DE3826682A1 - Phenoxyalkyl-substituted heteroaromatics, their preparation, and their use for controlling pests - Google Patents
Phenoxyalkyl-substituted heteroaromatics, their preparation, and their use for controlling pestsInfo
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- DE3826682A1 DE3826682A1 DE3826682A DE3826682A DE3826682A1 DE 3826682 A1 DE3826682 A1 DE 3826682A1 DE 3826682 A DE3826682 A DE 3826682A DE 3826682 A DE3826682 A DE 3826682A DE 3826682 A1 DE3826682 A1 DE 3826682A1
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- phenoxyalkyl
- substituted
- alkyl
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- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
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- 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
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- C07D233/56—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 only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
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- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
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- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
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- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
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- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
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- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles 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 in position 2
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- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles 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 in position 2
- C07D235/26—Oxygen atoms
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- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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Abstract
Description
Die vorliegende Erfindung betrifft neue phenoxyalkylsubstituierte Heteroaromaten der allgemeinen Formel IThe present invention relates to new phenoxyalkyl substituted Heteroaromatics of the general formula I
in der die Substituenten die folgende Bedeutung haben:in which the substituents have the following meaning:
A ein gegebenenfalls substituierter Heteroaromat mit 6 Ringgliedern und
1, 2 oder 3 Stickstoffatomen
R¹ Wasserstoff, Halogen oder C₁-C₃-Alkyl,
R² Wasserstoff oder C₁-C₄-Alkyl und
Q ein Fünfringheteroaromat, der über ein C-Atom gebunden ist 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.A is an optionally substituted heteroaromatic with 6 ring members and 1, 2 or 3 nitrogen atoms
R¹ is hydrogen, halogen or C₁-C₃-alkyl,
R² is hydrogen 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.
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.
In der EP-A-92 706, DE-A-34 08 528 und den japanischen Anmeldungen JP 57/175177, JP 57/175179 und JP 59/98083 werden phenoxyalkylsubstituierte Heteroaromaten als herbizide Wirkstoffe beschrieben; einen Hinweis auf insektizide Wirkung findet man in diesen Schriften nicht.In EP-A-92 706, DE-A-34 08 528 and Japanese applications JP 57/175177, JP 57/175179 and JP 59/98083 are phenoxyalkyl substituted Heteroaromatics described as herbicidal active ingredients; one There is no evidence of insecticidal activity in these documents.
Überraschenderweise wurde nun gefunden, daß sich die eingangs definierten neuen phenoxyalkylsubstituierten Heteroaromaten hervorragend zur Bekämpfung von Schädlingen eignen.Surprisingly, it has now been found that those defined at the outset new phenoxyalkyl-substituted heteroaromatics excellent for combating of 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 Fünfringhetaroaromaten 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 five-ring hetaro aromatic 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 Reaktionsgleichung 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 reaction equation, the radical Y is a conventional one Leaving group, such as 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.
Die Phenole II sind zum Teil aus CH-A-6 52 714, Res. Discl. 214, 32 (1982) und DE-A-33 20 534 bekannt, oder können nach den dort beschriebenen Methoden hergestellt werden.The phenols II are partly from CH-A-6 52 714, Res. Discl. 214, 32 (1982) and DE-A-33 20 534 known, or can according to those described there Methods are made.
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 beispielsweise 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, 286, 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 for example 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. Comprehensive Heterocyclic Chemistry, R. Katritzky and W. Rees, Vol. 6, p. 166, 177, 235, 286, 425 ff, Pergamon Press, 1984; of imidazole derivatives e.g. B. in Advances in Heterocyclic Chemistry, vol. 27, pp. 242 ff, 1980; from Pyrazole derivatives e.g. B. in 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, p. 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 Verbindung 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 daraus vorteilhaft sein.For the preparation of the compound 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 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 Diethylether, 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 ether, 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:The individual substituents in formula I have the following meanings:
A ein gegebenenfalls substituierter Heteroaromat mit 6 Ringgliedern und 1, 2 oder 3 Stickstoffatomen, beispielsweise der allgemeinen Formeln IVa bis IVeA is an optionally substituted heteroaromatic with 6 ring members and 1, 2 or 3 nitrogen atoms, for example the general one Formulas IVa to IVe
wobei als Heteroaromaten bevorzugt Pyridin-2-yl, Pyridin-3-yl, Pyridin-4-yl, Pyrimidin-2-yl, Pyrimidin-4-yl, Pyrimidin-5-yl, Pyridazin-3-yl, Pyridazin-4-yl, Pyrazin-2-yl, Pyrazin-3-yl, 1,3,5-Triazin-2-yl und besonders bevorzugt Pyridin-2-yl, Pyrimidin-2-yl, Pyrimidin-4-yl, Pyrimidin-5-yl, Pyridazin-3-yl und Pyrazin-2-yl zu nennen sind und als Reste R³ unabhängig voneinander bevorzugt,preferably pyridin-2-yl, pyridin-3-yl, Pyridin-4-yl, pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl, Pyridazin-3-yl, pyridazin-4-yl, pyrazin-2-yl, pyrazin-3-yl, 1,3,5-triazin-2-yl and particularly preferably pyridin-2-yl, Pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl, pyridazin-3-yl and Pyrazin-2-yl and R³ are independent of each other prefers,
- - Wasserstoff,- hydrogen,
- - Halogen wie Fluor, Chlor und Brom, insbesondere Fluor und Chlor,Halogen such as fluorine, chlorine and bromine, in particular fluorine and chlorine,
- - unverzweigtes oder verzweigtes C₁-C₄-Alkyl, wie Methyl, Ethyl, Propyl, Butyl, insbesondere unverzweigtes Alkyl wie Methyl und Ethyl oder verzweigtes Alkyl wie Isopropyl, Isobutyl und sec.-Butyl,unbranched or branched C₁-C₄ alkyl, such as methyl, ethyl, propyl, Butyl, especially unbranched alkyl such as methyl and ethyl or branched alkyl such as isopropyl, isobutyl and sec-butyl,
- - unverzweigtes oder verzweigtes C₁-C₃-Halogenalkyl, insbesondere Fluor- und Chloralkyl wie Fluormethyl, Difluormethyl, Trifluormethyl, Pentafluorethyl, 2,2,2-Trifluorethyl, Chlormethyl, Dichlormethyl, Trichlormethyl und 2,2,2-Trichlorethyl,- Unbranched or branched C₁-C₃ haloalkyl, in particular Fluoro and chloroalkyl such as fluoromethyl, difluoromethyl, trifluoromethyl, Pentafluoroethyl, 2,2,2-trifluoroethyl, chloromethyl, dichloromethyl, Trichloromethyl and 2,2,2-trichloroethyl,
- - unverzweigtes oder verzweigtes C₁-C₄-Alkoxy, insbesondere Methoxy, Ethoxy und Isopropyloxy,unbranched or branched C₁-C₄ alkoxy, especially methoxy, Ethoxy and isopropyloxy,
- - unverzweigtes oder verzweigtes C₁-C₃-Halogenalkoxy, insbesondere Fluor- und Chloralkoxy wie Trifluormethoxy, Trichlormethoxy, 1,1,2,2-Tetrafluorethoxy und Pentafluorethoxy,- Unbranched or branched C₁-C₃ haloalkoxy, in particular Fluoro and chloroalkoxy such as trifluoromethoxy, trichloromethoxy, 1,1,2,2-tetrafluoroethoxy and pentafluoroethoxy,
- - C₃-C₆-Cycloalkyl wie Cyclopropyl, Cyclobutyl, Cyclopentyl, Cyclohexyl, insbesondere Cyclopropyl,- C₃-C₆-cycloalkyl such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, especially cyclopropyl,
- - Cyano und- Cyano and
- - Nitro- Nitro
in Frage kommen,
R¹ - Wasserstoff,
- Halogen wie Fluor, Chlor und Brom, bevorzugt Fluor und Chlor,
- unverzweigtes oder verzweigtes C₁-C₃-Alkyl wie Methyl, Ethyl und
Isopropyl,
R² - Wasserstoff,
- C₁-C₄-Alkyl wie Methyl, Ethyl, Propyl, Isopropyl, Butyl,
besonders bevorzugt Methyl,
Q - ein gegebenenfalls substituierter Fünfringheteroaromat mit 1 bis
4, insbesondere 1, 2 und 3 Heteroatomen wie Stickstoff, Schwefel
oder Sauerstoff, bevorzugt gegebenenfalls substituiertes Thiophen-
2-yl, Thiophen-3-yl, Thiazol-2-yl, Thiazol-4-yl, Thiazol-
5-yl, Oxazol-2-yl, Oxazol-4-yl, Oxazol-5-yl, Imidazol-2-yl,
Imidazol-4-yl, Imidazol-5-yl, Isothiazol-3-yl, Isothiazol-4-yl,
Isothiazol-5-yl, Pyrazol-3-yl, Pyrazol-4-yl, Isoxazol-3-yl,
Isoxazol-5-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, 1,3,4-Thiadiazol-2-yl, 1,3,4-Oxadiazol-2-yl,
1,2,4-Oxadiazol-3-yl, Isoxazol-3-yl und Isoxazol-5-yl.come into question
R¹ - hydrogen,
Halogen such as fluorine, chlorine and bromine, preferably fluorine and chlorine,
- Unbranched or branched C₁-C₃ alkyl such as methyl, ethyl and isopropyl,
R² - hydrogen,
- C₁-C₄-alkyl such as methyl, ethyl, propyl, isopropyl, butyl, particularly preferably methyl,
Q - an optionally substituted five-ring heteroaromatic with 1 to 4, in particular 1, 2 and 3, heteroatoms such as nitrogen, sulfur or oxygen, preferably optionally substituted thiophene-2-yl, thiophene-3-yl, thiazol-2-yl, thiazol-4- yl, thiazol-5-yl, oxazol-2-yl, oxazol-4-yl, oxazol-5-yl, imidazol-2-yl, imidazol-4-yl, imidazol-5-yl, isothiazol-3-yl, Isothiazol-4-yl, isothiazol-5-yl, pyrazol-3-yl, pyrazol-4-yl, isoxazol-3-yl, isoxazol-5-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, 1,3,4-thiadiazol-2-yl, 1,3,4-oxadiazol-2-yl, 1,2, 4-oxadiazol-3-yl, isoxazol-3-yl and isoxazol-5-yl.
Der Fünfringheteroaromat kann gegebenenfalls ein- oder mehrfach substituiert sein mit:The five-ring heteroaromatic can optionally be substituted one or more times be with:
- - Halogen, bevorzugt Fluor, Chlor und Brom, besonders bevorzugt Chlor und Brom,- Halogen, preferably fluorine, chlorine and bromine, particularly preferably chlorine and bromine,
- - C₁-C₈-Alkyl, bevorzugt C₁-C₄-Alkyl, besonders bevorzugt Methyl, Ethyl, Isopropyl und tert.-Butyl,- C₁-C₈-alkyl, preferably C₁-C₄-alkyl, particularly preferably methyl, ethyl, Isopropyl and tert-butyl,
- - C₂-C₈-Alkenyl, bevorzugt C₂-C₄-Alkenyl, besonders bevorzugt Ethylen, 1-Methyl-ethen-1-yl, Propen-1-yl, 2-Methyl-propen-1-yl,- C₂-C₈ alkenyl, preferably C₂-C₄ alkenyl, particularly preferably ethylene, 1-methyl-ethen-1-yl, propen-1-yl, 2-methyl-propen-1-yl,
- - C₁-C₄-Halogenalkyl, bevorzugt Fluor oder Chlor substituiertes C₁-C₂-Halogenalkyl, besonders bevorzugt Trifluormethyl, 2,2,2-Trifluorethyl,- C₁-C₄ haloalkyl, preferably fluorine or chlorine substituted C₁-C₂-haloalkyl, particularly preferably trifluoromethyl, 2,2,2-trifluoroethyl,
- - C₁-C₈-Alkoxy, bevorzugt C₁-C₃-Alkoxy, besonders bevorzugt Methoxy, Ethoxy, n-Propyloxy und Isopropyloxy,- C₁-C₈-alkoxy, preferably C₁-C₃-alkoxy, particularly preferably methoxy, Ethoxy, n-propyloxy and isopropyloxy,
- - C₁-C₈-Alkylthio, bevorzugt C₁-C₃-Alkylthio, besonders bevorzugt Methylthio, Ethylthio, n-Propylthio und Isopropylthio, - C₁-C₈-alkylthio, preferably C₁-C₃-alkylthio, particularly preferred Methylthio, ethylthio, n-propylthio and isopropylthio,
- - C₂-C₈-Alkoxyalkyl, bevorzugt C₂-C₄-Alkoxyalkyl, besonders bevorzugt Methoxymethyl, 1-Methoxyethyl, 2-Methoxyethyl, 1-Methoxypropyl,- C₂-C₈-alkoxyalkyl, preferably C₂-C₄-alkoxyalkyl, particularly preferred Methoxymethyl, 1-methoxyethyl, 2-methoxyethyl, 1-methoxypropyl,
- - C₃-C₈-Cycloalkyl, bevorzugt C₃-C₅-Cycloalkyl, besonders bevorzugt Cyclopropyl, Cyclobutyl und Cyclopentyl.- C₃-C₈-cycloalkyl, preferably C₃-C₅-cycloalkyl, particularly preferred Cyclopropyl, cyclobutyl and cyclopentyl.
Die phenoxyalkylsubstituierten Heteroaromaten 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 heteroaromatics 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), 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 (Forleule),
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 cochloeariae (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 Zweiflüger (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);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 wrapper), Tortrix viridana (oak wrapper), Clysia ambiguella (hay and sour worm); Evetria buoliana (pine shoot winder), Polychrosis botrana (crossed grape wrap), Cydia pomonella (fruit made), Laspeyresia molesta (peach shoot borer), Laspeyresia funebrana (plum wrapper), Ostrinia nubilalis (corn borer), Loxostegeuelliellicali (St suppressalis (rice stalk borer), Galleria mellonella (wax moth), Malacosoma neustria (ring spinner), Dendrolimus pini (pine spinner), Thaumatopoea ptiyocampa (pine procession spinner), Phalera bucephala (moon spot), Cheimatobia brumata (small frost spanner) (small frost spanner) (small frost spanner) (small frost spanner) piniarius (pine tensioner), Hyphantria cunea (white bear spinner), Agrotis segetum (winter seed owl), Agrotis ypsilon (Ypsiloneule), Barathra brassicae (coal owl), Cirphis unipuncta (army worm), Prodenia litura (cotton caterpillar), Laphygmaer, Laphygma Panolis flammea (Forleule), Earias insulana (Cotton Capsule Worm), Plusia gamma (Gammaeule), Alabama ar gillacea (cotton 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 cochloeariae (Horseradish Leaf Beetle), Phyllotreta nemorum (Cabbage Flea), Chaetocnema tibialis (Beet Flea Beetle), Phyllophalicaotica (Phyllodophelica), Phylloalphaica, Phyllodaltaphotica beetle, Phyllodophelica beetle flea beetle (Diabola flea beetle), Phylloalphaica (Rhodichlora flotilla), Phylloalphaicaphotus ), Cassida nebulosa (misty tortoise beetle), Bruchus lenti s (lenticular beetle), Bruchus rufimanus (horse bean beetle), Bruchus pisorum (pea beetle), Sitona lineatus (lined leaf beetle), Ortiorrhynchus sulcatus (furrowed Lappelweed), Otiorrhynchus ovatus (strawberry root, Rotteleberries), betel , Anthonomus pomorum (apple blossom engraver), Anthonomus grandis (capsule beetle), Ceuthorrhynchus assimilis (cabbage weevil), Ceuthorrynchus napi (large cabbage weevil), Sitophilus granaria (grain beetle), Anisandrus dispar (unequaled wood borkops typographers) Blaster (I), );
from the order of the two-winged birds (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 rose (turnip wasp), Hoplocampa minuta (plum saw wasp), Monomorium pharaonis (pharaoh ant), Solenopsis geminata (fire ant), Atta sexdens (leaf cutter ant);
aus der Ordnung der Wanzen (Heteroptera) beispielsweise Nezara viridula
(Grüne Reiswanze), Eurygaster integriceps (Asiatische Getreidewande),
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 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 (Mauwurfsgrille), 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).from the order of the bugs (Heteroptera), for example Nezara viridula (green rice bug), Eurygaster integriceps (Asian cereal wall), 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 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 (barn cricket), Tachycines asynamorus (greenhouse insect), Locusta migratoria (mantis grasshopper) (Stauronotkan maroccanus peregrine maroccanus) 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 dispsaci, Ditylenchus destructor, Pratylenchus neglectus, Pratylenchus penetrans, Paratylenchus goodeyi, Paratylenchus curvitatus sowie Tylenchlorhynchus 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, Cyst-forming nematodes, e.g. B. Globodera rostochiensis, heterodera schacutii, Heterodera avenae, Heterodera glycinae, Heterodera triflolii, Stick and leaf flakes, e.g. B. Ditylenchus dispsaci, Ditylenchus destructor, Pratylenchus neglectus, Pratylenchus penetrans, Paratylenchus goodeyi, Paratylenchus curvitatus and Tylenchlorhynchus 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 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, sprinkles, granules by spraying, Nebulization, dusting, scattering or pouring can be used. The Forms of application depend entirely on the purposes of use; they should in any case be the finest possible distribution of the invention Ensure active ingredients.
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 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, Aklylarylpolyetheralkohole, Isotridecylalkohol, Fettalkoholethylenoxid- Kondensate, ethoxyliertes Rizinusöl, Polyoxyethylenalkylether, ethoxyliertes Polyoxypropylen, Laurylalkoholpolylglykoletheracetal, Sorbitester, Lignin, Sulfitablaugen und Methylcellulose in Betracht.Alkali, alkaline earth, ammonium salts come as surface-active substances of 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, Aklylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol ethylene oxide Condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers, ethoxylated polyoxypropylene, lauryl alcohol polyglycol ether acetal, Sorbitol ester, lignin, sulfite waste liquor and methyl cellulose in Consider.
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, ureas and herbal products, such as corn 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. 3 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. 3 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. 22 werden mit einer Mischung aus 92 Gew.-Teilen pulverförmigen 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. 22 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. 79 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. 79 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. 3 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. 3 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 adduct of 40 moles of ethylene oxide to 1 mole of castor oil consists.
- V. 80 Gew.-Teile der Verbindung Nr. 22 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. 22 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 Erfolgt 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 be used with success in the ultra-low-volume process (ULV) can be used, whereby it is 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.
3,5 g 4-(6-Chlor-2-pyridinyloxy)phenol und 3,2 g Kaliumcarbonat werden in 100 ml trockenem Dimethylformamid 1 Stunde bei 60°C gerührt. Anschließend werden 6,5 g 5-Brom-2-chlormethylthiophen in 30 ml trockenem Dimethylformamid zugetropft. Man rührt 6 Stunden bei 80°C und über Nacht bei Raumtemperatur (ca. 20°C) nach. Zur Aufarbeitung gießt man in 200 ml Eiswasser. Das ausgefallene Rohprodukt wird abgesaugt und aus n-Hexan/Essigester = 4/1 umkristallisiert. Man erhält 3,1 g 2-[4-(6-Chlor-2-pyridinyloxy)phenoxymethyl]5- bromthiophen mit Fp.: 78-80°C.3.5 g of 4- (6-chloro-2-pyridinyloxy) phenol and 3.2 g of potassium carbonate are added 100 ml of dry dimethylformamide stirred at 60 ° C for 1 hour. Subsequently 6.5 g of 5-bromo-2-chloromethylthiophene in 30 ml of dry dimethylformamide dripped. The mixture is stirred at 80 ° C. for 6 hours and at room temperature overnight (approx. 20 ° C) after. For working up, pour into 200 ml of ice water. The precipitated crude product is suctioned off and from n-hexane / ethyl acetate = 4/1 recrystallized. 3.1 g of 2- [4- (6-chloro-2-pyridinyloxy) phenoxymethyl] 5- are obtained. bromothiophene with mp: 78-80 ° C.
Zu 1,3 g 100%igem Natriumhydrid in 40 ml trockenem Dimethylformamid tropft man bei Raumtemperatur (ca. 20°C) 11,1 g 4-(6-Chlor-2-pyridinyloxy)phenol in 100 ml trockenem Dimethylformamid. Zur Vervollständigung der exothermen Reaktion (Wasserstoffentwicklung) rührt man 30 Minuten bei 50°C nach. Anschließend tropft man bei Raumtemperatur (ca. 20°C) 7,9 g 5-Chlormethyl- 3-cyclopropylisoxazol in 30 ml trockenem Dimethylformamid zu. Man rührt 2 Stunden bei 60°C und über Nacht bei Raumtemperatur ca. 20°C) nach. Zur Aufarbeitung gießt man in 200 ml Eiswasser und extrahiert die Lösung 3mal mit Methyl-tert.-butylether. Die organische Phase wird anschließend 2mal mit 2n-Natronlauge, 2mal mit Wasser und einmal mit gesättigter Kochsalzlösung gewaschen. Nach dem Trocknen über Natriumsulfat wird das Lösungsmitel im Vakuum verdampft. Das Rohprodukt wird aus Methanol umkristallisiert. Man erhält 13,5 g 5-[4-(6-Chlor-2-pyridinyloxy) phenoxymethyl]3-cyclopropylisoxazol mit Fp.: 128-130°C. To 1.3 g of 100% sodium hydride in 40 ml of dry dimethylformamide 11.1 g of 4- (6-chloro-2-pyridinyloxy) phenol are added dropwise at room temperature (about 20 ° C.) in 100 ml of dry dimethylformamide. To complete the exothermic reaction (evolution of hydrogen) is stirred at 50 ° C. for 30 minutes to. Then drop in at room temperature (approx. 20 ° C.) 7.9 g of 5-chloromethyl 3-cyclopropylisoxazole in 30 ml of dry dimethylformamide. Man stir for 2 hours at 60 ° C and overnight at room temperature approx. 20 ° C) to. For working up, pour into 200 ml of ice water and extract the Solution 3 times with methyl tert-butyl ether. The organic phase will then twice with 2N sodium hydroxide solution, twice with water and once with saturated saline. After drying over sodium sulfate the solvent is evaporated in vacuo. The raw product is made Recrystallized methanol. 13.5 g of 5- [4- (6-chloro-2-pyridinyloxy) are obtained phenoxymethyl] 3-cyclopropylisoxazole with mp: 128-130 ° C.
Zu 0,6 g 100%igem Natriumhydrid in 20 ml trockenem Dimethylformamid tropft man bei Raumtemperatur (ca. 20°C) 4,9 g 4-(6-Chlor-2-pyridinyloxy) phenol in 40 ml trockenem Dimethylformamid. Zur Vervollständigung der exothermen Reaktion (Wasserstoffentwicklung) rührt man 30 Minuten bei 50°C nach. Anschließend tropft man bei Raumtemperatur (ca. 20°C) 4 g 5-Chlormethyl- 2-ethoxy-1,3,4-thiadiazol in 20 ml trockenem Dimethylformamid zu und rührt 2 Stunden bei 60°C und über Nacht bei Raumtemperatur (ca. 20°C) nach. Zur Aufarbeitung gießt man in 200 ml Eiswasser. Das ausgefallene Rohprodukt wird abgesaugt und aus Isopropanol umkristallisiert. Man erhält 5,4 g 5-[4-(6-Chlor-2-pyridinyloxy)phenoxymethyl]-2-ethoxy-1,3,4-thiadiazo-l mit Fp.: 92°C-94°C.To 0.6 g of 100% sodium hydride in 20 ml of dry dimethylformamide 4.9 g of 4- (6-chloro-2-pyridinyloxy) are added dropwise at room temperature (approx. 20 ° C.) phenol in 40 ml dry dimethylformamide. To complete the exothermic reaction (evolution of hydrogen) is stirred at 50 ° C. for 30 minutes to. 4 g of 5-chloromethyl- are then added dropwise at room temperature (about 20.degree. 2-ethoxy-1,3,4-thiadiazole in 20 ml of dry dimethylformamide and stirred for 2 hours at 60 ° C and overnight at room temperature (approx. 20 ° C) to. For working up, pour into 200 ml of ice water. The fancy The crude product is filtered off and recrystallized from isopropanol. You get 5.4 g of 5- [4- (6-chloro-2-pyridinyloxy) phenoxymethyl] -2-ethoxy-1,3,4-thiadiazo-l with mp: 92 ° C-94 ° C.
Entsprechend dieser Herstellvorschriften können die in der folgenden Tabelle beschriebenen Verbindungen I hergestellt werden. Die Substitutionsstellen an den Heteroaromaten sind jeweils durch einen Punkt gekennzeichnet.According to these manufacturing instructions, the following can Compounds I described in the table can be prepared. The Substitution sites on the heteroaromatics are each with a dot featured.
Die ohne Angabe physikalischer Kenngrößen in der nachstehenden Tabelle 1 aufgeführten Verbindungen I können aus entsprechenden Vorprodukten ohne weiteres erhalten werden und lassen eine gleichartige Wirkung erwarten. The without specifying physical parameters in Table 1 below Compounds I listed can be obtained from corresponding precursors without more can be obtained and a similar effect can be expected.
Claims (5)
R¹ Wasserstoff, Halogen oder C₁-C₃-Alkyl,
R² Wasserstoff oder C₁-C₄-Alkyl und
Q ein Fünfringheteroaromat, der über ein C-Atom gebunden ist und gegebenenfalls ein- oder mehrfach mit Halogen, C₁-C₆-Alkyl, C₂-C₈-Alkenyl, C₁-C₄-Halogenalkyl, C₁-C₈-Alkoxy, C₁-C₈-Alkylthio, C₂-C₈-Alkoxyalkyl oder C₃-C₁₀-Cycloalkyl substituiert ist.Phenoxyalkyl-substituted heteroaromatics of the general formula I in which the substituents have the following meaning: A is an optionally substituted heteroaromatic with 6 ring members and 1, 2 or 3 nitrogen atoms
R¹ is hydrogen, halogen or C₁-C₃-alkyl,
R² is hydrogen 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-C₆-alkyl, C₂-C₈-alkenyl, C₁-C₄-haloalkyl, C₁-C₈-alkoxy, C₁-C₈-alkylthio , C₂-C₈-alkoxyalkyl or C₃-C₁₀-cycloalkyl is substituted.
Priority Applications (16)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3826682A DE3826682A1 (en) | 1988-08-05 | 1988-08-05 | Phenoxyalkyl-substituted heteroaromatics, their preparation, and their use for controlling pests |
| EP89114056A EP0353674B1 (en) | 1988-08-05 | 1989-07-29 | Phenoxyalkyl-substituted heteroaromates, process for their preparation and their use in combating pests |
| DE58907554T DE58907554D1 (en) | 1988-08-05 | 1989-07-29 | Phenoxyalkyl-substituted heteroaromatics, process for their preparation and their use for controlling pests. |
| ES89114056T ES2051939T3 (en) | 1988-08-05 | 1989-07-29 | Phenoxyalkyl substituted aromatics, procedures for obtaining and using them for the fight against plagues. |
| NZ230188A NZ230188A (en) | 1988-08-05 | 1989-08-03 | Phenoxyalkyl derivatives substituted with two heterocyclic groups,and pesticidal compositions |
| ZA895953A ZA895953B (en) | 1988-08-05 | 1989-08-04 | Phenoxyalkyl-substituted heteroaromatics and their use for controlling pests |
| US07/389,815 US4996216A (en) | 1988-08-05 | 1989-08-04 | Phenoxyalkyl-substituted heteroaromatics and their use for controlling pests |
| JP1201490A JP2760853B2 (en) | 1988-08-05 | 1989-08-04 | Phenoxyalkyl-substituted heteroaromatic compounds, pest control agents and control methods using the same |
| AU39299/89A AU616547B2 (en) | 1988-08-05 | 1989-08-04 | Phenoxyalkyl-substituted heteroaromatics and their use for controlling pests |
| CA000607643A CA1336095C (en) | 1988-08-05 | 1989-08-04 | Phenoxyalkyl-substituted heteroaromatics and their use for controlling pests |
| KR1019890011244A KR0125578B1 (en) | 1988-08-05 | 1989-08-05 | Phenoxyalkyl-substituted heteroaromatic compounds and methods for preparing the same, and pesticides containing the same |
| US07/606,813 US5132308A (en) | 1988-08-05 | 1990-10-31 | Phenoxyalkyl-substituted heteroaromatics and their use for controlling pests |
| US07/834,839 US5180727A (en) | 1988-08-05 | 1992-02-13 | Phenoxyalkyl-substituted heteroaromatics and their use for controlling pests |
| US07/932,061 US5264434A (en) | 1988-08-05 | 1992-08-19 | Phenoxyalkyl-substituted heteroaromatics and their use for controlling pests |
| US08/087,482 US5300502A (en) | 1988-08-05 | 1993-07-08 | Phenoxyalkyl-substituted heteroaromatics and their use for controlling pests |
| US08/162,601 US5416100A (en) | 1988-08-05 | 1993-12-07 | Phenoxyalkyl-substituted heteroaromatics and their use for controlling pests |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3826682A DE3826682A1 (en) | 1988-08-05 | 1988-08-05 | Phenoxyalkyl-substituted heteroaromatics, their preparation, and their use for controlling pests |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3826682A1 true DE3826682A1 (en) | 1990-02-08 |
Family
ID=6360328
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE3826682A Withdrawn DE3826682A1 (en) | 1988-08-05 | 1988-08-05 | Phenoxyalkyl-substituted heteroaromatics, their preparation, and their use for controlling pests |
Country Status (2)
| Country | Link |
|---|---|
| DE (1) | DE3826682A1 (en) |
| ZA (1) | ZA895953B (en) |
-
1988
- 1988-08-05 DE DE3826682A patent/DE3826682A1/en not_active Withdrawn
-
1989
- 1989-08-04 ZA ZA895953A patent/ZA895953B/en unknown
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| Publication number | Publication date |
|---|---|
| ZA895953B (en) | 1991-04-24 |
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