DE3825822A1 - Phenoxyalkyl-substituted 5-membered ring-heteroaromatics, processes for their preparation, and pesticides containing them - Google Patents

Phenoxyalkyl-substituted 5-membered ring-heteroaromatics, processes for their preparation, and pesticides containing them

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Publication number
DE3825822A1
DE3825822A1 DE19883825822 DE3825822A DE3825822A1 DE 3825822 A1 DE3825822 A1 DE 3825822A1 DE 19883825822 DE19883825822 DE 19883825822 DE 3825822 A DE3825822 A DE 3825822A DE 3825822 A1 DE3825822 A1 DE 3825822A1
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DE
Germany
Prior art keywords
alkyl
substituted
phenoxyalkyl
cycloalkyl
haloalkyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
DE19883825822
Other languages
German (de)
Inventor
Hans-Juergen Dr Neubauer
Uwe Dr Kardorff
Joachim Dr Leyendecker
Christoph Dr Kuenast
Peter Dr Hofmeister
Wolfgang Dr Krieg
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF SE
Original Assignee
BASF SE
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
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Publication date
Application filed by BASF SE filed Critical BASF SE
Priority to DE19883825822 priority Critical patent/DE3825822A1/en
Priority to US07/379,956 priority patent/US5013847A/en
Priority to CA000605747A priority patent/CA1338938C/en
Priority to DE58908492T priority patent/DE58908492D1/en
Priority to EP89113498A priority patent/EP0353571B1/en
Priority to ES89113498T priority patent/ES2063082T3/en
Priority to JP1194448A priority patent/JPH0288559A/en
Priority to KR1019890010783A priority patent/KR0125577B1/en
Publication of DE3825822A1 publication Critical patent/DE3825822A1/en
Priority to US07/658,241 priority patent/US5212194A/en
Priority to US07/942,387 priority patent/US5342849A/en
Withdrawn legal-status Critical Current

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Abstract

Phenoxyalkyl-substituted heteroaromatics of the formula I <IMAGE> in which R<1> is C1-C12-alkyl, C2-C12-alkenyl, C2-C12-alkynyl, C1 -C12-haloalkyl, C2-C12-haloalkenyl, C2-C12-haloalkynyl, C3-C12-alkoxyalkyl, C3-C8-cycloalkyl, C4-C12-cycloalkylalkyl, C3-C8-halocycloalkyl, C4-C12-halocycloalkylalkyl, C4-C12-cycloalkylhaloalkyl or C4-C12-halocycloalkylhaloalkyl, R<2> is hydrogen or C1-C4-alkyl, X is O, S or SO2, Z is hydrogen, halogen or C1-C4-alkyl and Q is a 5-membered heteroaromatic ring which is optionally mono- or polysubstituted by halogen, C1-C8-alkyl, C2-C8-alkenyl, C1-C4-haloalkyl, C1-C8-alkoxy, C1-C8-alkylthio, C2-C8-alkoxyalkyl, or C3-C10 -cycloalkyl, processes for their preparation, and their use for controlling pests.

Description

Die vorliegende Erfindung betrifft neue phenoxyalkylsubstituierte 5-Ring- Heteroaromaten der allgemeinen Formel IThe present invention relates to new phenoxyalkyl-substituted 5-ring Heteroaromatics of the general formula I

in der
R¹ C₁-C₁₂-Alkyl, C₂-C₁₂-Alkenyl, C₂-C₁₂-Alkinyl, C₁-C₁₂-Halogenalkyl, C₂-C₁₂-Halogenalkenyl, C₂-C₁₂-Halogenalkinyl, C₃-C₁₂-Alkoxyalkyl, C₃-C₈-Cycloalkyl, C₄-C₁₂-Cycloalkyl-alkyl, C₃-C₈-Halogencycloalkyl, C₄-C₁₂-Halogencycloalkyl-alkyl, C₄-C₁₂-Cycloalkyl-halogenalkyl oder C₄-C₁₂-Halogencycloalkyl-halogenalkyl,
R² Wasserstoff oder C₁-C₄-Alkyl,
X O, S oder SO₂,
Z Wasserstoff, Halogen oder C₁-C₄-Alkyl und
Q einen 5-Ring-Heteroaromaten, der gegebenenfalls ein oder mehrfach mit Halogen, C₁-C₈-Alkyl, C₂-C₈-Alkenyl, C₁-C₄-Halogenalkyl, C₁-C₈-Alkoxy, C₁-C₈-Alkylthio, C₂-C₈-Alkoxyalkyl oder C₃-C₁₀-Cycloalkyl substituiert ist, bedeuten.in the
R¹ C₁-C₁₂-alkyl, C₂-C₁₂-alkenyl, C₂-C₁₂-alkynyl, C₁-C₁₂-haloalkyl, C₂-C₁₂-haloalkenyl, C₂-C₁₂-haloalkynyl, C₃-C₁₂-alkoxyalkyl, C₃-C₈-cycloalkyl, C₄ -C₁₂-cycloalkyl-alkyl, C₃-C₈-halocycloalkyl, C₄-C₁₂-halocycloalkyl-alkyl, C₄-C₁₂-cycloalkyl-haloalkyl or C₄-C₁₂-halocycloalkyl-haloalkyl,
R² is hydrogen or C₁-C₄ alkyl,
XO, S or SO₂,
Z is hydrogen, halogen or C₁-C₄-alkyl and
Q is a 5-ring heteroaromatic compound which may be substituted one or more times with halogen, C₁-C₈-alkyl, C₂-C₈-alkenyl, C₁-C₄-haloalkyl, C₁-C₈-alkoxy, C₁-C₈-alkylthio, C₂-C₈- Alkoxyalkyl or C₃-C₁₀ cycloalkyl is substituted.

Außerdem betrifft die Erfindung die Herstellung der Verbindungen I, Schädlingsbekämpfungsmittel, die die Verbindungen I als Wirkstoffe enthalten sowie ein Verfahren zur Bekämpfung von Schädlingen.The invention also relates to the preparation of the compounds I, Pesticides containing the compounds I as active ingredients contain as well as a method for controlling pests.

In EP-A 02 03 798 ist beispielsweise in 2-Stellung phenoxyethoxysubstituiertes 1,3-Thiazol der Struktur AIn EP-A 02 03 798, for example, phenoxyethoxy is substituted in the 2-position 1,3-thiazole of structure A

beschrieben. Phenoxymethylsubstituierte Heteroatome sind aus DE-A 25 16 331 und EP-A 2 39 047 bekannt. Die insektizide Wirkung dieser Verbindungen läßt jedoch zu wünschen übrig. described. Phenoxymethyl-substituted heteroatoms are out DE-A 25 16 331 and EP-A 2 39 047 are known. The insecticidal effects of this Connections, however, leave something to be desired.  

Der Erfindung lag daher die Aufgabe zugrunde, neue substituierte Heteroaromaten mit verbesserter Wirkung bereitzustellen.The invention was therefore based on the object of new substituted heteroaromatics to provide with improved effect.

Demgemäß wurden die eingangs definierten phenoxyalkylsubstituierten 5-Ring-Heteroaromaten I sowie Verfahren zu deren Herstellung gefunden. Die Verbindungen I eignen sich hervorragend zur Bekämpfung von Schädlingen.Accordingly, the phenoxyalkyl-substituted 5-ring heteroaromatics defined at the outset I and methods for their production found. The Compounds I are ideal for controlling pests.

Die Verbindungen I sind nach folgender Methode erhältlich:The compounds I can be obtained by the following method:

Die Umsetzung erfolgt zwischen einem Phenol II und einem 5-Ring-Heteroaromaten III in Gegenwart einer Base im Temperaturbereich von (-20) bis 250°C, vorzugsweise von 20 bis 120°C, nach folgender Reaktionsgleichung:The reaction takes place between a phenol II and a 5-ring heteroaromatic III in the presence of a base in the temperature range from (-20) to 250 ° C, preferably from 20 to 120 ° C, according to the following reaction equation:

Anstelle des Phenols II plus Base kann auch das Phenolatanion von II direkt mit III umgesetzt werden.Instead of the phenol II plus base, the phenolate anion of II can be implemented directly with III.

In der obigen Gleichung bedeutet der Rest Y eine an sich übliche Abgangsgruppe, wie beispielsweise einen Sulfonsäurerest oder ein Halogen. Unter den Sulfonsäureresten sind Methansulfonyl, Trifluormethansulfonyl und p-Toluolsulfonyl, unter den Halogenen sind Chlor und Brom bevorzugt; besonders bevorzugt wird Chlor.In the above equation, the radical Y denotes a leaving group which is customary per se, such as a sulfonic acid residue or a halogen. Under the sulfonic acid residues are methanesulfonyl, trifluoromethanesulfonyl and p-toluenesulfonyl, among the halogens chlorine and bromine are preferred; chlorine is particularly preferred.

Die Phenole II sind zum Teil aus Houben/Weyl, Bd. VI, 3, Methoden der org. Chemie, Thieme Verlag, 1965, 49 ff., bekannt oder können nach den dort beschriebenen Methoden hergestellt werden.The phenols II are partly from Houben / Weyl, Vol. VI, 3, methods of org. Chemie, Thieme Verlag, 1965, 49 ff., Known or can there according to described methods are produced.

Die Heteroaromaten III sind entweder bekannt und teilweise kommerziell erhältlich oder lassen sich nach allgemein bekannten chemischen Verfahren herstellen. Verfahren zur Herstellung von Thiophenderivaten finden sich z. B. in Comprehensive Heterocyclic Chemistry, R. Katritzky und W. Rees, Vol. 4, S. 863 ff., Pergamon Press, 1984; von Furanderivaten, z. B. in DE-A 35 14 384, DE-A 35 46 371 oder Advances in Heterocyclic Chemistry, Vol. 30, S. 167 ff., 1982; von Pyrrolderivaten z. B. in Comprehensive Heterocyclic Chemistry, R. Katritzky und W. Rees, Vol. 4, S. 201 ff., Pergamon Press, 1984, von Thiazolderivaten, Oxazolderivaten, Isothiazolderivaten, Thiadiazolderivaten und Oxadiazolderivaten z. B. in Comprehensive Heterocyclic Chemistry, R. Katritzky und W. Rees, Vol. 6, S. 166, 177, 235, 386, 425 ff., Pergamon Press, 1984; von Imidazolderivaten z. B. in Advances in Heterocyclic Chemistry, Vol. 27, S. 242 ff., 1980; von Pyrazolderivaten z. B. in Heteroaromatic Nitrogen Compounds, The Azoles, S. 31 ff., Cambridge University Press, 1976; von Triazolderivaten z. B. in Comprehensive Heterocyclic Chemistry, R. Katritzky und W. Rees, Vol. 5, S. 733 ff., Pergamon Press, 1984; von Isoxazolderivaten z. B. in DE-A 25 49 962 und DE-A 27 54 832.The heteroaromatics III are either known and in some cases commercial available or can be according to generally known chemical processes produce. Processes for the preparation of thiophene derivatives can be found e.g. B. in Comprehensive Heterocyclic Chemistry, R. Katritzky and W. Rees, Vol. 4, pp. 863 ff., Pergamon Press, 1984; of furan derivatives, e.g. B. in DE-A 35 14 384, DE-A 35 46 371 or Advances in Heterocyclic Chemistry, Vol. 30, pp. 167 ff., 1982; of pyrrole derivatives e.g. B. Comprehensive Heterocyclic Chemistry, R. Katritzky and W. Rees, Vol. 4, pp. 201 ff., Pergamon Press, 1984, of thiazole derivatives, oxazole derivatives, isothiazole derivatives, Thiadiazole derivatives and oxadiazole derivatives z. B. in Comprehensive Heterocyclic Chemistry, R. Katritzky and W. Rees, Vol. 6,  Pp. 166, 177, 235, 386, 425 ff., Pergamon Press, 1984; of imidazole derivatives e.g. B. in Advances in Heterocyclic Chemistry, Vol. 27, pp. 242 ff., 1980; of pyrazole derivatives e.g. B. Heteroaromatic Nitrogen Compounds, The Azoles, pp. 31 ff., Cambridge University Press, 1976; of triazole derivatives e.g. B. in Comprehensive Heterocyclic Chemistry, R. Katritzky and W. Rees, Vol. 5, pp. 733 ff., Pergamon Press, 1984; of isoxazole derivatives e.g. B. in DE-A 25 49 962 and DE-A 27 54 832.

Man setzt normalerweise mindestens äquivalente Mengen einer Base, bezogen auf II, zu II und/oder III zu, kann aber diese auch im Überschuß oder gegebenenfalls auch als Lösungsmittel verwenden. Als Basen eignen sich beispielsweise Hydroxide von Alkali- und Erdalkalimetallen wie Natriumhydroxid, Kaliumhydroxid und Calciumhydroxid; Alkoholate von Alkali- und Erdalkalimetallen wie Natriummethylat, Natriumethylat, Calciummethanolat oder Kalium-tert.-butylat; Alkali- oder Erdalkalimetallhydride wie Natriumhydrid, Kaliumhydrid oder Calciumhydrid; Alkali- oder Erdalkalicarbonate wie Natriumcarbonat, Kaliumcarbonat oder Calciumcarbonat; aliphatische Amine wie Dimethylamin, Triethylamin oder Diisopropylamin; heterocyclische Amine wie Piperidin, Piperazin oder Pyrrolidin; aromatische Amine wie Pyridin oder Pyrrol und gegebenenfalls auch Alkyllithium-Verbindungen wie n-Butyllithium.Normally at least equivalent amounts of a base are used to II, II and / or III, but these can also be in excess or optionally also use as a solvent. Are suitable as bases for example hydroxides of alkali and alkaline earth metals such as sodium hydroxide, Potassium hydroxide and calcium hydroxide; Alcoholates of alkali and Alkaline earth metals such as sodium methylate, sodium ethylate, calcium methoxide or potassium tert-butoxide; Alkali or alkaline earth metal hydrides such as Sodium hydride, potassium hydride or calcium hydride; Alkali or alkaline earth carbonates such as sodium carbonate, potassium carbonate or calcium carbonate; aliphatic amines such as dimethylamine, triethylamine or diisopropylamine; heterocyclic amines such as piperidine, piperazine or pyrrolidine; aromatic amines such as pyridine or pyrrole and optionally also Alkyl lithium compounds such as n-butyllithium.

Zur Herstellung der erfindungsgemäßen Verbindungen I nach der vorstehend beschriebenen Methode setzt man die Ausgangsstoffe üblicherweise in stöchiometrischem Verhältnis ein. Ein Überschuß des einen oder anderen kann in Einzelfällen aber durchaus vorteilhaft sein.For the preparation of the compounds I according to the above The method described usually sets the starting materials in stoichiometric ratio. An excess of one or the other can be quite advantageous in individual cases.

Die Umsetzung wird zweckmäßigerweise in einem Lösungsmittel oder Verdünnungsmittel durchgeführt. Hierzu eignen sich beispielsweise aliphatische Kohlenwasserstoffe wie n-Pentan, n-Hexan, das Hexan-Isomerengemisch und Petrolether; aromatische Kohlenwasserstoffe wie Benzol, Toluol, die Xylole und deren Isomerengemische, Benzin; Alkohole wie Methanol, Ethanol, n-Propanol und Isopropanol; Ether wie Diethyl-, Di-n- butylether, Methyl-tert.-butylether, Tetrahydrofuran und Dioxan; Ketone wie Aceton, Methylethylketon und Methylisopropylketon; Nitrile wie Acetonitril und Propionitril; aprotische dipolare Lösungsmittel wie Dimethylformamid, Dimethylsulfoxid oder Pyridin. Auch Gemische dieser Stoffe können als Lösungs- und Verdünnungsmittel verwendet werden.The reaction is conveniently carried out in a solvent or Diluent carried out. For example, are suitable for this aliphatic hydrocarbons such as n-pentane, n-hexane, the hexane isomer mixture and petroleum ether; aromatic hydrocarbons such as benzene, Toluene, the xylenes and their isomer mixtures, gasoline; Alcohols like Methanol, ethanol, n-propanol and isopropanol; Ethers such as diethyl, di-n butyl ether, methyl tert-butyl ether, tetrahydrofuran and dioxane; Ketones such as acetone, methyl ethyl ketone and methyl isopropyl ketone; Nitriles like Acetonitrile and propionitrile; aprotic dipolar solvents such as Dimethylformamide, dimethyl sulfoxide or pyridine. Mixtures of these Substances can be used as solvents and thinners.

Die Umsetzungen verlaufen gewöhnlich oberhalb von -20°C mit ausreichenden Geschwindigkeiten. 120°C müssen im allgemeinen nicht überschritten werden. Da sie in einigen Fällen unter Wärmeentwicklung verlaufen, kann es von Vorteil sein, Kühlmöglichkeiten vorzusehen. The reactions usually proceed above -20 ° C with sufficient Speeds. In general, 120 ° C do not have to be exceeded. As they develop heat in some cases, it can develop from Be advantageous to provide cooling options.  

Die Reaktionsgemische werden in üblicher Weise aufgearbeitet, z. B. durch Versetzen mit Wasser, Trennen der Phasen und Säulenchromatographie. Die neuen Verbindungen der Formel I fallen teilweise in Form farbloser oder schwach bräunlich gefärbter, zäher Öle an, die sich durch längeres Erwärmen unter vermindertem Druck auf mäßig erhöhte Temperatur ("Andestillieren") von den letzten flüchtigen Anteilen befreien und auf diese Weise reinigen lassen. Erhält man die Verbindungen der Formel I in kristalliner Form, so kann ihre Reinigung durch Umkristallisieren erfolgen.The reaction mixtures are worked up in a conventional manner, for. B. by Mix with water, separate the phases and column chromatography. The new compounds of formula I fall partly in the form of colorless or slightly brownish, viscous oils, which are characterized by prolonged Warm under reduced pressure to moderately elevated temperature ("Andestillieren") free from the last volatile components and open let it clean this way. Obtaining the compounds of formula I in crystalline form, it can be purified by recrystallization respectively.

Die Substituenten in Formel I haben im einzelnen folgende Bedeutung:
R¹ - unverzweigtes oder verzweigtes C₁-C₁₂-Alkyl, bevorzugt C₁-C₈- Alkyl, besonders bevorzugt verzweigte C₃-C₈-Alkyl, wie Isopropyl, Isobutyl, sec.-Butyl, tert.-Butyl, Isopentyl, 1-Methyl-butyl, Isohexyl, 1-Methyl-pentyl, Isoheptyl, 1-Methyl-hexyl, 1-Methyl- heptyl, 1,3-Dimethyl-butyl, 1,2-Dimethyl-butyl, 3-Methyl-pentyl, 4-Methyl-butyl, 1-Ethyl-propyl und 1-Ethyl-butyl,
- unverzweigtes oder verzweigtes C₂-C₁₂-Alkenyl, bevorzugt C₂-C₈- Alkenyl, besonders bevorzugt C₃-C₆-Alkenyl wie Allyl, 1-Methyl- allyl, 1,3-Dimethyl-but-2-enyl, 1-Methyl-but-2-enyl und But-3-enyl,
- unverzweigtes oder verzweigtes C₂-C₁₂-Alkinyl, bevorzugt C₂-C₈- Alkinyl, besonders bevorzugt C₂-C₄-Alkinyl wie Ethinyl, Prop-1- inyl, Prop-2-inyl, 1-Methyl-prop-2-inyl, But-2-inyl und But-3-inyl,
- unverzweigtes oder verzweigtes C₂-C₁₂-Halogenalkyl, bevorzugt C₁-C₄-Halogenalkyl, besonders bevorzugt C₁-C₄-Fluor- und Chloralkyl wie Trifluormethyl, Difluormethyl, Fluormethyl, Trichlormethyl, Pentafluormethyl, 2,2,2-Trifluorethyl, 2,2,2-Trichlorethyl, 1-Fluormethyl-2-fluor-ethyl, 1-Chlormethyl-2-chlor-ethyl und 2-Fluor-1-methyl-propyl,
- unverzweigtes oder verzweigtes C₂-C₁₂-Halogenalkenyl, bevorzugt C₂-C₄-Halogenalkenyl, besonders bevorzugt C₂-C₄-Fluor- und Chloralkenyl wie 1,2,2-Trifluorethenyl, 1,2,2-Trichlorethenyl, 3,3-Difluorprop-2-enyl und 3,3-Dichlorprop-2-enyl,
- unverzweigtes oder verzweigtes C₂-C₁₂-Halogenalkinyl, bevorzugt C₂-C₄-Halogenalkinyl, besonders bevorzugt C₂-C₄-Fluor- und Chloralkinyl wie Fluorethinyl, Chlorethinyl, 3-Fluorprop-2-inyl und 3-Chlorprop-2-inyl,
- unverzweigtes oder verzweigtes C₃-C₁₂-Alkoxyalkyl, bevorzugt C₃-C₉-Alkoxyalkyl, besonders bevorzugt C₁-C₄-alkoxysubstituierte C₁-C₅-Alkoxyalkyl wie beispielsweise 2-Methoxyethyl, 2-Methoxypropyl, 3-Methoxyprop-2-yl, 3-Methoxybutyl, 4-Methoxybut-2-yl, 4-Methoxybut-3-yl, 5-Methoxypent-3-yl, 2-Ethoxyethyl, 2-Ethoxypropyl, 3-Ethoxypropyl, 3-Ethoxybutyl, 3-Ethoxybut-2-yl, 5-Ethoxypent-2-yl, 2-Propoxyethyl, 2-Propoxypropyl, 3-Propoxybutyl, Butoxymethyl oder 2-Butoxyprop-2-yl,
- C₃-C₈-Cycloalkyl, bevorzugt für C₃-C₆-Cycloalkyl, wie Cyclopropyl, Cyclobutyl, Cyclopentyl und Cyclohexyl,
- C₄-C₁₂-Cycloalkyl-alkyl, bevorzugt C₄-C₈-Cycloalkyl-alkyl, z. B. C₃-C₆-Cycloalkyl substituiertes C₁- oder C₂-Alkyl wie Cyclopropyl- methyl, Cyclopropyl-ethyl, Cyclobutyl-methyl, Cyclopentyl- methyl, Cyclohexyl-methyl und Cyclohexyl-ethyl,
- C₃-C₈-Halogencycloalkyl, bevorzugt C₃-C₆-Halogencycloalkyl, besonders bevorzugt C₃-C₆-Fluor- und Chlorcycloalkyl wie 2,2-Difluorcyclopropyl oder 2,2-Dichlorcyclopropyl,
- C₄-C₁₂-Cycloalkyl-halogenalkyl, bevorzugt C₄-C₈-Cycloalkyl- halogenalkyl, besonders bevorzugt C₄-C₈-Cycloalkyl-fluor- oder -chloralkyl wie 2-Cyclopropyl-2-chlorethyl und 2-Cyclopropyl- 1,1-difluorethyl,
- C₄-C₁₂-Halogencycloalkyl-halogenalkyl, bevorzugt C₄-C₈-Halogencycloalkyl- halogenalkyl, besonders bevorzugt C₄-C₈-Fluor- und Chlorcycloalkyl-fluor- und -chloralkyl wie 2,2-Dichlorcyclopropyl- 2-chlorethyl,
R² - bevorzugt Wasserstoff,
- C₁-C₄-Alkyl wie Methyl, Ethyl, Propyl, Isopropyl oder Butyl, besonders bevorzugt Methyl,
X - O, S oder SO₂, bevorzugt O und S, besonders bevorzugt O,
Z - Wasserstoff, Halogen, bevorzugt Fluor, Chlor und Brom, besonders bevorzugt Fluor und Chlor,
- C₁-C₄-Alkyl wie Methyl, Ethyl, Propyl, Isopropyl, Butyl, besonders bevorzugt Methyl und Ethyl,
Q - ein gegebenenfalls substituierter 5-Ring-Heteroaromat mit 1 bis 4, insbesondere 1 und 2 Heteroatomen wie Stickstoff, Schwefel oder Sauerstoff, bevorzugt Thiophen-2-yl, Thiophen-3-yl, Thiazol- 5-yl, Thiazol-4-yl, Thiazol-2-yl, Oxazol-5-yl, Oxazol-4-yl, Oxazol-2-yl, Imidazol-5-yl, Imidazol-4-yl, Imidazol-2-yl, Isothiazol- 5-yl, Isothiazol-3-yl, Pyrazol-3-yl, Pyrazol-4-yl, Pyrazol-5-yl, Isoxazol-5-yl, Isoxazol-3-yl, 1,3,4-Thiadiazol-2- yl, 1,3,4-Oxadiazol-2-yl, 1,2,4-Oxadiazol-3-yl, 1,3,4-Triazol-2- yl, 1,2,4-Thiadiazol-3-yl, besonders bevorzugt Thiophen-2-yl, Thiophen-3-yl, Thiazol-4-yl, Imidazol-5-yl, Pyrazol-3-yl, 1,3,4-Thiadiazol-2-yl, 1,3,4-Oxadiazol-2-yl, 1,2,4-Oxadiazol-3- yl, Isoxazol-5-yl und Isoxazol-3-yl.The individual substituents in formula I have the following meanings:
R¹ - unbranched or branched C₁-C₁₂ alkyl, preferably C₁-C₈ alkyl, particularly preferably branched C₃-C₈ alkyl, such as isopropyl, isobutyl, sec-butyl, tert-butyl, isopentyl, 1-methyl-butyl, Isohexyl, 1-methylpentyl, isoheptyl, 1-methylhexyl, 1-methylheptyl, 1,3-dimethylbutyl, 1,2-dimethylbutyl, 3-methylpentyl, 4-methylbutyl, 1-ethyl-propyl and 1-ethyl-butyl,
- Unbranched or branched C₂-C₁₂ alkenyl, preferably C₂-C₈ alkenyl, particularly preferably C₃-C₆ alkenyl such as allyl, 1-methyl-allyl, 1,3-dimethyl-but-2-enyl, 1-methyl-but -2-enyl and but-3-enyl,
- Unbranched or branched C₂-C₁₂-alkynyl, preferably C₂-C₈-alkynyl, particularly preferably C₂-C₄-alkynyl such as ethynyl, prop-1-ynyl, prop-2-ynyl, 1-methyl-prop-2-ynyl, but -2-inyl and but-3-ynyl,
- Unbranched or branched C₂-C₁₂-haloalkyl, preferably C₁-C₄-haloalkyl, particularly preferably C₁-C₄-fluoro and chloroalkyl such as trifluoromethyl, difluoromethyl, fluoromethyl, trichloromethyl, pentafluoromethyl, 2,2,2-trifluoroethyl, 2,2, 2-trichloroethyl, 1-fluoromethyl-2-fluoro-ethyl, 1-chloromethyl-2-chloro-ethyl and 2-fluoro-1-methyl-propyl,
- Unbranched or branched C₂-C₁₂-haloalkenyl, preferably C₂-C₄-haloalkenyl, particularly preferably C₂-C₄-fluoro and chloroalkenyl such as 1,2,2-trifluoroethenyl, 1,2,2-trichloroethenyl, 3,3-difluoroprop- 2-enyl and 3,3-dichloroprop-2-enyl,
- Unbranched or branched C₂-C₁₂-haloalkynyl, preferably C₂-C₄-haloalkynyl, particularly preferably C₂-C₄-fluoro and chloroalkynyl such as fluoroethynyl, chloroethynyl, 3-fluoroprop-2-ynyl and 3-chloroprop-2-ynyl,
- Unbranched or branched C₃-C₁₂-alkoxyalkyl, preferably C₃-C₉-alkoxyalkyl, particularly preferably C₁-C₄-alkoxy-substituted C₁-C₅-alkoxyalkyl such as 2-methoxyethyl, 2-methoxypropyl, 3-methoxyprop-2-yl, 3-methoxybutyl , 4-methoxybut-2-yl, 4-methoxybut-3-yl, 5-methoxypent-3-yl, 2-ethoxyethyl, 2-ethoxypropyl, 3-ethoxypropyl, 3-ethoxybutyl, 3-ethoxybut-2-yl, 5 -Ethoxypent-2-yl, 2-propoxyethyl, 2-propoxypropyl, 3-propoxybutyl, butoxymethyl or 2-butoxyprop-2-yl,
- C₃-C₈-cycloalkyl, preferably for C₃-C₆-cycloalkyl, such as cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl,
- C₄-C₁₂-cycloalkyl-alkyl, preferably C₄-C₈-cycloalkyl-alkyl, e.g. B. C₃-C₆-cycloalkyl substituted C₁- or C₂-alkyl such as cyclopropyl-methyl, cyclopropyl-ethyl, cyclobutyl-methyl, cyclopentyl-methyl, cyclohexyl-methyl and cyclohexyl-ethyl,
- C₃-C₈-halocycloalkyl, preferably C₃-C₆-halocycloalkyl, particularly preferably C₃-C₆-fluoro and chlorocycloalkyl such as 2,2-difluorocyclopropyl or 2,2-dichlorocyclopropyl,
- C₄-C₁₂-cycloalkyl-haloalkyl, preferably C₄-C₈-cycloalkyl-haloalkyl, particularly preferably C₄-C₈-cycloalkyl-fluoro or -chloroalkyl such as 2-cyclopropyl-2-chloroethyl and 2-cyclopropyl-1,1-difluoroethyl,
- C₄-C₁₂-halocycloalkyl-haloalkyl, preferably C₄-C₈-halocycloalkyl-haloalkyl, particularly preferably C₄-C₈-fluoro and chlorocycloalkyl-fluoro and chloroalkyl such as 2,2-dichlorocyclopropyl-2-chloroethyl,
R² - preferably hydrogen,
- C₁-C₄-alkyl such as methyl, ethyl, propyl, isopropyl or butyl, particularly preferably methyl,
X - O, S or SO₂, preferably O and S, particularly preferably O,
Z - hydrogen, halogen, preferably fluorine, chlorine and bromine, particularly preferably fluorine and chlorine,
- C₁-C₄-alkyl such as methyl, ethyl, propyl, isopropyl, butyl, particularly preferably methyl and ethyl,
Q - an optionally substituted 5-ring heteroaromatic with 1 to 4, in particular 1 and 2, heteroatoms such as nitrogen, sulfur or oxygen, preferably thiophene-2-yl, thiophene-3-yl, thiazol-5-yl, thiazol-4- yl, thiazol-2-yl, oxazol-5-yl, oxazol-4-yl, oxazol-2-yl, imidazol-5-yl, imidazol-4-yl, imidazol-2-yl, isothiazol-5-yl, Isothiazol-3-yl, pyrazol-3-yl, pyrazol-4-yl, pyrazol-5-yl, isoxazol-5-yl, isoxazol-3-yl, 1,3,4-thiadiazol-2-yl, 1, 3,4-oxadiazol-2-yl, 1,2,4-oxadiazol-3-yl, 1,3,4-triazol-2-yl, 1,2,4-thiadiazol-3-yl, particularly preferably thiophene 2-yl, thiophene-3-yl, thiazol-4-yl, imidazol-5-yl, pyrazol-3-yl, 1,3,4-thiadiazol-2-yl, 1,3,4-oxadiazol-2- yl, 1,2,4-oxadiazol-3-yl, isoxazol-5-yl and isoxazol-3-yl.

Der Fünfringhetarylrest kann gegebenenfalls ein- oder mehrfach substituiert sein mit:
- Halogen, bevorzugt Fluor, Chlor und Brom, besonders bevorzugt Chlor und Brom,
- C₁-C₈-Alkyl, bevorzugt C₁-C₄-Alkyl, besonders bevorzugt Methyl, Ethyl, Isopropyl, tert.-Butyl,
- C₂-C₈-Alkenyl, bevorzugt C₂-C₄-Alkenyl, besonders bevorzugt Ethenyl, 1-Methyl-ethenyl, Propenyl, 2-Methyl-propenyl,
- C₁-C₄-Halogenalkyl, bevorzugt mit Fluor oder Chlor substituiertes C₁-C₂-Halogenalkyl, besonders bevorzugt Trifluormethyl, 2,2,2-Trifluoreth- 1-yl,
- C₁-C₈-Alkoxy, bevorzugt C₁-C₃-Alkoxy, besonders bevorzugt Methoxy, Ethoxy, n-Propyloxy und Isopropyloxy,
- C₁-C₈-Alkylthio, bevorzugt C₁-C₃-Alkylthio, besonders bevorzugt Methylthio, Ethylthio, n-Propylthio und Isopropylthio,
- C₂-C₈-Alkoxyalkyl, bevorzugt C₂-C₄-Alkoxyalkyl, besonders bevorzugt Methoxymethyl, 1-Methoxyethyl, 2-Methoxyethyl, 1-Methoxy-propyl,
- C₃-C₈-Cycloalkyl, bevorzugt C₃-C₅-Cycloalkyl wie Cyclopropyl, Cyclobutyl und Cyclopentyl.The five-ring hetaryl radical can optionally be substituted one or more times with:
Halogen, preferably fluorine, chlorine and bromine, particularly preferably chlorine and bromine,
- C₁-C₈-alkyl, preferably C₁-C₄-alkyl, particularly preferably methyl, ethyl, isopropyl, tert-butyl,
- C₂-C₈-alkenyl, preferably C₂-C₄-alkenyl, particularly preferably ethenyl, 1-methyl-ethenyl, propenyl, 2-methyl-propenyl,
- C₁-C₄-haloalkyl, preferably C₁-C₂-haloalkyl substituted with fluorine or chlorine, particularly preferably trifluoromethyl, 2,2,2-trifluoroeth-1-yl,
- C₁-C₈-alkoxy, preferably C₁-C₃-alkoxy, particularly preferably methoxy, ethoxy, n-propyloxy and isopropyloxy,
- C₁-C₈-alkylthio, preferably C₁-C₃-alkylthio, particularly preferably methylthio, ethylthio, n-propylthio and isopropylthio,
- C₂-C₈-alkoxyalkyl, preferably C₂-C₄-alkoxyalkyl, particularly preferably methoxymethyl, 1-methoxyethyl, 2-methoxyethyl, 1-methoxypropyl,
- C₃-C₈-cycloalkyl, preferably C₃-C₅-cycloalkyl such as cyclopropyl, cyclobutyl and cyclopentyl.

Die erfindungsgemäßen Verbindungen I können ein oder mehrere Asymmetriezentren im Substituenten R¹ enthalten. Die vorliegende Erfindung schließt alle möglichen Stereoisomeren wie Diastereomeren, Enantiomeren sowie Diastereomeren- und Enantiomerengemische ein. Bei den in den Beispielen angegebenen Verbindungen handelt es sich um das jeweilige racemische Gemisch.The compounds I according to the invention can have one or more centers of asymmetry contained in the substituent R¹. The present invention includes all possible stereoisomers such as diastereomers, enantiomers and  Mixtures of diastereomers and enantiomers. In the case of the examples specified compounds are the respective racemic Mixture.

Die phenoxyalkylsubstituierten Heteroderivate der allgemeinen Formel I sind geeignet, Schädlinge aus der Klasse der Insekten, Spinnentiere und Nematoden wirksam zu bekämpfen. Sie können im Pflanzenschutz sowie auf dem Hygiene-, Vorratsschutz- und Veterinärsektor als Schädlingsbekämpfungsmittel eingesetzt werden.The phenoxyalkyl-substituted hetero derivatives of the general formula I are suitable from the class of insects, arachnids and Combat nematodes effectively. You can in crop protection as well as on the Hygiene, storage protection and veterinary sector as pesticides be used.

Zu den schädlichen Insekten gehören
aus der Ordnung der Schmetterlinge (Lepidoptera) beispielsweise Plutella maculipennis (Kohlschabe), Leucoptera coffeella (Kaffeemotte), Hyponomeuta malinellus (Apfelbaumgespinstmotte), Argyresthia conjugella (Apfelmotte), Sitotroga cerealella (Getreidemotte), Phthorimaea operculella (Kartoffelmotte), Capua reticulana (Apfelschalenwickler), Sparganothis pilleriana (Springwurm), Cacoecia murinana (Tannentriebwickler), Tortix viridana (Eichenwickler), Clysia ambiguella (Heu- und Sauerwurm), Evetria buoliana (Kieferntriebwickler), Polychrosis botrana (Bekreuzter Traubenwickler), Cydia pomonella (Obstmade), Laspeyresia molesta (Pfirsichtriebbohrer), Laspeyresia funebrana (Pflaumenwickler), Ostrinia nubilalis (Maiszünsler), Loxostege sticticalis (Rübenzünsler), Ephestia kuehniella (Mehlmotte), Chilo suppressalis (Reisstengelbohrer), Galleria mellonella (Wachsmotte), Malacosoma neustria (Ringelspinner), Dendrolimus pini (Kiefernspinner) Thaumatopoea ptiyocampa (Pinienprozessionsspinner), Phalera bucephala (Mondfleck), Cheimatobia brumata (Kleiner Frostspanner), Hibernia defoliaria (Großer Frostspanner), Bupalus piniarius (Kiefernspanner), Hyphantria cunea (Weißer Bärenspinner), Agrotis segetum (Wintersaateule), Agrotis ypsilon (Ypsiloneule), Barathra brassicae (Kohleule), Cirphis unipuncta (Heerwurm), Prodenia litura (Baumwollraupe), Laphygma exigua (Rüben-Heerwurm), Panolis flammea (Floreule), Earias insulana (Baumwollkapselwurm), Plusia gamma (Gammaeule), Alabama argillacea (Baumwollblattwurm), Lymantria dispar (Schwammspinner), Lymantria monacha (Nonne), Pieris brassicae (Kohlweißling), Aporia crataegi (Baumweißling);
aus der Ordnung der Käfer (Coleoptera) beispielsweise Blitophaga undata (Schwarzer Rübenaaskäfer), Melanotus communis (Drahtwurm), Limonius californicus (Drahtwurm), Agriotes lineatus (Saatschnellkäfer), Agriotes obscurus (Humusschnellkäfer), Agrilus sinuatus (Birnbaum-Prachtkäfer), Meligethes aeneus (Rapsglanzkäfer), Atomaria linearis (Moosknopfkäfer), Epilachna varivestis (Mexikanischer Bohnenkäfer), Phyllopertha horticola (Junikäfer), Popillia japonica (Japankäfer), Melolontha melolontha (Feldmaikäfer), Melolontha hippocastani (Waldmaikäfer), Amphimallus solstitialis (Brachkäfer), Crioceris asparagi (Spargelhähnchen), Lema melanopus (Getreidehähnchen), Leptinotarsa decemlineata (Kartoffelkäfer), Phaedon cochleariae (Meerrettich-Blattkäfer), Phyllotreta nemorum (Kohlerdfloh), Chaetocnema tibialis (Rübenflohkäfer), Phylloides chrysocephala (Raps-Flohkäfer), Diabrotica 12-punctata (Südlicher Maiswurzelwurm), Cassida nebulosa (Nebliger Schildkäfer), Bruchus lentis (Linsenkäfer), Bruchus rufimanus (Pferdebohnenkäfer), Bruchus pisorum (Erbsenkäfer), Sitona lineatus (Liniierter Blattrandkäfer), Orthiorrhynchus sulcatus (Gefurchter Lappenrüßler), Otiorrhynchus ovatus (Erdbeerwurzelrüßler), Hylobies abietis (Großer Brauner Rüsselkäfer), Byctiscus betulae (Rebenstecher), Anthonomus pomorum (Apfelblütenstecher), Anthonomus grandis (Kapselkäfer), Ceuthorrhynchus assimilis (Kohlschotenrüßler), Ceuthorrynchus napi (Großer Kohltriebrüßler), Sitophilus granaria (Kornkäfer), Anisandrus dispar (Ungleicher Holzborkenkäfer), Ips typographus (Buchdrucker), Blastophagus piniperda (Gefurchter Waldgärtner);
aus der Ordnung der Zweiflügler (Diptera) beispielsweise Lycoria pectoralis, Mayetiola destructor (Hessenfliege), Basineura brassicae (Kohlschoten-Gallmücke), Contarinia tritici (Gelbe Weizen-Gallmücke), Haplodiplosis equestris (Sattelmücke), Tipula paludosa (Wiesenschnake), Tipula oleracea (Kohlschnake), Dacus cucurbitae (Melonenfliege), Dacus oleae (Olivenfliege), Ceratitis capitata (Mittelmeerfruchtfliege), Rhagoletis cerasi (Kirschfruchtfliege), Rhagoletis pomonella (Apfelmade), Anastrepha ludens (Mexikanische Fruchtfliege), Oscinella frit (Fritfliege), Phorbia coarctata (Brachfliege), Phorbia antiqua (Zwiebelfliege), Phorbia brassicae (Kleine Kohlfliege), Pegomya hysocyami (Rübenfliege), Anopheles maculipennis, Culex pipiens, Aedes aegypti (Gelbfiebermücke), Aedes vexans, Tabanus bovinus (Rinderbremse), Tipula paludosa (Wiesenschnake), Musca domestica (Stubenfliege), Fannia canicularis (Kleine Stubenfliege), Muscina stabulans, Glossina morsitans (Tsetse-Fliege), Oestrus ovis, Chrysomya macellaria, Chrysomya hominivorax, Lucilia cuprina, Lucilia sericata, Hypoderma lineata;
aus der Ordnung der Hautflügler (Hymenoptera) beispielsweise Athalia rosa (Rübenblattwespe), Hoplocampa minuta (Pflaumensägewespe), Monomorium pharaonis (Pharaoameise), Solenopsis geminata (Feuerameise), Atta sexdens (Blattscheiderameise);
aus der Ordnung der Wanzen (Heteroptera) beispielsweise Nezara viridula (Grüne Reiswanze), Eurygaster integriceps (Asiatische Getreidewanze), Blissus leucopterus (Chinch bug), Dysdercus cingulatus (Kapok-Wanze), Dysdercus intermedius (Baumwollwanze), Piesma quadrata (Rübenwanze), Lygus pratensis (Gemeine Wiesenwanze);
aus der Ordnung der Pflanzensauger (Homoptera) beispielsweise Perkinsiella saccharicida (Zuckerrohrzikade), Nilaparvata lugens (Braune Zikade), Empoasca fabae (Kartoffelzikade), Psylla mali (Apfelblattsauger), Psylla piri (Birnblattsauger), Trialeurodes vaporariorum (Weiße Fliege), Aphis fabae (Schwarze Bohnenlaus), Aphis pomi (Grüne Apfellaus), Aphis sambuci (Holunderblattlaus), Aphidula nasturtii (Kreuzdornblattlaus), Cerosipha gossypii (Gurkenblattlaus), Sappaphis mali (Rosige Apfellaus), Sappaphis mala (Mehlige Birnblattlaus), Dyasphis radicola (Mehlige Apfelfaltenlaus), Brachycaudus cardui (Große Pflaumenblattlaus), Brevicoryne brassicae (Kohlblattlaus), Phorodon humuli (Hopfenblattlaus), Rhopalomyzus ascalonicus (Zwiebellaus), Myzodes persicae (Grüne Pfirsichlaus), Myzus cerasi (Schwarze Sauerkirschenlaus), Dysaulacorthum pseudosolani (Gefleckte Kartoffellaus), Acyrthosiphon onobrychis (Grüne Erbsenlaus), Macrosiphon rosae (Große Rosenblattlaus), Megoura viciae (Wickenlaus), Schizoneura lanuginosa (Birnenblattlaus), Pemphigus bursarius (Salatwurzellaus), Dreyfusia nordmannianae (Tannentrieblaus), Dreyfusia piceae (Weißtannenstammlaus), Adelges laricis (Rote Fichtengallenlaus), Viteus vitifolii (Reblaus);
aus der Gattung der Termiten (Isoptera) beispielsweise Reticulitermes lucifugus, Calotermes flavicollis, Leucotermes flavipes, Termes natalensis;
aus der Ordnung der Geradflügler (Orthoptera) beispielsweise Forficula auricularia (Gemeiner Ohrwurm), Acheta domestica (Heimchen), Gryllotalpa gryllotalpa (Maulwurfsgrille), Tachycines asynamorus (Gewächshausschrecke), Locusta migratoria (Wanderheuschrecke), Stauronotus maroccanus (Marokkanische Wanderheuschrecke), Schistocerca peregrina (Wanderheuschrecke), Nomadacris septemfasciata (Wanderheuschrecke), Melanoplus spretus (Felsengebirgsheuschrecke), Melanoplus femur-rubrum (Rotbeinige Heuschrecke), Blatta orientalis (Küchenschabe), Blattella germanica (Deutsche Schabe), Periplaneta americana (Amerikanische Schabe), Blabera gigantes (Riesenschabe).Harmful insects include
from the order of the butterflies (Lepidoptera), for example Plutella maculipennis (cabbage cockroach), Leucoptera coffeella (coffee moth), Hyponomeuta malinellus (apple tree spider moth), Argyresthia conjugella (apple moth), Sitotroga cerealella (cereal moth), Phthorimaallerotteulcanaella (potato mousse) opera (Capha , Sparganothis pilleriana (springworm), Cacoecia murinana (pine shoots), Tortix viridana (oak rolls), Clysia ambiguella (hay and sour worms), Evetria buoliana (pine shoots), Polychrosis botrana (crossed grape rolls), Cydia pomonta (Obstmade Peach shoot borer), Laspeyresia funebrana (plum wrapper), Ostrinia nubilalis (corn borer), Loxostege sticticalis (beet borer), Ephestia kuehniella (flour moth), Chilo suppressalis (rice stalk borer), Galleria melloninneria, Malos (ring moth spider), Malo (spelled mole spelled), (ring moth spider), Malo (spelled moles) spider Thaumatopoea ptiyocampa (pine processionary moth), P halera bucephala (moon spot), Cheimatobia brumata (little frost tree), Hibernia defoliaria (big frost tree), Bupalus piniarius (pine tree tree), Hyphantria cunea (white bear spinner), Agrotis segetum (winter seed owl), Agrotis ypsuleulee (Ypsatoneoneulee) (Ypsatoneoneuleule) (barley charcoal) , Cirphis unipuncta (army worm), Prodenia litura (cotton caterpillar), Laphygma exigua (beet armyworm), Panolis flammea (floridae), Earias insulana (cotton capsule worm), Plusia gamma (gammaeule), Alabama argillacea (cotton leaf worm) dis, Lymantrammspurmia dis, Lyman , Lymantria monacha (nun), Pieris brassicae (white cabbage), Aporia crataegi (white tree);
from the order of the beetles (Coleoptera), for example, Blitophaga undata (black beet beetle), Melanotus communis (wireworm), Limonius californicus (wireworm), Agriotes lineatus (seed snap beetle), Agriotes obscurus (humus snap beetle), Agrilus sinusatus (Birnbaum) (Rapeseed beetle), Atomaria linearis (moss button beetle), Epilachna varivestis (Mexican bean beetle), Phyllopertha horticola (June beetle), Popillia japonica (Japan beetle), Melolontha melolontha (Feldmaikäfer), Melolontha (Crimagallusferi) (Melakonella) hippoca Asparagus Chicken), Lema melanopus (Cereal Chicken), Leptinotarsa decemlineata (Colorado Beetle), Phaedon cochleariae (Horseradish Leaf Beetle), Phyllotreta nemorum (Cabbage Flea), Chaetocnema tibialis (Beet Flea Beetle), Phyllophalicaotica (Phurzlocephalica), Phylloalphaicaphotus (Maize Flea Beetle), Phylloalphaica Phaedrocephalosaurus, Phylloalphaica (Rhododendron beetle), Phylloalphaica Phaedrocephalosaurus, Phylloa Phaelodica (Phylloxaea), Phylloa Phalodata (Rhododendron beetle), Phylloalphaica (Rhododendronica), Phylloalphaica, Phoelodalphaica ), Cassida nebulosa (misty tortoise beetle), Bruchus lentis (Lentil beetle), Bruchus rufimanus (horse bean beetle), Bruchus pisorum (pea beetle), Sitona lineatus (lined leaf beetle), Orthiorrhynchus sulcatus (furrowed Lappelweeder), Otiorrhynchus ovatus (strawberry root, Rotteleberriesbenis), betel beetrootenzisferferisisferferisisferferisisferferisisferferisisferferisisferyliselferisisferferisisferferiseberriesebisiesferlisiesferlisiesferlisiesferlisiesferlisiesferlisiesferlisiesferlisiesferlisiesferlisiesferlisiesferlisiesferlisiesferlisiesferlisiesferlisiesferlisiesferlisiesferlisiesferlisiesferlisiesferlisiesferlisiesferlisiesferlisbotti Anthonomus pomorum (apple blossom engraver), Anthonomus grandis (capsule beetle), Ceuthorrhynchus assimilis (cabbage weevil), Ceuthorrynchus napi (large cabbage weevil), Sitophilus granaria (grain beetle), Anisandrus dispar (uneven woodbark beetle) ;
from the order of the two-winged species (Diptera), for example Lycoria pectoralis, Mayetiola destructor (Hessian fly), Basineura brassicae (cabbage gall gnat), Contarinia tritici (yellow wheat gall mosquito), Haplodiplosis equestris (saddle gnat), Tipula paludosa (meadow snake), Tipula Cabbage schnapps), Dacus cucurbitae (melon fly), Dacus oleae (olive fly), Ceratitis capitata (Mediterranean fruit fly), Rhagoletis cerasi (cherry fruit fly), Rhagoletis pomonella (apple maggot), Anastrepha ludens (Mexican fruit fly), Oscitachella fritta ), Phorbia antiqua (onion fly), Phorbia brassicae (small cabbage fly), Pegomya hysocyami (beet fly), Anopheles maculipennis, Culex pipiens, Aedes aegypti (yellow fever mosquito), Aedes vexans, Tabanus bovinus (cattle brake), Mushroom domestica), Tipula palakeosa (Housefly), Fannia canicularis (small housefly), Muscina stabulans, Glossina morsitans (Tsetse fly), oestrus ovis , Chrysomya macellaria, Chrysomya hominivorax, Lucilia cuprina, Lucilia sericata, Hypoderma lineata;
from the order of the hymenoptera (Hymenoptera), for example Athalia rosa (beet sawfly), Hoplocampa minuta (plum saw wasp), Monomorium pharaonis (pharaoh ant), Solenopsis geminata (fire ant), Atta sexdens (leaf sheath ant);
from the order of the bugs (Heteroptera), for example Nezara viridula (green rice bug), Eurygaster integriceps (Asian grain bug), Blissus leucopterus (Chinch bug), Dysdercus cingulatus (Kapok bug), Dysdercus intermedius (cotton bug), Piesma quadrata (beet bug), Lygus pratensis (common meadow bug);
from the order of the plant suckers (Homoptera), for example Perkinsiella saccharicida (sugar cane leafhopper), Nilaparvata lugens (brown leafhopper), Empoasca fabae (potato leafhopper), Psylla mali (apple leaf suction device), Psylla piri (pear leaf suction device), Trialeuris fumeariorum (Trialeuris fumeariorum) (Trialeuris vaporie) Black Bean Louse), Aphis pomi (Green Apple Lice), Aphis sambuci (Elder Aphid), Aphidula nasturtii (Buckthorn Aphid), Cerosipha gossypii (Cucumber Aphid), Sappaphis mali (Rosy Apple Aphid), Sappaphis mala (Mealy Pear Louse Aphid), Dypfalta Aphid Brachycaudus cardui (Great Plum Aphid), Brevicoryne brassicae (Cabbage Aphid), Phorodon humuli (Hop Aphid), Rhopalomyzus ascalonicus (Onion Louse), Myzodes persicae (Green Peach Louse), Myzus cerasi (Black Sour Cherry Lice), Dysaulacorthum Pseudosrryonis (Pseudosrellus oni), Pseudosrellus oni (Pseudosrellus) Pea Louse), Macrosiphon rosae (Large Rose Aphid), Megoura viciae (Wickenlaus) , Schizoneura lanuginosa (pear aphid), Pemphigus bursarius (lettuce root louse), Dreyfusia nordmannianae (fir tree louse), Dreyfusia piceae (silver fir tree louse), Adelges laricis (red spruce gall louse), Viteus vitifolii (phylloxera);
from the genus termites (Isoptera), for example Reticulitermes lucifugus, Calotermes flavicollis, Leucotermes flavipes, Termes natalensis;
from the order of the straight winged wing (Orthoptera), for example, Forficula auricularia (common earwig), Acheta domestica (crickets), Gryllotalpa gryllotalpa (mole cricket), Tachycines asynamorus (greenhouse insect), Locusta migratoria (mantis grasshopper), Stauronotkan maroccanus peregrine (Moroccan migrant) Grasshopper), Nomadacris septemfasciata (grasshopper), Melanoplus spretus (rock grasshopper), Melanoplus femur-rubrum (red-legged grasshopper), Blatta orientalis (cockroach), Blattella germanica (German cockroach), Periplaneta americana (American cockroach).

Zur Klasse der Arachnoidea gehören Spinntentiere (Acarina), beispielsweise Ixodes ricinus (Holzbock), Ornithodorus moubata, Amblyomma americanum, Dermacentor silvarum, Boophilus microplus, Tetranychus telarius, Tetranychus pacificus, Paratetranychus pilosus, Bryobia praetiosa. The arachnoid class includes arachnids (Acarina), for example Ixodes ricinus (woodbuck), Ornithodorus moubata, Amblyomma americanum, Dermacentor silvarum, Boophilus microplus, Tetranychus telarius, Tetranychus pacificus, Paratetranychus pilosus, Bryobia praetiosa.  

Zur Klasse der Nematoden zählen beispielsweise Wurzelgallennematoden, z. B. Meloidogyne incognita, Meloidogyne hapla, Meloidogyne javanica, Zysten bildende Nematoden, z. B. Globodera rostochiensis, Heterodera schacutii, Heterodera avenae, Heterodera glycinae, Heterodera triflolii, Stock- und Blattälchen, z. B. Ditylenchus dipsaci, Ditylenchus destructor, Pratylenchus neglectus, Pratylenchus penetrans, Paratylenchus goodeyi, Paratylenchus curvitatus sowie Tylenchorhynchus dubius, Tylenchorhynchus claytoni, Rotylenchus robustus, Heliocotylenchus multicinctus, Radopholus similis, Belonolaimus longicaudatus, Longidorus elongatus, Trichodorus primitivus.The class of nematodes includes, for example, root gall nematodes, e.g. B. Meloidogyne incognita, Meloidogyne hapla, Meloidogyne javanica, cysts forming nematodes, e.g. B. Globodera rostochiensis, Heterodera schacutii, Heterodera avenae, Heterodera glycinae, Heterodera triflolii, stick and Leaf flakes, e.g. B. Ditylenchus dipsaci, Ditylenchus destructor, Pratylenchus neglectus, Pratylenchus penetrans, Paratylenchus goodeyi, Paratylenchus curvitatus and Tylenchorhynchus dubius, Tylenchorhynchus claytoni, Rotylenchus robustus, Heliocotylenchus multicinctus, Radopholus similis, Belonolaimus longicaudatus, Longidorus elongatus, Trichodorus primitive.

Die Wirkstoffe können als solche in Form ihrer Formulierungen oder den daraus bereiteten Anwendungsformen, z. B. in Form von direkt versprühbaren Lösungen, Pulvern, Suspensionen oder Dispersionen, Emulsionen, Öldispersionen, Pasten, Stäubemitteln, Streumitteln, Granulaten durch Versprühen, Vernebeln, Verstäuben, Verstreuen oder Gießen angewendet werden. Die Anwendungsformen richten sich ganz nach den Verwendungszwecken; sie sollten in jedem Fall möglichst die feinste Verteilung der erfindungsgemäßen Wirkstoffe gewährleisten.The active ingredients can be used as such in the form of their formulations or use forms prepared from it, e.g. B. in the form of directly sprayable Solutions, powders, suspensions or dispersions, emulsions, Oil dispersions, pastes, dusts, spreading agents, granules Spraying, atomizing, dusting, scattering or pouring applied will. The application forms depend entirely on the purposes; in any case, they should have the finest possible distribution of the Ensure active ingredients according to the invention.

Zur Herstellung von direkt versprühbaren Lösungen, Emulsionen, Pasten oder Öldispersionen kommen Mineralölfraktionen von mittlerem bis hohem Siedepunkt, wie Kerosin oder Dieselöl, ferner Kohlenteeröle sowie Öle pflanzlichen oder tierischen Ursprungs, aliphatische, cyclische und aromatische Kohlenwasserstoffe, z. B. Benzol, Toluol, Xylol, Paraffin, Tetrahydronaphthalin, alkylierte Naphthaline oder deren Derivate, Methanol, Ethanol, Propanol, Butanol, Chloroform, Tetrachlorkohlenstoff, Cyclohexanol, Cyclohexanon, Chlorbenzol, Isophoron, stark polare Lösungsmittel, z. B. Dimethylformamid, Dimethylsulfoxid, N-Methylpyrrolidon, Wasser, in Betracht.For the production of directly sprayable solutions, emulsions, pastes or oil dispersions come mineral oil fractions from medium to high Boiling point, such as kerosene or diesel oil, as well as coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g. B. benzene, toluene, xylene, paraffin, Tetrahydronaphthalene, alkylated naphthalenes or their derivatives, Methanol, ethanol, propanol, butanol, chloroform, carbon tetrachloride, Cyclohexanol, cyclohexanone, chlorobenzene, isophorone, strongly polar solvents, e.g. B. dimethylformamide, dimethyl sulfoxide, N-methylpyrrolidone, Water.

Wäßrige Anwendungsformen können als Emulsionskonzentrate, Pasten oder netzbare Pulver (Spritzpulver, Öldispersionen) durch Zusatz von Wasser bereitet werden. Zur Herstellung von Emulsionen, Pasten oder Öldispersionen können die Substanzen als solche oder in einem Öl oder Lösungsmittel gelöst, mittels Netz-, Haft-, Dispergier- oder Emulgiermittel in Wasser homogenisiert werden. Es können aber auch aus wirksamer Substanz Netz-, Haft-, Dispergier- oder Emulgiermittel und eventuell Lösungsmittel oder Öl bestehende Konzentrate hergestellt werden, die zur Verdünnung mit Wasser geeignet sind. Aqueous application forms can be used as emulsion concentrates, pastes or wettable powders (wettable powders, oil dispersions) by adding water be prepared. For the production of emulsions, pastes or Oil dispersions can be the substances as such or in an oil or Solvent dissolved, using wetting agents, adhesives, dispersants or emulsifiers be homogenized in water. But it can also be more effective Substance wetting, adhesive, dispersing or emulsifying agent and possibly Solvents or oil existing concentrates are produced, which are used for Dilution with water are suitable.  

Als oberflächenaktive Stoffe kommen Alkali-, Erdalkali-, Ammoniumsalze von Ligninsulfonsäure, Naphthalinsulfonsäure, Phenolsulfonsäure, Alkylarylsulfonate, Alkylsulfate, Alkylsulfonate, Alkali- und Erdalkalisalze der Dibutylnaphthalinsulfonsäure, Laurylethersulfat, Fettalkoholsulfate, fettsaure Alkali- und Erdalkali, Salze sulfatierter Hexadecanole, Heptadecanole, Octadecanole, Salze von sulfaltiertem Fettalkoholglykolether, Kondensationsprodukte von sulfoniertem Naphthalin und Naphthalinderivaten mit Formaldehyd, Kondensationsprodukte des Naphthalins bzw. der Naphthalinsulfonsäuren mit Phenol und Formaldehyd, Polyoxyethylenoctylphenolether, ethoxyliertes Isooctylphenol, Octylphenol, Nonylphenon, Alkylphenolpolyglykolether, Tributylphenylpolyglykolether, Alkylarylpolyetheralkohole, Isotridecylalkohol, Fettalkoholethylenoxid-Kondensate, ethoxyliertes Rizinusöl, Polyoxyethylenalkylether, ethoxyliertes Polyoxypropylen, Laurylalkoholpolylglykoletheracetal, Sorbitester, Lignin, Sulfitablaugen und Methylcellulose in Betracht.Alkali, alkaline earth, ammonium salts come from as surface-active substances Ligninsulfonic acid, naphthalenesulfonic acid, phenolsulfonic acid, alkylarylsulfonates, Alkyl sulfates, alkyl sulfonates, alkali and alkaline earth salts Dibutylnaphthalenesulfonic acid, lauryl ether sulfate, fatty alcohol sulfates, fatty acid alkali and alkaline earth, salts of sulfated hexadecanols, heptadecanols, Octadecanols, salts of sulfated fatty alcohol glycol ether, Condensation products of sulfonated naphthalene and naphthalene derivatives with formaldehyde, condensation products of naphthalene or Naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctylphenol, octylphenol, nonylphenone, Alkylphenol polyglycol ether, tributylphenyl polyglycol ether, alkylaryl polyether alcohols, Isotridecyl alcohol, fatty alcohol ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ether, ethoxylated polyoxypropylene, Lauryl alcohol polyglycol ether acetal, sorbitol ester, lignin, Leaches of sulfite and methyl cellulose into consideration.

Pulver-, Streu- und Stäubemittel können durch Mischen oder gemeinsames Vermahlen der wirksamen Substanzen mit einem festen Trägerstoff hergestellt werden.Powders, materials for spreading and dusts can be mixed or combined Grinding the active substances with a solid carrier getting produced.

Granulate, z. B. Umhüllungs-, Imprägnierungs- und Homogengranulate, können durch Bindung der Wirkstoffe an feste Trägerstoffe hergestellt werden. Feste Trägerstoffe sind z. B. Mineralerden, wie Silicagel, Kieselsäuren, Kieselgele, Silikate, Talkum, Kaolin, Attaclay, Kalkstein, Kalk, Kreide, Bolus, Löß, Ton, Dolomit, Diatomeenerde, Calcium- und Magnesiumsulfat, Magnesiumoxid, gemahlene Kunststoffe, Düngemittel, wie z. B. Ammoniumsulfat, Ammoniumphosphat, Ammoniumnitrat, Harnstoffe und pflanzliche Produkte, wie Getreidemehl, Baumrinden-, Holz- und Nußschalenmehl, Cellulosepulver und andere feste Trägerstoffe.Granules, e.g. B. coating, impregnation and homogeneous granules by binding the active ingredients to solid carriers. Solid carriers are e.g. B. mineral earths, such as silica gel, silicas, Silica gels, silicates, talc, kaolin, attaclay, limestone, lime, chalk, Bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, Magnesium oxide, ground plastics, fertilizers such. B. ammonium sulfate, Ammonium phosphate, ammonium nitrate, urea and vegetable Products such as flour, tree bark, wood and nutshell flour, Cellulose powder and other solid carriers.

Die Formulierungen enthalten im allgemeinen zwischen 0,1 und 95 Gew.-% Wirkstoff, vorzugsweise zwischen 0,5 und 90 Gew.-%.The formulations generally contain between 0.1 and 95% by weight Active ingredient, preferably between 0.5 and 90 wt .-%.

Beispiele für Formulierungen sind:Examples of formulations are:

  • I. 5 Gew.-Teile der Verbindung Nr. 1 mit 95 Gew.-Teilen feinteiligem Kaolin innig vermischt. Man erhält auf diese Weise ein Stäubemittel, das 3 Gew.-% des Wirkstoffs enthält.I. 5 parts by weight of compound no. 1 with 95 parts by weight finely divided kaolin mixed intimately. You get this way a dust containing 3% by weight of the active ingredient.
  • II. 30 Gew.-Teile der Verbindung Nr. 10 werden mit einer Mischung aus 92 Gew.-Teilen pulverförmigem Kieselsäuregel und 8 Gew.-Teilen Paraffinöl, das auf die Oberfläche dieses Kieselsäuregels gesprüht wurde, innig vermischt. Man erhält auf diese Weise eine Aufbereitung des Wirkstoffs mit guter Haftfähigkeit. II. 30 parts by weight of compound no. 10 are mixed with 92 parts by weight of powdered silica gel and 8 parts by weight Paraffin oil that is sprayed onto the surface of this silica gel was mixed intimately. You get one in this way Preparation of the active ingredient with good adhesiveness.  
  • III. 10 Gew.-Teile der Verbindung Nr. 69 werden in einer Mischung gelöst, die aus 90 Gew.-Teilen Xylol, 6 Gew.-Teilen des Anlagerungsproduktes von 8 bis 10 Mol Ethylenoxid an 1 Mol Ölsäure- N-monoethanolamid, 2 Gew.-Teilen Calciumsalz der Dodecylbenzolsulfonsäure und 2 Gew.-Teilen des Anlagerungsproduktes von 40 Mol Ethylenoxid an 1 Mol Ricinusöl besteht.III. 10 parts by weight of compound no. 69 are mixed dissolved that from 90 parts by weight of xylene, 6 parts by weight of the adduct from 8 to 10 moles of ethylene oxide to 1 mole of oleic acid N-monoethanolamide, 2 parts by weight of calcium salt of dodecylbenzenesulfonic acid and 2 parts by weight of the adduct of 40 moles There is ethylene oxide in 1 mol of castor oil.
  • IV. 20 Gew.-Teile der Verbindung Nr. 49 werden in einer Mischung gelöst, die aus 60 Gew.-Teilen Cyclohexanon, 30 Gew.-Teilen Isobutanol, 5 Gew.-Teilen des Anlagerungsproduktes von 7 Mol Ethylenoxid an 1 Mol Isooctylphenol und 5 Gew.-Teilen des Anlagerungsproduktes von 40 Mol Ethylenoxid an 1 Mol Ricinusöl besteht.IV. 20 parts by weight of compound no. 49 are mixed dissolved, from 60 parts by weight of cyclohexanone, 30 parts by weight Isobutanol, 5 parts by weight of the adduct of 7 moles Ethylene oxide in 1 mole of isooctylphenol and 5 parts by weight of the Addition product of 40 moles of ethylene oxide with 1 mole of castor oil consists.
  • V. 80 Gew.-Teile der Verbindung Nr. 1 werden mit 3 Gew.-Teilen des Natriumsalzes der Diisobutylnaphthalin-alpha-sulfonsäure, 10 Gew.-Teilen des Natriumsalzes einer Ligninsulfonsäure aus einer Sulfit-Ablauge und 7 Gew.-Teilen pulverförmigem Kieselsäuregel gut vermischt und in einer Hammermühle vermahlen.V. 80 parts by weight of compound no. 1 are mixed with 3 parts by weight of the Sodium salt of diisobutylnaphthalene-alpha-sulfonic acid, 10 parts by weight of the sodium salt of a lignosulfonic acid a sulfite waste liquor and 7 parts by weight of powdered silica gel well mixed and ground in a hammer mill.

Die Wirkstoffkonzentrationen in den anwendungsfertigen Zubereitungen können in größeren Bereichen variiert werden. Im allgemeinen liegen sie zwischen 0,0001 und 10%, vorzugsweise zwischen 0,01 und 1%. Die Wirkstoffe können auch mit gutem Erfolg im Ultra-Low-Volume-Verfahren (ULV) verwendet werden, wobei es möglich ist, Formulierungen mit mehr als 95 Gew.-% Wirkstoff oder sogar den Wirkstoff ohne Zusätze auszubringen.The active ingredient concentrations in the ready-to-use preparations can be varied in larger areas. In general, they lie between 0.0001 and 10%, preferably between 0.01 and 1%. The active ingredients can also with good success in the ultra-low-volume process (ULV) can be used, it being possible to use formulations with more than 95% by weight of active ingredient or even the active ingredient without additives.

Die Aufwandmenge an Wirkstoff beträgt unter Freilandbedingungen 0,001 bis 10, insbesondere 0,1 bis 2, vorzugsweise 0,01 bis 1 kg/ha.The amount of active substance applied is 0.001 to under outdoor conditions 10, in particular 0.1 to 2, preferably 0.01 to 1 kg / ha.

Zu den Wirkstoffen können Öle verschiedenen Typs, Herbizide, Fungizide, andere Schädlingsbekämpfungsmittel, Bakterizide, gegebenenfalls auch erst unmittelbar vor der Anwendung (Tankmix), zugesetzt werden. Diese Mittel können zu den erfindungsgemäßen Mitteln im Gewichtsverhältnis 1 : 10 bis 10 : 1 zugemischt werden.Oils of various types, herbicides, fungicides, other pesticides, bactericides, if necessary first immediately before use (tank mix). This means can to the agents according to the invention in a weight ratio of 1:10 to 10: 1 can be added.

HerstellungsbeispieleManufacturing examples 5-[4-(sec-Butoxy)-phenoxymethyl]-3-methyl-isoxazol5- [4- (sec-butoxy) phenoxymethyl] -3-methyl-isoxazole (Bsp.-Nr. 1 der nachfolgenden Tabelle)(E.g. No. 1 of the following table)

5,0 g 4-sec-Butyloxyphenol werden in 80 ml absolutem Dimethylformamid vorgelegt und mit 4,6 g wasserfreiem Kaliumcarbonat 1 Stunde bei 80°C gerührt. Anschließend tropft man bei dieser Temperatur 3,9 g 5-Chlormethyl- 3-methyl-isoxazol zu und läßt noch 7 Stunden bei 90°C nachrühren. Zur Aufarbeitung wird der Ansatz in 300 ml Eiswasser eingerührt, dreimal mit je 100 ml Methyl-tert.-butylether extrahiert und die organische Phase zweimal mit je 50 ml 2 N Natronlauge und anschließend dreimal mit je 50 ml Wasser gewaschen. Nach Trocknen über Natriumsulfat und Abziehen des Lösungsmittels im Vakuum erhält man 6,6 g 5-[4-(sec-Butyloxy)-phenoxymethyl]- 3-methyl-isoxazol, welches nach Chromatographie über Kieselgel mit Toluol/Essigester = 1/1 ¹H-NMR-spektroskopisch rein als viskoses Öl anfällt.
250-MHz-¹H-NMR in CDCl₃ [ppm] (charakteristische Signale): 1.21 (d); 5.08 (s); 6.15 (s).5.0 g of 4-sec-butyloxyphenol are placed in 80 ml of absolute dimethylformamide and stirred with 4.6 g of anhydrous potassium carbonate at 80 ° C. for 1 hour. Then 3.9 g of 5-chloromethyl-3-methyl-isoxazole are added dropwise at this temperature and the mixture is stirred for a further 7 hours at 90.degree. For working up, the mixture is stirred into 300 ml of ice water, extracted three times with 100 ml of methyl tert-butyl ether and the organic phase is washed twice with 50 ml of 2N sodium hydroxide solution and then three times with 50 ml of water. After drying over sodium sulfate and stripping off the solvent in vacuo, 6.6 g of 5- [4- (sec-butyloxy) phenoxymethyl] - 3-methyl-isoxazole are obtained, which after chromatography on silica gel with toluene / ethyl acetate = 1/1 1 H -NMR-spectroscopically pure as a viscous oil.
250 MHz 1 H NMR in CDCl 3 [ppm] (characteristic signals): 1.21 (d); 5.08 (s); 6.15 (s).

5-[4-(sec-Butylthio)-phenoxymethyl]-3-cyclopropyl-isoxazol5- [4- (sec-Butylthio) phenoxymethyl] -3-cyclopropyl-isoxazole (Bsp.-Nr. 10 der nachfolgenden Tabelle)(E.g. No. 10 of the following table)

0,79 g Natriumhydrid werden unter Stickstoff in 50 ml absolutem Dimethylformamid vorgelegt. Hierzu tropft man bei Raumtemperatur 5,5 g 4-sec- Butyl-thiophenol in 20 ml absolutem Dimethylformamid gelöst zu und rührt anschließend noch 0,5 Stunden bei 60°C nach. Anschließend werden bei dieser Temperatur 5,8 g 5-Chlormethyl-3-cyclopropyl-isoxazol in 20 ml absolutem Dimethylformamid zugetropft und nach beendeter Zugabe noch 3 Stunden bei 90°C nachgerührt. Analoge Aufarbeitung wie im vorangegangenen Beispiel liefert nach Chromatographie über Kieselgel mit Toluol/Essigester = 1/1 7,9 g 5-[4-(sec-Butylthio)-phenoxymethyl]-3- cyclopropyl-isoxazol als hellgelbes Öl.
250-MHz-¹H-NMR in CDCl₃ [ppm] (charakteristische Signale): 1.22 (d); 5.09 (s); 6.01 (s). 0.79 g of sodium hydride are placed under nitrogen in 50 ml of absolute dimethylformamide. 5.5 g of 4-sec-butyl-thiophenol dissolved in 20 ml of absolute dimethylformamide are added dropwise at room temperature and the mixture is then stirred at 60 ° C. for a further 0.5 hour. 5.8 g of 5-chloromethyl-3-cyclopropyl-isoxazole in 20 ml of absolute dimethylformamide are then added dropwise at this temperature and, after the addition has ended, the mixture is stirred at 90 ° C. for a further 3 hours. Working up analogously to that in the previous example gives, after chromatography on silica gel with toluene / ethyl acetate = 1/1, 7.9 g of 5- [4- (sec-butylthio) phenoxymethyl] -3-cyclopropyl-isoxazole as a light yellow oil.
250 MHz 1 H NMR in CDCl 3 [ppm] (characteristic signals): 1.22 (d); 5.09 (s); 6.01 (s).

2-[4-(sec-Butyloxy)-phenoxymethyl]-5-bromthiophen2- [4- (sec-butyloxy) phenoxymethyl] -5-bromothiophene (Bsp.-Nr. 49 der nachfolgenden Tabelle)(E.g. No. 49 of the following table)

6,64 g 4-(sec-Butyloxy)-phenol und 5,52 g Kaliumcarbonat werden in 50 ml trockenem Dimethylformamid 1 Stunde auf 70°C erhitzt. Anschließend tropft man 8,46 g 5-Brom-2-chlormethylthiophen in 20 ml trockenem Dimethylformamid zu. Man rührt 6 Stunden bei 80°C und über Nacht bei Raumtemperatur (ca. 20°C) nach. Zur Aufarbeitung gießt man in 100 ml Eiswasser und extrahiert dreimal mit Essigester und trocknet die organischen Phasen über Magnesiumsulfat. Nach dem Verdampfen des Lösungsmittels wird das Rohprodukt durch Chromatographie an Kieselgel mit n-Hexan/Essigester = 4/1 als Eluent gereinigt. Man erhält 6,3 g 2-[4-(sec-Butyloxy)-phenoxymethyl]- 5-brom-thiophen als farbloses Öl.
250-MHz-¹H-NMR in CDCl₃ [ppm] (charakteristische Signale): 0.99 (t); 1.28 (d); 5.09 (s).6.64 g of 4- (sec-butyloxy) phenol and 5.52 g of potassium carbonate are heated at 70 ° C. for 1 hour in 50 ml of dry dimethylformamide. 8.46 g of 5-bromo-2-chloromethylthiophene in 20 ml of dry dimethylformamide are then added dropwise. The mixture is stirred for 6 hours at 80 ° C and overnight at room temperature (about 20 ° C). For working up, it is poured into 100 ml of ice water and extracted three times with ethyl acetate and the organic phases are dried over magnesium sulfate. After evaporation of the solvent, the crude product is purified by chromatography on silica gel with n-hexane / ethyl acetate = 4/1 as the eluent. 6.3 g of 2- [4- (sec-butyloxy) phenoxymethyl] -5-bromothiophene are obtained as a colorless oil.
250 MHz 1 H NMR in CDCl 3 [ppm] (characteristic signals): 0.99 (t); 1.28 (d); 5.09 (s).

5-[4-(sec-Butyloxy)-phenoxymethyl]-3-cyclopropyl-1,2,4-oxadiazol5- [4- (sec-butyloxy) phenoxymethyl] -3-cyclopropyl-1,2,4-oxadiazole (Bsp.-Nr. 69 der nachfolgenden Tabelle)(E.g. No. 69 in the table below)

5 g 4-(sec-Butyloxy)-phenol und 6,2 g Kaliumcarbonat werden in 50 ml trockenem Dimethylformamid 1 Stunde bei 80°C gerührt. Anschließend werden 4,8 g 5-Chlormethyl-3-cyclopropyl-1,2,4-oxadiazol zu 20 ml trockenem Dimethylformamid zugetropft und 8 Stunden bei 80°C und über Nacht bei Raumtemperatur (ca. 20°C) nachgerührt. Zur Aufarbeitung gießt man in 100 ml Wasser und extrahiert dreimal mit Essigester und trocknet die organischen Phasen über Magnesiumsulfat. Nach dem Verdampfen des Lösungsmittels wird das Rohprodukt durch Chromatographie am Kieselgel mit n-Hexan/Essigester = 4/1 als Eluent gereinigt. Man erhält 6,7 g 5-[4-(sec- Butyloxy)-phenoxymethyl]-3-cyclopropyl-1,2,4-oxydiazol als farbloses Öl.
250-MHz-¹H-NMR in CDCl₃ [ppm] (charakteristische Signale): 1.50-1.82 (m); 2.04-2.18 (m); 5.13 (s). 5 g of 4- (sec-butyloxy) phenol and 6.2 g of potassium carbonate are stirred in 50 ml of dry dimethylformamide at 80 ° C. for 1 hour. 4.8 g of 5-chloromethyl-3-cyclopropyl-1,2,4-oxadiazole are then added dropwise to 20 ml of dry dimethylformamide and the mixture is stirred at 80 ° C. for 8 hours and at room temperature (approx. 20 ° C.) overnight. For working up, it is poured into 100 ml of water and extracted three times with ethyl acetate and the organic phases are dried over magnesium sulfate. After evaporation of the solvent, the crude product is purified by chromatography on silica gel with n-hexane / ethyl acetate = 4/1 as the eluent. 6.7 g of 5- [4- (sec-butyloxy) phenoxymethyl] -3-cyclopropyl-1,2,4-oxydiazole are obtained as a colorless oil.
250 MHz 1 H NMR in CDCl 3 [ppm] (characteristic signals): 1.50-1.82 (m); 2.04-2.18 (m); 5.13 (s).

AnwendungsbeispieleExamples of use

In den folgenden Beispielen wurden die erfindungsgemäßen Verbindungen bzw. sie enthaltende Mittel hinsichtlich ihrer Wirkung auf Schädlinge mit den nachstehenden Verbindungen des Standes der Technik verglichen:In the following examples, the compounds or agents containing them with regard to their action on pests with the the following prior art compounds compared:

Die Reinheit der Vergleichssubstanzen entsprach derjenigen der erfindungsgemäßen Verbindungen und lag bei mindestens 90 bis 95%. Die Konzentrationen, bei denen die untersuchten Verbindungen eine 100%ige Mortalität bzw. Hemmung bewirken, sind die jeweiligen Minimalkonzentrationen. Bei jeder Konzentration werden mindestens zwei Versuche durchgeführt.The purity of the comparison substances corresponded to that of the invention Compounds and was at least 90 to 95%. The Concentrations at which the investigated compounds are 100% The respective minimum concentrations cause mortality or inhibition. At each concentration there will be at least two attempts carried out.

Beispiel AExample A Dysdercus intermedius (Baumwollwanze), ovizide WirkungDysdercus intermedius (cotton bug), ovicidal effect

Stecketiketten wurden am oberen Rand mit Klebestreifenstücken (ca. 0,8 cm) beklebt. 24 Stunden vor Versuchsbeginn wurden die Eier durch Eintauchen in das "Sammelgefäß" an dem Klebestreifenrand befestigt.Plant labels were attached to the upper edge with pieces of adhesive tape (approx. 0.8 cm) pasted. 24 hours before the start of the experiment, the eggs were immersed in the "collecting vessel" attached to the edge of the adhesive tape.

Die Eier wurden für ca. 5 Sekunden in die wäßrige Wirkstoffaufbereitung getaucht, anschließend ließ man auf Filterpapier abtropfen. Dabei sollten die Eier nicht auf das Papier gelegt werden.The eggs were placed in the aqueous active ingredient preparation for about 5 seconds dipped, then allowed to drain on filter paper. It should the eggs are not laid on the paper.

Die zurechtgeschnittenen Etiketten wurden in Plastikpaletten gestellt, Klebstreifen nach oben. Eine halbe mit Wasser durchfeuchtete Watterolle wurde in den Becher gelegt, um Austrocknung zu vermeiden und die Palette mit einer Glasplatte abgedeckt.The cut labels were put in plastic pallets, Adhesive tape facing up. Half a cotton roll soaked in water was placed in the cup to avoid drying out and the pallet covered with a glass plate.

Nach ca. 8 Tagen wurde bonitiert. (Bei der Kontrolle müssen die Larven geschlüpft sein.)After approx. 8 days, ratings were given. (The larvae must be checked hatched.)

Beurteilt wurde die Schlupfhemmung in %. The slip inhibition was assessed in%.  

Bei diesem Versuch wurde mit den Verbindungen 1, 4 und 7 eine Schlupfhemmung von 80% Wirkstoffkonzentration von 400 ppm und darunter erzielt, während die Vergleichsverbindung B bei 1000 ppm keine Schlupfhemmung bewirkte.In this experiment, compounds 1, 4 and 7 inhibited slip of 80% active ingredient concentration of 400 ppm and below achieved, while the comparison compound B at 1000 ppm no slip inhibition caused.

Beispiel BExample B Caenorhabditis elegans (Nematoden), KontaktversuchCaenorhabditis elegans (nematodes), contact attempt

Auf die Oberfläche eines Nährbodens (5 ml in Kunststoffpetrischälchen ⌀ 35 mm, Höhe 10 mm) gab man 0,5 ml der acetonischen Wirkstofflösung. Nach Verdunsten des Acetons infizierte man mit 30 µl E-Coli-Bakterien und 50 µl Nematodensuspension. Nach 48 h ermittelte man die Kontaktwirkung in % Mortalität.On the surface of a culture medium (5 ml in plastic petri dishes ⌀ 35 mm, height 10 mm) were given 0.5 ml of the acetone active ingredient solution. To Evaporation of the acetone was infected with 30 µl E-Coli bacteria and 50 µl Nematode suspension. After 48 hours, the contact effect was determined in % Mortality.

Bei einer Wirkstoffkonzentration von 100 ppm wurde mit den Verbindungen der Beispiele 2, 3, 4, 5 und 49 eine Mortalitätsrate von 100% erzielt, während die Vergleichsmittel B und C bei dieser Konzentration praktisch unwirksam waren, d. h. eine Mortalitätsrate von weniger als 60% aufwiesen.At an active ingredient concentration of 100 ppm with the compounds Examples 2, 3, 4, 5 and 49 achieved a mortality rate of 100%, while comparative agents B and C are practical at this concentration were ineffective, d. H. had a mortality rate of less than 60%.

Claims (5)

1. Phenoxyalkylsubstituierte 5-Ring-Heteroaromaten der Formel I in der
R¹ C₁-C₁₂-Alkyl, C₂-C₁₂-Alkenyl, C₂-C₁₂-Alkinyl, C₁-C₁₂-Halogenalkyl, C₂-C₁₂-Halogenalkenyl, C₂-C₁₂-Halogenalkinyl, C₃-C₁₂- Alkoxyalkyl, C₃-C₈-Cycloalkyl, C₄-C₁₂-Cycloalkyl-alkyl, C₃-C₈- Halogencycloalkyl, C₄-C₁₂-Halogencycloalkyl-alkyl, C₄-C₁₂-Cycloalkyl- halogenalkyl oder C₄-C₁₂-Halogencycloalkyl-halogenalkyl,
R² Wasserstoff oder C₁-C₄-Alkyl,
X O, S oder SO₂,
Z Wasserstoff, Halogen oder C₁-C₄-Alkyl und
Q einen Fünf-Ring-Heteroaromaten, der über ein C-Atom gebunden und gegebenenfalls ein oder mehrfach mit Halogen, C₁-C₈-Alkyl, C₂-C₈-Alkenyl, C₁-C₄-Halogenalkyl, C₁-C₈-Alkoxy, C₁-C₈-Alkylthio, C₂-C₈-Alkoxyalkyl oder C₃-C₁₀-Cycloalkyl substituiert ist, bedeuten.1. Phenoxyalkyl-substituted 5-ring heteroaromatics of the formula I. in the
R¹ C₁-C₁₂-alkyl, C₂-C₁₂-alkenyl, C₂-C₁₂-alkynyl, C₁-C₁₂-haloalkyl, C₂-C₁₂-haloalkenyl, C₂-C₁₂-haloalkynyl, C₃-C₁₂- alkoxyalkyl, C₃-C₈-cycloalkyl, C₄ -C₁₂-cycloalkyl-alkyl, C₃-C₈- halocycloalkyl, C₄-C₁₂-halocycloalkyl-alkyl, C₄-C₁₂-cycloalkyl-haloalkyl or C₄-C₁₂-halocycloalkyl-haloalkyl,
R² is hydrogen or C₁-C₄ alkyl,
XO, S or SO₂,
Z is hydrogen, halogen or C₁-C₄-alkyl and
Q is a five-ring heteroaromatic bonded via a carbon atom and optionally one or more times with halogen, C₁-C₈-alkyl, C₂-C₈-alkenyl, C₁-C₄-haloalkyl, C₁-C₈-alkoxy, C₁-C₈ -Alkylthio, C₂-C₈-alkoxyalkyl or C₃-C₁₀-cycloalkyl is substituted. 2. Verfahren zur Herstellung der phenoxyalkylsubstituierten 5-Ring- Heteroaromaten der Formel I gemäß Anspruch 1, dadurch gekennzeichnet, daß man ein entsprechendes Phenol II mit einem 5-Ring-Heteroaromaten der Formel III in der Y für eine Abgangsgruppe steht, in Gegenwart einer Base oder das Phenolatanion von II direkt mit III umsetzt. 2. A process for the preparation of the phenoxyalkyl-substituted 5-ring heteroaromatics of the formula I according to claim 1, characterized in that a corresponding phenol II with a 5-ring heteroaromatic compound of the formula III in which Y represents a leaving group, in the presence of a base or the phenolate anion of II is reacted directly with III. 3. Schädlingsbekämpfungsmittel, enthaltend einen phenoxyalkylsubstituierten 5-Ring-Heteroaromaten der Formel I gemäß Anspruch 1 neben hierfür üblichen Trägerstoffen.3. Pesticide containing a phenoxyalkyl substituted 5-ring heteroaromatics of the formula I according to claim 1 in addition to the usual carriers. 4. Schädlingsbekämpfungsmittel gemäß Anspruch 3, enthaltend 0,1 bis 95 Gew.-% eines phenoxyalkylsubstituierten 5-Ring-Heteroaromaten der Formel I gemäß Anspruch 1.4. pesticide according to claim 3, containing 0.1 to 95 wt .-% of a phenoxyalkyl-substituted 5-ring heteroaromatic Formula I according to claim 1. 5. Verfahren zur Bekämpfung von Schädlingen, dadurch gekennzeichnet, daß man eine für Schädlinge wirksame Menge eines phenoxyalkylsubstituierten 5-Ring-Heteroaromaten der Formel I gemäß Anspruch 1 auf Schädlinge bzw. deren Lebensraum einwirken läßt.5. A method for controlling pests, characterized in that an effective amount of a phenoxyalkyl substituted for pests 5-ring heteroaromatics of the formula I according to claim 1 Pests or their habitat.
DE19883825822 1988-07-29 1988-07-29 Phenoxyalkyl-substituted 5-membered ring-heteroaromatics, processes for their preparation, and pesticides containing them Withdrawn DE3825822A1 (en)

Priority Applications (10)

Application Number Priority Date Filing Date Title
DE19883825822 DE3825822A1 (en) 1988-07-29 1988-07-29 Phenoxyalkyl-substituted 5-membered ring-heteroaromatics, processes for their preparation, and pesticides containing them
US07/379,956 US5013847A (en) 1988-07-29 1989-07-14 Phenoxyalkyl-substituted heteroaromatics and a method for controlling pests
CA000605747A CA1338938C (en) 1988-07-29 1989-07-14 Phenoxyalkyl-substituted heteroaromatics and a method for controlling pests
ES89113498T ES2063082T3 (en) 1988-07-29 1989-07-22 Phenoxyalkyl substituted aromatics, procedure for obtaining and using them as pesticide agents.
EP89113498A EP0353571B1 (en) 1988-07-29 1989-07-22 Phenoxyalkyl-substituted heteroaromates, process for their preparation and their use as pesticides
DE58908492T DE58908492D1 (en) 1988-07-29 1989-07-22 Phenoxyalkyl-substituted heteroaromatics, process for their preparation and their use as pesticides.
JP1194448A JPH0288559A (en) 1988-07-29 1989-07-28 Phenoxyalkyl substituted heteroaromatic compound, its production and use thereof for controlling harmful insects
KR1019890010783A KR0125577B1 (en) 1988-07-29 1989-07-29 Phenoxyalkyl-substituted heteroaromatic compounds and methods for preparing the same, and pesticides containing the same
US07/658,241 US5212194A (en) 1988-07-29 1991-02-20 Phenoxyalkyl-substituted heteroaromatics and a method for controlling pests
US07/942,387 US5342849A (en) 1988-07-29 1992-09-09 Phenoxyalkyl-substituted heteroaromatics and a method for controlling pests

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