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DK165972B - Optisk aktive phenoxyphenoxyalkoholer - Google Patents

Optisk aktive phenoxyphenoxyalkoholer Download PDF

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Publication number
DK165972B
DK165972B DK001591A DK1591A DK165972B DK 165972 B DK165972 B DK 165972B DK 001591 A DK001591 A DK 001591A DK 1591 A DK1591 A DK 1591A DK 165972 B DK165972 B DK 165972B
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DK
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Prior art keywords
compound
methyl
millimoles
phenoxyphenoxy
optically active
Prior art date
Application number
DK001591A
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English (en)
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DK1591A (da
DK165972C (da
DK1591D0 (da
Inventor
Sumio Nishida
Makoto Hatakoshi
Hirosi Kisida
Noritada Matsuo
Original Assignee
Sumitomo Chemical Co
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Publication of DK1591A publication Critical patent/DK1591A/da
Publication of DK1591D0 publication Critical patent/DK1591D0/da
Publication of DK165972B publication Critical patent/DK165972B/da
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Publication of DK165972C publication Critical patent/DK165972C/da

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
    • C07D213/64—One oxygen atom attached in position 2 or 6
    • 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
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • 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
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • 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
    • A01N43/58—1,2-Diazines; Hydrogenated 1,2-diazines
    • 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
    • A01N43/60—1,4-Diazines; Hydrogenated 1,4-diazines
    • 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
    • A01N43/66—1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms
    • 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
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
    • 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
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/86—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/257—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings
    • C07C43/29—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings containing halogen
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    • C07C43/02—Ethers
    • C07C43/257—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings
    • C07C43/295—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings containing hydroxy or O-metal groups
    • C—CHEMISTRY; METALLURGY
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
    • C07D213/30—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
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    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/62—Oxygen or sulfur atoms
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    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/62—Oxygen or sulfur atoms
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    • C—CHEMISTRY; METALLURGY
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
    • C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
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    • C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/32—One oxygen, sulfur or nitrogen atom
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    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
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    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
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    • C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
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    • C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
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    • C07D277/08—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D277/12—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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    • C07D279/04—1,3-Thiazines; Hydrogenated 1,3-thiazines
    • C07D279/06—1,3-Thiazines; Hydrogenated 1,3-thiazines not condensed with other rings

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Environmental Sciences (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Zoology (AREA)
  • Pest Control & Pesticides (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Pyridine Compounds (AREA)
  • Thiazole And Isothizaole Compounds (AREA)
  • Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
  • Pyrane Compounds (AREA)

Description

DK 165972B
Den foreliggende opfindelse angår hidtil ukendte optisk aktive phe-noxyphenoxyalkoholer, som er mellemprodukter ved fremstilling af nitrogenholdige heterocycliske forbindelser.
De optisk aktive alkoholer ifølge opfindelsen er ejendommelige ved, 5 at de er en (S)-(+)-isomer af forbindelsen med formlen CH3 (R) -(-)-isomer af forbindelsen med formlen ch3 10 (S) -(+)-isomer af forbindelsen med formlen CH, _ __ j 3 ^Vo-^m-o-ch-ch2-oh eller (R)-(-)-isomer af forbindelsen med formlen 15 f1
°~CB~CH2~°H
De nitrogenholdige heterocycliske forbindelser, ved hvis fremstilling forbindelserne ifølge opfindelsen er mellemprodukter, har den almene formel I
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2 hvor
Rj^ betegner en af nedenstående grupper 5 ψ-*> p-* (R8}£ ' R10 ' R12 ' r14 p‘“ -½¾ R16 ' *21 *20 (hvor Ry, Rg, R9, Ri0, R^, Ri2, R13) R14, R15, Rifi og R1? har samme eller forskellig betydning og hver betegner et hydrogenatom, et halogenatom, alkyl, C^^-alkoxy, C^^-alkylthio, trifluormethyl 10 eller nitro, R^g, R^^, R2Q og R21 har samme eller forskellig betydning og hver betegner et hydrogenatom eller en methylgruppe, k betegner 0 eller 1, og 1 betegner et tal 0-3); og Ry og R3 har forskellig betydning og hver betegner et hydrogenatom eller en methylgruppe.
15 Det ovenfor anvendte udtryk "halogen" betegner chlor, brom, iod og fluor.
Blandt de nitrogenholdige heterocycliske forbindelser foretrækkes sådanne med formlen I, hvor R^ betegner en af nedenstående grupper
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3 "få-*- Ίώ-*» .Λ , ' \ ler £ ^Κ12 (hvor Ry, Rg, R^, og R^y hver for sig betegner et hydrogeneller fluoratom, og 1 har den ovenfor anførte betydning).
5 Organophosphor-insekticider, organo-chlorerede insekticider, carba-matinsekticider, etc, har bidraget meget til forebyggelse og udryddelse af skadelige insekter. Nogle af disse insekticider har imidlertid høj toxicitet. Deres eftervirkning forårsager endvidere undertiden uønsket abnorraalitet i insekternes økosystem. Endvidere er der 10 hos stuefluer, "planthoppers", cikader, risborelarver, etc. iagttaget resistens mod insekticiderne.
For at løse de ovennævnte problemer er der udført intense undersøgelser for at frembringe et udmærket insekticid, som ved lav koncentration viser en høj forebyggende virkning, der kan tillægges en 15 juvenilhormonagtig virkning; som et resultat heraf har det nu vist sig, at de nitrogenholdige heterocycliske forbindelser med den almene formel I kan anvendes til bekæmpelse af insekter i landbrugsområder, skovområder, kornmagasiner, i oplagrede produkter, i sanitære installationer, etc.
20 Som insekticid med juvenilhormonagtig virkning kendes "raethopren" (USA-patent nr. 3.904.662 og 3.912.815). Denne kendte forbindelses insekticide virkning er stadig ikke helt tilfredsstillende.
De nitrogenholdige heterocycliske forbindelser med den almene formel I viser en juvenilhormonagtig bekæmpende virkning og kan derfor 25 anvendes i lav koncentration til bekæmpelse af mange forskellige insekter hørende til Coleoptera, Lepidoptera, Hemiptera, Dictyoptera,
Diptera, etc., samt spindemider (Teranychidae) hørende til gruppen Acarina inden for landbrugsområder, skovområder, kornmagasiner, i oplagrede produkter, sanitære installationer, etc.
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4 I tysk offentliggørelsesskrift nr. 2.516.331 beskrives bl.a. phe-noxyphenoxyalkylpyridylforbindelser med insekticid virkning. I de i det følgende anførte testeksempler 2 og 3 er beskrevet sammenlignende forsøg, hvor nitrogeriholdige heterocycliske forbindelser med form-5 len I, der er fremstillet ud fra optisk aktive phenoxyphenoxyalkoho-ler ifølge opfindelsen, er sammenlignet med bl.a. en af de nærmest beslægtede forbindelser fra det tyske offentliggørelsesskrift, i testeksemplerne betegnet forbindelse F. Det fremgår af forsøgsresultaterne, at de nitrogenholdige heterocycliske forbindelser, der er 10 fremstillet ud fra forbindelserne ifølge opfindelsen, har en overraskende, overlegen insecticid virkning i forhold til den fra det tyske offentliggørelsesskrift kendte forbindelse F.
De optisk aktive alkoholer ifølge opfindelsen kan fremstilles på i og for sig kendt måde, og typiske eksempler på deres fremstilling og 15 videre omdannelse til andre mellemprodukter er vist nedenfor:
Fremgangsmåde (1) φ _—-» ?3 ,0-W,
Br-CH-CH. x o-w1
VII
λ-λ r—\ *3 CH3MgBr // \yo-// \y_o-cH-cHo ——-> \ —/ \—/ eller LiAlH4
VIII
/7 λ / \ Ko // /V \\ t3 I2
\—/°' \ _ /°“CH"CH“0H IV
pBr3 V, ^^-0-^^-O-CH-iH-Ai eller H.C-^VsOjCl/ |^J|
II
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5 (hvor E-2 og R3 har den ovenfor anførte betydning, betegner en alkylgruppe, og betegner Br eller tosyloxy).
Fremgangsmåde (2) 0-O^OH ♦ (VI) (XI) y-V __ CH, (>-O0-ch2 -ch-oh eller H3C-^J^-S02C1/ (^j) 5 (hvor har den ovenfor anførte betydning).
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6
Fremgangsmåde (3) C3"°"^-3"OH ““-^ Q-o-Q-o-tn-^o-w, CH3o
Br-CH-C-O-W-
XIV
VI
XIII
LiAlH4 t^ CH3
* r^-0-^A-0-CH-CH2-0H
-^
eller H,C^02C1/ Q W W
(hvor Aj_ har den ovenfor anførte betydning, og W2 betegner en alkyl* 5 gruppe).
En af de optisk aktive alkoholer ifølge opfindelsen, nemlig (S)-(+)-l-methyl-2-(4-phenoxy-phenoxy)ethanol, kan fremstilles på følgende måde:
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7 f3 (f°J Γ3 Π
Wtt OH p-toW.....^ 'Λ°ΤΝΛ;
O H sulfonsyre 0 H
((S)-L-ethyl lactat) ρ· n ι·ιαιη4 hoch2—c. o ^K0J w____
E
/-Λ ?H3 Γ^Ί fW>0H
h3c^so2-o-ch2-^.XJ . -»
H
CH3 p-toluen-
H
CH3 0.o^).o-ch2-|...oh
H
5 På lignende måde fremstilles (R)-(-)-1-methyl-2-(4-phenoxyphenoxy)-ethanol ud fra (R)-D-ethyllactat.
(R)-(-)- eller (S)-(+)-isomeren af l-methyl-2-(4-phenoxyphenoxy)-ethanol kan omdannes til sin tilsvarende anden stereoisomer ved nedenstående trin:
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8 CH, R-SO-Cl/organisk CM>°-CH2-Noh " %
H
(R)- (-)-isomer 0 ^pw-P —_>
W V=/ 2 ->OSO,R
H * ch3 yT\ JT\ I 0 hydrolyse // \W/ >o-ch — α || -> v=/ V=/ 1 -O-C-CH,
H J
ch3
H
(S)-(+)-isomer hvor R betegner en p-tolylgruppe eller en methylgruppe, og M' betegner et natrium- eller kaliumatom.
5 Typiske eksempler på den videre omdannelse af de ovenfor beskrevne mellemprodukter til de nitrogenholdige heterocycliske forbindelser I er anført nedenfor:
Fremgangsmåde A
En forbindelse med den ovenfor anførte almene formel II omsættes med 10 en forbindelse med den almene formel III
H-O-Ri III
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9 hvor Rj_ har den ovenfor anførte betydning, eller et alkalimetalsalt deraf til dannelse af en nitrogenholdig heterocyclisk forbindelse I.
Denne omsætning foretages normalt i nærværelse eller fravær af et inert opløsningsmiddel (fx dimethylformamid, dimethylsulfoxid, te-5 trahydrofuran, dimethoxyethan eller toluen) i nærværelse af et syrebindende middel, fx et alkalimetal, et alkalimetalhydrid, et alkali-metalamid, et alkalimetalhydroxid, et alkalimetalcarbonat, alkyl-lithium eller en organisk base ved en temperatur på mellem -70eC og reaktionsblandingens kogetemperatur, fortrinsvis ved mellem stuetem-10 peratur og 110°C, i et tidsrum på 0,5-24 timer. For at fremskynde reaktionen kan der anvendes en faseoverførselskatalysator, fx ben-zyltriethylammoniumchlorid eller tetra-n-butylammoniumbromid. I dette tilfælde kan vand anvendes som opløsningsmiddel.
Molforholdet mellem forbindelsen II og forbindelsen III ligger nor-15 malt på 1:1-10, fortrinsvis på 1:1,1-1,5.
Fremgangsmåde B
En forbindelse med den ovenfor anførte almene formel IV eller et alkalimetalsalt deraf omsættes med en forbindelse med den almene formel V
20 A2-Ri V
hvor Ri har den ovenfor anførte betydning, og A2 betegner et halogenatom, til dannelse af en nitrogenholdig heterocyclisk forbindelse I.
Reaktionen foretages normalt i fraværelse eller nærværelse af et 25 inert opløsningsmiddel (fx dimethylformamid, dimethylsulfoxid, tetra-hydrofuran, dimethoxyethan eller toluen) i nærværelse af et syrebindende middel, fx et alkalimetal, et alkalimetalhydrid, et alkalimetal-amid, et alkalimetalhydroxid, et alkalimetalcarbonat, alkyllithium eller en organisk base, ved en temperatur på mellem -30°C og reak-30 tionsblandingens koge temperatur, fortrinsvis mellem stuetemperatur og
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10 110eC, i et tidsrum på 0,5-24 timer. For at fremskynde reaktionen kan der anvendes en faseovergangskatalysator såsom benzyltriethylammo-niumchlorid eller te tra-n-butylammoniumb romid. I dette tilfælde kan vand anvendes som opløsningsmiddel.
5 Molforholdet mellem forbindelsen IV og forbindelsen V ligger normalt på 1:0,5-10, fortrinsvis på 1:0,8-5,0.
Ved de ovennævnte fremgangsmåder kan isolering af den dannede ni-trogenholdige heterocycliske forbindelse I fra reaktionsblandingen og rensningen af den isolerede nitrogenholdige heterocycliske forbindel-10 se I foretages på i og for sig kendt måde. Fx kan rensningen foretages ved omkrystallisation, chromatografi, etc.
Den nitrogenholdige heterocycliske forbindelse I har, ligesom de optisk aktive alkoholer ifølge opfindelsen, optiske isomerer ved de carbonatomer, hvortil grupperne 1¾ og R3 er knyttet. Desuden har de 15 nitrogenholdige heterocycliske forbindelser I et ensomt elektronpar på nitrogenatomet, så at nogle af dem kan danne salte med syrer.
Eksempler på syrer er uorganiske syrer (fx saltsyre, brombrintesyre og svovlsyre) og organiske syrer (fx trifluoreddikesyre og trich-loreddikesyre), etc.
20 Udførelsesformer for fremstillingen af forbindelserne ifølge opfindelsen illustreres i nedenstående eksempler, og anvendelsen af forbindelserne ifølge opfindelsen illustreres i nedenstående anvendelseseksempel: EKSEMPEL 1 25 Fremstilling af (S)-(+)-l-methyl-2-(4-phenoxyphenoxy)ethanol:
En opløsning af 2,14 g (11,5 millimol) 4-phenoxyphenol i 7 ml toluen hældtes ud i 3 ml af en vandig opløsning af 0,92 g (23,0 millimol) natriumhydroxid, og 1,0 g (17,24 millimol) (S)-(-)-propylenoxid (et 20 reagens fremstillet af Aldrich; [a] D = -7,2° (c = 1 i CHCI3)) til-30 sattes under omrøring. Til den vundne blanding sattes 185 mg tetra-n-butylammoniumbromid, og blandingen omrørtes ved stuetemperatur i 12
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11 timer efterfulgt af tilsætning af 1 g (S)-(-)-propylenoxid. Efter omrøring ved stuetemperatur i 6 timer omrørtes reaktionsblandingen kraftigt under tilsætning af 20 ml vand og 20 ml toluen. Toluenfasen blev fraskilt og vasket med en 20%'s vandig natriumhydroxidopløsning 5 og en vandig natriumchloridopløsning i den angivne rækkefølge og tørret over magnesiumsulfat. Fjernelse af opløsningsmidlet gav 2,35 g råt (S)-(+)-l-methyl-2-(4-phenoxyphenoxy)ethanol, som blev yderligere renset ved søjlechromatografi på silicagel, hvorved man fik 1,97 g 23 (S)-(+)-l-methyl-2-(4-phenoxyphenoxy)ethanol, [c«] d » +14,0° (c - 1 i 10 CHC13). ee: 72,9%.
EKSEMPEL 2
Dette eksempel belyser fremstilling af (S)-l-methyl-2-(4-phenoxyphe-noxy)ethyl acetat (som ved hydrolyse, jfr. ovenfor, kan omdannes til den frie alkohol) via (R)-l-methyl-2-(4-phenoxyphenoxy)ethyl methan-15 sulfonat:
En blanding af 82 mg (1,0 millimol) vandfrit natriumacetat, 250 mg (0,78 millimol; ee: 99,4%) (R)-l-methyl-2-(4-phenoxyphenoxy)ethyl methansulfonat og 5 ml dimethylformamid omrørtes ved en indre temperatur på 100-110°C i 5 timer. Efter at blandingen havde fået lov at 20 afkøle, tilsattes isvand, og reaktionsblandingen blev ekstraheret 3 gange med toluen. Toluenfasen blev tørret over vandfrit magnesiumsulfat. Opløsningsmidlet blev fjernet og remanensen renset ved tyndt- lagschromatografi under anvendelse af silicagel, hvorved man fik 23 158 mg (S)-(-)-l-methyl-2-(4-phenoxyphenoxy)ethyl acetat, [a] p * 25 -30,6° (c»li CHCI3). ee: 88,8%. ·
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12
ANVENDELSESEKSEMPEL
Fremstilling af forbindelse nr. 20 (fremgangsmåde B): 1) (S)-L-Ethyl lactat-tetrahydropyranylether 4,0 g (34 millimol) L-ethyllactat og 3,7 g (44 millimol) dihydropyran 5 opløstes i 20 ml tør diethylether. Til den resulterende blanding dryppedes en opløsning af 50 mg p-toluensulfonsyre i 2 ml tør ether ved en indre temperatur på 0°C, og blandingen omrør tes ved samme temperatur i 2 timer og ved 20°C i 12 timer. Reaktionsblandingen blev. hældt ud i en isafkølet 5Z's vandig kaliumcarbonatopløsning og rys-10 tet. Etherfasen blev fraskilt, vasket med vandig natriumchloridopløsning dg tørret over vandfrit magnesiumsulfat. Ved fjernelse af ether fik man 6,6 g næsten ren (S)-L-ethyl lactat-tetrahydropyranylether i form af en lysegul væske, n22,j) = 1,4395; [a]2p = -54,3° (c = 0,56 i CHC13).
15 2) (S)-2-(Tetrahydropyranyloxy)-l-propanol
Til en opløsning af 1,5 g (40 millimol) lithiumaluminiumhydrid i 50 ml tør ether dryppedes 6,6 g (33 millimol) af den i 1) vundne (S)-L-ethyl lactat-tetrahydropyranylether ved en indre temperatur på 0-10°C, og blandingen omrørtes ved samme temperatur i 1 time og ved 20 20°C i 1 time. Reaktionsblandingen blev derefter hældt ud i en is afkølet vandig ammoniumchloridopløsning og ekstraheret med ether.
Etherfasen blev vasket med vandig natriumchloridopløsning og tørret over vandfrit magnesiumsulfat. Fjernelse af ether gav 4,2 g (S)-2- 22 5 (tetrahydropyranyloxy)-l-propanol i form af en lysegul væske, n ’q = 25 1,4552; [a]2J - -5,3“ (c - 0,51 i CHCI3).
-1 IR-Spektrum (film): * 3400, 2930, 1080 og 1020 (kraftig) cm 3) (S)-2-(Tetrahydropyranyloxy)-l-propyl p-toluensulfonat 5,5 g (30 millimol) p-toluensulfonylchlorid sattes til en opløsning af 4,2 g (28 millimol) af det som beskrevet under 2) vundne (S)-30 2-(tetrahydropyranyloxy)-1-propanol i 7 g pyridin ved en temperatur på 0-5°C, og den resulterende blanding fik lov at henstå ved 0“C i 12
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13 timer. Reaktionsblandingen blev hældt ud i isvand og ekstraheret med ethylacetat. Ethylacetatfasen blev vasket med vand 5 gange og derefter med en vandig natriumchloridopløsning og tørret over vandfrit magnesiumsulfat. Fjernelse af opløsningsmidlet gav 6,8 g (S)-2-(te-5 trahydropyranyloxy)-1-propyl p-toluensulfonat i form af en lysegul væske.
1HNMR-Spektrum (CDC13, TMS): 6 (ppm) = 1,13 (3H, m), 1,3-1,8 (6H), 2.39 (3H, s), 3,2-4,2 (5H), 4,52 (IH, bred m), 7,0-8,0 (4H).
4) (S)-l-Methyl-2-(4-phenoxyphenoxy)ethanol 10 Til en suspension af 0,84 g (21 millimol; 60%'s i olie) natriumhydrid i 20 ml dimethylformamid sattes gradvis 4,20 g (23 millimol) 4-phen-oxyphenol under isafkøling, og blandingen omrørtes ved 20°C i 1 time.
6.39 g (20 millimol) af det som beskrevet under 3) vundne (S)-2-(te-trahydropyranyloxy)-1-propyl p-toluensulfonat tilsattes, og den 15 resulterende blanding omrørtes ved en indre temperatur på 70 ®C i 7 timer. Reaktionsblandingen blev derefter hældt ud i isvand og ekstraheret 2 gange med ether. Etherfasen blev vasket med en 3%'s vandig natriumhydroxidopløsning til fjernelse af ikke-orasat 4-phenoxyphenol. Etherfasen blev vasket med en vandig natriumchloridopløsning og 20 tørret over vandfrit magnesiumsulfat. Efter fjernelse af opløsningsmidlet sattes 50 ml methanol og 50 mg p-toluensulfonsyre til remanensen efterfulgt af omrøring ved 20°C i 1 time. Reaktionsblandingen blev hældt ud i vandig natriumhydrogencarbonatopløsning og ekstraheret 2 gange med ethylacetat. Ethylacetatfasen blev vasket med van-25 dig natriumchloridopløsning og tørret over vandfrit magnesiumsulfat.
Efter fjernelse af opløsningsmidlet blev remanensen renset ved søjle-chromatografi over silicagel, hvorved man fik 2,30 g (S)-l-methyl-2-(4-phenoxyphenoxy)ethano1 i form af hvide krystaller, smeltepunkt 73,6‘C; [a]2p - +18,5°C (c = 1,0 i CHCI3).
30 5) (S)-2-[l-Methyl-2-(4-phenoxyphenoxy)ethoxy]pyridin
Til en suspension af 80 mg (2,0 millimol; 60%'s i olie) natriumhydrid i 5 ml dimethylformamid sattes 500 mg (2,0 millimol) af det som beskrevet under 4) vundne (S)-l-methyl-2-(4-phenoxyphenoxy)ethanol ved
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14 en indre temperatur på 0°C, og den resulterende blanding omrørtes ved 0°C i 30 minutter og ved 20°C i 1 time. 280 mg (2,9 millimol) 2- fluorpyridin tilsattes, og omrøringen fortsattes ved 20°C i 12 timer.
Reaktionsblandingen blev hældt ud i isvand og ekstraheret 2 gange med 5 ethylacetat. Ethylacetatfasen blev vasket med vandig natriumchlorid- opløsning og tørret over vandfrit magnesiumsulfat. Efter fjernelse af opløsningsmidlet blev remanensen renset ved søj lechromatografi på silicagel, hvorved man fik 370 mg (S)-2-[l-methyl-2- (4-phenoxyphen- 23 23 oxy)ethoxy]pyridin i form af en lysegul væske, N j = 1,5828; [e] p = 10 -33,8°C (c - 0,34 i CHC13).
På samme måde som ovenfor beskrevet blev der fremstillet nitrogen-holdige heterocycliske slutforbindelser I og mellemprodukter hertil.
Nogle typiske eksempler herpå er vist i tabel I-II.
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15 R-3 R0 TABEL I -CH-0
Forbin- Rj^ R2 R3 Fysisk konstant delse nr.
(R/S - 99,7/0,3) ((R)-lsomer lal” “ +3V* (CHC13> c - 0,34)
H
20 ._. _^ t (R/S - 1,8/98,2) ((S)-lsoner la)” - -33,8* (CHC13, c - 0,34)
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16
Tabel I fortsat
Forbin- R^ R2 R3 Fysisk konstant delse nr.
/f ^ r\ ff \ f/l * λ ςκ> 1-^3 (R/S · 94,5/5,5) ((R)-isomer ng3 = +7,0° (CHC13) c - 0,20) 132 /T\ Λ n (R/S - 28,9/71,1) ((S)-ieotner nj3 = -4,4° (CHCI3, c = 0,64)
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17 4J ® “ e η co {» o —» β λ a — ® *
JjiriiH r—t <~l ·Η O Γ*0
m ·. - *«#>**,, OP
c CO II OP cr. 11 e**3 m II ® ti 0*-l r-4 CN CN ’«ί* t" 5 + o«n i υ ^ + u r* i ° * ” k k (N O' w || k vo || * σ> || ·. *<r il * co 7n ro σ> co 9\ ro p
Jj η Η η h ro ιΗ ίΓϊ^Τΐ ω (N Q O ·· CM Q O ·· (N Q y ·· sL^SC* r—, S3 · i—I ΓΠ · 1—1®· h SUd) S5UQJ oUO 8^0) ” MWQ) t_> w Q) 1—i *-* Φ *—1 ^ 0 H M H ^ O) φ fl) d) i 6 I g 0 o o o n to to oi •Η *H ·Η ·Η
1 I I I
w 2 w e< as 5 s g o p o o
ro ,» ro ^ tM CM
5—u’-^tas 5—u-'""X J3 (,5 \ \ sT S' aP y
\ \ U—O «""'33 u-U—« S
as B \ \ n υ u \ \ o i \ \ \ +) o o o o S 0 Φ 0 0 o o o o i oooo <0 ^_______ * ro Tf in vo <P in in in in o u H H H ^ ti c
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18
Nedenfor er anført nogle typiske testdata, som viser den fremragende insektbekæmpende virkning af de nitrogenholdige heterocycliske forbindelser I. De til sammenligning anvendte forbindelser er:
Forbindelse 5 nr. Kemisk struktur Bemærkninger A q 0 Kendt som "metho- / ν ιΑΑΛ ρ""*! æA-paEent- skrifter nr.
j_q 3.904.662 og 3.912.815
Forbindelse beskrevet \=y i ikke-behandlet ja pansk publiceret pa- j_5 tent ansøgning nr.
157522/1975 r /J'"λ -Jf Ti Forbindelse beskrevet W W ^ 1 tysk offentlig- gørelsesskrift nr.
20 2.616.755 F Forbindelse beskre- J vet i tysk offent liggørelsesskrift nr. 2516331 25 _ __:- I hvert af testeksemplerne er præparatet, der testes, fremstillet ifølge nedenstående formuleringseksempel 1: FORMULERINGSEKSEMPEL 1 20 dele af den pågældende forbindelse, 20 dele af en emulgator (en 30 blanding af polyoxyethylen-styreneret phenylether, polyoxy-
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19 ethylen-styreneret phenyletherpolymer og et alkylarylsulfonat) og 60 dele xylen blandes grundigt til dannelse af et emulgerbart koncentrat.
TESTEKSEMPEL 1 5 Et eraulgerbart koncentrat fremstillet ifølge formuleringseksempel 1 blev fortyndet med vand til dannelse af en 400 ganges fortynding.
0,7 ml fortyndet væske blev sat til 100 ml destilleret vand. Larver i sidste stadie af almindelig myg (Culex pipiens pallens) blev sat ud heri og opdrættet i 7 dage indtil emergens. Emergensgraden blev iagt-10 taget (to replikationer). Resultaterne er vist i tabel III.
Tabel III
Testforbindelse Koncentration Emergensgrad nr. (ppm) (%) 15 19 3,5 0 20 3,5 ' 0 131 3,5 0 132 3,5 0 20 A 3,5 0
Ubehandlet - 90 TESTEKSEMPEL 2 25 Et emulgerbart koncentrat fremstillet ifølge formuleringseksempel 1 blev fortyndet med vand til en bestemt fortynding. 0,5 ml af den fortyndede væske blev sat til 100 ml destilleret vand. Tyve larver i sidste trin af almindelig myg (Culex pipiens pallens) blev sat ud deri og opdrættet i 7 dage indtil emergens. Den koncentration, der 30 fremkaldte 50%'s inhibering af emergensen (IC,.q) (PPm) blev bestemt (to replikationer). Resultaterne er vist i tabel IV, hvor ΡΙ,-q svarer til -log IC5Q.
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20
Tabel IV
Testforbindelse nr. PI^q 19 3,9 5 20 4,4 A 3,7 B 1,1 C 1,6 10 F 0,3 TESTEKSEMPEL 3 2 g pulveriseret dyrefoder blev blandet grundigt med 14 g klid. Et emulgerbart koncentrat fremstillet som i formuleringseksempel 1 blev 15 fortyndet med vand til den ønskede koncentration, og 28 ml af den fortyndede væske blev sat til den ovennævnte blanding. Den vundne blanding blev omrørt grundigt til dannelse af en kunstig ernæring. 30 stuefluelarver (Musca domestica) fik lov at vokse deri indtil puppedannelse. Pupperne blev anbragt i et plastbæger, og emergensgraden 20 blev bestemt. Den procentvise emergensinhibering blev beregnet ved følgende ligning:
Emergens- Emergensgrad i behandlet ansats
inhibering ^ Emergensgrad i ubehandlet ansats ^ X
(%) 25 Resultaterne er anført i tabel V.

Claims (2)

10 B 36 15 0 CO 0 0 F 10 5 0
15 Optisk aktiv phenoxyphenoxyalkohol, kendetegnet ved, at den er en (S)-(+)-isomer af forbindelsen med formlen ch3 20 (R)-(-)-isomer af forbindelsen med formlen CH- (S)-(+)-isomer af forbindelsen med formlen DK 165972B 22 T3 f>^0-CH-CH2-0H eller (R)- () - isomer af forbindelsen med formlen <[H3 ^0^0-CH-CH2-OH 5
DK001591A 1983-04-25 1991-01-04 Optisk aktive phenoxyphenoxyalkoholer DK165972C (da)

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DK001491A DK165740C (da) 1983-04-25 1991-01-04 Fluorsubstituerede phenoxyphenoxyalkoholer
DK001591A DK165972C (da) 1983-04-25 1991-01-04 Optisk aktive phenoxyphenoxyalkoholer
DK001691A DK165443C (da) 1983-04-25 1991-01-04 4-(3,5-difluorphenoxy)phenol
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Families Citing this family (98)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS59199673A (ja) 1983-04-25 1984-11-12 Sumitomo Chem Co Ltd 含窒素複素環化合物、その製造法およびそれを有効成分とする有害生物防除剤
JPH0739394B2 (ja) * 1985-05-30 1995-05-01 住友化学工業株式会社 含窒素複素環化合物およびそれを有効成分として含有する有害生物防除剤
DE3681109D1 (de) * 1985-07-18 1991-10-02 Sandoz Ag Stickstoffhaltige heterozyklische verbindungen.
GB8611617D0 (en) * 1986-05-13 1986-06-18 Shell Int Research Fungicides
DE3712752A1 (de) * 1987-04-15 1988-11-03 Hoechst Ag Heterocyclische neophananaloga, verfahren zu ihrer herstellung und ihre verwendung als schaedlingsbekaempfungsmittel
EP0331529A3 (en) * 1988-03-03 1991-11-21 Ube Industries, Ltd. Diphenyl ether derivatives, process for producing the same and insecticide and acaricide containing the same as active ingredient
DE3825172A1 (de) * 1988-07-23 1990-01-25 Bayer Ag, 5090 Leverkusen Mittel zur bekaempfung von floehen
DE3825173A1 (de) * 1988-07-23 1990-03-22 Bayer Ag Substituierte tricyclische verbindungen, verfahren zu ihrer herstellung und ihre verwendung als insektizide
DE3828820A1 (de) * 1988-08-25 1990-03-22 Bayer Ag Substituierte pyridine, verfahren zu ihrer herstellung und ihre verwendung als insektizide
AU617229B2 (en) * 1988-12-27 1991-11-21 Sumitomo Chemical Company, Limited Pyrazole compounds, and their production and use
EP0388682A1 (de) * 1989-03-15 1990-09-26 Bayer Ag Substituierte Heteroarylphenylether, Verfahren zu ihrer Herstellung und ihre Verwendung als Insektizide
JPH0334951A (ja) * 1989-06-30 1991-02-14 Sumitomo Chem Co Ltd アルコール誘導体の製造法および分離取得方法
NZ238817A (en) * 1990-07-18 1992-09-25 Sumitomo Chemical Co Pyrimidine derivatives, preparation and use as insecticides, acaricides and fungicides
US5236924A (en) * 1990-07-18 1993-08-17 Sumitomo Chemical Co., Ltd. Pyrimidine derivatives and fungicides and/or acaricides containing them as active ingredient
DE4033484A1 (de) * 1990-10-20 1992-04-23 Basf Ag Hydrochinondiether, verfahren zu ihrer herstellung und ihre verwendung zur schaedlingsbekaempfung
DE4131924A1 (de) * 1991-09-25 1993-07-08 Hoechst Ag Substituierte 4-alkoxypyrimidine, verfahren zu ihrer herstellung und ihre verwendung als schaedlingsbekaempfungsmittel
US5439924A (en) * 1991-12-23 1995-08-08 Virbac, Inc. Systemic control of parasites
AU660205B2 (en) * 1991-12-23 1995-06-15 Virbac, Inc Systemic control of parasites
US5632999A (en) * 1993-08-18 1997-05-27 Virbac, Inc. Sustained release pyriproxifen compositions for parasite control
US5883262A (en) * 1994-04-22 1999-03-16 Sumitomo Chemical Company, Limited Ether compounds and their use
US5942525A (en) * 1995-05-11 1999-08-24 Ecto Development Corporation Spot treatment of animals with pyriproxyfen and an insecticide
CO4750805A1 (es) * 1995-12-13 1999-03-31 Sumitomo Chemical Co Compuesto para champu
JPH10130104A (ja) * 1996-11-01 1998-05-19 Sumitomo Chem Co Ltd 農薬乳剤
ES2359973T3 (es) 1998-03-19 2011-05-30 MERCK SHARP &amp; DOHME CORP. Composiciones poliméricas líquidas para la liberación controlada de sustancias bioactivas.
US7045519B2 (en) * 1998-06-19 2006-05-16 Chiron Corporation Inhibitors of glycogen synthase kinase 3
KR100581199B1 (ko) 1998-06-19 2006-05-17 카이론 코포레이션 글리코겐 신타제 키나제 3의 억제제
TWI221082B (en) 1999-04-14 2004-09-21 Sumitomo Chemical Co Pesticidal compositions
WO2001006853A2 (en) * 1999-07-23 2001-02-01 Bioparken As Novel juvenile hormone analogues and their use as antifouling agents
EP1204413A2 (en) * 1999-07-23 2002-05-15 Bioparken AS Control of crustacean infestation of aquatic animals
JP4288794B2 (ja) 1999-10-26 2009-07-01 住友化学株式会社 殺虫・殺ダニ組成物
DE19953775A1 (de) 1999-11-09 2001-05-10 Bayer Ag Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften
US6200584B1 (en) 1999-12-03 2001-03-13 Wellmark International Insect control by insect growth regulators broadcast by volatilization
US6787342B2 (en) 2000-02-16 2004-09-07 Merial Limited Paste formulations
EP1304036B1 (en) * 2000-07-06 2007-01-03 Sumitomo Chemical Company, Limited Insecticides
JP4604391B2 (ja) * 2000-07-06 2011-01-05 住友化学株式会社 害虫防除剤組成物
JP2002363121A (ja) * 2001-04-06 2002-12-18 Sumitomo Chem Co Ltd 光学活性１−（４−フェノキシフェノキシ）−２−プロパノールの製造法
JP4701538B2 (ja) 2001-05-21 2011-06-15 住友化学株式会社 農業害虫防除剤組成物
US7262214B2 (en) 2003-02-26 2007-08-28 Merial Limited 1-N-arylpyrazole derivatives in prevention of arthropod-borne and mosquito-borne diseases
AU2005239726C1 (en) * 2004-12-14 2010-11-18 Sumitomo Chemical Company, Limited Pesticidal composition comprising pyriproxyfen
US8362086B2 (en) 2005-08-19 2013-01-29 Merial Limited Long acting injectable formulations
JP5433412B2 (ja) 2006-07-05 2014-03-05 アヴェンティス アグリカルチャ １−アリール−５−アルキルピラゾール誘導体化合物、その作製方法及び使用方法
JP5266638B2 (ja) * 2006-12-20 2013-08-21 住友化学株式会社 農薬乳剤
DK2155699T5 (da) 2007-05-15 2017-05-22 Merial Inc Arylazol-2-yl-cyanoethylamino-forbindelser, fremgangsmåde til fremstilling og fremgangsmåde til anvendelse deraf
DE102007045957A1 (de) 2007-09-26 2009-04-09 Bayer Cropscience Ag Wirkstoffkombinationen mit insektiziden und akarziden Eigenschaften
EP2127522A1 (de) 2008-05-29 2009-12-02 Bayer CropScience AG Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften
MX2011005011A (es) 2008-11-14 2011-07-29 Merial Ltd Compuestos de arilazol-2-il-cianoetilamino enantiomericamente enriquecidos, metodo de elaboracion y de uso de los mismos.
KR101660068B1 (ko) 2008-11-19 2016-09-26 메리얼 인코포레이티드 기생충 감염 치료를 위한 1-아릴피라졸 단독 또는 포름아미딘과의 조합을 포함하는 조성물
JP5595412B2 (ja) 2008-12-04 2014-09-24 メリアル リミテッド 二量体アベルメクチン及びミルベマイシン誘導体
EP2410849A1 (de) 2009-03-25 2012-02-01 Bayer CropScience AG Wirkstoffkombinationen mit insektiziden und akariziden eigenschaften
MX2012001170A (es) 2009-07-30 2012-07-20 Merial Ltd Compuestos de 4-amino-tieno [2,3-d]pirimidina insecticidas y metodos para su uso.
EP2507209B1 (en) 2009-12-04 2015-07-08 Merial, Inc. Pesticidal bis-organosulfur compounds
EA021522B9 (ru) 2009-12-17 2016-08-31 Мериал Лимитед Противопаразитарные дигидроазоловые соединения и содержащие их композиции
BR112012014933B1 (pt) 2009-12-17 2020-10-27 Merial, Inc. composições que compreendem compostos lactonas macrocíclicas e spirodioxepinoindóis
UA108641C2 (uk) 2010-04-02 2015-05-25 Паразитицидна композиція, яка містить чотири активних агенти, та спосіб її застосування
EP2382865A1 (de) 2010-04-28 2011-11-02 Bayer CropScience AG Synergistische Wirkstoffkombinationen
WO2012043372A1 (ja) 2010-09-29 2012-04-05 東海ゴム工業株式会社 水系ホース用ゴム組成物およびそれを用いて得られる水系ホース
MX2013005414A (es) 2010-11-16 2013-08-29 Centre Nat Rech Scient Derivados de monensina novedosos para el tratamiento y prevencion de infecciones por protozoarios.
CN102246758A (zh) * 2011-06-04 2011-11-23 海利尔药业集团股份有限公司 一种杀虫组合物
EA201400058A1 (ru) 2011-06-27 2014-07-30 Мериал Лимитед Соединения и композиции на основе амидопиридиловых эфиров и их применение против паразитов
US20120329832A1 (en) 2011-06-27 2012-12-27 Jean Delaveau Novel Insect-Repellent Coumarin Derivatives, Syntheses, and Methods of Use
RS61048B1 (sr) 2011-09-12 2020-12-31 Boehringer Ingelheim Animal Health Usa Inc Paraziticidne kompozicije koje sadrže izoksazolin aktivni agens, postupak i njihove primene
WO2013044118A2 (en) 2011-09-23 2013-03-28 Merial Limited Indirect modeling of new repellent molecules active against insects, acarids, and other arthropods
WO2013074892A1 (en) 2011-11-17 2013-05-23 Merial Limited Compositions comprising an aryl pyrazole and a substituted imidazole, methods and uses thereof
ES2978407T3 (es) 2011-12-02 2024-09-12 Boehringer Ingelheim Vetmedica Gmbh Formulaciones de moxidectina inyectables de acción prolongada
ES2720201T3 (es) 2012-02-06 2019-07-18 Merial Inc Composiciones parasiticidas orales veterinarias que comprenden agentes activos de acción sistémica y usos de las mismas
JO3626B1 (ar) 2012-02-23 2020-08-27 Merial Inc تركيبات موضعية تحتوي على فيبرونيل و بيرميثرين و طرق استخدامها
SG11201406730RA (en) 2012-04-20 2014-11-27 Merial Ltd Parasiticidal compositions comprising benzimidazole derivatives, methods and uses thereof
EA030814B1 (ru) 2012-11-20 2018-10-31 Мериал, Инк. Антигельминтные соединения, композиции и способы их применения
SG11201603430XA (en) 2013-11-01 2016-05-30 Merial Ltd Antiparasitic and pesticidal isoxazoline compounds
AU2015247463B2 (en) 2014-04-17 2018-03-29 Basf, Se Use of malononitrile compounds for protecting animals from parasites
WO2015179414A1 (en) 2014-05-19 2015-11-26 Merial, Inc. Anthelmintic compounds
ES2723969T3 (es) 2014-06-19 2019-09-04 Merial Inc Composiciones parasiticidas que comprenden derivados de indol, procedimientos y usos de las mismas
AU2015339096B2 (en) 2014-10-31 2018-08-02 Boehringer Ingelheim Animal Health USA Inc. Parasiticidal composition comprising fipronil
CN105724395B (zh) * 2014-12-09 2018-05-25 沈阳中化农药化工研发有限公司 一种二元杀虫剂组合物及其应用
UY36570A (es) 2015-02-26 2016-10-31 Merial Inc Formulaciones inyectables de acción prolongada que comprenden un agente activo isoxazolina, métodos y usos de las mismas
SG10202103403SA (en) 2015-05-20 2021-05-28 Boehringer Ingelheim Animal Health Usa Inc Anthelmintic depsipeptide compounds
CN105076138B (zh) * 2015-08-21 2017-08-04 山东农业大学 一种虫螨腈和吡丙醚的杀虫组合物及其制剂与应用
CN105330519A (zh) * 2015-12-09 2016-02-17 上海生农生化制品有限公司 一种1-(4-苯氧基苯基)-2-丙醇的合成方法
CN105503712B (zh) * 2015-12-11 2019-01-18 中国农业大学 一种吡乙苯醚肟酯化合物及其制备方法与应用
CN105601564A (zh) * 2015-12-21 2016-05-25 江西安利达化工有限公司 一种吡丙醚类化合物的制备方法
UY37137A (es) 2016-02-24 2017-09-29 Merial Inc Compuestos antiparasitarios de isoxazolina, formulaciones inyectables de acción prolongada que los comprenden, métodos y usos de los mismos
WO2018039508A1 (en) 2016-08-25 2018-03-01 Merial, Inc. Method for reducing unwanted effects in parasiticidal treatments
WO2018071535A1 (en) 2016-10-14 2018-04-19 Merial, Inc. Pesticidal and parasiticidal vinyl isoxazoline compounds
US11382949B2 (en) 2016-11-16 2022-07-12 Boehringer Ingelheim Animal Health USA Inc. Anthelmintic depsipeptide compounds
CN106538587A (zh) * 2016-11-26 2017-03-29 佛山市普尔玛农化有限公司 含有双丙环虫酯和吡丙醚的农药组合物
WO2019005700A1 (en) 2017-06-26 2019-01-03 Merial, Inc. DOUBLE-ACTING PARASITICIDE GRANULATE COMPOSITIONS, METHODS AND USES THEREOF
WO2019036407A1 (en) 2017-08-14 2019-02-21 Merial, Inc. PYRAZOLE-ISOXAZOLINE COMPOUNDS WITH PESTICIDE AND PARASITICIDE ACTIVITY
CN107827716A (zh) * 2017-09-28 2018-03-23 大连天源基化学有限公司 1‑(4‑苯氧苯氧基)‑2‑丙醇生产中釜残的处理方法
IL279977B2 (en) 2018-07-09 2024-06-01 Boehringer Ingelheim Animal Health Usa Inc Heterocyclic anthelmintic compounds
US11773066B2 (en) 2018-11-20 2023-10-03 Boehringer Ingelheim Animal Health USA Inc. Indazolylcyanoethylamino compound, compositions of same, method of making, and methods of using thereof
CN109503471B (zh) * 2018-11-23 2022-08-26 江苏龙灯化学有限公司 一种吡丙醚的晶型及其制备方法和用途
WO2020180635A1 (en) 2019-03-01 2020-09-10 Boehringer Ingelheim Animal Health USA Inc. Injectable clorsulon compositions, methods and uses thereof
US11560388B2 (en) 2019-03-19 2023-01-24 Boehringer Ingelheim Vetmedica Gmbh Anthelmintic aza-benzothiophene and aza-benzofuran compounds
CA3183100A1 (en) 2020-05-29 2021-12-02 Boehringer Ingelheim Pharma Gmbh & Co. Kg Anthelmintic heterocyclic compounds
WO2022140728A1 (en) 2020-12-21 2022-06-30 Boehringer Ingelheim Animam Health Usa Inc. Parasiticidal collar comprising isoxazoline compounds
JP2025507585A (ja) 2022-02-17 2025-03-21 ベーリンガー インゲルハイム フェトメディカ ゲーエムベーハー 流体製品メーラーを提供する方法及びシステム
JP7693634B2 (ja) 2022-12-16 2025-06-17 株式会社神戸製鋼所 通電部品、溶接トーチ、溶接システム、通電部品の設計方法及びコンタクトチップ
WO2025257633A1 (en) 2024-06-12 2025-12-18 Boehringer Ingelheim Vetmedica Gmbh Long-acting castor oil-containing injectable formulations and methods of use thereof

Family Cites Families (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1929870A (en) * 1932-10-11 1933-10-10 William B Pine Process for making esters from olefines
US3814774A (en) * 1971-02-16 1974-06-04 Pennwalt Corp 3,5-dichloro-2-pyridoxyethyl ethers
US4061683A (en) * 1973-01-31 1977-12-06 Ciba-Geigy Corporation Diphenyl ether derivatives
DE2516515A1 (de) * 1974-04-18 1975-10-30 Ciba Geigy Ag Phenoxy-phenylaether
DE2516331A1 (de) * 1974-04-18 1975-11-06 Ciba Geigy Ag Phenylaralkyl-aether und -thioaether
DE2520177A1 (de) * 1974-05-09 1975-11-27 Ciba Geigy Ag Diaether
DE2616755A1 (de) * 1975-04-18 1976-10-28 Ciba Geigy Ag Diaether, verfahren zu ihrer herstellung und ihre verwendung
IT1063074B (it) * 1976-03-17 1985-02-11 Lpb Ist Farm Ammidi di acidi(z-pirimidiniltio)al canoici quali agent antilipemici
DE2611695A1 (de) * 1976-03-19 1977-09-29 Hoechst Ag Herbizide mittel
GB1579839A (en) * 1977-04-16 1980-11-26 Lafon Labor Chlorophenoxybenzene derivatives
DE3004610A1 (de) * 1980-02-08 1981-08-13 Hoechst Ag, 6000 Frankfurt Verfahren zur herstellung von 4-phenoxyphenolen
DE3044010A1 (de) * 1980-11-22 1982-06-24 Hoechst Ag, 6000 Frankfurt Phenoxybenzylester, ihre herstellung und ihre verwendung als pflanzenschutzmittel und im veterinaermedizinischen bereich
EP0072475B1 (de) * 1981-08-17 1986-08-20 F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft Carbaminsäureester, Verfahren zu deren Herstellung, Schädlingsbekämpfungsmittel, die diese Verbindungen als Wirkstoffe enthalten, sowie Verwendung solcher Verbindungen und Mittel zur Bekämpfung von Schädlingen
JPS59199673A (ja) 1983-04-25 1984-11-12 Sumitomo Chem Co Ltd 含窒素複素環化合物、その製造法およびそれを有効成分とする有害生物防除剤
JPH0658512B2 (ja) * 1985-04-12 1994-08-03 富士写真フイルム株式会社 ハロゲン化銀写真感光材料
EP0223406B1 (en) * 1985-10-15 1990-08-29 Kumiai Chemical Industry Co., Ltd. Pyrimidine derivatives and herbicidal uses thereof

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MY8600647A (en) 1986-12-31
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DK1491A (da) 1991-01-04
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KR910007963B1 (ko) 1991-10-04
DK162091B (da) 1991-09-16
DK205584D0 (da) 1984-04-24
GB2140010B (en) 1986-01-08
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IL87772A (en) 1989-09-28
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US4970222A (en) 1990-11-13
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US4879292A (en) 1989-11-07
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DK207291A (da) 1991-12-27
GB8410240D0 (en) 1984-05-31
US4751225A (en) 1988-06-14
DK207291D0 (da) 1991-12-27
DK165443B (da) 1992-11-30
GB2140010A (en) 1984-11-21
BR8401940A (pt) 1984-12-04
IN159713B (da) 1987-06-06

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