DE3642466A1 - N-Benzoyl-N'-3,5-dichloro-2-fluoro-4-(3-trifluoromethyl)phenoxy-ph enylureas, their preparation, and their use for controlling pests - Google Patents

Abstract

N-Benzoyl-N'-3,5-dichloro-2-fluoro-4-(3-trifluoromethyl)phenoxy-phe nylureas of the formula I <IMAGE> in which R<1> denotes fluorine, chlorine or bromine, R<2> denotes fluorine, chlorine or hydrogen, their preparation and their use as pesticides.

Description

The invention relates to N-benzoyl-N'-3,5-dichloro-2-fluoro-4- (3-trifluoromethyl) phenoxyphenylureas, Process for their preparation and Pesticides that use these compounds as active ingredients contain.

Compounds of the N-benzoyl-N'-phenylurea type can be used as Insecticides are used (J. Agr. Food Chem. 21, 348 [1973]; cf. also DE-A-21 23 236 and US-A-43 99 152).

It was found that N-benzoyl-N'-3,5-dichloro-2-fluoro-4- (3- trifluoromethyl) phenoxyphenylureas of the general formula I

in which means

R1 fluorine, chlorine, bromine, R2 fluorine, chlorine or hydrogen

with the proviso that either R¹ and R² fluorine or chlorine or R¹ chlorine and R² means hydrogen, insecticidal and acaricidal are very effective.

DE-A-30 44 055 and EP-A-52 833 are benzoylureas similar structure against animal pests known. These connections are described by the general formula (A)

in the  

X for oxygen or sulfur, Y for chlorine or fluorine or For hydrogen, chlorine or fluorine

stands.

Surprisingly, the compounds of the invention show despite their Similarity to the known compounds is clearly superior Effect.

The N-benzoyl-N'-3,5-dichloro-2-fluoro-4- (3- trifluoromethyl) phenoxyphenylureas in any way necessary to manufacture of the corresponding known compounds can be used. For example, you can a compound of formula II

with a corresponding benzoyl isocyanate of the formula III

or if the required starting materials II or III are not available or stand too expensive, a corresponding compound of formula IV

with a compound of formula V

implement.

Such reactions, appropriate conditions, solvents and others Notes are e.g. B. described in DE-A-21 23 236.

The implementations are partly quantitative and mostly deliver from uniform products in advance, if necessary, the usual Methods for cleaning, e.g. B. recrystallization applied. To elemental analysis, melting point, IR and NMR spectrum.

To carry out the first-mentioned method, the substituted aniline II together with a solvent or diluent submitted and added a stoichiometric amount of isocyanate III. The Implementation usually takes no more than 2 hours. The other Procedure requires i. a. a reaction time of 2 to 6 hours, where the addition of a catalyst such as triethylamine or dibutyltin diacetate can be advantageous.

The benzoyl isocyanates III are known compounds; you can z. B. according to the regulations in J. Org. Chem. 28, 1805 to 1811 (1963) or J. Agr. Food Chem. 21, 348 (1973).

The 3,5-dichloro-2-fluoro-4- (3-trifluoromethyl) - used as starting material phenoxyphenylamine II and the corresponding isocyanates V are new. they can by using conventional methods from the corresponding nitrobenzenes Reduction can be produced (Houben-Weyl, methods of organic Chemie, XI / 1, pp. 360 ff. [1975]). The corresponding nitrobenzenes in turn are obtained by reacting 3,5-dichloro-2,4-difluoronitrobenzene with 3-trifluoromethylphenol or its salt by known methods. 3,5-dichloro-2-fluoro-4- (3-trifluoromethyl) phenoxyphenylamine II can be used in the corresponding isocyanate V are transferred (cf. Weygard Hilgetag, Organic chemical experimentation, 1970; DE-OS 25 38 178).

Manufacturing examples A. 3,5-dichloro-2-fluoro-4- (3-trifluoromethyl) phenoxynitrobenzene

23.9 g (0.11 mol) of 3,5-dichloro-2,4-difluoronitrobenzene with 17.3 g (0.10 mol) 3-trifluoromethylphenol and 4.8 g (0.12 mol) NaOH in 150 ml Section. DMSO stirred at 120 ° C for 10 hours. After cooling, pour in Ice water and extracted with petroleum ether. 34 g of crude product are obtained, which by means of column chromatography on silica gel Toluene / ethyl acetate (8: 2) is cleaned; Yield 28.3 g (yellow, viscous oil).

B. 3,5-dichloro-2-fluoro-4- (3-trifluoromethyl) phenoxyphenylamine

28.3 g of the product obtained according to A. are abs. In 150 ml. THF with 2 g of Raney nickel are hydrogenated at room temperature and 0.3 bar H₂ pressure. Man separates from the catalyst, evaporates to give 26.4 g of crude product, which by means of column chromatography on silica gel Toluene / ethyl acetate (9: 1) is cleaned as the eluent.

C. N-2,6-difluorobenzoyl-N'-3,5-dichloro-2-fluoro-4- (3-trifluoromethyl) phenoxyphenylurea (Example 1)

To a solution of 4.5 g (0.013 mol) of the product obtained according to B. in 50 ml abs. THF is added dropwise at room temperature to 2.4 g (0.013 mol) 2,6-difluorobenzoyl isocyanate. The mixture is then stirred at 45 ° C. for 2 hours and, after cooling to 0 ° C., mixed with 100 ml of n-pentane and suction filtered. After drying, 4.55 g (67% of the arithmetically possible Yield) N-2,6-difluorobenzoyl-N'-3,5-dichloro-2-fluoro-4- (3-trifluoromethyl) phen-oxyphenylurea from melting point 186 to 188 ° C (Compound 1 of the table below).

The N-benzoyl-N'-3,5-dichloro-2-fluoro-4- (3-trifluoromethyl) phenoxyphenylureas of the formula I are suitable for pests from the class of Effectively control insects, arachnids and nematodes. you can in Plant protection as well as in the hygiene, protection of stocks and veterinary sector can be used as pesticides.

Harmful insects belong to the order of the butterflies
(Lepidoptera) for example Plutella maculipennis (cabbage cockroach), Leucoptera coffeella (coffee moth), Hyponomeuta malinellus (apple tree spider moth), Argyresthia conjugella (apple moth), Sitotroga cerealella (grain moth), Phthorimaea operculella (potato moth mothler) (Apple Sparschelothule moth), Capua ), Cacoecia murinana (pine shoot winder), Tortrix viridana (oak winder), Clysia ambiguella (hay and sour worm), Evetria buoliana (pine shoot winder), Polychrosis botrana (crossed grape winder), Cydia pomonella (fruit-made), funp (Plum wrapper), Ostrinia nubilalis (European corn borer), Loxostege sticticalis (European corn borer), Ephestia kuehniella (flour moth), Chilo suppressalis (rice stalk borer), Galleria mellonella (wax moth), Thacosoma neustria (ringed spinner) pinna spinnero pinna spinnera, pomegranate spinner) ), Phalera bucephala (moon spot), Cheima tobia brumata (Little Frost Tree), Hibernia defoliaria (Big Frost Tree), Bupalus piniarius (Pine Tree Tree), Hyphantria cunea (White Bear Spinner), Agrotis segetum (Winter Saateule), Agrotis ypsilon (Ypsiloneule), Barathra brassicair (Kohlule) , Prodenia litura (caterpillar), Laphygma exigua (beet armyworm), Panolis flammea (Forleule), Earias insulana (cotton capsule worm), Plusia gamma (Gammaeule), Alabama argillacea (cotton leaf worm), Lymantria dispar (sponge spinner), Lymantria monach , Pieris brassicae (cabbage white butterfly), Aporia crataegi (tree white butterfly);
from the order of the beetles (Coleoptera), for example, Blitophaga undata (black beet beetle), Melanotus communis (wireworm), Limonius californicus (wireworm), Agriotes lineatus (seed snap beetle), Agriotes obscurus (humus snap beetle), Agrilus sinusatus (Birnbaum) (Rapeseed beetle), Atomaria linearis (moss button beetle), Epilachna varivestis (Mexican bean beetle), Phyllopertha horticola (June beetle), Popillia japonica (Japan beetle), Melolontha melolontha (Feldmaikäfer), Melolontha (Crimagallusferi) Brachocalli ferris (Maikikallisferi) Brachocalli Asparagus Chicken), Lema melanopus (Cereal Chicken), Leptinotarsa decemlineata (Colorado Beetle), Phaedon cochleariae (Horseradish Leaf Beetle), Phyllotreta nemorum (Cabbage Flea), Chaetocnema tibialis (Beet Flea Beetle) Rape, Phyllophalicaotica Role, Phyllophalosaurus Rape, Phyllophalica Beetle (Maize Flea Beetle), Phylloalphaica Rape, Phyllophalica Beetle (Maize Flea Beetle), Phylloalphaica Rape, Phyllophalica Beetle ), Cassida nebulosa (misty tortoise beetle), Bruchus lentis (lenticular beetle), Bruchus rufimanus (horse bean beetle), Bruchus pisorum (pea beetle), Sitona lineatus (lined leaf beetle), Ortiorrhynchus sulcatus (furrowed rag weevil), Otiorrhynchus ovatus (strawberry root weevil) (Apfelbelüssel (big apple), betle beetle rye) (betel beetroot), betel beetle rye (betel beetroot), betel beetle rye (betel beetroot), betel beetle rye (betel beetroot), betel beetle rye (betel beetroot), betel beetle rye (beti , Anthonomus grandis (capsule beetle), Ceuthorrhynchus assimilis (cabbage pod weevil), Ceuthorrynchus napi (large cabbage weevil), Sitophilus granaria (grain beetle), Anisandrus dispar (uneven wood bark beetle), Ips typographus (printer printer)
from the order of the two-winged species (Diptera), for example Lycoria pectoralis, Mayetiola destructor (Hessian fly), Basineura brassicae (cabbage gall gnat), Contarinia tritici (yellow wheat gall mosquito), Haplodiplosis equestris (saddle gnat), Tipula paludosa (meadow snake), Tipula Cabbage schnapps), Dacus cucurbitae (melon fly), Dacus oleae (olive fly), Ceratitis capitata (Mediterranean fruit fly), Rhagoletis cerasi (cherry fruit fly), Rhagoletis pomonella (apple maggot), Anastrepha ludens (Mexican fruit fly), Oscitachella fritta ), Phorbia antiqua (onion fly), Phorbia brassicae (small cabbage fly), Pegomya hysocyami (beet fly), Anopheles maculipennis, Culex pipiens, Aedes aegypti (yellow fever mosquito), Aedes vexans, Tabanus bovinus (cattle brake), Mushroom domestica), Tipula palakeosa (Housefly), Fannia canicularis (small housefly), Muscina stabulans, Glossina morsitans (Tsetse fly), Oestrus ovis, Chry somya macellaria, Chrysomya hominivorax, Lucilia cuprina, Lucilia sericata, Hypoderma lineata;
from the order of the hymenoptera (Hymenoptera), for example Athalia rose (turnip wasp), Hoplocampa minuta (plum saw wasp), Monomorium pharaonis (pharaoh ant), Solenopsis geminata (fire ant), Atta sexdens (leaf cutter ant);
from the order of the bugs (Heteroptera), for example Nezara viridula (green rice bug), Eurygaster integriceps (Asian grain bug), Blissus leucopterus (Chinch bug), Dysdercus cingulatus (Kapok bug), Dysdercus intermedius (cotton bug), Piesma quadrata (beet bug), Lygus pratensis (common meadow bug);
from the order of the plant suckers (Homoptera), for example Perkinsiella saccharicida (sugar cane leafhopper), Nilaparvata lugens (brown leafhopper), Empoasca fabae (potato leafhopper), Psylla mali (apple leaf suction device), Psylla piri (pear leaf suction device), Trialeuris fumeariorum (Trialeuris fumeariorum) (Trialeuris vaporie) Black Bean Louse), Aphis pomi (Green Apple Lice), Aphis sambuci (Elder Aphid), Aphidula nasturtii (Buckthorn Aphid), Cerosipha gossypii (Cucumber Aphid), Sappaphis mali (Rosy Apple Aphid), Sappaphis mala (Mealy Pear Louse Aphid), Dappaphis Brachycaudus cardui (Great Plum Aphid), Brevicoryne brassicae (Cabbage Aphid), Phorodon humuli (Hop Aphid), Rhopalomyzus ascalonicus (Onion Louse), Myzodes persicae (Green Peach Louse), Myzus cerasi (Black Sour Cherry Lice), Dysaulacorthum Pseudosrryonis (Pseudosrellus oni), Pseudosrellus oni (Pseudosrellus) Pea Louse), Macrosiphon rosae (Large Rose Aphid), Megoura viciae (Wickenlaus), Schizo neura lanuginosa (pear aphid), Pemphigus bursarius (lettuce root louse), Dreyfusia nordmannianae (pine shoot louse), Dreyfusia piceae (silver fir stem louse), Adelges laricis (red spruce gall louse), Viteus vitifolii (vine louse);
from the order of the termites (Isoptera), for example Reticulitermes lucifugus, Calotermes flavicollis, Leucotermes flavipes, Termes natalensis;
from the order of the straight winged wing (Orthoptera), for example, Forficula auricularia (common earwig), Acheta domestica (crickets), Gryllotalpa gryllotalpa (mole cricket), Tachycines asynamorus (greenhouse insect), Locusta migratoria (mantis grasshopper), Stauronotkan maroccanus peregrine (Moroccan migrant) Grasshopper), Nomadacris septemfasciata (grasshopper), Melanoplus spretus (rock grasshopper), Melanoplus femur-rubrum (red-legged grasshopper), Blatta orientalis (cockroach), Blattella germanica (German cockroach), Periplaneta americana (American cockroach).

The arachnoid class includes arachnids (Acarina), for example Ixodes ricinus (woodbuck), Ornithodorus moubata, Amblyomma americanum, Dermacentor silvarum, Boophilus microplus, Tetranychus telarius, Tetranychus pacificus, Paratetranychus pilosus, Bryobia praetiosa.

The class of Nemathelminthes include, for example Root gall nematodes, e.g. B. Meloidogyne incognita, Meloidogyne hapla, Meloidogyne javanica, cyst-forming nematodes, e.g. B. Globodera rostochiensis, heterodera schatii, heterodera avenae, heterodera glycinae, Hetrodera triflolii, stick and leaf flakes, e.g. B. Ditylenchus dipsaci, Ditylenchus destructor, Pratylenchus neglectus, Pratylenchus penetrans,  Partylenchus goodeyi, Paratylenchus curvitatus and Tylenchorhynchus dubius, Tylenchorhynchus claytoni, Rotylenchus robustus, Heliocotylenchus multicinctus, Radopholus similis, Belonolaimus longicaudatus, Longidorus elongatus, Trichodorus primitivus.

The active ingredients as such, in the form of their formulations or from it prepared possible applications, e.g. B. in the form directly sprayable solutions, powders, suspensions or dispersions, Emulsions, oil dispersions, pastes, dusts, spreading agents, Granules by spraying, atomizing, dusting, scattering or pouring be applied. The application forms depend entirely on the Purposes: in any case, they should be the finest Ensure distribution of the active ingredients according to the invention.

For the production of directly sprayable solutions, emulsions, pastes or Oil dispersions come from medium to high mineral oil fractions Boiling point, such as kerosene or diesel oil, as well as coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g. B. benzene, toluene, xylene, paraffin, Tetrahydronaphthalene, alkylated naphthalenes or their derivatives, Methanol, ethanol, propanol, butanol, chloroform, carbon tetrachloride, Cyclohexanol, cyclohexanone, chlorobenzene, isophorone, strongly polar Solvents, e.g. B. dimethylformamide, dimethyl sulfoxide, N-methylpyrrolidone, water.

Aqueous application forms can be used as emulsion concentrates, pastes or wettable powders (wettable powders, oil dispersions) by adding water be prepared. For the production of emulsions, pastes or Oil dispersions can be the substances as such or in an oil or Solvent dissolved, by means of wetting, adhesive, dispersing or Emulsifiers can be homogenized in water. But it can also be made active substance wetting, adhesive, dispersing or emulsifying agent and possibly concentrates containing solvents or oil are produced, which are suitable for dilution with water.

Alkali, alkaline earth, ammonium salts come from as surface-active substances Ligninsulfonic acid, naphthalenesulfonic acid, phenolsulfonic acid, Alkylarylsulfonate, alkyl sulfates, alkyl sulfonates, alkali and Alkaline earth metal salts of dibutylnaphthalenesulfonic acid, lauryl ether sulfate, Fatty alcohol sulfates, fatty acid alkali and alkaline earth, sulfated salts Hexadecanols, heptadecanols, octadecanols, salts of sulfated Fatty alcohol glycol ether, condensation products of sulfonated naphthalene and naphthalene derivatives with formaldehyde, condensation products of  Naphthalene or naphthalene sulfonic acids with phenol and formaldehyde, Polyoxyethylene octylphenol ether, ethoxylated isooctylphenol, octylphenol, Nonylphenone, alkylphenol polyglycol ether, tributylphenyl polyglycol ether, Alkylaryl polyether alcohols, isotridecyl alcohol, Fatty alcohol ethylene oxide condensates, ethoxylated castor oil, Polyoxyethylene alkyl ether, ethoxylated polyoxypropylene, Lauryl alcohol polyglycol ether acetal, sorbitol ester, lignin, sulfite waste liquor and methyl cellulose.

Powders, materials for spreading and dusts can be mixed or combined Grinding the active substances with a solid carrier getting produced.

Examples of formulations are:

I.5 parts by weight of compound no.1 are with 95 parts by weight finely divided kaolin mixed intimately. You get this way a dust containing 3% by weight of the active ingredient. II.30 parts by weight of compound No. 5 are mixed with a mixture of 92 parts by weight of powdered silica gel and 8 parts by weight Paraffin oil that is sprayed onto the surface of this silica gel was mixed intimately. You get one in this way Preparation of the active ingredient with good adhesiveness. III.10 parts by weight of compound no. 1 are in a mixture dissolved that from 90 parts by weight of xylene, 6 parts by weight of the adduct from 8 to 10 moles of ethylene oxide to 1 mole of oleic acid N-monoethanolamide, 2 parts by weight of calcium salt of dodecylbenzenesulfonic acid and 2 parts by weight of the adduct of 40 moles There is ethylene oxide in 1 mol of castor oil. IV.20 parts by weight of compound no. 5 are in a mixture dissolved, from 60 parts by weight of cyclohexanone, 30 parts by weight Isobutanol, 5 parts by weight of the adduct of 7 moles Ethylene oxide in 1 mole of isooctylphenol and 5 parts by weight of the adduct of 40 moles of ethylene oxide to 1 mole of castor oil consists. V.80 parts by weight of compound no. 1 are mixed with 3 parts by weight of the Sodium salt of diisobutylnaphthalene-alpha-sulfonic acid, 10 parts by weight of the sodium salt of a lignosulfonic acid a sulfite waste liquor and 7 parts by weight of powdered silica gel well mixed and ground in a hammer mill.

Granules, e.g. B. coating, impregnation and homogeneous granules by binding the active ingredients to solid carriers. Solid carriers are e.g. B. mineral earths, such as silica gel, silicas, Silica gels, silicates, talc, kaolin, attaclay, limestone, lime, chalk, Bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, Magnesium oxide, ground plastics, fertilizers such. B. ammonium sulfate, Ammonium phosphate, ammonium nitrate, ureas and herbal products, such as corn flour, tree bark, wood and nutshell flour, cellulose powder and other solid carriers.

The formulations generally contain between 0.1 and 95% by weight Active ingredient, preferably between 0.5 and 90 wt .-%.

The active ingredient concentrations in the ready-to-use preparations can be varied in larger areas.

Generally they are between 0.0001 and 10%, preferably between 0.01 and 1%. The active ingredients can also be used successfully in the Ultra-low-volume (ULV) processes are used, whereby it is possible Formulations with more than 95 wt .-% active ingredient or even the active ingredient without applying additives.

The amount of active ingredient applied under field conditions is 0.2 to 10, preferably 0.5 to 2.0 kg / ha.

Oils of various types, herbicides, fungicides, other pesticides, bactericides, if necessary first immediately before use (tank mix). This means can to the agents according to the invention in a weight ratio of 1:10 to 10: 1 can be added.

For example, the following agents can be added: 1,2-dibromo-3- chloropropane, 1,3-dichloropropene, 1,3-dichloropropene + 1,2-dichloropropane, 1,2-dibromoethane, 2-sec.-butyl-phenyl-N-methylcarbamate, o-chlorophenyl-N- methyl carbamate, 3-isopropyl-5-methylphenyl-N-methyl carbamate, o-isopropoxyphenyl-N-methyl carbamate, 3,5-dimethyl-4-methylmercapto-phenyl-N- methyl carbamate, 4-dimethylamino-3,5-xylyl-N-methyl carbamate, 2- (1,3-dioxolan-2-yl) phenyl-N-methyl carbamate, 1-naphthyl-N-methylcarbamate, 2,3-dihydro-2,2-dimethyl-benzofuran-7-yl-N-methylcarbamate, 2,2-dimethyl-1,3- benzodioxol-4-yl-N-methyl carbamate, 2-dimethylamino-5,6-dimethyl-4-pyrimidinyl dimethyl carbamate, 2-methyl-2- (methylthio) propionaldehyde-O- (methylcarbamoyl) oxime, S-methyl-N [(methylcarbamoyl) -oxy] thio-acetimidate, Methyl-N ′, N′-dimethyl-N - [(methylcarbamoyl) oxy] -1-thiooxamidate, N- (2-  Methylchlorophenyl) -N ′, N′-dimethylformamidine, tetrachlorothiophene, 1- (2,6- Difluorobenzoyl) -3- (4-chlorophenyl) urea, O, O-dimethyl-O- (p-nitrophenyl) phosphorothioate, O, O-diethyl-O- (p-nitrophenyl) phosphorothioate, O-ethyl-O (p-nitrophenyl) phenyl phosphonothioate, O, O-dimethyl-O- (3- methyl 4-nitrophenyl) phosphorothioate, O, O-diethyl-O- (2,4-dichlorophenyl) - phosphorothioate, O-ethyl-O- (2,4-dichlorophenyl) phenyl phosphonothioate, O, O-dimethyl-O- (2,4,5-trichlorophenyl) phosphorothioate, O-ethyl-O- (2,4,5- trichlorophenyl) ethyl phosphorothioate, O, O-dimethyl-O- (4-bromo-2,5-dichlorophenyl) phosphorothioate, O, O-dimethyl-O- (2,5-dichloro-4-iodophenyl) - phosphorothioate, O, O-dimethyl-O- (3-methyl-4-methylthiophenyl) phosphorothioate, O-ethyl-O- (3-methyl-4-methylthiophenyl) isopropylphosphoramidate, O, O-diethyl-O- (p-methylsulfinyl-phenyl) phosphorothioate, O-ethyl S-phenyl-ethyl-phosphonodithioate, O, O-diethyl- [2-chloro-1- (2,4-dichlorophenyl) vinyl] phosphate, O, O-dimethyl- [2-chloro-1- (2,4,5-trichlorophenyl)] vinyl phosphate, O, O-dimethyl-S- (1'-phenyl) ethyl acetate phosphorodithioate, Bis (dimethylamino) fluorophosphine oxide, octamethyl pyrophosphoramide, O, O, O, O-tetraethyldithio-pyrophosphate, S-chloromethyl-O, O-diethyl- phosphorodithioate, O-ethyl-S, S-dipropyl-phosphorodithioate, O, O-dimethyl-O- 2,2-dichlorovinyl phosphate, O, O-dimethyl-1,2-dibromo-2,2-dichloroethyl phosphate, O, O-dimethyl-2,2,2-trichloro-1-hydroxyethylphosphonate, O, O-Di methyl S- [1,2-biscarbethoxy-ethyl- (1)] phosphorodithioate, O, O-dimethyl-O- (1-methyl-2-carbmethoxy-vinyl) phosphate, O, O-dimethyl-S- (N-methyl-carbamoyl-methyl) -phosphorodithioate, O, O-dimethyl-S- (N-methylcarbamoyl- methyl) phosphorothioate, O, O-dimethyl-S- (N-methoxyethyl-carbamoylmethyl) - phosphorodithioate, O, O-dimethyl-S- (N-formyl-N-methyl-carbamoyl-methyl) - phosphorodithioate, O, O-dimethyl-O- (1-methyl-2- (methyl-carbamoyl) vinyl] phosphate, O, O-dimethyl-O - [(1-methyl-2-dimethylcarbamoyl) vinyl] phosphate, O, O-dimethyl-O - [(1-methyl-2-chloro-2-diethylcarbamoyl) vinyl] phosphate, O, O-dimethyl-S- (ethyltiomethyl) phosphorodithioate, O, O-diethyl-S- [(p-chlorophenylthio) methyl] phosphorodithioate, O, O-dimethyl-S- (2-ethylthioethyl) phosphorothioate, O, O-dimethyl-S- (2-ethylthioethyl) phosphorodithioate, O, O-dimethyl-S- (2-ethylsulfinyl-ethyl) phosphorothioate, O, O-diethyl-S- (2-ethylthio-ethyl) phosphorodithioate, O, O-diethyl-S- (2-ethylsulfinyl-ethyl) phosphorothioate, O, O-diethyl-thiophosphoryliminophenyl) acetonitrile, O, O-diethyl-S- (2-chloro-1-phthalimidoethyl) phosphorodithioate, O, O-Diethyl-S- [6-chloro-benzoxazolon- (2) -yl (3)] - methyldithiophosphate, - O, O-dimethyl-S- [2-methoxy-1,3,4-thiadiazole-5- [4H] -onyl- (4) -methyl] -p-phosphorodithioate, O, O-diethyl-O- [3,5,6-trichloropyridyl- (2)] - phosphorothioate, O, O- Diethyl-O- (2-pyrazinyl) phosphorotioate, O, O-diethyl-O- [2-isopropyl-4- methyl pyrimidinyl (6)] - phosphorothioate, O, O-diethyl-O- [2- (diethylamino) - 6-methyl-4-pyrimidinyl] thionophosphate, O, O-dimethyl-S- (4-oxo-1,2,3-benzotriazine-3- [4H] -yl-methyl) -phosphord-ithioate, O, O-dimethyl-S - [(4,6-diamino-1,3,5-triazin-2-yl) methyl] phosphorodithioate, O, O-diethyl- (1-  phenyl-1,2,4-triazol-3-yl) thionophosphate, O, S-dimethyl-phosphorus amidothioate, O, S-dimethyl-N-acetyl-phosphoramidothioate, alpha-hexachlorocyclohexane, 1,1-di- (p-methoxyphenyl) -2,2,2-trichloroethane, 6,7,8,9,10,10-hexachlo-ro- 1,5,5a, 6,9,9a-hexahydro-6,9-methano-2,4,3-benzodioxa-thiepin-3- oxide, pyrethrins, DL-2-allyl-3-methyl-cyclopenten- (2) -one- (1) -yl- (4) -DL- cis, -trans-chrysanthemate, 5-benzyl-furyl- (3) -methyl-DL-cis, -trans-chrysanthemum, 3-phenoxybenzyl (±) -cis, -trans-2,2-dimethyl-3- (2,2-dichlorovinyl) -cycl-opropan carboxylate, alpha-cyano-3-phenoxybenzyl (±) -cis, -trans- 2,2-dimethyl-3- (2,2-dichlorovinyl) cyclopropanecarboxylate, (s) -alpha- Cyano-3-phenoxybenzyl-cis (1R, 3R) -2,2-dimethyl-3- (2,2-dibromovinyl) -cy-clopropanecarboxylate, 3,4,5,6-tetrahydrophthalimidoethyl-DL-cis, -trans-chrysanthemate, 2-methyl-5- (2-propynyl) -3-furylmethyl chrysanthemate, (alpha- Cyano-3-phenoxybenzyl) alpha-isopropyl-4-chlorophenylacetate.

In the following application examples, the the following known active ingredients:

Comparative agent I (diflubenzuron):

Comparative means II (Teflubenzuron):

Comparative means III (Example 20 from EP 1 01 990):

Musca domestica (houseflies), chemosterilization

Approx. 100 hatchable house fly dolls are placed in plastic containers set with 8.5 l volume. You will receive 2 g of feed consisting of

6 parts granulated sugar 6 parts dry milk 1 part ice powder

to which 20 mg of the active ingredient was added in organic solution (= 1%). The solvent was removed again.

Sufficient water is added to pulp in 100 ml Plastic cups offered. The animals stay in these cages for about 8 days at 22 ° C and day and night rhythm.

On the 8th day, you put an ice tray with skimmed milk Pulp in the cages. This will take place within the next 24 hours the ice shelf.

When setting the ice storage containers, the feeding poison effect is based on the dead flies judged.

After 3 to 4 days, the development of the eggs on the cotton wool judged.

Tineola bisselliella (clothes moth), attempted breeding

The tests were carried out on 3.2 g of a woolen fabric (10 × 20 cm).

At the beginning of the test, the wool fabric is treated with the acetone Active ingredient solution, 3.2 ml must be added dropwise.

Then you dust some clothes moth breeding food on the wool fabric and add 30 mg of moth eggs. The fabric is now rolled up and in kept in a closed 1 liter mason jar. The feeding activity of the larvae can be determined after approx. 8 weeks. After another 14 days the moths begin to hatch.

Test temperature 22 to 24 ° C.

Blatta orientalis (cockroach), breeding attempt

The test is carried out in 1 liter glasses on 50 cockroaches in the 1st larval stage. A Frame made of 5 horizontal cardboard discs (6 × 6 cm) offers the animals Hiding places.

The active ingredient is absorbed through the feed. This consists of 20 g cold-mixed carrot porridge in petri dishes (⌀ 5 cm). In addition receive water on cellulose in plastic cups (content 25 ml). The Observation time extends over two molting phases - 3 weeks. Here must be replenished weekly with freshly prepared porridge.

The assessment takes place weekly.

Tetranchus telarius (spider mite), experiments with counted switches

Potted bush beans are in the spray booth on the turntable with the aqueous preparation of active ingredients sprayed to runoff. After drying you punch out pieces of sheet with a diameter of 25 mm with a cork drill Spread. They are placed on pieces of pulp, which are in on the sides Hanging water.

The sheet punches are each occupied with 10 adult females. After 5 and The evaluation is carried out for 10 days, counting eggs, larvae and adults will.

Agrotis ypsilon (caterpillar), inhibition of development (Test on treated medium)

100 g of the standard nutrient medium for Agrotis are filled in 250 ml beakers and carefully mixed warm with the aqueous active ingredient preparation.

After cooling, each container is covered with 10 L3 beads (1.5 to 1.8 cm) and store it at 23 ° C. Pupation and hatching of the moths are assessed.

At least 2 cups must be prepared per concentration.

Aedes aegypti (yellow fever mosquito), attempted breeding

200 ml of tap water in a 250 ml plastic cup are mixed with the Active ingredient preparation mixed and then with 20 to 30 mosquito larvae in the 3rd to 4th larval stage occupied.  

The vessels are at 25 ° C. Pupation and hatching are observed Imagines, which takes place after 10 to 12 days.

During the observation period, use powdered tetramine once fed.

Claims (7)

1. N-benzoyl-N'-3,5-dichloro-2-fluoro-4- (3-trifluoromethyl) phenoxyphenylureas, of the formula I. in which means: R¹Fluor, chlorine, bromine, R²Fluor, chlorine or hydrogen. 2. A process for the preparation of N-benzoyl-N'-3,5-dichloro-2-fluoro-4- (3-trifluoromethyl) phenoxyphenylureas (I) according to claim 1, characterized in that a corresponding 3,5-dichloro -2-fluoro-4- (3-trifluoromethyl) phenoxyphenylamine II with a corresponding benzoyl isocyanate of the formula III implements. 3. A process for the preparation of N-benzoyl-N'-3,5-dichloro-2-fluoro-4- (3-trifluoromethyl) phenoxyphenylureas (I) according to claim 1, characterized in that a corresponding benzamide IV with a corresponding isocyanate V implement. 4. pesticides containing an active ingredient of the formula I. according to claim 1. 5. Pesticides containing a solid or liquid Carrier and / or at least one further active ingredient and one Active ingredient of formula I according to claim 1. 6. Use of the N-benzoyl-N'-3,5-dichloro-2-fluoro-4- (3-trifluoromethyl) - phenoxyphenylureas of the formula I according to claim 1 or agents according to claim 4 or 5 for controlling pests, in particular Insects and acarids. 7. Methods for controlling pests, especially insects and Acarids, characterized in that an effective amount of a N-Benzoyl-N'-3,5-dichloro-2-fluoro-4- (3-trifluoromethyl) phenoxyphenylurea of formula I according to claim 1 on pests and / or whose habitat has an impact.