DE3906772A1 - Substituted N-hydroxypyrazoles, their preparation, and their use for controlling pests - Google Patents
Substituted N-hydroxypyrazoles, their preparation, and their use for controlling pestsInfo
- Publication number
- DE3906772A1 DE3906772A1 DE3906772A DE3906772A DE3906772A1 DE 3906772 A1 DE3906772 A1 DE 3906772A1 DE 3906772 A DE3906772 A DE 3906772A DE 3906772 A DE3906772 A DE 3906772A DE 3906772 A1 DE3906772 A1 DE 3906772A1
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- Prior art keywords
- substituted
- alkyl
- hydroxypyrazoles
- hydrogen
- weight
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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
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- 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
- C07D231/14—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 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
- C07D231/16—Halogen atoms or nitro radicals
-
- 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
- C07D233/56—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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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
Abstract
Description
Die vorliegende Erfindung betrifft neue substituierte N-Hydroxypyrazole der allgemeinen Formel I,The present invention relates to new substituted N-hydroxypyrazoles of the general formula I,
in der die Substituenten die folgende Bedeutung haben:in which the substituents have the following meaning:
Z, X O, S, SO₂, CH₂,
R¹, R² Wasserstoff, C₁-C₃-Alkyl,
R³ Wasserstoff, Halogen, C₁-C₃-Alkyl,
R⁴, R⁵, R⁶ Wasserstoff, Halogen, C₁-C₄-Alkyl, C₁-C₄-Alkoxy, C₁-C₄-
Halogenalkyl, C₁-C₄-Halogenalkoxy,
n 0, 1, 2,
z 1, 2, 3.Z, X O, S, SO₂, CH₂,
R¹, R² are hydrogen, C₁-C₃-alkyl,
R³ is hydrogen, halogen, C₁-C₃-alkyl,
R⁴, R⁵, R⁶ are hydrogen, halogen, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkyl, C₁-C₄-haloalkoxy,
n 0, 1, 2,
z 1, 2, 3.
Außerdem betrifft die vorliegende Erfindung die Herstellung der Verbindungen I, Schädlingsbekämpfungsmittel, die die Verbindungen I enthalten und ein Verfahren zur Bekämpfung von Schädlingen.The present invention also relates to the preparation of the compounds I, pesticides containing the compounds I and a method of pest control.
Aus GB-A-21 15 812 sind gewisse 0-substituierte Oxime bekannt. Die insektizide Wirkung der dort beschriebenen Verbindungen ist jedoch unbefriedigend. Auch die in der EP-A-2 89 919 (DE-A-37 14 709) beschriebenen (p-Phenoxy- phenoxy)-methyl-pyrazole sind unter bestimmten Bedingungen, z. B. niedrigen Aufwandmengen, in ihrer insektiziden Wirkung nicht immer befriedigend.From GB-A-21 15 812 certain 0-substituted oximes are known. The insecticide However, the action of the compounds described there is unsatisfactory. The (p-phenoxy-) described in EP-A-2 89 919 (DE-A-37 14 709) phenoxy) methyl pyrazoles are under certain conditions, e.g. B. low Application rates, their insecticidal activity is not always satisfactory.
Der Erfindung lag die Aufgabe zugrunde, neue insektizide Wirkstoffe auf Basis von N-Hydroxypyrazolen zur Verfügung zu stellen, die in ihrer Wirkung bekannten Verbindungen überlegen sind. The invention was based on the object, new insecticidal active ingredients To provide basis of N-hydroxypyrazoles, which in their effect known connections are superior.
Demgemäß wurde gefunden, daß die eingangs definierten substituierten N- Hydroxypyrazole der Formel I sich ausgezeichnet zur Bekämpfung von Schädlingen eignen.Accordingly, it was found that the substituted N- Hydroxypyrazoles of the formula I are excellent for combating pests own.
Die Herstellung der erfindungsgemäßen N-Hydroxypyrazole I erfolgt durch Umsetzung von Verbindungen der Formel IIThe preparation of the N-hydroxypyrazoles I according to the invention is carried out by reacting compounds of the formula II
in der Y eine nukleophil verdrängbare Abgangsgruppe bedeutet, mit einem N-Hydroxypyrazol der allgemeinen Formel IIIin which Y represents a nucleophilically displaceable leaving group, with a N-hydroxypyrazole of the general formula III
in Gegenwart einer Base oder direkt mit dem Alkoholat.in the presence of a base or directly with the alcoholate.
Die Umsetzung kann im Temperaturbereich von (-20) bis 250°C, vorzugsweise 20 bis 120°C nach folgender Reaktionsgleichung erfolgen:The reaction can be in the temperature range from (-20) to 250 ° C, preferably 20 to 120 ° C according to the following reaction equation:
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 benötigten Zwischenprodukte II sind literaturbekannt und können beispielsweise nach den in GB-A-21 15 812 beschriebenen Verfahren hergestellt werden.The required intermediates II are known from the literature and can, for example prepared by the method described in GB-A-21 15 812 will.
Die N-Hydroxypyrazole sind z. T. ebenfalls bekannt und lassen sich gegebenenfalls analog dem in US 44 92 689 beschriebenen Verfahren herstellen.The N-hydroxypyrazoles are e.g. T. also known and if necessary produce analogously to the process described in US Pat. No. 4,492,689.
Man setzt normalerweise mindestens äquivalente Mengen einer Base, bezogen auf III, 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 III, 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 durchaus 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 quite advantageous in individual cases.
Die Umsetzung wird zweckmäßigerweise in einem Lösungsmittel oder Verdünnungsmittel durchgeführt. Hierzu eignen sich beispielsweise aliphatische Kohlenwasserstoffe wie n-Pentan, n-Hexan, das Hexan-Isomerengemisch und Petrolether; aromatische Kohlenwasserstoffe wie Benzol, Toluol, die Xylole und deren Isomerengemische, Benzin; Alkohole wie Methanol, Ethanol, n-Propanol und Isopropanol; Ether wie 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. Aliphatic, for example, are suitable for this 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 such as 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 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.
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. Since they develop heat in some cases, it can 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 und vermindertem Druck auf mäßig erhöhter 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-colored, viscous oils, which are caused by prolonged heating and reduced pressure at moderately elevated temperature ("distillation") rid of the last volatile parts and in this way get cleaned. The compounds of formula I are obtained in crystalline form Form, they can be cleaned by recrystallization.
Die Substituenten der Formel I haben im einzelnen folgende Bedeutung:The individual substituents of the formula I have the following meanings:
Z, X O, S, SO₂, CH₂, bevorzugt O und S, besonders bevorzugt O,
R¹, R² Wasserstoff, C₁-C₃-Alkyl wie Methyl, Ethyl, Propyl, i-Propyl,
bevorzugt Wasserstoff und C₁-C₂-Alkyl, besonders
bevorzugt Wasserstoff und Methyl,
R³ Wasserstoff, Halogen, C₁-C₃-Alkyl wie für R¹ genannt, bevorzugt
Wasserstoff, Chlor und Brom, besonders bevorzugt Wasserstoff,
Methyl und Chlor,
R⁴, R⁵, R⁶ Wasserstoff, Halogen, besonders bevorzugt Wasserstoff,
Chlor, Brom und Fluor,
C₁-C₄-Alkyl, bevorzugt C₁-C₃-Alkyl, besonders bevorzugt
Methyl, Ethyl und i-Propyl,
C₁-C₄-Alkoxy wie Methoxy, Ethoxy, Propoxy, Butoxy, bevorzugt
Methoxy und Ethoxy,
C₁-C₄-Halogenalkyl, z. B. Fluor- oder Chloralkyl, bevorzugt
C₁-C₂-Fluoralkyl, besonders bevorzugt Trifluormethyl,
C₁-C₄-Halogenalkoxy, bevorzugt C₁-C₃-Fluoralkoxy, besonders
bevorzugt Difluormethoxy, Trifluormethoxy, 1,1,2,2-Tetrafluorethoxy,
n: die Zahlen 0, 1, 2, bevorzugt 0 und 1, besonders bevorzugt
0,
z: die Zahlen 1, 2, 3, bevorzugt 1 und 2, besonders bevorzugt
1.Z, X O, S, SO₂, CH₂, preferably O and S, particularly preferably O,
R¹, R² are hydrogen, C₁-C₃-alkyl such as methyl, ethyl, propyl, i-propyl, preferably hydrogen and C₁-C₂-alkyl, particularly preferably hydrogen and methyl,
R³ is hydrogen, halogen, C₁-C₃-alkyl as mentioned for R¹, preferably hydrogen, chlorine and bromine, particularly preferably hydrogen, methyl and chlorine,
R⁴, R⁵, R⁶ hydrogen, halogen, particularly preferably hydrogen, chlorine, bromine and fluorine,
C₁-C₄-alkyl, preferably C₁-C₃-alkyl, particularly preferably methyl, ethyl and i-propyl,
C₁-C₄ alkoxy such as methoxy, ethoxy, propoxy, butoxy, preferably methoxy and ethoxy,
C₁-C₄ haloalkyl, e.g. B. fluoro or chloroalkyl, preferably C₁-C₂ fluoroalkyl, particularly preferably trifluoromethyl,
C₁-C₄-haloalkoxy, preferably C₁-C₃-fluoroalkoxy, particularly preferably difluoromethoxy, trifluoromethoxy, 1,1,2,2-tetrafluoroethoxy,
n : the numbers 0, 1, 2, preferably 0 and 1, particularly preferably 0,
z : the numbers 1, 2, 3, preferably 1 and 2, particularly preferably 1.
Die erfindungsgemäßen Verbindungen I können ein oder mehrere Asymmetriezentren enthalten. Die vorliegende Erfindung schließt alle möglichen Stereoisomeren, Diastereomeren, Enantiomeren, Diastereomeren- und Enantiomerengemische ein.The compounds I according to the invention can have one or more centers of asymmetry contain. The present invention includes all possible Stereoisomers, diastereomers, enantiomers, mixtures of diastereomers and enantiomers a.
Die substituierten N-Hydroxypyrazole 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 substituted N-hydroxypyrazoles of the general formula I are suitable Pests from the class of insects, arachnids and nematodes fight effectively. They can be used in crop protection as well as on hygiene, Storage protection and veterinary sector used as a pesticide will.
Zu den schädlichen Insekten gehören aus der Ordnung der Schmetterlinge (Lepidoptera) beispielsweise Agrotis ypsilon, Agrotis segetum, Alabama argillacea, Anticarsia gemmatalis, Argyresthia conjugella, Autographa gamma, Bupalus piniarius, Cacoecia murinana, Capua reticulana, Cheimatobia brumata, Choristoneura fumiferana, Choristoneura occidentalis, Cirphis unipuncta, Cydia pomonella, Dendrolimus pini, Diaphania nitidalis, Diatraea grandiosella, Earias insulana, Elasmopalpus lignosellus, Eupoecilia ambiguella, Evetria bouliana, Feltia subterranea, Galleria mellonella, Grapholita funebrana, Grapholita molesta, Heliothis armigera, Heliothis virescens, Heliothis zea, Hellula undalis, Hibernia defoliaria, Hyphantria cunea, Hyponomeuta malinellus, Keifferia lycopersicella, Lambdina fiscellaria, Laphygma exigua, Leucoptera coffeella, Leucoptera scitella, Lithocolletis blancardella, Lobesia botrana, Loxostege sticticalis, Lymantria dispar, Lymantria monacha, Lyonetia clerkella, Malacosoma neustria, Mamestra brassicae, Orgyia pseudotsugata, Ostrinia nubilalis, Panolis flamea, Pectinophora gossypiella, Peridroma saucia, Phalera bucephala, Phthorimaea operculella, Phyllocnistis citrella, Pieris brassicae, Plathypena scarbra, Plutella xylostella, Pseudoplusia includens, Phyacionia frustrana, Scrobiapalpula absoluta, Sitotroga cerelella, Sparganothis pilleriana, Spodoptera frugiperda, Spodoptera littoralis, Spodoptera litura, Thaumatopoea pityocampa, Tortrix viridana, Trichoplusia ni, Zeiraphera canadensis.Harmful insects belong to the order of the butterflies (Lepidoptera) for example Agrotis ypsilon, Agrotis segetum, Alabama argillacea, Anticarsia gemmatalis, Argyresthia conjugella, Autographa gamma, Bupalus piniarius, Cacoecia murinana, Capua reticulana, Cheimatobia brumata, Choristoneura fumiferana, Choristoneura occidentalis, Cirphis unipuncta, Cydia pomonella, Dendrolimus pini, Diaphania nitidalis, Diatraea grandiosella, Earias insulana, Elasmopalpus lignosellus, Eupoecilia ambiguella, Evetria bouliana, Feltia subterranea, Galleria mellonella, Grapholita funebrana, Grapholita molesta, Heliothis armigera, Heliothis virescens, Heliothis zea, Hellula undalis, Hibernia defoliaria, Hyphantria cunea, Hyponomeuta malinellus, Keifferia lycopersicella, Lambdina fiscellaria, Laphygma exigua, Leucoptera coffeella, Leucoptera scitella, Lithocolletis blancardella, Lobesia botrana, Loxostege sticticalis, Lymantria dispar, Lymantria monacha, Lyonetia clerkella, Malacosoma neustria, Mamestra brassicae, Orgyia pseudotsugata, Ostrinia nubilalis, Panolis flamea, Pectinophora gossypiella, Peridroma saucia, Phalera bucephala, Phthorimaea operculella, Phyllocnistis citrella, Pieris brassicae, Plathypena scarbra, Plutella xylostella, Pseudoplusia includens, Phyacionia frustrana, Scrobiapalpula absoluta, Sitotroga cerelella, Sparganothis pilleriana, Spodoptera frugiperda, Spodoptera littoralis, Spodoptera litura, Thaumatopoea pityocampa, Tortrix viridana, Trichoplusia ni, Zeiraphera canadensis.
Aus der Ordnung der Käfer (Coleoptera) beispielsweise Agrilus sinuatus, Agriotes lineatus, Agriotes obscurus, Amphimallus solstitialis, Anisandrus dispar, Anthonomus grandis, Anthonomus pomorum, Atomaria linearis, Blastophagus piniperda, Blitophaga undata, Bruchus rufimanus, Bruchus pisorum, Bruchus lentis, Byctiscus betulae, Cassida nebulosa, Cerotoma trifurcata, Ceuthorrhynchus assimilis, Ceuthorrynchus napi, Chaetocnema tibialis, Conoderus vespertinus, Crioceris asparagi, Diabrotica longicornis, Diabrotica 12-punctata, Diabrotica virgifera, Epilachna varivestis, Epitrix hirtipennis, Eutinobothrus brasiliensis, Hylobius abietis, Hypera brunneipennis, Hypera postica, Ips typographus, Lema bilineata, Lema melanopus, Leptinotarsa decemlineata, Limonius californicus, Lissorhoptrus oryzophilus, Melanotus communis, Meligethes aeneus, Melolontha hippocastani, Melolontha melolontha, Onlema oryzae, Ortiorrhynchus sulcatus, Ortiorrhynchus ovatus, Phaedon cochleariae, Phyllotreta chrysocephala, Phyllophaga sp., Phyllopertha horticola, Phyllotreta nemorum Phyllotreta striolata, Popillia japonica, Sitona lineatus, Sitophilus granaria.From the order of the beetles (Coleoptera), for example Agrilus sinuatus, Agriotes lineatus, Agriotes obscurus, Amphimallus solstitialis, Anisandrus dispar, anthonomus grandis, anthonomus pomorum, atomaria linearis, Blastophagus piniperda, Blitophaga undata, Bruchus rufimanus, Bruchus pisorum, Bruchus lentis, Byctiscus betulae, Cassida nebulosa, Cerotoma trifurcata, Ceuthorrhynchus assimilis, Ceuthorrynchus napi, Chaetocnema tibialis, Conoderus vespertinus, Crioceris asparagi, Diabrotica longicornis, Diabrotica 12-punctata, Diabrotica virgifera, Epilachna varivestis, Epitrix hirtipennis, Eutinobothrus brasiliensis, Hylobius abietis, Hypera brunneipennis, Hypera postica, Ips typographus, Lema bilineata, Lema melanopus, Leptinotarsa decemlineata, Limonius californicus, Lissorhoptrus oryzophilus, Melanotus communis, Meligethes aeneus, Melolontha hippocastani, Melolontha melolontha, Onlema oryzae, Ortiorrhynchus sulcatus, Ortiorrhynchus ovatus, Phaedon cochleariae, Phyllotreta chrysocephala, Phyllophaga sp., Phyllopertha horticola, Phyllotreta nemorum Phyllotreta striolata, Popillia japonica, Sitona lineatus, Sitophilus granaria.
Aus der Ordnung der Zweiflügler (Diptera) beispielsweise Aedes aegypti, Aedes vexans, Anastrepha ludens, Anopheles maculipennis, Ceratitis capitata, Chrysomya bezziana, Chrysomya hominivorax, Chrysomya macellaria, Contarinia sorghicola, Cordylobia anthropophaga, Culex pipiens, Dacus cucurbitae, Dacus oleae, Dasineura brassicae, Fannia canicularis, Gasterophilus intestinalis, Glossia morsitans, Haematobia irritans, Haplodiplosis equestris Hylemyia platura, Hypoderma lineata, Liriomyza sativae, Liriomyza trifolii, Lucilia caprina, Lucilia cuprina, Lucilia sericata, Lycoria pectoralis, Mayetiola destructor, Musca domestica, Muscina stabulans, Oestrus ovis, Oscinella frit, Pegomya hysocyami, Phorbia antiqua, Phorbia brassicae, Phorbia coarctata, Rhagoletis cerasi, Rhagoletis pomonella, Tabanus bovinus, Tipula oleracea, Tipua paludosa.From the order of the two-winged species (Diptera), for example Aedes aegypti, Aedes vexans, Anastrepha ludens, Anopheles maculipennis, ceratitis capitata, Chrysomya bezziana, Chrysomya hominivorax, Chrysomya macellaria, Contarinia sorghicola, Cordylobia anthropophaga, Culex pipiens, Dacus cucurbitae, Dacus oleae, Dasineura brassicae, Fannia canicularis, Gasterophilus intestinalis, Glossia morsitans, Haematobia irritans, Haplodiplosis equestris Hylemyia platura, Hypoderma lineata, Liriomyza sativae, Liriomyza trifolii, Lucilia caprina, Lucilia cuprina, Lucilia sericata, Lycoria pectoralis, Mayetiola destructor, Musca domestica, Muscina stabulans, Oestrus ovis, Oscinella frit, Pegomya hysocyami, Phorbia antiqua, Phorbia brassicae, Phorbia coarctata, Rhagoletis cerasi, Rhagoletis pomonella, Tabanus bovinus, Tipula oleracea, Tipua paludosa.
Aus der Ordnung der Thripse (Thysanoptera) beispielsweise Frankliniella fusca, Frankliniella occidentalis, Frankliniella tritici, Scirtothrips citri, Thrips oryzae, Thrips palmi, Thrips tabaci.From the order of the thrips (Thysanoptera), for example Frankliniella fusca, Frankliniella occidentalis, Frankliniella tritici, Scirtothrips citri, Thrips oryzae, Thrips palmi, Thrips tabaci.
Aus der Ordnung der Hautflügler (Hymenoptera) beispielsweise Athalia rosae, Atta cephalotes, Atta sexdens, Atta texana, Hoplocampa minuta, Hoplocampa testudinea, Monomorium pharaonis, Solenopsis geminata, Solenopsis invicta.From the order of the hymenoptera (Hymenoptera), for example, Athalia pink, Atta cephalotes, Atta sexdens, Atta texana, Hoplocampa minuta, Hoplocampa testudinea, Monomorium pharaonis, Solenopsis geminata, Solenopsis invicta.
Aus der Ordnung der Wanzen (Heteroptera) beispielsweise Acrosternum hilare, Blissus leucopterus, Cyrtopeltis notatus, Dysdercus cingulatus, Dysdercus intermedius, Eurygaster integriceps, Euchistus impictiventris, Leptoglossus phyllopus, Lygus lineolaris, Lygus pratensis, Nezara viridula, Piesma quadrata, Solubea insularis, Thyanta perditor.From the order of the bugs (Heteroptera), for example, Acrosternum hilare, Blissus leucopterus, Cyrtopeltis notatus, Dysdercus cingulatus, Dysdercus intermedius, Eurygaster integriceps, Euchistus impictiventris, Leptoglossus phyllopus, Lygus lineolaris, Lygus pratensis, Nezara viridula, Piesma quadrata, Solubea insularis, Thyanta perditor.
Aus der Ordnung der Pflanzensauger (Homoptera) beispielsweise Acyrthosiphon onobrychis, Adelges laricis, Aphidula nasturtii, Aphis fabae, Aphis pomi, Aphis sambuci, Brachycaudus cardui, Brevicoryne brassicae, Cerosipha gossypii, Dreyfusia nordmannianae, Dreyfusia piceae, Dyasphis radicola, Dysaulacorthum pseudosolani, Empoasca fabae, Macrosiphum avenae, Macrosiphum euphorbiae, Macrosiphon rosae, Megoura viciae, Metopolophium dirhodum, Myzodes persicae, Myzus cerasi, Nilaparvata lugens, Pemphigus bursarius, Perkinsiella saccharicida, Phorodon humuli, Psylla mali, Psylla piri, Rhopalomyzus ascalonicus, Rhopalosiphum maidis, Sappahis mala, Sappahis mali, Schizaphis graminum, Schizoneura lanuginosa, Trialeurodes vaporariorum, Viteus vitifolii.From the order of the plant suckers (Homoptera) for example Acyrthosiphon onobrychis, Adelges laricis, Aphidula nasturtii, Aphis fabae, Aphis pomi, Aphis sambuci, Brachycaudus cardui, Brevicoryne brassicae, Cerosipha gossypii, Dreyfusia nordmannianae, Dreyfusia piceae, Dyasphis radicola, Dysaulacorthum pseudosolani, Empoasca fabae, Macrosiphum avenae, Macrosiphum euphorbiae, Macrosiphon rosae, Megoura viciae, Metopolophium dirhodum, Myzodes persicae, Myzus cerasi, Nilaparvata lugens, Pemphigus bursarius, Perkinsiella saccharicida, Phorodon humuli, Psylla mali, Psylla piri, Rhopalomyzus ascalonicus, Rhopalosiphum maidis, Sappahis mala, Sappahis mali, Schizaphis graminum, Schizoneura lanuginosa, Trialeurodes vaporariorum, Viteus vitifolii.
Aus der Ordnung der Termiten (Isoptera) beispielsweise Calotermes flavicollis, Leucotermes flavipes, Reticulitermes lucifugus, Termes natalensis.From the order of the termites (Isoptera), for example, Calotermes flavicollis, Leucotermes flavipes, Reticulitermes lucifugus, Termes natalensis.
Aus der Ordnung der Geradflügler (Orthoptera) beispielsweise Acheta domestica, Blatta orientalis, Blattella germanica, Forficula auricularia, Gryllotalpa gryllotalpa, Locusta migratoria, Melanoplus birittatus, Melanoplus femur-rubrum, Melanoplus mexicanus, Melanoplus sanguinipes, Melanoplus spretus, Nomadacris septemfasciata, Periplaneta americana, Schistocerca americana, Schistocerca peregrina, Stauronotus maroccanus, Tachycines asynamorus.From the order of the straight wing aircraft (Orthoptera), for example Acheta domestica, Blatta orientalis, Blattella germanica, Forficula auricularia, Gryllotalpa gryllotalpa, Locusta migratoria, Melanoplus birittatus, Melanoplus femur-rubrum, Melanoplus mexicanus, Melanoplus sanguinipes, Melanoplus spretus, Nomadacris septemfasciata, Periplaneta americana, Schistocerca americana, Schistocerca peregrina, Stauronotus maroccanus, Tachycines asynamorus.
Zur Klasse der Arachnoidea gehören Spinnentiere (Acarina) beispielsweise Amblyomma americanum, Amglyomma variegatum, Argas persicus, Boophilus annulatus, Boophilus decoloratus, Boophilus microplus, Brevipalpus phoenicis, Bryobia praetiosa, Dermacentor silvarum, Eotetranychus carpini, Eriophyes sheldoni, Hyalomma truncatum, Ixodes ricinus, Ixodes rubicundus, Ornithodorus moubata, Otobins megnini, Paratetranychus pilosus, Permanyssus gallinae, Phyllocaptrata oleivora, Polyphagotarsonemus latus, Psoroptes ovis, Phipicephalus appendiculatus, Rhipicephalus evertsi, Saccoptes scabiei, Tetranychus cinnabarinus, Tetranychus kanzawai, Tetranychus pacificus, Tetranychus telarius, Tetranychus urticae.The arachnoid class includes arachnids (Acarina), for example Amblyomma americanum, Amglyomma variegatum, Argas persicus, Boophilus annulatus, Boophilus decoloratus, Boophilus microplus, Brevipalpus phoenicis, Bryobia praetiosa, Dermacentor silvarum, Eotetranychus carpini, Eriophyes sheldoni, Hyalomma truncatum, Ixodes ricinus, Ixodes rubicundus, Ornithodorus moubata, Otobins megnini, Paratetranychus pilosus, Permanyssus gallinae, Phyllocaptrata oleivora, Polyphagotarsonemus latus, Psoroptes ovis, Phipicephalus appendiculatus, Rhipicephalus evertsi, Saccoptes scabiei, Tetranychus cinnabarinus, Tetranychus kanzawai, Tetranychus pacificus, Tetranychus telarius, Tetranychus urticae.
Zur Klasse der Nematoden zählen beispielsweise Wurzelgallennematoden, z. B. Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica, Zysten bildende Nematoden, z. B. Globodera rostochiensis, Heterodera avenae, Hetrodera glycinae, Heterodera schachtii, Heterodera trifolii, Stock- und Blattälchen, z. B. Belonolaimus longicaudatus, Ditylenchus destructor, Ditylenchus dipsaci, Heliocotylenchus multicinctus, Longidorus elongatus, Radopholus similis, Rotylenchus robustus, Trichodorus primitivus, Tylenchorhynchus claytoni, Tylenchorhynchus dubius, Pratylenchus neglectus, Pratylenchus penetrans, Pratylenchus curvitatus, Pratylenchus goodeyi.The class of nematodes includes, for example, root gall nematodes, e.g. B. Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica, cysts forming nematodes, e.g. B. Globodera rostochiensis, Heterodera avenae, Hetrodera glycinae, Heterodera schachtii, Heterodera trifolii, stick and Leaf flakes, e.g. B. Belonolaimus longicaudatus, Ditylenchus destructor, Ditylenchus dipsaci, Heliocotylenchus multicinctus, Longidorus elongatus, Radopholus similis, Rotylenchus robustus, Trichodorus primitivus, Tylenchorhynchus claytoni, Tylenchorhynchus dubius, Pratylenchus neglectus, Pratylenchus penetrans, Pratylenchus curvitatus, Pratylenchus goodeyi.
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 application forms depend entirely on the purposes; they should in any case the finest possible distribution of the active ingredients according to the invention guarantee.
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, in Consider.
Wäßrige Anwendungsformen können aus Emulsionskonzentraten, Pasten oder netzbaren Pulvern (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 made from 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 use the substances as such or in an oil or solvent dissolved, by means of wetting, adhesive, dispersing or emulsifying agents in Water can be homogenized. But it can also be made from effective substance Wetting agents, adhesives, dispersants or emulsifiers and possibly solvents or oil existing concentrates are made to be diluted 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 Erdalkalisalze, Salze sulfatierter Hexadecanole, Heptadecanole, Octadecanole, Salze von sulfatiertem Fettalkoholglykolether, Kondensationsprodukte von sulfoniertem Naphthalin und Naphthalinderivaten mit Formaldehyd, Kondensationsprodukte des Naphthalins bzw. der Naphthalinsulfonsäure mit Phenol und Formaldehyd, Polyoxyethylenoctylphenolether, ethoxyliertes Isooctylphenol, Octylphenol, Nonylphenol, 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 as surface-active substances of ligninsulfonic acid, naphthalenesulfonic acid, phenolsulfonic acid, alkylarylsulfonates, Alkyl sulfates, alkyl sulfonates, alkali and alkaline earth salts dibutylnaphthalenesulfonic acid, lauryl ether sulfate, fatty alcohol sulfates, fatty acid alkali and alkaline earth salts, salts of sulfated hexadecanols, Heptadecanols, octadecanols, salts of sulfated fatty alcohol glycol ether, Condensation products of sulfonated naphthalene and naphthalene derivatives with formaldehyde, condensation products of naphthalene or Naphthalenesulfonic acid with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctylphenol, octylphenol, nonylphenol, 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 will.
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 with 95 parts by weight of finely divided Kaolin mixed intimately. You get one in this way Dusts containing 3% by weight of the active ingredient.
- II. 30 Gew.-Teile der Verbindung Nr. 2 werden mit einer Mischung aus 92 Gew.-Teilen pulverförmigem Kieselsäuregel und 8 Gew.-Teilen Paraffinöl, das auf die Oberfläche dieses Kieselsäuregels gesprüht wurde, innig vermischt. Man erhält auf diese Weise eine Aufbereitung des Wirkstoffs mit guter Haftfähigkeit.II. 30 parts by weight of compound no. 2 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. 4 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 Rizinusöl besteht.III. 10 parts by weight of compound no. 4 are dissolved in a mixture, 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 mole of castor oil.
- IV. 20 Gew.-Teile der Verbindung Nr. 5 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 Rizinusöl besteht.IV. 20 parts by weight of compound no. 5 are dissolved in a mixture, made from 60 parts by weight of cyclohexanone, 30 parts by weight of 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.
- V. 80 Gew.-Teile der Verbindung Nr. 8 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. 8 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.
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 Magnsiumsulfat, Magnesiumoxid, gemahlene Kunststoffe, Düngemittel, wie z. B. Ammoniumsulfat, Ammoniumphosphat, Ammoniumnitrat, Harnstoffe und pflanzliche Produkte, wie Getreidemehl, Baumrinden-, Holz- und Nußschalenmehl, Cellulosepulver und andere feste Trägerstoffe.Granules, e.g. B. coating, impregnation and homogeneous granules by binding the active ingredients to solid carriers. Solid carriers are e.g. B. mineral earths, such as silica gel, silicas, Silica gels, silicates, talc, kaolin, attaclay, limestone, lime, chalk, Bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, Magnesium oxide, ground plastics, fertilizers such. B. ammonium sulfate, Ammonium phosphate, ammonium nitrate, urea and vegetable Products such as flour, tree bark, wood and nutshell flour, cellulose powder and other solid carriers.
Die Formulierungen enthalten im allgemeinen zwischen 0,1 und 95 Gew.-% Wirkstoff, vorzugsweise zwischen 0,5 und 90 Gew.-%.The formulations generally contain between 0.1 and 95% by weight Active ingredient, preferably between 0.5 and 90 wt .-%.
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%. Generally they are between 0.0001 and 10%, preferably between 0.01 and 1%.
Die Wirkstoffe können auch mit gutem Erfolg im Ultra-Low-Volume-Verfahren (ULV) verwendet werden, wobei es möglich ist, Formulierungen mit mehr als 95 Gew.-% Wirkstoff oder sogar den Wirkstoff ohne Zusätze auszubringen.The active ingredients can also be used with great 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 0,01 bis 10, vorzugsweise 0,05 bis 2,0 kg/ha.The amount of active ingredient applied under field conditions is 0.01 to 10, preferably 0.05 to 2.0 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.
Zur Suspension von 0,3 g Natriumhydrid in 10 ml Dimethylformamid tropft man unter Kühlung bei 0°C die Lösung aus 1,0 g N-Hydroxypyrazol in 10 ml Dimethylformamid zu. Man läßt noch 1 Stunde nachrühren und versetzt anschließend mit der Lösung von 4,7 g 2-(4-Phenoxyphenoxy)-ethyl-p-toluolsulfonat in 50 l Dimethylformamid. Der Reaktionsansatz wird noch 12 Stunden bei Raumtemperatur gerührt und anschließend auf 250 ml Eiswasser gegossen. Zur Aufarbeitung wird dreimal mit Methyl-tert.-butylether extrahiert, die vereinigten Extrakte mit 1 N Natronlauge und schließlich mit Wasser gewaschen. Nach Trocknen der organischen Phase mit Natriumsulfat, Abziehen des Lösungsmittels im Vakuum und Chromatographie des verbleibenden Rückstandes über Kieselgel mit Toluol als Laufmittel erhält man 2,7 g N-[2-(4-Phenoxyphenoxy)-ethoxy]-pyrazol mit einem Schmelzpunkt von Fp. 83-85°C. The solution of 1.0 g of N-hydroxypyrazole in 10 ml of dimethylformamide is added dropwise to the suspension of 0.3 g of sodium hydride in 10 ml of dimethylformamide while cooling at 0 ° C. The mixture is stirred for a further 1 hour and then a solution of 4.7 g of 2- (4-phenoxyphenoxy) ethyl p-toluenesulfonate in 50 l of dimethylformamide is added. The reaction mixture is stirred for a further 12 hours at room temperature and then poured onto 250 ml of ice water. For working up, the mixture is extracted three times with methyl tert-butyl ether, and the combined extracts are washed with 1 N sodium hydroxide solution and finally with water. After drying the organic phase with sodium sulfate, stripping off the solvent in vacuo and chromatography of the remaining residue over silica gel with toluene as the eluent, 2.7 g of N- [2- (4-phenoxyphenoxy) ethoxy] pyrazole with a melting point of mp 83-85 ° C.
Claims (6)
Z, X O, S, SO₂, CH₂,
R¹, R² Wasserstoff, C₁-C₃-Alkyl,
R³ Wasserstoff, Halogen, C₁-C₃-Alkyl,
R⁴, R⁵, R⁶ Wasserstoff, Halogen, C₁-C₄-Alkyl, C₁-C₄-Alkoxy, C₁-C₄- Halogenalkyl, C₁-C₄-Halogenalkoxy,
n 0, 1, 2,
z 1, 2, 3.1. Substituted N-hydroxypyrazoles of the general formula I in which the substituents have the following meaning:
Z, X O, S, SO₂, CH₂,
R¹, R² are hydrogen, C₁-C₃-alkyl,
R³ is hydrogen, halogen, C₁-C₃-alkyl,
R⁴, R⁵, R⁶ are hydrogen, halogen, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkyl, C₁-C₄-haloalkoxy,
n 0, 1, 2,
z 1, 2, 3.
Y eine nukleophil verdrängbare Abgangsgruppe bedeutet,
mit einem N-Hydroxypyrazol der allgemeinen Formel III in Gegenwart einer Base oder mit dem Alkoholat direkt umsetzt. 2. A process for the preparation of the substituted N-hydroxypyrazoles of the formula I according to claim 1, characterized in that an appropriately substituted compound II wherein
Y represents a nucleophilically displaceable leaving group,
with an N-hydroxypyrazole of the general formula III in the presence of a base or directly with the alcoholate.
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3906772A DE3906772A1 (en) | 1989-03-03 | 1989-03-03 | Substituted N-hydroxypyrazoles, their preparation, and their use for controlling pests |
| CA002010715A CA2010715C (en) | 1989-03-03 | 1990-02-22 | Substituted n-hydroxypyrazoles and n-hydroxytriazoles for controlling pests |
| ES90103758T ES2052087T3 (en) | 1989-03-03 | 1990-02-26 | N-HYDROXYPYRAZOLES AND N-HYDROXYTRIAZOLES SUBSTITUTED, PROCEDURE FOR THEIR OBTAINING AND USE FOR THE FIGHT AGAINST PESTS. |
| EP90103758A EP0388665B1 (en) | 1989-03-03 | 1990-02-26 | Substituted N-hydroxypyrazoles and N-hydroxy-triazoles and their use in combatting parasites |
| DK90103758.0T DK0388665T3 (en) | 1989-03-03 | 1990-02-26 | Substituted N-hydroxypyrazoles and N-hydroxytriazoles, methods for their preparation and their use in the control of harmful organisms |
| DE59005498T DE59005498D1 (en) | 1989-03-03 | 1990-02-26 | Substituted N-hydroxypyrazoles and N-hydroxytriazoles, processes for their preparation and their use for controlling pests. |
| JP2049717A JP2786299B2 (en) | 1989-03-03 | 1990-03-02 | Substituted N-hydroxypyrazoles and N-hydroxytriazoles and their use for controlling pests |
| KR1019900002866A KR0150451B1 (en) | 1989-03-03 | 1990-03-03 | Substituted n-hydroxypyrazoles and n-hydroxy-triazoles for controlling pests |
| US07/638,011 US5120756A (en) | 1989-03-03 | 1991-01-07 | Substituted n-hydroxypyrazoles and n-hydroxy-triazoles for controlling pests |
| US07/825,357 US5173501A (en) | 1989-03-03 | 1992-01-24 | Substituted N-hydroxypyrazoles and N-hydroxytriazoles for controlling pests |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3906772A DE3906772A1 (en) | 1989-03-03 | 1989-03-03 | Substituted N-hydroxypyrazoles, their preparation, and their use for controlling pests |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3906772A1 true DE3906772A1 (en) | 1990-09-13 |
Family
ID=6375422
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE3906772A Withdrawn DE3906772A1 (en) | 1989-03-03 | 1989-03-03 | Substituted N-hydroxypyrazoles, their preparation, and their use for controlling pests |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE3906772A1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0486804A2 (en) * | 1990-10-20 | 1992-05-27 | BASF Aktiengesellschaft | Hydroquinonediethers, processes for their preparation, and their use in combatting pests |
-
1989
- 1989-03-03 DE DE3906772A patent/DE3906772A1/en not_active Withdrawn
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0486804A2 (en) * | 1990-10-20 | 1992-05-27 | BASF Aktiengesellschaft | Hydroquinonediethers, processes for their preparation, and their use in combatting pests |
| EP0486804A3 (en) * | 1990-10-20 | 1992-09-02 | Basf Aktiengesellschaft | Hydroquinonediethers, processes for their preparation, and their use in combatting pests |
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