AR093977A1 - Proceso para la preparacion de 4-amino-5-fluoro-3-cloro-6-picolinatos (sustituidos) - Google Patents
Proceso para la preparacion de 4-amino-5-fluoro-3-cloro-6-picolinatos (sustituidos)Info
- Publication number
- AR093977A1 AR093977A1 ARP130104694A ARP130104694A AR093977A1 AR 093977 A1 AR093977 A1 AR 093977A1 AR P130104694 A ARP130104694 A AR P130104694A AR P130104694 A ARP130104694 A AR P130104694A AR 093977 A1 AR093977 A1 AR 093977A1
- Authority
- AR
- Argentina
- Prior art keywords
- formula
- fluoro
- amino
- substituted
- chloro
- Prior art date
Links
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 abstract 6
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 abstract 6
- UJYCPEJVJKAWMO-UHFFFAOYSA-N 4-amino-5-chloro-3-fluoropyridine-2-carboxylic acid Chemical compound NC1=C(Cl)C=NC(C(O)=O)=C1F UJYCPEJVJKAWMO-UHFFFAOYSA-N 0.000 abstract 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 4
- 239000002798 polar solvent Substances 0.000 abstract 3
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 abstract 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 2
- -1 4-amino -5-fluoro-3-chloro-6-picolinaldehyde Chemical compound 0.000 abstract 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 abstract 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 abstract 2
- 229910052783 alkali metal Inorganic materials 0.000 abstract 2
- 239000002585 base Substances 0.000 abstract 2
- TZUYFNORLRBWLP-UHFFFAOYSA-N ethanimidoyl chloride Chemical compound CC(Cl)=N TZUYFNORLRBWLP-UHFFFAOYSA-N 0.000 abstract 2
- 125000001841 imino group Chemical group [H]N=* 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 abstract 2
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 abstract 1
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 abstract 1
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 abstract 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 1
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 abstract 1
- 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 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 229910001516 alkali metal iodide Inorganic materials 0.000 abstract 1
- 229910000318 alkali metal phosphate Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 229910001919 chlorite Inorganic materials 0.000 abstract 1
- 229910052619 chlorite group Inorganic materials 0.000 abstract 1
- GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 abstract 1
- 230000001351 cycling effect Effects 0.000 abstract 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 abstract 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 abstract 1
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract 1
- 239000011707 mineral Substances 0.000 abstract 1
- 150000007522 mineralic acids Chemical class 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 239000003880 polar aprotic solvent Substances 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 125000005270 trialkylamine group Chemical group 0.000 abstract 1
Classifications
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- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Reivindicación 1: Un proceso para la preparación de un 4-amino-5-fluoro-3-cloro-6-picolinato (sustituido) de la fórmula (1) donde R¹ representa al alquilo C₁₋₄, ciclopropilo, alquenilo C₂₋₄ o fenilo sustituidos con desde 1 a 4 sustituyentes seleccionados en forma independiente del halógeno, alquilo C₁₋₄, haloalquilo C₁₋₄, alcoxi C₁₋₄ o haloalcoxi C₁₋₄ y R² representa al alquilo C₁₋₁₂ o un arilalquilo C₇₋₁₁ sustituido o no sustituido, que comprende los siguientes pasos: a) contactar ácido trifluoroacético con p-metoxianilina en presencia de una triarilfosfina y una base trialquilamina en solvente de tetracloruro de carbono para producir un cloruro de acetimidoílo de la fórmula (2); b) contactar el cloruro de acetimidoílo de la fórmula (2) con un 3,3-dialcoxiprop-1-ino (fórmula (3)) donde R³ representa al alquilo C₁₋₄, en presencia de yoduro de cobre(I), un yoduro de metal alcalino y un fosfato de metal alcalino en un solvente aprótico polar para producir un (imino)pent-2-ino dialquil acetal de la fórmula (4) donde R³ es como se definió anteriormente; c) ciclar el (imino)pent-2-ino dialquilo acetal de la fórmula (4) con una amina de la fórmula (5) donde R¹ es conforme se definió anteriormente, en presencia de una base de metal álcali inorgánica en un solvente polar aprótico a temperatura desde alrededor de ambiente hasta alrededor de 100ºC para producir un 4-(4-metoxifenilo)amino-5-fluoro-6-piridina(sustituida)-2-dialquilo acetal de la fórmula (6) donde R¹ y R³ son como se definieron anteriormente; d) clorar el 4-(4-metoxifenilo)amino-5-fluoro-6-piridina(sustituida)-2-dialquilo acetal de la fórmula (6) con 1,3-dicloro-5,5-dimetilimidazolidin-2,4-diona fórmula (7) en un solvente a polar para producir el 4-amino-5-fluoro-3-cloro-6-piridina (sustituida)-2-dialquilo acetal protegido de la fórmula (8) donde R¹ y R³ son como se definieron anteriormente; e) desproteger e hidrolizar el 4-amino-5-fluoro-3-cloro-6-piridina(sustituido)-2-dialquilo acetal protegido de la fórmula (8) con un ácido mineral en un solvente polar para producir el 4-amino-5-fluoro-3-cloro-6-picolinaldehído (sustituido) de la fórmula (9) donde R¹ es conforme se definió anteriormente; f) oxidar el 4-amino-5-fluoro-3-cloro-6-piconilaldehído (sustituido) de la fórmula (9) con un clorito de metal alcalino en presencia de un ácido inorgánico y un depurador de ácido hipocloroso en un solvente de alcohol acuoso para producir un 4-amino-5-fluoro-3-cloro-6-ácido picolínico (sustituido) de la fórmula (10) donde R¹ es como se definió anteriormente; y g) esterificar al 4-amino-5-fluoro-3-cloro-6-ácido picolínico (sustituido) de la fórmula (10) con un componente de la fórmula R²X donde X representa a OH, Cl, Br, o I, y R² es como se definió anteriormente para producir un 4-amino-5-fluoro-3-cloro-6-picolinato (sustituido) de la fórmula (1).
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261736835P | 2012-12-13 | 2012-12-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR093977A1 true AR093977A1 (es) | 2015-07-01 |
Family
ID=50931650
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP130104694A AR093977A1 (es) | 2012-12-13 | 2013-12-13 | Proceso para la preparacion de 4-amino-5-fluoro-3-cloro-6-picolinatos (sustituidos) |
Country Status (16)
| Country | Link |
|---|---|
| US (3) | US9212141B2 (es) |
| EP (1) | EP2931043B1 (es) |
| JP (1) | JP6310939B2 (es) |
| KR (1) | KR20150093799A (es) |
| CN (1) | CN104994733B (es) |
| AR (1) | AR093977A1 (es) |
| AU (1) | AU2013359255B2 (es) |
| BR (1) | BR102013032003A2 (es) |
| CA (1) | CA2895180A1 (es) |
| IL (1) | IL239225A (es) |
| MX (1) | MX2015007526A (es) |
| NZ (1) | NZ708680A (es) |
| PL (1) | PL2931043T3 (es) |
| RU (1) | RU2653855C2 (es) |
| WO (1) | WO2014093588A1 (es) |
| ZA (1) | ZA201504166B (es) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2013359255B2 (en) * | 2012-12-13 | 2017-01-05 | 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） |
| TW201609652A (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（三） |
| TW201524956A (zh) * | 2013-11-12 | 2015-07-01 | Dow Agrosciences Llc | 用於氟化化合物之過程（二） |
| 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 |
| RU2018130270A (ru) * | 2016-01-22 | 2020-02-25 | ДАУ АГРОСАЙЕНСИЗ ЭлЭлСи | Способ получения 4-алкокси-3-ацетоксипиколиновых кислот |
| KR102384531B1 (ko) * | 2016-07-07 | 2022-04-08 | 코르테바 애그리사이언스 엘엘씨 | 4-알콕시-3-(아실 또는 알킬)옥시피콜린아미드의 제조 방법 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 (uk) * | 2003-04-02 | 2008-04-10 | Дау Агросайенсиз Ллс | 6-алкіл або алкеніл-4-амінопіколінати гербіцидна композиція, спосіб боротьби з небажаною рослинністю |
| WO2006062979A1 (en) * | 2004-12-06 | 2006-06-15 | E.I. Dupont De Nemours And Company | Herbicidal 6-cyclopropyl-substitute 4-aminopicolinic acid derivatives |
| JP5059779B2 (ja) | 2006-01-13 | 2012-10-31 | ダウ アグロサイエンシィズ エルエルシー | ６−（多置換アリール）−４−アミノピコリネートおよび除草剤としてのそれらの使用 |
| NZ607580A (en) * | 2010-09-29 | 2015-01-30 | Intervet Int Bv | N-heteroaryl compounds |
| 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 |
| AU2013359255B2 (en) * | 2012-12-13 | 2017-01-05 | Dow Agrosciences Llc | Process for the preparation of 4-amino-5-fluoro-3-chloro-6-(substituted)picolinates |
-
2013
- 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 KR KR1020157018306A patent/KR20150093799A/ko not_active Application Discontinuation
- 2013-12-12 MX MX2015007526A patent/MX2015007526A/es unknown
- 2013-12-12 JP JP2015547527A patent/JP6310939B2/ja not_active Expired - Fee Related
- 2013-12-12 EP EP13861549.7A patent/EP2931043B1/en not_active Not-in-force
- 2013-12-12 CN CN201380064521.7A patent/CN104994733B/zh not_active Expired - Fee Related
- 2013-12-12 NZ NZ708680A patent/NZ708680A/en not_active IP Right Cessation
- 2013-12-12 WO PCT/US2013/074600 patent/WO2014093588A1/en active Application Filing
- 2013-12-12 RU RU2015127993A patent/RU2653855C2/ru not_active IP Right Cessation
- 2013-12-12 PL PL13861549T patent/PL2931043T3/pl unknown
- 2013-12-12 US US14/104,197 patent/US9212141B2/en not_active Expired - Fee Related
- 2013-12-12 BR BR102013032003-0A patent/BR102013032003A2/pt not_active Application Discontinuation
- 2013-12-13 AR ARP130104694A patent/AR093977A1/es active IP Right Grant
-
2014
- 2014-06-13 US US14/304,345 patent/US9822077B2/en not_active Expired - Fee Related
-
2015
- 2015-06-04 IL IL239225A patent/IL239225A/en not_active IP Right Cessation
- 2015-06-09 ZA ZA2015/04166A patent/ZA201504166B/en unknown
-
2017
- 2017-08-23 US US15/683,813 patent/US9981911B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CN104994733A (zh) | 2015-10-21 |
| PL2931043T3 (pl) | 2018-01-31 |
| JP2016504319A (ja) | 2016-02-12 |
| US20140171653A1 (en) | 2014-06-19 |
| BR102013032003A2 (pt) | 2014-10-21 |
| CN104994733B (zh) | 2017-03-15 |
| US9981911B2 (en) | 2018-05-29 |
| US20140296533A1 (en) | 2014-10-02 |
| US9212141B2 (en) | 2015-12-15 |
| IL239225A0 (en) | 2015-07-30 |
| RU2653855C2 (ru) | 2018-05-15 |
| US9822077B2 (en) | 2017-11-21 |
| MX2015007526A (es) | 2015-10-14 |
| EP2931043A4 (en) | 2016-06-08 |
| US20170349549A1 (en) | 2017-12-07 |
| JP6310939B2 (ja) | 2018-04-11 |
| AU2013359255B2 (en) | 2017-01-05 |
| ZA201504166B (en) | 2016-11-30 |
| IL239225A (en) | 2017-12-31 |
| KR20150093799A (ko) | 2015-08-18 |
| NZ708680A (en) | 2018-05-25 |
| EP2931043B1 (en) | 2017-08-02 |
| WO2014093588A1 (en) | 2014-06-19 |
| CA2895180A1 (en) | 2014-06-19 |
| EP2931043A1 (en) | 2015-10-21 |
| RU2015127993A (ru) | 2017-01-18 |
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