HU202220B - Process for producing 2,2-difluoro-4-amino-1,3-benzodioxole - Google Patents
Process for producing 2,2-difluoro-4-amino-1,3-benzodioxole Download PDFInfo
- Publication number
- HU202220B HU202220B HU893975A HU397589A HU202220B HU 202220 B HU202220 B HU 202220B HU 893975 A HU893975 A HU 893975A HU 397589 A HU397589 A HU 397589A HU 202220 B HU202220 B HU 202220B
- Authority
- HU
- Hungary
- Prior art keywords
- benzodioxole
- difluoro
- amino
- producing
- preparation
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 3
- RXIKYXZKSIARLN-UHFFFAOYSA-N 2,2-difluoro-1,3-benzodioxol-4-amine Chemical compound NC1=CC=CC2=C1OC(F)(F)O2 RXIKYXZKSIARLN-UHFFFAOYSA-N 0.000 title claims 2
- 238000002360 preparation method Methods 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 235000011114 ammonium hydroxide Nutrition 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- -1 difluoro-4-amino-1,3-benzodioxole Chemical compound 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- DBUAYOWCIUQXQW-UHFFFAOYSA-N 1,3-benzodioxole-4-carboxylic acid Chemical compound OC(=O)C1=CC=CC2=C1OCO2 DBUAYOWCIUQXQW-UHFFFAOYSA-N 0.000 description 1
- ODNBVEIAQAZNNM-UHFFFAOYSA-N 1-(6-chloroimidazo[1,2-b]pyridazin-3-yl)ethanone Chemical compound C1=CC(Cl)=NN2C(C(=O)C)=CN=C21 ODNBVEIAQAZNNM-UHFFFAOYSA-N 0.000 description 1
- PRTGZKWYZVEGQI-UHFFFAOYSA-N 2,2-dichloro-1,3-benzodioxole-4-carbonyl chloride Chemical compound ClC(=O)C1=CC=CC2=C1OC(Cl)(Cl)O2 PRTGZKWYZVEGQI-UHFFFAOYSA-N 0.000 description 1
- ZWZPONMLVROOLH-UHFFFAOYSA-N 2,2-difluoro-1,3-benzodioxole-4-carbonyl fluoride Chemical compound FC(=O)C1=CC=CC2=C1OC(F)(F)O2 ZWZPONMLVROOLH-UHFFFAOYSA-N 0.000 description 1
- LJGCAWPZURVJEZ-UHFFFAOYSA-N 2,2-difluoro-1,3-benzodioxole-4-carboxamide Chemical compound NC(=O)C1=CC=CC2=C1OC(F)(F)O2 LJGCAWPZURVJEZ-UHFFFAOYSA-N 0.000 description 1
- GUNJVIDCYZYFGV-UHFFFAOYSA-K Antimony trifluoride Inorganic materials F[Sb](F)F GUNJVIDCYZYFGV-UHFFFAOYSA-K 0.000 description 1
- WKHXPBPENLHARS-UHFFFAOYSA-N C1=CC(=C(C2=C1OC(O2)Cl)C(=O)Cl)Cl Chemical compound C1=CC(=C(C2=C1OC(O2)Cl)C(=O)Cl)Cl WKHXPBPENLHARS-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 230000000895 acaricidal effect Effects 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- RAIZEWRUXAWJMU-UHFFFAOYSA-N n-[2,4-dinitro-6-(trifluoromethyl)phenyl]-2,2-difluoro-1,3-benzodioxol-4-amine Chemical compound FC(F)(F)C1=CC([N+](=O)[O-])=CC([N+]([O-])=O)=C1NC1=CC=CC2=C1OC(F)(F)O2 RAIZEWRUXAWJMU-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
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
-
- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/24—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms
- A01N43/26—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings
- A01N43/28—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings with two hetero atoms in positions 1,3
- A01N43/30—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings with two hetero atoms in positions 1,3 with two oxygen atoms in positions 1,3, condensed with a carbocyclic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- 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)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
Description
A találmány tárgya eljárás fungicid és akaricid készítmények hatóanyagaként alkalmazott 2,2-difiuor-4-(2’,4’-dinitro-6’-/trifluor-metil/-anilino)-l,3-benzodioxol előállításához szolgáló 2,2-difluor-4-amino-l,3-benzodioxol előállítására.
A (II) képletű vegyület új. Előállítása Hofmann-féle lebontással történhet, azaz 2,2-difluor-4-kaibamoil-l ,3-bcnzodioxol brómmal való reagáltatása útján vizes alkálifém-hidroxid jelenlétében, az 1. reakcióvázlat szerint.
Az eljárást Yagupolskii M. L. és munkatársai leírása szerint hajtjuk végre [Zhur. Obshch, Khym. 57, 628 (1981)].
A (II) képletű vegyület előállítására szolgáló (I) képletű kiindulóanyagot több lépésben állítjuk elő 4-karboxi-l,3-benzodioxolból kiindulva, a 2-4. reakcióvázlatokban feltüntetett reakciók szerint [Perkin W. H. és Trikojus V. M., J. Chem. Soc. 1926, (2925)].
l.péida
2.2- Difluor-4-amino-l ,3-benzodioxol előállítása
1. reakcióvázlat
120 g kálium-hidroxid 780 ml vízzel készült oldatába 0*C-on brómot csepegtetünk. Utána 50,8 g 2,2-difluor-4-karbamoil-l,3-benzodioxolt adunk hozzá és a reakcióelegyet szobahőmérsékleten 30 percig keverjük, majd 45 percig 80 ’C-on melegítjük. Az oldatot 400 ml vízzel hígítjuk és vízgőzdesztillációt alkalmazva lepároljuk. A desztillátumot dietil-éterrel extraháljuk és nátrium-szulfát felett szárítjuk. Az oldószert lepárolva 38,1 g címben megadott vegyületet kapunk sárgás olaj alakjában, melynek törésmutatója [a] £ = 1,4955.
2. példa
2.2- Diklór-4-(klór-karbonil)-l,3-benzodioxol előállítása
2. reakcióvázlat g 4-karboxi-l,3-benzodioxolt 150 g foszfor-pentakloriddal összekeverünk és 70 *C-ra melegítünk. 3,5 óra múlva a hőmérsékletet 90 ’C-ig emeljük és 12 órán át ezen a hőmérsékleten tartjuk a keveréket.
Ezután az illékony komponenseket 110 ’C hőmérsékleten és 2000 Pa nyomáson lepároljuk és a maradékot nagyvákuumban desztilláljuk. 45 g címben megadott vegyületet kapunk sárgás szilárd anyag alakjában.
3. példa
2.2- Difluor-4-(fluor-karbonil-l ,3-benzodioxol előállítása
3. reakcióvázlat
59,4 g 2,2-diklór-4-(klór-karbonil)-l,3-benzodioxolhoz lepárlókészülékben 55,7 g antimon-trifluoridot adunk, ekkor a reakció azonnal megindul. A reakció fenntartása céljából a hőmérsékletet lassan emeljük, miközben a vákuumot lassan, fokozatosan növeljük. 105117 ’C-on és 6666 Pa nyomáson 59,6 g piros olaj desztillál át. A párlatot 100 ml dietil-éterben felvesszük, 2 x 150 ml félig telített sósavoldattal, majd vízzel mossuk. Az éteres oldat szárítása után az oldószert lepároljuk. 42,0 g címben megadott vegyületet kapunk.
4. példa
2.2- Difluor-4-karbamoil-l ,3-benzodioxol előállítása
4. reakcióvázlat
63,6 g 2,2-difluor-4-(fluor-karbonil)-l,3-benzodioxolhoz jeges hűtés és keverés közben 120 ml tömény (251%) ammóniaoldatot csepegtetünk. Néhány óra alatt kristálypép képződik, melyet leszűrünk, és egymás után híg ammóniaoldattal és vízzel mossuk. 51 g 2,2-difluor-4-karbamoil-13-benzodioxolt kapunk; olvadáspont: 129,5-131 ’C.
Claims (1)
- Eljárás (II) képletű 2,2-difluor-4-amino-l,3-benzodioxol előállítására, azzal jellemezve, hogy (I) képletű vegyülcten brómmal, vizes alkálifém-hidroxid-oldat jelenlétében Hofmann-féle lebontást hajtunk végre.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH143485 | 1985-04-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU202220B true HU202220B (en) | 1991-02-28 |
Family
ID=4210371
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU861358A HU198704B (en) | 1985-04-03 | 1986-04-02 | Fungicide and acaricide composition and process for producing 2,2-difluoro-4-/2;4'-dinitro-6'-/trifluoro-methyl/-anilino/-1,3-benzodioxol as active component |
| HU893975A HU202220B (en) | 1985-04-03 | 1986-04-02 | Process for producing 2,2-difluoro-4-amino-1,3-benzodioxole |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU861358A HU198704B (en) | 1985-04-03 | 1986-04-02 | Fungicide and acaricide composition and process for producing 2,2-difluoro-4-/2;4'-dinitro-6'-/trifluoro-methyl/-anilino/-1,3-benzodioxol as active component |
Country Status (16)
| Country | Link |
|---|---|
| US (2) | US4722935A (hu) |
| EP (1) | EP0198797B1 (hu) |
| JP (1) | JPS61229876A (hu) |
| KR (1) | KR860008160A (hu) |
| AR (1) | AR240927A1 (hu) |
| AT (1) | ATE49963T1 (hu) |
| AU (1) | AU592555B2 (hu) |
| BR (1) | BR8601482A (hu) |
| CA (1) | CA1242735A (hu) |
| DE (1) | DE3668618D1 (hu) |
| ES (2) | ES8800677A1 (hu) |
| GB (1) | GB2173793B (hu) |
| HU (2) | HU198704B (hu) |
| IL (1) | IL78320A (hu) |
| PT (1) | PT82308B (hu) |
| ZA (1) | ZA862414B (hu) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8705258D0 (en) * | 1987-03-06 | 1987-04-08 | Betka M | Drinking vessels |
| US5194628A (en) * | 1988-03-18 | 1993-03-16 | Ciba-Geigy Corporation | Process for the preparation of substituted difluorobenzo-1,3-dioxoles |
| US5420301A (en) * | 1988-03-18 | 1995-05-30 | Ciba-Geigy Corporation | Process for the preparation of substituted difluorobenzo-1,3-dioxoles |
| CH687877A5 (de) * | 1988-03-18 | 1997-03-14 | Ciba Geigy Ag | 2,2-Difluorbenzo-1,3-dioxol-4-carbaldehyd. |
| US5374637A (en) * | 1989-03-22 | 1994-12-20 | Janssen Pharmaceutica N.V. | N-(3-hydroxy-4-piperidinyl)(dihydrobenzofuran, dihydro-2H-benzopyran or dihydrobenzodioxin)carboxamide derivatives |
| DE4133156A1 (de) * | 1991-10-07 | 1993-04-08 | Bayer Ag | Verfahren zur herstellung von fluorsubstituierten aminobenzodioxolen und -benzodioxanen und neue zwischenprodukte |
| DE4133157A1 (de) * | 1991-10-07 | 1993-04-08 | Bayer Ag | In 4-stellung substituierte derivate von 2,2-dihalogenbenzo (1,3) dioxolen, verfahren zu ihrer herstellung ung ihrer verwendung |
| CA2109514A1 (en) * | 1992-05-22 | 1993-11-23 | Hermann Rempfler | N-(difluoro benzodioxolyl)-2-pyrrolidones, as herbicides |
| TW269680B (hu) * | 1992-11-05 | 1996-02-01 | Ciba Geigy | |
| WO1996011190A1 (de) * | 1994-10-06 | 1996-04-18 | Bayer Aktiengesellschaft | Substituierte biphenyloxazoline |
| DE69509558T2 (de) * | 1994-12-02 | 1999-10-07 | Novartis Ag, Basel | Karbamat herbizide |
| CN109232543A (zh) * | 2018-08-28 | 2019-01-18 | 李金铃 | 一种杀菌剂及其应用 |
| CN109020965A (zh) * | 2018-08-28 | 2018-12-18 | 李金铃 | 一种杀菌剂及其应用 |
| CN109053703A (zh) * | 2018-08-28 | 2018-12-21 | 李金铃 | 一种杀菌剂及其应用 |
| CN109134442A (zh) * | 2018-08-28 | 2019-01-04 | 李金铃 | 一种杀菌剂及其应用 |
| CN109053704A (zh) * | 2018-08-28 | 2018-12-21 | 李金铃 | 一种杀菌剂及其应用 |
| CN109020964A (zh) * | 2018-08-28 | 2018-12-18 | 李金铃 | 一种杀菌剂及其应用 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2823168A1 (de) * | 1978-05-26 | 1979-11-29 | Bayer Ag | 5-arylamino-2,2-difluor-benzodioxole, verfahren zu ihrer herstellung und ihre verwendung zur schaedlingsbekaempfung |
-
1986
- 1986-03-25 US US06/843,533 patent/US4722935A/en not_active Expired - Fee Related
- 1986-03-26 DE DE8686810145T patent/DE3668618D1/de not_active Expired - Lifetime
- 1986-03-26 AT AT86810145T patent/ATE49963T1/de not_active IP Right Cessation
- 1986-03-26 GB GB08607566A patent/GB2173793B/en not_active Expired
- 1986-03-26 EP EP86810145A patent/EP0198797B1/de not_active Expired - Lifetime
- 1986-03-28 IL IL78320A patent/IL78320A/xx unknown
- 1986-04-01 PT PT82308A patent/PT82308B/pt not_active IP Right Cessation
- 1986-04-01 CA CA000505550A patent/CA1242735A/en not_active Expired
- 1986-04-01 AR AR303537A patent/AR240927A1/es active
- 1986-04-02 KR KR1019860002496A patent/KR860008160A/ko not_active Ceased
- 1986-04-02 ZA ZA862414A patent/ZA862414B/xx unknown
- 1986-04-02 AU AU55579/86A patent/AU592555B2/en not_active Ceased
- 1986-04-02 ES ES553624A patent/ES8800677A1/es not_active Expired
- 1986-04-02 HU HU861358A patent/HU198704B/hu not_active IP Right Cessation
- 1986-04-02 HU HU893975A patent/HU202220B/hu unknown
- 1986-04-02 BR BR8601482A patent/BR8601482A/pt unknown
- 1986-04-03 JP JP61077524A patent/JPS61229876A/ja active Pending
-
1987
- 1987-07-31 ES ES557639A patent/ES8801645A1/es not_active Expired
- 1987-10-09 US US07/106,303 patent/US4859783A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| AU5557986A (en) | 1986-10-09 |
| ES8800677A1 (es) | 1987-11-16 |
| IL78320A (en) | 1991-08-16 |
| GB2173793A (en) | 1986-10-22 |
| GB8607566D0 (en) | 1986-04-30 |
| HUT41213A (en) | 1987-04-28 |
| EP0198797A2 (de) | 1986-10-22 |
| DE3668618D1 (de) | 1990-03-08 |
| ES557639A0 (es) | 1988-02-16 |
| BR8601482A (pt) | 1986-12-09 |
| EP0198797B1 (de) | 1990-01-31 |
| KR860008160A (ko) | 1986-11-12 |
| US4722935A (en) | 1988-02-02 |
| AR240927A2 (es) | 1991-03-27 |
| ZA862414B (en) | 1986-11-26 |
| HU198704B (en) | 1989-11-28 |
| EP0198797A3 (en) | 1987-08-26 |
| AU592555B2 (en) | 1990-01-18 |
| AR240927A1 (es) | 1991-03-27 |
| ATE49963T1 (de) | 1990-02-15 |
| CA1242735A (en) | 1988-10-04 |
| GB2173793B (en) | 1989-01-25 |
| PT82308A (en) | 1986-05-01 |
| ES8801645A1 (es) | 1988-02-16 |
| US4859783A (en) | 1989-08-22 |
| PT82308B (pt) | 1988-07-29 |
| ES553624A0 (es) | 1987-11-16 |
| JPS61229876A (ja) | 1986-10-14 |
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