JPH0149324B2 - - Google Patents
Info
- Publication number
- JPH0149324B2 JPH0149324B2 JP8831685A JP8831685A JPH0149324B2 JP H0149324 B2 JPH0149324 B2 JP H0149324B2 JP 8831685 A JP8831685 A JP 8831685A JP 8831685 A JP8831685 A JP 8831685A JP H0149324 B2 JPH0149324 B2 JP H0149324B2
- Authority
- JP
- Japan
- Prior art keywords
- acid
- ether
- reaction
- add
- lactam
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 239000005648 plant growth regulator Substances 0.000 claims description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 11
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 150000003951 lactams Chemical class 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- NGSWKAQJJWESNS-UHFFFAOYSA-N 4-coumaric acid Chemical compound OC(=O)C=CC1=CC=C(O)C=C1 NGSWKAQJJWESNS-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical compound O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 3
- 230000018044 dehydration Effects 0.000 description 3
- 238000006297 dehydration reaction Methods 0.000 description 3
- 150000004702 methyl esters Chemical class 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- JLIDBLDQVAYHNE-YKALOCIXSA-N (+)-Abscisic acid Chemical compound OC(=O)/C=C(/C)\C=C\[C@@]1(O)C(C)=CC(=O)CC1(C)C JLIDBLDQVAYHNE-YKALOCIXSA-N 0.000 description 2
- XQXPVVBIMDBYFF-UHFFFAOYSA-N 4-hydroxyphenylacetic acid Chemical compound OC(=O)CC1=CC=C(O)C=C1 XQXPVVBIMDBYFF-UHFFFAOYSA-N 0.000 description 2
- 229930192334 Auxin Natural products 0.000 description 2
- 229930191978 Gibberellin Natural products 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 239000002363 auxin Substances 0.000 description 2
- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- 239000003448 gibberellin Substances 0.000 description 2
- IXORZMNAPKEEDV-OBDJNFEBSA-N gibberellin A3 Chemical class C([C@@]1(O)C(=C)C[C@@]2(C1)[C@H]1C(O)=O)C[C@H]2[C@]2(C=C[C@@H]3O)[C@H]1[C@]3(C)C(=O)O2 IXORZMNAPKEEDV-OBDJNFEBSA-N 0.000 description 2
- 230000012010 growth Effects 0.000 description 2
- 239000003630 growth substance Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 230000001035 methylating effect Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- NMHMNPHRMNGLLB-UHFFFAOYSA-N phloretic acid Chemical compound OC(=O)CCC1=CC=C(O)C=C1 NMHMNPHRMNGLLB-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 125000001325 propanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- OKDGRDCXVWSXDC-UHFFFAOYSA-N 2-chloropyridine Chemical class ClC1=CC=CC=N1 OKDGRDCXVWSXDC-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 241000219094 Vitaceae Species 0.000 description 1
- 230000000397 acetylating effect Effects 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- -1 alkali metal salt Chemical class 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- UQHKFADEQIVWID-UHFFFAOYSA-N cytokinin Natural products C1=NC=2C(NCC=C(CO)C)=NC=NC=2N1C1CC(O)C(CO)O1 UQHKFADEQIVWID-UHFFFAOYSA-N 0.000 description 1
- 239000004062 cytokinin Substances 0.000 description 1
- FCRACOPGPMPSHN-UHFFFAOYSA-N desoxyabscisic acid Natural products OC(=O)C=C(C)C=CC1C(C)=CC(=O)CC1(C)C FCRACOPGPMPSHN-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 230000035784 germination Effects 0.000 description 1
- 235000021021 grapes Nutrition 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-N methyl sulfate Chemical compound COS(O)(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-N 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 239000003375 plant hormone Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000006227 trimethylsilylation reaction Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Other In-Based Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Pyrrole Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8831685A JPS61246105A (ja) | 1985-04-23 | 1985-04-23 | 植物生長調節剤 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8831685A JPS61246105A (ja) | 1985-04-23 | 1985-04-23 | 植物生長調節剤 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61246105A JPS61246105A (ja) | 1986-11-01 |
| JPH0149324B2 true JPH0149324B2 (zh) | 1989-10-24 |
Family
ID=13939522
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP8831685A Granted JPS61246105A (ja) | 1985-04-23 | 1985-04-23 | 植物生長調節剤 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61246105A (zh) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0294053B1 (en) * | 1987-06-04 | 1994-08-10 | Taki Chemical Co., Ltd. | Composition for agricultural use |
| JPH01151503A (ja) * | 1987-12-08 | 1989-06-14 | Taki Chem Co Ltd | 植物生長調節剤 |
| US11878971B2 (en) | 2020-12-29 | 2024-01-23 | Huscion Co., Ltd. | Piperlongumine-based compound and immuno regulator comprising the same |
| EP4277896A1 (en) * | 2021-01-14 | 2023-11-22 | B.G. Negev Technologies and Applications Ltd., at Ben-Gurion University | Anti-quorum sensing, anti-biofilm, and inflammation attenuating compounds, compositions, and methods of using same |
-
1985
- 1985-04-23 JP JP8831685A patent/JPS61246105A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS61246105A (ja) | 1986-11-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0061386B1 (fr) | Acides ((2-oxo-3-tétrahydrothiénylcarbamoyl)-alkylthio) acétiques, leurs sels et leurs esters, leur procédé de préparation et les compositions pharmaceutiques en contenant | |
| CN107473962A (zh) | 一种(r)‑2‑(4‑氯‑2‑甲基苯氧)丙酸辛酯阻根剂的制备方法 | |
| CN110305010A (zh) | 一种2,5-二甲基苯乙酸的制备方法 | |
| JPH039899B2 (zh) | ||
| HU186526B (en) | Process for producing optically active 1-alkanone derivatives substituted at the 1 position with and aromatic group | |
| JPH0149324B2 (zh) | ||
| SU495826A3 (ru) | Способ получени аминоспиртов | |
| CN104072455B (zh) | 6-芳氧乙酰氧基橙酮类化合物及其在农药上的应用 | |
| DE60204014T2 (de) | Chlormethylierung von thiophen | |
| JPH0149323B2 (zh) | ||
| JPH0466229B2 (zh) | ||
| US2818425A (en) | 4-(chlorophenoxy) valeric acids | |
| JP2958434B2 (ja) | 含フッ素β−インドール酪酸類 | |
| JPH07100691B2 (ja) | 置換含フッ素β‐インドール酪酸類及びそれを有効成分として含有する植物生長調節剤 | |
| US4244731A (en) | Method for controlling the growth of plants | |
| JPH0513946B2 (zh) | ||
| JPS5835505B2 (ja) | Ｎ−（α−メチル−ベンジル）−脂肪酸アミド | |
| CN1041936A (zh) | 家蝇性诱剂合成方法 | |
| TW381083B (en) | Process for the preparation of substituted pyrimidines | |
| US4629497A (en) | Certain 1-(N-methylsulfonamido)-prop-2-yl 2-/4-(pyrid-2-yloxy)phenoxy/-propionate derivatives and their use for increasing recoverable sugar contained in sugar cane | |
| BE818471A (fr) | Procede pour preparer des 1-aralkyl-4-amino-methylpiperidine-4-ols | |
| JPS63270661A (ja) | １−〔２−（４−ヒドロキシベンゾイル）エタノイル〕−２−ピペリドン及びその製造法並びにそれを有効成分とするアルコ−ル発酵促進剤 | |
| JPH0149681B2 (zh) | ||
| Smith et al. | Structural requirements for phenylalanine antagonism | |
| KR0126545B1 (ko) | 신규한 불소치환 아브시스산 유도체 및 그를 포함하는 식물생장조절제 |