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

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

in

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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.

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 .

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.

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.

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.

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

It has now surprisingly been found that the compounds of the invention have a better insecticidal effect compared to

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2 the closely related known compounds.

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.

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)

X

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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.

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.

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, etherifying the resulting 2-halo-6-tri-4

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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.

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.

They are primarily suitable for the control of pests on plants and animals.

The present invention therefore also relates to a pesticide peculiar to that of the characterizing part of claim 10.

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.

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.

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.

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.

In addition to a particularly beneficial effect against flies, such as

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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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.

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.

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).

As 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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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.

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.

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.

Suitable anionic surfactants can be both so-called water-soluble soaps and also water-soluble synthetic surfactants.

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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However, so-called synthetic surfactants are often used, especially fatty sulfonates, fatty sulfates, sulfonated benzimidazole derivatives or alkylarylsulfonates.

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.

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.

Examples of nonionic surfactants include nonylphenol polyethoxyethanols, castor oil polyglycol ethers, polypropylene

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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.

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.

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.

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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The invention is further illustrated in the following examples.

Example 1.

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).

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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Similarly, the following compounds of formula I are also prepared:

Compound 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 P

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

P P

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

Example 2.

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).

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).

In the same manner as described above, the following compounds of formula I are also prepared: 12

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Compound 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

Example 3

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)

Active substance or combination of active substances 25% 50% 75%

Sodium lignin sulfonate 5% 5% -

Sodium lauryl sulfate 3% - 5%

Sodium diisobutylnaphthalene sulfonate - 6% 10%

Ocylphenylpolyethylene glycol ether (7-8 moles of ethylene oxide) - 2% High-dispersion silicic acid 5% 10% 10%

Kaolin 62% 27% 13

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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.

A spray powder is obtained which can be diluted with water to suspend 5 pensions of any desired concentration.

2. Emulsion concentrate

Active substance or combination of active substances 10%

Octylphenol polyethylene glycol ether (4-5 moles of ethylene oxide) 3%

Calcium dodecylbenzenesulfonate 3%

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

Cyclohexanone 30% Xylene mixture 50%

From this concentrate, emulsions of any desired concentration can be prepared by dilution with water.

3. Powder preparation a) b)

Active substance or combination of 20 active substances 5% 8%

Talc 95%

Kaolin - 92%

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. Extruder granules

Active substance or combination of active substances 10%

Sodium lignin sulfonate 2% Carboxymethyl cellulose 1%

Kaolin 87%

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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. Wrapping granules 5 Active substance or combination of active substances 3%

Polyethylene Glycol (Molecular Weight 200) 3%

Kaolin 94%

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. Suspension concentrate

Active substance or combination of 15 active substances 40%

Ethylene glycol 10%

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

Sodium lignin sulfonate 10% Carboxymethyl cellulose 1% 37% aqueous formaldehyde solution 0.2%

Silicone oil in the form of a 75% aqueous emulsion 0.8%

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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Example 4

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 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 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.

Compounds of formula I according to Examples 1 and 2 exhibit good effect in the above test.

Example 5

Effect against Lucilia sericata

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.

The compounds of formula I according to Examples 1 and 2 show good effect against Lucilia sericata in this test.

Example 6

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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.

The compounds of formula I according to Examples 1 and 2 show good effect in this test.

Example 7

Insecticidal poison effect

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.

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.

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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Example 8.

Effect on Spodoptera littoralis and Heliothis virescens (larvae and eggs) _

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.

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.

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).

Compounds of formula I according to Examples 1 and 2 show good overall efficacy in this test.

Example 9

0Vidid effect on Spodoptera littoralis Eggs of Spodoptera littoralis laid on filter paper are excised 18

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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).

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%.

After 5 days, the hatching rate is determined, ie. the number of larvae that have evolved from the treated eggs.

Compounds of formula I according to Examples 1 and 2 show good effect in this test.

Example 10.

Ovicidal effect on Epilachna varivestis

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 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.

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.

Compounds of formula I according to Examples 1 and 2 show good effect in this test.

Example 11.

Ovicidal effect on Heliothis virescens and Leptinotarsa decemlineata_ 30 Corresponding amounts of moisturizing powder formulation containing 19

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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. .

In the emulsions containing the test compounds, 5 one day old eggs of Heliothis are immersed on "Cellophan" ® or eggs of

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.

Compounds of formula I according to Examples 1 and 2 show good effect in this test.

Example 12.

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.

Compounds of formula I according to Examples 1 and 2 show good effect in this test.

Example 13

Action 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 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).

Compounds Nos. 1, 2, 6 and 7 give the effect (mortality) of 80-100% in this test.

Example 14.

Effect against plant harmful acarides: Tetranychus urticae (OP-sensitive) and Tetranychus cinnabarinus (OP-tolerant)

The 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 tolerant). (Tolerance refers to compatibility with Diazinon).

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.

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 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.

Compounds of formula I according to Examples 1 and 2 in this experiment show good effect against Tetranychus urticae and Tetranychus cinnabarinus.

Example 15

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Influence of reproduction on Anthonomus grandis

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 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.

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.

Compounds of formula I according to Examples 1 and 2 show a good propagation-reducing effect in this test.

Claims (12)

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. 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. 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. Compound 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 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. Compound according to claim 6, characterized in that it has the formula T fr · * ... / COSHCONH - (γ-O-CF 2 CHFCF 1 i). Compound according to claim 6, characterized in that it has the formula • I ·· / CONHCONH - {y- O-CF2CHFCF3 Af3 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. 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. 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. Use according to claim 11 for the control of plant harmful insects of the order Acarina. 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.