FI75817C - Oxiranderivat och foerfarande foer deras framstaellning. - Google Patents
Oxiranderivat och foerfarande foer deras framstaellning. Download PDFInfo
- Publication number
- FI75817C FI75817C FI861206A FI861206A FI75817C FI 75817 C FI75817 C FI 75817C FI 861206 A FI861206 A FI 861206A FI 861206 A FI861206 A FI 861206A FI 75817 C FI75817 C FI 75817C
- Authority
- FI
- Finland
- Prior art keywords
- formula
- preparation
- oxiranderivat
- foerfarande foer
- och foerfarande
- Prior art date
Links
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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
-
- 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
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/04—Compounds containing oxirane rings containing only hydrogen and carbon atoms in addition to the ring oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/08—Compounds containing oxirane rings with hydrocarbon radicals, substituted by halogen atoms, nitro radicals or nitroso radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
- C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
- C07D303/22—Ethers with hydroxy compounds containing no oxirane rings with monohydroxy compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Epoxy Compounds (AREA)
Description
7581 7
Oksiraanijohdannaisia ja menetelmä niiden valmistamiseksi
Jakamalla erotettu patenttihakemuksesta 823893 5 Keksintö koskee uusia oksiraanijohdannaisia ja mene telmää niiden valmistamiseksi. Näillä oksiraanijohdannaisilla on kaava (II) / Γ) \—CH=CH-C-C (CH-,) 10 A__/ /\ <«> z ^ 0 — CH.
m * jossa Z on kloori, fluori tai metyyli ja 15 m on 1 tai 2.
Keksinnön mukaisia oksiraanijohdannaisia voidaan käyttää välituotteina valmistettaessa patenttihakemuksessa 823893 esitettyjä uusia 1-hydroksietyyliatsolijohdannaisia, joilla on kaava (I) 20
/—\ °H
( O /— CH=CH-C-C(CH0) C„2 m .N.
25 O
jossa Z ja m ovat edellä määritellyt ja X on typpiatomi tai CH-ryhmä sekä niiden happosuoloja ja metallikomplekse-ja. Kaavan (I) mukaiset 1-hydroksietyyliatsolijohdannaiset ovat käyttökelpoisia kasvien kasvua säätelevinä aineina ja 30 sienimyrkkyinä. Niiden ominaisuuksia ja valmistusta kaavan (II) mukaisista oksiraanijohdannaisista on selostettu patenttihakemuksessa 823893. Kaavan (I) mukaisia yhdisteitä saadaan saattamalla kaavan (II) mukainen oksiraanijohdannainen reagoimaan atsolin kanssa, jolla on kaava (III)
35 H
/Ν·Νλ (III) ϋ 2 75817 jossa X on edellä määritelty.
Kaavan (II) mukaisia oksiraaneja valmistetaan keksinnön mukaisesti antamalla ketonien, joilla on kaava (IV) 5 —CH=CH-C-C(CH3) 3 (IV)
Zm C
jossa Z ja m ovat edellä määritellyt, reagoida joko 10 χ) dimetyylioksosulfoniummetylidin, jolla on kaava (V) 4 + £- (CH3)2SOCH2 (v) 15 kanssa laimennusaineen läsnäollessa, tai P>) trimetyylisulfoniummetyylisulfaatin, jolla on kaava (VI) _ ( + ) (-) (ch3)3s ch3so4 (VI) 20 kanssa inertin orgaanisen liuottimen ja emäksen läsnäollessa.
Kaavan (II) mukaisten oksiraanien valmistuksessa lähtöaineina tarvittavat kaavan (IV) mukaiset ketonit ovat tunnettuja (vrt. DE-PS 2 201 063, DE-OS 2 705 678, DE-OS 25 2 737 489, Tetrahedron 31 (1975) 3, Chemical Abstracts 84,73906η) tai ne voidaan valmistaa periaatteessa tunnetuilla menetelmillä.
Valmistusvaihtoehdossa bO tarvittava dimetyyliokso-sulfoniummetylidi, jolla on kaava (V), on samoin tunnettu 30 (vrt.J. Amer. Chem. Soc. 87 (1965) 1363-1364). Sitä käytetään yllä mainitussa reaktiossa vasta valmistettuna; annetaan trimetyylioksosulfoniumjodidin reagoida natriumhyd-ridin tai natriumamidin kanssa laimennusaineen läsnäollessa.
Valmistusvaihtoehdossa (fi) tarvittava trimetyylisul-35 foniummetyylisulfaatti, jolla on kaava (VI), on samoin tunnettu (vrt. Heterocycles 8 (1977) 397) . Sitä käytetään yllä
II
3 7581 7 mainitussa reaktiossa myöskin juuri valmistettuna dimetyy-lisulfidin ja dimetyylisulfaatin välisellä reaktiolla.
Kaavan (II) mukaisten oksiraanien valmistusvaihtoehdossa ίχ) voidaan käyttää laimennusaineena esim. dime-5 tyylisulfoksidia.
Reaktiolämpötilat voivat yllä mainitussa valmistus-vaihtoehdossa (o() vaihdella melko laajalla alueella. Yleensä käytetään lämpötiloja 20-80°C.
Kaavan (II) mukaisten oksiraanien valmistus menetel-10 mällä (cyj sekä synteesituotteen eristäminen saaduista reak-tioseoksista suoritetaan tavanomaisilla menetelmillä (vrt.
J. Amer. Chem. Soc. 87 (1965) 1363-1364).
Valmistettaessa oksiraaneja, joilla on kaava (II), menetelmällä (/») voidaan käyttää inerttinä orgaanisena 15 liuottimena esim. asetonitriiliä.
Valmistusvaihtoehdossa (Λ) voidaan käyttää emäksenä voimakkaita epäorgaanisia ja orgaanisia emäksiä. Esimerkiksi natriummetylaatia voidaan käyttää.
Reaktiolämpötilat voivat yllä mainitussa valmistus-20 vaihtoehdossa (^*>) vaihdella tietyissä rajoissa. Yleensä käytetään lämpötiloja 0-60°C, edullisesti huoneenlämpötilaa.
Kaavan (II) mukaisten oksiraanien valmistus menetelmällä (/1) sekä synteesituotteiden eristäminen suoritetaan tavanomaisilla menetelmillä (vrt. Heterocycles 8(1977)397). 25 Kaavan (II) mukaiset oksiraanit voidaan kaavan (I) mukaisten yhdisteiden valmistusmenetelmässä mahdollisesti käyttää eristämättä suoraan edelleen.
Keksintöä valaistaan lähemmin seuraavilla esimerkeillä.
30 Esimerkki 1 cx-^c^.ay, O—CH2 35 189 ml (2,0 mol) dimetyylisulfaattia liuotettuna 1200 ml:aan absoluuttista asetonitriiliä sekoitetaan huo- 4 7581 7 neen lämpötilassa 162 ml:aan (2,2 mol) liuotettuun dimetyy-lisulfidia, joka on liuotettu 400 ml:aan absoluuttista asetonitriiliä. Reaktioseosta sekoitetaan huoneen lämpötilassa yön yli. Sen jälkeen lisätään 118,8 g (2,2 mol) nat-5 riummetylaattia. Sekoitetaan 30 minuuttia ja lisätään sitten 30 minuutin aikana pisaroittain 267 g (1,2 mol) 1—(4— kloorifenyyli)-4,4-dimetyyli-but-l-en-3-onia 600 ml:ssa absoluuttista asetonitriiliä. Reaktioseosta sekoitetaan yön yli. Sen jälkeen seos haihdutetaan, jäännös uutetaan veden ja etyyliasetaatin seoksella, orgaaninen faasi otetaan talteen, pestään kahdesti vedellä ja kerran kyllästetyllä natriumkloridiliuoksella, kuivataan natriumsulfaa-tilla, haihdutetaan ja jäännös tislataan alipaineessa. Saadaan 2-(4-kloorifenyylietenyyli)-2-tert-butyylioksiraa-15 ni kiinteänä aineena, jonka sp. on 61 - 62,5°C.
Samalla tavalla saadaan seuraavat kaavan (II) mukaiset yhdisteet:
Taulukko 2 20 J&)-Y'C7C\(CH3·3 (ii)
Zm 0_CH2
Esim. Z Y Kiehumispiste no__™__(°C) /mm H_ 25 II-2 2,4-Cl2 -CH=CH- II-3 4-CH3 -CH=CH- ei eristetty II-4 4-F -CH=CH— 75/0,005 II-5 2-CH3 -CH=CH- 71-74/0,01 II-6 2,6-Cl2 -CH=CH- ^0 Kaavan (I) mukaisen lopputuotteen valmistus kaavan (II) mukaisesta oksiraanijohdannaisesta
/^y ?H
Cl—< (^)/~0Η=0Η-α-0(0Η3) 3 (I) 35 iH2
N
Of
II
5 7581 7 17,75 g (0,075 mol) 2-(4-kloorifenyylietenyyli)-2-tert-butyylioksiraania ja 6,8 g (0,1 mol) imidatsolia liuotettuna 30 ml:aan etanolia kuumennetaan 20 tuntia 150°C:ssa pommiputkessa. Sen jälkeen reaktioseos haihdutetaan ja ki-5 teinen jäännös sekoitetaan eetteriin. Kiinteä jäännös imu-suodatetaan ja uudelleenkiteytetään asetonitriilistä. Saadaan 1-(4-kloorifenyyli)-4,4-dimetyyli-3-(imidatsol-1-yylimetyyli)-l-penten-3-olia, jonka sp. on 158,5 - 162°C.
Claims (3)
1. Oksiraanijohdannaiset, joilla on kaava (II), -CH=CH^-C(CH3)3 (II) m n2 jossa Z on kloori, fluori tai metyyli ja 10 m on 1 tai 2.
2. Menetelmä oksiraanijohdannaisten valmistamiseksi, joilla on kaava (II), 15 /qWch-CH-£-C<CH3)3 (II) z ^ ' o—im, jossa Z on kloori, fluori tai metyyli ja m on 1 tai 2, 20 tunnettu siitä, että annetaan ketonien, joilla on kaava (IV), (C/-CH=CH-C-C(CH3)
3 (IV) z ' o 25 m jossa Z ja m ovat edellä määritellyt reagoida joko χ) dimetyylisulfoniummetylidin, jolla on kaava (V), 30 ~r+<f- <ch3)2soch, (V) kanssa laimennusaineen läsnäollessa tai fi) trimetyylisulfoniummetyylisulfaatin, jolla on kaava (VI) — — 35 (ch3)3s) ch3so4(-) (VI) kanssa inertin orgaanisen liuottimen ja emäksen läsnäollessa· II
Applications Claiming Priority (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19803018866 DE3018866A1 (de) | 1980-05-16 | 1980-05-16 | 1-hydroxyethyl-azol-derivate, verfahren zu ihrer herstellung sowie ihre verwendung als pflanzenwachstumsregulatoren und fungizide |
DE3018866 | 1980-05-16 | ||
DE19813106076 DE3106076A1 (de) | 1981-02-19 | 1981-02-19 | 1-hydroxyethyl-azol-derivate, verfahren zu ihrer herstellung sowie ihre verwendung als pflanzenwachstumsregulatoren und fungizide |
DE3106076 | 1981-02-19 | ||
FI823893 | 1982-11-12 | ||
FI823893A FI71732C (fi) | 1980-05-16 | 1982-11-12 | 1-hydroxietylazolderivat, deras framstaellningsfoerfarande och anvaendning som tillvaextregulerande medel foer vaexter och som fungicider. |
Publications (4)
Publication Number | Publication Date |
---|---|
FI861206A FI861206A (fi) | 1986-03-21 |
FI861206A0 FI861206A0 (fi) | 1986-03-21 |
FI75817B FI75817B (fi) | 1988-04-29 |
FI75817C true FI75817C (fi) | 1988-08-08 |
Family
ID=25785513
Family Applications (3)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
FI811472A FI73421C (fi) | 1980-05-16 | 1981-05-13 | 1-hydroxietylazolderivat, deras framstaellningsfoerfarande och anvaendning som vaextlighet reglerande medel samt som fungicider. |
FI861206A FI75817C (fi) | 1980-05-16 | 1986-03-21 | Oxiranderivat och foerfarande foer deras framstaellning. |
FI861230A FI861230A0 (fi) | 1980-05-16 | 1986-03-24 | 1-hydroxietylazolderivat, deras framsaollningsfoerfarande och anvaendning som vaextlighet reglerande medel samt som fungicider. |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
FI811472A FI73421C (fi) | 1980-05-16 | 1981-05-13 | 1-hydroxietylazolderivat, deras framstaellningsfoerfarande och anvaendning som vaextlighet reglerande medel samt som fungicider. |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
FI861230A FI861230A0 (fi) | 1980-05-16 | 1986-03-24 | 1-hydroxietylazolderivat, deras framsaollningsfoerfarande och anvaendning som vaextlighet reglerande medel samt som fungicider. |
Country Status (24)
Country | Link |
---|---|
US (8) | US4532341A (fi) |
EP (3) | EP0087148B1 (fi) |
JP (2) | JPH02167273A (fi) |
AR (2) | AR227310A1 (fi) |
AT (3) | ATE18666T1 (fi) |
AU (3) | AU542623B2 (fi) |
BR (1) | BR8103049A (fi) |
CA (2) | CA1341164C (fi) |
DD (2) | DD158847A5 (fi) |
DE (1) | DE3164696D1 (fi) |
DK (4) | DK158152C (fi) |
EG (1) | EG14836A (fi) |
ES (1) | ES502234A0 (fi) |
FI (3) | FI73421C (fi) |
GR (1) | GR78229B (fi) |
HU (3) | HU191671B (fi) |
IE (3) | IE52451B1 (fi) |
IL (6) | IL62863A (fi) |
NL (1) | NL971022I2 (fi) |
NZ (4) | NZ209126A (fi) |
OA (1) | OA06809A (fi) |
PH (3) | PH17636A (fi) |
PT (1) | PT72979B (fi) |
TR (4) | TR22691A (fi) |
Families Citing this family (198)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0052424B2 (en) * | 1980-11-19 | 1990-02-28 | Imperial Chemical Industries Plc | Triazole compounds, a process for preparing them, their use as plant fungicides and fungicidal compositions containing them |
HU187399B (en) * | 1980-12-24 | 1985-12-28 | Sumitomo Chemical Co | Process for preparing imidazolyl-propanol derivatives |
GR78218B (fi) * | 1981-07-02 | 1984-09-26 | Ciba Geigy Ag | |
US4435399A (en) * | 1981-07-18 | 1984-03-06 | Pfizer Inc. | 2-Aryl-1-(imidazol-1-yl)-8-(4-piperazin-1-ylphenoxy) octan-2-ol antifungal agents |
DE3145857A1 (de) * | 1981-11-19 | 1983-05-26 | Bayer Ag, 5090 Leverkusen | Alkylcyloalkyl-triazolylmethyl-ketone und verfahreen zu ihrer herstellung |
DE3202601A1 (de) * | 1982-01-27 | 1983-08-04 | Bayer Ag, 5090 Leverkusen | Substituierte 1 -hydroxyalkyl-azolyl-derivate, verfahren zu ihrer herstellung sowie ihrer verwendung als fungizide und pflanzenwachstumsregulatoren |
DE3202604A1 (de) * | 1982-01-27 | 1983-08-04 | Bayer Ag, 5090 Leverkusen | Ether-derivate von substituierten 1-hydroxyalkyl-azolen, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide und pflanzenwachstumsregulatoren |
DE3202613A1 (de) * | 1982-01-27 | 1983-08-04 | Bayer Ag, 5090 Leverkusen | Antimykotische mittel |
US4940481A (en) * | 1982-03-04 | 1990-07-10 | Ciba-Geigy Corporation | Microbicidal and growth regulating compositions |
US5236953A (en) * | 1982-04-14 | 1993-08-17 | Imperial Chemical Industries Plc | Alkene, alkyne or cycloalkylene derivatives |
GB8504093D0 (en) * | 1985-02-18 | 1985-03-20 | Ici Plc | Alkene alkyne/cycloalkylene derivatives |
EP0097426B1 (en) * | 1982-06-14 | 1988-09-07 | Imperial Chemical Industries Plc | Triazole compounds |
DE3229274A1 (de) * | 1982-08-05 | 1984-02-09 | Bayer Ag, 5090 Leverkusen | Substituierte azolylvinyl-ketone und -carbinole |
DE3232647A1 (de) * | 1982-09-02 | 1984-03-08 | Bayer Ag, 5090 Leverkusen | Substituierte tert.-butanol-derivate, verfahren zu ihrer herstellung und diese enthaltende antimykotische mittel |
DE3237400A1 (de) * | 1982-10-08 | 1984-04-12 | Bayer Ag, 5090 Leverkusen | Substituierte 1-hydroxyethyl-triazolyl-derivate |
US4505919A (en) * | 1982-10-09 | 1985-03-19 | Pfizer Inc. | Antifungal S-arylmethyl- and S-heterocyclylmethyl ethers of 2-aryl-3-mercapto-1-(1H-1,2,4-triazol-1-yl) propan-2-ols |
ATE48995T1 (de) * | 1983-01-10 | 1990-01-15 | Ciba Geigy Ag | Fluorazolyl-propanol-derivate als mikrobizide und wuchsregulierende mittel. |
EP0117100B1 (en) * | 1983-02-16 | 1986-12-10 | Pfizer Limited | Triazole antifungal agents |
DE3307217A1 (de) * | 1983-03-02 | 1984-09-06 | Bayer Ag, 5090 Leverkusen | Substituierte 1,3-diazolyl-2-propanole, verfahren zu ihrer herstellung und ihre verwendung als antimykotische mittel |
DE3311702A1 (de) * | 1983-03-30 | 1984-10-04 | Bayer Ag, 5090 Leverkusen | Fungizide mittel, verfahren zu ihrer herstellung und deren verwendung |
DE3315681A1 (de) * | 1983-04-29 | 1984-10-31 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von oxiranen |
DE3315524A1 (de) * | 1983-04-29 | 1984-10-31 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von oxiranen |
DE3315619A1 (de) * | 1983-04-29 | 1984-10-31 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von oxiranen |
DE3315510A1 (de) * | 1983-04-29 | 1984-10-31 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von oxiranen |
DE3315808A1 (de) * | 1983-04-30 | 1984-10-31 | Bayer Ag, 5090 Leverkusen | Antivirale mittel |
GB2143815B (en) * | 1983-05-19 | 1988-01-20 | Ciba Geigy Ag | Process for the preparation of micro biocidal 1-triazolylethyl ether derivatives |
DE3321158A1 (de) * | 1983-06-11 | 1984-12-13 | Bayer Ag, 5090 Leverkusen | Azolylmethyl-thienyl-carbinol-derivate |
US5198231A (en) * | 1983-09-16 | 1993-03-30 | Bayer Aktiengesellschaft | Fungicidal agents |
DE3333411A1 (de) * | 1983-09-16 | 1985-04-04 | Bayer Ag, 5090 Leverkusen | Fungizide mittel |
DE3333412A1 (de) | 1983-09-16 | 1985-04-04 | Bayer Ag, 5090 Leverkusen | Fungizide mittel |
US5250560A (en) * | 1983-09-16 | 1993-10-05 | Bayer Aktiengesellschaft | Fungicidal agents |
DE3334779A1 (de) * | 1983-09-26 | 1985-04-11 | Bayer Ag, 5090 Leverkusen | Hydroxyethyl-azol-derivate |
DE3342692A1 (de) * | 1983-11-25 | 1985-06-05 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von ss-hydroxyethyl-(1,2,4-triazol)-derivaten |
DE3401714A1 (de) * | 1984-01-19 | 1985-07-25 | Celamerck Gmbh & Co Kg, 6507 Ingelheim | Neuartige azole mit enoletherstruktur, ihre herstellung und verwendung |
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-
1981
- 1981-04-13 AU AU69456/81A patent/AU542623B2/en not_active Expired
- 1981-05-02 AT AT83101614T patent/ATE18666T1/de not_active IP Right Cessation
- 1981-05-02 EP EP83101614A patent/EP0087148B1/de not_active Expired
- 1981-05-02 EP EP82108279A patent/EP0072580B1/de not_active Expired
- 1981-05-02 AT AT81103322T patent/ATE8391T1/de active
- 1981-05-02 AT AT82108279T patent/ATE25522T1/de not_active IP Right Cessation
- 1981-05-02 DE DE8181103322T patent/DE3164696D1/de not_active Expired
- 1981-05-02 EP EP81103322A patent/EP0040345B1/de not_active Expired
- 1981-05-06 PT PT72979A patent/PT72979B/pt unknown
- 1981-05-11 PH PH25615A patent/PH17636A/en unknown
- 1981-05-12 EG EG259/81A patent/EG14836A/xx active
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- 1981-05-13 NZ NZ209126A patent/NZ209126A/en unknown
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- 1981-05-13 DD DD81244788A patent/DD205602A5/de not_active IP Right Cessation
- 1981-05-14 TR TR2530/84A patent/TR22691A/xx unknown
- 1981-05-14 GR GR64959A patent/GR78229B/el unknown
- 1981-05-14 TR TR2532/84A patent/TR22396A/xx unknown
- 1981-05-14 TR TR22042A patent/TR22042A/xx unknown
- 1981-05-14 ES ES502234A patent/ES502234A0/es active Granted
- 1981-05-14 TR TR2531/84A patent/TR22400A/xx unknown
- 1981-05-15 OA OA57402A patent/OA06809A/xx unknown
- 1981-05-15 IE IE957/86A patent/IE52451B1/en unknown
- 1981-05-15 HU HU842227A patent/HU191671B/hu not_active IP Right Cessation
- 1981-05-15 IE IE1093/81A patent/IE52450B1/en not_active IP Right Cessation
- 1981-05-15 AR AR285338A patent/AR227310A1/es active
- 1981-05-15 HU HU811362A patent/HU188092B/hu unknown
- 1981-05-15 CA CA000617114A patent/CA1341164C/en not_active Expired - Lifetime
- 1981-05-15 BR BRPI8103049-5A patent/BR8103049A/pt not_active IP Right Cessation
- 1981-05-15 IE IE958/86A patent/IE52452B1/en unknown
- 1981-05-15 HU HU842226A patent/HU191148B/hu not_active IP Right Cessation
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1982
- 1982-05-11 AR AR289367A patent/AR229527A1/es active
- 1982-11-09 PH PH28114A patent/PH25843A/en unknown
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1983
- 1983-05-31 PH PH28986A patent/PH25782A/en unknown
- 1983-06-06 US US06/499,679 patent/US4532341A/en not_active Expired - Lifetime
- 1983-11-08 US US06/549,867 patent/US4897107A/en not_active Expired - Lifetime
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1984
- 1984-06-18 US US06/621,968 patent/US4723984A/en not_active Expired - Lifetime
- 1984-12-04 AU AU36293/84A patent/AU560022B2/en not_active Ceased
- 1984-12-04 AU AU36292/84A patent/AU556515B2/en not_active Ceased
-
1985
- 1985-01-28 US US06/695,610 patent/US4626595A/en not_active Expired - Lifetime
- 1985-02-06 DK DK54285A patent/DK54285A/da not_active Application Discontinuation
- 1985-02-06 DK DK54385A patent/DK54385A/da not_active Application Discontinuation
- 1985-02-06 DK DK054185A patent/DK163507C/da not_active IP Right Cessation
- 1985-05-08 US US06/732,191 patent/US4911746A/en not_active Expired - Fee Related
- 1985-05-08 US US06/732,193 patent/US4871390A/en not_active Expired - Fee Related
- 1985-05-08 US US06/732,194 patent/US4789672A/en not_active Expired - Fee Related
- 1985-06-14 IL IL75521A patent/IL75521A0/xx unknown
- 1985-06-14 IL IL75520A patent/IL75520A0/xx not_active IP Right Cessation
- 1985-06-14 IL IL75519A patent/IL75519A0/xx unknown
-
1986
- 1986-03-21 FI FI861206A patent/FI75817C/fi not_active IP Right Cessation
- 1986-03-24 FI FI861230A patent/FI861230A0/fi not_active Application Discontinuation
-
1987
- 1987-06-05 US US07/058,479 patent/US4904298A/en not_active Expired - Lifetime
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1989
- 1989-11-22 JP JP1302307A patent/JPH02167273A/ja active Granted
- 1989-11-22 JP JP1302308A patent/JPH02167270A/ja active Granted
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1997
- 1997-07-24 NL NL971022C patent/NL971022I2/nl unknown
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2005
- 2005-08-15 CA CA000377689A patent/CA1341521C/en not_active Expired - Fee Related
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Owner name: BAYER AKTIENGESELLSCHAFT |