DE3640878A1 - Furancarboxylic esters, process for their preparation, and their use as pesticides - Google Patents

Furancarboxylic esters, process for their preparation, and their use as pesticides

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Publication number
DE3640878A1
DE3640878A1 DE19863640878 DE3640878A DE3640878A1 DE 3640878 A1 DE3640878 A1 DE 3640878A1 DE 19863640878 DE19863640878 DE 19863640878 DE 3640878 A DE3640878 A DE 3640878A DE 3640878 A1 DE3640878 A1 DE 3640878A1
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Prior art keywords
furan
formula
halogen
alkyl
carboxylic acid
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DE19863640878
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German (de)
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Hans-Juergen Dr Neubauer
Rainer Dr Buerstinghaus
Wolfgang Dr Seppelt
Peter Dr Hofmeister
Christoph Dr Kuenast
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BASF SE
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BASF SE
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Priority to DE19863640878 priority Critical patent/DE3640878A1/en
Priority to IL83513A priority patent/IL83513A/en
Priority to CA000544358A priority patent/CA1283923C/en
Priority to DE8787112318T priority patent/DE3773595D1/en
Priority to AT87112318T priority patent/ATE68179T1/en
Priority to EP87112318A priority patent/EP0258790B1/en
Priority to BR8704439A priority patent/BR8704439A/en
Priority to KR870009557A priority patent/KR880002855A/en
Publication of DE3640878A1 publication Critical patent/DE3640878A1/en
Priority to US07/338,562 priority patent/US4920110A/en
Withdrawn legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D307/70—Nitro radicals
    • C07D307/71—Nitro radicals attached in position 5
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/24—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D333/42—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms with nitro or nitroso radicals directly attached to ring carbon atoms
    • C07D333/44—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms with nitro or nitroso radicals directly attached to ring carbon atoms attached in position 5

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Furan Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

Furancarboxylic esters of the general formula Ia or Ib <IMAGE> in which n, R<1>, R<2> and R<3> have the following meanings: n is the number 0 or 1 and R<1>, R<2> and R<3>, in each case independently of one another, are identical or different radicals from the group comprising H, Cl, Br, NO2, branched or unbranched C1-C4-alkyl or -alkenyl, optionally substituted by halogen, and also phenyl which is optionally substituted by halogen, alkyl or alkoxy, a process for the preparation of the furan derivatives of the formula Ia or Ib, and their use as pesticides.

Description

Es ist bekannt, daß gewisse Verbindungen, die acetylenisch ungesättigte Molekülbestandteile, z. B. Propiolsäure (Propincarbonsäure) enthalten, zur Milbenbekämpfung verwendet werden können (US-PS 40 24 278 und 39 96 380). Auch die Modifizierung von Pyrethroiden durch Einbau acetylenisch ungesättigter Bindungen ist versucht worden (Proparthrin, Prothrin).It is known that certain compounds that are acetylenically unsaturated Molecular components, e.g. B. contain propiolic acid (propynecarboxylic acid) for Mite control can be used (US Pat. Nos. 40 24 278 and 39 96 380). Also the modification of pyrethroids by incorporation acetylenic unsaturated bonds have been tried (propartin, prothrin).

Es wurde nun eine neue Klasse von Verbindungen völlig anderer Struktur gefunden, die als Propargylester von Furancarbonsäuren aufzufassen sind und die allgemeine Formeln Ia bzw. Ib haben,A new class of connections with a completely different structure now became found, which are to be understood as propargylic esters of furan carboxylic acids and have the general formulas Ia and Ib,

worin n, R¹, R², R³ folgende Bedeutung haben:where n , R¹, R², R³ have the following meaning:

ndie Zahl 0 oder 1 R¹, R², R³jeweils unabhängig voneinander gleiche oder verschiedene Reste aus der Gruppe H, Cl, Br, NO₂, verzweigtes oder unverzweigtes C₁-C₄-Alkyl oder -Alkenyl, die gegebenenfalls mit Halogen substituiert sein können, und für Phenyl, das gegebenenfalls mit Halogen, Alkyl oder Alkoxy substituiert ist. n the number 0 or 1 R¹, R², R³ each independently the same or different radicals from the group H, Cl, Br, NO₂, branched or unbranched C₁-C₄ alkyl or alkenyl, which may optionally be substituted by halogen, and for Phenyl, which is optionally substituted with halogen, alkyl or alkoxy.

Es wurde gefunden, daß die Verbindungen der Formel Ia, Ib insektizid, akarizid und besonders ovizid bzw. ovolarvizid sehr gut wirksam und bekannten Wirkstoffen ähnlicher Struktur bzw. gleicher Wirkungsrichtung überlegen sind.It has been found that the compounds of the formula Ia, Ib are insecticidal, acaricidal and especially ovicidal or ovolarvizid very effective and known active substances with a similar structure or the same direction of action are superior.

Die Furanderivate der Formel Ia bzw. Ib können durch Umsetzung entsprechender Carbonsäure IIa bzw. IIb mit Propargylalkohol leicht erhalten werden (vgl. Houben-Weyl, Methoden der organ. Chemie, Band VIII, S. 516 ff., Georg Thieme Verlag, Stuttgart 1952). The furan derivatives of the formula Ia or Ib can be converted corresponding carboxylic acid IIa or IIb with propargyl alcohol easily can be obtained (cf. Houben-Weyl, Methods of Organic Chemistry, Volume VIII, P. 516 ff., Georg Thieme Verlag, Stuttgart 1952).  

Die benötigten Furancarbonsäuren und der großtechnisch erzeugte Propargyl­ alkohol sind ebenfalls leicht erhältlich. Die Umsetzung kann in an sich bekannter Weise durch Zusatz von Katalysatoren wie Schwefelsäure, Halogen­ wasserstoff, Sulfonsäure, sauren Ionenaustauschern beschleunigt und das Veresterungsgleichgewicht in gewünschtem Sinne verschoben werden, indem man dem Reaktionsgemisch das Wasser oder den Ester Ia, b entzieht, z. B. dadurch azeotrope Destillation oder durch Bindung des Wassers an Schwefel­ oder Halogenwasserstoffsäure.The required furan carboxylic acids and the large-scale propargyl alcohol is also readily available. The implementation can in itself known manner by adding catalysts such as sulfuric acid, halogen accelerated hydrogen, sulfonic acid, acidic ion exchangers and that Esterification equilibrium can be shifted in the desired sense by the water or the ester Ia, b is withdrawn from the reaction mixture, for. B. thereby azeotropic distillation or by binding the water to sulfur or hydrohalic acid.

Ebensogut kann man entsprechende Carbonsäurehalogenide IIIa bzw. IIIb, in denen Halogen für Fluor, Chlor oder Brom steht, mit Propargylalkohol in Gegenwart eines Säureacceptors umsetzen (vgl. Houben-Weyl, Methoden der organischen Chemie, Band VIII, S. 543 ff., Georg Thieme Verlag, Stuttgart, 1952). Corresponding carboxylic acid halides IIIa or IIIb, in where halogen is fluorine, chlorine or bromine, with propargyl alcohol in Implement the presence of an acid acceptor (see Houben-Weyl, Methods der organic chemistry, volume VIII, p. 543 ff., Georg Thieme Verlag, Stuttgart, 1952).  

Als Säurebindemittel eignen sich die üblichen basischen Mittel, insbesondere aliphatische, aromatische und heterocyclische Amine, z. B. Tritethylamin, Dimethylamin, Piperidin, Diazabicoyclooctan, Dimethylanilin, Dimethylbenzylamin, Pyridin, Lutidin, Dimethylaminopyridin. Auch Alkali­ metallcarbonate, wie Natrium- oder Kaliumcarbonat eignen sich als Säureacceptoren.The usual basic agents are suitable as acid binders, in particular aliphatic, aromatic and heterocyclic amines, e.g. B. Tritethylamine, dimethylamine, piperidine, diazabicoyclooctane, dimethylaniline, Dimethylbenzylamine, pyridine, lutidine, dimethylaminopyridine. Alkali too metal carbonates such as sodium or potassium carbonate are suitable Acid acceptors.

Die Umsetzung kann in einem Lösungs- oder Verdünnungsmittel vorgenommen werden. Hierzu sind teilweise die angeführten Säureacceptoren selbst oder beispielsweise folgende Lösungs- oder Verdünnungsmittel oder Gemische derselben geeignet:The reaction can be carried out in a solvent or diluent will. To this end, the acid acceptors mentioned are themselves or for example the following solvents or diluents or mixtures same suitable:

Aliphatische und aromatische, gegebenenfalls chlorierte Kohlenwasser­ stoffe, wie Petrolether, Benzol, Toluol, Xylol, Benzin, Dichlormethan, Chloroform, Tetrachlormethan, 1,2-Dichlormethan, Chlorbenzol, Ether wie Diethyl- und Di-n-butylether, Methyl-tert.-butylether, Tetrahydrofuran, Dioxan; Ketone beispielsweise Aceton, Methylethylketon, Methylisopropyl­ keton; ferner Nitrile wie Acetonitril und Propionitril.Aliphatic and aromatic, optionally chlorinated hydrocarbons substances such as petroleum ether, benzene, toluene, xylene, gasoline, dichloromethane, Chloroform, carbon tetrachloride, 1,2-dichloromethane, chlorobenzene, ethers such as Diethyl and di-n-butyl ether, methyl tert-butyl ether, tetrahydrofuran, Dioxane; Ketones for example acetone, methyl ethyl ketone, methyl isopropyl ketone; also nitriles such as acetonitrile and propionitrile.

Überlicherweise setzt man die Ausgangsstoffe in stöchiometrischem Verhältnis ein. Ein Überschuß des einen oder anderen kann in Einzelfällen aber durchaus vorteilhaft sein. Usually the starting materials are set in stoichiometric Ratio. An excess of one or the other can occur in individual cases but be quite advantageous.  

Die Umsetzung verläuft gewöhnlich oberhalb von 0°C mit ausreichender Geschwindigkeit, meist unter Wärmeentwicklung; es kann von Vorteil sein, eine Kühlmöglichkeit vorzusehen.The reaction usually proceeds above 0 ° C with sufficient Speed, mostly under heat; it can be beneficial to provide a cooling facility.

Die erfindungsgemäßen Furancarbonsäureester können außerdem nach praktisch allen anderen bekannten Verfahren der Estersynthese hergestellt werden, beispielsweise durch Umsetzung von entsprechenden Carbonsäureanhydriden [vgl. Houben-Weyl a.a.O., S. 478) mit Propargylalkohol, durch Umsetzung von entsprechenden Carbonsäuresalzen mit Propargylhalogeniden, durch Umesterungsaktionen (vgl. Houben-Weyl a.a.O., S. 508 bis 628; C. Ferri, Reaktionen der organischen Synthese, S. 446 ff., Georg Thieme Verlag, Stuttgart 1978; S. Patai, The Chemistry of Carboxylic Acids and Esters, S. 505 ff., Interscience Publishers, London, 1969).The furan carboxylic acid esters according to the invention can also be practical all other known processes of ester synthesis are prepared, for example by reacting corresponding carboxylic acid anhydrides [see. Houben-Weyl op. Cit., P. 478) with propargyl alcohol, by reaction of corresponding carboxylic acid salts with propargyl halides Transesterification campaigns (cf. Houben-Weyl op. Cit., Pp. 508 to 628; C. Ferri, Reactions in Organic Synthesis, pp. 446 ff., Georg Thieme Verlag, Stuttgart 1978; S. Patai, The Chemistry of Carboxylic Acids and Esters, Pp. 505 ff., Interscience Publishers, London, 1969).

Die erfindungsgemäßen Furanderivate mit n=1 können außerdem aus entsprechend substituierten Furanaldehyden durch Kondensation mit dem geeignet aktivierten Essigsäureester hergestellt werden (vgl. J. Org. Chem. of VSSR (1979), 2309).The furan derivatives according to the invention with n = 1 can also be prepared from appropriately substituted furan aldehydes by condensation with the suitably activated acetic acid ester (cf. J. Org. Chem. Of VSSR (1979), 2309).

Die als Ausgangsmaterial benötigten Carbonsäuren IIa bzw. IIb sind bekannt und oftmals handelsüblich. Andernfalls lassen sie sich nach allgemein bekannten chemischen Verfahren herstellen. Die in einigen der nachstehenden Beispiele verwendeten Carbonsäurechloride wurden z. T. nach Houben-Weyl a.a.O., S. 463 ff. aus den entsprechenden Carbonsäuren erhalten.The carboxylic acids IIa and IIb required as starting material are known and often commercially available. Otherwise, let them be general produce known chemical processes. The in some of the The following examples used carboxylic acid chlorides were e.g. T. after Houben-Weyl op. Cit., P. 463 ff. From the corresponding carboxylic acids receive.

Die Verbindungen der Formel Ia bzw. Ib fallen meist als ölige Verbindungen oder als Feststoffe an. Im folgenden werden daher von den jeweils hergestellten Stoffen die Schmelzintervalle oder Brechungsindices angegeben. Die ohne Angabe solcher Kenngrößen nachstehend aufgeführten Verbindungen können aus entsprechenden Rohstoffen ohne weiteres erhalten werden; sie lassen eine gleichartige Wirkung erwarten.The compounds of the formula Ia or Ib mostly fall as oily compounds or as solids. The following are therefore of each manufactured substances the melting intervals or refractive indices specified. The ones listed below without specifying such parameters Compounds can easily be obtained from appropriate raw materials will; they can be expected to have a similar effect.

Beispiele für die Herstellung von erfindungsgemäßen Stoffen Ia, bExamples for the production of substances Ia, b Verbindung Nr. 5 der nachfolgenden TabelleCompound No. 5 of the table below

Die Lösung von 1,8 g Propargylalkohol in 15 ml abs. Pyridin wird auf 5°C gekühlt und portionsweise mit 5,2 g 5-Chlorfuran-2-carbonsäurechlorid versetzt. Man läßt noch 12 h bei Raumtemperatur rühren, gießt in 100 ml Eiswasser und stellt mit konz. HCl auf pH 2 ein. Es wird dreimal mit Ether extrahiert und die vereinigten Extrakte mit 10prozentiger Natriumhydrogen­ carbonat-Lösung und Wasser gewaschen. Nach Trocknen über Natriumsulfat, Abziehen des Solvens i. V. und Umkristallisieren aus Methanol erhält man 2,2 g 5-Chlorfuran-2-carbonsäurepropargylester mit Schmelzpunkt Fp: 58 bis 60°C.The solution of 1.8 g propargyl alcohol in 15 ml abs. Pyridine is at 5 ° C cooled and in portions with 5.2 g of 5-chlorofuran-2-carboxylic acid chloride transferred. The mixture is stirred for a further 12 h at room temperature and poured into 100 ml Ice water and provides with conc. HCl to pH 2. It is used three times with ether extracted and the combined extracts with 10 percent sodium hydrogen carbonate solution and water washed. After drying over sodium sulfate,  Removing the solvent i. V. and recrystallization from methanol are obtained 2.2 g of 5-chlorofuran-2-carboxylic acid propargyl ester with melting point mp: 58 to 60 ° C.

Verbindung Nr. 14 der nachfolgenden TabelleCompound No. 14 in the table below

Die Lösung von 11,5 g 3-(5-Methylfuran-2-yl)-propensäurechlorid in 30 ml abs. Tetrahydrofuran wird unter Kühlung bei 0 bis 5°C mit 4,2 g Propargyl­ alkohol und 20 ml Pyridin versetzt. Man läßt noch 12 Stunden bei Raumtemperatur rühren, filtriert vom ausgefallenen Hydrochlorid ab, engt i. V. ein und nimmt in 200 ml Essigester und 50 ml Wasser auf. Es wird dreimal mit Wasser gewaschen, über Na₂SO₄ getrocknet, das Solvens i. V. abgezogen und der Rückstand chromatographisch (Toluol/Essigester = 1/2) gereinigt. Man erhält 10,9 g 3-(5-Methylfuran-2-yl)-propensäurepropargyl­ ester, Brechungsindex n=1,578.The solution of 11.5 g of 3- (5-methylfuran-2-yl) propenyl chloride in 30 ml of abs. Tetrahydrofuran is mixed with cooling at 0 to 5 ° C with 4.2 g of propargyl alcohol and 20 ml of pyridine. The mixture is stirred for a further 12 hours at room temperature, filtered off from the precipitated hydrochloride, evaporated down i. V. and takes up in 200 ml of ethyl acetate and 50 ml of water. It is washed three times with water, dried over Na₂SO₄, the solvent i. V. deducted and the residue purified by chromatography (toluene / ethyl acetate = 1/2). 10.9 g of 3- (5-methylfuran-2-yl) propenoic acid propargyl ester are obtained, refractive index n = 1.578.

Verbindung Nr. 22 der nachfolgenden TabelleCompound No. 22 in the table below

6,8 g Propargylalkohol werden in 20 ml absolutem Pyridin gelöst. Nach Zugabe von 17,0 g 2,5-Dimethylfuran-3-carbonsäurechlorid bei höchstens 5°C läßt man 8 Stunden bei Raumtemperatur rühren. Man fügt 100 ml Diethylether zu, saugt ab und engt i. V. ein. Der Rückstand wird in 150 ml Essigester aufgenommen, mit Wasser ausgeschüttelt und die organische Phase über Natriumsulfat getrocknet. Nach Abziehen des Solvens i. V. wird aus n-Propanol/Wasser umkristallisiert. Man erhält 12,5 g 2,5-Dimethylfuran­ 3-carbonsäurepropargylester. Schmelzpunkt Fp.: 35 bis 37°C.6.8 g of propargyl alcohol are dissolved in 20 ml of absolute pyridine. To Add 17.0 g of 2,5-dimethylfuran-3-carboxylic acid chloride at a maximum of 5 ° C is allowed to stir for 8 hours at room temperature. 100 ml of diethyl ether are added to, sucks off and constricts i. V. a. The residue is dissolved in 150 ml of ethyl acetate taken up, shaken out with water and the organic phase over Dried sodium sulfate. After removing the solvent i. V. is out re-crystallized n-propanol / water. 12.5 g of 2,5-dimethylfuran are obtained 3-carboxylic acid propargylic ester. Melting point: 35 to 37 ° C.

Tabelle table

Claims (6)

1. Furancarbonsäureester der allgemeinen Formel Ia bzw. Ib worin n, R¹, R², R³ folgende Bedeutung haben:ndie Zahl 0 oder 1 R¹, R², R³jeweils unabhängig voneinander gleiche oder verschiedene Reste aus der Gruppe H, Cl, Br, NO₂, verzweigtes oder unverzweigtes C₁-C₄-Alkyl oder -Alkenyl, die gegebenenfalls mit Halogen substituiert sein können, und für Phenyl, das gegebenenfalls mit Halogen, Alkyl oder Alkoxy substituiert ist.1. furan carboxylic acid esters of the general formula Ia or Ib wherein n , R¹, R², R³ have the following meaning: n the number 0 or 1 R¹, R², R³ each independently of the same or different radicals from the group H, Cl, Br, NO₂, branched or unbranched C₁-C₄-alkyl or - Alkenyl, which may optionally be substituted by halogen, and phenyl, which may be substituted by halogen, alkyl or alkoxy. 2. Verfahren zur Herstellung der Furanderivate der Formel Ia bzw. Ib gemäß Anspruch 1, dadurch gekennzeichnet, daß man eine entsprechende Carbonsäure IIa bzw. IIb mit Propargylalkohol umsetzt, oder daß man ein entsprechendes Säure­ halogenid IIIa bzw. IIIb mit Propargylalkohol, gegebenenfalls in Gegenwart eines Säureacceptors umsetzt. 2. A process for the preparation of the furan derivatives of the formula Ia or Ib according to claim 1, characterized in that a corresponding carboxylic acid IIa or IIb reacted with propargyl alcohol, or that a corresponding acid halide IIIa or IIIb with propargyl alcohol, optionally in the presence of an acid acceptor. 3. Schädlingsbekämpfungsmittel, enthaltend eine Verbindung gemäß Anspruch 1.3. Pesticide containing a compound according to Claim 1. 4. Schädlingsbekämpfungsmittel, enthaltend einen festen oder flüssigen Trägerstoff und mindestens ein Furanderivat gemäß Anspruch 1.4. Pesticides containing a solid or liquid Carrier and at least one furan derivative according to claim 1. 5. Verwendung von Furanderivaten der Formel Ia bzw. Ib gemäß Anspruch 1 bis 3 als Insektizid, Akarizid und insbesondere Ovizid.5. Use of furan derivatives of the formula Ia or Ib according to claim 1 to 3 as an insecticide, acaricide and especially ovicide. 6. Verfahren zur Bekämpfung von Schädlingen, dadurch gekennzeichnet, daß man eine wirksame Menge des Furanderivats der Formel Ia bzw. Ib gemäß Anspruch 1 bis 3 auf Schädlinge bzw. deren Lebensraum einwirken läßt.6. A method for controlling pests, characterized in that an effective amount of the furan derivative of the formula Ia or Ib according to Claims 1 to 3 can act on pests or their habitat.
DE19863640878 1986-08-30 1986-11-29 Furancarboxylic esters, process for their preparation, and their use as pesticides Withdrawn DE3640878A1 (en)

Priority Applications (9)

Application Number Priority Date Filing Date Title
DE19863640878 DE3640878A1 (en) 1986-11-29 1986-11-29 Furancarboxylic esters, process for their preparation, and their use as pesticides
IL83513A IL83513A (en) 1986-08-30 1987-08-12 Propargyl furan - and thiophenecarboxylates, their preparation and their use for combating insects, arachnides and nematodes
CA000544358A CA1283923C (en) 1986-08-30 1987-08-12 Propargyl furan- and thiophenecarboxylates
DE8787112318T DE3773595D1 (en) 1986-08-30 1987-08-25 Furan- und thiophencarbonsaeurepropargylester.
AT87112318T ATE68179T1 (en) 1986-08-30 1987-08-25 FURANIC AND THIOPHENECARBONIC ACID PROPARGYLESTER.
EP87112318A EP0258790B1 (en) 1986-08-30 1987-08-25 Furan- or thiophenecarboxylic-acid propargyl esters
BR8704439A BR8704439A (en) 1986-08-30 1987-08-27 INSECTICIDAL COMPOSITIONS BASED ON NEW PROPARGILIC ESTERS OF FURANO-AND THIOFENO-CARBOXOLIC ACIDS (1A, RESPECTIVELY IB), AND, PROCESS FOR OBTAINING THOSE COMPOUNDED (1A OR 1B)
KR870009557A KR880002855A (en) 1986-08-30 1987-08-29 Propargyl Furan- and Thiophencarboxylate
US07/338,562 US4920110A (en) 1986-08-30 1989-04-14 Propargyl furan- and thiophenecarboxylates

Applications Claiming Priority (1)

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DE19863640878 DE3640878A1 (en) 1986-11-29 1986-11-29 Furancarboxylic esters, process for their preparation, and their use as pesticides

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