DD257255A5 - Verfahren zur herstellung von neuen mono- oder di-(aryloxyethyl)succinaten - Google Patents
Verfahren zur herstellung von neuen mono- oder di-(aryloxyethyl)succinaten Download PDFInfo
- Publication number
- DD257255A5 DD257255A5 DD86304091A DD30409186A DD257255A5 DD 257255 A5 DD257255 A5 DD 257255A5 DD 86304091 A DD86304091 A DD 86304091A DD 30409186 A DD30409186 A DD 30409186A DD 257255 A5 DD257255 A5 DD 257255A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- succinate
- methyl
- hydrogen
- ethyl
- aryloxyethyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 11
- 238000002360 preparation method Methods 0.000 title claims abstract description 7
- 150000003890 succinate salts Chemical class 0.000 title claims 3
- 239000000203 mixture Substances 0.000 claims abstract description 31
- -1 phenoxyethyl groups Chemical group 0.000 claims abstract description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 10
- 239000001257 hydrogen Substances 0.000 claims abstract description 10
- 230000008635 plant growth Effects 0.000 claims abstract description 9
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229940014800 succinic anhydride Drugs 0.000 claims abstract description 8
- 239000004480 active ingredient Substances 0.000 claims abstract description 7
- 230000001105 regulatory effect Effects 0.000 claims abstract description 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract 6
- 150000003839 salts Chemical class 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 abstract description 15
- 150000001875 compounds Chemical class 0.000 abstract description 14
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 abstract description 12
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 abstract description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract description 4
- QZFAJHYRQCRHGT-UHFFFAOYSA-N 4-oxo-4-(2-phenoxyethoxy)butanoic acid Chemical compound OC(=O)CCC(=O)OCCOC1=CC=CC=C1 QZFAJHYRQCRHGT-UHFFFAOYSA-N 0.000 abstract description 3
- 150000003900 succinic acid esters Chemical class 0.000 abstract description 3
- LYJSRGNYLMKMOP-UHFFFAOYSA-N 2-(2,4,5-trichlorophenoxy)propan-1-ol Chemical compound OCC(C)OC1=CC(Cl)=C(Cl)C=C1Cl LYJSRGNYLMKMOP-UHFFFAOYSA-N 0.000 abstract description 2
- 230000033228 biological regulation Effects 0.000 abstract description 2
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- 239000011541 reaction mixture Substances 0.000 abstract description 2
- KYWMFBIXDBIJSY-UHFFFAOYSA-N bis(2-naphthalen-1-yloxyethyl) butanedioate Chemical compound C1=CC=C2C(OCCOC(CCC(=O)OCCOC=3C4=CC=CC=C4C=CC=3)=O)=CC=CC2=C1 KYWMFBIXDBIJSY-UHFFFAOYSA-N 0.000 abstract 2
- RINCXYDBBGOEEQ-UHFFFAOYSA-N succinic anhydride Chemical class O=C1CCC(=O)O1 RINCXYDBBGOEEQ-UHFFFAOYSA-N 0.000 abstract 1
- 241000196324 Embryophyta Species 0.000 description 17
- 239000013543 active substance Substances 0.000 description 13
- 230000012010 growth Effects 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 244000141359 Malus pumila Species 0.000 description 9
- 235000011430 Malus pumila Nutrition 0.000 description 9
- 235000015103 Malus silvestris Nutrition 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 238000011282 treatment Methods 0.000 description 8
- 239000000460 chlorine Substances 0.000 description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
- DKMROQRQHGEIOW-UHFFFAOYSA-N Diethyl succinate Chemical compound CCOC(=O)CCC(=O)OCC DKMROQRQHGEIOW-UHFFFAOYSA-N 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 150000005690 diesters Chemical class 0.000 description 4
- 230000017260 vegetative to reproductive phase transition of meristem Effects 0.000 description 4
- NOQGZXFMHARMLW-UHFFFAOYSA-N Daminozide Chemical compound CN(C)NC(=O)CCC(O)=O NOQGZXFMHARMLW-UHFFFAOYSA-N 0.000 description 3
- 240000008415 Lactuca sativa Species 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 244000046052 Phaseolus vulgaris Species 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 239000005648 plant growth regulator Substances 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- 230000000638 stimulation Effects 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 240000008067 Cucumis sativus Species 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 235000003228 Lactuca sativa Nutrition 0.000 description 2
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 235000013399 edible fruits Nutrition 0.000 description 2
- 235000015203 fruit juice Nutrition 0.000 description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000012258 stirred mixture Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- UDPGUMQDCGORJQ-UHFFFAOYSA-N (2-chloroethyl)phosphonic acid Chemical compound OP(O)(=O)CCCl UDPGUMQDCGORJQ-UHFFFAOYSA-N 0.000 description 1
- VZLMIORNRMGZJC-UHFFFAOYSA-N 1-naphthalen-2-yloxyethanol Chemical compound C1=CC=CC2=CC(OC(O)C)=CC=C21 VZLMIORNRMGZJC-UHFFFAOYSA-N 0.000 description 1
- DSUPUOGOCIFZBG-UHFFFAOYSA-N 2-(phenylcarbamoyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(=O)NC1=CC=CC=C1 DSUPUOGOCIFZBG-UHFFFAOYSA-N 0.000 description 1
- QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 235000009849 Cucumis sativus Nutrition 0.000 description 1
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 1
- 239000005975 Daminozide Substances 0.000 description 1
- 231100000674 Phytotoxicity Toxicity 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000003306 harvesting Methods 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000002420 orchard Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 229960005323 phenoxyethanol Drugs 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000000885 phytotoxic effect Effects 0.000 description 1
- 230000005070 ripening Effects 0.000 description 1
- 230000002786 root growth Effects 0.000 description 1
- 235000012045 salad Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000005082 stem growth Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000009105 vegetative growth Effects 0.000 description 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
- A01N39/00—Biocides, pest repellants or attractants, or plant growth regulators containing aryloxy- or arylthio-aliphatic or cycloaliphatic compounds, containing the group or, e.g. phenoxyethylamine, phenylthio-acetonitrile, phenoxyacetone
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/HU1986/000036 WO1986007354A1 (en) | 1985-06-03 | 1986-06-03 | New succinic acid derivatives, plant growth regulating compositions containing them and a process for the preparation thereof |
| EP86903535A EP0224551A1 (en) | 1985-06-03 | 1986-06-03 | New succinic acid derivatives, plant growth regulating compositions containing them and a process for the preparation thereof |
| US07/018,903 US4846883A (en) | 1985-06-03 | 1986-06-03 | Succinic acid derivatives and plant growth regulating compositions containing them |
| DD86304091A DD257255A5 (de) | 1985-06-03 | 1986-06-10 | Verfahren zur herstellung von neuen mono- oder di-(aryloxyethyl)succinaten |
| DD86291160A DD254877A5 (de) | 1985-06-03 | 1986-06-10 | Zusammensetzung und verfahren zur regulierung des pflanzenwachstums |
| CS864323A CS261895B2 (en) | 1985-06-03 | 1986-06-11 | Agent for plants growth regulation and method of efficient substance production |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU214285A HU193768B (en) | 1985-06-03 | 1985-06-03 | Compositions for controlling growth of plants containing derivatives of succinic acid and process for producing succinic acid derivatives |
| DD86304091A DD257255A5 (de) | 1985-06-03 | 1986-06-10 | Verfahren zur herstellung von neuen mono- oder di-(aryloxyethyl)succinaten |
| DD86291160A DD254877A5 (de) | 1985-06-03 | 1986-06-10 | Zusammensetzung und verfahren zur regulierung des pflanzenwachstums |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD257255A5 true DD257255A5 (de) | 1988-06-08 |
Family
ID=27179886
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD86304091A DD257255A5 (de) | 1985-06-03 | 1986-06-10 | Verfahren zur herstellung von neuen mono- oder di-(aryloxyethyl)succinaten |
| DD86291160A DD254877A5 (de) | 1985-06-03 | 1986-06-10 | Zusammensetzung und verfahren zur regulierung des pflanzenwachstums |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD86291160A DD254877A5 (de) | 1985-06-03 | 1986-06-10 | Zusammensetzung und verfahren zur regulierung des pflanzenwachstums |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US4846883A (cs) |
| EP (1) | EP0224551A1 (cs) |
| CS (1) | CS261895B2 (cs) |
| DD (2) | DD257255A5 (cs) |
| WO (1) | WO1986007354A1 (cs) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2290809C2 (ru) * | 2005-03-25 | 2007-01-10 | Иван Семёнович Новиков | Стимулятор плодообразования "томатон" |
| US20070130991A1 (en) * | 2005-12-14 | 2007-06-14 | Chevron U.S.A. Inc. | Liquefaction of associated gas at moderate conditions |
| US7786057B2 (en) * | 2007-02-08 | 2010-08-31 | Infineum International Limited | Soot dispersants and lubricating oil compositions containing same |
| CN103281905B (zh) | 2010-12-21 | 2016-10-19 | 拜尔作物科学有限合伙公司 | 芽孢杆菌属的砂纸突变体及其用于增进植物生长、促进植物健康及控制疾病和害虫的方法 |
| MX2014002890A (es) | 2011-09-12 | 2015-01-19 | Bayer Cropscience Lp | Metodo para mejorar la salud y/o promover el crecimiento de una planta y/o mejorar la maduracion de frutos. |
| WO2020053667A1 (en) * | 2018-09-11 | 2020-03-19 | Shrikant Kumar Burje | Alternative oxidase activity stimulating chemical composition and a method for reducing hypoxia in plants |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE708768C (de) * | 1939-11-01 | 1941-07-29 | Hoffmann La Roche & Co Akt Ges | Verfahren zur Darstellung von sauren Estern der alkylierten 1, 4-Naphthohydrochinone |
| BE515031A (cs) * | 1951-11-03 | |||
| US3085078A (en) * | 1958-10-22 | 1963-04-09 | Thompson Chemical Company | Ester of a dicarboxylic acid and vinyl chloride resin plasticized therewith |
| US4036984A (en) * | 1974-04-30 | 1977-07-19 | Nissan Chemical Industries, Ltd. | Soil fungi inhibiting agent |
| US4456721A (en) * | 1982-12-02 | 1984-06-26 | Borg-Warner Chemicals, Inc. | Flame-retarded acrylonitrile-butadiene-styrene copolymer compositions comprising bis(beta-pentabromophenoxyethyl) succinate |
| DE3321529A1 (de) * | 1983-06-15 | 1984-12-20 | Bayer Ag, 5090 Leverkusen | Mittel zur regulierung des pflanzenwachstums |
-
1986
- 1986-06-03 WO PCT/HU1986/000036 patent/WO1986007354A1/en not_active Ceased
- 1986-06-03 US US07/018,903 patent/US4846883A/en not_active Expired - Fee Related
- 1986-06-03 EP EP86903535A patent/EP0224551A1/en not_active Withdrawn
- 1986-06-10 DD DD86304091A patent/DD257255A5/de not_active IP Right Cessation
- 1986-06-10 DD DD86291160A patent/DD254877A5/de not_active IP Right Cessation
- 1986-06-11 CS CS864323A patent/CS261895B2/cs unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP0224551A1 (en) | 1987-06-10 |
| WO1986007354A1 (en) | 1986-12-18 |
| DD254877A5 (de) | 1988-03-16 |
| CS261895B2 (en) | 1989-02-10 |
| CS432386A2 (en) | 1988-06-15 |
| US4846883A (en) | 1989-07-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ENJ | Ceased due to non-payment of renewal fee |