RU2015127993A - Способ получения 4-амино-5-фтор-3-хлор-6-(замещенных)пиколинатов - Google Patents
Способ получения 4-амино-5-фтор-3-хлор-6-(замещенных)пиколинатов Download PDFInfo
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- RU2015127993A RU2015127993A RU2015127993A RU2015127993A RU2015127993A RU 2015127993 A RU2015127993 A RU 2015127993A RU 2015127993 A RU2015127993 A RU 2015127993A RU 2015127993 A RU2015127993 A RU 2015127993A RU 2015127993 A RU2015127993 A RU 2015127993A
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- formula
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- alkyl
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- fluoro
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- 238000004519 manufacturing process Methods 0.000 title 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims 6
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims 6
- -1 4-amino-5-fluoro-3- chloro-6- (substituted) picolinaldehyde Chemical class 0.000 claims 5
- 150000001875 compounds Chemical class 0.000 claims 5
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims 4
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 4
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 4
- 229910052736 halogen Inorganic materials 0.000 claims 4
- 150000002367 halogens Chemical class 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- 125000001424 substituent group Chemical group 0.000 claims 4
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims 2
- 229910052783 alkali metal Inorganic materials 0.000 claims 2
- 239000002585 base Substances 0.000 claims 2
- 125000001841 imino group Chemical group [H]N=* 0.000 claims 2
- 239000003880 polar aprotic solvent Substances 0.000 claims 2
- 239000002798 polar solvent Substances 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims 2
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 claims 1
- 229910021595 Copper(I) iodide Inorganic materials 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 230000001476 alcoholic effect Effects 0.000 claims 1
- 229910001516 alkali metal iodide Inorganic materials 0.000 claims 1
- 229910000318 alkali metal phosphate Inorganic materials 0.000 claims 1
- 150000001340 alkali metals Chemical class 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 125000003710 aryl alkyl group Chemical group 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 238000005660 chlorination reaction Methods 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 229910001919 chlorite Inorganic materials 0.000 claims 1
- 229910052619 chlorite group Inorganic materials 0.000 claims 1
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 claims 1
- 238000010511 deprotection reaction Methods 0.000 claims 1
- 230000032050 esterification Effects 0.000 claims 1
- 238000005886 esterification reaction Methods 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 claims 1
- 229910052500 inorganic mineral Inorganic materials 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 239000011707 mineral Substances 0.000 claims 1
- 150000007522 mineralic acids Chemical class 0.000 claims 1
- 230000003647 oxidation Effects 0.000 claims 1
- 238000007254 oxidation reaction Methods 0.000 claims 1
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 claims 1
- 238000007363 ring formation reaction Methods 0.000 claims 1
- 125000005270 trialkylamine group Chemical group 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/02—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups
- C07C251/04—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C251/10—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of an unsaturated carbon skeleton
- C07C251/16—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of an unsaturated carbon skeleton containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
- C07D213/803—Processes of preparation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/02—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups
- C07C251/04—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C251/10—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of an unsaturated carbon skeleton
- C07C251/12—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of an unsaturated carbon skeleton being acyclic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen 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
- C07D213/72—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen 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
- C07D213/72—Nitrogen atoms
- C07D213/73—Unsubstituted amino or imino radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen 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
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Claims (54)
1. Способ получения 4-амино-5-фтор-3-хлор-6-(замещенных)пиколинатов формулы I
в которой
R1 представляет собой С1-С4алкил, циклопропил, С2-С4алкенил или фенил, замещенный 1-4 заместителями, независимо выбранными из галогена, С1-С4алкила, С1-С4галогеналкила, С1-С4алкокси или С1-С4галогеналкокси, и
R2 представляет собой С1-С12алкил или незамещенный или замещенный С7-С11арилалкил,
включающий следующие стадии:
а) контактирование трифторуксусной кислоты с п-метоксианилином в присутствии триарилфосфина и триалкиламинового основания в растворителе четыреххлористый углерод для образования ацетимидоилхлорида формулы А
b) контактирование ацетимидоилхлорида формулы А с 3,3-диалкоксипроп-1-ином (формула В)
в которой R3 представляет собой С1-С4алкил,
в присутствии иодида меди(I), иодида щелочного металла и фосфата щелочного металла в полярном апротонном растворителе для получения (имино)пент-2-индиалкилацеталя формулы С
в которой R3 является таким, как определено ранее;
с) циклизация (имино)пент-2-индиалкилацеталя формулы С с амином формулы D
в которой R1 является таким, как определено ранее,
в присутствии неорганического основания щелочного металла в полярном апротонном растворителе при температуре приблизительно от комнатной до приблизительно 100°С для образования 4-(4-метоксифенил)амино-5-фтор-6-(замещенный)пиридин-2-диалкилацеталя формулы Е
в которой R1 и R3 являются такими, как определено ранее;
d) хлорирование 4-(4-метоксифенил)амино-5-фтор-6-(замещенный)пиридин-2-диалкилацеталя формулы Е посредством 1,3-дихлор-5,5-диметилимидазолидин-2,4-диона (формулы F)
в полярном растворителе для получения защищенного 4-амино-5-фтор-3-хлор-6-(замещенный)пиридин-2-диалкилацеталя формулы G
в которой R1 и R3 являются такими, как определено ранее;
е) удаление защиты и гидролиз защищенного 4-амино-5-фтор-3-хлор-6-(замещенный)пиридин-2-диалкилацеталя формулы G с помощью минеральной кислоты в полярном растворителе для получения 4-амино-5-фтор-3-хлор-6-(замещенный)пиколинальдегида формулы Н
в которой R1 является таким, как определено ранее;
f) окисление 4-амино-5-фтор-3-хлор-6-(замещенный)пиколинальдегида формулы Н хлоритом щелочного металла в присутствии неорганической кислоты и акцептора гипохлористой кислоты в водном спиртовом растворителе для получения 4-амино-5-фтор-3-хлор-6-(замещенной)пиколиновой кислоты формулы J
в которой R1 является таким, как определено ранее; и
g) этерификация 4-амино-5-фтор-3-хлор-6-(замещенной)пиколиновой кислоты формулы J соединением формулы
R2X
в которой
Х представляет собой ОН, Cl, Br или I, и
R2 является таким, как определено ранее,
для получения 4-амино-5-фтор-3-хлор-6-(замещенного)пиколината формулы I.
2. Соединение формулы С
в которой R3 представляет собой С1-С4алкил.
3. Соединение формулы Е
в которой
R1 представляет собой С1-С4алкил, циклопропил, С2-С4алкенил или фенил, замещенный 1-4 заместителями, независимо выбранными из галогена, С1-С4алкила, С1-С4галогеналкила, С1-С4алкокси или С1-С4галогеналкокси, и
R3 представляет собой С1-С4алкил.
4. Соединение формулы G
в которой
R1 представляет собой С1-С4алкил, циклопропил, С2-С4алкенил или фенил, замещенный 1-4 заместителями, независимо выбранными из галогена, С1-С4алкила, С1-С4галогеналкила, С1-С4алкокси или С1-С4галогеналкокси, и
R3 представляет собой С1-С4алкил.
5. Соединение формулы H
в которой
R1 представляет собой С1-С4алкил, циклопропил, С2-С4алкенил или фенил, замещенный 1-4 заместителями, независимо выбранными из галогена, С1-С4алкила, С1-С4галогеналкила, С1-С4алкокси или С1-С4галогеналкокси.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261736835P | 2012-12-13 | 2012-12-13 | |
| US61/736,835 | 2012-12-13 | ||
| PCT/US2013/074600 WO2014093588A1 (en) | 2012-12-13 | 2013-12-12 | Process for the preparation of 4-amino-5-fluoro-3-chloro-6-(substituted)picolinates |
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| Publication Number | Publication Date |
|---|---|
| RU2015127993A true RU2015127993A (ru) | 2017-01-18 |
| RU2653855C2 RU2653855C2 (ru) | 2018-05-15 |
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| RU2015127993A RU2653855C2 (ru) | 2012-12-13 | 2013-12-12 | Способ получения 4-амино-5-фтор-3-хлор-6-(замещенных)пиколинатов |
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| Country | Link |
|---|---|
| US (3) | US9212141B2 (ru) |
| EP (1) | EP2931043B1 (ru) |
| JP (1) | JP6310939B2 (ru) |
| KR (1) | KR20150093799A (ru) |
| CN (1) | CN104994733B (ru) |
| AR (1) | AR093977A1 (ru) |
| AU (1) | AU2013359255B2 (ru) |
| BR (1) | BR102013032003A2 (ru) |
| CA (1) | CA2895180A1 (ru) |
| IL (1) | IL239225A (ru) |
| MX (1) | MX2015007526A (ru) |
| NZ (1) | NZ708680A (ru) |
| PL (1) | PL2931043T3 (ru) |
| RU (1) | RU2653855C2 (ru) |
| WO (1) | WO2014093588A1 (ru) |
| ZA (1) | ZA201504166B (ru) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| EP2931043B1 (en) * | 2012-12-13 | 2017-08-02 | Dow AgroSciences LLC | Process for the preparation of 4-amino-5-fluoro-3-chloro-6-(substituted)picolinates |
| TW201609651A (zh) | 2013-11-12 | 2016-03-16 | 陶氏農業科學公司 | 用於氟化化合物之過程（一） |
| BR102014028164A2 (pt) * | 2013-11-12 | 2015-09-08 | Dow Agrosciences Llc | processo para fluoração de compostos |
| BR102014028162A2 (pt) | 2013-11-12 | 2015-09-08 | Dow Agrosciences Llc | processo para fluoração de compostos |
| TWI726900B (zh) | 2015-08-04 | 2021-05-11 | 美商陶氏農業科學公司 | 用於氟化化合物之過程 |
| US10259789B2 (en) * | 2016-01-22 | 2019-04-16 | Dow Agrosciences Llc | Process for the preparation of 4-alkoxy-3-acetoxypicolinic acids |
| PL3481200T3 (pl) * | 2016-07-07 | 2021-05-17 | Dow Agrosciences Llc | Sposoby wytwarzania 4-alkoksy-3-(acylo lub alkilo)oksypikolinamidów |
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| SU680613A3 (ru) * | 1971-12-07 | 1979-08-15 | Циба-Гейги Аг (Фирма) | Средство борьбы с насекомыми и клещами |
| PL212932B1 (pl) * | 2000-01-14 | 2012-12-31 | Dow Agrosciences Llc | Pochodne 4-aminopikolinianowe, kompozycja herbicydowa zawierajaca te zwiazki oraz sposób kontrolowania niepozadanej wegetacji |
| 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 |
| TW200307669A (en) * | 2002-04-15 | 2003-12-16 | Nippon Soda Co | Novel oxime o-ether compound, production process thereof, and agricultural or horticultural bactericide |
| UA82358C2 (ru) * | 2003-04-02 | 2008-04-10 | Дау Агросайенсиз Ллс | 6-алкил или фенил-4-аминопиколинаты, гербицидная композиция, способ борьбы с нежелательной растительностью |
| WO2006062979A1 (en) * | 2004-12-06 | 2006-06-15 | E.I. Dupont De Nemours And Company | Herbicidal 6-cyclopropyl-substitute 4-aminopicolinic acid derivatives |
| CA2626103C (en) | 2006-01-13 | 2013-07-30 | Dow Agrosciences Llc | 6-(poly-substituted aryl)-4-aminopicolinates and their use as herbicides |
| PL2621903T3 (pl) * | 2010-09-29 | 2017-08-31 | Intervet International B.V. | Związki n-heteroarylu |
| TWI529163B (zh) * | 2011-01-25 | 2016-04-11 | 陶氏農業科學公司 | 用於製備４－胺基－５－氟－３－鹵素－６－（經取代之）吡啶甲酸酯的方法 |
| TWI596088B (zh) | 2011-01-25 | 2017-08-21 | 陶氏農業科學公司 | ４－胺基－６－（經取代的苯基）吡啶甲酸酯及６－胺基－２－（經取代的苯基）－４－嘧啶羧酸酯之芳烷酯以及其等作為除草劑之用途 |
| EP2931043B1 (en) * | 2012-12-13 | 2017-08-02 | Dow AgroSciences LLC | Process for the preparation of 4-amino-5-fluoro-3-chloro-6-(substituted)picolinates |
-
2013
- 2013-12-12 EP EP13861549.7A patent/EP2931043B1/en not_active Not-in-force
- 2013-12-12 RU RU2015127993A patent/RU2653855C2/ru not_active IP Right Cessation
- 2013-12-12 AU AU2013359255A patent/AU2013359255B2/en not_active Ceased
- 2013-12-12 CA CA2895180A patent/CA2895180A1/en not_active Abandoned
- 2013-12-12 MX MX2015007526A patent/MX2015007526A/es unknown
- 2013-12-12 WO PCT/US2013/074600 patent/WO2014093588A1/en active Application Filing
- 2013-12-12 KR KR1020157018306A patent/KR20150093799A/ko not_active Application Discontinuation
- 2013-12-12 NZ NZ708680A patent/NZ708680A/en not_active IP Right Cessation
- 2013-12-12 JP JP2015547527A patent/JP6310939B2/ja not_active Expired - Fee Related
- 2013-12-12 BR BR102013032003-0A patent/BR102013032003A2/pt not_active Application Discontinuation
- 2013-12-12 PL PL13861549T patent/PL2931043T3/pl unknown
- 2013-12-12 CN CN201380064521.7A patent/CN104994733B/zh not_active Expired - Fee Related
- 2013-12-12 US US14/104,197 patent/US9212141B2/en not_active Expired - Fee Related
- 2013-12-13 AR ARP130104694A patent/AR093977A1/es active IP Right Grant
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2014
- 2014-06-13 US US14/304,345 patent/US9822077B2/en not_active Expired - Fee Related
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2015
- 2015-06-04 IL IL239225A patent/IL239225A/en not_active IP Right Cessation
- 2015-06-09 ZA ZA2015/04166A patent/ZA201504166B/en unknown
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Also Published As
| Publication number | Publication date |
|---|---|
| KR20150093799A (ko) | 2015-08-18 |
| CA2895180A1 (en) | 2014-06-19 |
| PL2931043T3 (pl) | 2018-01-31 |
| MX2015007526A (es) | 2015-10-14 |
| JP6310939B2 (ja) | 2018-04-11 |
| US20170349549A1 (en) | 2017-12-07 |
| NZ708680A (en) | 2018-05-25 |
| AR093977A1 (es) | 2015-07-01 |
| EP2931043A1 (en) | 2015-10-21 |
| RU2653855C2 (ru) | 2018-05-15 |
| EP2931043A4 (en) | 2016-06-08 |
| ZA201504166B (en) | 2016-11-30 |
| BR102013032003A2 (pt) | 2014-10-21 |
| JP2016504319A (ja) | 2016-02-12 |
| US20140171653A1 (en) | 2014-06-19 |
| CN104994733A (zh) | 2015-10-21 |
| IL239225A (en) | 2017-12-31 |
| AU2013359255B2 (en) | 2017-01-05 |
| US20140296533A1 (en) | 2014-10-02 |
| US9212141B2 (en) | 2015-12-15 |
| CN104994733B (zh) | 2017-03-15 |
| US9822077B2 (en) | 2017-11-21 |
| EP2931043B1 (en) | 2017-08-02 |
| IL239225A0 (en) | 2015-07-30 |
| US9981911B2 (en) | 2018-05-29 |
| WO2014093588A1 (en) | 2014-06-19 |
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