NO173543B - Akrylsyrederivater - Google Patents

Akrylsyrederivater Download PDF

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Publication number
NO173543B
NO173543B NO90903771A NO903771A NO173543B NO 173543 B NO173543 B NO 173543B NO 90903771 A NO90903771 A NO 90903771A NO 903771 A NO903771 A NO 903771A NO 173543 B NO173543 B NO 173543B
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NO
Norway
Prior art keywords
tolyl
imino
oxy
methoxy
acrylic acid
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NO90903771A
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English (en)
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NO173543C (no
NO903771L (no
NO903771D0 (no
Inventor
Hans Peter Isenring
Stephen Trah
Bettina Weiss
Original Assignee
Ciba Geigy Ag
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First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=25694315&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=NO173543(B) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag
Publication of NO903771L publication Critical patent/NO903771L/no
Publication of NO903771D0 publication Critical patent/NO903771D0/no
Publication of NO173543B publication Critical patent/NO173543B/no
Publication of NO173543C publication Critical patent/NO173543C/no

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D207/33—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D207/335—Radicals substituted by nitrogen atoms not forming part of a nitro radical
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    • A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
    • A01N35/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical at least one of the bonds to hetero atoms is to nitrogen
    • A01N35/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical at least one of the bonds to hetero atoms is to nitrogen containing a carbon-to-nitrogen double bond
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    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
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    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
    • A01N37/38—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system
    • A—HUMAN NECESSITIES
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    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
    • A01N37/50—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids the nitrogen atom being doubly bound to the carbon skeleton
    • A—HUMAN NECESSITIES
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    • A01N39/00—Biocides, pest repellants or attractants, or plant growth regulators containing aryloxy- or arylthio-aliphatic or cycloaliphatic compounds, containing the group or, e.g. phenoxyethylamine, phenylthio-acetonitrile, phenoxyacetone
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
    • 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
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/14—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one 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
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/24—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms
    • A01N43/26—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings
    • A01N43/28—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings with two hetero atoms in positions 1,3
    • A01N43/30—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings with two hetero atoms in positions 1,3 with two oxygen atoms in positions 1,3, condensed with a carbocyclic ring
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
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    • 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
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    • 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
    • A01N43/34—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
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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
    • A01N43/74—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
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    • A01N45/00—Biocides, pest repellants or attractants, or plant growth regulators, containing compounds having three or more carbocyclic rings condensed among themselves, at least one ring not being a six-membered ring
    • A01N45/02—Biocides, pest repellants or attractants, or plant growth regulators, containing compounds having three or more carbocyclic rings condensed among themselves, at least one ring not being a six-membered ring having three carbocyclic rings
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    • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C251/32—Oximes
    • C07C251/50—Oximes having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals
    • C07C251/60—Oximes having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals of hydrocarbon radicals substituted by carboxyl groups
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    • C07C255/00—Carboxylic acid nitriles
    • C07C255/63—Carboxylic acid nitriles containing cyano groups and nitrogen atoms further bound to other hetero atoms, other than oxygen atoms of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C255/64—Carboxylic acid nitriles containing cyano groups and nitrogen atoms further bound to other hetero atoms, other than oxygen atoms of nitro or nitroso groups, bound to the same carbon skeleton with the nitrogen atoms further bound to oxygen atoms
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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
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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
    • C07D213/24—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
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Abstract

Oppfinnelsen vedrører nye forbindelser med formel .hvor X betyr en aldimino- eller ketiminogruppe, og deres fremstilling, fungicide midler som inneholder slike forbindelser som virkestoff, og anvendelse av virkestoffene, hhv. midlene for bekjempelse av sopp i landbruk og havebruk.

Description

Akrylsyrederivater
Foreliggende oppfinnelse vedrører aromatiske forbindelser, nemlig substituerte 2-fenyl-3-metoksyakrylsyremetylestere med den generelle formel I
hvor Ri og R2 uavhengig av hverandre betyr hydrogen; C1_12<->alkyl; C3-C6-cykloalkyl; <C>i_4-halogenalkyl; Ci-4-<a>lkoksy-<C>1_4-alkyl; <C>1_4-alkyltio-C1_4<->alkyl;
usubstituert eller substituert fenyl-C1-C4~alkenyl hvor substituentene er valgt fra gruppen som består av halogen og <C>1-C4~alkoksy;
usubstituert eller substituert fenyl-C1-C4~alkyl hvoi; substituentene er valgt fra gruppen som består av halogen, C1-C4~alkoksy og C1-C4-halogenalkyl;
usubstituert eller substituert fenyl idet de høyst 3 identiske eller forskjellige substituenter er valgt fra gruppen som består av halogen, C^- C^-alkyl, C^- C^-halogen-alkyl, Ci-C^-halogenalkoksy, fenoksy, fenyl, fenyltio, C-^-C4-alkyltio, metylendioksy og nitro;
naftyl; fluorenyl;
en heterocyklisk 5- eller 6-leddet gruppe med aromatisk karakter inneholdende 1 eller 2 heteroatomer valgt fra nitrogen, svovel og oksygen eller en slik gruppe som eventuelt er substituert med en eller to metyltio, metyl eller halogen, eller er en gruppe med en kondensert benzenkjerne, eller en gruppe som er bundet via metyl eller etenyl;
cyano eller én av gruppene (a) til (c)
hvor R3, R4, R5 og R6 i hvert enkelt tilfelle betyr hydrogen, C1-C4-alkyl eller fenyl;
R;L og R2 sammen med karbonatomet som de er bundet til, betyr en 6-leddet ring som eventuelt inneholder et oksygen- eller svovelatom og som kan inneholde én eller to kondenserte aromatiske ringer.
Forbindelsene ifølge oppfinnelsen har fungicide egenskaper og egner seg som fungicide virkestoffer, især for anvendelse i landbruket og havebruket.
Oppfinnelsen vedrører videre fungicider som inneholder slike forbindelser som virkestoffer, samt anvendelsen av slike forbindelser og midler for bekjempning av sopp i landbruket og i havebruket.
I ovennevnte formel I kan samtlige av gruppene "alkyl", "alkenyl" og "alkinyl", som sådanne eller som del av større grupper, f.eks. heteroarylalkyl, alt etter antall karbonatomer, være rettkjedede eller forgrenede. Dessuten kan alkenyl- og alkinylgruppene hver oppvise mer enn én dob-bel tbinding, hhv. trippelbinding. Et mulig forekommende halogenatom er fluor, klor, brom eller jod, hvorav fluor, klor og brom er foretrukket. En gruppe som f.eks. alkyl, som sådan, eller som del av en større gruppe, som hver har mer enn én halogensubstituent, kan oppvise like eller forskjellige halogenatomer. Med aryl menes især fenyl, naftyl, fenantryl eller fluorenyl, med heteroaryl menes hetero-cykliske grupper med aromatisk karakter, såsom pyrrolyl, pyridyl, furyl, tienyl, isoksazolyl, tiazolyl, imidazolyl, pyrimidinyl eller triazolyl, eller en slik gruppe med tilkondensert benzen, f.eks. kinolinyl, benzofuryl, benzo-tienyl eller dibenzofuryl. Dette gjelder også for aryl eller heteroaryl som del av en større gruppe, f.eks. aralkyl hhv. heteroarylalkyl. Aryl- og heteroarylgruppene kan hver oppvise én eller flere substituenter som på egnet måte er én eller flere substituenter utvalgt blant halogen C1_4-alkyl, C 1-4-halogenalkyl, <C>1_4-alkoksy-<C>1_4-alkyl, aryl-C^^-alkyl, heteroaryl-C1_4-alkyl, aryloksy-C1_4-alkyl, heteroaryloksy-CiL_4-alkyl, <C>2_4-alkenyl, aryl-<C>2_4-alkenyl, heteroaryl-C2_4-alkenyl, C2_4-alkinyl, C3_6-cykloalkyl, aryl, heteroaryl, —alkoksy, <C>i_4~halogenalkoksy, aryl-C1_4~<a>lkoksy, heteroaryl-<C>i_4~alkoksy, <C>2-4-alkenyloks<y>, C2_4-alkinyloksy, aryloksy, heteroaryloksy, C1_4-alkyltio, cyano nitro, en gruppe NR9R1<0>, en gruppe COR1<1>, en gruppe COOR<12> (hvor R<9>, R<1>0, R1<1> og R1<2> hver betyr <C>1_4-alkyl, aryl eller heteroaryl) .
Hvis det i forbindelsene med formel I foreligger asymmetriske karbonatomer, opptrer forbindelsene i optisk aktiv form. bare på grunn av at det forekommer en alifatisk dobbeltbinding og en iminodobbeltbinding opptrer forbindelsene i hvert fall i [E]- eller [Z]-form. Videre kan atropisomeri forekomme. Formel I skal omfatte alle disse mulige isomere former samt deres blandinger, f.eks. racemiske blandinger og enhver [E/Z]-blanding.
En spesiell gruppe av forbindelser med formel I består av de forbindelser med formel I hvor Z betyr en gruppe R<1>R<2>C=N-, hvor R<1> og R<2> uavhengig av hverandre betyr hydrogen, Cj_i2-alkyl, C;l_4-halogenalkyl, aryl-C1_4-alkyl, heteroaryl-C1_4-alkyl, C2_12-alkenyl, aryl-<C>2_4-alkenyl, heteroaryl-C2_4-alkenyl, <C>2_12-alkinyl, C3_6-cykloalkyl, aryl, heteroaryl, cyano eller én av de ovenfor angitte grupper (a) til, (d), eller R<1> og R<2> sammen med karbonatomet som de er bundet til, betyr en ring som er nærmere definert ovenfor.
Uavhengig av hverandre betyr R<1> i gruppen R<1>R<2>C=N- fortrinnsvis eventuelt substituert fenyl, hvorved eventuelt forekommende substituenter fortrinnsvis er inntil tre like eller forskjellige halogenatomer (især fluor, klor og/eller brom), <C>1_4-alkylgrupper (især metyl), C1_4~halogenalkylgrupper (især trifluormetyl) og/eller C^4-halogenalkoksygrupper (især trifluormetoksy), og R<2> er fortrinnsvis hydrogen, C1_14-alkyl (især metyl eller etyl), C1_4-halogenalkyl (især trifluormetyl) eller C3_6-cykloalkyl (især cyklopropyl).
Likeledes foretrukket betyr R<1> heteroaryl, især furyl som eventuelt er substituert med inntil to metylgrupper, tienyl som eventuelt er substituert med klor eller metyl, eller benzofuryl, og R<2> betyr metyl.
Generelt er [E]-formen av forbindelsene med formel I foretrukket i forhold til [Z]-formen.
Særlig foretrukne enkeltforbindelser med formel I er: 3-metoksy-2-[cx-{ [ (a-metylbenzyl)-imino]-oksy}-o-tolyl]-akrylsyrernetylester,
3-metoksy-2-[cx-{ [ (cx-metyl-3 ,5-di-trif luormetylbenzyl)-imino]-oksy}-o-tolyl]-akrylsyremetylester,
3-metoksy-2-[cx-{ [ (a-metyl-2-f luor-5-metylbenzyl) - imino]-oksy}-o-tolyl]-akrylsyremetylester,
1- [a-{[(l-[2-benzofuryl]-etyl)-imino]-oksy}-o-tolyl]-3-metoksy-akry1syremety1ester,
3-metoksy-2-[a-{[(3-nitrobenzyl)-imino]-oksy}-o-tolyl]-akrylsyremetylester,
3-metoksy-2-[cx-{ [ (oc-trif luormetylbenzyl)-imino]-oksy}-o-tolyl]-akrylsyremetylester,
3-metoksy-2-[a-{ [ (cx-metyl-4-f luorbenzyl) -imino] - oksy}-o-tolyl]-akrylsyremety1ester,
3-metoksy-2-[oc-{ [ (1-[2-tienyl] -etyl) -imino] -oksy}-o-tolyl]-akrylsyremetylester,
3-metoksy-2-[a-{[(a-metyl-4-klorbenzyl)-imino]-oksy}-o-tolyl]-akrylsyremetylester,
2- [a-{[(cx-cyklopropylbenzyl)-imino]-oksy}-o-tolyl]-3-metoksy-akrylsyremetylester,
2- [a-{[(1-[5-klor-2-tienyl]-etyl)-imino]-oksy}-o-toly1]-3-metoksy-akry1syremetylester,
3- metoksy-2-[a-{[(a-metyl-3-trifluormetylbenzyl)-imino]-oksy}-o-tolyl]-akrylsyremetylester,
3-metoksy-2-[0!-{ [ (a-metyl-3-brombenzyl)-imino]-oksy}-o-tolyl]-akrylsyremetylester,
2-[oc-{ [ (l-[3,5-dimetyl-2-furyl]-etyl) -imino]-oksy}-o-tolyl]-3-metoksy-akrylsyremetylester,
2- [a-([(1-[2,5-dimetyl-3-tienyl]-etyl)-imino]-oksy}-o-tolyl]-3-metoksy-akrylsyremetylester,
3- metoksy-2-[cx-{ [ (oc-metyl-3-klorbenzyl) -imino] -oksy}-o-tolyl]-akrylsyremetylester,
3-metoksy-2- [cx-{ [ (cx-metyl-3-metylbenzyl) -imino]-oksy}-o-tolyl]-akrylsyremetylester,
3-metoksy-2-[cx-{ [ (cx-metyl-4-metylbenzyl)-imino] - oksy}-o-tolyl]-akrylsyremetylester,
2- [a-{[(3-fluorbenzyl)-imino]-oksy}-o-tolyl]-3-metoksy-akrylsyrernetylester,
3- metoksy-2-[ cx-{[(cx-metyl-4-trif luormetylbenzyl)-imino]-oksy}-o-tolyl]-akrylsyremetylester,
3-metoksy-2-[oc-{ [ (cx-metyl-3-f luor-5-trif luormetylbenzyl) -imino]-oksy}-o-tolyl]-akrylsyremetylester,
3-metoksy-2-[ cx- {[ (oc-metyl-3-fluorbenzyl) -imino]-oksy}-o-tolyl]-akrylsyremetylester,
3-metoksy-2-[cx-{[ (cx-metyl-3-trif luormetoksybenzyl) - imino]-oksy}-o-tolyl]-akrylsyremetylester og
2-[cx-{ [ (oc-etyl-3-trif luormetylbenzyl) -imino] -oksy}-o-tolyl]-3-metoksy-akrylsyremetylester.
Ytterligere foretrukne enkeltforbindelser med formel I er: 2- [cx-{[ (1- [ 2-furyl ] -etyl) -imino] -oksy} -o-tolyl ] -3-metoksy-akrylsyremetylester, 3- metoksy-2-[cx-{ [ (1-[2-naftyl]-etyl)-imino]-oksy}-o-tolyl]-akrylsyremetylester, 2-[cx-{ [ (4-klorbenzyl) -imino] -oksy}-o-tolyl]-3-metoksy-akrylsyremetylester, 2- [cx-{ [ (2,4-diklorbenzyl) -imino]-oksy}-o-tolyl]-3-metoksy-akrylsyremetylester, 3- metoksy-2-[cx-{[ (cx-metyl-4-nitrobenzyl)-imino] - oksy}-o-tolyl]-akrylsyremetylester, 2- [cx-{ (benzylimino) -oksy}-o-tolyl]-3-metoksy-akryl-syremetylester , 3- metoksy-2-[a-{[(2-pyridylmetyl)-imino]-oksy}-o-tolyl]-akrylsyremetylester, 2-[cx-{ [ (cx-etylbenzyl)-imino]-oksy}-o-tolyl]-3-metoksy-akrylsyremetylester, 2-[a-{ [ (cx-etyl-4-klorbenzyl)-imino]-oksy}-o-tolyl]-3-metoksy-akry1syremetylester, 3 -metoksy-2 - [ a- {[ (cx- [ n-propy 1 ] -benzyl) - imino ] -oksy} - o-tolyl]-akrylsyremetylester,
2-[cx-{ [ (l-[benzoyl]-etyl) -imino]-oksy}-o-tolyl]-3-
metoksy-akrylsyremetylester,
3-metoksy-2-[cx-{ [ (cx-metyl- -fenylallyl)-imino]-oksy}-o-tolyl]-akrylsyremetylester,
3-metoksy-2-[a-{ [ (a-metyl-4-fenoksybenzyl)-imino]-oksy}-o-tolyl]-akrylsyremetylester,
2- [cx-{ [ (cx-cyklopropyl-4-klorbenzyl) -imino] -oksy}-o-tolyl]-3-metoksy-akrylsyremetylester,
3- metoksy-2-[cx-{[ (1-[2-pyridyl]-etyl)-imino]-oksy}-o-tolyl]-akrylsyremetylester,
3-metoksy-2-[a-{[(1-[3-pyridyl]-etyl)-imino]-oksy}-o-tolyl]-akrylsyremetylester,
3-metoksy-2-[cx-{ [ (1-[5-metyl-2-furyl]-etyl)-imino]-oksy}-o-tolyl]-akrylsyremetylester,
2- [cx-{ [ (dicyklopropylmetyl) -imino]-oksy}-o-tolyl]-3-metoksy-akrylsyremetylester,
3- metoksy-2-[a-{[(2-naftylmetyl)-imino]-oksy}-o-tolyl]-akrylsyremetylester,
3-metoksy-2-[a-{ [ (a-metyl-3-nitrobenzyl)-imino]-oksy}-o-tolyl]-akrylsyremetylester,
2- [cx-{ [ (l-[2,4-dimetyl-5-tiazolyl) -imino] -oksy}-o-tolyl]-3-metoksy-akrylsyremetylester,
3- metoksy-2-[a-{[ (cx-metyl-4-metoksybenzyl) -imino]-oksy}-o-tolyl]-akrylsyremetylester,
3-metoksy-2-[a-{[(a-metyl-3,4-diklorbenzyl)-imino]-oksy}-o-tolyl]-akrylsyremetylester,
3-metoksy-2-[a-{[(a-metyl-2-fluorbenzyl)-imino]-oksy}-o-tolyl]-akrylsyremetylester,
3-metoksy-2-[a-{[(a-metyl-2,4-dimetylbenzyl)-imino]-oksy}-o-tolyl]-akrylsyremetylester,
3-metoksy-2-[a-{[(a-metyl-4-etylbenzyl)-imino]-oksy}-o-tolyl]-akrylsyremetylester,
3-metoksy-2-[a-{[(a-metyl-3-etylbenzyl)-imino]-oksy}-o-tolyl]-akrylsyremetylester,
3-metoksy-2-[a-{[(a-metyl-3,4-dimetylbenzyl)-imino]-oksy}-o-tolyl]-akrylsyremetylester,
2- [a-{[(l-[5-brom-2-tienyl]-etyl)-imino]-oksy}-o-tolyl]-3-metoksy-akrylsyremetylester,
3- metoksy-2-[a-{[(1-[2-naftyl]-propyl)-imino]-oksy}-o-tolyl]-akrylsyremetylester og
2-[a-{[(a-cyklopropyl-2-naftylmetyl)-imino]-oksy}-o-
tolyl]-3-metoksy-akrylsyremetylester.
<y>tterligere eksempler på forbindelser med formel I er: 3-metoksy-2-[a-{[ (cx-metyl-2 , 3-dif luorbenzyl) -imino] - oksy}-o-tolyl]-akrylsyremetylester,
3-metoksy-2-[a-{[(a-metyl-2,4-difluorbenzyl)-imino]-oksy}-o-tolyl]-akrylsyremetylester,
3-metoksy-2-[a-{[(a-metyl-2,5-difluorbenzyl)-imino]-oksy}-o-tolyl]-akrylsyremetylester,
3-metoksy-2-[a-{[(a-metyl-3,4-difluorbenzyl)-imino]-oksy}-o-tolyl]-akrylsyremetylester,
3-metoksy-2-[a-{[(a-trifluormetylkarbonyl-2,3-diklorbenzyl)-imino]-oksy}-o-tolyl]-akrylsyremetylester,
3-metoksy-2-[a-{[(a-trifluormetyl-2,3-diklorbenzoyl-mety1)-imino]-oksy}-o-tolyl]-akrylsyremetylester,
3-metoksy-2-[a-{[(l-metyl-2-fenoksypropyl)-imino]-oksy}-o-tolyl]-akrylsyremetylester,
3-metoksy-2-[a-{[(l-metyl-2-[2-klorfenoksy]-propyl)-imino]-oksy}-o-tolyl]-akrylsyremetylester,
3-metoksy-2-[a-{[(l-metyl-2-fenyltiopropyl)-imino]-oksy}-o-tolyl]-akrylsyremetylester,
3-metoksy-2-[a-{[(a-trifluormetylkarbonyl-2-naftyl-metyl) -imino]-oksy}-o-tolyl]-akrylsyremetylester,
2-[a-{[(a-cyklopropylkarbony1-2-naftylmetyl)-imino]-oksy}-o-tolyl]-3-metoksy-akrylsyremetylester,
2-[a-{[(a-isopropyl-2-naftylmetyl)-imino]-oksy}-o-tolyl]-3-metoksy-akrylsyremetylester,
2- [a-{[(a-dimetylaminometyl-2-naftylmetyl)-imino]-oksy}-o-tolyl]-3-metoksy-akrylsyremetylester og
3- metoksy-2-[a-{[(2,4,4-trimetyl-l-cykloheksen-6-yl)-imino]-oksy}-o-tolyl]-akrylsyremetylester.
Fremgangsmåten ved fremstilling av forbindelsene ifølge oppfinnelsen er karakterisert ved at man omsetter et oksim X-OH, især et oksim med den generelle formel II
hvor R<1> og R<2> har ovennevnte betydning,
med et benzylalkoholderivat med den generelle formel
hvor U betyr en avgående gruppe.
Ved denne omsetning dreier det seg om en nukleofil substitu-sjon som kan utføres under vanlig gjeldende reaksjons-betingelser. Med avgangsgruppe U som finnes i benzylalkohol-derivatet med formel III, menes fortrinnsvis klor, brom, jod, mesyloksy eller tosyloksy. Omsetningen skjer hensiktsmessig i et inert organisk løsningsmiddel, såsom en cyklisk eter, f.eks. tetrahydrofuran eller dioksan, acetondimetylformamid eller dimetylsulfoksyd, i nærvær av en base, såsom natriumhydrid, natrium- eller kaliumkarbonat, et tertiært amin, f.eks. et trialkylamin, især diazabicyklononan eller diazabicykloundekan, eller sølvoksyd, ved temperaturer mellom 2 0°C og 80°C, fortrinnsvis i temperaturområdet 0°C til 2CC.
Alternativt kan omsetningen skje under faseoverførings-katalyse i et organisk løsningsmiddel, f.eks. metylenklorid, i nærvær av en vandig basisk løsning, f.eks. natriumhydrok-sydløsning, samt en faseoverføringskatalysator, som f.eks. tetrabutylammoniumhydrogensulfat, ved værelsestemperatur.
Separeringen og rensingen av de således fremstilte forbindelser med formel I kan skje etter i og for seg kjente metoder. Likeledes etter i og for seg kjente metoder kan mulig forekommende isomerblandinger, f.eks. E/Z-isomerblandinger, separeres i de rene isomerer, f.eks. ved kromatografi eller fraksjonert krystallisering.
Oksimene X-OH, f.eks. med formel II, som anvendes som utgangsmaterialer i fremgangsmåten ifølge oppfinnelsen, er enten kjent eller kan fremstilles etter i og for seg kjente metoder, f.eks. ved å omsette den tilsvarende karbonylforbin-delse R^I^CsO med hydroksylaminhydroklorid i nærvær av en base, f.eks. natrium- eller kaliumhydroksyd eller pyridin. Ytterligere metoder finnes beskrevet i Houben-Weyl, "Methoden der Organischen Chemie", bind X/4, side 3-3 08 (1968)
("Herstellung und Umwandlung von Oximen").
Likeledes kan utgangsmaterialene med formel III fremstilles på i og for seg kjent måte, f.eks. som beskrevet i den euro-peiske patentpublikasjon nr. 203.606 (BASF) og i den der siterte litteratur.
Forbindelsene ifølge oppfinnelsen har fungicid virkning og kan derfor anvendes ved bekjempning av sopp i landbruket, i havebruket samt i den trebearbeidende industri. De egner seg spesielt for hemning av veksten eller for tilintetgjørelse av fytopatogene sopper på plantedeler, f.eks. blad, stengler, røtter, knoller, frukter eller blomster, og på sæd samt av skadesopp som opptrer i jordbunnen. Videre kan man bekjempe trenedbrytende og tremisfarvende sopper med forbindelsene ifølge oppfinnelsen. Forbindelsene ifølge oppfinnelsen er f.eks. virksomme ved bekjempning av sopp av klassene Deutero-mycetes, Ascomycetes, Basidiomycetes og Phycomycetes.
Spesielt egner forbindelsene ifølge oppfinnelsen seg for bekjempning av følgende skadeorganismer: Ekte melduggsopper (f.eks. Erysiphe graminis, Erysiphe cichoracearum, Puccinia coronata, Puccinia striiformis, Puccinia arachidis, Hemileia vastatrix, Uromyces fabae), skurvsopper (f.eks. Venturia inaequalis),
Cercospora spp. (f.eks. Cercospora arachidicola, Cercospora beticola),
Mycosphaerella spp. (f.eks. Mycosphaerella fijiensis), Alternaria spp. (f.eks. Alternaria brassicae, Alternaria mali),
Septoria spp. (f.eks. Septoria nodorum),
Helminthosporium spp. (f.eks. Helminthosporium teres,
Helminthosporium oryzea),
Plasmopara spp. (f.eks. Plasmopara viticola), Pseudoperonospora spp. (f.eks. Pseudoperonospora cubensis), Phytophtora spp. (f.eks. Phytophtora infestans), Pseudocercosporella spp. (f.eks. Pseudocercosporella herpo-trichoides),
Piricularia spp. (f.eks. Piricularia oryzae).
Videre virker forbindelsene f.eks. mot soppene av artene Tilletia, Ustilago, Rhizoctonia, Verticillium, Fusarium, Pythium, Gaeumannomyces, Sclerotinia, Monilia, Botrytis, Peronospora, Bremia, Gloeosporium, Cercosporidium, Penicil-lium, Ceratocystis, Rhynchosporium, Pyrenophora, Diaporthe, Ramularia og Leptosphaeria. Visse representanter for forbindelsene ifølge oppfinnelsen har dessuten virkning mot treskadende sopper, som f.eks. av artene Coniophora, Gloeophyllum, Poria, Merulius, Trametes, Aureobasidium, Sclerophoma og Trichoderma.
Forbindelsene ifølge oppfinnelsen utmerker seg ved profyl-aktisk og kurerende virkning.
Forbindelsene ifølge oppfinnelsen virker mot fytopatogene sopper under drivhusbetingelser allerede ved konsentrasjoner på 0,5 mg til 500 mg virkestoff pr. liter sprøytevæske. På friland anvendes med fordel doseringer på 20 g til 1 kg virkestoff med formel I pr. hektar og behandling. For bekjempning av sæd- eller jordbårne sopper i beisfrem-gangsmåten anvendes med fordel doseringer på 0,01 g til 1,0 g virkestoff med formel I pr. kg frø.
Forbindelsene ifølge oppfinnelsen kan formuleres til de forskjelligste midler, f.eks. løsninger, suspensjoner, emulsjoner, emulgerbare konsentrater og pulverformige preparater. De fungicide midler ifølge oppfinnelsen er karakterisert ved at de inneholder en effektiv mengde av minst én forbindelse med den generelle formel I som definert ovenfor, samt formuleringshjelpestoffer. Midlene inneholder fortrinnsvis minst ett av de følgende formuleringshjelpestoffer: Faste bærerstoffer; løsnings- hhv. dispergeringsmidler; tensider (fuktemidler og emulgatorer); dispergeringsmidler (uten tensidvirkning); og stabilisatorer.
Som faste bærerstoffer kommer hovedsakelig på tale: naturlige mineralstoffer, såsom kaolin, leire, kiselgur, talkum, bento-nitt, kritt, f.eks. slemmekritt, magnesiumkarbonat, kalksten, kvarts, dolomitt, attapulgitt, montmorillonitt og diatomé-jord; syntetiske mineralstoffer, såsom høydispers kiselsyre, aluminiumoksyd og silikater; organiske stoffer, såsom cellulose, stivelse, urinstoff og kunstharpikser; og gjødningsmidler, såsom fosfater og nitrater, hvorved slike bærerstoffer kan foreligge f.eks. som granulater eller pulvere.
Som løsnings- hhv. dispergeringsmidler kommer hovedsakelig på tale: aromater, såsom toluen, xylen, benzen og alkyl-naftaliner; klorerte aromater og klorerte alifatiske hydrokarboner, såsom klorbenzen, kloretylen og metylenklorid; alifatiske hydrokarboner, såsom cykloheksan og paraffiner, f.eks. jordoljefraksjoner; alkoholer, såsom butanol og glykol, samt deres etere og estere; ketoner, såsom aceton, metyletylketon, metylisobutylketon og cykloheksanon; og sterkt polare løsnings- hhv. dispergeringsmidler, såsom dimetylformamid, 1-metylpyrrolidon og dimetylsulfoksyd, hvorved slike løsnings- hhv. dispergeringsmidler fortrinnsvis oppviser flammepunkt på minst 30°C og kokepunkt på minst 50°C, og vann. Aktuelle som løsnings- hhv. dispergeringsmidler er også såkalte flytende, gassformige fortynnings-midler eller bærerstoffer som er slike produkter som ved værelsestemperatur og under normalt trykk er gassformige. Eksempler på slike produkter er især aerosol-drivgasser, såsom halogenerte hydrokarboner, f.eks. diklordifluormetan. I tilfelle man anvender vann som løsningsmiddel, kan f.eks. også organiske løsningsmidler anvendes som hjelpeløsnings-midler.
Tensidene (fuktemidler og emulgatorer) kan være ikke-ioniske forbindelser, såsom kondensasjonsprodukter av fettsyrer, fettalkoholer eller fettsubstituerte fenoler med etylenoksyd; fettsyreestere og -etere av sukkere, eller flerverdige alkoholer; produkter som er erholdt av sukkere eller flerverdige alkoholer ved kondensasjon med etylenoksyd; blokkpolymerer av etylenoksyd og propylenoksyd; eller alkyldimetylaminoksyd.
Tensidene kan også være anioniske forbindelser, såsom såper; fettsulfatestere, f.eks. dodecylnatriumsulfat, oktadecyl-natriumsulfat og cetylnatriumsulfat; alkylsulfonater, arylsulfonater og fettaromatiske sulfonater, såsom alkyl-benzensulfonat, f.eks. kalsiumdodecylbenzensulfonat, og butylnaftalinsulfonater; og kompleksere fettsulfonater, f.eks. amidkondensasjonsproduktene av oljesyre og N-metyl-taurin og natriumsulfonatet av dioktylsuccinat.
Tensidene kan også være kationiske forbindelser, såsom alkyl-dimetylbenzylammoniumklorider, dialkylmetylammoniumklorider, alkyltrimetylammoniumklorider og etoksylerte kvaternære ammoniumklorider.
Som dispergeringsmidler (uten tensidvirkning) kommer hovedsakelig på tale: lignin, natrium- og ammoniumsalter av ligninsulfonsyre, natriumsalter av maleinsyreanhydrid-diisobutylen-kopolymerer, natrium- og ammoniumsalter av sulfonerte polykondensasjonsprodukter av naftalin og formaldehyd, og sulfittavluter.
Som dispergeringsmidler som egner seg spesielt som fortyk-nings- hhv. antiklumpemidler, kan f.eks. metylcellulose, karboksymetylcellulose, hydroksyetylcellulose, polyvinyl-alkohol og alginater, kaseinater og blodalbumin anvendes.
Eksempler på egnede stabilisatorer er syrebindende midler, f.eks. epiklorhydrin, fenylglycideter og soyaepoksyder; antioksydanter, f.eks. gallussyreestere og butylhydroksy-toluen; UV-absorberere, f.eks. substituerte benzofenoner, difenylakrylnitrilsyreestere og kanelsyreestere; og deak-tivatorer, f.eks. salter av etylendiamintetraeddiksyre og polyglykoler.
De fungicide midler ifølge oppfinnelsen kan inneholde, ved siden av virkestoffene med formel I, også andre virkestoffer, f.eks. andre fungicide midler, insekticide og akaricide midler, baktericider, plantevekstregulatorer og gjødnings-midler. Slike kombinasjonsmidler egner seg for utvidelse av virkningsspekteret og for spesifikk innflytelse på plante-veksten .
I alminnelighet inneholder de fungicide midler ifølge oppfinnelsen, alt etter sin art, mellom 0,0001 og 85 vekt% av én eller flere forbindelser ifølge oppfinnelsen som virkestoff. De kan også foreligge i en form som gjør dem egnet for lagring og transport. I slike former, f.eks. emulgerbare konsentrater, er virkestoffkonsentrasjonen vanligvis i det høyere område av det ovennevnte konsentrasjonsintervall. Disse former kan da fortynnes med det samme eller andre formuleringshjelpestoffer til virkestoffkonsentrasjonen som egner seg for praktisk bruk, og slike konsentrasjoner ligger vanligvis i det lavere område av ovennevnte konsentrasjonsintervall. Emulgerbare konsentrater inneholder vanligvis 5 til 85 vekt%, fortrinnsvis 25 til 75 vekt%, av forbin-delsen (e) ifølge oppfinnelsen. Som anvendelsesformer kommer f.eks. bruksferdige løsninger, emulsjoner, suspensjoner som egner seg f.eks. som sprøytevæsker, på tale. I slike sprøytevæsker kan f.eks. konsentrasjonen ligge mellom 0,0001 og 20 vekt%. I ultralawolum-fremgangsmåten kan det formuleres sprøytevæsker hvor virkestoffkonsentrasjonen fortrinnsvis er fra 0,5 til 2 0 vekt%, mens sprøytevæsker som er formulert i lavvolum-fremgangsmåten og i høyvolum-fremgangsmåten fortrinnsvis oppviser en virkestoffkonsentrasjon på 0,02 til 1,0, hhv. 0,002 til 0,1 vekt%.
De fungicide midler ifølge oppfinnelsen kan fremstilles ved at man blander minst én forbindelse ifølge oppfinnelsen med formuleringshjelpestoffer.
Fremstillingen av midler kan utføres på kjent måte, f.eks. ved å blande virkestoffet med faste bærerstoffer, ved oppløs-ning eller suspendering i egnede løsnings- hhv. dispergeringsmidler, eventuelt under anvendelse av tensider som fuktemidler eller emulgatorer eller av dispergeringsmidler, ved fortynning av allerede tilberedte emulgerbare konsentrater med løsnings- hhv. dispergeringsmidler, osv.
Når det gjelder pulverformige midler, kan virkestoffet blandes med et fast bærerstoff, f.eks. ved sammenmaling; eller man kan impregnere det faste bærerstoff med en løsning eller suspensjon av virkestoffet og deretter fjerne løsnings-hhv. dispergeringsmidlet ved inndunstning, oppvarming eller ved avsugning under redusert trykk. Ved tilsetning av tensider hhv. dispergeringsmidler kan man gjøre slike pulverformige midler lett fuktige med vann, slik at de kan overføres i vandige suspensjoner som egner seg f.eks. som sprøytemidler.
Forbindelsene ifølge oppfinnelsen kan også blandes med et tensid og et fast bærerstoff under dannelse av et fuktig pulver som kan dispergeres i vann, eller de kan blandes med et fast forgranulert bærerstoff under dannelse av et granulatformig produkt.
Når man ønsker det, kan en forbindelse ifølge oppfinnelsen oppløses i et løsningsmiddel som ikke er blandbart med vann, f.eks. et alicyklisk keton, som med fordel inneholder en oppløst emulgator, slik at løsningen virker selvemulgerende ved tilsetning til vann. På den annen side kan virkestoffet blandes med en emulgator, og blandingen kan så fortynnes med vann til den ønskede konsentrasjon. Da kan virkestoffet løses i et løsningsmiddel og deretter blandes med en emulgator. En slik blanding kan likeledes fortynnes med vann til den ønskede konsentrasjon. På denne måte erholder man emulgerbare konsentrater hhv. bruksferdige emulsjoner.
Anvendelsen av midlene ifølge oppfinnelsen kan skje ifølge applikasjonsmetoder som er vanlige i plantevern hhv. i landbruket. Fremgangsmåten ifølge oppfinnelsen for bekjempning av sopp er karakterisert ved at man behandler det som skal beskyttes, f.eks. planter, plantedeler hhv. frø, med en effektiv mengde av en forbindelse ifølge oppfinnelsen hhv. et middel ifølge oppfinnelsen.
Følgende eksempler illustrerer oppfinnelsen.
I. Fremstilling av virkestoff med formel I:
Eksempel 1
Til 0,19 g (7,7 mmol) natriumhydrid i 20 ml dimetylformamid tilsettes ved 0° 2,0 g (7,0 mmol) 2-(cx-brom-o-tolyl)-3-metoksyakrylsyremetylester og 0,95 g (7,0 mmol) acetofenon-oksim. Etter 10 minutters omrøring av reaksjonsblandingen tilsettes mettet natriumhydrogenkarbonatløsning, og blandingen ekstraheres tre ganger med etylacetat. De organiske faser tørkes over vannfritt natriumsulfat. Etter avdestillering av løsningsmidlet renses den gjenværende olje på kiselgel under anvendelse av dietyleter/n-heksan (1:1) som elueringsmiddel kromatografisk. Man erholder på denne måte [E]-3-metoksy-2-[cx-{ [ (cx-metylbenzyl) -imino]-oksy}-o-tolyl]-akrylsyremetyl-ester som en gul olje.
Eksempel 2
3,67 g (13,2 mmol) 2-(a-brom-o-tolyl)-3-metoksyakrylsyre-metylester og 3,0 g (13,2 mmol) 4-fenoksyacetofenonoksim i 13 ml metylenklorid røres intensivt med 13 ml 2,2N natrium-hydroksydløsning og 5,7 g tetrabutylammoniumhydrogensulfat i ti minutter ved værelsestemperatur. Så tilsetter man samme mengde metylenklorid, 2,2N natriumhydroksydløsning og tetrabutylammoniumhydrogensulfat og rører ytterligere i ti minutter. Deretter tilsettes enda en gang samme mengde 2,2N natriumhydroksydløsning og tetrabutylammoniumhydrogensulfat og etter ytterligere ti minutters omrøring mettet natrium-hydrogenkarbonatløsning .
Man ekstraherer blandingen tre ganger med etylacetat, vasker de sammenslåtte, organiske faser med mettet natriumkloridløs-ning og tørker dem over vannfritt natriumsulfat. Etter avdestillering av løsningsmidlet renses den gjenværende olje kromatografisk på kiselgel under anvendelse av n-heksan/di-etyleter (4:1) som elueringsmiddel.
På denne måte erholder man [E]-3-metoksy-2-[a-{[(a-metyl-4-fenoksybenzyl)-imino]-oksy}-o-tolyl]-akrylsyremetylester som en gul olje.
Eksempel 3- 244
Analogt med fremgangsmåten som er beskrevet i eksempel 1 ("metode 1") eller eksempel 2 ("metode 2") erholder man utgående fra 2-(cx-brom-o-tolyl) - 3-metoksyakryl syremetyl ester og det tilsvarende oksim med formel II de forbindelser med formel I som er oppført i følgende tabell:
II. Formuleringseksempler
Eksempel 245
Et emulgerbart konsentrat har følgende sammensetning:
Virkestoffet og emulgatorene oppløses i løsningsmidlet og i løsningsformidleren. Ved emulgering av dette konsentrat i vann kan det fremstilles en bruksferdig sprøytevæske av enhver konsentrasjon.
Eksempel 246
Et sprøytepulver har følgende sammensetning:
Ingrediensene blandes med hverandre, og det hele males fint i en egnet mølle. Ved dispergering av blandingen i vann får man en suspensjon som egner seg som bruksferdig sprøytevæske.

Claims (8)

1. Forbindelser karakterisert ved den generelle formel I hvor R± og R2 uavhengig av hverandre betyr hydrogen; C-l_12-alkyl; C3-C6-cykloalkyl; <C>1_4-halogenalkyl; C1_4-alkoksy-Ci_4-alkyl; <C>1_4-alkyltio-C1_4-alkyl; usubstituert eller substituert fenyl-Ci~C4-alkenyl hvor substituentene er valgt fra gruppen som består av halogen og Ci-C4-alkoksy; usubstituert eller substituert fenyl-Ci-C4-alkyl hvor substituentene er valgt fra gruppen som består av halogen, Ci~C4-alkoksy og Ci-C4-halogenalkyl; usubstituert eller substituert fenyl idet de høyst 3 identiske eller forskjellige substituenter er valgt fra gruppen som består av halogen, Ci-C4-alkyl,Ci-C4-halogen-alkyl, C1-C4-halogenalkoksy, fenoksy, fenyl, fenyltio, C^ C4-alkyltio, metylendioksy og nitro; naftyl; fluorenyl; en heterocyklisk 5- eller 6-leddet gruppe med aromatisk karakter inneholdende 1 eller 2 heteroatomer valgt fra nitrogen, svovel og oksygen eller en slik gruppe som eventuelt er substituert med en eller to metyltio, metyl eller halogen, eller er en gruppe med en kondensert benzenkjerne, eller en gruppe som er bundet via metyl eller etenyl; cyano eller én av gruppene (a) til (c) hvor R3, R4, R5 og R6 i hvert enkelt tilfelle betyr hydrogen, Ci-C4-alkyl eller fenyl; R-L og R2 sammen med karbonatomet som de er bundet til, betyr en 6-leddet ring som eventuelt inneholder et oksygen-eller svovelatom og som kan inneholde én eller to kondenserte aromatiske ringer.
2. Forbindelser ifølge krav 1, karakterisert ved at betyr eventuelt substituert fenyl, idet de opp til tre identiske eller forskjellige substituenter er valgt fra gruppen som består av halogen, C1-C4-alkyl, C1-C4-halogenalkyl og Ci~C4-alkoksy, og R2 betyr hydrogen, C^-^-alkyl' Ci_4-halogen-alkyl eller C3-Cg-cykloalkyl.
3. Forbindelser ifølge krav 1, karakterisert ved at R^ betyr furyl som eventuelt er substituert med opp til to metylgrupper, tienyl som eventuelt er substituert med klor eller metyl, eller benzofuryl, og R2 betyr metyl.
4. Forbindelser ifølge et av kravene 1-3, karakterisert ved at de foreligger i [E]-isomer form.
5. Forbindelser ifølge krav 1, karakterisert ved at de er: 3-metoksy-2- [cx-{ [.(a-metylbenzyl) -imino]-oksy}-o-tolyl]-akrylsyremetylester, 3-metoksy-2-[cx-{[ (a-metyl-3,5-di-trifluormetylbenzyl)-imino ] -oksy} -o-tolyl ] -akrylsyremetylester,3-metoksy-2-[a-{[(a-metyl-2-fluor-5-metylbenzyl)-imino]-oksy}-o-tolyl]-akrylsyremetylester, l-[a-{ [(l-[2-benzofuryl]-etyl)-imino]-oksy}-o-tolyl]-3-metoksy-akrylsyremetylester, 3-metoksy-2-[a-{[(3-nitrobenzyl)-imino]-oksy}-o-tolyl]-akrylsyremetylester, 3-metoksy-2-[a-{[(a-trifluormetylbenzyl)-imino]-oksy}-o- tolyl]-akrylsyremetylester, 3-metoksy-2-[a-{[ (a-metyl-4-fluorbenzyl)-imino]-oksy}-o-tolyl]-akrylsyremetylester, 3-metoksy-2-[cx-{ [ (1-[2-tienyl]-etyl) -imino] -oksy}-o-tolyl] - akrylsyremetylester,3-metoksy-2-[a-{[ (a-metyl-4-klorbenzyl)-imino]-oksy}-o-tolyl]-akrylsyremetylester, 2-[cx-{ [ (a-cyklopropylbenzyl)-imino]-oksy}-o-tolyl]-3-metoksy-akry1syremetylester,
2- [cx-{ [ (l-[5-klor-2-tienyl]-etyl) -imino]-oksy}-o-tolyl]-3-metoksy-akrylsyrernetylester,
3- metoksy-2-[cx-{ [ (cx-metyl-3-tr i f luormetylbenzyl) -imino]-oksy}-o-tolyl]-akrylsyremetylester, 3-metoksy-2-[cx-{[ (a-metyl-3-brombenzyl) -imino]-oksy}-o-tolyl]-akrylsyremetylester, 2-[a-{[(1-[3,5-dimetyl-2-furyl]-etyl)-imino]-oksy}-o-tolyl ] -3-metoksy-akrylsyremetylester,
2- [a-{[(1-[2,5-dimetyl-3-tienyl]-etyl)-imino]-oksy}-o-tolyl]-3 -met oksy- akry 1 syremety 1 es ter,
3- metoksy-2-[a-{[(a-metyl-3-klorbenzyl)-imino]-oksy}-o-tolyl]-akrylsyremetylester, 3-metoksy-2-[a-{[(a-metyl-3-metylbenzyl)-imino]-oksy}-o-tolyl]-akrylsyremetylester, 3-metoksy-2-[a-{[(a-metyl-3,4-metylendioksybenzyl)-imino]-oksy}-o-tolyl]-akrylsyremetylester og
2- [a-{[(3-fluorbenzyl)-imino]-oksy}-o-tolyl]-3-metoksy-akrylsyremetylester .
6. Forbindelser ifølge krav 1, karakterisert ved at de er:
3- metoksy-2-[a-{[(a-metyl-4-trifluormetylbenzyl)-imino]-oksy}-o-tolyl]-akrylsyremetylester, 3-metoksy-2-[a-{[(a-metyl-3-fluor-5-trifluormetylbenzyl)-imino]-oksy}-o-tolyl]-akrylsyremetylester, 3-metoksy-2-[a-{[(a-metyl-3-fluorbenzyl)-imino]-oksy}-o-tolyl]-akrylsyremetylester, 3-metoksy-2-[a-{[(a-metyl-3-trifluormetoksybenzyl)-imino]-oksy}-o-tolyl]-akrylsyremetylester og 2-[a-{ [ (oc-etyl-3-trifluormetylbenzyl) -imino]-oksy}-o-tolyl]-3-metoksy-akrylsyremetylester. 7. Fungicid middel, karakterisert ved at det inneholder en effektiv mengde av minst én forbindelse med den generelle formel I hvor R! og R2 uavhengig av hverandre betyr hydrogen; C1_12~ alkyl; C3-C6-cykloalkyl; <C>1_4-halogenalkyl; C1_4-alkoksy-C1_4-alkyl; C1_4-alkyltio-C1_4-alkyl; usubstituert eller substituert fenyl-Ci~C4-alkenyl hvor substituentene er valgt fra gruppen som består av halogen og C^-C^-alkoksy; usubstituert eller substituert fenyl-Ci~C4-alkyl hvor substituentene er valgt fra gruppen som består av halogen, C1-C4-alkoksy og C1-C4-halogenalkyl; usubstituert eller substituert fenyl idet de høyst 3 identiske eller forskjellige substituenter er valgt fra gruppen som består av halogen, C1-C4-alkyl,C1-C4-halogen-alkyl, C1-C4-halogenalkoksy, fenoksy, fenyl, fenyltio, C;l-C4-alkyltio, metylendioksy og nitro; naftyl; fluorenyl; en heterocyklisk 5- eller 6-leddet gruppe med aromatisk karakter inneholdende 1 eller 2 heteroatomer valgt fra nitrogen, svovel og oksygen eller en slik gruppe som eventuelt er substituert med en eller to metyltio, metyl eller halogen, eller er en gruppe med en kondensert benzenkjerne, eller en gruppe som er bundet via metyl eller etenyl; cyano eller én av gruppene (a) til (c) hvor R3, R4, R5 og R6 i hvert enkelt tilfelle betyr hydrogen, C-^-C^-alkyl eller fenyl; R"L og R2 sammen med karbonatomet som de er bundet til, betyr en 6-leddet ring som eventuelt inneholder et oksygen-eller svovelatom og som kan inneholde én eller.to kondenserte aromatiske ringer, sammen med et egnet formuleringshjelpestoff.
8. Anvendelse av en forbindelse ifølge ett av kravene 1-6, hhv. et middel ifølge krav 7, for bekjempelse av sopp i landbruk og havebruk.
NO903771A 1988-12-29 1990-08-28 Akrylsyrederivater NO173543C (no)

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FI904230A0 (fi) 1990-08-27
CA2005345A1 (en) 1990-06-29
AU4639089A (en) 1990-08-01
ATE117983T1 (de) 1995-02-15
KR100187541B1 (ko) 1999-06-01
HUT55951A (en) 1991-07-29
HU216144B (hu) 1999-04-28
EP0403618B2 (de) 2004-04-28
NO173543C (no) 1993-12-29
DE58908972D1 (de) 1995-03-16
NO903771L (no) 1990-08-28
EP0403618A1 (de) 1990-12-27
NZ231891A (en) 1992-08-26
JPH03503056A (ja) 1991-07-11
PT92753B (pt) 1995-12-29
EP0403618B1 (de) 1995-02-01
WO1990007493A1 (de) 1990-07-12
DK206290A (da) 1990-08-28
HU900284D0 (en) 1991-05-28
MX9202638A (es) 1992-06-30
BR8907287A (pt) 1991-03-12
DK206290D0 (da) 1990-08-28
ES2067570T3 (es) 1995-04-01
JP2907540B2 (ja) 1999-06-21
NO903771D0 (no) 1990-08-28
KR910700228A (ko) 1991-03-14
PT92753A (pt) 1990-06-29

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