RU2016132765A - (s)-3`-метилабсцизовая кислота и ее эфиры - Google Patents
(s)-3`-метилабсцизовая кислота и ее эфиры Download PDFInfo
- Publication number
- RU2016132765A RU2016132765A RU2016132765A RU2016132765A RU2016132765A RU 2016132765 A RU2016132765 A RU 2016132765A RU 2016132765 A RU2016132765 A RU 2016132765A RU 2016132765 A RU2016132765 A RU 2016132765A RU 2016132765 A RU2016132765 A RU 2016132765A
- Authority
- RU
- Russia
- Prior art keywords
- compound according
- compound
- lower alkyl
- represents hydrogen
- nhc
- Prior art date
Links
- 239000002253 acid Substances 0.000 title claims 2
- 150000002170 ethers Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 11
- 125000000217 alkyl group Chemical group 0.000 claims 7
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims 2
- 150000002431 hydrogen Chemical group 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 claims 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-L L-tartrate(2-) Chemical compound [O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O FEWJPZIEWOKRBE-JCYAYHJZSA-L 0.000 claims 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 1
- 239000003513 alkali Substances 0.000 claims 1
- -1 alkaline earth metal cation Chemical class 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000004946 alkenylalkyl group Chemical group 0.000 claims 1
- 239000002168 alkylating agent Substances 0.000 claims 1
- 229940100198 alkylating agent Drugs 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 125000005038 alkynylalkyl group Chemical group 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 150000001449 anionic compounds Chemical class 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 239000002585 base Substances 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 1
- 125000004366 heterocycloalkenyl group Chemical group 0.000 claims 1
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- 229910001412 inorganic anion Inorganic materials 0.000 claims 1
- 230000003993 interaction Effects 0.000 claims 1
- 239000012022 methylating agents Substances 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 150000002891 organic anions Chemical class 0.000 claims 1
- 230000008635 plant growth Effects 0.000 claims 1
- 125000001453 quaternary ammonium group Chemical group 0.000 claims 1
- 230000026267 regulation of growth Effects 0.000 claims 1
- 230000001105 regulatory effect Effects 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 229940095064 tartrate Drugs 0.000 claims 1
Classifications
-
- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/06—Unsaturated carboxylic acids or thio analogues thereof; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01G—HORTICULTURE; CULTIVATION OF VEGETABLES, FLOWERS, RICE, FRUIT, VINES, HOPS OR SEAWEED; FORESTRY; WATERING
- A01G7/00—Botany in general
- A01G7/06—Treatment of growing trees or plants, e.g. for preventing decay of wood, for tingeing flowers or wood, for prolonging the life of plants
-
- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/42—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing within the same carbon skeleton a carboxylic group or a thio analogue, or a derivative thereof, and a carbon atom having only two bonds to hetero atoms with at the most one bond to halogen, e.g. keto-carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
- C07C403/20—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by carboxyl groups or halides, anhydrides, or (thio)esters thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/76—Unsaturated compounds containing keto groups
- C07C59/80—Unsaturated compounds containing keto groups containing rings other than six-membered aromatic rings
- C07C59/82—Unsaturated compounds containing keto groups containing rings other than six-membered aromatic rings the keto group being part of a ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
- C07C69/738—Esters of keto-carboxylic acids or aldehydo-carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Environmental Sciences (AREA)
- Wood Science & Technology (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Zoology (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Health & Medical Sciences (AREA)
- Forests & Forestry (AREA)
- Biodiversity & Conservation Biology (AREA)
- Ecology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Botany (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Cultivation Of Plants (AREA)
- Chemical Kinetics & Catalysis (AREA)
Claims (15)
1. Соединение формулы I
в которой R представляет собой водород, замещенный или незамещенный алкил, циклоалкил, гетероциклоалкил, алкенилалкил, алкинилалкил, алкенил, циклоалкенил, гетероциклоалкенил, алкинил, арил, гетероарил, арилалкил или гетероарилалкил,
и его соли.
2. Соединение по п. 1, в котором R представляет собой водород.
3. Соединение по п. 1, в котором R представляет собой алкил.
4. Соединение по п. 3, в котором R представляет собой низший алкил.
5. Соединение по п. 3, в котором R независимо замещен, по меньшей мере, одним из -OH, -NH2, -SH, галогена, -CN, -NR1R2, -OR1, -SR1, -S(O)R1, -SO2R1, -C(O)R1, -C(O)NR1R2, -NHC(O)R1, -NHSO2R1, -NHC(O)OR3, -SO2NR1R2, или -NHC(O)NR1R2, где каждый из R1 и R2 независимо представляет собой водород или низший алкил, и R3 представляет собой низший алкил.
6. Соединение по п. 1, где соль содержит катион щелочного или щелочноземельного металла, протонированный амин (+NHR4R5R6), где каждый из R4, R5 и R6 независимо представляет собой водород, низший алкил, аралкил или четвертичный аммониевый ион (+NR7R8R9R10), в котором каждый из R7, R8, R9 и R10 независимо представляет собой низший алкил или низший аралкил.
7. Соединение по п. 1, где соль содержит неорганический анион, выбранный из группы, включающей в себя хлорид (Cl-), бромид (Br-), йодид (I-), сульфат (SO4 2-) и гидросульфат (HSO4-), и так далее, или органический анион, выбранный из группы, включающей в себя формиат (HCO2 -), ацетат (CH3CO2 -), тартрат (-CO2CH(OH)CH(OH)CO2 -), метансульфонат (CH3SO3 -) и толилсульфонат (CH3C6H4SO3 -), и в котором R содержит основной атом азота.
8. Способ регулирования роста растений, включающий применение эффективного количества соединения по п. 1 к растению, нуждающемуся в регулировании роста.
9. Способ получения соединения по п. 1, включающий:
a. введение во взаимодействие (S)-абсцизовой кислоты с алкилирующим агентом с образованием сложного эфира,
b. обработку соединения, полученного на стадии а., основанием и метилирующим агентом в растворителе,
c. и необязательный гидролиз соединений, полученных на стадии b.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201461925764P | 2014-01-10 | 2014-01-10 | |
| US61/925,764 | 2014-01-10 | ||
| PCT/US2015/010726 WO2015106050A1 (en) | 2014-01-10 | 2015-01-09 | (s)-3'-methyl-abscisic acid and esters thereof |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| RU2016132765A true RU2016132765A (ru) | 2018-02-14 |
| RU2016132765A3 RU2016132765A3 (ru) | 2018-09-03 |
| RU2685727C2 RU2685727C2 (ru) | 2019-04-23 |
Family
ID=53520758
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2016132765A RU2685727C2 (ru) | 2014-01-10 | 2015-01-09 | (s)-3'-метилабсцизовая кислота и ее эфиры |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US9326508B2 (ru) |
| EP (1) | EP3091837B1 (ru) |
| JP (3) | JP2017509590A (ru) |
| CN (2) | CN106132207A (ru) |
| AR (1) | AR099070A1 (ru) |
| AU (1) | AU2015204644B2 (ru) |
| BR (1) | BR112016015849B1 (ru) |
| CA (1) | CA2936093A1 (ru) |
| CL (1) | CL2016001745A1 (ru) |
| ES (1) | ES2912185T3 (ru) |
| IL (1) | IL246450B (ru) |
| MX (1) | MX358078B (ru) |
| PE (1) | PE20161226A1 (ru) |
| PH (1) | PH12016501326A1 (ru) |
| RU (1) | RU2685727C2 (ru) |
| WO (1) | WO2015106050A1 (ru) |
| ZA (1) | ZA201604594B (ru) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106470546B (zh) * | 2014-07-08 | 2019-05-14 | 瓦伦特生物科学公司 | 3′-取代的脱落酸衍生物 |
| WO2016187369A1 (en) * | 2015-05-19 | 2016-11-24 | Valent Biosciences Corporation | (s)-abscisic acid derivatives for thinning |
| US10314307B2 (en) | 2015-05-19 | 2019-06-11 | Valent Biosciences Llc | (S)-abscisic acid derivatives for improving plant stress tolerance |
| US12063929B2 (en) * | 2018-11-19 | 2024-08-20 | University Of Saskatchewan | 3′-alkynyl abscisic acid derivatives as ABA antagonists |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5518995A (en) | 1988-12-01 | 1996-05-21 | National Research Council Of Canada | Use of compounds to enhance synchrony of germination and emergence in plants |
| JP2903778B2 (ja) * | 1991-06-24 | 1999-06-14 | 東レ株式会社 | アブシジン酸類縁体および植物生長調節剤 |
| RU2085077C1 (ru) * | 1992-09-16 | 1997-07-27 | Товарищество с ограниченной ответственностью "Биотэк" | Способ получения абсцизовой кислоты |
| US5481034A (en) * | 1994-05-02 | 1996-01-02 | Korea Research Institute Of Chemical Technology | Fluorinated abscisic acid derivatives and plant growth regulator thereof |
| JP3529793B2 (ja) * | 1995-12-21 | 2004-05-24 | ナショナル リサーチ カウンシル オブ カナダ | Ｈｙｐｅｒａｂａｓ：８’―メチル又は９’―メチル炭素原子に不飽和炭素置換基を有する生物学的に活性なアブシジン酸類似体 |
| CA2566455C (en) | 2004-05-10 | 2013-01-08 | National Research Council Of Canada | Synthesis and biological activity of bicyclic aba analogs |
| MX2011000930A (es) | 2008-07-24 | 2011-03-15 | Valent Biosciences Corp | Sales, composiciones liquidas acuosas que contienen sales de acido s- (+) -abscisico y metodos de su preparacion. |
| WO2011163029A2 (en) * | 2010-06-21 | 2011-12-29 | The Board Of Trustees Of The Leland Stanford Junior University | Alkenyl substituted cycloaliphatic compounds as chemical inducers of proximity |
| WO2012037563A1 (en) | 2010-09-17 | 2012-03-22 | Valent Biosciences Corporation | Compositions of abscisic acid for animal health |
| WO2013123164A1 (en) | 2012-02-14 | 2013-08-22 | Wilson John Hugh Mccleery | Method to increase plant yield |
| US8901153B2 (en) | 2012-04-27 | 2014-12-02 | Dow Agrosciences, Llc. | Pesticidal compositions and processes related thereto |
-
2015
- 2015-01-09 CN CN201580003697.0A patent/CN106132207A/zh active Pending
- 2015-01-09 RU RU2016132765A patent/RU2685727C2/ru active
- 2015-01-09 US US14/593,597 patent/US9326508B2/en active Active
- 2015-01-09 MX MX2016009073A patent/MX358078B/es active IP Right Grant
- 2015-01-09 BR BR112016015849-0A patent/BR112016015849B1/pt active IP Right Grant
- 2015-01-09 AU AU2015204644A patent/AU2015204644B2/en active Active
- 2015-01-09 AR ARP150100064A patent/AR099070A1/es active IP Right Grant
- 2015-01-09 CN CN202110141884.2A patent/CN112920051A/zh active Pending
- 2015-01-09 PE PE2016001096A patent/PE20161226A1/es unknown
- 2015-01-09 WO PCT/US2015/010726 patent/WO2015106050A1/en not_active Ceased
- 2015-01-09 ES ES15735075T patent/ES2912185T3/es active Active
- 2015-01-09 CA CA2936093A patent/CA2936093A1/en not_active Abandoned
- 2015-01-09 JP JP2016545804A patent/JP2017509590A/ja active Pending
- 2015-01-09 EP EP15735075.2A patent/EP3091837B1/en active Active
-
2016
- 2016-06-26 IL IL246450A patent/IL246450B/en active IP Right Grant
- 2016-07-04 PH PH12016501326A patent/PH12016501326A1/en unknown
- 2016-07-06 ZA ZA2016/04594A patent/ZA201604594B/en unknown
- 2016-07-07 CL CL2016001745A patent/CL2016001745A1/es unknown
-
2019
- 2019-02-20 JP JP2019027928A patent/JP2019108344A/ja active Pending
-
2020
- 2020-10-06 JP JP2020169076A patent/JP2021008495A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| BR112016015849A2 (ru) | 2017-08-08 |
| PH12016501326A1 (en) | 2017-02-06 |
| CL2016001745A1 (es) | 2017-05-19 |
| AR099070A1 (es) | 2016-06-29 |
| EP3091837A1 (en) | 2016-11-16 |
| EP3091837B1 (en) | 2022-03-09 |
| ZA201604594B (en) | 2017-08-30 |
| RU2685727C2 (ru) | 2019-04-23 |
| IL246450B (en) | 2020-11-30 |
| CA2936093A1 (en) | 2015-07-16 |
| EP3091837A4 (en) | 2017-09-20 |
| BR112016015849B1 (pt) | 2022-02-08 |
| JP2019108344A (ja) | 2019-07-04 |
| AU2015204644A1 (en) | 2016-07-14 |
| JP2021008495A (ja) | 2021-01-28 |
| ES2912185T3 (es) | 2022-05-24 |
| CN112920051A (zh) | 2021-06-08 |
| MX2016009073A (es) | 2016-09-09 |
| US9326508B2 (en) | 2016-05-03 |
| IL246450A0 (en) | 2016-08-31 |
| US20150197479A1 (en) | 2015-07-16 |
| WO2015106050A1 (en) | 2015-07-16 |
| PE20161226A1 (es) | 2016-11-12 |
| RU2016132765A3 (ru) | 2018-09-03 |
| MX358078B (es) | 2018-08-03 |
| AU2015204644B2 (en) | 2018-06-28 |
| CN106132207A (zh) | 2016-11-16 |
| JP2017509590A (ja) | 2017-04-06 |
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