NO173543B - ACRYLIC ACID DERIVATIVES - Google Patents

ACRYLIC ACID DERIVATIVES 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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Norway
Prior art keywords
tolyl
imino
oxy
methoxy
acrylic acid
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NO90903771A
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Norwegian (no)
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NO903771D0 (en
NO903771L (en
NO173543C (en
Inventor
Hans Peter Isenring
Stephen Trah
Bettina Weiss
Original Assignee
Ciba Geigy Ag
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Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag
Publication of NO903771D0 publication Critical patent/NO903771D0/en
Publication of NO903771L publication Critical patent/NO903771L/en
Publication of NO173543B publication Critical patent/NO173543B/en
Publication of NO173543C publication Critical patent/NO173543C/en

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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
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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
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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
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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
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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
    • A01N43/24—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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    • 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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    • A01N43/62—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms three- or four-membered rings or rings with more than six members
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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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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • 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
    • C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
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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

Novel compounds of formula (I), where X is an aldimino or ketimino group, process for manufacturing them, fungicides containing these compounds as active substances, and the use of these active substances and fungicides to destroy fungi in agriculture and gardening.

Description

Akrylsyrederivater Acrylic acid derivatives

Foreliggende oppfinnelse vedrører aromatiske forbindelser, nemlig substituerte 2-fenyl-3-metoksyakrylsyremetylestere med den generelle formel I The present invention relates to aromatic compounds, namely substituted 2-phenyl-3-methoxyacrylic acid methyl esters with the general formula 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; wherein R 1 and R 2 are independently hydrogen; C1_12<->alkyl; C3-C6 cycloalkyl; <C>1-4-haloalkyl; C 1-4 -<a>lkoxy-<C>1-4 -alkyl; <C>1-4-alkylthio-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; unsubstituted or substituted phenyl-C1-C4~alkenyl wherein the substituents are selected from the group consisting of halogen and <C>1-C4~ alkoxy;

usubstituert eller substituert fenyl-C1-C4~alkyl hvoi; substituentene er valgt fra gruppen som består av halogen, C1-C4~alkoksy og C1-C4-halogenalkyl; unsubstituted or substituted phenyl-C1-C4-alkyl Hvoi; the substituents are selected from the group consisting of halogen, C 1 -C 4 - alkoxy and C 1 -C 4 -haloalkyl;

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; unsubstituted or substituted phenyl, the maximum of 3 identical or different substituents being selected from the group consisting of halogen, C₁-C₁-alkyl, C₁-C₁-halogeno-alkyl, C₁-C₁-halogeno-alkyloxy, phenoxy, phenyl, phenylthio, C 1 -C 4 alkylthio, methylenedioxy and nitro;

naftyl; fluorenyl; naphthyl; 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; a heterocyclic 5- or 6-membered group of aromatic character containing 1 or 2 heteroatoms selected from nitrogen, sulfur and oxygen or such a group optionally substituted with one or two methylthio, methyl or halogen, or is a group with a condensed benzene nucleus , or a group attached via methyl or ethenyl;

cyano eller én av gruppene (a) til (c) cyano or one of groups (a) to (c)

hvor R3, R4, R5 og R6 i hvert enkelt tilfelle betyr hydrogen, C1-C4-alkyl eller fenyl; where R 3 , R 4 , R 5 and R 6 in each case means hydrogen, C 1 -C 4 alkyl or phenyl;

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. R;L and R2 together with the carbon atom to which they are attached mean a 6-membered ring which optionally contains an oxygen or sulfur atom and which may contain one or two condensed aromatic rings.

Forbindelsene ifølge oppfinnelsen har fungicide egenskaper og egner seg som fungicide virkestoffer, især for anvendelse i landbruket og havebruket. The compounds according to the invention have fungicidal properties and are suitable as fungicidal active substances, especially for use in agriculture and horticulture.

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. The invention further relates to fungicides containing such compounds as active ingredients, as well as the use of such compounds and agents for combating fungi in agriculture and horticulture.

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) . In the above-mentioned formula I, all of the groups "alkyl", "alkenyl" and "alkynyl", as such or as part of larger groups, e.g. heteroarylalkyl, depending on the number of carbon atoms, be straight-chain or branched. In addition, the alkenyl and alkynyl groups can each exhibit more than one double bond, resp. triple bond. A possible halogen atom is fluorine, chlorine, bromine or iodine, of which fluorine, chlorine and bromine are preferred. A group such as alkyl, as such, or as part of a larger group, each having more than one halogen substituent, may have the same or different halogen atoms. By aryl is meant in particular phenyl, naphthyl, phenanthryl or fluorenyl, by heteroaryl is meant heterocyclic groups with an aromatic character, such as pyrrolyl, pyridyl, furyl, thienyl, isoxazolyl, thiazolyl, imidazolyl, pyrimidinyl or triazolyl, or such a group with condensed benzene, e.g. quinolinyl, benzofuryl, benzothienyl or dibenzofuryl. This also applies to aryl or heteroaryl as part of a larger group, e.g. aralkyl or heteroarylalkyl. The aryl and heteroaryl groups can each have one or more substituents which are suitably one or more substituents selected from halo C1-4-alkyl, C 1-4-haloalkyl, <C>1-4-alkoxy-<C>1-4-alkyl, aryl- C 2 -alkyl, heteroaryl-C 1-4 -alkyl, aryloxy-C 1-4 -alkyl, heteroaryloxy-C 1-4 -alkyl, <C>2-4-alkenyl, aryl-<C>2-4-alkenyl, heteroaryl-C 2-4-alkenyl, C 2-4-alkynyl, C3_6-Cycloalkyl, Aryl, Heteroaryl, —Alkoxy, <C>i_4~halo alkoxy, Aryl-C1_4~<a>lkoxy, Heteroaryl-<C>i_4~Alkoxy, <C>2-4-alkenyloxy<y>, C2_4- alkynyloxy, aryloxy, heteroaryloxy, C1_4-alkylthio, cyano nitro, a group NR9R1<0>, a group COR1<1>, a group COOR<12> (wherein R<9>, R<1>0, R1<1> and R1<2> each means <C>1-4-alkyl, aryl or 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. If asymmetric carbon atoms are present in the compounds of formula I, the compounds appear in an optically active form. just because an aliphatic double bond and an imino double bond occur, the compounds appear in any case in the [E] or [Z] form. Furthermore, atropisomerism can occur. Formula I shall include all these possible isomeric forms as well as their mixtures, e.g. racemic mixtures and any [E/Z] mixture.

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. A special group of compounds of formula I consists of those compounds of formula I where Z means a group R<1>R<2>C=N-, where R<1> and R<2> independently of each other mean hydrogen, Cj_i2 -alkyl, C;1-4-haloalkyl, aryl-C1-4-alkyl, heteroaryl-C1-4-alkyl, C2-12-alkenyl, aryl-<C>2-4-alkenyl, heteroaryl-C2-4-alkenyl, <C>2-12-alkynyl, C3-6-cycloalkyl , aryl, heteroaryl, cyano or one of the above-mentioned groups (a) to (d), or R<1> and R<2> together with the carbon atom to which they are attached means a ring which is further defined above.

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). Independently of each other, R<1> in the group R<1>R<2>C=N- preferably means optionally substituted phenyl, whereby optionally occurring substituents are preferably up to three identical or different halogen atoms (especially fluorine, chlorine and/or bromine), <C>1_4-alkyl groups (especially methyl), C1_4-haloalkyl groups (especially trifluoromethyl) and/or C^4-haloalkyl groups (especially trifluoromethoxy), and R<2> is preferably hydrogen, C1_14-alkyl (especially methyl or ethyl), C1-4-haloalkyl (especially trifluoromethyl) or C3-6-cycloalkyl (especially cyclopropyl).

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. Likewise preferably, R<1> means heteroaryl, especially furyl which is optionally substituted with up to two methyl groups, thienyl which is optionally substituted with chlorine or methyl, or benzofuryl, and R<2> means methyl.

Generelt er [E]-formen av forbindelsene med formel I foretrukket i forhold til [Z]-formen. In general, the [E] form of the compounds of formula I is preferred over the [Z] form.

Særlig foretrukne enkeltforbindelser med formel I er: 3-metoksy-2-[cx-{ [ (a-metylbenzyl)-imino]-oksy}-o-tolyl]-akrylsyrernetylester, Particularly preferred single compounds of formula I are: 3-methoxy-2-[cx-{[(α-methylbenzyl)-imino]-oxy}-o-tolyl]-acrylic acid methyl ester,

3-metoksy-2-[cx-{ [ (cx-metyl-3 ,5-di-trif luormetylbenzyl)-imino]-oksy}-o-tolyl]-akrylsyremetylester, 3-Methoxy-2-[cx-{[(cx-methyl-3,5-di-trifluoromethylbenzyl)-imino]-oxy}-o-tolyl]-acrylic acid methyl ester,

3-metoksy-2-[cx-{ [ (a-metyl-2-f luor-5-metylbenzyl) - imino]-oksy}-o-tolyl]-akrylsyremetylester, 3-Methoxy-2-[cx-{[(α-methyl-2-fluoro-5-methylbenzyl)-imino]-oxy}-o-tolyl]-acrylic acid methyl ester,

1- [a-{[(l-[2-benzofuryl]-etyl)-imino]-oksy}-o-tolyl]-3-metoksy-akry1syremety1ester, 1- [α-{[(1-[2-benzofuryl]-ethyl)-imino]-oxy}-o-tolyl]-3-methoxy-acrylic acid methyl ester,

3-metoksy-2-[a-{[(3-nitrobenzyl)-imino]-oksy}-o-tolyl]-akrylsyremetylester, 3-Methoxy-2-[α-{[(3-nitrobenzyl)-imino]-oxy}-o-tolyl]-acrylic acid methyl ester,

3-metoksy-2-[cx-{ [ (oc-trif luormetylbenzyl)-imino]-oksy}-o-tolyl]-akrylsyremetylester, 3-Methoxy-2-[cx-{[(oc-trifluoromethylbenzyl)-imino]-oxy}-o-tolyl]-acrylic acid methyl ester,

3-metoksy-2-[a-{ [ (cx-metyl-4-f luorbenzyl) -imino] - oksy}-o-tolyl]-akrylsyremety1ester, 3-Methoxy-2-[a-{[(c-methyl-4-fluorobenzyl)-imino]-oxy}-o-tolyl]-acrylic acid methyl ester,

3-metoksy-2-[oc-{ [ (1-[2-tienyl] -etyl) -imino] -oksy}-o-tolyl]-akrylsyremetylester, 3-Methoxy-2-[oc-{[(1-[2-thienyl]-ethyl)-imino]-oxy}-o-tolyl]-acrylic acid methyl ester,

3-metoksy-2-[a-{[(a-metyl-4-klorbenzyl)-imino]-oksy}-o-tolyl]-akrylsyremetylester, 3-Methoxy-2-[α-{[(α-methyl-4-chlorobenzyl)-imino]-oxy}-o-tolyl]-acrylic acid methyl ester,

2- [a-{[(cx-cyklopropylbenzyl)-imino]-oksy}-o-tolyl]-3-metoksy-akrylsyremetylester, 2- [α-{[(c-cyclopropylbenzyl)-imino]-oxy}-o-tolyl]-3-methoxy-acrylic acid methyl ester,

2- [a-{[(1-[5-klor-2-tienyl]-etyl)-imino]-oksy}-o-toly1]-3-metoksy-akry1syremetylester, 2- [α-{[(1-[5-chloro-2-thienyl]-ethyl)-imino]-oxy}-o-tolyl]-3-methoxy-acrylic acid methyl ester,

3- metoksy-2-[a-{[(a-metyl-3-trifluormetylbenzyl)-imino]-oksy}-o-tolyl]-akrylsyremetylester, 3- methoxy-2-[α-{[(α-methyl-3-trifluoromethylbenzyl)-imino]-oxy}-o-tolyl]-acrylic acid methyl ester,

3-metoksy-2-[0!-{ [ (a-metyl-3-brombenzyl)-imino]-oksy}-o-tolyl]-akrylsyremetylester, 3-Methoxy-2-[O!-{[(α-methyl-3-bromobenzyl)-imino]-oxy}-o-tolyl]-acrylic acid methyl ester,

2-[oc-{ [ (l-[3,5-dimetyl-2-furyl]-etyl) -imino]-oksy}-o-tolyl]-3-metoksy-akrylsyremetylester, 2-[oc-{[(1-[3,5-dimethyl-2-furyl]-ethyl)-imino]-oxy}-o-tolyl]-3-methoxy-acrylic acid methyl ester,

2- [a-([(1-[2,5-dimetyl-3-tienyl]-etyl)-imino]-oksy}-o-tolyl]-3-metoksy-akrylsyremetylester, 2- [α-([(1-[2,5-dimethyl-3-thienyl]-ethyl)-imino]-oxy}-o-tolyl]-3-methoxy-acrylic acid methyl ester,

3- metoksy-2-[cx-{ [ (oc-metyl-3-klorbenzyl) -imino] -oksy}-o-tolyl]-akrylsyremetylester, 3-Methoxy-2-[cx-{[(oc-methyl-3-chlorobenzyl)-imino]-oxy}-o-tolyl]-acrylic acid methyl ester,

3-metoksy-2- [cx-{ [ (cx-metyl-3-metylbenzyl) -imino]-oksy}-o-tolyl]-akrylsyremetylester, 3-Methoxy-2-[cx-{[(cx-methyl-3-methylbenzyl)-imino]-oxy}-o-tolyl]-acrylic acid methyl ester,

3-metoksy-2-[cx-{ [ (cx-metyl-4-metylbenzyl)-imino] - oksy}-o-tolyl]-akrylsyremetylester, 3-Methoxy-2-[cx-{[(cx-methyl-4-methylbenzyl)-imino]-oxy}-o-tolyl]-acrylic acid methyl ester,

2- [a-{[(3-fluorbenzyl)-imino]-oksy}-o-tolyl]-3-metoksy-akrylsyrernetylester, 2- [α-{[(3-fluorobenzyl)-imino]-oxy}-o-tolyl]-3-methoxy-acrylic acid ethyl ester,

3- metoksy-2-[ cx-{[(cx-metyl-4-trif luormetylbenzyl)-imino]-oksy}-o-tolyl]-akrylsyremetylester, 3-Methoxy-2-[ cx-{[(cx-methyl-4-trifluoromethylbenzyl)-imino]-oxy}-o-tolyl]-acrylic acid methyl ester,

3-metoksy-2-[oc-{ [ (cx-metyl-3-f luor-5-trif luormetylbenzyl) -imino]-oksy}-o-tolyl]-akrylsyremetylester, 3-Methoxy-2-[oc-{[(cx-methyl-3-fluoro-5-trifluoromethylbenzyl)-imino]-oxy}-o-tolyl]-acrylic acid methyl ester,

3-metoksy-2-[ cx- {[ (oc-metyl-3-fluorbenzyl) -imino]-oksy}-o-tolyl]-akrylsyremetylester, 3-Methoxy-2-[ cx-{[ (oc-methyl-3-fluorobenzyl)-imino]-oxy}-o-tolyl]-acrylic acid methyl ester,

3-metoksy-2-[cx-{[ (cx-metyl-3-trif luormetoksybenzyl) - imino]-oksy}-o-tolyl]-akrylsyremetylester og 3-Methoxy-2-[cx-{[ (cx-methyl-3-trifluoromethoxybenzyl)-imino]-oxy}-o-tolyl]-acrylic acid methyl ester and

2-[cx-{ [ (oc-etyl-3-trif luormetylbenzyl) -imino] -oksy}-o-tolyl]-3-metoksy-akrylsyremetylester. 2-[cx-{ [ (oc-ethyl-3-trifluoromethylbenzyl)-imino]-oxy}-o-tolyl]-3-methoxy-acrylic acid methyl ester.

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, Further preferred single compounds of formula I are: 2-[cx-{[ (1-[2-furyl]-ethyl)-imino]-oxy}-o-tolyl]-3-methoxy-acrylic acid methyl ester, 3-methoxy-2- [cx-{ [ (1-[2-naphthyl]-ethyl)-imino]-oxy}-o-tolyl]-acrylic acid methyl ester, 2-[cx-{ [ (4-chlorobenzyl)-imino]-oxy}-o-tolyl]-3-methoxy-acrylic acid methyl ester, 2- [cx-{ [ (2,4-dichlorobenzyl)-imino]-oxy} -o-tolyl]-3-methoxy-acrylic acid methyl ester, 3- methoxy-2-[cx-{[ (cx-methyl-4-nitrobenzyl)-imino] - oxy}-o-tolyl]-acrylic acid methyl ester, 2- [cx -{ (benzylimino) -oxy}-o-tolyl]-3-methoxy-acrylic acid methyl ester , 3- methoxy-2-[a-{[(2-pyridylmethyl)-imino]-oxy}-o-tolyl]- acrylic acid methyl ester, 2-[cx-{ [ (cx-ethylbenzyl)-imino]-oxy}-o-tolyl]-3-methoxy-acrylic acid methyl ester, 2-[a-{ [ (cx-ethyl-4-chlorobenzyl)-imino]- oxy}-o-tolyl]-3-methoxy-acrylic acid methyl ester, 3-methoxy-2-[ a- {[ (cx- [ n-propy 1 ]-benzyl)- imino ]-oxy}- o -tolyl]-acrylic acid methyl ester ,

2-[cx-{ [ (l-[benzoyl]-etyl) -imino]-oksy}-o-tolyl]-3- 2-[cx-{ [ (l-[benzoyl]-ethyl)-imino]-oxy}-o-tolyl]-3-

metoksy-akrylsyremetylester, methoxy acrylic acid methyl ester,

3-metoksy-2-[cx-{ [ (cx-metyl- -fenylallyl)-imino]-oksy}-o-tolyl]-akrylsyremetylester, 3-Methoxy-2-[cx-{[(cx-methyl--phenylallyl)-imino]-oxy}-o-tolyl]-acrylic acid methyl ester,

3-metoksy-2-[a-{ [ (a-metyl-4-fenoksybenzyl)-imino]-oksy}-o-tolyl]-akrylsyremetylester, 3-Methoxy-2-[a-{[(a-methyl-4-phenoxybenzyl)-imino]-oxy}-o-tolyl]-acrylic acid methyl ester,

2- [cx-{ [ (cx-cyklopropyl-4-klorbenzyl) -imino] -oksy}-o-tolyl]-3-metoksy-akrylsyremetylester, 2-[cx-{[(cx-cyclopropyl-4-chlorobenzyl)-imino]-oxy}-o-tolyl]-3-methoxy-acrylic acid methyl ester,

3- metoksy-2-[cx-{[ (1-[2-pyridyl]-etyl)-imino]-oksy}-o-tolyl]-akrylsyremetylester, 3- methoxy-2-[cx-{[ (1-[2-pyridyl]-ethyl)-imino]-oxy}-o-tolyl]-acrylic acid methyl ester,

3-metoksy-2-[a-{[(1-[3-pyridyl]-etyl)-imino]-oksy}-o-tolyl]-akrylsyremetylester, 3-Methoxy-2-[α-{[(1-[3-pyridyl]-ethyl)-imino]-oxy}-o-tolyl]-acrylic acid methyl ester,

3-metoksy-2-[cx-{ [ (1-[5-metyl-2-furyl]-etyl)-imino]-oksy}-o-tolyl]-akrylsyremetylester, 3-Methoxy-2-[cx-{ [ (1-[5-methyl-2-furyl]-ethyl)-imino]-oxy}-o-tolyl]-acrylic acid methyl ester,

2- [cx-{ [ (dicyklopropylmetyl) -imino]-oksy}-o-tolyl]-3-metoksy-akrylsyremetylester, 2- [cx-{ [ (dicyclopropylmethyl)-imino]-oxy}-o-tolyl]-3-methoxy-acrylic acid methyl ester,

3- metoksy-2-[a-{[(2-naftylmetyl)-imino]-oksy}-o-tolyl]-akrylsyremetylester, 3- methoxy-2-[α-{[(2-naphthylmethyl)-imino]-oxy}-o-tolyl]-acrylic acid methyl ester,

3-metoksy-2-[a-{ [ (a-metyl-3-nitrobenzyl)-imino]-oksy}-o-tolyl]-akrylsyremetylester, 3-Methoxy-2-[a-{[(a-methyl-3-nitrobenzyl)-imino]-oxy}-o-tolyl]-acrylic acid methyl ester,

2- [cx-{ [ (l-[2,4-dimetyl-5-tiazolyl) -imino] -oksy}-o-tolyl]-3-metoksy-akrylsyremetylester, 2- [cx-{ [ (1-[2,4-dimethyl-5-thiazolyl)-imino]-oxy}-o-tolyl]-3-methoxy-acrylic acid methyl ester,

3- metoksy-2-[a-{[ (cx-metyl-4-metoksybenzyl) -imino]-oksy}-o-tolyl]-akrylsyremetylester, 3-Methoxy-2-[a-{[(c-methyl-4-methoxybenzyl)-imino]-oxy}-o-tolyl]-acrylic acid methyl ester,

3-metoksy-2-[a-{[(a-metyl-3,4-diklorbenzyl)-imino]-oksy}-o-tolyl]-akrylsyremetylester, 3-Methoxy-2-[α-{[(α-methyl-3,4-dichlorobenzyl)-imino]-oxy}-o-tolyl]-acrylic acid methyl ester,

3-metoksy-2-[a-{[(a-metyl-2-fluorbenzyl)-imino]-oksy}-o-tolyl]-akrylsyremetylester, 3-Methoxy-2-[α-{[(α-methyl-2-fluorobenzyl)-imino]-oxy}-o-tolyl]-acrylic acid methyl ester,

3-metoksy-2-[a-{[(a-metyl-2,4-dimetylbenzyl)-imino]-oksy}-o-tolyl]-akrylsyremetylester, 3-Methoxy-2-[α-{[(α-methyl-2,4-dimethylbenzyl)-imino]-oxy}-o-tolyl]-acrylic acid methyl ester,

3-metoksy-2-[a-{[(a-metyl-4-etylbenzyl)-imino]-oksy}-o-tolyl]-akrylsyremetylester, 3-Methoxy-2-[α-{[(α-methyl-4-ethylbenzyl)-imino]-oxy}-o-tolyl]-acrylic acid methyl ester,

3-metoksy-2-[a-{[(a-metyl-3-etylbenzyl)-imino]-oksy}-o-tolyl]-akrylsyremetylester, 3-Methoxy-2-[α-{[(α-methyl-3-ethylbenzyl)-imino]-oxy}-o-tolyl]-acrylic acid methyl ester,

3-metoksy-2-[a-{[(a-metyl-3,4-dimetylbenzyl)-imino]-oksy}-o-tolyl]-akrylsyremetylester, 3-Methoxy-2-[α-{[(α-methyl-3,4-dimethylbenzyl)-imino]-oxy}-o-tolyl]-acrylic acid methyl ester,

2- [a-{[(l-[5-brom-2-tienyl]-etyl)-imino]-oksy}-o-tolyl]-3-metoksy-akrylsyremetylester, 2- [α-{[(1-[5-bromo-2-thienyl]-ethyl)-imino]-oxy}-o-tolyl]-3-methoxy-acrylic acid methyl ester,

3- metoksy-2-[a-{[(1-[2-naftyl]-propyl)-imino]-oksy}-o-tolyl]-akrylsyremetylester og 3- methoxy-2-[α-{[(1-[2-naphthyl]-propyl)-imino]-oxy}-o-tolyl]-acrylic acid methyl ester and

2-[a-{[(a-cyklopropyl-2-naftylmetyl)-imino]-oksy}-o- 2-[α-{[(α-cyclopropyl-2-naphthylmethyl)-imino]-oxy}-o-

tolyl]-3-metoksy-akrylsyremetylester. tolyl]-3-methoxy-acrylic acid methyl ester.

<y>tterligere eksempler på forbindelser med formel I er: 3-metoksy-2-[a-{[ (cx-metyl-2 , 3-dif luorbenzyl) -imino] - oksy}-o-tolyl]-akrylsyremetylester, Further examples of compounds of formula I are: 3-methoxy-2-[a-{[(c-methyl-2,3-difluorobenzyl)-imino]-oxy}-o-tolyl]-acrylic acid methyl ester,

3-metoksy-2-[a-{[(a-metyl-2,4-difluorbenzyl)-imino]-oksy}-o-tolyl]-akrylsyremetylester, 3-Methoxy-2-[α-{[(α-methyl-2,4-difluorobenzyl)-imino]-oxy}-o-tolyl]-acrylic acid methyl ester,

3-metoksy-2-[a-{[(a-metyl-2,5-difluorbenzyl)-imino]-oksy}-o-tolyl]-akrylsyremetylester, 3-Methoxy-2-[α-{[(α-methyl-2,5-difluorobenzyl)-imino]-oxy}-o-tolyl]-acrylic acid methyl ester,

3-metoksy-2-[a-{[(a-metyl-3,4-difluorbenzyl)-imino]-oksy}-o-tolyl]-akrylsyremetylester, 3-Methoxy-2-[α-{[(α-methyl-3,4-difluorobenzyl)-imino]-oxy}-o-tolyl]-acrylic acid methyl ester,

3-metoksy-2-[a-{[(a-trifluormetylkarbonyl-2,3-diklorbenzyl)-imino]-oksy}-o-tolyl]-akrylsyremetylester, 3-Methoxy-2-[α-{[(α-trifluoromethylcarbonyl-2,3-dichlorobenzyl)-imino]-oxy}-o-tolyl]-acrylic acid methyl ester,

3-metoksy-2-[a-{[(a-trifluormetyl-2,3-diklorbenzoyl-mety1)-imino]-oksy}-o-tolyl]-akrylsyremetylester, 3-Methoxy-2-[α-{[(α-trifluoromethyl-2,3-dichlorobenzoyl-methyl)-imino]-oxy}-o-tolyl]-acrylic acid methyl ester,

3-metoksy-2-[a-{[(l-metyl-2-fenoksypropyl)-imino]-oksy}-o-tolyl]-akrylsyremetylester, 3-Methoxy-2-[α-{[(1-methyl-2-phenoxypropyl)-imino]-oxy}-o-tolyl]-acrylic acid methyl ester,

3-metoksy-2-[a-{[(l-metyl-2-[2-klorfenoksy]-propyl)-imino]-oksy}-o-tolyl]-akrylsyremetylester, 3-Methoxy-2-[α-{[(1-methyl-2-[2-chlorophenoxy]-propyl)-imino]-oxy}-o-tolyl]-acrylic acid methyl ester,

3-metoksy-2-[a-{[(l-metyl-2-fenyltiopropyl)-imino]-oksy}-o-tolyl]-akrylsyremetylester, 3-Methoxy-2-[α-{[(1-methyl-2-phenylthiopropyl)-imino]-oxy}-o-tolyl]-acrylic acid methyl ester,

3-metoksy-2-[a-{[(a-trifluormetylkarbonyl-2-naftyl-metyl) -imino]-oksy}-o-tolyl]-akrylsyremetylester, 3-Methoxy-2-[α-{[(α-trifluoromethylcarbonyl-2-naphthyl-methyl)-imino]-oxy}-o-tolyl]-acrylic acid methyl ester,

2-[a-{[(a-cyklopropylkarbony1-2-naftylmetyl)-imino]-oksy}-o-tolyl]-3-metoksy-akrylsyremetylester, 2-[α-{[(α-cyclopropylcarbonyl-2-naphthylmethyl)-imino]-oxy}-o-tolyl]-3-methoxy-acrylic acid methyl ester,

2-[a-{[(a-isopropyl-2-naftylmetyl)-imino]-oksy}-o-tolyl]-3-metoksy-akrylsyremetylester, 2-[α-{[(α-isopropyl-2-naphthylmethyl)-imino]-oxy}-o-tolyl]-3-methoxy-acrylic acid methyl ester,

2- [a-{[(a-dimetylaminometyl-2-naftylmetyl)-imino]-oksy}-o-tolyl]-3-metoksy-akrylsyremetylester og 2- [α-{[(α-dimethylaminomethyl-2-naphthylmethyl)-imino]-oxy}-o-tolyl]-3-methoxy-acrylic acid methyl ester and

3- metoksy-2-[a-{[(2,4,4-trimetyl-l-cykloheksen-6-yl)-imino]-oksy}-o-tolyl]-akrylsyremetylester. 3-Methoxy-2-[α-{[(2,4,4-trimethyl-1-cyclohexen-6-yl)-imino]-oxy}-o-tolyl]-acrylic acid methyl ester.

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 The process for preparing the compounds according to the invention is characterized by reacting an oxime X-OH, in particular an oxime with the general formula II

hvor R<1> og R<2> har ovennevnte betydning, where R<1> and R<2> have the above meaning,

med et benzylalkoholderivat med den generelle formel with a benzyl alcohol derivative of the general formula

hvor U betyr en avgående gruppe. where U means a leaving group.

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. This reaction involves a nucleophilic substitution which can be carried out under normally applicable reaction conditions. By leaving group U found in the benzyl alcohol derivative of formula III, is meant preferably chlorine, bromine, iodine, mesyloxy or tosyloxy. The reaction conveniently takes place in an inert organic solvent, such as a cyclic ether, e.g. tetrahydrofuran or dioxane, acetone dimethylformamide or dimethylsulfoxide, in the presence of a base such as sodium hydride, sodium or potassium carbonate, a tertiary amine, e.g. a trialkylamine, especially diazabicyclononane or diazabicycloundecane, or silver oxide, at temperatures between 20°C and 80°C, preferably in the temperature range 0°C to 2°C.

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. Alternatively, the reaction can take place during phase transfer catalysis in an organic solvent, e.g. methylene chloride, in the presence of an aqueous basic solution, e.g. sodium hydroxide solution, as well as a phase transfer catalyst, such as tetrabutylammonium hydrogen sulfate, at room temperature.

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. The separation and purification of the thus prepared compounds of formula I can take place according to methods known per se. Likewise, according to methods known per se, possible isomer mixtures, e.g. E/Z isomer mixtures are separated into the pure isomers, e.g. by chromatography or fractional crystallization.

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) The oximes X-OH, e.g. with formula II, which are used as starting materials in the method according to the invention, are either known or can be prepared according to methods known per se, e.g. by reacting the corresponding carbonyl compound R^I^CsO with hydroxylamine hydrochloride in the presence of a base, e.g. sodium or potassium hydroxide or pyridine. Further methods are described in Houben-Weyl, "Methoden der Organischen Chemie", volume X/4, pages 3-3 08 (1968)

("Herstellung und Umwandlung von Oximen"). ("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. Likewise, the starting materials with formula III can be prepared in a manner known per se, e.g. as described in European Patent Publication No. 203,606 (BASF) and in the literature cited therein.

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. The compounds according to the invention have a fungicidal effect and can therefore be used to combat fungi in agriculture, in horticulture and in the woodworking industry. They are particularly suitable for inhibiting growth or for destroying phytopathogenic fungi on plant parts, e.g. leaves, stems, roots, tubers, fruits or flowers, and on seeds as well as from harmful fungi that occur in the soil. Furthermore, wood-degrading and wood-discoloring fungi can be combated with the compounds according to the invention. The compounds according to the invention are e.g. effective in combating fungi of the classes Deuteromycetes, Ascomycetes, Basidiomycetes and 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), In particular, the compounds according to the invention are suitable for combating the following harmful organisms: Powdery mildew fungi (e.g. Erysiphe graminis, Erysiphe cichoracearum, Puccinia coronata, Puccinia striiformis, Puccinia arachidis, Hemileia vastatrix, Uromyces fabae), scab fungi (e.g. Venturia inaequalis) ,

Cercospora spp. (f.eks. Cercospora arachidicola, Cercospora beticola), Cercospora spp. (e.g. Cercospora arachidicola, Cercospora beticola),

Mycosphaerella spp. (f.eks. Mycosphaerella fijiensis), Alternaria spp. (f.eks. Alternaria brassicae, Alternaria mali), Mycosphaerella spp. (e.g. Mycosphaerella fijiensis), Alternaria spp. (e.g. Alternaria brassicae, Alternaria mali),

Septoria spp. (f.eks. Septoria nodorum), Septoria spp. (eg Septoria nodorum),

Helminthosporium spp. (f.eks. Helminthosporium teres, Helminthosporium spp. (e.g. Helminthosporium teres,

Helminthosporium oryzea), 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), Plasmopara spp. (e.g. Plasmopara viticola), Pseudoperonospora spp. (e.g. Pseudoperonospora cubensis), Phytophtora spp. (e.g. Phytophtora infestans), Pseudocercosporella spp. (e.g. Pseudocercosporella herpo-trichoides),

Piricularia spp. (f.eks. Piricularia oryzae). Piricularia spp. (eg 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. Furthermore, the compounds work e.g. against the fungi of the species Tilletia, Ustilago, Rhizoctonia, Verticillium, Fusarium, Pythium, Gaeumannomyces, Sclerotinia, Monilia, Botrytis, Peronospora, Bremia, Gloeosporium, Cercosporidium, Penicillium, Ceratocystis, Rhynchosporium, Pyrenophora, Diaporthe, Ramularia and Leptosphaeria. Certain representatives of the compounds according to the invention also have an effect against wood-damaging fungi, such as e.g. of the species Coniophora, Gloeophyllum, Poria, Merulius, Trametes, Aureobasidium, Sclerophoma and Trichoderma.

Forbindelsene ifølge oppfinnelsen utmerker seg ved profyl-aktisk og kurerende virkning. The compounds according to the invention are distinguished by prophylactic and curative action.

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. The compounds according to the invention work against phytopathogenic fungi under greenhouse conditions already at concentrations of 0.5 mg to 500 mg of active substance per liter of spray liquid. In the open field, dosages of 20 g to 1 kg of active ingredient with formula I per hectares and treatment. For the control of seed- or soil-borne fungi in the pickling method, dosages of 0.01 g to 1.0 g of active substance with formula I per kg of seeds.

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. The compounds according to the invention can be formulated into a wide variety of agents, e.g. solutions, suspensions, emulsions, emulsifiable concentrates and powdered preparations. The fungicidal agents according to the invention are characterized in that they contain an effective amount of at least one compound of the general formula I as defined above, as well as formulation aids. The agents preferably contain at least one of the following formulation aids: Solid carriers; solution or dispersants; surfactants (wetting agents and emulsifiers); dispersants (without surfactant action); and stabilizers.

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. As solid carriers, the following are mainly mentioned: natural mineral substances, such as kaolin, clay, diatomaceous earth, talc, bentonite, chalk, e.g. chalk, magnesium carbonate, limestone, quartz, dolomite, attapulgite, montmorillonite and diatomaceous earth; synthetic mineral substances, such as highly dispersed silicic acid, alumina and silicates; organic substances, such as cellulose, starch, urea and synthetic resins; and fertilisers, such as phosphates and nitrates, whereby such carrier substances can be present, e.g. as granules or powders.

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. As a solution dispersants are mainly mentioned: aromatics, such as toluene, xylene, benzene and alkyl-naphthalenes; chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzene, chloroethylene and methylene chloride; aliphatic hydrocarbons, such as cyclohexane and paraffins, e.g. petroleum fractions; alcohols, such as butanol and glycol, as well as their ethers and esters; ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone and cyclohexanone; and strongly polar solutions, respectively. dispersants, such as dimethylformamide, 1-methylpyrrolidone and dimethylsulfoxide, whereby such solutions or dispersants preferably have a flash point of at least 30°C and a boiling point of at least 50°C, and water. Current as a solution or dispersants are also so-called liquid, gaseous diluents or carrier substances which are products which are gaseous at room temperature and under normal pressure. Examples of such products are especially aerosol propellants, such as halogenated hydrocarbons, e.g. dichlorodifluoromethane. If water is used as a solvent, e.g. organic solvents are also used as auxiliary solvents.

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. The surfactants (wetting agents and emulsifiers) can be non-ionic compounds, such as condensation products of fatty acids, fatty alcohols or fat-substituted phenols with ethylene oxide; fatty acid esters and ethers of sugars, or polyhydric alcohols; products obtained from sugars or polyhydric alcohols by condensation with ethylene oxide; block polymers of ethylene oxide and propylene oxide; or alkyldimethylamine oxide.

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. The surfactants can also be anionic compounds, such as soaps; fatty sulfate testers, e.g. dodecyl sodium sulfate, octadecyl sodium sulfate and cetyl sodium sulfate; alkyl sulfonates, aryl sulfonates and fatty aromatic sulfonates, such as alkyl benzene sulfonate, e.g. calcium dodecylbenzene sulfonate, and butyl naphthalene sulfonates; and complex fatty sulphonates, e.g. the amide condensation products of oleic acid and N-methyl-taurine and the sodium sulphonate of dioctyl succinate.

Tensidene kan også være kationiske forbindelser, såsom alkyl-dimetylbenzylammoniumklorider, dialkylmetylammoniumklorider, alkyltrimetylammoniumklorider og etoksylerte kvaternære ammoniumklorider. The surfactants can also be cationic compounds, such as alkyldimethylbenzylammonium chlorides, dialkylmethylammonium chlorides, alkyltrimethylammonium chlorides and ethoxylated quaternary ammonium chlorides.

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. As dispersants (without surfactant action) the following are mainly mentioned: lignin, sodium and ammonium salts of ligninsulfonic acid, sodium salts of maleic anhydride-diisobutylene copolymers, sodium and ammonium salts of sulfonated polycondensation products of naphthalene and formaldehyde, and sulfite liquors.

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. As dispersants which are particularly suitable as thickeners or anti-caking agents, can e.g. methyl cellulose, carboxymethyl cellulose, hydroxyethyl cellulose, polyvinyl alcohol and alginates, caseinates and blood albumin are used.

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. Examples of suitable stabilizers are acid-binding agents, e.g. epichlorohydrin, phenylglycid ethers and soy epoxides; antioxidants, e.g. gallic acid esters and butyl hydroxytoluene; UV absorbers, e.g. substituted benzophenones, diphenylacrylonitrile esters and cinnamic esters; and deactivators, e.g. salts of ethylenediaminetetraacetic acid and polyglycols.

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 . The fungicidal agents according to the invention may contain, in addition to the active substances of formula I, also other active substances, e.g. other fungicidal agents, insecticidal and acaricidal agents, bactericides, plant growth regulators and fertilisers. Such combination agents are suitable for expanding the spectrum of action and for specific influence on plant growth.

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%. In general, the fungicidal agents according to the invention contain, depending on their nature, between 0.0001 and 85% by weight of one or more compounds according to the invention as active ingredient. They can also be in a form that makes them suitable for storage and transport. In such forms, e.g. emulsifiable concentrates, the active substance concentration is usually in the higher range of the above-mentioned concentration interval. These forms can then be diluted with the same or other formulation aids to the active ingredient concentration that is suitable for practical use, and such concentrations are usually in the lower range of the above-mentioned concentration interval. Emulsifiable concentrates usually contain 5 to 85% by weight, preferably 25 to 75% by weight, of the compound (e) according to the invention. As forms of application, e.g. ready-to-use solutions, emulsions, suspensions that are suitable for e.g. as injection fluids, in speech. In such spray liquids, e.g. the concentration lies between 0.0001 and 20% by weight. In the ultra-low volume method, injectable liquids can be formulated where the active ingredient concentration is preferably from 0.5 to 20% by weight, while injectable liquids which are formulated in the low-volume method and in the high-volume method preferably have an active ingredient concentration of 0.02 to 1.0, respectively . 0.002 to 0.1% by weight.

De fungicide midler ifølge oppfinnelsen kan fremstilles ved at man blander minst én forbindelse ifølge oppfinnelsen med formuleringshjelpestoffer. The fungicidal agents according to the invention can be prepared by mixing at least one compound according to the invention with formulation aids.

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. The production of agents can be carried out in a known manner, e.g. by mixing the active substance with solid carriers, by dissolving or suspending in suitable solutions or dispersing agents, possibly using surfactants as wetting agents or emulsifiers or of dispersing agents, by diluting already prepared emulsifiable concentrates with solution or dispersants, etc.

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. In the case of powdered agents, the active ingredient can be mixed with a solid carrier, e.g. by grinding together; or one can impregnate the solid carrier substance with a solution or suspension of the active substance and then remove the solution or the dispersant by evaporation, heating or by suction under reduced pressure. By adding surfactants or dispersing agents, such powdery agents can be slightly moistened with water, so that they can be transferred into aqueous suspensions which are suitable, e.g. as pesticides.

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. The compounds according to the invention can also be mixed with a surfactant and a solid carrier to form a moist powder that can be dispersed in water, or they can be mixed with a solid pre-granulated carrier to form a granular product.

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. When desired, a compound according to the invention can be dissolved in a solvent which is not miscible with water, e.g. an alicyclic ketone, which advantageously contains a dissolved emulsifier, so that the solution acts as a self-emulsifier when added to water. On the other hand, the active substance can be mixed with an emulsifier, and the mixture can then be diluted with water to the desired concentration. Then the active ingredient can be dissolved in a solvent and then mixed with an emulsifier. Such a mixture can also be diluted with water to the desired concentration. In this way, emulsifiable concentrates or ready-to-use emulsions.

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. The agents according to the invention can be used according to application methods that are common in plant protection or in agriculture. The method according to the invention for combating fungi is characterized by treating what is to be protected, e.g. plants, plant parts or seeds, with an effective amount of a compound according to the invention or an agent according to the invention.

Følgende eksempler illustrerer oppfinnelsen. The following examples illustrate the invention.

I. Fremstilling av virkestoff med formel I: I. Preparation of active substance with formula I:

Eksempel 1 Example 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. To 0.19 g (7.7 mmol) sodium hydride in 20 ml dimethylformamide is added at 0° 2.0 g (7.0 mmol) 2-(cx-bromo-o-tolyl)-3-methoxyacrylic acid methyl ester and 0.95 g (7.0 mmol) acetophenone oxime. After stirring the reaction mixture for 10 minutes, saturated sodium bicarbonate solution is added, and the mixture is extracted three times with ethyl acetate. The organic phases are dried over anhydrous sodium sulfate. After distilling off the solvent, the remaining oil is purified chromatographically on silica gel using diethyl ether/n-hexane (1:1) as eluent. In this way, [E]-3-methoxy-2-[cx-{[(cx-methylbenzyl)-imino]-oxy}-o-tolyl]-acrylic acid methyl ester is obtained as a yellow oil.

Eksempel 2 Example 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 . 3.67 g (13.2 mmol) of 2-(α-bromo-o-tolyl)-3-methoxyacrylic acid methyl ester and 3.0 g (13.2 mmol) of 4-phenoxyacetophenoxime in 13 ml of methylene chloride are stirred intensively with 13 ml 2.2N sodium hydroxide solution and 5.7 g of tetrabutylammonium hydrogen sulfate for ten minutes at room temperature. The same amount of methylene chloride, 2.2N sodium hydroxide solution and tetrabutylammonium hydrogen sulphate are then added and stirred for a further ten minutes. The same amount of 2.2N sodium hydroxide solution and tetrabutylammonium hydrogen sulphate are then added once more and after a further ten minutes of stirring saturated sodium hydrogen carbonate solution.

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. The mixture is extracted three times with ethyl acetate, the combined organic phases are washed with saturated sodium chloride solution and dried over anhydrous sodium sulfate. After distilling off the solvent, the remaining oil is purified chromatographically on silica gel using n-hexane/diethyl ether (4:1) as eluent.

På denne måte erholder man [E]-3-metoksy-2-[a-{[(a-metyl-4-fenoksybenzyl)-imino]-oksy}-o-tolyl]-akrylsyremetylester som en gul olje. In this way, [E]-3-methoxy-2-[α-{[(α-methyl-4-phenoxybenzyl)-imino]-oxy}-o-tolyl]-acrylic acid methyl ester is obtained as a yellow oil.

Eksempel 3- 244 Example 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: Analogously to the method described in example 1 ("method 1") or example 2 ("method 2"), starting from 2-(cx-bromo-o-tolyl)-3-methoxyacrylic acid methyl ester and the corresponding oxime with formula II the compounds of formula I listed in the following table:

II. Formuleringseksempler II. Formulation examples

Eksempel 245 Example 245

Et emulgerbart konsentrat har følgende sammensetning: An emulsifiable concentrate has the following composition:

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. The active substance and the emulsifiers are dissolved in the solvent and in the diluent. By emulsifying this concentrate in water, a ready-to-use spray liquid of any concentration can be produced.

Eksempel 246 Example 246

Et sprøytepulver har følgende sammensetning: A spray powder has the following composition:

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. The ingredients are mixed together, and the whole thing is finely ground in a suitable mill. By dispersing the mixture in water, a suspension is obtained which is suitable as a ready-to-use spray liquid.

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.1. Compounds characterized by the general formula I wherein R ± and R 2 independently of each other are hydrogen; C-1-12 alkyl; C3-C6 cycloalkyl; <C>1-4-haloalkyl; C 1-4 -Alkoxy-C 1-4 -Alkyl; <C>1-4-alkylthio-C1-4-alkyl; unsubstituted or substituted phenyl-C1-C4-alkenyl wherein the substituents are selected from the group consisting of halogen and C1-C4-alkoxy; unsubstituted or substituted phenyl C 1 -C 4 -alkyl wherein the substituents are selected from the group consisting of halogen, C 1 -C 4 -alkyl and C 1 -C 4 -haloalkyl; unsubstituted or substituted phenyl, the maximum of 3 identical or different substituents being selected from the group consisting of halogen, C1-C4-alkyl, C1-C4-halogeno-alkyl, C1-C4-halogeno-alkyl, phenoxy, phenyl, phenylthio, C1-C4 -alkylthio, methylenedioxy and nitro; naphthyl; fluorenyl; a heterocyclic 5- or 6-membered group of aromatic character containing 1 or 2 heteroatoms selected from nitrogen, sulfur and oxygen or such a group optionally substituted with one or two methylthio, methyl or halogen, or is a group with a condensed benzene nucleus , or a group attached via methyl or ethenyl; cyano or one of groups (a) to (c) where R 3 , R 4 , R 5 and R 6 in each case means hydrogen, C 1 -C 4 alkyl or phenyl; R-L and R2 together with the carbon atom to which they are attached mean a 6-membered ring which optionally contains an oxygen or sulfur atom and which may contain one or two condensed aromatic rings. 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.2. Compounds according to claim 1, characterized in that means optionally substituted phenyl, the up to three identical or different substituents being selected from the group consisting of halogen, C1-C4-alkyl, C1-C4-halogenoalkyl and C1~C4-alkoxy , and R 2 means hydrogen, C 1-4 alkyl, C 1-4 haloalkyl or C 3 -C 8 cycloalkyl. 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.3. Compounds according to claim 1, characterized in that R 1 means furyl which is optionally substituted with up to two methyl groups, thienyl which is optionally substituted with chlorine or methyl, or benzofuryl, and R 2 means methyl. 4. Forbindelser ifølge et av kravene 1-3, karakterisert ved at de foreligger i [E]-isomer form.4. Compounds according to one of claims 1-3, characterized in that they are in [E]-isomeric 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,5. Compounds according to claim 1, characterized in that they are: 3-methoxy-2-[cx-{ [.(a-methylbenzyl)-imino]-oxy}-o-tolyl]-acrylic acid methyl ester, 3-methoxy-2- [cx-{[ (a-methyl-3,5-di-trifluoromethylbenzyl)-imino]-oxy}-o-tolyl]-acrylic acid methyl ester,3-methoxy-2-[a-{[(a-methyl-2- fluoro-5-methylbenzyl)-imino]-oxy}-o-tolyl]-acrylic acid methyl ester, l-[a-{ [(l-[2-benzofuryl]-ethyl)-imino]-oxy}-o-tolyl]- 3-Methoxy-acrylic acid methyl ester, 3-Methoxy-2-[a-{[(3-nitrobenzyl)-imino]-oxy}-o-tolyl]-acrylic acid methyl ester, 3-Methoxy-2-[a-{[(a- trifluoromethylbenzyl)-imino]-oxy}-o-tolyl]-acrylic acid methyl ester, 3-methoxy-2-[a-{[ (a-methyl-4-fluorobenzyl)-imino]-oxy}-o-tolyl]-acrylic acid methyl ester, 3-Methoxy-2-[cx-{ [ (1-[2-thienyl]-ethyl)-imino]-oxy}-o-tolyl]-acrylic acid methyl ester,3-methoxy-2-[a-{[ (a- methyl-4-chlorobenzyl)-imino]-oxy}-o-tolyl]-acrylic acid methyl ester, 2-[c-{ [ (α-cyclopropylbenzyl)-imino]-oxy}-o-tolyl]-3-methoxy-acrylic acid methyl ester, 2- [cx-{ [ (l-[5-klor-2-tienyl]-etyl) -imino]-oksy}-o-tolyl]-3-metoksy-akrylsyrernetylester,2- [cx-{ [ (1-[5-chloro-2-thienyl]-ethyl)-imino]-oxy}-o-tolyl]-3-methoxy-acrylic acid ethyl ester, 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,3-Methoxy-2-[cx-{ [ (cx-methyl-3-trifluoromethylbenzyl)-imino]-oxy}-o-tolyl]-acrylic acid methyl ester, 3-Methoxy-2-[cx-{[ (a- methyl-3-bromobenzyl)-imino]-oxy}-o-tolyl]-acrylic acid methyl ester, 2-[α-{[(1-[3,5-dimethyl-2-furyl]-ethyl)-imino]-oxy} -o-tolyl]-3-methoxy-acrylic acid methyl ester, 2- [a-{[(1-[2,5-dimetyl-3-tienyl]-etyl)-imino]-oksy}-o-tolyl]-3 -met oksy- akry 1 syremety 1 es ter,2- [α-{[(1-[2,5-dimethyl-3-thienyl]-ethyl)-imino]-oxy}-o-tolyl]-3-methoxy- acry 1 acid methyl 1 ester, 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 og3- Methoxy-2-[a-{[(a-methyl-3-chlorobenzyl)-imino]-oxy}-o-tolyl]-acrylic acid methyl ester, 3-Methoxy-2-[a-{[(a-methyl- 3-Methylbenzyl)-imino]-oxy}-o-tolyl]-acrylic acid methyl ester, 3-Methoxy-2-[a-{[(a-methyl-3,4-methylenedioxybenzyl)-imino]-oxy}-o-tolyl ]-acrylic acid methyl ester and 2- [a-{[(3-fluorbenzyl)-imino]-oksy}-o-tolyl]-3-metoksy-akrylsyremetylester .2- [α-{[(3-fluorobenzyl)-imino]-oxy}-o-tolyl]-3-methoxy-acrylic acid methyl ester . 6. Forbindelser ifølge krav 1, karakterisert ved at de er:6. Compounds according to claim 1, characterized in that they are: 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.3-Methoxy-2-[α-{[(α-methyl-4-trifluoromethylbenzyl)-imino]-oxy}-o-tolyl]-acrylic acid methyl ester, 3-methoxy-2-[α-{[(α-methyl- 3-fluoro-5-trifluoromethylbenzyl)-imino]-oxy}-o-tolyl]-acrylic acid methyl ester, 3-methoxy-2-[a-{[(a-methyl-3-fluorobenzyl)-imino]-oxy}-o -tolyl]-acrylic acid methyl ester, 3-methoxy-2-[a-{[(a-methyl-3-trifluoromethoxybenzyl)-imino]-oxy}-o-tolyl]-acrylic acid methyl ester and 2-[a-{ [ (oc- ethyl 3-trifluoromethylbenzyl)-imino]-oxy}-o-tolyl]-3-methoxy-acrylic acid methyl ester. 7. Fungicidal agent, characterized in that it contains an effective amount of at least one compound of the general formula I where R! and R 2 independently of each other means hydrogen; C1_12~ alkyl; C3-C6 cycloalkyl; <C>1-4-haloalkyl; C 1-4 -Alkoxy-C 1-4 -Alkyl; C 1-4 alkylthio-C 1-4 alkyl; unsubstituted or substituted phenyl-C 1 -C 4 -alkenyl wherein the substituents are selected from the group consisting of halogen and C 1 -C 4 -alkoxy; unsubstituted or substituted phenyl-C 1 -C 4 alkyl wherein the substituents are selected from the group consisting of halogen, C 1 -C 4 alkoxy and C 1 -C 4 haloalkyl; unsubstituted or substituted phenyl, the maximum of 3 identical or different substituents being selected from the group consisting of halogen, C1-C4-alkyl, C1-C4-halo-alkyl, C1-C4-halogeno-alkyl, phenoxy, phenyl, phenylthio, C;l -C 4 -alkylthio, methylenedioxy and nitro; naphthyl; fluorenyl; a heterocyclic 5- or 6-membered group of aromatic character containing 1 or 2 heteroatoms selected from nitrogen, sulfur and oxygen or such a group optionally substituted with one or two methylthio, methyl or halogen, or is a group with a condensed benzene nucleus , or a group attached via methyl or ethenyl; cyano or one of groups (a) to (c) where R 3 , R 4 , R 5 and R 6 in each case means hydrogen, C 1 -C 4 alkyl or phenyl; R"L and R2 together with the carbon atom to which they are attached mean a 6-membered ring which optionally contains an oxygen or sulfur atom and which may contain one or two condensed aromatic rings, together with a suitable formulation excipient. 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.8. Use of a compound according to one of claims 1-6, respectively. an agent according to claim 7, for combating fungi in agriculture and horticulture.
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