DK165740B - Fluorsubstituerede phenoxyphenoxyalkoholer - Google Patents

Fluorsubstituerede phenoxyphenoxyalkoholer Download PDF

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Publication number
DK165740B
DK165740B DK001491A DK1491A DK165740B DK 165740 B DK165740 B DK 165740B DK 001491 A DK001491 A DK 001491A DK 1491 A DK1491 A DK 1491A DK 165740 B DK165740 B DK 165740B
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compound
difluorophenoxy
mixture
phenoxy
compounds
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DK001491A
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DK1491D0 (da
DK1491A (da
DK165740C (da
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Sumio Nishida
Makoto Hatakoshi
Hirosi Kisida
Noritada Matsuo
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Sumitomo Chemical Co
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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
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    • 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
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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
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    • 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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    • 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
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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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    • C07D213/02—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
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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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    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
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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
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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
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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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    • C07D251/26—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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    • 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)
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  • 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)
  • Pyrane Compounds (AREA)
  • Thiazole And Isothizaole Compounds (AREA)
  • Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)

Description

i
DK 165740 B
Den foreliggende opfindelse angår hidtil ukendte fluorsubstituerede phenoxyphenoxyalkoholer, som er mellemprodukter ved fremstilling af nitrogenholdige heterocycliske forbindelser.
De fluorsubstituerede phenoxyphenoxyalkoholer ifølge opfindelsen er 5 ejendommelige ved, at de har den almene formel F\__ __ R, R0 i/ \ I2 // \\-0-T 'Vo-CH-CH-OH F/ hvor R2 og R3 har samme eller forskellig betydning og hver betegner et hydrogenatom eller en methylgruppe.
De nitrogenholdige heterocycliske forbindelser, ved hvis fremstilling forbindelserne ifølge opfindelsen er mellemprodukter, har den almene 10 formel I, FV_ __ r3 r2 ft λ 2 1 ^ \ / 0 \ /·°”0Η"0Η~°“Ηχ hvor R^ betegner en af nedenstående grupper 'ft-' fi-*» 'ft-’» (Rg)^ ' R10 ' R12 ' R14 VY*15 'yS ΥΥ^ίί -R17 eller R16 ' R21 R20
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2 (hvor R7, Rg, R9 j ^qi ®12’ ^13' ^4’ ^15’ ^16 ^17 samme eller forskellig betydning og hver betegner et hydrogenatom, et halogenatom, alkyl, ^-alkoxy, ^-alkylthio, trifluormethyl eller nitro, R^g, R^g, R^q og R^^ har samme eller forskellig betyd-5 ning og hver betegner et hydrogenatom eller en methylgruppe, k betegner 0 eller 1, og 1 betegner et tal 0-3); og R2 og R3 har samme eller forskellig betydning og. hver betegner et hydrogenatom eller en methylgruppe.
Det ovenfor anvendte udtryk "halogen” betegner chlor, brom, iod og 10 fluor.
Blandt de nitrogenholdige heterocycliske forbindelser foretrækkes sådanne med formlen I, hvor R^ betegner en af nedenstående grupper "ώ-*7 Ύ^~Εΐ1 ΊΟ-*17 (Rg)^ R12 15 (hvor R7, Rg, R^, Rj^ og R^ hver for sig betegner et hydrogeneller fluor atom, og 1 har den ovenfor anførte betydning).
Organophosphor-insekticider, organorchlorerede insekticider, carba-matinsekticider, etc. har bidraget meget til forebyggelse og udryd -20 delse af skadelige insekter. Nogle af disse insekticider har imidlertid høj toxicitet. Deres eftervirkning forårsager endvidere undertiden uønsket abnormalitet i insekternes økosystem. Endvidere er der hos stuefluer, "planthoppers", cikader, risborelarver, etc. iagttaget resistens mod insekticiderne.
25 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 juvenilhormonagtig virkning; som et resultat heraf har det nu vist sig, at de nitrogenholdige heterocycliske forbindelser med den almene 30 formel I kan anvendes til bekæmpelse af insekter i landbrugsområder, /
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3 skovområder, kornmagasiner, i oplagrede produkter, i sanitære installationer, etc.
Som insekticid med juvenilhormonagtig virkning kendes "methopren" (USA-patent nr. 3,904.662 og 3.912.815), Denne kendte forbindelses 5 insekticide virkning er stadig ikke helt tilfredsstillende.
De nitrogenholdige heterocycliske forbindelser med den almene formel I viser en juvenilhormonagtig bekæmpende virkning og kan derfor anvendes i lav koncentration til bekæmpelse af mange forskellige insekter hørende til Coleoptera, Lepidoptera, Hemiptera, Dictyoptera, 10 Diptera, etc., samt spindemider (Teranychidae) hørende til gruppen Acarina inden for landbrugsområder, skovområder, kornmagasiner, i oplagrede produkter, sanitære installationer, etc.
I tysk offentliggørelsesskrift nr. 2.516.331 beskrives bl.a. phe-noxyphenoxyalkylpyridylforbindelser med insecticid virkning. I de i 15 det følgende anførte testeksempler 2 og 3 er beskrevet sammenlignende forsøg, hvor nitrogenholdige heterocycliske forbindelser med formlen I, der er fremstillet ud fra fluorsubstituerede phenoxyphenoxyalkoho-ler ifølge opfindelsen, er sammenlignet med bl.a. en af de nærmest beslægtede forbindelser fra det tyske offentliggørelsesskrift, i 20 testeksempleme betegnet forbindelse F. Det fremgår af forsøgsresultaterne, at de nitrogenholdige heterocycliske forbindelser, der er fremstillet ud fra forbindelserne ifølge opfindelsen, har en overraskende, overlegen insecticid virkning i forhold til den fra det tyske offentliggørelsesskrift kendte forbindelse F.
25 I EP offentliggørelsesskrift nr. 72.475 er beskrevet enkelte udgangsforbindelser, der er nært beslægtede med forbindelserne ifølge opfindelsen, men som er monofluorsubstituerede, og som anvendes til fremstilling af en anden type slutprodukter end de nitrogenholdige heterocycliske forbindelser med formlen I.
30 De fluorsubstituerede phenoxyphenoxyalkoholer ifølge opfindelsen kan fremstilles på i og for sig kendt måde, og typiske eksempler på deres fremstilling og videre omdannelse til andre mellemprodukter er vist nedenfor:
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4
Fremgangsmåde (1) F\_ h3o® 0.0-O-0H -—->
p' f3 ,0-WL
Br-CH-CH x VI
VII
W /T\. ^ CH MgEr // \\-o-i7 'Vo-ch-cho ---> W \=y eller LiAlH^
F VIII
Fv V—\ __k R-j R-, ft \ ft \ I3 l3
sf y~Q~(/ y-O-CH-CH-OH
F/ IV F\ >Br3 <3'2 > \-.f/-°-CH-CH-Ai
eller H^C OHS02C1/ O
n (hvor R2 og R3 har den ovenfor anførte betydning, betegner en 5 alkylgruppe, og betegner Br eller tosyloxy).
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5
Fremgangsmåde (2)
F\ R
//—\ /7~\ I 2 base (' \\-CK' 7“ OH + CH„—CH -> yr W \y (VI) (XI) F.
μ \ ff λ 12
\_/~° \_/~°~CH2-CH-OH
PBr- F\ , Rn __3_ Y—v fTl\ 12
In > \ f°\ f~ 0-CH2“CH-A! eller H3C-^-S02Cl/ Qj) J/=' (hvor R2 og har den ovenfor anførte betydning).
5 Fremgangsmåde (3) F.
// \ ff base V__ \ Pi
< 7-0-(' 'Voh _ \ h \ f/ \ 13 II
\—/ Λ—/ ^ U y-o-f t-o-ch-c-o-w2 f2 8
Br-CH-C-0-W2 F
VI XIII XIV
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6
LiAlH, F\ _ R, --' Q-o^°-«-®2-oh PBr. F\_ ,__ Ro 3 _ V-~\ r—\ 13 “ > // n-O-V y-0-CH-CH2-A1
eller HjC-ØksOjCI/ Q pW
(hvor Rj og A^ har den ovenfor anførte betydning, og W2 betegner en alkylgruppe).
Forbindelsen VI kan fremstilles på i og for sig kendt måde (jfr. .
Angew. Chem. 52, 1938, s. 915; publiceret japansk patentansøgning 5 (ikke-behandlet) nr. 62033/1980). Et typisk eksempel på fremstilling af forbindelsen VI, 4-(3,5-difluorphenoxy)phenol, er illustreret nedenfor:
F
\-> j-V kobber eller en forbin- F + M0 \ delse dermed ^o^ocHa ———» (hvor M betegner et alkalimetalatom).
Typiske eksempler på den videre omdannelse af de ovenfor beskrevne 10 mellemprodukter til de nitrogenholdige heterocycliske forbindelser I er anført nedenfor:
Fremgangsmåde A
En forbindelse med den ovenfor anførte almene formel II omsættes med en forbindelse med den almene formel III
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7 H-0-% 111 hvor R^ 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 5 inert opløsningsmiddel (fx dimethylformamid, dimethylsulfoxid, te-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 -70°C og 10 reaktionsblandingens kogetemperatur, fortrinsvis ved mellem stuetemperatur 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.
15 Molforholdet mellem forbindelsen II og forbindelsen III ligger normalt 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 20 formel V
A2-Ri V
hvor Rj^ har den ovenfor anførte betydning, og A2 betegner et halogenatom, til dannelse af en nitrogenholdig heterocyclisk forbindelse I.
25 Reaktionen foretages normalt i fraværelse eller nærværelse af et inert opløsningsmiddel (fx dimethylformamid, dimethylsulfoxid, tetra-hydrofuran, dime thoxye than eller toluen) i nærværelse af et syrebindende middel, fx et alkalimetal, et alkalimetalhydrid, et alkalimetal-amid, et alkalimetalhydroxid, et alkalimetalcarbonat, alkyllithium 8
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eller en organisk base, ved en temperatur på mellem -30°C og reaktionsblandingens kogetemperatur, fortrinsvis mellem stuetemperatur og 110“C, i et tidsrum på 0,5-24 timer. For at fremskynde reaktionen kan der anvendes en faseovergangskatalysator såsom benzyltriethylammo-5 niumchlorid eller tetra-n-butylammoniumbroraid. I dette tilfælde kan vand anvendes som opløsningsmiddel.
Molforholdet mellem forbindelsen XV 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-10 trogehholdige heterocycliske forbindelse I fra reaktionsblandingen og rensningen af den isolerede nitrogehholdige heterocycliske forbindelse I foretages på i og for sig kendt måde. Fx kan rensningen foretages ved omkrystallisation, chromatografi, etc.
Den nitrogenholdige heterocycliske forbindelse I har optiske isomerer 15 ved de carbonatomer, hvortil grupperne R2 og R3 er knyttet, når mindst én af R2 og R3 betegner methyl. Desuden har de 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 20 organiske syrer (fx trifluoreddikesyre og trichloreddikesyre), etc.
Udførelsesformer for fremstillingen af forbindelserne ifølge opfindelsen illustreres i nedenstående eksempler, omdannelsen af forbindelserne til andre mellemprodukter illustreres i nedenstående referenceeksempler, og anvendelsen af forbindelserne ifølge opfindelsen 25 illustreres i nedenstående anvendelseseksempel: EKSEMPEL 1
Fremstilling af 4-(3,5-difluorphenoxy)anisol: 7,56 g (0,189 millimol; 602's i olie) natriumhydrid blev vasket med n-hexan til fjernelse af olien, og 100 ml N,N-dime thyl formamid til-30 sattes til dannelse af en suspension. Til den således fremstillede 9 DK 16574Ub suspension sattes gradvis og under omrøring 25,84 g (0,208 mol) 4-methoxyphenol, og omrøring fortsattes, indtil hydrogengasudviklingen ophørte. 30,00 g (0,227 mol) 1,3,5-trifluorbenzen og 0,50 g cuprochlorid tilsattes. Den resulterende blanding blev opvarmet til 5 kogning under tilbagesvaling i 8 timer under omrøring. Efter at blandingen havde fået lov at afkøle, blev den hældt ud i isvand og ekstraheret med toluen. Toluenfasen blev tørret over vandfrit magnesiumsulfat. Opløsningsmidlet blev fjernet og den resterende olie destilleret under reduceret tryk, hvorved man fik 25,42 g 4-(3,5-10 difluorphenoxy)anisol, kogepunkt 98,5eC/0,2 mm Hg.
Fremstilling af 4-(3,5-difluorphenoxy)phenol:
En blanding af 22,0 g (0,093 mol) 4-(3,5-difluorphenoxy)anisol, 200 ml eddikesyre og 200 ml af en 47%'s vandig hydrogenbromidopløs-ning blev opvarmet til kogning under tilbagesvaling under omrøring i 15 8 timer. Efter at blandingen havde fået lov at afkøle, blev den hældt ud i isvand og ekstraheret med en blanding af ether og n-hexan i forholdet 1:2. Den organiske fase blev vasket 3 gange med vand og tørret over vandfrit magnesiumsulfat. Fjernelse af opløsningsmidlet gav 20,27 g 4-(3,5-difluorphenoxy)phenol.
20 Fremstilling af 2-[4-(3,5-difluorphenoxy)phenoxy]ethanol: 9,0 g (40,5 millimol) 4-(3,5-difluorphenoxy)phenol sattes til en ethanolisk opløsning af natriumethoxid fremstillet ud fra 40 ml ethanol og 939 mg (40,9 millimol) natrium. Til den resulterende opløsning sattes 3,26 g (40,5 millimol) 2-chlorethanol dråbevis under 25 omrøring og under kogning under tilbagesvaling. Efter endt tilsætning omrørtes den resulterende blanding under kogning under tilbagesvaling i 4 timer. Efter at blandingen havde fået lov at afkøle, blev ethano-let fjernet og den resterende olie opløst i toluen. Toluenfasen blev vasket én gang med vand, 2 gange med en 20%'s vandig kaliumhydroxid-30 opløsning og én gang med en mættet vandig natriumchloridopløsning i den angivne rækkefølge og tørret over vandfrit magnesiumsulfat.
Fjernelse af opløsningsmidlet gav 6,50 g 2-[4-(3,5-difluorphenoxy)-phenoxy]e thano1.
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10 EKSEMPEL 2
Fremstilling af l-methyl-2- [4- (3,5-difluorphenoxy)phenoxy ] ethanol: 3,0 g (13,5 millimol) 4-(3,5-difluorphenoxy)phenol sattes til en ethanolisk opløsning af natriumethoxid fremstillet ud fra 15 ml 5 ethanol og 313 mg (13,6 millimol) natrium. Til den resulterende opløsning sattes 1,60 g (16,9 millimol) l-chlor-2-propanol dråbevis under omrøring og under kogning under tilbagesvaling. Efter endt tilsætning omrørtes den resulterende blanding under kogning under tilbagesvaling i 5 timer. Efter afkøling blev ethanolet fjernet, og 10 den resterende olie opløstes i toluen. Toluenfasen blev vasket én gang med vand, 2 gange med en 202's vandig kaliumhydroxidopløsning og én gang med mættet vandig natriumchloridopløsning i den angivne rækkefølge og tørret over vandfrit magnesiumsulfat. Fjernelse af opløsningsmidlet gav 2,24 g l-methyl-2-[4-(3,5-difluorphenoxy)phen-15 oxy]ethanol.
EKSEMPEL 3
Fremstilling af 2-methyl-2-[4-(3,5-difluorphenoxy)phenoxy]ethanol:
En blanding af 11,1 g (50,0 millimol) 4-(3,5-difluorphenoxy)phenol, 9,96 g (55,0 millimol) ethyl 2-brompropionat, 7,25 g (52,5 millimol) 20 kaliumcarbonat og 50 ml Ν,Ν-dimethylformamid omrørtes ved en indre temperatur på 70-80°C i 3 timer. Efter at have fået lov til at afkøle blev reaktionsblandingen hældt ud i isvand og ekstraheret med toluen. Toluenfasen blev tørret over vandfrit magnesiumsulfat og opløsningsmidlet fjernet, hvorved man fik 15,6 g ethyl 2-[4-(3,5-difluorphen-25 oxy)phenoxy]propionat.
15,6 g af det således vundne ethyl 2-[4-(3,5-difluorphenoxy)phen-oxy]propionat opløstes i 10 ml diethylether. Den resulterende opløsning sattes dråbevis til en suspension af 1,38 g (36,3 millimol) li-thiumaluminiumhydrid i 70 ml diethylether under omrøring ved en indre 30 temperatur på mellem -20 og -10eC. Efter endt tilsætning fortsattes omrøringen i 1 time, medens den indre temperatur holdtes på0-5eC.
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11
Reaktionsblandingen blev hældt ud i en blanding af is og saltsyre og ekstraheret med ether. Etherfasen blev tørret over vandfrit magnesiumsulfat og opløsningsmidlet fjernet, hvorved man fik 12,6 g 2-methyl-2-[4-(3,5-difluorphenoxy)phenoxy]ethanol.
5 REFERENCEEKSEMPEL 1
Fremstilling af 2-[4-(3,5-difluorphenoxy)phenoxy]ethylbromid:
Til en blanding af 1,00 g (3,76 millimol) 2-[4-(3,5-difluorphenoxy)-phenoxy]ethanol og 50 ml n-hexan sattes gradvis 0,71 g (2,63 millimol) phosphortribromid under omrøring og under isafkøling. Efter endt 10 tilsætning blev temperaturen hævet til stuetemperatur, og omrøringen fortsattes ved samme temperatur i 30 minutter efterfulgt af omrøring under kogning under tilbagesvaling i 1 time. Efter at blandingen havde fået lov til at afkøle, blev den øvre n-hexanfase isoleret ved dekantering, og n-hexanfasen blev vasket 2 gange med vand, 3 gange 15 med vandig natriumcarbonatopløsning og 1 gang med mættet vandig natriumchloridopløsning i den angivne rækkefølge og tørret over vandfrit magnesiumsulfat. Fjernelse af opløsningsmidlet gav 915 mg 2-[4-(3,5-difluorphenoxy)phenoxy]ethylbromid.
REFERENCEEKSEMPEL 2 20 Fremstilling af 2-[4-(3,5-difluorphenoxy)phenoxy]ethyl p-toluensul-fonat:
Til en opløsning af 2,66 g (10,0 millimol) 2-[4-(3,5-difluorphenoxy)-phenoxy]ethanol i 2,8 g pyridin sattes gradvis 1,91 g (10,0 millimol) p-toluensulfonylchlorid under omrøring og under afkøling til -20°C, 25 og den resulterende blanding fik lov at henstå i køleskab natten over. Til reaktionsblandingen sattes diethylether, og der blev vasket med fortyndet saltsyre, indtil den vandige fase blev sur, hvorefter der blev vasket med en vandig natriumhydrogencarbonatopløsning og en mættet vandig natriumchloridopløsning. Den vundne etherfase blev 30 tørret over vandfrit magnesiumsulfat og opløsningsmidlet fjernet,
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12 hvorved man fik 3,90 g 2-[4-(3,5-difluorphenoxy)phenoxy]ethyl p-tolu-ensulfonat.
ANVENDELSESEKSEMPEL
Fremstilling af forbindelse nr. 12 (fremgangsmåde B): 5 Til en suspension af 20 mg (0,5 millimol; 60%'s i olie) natriumhydrid i 1 ml dimethylformamid dryppedes en opløsning af 140 mg (0,5 millimol) L-methyl-2-[4-(3,5-difluorphenoxy)phenoxy]ethanol i 1 ml dimethylformamid under omrøring, og omrøringen fortsattes ved stuetemperatur, indtil hydrogengasudviklingen ophørte. 97 mg (1,0 millimol) 10 2-fluorpyridin tildryppedes, og blandingen omrørtes ved stuetemperatur natten over. Reaktionsblandingen blev hældt ud i 40 ml vand og ekstraheret 3 gange med 20 ml toluen. Toluenfasen blev tørret over vandfrit magnesiumsulfat og opløsningsmidlet fjernet ved afdampning. Remanensen blev renset ved søj lechromatografi på silicagel, hvorved 15 man fik 129 mg 2 -{l-methyl-2-[4-(3,5-difluorphenoxy)phenoxy]ethoxy)- 19 0 pyridin i form af en lysegul væske, n ’j) *= 1,5602.
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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13 TABELI F R_ R, Γ\ Æ~\ I3 l2 V=/ °V—/ °™CH“CH"°~Ri
Forbindelse R, r r Fysisk nr. 23 konstant 12 CH3 H r£9'0 1,5602 V1 39 CH3 H 1,5611
62 Η H smp. 80,6*C
XJ
65 « Η H smp. 91,2’c u
68 Η H smp. 7A;2*C
Til 69 CIL H n?9,° 1,5599
TD
73 H CH3 1,5568 76 H CHa 1,5584 TABEL I - fortsat
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14
Forbindelse R, p £ Fysisk nr. 23 konstant
79 H CH3 SJnP* 75;0*C
80 Ύ-li H H ^1° 1,5953 82 Η H ^3'° 1,5954 84 sJk Η Η -ί3'5 1*5950 86 'xi H CH3 "”3'5 1,5859
87 H CH3 1,58M
88 H C, n£3'0 1,5858 93 s^.5^ CHj H n£4'5 1,5859 94 NJ^j) CH3 " "i)4'5 1,5838 TABEL I - fortsat 15
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Forbindelse R^ r r Fysisk nr. 23 konstant 95 CU3 H 1,5850
99 Η H smP· 87, h’C
101 H ch3 %5'° L5468
T
25,0 ,
103 CH3 H ^ 84 F
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16 3 V £
H O W
H> M. w 0“
•b lo to lj 'to u> lo ω^4* fD
o lo οο ·υ σ> ui b u> t-"
3 H
α H
ro )-· 01 ro
a a a o o O
i-iHUKfCK *1 „ . . vv o
a a a a a a T r a I
to to O O to Y
. ø 0 G
a a a a a a o o a 1 to to a O ω ,J = a ω 333 3 33 3 3*Ό DIODMOMDWDNDM OM OM *<
<r> co ui vo co lo lo lo M
*·****·**·*» · » H- ui ui ui ui o o ui ui w Μ Μ Η> H-* Μ H* (-* I-· ^ ^ ^ ·» ^
ui ui ui ui ui ui ui ui O
b A. UI LO LO .U UI LO 3
Ό UI CO UI LO Ό LO OL W
LO LO LO LO f—1 U1 03 .b ft
OJ
3 ft
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17 i-3 3 *3 0? 10 g* ^ Μ Μ m h* *-* · H m Χχ X» Jx O' CTl U1 X» LO to b-> H·
3 H
(L H
(0 t~“ i-t M J? 0) 2 o o o *1 CO CO O rf o o o «
O O O W [O NJ JD
CO CO CO i i i JO (Ι Ο O O Xs. »-* to to Μ Π ΐίΐΊίΤ^Ί η o o I . I li a æ a oj ω ui t o n o 35 33 35 U) U) U) H Hl χ
η η X
33 35 33 33 35 35 . 9
LO LO tO
0 η n 9 K , 35 33 33 33 35 * ^ —w LO Ui LO a w
O—-33 33 to I
JO
H* “ 3 3 3 3 3 3 ^ D to O w D W OM OM O to σ> ca -o oo -J •Jr,.
- - "· ω un o un o un o1 Η» Η* I-* t-* t-“ ►“*
— -.·«» -* — *"· Q
Xx ΟΧ XX UI Ul un ~ •O -J co un Χχ <Λ r! LO Μ Xx O uo to “i to un cn oo o h* 3 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 Kemisk struktur Bemærkninger 5______ q Kendt som "methopren"; ^ /®\. i I I ft JL USA-patentskrifter nr.
7 3.904.662 og 3.912.815 Q Forbindelse beskrevet i // Λ ft Λ Π ikke-behandlet japansk io b (/ \Vo-v \>o Ly \ —/ \_/ publiceret patentan søgning nr. 157522/1975 g^^*. Forbindelse beskrevet i /7~\ /7~~\ U tysk offentliggørelses- c (/ \Vo·/' 'Vo \_/ \_/ skrift nr. 2.616.755
Forbindelse beskrevet i F j) tysk offentliggørelses- 15 \zJ \=J skrift nr. 2516331
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19 I hvert af testeksemplerne er præparatet, der testes, fremstillet ifølge nedenstående formuleringseksempel 1: FORMULERINGSEKSEMPEL 1 20 dele af hver den pågældende forbindelse, 20 dele af en emulgator 5 (en blanding af polyoxyethylen-styreneret phenylether, polyoxy- ethylen-styreneret phenyletherpolymer og et alkylarylsulfonat) og 60 dele xylen blandes grundigt til dannelse af et emulgerbart koncentrat.
TESTEKSEMPEL 1 10 Et emulgerbart 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-15 taget (to replikationer). Resultaterne er vist i tabel III.
Tabel III
Testforbindelse Koncentration Emergensgrad nr. (ppm) (Z) 20 12 3,5 0 39 3,5 0 62 3,5 0 65 3,5 0 68 3,5 0 25 69 3,5 0 73 3,5 0 76 3,5 0 79 3,5 0 80 3,5 0 30 82 3,5 0 TABEL III fortsat 20
DK 165740 B
84 3,5 0 86 3,5 0 87 3,5 0 5 88 3,5 0 93 3,5 0 94 3,5 0 95 3,5 0 99 3,5 0 10 101 3,5 0 103 3,5 0 A 3,5 0 15 Ubehandlet - 90 TESTEKSEMPEL 2
Et emulgerbart koncentrat fremstillet ifølge formuleringseksempel 1 blev fortyndet med vand til en bestemt fortynding. 0,5 ml af den for-20 tyndede 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 fremkaldte 50%'s inhibering af emergensen (IC,.q) (ppm) blev bestemt (to replikationer). Resultaterne er vist i tabel IV, hvor PI^ svarer 25 til -log IC5Q.
21 DK Ί6574Ub
Tabel IV
Testforbindelse nr. PI^q 95 4,2 5 _ A 3,7 B 1,1 C 1,6 F 0,3 10 ______ TESTEKSEMPEL 3 2 g pulveriseret dyrefoder blev blandet grundigt med 14 g klid. Et emulgerbart koncentrat fremstillet som i formuleringseksempel 1 blev fortyndet med vand til den ønskede koncentration, og 28 ml af den 15 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 blev bestemt. Den procentvise emergensirihibering blev beregnet ved 20 følgende ligning:
Emergens- Emergensgrad i behandlet ansats
inhibering ” ^ Emergensgrad i ubehandlet ansats ^ X
(2)
Resultaterne er anført i tabel V.
DK 165740 B
Tabel V
'22
Testforbindelse Emergensirihibering (%) nr. 3 ppm 1 ppm 0,3 ppm 5 12 100 100 100 39 100 100 97 62 100 100 89 68 100 100 89 69 100 100 100 10 73 100 100 96 76 100 100 100 79 100 100 95 82 100 89 41 84 100 67 16 15 99 100 100 92 101 100 . 100 40 103 100 100 92 A * 60 13 2 20 B 36 15 0 G 0 0 0 F 10 5 0 TESTEKSEMPEL 4 25 Voksne individer af røde hunspindemider (Tetranychus ciimabarinus) fik lov at leve på fire blade (10 mider/blad) af snittebønner 5 dage efter plantning i potterne, og de voksne dyr blev holdt ved 27“C i en pyrostat. Efter 6 dage blev en 400 ganges fortynding (500 ppm) af det emulgerbare koncentrat fremstillet ifølge formuleringseksempel 1 30 sprøjtet over potterne, der var placeret på et drejeligt bord, med et udsprøjtet volumen på 10 ml/potte, og der blev tillige påført 2 ml fortyndet væske på jorden i hver potte. Otte dage derefter blev antallet af voksne individer talt, og den insektbekæmpende virkning blev bedømt efter følgende skala:
DK 165740 B
23 ++: 0-9 voksne dyr på et blad +: 10-30 voksne dyr på et blad -: mere end 31 voksne dyr på et blad
Resultaterne er vist i tabel VI.
5 Tabel VI
Testforbindelse nr. Bedømmelse 80 ++
10 B
C
Ubehandlet

Claims (2)

1. Fluorsubstitueret phenoxyphenoxyalkohol, kendetegnet ved, at den har den almene formel F\ _ R-3 R9 )/ \ /) \ ^ i ^ V y-0-\ y-O-CH-CH-OH F/ hvor R2 og R3 har samme eller forskellig betydning og hver betegner 5 et hydrogenatom eller en methylgruppe.
2. Fluorsubstitueret phenoxyphenoxyalkoho 1 ifølge krav 1, kendetegnet ved, at den har formlen F. \—/ °\.,/0"0Η2 -CH2 -OH F. CH3 P)~\ /_\ f3 vj/ 0 V- /°"CH2”^H"0H
DK001491A 1983-04-25 1991-01-04 Fluorsubstituerede phenoxyphenoxyalkoholer DK165740C (da)

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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
JPH0651684B2 (ja) * 1985-10-15 1994-07-06 クミアイ化学工業株式会社 ピリミジン誘導体および除草剤

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DK162091B (da) 1991-09-16
OA07710A (fr) 1985-08-30
JPS59199673A (ja) 1984-11-12
GB2158439A (en) 1985-11-13
KR910007963B1 (ko) 1991-10-04
SG101787G (en) 1988-07-15
GB8513656D0 (en) 1985-07-03
PH19386A (en) 1986-04-07
IL71613A0 (en) 1984-07-31
ZA842848B (en) 1984-12-24
EP0128648B1 (en) 1988-08-17
EP0246713A2 (en) 1987-11-25
EP0246713B1 (en) 1992-03-04
DK165443B (da) 1992-11-30
BR8401940A (pt) 1984-12-04
GB8410240D0 (en) 1984-05-31
DK1491D0 (da) 1991-01-04
KR840008343A (ko) 1984-12-14
GB2140010A (en) 1984-11-21
IL87772A0 (en) 1989-02-28
SG101687G (en) 1988-06-03
DE3473446D1 (en) 1988-09-22
CA1231945A (en) 1988-01-26
NZ207897A (en) 1987-09-30
DK165443C (da) 1993-04-13
SA90100085B1 (ar) 2004-01-24
GB2140010B (en) 1986-01-08
IN159713B (da) 1987-06-06
DK1591D0 (da) 1991-01-04
IL87772A (en) 1989-09-28
MY8600647A (en) 1986-12-31
IL71613A (en) 1989-09-28
DK165972C (da) 1993-07-26
IL82059A (en) 1989-09-28
DK1491A (da) 1991-01-04
DK165972B (da) 1993-02-22
DK1691A (da) 1991-01-04
DK1591A (da) 1991-01-04
NL971041I1 (nl) 1998-01-05
DK207291A (da) 1991-12-27
AU566515B2 (en) 1987-10-22
DK207291D0 (da) 1991-12-27
IL82059A0 (en) 1987-10-20
DE3485546D1 (de) 1992-04-09
AU2706184A (en) 1984-11-01
DK205584A (da) 1984-10-26
DK165740C (da) 1993-06-14
US4879292A (en) 1989-11-07
DK205584D0 (da) 1984-04-24
GB2158439B (en) 1987-07-29
US4751225A (en) 1988-06-14
US4970222A (en) 1990-11-13
EP0246713A3 (en) 1988-07-20
DK1691D0 (da) 1991-01-04
IN162043B (da) 1988-03-19
DK162091C (da) 1992-02-24
EP0128648A1 (en) 1984-12-19

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