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DE3713337A1 - [(p-Phenoxy)phenoxy]methylisoxazoles - Google Patents

[(p-Phenoxy)phenoxy]methylisoxazoles

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Publication number
DE3713337A1
DE3713337A1 DE19873713337 DE3713337A DE3713337A1 DE 3713337 A1 DE3713337 A1 DE 3713337A1 DE 19873713337 DE19873713337 DE 19873713337 DE 3713337 A DE3713337 A DE 3713337A DE 3713337 A1 DE3713337 A1 DE 3713337A1
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Germany
Prior art keywords
alkyl
phenoxy
methyl
aryl
dimethyl
Prior art date
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Application number
DE19873713337
Other languages
German (de)
Inventor
Hans Dr Theobald
Christoph Dr Kuenast
Peter Dr Hofmeister
Hans-Juergen Dr Neubauer
Thomas Dr Kuekenhoehner
Wolfgang Dr Krieg
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BASF SE
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BASF SE
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Priority to DE19873713337 priority Critical patent/DE3713337A1/en
Priority to AT88105990T priority patent/ATE88702T1/en
Priority to ES88105990T priority patent/ES2054725T3/en
Priority to EP88105990A priority patent/EP0287959B1/en
Priority to DE8888105990T priority patent/DE3880544D1/en
Priority to IL86098A priority patent/IL86098A/en
Priority to JP63095803A priority patent/JP2534315B2/en
Priority to US07/184,122 priority patent/US4943584A/en
Priority to HU882015A priority patent/HU202364B/en
Priority to CA000564555A priority patent/CA1331619C/en
Priority to BR8801878A priority patent/BR8801878A/en
Priority to SU4355533A priority patent/SU1655293A3/en
Priority to ZA882757A priority patent/ZA882757B/en
Priority to KR1019880004526A priority patent/KR960010354B1/en
Publication of DE3713337A1 publication Critical patent/DE3713337A1/en
Priority to MX9203407A priority patent/MX9203407A/en
Withdrawn legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
    • C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
    • C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
    • C07D261/08—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
    • C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
    • C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
    • C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
    • C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
    • C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
    • C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more 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
    • C07D261/12—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
    • C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
    • C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
    • C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
    • C07D271/10—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
    • C07D275/02—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D277/24—Radicals substituted by oxygen atoms
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    • 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
    • C07D307/40—Radicals substituted by oxygen atoms
    • C07D307/42—Singly bound oxygen atoms
    • 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
    • C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
    • C07D333/16—Radicals substituted by singly bound hetero atoms other than halogen by oxygen atoms

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Abstract

[(p-Phenoxy)phenoxy]methylisoxazoles of the general formula I <IMAGE> in which R<1>, R<2> and R<3> are hydrogen, halogen, C1-C8-alkyl, C1-C8-alkoxy, C1-C4-haloalkyl, C1-C4-haloalkoxy, nitro or cyano, R<4> is hydrogen or C1-C4-alkyl, R<5> is hydrogen, halogen, C1-C8-alkyl or C2-C8-alkenyl, R<6> is hydrogen, C1-C8-alkyl, C2-C8-alkenyl, C1-C4-haloalkyl, C2-C8-alkoxyalkyl, C3-C10-cycloalkyl, aryl, C7-C20-arylalkyl, or is aryl or C7-C20-arylalkyl, each of which is mono- to trisubstituted in the aryl moiety by halogen, C1-C8-alkyl, C1-C8-alkoxy, C1-C4-haloalkyl, C1-C4-haloalkoxy or cyano or mono- to disubstituted by nitro, and processes for their preparation and their use for controlling pests.

Description

Die vorliegende Erfindung betrifft neue [(p-Phenoxy)-phenoxy]-methyl-isoxazole der allgemeinen Formel IThe present invention relates to new [(p-phenoxy) phenoxy] methyl isoxazoles of the general formula I

in der die Substituentenin which the substituents

R¹, R², R³Wasserstoff, Halogen, C₁-C₈-Alkyl, C₁-C₈-Alkoxy, C₁-C₄-Halogenalkyl, C₁-C₄-Halogenalkoxy, Nitro oder Cyano, R⁴Wasserstoff oder C₁-C₄-Alkyl, R⁵Wasserstoff, Halogen, C₁-C₈-Alkyl oder C₂-C₈-Alkenyl, R⁶Wasserstoff, C₁-C₈-Alkyl, C₂-C₈-Alkenyl, C₁-C₄-Halogenalkyl, C₂-C₈-Alkoxy-alkyl, C₃-C₁₀-Cycloalkyl, Aryl, C₇-C₂₀-Aryl-alkyl oder im Arylteil ein- bis dreifach durch Halogen, C₁-C₈-Alkyl, C₁-C₈-Alkoxy, C₁-C₄-Halogenalkyl, C₁-C₄-Halogenalkoxy oder Cyano, oder ein- bis zweifach durch Nitro substituiertes Aryl oder C₇-C₂₀-Aryl-alkyl, bedeuten.R¹, R², R³hydrogen, halogen, C₁-C₈-alkyl, C₁-C₈-alkoxy, C₁-C₄ haloalkyl, C₁-C₄ haloalkoxy, nitro or cyano, R⁴hydrogen or C₁-C₄alkyl, R⁵hydrogen, halogen, C₁-C₈-alkyl or C₂-C₈-alkenyl, R⁶hydrogen, C₁-C₈-alkyl, C₂-C₈-alkenyl, C₁-C₄-haloalkyl, C₂-C₈-alkoxy-alkyl, C₃-C₁₀-cycloalkyl, aryl, C₇-C₂₀-aryl-alkyl or in the aryl part one to three times by halogen, C₁-C₈-alkyl, C₁-C₈ alkoxy, C₁-C₄ haloalkyl, C₁-C₄ haloalkoxy or cyano, or aryl which is mono- or disubstituted by nitro or C₇-C₂₀-aryl-alkyl mean.

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 included, as well as a method for controlling pests.

Aus DE-C-23 04 962, DE-B-23 22 853, DE-C-24 18 295, DE-A-29 42 989 und JP 80/124 460 sind zahlreiche p-Phenoxy-phenoxyverbindungen bekannt, jedoch enthalten diese Verbindungen keinen Alkyl-isoxazolrest. Die Wirkung dieser Verbindungen läßt zu wünschen übrig.From DE-C-23 04 962, DE-B-23 22 853, DE-C-24 18 295, DE-A-29 42 989 and JP 80/124 460 numerous p-phenoxy-phenoxy compounds are known, however, these compounds do not contain an alkyl isoxazole residue. The effect these connections leave something to be desired.

Der Erfindung lag daher die Aufgabe zugrunde, neue p-Phenoxy-phenoxy- verbindungen mit verbesserter Wirkung bereitzustellen.The object of the invention was therefore to develop new p-phenoxy-phenoxy to provide compounds with improved effect.

Demgemäß wurden die eingangs definierten neuen p-Phenoxy-phenoxy- verbindungen I sowie Verfahren zu deren Herstellung gefunden. Ferner wurde gefunden, daß sich die Verbindungen I zur Bekämpfung von Schädlingen eignen. Accordingly, the new p-phenoxy-phenoxy- Compounds I and methods for their preparation found. Furthermore found that the compounds I for controlling pests own.  

Die Verbindungen I sind nach folgenden Methoden erhältlich:The compounds I can be obtained by the following methods:

a) Die Umsetzung erfolgt zwischen einem (p-Phenoxy)-phenol II und einem Isoxazol III in Gegenwart einer Base im Temperaturbereich von (-20) bis 250°C, vorzugsweise von 20 bis 120°C nach folgender Reaktionsgleichung:a) The reaction takes place between a (p-phenoxy) phenol II and a Isoxazole 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:

Die (p-Phenoxy)-phenole II sind z. Teil aus Houben/Weyl, Bd VI, 3, Methoden der org. Chemie, Thieme-Verlag, 1965, 585 ff bekannt oder können nach den dort beschriebenen Methoden hergestellt werden.The (p-phenoxy) phenols II are e.g. Part from Houben / Weyl, Vol VI, 3, Methods of org. Chemie, Thieme-Verlag, 1965, 585 ff known or can be produced according to the methods described there.

Die Isoxazole III sind zum Teil aus DE-A-25 49 962 und DE-A-27 54 832 bekannt oder können nach den dort beschriebenen Methoden erhalten werden. Man setzt normalerweise mindestens equivalente Mengen einer Base 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. The isoxazoles III are partly from DE-A-25 49 962 and DE-A-27 54 832 known or can be obtained by the methods described there will. Normally at least equivalent amounts of one are used Base to II and / or III too, 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.  

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 Mixture of hexane isomers and petroleum ether; aromatic hydrocarbons, such as benzene, toluene, the xylenes and their isomer mixtures, gasoline; Alcohols such as methanol, ethanol, n-propanol and isopropanol; Ether, 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 such as acetonitrile and propionitrile; aprotic dipolar solvents such as dimethylformamide, Dimethyl sulfoxide or pyridine. Mixtures of these substances can also be used as Solvents and thinners are used.

b) Die Umsetzung erfolgt zwischen einem Phenolatanion von II und einem Isoxazol III in einem Temperaturbereich von (-20) bis 120°C, vorzugsweise von (-20) bis 80°C nach folgender Reaktionsgleichung:b) The reaction takes place between a phenolate anion of II and one Isoxazole III in a temperature range from (-20) to 120 ° C, preferably from (-20) to 80 ° C according to the following reaction equation:

Man arbeitet normalerweise mit equimolaren Mengen II und III, kann aber auch im Überschuß der einen oder anderen Komponente arbeiten.You normally work with equimolar amounts II and III but also work in excess of one or the other component.

Die Anionen der (p-Phenoxy)-phenole II lassen sich in situ aus den in Houben/Weyl (s. o.) bekannten oder nach den dort beschriebenen Methoden herstellbaren Phenolen II, z. B. durch Einwirkung eines Hydrids, wie beispielsweise Natrium-, Kalium- oder Calciumhydrid auf IIIa in Form entsprechender Salze, generieren.The anions of the (p-phenoxy) phenols II can be obtained in situ from the in Houben / Weyl (see above) known or according to the methods described there producible phenols II, e.g. B. by the action of a hydride, such as for example sodium, potassium or calcium hydride on IIIa in the form corresponding salts.

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; aromatisch Kohlenwasserstoffe, wie Benzol, Toluol, die Xylole und deren Isomerengemische und Benzin, Ether, wie Diethyl-, Di-n-Butylether, Methyl-tert.-butylether, Tetrahydrofuran und Dioxan; Ketone, wie Aceton, Methylethylketon und Methylisopropylketon; 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  Mixture of hexane isomers and petroleum ether; aromatic hydrocarbons, such as Benzene, toluene, the xylenes and their isomer mixtures and petrol, ether, 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; aprotic dipolar solvents such as dimethylformamide, dimethyl sulfoxide or pyridine. Mixtures of these substances can also be used as solutions and Thinners are used.

In beiden Fallgestaltungen bedeutet der Rest X eine 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 both cases, the radical X means a leaving group, such as for example a sulfonic acid residue or a halogen. Among the Sulfonic acid residues are methanesulfonyl, trifluoromethanesulfonyl and p-toluenesulfonyl, among the halogens chlorine and bromine are preferred; chlorine is particularly preferred.

Zur Herstellung der erfindungsgemäßen Verbindungen I nach den vorstehend beschriebenen Methoden 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 methods described usually place the starting materials in stoichiometric ratio. An excess of one or the other can be quite advantageous in individual cases.

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 Umkristallisation 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.

Der Isoxazolrest in Formel I ist üblicherweise in 4- oder 5-Stellung durch den p-Phenoxy-phenoxyrest substituiert. Die Substituenten in Formel I haben im einzelnen folgende Bedeutungen:The isoxazole radical in formula I is usually in the 4- or 5-position substituted the p-phenoxy-phenoxy radical. The substituents in formula I. have the following meanings:

R¹- bevorzugt Wasserstoff,
- Halogen, bevorzugt Fluor und Chlor, besonders bevorzugt Fluor und Chlor in para-Stellung
-C₁-C₈-Alkyl, bevorzugt C₁-C₆-Alkyl, besonders bevorzugt C₁-C₄-Alkyl in para-Stellung, wie p-Methyl, p-Ethyl, p-(n-Propyl), p-(iso-Propyl), p-(iso-Butyl) und p-(tert.-Butyl),
- C₁-C₈-Alkoxy, bevorzugt C₁-C₄-Alkoxy, besonders bevorzugt C₁-C₂-Alkoxy in para-Stellung, wie p-Methoxy und p-Ethoxy,
- C₁-C₄-Halogenalkyl, bevorzugt C₁-C₂-Fluor- und Chloralkyl, besonders bevorzugt p-Trifluormethyl und p-Trichlormethyl,
- C₁-C₄-Halogenalkoxy, bevorzugt C₁-C₂-Fluor- und Chloralkoxy, besonders bevorzugt p-Trifluormethoxy und p-Trichlormethoxy,
- Nitro,
- Cyano, R², R³- bevorzugt Wasserstoff,
- Halogen, bevorzugt Fluor und Chlor,
- C₁-C₈-Alkyl, bevorzugt C₁-C₄-Alkyl, besonders bevorzugt C₁-C₂-Alkyl, wie Methyl und Ethyl,
- C₁-C₈-Alkoxy, bevorzugt C₁-C₄-Alkoxy, besonders bevorzugt C₁-C₂-Alkoxy, wie Methoxy und Ethoxy,
- C₁-C₄-Halogenalkyl, bevorzugt C₁-C₂-Fluor- und Chloralkyl, besonders bevorzugt Trifluormethyl und Trichlormethyl,
- C₁-C₄-Halogenalkoxy, bevorzugt C₁-C₂-Fluor- und Chloralkoxy, besonders bevorzugt Trifluormethoxy und Trichlormethoxy,
- Nitro,
- Cyano, R⁴- bevorzugt Wasserstoff,
- C₁-C₄-Alkyl, bevorzugt C₁-C₂-Alkyl, besonders bevorzugt Methyl, R⁵- Wasserstoff, bevorzugt Wasserstoff in 4-Position,
- Halogen, bevorzugt Fluor, Chlor und Brom, besonders bevorzugt Brom in 5-Position,
- C₁-C₈-Alkyl, bevorzugt C₁-C₄-Alkyl, besonders bevorzugt Methyl in 5-Position,
- C₂-C₈-Alkenyl, bevorzugt C₂-C₄-Alkenyl, besonders bevorzugt Vinyl, Methylvinyl und Dimethylvinyl, R₆- Wasserstoff
- C₁-C₈-Alkyl, bevorzugt C₁-C₄-Alkyl, wie Methyl, Ethyl, n-Propyl, iso-Propyl, n-Butyl, iso-Butyl, sec.-Butyl und tert.-Butyl,
- C₂-C₈-Alkenyl, bevorzugt C₂-C₅-Alkenyl, besonders bevorzugt C₂-C₅-Alkenyl in 3-Position, wie 3-Vinyl und 3-(2,2-Dimethyl)-vinyl,
- C₁-C₄-Halogenalkyl, bevorzugt C₁-C₂-Fluor- und Chloralkyl, besonders bevorzugt 3-Trifluormethyl und 3-Trichlormethyl,
-C₂-C₈-Alkoxy-alkyl, bevorzugt C₂-C₄-Alkoxy-alkyl, besonders bevorzugt C₂-C₄-Alkoxy-alkyl in 3-Position, wie
3-(Methoxy-methyl), 3-(Methoxy-2-ethyl), 3-(Methoxy-methyl) und iso-Propoxy-methyl,
- C₃-C₁₀-Cycloalkyl, bevorzugt Cyclopropyl, Cyclopentyl, Cyclohexyl und Cyclooctyl,
- Aryl, bevorzugt Phenyl und Naphthyl, besonders bevorzugt Phenyl,
- C₇-C₂₀-Aryl-alkyl, bevorzugt C₇-C₁₀-Phenyl-alkyl, wie Benzyl und Phenethyl,
- ein- bis dreifach durch Halogen substituiertes Aryl, bevorzugt durch Fluor oder Chlor monosubstituiertes Phenyl,
- ein- bis dreifach durch C₁-C₈-Alkyl substituiertes Aryl, bevorzugt durch C₁-C₄-Alkyl monosubstituiertes Phenyl, besonders bevorzugt durch C₁-C₂-Alkyl monosubstituiertes Phenyl, wie 4-Methylphenyl und 4-Ethylphenyl,
- ein- bis dreifach durch C₁-C₈-Alkoxy substituiertes Aryl, bevorzugt durch C₁-C₄-Alkoxy monosubstituiertes Phenyl, besonders bevorzugt durch C₁-C₂-Alkoxy monosubstituiertes Phenyl, wie 4-Methoxyphenyl und 4-Ethoxyphenyl,
- ein- bis dreifach durch C₁-C₄-Halogenalkyl substituiertes Aryl, bevorzugt durch C₁-C₂-Fluor- und Chloralkyl monosubstituiertes Phenyl, besonders bevorzugt durch Trifluormethyl und Trichlorethyl monosubstituiertes Phenyl, wie 4-Trifluormethoylphenyl und 4-Trichlormethylphenyl,
- ein- bis dreifach durch C₁-C₄-Halogenalkoxy substituiertes Aryl, bevorzugt durch C₁-C₂-Fluor- und Chloralkoxy monosubstituiertes Phenyl, besonders bevorzugt durch Trifluormethoxy und Trichlormethoxy monosubstituiertes Phenyl, wie Trifluormethoxyphenyl und 4-Trichlormethoxyphenyl,
- ein- bis dreifach durch Cyano substituiertes Aryl, bevorzugt durch Cyano monosubstituiertes Phenyl, wie 4-Cyanophenyl,
- ein- bis zweifach durch Nitro substituiertes Aryl, bevorzugt durch Nitro monosubstituiertes Phenyl, wie 3-Nitrophenyl,
- im Arylteil ein- bis dreifach durch Halogen substituiertes C₇-C₂₀-Aryl-alkyl, bevorzugt im Phenylteil durch Fluor oder Chlor monosubstituiertes C₇-C₁₀-Phenyl-alkyl, wie 4-Fluorbenzyl und 4-Chlorbenzyl,
- im Arylteil ein- bis dreifach durch C₁-C₈-Alkyl substituiertes C₇-C₂₀-Aryl-alkyl, bevorzugt im Phenylteil durch C₁-C₄-Alkyl monosubstituiertes C₇-C₁₀-Phenyl-alkyl, besonders bevorzugt im Phenylteil durch C₁-C₂-Alkyl monosubstituiertes C₇-C₁₀-Phenylalkyl, wie 4-Methylphenyl, 4-Ethylbenzyl und 4-Methylphenethyl,
- im Arylteil ein- bis dreifach durch C₁-C₈-Alkoxy substituiertes C₇-C₂₀-Aryl-alkyl, bevorzugt im Phenylteil C₁-C₄-Alkoxy monosubstituiertes C₇-C₁₀-Phenylalkyl, besonders bevorzugt im Phenylteil durch C₁-C₂-Alkoxy monosubstituiertes C₇-C₁₀-Phenylalkyl, wie 4-Methoxybenzyl, 4-Ethoxybenzyl und 4-Methoxyphenethyl,
- im Arylteil ein- bis dreifach durch C₁-C₄-Halogenalkyl substituiertes C₇-C₂₀-Aryl-alkyl, bevorzugt im Phenylteil C₁-C₂-Fluor- und Chloralkyl monosubstituiertes C₇-C₁₀-Phenylalkyl, besonders bevorzugt im Phenylteil durch Trifluormethyl und Trichlormethyl monosubstituiertes C₇-C₁₀-Phenylalkyl, wie 4-Trifluormethylbenzyl und 4-Trichlor­ methylbenzyl,
- im Arylteil ein- bis dreifach durch C₁-C₄-Halogenalkoxy substituiertes C₇-C₂₀-Aryl-alkyl, bevorzugt im Phenylteil durch C₁-C₂-Halogenalkyl monosubstituiertes C₇-C₁₀-Phenyl-alkyl, besonders bevorzugt durch Trifluormethyl und Trichlormethyl monosubstituiertes C₇-C₁₀-Phenylalkyl, wie 4-Trifluormethoxybenzyl und 4-Trichlormethoxybenzyl,
- im Arylteil ein- bis dreifach durch Cyano substituiertes C₇-C₂₀-Aryl-alkyl, bevorzugt im Phenylteil durch Cyano monosubstituiertes C₇-C₁₀-Phenyl-alkyl, wie 4-Cyanobenzyl und 4-Cyanophenethyl,
- im Arylteil ein- bis dreifach durch Nitro substituiertes C₇-C₂₀-Aryl-alkyl, bevorzugt durch Nitro monosubstituiertes C₇-C₁₀-Phenyl-alkyl, wie 3-Nitrobenzyl.R¹- preferably hydrogen,
- Halogen, preferably fluorine and chlorine, particularly preferably fluorine and chlorine in the para position
-C₁-C₈-alkyl, preferably C₁-C₆-alkyl, particularly preferably C₁-C₄-alkyl in para position, such as p-methyl, p-ethyl, p- (n-propyl), p- (iso-propyl) , p- (iso-butyl) and p- (tert-butyl),
- C₁-C₈-alkoxy, preferably C₁-C₄-alkoxy, particularly preferably C₁-C₂-alkoxy in para position, such as p-methoxy and p-ethoxy,
- C₁-C₄-haloalkyl, preferably C₁-C₂-fluoro and chloroalkyl, particularly preferably p-trifluoromethyl and p-trichloromethyl,
- C₁-C₄-haloalkoxy, preferably C₁-C₂-fluoro and chloroalkoxy, particularly preferably p-trifluoromethoxy and p-trichloromethoxy,
- nitro,
- cyano, R², R³- preferably hydrogen,
Halogen, preferably fluorine and chlorine,
- C₁-C₈-alkyl, preferably C₁-C₄-alkyl, particularly preferably C₁-C₂-alkyl, such as methyl and ethyl,
- C₁-C₈-alkoxy, preferably C₁-C₄-alkoxy, particularly preferably C₁-C₂-alkoxy, such as methoxy and ethoxy,
- C₁-C₄-haloalkyl, preferably C₁-C₂-fluoro and chloroalkyl, particularly preferably trifluoromethyl and trichloromethyl,
- C₁-C₄-haloalkoxy, preferably C₁-C₂-fluoro and chloroalkoxy, particularly preferably trifluoromethoxy and trichloromethoxy,
- nitro,
- Cyano, R⁴- preferably hydrogen,
- C₁-C₄-alkyl, preferably C₁-C₂-alkyl, particularly preferably methyl, R⁵- hydrogen, preferably hydrogen in the 4-position,
Halogen, preferably fluorine, chlorine and bromine, particularly preferably bromine in the 5-position,
- C₁-C₈-alkyl, preferably C₁-C₄-alkyl, particularly preferably methyl in the 5-position,
- C₂-C₈ alkenyl, preferably C₂-C₄ alkenyl, particularly preferably vinyl, methyl vinyl and dimethyl vinyl, R₆- hydrogen
- C₁-C₈-alkyl, preferably C₁-C₄-alkyl, such as methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl and tert-butyl,
- C₂-C₈-alkenyl, preferably C₂-C₅-alkenyl, particularly preferably C₂-C₅-alkenyl in the 3-position, such as 3-vinyl and 3- (2,2-dimethyl) vinyl,
- C₁-C₄-haloalkyl, preferably C₁-C₂-fluoro and chloroalkyl, particularly preferably 3-trifluoromethyl and 3-trichloromethyl,
-C₂-C₈-alkoxy-alkyl, preferably C₂-C₄-alkoxy-alkyl, particularly preferably C₂-C₄-alkoxy-alkyl in the 3-position, such as
3- (methoxy-methyl), 3- (methoxy-2-ethyl), 3- (methoxy-methyl) and iso-propoxy-methyl,
- C₃-C₁₀ cycloalkyl, preferably cyclopropyl, cyclopentyl, cyclohexyl and cyclooctyl,
Aryl, preferably phenyl and naphthyl, particularly preferably phenyl,
- C₇-C₂₀-aryl-alkyl, preferably C₇-C₁₀-phenyl-alkyl, such as benzyl and phenethyl,
aryl monosubstituted to trisubstituted by halogen, preferably phenyl monosubstituted by fluorine or chlorine,
- Aryl mono- to trisubstituted by C₁-C₈-alkyl, preferably phenyl monosubstituted by C₁-C₁-alkyl, particularly preferably phenyl monosubstituted by C₁-C₂-alkyl, such as 4-methylphenyl and 4-ethylphenyl,
- Aryl mono- to trisubstituted by C₁-C₁-alkoxy, preferably phenyl monosubstituted by C₁-C₄-alkoxy, particularly preferably phenyl monosubstituted by C₁-C₂-alkoxy, such as 4-methoxyphenyl and 4-ethoxyphenyl,
- Aryl mono- to trisubstituted by C₁-C₁-haloalkyl, preferably phenyl monosubstituted by C₁-C₂-fluoro and chloroalkyl, particularly preferably phenyl monosubstituted by trifluoromethyl and trichloroethyl, such as 4-trifluoromethoylphenyl and 4-trichloromethylphenyl,
- Aryl mono- to trisubstituted by C₁-C₄-haloalkoxy, preferably phenyl monosubstituted by C₁-C₂-fluoro and chloroalkoxy, particularly preferably monosubstituted phenyl by trifluoromethoxy and trichloromethoxy, such as trifluoromethoxyphenyl and 4-trichloromethoxyphenyl,
aryl monosubstituted to trisubstituted by cyano, preferably phenyl monosubstituted by cyano, such as 4-cyanophenyl,
aryl monosubstituted or disubstituted by nitro, preferably phenyl monosubstituted by nitro, such as 3-nitrophenyl,
- C₇-C₂ Ar-aryl-alkyl mono- to trisubstituted by halogen in the aryl part, preferably Cos-C₁₀-phenyl-alkyl monosubstituted by fluorine or chlorine in the phenyl part, such as 4-fluorobenzyl and 4-chlorobenzyl,
- In the aryl part mono- to trisubstituted by C₁-C₈-alkyl C₈-C₂₀-aryl-alkyl, preferably in the phenyl part by C₁-C₄-alkyl monosubstituted C₇-C₁₀-phenyl-alkyl, particularly preferably in the phenyl part by C₁-C₂-alkyl monosubstituted C₇-C₁₀ phenylalkyl, such as 4-methylphenyl, 4-ethylbenzyl and 4-methylphenethyl,
- C₇-C₂₀-aryl-alkyl which is mono- to trisubstituted by C₁-C₈-alkoxy in the aryl part, C₇-C₁-alkoxy monosubstituted in the phenyl part C₁-C₁₀-phenylalkyl, particularly preferably C₇-C₂-alkoxy monosubstituted in the phenyl part by C₁-C₂-alkoxy C₁₀-phenylalkyl, such as 4-methoxybenzyl, 4-ethoxybenzyl and 4-methoxyphenethyl,
- In the aryl part mono- to trisubstituted by C₁-C₄-haloalkyl C₇-C₂₀-aryl-alkyl, preferably in the phenyl part C₁-C₂-fluoro and chloroalkyl monosubstituted C₇-C₁₀-phenylalkyl, particularly preferably in the phenyl part by trifluoromethyl and trichloromethyl-substituted C₇ -C₁₀-phenylalkyl, such as 4-trifluoromethylbenzyl and 4-trichloromethylbenzyl,
- In the aryl part mono- to trisubstituted by C₁-C₄-haloalkoxy Coxy-C₂₀-aryl-alkyl, preferably in the phenyl part by C₁-C₂-haloalkyl monosubstituted C₇-C₁₀-phenyl-alkyl, particularly preferably by trifluoromethyl and trichloromethyl-monosubstituted C₇-C₁₀ Phenylalkyl, such as 4-trifluoromethoxybenzyl and 4-trichloromethoxybenzyl,
- In the aryl part mono- to trisubstituted by cyano-substituted C₇-C₂₀-aryl-alkyl, preferably in the phenyl part by cyano monosubstituted C₇-C₁₀-phenyl-alkyl, such as 4-cyanobenzyl and 4-cyanophenethyl,
- In the aryl part mono- to trisubstituted by nitro C₇-C₂₀-aryl-alkyl, preferably monosubstituted by nitro C₇-C₁₀-phenyl-alkyl, such as 3-nitrobenzyl.

Im Gegensatz zu den meisten bisher bekannten Wirkstoffen, die als Kontakt- oder Fraßgifte die Tiere töten, lähmen oder vertreiben, wirken die meisten der Verbindungen der Formel I entwicklungsstörend auf den tierischen Organismus. Bei Insekten wird beispielsweise die Umwandlung zur Imago, die Ablage von entwicklungsfähigen Eiern und die Entwicklung von abgelegten Eiern gestört und dadurch die Generationsfolge unterbrochen. Für Wirbeltiere sind die erfindungsgemäßen Wirkstoffe praktisch ungiftig. Die meisten der Verbindungen der Formel I werden überdies leicht zu Stoffen abgebaut, die in der natürlichen Umgebung vorkommen und von Mikroorganismen weiter zerlegt werden. In contrast to most of the previously known active ingredients, which as Contact or feeding poisons that kill, paralyze or drive away animals work most of the compounds of formula I impair development on the animal organism. In the case of insects, for example, the conversion to Imago, the storage of viable eggs and the development of eggs are disturbed and thereby the sequence of generations interrupted. The active compounds according to the invention are for vertebrates practically non-toxic. Most of the compounds of formula I are moreover easily degraded to substances in the natural environment occur and are further broken down by microorganisms.  

Die [(p-Phenoxy)-phenoxy]-methyl-isoxazole der allgemeinen Formel I sind geeignet, Schädlinge aus der Klasse der Insekten, Spinnentieren und Nematoden wirksam zu bekämpfen. Sie können im Pflanzenschutz sowie auf dem Hygiene-, Vorratsschutz- und Veterinärsektor als Schädlingsbekämpfungsmittel eingesetzt werden.The [(p-phenoxy) phenoxy] methyl isoxazoles of the general formula I are suitable for pests 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), Tortrix 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), Ortiorrhynchus 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 rose (Rübenblattwespe), Hoplocampa minuta (Pflaumensägewespe), Monomorium pharaonis (Pharaoameise), Solenopsis geminata (Feuerameise), Atta sexdens (Blattschneiderameise);
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 Bohnenblattlaus), 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 Ordnung 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).The harmful insects from the order of the butterflies (Lepidoptera) include, for example, Plutella maculipennis (cabbage cockroach), Leucoptera coffeella (coffee moth), Hyponomeuta malinellus (apple tree spider moth), Argyresthia conjugella (apple moth), Sitotroga cerealella (cereal moth opera), Phulellaima moth Capua reticulana (apple peel wrapper), Sparganothis pilleriana (springworm), Cacoecia murinana (pine shoot winder), Tortrix viridana (oak wrap), Clysia ambiguella (hay and sour worm), Evetria buoliana (pine shoot winder), Polychrosis Traubeniawick (Bekreuza), Bekreuz ), Laspeyresia molesta (peach shoots), Laspeyresia funebrana (plum wrappers), Ostrinia nubilalis (European corn borer), Loxostege sticticalis (European corn borer), Ephestia kuehniella (flour moth), Chilo suppressalis (rice stem angel sponges), Mala moss spider, Maleria mottle sponges, Maleria mottle sponges, Maleria mottle sponges, Ringeria angel sponges, Maleria mottle sponges Dendrolimus pini (pine moth), Thaumatopoea ptiyo campa (pine processionary moth), Phalera bucephala (moon spot), Cheimatobia brumata (small frost tree), Hibernia defoliaria (large frost tree), Bupalus piniarius (pine tree tree), Hyphantria cunea (white bear tree), Agrotis segeton (Wintersaisuleilule) (winter seed pellet) Barathra brassicae (coal owl), Cirphis unipuncta (army worm), Prodenia litura (cotton caterpillar), Laphygma exigua (beet armyworm), Panolis flammea (floridae), Earias insulana (cotton capsule worm), Plusia gamma (gammaeule), Alabama leaf worm, Lymantria dispar (sponge moth), Lymantria monacha (nun), Pieris brassicae (cabbage white butterfly), Aporia crataegi (tree white butterfly); 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 (lenticular beetle), Bruchus rufimanus (horse bean beetle), Bruchus pisorum (pea beetle), Sitona lineatus (lined leaf beetle), Ortiorrhynchus sulcatus (furrowed rag weevil), Otiorrhynchus ovatus (strawberry root weevil) (Apfelbelüssel (big apple), betle beetle rye) (betel beetroot), betel beetle rye (betel beetroot), betel beetle rye (betel beetroot), betel beetle rye (betel beetroot), betel beetle rye (betel beetroot), betel beetle rye (beti , Anthonomus grandis (capsule beetle), Ceuthorrhynchus assimilis (cabbage pod weevil), Ceuthorrynchus napi (large cabbage weevil), Sitophilus granaria (grain beetle), Anisandrus dispar (uneven wood bark beetle), Ips typographus (printer printer)
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, Chry somya macellaria, Chrysomya hominivorax, Lucilia cuprina, Lucilia sericata, Hypoderma lineata;
from the order of the hymenoptera (Hymenoptera), for example Athalia rose (turnip wasp), Hoplocampa minuta (plum saw wasp), Monomorium pharaonis (pharaoh ant), Solenopsis geminata (fire ant), Atta sexdens (leaf cutter ant);
from the order of the bugs (Heteroptera), for example Nezara viridula (green rice bug), Eurygaster integriceps (Asian cereal 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 aphid), Aphis pomi (green apple aphid), Aphis sambuci (elderberry aphid), Aphidula nasturtii (buckthorn aphid), Cerosipha gossypii (cucumber aphid), Sappaphis mali (rosy apple aphid), Sappaphis mala (floury pear louse aphid), Dappaphis mala (Mehlige Pearleaf aphid), Dappaphis mala 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 (vine louse);
from the order of the 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 Spinnentiere (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 as well Tylenchorhynchus dubius, Tylenchorhynchus claytoni, Rotylenchus robustus, Heliocotylenchus multicinctus, Radopholus similis, Belonolaimus longicaudatus, Longidorus elongatus, Trichodorus primitivus.

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 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 Uses; in any case, they should be the finest Ensure distribution of the 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 from medium to high mineral oil fractions 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 Lösungsmittel gelöst, mittels Netz-, Haft-, Dispergier- oder Öldispersionen können die Substanzen als solche oder in einem Öl 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 Solvent dissolved, by means of wetting, adhesive, dispersing or Oil dispersions can be the substances as such or in an oil or Emulsifiers can be homogenized in water. But it can also be made active substance wetting, adhesive, dispersing or emulsifying agent and possibly concentrates containing solvents or oil are produced, which are suitable for dilution with water.

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 sulfatiertem 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, Laurylalkoholpolyglykoletheracetal, Sorbitester, Lignin, Sulfitablaugen und Methylcellulose in Betracht.Alkali, alkaline earth, ammonium salts come from as surface-active substances Ligninsulfonic acid, naphthalenesulfonic acid, phenolsulfonic acid, Alkylarylsulfonate, alkyl sulfates, alkyl sulfonates, alkali and Alkaline earth metal salts of dibutylnaphthalenesulfonic acid, lauryl ether sulfate,  Fatty alcohol sulfates, fatty acid alkali and alkaline earth, sulfated salts 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 naphthalene sulfonic 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, sulfite waste liquor and methyl cellulose.

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. Ammoniumsul­ fat, Ammoniumphosphat, Ammoniumnitrat, Harnstoffe und pflanzliche Pro­ dukte, wie Getreidemehl, Baumrinden-, Holz- und Nußschalenmehl, Cellu­ losepulver 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 sul fat, ammonium phosphate, ammonium nitrate, ureas and herbal pro products such as flour, tree bark, wood and nutshell flour, cellu loose 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 werden 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 are mixed 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. 1 werden mit einer Mischung aus 92 Gew.-Teilen pulverförmigem Kieselsäuregel und 8 Gew.-Teilen Paraffinöl, das auf die Oberfläche dieses Kieselsäuregels ge­ sprüht wurde, innig vermischt. Man erhält auf diese Weise eine Aufbereitung des Wirkstoffs mit guter Haftfähigkeit. II. 30 parts by weight of compound no. 1 are mixed with a mixture of 92 parts by weight of powdered silica gel and 8 parts by weight Paraffin oil that ge on the surface of this silica gel was sprayed, intimately mixed. You get one in this way Preparation of the active ingredient with good adhesiveness.  
  • III. 10 Gew.-Teile der Verbindung Nr. 1 werden in einer Mischung gelöst, die aus 90 Gew.-Teilen Xylol, 6 Gew.-Teilen des Anlage­ rungsproduktes von 8 bis 10 Mol Ethylenoxid an 1 Mol Ölsäure- N-monoethanolamid, 2 Gew.-Teilen Calciumsalz der Dodecylbenzol­ sulfonsäure und 2 Gew.-Teilen des Anlagerungsproduktes von 40 Mol Ethylenoxid an 1 Mol Ricinusöl besteht.III. 10 parts by weight of compound No. 1 are mixed solved that from 90 parts by weight of xylene, 6 parts by weight of the plant product of 8 to 10 moles of ethylene oxide in 1 mole of oleic acid N-monoethanolamide, 2 parts by weight of calcium salt of dodecylbenzene sulfonic acid and 2 parts by weight of the adduct of 40 mol There is ethylene oxide in 1 mol of castor oil.
  • IV. 20 Gew.-Teile der Verbindung Nr. 1 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 Anlagerungs­ produktes von 40 Mol Ethylenoxid an 1 Mol Ricinusöl besteht.IV. 20 parts by weight of compound No. 1 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 pulverförmige Kiesel­ säuregel 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 pebbles well mixed acidic gel and ground in a hammer mill.

Die Wirkstoffkonzentrationen in den anwendungsfertigen Zubereitungen können in größeren Bereichen variiert werden.The active ingredient concentrations in the ready-to-use preparations can be varied in larger areas.

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.Generally they are between 0.0001 and 10%, preferably between 0.01 and 1%. The active ingredients can also be used successfully in the Ultra-low-volume (ULV) processes are used, whereby it is possible Formulations with more than 95 wt .-% active ingredient or even the active ingredient without applying additives.

Die Aufwandmenge an Wirkstoff beträgt unter Freilandbedingungen 0,02 bis 10, vorzugsweise 0,1 bis 0,5 kg/ha.The amount of active ingredient applied under field conditions is 0.02 to 10, preferably 0.1 to 0.5 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.Various types of oils, herbicides, fungicides, other pesticides, bactericides, if necessary also 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.

Beispielsweise können folgende Mittel zugemischt werden:For example, the following agents can be added:

1,2-Dibrom-3- chlorpropan, 1,3-Dichlorpropen, 1,3-Dichlorpropen + 1,2-Dichlorpropan, 1,2-Dibromethan, 2-sec.-Butyl-phenyl-N-methylcarbamat, o-Chlorphenyl-N- methylcarbamat, 3-Isopropyl-5-methylphenyl-N-methylcarbamat, o-Isopropoxyphenyl-N-methylcarbamat, 3,5-Dimethyl-4-methylmercapto-phenyl-N- methylcarbamat, 4-Dimethylamino-3,5-xylyl-N-methylcarbamat, 2-(1,3-Dioxolan- 2-yl)-phenyl-N-methylcarbamat, 1-Naphthyl-N-methylcarbamat, 2,3-Di­ hydro-2,2-dimethyl-benzofuran-7-yl-N-methylcarbamat, 2,2-Dimethyl-1,3- benzodioxol-4-yl-N-methylcarbamat, 2-Dimethylamino-5,6-dimethyl-4-pyrimi­ dinyl-dimethylcarbamat, 2-Methyl-2-(methylthio)-propionaldehyd-O-(methyl­ carbamoyl)-oxim, S-Methyl-N[(methylcarbamoyl)-oxyl]-thio-acetimidat, Methyl-N′,N′-dimethyl-N[(methylcarbamoyl)-oxy]-1-thiooxamidat, N-(2- Methylchlorphenyl)-N′,N′-dimethylformamidin, Tetrachlorthiophen, 1-(2,6- Difluor-benzoyl)-3-(4-chlorphenyl)-harnstoff, O,O-Dimethyl-O-(p-nitro­ phenyl)-phosphorthioat, O,O-Diethyl-O-(p-nitrophenyl)-phosphorthioat, O-Ethyl-O-(p-nitrophenyl)-phenyl-phosphonothioat, O,O-Dimethyl-O-(3- methyl-4-nitrophenyl)-phosphorthioat, O,O-Diethyl-O-(2,4-dichlorphenyl)- phosphorthioat, O-Ethyl-O-(2,4-dichlorphenyl)-phenyl-phosphonothioat, O,O-Dimethyl-O-(2,4,5-trichlorphenyl)-phosphorthioat, O-Ethyl-O-(2,4,5-trichlorphenyl)-ethyl-phosphorthioat, O,O-Dimethyl-O-(4-brom-2,5-di­ chlorphenyl)-phosphorthioat, O,O-Dimethyl-O-(2,5-dichlor-4-jodphenyl)- phosphorthioat, O,O-Dimethyl-O-(3-methyl-4-methylthiophenyl)-phosphorthioat, O-Ethyl-O-(3-methyl-4-methylthiophenyl)-isopropyl-phosphoramidat, O,O-Diethyl-O-(p-methylsulfinyl-phenyl)-phosphorthioat, O-Ethyl- S-phenyl-ethyl-phosphonodithioat, O,O-Diethyl-[2-chlor-1-(2,4-dichlor­ phenyl)-vinyl]-phosphat, O,O-Dimethyl-[2-chlor-1-(2,4,5,-trichlor­ phenyl)]-vinylphosphat, O,O-Dimethyl-S-(1′-phenyl)-ethylacetat-phosphordi­ thioat, Bis-(dimethylamino)-fluorphosphinoxid, Octamethyl-pyrophosphor­ amid, O,O,O,O-Tetraethyldithio-pyrophosphat, S-Chlormethyl-O,O-diethyl­ phosphordithioat, O-Ethyl-S,S-dipropyl-phosphordithioat, O,O-Dimethyl-O- 2,2-dichlorvinyl-phosphat, O,O-Dimethyl-1,2-dibrom-2,2-dichlorethylphosphat, O,O-Dimethyl-2,2,2-trichlor-1-hydroxy-ethylphosphonat, O,O-Di­ methyl-S-[1,2-biscarbethoxy-ethyl-(1)]-phosphordithioat, O,O-Dimethyl-O- (1-methyl-2-carbmethoxy-vinyl)-phosphat, O,O-Dimethyl-S-(N-methyl-car­ bamoyl-methyl)-phosphordithioat, O,O-Dimethyl-S-(N-methylcarbamoyl­ methyl)-phosphorthioat, O,O-Dimethyl-S-(N-methoxyethyl-carbamoylmethyl)- phosphordithioat, O,O-Dimethyl-S-(N-formyl-N-methyl-carbamoyl-methyl)- phosphordithioat, O,O-Dimethyl-O-[1-methyl-2-(methyl-carbamoyl)-vinyl]- phosphat, O,O-Dimethyl-O-[1-methyl-2-dimethylcarbamoyl)-vinyl]-phosphat, O,O-Dimethyl-O-[(1-methyl-2-chlor-2-diethylcarbamoyl)-vinyl]-phospha-t, O,O-Diethyl-S-(ethylthiomethyl)-phosphordithioat, O,O-Diethyl-S- [(p-chlorphenylthio)-methyl]-phosphordithioat, O,O-Dimethyl-S-(2-ethyl­ thioethyl)-phosphorthioat, O,O-Dimethyl-S-(2-ethylthioethyl)-phosphordithioat, O,O-Dimethyl-S-(2-ethylsulfinyl-ethyl)-phosphorthioat, O,O-Di­ ethyl-S-(2-ethylthio-ethyl)-phosphordithioat, O,O-Diethyl-S-(2-ethylsulfinyl- ethyl)-phosphorthioat, O,O-Diethyl-thiophosphoryliminophenyl)-ace­ tonitril, O,O-Diethyl-S-(2-chlor-1-phthalimidoethyl)-phosphordithioat, O,O-Diethyl-S-[6-chlor-benzoxazolon-(2)-yl(3)]-methyldithiophosphat,- O,O-Dimethyl-S-[2-methoxy-1,3,4-thiadiazol-5-[4H]-onyl-(4)-methyl]- phosphordithioat, O,O-Diethyl-O-[3,5,6-trichlor-pyridyl-(2)]-phosphorthioat, O,O-Diethyl-O-(2-pyrazinyl)-phosphorthioat, O,O-Diethyl-O-[2-isopropyl-4- methyl-pyrimidinyl(6)]-phosphorthioat, O,O-Diethyl-O-[2-(diethylamino)- 6-methyl-4-pyrimidinyl]-thionophosphat, O,O-Dimethyl-S-(4-oxo-1,2,3-benzo­ triazin-3-[4H]-yl-methyl)-phosphordithioat, O,O-Dimethyl-S-[(4,6-di­ amino-1,3,5-triazin-2-yl)-methyl]-phosphordithioat, O,O-Diethyl-(1- phenyl-1,2,4-triazol-3-yl)-thionophosphat, O,S-Dimethyl-phosphor-amido­ thioat, O,S-Dimethyl-N-acetyl-phosphoramidothioat, alpha-Hexachlorcyclo­ hexan, 1,1-Di-(p-methoxyphenyl)-2,2,2-trichlor-ethan, 6,7,8,9,10,10-Hexa­ chloro-1,5,5a,6,9,9a-hexahydro-6,9-methano-2,4,3-benzodioxa-thiepin--3- oxid-Pyrethrine, DL-2-Allyl-3-methyl-cyclopenten-(2)-on-(1)-yl-(4)-DL- cis,-trans-chrysanthemat, 5-Benzyl-furyl-(3)-methyl-DL-cis, -trans-chry­ santhemat, 3-Phenoxybenzyl(±)-cis, -trans-2,2-dimethyl-3-(2,2-dichlor­ vinyl)-cyclopropancarboxylat, alpha-Cyano-3-phenoxybenzyl(±)-cis, -trans- 2,2-dimethyl-3-(2,2-dichlorvinyl)-cyclopropancarboxylat, (s)-alpha- Cyano-3-phenoxybenzyl-cis(1R, 3R)-2,2-dimethyl-3-(2,2-dibromvinyl)-cyclo­ propancarboxylat, 3,4,5,6-Tetrahydrophthalimidoethyl-DL-cis, -trans-chry­ santhemat, 2-Methyl-5-(2-propinyl)-3-furylmethyl-chrysanthemat, (alpha- Cyano-3-phenoxybenzyl)-alpha-isopropyl-4-chlorphenylacetat.
1,2-dibromo-3-chloropropane, 1,3-dichloropropene, 1,3-dichloropropene + 1,2-dichloropropane, 1,2-dibromoethane, 2-sec-butyl-phenyl-N-methylcarbamate, o-chlorophenyl -N-methyl carbamate, 3-isopropyl-5-methylphenyl-N-methyl carbamate, o-isopropoxyphenyl-N-methyl carbamate, 3,5-dimethyl-4-methylmercapto-phenyl-N-methyl carbamate, 4-dimethylamino-3,5-xylyl -N-methylcarbamate, 2- (1,3-dioxolan- 2-yl) -phenyl-N-methylcarbamate, 1-naphthyl-N-methylcarbamate, 2,3-di hydro-2,2-dimethyl-benzofuran-7- yl-N-methylcarbamate, 2,2-dimethyl-1,3-benzodioxol-4-yl-N-methylcarbamate, 2-dimethylamino-5,6-dimethyl-4-pyrimidinyl-dimethylcarbamate, 2-methyl-2- ( methylthio) propionaldehyde-O- (methyl carbamoyl) oxime, S-methyl-N [(methylcarbamoyl) -oxy] thio-acetimidate, methyl-N ′, N′-dimethyl-N [(methylcarbamoyl) -oxy] - 1-thiooxamidate, N- (2-methylchlorophenyl) -N ′, N′-dimethylformamidine, tetrachlorothiophene, 1- (2,6-difluorobenzoyl) -3- (4-chlorophenyl) urea, O, O-dimethyl- O- (p-nitro phenyl) phosphorothioate, O, O-diethyl-O- (p-nitrophenyl) phosphor hioate, O-ethyl-O- (p-nitrophenyl) phenyl phosphonothioate, O, O-dimethyl-O- (3-methyl-4-nitrophenyl) phosphorothioate, O, O-diethyl-O- (2.4 -dichlorophenyl) - phosphorothioate, O-ethyl-O- (2,4-dichlorophenyl) -phenyl-phosphonothioate, O, O-dimethyl-O- (2,4,5-trichlorophenyl) -phosphorothioate, O-ethyl-O- (2,4,5-trichlorophenyl) ethyl phosphorothioate, O, O-dimethyl-O- (4-bromo-2,5-di chlorophenyl) phosphorothioate, O, O-dimethyl-O- (2,5- dichloro-4-iodophenyl) phosphorothioate, O, O-dimethyl-O- (3-methyl-4-methylthiophenyl) phosphorothioate, O-ethyl-O- (3-methyl-4-methylthiophenyl) isopropyl phosphoramidate, O , O-diethyl-O- (p-methylsulfinyl-phenyl) phosphorothioate, O-ethyl-S-phenyl-ethyl-phosphonodithioate, O, O-diethyl- [2-chloro-1- (2,4-dichlorophenyl) -vinyl] phosphate, O, O-dimethyl- [2-chloro-1- (2,4,5, -trichlorophenyl)] - vinyl phosphate, O, O-dimethyl-S- (1'-phenyl) ethyl acetate -phosphordi thioate, bis- (dimethylamino) -fluorophosphine oxide, octamethyl-pyrophosphoramide, O, O, O, O-tetraethyldithio-pyrophosphate, S-chloromethyl-O, O-diethyl phosphorodite hioate, O-ethyl-S, S-dipropyl-phosphorodithioate, O, O-dimethyl-O-2,2-dichlorovinyl-phosphate, O, O-dimethyl-1,2-dibromo-2,2-dichloroethyl phosphate, O, O-dimethyl-2,2,2-trichloro-1-hydroxyethylphosphonate, O, O-dimethyl-S- [1,2-biscarbethoxy-ethyl- (1)] -phosphorodithioate, O, O-dimethyl-O - (1-methyl-2-carbmethoxy-vinyl) phosphate, O, O-dimethyl-S- (N-methyl-car bamoyl-methyl) -phosphorodithioate, O, O-dimethyl-S- (N-methylcarbamoyl methyl) -phosphorthioate, O, O-Dimethyl-S- (N-methoxyethyl-carbamoylmethyl) - phosphorodithioate, O, O-Dimethyl-S- (N-formyl-N-methyl-carbamoyl-methyl) - phosphorodithioate, O, O-Dimethyl -O- [1-methyl-2- (methyl-carbamoyl) vinyl] phosphate, O, O-dimethyl-O- [1-methyl-2-dimethylcarbamoyl) vinyl] -phosphate, O, O-dimethyl- O - [(1-methyl-2-chloro-2-diethylcarbamoyl) vinyl] -phosphate, O, O-diethyl-S- (ethylthiomethyl) -phosphorodithioate, O, O-diethyl-S- [(p- chlorophenylthio) methyl] -phosphorodithioate, O, O-Dimethyl-S- (2-ethylthioethyl) -phosphorothioate, O, O-Dimethyl-S- (2-ethylthioethyl) -phosphorodithioate, O, O-Dimethyl- S- (2-ethylsulfinyl-ethyl) phosphorothioate, O, O-diethyl S- (2-ethylthio-ethyl) phosphorodithioate, O, O-Diethyl S- (2-ethylsulfinyl-ethyl) phosphorothioate, O , O-Diethyl-thiophosphoryliminophenyl) -ace tonitrile, O, O-Diethyl-S- (2-chloro-1-phthalimidoethyl) -phosphorodithioate, O, O-Diethyl-S- [6-chloro-benzoxazolone- (2) - yl (3)] - methyldithiophosphate, - O, O-Dimethyl-S- [2-methoxy-1,3,4-thiadiazole-5- [4H] -onyl- (4) -methyl] - phosphorodithioate, O, O -Diethyl-O- [3,5,6-trichloropyridyl- (2)] - phosphorothioate, O, O-diethyl-O- (2-pyrazinyl) -phosphorthioate, O, O-diethyl-O- [2- isopropyl-4-methyl-pyrimidinyl (6)] - phosphorothioate, O, O-diethyl-O- [2- (diethylamino) - 6-methyl-4-pyrimidinyl] -thionophosphate, O, O-dimethyl-S- (4th -oxo-1,2,3-benzotriazine-3- [4H] -yl-methyl) -phosphorodithioate, O, O-Dimethyl-S - [(4,6-di amino-1,3,5-triazine 2-yl) -methyl] -phosphorodithioate, O, O-diethyl- (1-phenyl-1,2,4-triazol-3-yl) -thionophosphate, O, S-dimethyl-phosphoramido thioate, O, S -Dimethyl-N-acetyl-phosphoramidothioate, alpha-hexachlorocyclohexane, 1,1-di- (p-metho xyphenyl) -2,2,2-trichloroethane, 6,7,8,9,10,10-hexa chloro-1,5,5a, 6,9,9a-hexahydro-6,9-methano-2, 4,3-benzodioxa-thiepin - 3-oxide-pyrethrins, DL-2-allyl-3-methyl-cyclopenten- (2) -one- (1) -yl- (4) -DL- cis, -trans- chrysanthemum, 5-benzyl-furyl- (3) -methyl-DL-cis, -trans-chrysanthate, 3-phenoxybenzyl (±) -cis, -trans-2,2-dimethyl-3- (2,2-dichlor vinyl) -cyclopropanecarboxylate, alpha-cyano-3-phenoxybenzyl (±) -cis, -trans-2,2-dimethyl-3- (2,2-dichlorovinyl) -cyclopropanecarboxylate, (s) -alpha-cyano-3-phenoxybenzyl -cis (1R, 3R) -2,2-dimethyl-3- (2,2-dibromovinyl) -cyclopropane carboxylate, 3,4,5,6-tetrahydrophthalimidoethyl-DL-cis, -trans-chryanthate, 2-methyl -5- (2-propynyl) -3-furylmethyl chrysanthemate, (alpha- cyano-3-phenoxybenzyl) alpha-isopropyl-4-chlorophenyl acetate.

HerstellungsbeispielManufacturing example 5-[(p-Phenoxy)-phenoxy-methyl]-3-methyl-isoxazol (Verbindung 1)5 - [(p-phenoxy) phenoxy-methyl] -3-methyl-isoxazole (Compound 1)

Zu 3,1 g Natriumhydrid (85%ig in Paraffin) in 100 ml Dimethylsulfoxid wird bei 10 bis 20°C 18,6 g p-Phenoxyphenol in 50 ml Dimethylsulfoxid getropft, 30 Minuten bei 50°C gerührt und anschließend bei 15 bis 20°C 3-Methyl-5-chlormethylisoxazol zugetropft. Nach 8 Stunden bei 70°C wird wie üblich aufgearbeitet und man erhält 26,7 g Verbindung 1; Fp.: 48 bis 51°C.To 3.1 g of sodium hydride (85% in paraffin) in 100 ml of dimethyl sulfoxide is 18.6 g of p-phenoxyphenol in 50 ml of dimethyl sulfoxide at 10 to 20 ° C. added dropwise, stirred at 50 ° C. for 30 minutes and then at 15 to 20 ° C. 3-Methyl-5-chloromethylisoxazole added dropwise. After 8 hours at 70 ° C worked up as usual and 26.7 g of compound 1 are obtained; Fp .: 48 bis 51 ° C.

Analyse: C₁₇H₁₅O₃N (281)
Ber.:C 72,6 H 5,4 N 5,0 Gef.:C 73,0 H 5,6 N 4,8Analysis: C₁₇H₁₅O₃N (281)
Calc: C 72.6 H 5.4 N 5.0 Found: C 73.0 H 5.6 N 4.8

Die in den Tabellen 1 und 2 zusammengefaßten Verbindungen I (Ia und Ib) sind auf analoge Weise hergestellt worden oder können auf diese Weise erhalten werden. The compounds I (Ia and Ib) summarized in Tables 1 and 2 have been prepared in an analogous manner or can be obtained in this way.

AnwendungsbeispieleExamples of use

Die Konzentrationen, bei denen die untersuchten Verbindungen eine 100%ige Mortalität bzw. Hemmung bewirken, sind die jeweiligen Minimalkonzen­ trationen. Bei jeder Konzentration wurden mindestens 2 Versuche angesetzt.The concentrations at which the compounds tested are 100% The respective minimum concentrations cause mortality or inhibition trations. At least 2 attempts were made at each concentration.

Beispiel AExample A Dysdercus intermedius (Baumwollwanze), ZuchtversuchDysdercus intermedius (cotton bug), breeding attempt

Petrischalen von 10 cm Durchmesser werden mit 1 ml der acetonischen Wirk­ stofflösung ausgekleidet. Nach Verdunsten des Lösungsmittels besetzt man die Schalen mit je 20 Larven des vorletzten Stadiums. Nach 24 Stunden überführt man die überlebenden Tiere in 1 l-Gläser, die 200 g sterilen Quarzsand (Korngröße 0 bis 3 mm) enthalten. Dieser Sand wurde vor Versuchsbeginn mit 25 ml der wäßrigen Wirkstoffaufbereitung angegossen. Als Futter bietet man gequollene Baumwollsamen, die wöchentlich gewechselt werden. Ebenfalls wöchentlich feuchtet man den Sand mit reinem Wasser an.Petri dishes with a diameter of 10 cm are mixed with 1 ml of the acetone fabric solution lined. After the solvent has evaporated, it is filled the shells with 20 larvae of the penultimate stage. After 24 hours Transfer the surviving animals into 1 liter jars, which are 200 g sterile Quartz sand (grain size 0 to 3 mm) included. This sand was before Start the experiment with 25 ml of the aqueous active ingredient preparation. The feed is swollen cotton seeds that are changed weekly will. Also weekly, the sand is moistened with pure water.

Die Versuchstemperatur beträgt 25 bis 27°C. Die Beobachtungszeit erstreckt sich bis zum Schlüpfen der Eier in den Kontrollen. Beurteilt wird:The test temperature is 25 to 27 ° C. The observation period extends until the eggs hatch in the controls. The following is assessed:

  • 1. wöchentlich die Mortalität1. weekly mortality
  • 2. Häutung zum Adulten und Registrierung etwaiger Mißbildungen2. Molting for adults and registration of any malformations
  • 3. Eiablage3. Egg laying
  • 4. Eischlupf4. Egg hatching

In diesem Versuch lag die mortale Dosis der Verbindung Nr. 1 bei 10 ppm. In this experiment, the mortal dose of Compound No. 1 was 10 ppm.  

Beispiel BExample B Ovizide Wirkung bei Dysdercus intermedius (Baumwollwanze)Ovicidal effects in Dysdercus intermedius (cotton bug)

Stecketiketten mit einem ca. 8 mm breiten Klebestreifen werden 24 Stunden vor dem Versuchsbeginn in ein mit Baumwollwanzen-Eiern gefülltes Sammelgefäß eingetaucht. Die bei diesem Vorgang auf der Steckkarte haften gebliebenen Eier werden für ca. 5 Sekunden in die wäßrige Wirkstoffaufbereitung eingetaucht und auf einem Filterpapier abtropfen lassen, ohne daß die Eier das Filterpapier berühren. Anschließend werden die Stecketiketten mit dem Klebstreifen nach oben in Plastikpaletten gestellt, die eine mit Wasser durchfeuchtete halbe Watterolle enthalten, und mit einer Glasplatte abgedeckt. Nach dem Schlupf der Larven im Kontrollversuch (nach ca. 8 Tagen) wird bonitiert.Plant labels with an approx. 8 mm wide adhesive strip last 24 hours before starting the experiment into a one filled with cotton bug eggs Immersion container immersed. Which stick to the card during this process Any remaining eggs are soaked in the water for about 5 seconds Active ingredient preparation immersed and drained on a filter paper leave without the eggs touching the filter paper. Then be the stick-on labels with the adhesive tape facing up in plastic pallets which contain a half cotton roll soaked in water, and covered with a glass plate. After the hatching of the larvae in Control attempt (after approx. 8 days) is rated.

In diesem Versuch lag die mortale Dosis der Verbindung Nr. 1 bei 0,002%.In this experiment, the mortal dose of Compound No. 1 was 0.002%.

Beispiel CExample C Wirkung auf die Eiablage von Epilachna varivestis (Mexikanischer Bohnenkäfer)Effect on the egg laying of Epilachna varivestis (Mexican Bean beetle)

Gruppen von je 20 Eiern des Mexikanischen Bohnenkäfers werden mit ihrer Blattunterlage für 3 Sekunden in die wäßrige Wirkstoffaufbereitung getaucht. Anschließend plaziert man sie auf einem aufgefeuchteten Filterpapier in Kunststoff-Käfige. Registriert wird der Schlupf lebensfähiger Larven - was an der Annahme des gebotenen Futters zu erkennen ist.Groups of 20 Mexican Bean Beetle eggs each with their Sheet support for 3 seconds in the aqueous preparation of active ingredient submerged. Then you place them on a moistened Filter paper in plastic cages. The slip is registered viable larvae - what about accepting the offered food too is recognizable.

In diesem Versuch lag die mortale Dosis der Verbindung Nr. 1 bei 0,02 ppm. In this experiment, the mortal dose of Compound No. 1 was 0.02 ppm.  

Beispiel DExample D Entwicklungshemmung von Heliothis virescens auf behandeltem NährbodenInhibition of development of Heliothis virescens on treated medium

100 g des Standard-Nährbodens für Heliothis werden in 250 ml-Becher gefüllt und warm mit der wäßrigen Wirkstoffaufbereitung sorgfältig gemischt. Nach Erkalten belegt man jedes Gefäß mit 10 Raupen im dritten Larvenstadium (1,5 bis 1,8 cm) und lagert sie bei 23°C. Beurteilt wird Verpuppung und Schlupf der Falter.100 g of the standard medium for Heliothis are placed in 250 ml beakers filled and warm with the aqueous active ingredient preparation carefully mixed. After cooling, each container is covered with 10 caterpillars in the third Larval stage (1.5 to 1.8 cm) and store at 23 ° C. Is judged The pupae pupate and hatch.

Bei diesem Versuch lag die mortale Dosis der Verbindung Nr. 1 bei 1 ppm.In this trial, the mortal dose of Compound No. 1 was 1 ppm.

Claims (5)

1. [(p-Phenoxy)-phenoxy]-methyl-isoxazole der allgemeinen Formel I in der die Substituenten die folgende Bedeutung haben:R¹, R², R³Wasserstoff, Halogen, C₁-C₈-Alkyl, C₁-C₈-Alkoxy, C₁-C₄-Halogenalkyl, C₁-C₄-Halogenalkoxy, Nitro oder Cyano, R⁴Wasserstoff oder C₁-C₄-Alkyl, R⁵Wasserstoff, Halogen, C₁-C₈-Alkyl oder C₂-C₈-Alkenyl, R⁶Wasserstoff, C₁-C₈-Alkyl, C₂-C₈-Alkenyl, C₁-C₄-Halogenalkyl, C₂-C₈-Alkoxy-alkyl, C₃-C₁₀-Cycloalkyl, Aryl, C₇-C₂₀-Aryl-alkyl oder im Arylteil ein- bis dreifach durch Halogen, C₁-C₈-Alkyl, C₁-C₈-Alkoxy, C₁-C₄-Halogenalkyl, C₁-C₄-Halogenalkoxy oder Cyano, oder ein- bis dreifach durch Nitro substituiertes Aryl oder C₇-C₂₀-Aryl-alkyl.1. [(p-phenoxy) phenoxy] methyl isoxazoles of the general formula I in which the substituents have the following meaning: R¹, R², R³hydrogen, halogen, C₁-C₈-alkyl, C₁-C₈-alkoxy, C₁-C₄-haloalkyl, C₁-C₄-haloalkoxy, nitro or cyano, R⁴hydrogen or C₁-C₄ -Alkyl, R⁵hydrogen, halogen, C₁-C₈-alkyl or C₂-C₈-alkenyl, R⁶hydrogen, C₁-C₈-alkyl, C₂-C₈-alkenyl, C₁-C₄-haloalkyl, C₂-C₈-alkoxy-alkyl, C₃-C₁₀ -Cycloalkyl, aryl, C₇-C₂₀-aryl-alkyl or in the aryl part one to three times by halogen, C₁-C₈-alkyl, C₁-C₈-alkoxy, C₁-C₄-haloalkyl, C₁-C₄-haloalkoxy or cyano, or a - Aryl or C₇-C₂₀-aryl-alkyl substituted three times by nitro. 2. Verfahren zur Herstellung der [(p-Phenoxy)-phenoxy]-methyl-isoxazole der allgemeinen Formel I gemäß Anspruch 1, dadurch gekennzeichnet, daß man in an sich bekannter Weise
  • a) (p-Phenoxy)-phenole II mit einem Isoxazol der Formel III in der X für eine Abgangsgruppe steht, in Gegenwart einer Base oder
  • b) ein Phenolatanion von II mit einem Isoxazol III umsetzt.
2. Process for the preparation of the [(p-phenoxy) phenoxy] methyl isoxazoles of the general formula I according to claim 1, characterized in that in a manner known per se
  • a) (p-phenoxy) phenols II with an isoxazole of formula III in which X represents a leaving group, in the presence of a base or
  • b) a phenolate anion of II reacted with an isoxazole III.
3. Schädlingsbekämpfungsmittel, enthaltend ein [(p-Phenoxy)-phenoxy]- methyl-isoxazol gemäß Anspruch 1 neben hierfür üblichen Trägerstoffen.3. Pesticides containing a [(p-phenoxy) phenoxy] - methyl-isoxazole according to claim 1 in addition to the usual carriers. 4. Schädlingsbekämpfungsmittel nach Anspruch 3, dadurch gekennzeichnet, daß es 0,1 bis 95 Gew.-% eines [(p-Phenoxy)-phenoxy]-methyl-isoxazols der Formel I enthält.4. pesticide according to claim 3, characterized in that it is 0.1 to 95 wt .-% of a [(p-phenoxy) phenoxy] methyl isoxazole of formula I contains. 5. Verfahren zur Bekämpfung von Schädlingen, dadurch gekennzeichnet, daß man die Schädlinge und/oder die von Schädlingen freizuhaltenden Flächen und/oder Räume mit einer für Schädlinge wirksamen Menge eines [(p-Phenoxy)-phenoxy]-methyl-isoxazols der Formel I gemäß Anspruch 1 behandelt.5. A method for controlling pests, characterized in that the pests and / or those to be kept free from pests Areas and / or rooms with an effective amount for pests [(p-Phenoxy) phenoxy] methyl isoxazole of the formula I according to claim 1 treated.
DE19873713337 1987-04-21 1987-04-21 [(p-Phenoxy)phenoxy]methylisoxazoles Withdrawn DE3713337A1 (en)

Priority Applications (15)

Application Number Priority Date Filing Date Title
DE19873713337 DE3713337A1 (en) 1987-04-21 1987-04-21 [(p-Phenoxy)phenoxy]methylisoxazoles
AT88105990T ATE88702T1 (en) 1987-04-21 1988-04-14 P-PHENOXY-PHENOXYMETHYL FIVE-RINGED HETEROAROMATICS
ES88105990T ES2054725T3 (en) 1987-04-21 1988-04-14 RING HETEROAROMATES OF FIVE MEMBERS OF P-PHENOXY-PHENOXIMETHYL.
EP88105990A EP0287959B1 (en) 1987-04-21 1988-04-14 P-phenoxy--phenoxymethyl substituted five membered heteroaromatics
DE8888105990T DE3880544D1 (en) 1987-04-21 1988-04-14 P-PHENOXY-PHENOXYMETHYL-FUENFRING-HETEROAROMAT.
IL86098A IL86098A (en) 1987-04-21 1988-04-18 (p-phenoxyphenoxy)-methyl-five-membered heteroaromatic compounds,their preparation and their use as insecticides,spidercides and/or nematocides
US07/184,122 US4943584A (en) 1987-04-21 1988-04-20 (p-Phenoxyphenoxy)-methyl-five-membered hetaryls
JP63095803A JP2534315B2 (en) 1987-04-21 1988-04-20 Novel (p-phenoxy-phenoxy) -methyl 5-membered heteroaromatic compound
HU882015A HU202364B (en) 1987-04-21 1988-04-20 Insecticide compositions containing (p-phenoxy-phenoxy)-methyl-heteroaromatic compounds as active components and process for producing the active components
CA000564555A CA1331619C (en) 1987-04-21 1988-04-20 (p-phenoxyphenoxy)-methyl-fivemembered hetaryls
BR8801878A BR8801878A (en) 1987-04-21 1988-04-20 PROCESS FOR OBTAINING COMPOUNDS (P-FENOXI-FENOXI) -PENTAMEMBERED AROMATIC METHYL AND PESTICIDED COMPOSITES BASED ON THE SAME
SU4355533A SU1655293A3 (en) 1987-04-21 1988-04-20 Remedy for struggle against insects
ZA882757A ZA882757B (en) 1987-04-21 1988-04-20 (p-phenoxyphenoxy)-methyl-five-membered hetaryls
KR1019880004526A KR960010354B1 (en) 1987-04-21 1988-04-21 (p-phenoxy-phenoxy)-methyl-five-membered hetaryls
MX9203407A MX9203407A (en) 1987-04-21 1992-06-25 (P-PHENOXIFENOXI) -HETEROARILS OF FIVE MEMBERS.

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE19873713337 DE3713337A1 (en) 1987-04-21 1987-04-21 [(p-Phenoxy)phenoxy]methylisoxazoles

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DE3713337A1 true DE3713337A1 (en) 1988-11-10

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DE (1) DE3713337A1 (en)
ZA (1) ZA882757B (en)

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