TW201114768A - Herbicidal compounds - Google Patents
Herbicidal compounds Download PDFInfo
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- TW201114768A TW201114768A TW099134166A TW99134166A TW201114768A TW 201114768 A TW201114768 A TW 201114768A TW 099134166 A TW099134166 A TW 099134166A TW 99134166 A TW99134166 A TW 99134166A TW 201114768 A TW201114768 A TW 201114768A
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 1133
- 230000002363 herbicidal effect Effects 0.000 title claims abstract description 18
- -1 heterobicyclic carboxylic acid derivatives Chemical class 0.000 claims abstract description 357
- 239000000203 mixture Substances 0.000 claims abstract description 150
- 150000003839 salts Chemical class 0.000 claims abstract description 17
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 199
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine group Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 136
- 239000007789 gas Chemical group 0.000 claims description 135
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 122
- 238000000034 method Methods 0.000 claims description 63
- 125000000217 alkyl group Chemical group 0.000 claims description 59
- 229910052739 hydrogen Inorganic materials 0.000 claims description 49
- 241000196324 Embryophyta Species 0.000 claims description 42
- 239000001257 hydrogen Substances 0.000 claims description 41
- 125000001424 substituent group Chemical group 0.000 claims description 40
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 35
- 125000006413 ring segment Chemical group 0.000 claims description 33
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 32
- 229910052736 halogen Inorganic materials 0.000 claims description 28
- 125000003545 alkoxy group Chemical group 0.000 claims description 27
- 125000003118 aryl group Chemical group 0.000 claims description 26
- 229910052760 oxygen Inorganic materials 0.000 claims description 26
- 239000001301 oxygen Substances 0.000 claims description 26
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 25
- 229910052757 nitrogen Inorganic materials 0.000 claims description 24
- 150000001412 amines Chemical class 0.000 claims description 23
- 150000002367 halogens Chemical class 0.000 claims description 23
- 229910052799 carbon Inorganic materials 0.000 claims description 21
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 20
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 18
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 claims description 18
- 239000004009 herbicide Substances 0.000 claims description 18
- 229910052717 sulfur Inorganic materials 0.000 claims description 18
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 17
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 15
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- 125000001188 haloalkyl group Chemical group 0.000 claims description 14
- 125000005843 halogen group Chemical group 0.000 claims description 14
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- 125000001072 heteroaryl group Chemical group 0.000 claims description 12
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 11
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- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 6
- 125000006826 (C2-C7) alkylcarbonyloxy group Chemical group 0.000 claims description 6
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- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
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- 125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 claims description 4
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- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims description 2
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- 229910000416 bismuth oxide Inorganic materials 0.000 claims 1
- 238000001354 calcination Methods 0.000 claims 1
- TYIXMATWDRGMPF-UHFFFAOYSA-N dibismuth;oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Bi+3].[Bi+3] TYIXMATWDRGMPF-UHFFFAOYSA-N 0.000 claims 1
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- 239000004480 active ingredient Substances 0.000 abstract description 31
- 230000008635 plant growth Effects 0.000 abstract description 6
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- 238000006243 chemical reaction Methods 0.000 description 143
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- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 71
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- 239000002585 base Substances 0.000 description 68
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- 238000012512 characterization method Methods 0.000 description 64
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 60
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 59
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- PQTBTIFWAXVEPB-UHFFFAOYSA-N sulcotrione Chemical compound ClC1=CC(S(=O)(=O)C)=CC=C1C(=O)C1C(=O)CCCC1=O PQTBTIFWAXVEPB-UHFFFAOYSA-N 0.000 description 1
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- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
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- 125000005490 tosylate group Chemical group 0.000 description 1
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- XOPFESVZMSQIKC-UHFFFAOYSA-N triasulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)OCCCl)=N1 XOPFESVZMSQIKC-UHFFFAOYSA-N 0.000 description 1
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- YMXOXAPKZDWXLY-QWRGUYRKSA-N tribenuron methyl Chemical group COC(=O)[C@H]1CCCC[C@@H]1S(=O)(=O)NC(=O)N(C)C1=NC(C)=NC(OC)=N1 YMXOXAPKZDWXLY-QWRGUYRKSA-N 0.000 description 1
- SANWDQJIWZEKOD-UHFFFAOYSA-N tributyl(furan-2-yl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=CC=CO1 SANWDQJIWZEKOD-UHFFFAOYSA-N 0.000 description 1
- QAHMAFPUBBWUIS-UHFFFAOYSA-N tributyl(prop-2-ynyl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C=C=C QAHMAFPUBBWUIS-UHFFFAOYSA-N 0.000 description 1
- REEQLXCGVXDJSQ-UHFFFAOYSA-N trichlopyr Chemical compound OC(=O)COC1=NC(Cl)=C(Cl)C=C1Cl REEQLXCGVXDJSQ-UHFFFAOYSA-N 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
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- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- AKTQJCBOGPBERP-UHFFFAOYSA-N triflusulfuron Chemical compound FC(F)(F)COC1=NC(N(C)C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2C)C(O)=O)=N1 AKTQJCBOGPBERP-UHFFFAOYSA-N 0.000 description 1
- IMEVJVISCHQJRM-UHFFFAOYSA-N triflusulfuron-methyl Chemical group COC(=O)C1=CC=CC(C)=C1S(=O)(=O)NC(=O)NC1=NC(OCC(F)(F)F)=NC(N(C)C)=N1 IMEVJVISCHQJRM-UHFFFAOYSA-N 0.000 description 1
- 125000004953 trihalomethyl group Chemical group 0.000 description 1
- PLSARIKBYIPYPF-UHFFFAOYSA-H trimagnesium dicitrate Chemical compound [Mg+2].[Mg+2].[Mg+2].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O.[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O PLSARIKBYIPYPF-UHFFFAOYSA-H 0.000 description 1
- IEDVJHCEMCRBQM-UHFFFAOYSA-N trimethoprim Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(=NC(N)=NC=2)N)=C1 IEDVJHCEMCRBQM-UHFFFAOYSA-N 0.000 description 1
- 229960001082 trimethoprim Drugs 0.000 description 1
- CCRMAATUKBYMPA-UHFFFAOYSA-N trimethyltin Chemical compound C[Sn](C)C.C[Sn](C)C CCRMAATUKBYMPA-UHFFFAOYSA-N 0.000 description 1
- RVKCCVTVZORVGD-UHFFFAOYSA-N trinexapac-ethyl Chemical group O=C1CC(C(=O)OCC)CC(=O)C1=C(O)C1CC1 RVKCCVTVZORVGD-UHFFFAOYSA-N 0.000 description 1
- WIOADUFWOUUQCV-UHFFFAOYSA-N triphenylphosphanium dichloride Chemical compound [Cl-].[Cl-].C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 WIOADUFWOUUQCV-UHFFFAOYSA-N 0.000 description 1
- KVEQCVKVIFQSGC-UHFFFAOYSA-N tritosulfuron Chemical compound FC(F)(F)C1=NC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(F)(F)F)=N1 KVEQCVKVIFQSGC-UHFFFAOYSA-N 0.000 description 1
- 235000016788 valerian Nutrition 0.000 description 1
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Classifications
-
- 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)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
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| CA (1) | CA2773604A1 (enExample) |
| GB (1) | GB0917934D0 (enExample) |
| IN (1) | IN2012DN02075A (enExample) |
| TW (1) | TW201114768A (enExample) |
| WO (1) | WO2011045561A2 (enExample) |
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| GB0902474D0 (en) * | 2009-02-13 | 2009-04-01 | Syngenta Ltd | Chemical compounds |
| CN103271040B (zh) * | 2013-06-05 | 2015-03-11 | 江苏龙灯化学有限公司 | 一种协同除草组合物 |
| TW201625635A (zh) | 2014-11-21 | 2016-07-16 | 默沙東藥廠 | 作為可溶性鳥苷酸環化酶活化劑之三唑并吡基衍生物 |
| BR112019013266B1 (pt) | 2016-12-27 | 2022-10-11 | Nihon Nohyaku Co., Ltd | Composto de 4h-pirrolopiridina ou o sal deste, uso do mesmo, métodos para uso de um inseticida agrícola e hortícola e para controle de pragas agrícolas e hortícolas, composição compreendendo o dito composto e seu uso |
| WO2020035138A1 (en) * | 2018-08-14 | 2020-02-20 | Cmblu Projekt Ag | Redox-active compounds and uses thereof |
| TWI895986B (zh) * | 2018-12-20 | 2025-09-01 | 美商Ｋｓｑ治療公司 | 經取代之吡唑并嘧啶及經取代之嘌呤以及其作為泛素特異性加工蛋白酶１（ｕｓｐ１）抑制劑的用途 |
| CN114450270B (zh) * | 2019-07-30 | 2025-05-06 | 安道麦阿甘有限公司 | 砜吡草唑的制备方法和中间体 |
| CN111763220B (zh) * | 2020-07-13 | 2021-06-01 | 湖南科技大学 | 一种9,10-二取代-3,1-苯并噁嗪并咪唑啉酮类化合物及其制备方法和用途 |
| IL302352A (en) | 2020-10-30 | 2023-06-01 | Ksq Therapeutics Inc | Solid state forms of substituted pyrazolopyrimidines and uses thereof |
| CN114044796A (zh) * | 2021-11-18 | 2022-02-15 | 鄂尔多斯应用技术学院 | 一种四取代烯丙基叠氮化合物的立体选择性合成方法 |
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| BR8600161A (pt) | 1985-01-18 | 1986-09-23 | Plant Genetic Systems Nv | Gene quimerico,vetores de plasmidio hibrido,intermediario,processo para controlar insetos em agricultura ou horticultura,composicao inseticida,processo para transformar celulas de plantas para expressar uma toxina de polipeptideo produzida por bacillus thuringiensis,planta,semente de planta,cultura de celulas e plasmidio |
| US4834908A (en) | 1987-10-05 | 1989-05-30 | Basf Corporation | Antagonism defeating crop oil concentrates |
| CA2005658A1 (en) | 1988-12-19 | 1990-06-19 | Eliahu Zlotkin | Insecticidal toxins, genes encoding these toxins, antibodies binding to them and transgenic plant cells and plants expressing these toxins |
| DE69018772T2 (de) | 1989-11-07 | 1996-03-14 | Pioneer Hi Bred Int | Larven abtötende Lektine und darauf beruhende Pflanzenresistenz gegen Insekten. |
| UA48104C2 (uk) | 1991-10-04 | 2002-08-15 | Новартіс Аг | Фрагмент днк, який містить послідовність,що кодує інсектицидний протеїн, оптимізовану для кукурудзи,фрагмент днк, який забезпечує направлену бажану для серцевини стебла експресію зв'язаного з нею структурного гена в рослині, фрагмент днк, який забезпечує специфічну для пилку експресію зв`язаного з нею структурного гена в рослині, рекомбінантна молекула днк, спосіб одержання оптимізованої для кукурудзи кодуючої послідовності інсектицидного протеїну, спосіб захисту рослин кукурудзи щонайменше від однієї комахи-шкідника |
| CN1098717A (zh) * | 1993-06-01 | 1995-02-15 | 日本曹达株式会社 | 嘧啶衍生物 |
| US5530195A (en) | 1994-06-10 | 1996-06-25 | Ciba-Geigy Corporation | Bacillus thuringiensis gene encoding a toxin active against insects |
| WO1997034485A1 (en) | 1996-03-15 | 1997-09-25 | Novartis Ag | Herbicidal synergistic composition and method of weed control |
| CN1281591C (zh) | 2000-01-14 | 2006-10-25 | 美国陶氏益农公司 | 4－氨基吡啶甲酸酯和它们作为除草剂的应用 |
| AR031027A1 (es) | 2000-10-23 | 2003-09-03 | Syngenta Participations Ag | Composiciones agroquimicas |
| AR037228A1 (es) | 2001-07-30 | 2004-11-03 | Dow Agrosciences Llc | Compuestos del acido 6-(aril o heteroaril)-4-aminopicolinico, composicion herbicida que los comprende y metodo para controlar vegetacion no deseada |
| WO2003052073A2 (en) | 2001-12-17 | 2003-06-26 | Syngenta Participations Ag | Novel corn event |
| SE0201980D0 (sv) | 2002-06-24 | 2002-06-24 | Astrazeneca Ab | Novel compounds |
| UA82358C2 (uk) | 2003-04-02 | 2008-04-10 | Дау Агросайенсиз Ллс | 6-алкіл або алкеніл-4-амінопіколінати гербіцидна композиція, спосіб боротьби з небажаною рослинністю |
| UA81177C2 (uk) | 2003-08-04 | 2007-12-10 | Дау Агросайєнсіз Ллс | 6-(1,1-дифторалкіл)-4-амінопіколінати та їх використання як гербіцидів |
| TWI355894B (en) | 2003-12-19 | 2012-01-11 | Du Pont | Herbicidal pyrimidines |
| WO2006062979A1 (en) | 2004-12-06 | 2006-06-15 | E.I. Dupont De Nemours And Company | Herbicidal 6-cyclopropyl-substitute 4-aminopicolinic acid derivatives |
| CN100344628C (zh) * | 2005-03-29 | 2007-10-24 | 沈阳化工研究院 | 吡唑并嘧啶酮类化合物及其应用 |
| CN100335481C (zh) * | 2005-10-11 | 2007-09-05 | 华中师范大学 | 一类具有杀菌除草活性的多取代吡啶并[4,3－d]嘧啶及制备 |
| TWI396505B (zh) | 2006-01-13 | 2013-05-21 | Dow Agrosciences Llc | ２-（聚-經取代芳基）-６-胺-５-鹵-４-嘧啶羧酸及其作為除草劑之用途 |
| CA2666624C (en) * | 2006-10-19 | 2015-12-29 | Signal Pharmaceuticals, Llc | Heteroaryl compounds, compositions thereof, and use thereof as protein kinase inhibitors |
| ATE500230T1 (de) | 2007-08-30 | 2011-03-15 | Dow Agrosciences Llc | 2-(substituierte phenyl)-6-amino-5-alkoxy-, thioalkoxy- und aminoalkyl-4-pyrimidincarboxylate und ihre verwendung als herbizide |
| GB0718433D0 (en) * | 2007-09-21 | 2007-10-31 | Vernalis R&D Ltd | New chemical compounds |
| ES2391081T3 (es) | 2007-10-02 | 2012-11-21 | Dow Agrosciences, Llc | Ácidos 4-amino-picolínicos sustituidos y su uso como herbicidas |
| GB0725218D0 (en) | 2007-12-24 | 2008-02-06 | Syngenta Ltd | Chemical compounds |
| GB0902474D0 (en) | 2009-02-13 | 2009-04-01 | Syngenta Ltd | Chemical compounds |
-
2009
- 2009-10-13 GB GBGB0917934.2A patent/GB0917934D0/en not_active Ceased
-
2010
- 2010-10-07 TW TW099134166A patent/TW201114768A/zh unknown
- 2010-10-08 CN CN2010800462265A patent/CN102574849A/zh active Pending
- 2010-10-08 BR BR112012008530A patent/BR112012008530A2/pt not_active IP Right Cessation
- 2010-10-08 WO PCT/GB2010/001890 patent/WO2011045561A2/en not_active Ceased
- 2010-10-08 AU AU2010308158A patent/AU2010308158A1/en not_active Abandoned
- 2010-10-08 IN IN2075DEN2012 patent/IN2012DN02075A/en unknown
- 2010-10-08 US US13/502,054 patent/US20120202690A1/en not_active Abandoned
- 2010-10-08 CA CA2773604A patent/CA2773604A1/en not_active Abandoned
- 2010-10-08 EP EP10763404A patent/EP2488518A2/en not_active Withdrawn
- 2010-10-13 AR ARP100103736A patent/AR078623A1/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IN2012DN02075A (enExample) | 2015-08-21 |
| CN102574849A (zh) | 2012-07-11 |
| EP2488518A2 (en) | 2012-08-22 |
| AR078623A1 (es) | 2011-11-23 |
| AU2010308158A1 (en) | 2012-04-05 |
| WO2011045561A3 (en) | 2011-06-16 |
| WO2011045561A2 (en) | 2011-04-21 |
| CA2773604A1 (en) | 2011-04-21 |
| BR112012008530A2 (pt) | 2015-09-22 |
| US20120202690A1 (en) | 2012-08-09 |
| GB0917934D0 (en) | 2009-11-25 |
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