DE3511550A1 - Pesticides based on carboximidates - Google Patents

Pesticides based on carboximidates

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Publication number
DE3511550A1
DE3511550A1 DE19853511550 DE3511550A DE3511550A1 DE 3511550 A1 DE3511550 A1 DE 3511550A1 DE 19853511550 DE19853511550 DE 19853511550 DE 3511550 A DE3511550 A DE 3511550A DE 3511550 A1 DE3511550 A1 DE 3511550A1
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Germany
Prior art keywords
alkyl
carbamoyl
spp
halogenated
ethyl ester
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Withdrawn
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DE19853511550
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German (de)
Inventor
Werner Dr. 6239 Eppstein Knauf
Volker Dr. 6233 Kelkheim Koch
Anna Dr. 6000 Frankfurt Waltersdorfer
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Hoechst AG
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Hoechst AG
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Priority to DE19853511550 priority Critical patent/DE3511550A1/en
Publication of DE3511550A1 publication Critical patent/DE3511550A1/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
    • A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
    • A01N55/02—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur containing metal atoms
    • A01N55/04—Tin
    • 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
    • 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
    • A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
    • 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
    • A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
    • A01N57/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds
    • A01N57/12—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds containing acyclic or cycloaliphatic radicals
    • 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
    • A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
    • A01N57/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds
    • A01N57/16—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds containing heterocyclic radicals

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  • 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)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

Pesticides containing a compound of the formula I <IMAGE> in which R1 represents H, halogen, alkyl or alkoxy, each of which can be halogenated; R2 represents (halogenated) alkyl; R3 represents H, halogen, alkyl, alkoxy or alkylmercapto, each of which can be halogenated; a substituted, optionally cyclic, amino radical; m and n represent a number from 1 to 5, with the proviso that, if (R1)m denotes 2,6-difluoro, (R3)n must not exclusively represent halogen or halogenated (C1-C6)alkyl, in combination with an insecticide selected from the group of the phosphoric esters, carbamates, carboxylates, formamidines or tin compounds or with other specific insecticides, display surprising synergistic effects upon use.

Description

Schädlingsbekämpfungsmittel auf der Basis von Carboximid-Carboximide-based pesticides

säureestern Gegenstand der vorliegenden Erfindung sind Schädlingsbekämpfungsmittel, gekennzeichnet durch einen Gehalt an einer Verbindung der Formel I, worin R1 jeweils unabhängig voneinander Wasserstoff; Halogen; (C1-C6)Alkyl, (C1-C6)Alkoxy, welche ein- oder mehrfach halogeniert sein können, R2 (C1-C6)Alkyl, welches ein- oder mehrfach halogeniert sein kann, R3 jeweils unabhängig voneinander Wasserstoff; Halogen; (C1-C6)Alkyl, (C1-C6)Alkoxy, (C1-C6)Alkylmercapto, wobei diese drei Reste ein- oder mehrfach halogeniert sein können; einen Rest der Formel NR4R5, wobei R4 und R5 unabhängig voneinander (C1-C6)Alkyl, bedeutet, das ein- oder mehrfach halogeniert sein kann oder R4 und R5 zusammen mit dem gemeinsamen N-Atom einen gesättigten 5- oder 6-Ring bilden, der Sauerstoff, Schwefel oder NR6 als Ringglied enthalten und durch (C1-C3)Alkyl substituiert sein kann, wobei R6 (C1-C3)Alkyl bedeutet und m,n unabhängig voneinander eine Zahl von 1 bis 5 bedeutet, mit der Maßgabe, daß wenn (R1)m 2,6-Difluor bedeutet, (R3)n nicht ausschließlich für Halogen oder halogeniertes (C1-C6)Alkyl stehen darf, in Kombination mit einem Insektizid aus der Gruppe der Phosphorsäureester, Carbamate, Carbonsäureester, Formamidine oder Zinnverbindungen oder mit einem anderen speziellen insektiziden Wirkstoff.acid esters The present invention relates to pesticides, characterized by a content of a compound of the formula I, in which R1 each independently of one another is hydrogen; Halogen; (C1-C6) alkyl, (C1-C6) alkoxy, which can be halogenated one or more times, R2 (C1-C6) alkyl, which can be halogenated one or more times, R3 in each case independently of one another hydrogen; Halogen; (C1-C6) alkyl, (C1-C6) alkoxy, (C1-C6) alkylmercapto, it being possible for these three radicals to be halogenated one or more times; a radical of the formula NR4R5, where R4 and R5 are independently (C1-C6) alkyl, which can be halogenated one or more times or R4 and R5 together with the common N atom form a saturated 5- or 6-membered ring, contain oxygen, sulfur or NR6 as a ring member and can be substituted by (C1-C3) alkyl, where R6 is (C1-C3) alkyl and m, n are independently a number from 1 to 5, with the proviso that if (R1) m 2,6-Difluor means, (R3) n may not exclusively stand for halogen or halogenated (C1-C6) alkyl, in combination with an insecticide from the group of phosphoric acid esters, carbamates, carboxylic acid esters, formamidines or tin compounds or with another special insecticidal active ingredient.

Als solche anderen speziellen Wirkstoffe seien genannt a- und ß-Avermectine, Bacillus thuringiensis, Bensultap, Binapacyl, Bisclofentezin, Buprofecin, Cartap, Cyromacin, Dicofol, Endosulfan, Ethoproxyfen, Fenoxycarb, Hexythiazox, 3-[2-(4-Ethoxyphenyl)-2-methyl-propoxymethyll 1 3-diphenylether (MTI-500), 5-[4-(4-Ethoxyphenyl)-4-methylpentyl]-2-fluor-1,3-diphenylether (MTI-800), 3- (2-Chlorphenyl ) -3-hydroxy-2- ( 2-phenyl-4-thiazolyl ) -propennitril (SN 72129), Thiocyclam, Kernpolyeder-und Granuloseviren.Other special active ingredients such as these include a- and ß-avermectins, Bacillus thuringiensis, Bensultap, Binapacyl, Bisclofentezin, Buprofecin, Cartap, Cyromacin, dicofol, endosulfan, ethoproxyfen, fenoxycarb, hexythiazox, 3- [2- (4-ethoxyphenyl) -2-methyl-propoxymethyll 1 3-diphenyl ether (MTI-500), 5- [4- (4-ethoxyphenyl) -4-methylpentyl] -2-fluoro-1,3-diphenyl ether (MTI-800), 3- (2-chlorophenyl) -3-hydroxy-2- (2-phenyl-4-thiazolyl) propenenitrile (SN 72129), thiocyclam, core polyhedron and granulosic viruses.

Überraschenderweise besitzen die erfindungsgemäßen Mittel überadditive, synergistische Effekte, d.h. die Wirkungen der Kombination sind höher als sie aufgrund der Wirkungen der Einzelkomponenten zu erwarten waren. Somit können die Aufwandmengen der Komponenten in der Mischung bezogen auf die Applikation der Einzelkomponenten deutlich verringert werden. Ein weiterer Vorteil der erfindungsgemäßen Kombinationen ist der, verglichen mit den Verbindungen der Formel I raschere Wirkungseintritt.Surprisingly, the agents according to the invention have superadditives, synergistic effects, i.e. the effects of the combination are higher than they are due to the effects of the individual components were to be expected. Thus, the application rates of the components in the mixture based on the application of the individual components can be significantly reduced. Another advantage of the combinations according to the invention is the faster onset of action compared to the compounds of formula I.

Von den erfindungsgemäß einzusetzenden Kombinationspartnern für die Verbindungen der Formel I seien genannt: 1. aus der Gruppe der Phosphorsäureester Azinphos-ethyl, Azinphos-methyl, 1-(4-Chlorphenyl)-4-(0-ethyl, S-propyl)phosphoryloxypyrazol (TIA-230), Chlorpyrifos, Coumaphos, Demeton, Demeton-S-methyl, Diazinon, Dichlorvos, Dimethoat, Ethoprophos, Etrimfos, Fenitrothion, Fenthion, Heptenophos, Parathion, Parathion-methyl, Phosalon, Pirimiphos-ethyl, Pirimiphos- methyl, Profenofos, Prothiofos, Sulprofos, Triazophos, Trichlorphon.Of the combination partners to be used according to the invention for Compounds of the formula I may be mentioned: 1. from the group of the phosphoric acid esters Azinphos-ethyl, azinphos-methyl, 1- (4-chlorophenyl) -4- (0-ethyl, S-propyl) phosphoryloxypyrazole (TIA-230), Chlorpyrifos, Coumaphos, Demeton, Demeton-S-methyl, Diazinon, Dichlorvos, Dimethoat, Ethoprophos, Etrimfos, Fenitrothion, Fenthion, Heptenophos, Parathion, Parathion-methyl, phosalone, pirimiphos-ethyl, pirimiphos- methyl, Profenofos, Prothiofos, Sulprofos, Triazophos, Trichlorphon.

2. aus der Gruppe der Carbamate Aldicarb, Bendiocarb, BPMC (2-(1-Nethylpropyl)phenyl methylcarbamat), Butocarboxim, Butoxicarboxim, Carbaryl, Carbofuran, Carbosulfan, Cloethocarb, Methomyl, Isoprocarb, Oxamyl, Pirimicarb, Promecarb, Propoxur, Thiodicarb.2. from the group of carbamates Aldicarb, Bendiocarb, BPMC (2- (1-Nethylpropyl) phenyl methylcarbamate), Butocarboxim, Butoxicarboxim, Carbaryl, Carbofuran, Carbosulfan, Cloethocarb, Methomyl, Isoprocarb, Oxamyl, Pirimicarb, Promecarb, Propoxur, Thiodicarb.

3. aus der Gruppe der Carbonsäureester Allethrin, Alphametrin, Bioallethrin, Bioresmethrin, Cycloprothrin, Cyfluthrin, Cyhalothrin, Cypermethrin, Deltamethrin, 2, 2-Dimethyl-3-(2-chlor-2-trifluormethyl vinyl)cyclopropancarbonsäure-(a-cyano-3-phenyl-2-methylbenzyl)ester (FMC 54800), Fenpropathrin, Fenfluthrin, Fenvalerat, Flucythrinate, Flumethrin, Fluvalinate, Permethrin, Resmethrin, Tralomethrin.3. from the group of carboxylic acid esters allethrin, alphametrin, bioallethrin, Bioresmethrin, Cycloprothrin, Cyfluthrin, Cyhalothrin, Cypermethrin, Deltamethrin, 2,2-Dimethyl-3- (2-chloro-2-trifluoromethyl vinyl) cyclopropanecarboxylic acid (α-cyano-3-phenyl-2-methylbenzyl) ester (FMC 54800), fenpropathrin, fenfluthrin, fenvalerate, flucythrinate, flumethrin, Fluvalinate, Permethrin, Resmethrin, Tralomethrin.

4. aus der Gruppe der Formamidine Amitraz, , Chlordimeform 5. aus der Gruppe der Zinnverbindungen Azocyclotin, Cyhexatin, Fenbutatinoxid Die Verbindungen der Formel I sind in der DE-OS 33 34 207 beschrieben. Bevorzugt von den Verbindungen der Formel I lassen sich folgende Wirkstoffe einsetzen: N-[N-(4-Chlorphenyl)carbamoyl3-2-fluorbenzearboximidsäureethylester N-EN-(4-Difluormethoxyphenyl)carbamoyl]-2-fluorbenzearboximidsäureethylester N-[N-(4-Difluormethoxyphenyl)carbamoyl]-2-chlorbenzearboximidsäureethylester N-[N-(4-Difluormethoxyphenyl)carbamoyl]-2,6-difluorbenzearboximidsäureethylester N-[N-(4-Difluormethoxyphenyl)carbamoyl]-2,4-dichlorbenzearboximidsäureethylester N-[N-(4-Chlordifluormethoxyphenyl)carbamoyl]-2,6-difluorbenzcarboximidsäureethylester N-[N-(4-Trifluormethoxyphenyl)carbamoyl]-2-fluorbenzearboximidsäureethylester N-[N-(4-Trifluormethoxyphenyl)carbamoyl]-2,6-difluorbenzcarboximidsäureethylester N-[N-(4-Trifluormethoxyphenyl)carbamoyl]-2,4-dichlorbenzcarboximidsäureethylester N-[N-(4-(1,1,2,2-tetrafluorethoxy)phenyl)carbamoyl]-2,6-difluorbenzcarboximidsäureethylester N-[N-(4-(1,1,2,3,3,3-hexafluor-1-propoxy)phenyl)carbamoyl]-2,6-difluorbenzcarboximidsäureethylester N-[N-(4-Trifluormethylmercaptophenyl)carbamoyl]-2,6-difluorbenzcarboximidsäureethylester N-[N-(4-Trifluormethylphenyl)carbamoyl]-2-fluorbenzearboximidsäureethylester N-[N-(4-Chlor-3-trifluormethylphenyl)carbamoyl]-2-fluorbenzcarboximidsäureethylester N-[N-(4-Chlor-3-trifluormethylphenyl)carbamoyl]-2-chlorbenzcarboximidsäureethylester N-[N-(3-Chlor-4-trifluormethoxy)carbamoyl]-2,6-difluorbenzcarboximidsäureethylester N-[N-(5-Chlor-4-(2-chlor-1,1,2-trifluorethylmercapto)-phenyl)carbamoyl]-2,6-difluorbenzcarboximidsäureethylester N-[N-(3-Chlor-4-(1 1 ,2,3,3,3-hexafluor-1-propoxy)-5-methylphenyl)carbamoyl]-2,6-difluorbenzearboximidsäureethylester N-[N-(3,5-Dichlor-4-difluormethoxyphenyl)carbamoyl]-2,6-difluorbenzcarboximidsäureethylester N-[N-(4-Chlordifluormethoxy-3,5-dichlorphenyl)carbamoyl]-2,6-difluorbenzcarboximidsäureethylester N-[N-(3,5-Dichlor-4-trifluormethoxyphenyl)carbamoyl3-2,6-difluorbenzcarboximidsäureethylester N-[N-(4-(2-Chlor-1,1,2-trifluorethoxy)-3,5-dichlorphenyl)-carbamoyl]-2-fluorbenzcarboximidsäureethylester N-[N-4-(2-Chlor-1,1,2-trifluorethoxy)-3,5-dichlorphenyl)-carbamoyl]-2-chlorbenzcarboximidsäureethylester N-[N-4-(2-Chlor-1,1,2-trifluorethoxy)-3,5-dichlorphenyl)-carbamoyl]-2,6-difluorbenzcarboximidsäureethylester N-[N-4-(2-Chlor-1,1,2-trifluorethoxy)-3,5-dichlorphenyl)-carbamoyl]-2-chlor-6-fluorbenzcarboximidsäureethylester N-[N-4-(2-Chlor-1,1,2-trifluorethoxy)-3,5-dichlorphenyl)-carbamoyl]-2,6-dichlorbenzcarboximidsäureethylester N-[N-4-(2-Chlor-1,1,2-trifluorethoxy)-3,5-dichlorphenyl)-carbamoyl]-2-methylbenzcarboximidsäureethylester N-[N-4-(2-Brom-1,1,2-trifluorethoxy)-3,5-dichlorphenyl)-carbamoyl]-2-fluorbenzcarboximidsäureethylester N-[N-4-(2-Brom-1,1,2-trifluorethoxy)-3,5-dichlorphenyl)-carbamoyl]-2-chlorbenzcarboximidsäureethylester N-[N-4-(2-Brom-1,1,2-trifluorethoxy)-3,5-dichlorphenyl)-carbamoyl]-2,6-difluorbenzcarboximidsäureethylester N-[N-(3,5-Dichlor-4-(1,1,2,2-tetrafluorethoxy)phenyl)-carbamoyl]-2-fluorbenzcarboximidsäureethylester N-[N-(3,5-Dichlor-4-(1,1,2,2-tetrafluorethoxy)phenyl)-carbamoyl]-2-chlorbenzcarboximidsäureethylester N-[N-(3,5-Dichlor-4-(1,1,2,2-tetrafluorethoxy)phenyl)-carbamoyl]-2,6-difluorbenzcarboximidsäureethylester N-[N-(3,5-Dichlor-4-(1,1,2,2-tetrafluorethoxy)phenyl)-carbamoyl]-2-methylbenzcarboximidsäureethylester N-[N-(3,5-Dichlor-4-(1,1,2,2-tetrafluorethoxy)phenyl)-carbamoyl]-2-trifluormethylbenzcarboximidsäureethylester N-[N-(3,5-Dichlor-4-(1,1,2,2-tetrafluorethoxy)phenyl)-carbamoyl]-2-fluorbenzcarboximidsäure1-propylester N-[N-(4-(2,2-Dibrom-1,1-difluorethoxy)-3,5-dichlorphenyl)-carbamoyl]-2,6-difluorcarboximidsäureethylester N-[N-(4-(2,2-Dichlor-1,1-difluorethoxy)-3,5-dichlorphenyl)-carbamoyl]-2,6-difluorbenzcarboximidsäureethylester N-[N-(4-(2-Chlor-1,1-difluorethoxy)-3,5-dichlorphenyl)-carbamoyl]-2,6-difluorbenzcarboximidsäureethylester N-[N-(3,5-Dichlor-4-pentafluorethoxyphenyl)carbamoyl]-2,6-difluorbenzcarboximidsäureethylester N-[N-(3,5-Dichlor-4-(1 1 ,2,3,3,3-hexafluor-1-propoxy)-phenyl) carbamoyl]-2-fluorbenzcarboximidsäureethylester N-[N-(3,5-Dichlor-4-(1,1,2,3,3,3-hexafluor-1-propoxy)-phenyl) carbamoyl]-2-chlorbenzcarboximidsäureethylester N-[N-(3,5-Dichlor-4-(1,1,2,3,3,3-hexafluor-1-propoxy)-phenyl) carbamoyl]-2 , 6-difluorbenzcarboximidsäureethylester N-[N-(3,5-Dichlor-4-(1,1,2,3,3,3-hexafluor-1-propoxy)-phenyl)carbamoyl]-2-methylbenzcarboximidsäureethylester N-[N-(3,5-Dichlor-4-(2,2,2-trifluorethoxy)phenyl) carbamoyl]-2 ,6-difluorbenzcarboximidsäureethylester N-[N-(3,5-Dichlor-4-(2,2,3,3,3-tetrafluor-1-propoxy)phenyl)-carbamoyl]-2-fluorbenzearboximidsäureethylester N-[N-(3,5-Dichlor-4-(2,2,3,3,3-tetrafluor-1-propoxy)phenyl) carbamoyl]-2,6-difluorbenzearboximidsäureethylester N-[N-(3,5-Dichlor-4-(2,2,3,4,4,4-heptafluor-1-butoxy)phenyl) carbamoyl]-2,6-difluorbenzcarboximidsäureethylester N-[N-(3,5-Dichlor-4-(2,2,3,3,4,4,4-heptafluor-1-butyloxy)-phenyl) carbamoyl]-2 , 6-difluorbenzcarboximidsäureethylester N-[N-(3,5-Dichlor-4-difluormethylmercaptophenyl)carbamoyl 3 2-fluorbenzcarboximidsäurecycloethylester N-[N-(3,5-Dichlor-4-trifluormethylmercaptophenyl)carbamoyl] 2,6-difluorbenzcarboximidsäureethylester N-[N-(3,5-Dichlor-4-(1,1,2,2-tetrafluorethylmpercapto)-phenyl)carbamoyl]-2 ,6-difluorbenzcarboximidsäureethylester N-[N-(3,5-Dichlor-4-(1,1,2,3-3,3-hexafluor-1-propylmpercapto)phenyl)carbamoyl]-2,6-difluorbenzearboximidsäureethylester N-[N-(3,5-Dichlor-4-(1-Pyrrolidinyl)phenyl)carbamoyl]-2-fluorbenzcarboximidsäureethylester N-[N-(3,5-Dichlor-4-(1-Pyrrolidinyl)phenyl)carbamoyl]-2 ,6-difluorbenzcarboximidsäureethylester N-[N-(3,5-Dichlor-4-(4-morpholinyl)phenyl)carbamoyl]-2,6-difluorbenzcarbximidsäureethylester N-[N-(3,5-Dichlor-4-(4-methyl-1-piperazinyl)phenyl)-carbamoyl]-2,6-difluorbenzcarboximidsäureethylester N-[N-(4-(2-Chlor-1,1,2-trifluorethoxy)-3,5-dichlor-2-fluorphenyl)carbamoyl]-2,6-difluorbenzearboximidsäureethylester N-[N-(3,5-Dichlor-2-fluor-4-(1,1,2,3,3,3-hexafluor-1-propyloxy)phenyl)carbamoyl]-2,6-difluorbenzcarboximidsäureethylester N-[N-(3,5-Dichlor-2,4-difluorphenyl)carbamoyl]-2-fluorbenzcarboximidsäureethylester N-[N-(3,5-Dichlor-2,4-difluorphenyl)carbamoyl]-2-chlor benzcarboximidsäureethylester N-[N-(4-(1,1,2,3,3,3-Hexafluor-1-propyloxy)-2,3,5-trichlorphenyl)carbamoyl]-2-fluorbenzearboximidsäureethylester N-[N-(4-(1,1,2,3,3,3-Hexafluor-1-propyloxy)-2,3,5-trichlorphenyl)carbamoyl]-2-chlorbenzearboximidsäureethylester N-[N-(4-(1,1,2,3,3,3-Hexafluor-1-propyloxy)-2,3,5-tri chlorphenyl)carbamoyl]-2,6-difluorbenscarboximidsäureethylester Besonders bevorzugt von den Verbindungen der Formel I sind die Wirkstoffe A bis F der Formel: Verbindung A : X¹ X=H, X2= F ; R4= CF2CHFCF3 Verbindung B : = R, X2= F ; R4= CF2CHF2 Verbindung C : X1= H, X2= Cl ; R4= CF2CHFCF3 Verbindung D : g1x2= F ; R4= CF2CHClF Verbindung E : X1 ,X2= F ; R4 CF2CHFCF3 Verbindung F : X1 ,X2= F ; R4= CF2CHF2 Die erfindungsgemäßen Mittel eignen sich bei guter Pflanzenverträglichkeit und günstiger Warmblütertoxizität zur Bekämpfung von tierischen Schädlingen, insbesondere Insekten, Spinnentieren und Nematoden, ganz besonders bevorzugt zur Bekämpfung von Insekten, sowie deren Entwicklungsstadien, die in der Landwirtschaft, in Forsten, im Vorrats- und Materialschutz sowie auf dem Hygienesektor vorkommen. Sie sind gegen normal sensible und resistente Arten sowie gegen alle oder einzelne Entwicklungsstadien wirksam. Zu den oben erwähnten Schädlingen gehören: Aus der Ordnung der Isopoda z.B. Oniscus asellus, Armadillidium vulgare, Porcellio scaber.4. from the group of the formamidines amitraz,, chlordimeform 5. from the group of the tin compounds azocyclotine, cyhexatin, fenbutatin oxide The compounds of the formula I are described in DE-OS 33 34 207. Of the compounds of the formula I, the following active ingredients can preferably be used: N- [N- (4-chlorophenyl) carbamoyl3-2-fluorobenzearboximidic acid ethyl ester N-EN- (4-difluoromethoxyphenyl) carbamoyl] -2-fluorobenzearboximidic acid ethyl ester N- [N- (4th -Difluoromethoxyphenyl) carbamoyl] -2-chlorobenzearboximidic acid ethyl ester N- [N- (4-Difluoromethoxyphenyl) carbamoyl] -2,6-difluorobenzearboximidic acid ethyl ester N- [N- (4-difluoromethoxyphenyl) carbamoyl] -2,4-dichloro-ethylbenzearboximidate (4-Chlorodifluoromethoxyphenyl) carbamoyl] -2,6-difluorobenzcarboximidic acid ethyl ester N- [N- (4-trifluoromethoxyphenyl) carbamoyl] -2-fluorobenzearboximidic acid ethyl ester N- [N- (4-trifluoromethoxyphenyl) carbamoyl] -2,6-difluoromethoxyphenyl) carbamoyl] -2,6-difluorobenzic acid ethyl carbox N- (4-Trifluoromethoxyphenyl) carbamoyl] -2,4-dichlorobenzecarboximidic acid ethyl ester N- [N- (4- (1,1,2,2-tetrafluoroethoxy) phenyl) carbamoyl] -2,6-difluorobenzecarboximidic acid ethyl ester N- [N- ( 4- (1,1,2,3,3,3-hexafluoro-1-propoxy) phenyl) carbamoyl] -2,6-difluorobenzarboximidic acid ethyl ester N- [N- (4- Trifluoromethyl mercaptophenyl) carbamoyl] -2,6-difluorobenzecarboximidic acid ethyl ester N- [N- (4-trifluoromethylphenyl) carbamoyl] -2-fluorobenzearboximidic acid ethyl ester N- [N- (4-chloro-3-trifluoromethylphenyl) carbamoyl] -2-fluorobenzarboximidic acid ethyl ester N- [N- (4-chloro-3-trifluoromethylphenyl) carbamoyl] -2-fluorobenzarboximidate ethyl ester - (4-Chloro-3-trifluoromethylphenyl) carbamoyl] -2-chlorobenzecarboximidic acid ethyl ester N- [N- (3-chloro-4-trifluoromethoxy) carbamoyl] -2,6-difluorobenzecarboximidic acid ethyl ester N- [N- (5-chloro-4- (2-chloro-1,1,2-trifluoroethylmercapto) -phenyl) carbamoyl] -2,6-difluorobenzecarboximidic acid ethyl ester N- [N- (3-chloro-4- (1 1, 2,3,3,3-hexafluoro- 1-propoxy) -5-methylphenyl) carbamoyl] -2,6-difluorobenzearboximidic acid ethyl ester N- [N- (3,5-dichloro-4-difluoromethoxyphenyl) carbamoyl] -2,6-difluorobenzarboximidic acid ethyl ester N- [N- (4-chlorodifluoromethoxy -3,5-dichlorophenyl) carbamoyl] -2,6-difluorobenzecarboximidic acid ethyl ester N- [N- (3,5-dichloro-4-trifluoromethoxyphenyl) carbamoyl3-2,6-difluorobenzecarboximidic acid ethyl ester N- [N- (4- (2-chloro -1,1,2-trifluoroethoxy) -3,5-dichlorophenyl) carbamoyl] -2-f Ethyl luobenzecarboximidate N- [N-4- (2-chloro-1,1,2-trifluoroethoxy) -3,5-dichlorophenyl) -carbamoyl] -2-chlorobenzarboximidic acid ethyl ester N- [N-4- (2-chloro-1,1 , 2-trifluoroethoxy) -3,5-dichlorophenyl) carbamoyl] -2,6-difluorobenzecarboximidic acid ethyl ester N- [N-4- (2-chloro-1,1,2-trifluoroethoxy) -3,5-dichlorophenyl) -carbamoyl ] -2-chloro-6-fluorobenzecarboximidic acid ethyl ester N- [N-4- (2-chloro-1,1,2-trifluoroethoxy) -3,5-dichlorophenyl) carbamoyl] -2,6-dichlorobenzecarboximidic acid ethyl ester N- [N- 4- (2-chloro-1,1,2-trifluoroethoxy) -3,5-dichlorophenyl) carbamoyl] -2-methylbenzcarboximidic acid ethyl ester N- [N-4- (2-bromo-1,1,2-trifluoroethoxy) - 3,5-dichlorophenyl) carbamoyl] -2-fluorobenzarboximidic acid ethyl ester N- [N-4- (2-bromo-1,1,2-trifluoroethoxy) -3,5-dichlorophenyl) -carbamoyl] -2-chlorobenzarboximidic acid ethyl ester N- [ N-4- (2-Bromo-1,1,2-trifluoroethoxy) -3,5-dichlorophenyl) -carbamoyl] -2,6-difluorobenzecarboximidic acid ethyl ester N- [N- (3,5-dichloro-4- (1, 1,2,2-tetrafluoroethoxy) phenyl) carbamoyl] -2-fluorobenzarboximidic acid ethyl ester N- [N- ( 3,5-dichloro-4- (1,1,2,2-tetrafluoroethoxy) phenyl) carbamoyl] -2-chlorobenzecarboximidic acid ethyl ester N- [N- (3,5-dichloro-4- (1,1,2,2 -tetrafluoroethoxy) phenyl) -carbamoyl] -2,6-difluorobenzcarboximidic acid ethyl ester N- [N- (3,5-dichloro-4- (1,1,2,2-tetrafluoroethoxy) phenyl) -carbamoyl] -2-methylbenzcarboximidic acid ethyl ester N- Ethyl [N- (3,5-dichloro-4- (1,1,2,2-tetrafluoroethoxy) phenyl) carbamoyl] -2-trifluoromethylbenzcarboximidate N- [N- (3,5-dichloro-4- (1.1 , 2,2-tetrafluoroethoxy) phenyl) carbamoyl] -2-fluorobenzarboximidic acid 1-propyl ester N- [N- (4- (2,2-dibromo-1,1-difluoroethoxy) -3,5-dichlorophenyl) carbamoyl] - 2,6-difluorocarboximidic acid ethyl ester N- [N- (4- (2,2-dichloro-1,1-difluoroethoxy) -3,5-dichlorophenyl) -carbamoyl] -2,6-difluorobenzecarboximidic acid ethyl ester N- [N- (4- (2-chloro-1,1-difluoroethoxy) -3,5-dichlorophenyl) carbamoyl] -2,6-difluorobenzecarboximidic acid ethyl ester N- [N- (3,5-dichloro-4-pentafluoroethoxyphenyl) carbamoyl] -2,6- ethyl difluorobenzarboximidate N- [N- (3,5-dichloro-4- (1 1, 2,3,3,3-hexafluoro-1-propoxy) -pheny l) carbamoyl] -2-fluorobenzecarboximidic acid ethyl ester N- [N- (3,5-dichloro-4- (1,1,2,3,3,3-hexafluoro-1-propoxy) -phenyl) carbamoyl] -2-chlorobenzecarboximidic acid ethyl ester N- [N- (3,5-dichloro-4- (1,1,2,3,3,3-hexafluoro-1-propoxy) -phenyl) carbamoyl] -2,6-difluorobenzecarboximidic acid ethyl ester N- [N- ( 3,5-dichloro-4- (1,1,2,3,3,3-hexafluoro-1-propoxy) -phenyl) carbamoyl] -2-methylbenzcarboximidic acid ethyl ester N- [N- (3,5-dichloro-4- (2,2,2-trifluoroethoxy) phenyl) carbamoyl] -2,6-difluorobenzecarboximidic acid ethyl ester N- [N- (3,5-dichloro-4- (2,2,3,3,3-tetrafluoro-1-propoxy)) phenyl) carbamoyl] -2-fluorobenzearboximidate, ethyl N- [N- (3,5-dichloro-4- (2,2,3,3,3-tetrafluoro-1-propoxy) phenyl) carbamoyl] -2,6-difluorobenzearboximidate Ethyl N- [N- (3,5-dichloro-4- (2,2,3,4,4,4-heptafluoro-1-butoxy) phenyl) carbamoyl] -2,6-difluorobenzecarboximidate N- [N- (3 , 5-dichloro-4- (2,2,3,3,4,4,4-heptafluoro-1-butyloxy) -phenyl) carbamoyl] -2,6-difluorobenzecarboximidic acid ethyl ester N- [N- (3,5-dichloro -4-difluoromethyl mercaptophenyl) carbamoyl 3 Cycloethyl 2-fluorobenzarboximidate N- [N- (3,5-dichloro-4-trifluoromethylmercaptophenyl) carbamoyl] ethyl 2,6-difluorobenzarboximidate N- [N- (3,5-dichloro-4- (1,1,2,2- tetrafluoroethylmpercapto) -phenyl) carbamoyl] -2, 6-difluorobenzarboximidic acid ethyl ester N- [N- (3,5-dichloro-4- (1,1,2,3-3,3-hexafluoro-1-propylmpercapto) phenyl) carbamoyl] Ethyl -2,6-difluorobenzearboximidate N- [N- (3,5-dichloro-4- (1-pyrrolidinyl) phenyl) carbamoyl] -2-fluorobenzarboximidic acid ethyl ester N- [N- (3,5-dichloro-4- (1- Pyrrolidinyl) phenyl) carbamoyl] 2,6-difluorobenzcarboximidic acid ethyl ester N- [N- (3,5-dichloro-4- (4-morpholinyl) phenyl) carbamoyl] -2,6-difluorobenzarboximidic acid ethyl ester N- [N- (3.5 -Dichloro-4- (4-methyl-1-piperazinyl) phenyl) -carbamoyl] -2,6-difluorobenzecarboximidic acid ethyl ester N- [N- (4- (2-chloro-1,1,2-trifluoroethoxy) -3.5) -dichlor-2-fluorophenyl) carbamoyl] -2,6-difluorobenzearboximidic acid ethyl ester N- [N- (3,5-dichloro-2-fluoro-4- (1,1,2,3,3,3-hexafluoro-1- propyloxy) phenyl) carbamoyl] -2,6-difluorobenzecarboximidic acid ethyl ter N- [N- (3,5-dichloro-2,4-difluorophenyl) carbamoyl] -2-fluorobenzecarboximidic acid, ethyl ester, N- [N- (3,5-dichloro-2,4-difluorophenyl) carbamoyl] -2-chlorobenzarboximidic acid, ethyl ester N- [N- (4- (1,1,2,3,3,3-hexafluoro-1-propyloxy) -2,3,5-trichlorophenyl) carbamoyl] -2-fluorobenzearboximidic acid ethyl ester N- [N- (4- Ethyl (1,1,2,3,3,3-hexafluoro-1-propyloxy) -2,3,5-trichlorophenyl) carbamoyl] -2-chlorobenzearboximidate N- [N- (4- (1,1,2,3 , 3,3-hexafluoro-1-propyloxy) -2,3,5-tri chlorophenyl) carbamoyl] -2,6-difluorobensecarboximidic acid ethyl ester Particularly preferred of the compounds of the formula I are the active ingredients A to F of the formula: Compound A: X¹, X = H, X2 = F; R4 = CF2CHFCF3 Compound B: = R, X2 = F; R4 = CF2CHF2 Compound C: X1 = H, X2 = Cl; R4 = CF2CHFCF3 Compound D: g1x2 = F; R4 = CF2CHClF Compound E: X1, X2 = F; R4 CF2CHFCF3 Compound F: X1, X2 = F; R4 = CF2CHF2 The agents according to the invention are suitable for combating animal pests, especially insects, arachnids and nematodes, very particularly preferably for combating insects, and their developmental stages, which are found in agriculture, in forests, in storage, if they are well tolerated by plants and have favorable warm-blooded toxicity. and material protection as well as in the hygiene sector. They are effective against normally sensitive and resistant species and against all or individual stages of development. The abovementioned pests include: From the order of the Isopoda, for example Oniscus asellus, Armadillidium vulgare and Porcellio scaber.

Aus der Ordnung der Diplopoda z.B. Blaniulus guttulatus.From the order of the Diplopoda, e.g. Blaniulus guttulatus.

Aus der Ordnung der Chilopoda z.B. Geophilus carpophagus, Scutigera spec.From the order of the Chilopoda, e.g. Geophilus carpophagus and Scutigera spec.

Aus der Ordnung der Symphyla z.B. Scutigerella immaculata.From the order of the Symphyla, e.g. Scutigerella immaculata.

Aus der Ordnung der Thysanura z.B. Bepisma saccharina.From the order of the Thysanura e.g. Bepisma saccharina.

Aus der Ordnung der Collembola z.B. Onychiurus armatus.From the order of the Collembola, e.g. Onychiurus armatus.

Aus der Ordnung der Orthoptera z.B. Blatta orientalis, Periplaneta americana, Leucophaea maderae, Blatella germanica, Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus differentialis, Schistocerca gregaria.From the order of the Orthoptera, e.g. Blatta orientalis, Periplaneta americana, Leucophaea maderae, Blatella germanica, Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus differentialis, Schistocerca gregaria.

Aus der Ordnung der Dermaptera z.B. Forficula auricularia.From the order of the Dermaptera, e.g. Forficula auricularia.

Aus der Ordnung der Isoptera z.B. Reticulitermes spp., Aus der Ordnung der Anoplura z.B. Phylloera vastatrix, Pemphigus spp., Pediculus humanus corporis, Haematopinus spp., Linognathus spp.From the order of the Isoptera, e.g. Reticulitermes spp., From the order the Anoplura e.g. Phylloera vastatrix, Pemphigus spp., Pediculus humanus corporis, Haematopinus spp., Linognathus spp.

Aus der Ordnung der Mallophaga z.B. Trichodectes spp., Damalinea spp.From the order of the Mallophaga, for example Trichodectes spp., Damalinea spp.

Aus der Ordnung der Thysanoptera z.B. Hercinothrips femoralis, Thrips tabaci.From the order of the Thysanoptera, e.g. Hercinothrips femoralis, Thrips tabaci.

Aus der Ordnung der Heteroptera z.B. Eurygaster spp., Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodnius prolixus, Triatoma spp.From the order of the Heteroptera, e.g. Eurygaster spp., Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodnius prolixus, Triatoma spp.

Aus der Ordnung der Homoptera z.B. Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Bravicornyne brassicae, Cryptomyzus ribis, Doralis fabae, Doralis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Macrosiphium avenae, Myzus spp., Phorodon humuli, Rhopalosiphum padi, Empoasca spp., Euscelus bilobatus, Nephotettix cincticeps, Lecanium corni, Saissetia oleae, iaodelphax striatellus, Nilaparvata lugens, Aonidiella auroantii, Aspidiotus hederae, Pseudococcus spp., Psylla spp.From the order of the Homoptera, e.g. Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Bravicornyne brassicae, Cryptomyzus ribis, Doralis fabae, Doralis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Macrosiphium avenae, Myzus spp., Phorodon humuli, Rhopalosiphum padi, Empoasca spp., Euscelus bilobatus, Nephotettix cincticeps, Lecanium corni, Saissetia oleae, iaodelphax striatellus, Nilaparvata lugens, Aonidiella auroantii, Aspidiotus hederae, Pseudococcus spp., Psylla spp.

Aus der Ordnung der tepidoptera z.B. Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletis blancardella, Hyponomeuta padella, Plutella maculipennis, Malacosoma neustria, Euproctis chrysorrhoea, Lymantria spp., Buceulatrix thurberiella, Phyllocnistis citrella, Agrotis spp, Euxoa spp., Feltia spp., Earias insulana, Heliothis spp., Laphygma exigua, Mamestra brassicae, Panolis flammea, Prodenia litura, Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Galleria mellonella, Cacoecia podana, Capua reticulana, Choristoneura fumiferana, Clysia anbiguella, Homona magnanima, Tortrix viridana.From the order of the tepidoptera, e.g. Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletis blancardella, Hyponomeuta padella, Plutella maculipennis, Malacosoma neustria, Euproctis chrysorrhoea, Lymantria spp., Buceulatrix thurberiella, Phyllocnistis citrella, Agrotis spp, Euxoa spp., Feltia spp., Earias insulana, Heliothis spp., Laphygma exigua, Mamestra brassicae, Panolis flammea, Prodenia litura, Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Galleria mellonella, Cacoecia podana, Capua reticulana, Choristoneura fumiferana, Clysia anbiguella, Homona magnanima, Tortrix viridana.

Aus der Ordnung der Coleoptera z.B. Anobium punctatum, Rhizopertha dominica, Bruchidius obtectus, Acanthoscelides obtectus, Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedon cochlearieae, Diabrotica spp., Psylliodes chrysocephala, Epilachna varivestis, Atomaria spp., Oryzaephilus surinamensis, Anthonomus spp., Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites sordidus, Ceuthorrhynchus assimilis, Hypera postica, Dermestes spp., Trogoderma spp., Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus, Ptinus spp., Niptus hololeucus, Gibbium psylloides Tribolium spp., Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha, Amphimallon solstitialis, Costelytra zealandica.From the order of the Coleoptera, e.g. Anobium punctatum, Rhizopertha dominica, Bruchidius obtectus, Acanthoscelides obtectus, Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedon cochlearieae, Diabrotica spp., Psylliodes chrysocephala, Epilachna varivestis, Atomaria spp., Oryzaephilus surinamensis, Anthonomus spp., Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites sordidus, Ceuthorrhynchus assimilis, Hypera postica, Dermestes spp., Trogoderma spp., Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus, Ptinus spp., Niptus hololeucus, Gibbium psylloides Tribolium spp., Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha, Amphimallon solstitialis, Costelytra zealandica.

Aus der Ordnung der Hymenoptera z.B. Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp.From the order of the Hymenoptera, for example Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp.

Aus der Ordnung der Diptera z.B. Aedes spp., Anopheles spp., Culex spp., Drosophila melanogaster, Musca spp., Fannia spp., Calliphora erythrocephala, Bucilia spp., Chrysomyia spp., Cuterebra spp., Gastrophilus spp., Hyppobosca spp., Stomoxys spp., Oestrus spp., Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinella frit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae, Tipula paludosa.From the order of the Diptera, for example, Aedes spp., Anopheles spp., Culex spp., Drosophila melanogaster, Musca spp., Fannia spp., Calliphora erythrocephala, Bucilia spp., Chrysomyia spp., Cuterebra spp., Gastrophilus spp., Hyppobosca spp., Stomoxys spp., Oestrus spp., Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinella frit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae, Tipula paludosa.

Aus der Ordnung der Siphonaptera z.B. Xenopsylla cheopis, Ceratophyllus spp.From the order of the Siphonaptera, e.g. Xenopsylla cheopis, Ceratophyllus spp.

Aus der Ordnung der Arachnida z.B. Scorpio maurus, Latrodectus mactans.From the order of the Arachnida, e.g. Scorpio maurus, Latrodectus mactans.

Die erfindungsgemäßen Mittel enthalten die Wirkstoffe im allgemeinen zu 1 - 95 Gew.-%. Sie können als Spritzpulver, emulgierbare Konzentrate, versprühbare Lösungen, Stäubemittel oder Granulate in den üblichen Zubereitungen angewendet werden.The agents according to the invention generally contain the active ingredients 1 to 95% by weight. They can be used as wettable powders, emulsifiable concentrates, sprayable Solutions, dusts or granules can be used in the usual preparations.

Spritzpulver sind in Wasser gleichmäßig dispergierbare Präparate, die neben dem Wirkstoff außer einem Verdünnungs- oder Inertstoff noch Netzmittel, z.B. polyoxethylierte Alkylphenole, polyoxethylierte Fettalkohole, Alkyl- oder Alkylphenol-sulfonate und Dispergiermittel, 6,6'-disulfonsaures Natrium, dibutylnaphthalinsulfonsaures Natrium oder auch oleylmethyltaurinsaures Natrium enthalten.Wettable powders are preparations that can be uniformly dispersed in water, which in addition to the active ingredient, besides a diluent or inert substance, also wetting agents, e.g. polyoxethylated alkylphenols, polyoxethylated fatty alcohols, alkyl or alkylphenol sulfonates and dispersants, sodium 6,6'-disulfonic acid, dibutylnaphthalenesulfonic acid Contain sodium or oleylmethyltauric acid sodium.

Emulgierbare Konzentrate werden durch Auflösen des Wirkstoffes in einem organischen Lösungsmittel, z.B. Butanol, Cyclohexanon, Dimethylformamid, Xylol oder auch höhersiedenden Aromaten oder Kohlenwasserstoffen unter Zusatz von einem oder mehreren Emulgatoren hergestellt. Als Emulgatoren können beispielsweise verwandt werden: Alkylarylsulfonsaure Calzium-Salze wie Ca-dodecylbenzolsulfonat oder nichtionische Emulgatoren wie Fettsäurepolyglykolester, Alkylarylpolyglykolether, Fettalkoholpolyglykolether, Propylenoxid-Ethylenoxid-Kondensationsprodukte, Alkylpolyether, Sorbitanfettsäureester, Polyoxyethylensorbitan-Fettsäureester oder Polyoxethylensorbitester.Emulsifiable concentrates are made by dissolving the active ingredient in an organic solvent, e.g. butanol, Cyclohexanone, dimethylformamide, Xylene or higher-boiling aromatics or hydrocarbons with the addition of one or more emulsifiers produced. As emulsifiers, for example are used: alkylarylsulfonic acid calcium salts such as calcium dodecylbenzenesulfonate or nonionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, Fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensation products, alkyl polyethers, Sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester or polyoxethylene sorbitol ester.

Stäubemittel erhält man durch Vermahlen des Wirkstoffes mit fein verteilten festen Stoffen, z.B. Talkum, natürlichen Tonen wie Kaolin, Bentonit, Poryphillit oder Diatomeenerde. Granulate können entweder durch Verdüsen des Wirkstoffes auf adsorptionsfähiges, granuliertes Inertmaterial hergestellt werden oder durch Aufbringen von Wirkstoffkonzentraten mittels Klebemitteln, z.B.Dusts are obtained by grinding the active ingredient with finely divided ones solid substances, e.g. talc, natural clays such as kaolin, bentonite, poryphillite or diatomaceous earth. Granules can either be sprayed on by the active ingredient adsorptive, granulated inert material are produced or by application of active ingredient concentrates by means of adhesives, e.g.

Polyvinylalkohol, polyacrylsaurem Natrium oder auch Mineralölen auf die Oberfläche von Trägerstoffen wie Sand, Kaolinite, oder von granuliertem Inertmaterial.Polyvinyl alcohol, polyacrylic acid sodium or mineral oils the surface of carrier materials such as sand, kaolinite, or granulated inert material.

Auch können geeignete Mittel in der für die Herstellung von Düngemittelgranulaten üblichen Weise - gewünschtenfalls in Mischung mit Düngemitteln - hergestellt werden.Suitable agents can also be used in the for the production of fertilizer granules in the usual way - if desired in a mixture with fertilizers.

Das Gewichtsverhältnis der Verbindungen der Formel I zum Kombinationspartner variiert im Bereich zwischen. 1:20 bis 1:1.The weight ratio of the compounds of the formula I to the combination partner varies in the range between. 1:20 to 1: 1.

Die nachfolgenden Beispiele dienen zur Erläuterung der Erfindung.The following examples serve to illustrate the invention.

Biologische Beispiele I Kombinationspartner: Phosphorsäureester Beispiel 1: Prüfobjekt: Aphis craccivora (Vollpopulation) Versuchspflanze: Vicia faba Art der Behandlung: Spritzen bis zum beginnenden Abtropfen Wirkstoffkonz. % Mortatlität nach Verbindung (ppm) 3d 7d Heptenophos 7,8 70 4G 3,9 50 40 2,0 50 30 A 63,0 20 0 31,0 0 0 16,0 0 0 Heptenophos + A 7,8 + 63,0 98 90 3,9 + 31,0 94 90 2,0 + 16,0 80 40 Beispiel 2: Prüfobjekt: Panonychus ulmi Versuchspflanze: Malus spp.Biological examples I Combination partner: phosphoric acid ester example 1: Test object: Aphis craccivora (full population) Test plant: Vicia faba Art of treatment: spraying until it starts to drip off, active ingredient conc. % Mortality after compound (ppm) 3d 7d Heptenophos 7.8 70 4G 3.9 50 40 2.0 50 30 A 63.0 20 0 31.0 0 0 16.0 0 0 Heptenophos + A 7.8 + 63.0 98 90 3.9 + 31.0 94 90 2.0 + 16.0 80 40 Example 2: Test object: Panonychus ulmi Test plant: Malus spp.

Art der Behandlung: Spritzen bis zum beginnenden Abtropfen Wirkstoffkonz. % Mortalität nach Verbindung (ppm) gd Triazophos 125 85 63 65 31 30 16 20 A 250 0 Triazophos + A 125 + 250 100 63 + 125 85 31 + 63 60 16 + 31 40 Beispiel 3: Prüfobjekt: Spodoptera littoralis (L III) auf festem Nährmedium Art der Behandlung: Spritzen mit 600 1 H20/ha Wirkstoffkonz. % Mortalität nach Verbindung (ppm) 7d Triazophos 16,0 10 7,8 0 A 1,25 80 0,6 0 Triazophos + A 16,0 + 1,25 100 7,8 + 0,6 30 II Kombinationspartner: Carbamate Beispiel 4: Prüfobjekt: Trialeurodes vaporariorum (Eier) Versuchspflanze: Phaseolus vulgaris Art der Behandlung: Spritzen bis zum beginnenden Abtropfen . Wirkstoffkonz. % Mortalität nach Verbindung (ppm) 14d Carbofuran 31 50 16 10 D 0,24 25 0,12 10 Carbofuran + D 31 + 0,24 95 16 + 0,12 50 III Kombinationspartner: Carbonsäureester Beispiel 5: Prüfobjekt: Spodoptera littoralis (L III) auf festem Nährmedium Art der Behandlung: Spritzen mit 600 1 H20/ha Wirkstoffkonz. % Mortalität nach Verbindung (ppm) 7d Decis 0,98 100 0,49 11 C 5,0 60 2,5 30 Decis + C 0,98 + 5,0 100 0,49 + 2,5 100 Beispiel 6: Prüfobjekt: Trialeurodes vaporariorum (Eier) Versuchspflanze: Phaseolus vulgaris Art der Behandlung: Spritzen bis zum beginnenden Abtropfen Wirkstoffkonz. % Mortalität nach Verbindung (ppm) 14d Decis 0,008 40 0,004 10 D 0,24 25 0,12 10 Decis + D 0,008 + 0,24 80 0,004 + 0,12 50 IV Kombinationspartner: Zinnverbindungen Beispiel 7: Prüfobjekt: Trialeurodes vaporariorum (Eier) Versuchspflanze: Phaseolus vulgaris Art der Behandlung: Spritzen bis zum beginnenden Abtropfen Verbindung Wirkstoffkonz. % Mortalität nach (ppm) 14d Cyhexatin 16 5 D 0,24 25 Cyhexatin + D 16 + 0,24 70 V Kombinationspartner anderer chemischer Struktur Beispiel 8: Prüfobjekt: Trialeurodes vaporariorum (Eier) Versuchspflanze: Phaseolus vulgaris Art der Behandlung: Spritzen bis zum beginnenden Abtropfen Wirkstoffkonz. % Mortalität nach Verbindung (ppm) 14d Binapacryl 31 50 16 15 8 0 E 0,24 30 0,12 20 0,06 5 Binapacryl + E 31 + 0,24 95 16 + 0,12 60 8 + 0,06 40 Beispiel 9: Prüfobjekt: Heliothis virescens (L III) auf festem Nährmedium Art der Behandlung: Spritzen mit 600 1 H20/ha Wirkstoffkonz. % Mortalität nach Verbindung (ppm) 14d Binapacryl 1000 0 500 0 A 50 80 25 40 Binapracryl + A 1000 + 50 100 500 + 25 40 Beispiel 10: PrUfobjekt: Spodoptera littoralis (L III) auf festem Nährmedium Art der Behandlung: Spritzen mit 600 1 H20/ha Wirkstoffkonz. % Mortalität nach Verbindung (ppm) 7d Endosulfan 31 100 16 10 7,8 0 A 2,5 90 1,25 80 0,6 0 Endosulfan + A 31 + 2,5 100 16 + 1,25 100 7,8 + 0,63 30 Verbindungen A, C, D, E s. S. 7Type of treatment: Injecting until it begins to drip off. % Mortality after compound (ppm) gd Triazophos 125 85 63 65 31 30 16 20 A 250 0 Triazophos + A 125 + 250 100 63 + 125 85 31 + 63 60 16 + 31 40 example 3: Test object: Spodoptera littoralis (L III) on solid nutrient medium Type of treatment: Spray with 600 1 H20 / ha active ingredient conc. % Mortality after compound (ppm) 7d Triazophos 16.0 10 7.8 0 A 1.25 80 0.6 0 Triazophos + A 16.0 + 1.25 100 7.8 + 0.6 30 II Combination partner: carbamates Example 4: Test object: Trialeurodes vaporariorum (Eggs) Test plant: Phaseolus vulgaris Type of treatment: Spraying up to beginning to drip off. Active ingredient conc. % Mortality after compound (ppm) 14d carbofuran 31 50 16 10 D 0.24 25 0.12 10 Carbofuran + D 31 + 0.24 95 16 + 0.12 50 III Combination partner: carboxylic acid ester Example 5: Test object: Spodoptera littoralis (L III) on a solid nutrient medium Type of treatment: spray with 600 1 H20 / ha active ingredient conc. % Mortality after compound (ppm) 7d Decis 0.98 100 0.49 11 C 5.0 60 2.5 30 Decis + C 0.98 + 5.0 100 0.49 + 2.5 100 Example 6: Test object: Trialeurodes vaporariorum (eggs) Test plant: Phaseolus vulgaris Type of treatment: Syringes concentration of active ingredient until it begins to drip off. % Mortality after compound (ppm) 14d Decis 0.008 40 0.004 10 D 0.24 25 0.12 10 Decis + D 0.008 + 0.24 80 0.004 + 0.12 50 IV Combination partner: tin compounds Example 7: Test object: Trialeurodes vaporariorum (eggs) Test plant: Phaseolus vulgaris Type of treatment: Syringes until it begins to drip compound active ingredient conc. % Mortality according to (ppm) 14d cyhexatin 16 5 D 0.24 25 cyhexatin + D 16 + 0.24 70 V combination partner different chemical structure Example 8: Test object: Trialeurodes vaporariorum (eggs) Test plant: Phaseolus vulgaris Type of treatment: spraying until the beginning Drip off active ingredient conc. % Mortality after compound (ppm) 14d Binapacryl 31 50 16 15 8 0 E 0.24 30 0.12 20 0.06 5 Binapacryl + E 31 + 0.24 95 16 + 0.12 60 8 + 0.06 40 Example 9: Test object: Heliothis virescens (L III) solid nutrient medium Type of treatment: spray with 600 1 H20 / ha active ingredient conc. % Mortality after compound (ppm) 14d Binapacryl 1000 0 500 0 A 50 80 25 40 Binapacryl + A 1000 + 50 100 500 + 25 40 Example 10: Test object: Spodoptera littoralis (L III) on solid nutrient medium Type of treatment: spray with 600 1 H20 / ha active ingredient conc. % Mortality after compound (ppm) 7d Endosulfan 31 100 16 10 7.8 0 A 2.5 90 1.25 80 0.6 0 Endosulfan + A 31 + 2.5 100 16 + 1.25 100 7.8 + 0.63 30 Compounds A, C, D, E see p. 7

Claims (3)

PATENTANSPRÜCHE 1. Schädlingsbekämpfungsmittel, dadurch gekennzeichnet, daß sie eine Verbindung der Formel I worin R1 jeweils unabhängig voneinander Wasserstoff; Halogen; (C1-C6)Alkyl, (C1-56)Alkoxy, welche ein- oder mehrfach halogeniert sein können, R2 (C1-C6)Alkyl, welches ein- oder mehrfach halogeniert sein kann, R3 jeweils unabhängig voneinander Wasserstoff; Halogen; (C1-C6)Alkyl, (C1-C6)Alkoxy, (C1-C6)Alkylmercapto, wobei diese drei Reste ein- oder mehrfach halogeniert sein können; NR4R5, wobei R4 und R5 unabhängig voneinander (C1-C6)Alkyl, bedeutet, das ein- oder mehrfach halogeniert sein kann oder R4 und R5 zusammen mit dem gemeinsamen N-Atom einen gesättigten 5- oder 6-Ring bilden, der Sauerstoff, Schwefel oder NR6 als Ringglied enthalten und durch (C1-C3)Alkyl substituiert sein kann, wobei R6 (C1-C3)Alkyl bedeutet und m,n unabhängig voneinander eine Zahl von 1 bis 5 bedeutet, mit der Maßgabe, daß wenn (Ri)m 2,6-Difluor bedeutet, (R3)n nicht ausschließlich für Halogen oder halogeniertes (C1-C6)Alkyl stehen darf, in Kombination mit einem Insektizid aus der Gruppe der Phosphorsäureester, Carbamate, Carbonsäureester, Formamidine oder Zinnverbindungen oder mit einem anderen insektiziden Wirkstoff, enthalten.PATENT CLAIMS 1. Pesticides, characterized in that they contain a compound of the formula I. in which R1 each independently of one another is hydrogen; Halogen; (C1-C6) alkyl, (C1-56) alkoxy, which can be halogenated one or more times, R2 (C1-C6) alkyl, which can be halogenated one or more times, R3 in each case independently of one another hydrogen; Halogen; (C1-C6) alkyl, (C1-C6) alkoxy, (C1-C6) alkylmercapto, it being possible for these three radicals to be halogenated one or more times; NR4R5, where R4 and R5 are independently (C1-C6) alkyl, which can be halogenated one or more times, or R4 and R5 together with the common N atom form a saturated 5- or 6-membered ring, oxygen, sulfur or contain NR6 as a ring member and can be substituted by (C1-C3) alkyl, where R6 denotes (C1-C3) alkyl and m, n independently of one another denote a number from 1 to 5, with the proviso that when (Ri) m 2,6-Difluor means that (R3) n may not only stand for halogen or halogenated (C1-C6) alkyl, in combination with an insecticide from the group of phosphoric acid esters, carbamates, carboxylic acid esters, formamidines or tin compounds or with another insecticidal active ingredient , contain. 2. Schädlingsbekämpfungsmittel gemäß Anspruch 1, dadurch gekennzeichnet, daß das Mischungsverhältnis der Komponente der Formel I zum Kombinationspartner im Bereich zwischen 20:1 bis 1:1 variiert.2. Pesticide according to claim 1, characterized in that that the mixing ratio of the component of the formula I to the combination partner varies in the range between 20: 1 to 1: 1. 3. Verfahren zur Bekämpfung von Schadinsekten und deren Entwicklungsstdien, dadurch gekennzeichnet, daß man auf diese oder ihren Lebensraum eine wirksame Menge eines Mittels gemäß Ansprüchen 1 oder 2 appliziert.3. Procedures for the control of harmful insects and their developmental stages, characterized in that an effective amount is applied to these or their habitat an agent according to claims 1 or 2 applied.
DE19853511550 1985-03-29 1985-03-29 Pesticides based on carboximidates Withdrawn DE3511550A1 (en)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0199945A2 (en) * 1985-03-23 1986-11-05 Hoechst Aktiengesellschaft Carbamoylarylcarboximide-acid esters, process for their preparation, compositions containing them and their use as pesticides

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0199945A2 (en) * 1985-03-23 1986-11-05 Hoechst Aktiengesellschaft Carbamoylarylcarboximide-acid esters, process for their preparation, compositions containing them and their use as pesticides
EP0199945A3 (en) * 1985-03-23 1988-08-03 Hoechst Aktiengesellschaft Carbamoylarylcarboximide-acid esters, process for their preparation, compositions containing them and their use as pesticides

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