FI75817C - Oxiranderivat och foerfarande foer deras framstaellning. - Google Patents

Oxiranderivat och foerfarande foer deras framstaellning. Download PDF

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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
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FI
Finland
Prior art keywords
formula
preparation
oxirane derivatives
derivatives
oxirane
Prior art date
Application number
FI861206A
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English (en)
Swedish (sv)
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FI75817B (fi
FI861206L (fi
FI861206A0 (fi
Inventor
Graham Holmwood
Karl Heinz Buechel
Klaus Luerssen
Paul-Ernst Frohberger
Wilhelm Brandes
Original Assignee
Bayer Ag
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Publication date
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First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=25785513&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=FI75817(C) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Priority claimed from DE19803018866 external-priority patent/DE3018866A1/de
Priority claimed from DE19813106076 external-priority patent/DE3106076A1/de
Priority claimed from FI823893A external-priority patent/FI71732C/fi
Application filed by Bayer Ag filed Critical Bayer Ag
Publication of FI861206L publication Critical patent/FI861206L/fi
Publication of FI861206A0 publication Critical patent/FI861206A0/fi
Publication of FI75817B publication Critical patent/FI75817B/fi
Application granted granted Critical
Publication of FI75817C publication Critical patent/FI75817C/fi

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    • 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

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  • 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)

6 75817
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
FI861206A 1980-05-16 1986-03-21 Oxiranderivat och foerfarande foer deras framstaellning. FI75817C (fi)

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
DE3106076 1981-02-19
DE19813106076 DE3106076A1 (de) 1981-02-19 1981-02-19 1-hydroxyethyl-azol-derivate, verfahren zu ihrer herstellung sowie ihre verwendung als pflanzenwachstumsregulatoren und fungizide
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
FI861206L FI861206L (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.
FI861230A FI861230L (fi) 1980-05-16 1981-05-13 1-hydroxietylazolderivat, deras framsaollningsfoerfarande och anvaendning som vaextlighet reglerande medel samt som fungicider.
FI861206A FI75817C (fi) 1980-05-16 1986-03-21 Oxiranderivat och foerfarande foer deras framstaellning.

Family Applications Before (2)

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.
FI861230A FI861230L (fi) 1980-05-16 1981-05-13 1-hydroxietylazolderivat, deras framsaollningsfoerfarande och anvaendning som vaextlighet reglerande medel samt som fungicider.

Country Status (24)

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US (8) US4532341A (fi)
EP (3) EP0072580B1 (fi)
JP (2) JPH02167270A (fi)
AR (2) AR227310A1 (fi)
AT (3) ATE25522T1 (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) HU191148B (fi)
IE (3) IE52451B1 (fi)
IL (6) IL75521A (fi)
NL (1) NL971022I2 (fi)
NZ (4) NZ209126A (fi)
OA (1) OA06809A (fi)
PH (3) PH17636A (fi)
PT (1) PT72979B (fi)
TR (4) TR22042A (fi)

Families Citing this family (199)

* Cited by examiner, † Cited by third party
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
CA1162540A (en) * 1980-12-24 1984-02-21 Ikutaro Saji Imidazolylpropanol compounds and their acid addition salts, and production and use thereof
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
DE3202613A1 (de) * 1982-01-27 1983-08-04 Bayer Ag, 5090 Leverkusen Antimykotische mittel
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
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.
DE3461637D1 (en) * 1983-02-16 1987-01-22 Pfizer Ltd 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
DE3315524A1 (de) * 1983-04-29 1984-10-31 Bayer Ag, 5090 Leverkusen Verfahren zur herstellung von oxiranen
DE3315681A1 (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
DE3315619A1 (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
US5250560A (en) * 1983-09-16 1993-10-05 Bayer Aktiengesellschaft Fungicidal agents
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
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
GB8406000D0 (en) * 1984-03-07 1984-04-11 Ici Plc Olefine derivatives
CN1008735B (zh) * 1984-11-02 1990-07-11 拜尔公司 以取代的氮杂茂基甲基-环丙基-甲醇衍生物为活性成分的组合物
EP0181529B1 (de) * 1984-11-02 1991-03-27 Bayer Ag Optisch aktives 2-(4-Chlorphenoxymethyl)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)-2-butanol, ein Verfahren zu dessen Herstellung und dessen Verwendung als Antimykotikum
DE3508909A1 (de) * 1985-03-13 1986-09-18 Bayer Ag, 5090 Leverkusen Piperazinylmethyl-1,2,4-triazolylmethyl-carbinole
US4863505A (en) * 1985-09-12 1989-09-05 Kureha Kagaku Kogyo Kabushiki Kaisha Novel derivative of azole, and agricultural and horticultural composition containing the same as an active incredient
DE3537817A1 (de) * 1985-10-24 1987-04-30 Bayer Ag Verfahren zur herstellung von oxiranen
DE3540525A1 (de) * 1985-11-15 1987-05-27 Bayer Ag Mittel zur regulierung des pflanzenwachstums
GB8603951D0 (en) * 1986-02-18 1986-03-26 Ici Plc Heterocyclic compounds
DE3702301A1 (de) * 1986-03-06 1987-09-10 Bayer Ag 2-hydroxyethyl-azol-derivate
ATE54312T1 (de) * 1986-03-06 1990-07-15 Bayer Ag 2-hydroxyethyl-azol-derivate.
US4952232A (en) * 1987-04-29 1990-08-28 E. I. Du Pont De Nemours And Company Antifungal carbinols
DE3621494A1 (de) * 1986-06-27 1988-01-07 Bayer Ag Verwendung von 1-aryl-3-hydroxy-3-alkyl-4-(1,2,4-triazol-1-yl) -butan-derivaten als mikrobizide fuer den materialschutz
DE3627673A1 (de) * 1986-08-14 1988-02-25 Bayer Ag Verfahren zur herstellung optisch aktiver 2-hydroxyethyl-azol-derivate
US5239089A (en) * 1986-11-10 1993-08-24 Kureha Kagaku Kogyo Kabushiki Kaisha Oxirane derivatives useful for making fungicidal azole compounds
JPH0625140B2 (ja) 1986-11-10 1994-04-06 呉羽化学工業株式会社 新規アゾール誘導体、その製造方法及び該誘導体の農園芸用薬剤
DE3700923A1 (de) * 1987-01-15 1988-07-28 Bayer Ag Fungizide wirkstoffkombination
DE3703082A1 (de) * 1987-02-03 1988-08-11 Bayer Ag Verfahren zur herstellung optisch aktiver 2-hydroxyethyl-azol-derivate
DE3716559A1 (de) * 1987-05-18 1988-12-01 Bayer Ag Hydroxyalkyl-triazolyl-derivate
DE3716560A1 (de) * 1987-05-18 1988-12-01 Bayer Ag Hydroxyalkyl-triazolyl-derivate
DE3716558A1 (de) * 1987-05-18 1988-12-01 Bayer Ag Hydroxyalkyl-azolyl-derivate
DE3812967A1 (de) * 1987-06-24 1989-01-05 Bayer Ag Azolylmethyl-cyclopropyl-derivate
DE3720998A1 (de) * 1987-06-25 1989-01-05 Bayer Ag Verwendung von 1-(4-chlorphenyl)-4,4-dimethyl-3- (1,2,4-triazol-1-yl-methyl)-pentan-3-ol zur bekaempfung von pseudocercosporella herpotrichoides
DE3813129A1 (de) * 1987-07-01 1989-01-12 Bayer Ag Hydroxyethyl-azolyl-derivate
DE3722133A1 (de) * 1987-07-04 1989-01-12 Bayer Ag Azolyl-tetrahydropyran-derivate
DE3813874A1 (de) * 1987-07-10 1989-01-19 Bayer Ag Hydroxyalkyl-azolyl-derivate
DE3724645A1 (de) * 1987-07-25 1989-02-02 Basf Ag Hydroxyethyl-azol-derivate und ihre verwendung als fungizide
DE3732385A1 (de) * 1987-09-25 1989-04-06 Bayer Ag Hydroxyalkylcyclopropyl1-1,2,4-triazolyl- oder -imidazolyl-derivate und ihre verwendung als antimykotische mittel
DE3733754A1 (de) * 1987-10-06 1989-04-20 Bayer Ag Verfahren zur herstellung von 1-(4-chlorphenyl)-3-(1,2,4-triazol-1-yl-methyl)-4,4-dimethyl-pentan-3-ol
DE3736651C2 (de) * 1987-10-29 1995-11-23 Bayer Ag Fungizide Wirkstoffkombinationen
DE3804981A1 (de) * 1988-02-18 1989-08-31 Bayer Ag Substituierte triazole
US5266586A (en) * 1988-02-18 1993-11-30 Bayer Aktiengesellschaft Fungicidal substituted triazoles
US5187178A (en) * 1988-02-18 1993-02-16 Bayer Aktiengesellschaft Fungicidal substituted triazoles
DE3809069A1 (de) * 1988-03-18 1989-09-28 Basf Ag Azolylmethylallylalkohole und diese enthaltende fungizide
DE3813253A1 (de) * 1988-04-20 1989-11-02 Bayer Ag Substituierte triazolylmethylcarbinole
DE3823174A1 (de) * 1988-07-08 1990-01-11 Bayer Ag Optisch aktive (1,3-oxathian-2-yl)-oxirane, ihre herstellung und verwendung als zwischenprodukte, sowie verfahren zur herstellung von optisch aktiven 2-hydroxyethyl-1,2,4-triazol-derivaten
DE3824435A1 (de) * 1988-07-19 1990-01-25 Bayer Ag, 51373 Leverkusen Substituierte 2,2-dihalogencyclopropyl-hydroxyethyl-1,2,4-triazole, verfahren sowie 2,2-dihalogencyclopropyl-oxirane, cyclopropylketone und halogenmethyl-cyclpropyl-ketone als zwischenprodukte zu ihrer herstellung, und ihre verwendung in fungiziden mitteln
DE3824434A1 (de) * 1988-07-19 1990-01-25 Bayer Ag, 51373 Leverkusen Substituierte 1-aryl-3-cycloalkyl-4-(1,2,4-triazol-1-yl)-but-1-in-3-ole, verfahren sowie substituierte 2-arylethinyl-2-cycloalkyl-oxirane und cycloalkyl-arylethinylketone als zwischenprodukte zu ihrer herstellung, und ihre verwendung in fungiziden mitteln
US5164464A (en) * 1989-01-17 1992-11-17 The Dow Chemical Company Vinyl ester resins containing mesogenic/rigid rodlike moieties
US5024785A (en) * 1989-01-17 1991-06-18 The Dow Chemical Company Liquid crystal/rigid rodlike polymer modified epoxy/vinyl ester resins
US4962163A (en) * 1989-01-17 1990-10-09 The Dow Chemical Company Vinyl ester resins containing mesogenic/rigid rodlike moieties
DE3905316A1 (de) * 1989-02-21 1990-08-23 Bayer Ag Cyclopropyl-hydroxyethyl-azolyl-derivate
DE3906556A1 (de) * 1989-03-02 1990-09-06 Desowag Materialschutz Gmbh Mittel oder konzentrat zum konservieren von holz oder holzwerkstoffen
DE3906771A1 (de) * 1989-03-03 1990-09-06 Basf Ag 1-hydroxi-1,2,4-triazolverbindungen und diese enthaltende fungizide
DE3910922C1 (fi) * 1989-04-05 1990-05-17 Bayer Ag, 5090 Leverkusen, De
DE3910921C1 (fi) 1989-04-05 1990-05-17 Bayer Ag, 5090 Leverkusen, De
DE3921163A1 (de) * 1989-06-28 1991-01-10 Bayer Ag Hydroxy-keto-azole
DE3934714A1 (de) * 1989-10-18 1991-04-25 Bayer Ag Fungizide wirkstoffkombinationen
DE4001115A1 (de) * 1990-01-17 1991-07-18 Bayer Ag Fungizide wirkstoffkombinationen
FR2662911B1 (fr) * 1990-06-12 1996-12-13 Rhone Poulenc Agrochimie Procede pour proteger les produits de multiplication des vegetaux et les vegetaux en resultant au moyen d'un triazolyl cyclopentanol.
DE4018927A1 (de) * 1990-06-13 1991-12-19 Bayer Ag Azolyl-propanol-derivate
US5230892A (en) * 1990-08-24 1993-07-27 Bayer Aktiengesellschaft Solid formulations
FR2668893A1 (fr) * 1990-11-13 1992-05-15 Rhone Poulenc Agrochimie Procede pour proteger les produits de multiplication des vegetaux a l'aide de triazolyl ou imidazolyl methyl allyl alcool et composes nouveaux pour mettre en óoeuvre le procede.
DK0487451T3 (da) * 1990-11-16 1996-05-06 Ciba Geigy Ag Mikrobicide midler
DE4113158A1 (de) * 1991-04-23 1992-10-29 Bayer Ag Mikrobizide wirkstoffkombinationen
DE4131205A1 (de) 1991-09-19 1993-03-25 Bayer Ag Wasserbasierte, loesungsmittel- und emulgatorfreie mikrobizide wirkstoffkombination
DE59206041D1 (de) * 1991-12-19 1996-05-23 Ciba Geigy Ag Mikrobizide
ATE160483T1 (de) * 1992-02-13 1997-12-15 Ciba Geigy Ag Fungizide mischungen auf der basis von triazol- fungiziden und 4,6-dimethyl-n-phenyl-2- pyrimidinamin
FR2690441A1 (fr) * 1992-04-08 1993-10-29 Rhone Poulenc Agrochimie Nouveaux dérivés triazole et imidazole fongicides.
FR2694161B1 (fr) * 1992-07-31 1995-06-09 Shell Int Research Compositions fongicides comprenant un derive de 1-hydroxyethyl azole et un alkoxylate d'un alcool aliphatique.
DE4300452A1 (de) * 1993-01-11 1994-07-14 Bayer Ag Mittel zur Hemmung des Pflanzenwachstums
DE4304172A1 (de) 1993-02-12 1994-08-25 Bayer Ag Fungizide Wirkstoffkombinationen
EP0613890A1 (en) * 1993-02-28 1994-09-07 Nihon Nohyaku Co., Ltd. Novel triazole compound, process for preparing the same and antifungal agent containing the same
EP0719260A1 (de) * 1993-09-16 1996-07-03 Bayer Ag Butenol-triazolyl derivate, deren herstellung und deren verwendung als mikrobizide
ATE136734T1 (de) * 1993-09-24 1996-05-15 Basf Ag Fungizide mischungen
DE4412332A1 (de) * 1994-04-11 1995-10-12 Bayer Ag Silyloxy-cyclopropyl-azolyl-Derivate
TW286264B (fi) 1994-05-20 1996-09-21 Ciba Geigy Ag
DE4426753A1 (de) 1994-07-28 1996-02-01 Bayer Ag Mittel zur Bekämpfung von Pflanzenschädlingen
US5591726A (en) * 1994-09-26 1997-01-07 American Cyanamid Company Heterocyclylalkyl diarylboron ester and thioester fungicidal agents
DE19505938A1 (de) * 1995-02-21 1996-08-22 Bayer Ag Verfahren zur Herstellung von 1-(4-Chlorphenyl)-4,4-dimethyl-pentan-3-on
DE19617282A1 (de) * 1996-04-30 1997-11-06 Bayer Ag Triazolyl-mercaptide
DE19617461A1 (de) 1996-05-02 1997-11-06 Bayer Ag Acylmercapto-triazolyl-Derivate
DE19619544A1 (de) * 1996-05-15 1997-11-20 Bayer Ag Triazolyl-Disulfide
DE19620408A1 (de) * 1996-05-21 1997-11-27 Bayer Ag Mercapto-imidazolyl-Derivate
DE19620407A1 (de) * 1996-05-21 1997-11-27 Bayer Ag Thiocyano-triazolyl-Derivate
DE19620590A1 (de) * 1996-05-22 1997-11-27 Bayer Ag Sulfonyl-mercapto-triazolyl-Derivate
US6297236B1 (en) 1998-04-06 2001-10-02 Bayer Aktiengesellschaft Fungicide active substance combinations
DE19716257A1 (de) * 1997-04-18 1998-10-22 Bayer Ag Fungizide Wirkstoffkombination
WO1999000013A2 (en) 1997-06-30 1999-01-07 Monsanto Company Microparticles containing agricultural active ingredients
DE19829113A1 (de) 1998-06-10 1999-12-16 Bayer Ag Mittel zur Bekämpfung von Pflanzenschädlingen
TR200102836T2 (tr) 1998-06-10 2002-06-21 Bayer Aktiengesellschaft Bitki zararlılarının kontrol edilmesi için bileşimler.
CN1177530C (zh) * 1998-06-17 2004-12-01 拜尔公司 防治植物害虫的组合物
DE19834028A1 (de) 1998-07-28 2000-02-03 Wolman Gmbh Dr Verfahren zur Behandlung von Holz gegen den Befall durch holzschädigende Pilze
ES2151847B1 (es) * 1998-10-07 2001-08-16 Rodriguez Juan Carlos Caubin Util para orinar las mujeres.
CZ301233B6 (cs) * 1999-12-13 2009-12-16 Bayer Aktiengesellschaft Fungicidní kombinace úcinných látek, zpusob hubení hub a použití techto kombinací úcinných látek a zpusob výroby fungicidních prostredku
DE10019758A1 (de) * 2000-04-20 2001-10-25 Bayer Ag Fungizide Wirkstoffkombinationen
DE10103832A1 (de) * 2000-05-11 2001-11-15 Bayer Ag Fungizide Wirkstoffkombinationen
DE10049804A1 (de) * 2000-10-09 2002-04-18 Bayer Ag Wirkstoffkombinationen mit fungiziden und akariziden Eigenschaften
DE10059605A1 (de) 2000-12-01 2002-06-06 Bayer Ag Fungizide Wirkstoffkombinationen
EA006319B1 (ru) * 2001-04-12 2005-10-27 Басф Акциенгезельшафт Комбинация действующих веществ с биорегуляторными свойствами
DE10141618A1 (de) * 2001-08-24 2003-03-06 Bayer Cropscience Ag Fungizide Wirkstoffkombinationen
CN1646014A (zh) * 2002-04-05 2005-07-27 巴斯福股份公司 基于苄胺肟衍生物和唑类的杀真菌混合物
DE10228104A1 (de) * 2002-06-24 2004-01-15 Bayer Cropscience Ag Fungizide Wirkstoffkombination
US20050245550A1 (en) * 2002-07-10 2005-11-03 Eberhard Ammermann Fungicidal mixtures based on the dithianon
KR101038848B1 (ko) * 2002-08-19 2011-06-02 바스프 에스이 카르복실산 함유 제제 및 그의 식물 재배 용도
WO2004043150A1 (de) 2002-11-12 2004-05-27 Basf Aktiengesellschaft Verfahren zur ertragssteigerung bei glyphosate resistenten leguminosen
DE10333373A1 (de) 2003-07-23 2005-02-10 Bayer Ag Fungizide Wirkstoffkombinationen
DE10335183A1 (de) * 2003-07-30 2005-02-24 Bayer Cropscience Ag Fungizide Wirkstoffkombinationen
DE10341945A1 (de) * 2003-09-11 2005-04-21 Bayer Cropscience Ag Verwendung von fungiziden Mitteln zur Beizung von Saatgut
US20070117813A1 (en) * 2003-10-01 2007-05-24 Tormo I Blasco Jordi Fungicidal mixtures
DE10347090A1 (de) 2003-10-10 2005-05-04 Bayer Cropscience Ag Synergistische fungizide Wirkstoffkombinationen
DE10349501A1 (de) 2003-10-23 2005-05-25 Bayer Cropscience Ag Synergistische fungizide Wirkstoffkombinationen
DE10349503A1 (de) 2003-10-23 2005-05-25 Bayer Cropscience Ag Fungizide Wirkstoffkombinationen
EP1563731A1 (en) 2004-02-12 2005-08-17 Bayer CropScience S.A. Fungicidal composition comprising a pyridylethylbenzamide derivative and a compound capable of inhibiting the ergosterol biosynthesis
EP2255629A3 (de) 2004-04-30 2012-09-19 Basf Se Fungizide Mischungen
DE102004049761A1 (de) 2004-10-12 2006-04-13 Bayer Cropscience Ag Fungizide Wirkstoffkombinationen
DE102005015677A1 (de) * 2005-04-06 2006-10-12 Bayer Cropscience Ag Synergistische fungizide Wirkstoffkombinationen
DE102005015850A1 (de) 2005-04-07 2006-10-12 Bayer Cropscience Ag Synergistische fungizide Wirkstoffkombinationen
DE102005026482A1 (de) 2005-06-09 2006-12-14 Bayer Cropscience Ag Wirkstoffkombinationen
EP2255648A3 (de) 2005-06-09 2011-03-02 Bayer CropScience AG Wirkstoffkombinationen
CN102057917B (zh) 2005-07-21 2013-03-20 先正达参股股份有限公司 杀真菌组合物
DE102005035300A1 (de) 2005-07-28 2007-02-01 Bayer Cropscience Ag Synergistische fungizide Wirkstoffkombinationen
SI1928240T1 (sl) 2005-09-09 2010-01-29 Basf Se Fungicidne meĺ anice na osnovi triazola
DE102006023263A1 (de) 2006-05-18 2007-11-22 Bayer Cropscience Ag Synergistische Wirkstoffkombinationen
CN101516863A (zh) * 2006-07-18 2009-08-26 阿斯利康(瑞典)有限公司 制备取代的2-乙酰基氨基-烷氧基苯的方法
CA2661170A1 (en) 2006-09-18 2008-03-27 Basf Se Pesticidal mixtures
US7772156B2 (en) * 2006-11-01 2010-08-10 Buckman Laboratories International, Inc. Microbicidal compositions including a cyanodithiocarbimate and a second microbicide, and methods of using the same
JP5266247B2 (ja) 2006-12-07 2013-08-21 ビーエーエスエフ ソシエタス・ヨーロピア 殺菌性トリアゾールおよびアルコキシル化アルコールを含む組成物およびキットならびにそれらの使用
WO2008071714A1 (en) 2006-12-15 2008-06-19 Rohm And Haas Company Mixtures comprising 1-methylcyclopropene
BR122019020360B1 (pt) 2007-02-06 2020-08-18 Basf Se misturas, composição pesticida, método para controlar fungos nocivos fitopatogênicos, método para proteger plantas do ataque ou infestação pelos insetos, acarídeos ou nematódeos e método para proteger semente
EA017621B1 (ru) 2007-04-23 2013-01-30 Басф Се Повышение продуктивности растений путем комбинирования химических веществ с трансгенными модификациями
SI2196089T1 (sl) 2007-04-25 2011-06-30 Syngenta Participations Ag Fungicidni sestavki
EP2000028A1 (de) * 2007-06-06 2008-12-10 Bayer CropScience Aktiengesellschaft Fungizide Wirkstoffkombinationen
ES2381320T3 (es) 2007-09-26 2012-05-25 Basf Se Composiciones fungicidas ternarias que comprenden boscalida y clorotalonil
DE102007045920B4 (de) 2007-09-26 2018-07-05 Bayer Intellectual Property Gmbh Synergistische Wirkstoffkombinationen
GB0823002D0 (en) * 2008-12-17 2009-01-28 Syngenta Participations Ag Isoxazoles derivatives with plant growth regulating properties
EP2100506A2 (en) 2009-01-23 2009-09-16 Bayer CropScience AG Uses of fluopyram
EP2410850A2 (de) 2009-03-25 2012-02-01 Bayer Cropscience AG Synergistische wirkstoffkombinationen
US20120088664A1 (en) 2009-06-18 2012-04-12 Basf Se Antifungal 1,2,4-triazolyl derivatives having a 5-sulfur subtituent
EA021808B1 (ru) 2009-07-08 2015-09-30 Байер Интеллектуэль Проперти Гмбх Производные фенил(окси/тио)алканола, способ борьбы с фитопатогенными вредными грибами, средство для борьбы с фитопатогенными вредными грибами и способы получения производных фенил(окси/тио)алканола
BR112012000170A2 (pt) * 2009-07-08 2019-09-24 Bayer Cropscience Ag derivados de fenil (oxi/tio) alcanol substituídos
AU2010272872B2 (en) 2009-07-16 2014-08-28 Bayer Intellectual Property Gmbh Synergistic active substance combinations containing phenyl triazoles
WO2011026796A1 (en) 2009-09-01 2011-03-10 Basf Se Synergistic fungicidal mixtures comprising lactylates and method for combating phytopathogenic fungi
WO2011076724A2 (en) * 2009-12-23 2011-06-30 Bayer Cropscience Ag Pesticidal compound mixtures
WO2011140620A1 (pt) * 2010-05-12 2011-11-17 Empresa Brasileira De Pesquisa Agropecuária - Embrapa Processo de produção, uso e composição fungicida compreendendo compostos obtidos a partir do líquido da casca da castanha de caju
KR20130100142A (ko) 2010-08-26 2013-09-09 바이엘 인텔렉쳐 프로퍼티 게엠베하 5-요오도트리아졸 유도체
BRPI1003373A2 (pt) 2010-09-29 2013-01-29 Fmc Quimica Do Brasil Ltda combinaÇÕes sinÉrgicas de triazàis, estrobirulinas e benzimidazàis, usos, formulaÇÕes, processos de produÇço e aplicaÇÕes utilizando a mesma
EP2646418B1 (de) 2010-11-30 2017-10-04 Bayer Intellectual Property GmbH Pyrimidin-derivate und ihre verwendung als schädlingsbekämpfungsmittel
EA201300731A1 (ru) 2010-12-20 2014-01-30 Басф Се Пестицидно активные смеси, которые содержат соединения пиразола
RU2013133873A (ru) 2010-12-21 2015-01-27 БАЙЕР КРОПСАЙЕНС ЭлПи ШЕРОХОВАТЫЕ МУТАНТЫ Bacillus И СПОСОБЫ ИХ ПРИМЕНЕНИЯ ДЛЯ УСКОРЕНИЯ РОСТА РАСТЕНИЙ, УЛУЧШЕНИЯ ЗДОРОВЬЯ РАСТЕНИЙ И БОРЬБЫ С БОЛЕЗНЯМИ И ВРЕДИТЕЛЯМИ
EP2481284A3 (en) 2011-01-27 2012-10-17 Basf Se Pesticidal mixtures
EP3378313A1 (en) 2011-03-23 2018-09-26 Basf Se Compositions containing polymeric, ionic compounds comprising imidazolium groups
AR085587A1 (es) 2011-04-13 2013-10-09 Bayer Cropscience Ag Combinaciones de compuestos activos
AR085588A1 (es) 2011-04-13 2013-10-09 Bayer Cropscience Ag Combinaciones de compuestos activos
JP2014525424A (ja) 2011-09-02 2014-09-29 ビーエーエスエフ ソシエタス・ヨーロピア アリールキナゾリノン化合物を含む農業用混合物
BR112014005654A2 (pt) 2011-09-12 2017-03-28 Bayer Cropscience Lp métodos para melhorar a saúde e promover o crescimento de uma planta e/ou de melhorar o amadurecimento da fruta
EP2782447A1 (de) * 2011-11-25 2014-10-01 Bayer Intellectual Property GmbH 2-iod-imidazol-derivate
ES2660132T3 (es) 2012-06-20 2018-03-20 Basf Se Compuestos de pirazol plaguicidas
US20150257383A1 (en) 2012-10-12 2015-09-17 Basf Se Method for combating phytopathogenic harmful microbes on cultivated plants or plant propagation material
CA2894264C (en) 2012-12-20 2023-03-07 BASF Agro B.V. Compositions comprising a triazole compound
EP2746258A1 (en) 2012-12-21 2014-06-25 Basf Se Substituted [1,2,4]triazole and imidazole compounds
EP2746257A1 (en) 2012-12-21 2014-06-25 Basf Se Substituted [1,2,4]triazole and imidazole compounds
EP2783569A1 (en) 2013-03-28 2014-10-01 Basf Se Compositions comprising a triazole compound
EP2835052A1 (en) 2013-08-07 2015-02-11 Basf Se Fungicidal mixtures comprising pyrimidine fungicides
EP2837287A1 (en) 2013-08-15 2015-02-18 Bayer CropScience AG Use of prothioconazole for increasing root growth of Brassicaceae
EP3041355B1 (de) 2013-09-03 2017-08-09 Bayer CropScience AG Verwendung fungizider wirkstoffe zur kontrolle von chalara fraxinea an eschenbäumen
EP3046915A1 (en) 2013-09-16 2016-07-27 Basf Se Fungicidal pyrimidine compounds
WO2015036059A1 (en) 2013-09-16 2015-03-19 Basf Se Fungicidal pyrimidine compounds
EP2979549A1 (en) 2014-07-31 2016-02-03 Basf Se Method for improving the health of a plant
AU2015334829B2 (en) 2014-10-24 2019-09-12 Basf Se Non-amphoteric, quaternisable and water-soluble polymers for modifying the surface charge of solid particles
EP2910126A1 (en) 2015-05-05 2015-08-26 Bayer CropScience AG Active compound combinations having insecticidal properties
CN107809906A (zh) 2015-07-02 2018-03-16 巴斯夫农业公司 包含三唑化合物的农药组合物
US20180310552A1 (en) 2015-10-27 2018-11-01 Bayer Cropscience Aktiengesellschaft Composition comprising a safener, a fungicide and metalaxyl
WO2018060093A1 (en) 2016-09-29 2018-04-05 Bayer Cropscience Aktiengesellschaft 1,5-substituted imidazole derivatives as fungicides for crop protection.
BR112023001601A2 (pt) 2020-07-30 2023-02-23 Pi Industries Ltd Composição de metominostrobina, tebuconazol e propinebe
WO2026017904A1 (en) 2024-07-19 2026-01-22 Syngenta Crop Protection Ag Pesticidal mixture

Family Cites Families (36)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3188324A (en) * 1958-11-19 1965-06-08 Sinclair Research Inc Neopentyl-substituted epoxy alcohols and chlorides
DE1568414A1 (de) * 1965-09-23 1970-04-02 Dow Chemical Co Verfahren zur Herstellung von Epoxyden aus Sulfoniumsalzen
DE1595582A1 (de) * 1966-01-07 1970-04-30 Hoechst Ag Verfahren zur Herstellung von Polyaethern
US3410810A (en) * 1966-05-03 1968-11-12 Goodrich Co B F Polymers of cyanoalkyl epoxy ethers
US3930835A (en) * 1970-08-06 1976-01-06 The Dow Chemical Company Pesticidal compositions and methods employing substituted oxirane compounds
DE2354444A1 (de) * 1973-10-31 1975-05-07 Merck Patent Gmbh Biphenylylaether und verfahren zu ihrer herstellung
US4000131A (en) * 1974-05-10 1976-12-28 Hoffmann-La Roche Inc. Process for preparing epoxide-cyclohexyl compound and resultant compound
DE2423987C2 (de) * 1974-05-17 1986-01-16 Bayer Ag, 5090 Leverkusen Metallkomplexe von Azolyläthern, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Fungizide
DE2431407C2 (de) * 1974-06-29 1982-12-02 Bayer Ag, 5090 Leverkusen 1,2,4-Triazol-1-yl-alkanone und -alkanole, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Fungizide
EG11779A (en) * 1974-11-19 1978-06-30 Janssen Pharmaceutica Nv Process for preparing of 1-(b-aryl-b-(r-oxy)-ethyl)imidazoles
US4085209A (en) * 1975-02-05 1978-04-18 Rohm And Haas Company Preparation and safening effect of 1-substituted imidazole metal salt complexes
CH614201A5 (en) * 1975-04-11 1979-11-15 Hoffmann La Roche Process for the preparation of epoxides
FI761174A7 (fi) * 1975-05-05 1976-11-06 Erba Carlo Spa
US4079143A (en) * 1975-08-26 1978-03-14 Imperial Chemical Industries Limited Fungicidal 1H-1,2,4-triazoles
IE44186B1 (en) * 1975-12-03 1981-09-09 Ici Ltd 1,2,4-triazolyl alkanols and their use as pesticides
DE2623129C3 (de) * 1976-05-22 1980-04-10 Nordmark-Werke Gmbh, 2000 Hamburg U-Diphenyl-3-(imidazol-l-yl) -propan-2-ole, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel
FR2370432A1 (fr) * 1976-11-16 1978-06-09 Ici Ltd Procede pour influencer la croissance des vegetaux par l'action de certains composes 1,2,4-triazoliques
US4123542A (en) * 1977-01-19 1978-10-31 Syntex (U.S.A.) Inc. Derivatives of N-alkyl imidazoles
US4366165A (en) * 1977-05-19 1982-12-28 Rohm And Haas Company 1 and 4-Arylcyanoalkyl-1,2,4-triazoles and fungicidal use
DE2736122A1 (de) * 1977-08-11 1979-02-22 Basf Ag Fungizide
US4246274A (en) * 1978-05-10 1981-01-20 Bayer Aktiengesellschaft Antimycotic hydroxypropyl-imidazoles
DE2851086A1 (de) * 1978-11-25 1980-06-04 Bayer Ag Hydroxypropyl-triazole, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel
DE2908378A1 (de) * 1979-03-03 1980-09-11 Hoechst Ag Derivate des 1,2,4-triazols
US4654332A (en) * 1979-03-07 1987-03-31 Imperial Chemical Industries Plc Heterocyclic compounds
US4551469A (en) * 1979-03-07 1985-11-05 Imperial Chemical Industries Plc Antifungal triazole ethanol derivatives
DE2920374A1 (de) * 1979-05-19 1980-11-20 Bayer Ag Fungizide mittel, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide
US4414210A (en) * 1979-10-02 1983-11-08 Rohm And Haas Company 2-Hydroxyarylethyltriazole fungicides
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
US4398942A (en) * 1980-12-22 1983-08-16 Rohm And Haas Company Herbicidally-active phenylacetonitriles
CA1162540A (en) * 1980-12-24 1984-02-21 Ikutaro Saji Imidazolylpropanol compounds and their acid addition salts, and production and use thereof
DE3102588A1 (de) * 1981-01-27 1982-08-12 Bayer Ag, 5090 Leverkusen Mittel zur hemmung des pflanzenwachstums
DE3279417D1 (en) * 1981-03-18 1989-03-09 Ici Plc Triazole compounds, a process for preparing them, their use as plant fungicides and fungicidal compositions containing them
DE3111238A1 (de) * 1981-03-21 1982-10-07 Bayer Ag, 5090 Leverkusen Substituierte triazolylmethyl-oxirane, verfahren zu ihrer herstellung sowie ihre verwendung als zwischenprodukte
DE3275088D1 (en) * 1981-08-19 1987-02-19 Ici Plc Triazole derivatives, processes for preparing them, compositions containing them and processes for combating fungi and regulating plant growth
GB2130322B (en) * 1982-09-17 1987-04-08 Nissin Kogyo Kk Vehicle load dependent braking
DE3237400A1 (de) * 1982-10-08 1984-04-12 Bayer Ag, 5090 Leverkusen Substituierte 1-hydroxyethyl-triazolyl-derivate

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DK158152B (da) 1990-04-02
HUT34170A (en) 1985-02-28
IL75520A0 (en) 1985-10-31
JPH02167270A (ja) 1990-06-27
FI75817B (fi) 1988-04-29
JPH0372217B2 (fi) 1991-11-18
HU188092B (en) 1986-03-28
ES8203859A1 (es) 1982-04-01
IL75521A (en) 1987-08-31
PT72979A (en) 1981-06-01
PH25782A (en) 1991-11-05
AU3629284A (en) 1985-04-04
FI861206L (fi) 1986-03-21
US4871390A (en) 1989-10-03
GR78229B (fi) 1984-09-26
FI73421B (fi) 1987-06-30
FI861206A0 (fi) 1986-03-21
JPH02167273A (ja) 1990-06-27
US4532341A (en) 1985-07-30
HU191671B (en) 1987-03-30
EG14836A (en) 1985-06-30
NZ207097A (en) 1986-06-11
NL971022I2 (nl) 1999-03-01
EP0072580A2 (de) 1983-02-23
ES502234A0 (es) 1982-04-01
US4789672A (en) 1988-12-06
TR22691A (tr) 1988-03-31
NL971022I1 (nl) 1997-10-01
IL75521A0 (en) 1985-10-31
AU3629384A (en) 1985-04-04
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AR227310A1 (es) 1982-10-15
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DK54185D0 (da) 1985-02-06
AR229527A1 (es) 1983-09-15
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US4897107A (en) 1990-01-30
DK54385D0 (da) 1985-02-06
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NZ209126A (en) 1986-06-11
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ATE25522T1 (de) 1987-03-15
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DE3164696D1 (en) 1984-08-16
DK158152C (da) 1990-08-27
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NZ207096A (en) 1986-06-11
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EP0072580B1 (de) 1987-02-25
FI811472L (fi) 1981-11-17
IE860957L (en) 1981-11-16
US4904298A (en) 1990-02-27
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PH25843A (fi) 1991-12-02
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US4626595A (en) 1986-12-02
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TR22400A (tr) 1987-03-31
NZ197083A (en) 1986-06-11
DK213081A (da) 1981-11-17
TR22042A (tr) 1986-02-05
US4911746A (en) 1990-03-27
FI861230A7 (fi) 1986-03-24
US4723984A (en) 1988-02-09
JPH0413349B2 (fi) 1992-03-09
FI861230L (fi) 1986-03-24
DK163507C (da) 1992-07-27
PT72979B (en) 1982-06-25
ATE8391T1 (de) 1984-07-15
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AU560022B2 (en) 1987-03-26
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DK54185A (da) 1985-02-06
ATE18666T1 (de) 1986-04-15

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