane Chemical compound CCCCOO AKUNSTOMHUXJOZ-UHFFFAOYSA-N 0.000 description 1
- 125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- GARHMFKENWNGGC-UHFFFAOYSA-N 3-(5-ethylsulfanyl-1,3,4-thiadiazol-2-yl)-1,1-dimethylurea Chemical compound CCSC1=NN=C(S1)NC(=O)N(C)C GARHMFKENWNGGC-UHFFFAOYSA-N 0.000 description 1
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- INLBFEGZOMVTHT-UHFFFAOYSA-N CCCCCOC(N1N=CSC1=S(=O)=O)=O Chemical compound CCCCCOC(N1N=CSC1=S(=O)=O)=O INLBFEGZOMVTHT-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- YIIMEMSDCNDGTB-UHFFFAOYSA-N Dimethylcarbamoyl chloride Chemical compound CN(C)C(Cl)=O YIIMEMSDCNDGTB-UHFFFAOYSA-N 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 241000209510 Liliopsida Species 0.000 description 1
- 235000019738 Limestone Nutrition 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 240000004296 Lolium perenne Species 0.000 description 1
- 244000042664 Matricaria chamomilla Species 0.000 description 1
- 235000007232 Matricaria chamomilla Nutrition 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- NPYPAHLBTDXSSS-UHFFFAOYSA-N Potassium ion Chemical compound [K+] NPYPAHLBTDXSSS-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 241000220261 Sinapis Species 0.000 description 1
- 240000003768 Solanum lycopersicum Species 0.000 description 1
- 235000021536 Sugar beet Nutrition 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 150000008107 benzenesulfonic acids Chemical class 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000003857 carboxamides Chemical class 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- YNAXGNQDDXYYPK-UHFFFAOYSA-N ethyl 3,4-dihydro-2H-pyrrole-4-carboxylate Chemical compound C(C)OC(=O)C1C=NCC1 YNAXGNQDDXYYPK-UHFFFAOYSA-N 0.000 description 1
- 241001233957 eudicotyledons Species 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical group 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([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
- 235000021374 legumes Nutrition 0.000 description 1
- 239000006028 limestone Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 210000001699 lower leg Anatomy 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- DADZWWSREWCZDJ-UHFFFAOYSA-N methyl 2h-1,3,4-thiadiazole-3-carboxylate Chemical compound COC(=O)N1CSC=N1 DADZWWSREWCZDJ-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 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
- 239000005645 nematicide Substances 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 210000002741 palatine tonsil Anatomy 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 231100000208 phytotoxic Toxicity 0.000 description 1
- 230000000885 phytotoxic effect Effects 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 235000012015 potatoes Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- DTGBJCJRBUGDIG-UHFFFAOYSA-N propan-2-yl 2h-1,3,4-thiadiazole-3-carboxylate Chemical compound CC(C)OC(=O)N1CSC=N1 DTGBJCJRBUGDIG-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 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
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000000725 suspension 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
- 150000003512 tertiary amines Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000002023 wood Substances 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)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (30)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19762621647 DE2621647A1 (de) | 1976-05-13 | 1976-05-13 | 2-(dimethylcarbamoylimino)-1,3,4- thiadiazolin-3-carbonsaeure-ester, verfahren zur herstellung dieser verbindungen sowie diese enthaltende herbizide mittel |
| LU76938A LU76938A1 (enExample) | 1976-05-13 | 1977-03-11 | |
| DK114477A DK114477A (da) | 1976-05-13 | 1977-03-16 | 2-(dimethylcarbamoylimino)-1,3,4-thiadiazolin-3-carboxylsyreestere fremgangsmade til fremstilling af disse forbindelser samt herbicide midler indeholdende disse forbindelser |
| CS771820A CS192480B2 (en) | 1976-05-13 | 1977-03-18 | Herbicide means and method of making the active substances |
| NL7703889A NL7703889A (nl) | 1976-05-13 | 1977-04-07 | S-(dimethylcarbamoylimino)-1,3,4-thiadiazoline- -3-carbonzuuresters, werkwijze voor het berei- den daarvan, alsmede werkwijze voor het berei- den van deze verbindingen bevattende herbiciden. |
| ES457730A ES457730A1 (es) | 1976-05-13 | 1977-04-12 | Procedimiento para la preparacion de esteres alcohilicos de acidos 2-(dimetilcarbamoilimino)-1,3,4-tiadiazolin-3-carbo- xilicos. |
| SU772468202A SU649320A3 (ru) | 1976-05-13 | 1977-04-12 | Способ получени эфиров 2-(диметилкарбамоилимино)-1,3,4-тиадиазолин 3-карбоновой кислоты |
| FI771298A FI771298A7 (enExample) | 1976-05-13 | 1977-04-25 | |
| BG036125A BG27716A3 (bg) | 1976-05-13 | 1977-04-26 | Хербицидно средство |
| SU772475610A SU648048A3 (ru) | 1976-05-13 | 1977-04-28 | Гербицидное средство |
| GB18232/77A GB1583271A (en) | 1976-05-13 | 1977-05-02 | Herbicidally active 2-(dimethylcarbamoylimino)-1,3,4-thiadiazolin-3-carboxylic acid esters process for their manufacture and their use |
| IL52033A IL52033A (en) | 1976-05-13 | 1977-05-05 | Herbicidally active 5-substituted 2-(dimethylcarbamoylimino)-1,3,4-thiadiazoline-3-carboxylic acid esters process for their manufacture and their use |
| IE928/77A IE45053B1 (en) | 1976-05-13 | 1977-05-06 | Herbicidally active 2-(dimethylcarbamoylimino)-1,3,4-thiadiazolin-3-carboxylic acid esters,process for their manufacture and their use |
| RO7790253A RO72224A (ro) | 1976-05-13 | 1977-05-07 | Procedeu pentru prepararea unor esteri ai acidului 2-(dimetilcarbamoilimino)-1,3,4-tiadiazolin-3-carboxilic |
| TR19696A TR19696A (tr) | 1976-05-13 | 1977-05-10 | Herbist olarak aktif 2-(dimetil-karbamoylimino)-1,3,4-tiyadiya-zolin-3 karboksilik asit esterleri,bunlarin imali usulue ve kullanilmalari |
| US05/795,642 US4169718A (en) | 1976-05-13 | 1977-05-10 | 2-(Dimethylcarbamoylimino)-1,3,4-thiadiazolin-3-carboxylic acid esters and herbicides containing the same |
| DD7700198870A DD130201A5 (de) | 1976-05-13 | 1977-05-11 | Herbizide mittel |
| PT66533A PT66533B (de) | 1976-05-13 | 1977-05-11 | 2-(dimethylcarbamoylimino)-1,3,4-thiadiazolin-3-carbonsaure-ester verfahren zur herstellung dieser verbindungen sowie diese enthaltende mittel |
| PL1977198027A PL102602B1 (pl) | 1976-05-13 | 1977-05-11 | Srodek chwastobojczy |
| AT336177A AT354802B (de) | 1976-05-13 | 1977-05-11 | Herbizide mittel |
| SE7705508A SE7705508L (sv) | 1976-05-13 | 1977-05-11 | 2-(dimetylkarbamoylimino)-1,3,4-tiadiazolin-3-karbonsyraestrar, sett att framstella dessa och herbicida medel innehallande dessa foreningar |
| GR53442A GR63745B (en) | 1976-05-13 | 1977-05-11 | Process for the preparation of 2-(dimethylocarbamoilimino)-1,3,4-thiadiazolin-3-hydrocarbon ester and weed killers means containing in these units |
| NO771675A NO771675L (no) | 1976-05-13 | 1977-05-12 | Herbicide midler. |
| CA278,440A CA1090808A (en) | 1976-05-13 | 1977-05-12 | Herbicidally active 2-(dimethylcarbamoylimino)-1,3,4- thiadiazolin-3-carboxylic acid esters |
| IT23469/77A IT1085078B (it) | 1976-05-13 | 1977-05-12 | Esteri dell'acido 2-(dimetilcarbammoilimmino)-1,3,4-tiadiazolin-3-carbossilico,procedimento per preparare tali composti,e mezzi erbicidi che li contengono |
| AU25133/77A AU2513377A (en) | 1976-05-13 | 1977-05-13 | 2-(dimethyl carbamoylimino)-1,3,4-thiadiazolin-3-carboxylic acid esters |
| ZA00772869A ZA772869B (en) | 1976-05-13 | 1977-05-13 | Herbicidally active 2-(dimethylcarbamoylimino)-1,3,4-thiadiazolin-3-carboxylic acid esters,process for their manufacture and their use |
| JP5523377A JPS52139062A (en) | 1976-05-13 | 1977-05-13 | 22*dimethylcarbamoylimino**1*3*44thiadiazolinee 33carboxylate* its preparation and herbicide containing same |
| BE177559A BE854614A (fr) | 1976-05-13 | 1977-05-13 | Esters d'acide 2-(dimethylcarbamoylimino)-1,3,4-thiadiazoline-3-carboxylique |
| FR7714692A FR2351110A1 (fr) | 1976-05-13 | 1977-05-13 | Carbamoylimino-2 thiadiazolines et produits herbicides qui en contiennent |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19762621647 DE2621647A1 (de) | 1976-05-13 | 1976-05-13 | 2-(dimethylcarbamoylimino)-1,3,4- thiadiazolin-3-carbonsaeure-ester, verfahren zur herstellung dieser verbindungen sowie diese enthaltende herbizide mittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2621647A1 true DE2621647A1 (de) | 1977-12-01 |
Family
ID=5978046
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19762621647 Withdrawn DE2621647A1 (de) | 1976-05-13 | 1976-05-13 | 2-(dimethylcarbamoylimino)-1,3,4- thiadiazolin-3-carbonsaeure-ester, verfahren zur herstellung dieser verbindungen sowie diese enthaltende herbizide mittel |
Country Status (29)
| Country | Link |
|---|---|
| US (1) | US4169718A (enExample) |
| JP (1) | JPS52139062A (enExample) |
| AT (1) | AT354802B (enExample) |
| AU (1) | AU2513377A (enExample) |
| BE (1) | BE854614A (enExample) |
| BG (1) | BG27716A3 (enExample) |
| CA (1) | CA1090808A (enExample) |
| CS (1) | CS192480B2 (enExample) |
| DD (1) | DD130201A5 (enExample) |
| DE (1) | DE2621647A1 (enExample) |
| DK (1) | DK114477A (enExample) |
| ES (1) | ES457730A1 (enExample) |
| FI (1) | FI771298A7 (enExample) |
| FR (1) | FR2351110A1 (enExample) |
| GB (1) | GB1583271A (enExample) |
| GR (1) | GR63745B (enExample) |
| IE (1) | IE45053B1 (enExample) |
| IL (1) | IL52033A (enExample) |
| IT (1) | IT1085078B (enExample) |
| LU (1) | LU76938A1 (enExample) |
| NL (1) | NL7703889A (enExample) |
| NO (1) | NO771675L (enExample) |
| PL (1) | PL102602B1 (enExample) |
| PT (1) | PT66533B (enExample) |
| RO (1) | RO72224A (enExample) |
| SE (1) | SE7705508L (enExample) |
| SU (2) | SU649320A3 (enExample) |
| TR (1) | TR19696A (enExample) |
| ZA (1) | ZA772869B (enExample) |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL293262A (enExample) * | 1962-05-28 | |||
| DE2124260A1 (de) * | 1971-05-15 | 1972-11-30 | Farbenfabriken Bayer AG, 5090 Le verkusen | Verfahren zur Herstellung von 4 sub stituierten 1,3,4 Thiadiazolon (5) yl (2) harnstoffen |
-
1976
- 1976-05-13 DE DE19762621647 patent/DE2621647A1/de not_active Withdrawn
-
1977
- 1977-03-11 LU LU76938A patent/LU76938A1/xx unknown
- 1977-03-16 DK DK114477A patent/DK114477A/da unknown
- 1977-03-18 CS CS771820A patent/CS192480B2/cs unknown
- 1977-04-07 NL NL7703889A patent/NL7703889A/xx not_active Application Discontinuation
- 1977-04-12 SU SU772468202A patent/SU649320A3/ru active
- 1977-04-12 ES ES457730A patent/ES457730A1/es not_active Expired
- 1977-04-25 FI FI771298A patent/FI771298A7/fi not_active Application Discontinuation
- 1977-04-26 BG BG036125A patent/BG27716A3/xx unknown
- 1977-04-28 SU SU772475610A patent/SU648048A3/ru active
- 1977-05-02 GB GB18232/77A patent/GB1583271A/en not_active Expired
- 1977-05-05 IL IL52033A patent/IL52033A/xx unknown
- 1977-05-06 IE IE928/77A patent/IE45053B1/en unknown
- 1977-05-07 RO RO7790253A patent/RO72224A/ro unknown
- 1977-05-10 TR TR19696A patent/TR19696A/xx unknown
- 1977-05-10 US US05/795,642 patent/US4169718A/en not_active Expired - Lifetime
- 1977-05-11 DD DD7700198870A patent/DD130201A5/xx unknown
- 1977-05-11 SE SE7705508A patent/SE7705508L/xx unknown
- 1977-05-11 PL PL1977198027A patent/PL102602B1/pl unknown
- 1977-05-11 AT AT336177A patent/AT354802B/de not_active IP Right Cessation
- 1977-05-11 PT PT66533A patent/PT66533B/pt unknown
- 1977-05-11 GR GR53442A patent/GR63745B/el unknown
- 1977-05-12 IT IT23469/77A patent/IT1085078B/it active
- 1977-05-12 NO NO771675A patent/NO771675L/no unknown
- 1977-05-12 CA CA278,440A patent/CA1090808A/en not_active Expired
- 1977-05-13 ZA ZA00772869A patent/ZA772869B/xx unknown
- 1977-05-13 JP JP5523377A patent/JPS52139062A/ja active Granted
- 1977-05-13 FR FR7714692A patent/FR2351110A1/fr active Pending
- 1977-05-13 AU AU25133/77A patent/AU2513377A/en not_active Expired
- 1977-05-13 BE BE177559A patent/BE854614A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| LU76938A1 (enExample) | 1977-07-14 |
| JPS5538342B2 (enExample) | 1980-10-03 |
| NL7703889A (nl) | 1977-11-15 |
| ATA336177A (de) | 1979-06-15 |
| IL52033A (en) | 1980-03-31 |
| IL52033A0 (en) | 1977-07-31 |
| ES457730A1 (es) | 1978-02-16 |
| GB1583271A (en) | 1981-01-21 |
| IE45053L (en) | 1977-11-13 |
| BG27716A3 (bg) | 1979-12-12 |
| DK114477A (da) | 1977-11-14 |
| NO771675L (no) | 1977-11-15 |
| SU649320A3 (ru) | 1979-02-25 |
| US4169718A (en) | 1979-10-02 |
| ZA772869B (en) | 1978-03-29 |
| PL102602B1 (pl) | 1979-04-30 |
| JPS52139062A (en) | 1977-11-19 |
| FR2351110A1 (fr) | 1977-12-09 |
| SE7705508L (sv) | 1977-11-14 |
| AU2513377A (en) | 1978-11-16 |
| DD130201A5 (de) | 1978-03-15 |
| SU648048A3 (ru) | 1979-02-15 |
| CS192480B2 (en) | 1979-08-31 |
| PT66533B (de) | 1978-10-17 |
| IE45053B1 (en) | 1982-06-16 |
| PL198027A1 (pl) | 1978-02-13 |
| TR19696A (tr) | 1979-10-11 |
| FI771298A7 (enExample) | 1977-11-14 |
| RO72224A (ro) | 1982-05-10 |
| AT354802B (de) | 1979-01-25 |
| BE854614A (fr) | 1977-11-14 |
| PT66533A (de) | 1977-06-01 |
| GR63745B (en) | 1979-12-04 |
| CA1090808A (en) | 1980-12-02 |
| IT1085078B (it) | 1985-05-28 |
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| 8139 | Disposal/non-payment of the annual fee |