ZA200606604B - An improved process for the preparation of N-([1,2,4]triazolopyrimidin-2-yl)aryl sulfonamides - Google Patents
An improved process for the preparation of N-([1,2,4]triazolopyrimidin-2-yl)aryl sulfonamides Download PDFInfo
- Publication number
- ZA200606604B ZA200606604B ZA200606604A ZA200606604A ZA200606604B ZA 200606604 B ZA200606604 B ZA 200606604B ZA 200606604 A ZA200606604 A ZA 200606604A ZA 200606604 A ZA200606604 A ZA 200606604A ZA 200606604 B ZA200606604 B ZA 200606604B
- Authority
- ZA
- South Africa
- Prior art keywords
- triazolopyrimidin
- mol
- formula
- reaction
- compound
- Prior art date
Links
- 125000004421 aryl sulphonamide group Chemical group 0.000 title claims abstract description 12
- 238000000034 method Methods 0.000 title claims description 24
- 238000002360 preparation method Methods 0.000 title claims description 22
- HWWYDZCSSYKIAD-UHFFFAOYSA-N 3,5-dimethylpyridine Chemical compound CC1=CN=CC(C)=C1 HWWYDZCSSYKIAD-UHFFFAOYSA-N 0.000 claims abstract description 42
- ITQTTZVARXURQS-UHFFFAOYSA-N 3-methylpyridine Chemical compound CC1=CC=CN=C1 ITQTTZVARXURQS-UHFFFAOYSA-N 0.000 claims abstract description 38
- -1 aromatic sulfonyl chlorides Chemical class 0.000 claims abstract description 32
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 20
- 150000001875 compounds Chemical class 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 230000003197 catalytic effect Effects 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- 125000001246 bromo group Chemical group Br* 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 abstract description 18
- 238000005859 coupling reaction Methods 0.000 abstract description 5
- 230000008878 coupling Effects 0.000 abstract description 4
- 238000010168 coupling process Methods 0.000 abstract description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 60
- 238000006243 chemical reaction Methods 0.000 description 27
- 239000007787 solid Substances 0.000 description 27
- 239000000203 mixture Substances 0.000 description 26
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 25
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- 125000003118 aryl group Chemical group 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- DBJPBHJHAPAUQU-UHFFFAOYSA-N 5,8-dimethoxy-[1,2,4]triazolo[1,5-c]pyrimidin-2-amine Chemical compound COC1=CN=C(OC)N2N=C(N)N=C12 DBJPBHJHAPAUQU-UHFFFAOYSA-N 0.000 description 9
- 238000001914 filtration Methods 0.000 description 9
- 239000003960 organic solvent Substances 0.000 description 9
- 239000003054 catalyst Substances 0.000 description 8
- 239000012066 reaction slurry Substances 0.000 description 8
- 239000002002 slurry Substances 0.000 description 8
- GLBQVJGBPFPMMV-UHFFFAOYSA-N sulfilimine Chemical compound S=N GLBQVJGBPFPMMV-UHFFFAOYSA-N 0.000 description 8
- 239000000460 chlorine Substances 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- DTNQLYAGRKNWMQ-UHFFFAOYSA-N 2-(2,2-difluoroethoxy)-6-(trifluoromethyl)benzenesulfonyl chloride Chemical compound FC(F)COC1=CC=CC(C(F)(F)F)=C1S(Cl)(=O)=O DTNQLYAGRKNWMQ-UHFFFAOYSA-N 0.000 description 5
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- DMKFWTCEKLNOKK-UHFFFAOYSA-N 2-methoxy-4-(trifluoromethyl)pyridine-3-sulfonyl chloride Chemical compound COC1=NC=CC(C(F)(F)F)=C1S(Cl)(=O)=O DMKFWTCEKLNOKK-UHFFFAOYSA-N 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 229940124530 sulfonamide Drugs 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000012190 activator Substances 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- 150000003456 sulfonamides Chemical class 0.000 description 3
- 125000004434 sulfur atom Chemical group 0.000 description 3
- 125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 description 2
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 230000006978 adaptation Effects 0.000 description 2
- 239000007810 chemical reaction solvent Substances 0.000 description 2
- 230000009849 deactivation Effects 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000012552 review Methods 0.000 description 2
- 238000010561 standard procedure Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 2
- 150000003513 tertiary aromatic amines Chemical class 0.000 description 2
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- WYLWTYLYGBOBNG-UHFFFAOYSA-N (5,8-dimethoxy-[1,2,4]triazolo[1,5-c]pyrimidin-2-yl)imino-dimethyl-$l^{4}-sulfane;hydrochloride Chemical compound Cl.COC1=CN=C(OC)N2N=C(N=S(C)C)N=C12 WYLWTYLYGBOBNG-UHFFFAOYSA-N 0.000 description 1
- NCYNKWQXFADUOZ-UHFFFAOYSA-N 1,1-dioxo-2,1$l^{6}-benzoxathiol-3-one Chemical compound C1=CC=C2C(=O)OS(=O)(=O)C2=C1 NCYNKWQXFADUOZ-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- SJEIPAUSEWIHJI-UHFFFAOYSA-N 5,7-dimethoxy-[1,2,4]triazolo[1,5-a]pyrimidin-2-amine Chemical compound N1=C(OC)C=C(OC)N2N=C(N)N=C21 SJEIPAUSEWIHJI-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 101100205847 Mus musculus Srst gene Proteins 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- QLOWGDIISXJREF-UHFFFAOYSA-N [1,2,4]triazolo[1,5-c]pyrimidine Chemical compound C1=CN=CN2N=CN=C21 QLOWGDIISXJREF-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000012320 chlorinating reagent Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 125000001891 dimethoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-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
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000004557 technical material Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YWBFPKPWMSWWEA-UHFFFAOYSA-O triazolopyrimidine Chemical compound BrC1=CC=CC(C=2N=C3N=CN[N+]3=C(NCC=3C=CN=CC=3)C=2)=C1 YWBFPKPWMSWWEA-UHFFFAOYSA-O 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US55702204P | 2004-03-26 | 2004-03-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200606604B true ZA200606604B (en) | 2008-01-30 |
Family
ID=34963841
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200606604A ZA200606604B (en) | 2004-03-26 | 2005-03-24 | An improved process for the preparation of N-([1,2,4]triazolopyrimidin-2-yl)aryl sulfonamides |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US7339058B2 (da) |
| EP (1) | EP1735309B1 (da) |
| JP (1) | JP4929155B2 (da) |
| KR (1) | KR101111014B1 (da) |
| CN (1) | CN100509812C (da) |
| AT (1) | ATE451370T1 (da) |
| AU (1) | AU2005230862B2 (da) |
| BR (1) | BRPI0509273B8 (da) |
| CA (1) | CA2558245C (da) |
| DE (1) | DE602005018182D1 (da) |
| DK (1) | DK1735309T3 (da) |
| IL (1) | IL178032A (da) |
| MX (1) | MXPA06010913A (da) |
| TW (1) | TWI337183B (da) |
| WO (1) | WO2005097793A1 (da) |
| ZA (1) | ZA200606604B (da) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103044431A (zh) * | 2012-10-22 | 2013-04-17 | 中国药科大学 | 制备五氟磺草胺的新方法 |
| CN103319489B (zh) * | 2013-07-12 | 2015-04-08 | 黑龙江大学 | 三唑并嘧啶磺酰胺化合物及合成方法和应用 |
| CN104341326A (zh) * | 2013-08-08 | 2015-02-11 | 天津诺维康生物技术有限公司 | 2-取代基-6-三氟甲基苯磺酰氯的制备方法 |
| CN107406450B (zh) * | 2015-03-10 | 2019-06-04 | 泸州东方农化有限公司 | 一种制备高纯度磺胺化合物的方法及其中间体 |
| CN105294515B (zh) * | 2015-11-13 | 2017-10-10 | 天津现代职业技术学院 | 2‑(2’,2’‑二氟乙氧基)‑6‑三氟甲基苯磺酰氯的制备方法 |
| CN105399746B (zh) * | 2015-12-28 | 2017-11-07 | 黑龙江凯奥科技开发有限公司 | 三唑并嘧啶磺酰胺化合物、含有该化合物的组合物及其应用 |
| GB2555635B (en) * | 2016-11-07 | 2022-04-13 | Rotam Agrochem Int Co Ltd | A novel form of penoxsulam, a process for its preparation and use of the same |
| CN108892671B (zh) * | 2018-08-20 | 2021-04-20 | 常州沃腾化工科技有限公司 | 一种啶磺草胺的制备方法 |
| CN108707109A (zh) * | 2018-08-29 | 2018-10-26 | 常州沃腾化工科技有限公司 | 一种2-甲氧基-4-三氟甲基吡啶-3-磺酰氯的制备方法 |
| EP3902786B1 (en) * | 2018-12-27 | 2022-12-14 | Corteva Agriscience LLC | Preparation of sulfonamide herbicide process intermediates |
| CN113272277A (zh) | 2018-12-27 | 2021-08-17 | 科迪华农业科技有限责任公司 | 磺酰胺除草剂方法中间体的制备 |
| CN110698363B (zh) * | 2019-01-28 | 2022-02-01 | 杭州师范大学 | 一种2-(2,2-二氟乙氧基)-6-(三氟甲基)苯磺酰氯的合成方法 |
| CN110563735B (zh) * | 2019-09-27 | 2022-03-29 | 江苏好收成韦恩农化股份有限公司 | 制备双氟磺草胺的方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5177206A (en) | 1991-10-08 | 1993-01-05 | Dowelanco | Process for the preparation of substituted N-(aryl)-1,2,4-triazolopyrimidine-2-sulfonamides |
| US5858924A (en) * | 1996-09-24 | 1999-01-12 | Dow Agrosciences Llc | N-( 1, 2, 4! triazoloazinyl) benzenesulfonamide and pyridinesulfonamide compounds and their use as herbicides |
| ZA9710197B (en) * | 1996-11-13 | 1999-05-12 | Dow Agrosciences Llc | N-arylsulfilimine compounds and their use as catalysts in the preparation of n-arylarylsulfonamide compounds |
| JP3911236B2 (ja) * | 2000-11-03 | 2007-05-09 | ダウ・アグロサイエンス・エル・エル・シー | Ｎ−（５，７−ジメトキシ［１，２，４］トリアゾロ［１，５−ａ］ピリミジン−２−イル）アリールスルホンアミド化合物及び除草剤としてのそれらの使用 |
| KR20040004427A (ko) * | 2000-11-03 | 2004-01-13 | 다우 아그로사이언시즈 엘엘씨 | 제초제로서의 ν-([1,2,4]트리아졸로아지닐)티오펜설폰아미드 화합물 |
-
2005
- 2005-03-24 AT AT05730076T patent/ATE451370T1/de active
- 2005-03-24 DE DE602005018182T patent/DE602005018182D1/de active Active
- 2005-03-24 WO PCT/US2005/009964 patent/WO2005097793A1/en not_active Application Discontinuation
- 2005-03-24 CN CNB2005800080109A patent/CN100509812C/zh active Active
- 2005-03-24 AU AU2005230862A patent/AU2005230862B2/en active Active
- 2005-03-24 CA CA2558245A patent/CA2558245C/en not_active Expired - Fee Related
- 2005-03-24 BR BRPI0509273A patent/BRPI0509273B8/pt active IP Right Grant
- 2005-03-24 US US11/088,448 patent/US7339058B2/en active Active
- 2005-03-24 ZA ZA200606604A patent/ZA200606604B/en unknown
- 2005-03-24 KR KR1020067019722A patent/KR101111014B1/ko active IP Right Grant
- 2005-03-24 DK DK05730076.6T patent/DK1735309T3/da active
- 2005-03-24 JP JP2007505212A patent/JP4929155B2/ja active Active
- 2005-03-24 MX MXPA06010913A patent/MXPA06010913A/es active IP Right Grant
- 2005-03-24 EP EP05730076A patent/EP1735309B1/en active Active
- 2005-03-25 TW TW094109293A patent/TWI337183B/zh active
-
2006
- 2006-09-12 IL IL178032A patent/IL178032A/en active IP Right Grant
Also Published As
| Publication number | Publication date |
|---|---|
| JP4929155B2 (ja) | 2012-05-09 |
| TWI337183B (en) | 2011-02-11 |
| AU2005230862A1 (en) | 2005-10-20 |
| CA2558245A1 (en) | 2005-10-20 |
| KR20070014135A (ko) | 2007-01-31 |
| IL178032A (en) | 2013-11-28 |
| WO2005097793A1 (en) | 2005-10-20 |
| CN100509812C (zh) | 2009-07-08 |
| JP2007530587A (ja) | 2007-11-01 |
| ATE451370T1 (de) | 2009-12-15 |
| US20050215570A1 (en) | 2005-09-29 |
| EP1735309B1 (en) | 2009-12-09 |
| CA2558245C (en) | 2012-01-03 |
| BRPI0509273B1 (pt) | 2015-12-22 |
| DK1735309T3 (da) | 2010-04-06 |
| US7339058B2 (en) | 2008-03-04 |
| BRPI0509273A (pt) | 2007-09-04 |
| MXPA06010913A (es) | 2006-12-15 |
| EP1735309A1 (en) | 2006-12-27 |
| DE602005018182D1 (de) | 2010-01-21 |
| KR101111014B1 (ko) | 2012-02-13 |
| CN1930164A (zh) | 2007-03-14 |
| IL178032A0 (en) | 2006-12-31 |
| BRPI0509273B8 (pt) | 2022-06-28 |
| TW200536842A (en) | 2005-11-16 |
| AU2005230862B2 (en) | 2010-12-23 |
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