DK161196B - N-N-N-O - Google Patents

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DK161196B
DK161196B DK395985A DK395985A DK161196B DK 161196 B DK161196 B DK 161196B DK 395985 A DK395985 A DK 395985A DK 395985 A DK395985 A DK 395985A DK 161196 B DK161196 B DK 161196B
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formula
compound
chlorine
fluorine
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DK395985A
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DK395985A (en
DK161196C (en
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Josef Ehrenfreund
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Ciba Geigy Ag
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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C273/00Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C273/02Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of urea, its salts, complexes or addition compounds
    • C07C273/06Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of urea, its salts, complexes or addition compounds from cyanamide or calcium cyanamide
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N47/00Biocides, 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
    • A01N47/08Biocides, 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
    • A01N47/28Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/34Ureas 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C275/00Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C275/46Derivatives 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
    • C07C275/48Y being a hydrogen or a carbon atom
    • C07C275/54Y being a carbon atom of a six-membered aromatic ring, e.g. benzoylureas

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Environmental Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Plant Pathology (AREA)
  • Pest Control & Pesticides (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Detergent Compositions (AREA)
  • Magnetic Resonance Imaging Apparatus (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Hydrogenated Pyridines (AREA)

Abstract

1. A compound of formula I see diagramm : EP0174274,P14,F4 wherein R1 is hydrogen or halogen and R2 and R3 are halogen.

Description

iin

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Den foreliggende opfindelse angår hidtil ukendte N-[3-halo-gen-4-(hexafluorpropyloxy)-5-trifluormethyl]-phenyl-N'-ben-zoylurinstoffer, fremgangsmåder til deres fremstilling# skade·’-dyrsbekæmpelsesmiddel, deres anvendelse til skadedyrsbekæm-5 pelse samt fremgangsmåde til bekæmpelse af insekter og individer af ordenen Acarina.The present invention relates to novel N- [3-halo gene-4- (hexafluoropropyloxy) -5-trifluoromethyl] -phenyl-N'-benzoylureas, methods for their preparation # pests · 'pesticides, their use in pest control -5 fur as well as method of controlling insects and individuals of the order Acarina.

Forbindelserne ifølge opfindelsen er ejendommelige ved, at de har den almene formel R, R-a __11 __I 3 / -CONHCONH-./ \.-0-CF2CHFCF3 (I) ~i2 10 hvori betyder hydrogen eller halogen, og R2 og R^ betyder halogen.The compounds of the invention are characterized in that they have the general formula R, Ra __11 __I 3 / -CONHCONH-./ \ .- 0-CF2CHFCF3 (I) -1,2 wherein hydrogen or halogen and R 2 and R 2 .

Ved halogen skal der indenfor rammerne af den foreliggende opfindelse forstås fluor, chlor og brom, især fluor og chlor for substituenterne R·^ og R2 og chlor og brom for substitu-15 enten R^.By halogen, within the scope of the present invention is meant fluorine, chlorine and bromine, especially fluorine and chlorine for the substituents R R and R₂ and chlorine and bromine for substituents R R.

Som følge af deres virkning ved skadedyrsbekæmpelse foretrækkes forbindelser med formlen I, hvori R^ betyder hydrogen, fluor eller chlor, R2 betyder fluor eller chlor, og betyder chlor.Because of their action in pest control, compounds of formula I are preferred wherein R 1 is hydrogen, fluorine or chlorine, R 2 is fluorine or chlorine, and is chlorine.

20 Specielt skal nævnes forbindelser med formlen I, hvori R^ betyder hydrogen, fluor eller chlor, R2 betyder fluor eller chlor, og R^ betyder brom.Particular mention should be made of compounds of formula I wherein R 1 is hydrogen, fluorine or chlorine, R 2 is fluorine or chlorine, and R 2 is bromine.

Fra beskrivelsen til EP-patentskrift nr. 23.884 kendes N-(4-halogenalkoxy-5-trifluormethylphenyl)-Ν'-benzoylurinstoffer, 25 som er usubstituerede i 3-stillingen. Disse kendte forbindelser er nært beslægtede med forbindelserne ifølge opfindelsen med den almene formel I, som i 3-stillingen i anilin-phenyl-ringen indeholder en halogensubstituent R^.From the specification of European Patent Specification No. 23,884 N- (4-haloalkoxy-5-trifluoromethylphenyl) -Ν'-benzoylureas are known which are unsubstituted at the 3-position. These known compounds are closely related to the compounds of the invention of general formula I which contain at the 3-position of the aniline phenyl ring a halogen substituent R

Det har nu overraskende vist sig, at forbindelserne ifølge 30 opfindelsen har en bedre insekticid virkning i forhold tilIt has now surprisingly been found that the compounds of the invention have a better insecticidal effect compared to

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2 de nært beslægtede kendte forbindelser.2 the closely related known compounds.

Forbindelserne med formlen I kan fremstilles under anvendelse af kendte fremgangsmåder, jvf. f.eks. DE-offentliggørel-sesskrift nr. 2.123.236 og nr. 2.601.780 samt beskrivelsen 5 til europæisk patentansøgning nr. 13.414.The compounds of formula I can be prepared using known methods, cf. DE Publication No. 2,123,236 and 2,601,780 and the specification 5 of European Patent Application No. 13,414.

Forbindelserne med formlen I kan således fremstilles ved en fremgangsmåde, der er ejendommelig ved, at man a) omsætter en forbindelse med formlen I -3 CF3CHFCF2-0- X ^>“NH2 (li) ST3 10 med en forbindelse med formlen J1 / X -C0-N=C=0 (III) R2 eller b) omsætter en forbindelse med formlen EL· li CF-CHFCF9-0-/ \-N=C=0 (IV) CF u 3 15 med en forbindelse med formlen J1 S \ -co-nh9 (V) X— s Δ R2 eller c) omsætter en forbindelse med formlen II med en forbindelse med formlen —f1 20 / X.-CONHCOOR (VI)Thus, the compounds of formula I can be prepared by a process which is characterized by: a) reacting a compound of formula I -3 CF3CHFCF2-0- X3> NH2 (l1) ST310 with a compound of formula J1 / X -C0-N = C = O (III) R 2 or b) react a compound of formula EL · l in CF-CHFCF9-0- / \ -N = C = O (IV) CF u 3 15 with a compound of formula J1 S \ -co-nh9 (V) X - s Δ R2 or c) react a compound of formula II with a compound of formula - f1 20 / X.-CONHCOOR (VI)

XX

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I de ovenfor anførte formler II, III, IV, V og VI har grupperne R^, R2 og Rg de ovenfor under formlen I angivne betydninger, og R betyder en eventuelt med halogen, fortrinsvis chlor, substitueret C^-Cg-alkylgruppe.In the above formulas II, III, IV, V and VI, the groups R 1, R 2 and R g have the meanings given above under the formula I and R is an optionally substituted C 1 -C 6 alkyl group with halogen, preferably chlorine.

5 De ovenfor omtalte fremgangsmåder a) til c) kan fortrinsvis gennemføres under almindeligt tryk og i nærværelse af et organisk opløsningsmiddel eller fortyndingsmiddel. Som opløsningsmidler eller fortyndingsmidler kan eksempelvis anvendes ethere og etheragtige forbindelser, såsom diethylether, di-10 propylether, dibutylether, dioxan, dimethoxyethan og tetra-hydrofuran, Ν,Ν-dialkylerede carboxylsyreamider, aliphatiske, aromatiske samt halogenerede carbonhydrider, især benzen, toluen, xylen, chloroform, methylenchlorid, carbontetrachlor-id og chlorbenzen, nitriler, såsom acetonitril eller propio-15 nitril, dimethylsulfoxid samt ketoner, f.eks. acetone, meth-ylethylketon, methylisopropylketon og methylisobutylketon. Fremgangsmåde a) gennemføres almindeligvis ved en temperatur i området fra -10 til 100°C, fortrinsvis mellem 15 og 25°C, eventuelt i nærværelse af en organisk base, f.eks. triethyl-20 amin. Gennemførelsen af fremgangsmåde b) sker ved en temperatur på fra 0 til 150°C, fortrinsvis ved det anvendte opløsningsmiddels kogepunkt, og eventuelt i nærværelse af en organisk base, såsom pyridin, og/eller under tilsætning af et alkalimetal eller jordalkalimetal, fortrinsvis natrium. *"' 25 Til omsætningen af urethanerne med formlen VI ifølge fremgangsmåde c) vælges sædvanligvis temperaturer mellem 60°C og reaktionsblandingens kogepunkt. Som opløsningsmidler anvendes først og fremmest aromatiske carbonhydrider, såsom toluen, xylen og chlorbenzen.The processes a) to c) mentioned above can preferably be carried out under ordinary pressure and in the presence of an organic solvent or diluent. As solvents or diluents, for example, ethers and ether-like compounds such as diethyl ether, dipropyl ether, dibutyl ether, dioxane, dimethoxyethane and tetrahydrofuran, Ν, Ν-dialkylated carboxylic acid amides, aliphatic, aromatic and halogenated hydrocarbons, especially benzene, , chloroform, methylene chloride, carbon tetrachloride and chlorobenzene, nitriles such as acetonitrile or propionitrile, dimethylsulfoxide, and ketones, e.g. acetone, methyl ethyl ketone, methyl isopropyl ketone and methyl isobutyl ketone. Process a) is generally carried out at a temperature in the range of -10 to 100 ° C, preferably between 15 and 25 ° C, optionally in the presence of an organic base, e.g. triethyl-20 amine. The process b) is carried out at a temperature of from 0 to 150 ° C, preferably at the boiling point of the solvent used, and optionally in the presence of an organic base such as pyridine, and / or with the addition of an alkali metal or alkaline earth metal, preferably sodium. For the reaction of the urethanes of formula VI according to process c), temperatures between 60 ° C and the boiling point of the reaction mixture are usually selected. As solvents, aromatic hydrocarbons such as toluene, xylene and chlorobenzene are used primarily as solvents.

30 Udgangsforbindelserne med de ovenfor anførte formler II, III, IV, V og VI er kendte forbindelser eller kan, i tilfælde af hidtil ukendte forbindelser, fremstilles under anvendelse af kendte fremgangsmåder. De substituerede aniliner med formlen II er hidtil ukendte forbindelser, som kan fremstilles ved frem-35 gangsmåder, der er kendt fra litteraturen, idet man eksempelvis hydrogenerer 2-halogen-6-trifluormethyl-4-nitro-phenol i nærværelse af eddikesyreanhydrid, jf. J.Org.Chem.The starting compounds of the above formulas II, III, IV, V and VI are known compounds or, in the case of novel compounds, can be prepared using known methods. The substituted anilines of formula II are novel compounds which can be prepared by methods known in the literature, for example hydrogenating 2-halo-6-trifluoromethyl-4-nitro-phenol in the presence of acetic anhydride, cf. J. Org.

27 (1962), 4660, og forethrer den dannede 2-halogen-6-tri- 427 (1962), 4660, etherifying the resulting 2-halo-6-tri-4

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fluormethyl-4-acetaminophenol med hexafluorpropylen analogt med fremgangsmåden ifølge J.Am.Chem.Soc., ]_3 (1951), 5831. Derefter fraspaltes N-acetylgruppen på sædvanlig måde - til dannelse af anilinen med formlen II.fluoromethyl-4-acetaminophenol with hexafluoropropylene, analogous to the method of J.Am.Chem.Soc.,] _3 (1951), 5831. Then the N-acetyl group is cleaved in the usual manner to form the aniline of formula II.

5 Det har vist sig, at forbindelserne ifølge opfindelsen med formlen I ved god planteforenelighed og ringe varmblodstoksicitet giver udmærkede resultater ved bekæmpelse af skadedyr.It has been found that the compounds of the invention of formula I, with good plant compatibility and poor warm blood toxicity, give excellent results in controlling pests.

De egner sig først og fremmest til bekæmpelse af skadedyr på planter og dyr.They are primarily suitable for the control of pests on plants and animals.

10 Den foreliggende opfindelse angår derfor også et skadedyrsbekæmpelsesmiddel, som er ejendommeligt ved det i den kendetegnende del af krav 10 anførte.The present invention therefore also relates to a pesticide peculiar to that of the characterizing part of claim 10.

Endvidere angår opfindelsen anvendelse af en forbindelse med den almene formel I til bekæmpelse af insekter og 15 individer af ordenen Acarina på dyr og planter.Furthermore, the invention relates to the use of a compound of the general formula I for the control of insects and individuals of the order Acarina in animals and plants.

Endelig angår opfindelsen en fremgangsmåde til bekæmpelse af insekter og individer af ordenen Acarina, som er ejendommelig ved det i den kendetegnende del af krav 14 anførte.Finally, the invention relates to a method for the control of insects and individuals of the order Acarina, which is characterized by the characterizing part of claim 14.

Forbindelserne med formlen I er især egnede til bekæmpelse 20 af insekter af ordnerne Lepidoptera, Doleoptera, Homoptera, Heteroptera, Diptera, Thysanoptera, Orthoptera, Anoplura, S.iphonaptera, Mallophaga, Thysanura, Isoptera, Psocoptera og Hymenoptera samt individer af ordenen Acarina.The compounds of formula I are particularly suitable for controlling insects of the order Lepidoptera, Doleoptera, Homoptera, Heteroptera, Diptera, Thysanoptera, Orthoptera, Anoplura, S.iphonaptera, Mallophaga, Thysanura, Isoptera, Psocoptera and Hymenoptera or individuals.

Den gode pesticide virkning ved forbindelserne ifølge opfin-25 delsen med formlen I svarer til en udryddelsesrate (mortalitet) på mindst 50-60% af de nævnte skadedyr.The good pesticidal effect of the compounds of the invention of formula I corresponds to an eradication rate (mortality) of at least 50-60% of said pests.

Foruden en særdeles gunstig virkning mod fluer, som f.eks.In addition to a particularly beneficial effect against flies, such as

Musca dQmestica, og myggelarver er forbindelserne med formlen I først og fremmest egnede til bekæmpelse af planteska-30 delige ædende insekter i pryd- og nytteplåntekulturer, især i bomuldskulturer, f.eks. Spodoptera littoralis og Heliothis virescens, samt i grøntsagskulturer, f.eks. Leptinotarsa de-cemlineata og Bieris brassicae.Musca dmmestica and mosquito larvae are the compounds of formula I which are primarily suitable for the control of plant-eating edible insects in ornamental and utility plant cultures, especially in cotton cultures, e.g. Spodoptera littoralis and Heliothis virescens, as well as in vegetable cultures, e.g. Leptinotarsa de-cemlineata and Bieris brassicae.

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Virkningen af forbindelserne ifølge opfindelsen eller midler indeholdende forbindelser ifølge opfindelsen kan gøres væsentligt mere bredspréktret ved tilsætning af andre insekticider og/ eller akaricider og tilpasses til givne omstændigheder. Som 5 tilsætningsstoffer kan eksempelvis anvendes forbindelser fra følgende stofklasser: organiske phosphorforbindelser, nitro-phenoler og derivater deraf, formamidiner, urinstoffer, car-bamater, pyrethroider, chlorerede carbonhydrider og Bacillus thuringiensis-præparater.The effect of the compounds of the invention or agents containing compounds of the invention can be made significantly more widespread by the addition of other insecticides and / or acaricides and adapted to given circumstances. For example, compounds of the following classes of substances can be used as 5 additives: organic phosphorus compounds, nitrophenols and derivatives thereof, formamidines, ureas, carbamates, pyrethroids, chlorinated hydrocarbons and Bacillus thuringiensis preparations.

10 Forbindelserne med formlen I anvendes i uforandret form eller fortrinsvis sammen med de i formuleringsteknikken anvendte hjælpemidler, og de forarbejdes derfor på kendt måde f.eks. til emulsionskoncentrater, direkte sprøjtbare eller fortyndelige opløsninger, fortyndede emulsioner, sprøjtepulvere, op-15 løselige pulvere, pudderpræparater, granulater samt indkapslinger i f.eks. polymere stoffer. Anvendelsesfremgangsmåderne, såsom udsprøjtning, tågedannelse, forstøvning, udstrø-ning eller udhældning, samt midlet vælges afhængigt af det tilstræbte formål og de givne forhold.The compounds of formula I are used in unchanged form or preferably together with the auxiliaries used in the formulation technique, and are therefore processed in a known manner e.g. for emulsion concentrates, directly sprayable or dilute solutions, diluted emulsions, spray powders, soluble powders, powder preparations, granules and enclosures in e.g. polymeric substances. The methods of use, such as spraying, misting, spraying, spraying or pouring, as well as the agent are selected depending on the purpose and conditions given.

20 Formuleringen, dvs. midlerne, tilberedningerne eller sammensætningerne, som indeholder det aktive stof med formlen I eller kombinationer af disse aktive stoffer med andre insekticider eller akaricider og eventuelt et fast eller flydende tilsætningsstof, fremstilles på kendt måde, f.eks. ved 25 grundig sammenblanding og/eller formaling af de aktive stoffer med strækkemidler, som f.eks. opløsningsmidler, faste bærestoffer og eventuelt overfladeaktive forbindelser (tensider) .The formulation, i.e. the agents, preparations or compositions containing the active substance of formula I or combinations of these active substances with other insecticides or acaricides and optionally a solid or liquid additive are prepared in known manner, e.g. by thoroughly mixing and / or grinding the active substances with excipients such as e.g. solvents, solid carriers and optionally surfactants (surfactants).

Som opløsningsmidler kan anvendes aromatiske carbonhydrider, 30 fortrinsvis fraktionerne Cg - C·^, som f.eks. xylenblandinger eller substituerede naphthalener, phtalsyreestere, såsom di-butyl- eller dioctylphthalat, aliphatiske carbonhydrider, såsom cyclohexan, paraffiner, alkoholer og glycoler samt deres ethere og estere, såsom ethanol, ethylenglycol, ethylengly- 6As solvents may be used aromatic hydrocarbons, preferably the fractions Cg - C ·, such as e.g. xylene mixtures or substituted naphthalenes, phthalic esters such as dibutyl or dioctyl phthalate, aliphatic hydrocarbons such as cyclohexane, paraffins, alcohols and glycols and their ethers and esters such as ethanol, ethylene glycol, ethylene glycol 6

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colmonomethyl- eller -ethylether, ketoner, såsom cyclohexa-non, stærkt polære opløsningsmidler, såsom N-methyl-2-pyrrol-idon, dimethylsulfoxid eller dimethylformamid,samt eventuelt epoxiderede planteolier, såsom epoxideret kokosolie eller 5 soyaolie, eller vand.columonomethyl or ethyl ether, ketones such as cyclohexanone, highly polar solvents such as N-methyl-2-pyrrolidone, dimethylsulfoxide or dimethylformamide, and optionally epoxidized plant oils such as epoxidized coconut oil or soybean oil, or water.

Som faste bærestoffer, f.eks. til pudderpræparater og disper-gerbare pulvere, anvendes i reglen naturligt stenmel, såsom calcit, talkum, kaolin, montmorillonit eller attapulgit. Til forbedring af de fysiske egenskaber kan der også tilsættes 10 højdisperse kiselsyrer og højdisperse absorptionsdygtige polymerisater. Som kornformige, adsorptionsdygtige granulatbærere anvendes porøse typer, f.eks. pimpsten, teglbrud, se-piolit eller bentonit, og som ikke-absorberende bærematerialer f.eks. calcit eller sand. Desuden kan der anvendes et 15 stort antal granulerede materialer af uorganisk eller organisk natur, især f.eks. dolomit eller findelte planterester.As solid carriers, e.g. For powder preparations and dispersible powders, natural stone flour, such as calcite, talc, kaolin, montmorillonite or attapulgite, is usually used. To improve the physical properties, 10 high-dispersion silicic acids and high-dispersion absorbent polymerizates can also be added. Porous types are used as granular adsorbable granular carriers, e.g. pumice, bricks, seepiolite or bentonite, and as non-absorbent carriers e.g. calcite or sand. In addition, a large number of granular materials of inorganic or organic nature can be used, especially e.g. dolomite or finely divided plant residues.

Som overfladeaktive forbindelser kan der afhængigt af arten af det aktive stof med formlen I eller kombinationer af de aktive stoffer med formlen I med andre insekticider eller akaricider, som skal formuleres, anvendes ikke-ioniske, kat-ionaktive og/eller anionaktive tensider med gode emulgerings-, dispergerings- og befugtningsegenskaber. Ved tensider forstås også tensidblandinger.As surfactants, depending on the nature of the active substance of formula I or combinations of the active substances of formula I with other insecticides or acaricides to be formulated, nonionic, cationic and / or anionic surfactants with good emulsifiers can be used. -, dispersing and wetting properties. Surfactants are also meant surfactant mixtures.

Egnede anioniske tensider kan være både såkaldte vandopløse-25 lige sæber og tillige vandopløselige syntetiske overfladeaktive forbindelser.Suitable anionic surfactants can be both so-called water-soluble soaps and also water-soluble synthetic surfactants.

Som sæber kan anvendes alkalimetal-, jordalkalimetal- og eventuelt substituerede ammoniumssal·te af højere fedtsyrer (C10”C 22)/ såsom f.eks. Na- eller K-saltene af olie- eller stea-30 rinsyre, eller af naturlige fedtsyreblandinger, der f.eks. kan udvindes af kokosolie eller talgolie. Som tensider skal endvidere nævnes fedtsyre-methyl-taurin-saltene samt modificerede og ikke-modificerede phospholipider.As soaps can be used alkali metal, alkaline earth metal and optionally substituted ammonium salts of higher fatty acids (C10 ”C22) / such as e.g. The Na or K salts of oleic or stearic acid, or of natural fatty acid mixtures, e.g. can be extracted from coconut oil or tallow oil. Also mentioned as surfactants are the fatty acid methyl taurine salts as well as modified and unmodified phospholipids.

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Ofte anvender man dog såkaldte syntetiske tensider, især fedt-sulfonater, fedtsulfater, sulfonerede benzimidazolderivater eller alkylarylsulfonater.However, so-called synthetic surfactants are often used, especially fatty sulfonates, fatty sulfates, sulfonated benzimidazole derivatives or alkylarylsulfonates.

Fedtsulfonaterne eller fedtsulfaterne foreligger i reglen 5 som alkalimetal-, jordalkalimetal- eller eventult substituerede ammoniumsalte og indeholder sædvanligvis en alkylgrup-pe med 8-22 carbonatomer, idet alkyl også omfatter alkyIdelen af acyIrester, f.eks. Na- eller Ca-saltet af ligninsulfonsyre, af dodecylsvovlsyreester eller en af naturlige fedtsyrer frem-10 stillet fedtalkoholsulfatblanding. Hertil hører også saltene af svovlsyreestrene og sulfonsyrerne af fedtalkohol-ethylen-oxid-addukter. De sulfonerede benzimidazolderivater indeholder fortrinsvis 2 sulfonsyregrupper og en fedtsyrerest med ca. 8-22 carbonatomer. Alkylarylsulfonater er eksempelvis 15 Na-, Ca- eller triethanolaminsaltene af dodecylbenzensulfon-syre, af dibutylnaphthalensulfonsyre eller af et naphthalen-sulfonsyre-formaldehydkondensationsprodukt. Der kan endvidere også anvendes tilsvarende phosphater, som f.eks. salte af phosphorsyreesteren af et p-nonylphenol-(4-14)-ethylenoxid-20 addukt.The fatty sulphonates or fatty sulphates are usually as alkali metal, alkaline earth metal or optionally substituted ammonium salts and usually contain an alkyl group of 8-22 carbon atoms, the alkyl also comprising the alkyl portion of acyl residues, e.g. The Na or Ca salt of lignin sulfonic acid, dodecyl sulfuric acid ester or a fatty alcohol sulfate mixture prepared from natural fatty acids. These include the salts of the sulfuric acid esters and sulfonic acids of fatty alcohol-ethylene oxide adducts. Preferably, the sulfonated benzimidazole derivatives contain 2 sulfonic acid groups and a fatty acid residue having about 8-22 carbon atoms. Alkylarylsulfonates are, for example, the Na, Ca or triethanolamine salts of dodecylbenzenesulfonic acid, of dibutylnaphthalenesulfonic acid or of a naphthalene sulfonic acid formaldehyde condensation product. Furthermore, similar phosphates can also be used, such as e.g. salts of the phosphoric acid ester of a p-nonylphenol (4-14) ethylene oxide adduct.

Som ikke-ioniske tensider anvendes i første række polyglycol-etherderivater af aliphatiske eller cycloaliphatiske alkoholer, mættede eller umættede fedtsyrer og alkylphenoler, som kan indeholde 3-30 glycolethergrupper og 8-20 carbonatomer 25 i den (aliphatiske) carbonhydridgruppe og 6-18 carbonatomer i alkylgruppen i alkylphenolerne. Andre egnede ikke-ioniske tensider er de vandopløselige polyethylenoxidaddukter af poly-propylenglycol, ethylendiaminopolypropylenglycol og alkylpo-lypropylenglycol med 1-10 carbonatomer i alkylkæden indehol-30 dende 20-250 ethylenglycolethergrupper og 10-100 propylen-glycolethergrupper. De nævnte forbindelser indeholder sædvanligvis 1-5 ethylenglycolenheder pr. propylenglycolenhed.As non-ionic surfactants, polyglycol ether derivatives of aliphatic or cycloaliphatic alcohols, saturated or unsaturated fatty acids and alkyl phenols, which may contain 3-30 glycol ether groups and 8-20 carbon atoms 25 in the (aliphatic) hydrocarbon group and 6-18 carbon atoms, are used primarily the alkyl group of the alkyl phenols. Other suitable nonionic surfactants are the water-soluble polyethylene oxide adducts of polypropylene glycol, ethylene diaminopolypropylene glycol and alkyl polypropylene glycol having 1-10 carbon atoms in the alkyl chain containing 20-250 ethylene glycol ether groups and 10-100 propylene glycol ether groups. The said compounds usually contain from 1 to 5 ethylene glycol units per liter. propylene glycol unit.

Som eksempler på ikke-ioniske tensider kan nævnes nonylphen-olpolyethoxyethanoler, ricinusoliepolyglycolethere, polypropExamples of nonionic surfactants include nonylphenol polyethoxyethanols, castor oil polyglycol ethers, polypropylene

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8 ylen-polyethylenoxidaddukter, tributylphenoxypolyethoxyethan-ol, polyethylenglycol og octylphenoxypolyethoxyethanol. Der kan endvidere også anvendes fedtsyreestere af polyoxyethylen-sorbitan/ såsom polyoxyethylensorbitantrioleat.8 ylene-polyethylene oxide adducts, tributylphenoxypolyethoxyethanol, polyethylene glycol and octylphenoxypolyethoxyethanol. Furthermore, fatty acid esters of polyoxyethylene sorbitan / such as polyoxyethylene sorbitan trioleate can also be used.

5 De kationiske tensider er først og fremmest kvaternære ammoniumsalte, der som N-substituent indeholder mindst en alkyl-gruppe med 8-22 carbonatomer og som yderligere substituenter lavere, eventuelt halogenerede alkylgrupper, benzylgrupper eller lavere hydroxyalkylgrupper. Saltene foreligger fortrins-10 vis som halogenider, methylsulfater eller ethylsulfater, f.eks. stearyltrimethylammoniumchloridet eller benzyl-di-(2-chlor-ethyl)-ethylammoniumbromidet.The cationic surfactants are primarily quaternary ammonium salts containing as N-substituent at least one alkyl group of 8-22 carbon atoms and as additional substituents lower, optionally halogenated alkyl groups, benzyl groups or lower hydroxyalkyl groups. The salts are preferably present as halides, methyl sulfates or ethyl sulfates, e.g. the stearyl trimethyl ammonium chloride or benzyl di- (2-chloroethyl) ethyl ammonium bromide.

De almindeligste tensider anvendt i formuleringsteknikken er bl.a. beskrevet i følgende publikationer: 15 "Mc Cutcheon's Detergents and Emulsifiers Annual" MC Publishing Corp., Ridgewood, New Jersey, 1979;The most common surfactants used in the formulation technique include described in the following publications: 15 "Mc Cutcheon's Detergents and Emulsifiers Annual" MC Publishing Corp., Ridgewood, New Jersey, 1979;

Dr. Helmut Stache "Tensid Taschenbuch", Carl Hanser Verlag Miinchen/Wien 1981.Dr. Helmut Stache "Tensid Taschenbuch", Carl Hanser Verlag Miinchen / Wien 1981.

De pesticide præparater indeholder i reglen 0,1 - 99%, især 20 0,1 - 95% aktivt stof med formlen I eller kombinationer af disse aktive stoffer med andre insekticider eller akaricider, 1 - 99,9% fast eller flydende tilsætningsstof og 0 - 25%, især 0,1 - 20% tensid. Medens handelsvaren er et koncentreret middel, anvender slutforbrugeren i reglen fortyndede for-25 muleringer, der har en væsentligt lavere koncentration af aktivt stof. Midlerne kan også indeholde andre tilsætningsstoffer, såsom stabilisatorer, skumdæmpende midler, viskositetsregulerende midler, bindemidler, hæftemidler samt gødningsstoffer eller andre aktive stoffer til opnåelse af særlige 30 virkninger.The pesticidal compositions generally contain from 0.1 to 99%, especially from 0.1 to 95% of active substance of formula I or combinations of these active substances with other insecticides or acaricides, 1 to 99.9% of solid or liquid additive and 0 - 25%, in particular 0.1 - 20% surfactant. While the commodity is a concentrated agent, the end consumer usually uses dilute formulations having a substantially lower concentration of active substance. The agents may also contain other additives, such as stabilizers, antifoaming agents, viscosity regulators, binders, adhesives, and fertilizers or other active substances to achieve particular effects.

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Opfindelsen illustreres nærmere i de efterfølgende eksempler.The invention is further illustrated in the following examples.

Eksempel 1.Example 1.

a) Fremstilling af udgangsforbindelsen 3-chlor-4-(1,1,2,3,3,3-hexafluorpropyloxy)-5-(trifluormethyl)-anilin; 5 42,2 g 3-chlor-4-(1,1,2,3,3,3-hexafluorpropyloxy)-5-(trifluor- methyl)-acetaminobenzen koges i en blanding af 200 ml koncentreret saltsyre og 400 ml ethanol i 16 timer med tilbagesvaling. Derefter afdestilleres størsteparten af opløsningsmidlet, der gøres basisk med 10%'s natriumhydroxidopløsning og 10 extraheres med ether. Efter tørring over natriumsulfat og afdampning af opløsningsmidlet i vakuum underkastes remanensen fraktioneres destillation. Man får den ønskede forbindelse i form af en gullig olie med et kogepunkt på 115-120°C ved -2 4 x 10 mm Hg (en forbindelse med formlen II).a) Preparation of the starting compound 3-chloro-4- (1,1,2,3,3,3-hexafluoropropyloxy) -5- (trifluoromethyl) aniline; 42.2 g of 3-chloro-4- (1,1,2,3,3,3-hexafluoropropyloxy) -5- (trifluoromethyl) -acetaminobenzene are boiled in a mixture of 200 ml of concentrated hydrochloric acid and 400 ml of ethanol. 16 hours of reflux. Then, the majority of the solvent is distilled off, made basic with 10% sodium hydroxide solution and extracted with ether. After drying over sodium sulfate and evaporation of the solvent in vacuo, the residue is subjected to fractionation distillation. The desired compound is obtained in the form of a yellowish oil having a boiling point of 115-120 ° C at -2 4 x 10 mm Hg (a compound of formula II).

15 b) Fremstilling af N-[3-chlor-4-(hexafluorpropyloxy)-5-tri-fluormethyl]-N*-2,6-difluorbenzoyl-urinstof; 3,6 g af den ovenfor under a) fremstillede 3-chlor-4-(hexafluorpropyloxy) -5- (trifluormethyl) -anilin sættes til 10 ml tør diethylether, og under omrøring tilsættes dråbevis ved 20 stuetemperatur 1,82 g 2,6-difluorbenzoylisocyanat. Efter 3 timers forløb frafiltreres det dannede krystallinske bundfald, som udvaskes med lidt ether. På denne måde fås den ønskede forbindelse med formlen \ /*“ CONHCONH—^ 0-CF2CHFCF3 i ip3 25 i form af hvide krystaller med smp. 162-163°C (forbindelse nr. 1).B) Preparation of N- [3-chloro-4- (hexafluoropropyloxy) -5-trifluoromethyl] -N * -2,6-difluorobenzoyl urea; 3.6 g of the 3-chloro-4- (hexafluoropropyloxy) -5- (trifluoromethyl) aniline prepared above under (a) are added to 10 ml of dry diethyl ether and, with stirring, 1.82 g of 2.6 are added dropwise. -difluorbenzoylisocyanat. After 3 hours, the crystalline precipitate formed is filtered off, which is washed out with a little ether. In this way, the desired compound of the formula \ / * “CONHCONH-O-CF2CHFCF3 in ip3 25 is obtained in the form of white crystals, m.p. 162-163 ° C (compound # 1).

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På tilsvarende måde fremstilles også følgende forbindelser med formlen I:Similarly, the following compounds of formula I are also prepared:

Forbindelse nr. Sap. I*Cl P p •V· ··· 2 ·ζ N- CONHCONH-·^ \-0-CF2CHFCF3 166-168 i 6f3 ?! 91 • at· ·· 5 3 \ y-comcom—ζ \-o-cf2chfcf3 i 49,5-151 CFjCompound No. Sap. I * Cl P p • V · ··· 2 · ζ N- CONHCONH- · ^ \ -0-CF2CHFCF3 166-168 i 6f3 ?! 91 • at · 3 · y-comcom — ζ \ -o-cf2chfcf3 at 49.5-151 CFj

T PT P

·· ··· 4 ·' \-CONHCONH-/ 0-CF2CHFCF3 118-120 '••f' '#·#' iti·· ··· 4 · '\ -CONHCONH- / 0-CF2CHFCF3 118-120' •• f '' # · # 'iti

P PP P

·· IB« 5 \ /*HCONHCONH—ζ O-CF2CHFCF3 191,5-193 ------ il &f3·· IB «5 \ / * HCONHCONH — ζ O-CF2CHFCF3 191.5-193 ------ il & f3

Eksempel 2.Example 2.

a) Fremstilling af udgangsforbindelsen 3-brom-4-(l,l,2,3,3,3-hexafluorpropyloxy) -5- (trifluormethyl) -anilin_ 22,7 g 3-brom-4-(1,1,2/3,3,3-hexafluorpropyloxy)-5-(tri-fluormethyl)-acetaminobenzen opvarmes i en blanding af 100 ml koncentreret saltsyre og 300 ml ethanol i 4 timer med tilbagesvaling. Derefter afdestilleres størsteparten 15 af opløsningsmidlet, hvorpå det gøres basisk med 10%'s natriumhydroxidopløsning og ekstraheres med ether. Efter tørring over natriumsulfat og afdampning af opløsningsmidlet i vakuum underkastes remanensen fraktioneret destillation. Man får den ønskede forbindelse i form af en gullig 20 olie med et kogepunkt på 115-120°C ved 5*10~2 mm Hg (en forbindelse med formlen II).a) Preparation of the starting compound 3-bromo-4- (1,1,2,3,3,3-hexafluoropropyloxy) -5- (trifluoromethyl) aniline 22.7 g of 3-bromo-4- (1,1,2 (3,3,3-Hexafluoropropyloxy) -5- (trifluoromethyl) acetaminobenzene is heated in a mixture of 100 ml of concentrated hydrochloric acid and 300 ml of ethanol for 4 hours at reflux. Then, most of the solvent 15 is distilled off, then basified with 10% sodium hydroxide solution and extracted with ether. After drying over sodium sulfate and evaporation of the solvent in vacuo, the residue is subjected to fractional distillation. The desired compound is obtained in the form of a yellowish oil having a boiling point of 115-120 ° C at 5 * 10 ~ 2 mm Hg (a compound of formula II).

11 DK 1611968 b) Fremstilling af N-[3-brom-4-(hexafluorpropyloxy)-5-trifluor-methyl]-N*-2,6-difluorbenzoyl-urinstof_ 3,5 g af det ovenfor under a) fremstillede 3-brom-4-(hexafluorpropyloxy) -5-(trifluormethyl)-anilin sættes til 10 ml tør 5 diethylether, hvorpå der under omrøring ved stuetemperatur foretages dråbevis tilsætning af 1,52 g 2,6 difluorbenzoyl-isocyanat. Efter 3 timers forløb frafiltreres det dannede krystallinske bundfald, som udvaskes med lidt ether. På denne måde fås den ønskede forbindelse med formlen T Tr •m· «· 10 / ^•-CONHCONH-/ \-o>CF2CHFCF3 I £f3 i form af hvide krystaller med smp. 145-147°C (forbindelse nr. 6).B) Preparation of N- [3-bromo-4- (hexafluoropropyloxy) -5-trifluoro-methyl] -N * -2,6-difluorobenzoyl-urea 3.5 g of the above-prepared 3- bromo-4- (hexafluoropropyloxy) -5- (trifluoromethyl) -aniline is added to 10 ml of dry diethyl ether and then added dropwise with 1.52 g of 2.6 difluorobenzoyl isocyanate while stirring at room temperature. After 3 hours, the crystalline precipitate formed is filtered off, which is washed out with a little ether. In this way, the desired compound of the formula T Tr • m · «· 10 / ^ • -CONHCONH- / \ -o> CF2CHFCF3 is obtained in the form of white crystals, m.p. 145-147 ° C (compound # 6).

På samme måde som beskrevet ovenfor fremstilles også følgende forbindelser med formlen I: 12In the same manner as described above, the following compounds of formula I are also prepared: 12

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Forbindelse nr. Smp. I**C] (jl ·· ··· 7 ·£ N- CONHCONH—( \-o-CFzCHFCF3 183,5-185 i 6f3 ?! ψ ·«· i«· 8 *( CONHCONH—^ y·-O-CF2CHFCF3 141-142 S.S \s ir3 T ?r ·· IB· 9 / CONHCONH—£ \_o-CF2CHFCF3 4f3 . ί1 Ί1 ·· ·Β· 10 ·{ \-CONHCONH—ζ >-0-CFaCHFCF3 έι hf 3Compound No. m.p. I ** C] (jl ·· ··· 7 · £ N- CONHCONH— (\ -o-CFzCHFCF3 183.5-185 i 6f3?! Ψ · «· i« · 8 * (CONHCONH— ^ y · - O-CF2CHFCF3 141-142 SS \ s ir3 T? R ·· IB · 9 / CONHCONH— £ \ _o-CF2CHFCF3 4f3. Ί1 Ί1 ·· · Β · 10 · {\ -CONHCONH — ζ> -0-CFaCHFCF3 έι hf 3

Eksempel 3.Example 3

Formuleringer for aktive stoffer med formlen I ifølge eksemplerne 1 og 2 eller kombinationer af disse aktive stoffer med andre insekticider eller akaricider (% = vægtprocent)_ 1) Sprøjtepulver a) b) c)Formulations for active substances of formula I according to Examples 1 and 2 or combinations of these active substances with other insecticides or acaricides (% = wt%) 1) Spray powder a) b) c)

Aktivt stof eller kombination af aktive stoffer 25% 50% 75%Active substance or combination of active substances 25% 50% 75%

Natriumligninsulfonat 5% 5% -Sodium lignin sulfonate 5% 5% -

Natriumlaurylsulfat 3% - 5%Sodium lauryl sulfate 3% - 5%

Natriumdiisobutylnaphthalen- sulfonat - 6% 10%Sodium diisobutylnaphthalene sulfonate - 6% 10%

Oc tylphenoIpolyethylenglyco1- ether (7-8 mol ethylenoxid) - 2% Højdispers kiselsyre 5% 10% 10%Ocylphenylpolyethylene glycol ether (7-8 moles of ethylene oxide) - 2% High-dispersion silicic acid 5% 10% 10%

Kaolin 62% 27% 13Kaolin 62% 27% 13

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Det aktive stof eller kombinationen af de aktive stoffer blandes med tilsætningsstofferne, og blandingen formales grundigt på et egnet formalingsapparatur.The active substance or combination of the active substances is mixed with the additives and the mixture is thoroughly ground on a suitable grinding apparatus.

Man får et sprøjtepulver, som kan fortyndes med vand til sus-5 pensioner af en vilkårlig ønsket koncentration.A spray powder is obtained which can be diluted with water to suspend 5 pensions of any desired concentration.

2. Emulsionskoncentrat2. Emulsion concentrate

Aktivt stof eller kombination af aktive stoffer 10%Active substance or combination of active substances 10%

Octylphenolpolyethylenglycolether 10 (4-5 mol ethylenoxid) 3%Octylphenol polyethylene glycol ether (4-5 moles of ethylene oxide) 3%

Calciumdodecylbenzensulfonat 3%Calcium dodecylbenzenesulfonate 3%

Ricinusoliepolyglycolether (36 mol ethylenoxid) 4%Castor oil polyglycol ether (36 moles of ethylene oxide) 4%

Cyclohexanon 30% 15 Xylenblanding 50%Cyclohexanone 30% Xylene mixture 50%

Af dette koncentrat kan der ved fortynding med vand fremstilles emulsioner af en vilkårlig ønsket koncentration.From this concentrate, emulsions of any desired concentration can be prepared by dilution with water.

3. Pudderpræparat a) b)3. Powder preparation a) b)

Aktivt stof eller kombination af 20 aktive stoffer 5% 8%Active substance or combination of 20 active substances 5% 8%

Talkum 95%Talc 95%

Kaolin - 92%Kaolin - 92%

Der fås brugsfærdige pudderpræparater ved blanding af det aktive stof med bærestoffet og formaling af den dannede blanding 25 i et egnet blandeapparatur.Ready-to-use powder compositions are obtained by mixing the active substance with the carrier and grinding the resulting mixture 25 into a suitable mixing apparatus.

4. Ekstrudergranulat4. Extruder granules

Aktivt stof eller kombination af aktive stoffer 10%Active substance or combination of active substances 10%

Natriumligninsulfonat 2% 30 Carboxymethylcellulose 1%Sodium lignin sulfonate 2% Carboxymethyl cellulose 1%

Kaolin 87%Kaolin 87%

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Det aktive stof blandes med tilsætningsstofferne, blandingen formales og fugtes med vand. Denne blanding ekstruderes, granuleres og tørres derpå i en luftstrøm.The active substance is mixed with the additives, the mixture is ground and wetted with water. This mixture is extruded, granulated and then dried in an air stream.

5. Omhylningsgranulat 5 Aktivt stof eller kombination af aktive stoffer 3%5. Wrapping granules 5 Active substance or combination of active substances 3%

Polyethylenglycol (molekylvægt 200) 3%Polyethylene Glycol (Molecular Weight 200) 3%

Kaolin 94%Kaolin 94%

Det fint formalede aktive stof eller kombinationen af de ak-10 tive stoffer påføres ensartet i et blandeapparatur på kaolin fugtet med polyethylenglycol. På denne måde fås støvfri om-hylningsgranulater.The finely ground active substance or the combination of the active substances is uniformly applied in a kaolin wetting compound with polyethylene glycol. In this way, dust-free envelope granules are obtained.

6. Suspensionskoncentrat6. Suspension concentrate

Aktivt stof eller kombination af 15 aktive stoffer 40%Active substance or combination of 15 active substances 40%

Ethylenglycol 10%Ethylene glycol 10%

Nonylphenolpolyethylenglycolether (15 mol ethylenoxid) 6%Nonylphenol polyethylene glycol ether (15 moles of ethylene oxide) 6%

Natriumligninsulfonat 10% 20 Carboxymethylcellulose 1% 37%'s vandig formaldehydopløsning 0,2%Sodium lignin sulfonate 10% Carboxymethyl cellulose 1% 37% aqueous formaldehyde solution 0.2%

Siliconeolie i form af en 75%'s vandig emulsion 0,8%Silicone oil in the form of a 75% aqueous emulsion 0.8%

Vand 32% 25 Det fint formalede aktive stof eller kombinationen af aktive stoffer blandes grundigt med tilsætningsstofferne. På denne måde fås et suspensionskoncentrat, hvoraf der ved fortynding med vand kan fremstilles suspensioner af en vilkårlig, ønsket koncentration.Water 32% 25 The finely ground active ingredient or combination of active substances is thoroughly mixed with the additives. In this way, a suspension concentrate is obtained from which, by dilution with water, suspensions of any desired concentration can be prepared.

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Eksempel 4.Example 4

Virkning mod Musca domestica 50 g frisk fremstillet næringssubstrat til maddiker indvejes i bægre. I 1 vægtprocent acetoneopløsning af det pågældende 5 aktive stof tilsættes en bestemt mængde af det i bægeret forekommende næringssubstrat ved hjælp af en pipette, således at man får en koncentration af aktivt stof på 400 ppm. Efter gen-nemblanding af substratet henstår bægeret til fordampning af acetonen i mindst 20 timer.Effect against Musca domestica Weigh 50 g of freshly prepared nutritional substrate for food drink into cups. In a 1% by weight acetone solution of the 5 active substance in question, a certain amount of the nutrient substrate contained in the beaker is added by means of a pipette to give a concentration of active substance of 400 ppm. After re-mixing the substrate, the beaker is allowed to evaporate the acetone for at least 20 hours.

10 Derpå anbringes 25 en dag gamle maddiker af Musca domestica i bægrene med det således behandlede næringssubstrat. Når maddikerne har forpuppet sig, adskilles de dannede pupper fra substratet ved udskylning med vand, hvorpå de deponeres Ϊ beholdere lukket med silåg.10 Then 25 one-day-old mads of Musca domestica are placed in the cups with the thus-treated nutrient substrate. After the pups have pupated, the pupae formed are separated from the substrate by rinsing with water, and they are deposited on Ϊ containers closed with a silage lid.

15 Antallet af udskyllede pupper bestemmes (toksisk indvirkning af det aktive stof på maddikeudviklingen). Efter 10 dages forløb bestemmes derefter antallet af fluer udklækket fra pupperne.15 The number of flushed pupae is determined (toxic effect of the active substance on the development of food). After 10 days, the number of flies hatched from the pupae is then determined.

Forbindelser med formlen I ifølge eksemplerne 1 og 2 udviser 20 god virkning ved ovenstående test.Compounds of formula I according to Examples 1 and 2 exhibit good effect in the above test.

Eksempel 5.Example 5

Virkning mod Lucilia sericataEffect against Lucilia sericata

Til 9 ml dyrkningsmedium sættes ved 50°C 1 ml vandig tilberedning indeholdende 0,5% aktivt stof. Derpå sættes ca. 30 frisk 25 udklækkede Lucilia sericata-larver til dyrkningsmediet. Efter henholdsvis 48 og 96 timer bestemmes den insekticide virkning ved bestemmelse af udryddelsesraten.To 9 ml of culture medium is added at 50 ° C 1 ml of aqueous preparation containing 0.5% active substance. Then approx. Thirty fresh 25 hatched Lucilia sericata larvae for the culture medium. After 48 and 96 hours, respectively, the insecticidal effect is determined by determining the eradication rate.

Forbindelserne med formlen I ifølge eksemplerne 1 og 2 viser god virkning mod Lucilia sericata ved denne test.The compounds of formula I according to Examples 1 and 2 show good effect against Lucilia sericata in this test.

Eksempel 6.Example 6

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Virkning mod Aedes aegypti På overfladen af 150 ml vand, som befinder sig i en beholder, anbringes ved hjælp af en pipette en sådan mængde 0,1%'s ace-5 toneopløsning af forsøgsforbindelsen, at der opnås en koncentration på 400 ppm. Efter afdampning af acetonen anbringes 30-40 2 dage gamle Aedes-larver i beholderen. Dødeligheden bedømmes efter henholdsvis 2 og 7 dages forløb.Effect against Aedes aegypti On the surface of 150 ml of water contained in a container, a quantity of 0.1% acetone solution of the test compound is applied by means of a pipette to obtain a concentration of 400 ppm. After evaporation of the acetone, 30-40 2-day-old Aedes larvae are placed in the vessel. Mortality is assessed after 2 and 7 days, respectively.

Forbindelserne med formlen I ifølge eksemplerne 1 og 2 viser 10 god virkning ved denne test.The compounds of formula I according to Examples 1 and 2 show good effect in this test.

Eksempel 7.Example 7

Insekticid ædegiftvirkningInsecticidal poison effect

Bomuldsplanter med en højde på ca. 20 cm sprøjtes med en vandig emulsion af forsøgsforbindelsen (fremstillet ud fra et 15 10%'s emulgerbart koncentrat), idet emulsionerne indeholder forsøgsforbindelsen i koncentrationer fra 0,75 til 400 ppm.Cotton plants with a height of approx. 20 cm are sprayed with an aqueous emulsion of the test compound (prepared from a 10% emulsifiable concentrate), the emulsions containing the test compound at concentrations from 0.75 to 400 ppm.

Efter tørring af sprøjtevæsken besættes bomuldsplanterne med Spodoptera littoralis-larver og Heliothis virescens-larver på tredje larvestadium. Forsøget gennemføres ved en temperatur 20 på 24°C og en relativ luftfugtighed på 60%. Med intervaller på 24 timer bestemmes dødeligheden samt udviklings- og hudskifte-forstyrrelser hos larverne.After drying the spray liquid, the cotton plants are infested with Spodoptera littoralis larvae and Heliothis virescens larvae at the third larval stage. The test is carried out at a temperature of 20 ° C and a relative humidity of 60%. At 24-hour intervals, mortality as well as developmental and skin-changing disorders of the larvae are determined.

Mod Spodoptera opnås en 80-100%'s virkning ved denne test med forbindelsen nr. 1, nr. 2 og nr. 4 ved 0,75 ppm og med forbin-25 delsen nr. 3, nr. 6, nr. 7 og nr. 8 ved 3,0 ppm. Mod Heliothis opnås en virkning på 80-100% med forbindelsen nr. 1 og nr. 6 ved 3,0 ppm, med forbindelsen nr. 2 og nr. 7 ved 12,5 ppm, med forbindelsen nr. 3 og nr. 8 ved 50 ppm og med forbindelsen nr. 4 ved 400 ppm.Against Spodoptera, an 80-100% effect is obtained in this test with compound # 1, # 2 and # 4 at 0.75 ppm and with compound # 3, # 6, # 7 and No. 8 at 3.0 ppm. Against Heliothis, an effect of 80-100% is obtained with compound # 1 and # 6 at 3.0 ppm, with compound # 2 and # 7 at 12.5 ppm, with compound # 3 and # 8 at 50 ppm and with compound # 4 at 400 ppm.

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Eksempel 8.Example 8.

Virkning på Spodoptera littoralis og Heliothis virescens (larver og æg)_Effect on Spodoptera littoralis and Heliothis virescens (larvae and eggs) _

Tre bomuldsplanter med en højde på ca. 15-20 cm dyrket i 5 potter sprøjtes med et flydende sprøjtepræparat, som indeholder forsøgsforbindelsen i en koncentration på 400 ppm.Three cotton plants with a height of approx. 15-20 cm grown in 5 pots is sprayed with a liquid spray preparation containing the test compound at a concentration of 400 ppm.

Efter tørring af sprøjtevæsken anbringes planterne i en metalbeholder med et rumfang på ca. 20 liter, som tildækkes med en glasplade. Fugtighedsindholdet i den tildækkede 10 beholders indre reguleres således, at der ikke dannes kondensvand. Der undgås direkte belysning af planterne. Derpå inficeres de tre planter på følgende måde: a) 50 larver af Spodoptera littoralis eller Heliothis virescens på første larvestadium, 15 b) 20 larver af Spodoptera littoralis eller Heliothis virescens på tredje larvestadium, c) to ægportioner af Spodoptera littoralis eller Heliothis virescens (til dette formål indesluttes 2 blade på en af bomuldsplanterne med en plexiglascylinder, som er 20 lukket i begge ender med gaze), to ægportioner af Spodoptera eller en del af et bomuldsblad med derpå lagte æg af Heliothis sættes til de indelukkede blade.After drying the spray liquid, the plants are placed in a metal container with a volume of approx. 20 liters, which is covered with a glass plate. The moisture content of the interior of the covered 10 container is regulated so that no condensation water is formed. Direct lighting of the plants is avoided. The three plants are then infected as follows: a) 50 larvae of Spodoptera littoralis or Heliothis virescens at first larval stage, 15 b) 20 larvae of Spodoptera littoralis or Heliothis virescens at third larval stage, c) two egg portions of Spodoptera littoralis or Heliothis virescens (to for this purpose, 2 leaves are enclosed on one of the cotton plants with a plexiglass cylinder, which is closed at both ends with gauze), two egg portions of Spodoptera or part of a cotton leaf with eggs of Heliothis laid thereon are added to the enclosed leaves.

Bedømmelsen foretages efter 4 og 5 dages forløb i forhold til ubehandlede kontroller under anvendelse af følgende kriterier: 25 a) antal af levende larver, b) udviklings- og hudskifteforstyrrelser hos larverne, c) ædeskader (skrabeædning og hulædning), d) udklækningsrate (antal larver udklækket af æggene).The assessment is performed after 4 and 5 days in relation to untreated controls using the following criteria: 25 a) number of live larvae, b) developmental and skin change disorders of the larvae, c) edema damage (scratching and hollowing), d) hatching rate (number larvae hatched by the eggs).

Forbindelser med formlen I ifølge eksemplerne 1 og 2 viser 30 god totalvirkning ved denne test.Compounds of formula I according to Examples 1 and 2 show good overall efficacy in this test.

Eksempel 9.Example 9

0vieid virkning på Spodoptera littoralis Æg af Spodoptera littoralis lagt på filterpapir udsnittes 180Vidid effect on Spodoptera littoralis Eggs of Spodoptera littoralis laid on filter paper are excised 18

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af papiret og neddyppes i en 0,05 vægtprocent 's opløsning af forsøgsforbindelsen i en blanding af acetone og vand (1:1).of the paper and immersed in a 0.05% by weight solution of the test compound in a mixture of acetone and water (1: 1).

De således behandlede æg udtages derefter af blandingen og deponeres i kunststofskåle ved en temperatur på 28°C og en 5 relativ luftfugtighed på 60%.The eggs thus treated are then removed from the mixture and deposited in plastic bowls at a temperature of 28 ° C and a relative humidity of 60%.

Efter 5 dages forløb bestemmes udklækningsraten, dvs. antallet af larver, som har udviklet sig af de behandlede æg.After 5 days, the hatching rate is determined, ie. the number of larvae that have evolved from the treated eggs.

Forbindelser med formlen I ifølge eksemplerne 1 og 2 viser god virkning ved denne test.Compounds of formula I according to Examples 1 and 2 show good effect in this test.

10 Eksempel 10.Example 10.

Ovicid virkning på Epilachna varivestisOvicidal effect on Epilachna varivestis

Der fremstilles en blanding af 20 vægtprocent aktivt stof, 70 vægtprocent xylen og 10 vægtprocent af en blanding af et reaktionsprodukt af en alkylphenol med ethylenoxid og 15 calcium-dodecylbenzensulfonat. Af dette koncentrat fremstilles vandige emulsioner indeholdende 800 ppm aktivt stof.A mixture of 20% by weight of active substance, 70% by weight xylene and 10% by weight of a reaction product of an alkyl phenol with ethylene oxide and 15 calcium dodecylbenzenesulfonate is prepared. From this concentrate aqueous emulsions containing 800 ppm of active substance are prepared.

Ca. 100 frisklagte æg af Epilachna varivestis (mexikansk bønnebille.) lagt på blade af Phaseolus vulgaris fugtes med den ovenfor beskrevne vandige emulsion (koncentration af 20 aktivt stof 800 ppm), hvorpå der foretages let tørring.Ca. 100 freshly laid eggs of Epilachna varivestis (Mexican bean beetle) laid on leaves of Phaseolus vulgaris are moistened with the above-described aqueous emulsion (concentration of 20 active substance 800 ppm), then lightly drying.

Æggene anbringes i en beluftet beholder, indtil de samtidig lagte ubehandlede kontrolæg er udklækkede. Under et binokular foretages bedømmelse med hensyn til bestemmelse af den procentvise udryddelse.The eggs are placed in an aerated container until the simultaneously laid untreated control eggs are hatched. During a binocular assessment is made with regard to determining the percentage extinction.

25 Forbindelser med formlen I ifølge eksemplerne 1 og 2 viser god virkning ved denne test.Compounds of formula I according to Examples 1 and 2 show good effect in this test.

Eksempel 11.Example 11.

Ovicid virkning på Heliothis virescens og Leptinotarsa decemlineata_ 30 Tilsvarende mængder fugtepulverformulering indeholdende 19Ovicidal effect on Heliothis virescens and Leptinotarsa decemlineata_ 30 Corresponding amounts of moisturizing powder formulation containing 19

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r 25 vægtprocent forsøgsforbindelse blandes med en sådan mængde vand, at der dannes en vandig emulsion med en koncentration af forsøgsforbindelsen på 800 ppm. .The 25% by weight test compound is mixed with an amount of water to form an aqueous emulsion with a concentration of the test compound of 800 ppm. .

I emulsionerne indeholdende forsøgsforbindelserne neddyppes 5 en dag gamle æg af Heliothis på "Cellophan"® eller æg afIn the emulsions containing the test compounds, 5 one day old eggs of Heliothis are immersed on "Cellophan" ® or eggs of

Leptinotarsa på kartoffelblade. Neddypningstiden er 3 minutter, hvorpå der foretages frasugning på rundfiltre. De således behandlede æg anbringes i petriskåle, som opbevares i mørke. Efter 6-8 dage bestemmes udklækningsgraden sammen-10 lignet med ubehandlede kontrolæg.Leptinotarsa on potato leaves. The immersion time is 3 minutes, after which suction on round filters is performed. The eggs thus treated are placed in petri dishes which are stored in the dark. After 6-8 days, the hatching rate is determined compared to untreated control eggs.

Forbindelser med formlen I ifølge eksemplerne 1 og 2 viser god virkning ved denne test.Compounds of formula I according to Examples 1 and 2 show good effect in this test.

Eksempel 12.Example 12.

Ovicid virkning på Laspeyresia pomonella (æg) 15 Æg lagt af Laspeyresia pomonella, som er højst 24 timer gamle, neddyppes på filtrerpapir i 1 minut i en vandig acetoneopløsning indeholdende forsøgsforbindelsen i en koncentration på 400 ppm. Efter tørring anbringes æggene i petriskåle, som henstår ved en temperatur på 28°C. Efter 6 dages forløb be-20 stemmes den procentvise udklækning af de behandlede æg.Ovicidal action on Laspeyresia pomonella (eggs) 15 Eggs laid by Laspeyresia pomonella, which is not more than 24 hours old, are immersed on filter paper for 1 minute in an aqueous acetone solution containing the test compound at a concentration of 400 ppm. After drying, place the eggs in petri dishes, which are left at a temperature of 28 ° C. After 6 days, the percentage hatching of the treated eggs is determined.

Forbindelser med formlen I ifølge eksemplerne 1 og 2 viser god virkning ved denne test.Compounds of formula I according to Examples 1 and 2 show good effect in this test.

Eksempel 13.Example 13

Virkning mod Anthonomus grandis (voksenindivider) 25 To bomuldsplanter dyrket i potter på 6-bladstadiet sprøjtes med vandige befugtelige emulsionspræparater, som indeholder forsøgsforbindelsen i en koncentration på 12,5 ppm. Efter tørring af sprøjtevæsken (ca. 1,5 timer) besættes hver plante med 10 voksne biller (Anthonomus grandis). Plasticcylindre, 30 hvis øvre åbninger er tildækket med gaze, anbringes derpå over de behandlede planter, hvorpå forsøgsdyrene er anbragtAction against Anthonomus grandis (adult) 25 Two cotton plants grown in pots at the 6-leaf stage are sprayed with aqueous wettable emulsion preparations containing the test compound at a concentration of 12.5 ppm. After drying the spray liquid (about 1.5 hours), each plant is infested with 10 adult beetles (Anthonomus grandis). Plastic cylinders, whose upper openings are covered with gauze, are then placed over the treated plants on which the test animals are placed

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20 for at undgå,at billerne skal vandre bort. De behandlede planter holdes ved en temperatur på 25°C og en relativ luftfugtighed på ca. 60%. Bedømmelsen foretages efter henholdsvis 2, 3, 4 og 5 dage med henblik på bedømmelse af den procentvise døde-5 lighed for de anvendte forsøgsdyr (procentvis rygliggende biller) samt antifeedant-virkningen (i forhold til ubehandlede kontrolbiller).20 to prevent the beetles from wandering away. The treated plants are maintained at a temperature of 25 ° C and a relative humidity of approx. 60%. The assessment is performed after 2, 3, 4 and 5 days, respectively, for the purpose of assessing the percentage mortality of the test animals used (percentage of smoking beetles) and the antifeedant effect (relative to untreated control beetles).

Forbindelser nr. 1, 2, 6 og 7 giver 80-100%'s virkning (dødelighed) ved denne test.Compounds Nos. 1, 2, 6 and 7 give the effect (mortality) of 80-100% in this test.

10 Eksempel 14.Example 14.

Virkning mod planteskadelige akarider: Tetranychus urticae (OP-følsomme) og Tetranychus cinnabarinus (OP-tolerante)Effect against plant harmful acarides: Tetranychus urticae (OP-sensitive) and Tetranychus cinnabarinus (OP-tolerant)

Primærbladene på Phaseolus vulgaris-planter belægges 16 timer før forsøgets begyndelse med et inficeret bladstykke fra en 15 massedyrkning af Tetranychus urticae (OP-følsomme) ellerThe primary leaves of Phaseolus vulgaris plants are coated 16 hours before the start of the experiment with an infected leaf piece from a 15 mass cultivation of Tetranychus urticae (OP sensitive) or

Tetranychus cinnabarinus (OP-tolerante). (Tolerancen refererer til foreneligheden overfor Diazinon).Tetranychus cinnabarinus (OP tolerant). (Tolerance refers to compatibility with Diazinon).

De således behandlede inficerede planter sprøjtes med en forsøgsopløsning, som indeholder forsøgsforbindelsen i en 20 koncentration på 400 ppm, indtil sprøjtevæsken drypper fra planterne.The thus treated infected plants are sprayed with a test solution containing the test compound at a concentration of 400 ppm until the spray liquid drips from the plants.

Efter 24 timers forløb og atter efter 7 dage bedømmes imagoer og larver (alle bevægelige stadier) under binokularet for levende og døde individer.After 24 hours and again after 7 days, images and larvae (all moving stages) are evaluated under the binocular for living and dead individuals.

25 Der anvendes én plante for hver koncentration og for hver forsøgsdyreart. Under forsøget henstår planterne i en væksthuskabine ved 25°C.25 One plant is used for each concentration and for each experimental animal species. During the experiment, the plants are left in a greenhouse at 25 ° C.

Forbindelser med formlen I ifølge eksemplerne 1 og 2 viser i dette forsøg god virkning mod Tetranychus urticae og 30 Tetranychus cinnabarinus.Compounds of formula I according to Examples 1 and 2 in this experiment show good effect against Tetranychus urticae and Tetranychus cinnabarinus.

Eksempel 15.Example 15

2121

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Påvirkning af formeringen hos Anthonomus grandisInfluence of reproduction on Anthonomus grandis

Voksne individer af Anthonomus grandis, som efter udklækningen højst er 24 timer gamle, overføres i grupper på 25 biller til 5 bure med gittervægge. Burene indeholdende billerne neddyppes straks i 5-10 sekunder i en acetoneopløsning, som indeholder forsøgsforbindelsen i en koncentration på 800 ppm. Når billerne atter er tørre, anbringes de med henblik på formering og æglægning i skåle, som er tildækkede, og som indeholder foder.Adult individuals of Anthonomus grandis, which after hatching are not more than 24 hours old, are transferred in groups of 25 beetles to 5 cages with lattice walls. The cages containing the beetle are immediately immersed for 5-10 seconds in an acetone solution containing the test compound at a concentration of 800 ppm. When the beetles are dry again, they are placed for feeding and egg laying in covered bowls containing feed.

10 Lagte æg udskilles to til tre gange ugentlig med rindende vand, optælles, desinficeres ved anbringelse i to til tre timer i et vandigt desinfektionsmiddel, hvorpå de deponeres i skåle, som indeholder en egnet larvediæt. Efter 7 dage undersøges det, om der er udviklet larver fra de deponerede æg.10 Eggs are secreted two to three times weekly with running water, counted, disinfected by placing for two to three hours in an aqueous disinfectant and then deposited in bowls containing a suitable larval diet. After 7 days, it is examined whether larvae have developed from the deposited eggs.

15 Til bedømmelse af varigheden af virkningen på formeringen af forsøgsforbindelserne testes billernes æglægning i et tidsrum på ca. 4 uger. Bedømmmelsen foretages ved hjælp af formindskelsen i antallet af lagte æg og de deraf klækkede larver sammenlignet med ubehandlede kontrolbiller.To evaluate the duration of the effect on the propagation of the test compounds, the egg laying of the beetles is tested for a period of approx. 4 weeks. The assessment is done by the reduction in the number of eggs laid and the hatched larvae compared to untreated control beetles.

20 Forbindelser med formlen I ifølge eksemplerne 1 og 2 viser en god formeringsnedsættende virkning ved denne test.Compounds of formula I according to Examples 1 and 2 show a good propagation-reducing effect in this test.

Claims (12)

1. N-[3-halogen-4-(hexafluorpropyloxy)-5-trifluormethyl]-phenyl-Ν'-benzoylurinstoffer, kendetegnet ved, at de har den almene formel J1 J3 5 / \-CONHCONH-/ S. -0-CF,CHFCF, (X) \—S ·\_/ 2 3 lx' r2 cf3 hvori R1 betyder hydrogen eller halogen, og R2 og R3 betyder halogen.N- [3-halogen-4- (hexafluoropropyloxy) -5-trifluoromethyl] -phenyl-Ν'-benzoylureas, characterized in that they have the general formula J1 J3 5 / - -CONHCONH- / S-0- CF, CHFCF, (X) \ -S · \ _ / 2 3 lx 'r2 cf3 wherein R 1 is hydrogen or halogen and R 2 and R 3 are halogen. 2. Forbindelse ifølge krav 1, kendetegnet ved, at R^ betyder hydrogen, fluor eller chlor, R2 betyder fluor 10 eller chlor, og R^ betyder chlor eller brom.A compound according to claim 1, characterized in that R 1 is hydrogen, fluorine or chlorine, R 2 is fluorine or chlorine and R 2 is chlorine or bromine. 3. Forbindelse ifølge krav 1, kendetegnet ved, at R^ betyder hydrogen, fluor eller chlor, R2 betyder fluor eller chlor, og R^ betyder chlor.A compound according to claim 1, characterized in that R 1 is hydrogen, fluorine or chlorine, R 2 is fluorine or chlorine, and R 2 is chlorine. 4. Forbindelse ifølge krav 3, kendetegnet ved, 15 at den har formlen T 9l •C N-CONHCONH—v 0-CF2CHFCF3 \-S V-/ i 5. . .....Forbindelse ifølge krav 3, kendetegnet ved, at den har formlen ί1 91 ·· I·· -CONHCONH- O-CF2CHFCF3 £ i?3 DK 161196 BCompound according to claim 3, characterized in that it has the formula T 9l • C N-CONHCONH-v 0-CF2CHFCF3 \ -S V- / i 5.. A compound according to claim 3, characterized in that it has the formula 91 ·· I ·· -CONHCONH- O-CF2CHFCF3 £ in 3 DK 161196 B 6. Forbindelse ifølge krav 2, kendetegnet ved, at R^ betyder hydrogen, fluor eller chlor, R2 betyder fluor eller chlor, og R^ betyder brom.A compound according to claim 2, characterized in that R 1 is hydrogen, fluorine or chlorine, R 2 is fluorine or chlorine, and R 2 is bromine. 7. Forbindelse ifølge krav 6, kendetegnet ved, 5 at den har formlen T fr ·* ... / COSHCONH—( y-O-CFzCHFCFi i i?.Compound according to claim 6, characterized in that it has the formula T fr · * ... / COSHCONH - (γ-O-CF 2 CHFCF 1 i). 8. Forbindelse ifølge krav 6, kendetegnet ved, at den har formlen • I ·· / CONHCONH—{ y- O-CF2CHFCF3 Af3Compound according to claim 6, characterized in that it has the formula • I ·· / CONHCONH - {y- O-CF2CHFCF3 Af3 9. Fremgangsmåde til fremstilling af en forbindelse med formlen I ifølge krav 1, kendetegnet ved, at man a) omsætter en forbindelse med formlen R-j i j cf3chfcf2-o-^' N.-NH2 (H) ^3 med en forbindelse med formlen »I 15 \ \-cO-N-C-O (III) å2 eller b) omsætter en forbindelse med formlen h CF3CHFCF2-0-^ -N=c=0 (IV) DK 161196B med en forbindelse med formlen ·' CO-SHi (V) • V· 4= eller c) omsætter en forbindelse med formlen II med en forbindelse 5 med formlen J1 CONHCOOR (VI) k idet i formlerne II, III, IV, V og VI grupperne R^, r2 og R3 har de ovenfor i krav 1 anførte betydninger, og R betyder en eventuelt med halogen substitueret C-^g-alkylgruppe.Process for the preparation of a compound of formula I according to claim 1, characterized in that a) reacting a compound of formula Rj in cf3chfcf2-o- 'N.-NH2 (H) ^ 3 with a compound of formula » In 15 µ-CO-NCO (III) Å 2 or b), a compound of formula h represents CF3CHFCF2-0- N = c = O (IV) DK 161196B with a compound of formula · CO-SHi (V) V · 4 = or c) translates a compound of formula II with a compound 5 of formula J1 CONHCOOR (VI) k, wherein in formulas II, III, IV, V and VI the groups R 1, R 2 and R 3 have the above claims. 1 and R is an optionally halogen-substituted C 1-6 alkyl group. 10. Skadedyrsbekæmpelsesmiddel, kendetegnet ved, 5 at det som aktiv komponent indeholder en forbindelse ifølge et af kravene 1-8 sammen med egnede bærestoffer og/eller andre tilsætningsstoffer.A pest control agent, characterized in that it contains as an active component a compound according to any one of claims 1-8 together with suitable carriers and / or other additives. 11. Anvendelse af en forbindelse ifølge et af kravene 1-8 til bekæmpelse af insekter og individer af ordenen Acarina på 10 dyr og planter.Use of a compound according to any one of claims 1-8 for the control of insects and individuals of the order Acarina on 10 animals and plants. 12. Anvendelse ifølge krav 11 til bekæmpelse af planteskade-lige insekter af ordenen Acarina.Use according to claim 11 for the control of plant harmful insects of the order Acarina. 13. Anvendelse ifølge krav 12 til bekæmpelse af planteskade-lige insekter af ordenen Acarina i bcnulds- og frugtkulturer. 15 1‘4. Fremgangsmåde til bekæmpelse af insekter og individer af ordenen Acarina, kendetegnet ved, at skadedyrene eller deres forskellige udviklingsstadier eller deres opholdssted behandles eller bringes i kontakt med en pesticidt virksom mængde af en forbindelse med formlen I ifølge et af kravene 20 1-8 eller med et middel, som foruden tilsætningsstoffer og bærestoffer indeholder en pesticidt virksom mængde af denne forbindelse.Use according to claim 12 for the control of plant-harmful insects of the order Acarina in vegetable and fruit cultures. 1'4. Method for controlling insects and individuals of the order Acarina, characterized in that the pests or their various stages of development or their place of residence are treated or brought into contact with a pesticide-effective amount of a compound of formula I according to any one of claims 20 1-8 or with a agent which contains, in addition to additives and carriers, a pesticide-effective amount of this compound.
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