DE2726684A1 - Insecticidal di:halo-benzoyl-phenylurea derivs. - useful for plant protection or textile preservation - Google Patents

Insecticidal di:halo-benzoyl-phenylurea derivs. - useful for plant protection or textile preservation

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Publication number
DE2726684A1
DE2726684A1 DE19772726684 DE2726684A DE2726684A1 DE 2726684 A1 DE2726684 A1 DE 2726684A1 DE 19772726684 DE19772726684 DE 19772726684 DE 2726684 A DE2726684 A DE 2726684A DE 2726684 A1 DE2726684 A1 DE 2726684A1
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Prior art keywords
halo
ocf2
phenylurea
formula
derivs
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DE19772726684
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German (de)
Inventor
Ludwig Dr Emmel
R Dipl Chem Dr Geuss
Gerhard Dipl Chem Dr Hoerlein
Hubert Dr Schoenowski
Anna Dr Waltersdorfer
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Hoechst AG
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Hoechst AG
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Priority to DE19772726684 priority Critical patent/DE2726684A1/en
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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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/34—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the groups, e.g. biuret; Thio analogues thereof; Urea-aldehyde condensation products
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C275/46—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups containing any of the groups, X being a hetero atom, Y being any atom, e.g. acylureas
    • C07C275/48—Y being a hydrogen or a carbon atom
    • C07C275/54—Y being a carbon atom of a six-membered aromatic ring, e.g. benzoylureas
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C323/39—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton at least one of the nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom
    • C07C323/43—Y being a hetero atom
    • C07C323/44—X or Y being nitrogen atoms

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Acylurea derivs. of formula (I) are new. In the formula, R1 and R2 are each halo; R3 is 1-4C alkoxy or alkylthio, or 2-4C alkenyloxy substd. by 2-6 halo. R4=H, halo or 1-2C alkyl. (I) are prepd. by reacting R1R2-phenyl-CoA and R3R4-phenyl-B-where one of A and B is NCO and the other NH2. (I) are insecticides, esp. useful as stomach poisons for caterpillars and larvae. They have low toxicity to warm-blooded animals and no phytotoxicity so can be used, in conventional formulations, in agricultural or horticultural applications, or to preserve textiles. A typical cpd. (I) is N-(2,6-dichlorobenzoyl)-N'-4-(1',2' -dichlorovinyloxy)phenylurea.

Description

Phenylbenzoylharnstoffderivate mit insektizider Wirkung sind inPhenylbenzoylurea derivatives with insecticidal activity are in

der Literatur bereits beschrieben (J. Agr. Food Chem. 21 (1973), 348; 24 (1976), 1, DT-OS 21 23 236).already described in the literature (J. Agr. Food Chem. 21 (1973), 348; 24 (1976), 1, DT-OS 21 23 236).

Es wurde nun gefunden, daß auch Verbindungen der allgemeinen Formel worin R1, R2 Halogen R3 (C1-C4)-Alkoxy, (C1-C4)-Alkylthio oder (C2-C4)-Alkenoxy, die durch 2 - 6 Halogenatome substituiert sind, R4 H, Halogen oder (C1-C2)-Alkyl bedeuten, eine ausgezeichnete insektizide Wirkung aufweisen.It has now been found that compounds of the general formula wherein R1, R2 halogen R3 (C1-C4) -alkoxy, (C1-C4) -alkylthio or (C2-C4) -alkenoxy, which are substituted by 2 - 6 halogen atoms, R4 H, halogen or (C1-C2) - Mean alkyl, have an excellent insecticidal effect.

Man erhält die erfindungsgemäßen Substanzen, in dem man Verbindungen der Formeln miteinander umsetzt, wobei jeweils einer der Reste A und B eine Isocyanatgruppe und der andere eine Aminogruppe darstellt.The substances according to the invention are obtained by adding compounds of the formulas reacted with one another, one of the radicals A and B being an isocyanate group and the other being an amino group.

Die Umsetzung der Phenylisocyanate bzw. Benzoylisocyanate mit einem Benzamid bzw. Anilin wird vorteilhaft bei einer Temperatur zwischen 400 und 1300C in einem inerten Lösungsmittel und in Gegenwart einer tertiären Base, wie z.B. Pyridin oder Tributylamin, durchgeführt. Als Lösungs- bzw. Verdünnungsmittel können z.B. Benzol, Toluol, Chlorbenzol, Dioxan etc. verwendet werden. Die als Ausgangsmaterialien benötigten Isocyanate, Benzamide und Aniline können nach literaturbekannten Methoden hergestellt werden. Benzoylisocyanate (A = NCO) entstehen z.B. durch Umsetzung von Benzamiden und Oxalylchlorid.The implementation of phenyl isocyanates or benzoyl isocyanates with a Benzamide or aniline is advantageous at a temperature between 400 and 1300C in an inert solvent and in the presence of a tertiary base such as pyridine or tributylamine. As solvents or diluents, e.g. Benzene, toluene, chlorobenzene, dioxane, etc. can be used. The as raw materials Isocyanates, benzamides and anilines required can be prepared using methods known from the literature getting produced. Benzoyl isocyanates (A = NCO) are formed, for example, by reacting Benzamides and oxalyl chloride.

Die Verbindungen entstehen in guten Ausbeuten. Sie sind im allgemeinen kristallin und können für die meisten Zwecke ohne weitere Reinigung verwendet werden.The compounds are produced in good yields. They are in general crystalline and can be used for most purposes without further purification.

Die erfindungsgemäßen Verbindungen sind wirksame Pestizide, insbesondere Insektizide und können gegen eine große Zahl von Schadinsekten, wie Schmetterlinge, Käfer, Fliegen, Heuschrecken, Wanzen und Schaben eingesetzt werden. Genannt seien z.B. Aedes aegypti, Leptinotarsa decemlineata, Pieris brassicae, Musca domestica, Schistacerca gregaria, Spodoptera littoralis und Oncopeltus fasuatus. Besonders wirksam sind sie gegen die Paupen- bzw.The compounds of the invention are effective pesticides, especially Insecticides and can be used against a large number of insect pests such as butterflies, Beetles, flies, grasshoppers, bed bugs and cockroaches are used. Be mentioned e.g. Aedes aegypti, Leptinotarsa decemlineata, Pieris brassicae, Musca domestica, Schistacerca gregaria, Spodoptera littoralis and Oncopeltus fasuatus. Particularly they are effective against the paupen resp.

Larvenstadien der genannten Insekten, wobei sie über den Magen aufgenommen werden. Da die Verbindungen eine äußerst geringe Warmblütertoxizität und keine Phytotoxizität bei Kulturpflanzen zeigen, eignen sie sich besonders zur Bekämpfung von Insekten die im Acker- und Gartenbau vorkommen, sowie zur Konservierung von Textilien.Larval stages of the insects mentioned, being ingested through the stomach will. Because the compounds have an extremely low toxicity to warm blooded animals and no phytotoxicity show in cultivated plants that they are particularly suitable for combating insects which occur in arable and horticultural fields, as well as for the preservation of textiles.

Die erfindungsgemäßen Mittel enthalten als Wirkstoffe die Verbindungen der allgemeinen Formel I im allgemeinen zu 2 - 80 Gew.-t.The agents according to the invention contain the compounds as active ingredients of the general formula I in general from 2 to 80 parts by weight.

Sie können als benetzbare Pulver, emulgierbare Konzentrate, versprühbare Lösungen, Stäubemittel oder Granulate in den üblichen Zubereitungen angewendet werden.They can be used as wettable powders, emulsifiable concentrates, sprayable Solutions, dusts or granules can be used in the usual preparations.

Benetzbare Pulver sind in Wasser gleichmäßig dispergierbare Präparate, die neben dem Wirkstoff außer einem Verdünnungs- oder Inertstoff noch Netzmittel, z.B. polyoxäthylierte Alkylphenole, polyoxäthylierte Oleyl- oder Stearylamine, Alkyl- oder Alkylphenylsulfonate, und Dispergiermittel, z.B. ligninsulfonsaures Natrium, 2,2'-dinaphthylmethan-6,6'-disulfonsaures Natrium, oder auch oleylmethyltaurinsaures Natrium enthalten.Wettable powders are preparations that can be uniformly dispersed in water, which, in addition to the active ingredient, apart from a diluent or inert substance, also wetting agents, e.g. polyoxyethylated alkylphenols, polyoxyethylated oleyl or stearylamines, alkyl or alkylphenylsulphonates, and dispersants, e.g. sodium lignosulphonic acid, Sodium 2,2'-dinaphthylmethane-6,6'-disulfonic acid, or oleylmethyltauric acid Contain sodium.

Emulgierbare Konzentrate werden durch Auflösen des Wirkstoffs in einem organischen Lösungsmittel, z.B. Butanol, Cyclohexanon, Dimethylformamid, Xylol oder auch höhersiedenden Aromaten erhalten, z.B. o-Dichlorbenzol, p-Cymol etc.Emulsifiable concentrates are made by dissolving the active ingredient in a organic solvents, e.g. butanol, cyclohexanone, dimethylformamide, xylene or also get higher-boiling aromatics, e.g. o-dichlorobenzene, p-cymene etc.

Stäubemittel erhält man durch Vermahlen des Wirkstoffes mit fein verteilten festen Stoffen, z.i3. Talkum, natürlichen Tonen wie Y'aolin, Bentonit, Pyrophillit oder Diatoneenerde.Dusts are obtained by grinding the active ingredient with finely divided ones solid substances, e.g. i3. Talc, natural clays such as y'aolin, bentonite, pyrophillite or diatomaceous earth.

V&rsprühbare Lösungen, wie sie vielfach in Sprühdosen gehandelt werden, enthalten den Wirkstoff in einem organischen Lösungsmittel gelöst, daneben befindet sichz.3. als Treibmittel ein Gemisch von Fluorchlorkohlenwasserstoffen.Sprayable solutions, as often traded in spray cans contain the active ingredient dissolved in an organic solvent, next to it is located at 3. a mixture of chlorofluorocarbons as propellant.

Granulate können entweder durch Verdüsen des Wirkstoffes auf adsorptionsfähiges, granuliertes Inertmaterial hergestellt werden oder durch Aufbringen von Wirkstoffkonzentraten mittels Klebemitteln, z.B. Polyvinylalkohol, poiyacrylsaurem Natrium oder auch Mineralölen auf die Oberfläche von Trägerstolfen, wie Sand, Kaolinite, oder von granuliertem Inertmaterial. Auch können geeignete Wirkstoffe in der für die Herstellung von Düngemittelgranalien üblichen Weise - ge'nschtenfalls in Mischung mit Düngemitteln - hergestellt werden.Granules can either be sprayed onto adsorptive, Granulated inert material can be produced or by applying active ingredient concentrates by means of adhesives, e.g. polyvinyl alcohol, polyacrylic acid sodium or mineral oils onto the surface of support poles such as sand, kaolinite, or granulated Inert material. Suitable active ingredients can also be used in the production of fertilizer granules in the usual way - if necessary in a mixture with fertilizers.

In benetzbaren Pulvern variiert die Wirkstoffkonzentration z.B.In wettable powders the active ingredient concentration varies e.g.

zwischen etwa 10 % und 80 , der Rest besteht aus den oben angegebenen Formulierungszusätzen. Bei emulgierbaren Konzentraten ist die Wirkstoffkonzentration etwa 10 0 bis 70 %. Staubförmige Formulierungen enthalten meistens 5 - 20 % an Wirkstoff, versprühbare Lösungen etwa 2 - 20 . Bei Granulaten hängt der Wirkstoffgehalt z.T. davon ab, ob die wirksame Verbindung flüssig oder fest vorliegt und welche Granulierhilfsmittel, Füllstoffe usw. verwendet werden.between about 10% and 80, the remainder being those given above Formulation additives. In the case of emulsifiable concentrates, the active ingredient concentration is about 10 0 to 70%. Dust-like formulations usually contain 5 - 20% active ingredient, sprayable solutions about 2 - 20. In the case of granules, the active ingredient content depends partly on depends on whether the active compound is liquid or solid and which granulation aids, Fillers, etc. can be used.

Zur Anwendung werden die handelsüblichen Konzentrate gegebenenfalls in üblicher Weise verdünnt, z.B. bei benetzbaren Pulvern und emulgierbaren Konzentraten mittels Wasser. Staubförmige und granulierte Zubereitungen sowie versprühbare Lösungen werden vor der Anwendung nicht mehr mit weiteren inerten Stoffen verdünnt.The commercially available concentrates are optionally used for use diluted in the usual way, e.g. in the case of wettable powders and emulsifiable concentrates by means of water. Dust-like and granulated preparations as well as sprayable solutions are no longer diluted with other inert substances before use.

Der erfindungsgemäße Wirkstoff kann mit anderen Insektiziden, Fungiziden, Nematoziden und Herbiziden kombiniert werden.The active ingredient according to the invention can be combined with other insecticides, fungicides, Nematocides and herbicides are combined.

HERSTELLUNG BEISPIELE Allgemeine Herstellungsvorschriften Methode A: Eine Suspension von 0,5 Mol eines halogensubstituierten Benzamids der Formel III in 250 ml trockenem 1,2-Dichloräthan wird mit 56 ml (0,65 Mol) Oxalylchlorid versetzt. Das Gemisch wird 20 Stunden am Rückfluß erhitzt. Das Lösungsmittel wird abdestilliert und das halogensubstituierte Benzoylisocyanat destillativ gereinigt.MANUFACTURING EXAMPLES General manufacturing instructions Method A: A suspension of 0.5 moles of a halogen-substituted benzamide of the formula III in 250 ml of dry 1,2-dichloroethane is mixed with 56 ml (0.65 mol) of oxalyl chloride offset. The mixture is refluxed for 20 hours. The solvent will distilled off and the halogen-substituted benzoyl isocyanate purified by distillation.

0,15 Nol des so erhaltenen halogensubstituierten Benzoylisocyanats der Formel IV werden in trockenem Benzol gelöst, 0,5 ml einer tertiären Sticks-toffbase wie Triäthylamin zugesetzt und dazu unter Rühren eine Lösung eines substituierten Anilins der Formel V (0,15 Mol) in 200 ml trockenem Benzol getropft. Die Reaktionstemperatur wird bei 400 - 500C gehalten. Nach 2 Stunden wird der kristalline Niederschlag abgesaugt und getrocknet. Er kann, falls notwendig, durch Umkristallisieren gereinigt werden.0.15 mol of the halogen-substituted benzoyl isocyanate thus obtained of formula IV are dissolved in dry benzene, 0.5 ml of a tertiary nitrogen base such as triethylamine added and a solution of a substituted one with stirring Aniline of the formula V (0.15 mol) was added dropwise to 200 ml of dry benzene. The reaction temperature is kept at 400 - 500C. After 2 hours, the crystalline precipitate is filtered off with suction and dried. If necessary, it can be purified by recrystallization.

Methode B: 0,5 Mol eines halogensubstituierten Benzamids der Formel III werden in 250 ml trockenem Benzol mit 0,5 ml einer tertiären Stickstoffbase wie Triäthylamin und 0,55 Nol eines substituierten Phenylisocyanats der Formel II 24 Stunden am Rückfluß erhitzt. Nach dem Abkühlen wird das kristalline Reaktionsprodukt abgesaugt, mit Benzol gewaschen und getrocknet.Method B: 0.5 mol of a halogen-substituted benzamide of the formula III are dissolved in 250 ml of dry benzene with 0.5 ml of a tertiary nitrogen base such as triethylamine and 0.55 mol of a substituted phenyl isocyanate of the formula II Heated under reflux for 24 hours. After cooling, it becomes the crystalline reaction product suctioned off, washed with benzene and dried.

Zur zusätzlichen Reinigung kann aus organischem Lösungsmittel umkristallisiert werden.For additional cleaning, it can be recrystallized from an organic solvent will.

Tabelle analog R1, 2 R3 R4 Fp. (°°C) Nr. Methode 1 A 3,5-C1 3-OCF2-CF2H H 164-166 2 B 3,5-C1 4-OCF2-CF2H 3-CH3 186-187 3 A 3,5-C1 4-OCF2-CFClH H 182-185 4 A 3,5-C1 3-OCF2-CFClH 4-C1 151-152 5 A 3,5-C1 4-OCF2-CF2H H 161-163 6 B 3,5-C1 4-OCF2-CFH-CF3 H 194-196 7 B 3,5-C1 4-OCF2H H 171-174 8 A 3,5-C1 4-SCF2-CFC1H H 176-178 9 A 3,5-C1 4-OCCl=CClH H 127-129 10 A 3,5-C1 4-OCF2-CFClH 3-C1 205-206 11 B 2,6-C1 4-SCFS H 210-213 12 A 2,6-C1 4-OCC1=CC1H H 175-178 13 A 2,6-C1 3-OCF2-CF2H H 199-202 14 B 2,6-C1 4-OCF2-CFClH H 190-191 15 h 2,6-C1 4-OCF2-CF2H H 191-192 16 A 2,6-C1 4-OCF2H H 193-194 17 B 2,6-C1 4-OCF2-CFH-CF3 H 186-187 18 B 2,6-C1 4-OCF2-CFC1H 3-C1 177-179 19 A 2,6-C1 4-OCF2-CF2H 3-CH3 165-166 20 A 2,6-C1 4-SCF2-CFClH H 197-198 21 | A | 2,6-Cl | 4-OCF2-CCl2H |3-CH3| 192-193 Tabelle (Fortsetzung) analog R1, 2 R3 R4 Fp. (°C) Beispiel 22 B 2,6-F 3-OCF2-CF2H H 175-176 23 B 2,6-F 4-OCF2-CFClH H 211-212 24 A 2,6-F 4-OCF2-CCl2H H 211-213 25 A 2,6-F 4-OCCl=CClH H 177-179 26 A 2,6-F 4-OCF2-CF2H H 226-227 27 A 2,6-F 4-OCF2H H 204-206 28 B 2,6-F 4-OCF2-CFH-CF3 H 207-208 29 B 2,6-F 4-OCF2-CFClH 3-Cl 197-198 30 A 2,6-F 4-OCF2-CF2H 3-CH3 195-196 31 A 2,6-F 4-OCF2-CCl2H 3-CH3 204-205 32 A 2,6-F 4-SCF2-CFC1H H 192-193 FROMULIERUNGSBEISPIELE Beispiel A: Ein in Wasser leicht dispergierbares benetzbares Pulver wird erhalten, indem man 25 Gew.-teile N-2,6-Dichlorbenzoyl-N'-4-(1',2'-dichlorvinyloxy)-phenylharnstoff als Wirkstoff, 64 Gew.-teile kaolinhaltigen Quarz als Inertstoff, 10 Gew.-teile ligninsulfonsaures Kalium und 1 Gew.-teil oleylmethyltaurinsaures Natrium als Netz- und Dispergiermittel mischt und in einer Stiftmühle mahlt.Tabel analogous to R1, 2 R3 R4 melting point (°° C) No. method 1A 3,5-C1 3-OCF2-CF2H H 164-166 2 B 3,5-C1 4-OCF2-CF2H3-CH3186-187 3 A 3,5-C1 4-OCF2-CFClH H 182-185 4 A 3,5-C1 3-OCF2-CFClH 4-C1 151-152 5 A 3,5-C1 4-OCF2-CF2H H 161-163 6 B 3,5-C1 4-OCF2-CFH-CF3 H 194-196 7 B 3,5-C1 4-OCF2H H 171-174 8 A 3,5-C1 4-SCF2-CFC1H H 176-178 9 A 3,5-C1 4-OCCl = CClH H 127-129 10 A 3,5-C1 4-OCF2-CFClH 3-C1 205-206 11 B 2,6-C1 4-SCFS H 210-213 12 A 2,6-C1 4-OCC1 = CC1H H 175-178 13 A 2,6-C1 3-OCF2-CF2H H 199-202 14 B 2,6-C1 4-OCF2-CFClH H 190-191 15hrs 2,6-C1 4-OCF2-CF2H H 191-192 16 A 2,6-C1 4-OCF2H H 193-194 17 B 2,6-C1 4-OCF2-CFH-CF3 H186-187 18 B 2,6-C1 4-OCF2-CFC1H 3-C1 177-179 19 A 2,6-C1 4-OCF2-CF2H3-CH3 165-166 20 A 2,6-C1 4-SCF2-CFClH H 197-198 21 | A | 2,6-Cl | 4-OCF2-CCl2H | 3-CH3 | 192-193 Table (continued) analogous to R1, 2 R3 R4 melting point (° C) example 22 B 2,6-F 3-OCF2-CF2H H 175-176 23 B 2,6-F 4-OCF2-CFClH H 211-212 24 A 2,6-F 4-OCF2-CCl2H H 211-213 25 A 2,6-F 4-OCCl = CClH H 177-179 26 A 2,6-F 4-OCF2-CF2H H 226-227 27 A 2,6-F 4-OCF2H H 204-206 28 B 2,6-F 4-OCF2-CFH-CF3 H 207-208 29 B 2,6-F4-OCF2-CFClH3-Cl197-198 30 A 2,6-F 4 -OCF2-CF2H3-CH3 195-196 31 A 2,6-F 4-OCF2-CCl2H 3-CH3 204-205 32 A 2,6-F 4-SCF2-CFC1H H 192-193 FROMULATION EXAMPLES Example A: A wettable powder which is easily dispersible in water is obtained by adding 25 parts by weight of N-2,6-dichlorobenzoyl-N'-4- (1 ', 2'-dichlorovinyloxy) phenylurea as active ingredient, 64 parts by weight . parts of kaolin-containing quartz as inert substance, 10 parts by weight of lignosulphonic acid potassium and 1 part by weight of oleylmethyltauric acid sodium as wetting and dispersing agent are mixed and ground in a pin mill.

Beispiel B: Ein Stäubemittel, das sich zur Anwendung gut eignet, wird erhalten, indem man 10 Gew.-teile N-2,6-Dichlorbenzoyl-N'-4-(1',2'-dichlorvinyloxy)-phenylharnstoff als Wirkstoff und 90 Gew.-teile Talkum als Inertstoff mischt und in einer Schlagmühle zerkleinert.Example B: A dust that is well suited for use is obtained by adding 10 parts by weight of N-2,6-dichlorobenzoyl-N'-4- (1 ', 2'-dichlorovinyloxy) phenylurea Mixes as active ingredient and 90 parts by weight of talc as inert and in a hammer mill crushed.

Beispiel C: Ein emulgierbares Konzentrat besteht aus 15 Gew.-teilen N-2,6-Dichlorbenzoyl-N'-4-(1',2'-dichlorvinyloxy)-phenylharnstoff als Wirkstoff, 75 Gew.-teilen Cyclohexanon als Lösungsmittel und 10 Gew.-teilen oxäthyliertes Nonylphenol (10 AeO) als Emulgator.Example C: An emulsifiable concentrate consists of 15 parts by weight N-2,6-dichlorobenzoyl-N'-4- (1 ', 2'-dichlorovinyloxy) -phenylurea as active ingredient, 75 parts by weight of cyclohexanone as solvent and 10 parts by weight of oxethylated nonylphenol (10 AeO) as an emulsifier.

Beispiel D: Ein Granulat besteht z.B. aus etwa 2 - 15 Gew.-teilen N-2,6-Dichlorobenzoyl-N'-4-(1',2'-dichlorvinyloxy)-phenylharnstoff als Wirkstoff und einem inerten Granulatträgermaterial wie z.B. Attapulgit, Bimsgranulat und/oder Quarzsand.Example D: A granulate consists e.g. of about 2-15 parts by weight N-2,6-dichlorobenzoyl-N'-4- (1 ', 2'-dichlorovinyloxy) phenylurea as an active ingredient and an inert granulate carrier material such as attapulgite, pumice granulate and / or Quartz sand.

BIOLOGISCHE BEISPIELE Beispiel I: 0,5 ml einer acetonischen Lösung der Verbindung aus Beispiel 12 wurden auf der Boden einer Petrischale (10 cm Durchmesser), die ein Salatblatt von 5 cm Durchmesser enthielt, verteilt.BIOLOGICAL EXAMPLES Example I: 0.5 ml of an acetone solution the compound from Example 12 were on the bottom of a Petri dish (10 cm diameter), which contained a lettuce leaf of 5 cm in diameter, distributed.

Nach Antrocknung des Belags erfolgte die Besetzung der Petrischalen mit je 5 Larven (4. Stadiwn) des Africanischen Baumwollwurms (Spodoptera littoralis) in vierfacher Wiederholung.After the coating had dried on, the Petri dishes were filled each with 5 larvae (4th stage) of the African cotton worm (Spodoptera littoralis) repeated four times.

Nach einem Zeitraum von 3 Tagen wurden die Larven unter Normalbedigungen gehalten. Die Endkontrolle erfolgte am 7. Tage nach der Behandlwßg. Die Ergebnisse gehen aus folgender Tabelle I hervor: Tabelle I Verbindung Dosis (ppm) % Mortalität am gemäß in der 7. Tag nach der Beispiel Lösung Behandlung 62,5 100 14 31,25 75 15,625 60 Kontrolle 0 5 After a period of 3 days, the larvae were kept under normal conditions. The final check was carried out on the 7th day after the treatment. The results are shown in Table I below: Table I Compound dose (ppm)% mortality on according to the 7th day after the Example solution treatment 62.5 100 14 31.25 75 15.625 60 Control 0 5

Claims (3)

Insektizide Mittel PATENTANSPRUCHE: 1. berbindungen der Formel worin R1, R2 Halogen R3 (C1-C4)-Alkoxy, (C1-C4)-Alkylthio oder (C2-C4)-Alkenoxy, die durch 2 - 6 Halogenatome substituiert sind, R4 H, Halogen oder (C1-C2)-Alkyl bedeuten.Insecticidal agents PATENT CLAIMS: 1. compounds of the formula wherein R1, R2 halogen R3 (C1-C4) -alkoxy, (C1-C4) -alkylthio or (C2-C4) -alkenoxy, which are substituted by 2 - 6 halogen atoms, R4 H, halogen or (C1-C2) - Mean alkyl. 2. Verfahren zur Herstellung von Verbindungen der Formel I, dadurch gekennzeichnet, daß man Verbindungen der Formeln miteinander umsetzt, wobei jeweils einer der Reste A und B eine Isocyanatgruppe und der andere eine Aminogruppe darstellt.2. Process for the preparation of compounds of the formula I, characterized in that compounds of the formulas reacted with one another, one of the radicals A and B being an isocyanate group and the other being an amino group. 3. Insektizide Mittel, gekennzeichnet durch einen Gehalt an einer Verbindung der Formel I.3. Insecticidal agents, characterized by a content of one Compound of formula I.
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Cited By (25)

* Cited by examiner, † Cited by third party
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DE3003112A1 (en) * 1979-02-01 1980-08-14 Ciba Geigy Ag PHENYL URINE
EP0014675A2 (en) * 1979-02-01 1980-08-20 Ciba-Geigy Ag Substituted N-phenyl-N'-benzoyl ureas, processes for their preparation, agents containing these compounds and their use in combating pests
EP0014676A2 (en) * 1979-02-01 1980-08-20 Ciba-Geigy Ag Substituted N-phenyl-N'-benzoyl ureas, processes for their preparation, agents containing these compounds and their use in combating pests
DE2928410A1 (en) * 1979-07-11 1981-01-29 Schering Ag ACYL UREAS, INSECTICIDAL AGENTS CONTAINING THESE COMPOUNDS AND METHOD FOR THE PRODUCTION THEREOF
US4339460A (en) 1979-02-01 1982-07-13 Ciba-Geigy Corporation Pesticidal N-[4-(3'-bromoallyloxy)-phenyl]-N'-benzoyl ureas
EP0071279A1 (en) * 1981-07-30 1983-02-09 The Dow Chemical Company Substituted N-aroyl N'-phenyl urea compounds
US4399152A (en) * 1980-04-03 1983-08-16 Duphar International B.V. Substituted benzoyl ureas as insecticides
EP0143302A2 (en) * 1983-10-27 1985-06-05 Nihon Tokushu Noyaku Seizo K.K. Benzoylurea derivatives and intermediates
EP0154508A2 (en) * 1984-02-27 1985-09-11 Takeda Chemical Industries, Ltd. Thiophenylureas, their production and use
US4560770A (en) * 1983-02-09 1985-12-24 Ciba-Geigy Corporation Pesticidal compositions based on N-pyrrolylphenyl-N'-benzoylurea compounds
EP0174274A1 (en) * 1984-08-31 1986-03-12 Ciba-Geigy Ag Phenylbenzoylurea derivatives
FR2578392A1 (en) * 1985-03-07 1986-09-12 Bayer Ag Benzoylurea-based products for the protection of plants against snails and slugs
EP0219460A2 (en) * 1985-10-14 1987-04-22 Ciba-Geigy Ag Benzoylphenyl ureas
EP0277748A1 (en) * 1987-02-04 1988-08-10 Sumitomo Chemical Company, Limited A benzoylurea derivative and its production and use
US4798837A (en) * 1984-10-18 1989-01-17 Ciba-Geigy Corporation Benzoylphenylureas
US4868215A (en) * 1982-07-26 1989-09-19 The Dow Chemical Company Substituted N-aroyl N'-phenyl urea compounds
US5001266A (en) * 1982-07-26 1991-03-19 The Dow Chemical Company Substituted aniline compounds
US5135953A (en) * 1984-12-28 1992-08-04 Ciba-Geigy Use of acyl urea compounds for controlling endoparasites and ectoparasites of warm-blooded animals
US5153224A (en) * 1984-10-18 1992-10-06 Ciba-Geigy Corporation Benzoylphenylureas
US5157155A (en) * 1987-02-04 1992-10-20 Sumitomo Chemical Company, Limited Benzoylurea derivative and its production and use
US5210100A (en) * 1984-08-31 1993-05-11 Ciba-Geigy Corporation Phenylbenzoylureas
US5264213A (en) * 1988-07-08 1993-11-23 Dowelanco Process for preparing highly active water-dispersible pesticides
WO1998019995A1 (en) * 1996-11-08 1998-05-14 Dow Agrosciences Llc New benzoylphenylurea insecticides ans methods of using them to control cockroaches
WO1998019543A1 (en) * 1996-11-08 1998-05-14 Dow Agrosciences Llc New benzoylphenylurea insecticides and methods of using certain benzoylphenylureas to control cockroaches, ants, fleas, and termites
WO1998019542A1 (en) * 1996-11-08 1998-05-14 Dow Agrosciences Llc New benzoylphenylurea insecticides and methods of using certain benzoylphenylureas to control cockroaches, ants, fleas, and termites

Cited By (38)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3003112A1 (en) * 1979-02-01 1980-08-14 Ciba Geigy Ag PHENYL URINE
EP0014675A2 (en) * 1979-02-01 1980-08-20 Ciba-Geigy Ag Substituted N-phenyl-N'-benzoyl ureas, processes for their preparation, agents containing these compounds and their use in combating pests
EP0014676A2 (en) * 1979-02-01 1980-08-20 Ciba-Geigy Ag Substituted N-phenyl-N'-benzoyl ureas, processes for their preparation, agents containing these compounds and their use in combating pests
EP0014676A3 (en) * 1979-02-01 1980-11-12 Ciba-Geigy Ag Substituted n-phenyl-n'-benzoyl ureas, processes for their preparation, agents containing these compounds and their use in combating pests
US4310548A (en) 1979-02-01 1982-01-12 Ciba-Geigy Corporation Pesticidal N-tetrafluorophenyl-N'-benzoyl ureas
US4339460A (en) 1979-02-01 1982-07-13 Ciba-Geigy Corporation Pesticidal N-[4-(3'-bromoallyloxy)-phenyl]-N'-benzoyl ureas
EP0014675B1 (en) * 1979-02-01 1983-11-30 Ciba-Geigy Ag Substituted n-phenyl-n'-benzoyl ureas, processes for their preparation, agents containing these compounds and their use in combating pests
US4505931A (en) * 1979-02-01 1985-03-19 Ciba-Geigy Corporation Pesticidal N-(4-alkenylthio)-phenyl-N'-benzoylureas
DE2928410A1 (en) * 1979-07-11 1981-01-29 Schering Ag ACYL UREAS, INSECTICIDAL AGENTS CONTAINING THESE COMPOUNDS AND METHOD FOR THE PRODUCTION THEREOF
US4399152A (en) * 1980-04-03 1983-08-16 Duphar International B.V. Substituted benzoyl ureas as insecticides
EP0071279A1 (en) * 1981-07-30 1983-02-09 The Dow Chemical Company Substituted N-aroyl N'-phenyl urea compounds
US5001266A (en) * 1982-07-26 1991-03-19 The Dow Chemical Company Substituted aniline compounds
US4868215A (en) * 1982-07-26 1989-09-19 The Dow Chemical Company Substituted N-aroyl N'-phenyl urea compounds
US4560770A (en) * 1983-02-09 1985-12-24 Ciba-Geigy Corporation Pesticidal compositions based on N-pyrrolylphenyl-N'-benzoylurea compounds
EP0143302A3 (en) * 1983-10-27 1985-12-18 Nihon Tokushu Noyaku Seizo K.K. Benzoylurea derivatives and intermediates
EP0143302A2 (en) * 1983-10-27 1985-06-05 Nihon Tokushu Noyaku Seizo K.K. Benzoylurea derivatives and intermediates
EP0154508A2 (en) * 1984-02-27 1985-09-11 Takeda Chemical Industries, Ltd. Thiophenylureas, their production and use
EP0154508A3 (en) * 1984-02-27 1986-06-11 Takeda Chemical Industries, Ltd. Thiophenylureas, their production and use
EP0174274A1 (en) * 1984-08-31 1986-03-12 Ciba-Geigy Ag Phenylbenzoylurea derivatives
US5210100A (en) * 1984-08-31 1993-05-11 Ciba-Geigy Corporation Phenylbenzoylureas
US5153224A (en) * 1984-10-18 1992-10-06 Ciba-Geigy Corporation Benzoylphenylureas
US4798837A (en) * 1984-10-18 1989-01-17 Ciba-Geigy Corporation Benzoylphenylureas
US5107017A (en) * 1984-10-18 1992-04-21 Ciba-Geigy Corporation Benzoylpenylureas
US4980506A (en) * 1984-10-18 1990-12-25 Ciba-Geigy Corporation Benzoylphenylureas
US5135953A (en) * 1984-12-28 1992-08-04 Ciba-Geigy Use of acyl urea compounds for controlling endoparasites and ectoparasites of warm-blooded animals
FR2578392A1 (en) * 1985-03-07 1986-09-12 Bayer Ag Benzoylurea-based products for the protection of plants against snails and slugs
EP0219460A2 (en) * 1985-10-14 1987-04-22 Ciba-Geigy Ag Benzoylphenyl ureas
EP0219460A3 (en) * 1985-10-14 1988-04-20 Ciba-Geigy Ag Benzoylphenyl ureas
US4985460A (en) * 1987-02-04 1991-01-15 Sumitomo Chemical Company, Limited Benzoylurea derivative and its production and use
AU617244B2 (en) * 1987-02-04 1991-11-21 Sumitomo Chemical Company, Limited Aniline compound and process for preparing the same
AU595417B2 (en) * 1987-02-04 1990-03-29 Sumitomo Chemical Company, Limited A benzoylurea derivative and its production and use
US4904696A (en) * 1987-02-04 1990-02-27 Sumitomo Chemical Company, Limited Benzoylurea derivative and its production and use
EP0277748A1 (en) * 1987-02-04 1988-08-10 Sumitomo Chemical Company, Limited A benzoylurea derivative and its production and use
US5157155A (en) * 1987-02-04 1992-10-20 Sumitomo Chemical Company, Limited Benzoylurea derivative and its production and use
US5264213A (en) * 1988-07-08 1993-11-23 Dowelanco Process for preparing highly active water-dispersible pesticides
WO1998019995A1 (en) * 1996-11-08 1998-05-14 Dow Agrosciences Llc New benzoylphenylurea insecticides ans methods of using them to control cockroaches
WO1998019543A1 (en) * 1996-11-08 1998-05-14 Dow Agrosciences Llc New benzoylphenylurea insecticides and methods of using certain benzoylphenylureas to control cockroaches, ants, fleas, and termites
WO1998019542A1 (en) * 1996-11-08 1998-05-14 Dow Agrosciences Llc New benzoylphenylurea insecticides and methods of using certain benzoylphenylureas to control cockroaches, ants, fleas, and termites

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