DK165972B - Optisk aktive phenoxyphenoxyalkoholer - Google Patents

Optisk aktive phenoxyphenoxyalkoholer Download PDF

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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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compound
methyl
millimoles
phenoxyphenoxy
optically active
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DK001591A
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DK1591A (da
DK165972C (da
DK1591D0 (da
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Sumio Nishida
Makoto Hatakoshi
Hirosi Kisida
Noritada Matsuo
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Sumitomo Chemical Co
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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
    • C07D213/60—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
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    • 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
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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
DK 165972 B
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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JP58073400A JPS59199673A (ja) 1983-04-25 1983-04-25 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

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DK205584A DK162091C (da) 1983-04-25 1984-04-24 Nitrogenholdige heterocycliske forbindelser, fremgangsmaade til fremstilling deraf, insekticid indeholdende disse samt anvendelse af forbindelserne som insekticidt middel
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
DK207291A DK207291A (da) 1983-04-25 1991-12-27 Nitrogenholdige heterocycliske forbindelser

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DK205584A DK162091C (da) 1983-04-25 1984-04-24 Nitrogenholdige heterocycliske forbindelser, fremgangsmaade til fremstilling deraf, insekticid indeholdende disse samt anvendelse af forbindelserne som insekticidt middel
DK001491A DK165740C (da) 1983-04-25 1991-01-04 Fluorsubstituerede phenoxyphenoxyalkoholer

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DK001691A DK165443C (da) 1983-04-25 1991-01-04 4-(3,5-difluorphenoxy)phenol
DK207291A DK207291A (da) 1983-04-25 1991-12-27 Nitrogenholdige heterocycliske forbindelser

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GB2140010A (en) 1984-11-21
AU2706184A (en) 1984-11-01
DK1591A (da) 1991-01-04
BR8401940A (pt) 1984-12-04
DK207291D0 (da) 1991-12-27
IN162043B (da) 1988-03-19
DK1491D0 (da) 1991-01-04
EP0128648A1 (en) 1984-12-19
DK205584A (da) 1984-10-26
DK162091B (da) 1991-09-16
IL71613A0 (en) 1984-07-31
NL971041I1 (nl) 1998-01-05
DE3473446D1 (en) 1988-09-22
ZA842848B (en) 1984-12-24
IL87772A (en) 1989-09-28
DK165740B (da) 1993-01-11
JPS59199673A (ja) 1984-11-12
IL82059A0 (en) 1987-10-20
DE3485546D1 (de) 1992-04-09
GB2158439A (en) 1985-11-13
KR840008343A (ko) 1984-12-14
GB2158439B (en) 1987-07-29
IL87772A0 (en) 1989-02-28
US4879292A (en) 1989-11-07
EP0246713B1 (en) 1992-03-04
OA07710A (fr) 1985-08-30
GB8410240D0 (en) 1984-05-31
CA1231945A (en) 1988-01-26
NZ207897A (en) 1987-09-30
AU566515B2 (en) 1987-10-22
SG101687G (en) 1988-06-03
US4970222A (en) 1990-11-13
DK165443B (da) 1992-11-30
DK1691D0 (da) 1991-01-04
SG101787G (en) 1988-07-15
DK1691A (da) 1991-01-04
EP0246713A2 (en) 1987-11-25
MY8600647A (en) 1986-12-31
KR910007963B1 (ko) 1991-10-04
IL71613A (en) 1989-09-28
DK165972C (da) 1993-07-26
PH19386A (en) 1986-04-07
US4751225A (en) 1988-06-14
DK162091C (da) 1992-02-24
IN159713B (da) 1987-06-06
GB2140010B (en) 1986-01-08
DK165443C (da) 1993-04-13
GB8513656D0 (en) 1985-07-03
EP0246713A3 (en) 1988-07-20
DK165740C (da) 1993-06-14
SA90100085B1 (ar) 2004-01-24
DK207291A (da) 1991-12-27
DK1491A (da) 1991-01-04
EP0128648B1 (en) 1988-08-17
DK1591D0 (da) 1991-01-04
DK205584D0 (da) 1984-04-24
IL82059A (en) 1989-09-28

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