JPS59148733A - β−フエノキシ−α−メチレンプロピオン酸誘導体 - Google Patents
β−フエノキシ−α−メチレンプロピオン酸誘導体Info
- Publication number
- JPS59148733A JPS59148733A JP2128183A JP2128183A JPS59148733A JP S59148733 A JPS59148733 A JP S59148733A JP 2128183 A JP2128183 A JP 2128183A JP 2128183 A JP2128183 A JP 2128183A JP S59148733 A JPS59148733 A JP S59148733A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- acid
- phenoxy
- compound
- acid derivative
- 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.)
- Granted
Links
- ZAGGZBMIXMCTKA-UHFFFAOYSA-N 2-(phenoxymethyl)prop-2-enoic acid Chemical class OC(=O)C(=C)COC1=CC=CC=C1 ZAGGZBMIXMCTKA-UHFFFAOYSA-N 0.000 title abstract description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 5
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 18
- 239000003795 chemical substances by application Substances 0.000 abstract description 7
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 abstract description 6
- 238000009833 condensation Methods 0.000 abstract description 4
- 230000005494 condensation Effects 0.000 abstract description 4
- 239000012442 inert solvent Substances 0.000 abstract description 4
- 230000008635 plant growth Effects 0.000 abstract description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract description 2
- 150000001412 amines Chemical class 0.000 abstract description 2
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- -1 thiophenyl ester Chemical class 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- 230000000694 effects Effects 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- 241000196324 Embryophyta Species 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 230000009036 growth inhibition Effects 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 230000000887 hydrating effect Effects 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000004809 thin layer chromatography Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- SYXLXURIAJHELR-UHFFFAOYSA-N 2-(phenoxymethyl)-n-phenylprop-2-enamide Chemical compound C=1C=CC=CC=1NC(=O)C(=C)COC1=CC=CC=C1 SYXLXURIAJHELR-UHFFFAOYSA-N 0.000 description 2
- RSQXDOLOVSUMOM-UHFFFAOYSA-N 2-(phenoxymethyl)prop-2-enoyl chloride Chemical compound ClC(=O)C(=C)COC1=CC=CC=C1 RSQXDOLOVSUMOM-UHFFFAOYSA-N 0.000 description 2
- KWNGIKVZXFFZNN-UHFFFAOYSA-M 2-chloro-1-methylpyridin-1-ium;4-methylbenzenesulfonate Chemical compound C[N+]1=CC=CC=C1Cl.CC1=CC=C(S([O-])(=O)=O)C=C1 KWNGIKVZXFFZNN-UHFFFAOYSA-M 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 2
- PXAJQJMDEXJWFB-UHFFFAOYSA-N acetone oxime Chemical compound CC(C)=NO PXAJQJMDEXJWFB-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 239000004020 conductor Substances 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- 230000012010 growth Effects 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 230000002829 reductive effect Effects 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- VIIIJFZJKFXOGG-UHFFFAOYSA-N 3-methylchromen-2-one Chemical compound C1=CC=C2OC(=O)C(C)=CC2=C1 VIIIJFZJKFXOGG-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 241001062872 Cleyera japonica Species 0.000 description 1
- 244000058871 Echinochloa crus-galli Species 0.000 description 1
- 235000008247 Echinochloa frumentacea Nutrition 0.000 description 1
- 206010053759 Growth retardation Diseases 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 241001474791 Proboscis Species 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- 235000005733 Raphanus sativus var niger Nutrition 0.000 description 1
- 235000006140 Raphanus sativus var sativus Nutrition 0.000 description 1
- 240000001970 Raphanus sativus var. sativus Species 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000004210 ether based solvent Substances 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000005089 fruit drop Effects 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- WFKDPJRCBCBQNT-UHFFFAOYSA-N n,2-dimethylprop-2-enamide Chemical compound CNC(=O)C(C)=C WFKDPJRCBCBQNT-UHFFFAOYSA-N 0.000 description 1
- IOMMMLWIABWRKL-WUTDNEBXSA-N nazartinib Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCC[C@H]1N1C2=C(Cl)C=CC=C2N=C1NC(=O)C1=CC=NC(C)=C1 IOMMMLWIABWRKL-WUTDNEBXSA-N 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 239000002373 plant growth inhibitor Substances 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- SMDQFHZIWNYSMR-UHFFFAOYSA-N sulfanylidenemagnesium Chemical compound S=[Mg] SMDQFHZIWNYSMR-UHFFFAOYSA-N 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 150000007970 thio esters Chemical class 0.000 description 1
- 150000003568 thioethers Chemical group 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2128183A JPS59148733A (ja) | 1983-02-10 | 1983-02-10 | β−フエノキシ−α−メチレンプロピオン酸誘導体 |
| EP84100497A EP0117412A1 (en) | 1983-01-18 | 1984-01-18 | Propene derivatives and their use as plant growth inhibitors |
| EP84100585A EP0118685A1 (en) | 1983-02-07 | 1984-01-20 | Propene derivatives and their use as plant growth inhibitors |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2128183A JPS59148733A (ja) | 1983-02-10 | 1983-02-10 | β−フエノキシ−α−メチレンプロピオン酸誘導体 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59148733A true JPS59148733A (ja) | 1984-08-25 |
| JPH0438740B2 JPH0438740B2 (enrdf_load_stackoverflow) | 1992-06-25 |
Family
ID=12050746
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2128183A Granted JPS59148733A (ja) | 1983-01-18 | 1983-02-10 | β−フエノキシ−α−メチレンプロピオン酸誘導体 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS59148733A (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2003048864A (ja) * | 2001-08-01 | 2003-02-21 | Nippon Shokubai Co Ltd | アリルエーテル誘導体の製造方法、該製法に供する前駆体および該製法により得られるアリルエーテル誘導体 |
-
1983
- 1983-02-10 JP JP2128183A patent/JPS59148733A/ja active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2003048864A (ja) * | 2001-08-01 | 2003-02-21 | Nippon Shokubai Co Ltd | アリルエーテル誘導体の製造方法、該製法に供する前駆体および該製法により得られるアリルエーテル誘導体 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0438740B2 (enrdf_load_stackoverflow) | 1992-06-25 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| SU628812A3 (ru) | Способ получени органических содинений | |
| PL104373B1 (pl) | Sposob wytwarzania nowych acyloanilin | |
| KR101182334B1 (ko) | 라말린의 합성방법 | |
| WO2021161200A1 (en) | Process for preparation of arthropodicidal anthranilamide compounds | |
| JP4257574B2 (ja) | Ｒ（＋）α−リポ酸の合成 | |
| JPH07116119B2 (ja) | 置換されたオキシムエーテル、該化合物の製法及び該化合物を含有する植物中の内因性エチレン含有量を低下させる生物学的生長調整剤 | |
| SU663267A3 (ru) | Способ борьбы с насекомыми,клещами и нематодами | |
| JPS59148733A (ja) | β−フエノキシ−α−メチレンプロピオン酸誘導体 | |
| WO1992013835A1 (en) | Salt of dithiocarbamic acid, production thereof, and production of isothiocyanate from said salt | |
| US3887615A (en) | Novel butanoic acid derivatives | |
| EP2647621B1 (en) | Method for producing sanshool | |
| RU2571417C2 (ru) | Способ получения n-замещенной 2-амино-4-(гидроксиметилфосфинил)-2-бутеновой кислоты | |
| US6147215A (en) | Process for producing 1-chlorocarbonyl-4-piperidinopiperidine or hydrochloride thereof | |
| KR0179459B1 (ko) | 디페록사민 제조에 사용된 중간체 | |
| SU1083906A3 (ru) | Способ получени фениловых сложных эфиров карбаминовой кислоты | |
| US3927062A (en) | Plant growth regulators | |
| RU2711231C1 (ru) | Способ получения регулятора роста растений N-(изопропоксикарбонил)-О-(4-хлорфенилкарбамоил)этаноламина | |
| HU201516B (en) | Process for producing 2-cyano-2-oximinoacetamide derivatives | |
| JPH0259818B2 (enrdf_load_stackoverflow) | ||
| US5510504A (en) | Process for the preparation of derivatives of bis(amino-methyl) phosphinic acid | |
| SU622398A3 (ru) | Способ получени производных оксима или их солей | |
| KR910000145B1 (ko) | N-(2-메톡시아세틸)-n-(2,6-자일릴)-d,l-알라닌 메틸에스테르의 제조방법 | |
| JP2671401B2 (ja) | α‐アミノチオアセトアミド誘導体およびその製造法 | |
| JPH0674250B2 (ja) | チオカルバメ−ト誘導体の製法 | |
| JPH0439464B2 (enrdf_load_stackoverflow) |