DK172396B1 - Thiophencarboxylsyrederivater, middel til bekæmpelse af væksten af uønsket vegetation, fremgangsmåde til bekæmpelse af uønsket vegetation samt mellemprodukter til fremstilling af de nævnte derivater - Google Patents
Thiophencarboxylsyrederivater, middel til bekæmpelse af væksten af uønsket vegetation, fremgangsmåde til bekæmpelse af uønsket vegetation samt mellemprodukter til fremstilling af de nævnte derivater Download PDFInfo
- Publication number
- DK172396B1 DK172396B1 DK471680A DK471680A DK172396B1 DK 172396 B1 DK172396 B1 DK 172396B1 DK 471680 A DK471680 A DK 471680A DK 471680 A DK471680 A DK 471680A DK 172396 B1 DK172396 B1 DK 172396B1
- Authority
- DK
- Denmark
- Prior art keywords
- aminosulfonyl
- aminocarbonyl
- methyl
- thiophenecarboxylate
- compound according
- Prior art date
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- 238000000034 method Methods 0.000 title claims description 22
- 238000002360 preparation method Methods 0.000 title claims description 22
- QERYCTSHXKAMIS-UHFFFAOYSA-N thiophene-2-carboxylic acid Chemical class OC(=O)C1=CC=CS1 QERYCTSHXKAMIS-UHFFFAOYSA-N 0.000 title claims description 4
- 239000000543 intermediate Substances 0.000 title description 12
- 150000001875 compounds Chemical class 0.000 claims description 106
- -1 ben2yl Chemical group 0.000 claims description 56
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 46
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 37
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 33
- 229910052739 hydrogen Inorganic materials 0.000 claims description 27
- 241000196324 Embryophyta Species 0.000 claims description 26
- 150000003839 salts Chemical class 0.000 claims description 18
- 239000007787 solid Substances 0.000 claims description 15
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 239000004615 ingredient Substances 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 239000003085 diluting agent Substances 0.000 claims description 9
- 229910052783 alkali metal Inorganic materials 0.000 claims description 8
- 150000001768 cations Chemical class 0.000 claims description 7
- VJQINSVXSJNRLA-UHFFFAOYSA-N methyl 3-isocyanatosulfonylthiophene-2-carboxylate Chemical group COC(=O)C=1SC=CC=1S(=O)(=O)N=C=O VJQINSVXSJNRLA-UHFFFAOYSA-N 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 239000004094 surface-active agent Substances 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 235000013339 cereals Nutrition 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 229910052727 yttrium Inorganic materials 0.000 claims description 4
- LYKUIUGQPNOYJA-UHFFFAOYSA-N methyl 3-[(4,6-dimethylpyrimidin-2-yl)carbamoylsulfamoyl]thiophene-2-carboxylate Chemical compound S1C=CC(S(=O)(=O)NC(=O)NC=2N=C(C)C=C(C)N=2)=C1C(=O)OC LYKUIUGQPNOYJA-UHFFFAOYSA-N 0.000 claims description 3
- PCZLYMBIMAWUKU-UHFFFAOYSA-N methyl 3-[(4-methoxy-6-methylpyrimidin-2-yl)carbamoylsulfamoyl]thiophene-2-carboxylate Chemical group S1C=CC(S(=O)(=O)NC(=O)NC=2N=C(OC)C=C(C)N=2)=C1C(=O)OC PCZLYMBIMAWUKU-UHFFFAOYSA-N 0.000 claims description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
- CXZUVBBHVXZADK-UHFFFAOYSA-N 2-[(4,6-dimethoxypyrimidin-2-yl)carbamoylsulfamoyl]thiophene-3-carboxylic acid Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C2=C(C=CS2)C(O)=O)=N1 CXZUVBBHVXZADK-UHFFFAOYSA-N 0.000 claims description 2
- PPNIPSUXSGUMNM-UHFFFAOYSA-N 2-[(4,6-dimethyl-1,3,5-triazin-2-yl)carbamoylsulfamoyl]thiophene-3-carboxylic acid Chemical compound CC1=NC(C)=NC(NC(=O)NS(=O)(=O)C2=C(C=CS2)C(O)=O)=N1 PPNIPSUXSGUMNM-UHFFFAOYSA-N 0.000 claims description 2
- IOHMHFKJCSVLLE-UHFFFAOYSA-N 2-[(4-methoxy-6-methylpyrimidin-2-yl)carbamoylsulfamoyl]thiophene-3-carboxylic acid Chemical compound COC1=CC(C)=NC(NC(=O)NS(=O)(=O)C2=C(C=CS2)C(O)=O)=N1 IOHMHFKJCSVLLE-UHFFFAOYSA-N 0.000 claims description 2
- RXDVGDJPGHECPY-UHFFFAOYSA-N 3-[(4,6-dimethoxy-1,3,5-triazin-2-yl)carbamoylsulfamoyl]thiophene-2-carboxylic acid Chemical compound COC1=NC(OC)=NC(NC(=O)NS(=O)(=O)C2=C(SC=C2)C(O)=O)=N1 RXDVGDJPGHECPY-UHFFFAOYSA-N 0.000 claims description 2
- RDHMDRUHVRPQGR-UHFFFAOYSA-N 3-[(4-methoxy-6-methylpyrimidin-2-yl)carbamoylsulfamoyl]thiophene-2-carboxylic acid Chemical compound COC1=CC(C)=NC(NC(=O)NS(=O)(=O)C2=C(SC=C2)C(O)=O)=N1 RDHMDRUHVRPQGR-UHFFFAOYSA-N 0.000 claims description 2
- RFXKYBPKWRIFHH-UHFFFAOYSA-N 4-[(4,6-dimethoxy-1,3,5-triazin-2-yl)carbamoylsulfamoyl]thiophene-3-carboxylic acid Chemical compound COC1=NC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CSC=2)C(O)=O)=N1 RFXKYBPKWRIFHH-UHFFFAOYSA-N 0.000 claims description 2
- JFUQWIQCPNTIHV-UHFFFAOYSA-N 4-[(4-methoxy-6-methylpyrimidin-2-yl)carbamoylsulfamoyl]thiophene-3-carboxylic acid Chemical compound COC1=CC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CSC=2)C(O)=O)=N1 JFUQWIQCPNTIHV-UHFFFAOYSA-N 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- ICFOUVRGGDFDRJ-UHFFFAOYSA-N methyl 2-[(4,6-dimethoxy-1,3,5-triazin-2-yl)carbamoylsulfamoyl]thiophene-3-carboxylate Chemical compound C1=CSC(S(=O)(=O)NC(=O)NC=2N=C(OC)N=C(OC)N=2)=C1C(=O)OC ICFOUVRGGDFDRJ-UHFFFAOYSA-N 0.000 claims description 2
- JXHGAJHKCDEAIJ-UHFFFAOYSA-N methyl 2-[(4,6-dimethylpyrimidin-2-yl)carbamoylsulfamoyl]thiophene-3-carboxylate Chemical compound C1=CSC(S(=O)(=O)NC(=O)NC=2N=C(C)C=C(C)N=2)=C1C(=O)OC JXHGAJHKCDEAIJ-UHFFFAOYSA-N 0.000 claims description 2
- GTAQAFRDXJPKPP-UHFFFAOYSA-N methyl 2-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)carbamoylsulfamoyl]thiophene-3-carboxylate Chemical compound C1=CSC(S(=O)(=O)NC(=O)NC=2N=C(OC)N=C(C)N=2)=C1C(=O)OC GTAQAFRDXJPKPP-UHFFFAOYSA-N 0.000 claims description 2
- CBPCIPRNQOUIBA-UHFFFAOYSA-N methyl 2-[(4-methoxy-6-methylpyrimidin-2-yl)carbamoylsulfamoyl]thiophene-3-carboxylate Chemical compound C1=CSC(S(=O)(=O)NC(=O)NC=2N=C(OC)C=C(C)N=2)=C1C(=O)OC CBPCIPRNQOUIBA-UHFFFAOYSA-N 0.000 claims description 2
- NWOCKRHNKMXDES-UHFFFAOYSA-N methyl 2-isocyanatosulfonylthiophene-3-carboxylate Chemical compound COC(=O)C=1C=CSC=1S(=O)(=O)N=C=O NWOCKRHNKMXDES-UHFFFAOYSA-N 0.000 claims description 2
- QFORSDYWCGBJKC-UHFFFAOYSA-N methyl 4-[(4,6-dimethoxypyrimidin-2-yl)carbamoylsulfamoyl]thiophene-3-carboxylate Chemical compound COC(=O)C1=CSC=C1S(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 QFORSDYWCGBJKC-UHFFFAOYSA-N 0.000 claims description 2
- AMVMVVIIRIWLKR-UHFFFAOYSA-N methyl 4-[(4,6-dimethylpyrimidin-2-yl)carbamoylsulfamoyl]thiophene-3-carboxylate Chemical compound COC(=O)C1=CSC=C1S(=O)(=O)NC(=O)NC1=NC(C)=CC(C)=N1 AMVMVVIIRIWLKR-UHFFFAOYSA-N 0.000 claims description 2
- DNGNDZKJWUVZAA-UHFFFAOYSA-N methyl 4-isocyanatosulfonylthiophene-3-carboxylate Chemical compound COC(=O)C1=CSC=C1S(=O)(=O)N=C=O DNGNDZKJWUVZAA-UHFFFAOYSA-N 0.000 claims description 2
- GDLNDKKCGJRBSE-UHFFFAOYSA-N propan-2-yl 3-[(4,6-dimethoxypyrimidin-2-yl)carbamoylsulfamoyl]thiophene-2-carboxylate Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C2=C(SC=C2)C(=O)OC(C)C)=N1 GDLNDKKCGJRBSE-UHFFFAOYSA-N 0.000 claims description 2
- 150000003512 tertiary amines Chemical class 0.000 claims description 2
- LOQQVLXUKHKNIA-UHFFFAOYSA-N thifensulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C2=C(SC=C2)C(O)=O)=N1 LOQQVLXUKHKNIA-UHFFFAOYSA-N 0.000 claims description 2
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 2
- UCJDCGANFAKTKA-UHFFFAOYSA-N 2,4-dimethyl-1,3,5-triazine Chemical compound CC1=NC=NC(C)=N1 UCJDCGANFAKTKA-UHFFFAOYSA-N 0.000 claims 2
- LSBIUXKNVUBKRI-UHFFFAOYSA-N 4,6-dimethylpyrimidine Chemical compound CC1=CC(C)=NC=N1 LSBIUXKNVUBKRI-UHFFFAOYSA-N 0.000 claims 1
- ZJCZPJKYNKWNFJ-UHFFFAOYSA-N 4-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)carbamoylsulfamoyl]thiophene-3-carboxylic acid Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CSC=2)C(O)=O)=N1 ZJCZPJKYNKWNFJ-UHFFFAOYSA-N 0.000 claims 1
- GGFJPYWUQCOYLQ-UHFFFAOYSA-N 4-methoxy-6-methylpyrimidine Chemical compound COC1=CC(C)=NC=N1 GGFJPYWUQCOYLQ-UHFFFAOYSA-N 0.000 claims 1
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- SJZZADIYRTWDIA-UHFFFAOYSA-N methyl 4-[(4,6-dimethoxy-1,3,5-triazin-2-yl)carbamoylsulfamoyl]thiophene-3-carboxylate Chemical compound COC(=O)C1=CSC=C1S(=O)(=O)NC(=O)NC1=NC(OC)=NC(OC)=N1 SJZZADIYRTWDIA-UHFFFAOYSA-N 0.000 claims 1
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- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- 244000098338 Triticum aestivum Species 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 1
- RKZXQQPEDGMHBJ-LIGJGSPWSA-N [(2s,3r,4r,5r)-2,3,4,5,6-pentakis[[(z)-octadec-9-enoyl]oxy]hexyl] (z)-octadec-9-enoate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](OC(=O)CCCCCCC\C=C/CCCCCCCC)[C@@H](OC(=O)CCCCCCC\C=C/CCCCCCCC)[C@H](OC(=O)CCCCCCC\C=C/CCCCCCCC)[C@@H](OC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC RKZXQQPEDGMHBJ-LIGJGSPWSA-N 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000003172 aldehyde group Chemical group 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000003178 anti-diabetic effect Effects 0.000 description 1
- 229940125708 antidiabetic agent Drugs 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 230000008033 biological extinction Effects 0.000 description 1
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 1
- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 159000000007 calcium salts Chemical class 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
- 239000004202 carbamide Substances 0.000 description 1
- STIAPHVBRDNOAJ-UHFFFAOYSA-N carbamimidoylazanium;carbonate Chemical compound NC(N)=N.NC(N)=N.OC(O)=O STIAPHVBRDNOAJ-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 150000003857 carboxamides Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003729 cation exchange resin Substances 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
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- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 229940125810 compound 20 Drugs 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
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- 150000001879 copper Chemical class 0.000 description 1
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- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
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- 230000003111 delayed effect Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
- 229910000397 disodium phosphate Inorganic materials 0.000 description 1
- 235000019800 disodium phosphate Nutrition 0.000 description 1
- ZDXLFJGIPWQALB-UHFFFAOYSA-M disodium;oxido(oxo)borane;chlorate Chemical compound [Na+].[Na+].[O-]B=O.[O-]Cl(=O)=O ZDXLFJGIPWQALB-UHFFFAOYSA-M 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N ethyl formate Chemical compound CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 210000003608 fece Anatomy 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000005243 fluidization Methods 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 244000304962 green bristle grass Species 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 231100000001 growth retardation Toxicity 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- XLYOFNOQVPJJNP-ZSJDYOACSA-N heavy water Substances [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 1
- 244000144980 herd Species 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 208000006278 hypochromic anemia Diseases 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- CYPPCCJJKNISFK-UHFFFAOYSA-J kaolinite Chemical compound [OH-].[OH-].[OH-].[OH-].[Al+3].[Al+3].[O-][Si](=O)O[Si]([O-])=O CYPPCCJJKNISFK-UHFFFAOYSA-J 0.000 description 1
- 229910052622 kaolinite Inorganic materials 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 239000010871 livestock manure Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 235000009973 maize Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- UJIIUCUOMQZQEG-UHFFFAOYSA-N methyl 2-[(4,6-dimethoxypyrimidin-2-yl)carbamoylsulfamoyl]thiophene-3-carboxylate Chemical compound C1=CSC(S(=O)(=O)NC(=O)NC=2N=C(OC)C=C(OC)N=2)=C1C(=O)OC UJIIUCUOMQZQEG-UHFFFAOYSA-N 0.000 description 1
- KMTDLXVYRNAWSN-UHFFFAOYSA-N methyl 3-[(4,6-dimethoxy-1,3,5-triazin-2-yl)carbamoylsulfamoyl]thiophene-2-carboxylate Chemical compound S1C=CC(S(=O)(=O)NC(=O)NC=2N=C(OC)N=C(OC)N=2)=C1C(=O)OC KMTDLXVYRNAWSN-UHFFFAOYSA-N 0.000 description 1
- SNKXJIBLPVIXNJ-UHFFFAOYSA-N methyl 3-[(4,6-dimethyl-1,3,5-triazin-2-yl)carbamoylsulfamoyl]thiophene-2-carboxylate Chemical compound S1C=CC(S(=O)(=O)NC(=O)NC=2N=C(C)N=C(C)N=2)=C1C(=O)OC SNKXJIBLPVIXNJ-UHFFFAOYSA-N 0.000 description 1
- PMXNPOJHBQDJKS-UHFFFAOYSA-N methyl 3-sulfamoylthiophene-2-carboxylate Chemical compound COC(=O)C=1SC=CC=1S(N)(=O)=O PMXNPOJHBQDJKS-UHFFFAOYSA-N 0.000 description 1
- QXVUDOHNWJNTRG-UHFFFAOYSA-N methyl 4-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)carbamoylsulfamoyl]thiophene-3-carboxylate Chemical compound COC(=O)C1=CSC=C1S(=O)(=O)NC(=O)NC1=NC(C)=NC(OC)=N1 QXVUDOHNWJNTRG-UHFFFAOYSA-N 0.000 description 1
- AWFXSRBUDZTROY-UHFFFAOYSA-N methyl 4-[(4-methoxy-6-methylpyrimidin-2-yl)carbamoylsulfamoyl]thiophene-3-carboxylate Chemical compound COC(=O)C1=CSC=C1S(=O)(=O)NC(=O)NC1=NC(C)=CC(OC)=N1 AWFXSRBUDZTROY-UHFFFAOYSA-N 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- 230000001035 methylating effect Effects 0.000 description 1
- 230000011987 methylation Effects 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- 230000002906 microbiologic effect Effects 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 229910000403 monosodium phosphate Inorganic materials 0.000 description 1
- 235000019799 monosodium phosphate Nutrition 0.000 description 1
- FSOBYBLQJMGDTH-UHFFFAOYSA-N n-(sulfonylmethyl)carbamoyl chloride Chemical class ClC(=O)NC=S(=O)=O FSOBYBLQJMGDTH-UHFFFAOYSA-N 0.000 description 1
- 230000017074 necrotic cell death Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 235000020030 perry Nutrition 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 230000019612 pigmentation Effects 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- NNEFRVXIJYPZJI-UHFFFAOYSA-N propan-2-yl 3-[(4-methoxy-6-methylpyrimidin-2-yl)carbamoylsulfamoyl]thiophene-2-carboxylate Chemical compound COC1=CC(C)=NC(NC(=O)NS(=O)(=O)C2=C(SC=C2)C(=O)OC(C)C)=N1 NNEFRVXIJYPZJI-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- LJXQPZWIHJMPQQ-UHFFFAOYSA-N pyrimidin-2-amine Chemical compound NC1=NC=CC=N1 LJXQPZWIHJMPQQ-UHFFFAOYSA-N 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012048 reactive intermediate Substances 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 150000008054 sulfonate salts Chemical class 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000004546 suspension concentrate Substances 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 150000003577 thiophenes Chemical class 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 1
- 229940035893 uracil Drugs 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 230000017260 vegetative to reproductive phase transition of meristem Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000001238 wet grinding Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D521/00—Heterocyclic compounds containing unspecified hetero rings
-
- 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
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/36—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof
-
- 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
- A01N47/40—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 a double or triple bond to nitrogen, e.g. cyanates, cyanamides
- A01N47/42—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 a double or triple bond to nitrogen, e.g. cyanates, cyanamides containing —N=CX2 groups, e.g. isothiourea
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US9872379A | 1979-11-30 | 1979-11-30 | |
| US9872379 | 1979-11-30 | ||
| US19626780A | 1980-10-22 | 1980-10-22 | |
| US19626780 | 1980-10-22 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DK471680A DK471680A (da) | 1981-05-31 |
| DK172396B1 true DK172396B1 (da) | 1998-05-18 |
Family
ID=26795021
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK471680A DK172396B1 (da) | 1979-11-30 | 1980-11-06 | Thiophencarboxylsyrederivater, middel til bekæmpelse af væksten af uønsket vegetation, fremgangsmåde til bekæmpelse af uønsket vegetation samt mellemprodukter til fremstilling af de nævnte derivater |
Country Status (24)
| Country | Link |
|---|---|
| EP (1) | EP0030142B1 (cs) |
| KR (1) | KR850000678B1 (cs) |
| AU (1) | AU536122B2 (cs) |
| BR (1) | BR8007674A (cs) |
| CA (1) | CA1189072A (cs) |
| CS (1) | CS250207B2 (cs) |
| DE (1) | DE3069777D1 (cs) |
| DK (1) | DK172396B1 (cs) |
| ES (1) | ES497298A0 (cs) |
| GB (1) | GB2065116B (cs) |
| GR (1) | GR72259B (cs) |
| HU (1) | HU193629B (cs) |
| IE (1) | IE50745B1 (cs) |
| IL (1) | IL61578A (cs) |
| NL (1) | NL971012I1 (cs) |
| NZ (1) | NZ195680A (cs) |
| PH (1) | PH18851A (cs) |
| PL (1) | PL127333B1 (cs) |
| PT (1) | PT72132B (cs) |
| RO (1) | RO81268B (cs) |
| SU (1) | SU1748629A3 (cs) |
| TR (1) | TR21804A (cs) |
| UA (1) | UA19062A (cs) |
| YU (1) | YU302580A (cs) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1994855A2 (en) | 2007-05-25 | 2008-11-26 | Unifor S.p.A. | Workstation system and workstation with multiple, adjustable height, work tops |
Families Citing this family (44)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4487626A (en) * | 1980-08-22 | 1984-12-11 | E. I. Du Pont De Nemours And Company | Herbicidal sulfonamides |
| US4441910A (en) * | 1981-03-24 | 1984-04-10 | E. I. Du Pont De Nemours And Company | Thiophene or furan herbicides |
| AU550945B2 (en) * | 1981-07-10 | 1986-04-10 | E.I. Du Pont De Nemours And Company | Triazolyl-(imidazolyl)-sulphonyl-ureas |
| US4494979A (en) * | 1981-07-24 | 1985-01-22 | E. I. Du Pont De Nemours And Company | Benzofuran sulfamates |
| BR8207267A (pt) * | 1981-12-17 | 1983-10-18 | Du Pont | Compostos composicao adequada e processo para controlar crescimento de vegetacao indesejada |
| ATE35265T1 (de) * | 1982-05-28 | 1988-07-15 | Ciba Geigy Ag | Neue sulfonyl(thio)harnstoffe, verfahren zu deren herstellung und deren verwendung als herbizide und/oder wachstumsregulatoren. |
| US4931081A (en) * | 1982-06-01 | 1990-06-05 | E. I. Du Pont De Nemours And Company | Herbicidal diazoles sulfonamides |
| DK246683A (da) * | 1982-06-01 | 1983-12-02 | Du Pont | Herbicider |
| MA19797A1 (fr) * | 1982-06-14 | 1983-12-31 | Ciba Geigy Ag | N-heterocyclosulfonyl -n- pyrimidinyl et triazinylurees . |
| EP0103537B1 (de) * | 1982-07-16 | 1987-07-08 | Ciba-Geigy Ag | N-Arylsulfonyl-N'-triazolylharnstoffe |
| GR79414B (cs) * | 1982-10-29 | 1984-10-22 | Du Pont | |
| IT1161220B (it) * | 1983-04-21 | 1987-03-18 | Montedison Spa | Diidro-benzofurano derivati ad attivita' erbicida |
| AU571869B2 (en) * | 1983-05-09 | 1988-04-28 | E.I. Du Pont De Nemours And Company | Pyridyl- and pyrimidyl- sulphonamides |
| EP0158600B1 (de) * | 1984-04-11 | 1991-04-03 | Ciba-Geigy Ag | Verfahren zur selektiven Unkrautbekämpfung in Nutzpflanzenkulturen |
| ATE55128T1 (de) * | 1984-04-11 | 1990-08-15 | Ciba Geigy Ag | N-heterocyclosulfonyl-n'-pyrimidinyl- und triazinylharnstoffe. |
| US4661147A (en) * | 1984-06-05 | 1987-04-28 | E. I. Du Pont De Nemours And Company | Herbicidal sulfonamides |
| US4769060A (en) * | 1985-04-29 | 1988-09-06 | E. I. Du Pont De Nemours And Company | Herbicidal sulfonamides |
| US4897108A (en) * | 1984-06-05 | 1990-01-30 | E. I. Du Pont De Nemours And Company | Herbicidal sulfonamides |
| US4892575A (en) * | 1984-06-07 | 1990-01-09 | E. I. Du Pont De Nemours And Company | Herbicidal sulfonamides |
| US4659369A (en) | 1984-08-27 | 1987-04-21 | E. I. Du Pont De Nemours And Company | Herbicidal acetals and ketals |
| AU4789685A (en) * | 1984-09-28 | 1986-04-10 | E.I. Du Pont De Nemours And Company | Heterocyclic sulphonamide derivatives |
| US4741758A (en) * | 1984-12-11 | 1988-05-03 | E. I. Du Pont De Nemours And Company | Herbicidal sulfonamides |
| US4895591A (en) * | 1984-12-11 | 1990-01-23 | E. I. Du Pont De Nemours And Company | Herbicidal sulfonamides |
| US4867783A (en) * | 1984-12-11 | 1989-09-19 | E. I. Du Pont De Nemours And Company | Herbicidal sulfonamides |
| US4786313A (en) * | 1984-12-11 | 1988-11-22 | E. I. Du Pont De Nemours And Company | Herbicidal sulfonamides |
| CA1232273A (en) * | 1984-12-11 | 1988-02-02 | James V. Hay | Herbicidal sulfonamides |
| US4743290A (en) * | 1986-04-21 | 1988-05-10 | E. I. Du Pont De Nemours And Company | Thiophenesulfonamide herbicides |
| US4877440A (en) * | 1985-05-29 | 1989-10-31 | E. I. Du Pont De Nemours And Company | Thiophenesulfonamide herbicides |
| US4732604A (en) * | 1985-08-29 | 1988-03-22 | E. I. Du Pont De Nemours And Company | Herbicidal sulfonamides |
| CA1309715C (en) * | 1986-05-02 | 1992-11-03 | Barry A. Wexler | Herbicidal heterocyclic sulfonamides |
| US5215570A (en) * | 1988-10-20 | 1993-06-01 | Ciba-Geigy Corporation | Sulfamoylphenylureas |
| DE3927140A1 (de) * | 1989-08-17 | 1991-02-21 | Bayer Ag | Selektive herbizide auf basis von sulfonylisothioharnstoffen |
| DE4232417A1 (de) * | 1992-09-28 | 1994-03-31 | Bayer Ag | Substituierte Thienylsulfonylharnstoffe |
| LT3943B (en) | 1993-12-23 | 1996-05-27 | Ciba Geigy Ag | Remedy for cultured plants protection, use of sulphamoyl-phenyl-carbamides for cultured plant protection, herbicidal preparation, process for preparing sulphamoyl-phenyl-carbamides |
| DE19608831A1 (de) * | 1996-03-07 | 1997-09-18 | Bayer Ag | Substituierte Thienylsulfonyl(thio)harnstoffe |
| DE19651037A1 (de) | 1996-12-09 | 1998-06-10 | Bayer Ag | Substituierte Thienyl(amino)sulfonyl(thio)harnstoffe |
| DE19937118A1 (de) | 1999-08-06 | 2001-02-08 | Bayer Ag | Substituierte Thienyl(amino)sulfonylharnstoffe |
| DE102004036550A1 (de) * | 2004-07-28 | 2006-03-23 | Bayer Cropscience Ag | Aminocarbonyl-substituierte Thienylsulfonylharnstoffe |
| EP1835807A1 (en) | 2004-12-17 | 2007-09-26 | Devgen N.V. | Nematicidal compositions |
| DE102004063192A1 (de) | 2004-12-29 | 2006-07-13 | Bayer Cropscience Ag | Verfahren zur Herstellung von substituierten Thiophensulfonylisocyanaten |
| EP2052606A1 (de) | 2007-10-24 | 2009-04-29 | Bayer CropScience AG | Herbizid-Kombination |
| DE102008037620A1 (de) | 2008-08-14 | 2010-02-18 | Bayer Crop Science Ag | Herbizid-Kombination mit Dimethoxytriazinyl-substituierten Difluormethansulfonylaniliden |
| CN102894004A (zh) * | 2012-09-26 | 2013-01-30 | 江苏省农业科学院 | 一种防除甘薯田杂草的除草剂组合物 |
| USD1038716S1 (en) * | 2022-08-04 | 2024-08-13 | Fourth Option Llc | Eating utensil |
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|---|---|---|---|---|
| NL7703809A (nl) * | 1976-04-07 | 1977-10-11 | Du Pont | Herbicide sulfonamiden. |
| US4169719A (en) * | 1976-04-07 | 1979-10-02 | E. I. Du Pont De Nemours And Co. | Herbicidal sulfonamides |
| DK358778A (da) * | 1977-09-19 | 1979-03-20 | Du Pont | Herbicide sulfonamider |
| US4257802A (en) * | 1977-10-06 | 1981-03-24 | E. I. Du Pont De Nemours And Company | Herbicidal sulfonamides |
| DK163123C (da) * | 1978-05-30 | 1992-06-09 | Du Pont | Benzensulfonylurinstoffer til anvendelse som herbicider eller plantevaekstregulatorer, praeparat indeholdende dem samt deres anvendelse |
| DK37880A (da) * | 1979-02-22 | 1980-08-23 | Du Pont | Herbicide sulfonamider |
-
1980
- 1980-11-06 DK DK471680A patent/DK172396B1/da active Protection Beyond IP Right Term
- 1980-11-20 UA UA4356634A patent/UA19062A/uk unknown
- 1980-11-25 BR BR8007674A patent/BR8007674A/pt not_active IP Right Cessation
- 1980-11-26 PH PH24905A patent/PH18851A/en unknown
- 1980-11-27 CA CA000365664A patent/CA1189072A/en not_active Expired
- 1980-11-27 AU AU64763/80A patent/AU536122B2/en not_active Expired
- 1980-11-28 PT PT72132A patent/PT72132B/pt unknown
- 1980-11-28 CS CS808287A patent/CS250207B2/cs unknown
- 1980-11-28 HU HU802839A patent/HU193629B/hu unknown
- 1980-11-28 PL PL1980228148A patent/PL127333B1/pl unknown
- 1980-11-28 ES ES497298A patent/ES497298A0/es active Granted
- 1980-11-28 IL IL61578A patent/IL61578A/xx not_active IP Right Cessation
- 1980-11-28 YU YU03025/80A patent/YU302580A/xx unknown
- 1980-11-28 DE DE8080304287T patent/DE3069777D1/de not_active Expired
- 1980-11-28 IE IE2489/80A patent/IE50745B1/en not_active IP Right Cessation
- 1980-11-28 NZ NZ195680A patent/NZ195680A/xx unknown
- 1980-11-28 EP EP80304287A patent/EP0030142B1/en not_active Expired
- 1980-11-28 GB GB8038270A patent/GB2065116B/en not_active Expired
- 1980-11-29 KR KR1019800004580A patent/KR850000678B1/ko not_active Expired
- 1980-11-29 GR GR63507A patent/GR72259B/el unknown
- 1980-11-29 RO RO102726A patent/RO81268B/ro unknown
- 1980-11-30 TR TR21804A patent/TR21804A/xx unknown
-
1988
- 1988-10-18 SU SU884356634A patent/SU1748629A3/ru active
-
1997
- 1997-07-16 NL NL971012C patent/NL971012I1/nl unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1994855A2 (en) | 2007-05-25 | 2008-11-26 | Unifor S.p.A. | Workstation system and workstation with multiple, adjustable height, work tops |
Also Published As
| Publication number | Publication date |
|---|---|
| UA19062A (uk) | 1997-12-25 |
| NZ195680A (en) | 1983-09-30 |
| NL971012I1 (nl) | 1997-09-01 |
| KR830004294A (ko) | 1983-07-09 |
| DK471680A (da) | 1981-05-31 |
| AU6476380A (en) | 1981-06-04 |
| RO81268A (ro) | 1985-02-28 |
| RO81268B (ro) | 1985-02-28 |
| IL61578A0 (en) | 1980-12-31 |
| ES8205764A1 (es) | 1982-06-16 |
| IE50745B1 (en) | 1986-07-09 |
| IE802489L (en) | 1981-05-30 |
| PT72132B (en) | 1982-07-30 |
| CS250207B2 (en) | 1987-04-16 |
| EP0030142B1 (en) | 1984-12-05 |
| EP0030142A3 (en) | 1981-08-12 |
| AU536122B2 (en) | 1984-04-19 |
| HU193629B (en) | 1987-11-30 |
| EP0030142A2 (en) | 1981-06-10 |
| GR72259B (cs) | 1983-10-07 |
| DE3069777D1 (en) | 1985-01-17 |
| KR850000678B1 (ko) | 1985-05-10 |
| YU302580A (en) | 1983-02-28 |
| CA1189072A (en) | 1985-06-18 |
| BR8007674A (pt) | 1981-06-09 |
| PH18851A (en) | 1985-10-21 |
| SU1748629A3 (ru) | 1992-07-15 |
| PL127333B1 (en) | 1983-10-31 |
| IL61578A (en) | 1987-08-31 |
| TR21804A (tr) | 1985-07-19 |
| PT72132A (en) | 1980-12-01 |
| GB2065116B (en) | 1983-10-26 |
| PL228148A1 (cs) | 1981-08-07 |
| GB2065116A (en) | 1981-06-24 |
| ES497298A0 (es) | 1982-06-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| B1 | Patent granted (law 1993) | ||
| CTFF | Application for supplementary protection certificate (spc) filed |
Spc suppl protection certif: CA 1998 00028 Filing date: 19981028 Extension date: 20041215 |
|
| PUP | Patent expired | ||
| CTFG | Supplementary protection certificate (spc) issued |
Free format text: PRODUCT NAME: THIFENSULFURON-METHYL Spc suppl protection certif: CA 1998 00029 Filing date: 19981028 |
|
| CTFW | Supplementary protection certificate (spc) withdrawn, refused or deemed withdrawn |
Free format text: PRODUCT NAME: THIFENSULFURON-METHYL + TRIBENURON-METHYL Spc suppl protection certif: CA 1998 00028 Filing date: 19981028 |