CH685090A5 - A method for controlling insects. - Google Patents

Description

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description

The invention relates to a method for controlling certain insects from the order Ho-moptera or from the order Lepidoptera, as claimed in claims 1 to 10, in which compounds of the formula

Ocv

- r \

(D,

where R is ethyl or propyl, corresponding insecticides, the active ingredient of which is selected from the compounds mentioned, as claimed in claim 11, a process for the preparation of these agents as claimed in claim 12, the use of these agents as in claim 14 claimed in the above-mentioned method for controlling insects and the use of the mentioned compounds as claimed in claim 13 for the preparation of these agents, the proviso being that (2R, 4S) -2-ethyl-4- (4-phenoxy) phenoxymethyl-1,3-dioxolane in completely enantiomerically pure form and in essentially enantiomerically pure form is excluded from the scope of all objects according to the invention.

In the context of the present invention, the above-mentioned (2R, 4S) enantiomer is then “in essentially enantiomerically pure form” and thus this enantiomer falls under the above-mentioned requirement, inter alia, if its proportion in a mixture of compounds of the formula I is at least 90%, based on the total number of molecules contained in this mixture.

In US 4,097,581 compounds of the formula

(n),

wherein Ri is hydrogen, Ci-C7-alkyl, C3-C6-cycloalkyl, C2-C3-alkenyl, C2-C3-alkynyl, C2-C4-methoxyalkyl, chloromethyl or benzyl and R2 is hydrogen or Ci-C6-aikyl or

Ri and R2 together form the group - (CH2) n-, where n is 4 or 5, or together with the carbon atom to which they are attached, the group of the formula ch3

) Ö (m)

CH (CH3) 2

mean as active ingredients in agents for promoting fruit abscess as well as active ingredients in pesticides, e.g. Insecticides proposed.

Compounds II are generally assigned activity against a large number of families of the insects, an analysis of these numerous families of insects listed in US Pat. No. 4,097,581 showing that these families in turn can be assigned to a large number of orders of the insects. Among other things, compounds Ii in US 4,097,581 are also said to have activity against insects from the nine families Aphididae, Delphacidae, Diaspididae, Pseudococcidae, Tineidae, Noctuidae, Lymantriidae, Pyraiidae and Galleriidae. Of these nine families, the first four belong to the Homoptera order and the others belong to the Lepidoptera order, but these two orders are not mentioned anywhere in US Pat. No. 4,097,581. An effectiveness of compounds I! against others, i.e. from the four families mentioned above, families from the order Homoptera are just as little disclosed in US 4,097,581 as an activity of compounds II against others, i.e. different from the five families mentioned above, families from the order Lepidoptera.

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In US 4,097,581 the activity of compounds II against insects of the nine families mentioned from the two orders Homoptera and Lepidoptera is only shown on a single representative of the family Pyralidae, which belongs to the order Lepidoptera, namely in (biological ) Example 5, which discloses the action of compounds II against the species Ephestia kuehniella. An activity of compounds II against even a single further member from the order Lepidoptera is, however, not shown in US 4,097,581. Rather, any genera from the order Lepidoptera and any other species from the order Lepidoptera are not even mentioned in US 4,097,581. Also in no way shown in US 4,097,581 is an activity of compounds II against even a single member of the order Homoptera. Rather, any genus from the Homoptera order and any species from the Homoptera order are not even mentioned in US 4,097,581. In contrast, however, US 4 097 581 uses nine further biological examples to demonstrate the activity of compounds II against a number of representatives from other families of insects which in turn belong to the Diptera, Heteroptera and Coleoptera orders. Six of these other biological examples relate to representatives from the Coleoptera order.

The user in the field of insect control, who evaluates compounds II for their potential application, will undoubtedly determine on the basis of the distribution of the 10 biological examples disclosed in US 4,097,581, which show the insecticidal activity of compounds II, on the individual orders of the insects that the only real focus of the insecticidal biological activity of the compounds II, which is disclosed in US Pat. No. 4,097,581, is clearly on their activity against representatives from families of insects from the order Coleoptera, since 6 of the 10 relevant biological examples are the combating of representatives from precisely this Order Coleoptera. When evaluating the compounds II on the basis of US Pat. No. 4,097,581, the user mentioned will undoubtedly also find that a second, but only comparatively vague, focus of the insect-killing biological action of the compounds II is based on their activity against representatives from families of insects of the Diptera order, since 2 of the 10 relevant biological examples still deal with the fight against representatives of the Diptera order. In the event of further evaluation of the compounds II, the user mentioned will finally undoubtedly also find that US 4,097,581 does not disclose any further focal points of the insect-killing biological action of the compounds II, since the remaining two relevant biological examples are uniform, i.e. with just one example each, distribute the effectiveness of compounds Ii against representatives of families of insects from the two orders Hemiptera and Lepidoptera.

Based on the disclosure of US 4,097,581, the user mentioned will therefore classify the compounds II as being primarily suitable for combating families of insects from the order Coleoptera and the compounds II - possibly - also for combating families of insects from the order Diptera will be shortlisted, however, the user will consider compounds II, if at all, at most marginally for the control of representatives of the five families of insects from the order Lepidoptera, which are listed in US Pat. No. 4,097,581 . For the control of representatives of families of insects from the order Homoptera, for which any biological example is missing in US Pat. No. 4,097,581, compounds II are virtually out of the question for the user mentioned in the light of the disclosure of US Pat. No. 4,097,581.

Unexpectedly and, in view of the disclosure of US Pat. No. 4,097,581 explained above, it has now been found that, in reality, the compounds I are in fact outstandingly suitable for controlling insects of certain families and genera from the Homoptera order and certain families from the Lepidoptera order , namely for the control of insects belonging to the order Homoptera, families Aleyrodidae, Cicadellidae, Coccidae, Marga-rodidae and Psyllidae, of insects of the genera Aonidiella, Aspidiotus, Aulacaspis, Chrysomphalus, Lepidosaphes, Parlatoria, Quadseudraspaspidis, from the family Diaspididae belonging to the order Homoptera, from insects of the genus Planococcus from the family Pseudococcidae belonging to the order Homoptera and from insects belonging to the order Lepidoptera, families Gracilariidae, Lyonetiidae, Olethreutidae, Psychidae and Tor-tricidae.

This excellent suitability of the compounds I for the control of insects of certain families and genera from the order Homoptera and certain families from the order Lepidoptera is so surprising because the compounds I fall under the scope of the compounds II disclosed by US 4,097,581 and, in the form of mixtures of diastereomers, even specifically in US 4,097,581 in the table in columns 9 and 10. However, in US 4,097,581, as stated above, there is no indication of the excellent activity according to the present invention, either with regard to the compounds II according to US 4,097,581, and certainly not with regard to the present compounds I, which as a special subgroup of the compounds II can be viewed, but which is not disclosed in US 4,097,581.

The control of insects of the type mentioned according to the invention is of great importance for the user in the field of insect control, since without their targeted control

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from these insects e.g. large economic losses, e.g. due to the damage caused by these insects to agricultural products.

In the context of the present invention, preference is given, on the one hand, to a process for controlling insects of the type according to the invention, in which compounds of the formula I in which R is ethyl are used.

On the other hand, a method for controlling is preferred within the scope of the present invention

(1) from insects of the Coccidae family, in particular the genera Ceroplastes, Pulvinaria and Saissetia, preferably the species Ceroplastes floridensis, Ceroplastes sinensis, Pulvinaria psidii and Sais-setia olea, in particular the species Ceroplastes floridensis, Ceroplastes sinensis and Saissetia oiea;

(2) from insects of the genera Aonidiella, Lepidosaphes, Parlatoria, Chrysomphalus, Aulacaspis, Aspidiotus, Selenaspidus, Pseudaulacaspis, Quadraspidiotus and Unaspis, preferably of the species Aonidiella aurantii, Lepidosaphes beckii, Lepidoslipidia, paris , Aulacaspis tubercularis, Aspidiotus hederae, Selenaspidus ar-ticulatus, Pseudaulacaspis pentagona, Quadraspidiotus perniciosus, Unaspis citri and Unaspis yanonenisis, in particular of the species Aonidiella auranti, Lepidosaphes becki, Pei from the family Diaspididae;

(3) from insects of the Margarodidae family, in particular of the genus Icerya, preferably of the species Icerya purchasi;

(4) from insects of the genus Planococcus from the family Pseudococcidae, the genus Psylla from the family Psyllidae and the genera Trialeurodes and Bemisia from the family Aleyrodidae, preferably of the species Planococcus ficus, Planococcus citri, Psylla pyri, Psylla pyricola-umeuros vaporarium and Bemisia tabaci, in particular of the species Psylla pyricola;

(5) from insects of the Olethreutidae family, in particular of the genera Cydia and Laspeyresia, preferably of the species Cydia pomonella, Laspeyresia molesta and Laspeyresia funebrana, in particular of the species Laspeyresia molesta;

(6) by insects of the Tortricidae family, in particular the genera Adoxophyes, Pandemis, Cacoecia and Eulia, preferably the species Adoxophyes reticulana, Pandemis heparana, Cacoecia costa-na, Cacoecia pronubana and Eulia sphaleropa, in particular the species Adoxophyes reticularana and Pandemisecepana pronubana;

(7) from insects of the Lyonetiidae family, in particular of the genera Leucoptera and Lyonetia, preferably of the species Leucoptera scitella and Lyonetia clerkella, in particular of the species Leucoptera scitella;

(8) from insects of the Gracilariidae family, in particular the genus Lithocolletis; preferred of the species Lithocolletis blancardella and Lithocolletis corylifoliella, in particular of the species Lithocolletis biancardel-la.

The compounds of formula I used according to the invention are known and e.g. in US 4,097,581.

In the field of insect control, the compounds I used according to the invention are beneficial and / or curatively valuable active ingredients, even at low application concentrations, with good warm-blood, fish and plant tolerance. The active substances used according to the invention are active against all or individual stages of development of normally sensitive, but also of resistant, animal insects of the type mentioned. The insecticidal activity of the active compounds used according to the invention can be direct, i.e. in killing the insects, which occurs immediately or only after some time, for example when molting, or indirectly, e.g. in a reduced egg deposition and / or hatching rate, the good effect corresponding to a mortality rate of at least 50 to 60%.

With the active ingredients used according to the invention, pests of such plants can be found in particular on plants, especially on useful and ornamental plants in agriculture, horticulture and in the forest, or on parts such as fruits, flowers, foliage, stems, bulbs or roots combat the type mentioned, ie contain or destroy, parts of the plant that later grow are still protected against these pests.

In particular crops of pome fruit, e.g. Apples or pears, stone fruit, e.g. Peaches, citrus, e.g. Lemons, oranges or grapefruits, vegetables, e.g. Potatoes, beans, tomatoes or cucumbers, pepper, olives, mango, wine, ornamental plants, nuts, guava, tea or avocado, especially from pome fruit, stone fruit, citrus fruits, vegetables, olives, mango, wine, ornamental plants and nuts, preferably from pome fruit , Stone fruit and citrus.

Further areas of application of the active compounds used according to the invention are the protection of stocks and stocks and of material, and in the hygiene sector in particular the protection of domestic and farm animals from pests of the type mentioned.

The invention therefore also relates to insecticides for use against pests of the type mentioned, such as emulsifiable concentrates, suspension concentrates to be selected depending on the desired objectives and given conditions, directly sprayable or dilutable solutions, spreadable pastes, diluted emulsions, wettable powders, soluble powders , dispersible powders, wettable powders, dusts, granules or encapsulations in polymeric substances which - at least - one of the active ingredients used according to the invention and - at least - one of the formulation tech

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conventional auxiliaries, such as extenders, e.g. Contain solvents or solid carriers, or such as surface-active compounds (surfactants).

As a solvent e.g. Suitable are: optionally partially hydrogenated aromatic hydrocarbons, preferably the fractions Cs to C12 of alkylbenzenes, such as xylene mixtures, alkylated naphthalenes or tetrahydronaphthalene, aliphatic or cycloaliphatic hydrocarbons, such as paraffins or cyclohexane, alcohols, such as ethanol, propanol or butanol, glycols and their ethers and esters such as propylene glycol, dipropylene glycol ether, ethylene glycol or ethylene glycol monomethyl or ethyl ether, ketones such as cyclohexanone, isophorone or diacetone alcohol, strongly polar solvents such as N-methylpyrrolid-2-one, dimethyl sulfoxide or N, N-dimethylformamide, Water, optionally epoxidized vegetable oils, such as optionally epoxidized rapeseed, castor, coconut or soybean oil, and silicone oils.

As solid carriers, e.g. natural dust, such as calcite, talc, kaolin, montmorillonite or attapulgite, is generally used for dusts and dispersible powders. To improve the physical properties, highly disperse silicas or highly disperse absorbent polymers can also be added. Porous types such as pumice, broken brick, sepiolite or bentonite are suitable as granular, adsorptive granulate carriers, and calcite or sand are suitable as non-sorptive carrier materials. In addition, a large number of granulated materials of inorganic or organic nature, in particular dolomite or comminuted plant residues, can be used.

Depending on the nature of the active ingredient to be formulated, suitable surface-active compounds are nonionic, cationic and / or anionic surfactants or surfactant mixtures with good emulsifying, dispersing and wetting properties. The surfactants listed below are only examples; the relevant literature describes many other surfactants which are customary in formulation technology and are suitable according to the invention.

Suitable nonionic surfactants are primarily polyglycol ether derivatives of aliphatic or cycloaliphatic alcohols, saturated or unsaturated fatty acids and alkylphenols, which contain 3 to 30 glycol ether groups and 8 to 20 carbon atoms in the (aliphatic) hydrocarbon radical and 6 to 18 carbon atoms in the alkyl radical of the alkylphenols can. Also suitable are water-soluble, 20 to 250 ethylene glycol ether and 10 to 100 propylene glycol ether groups containing polyethylene oxide adducts with polypropylene glycol, ethylenediaminopolypropylene glycol and alkylpolypropylene glycol with 1 to 10 carbon atoms in the alkyl chain. The compounds mentioned usually contain 1 to 5 ethylene glycol units per propylene glycol unit. Examples include nonylphenol polyethoxyethanols, castor oil polyglycol ether; Poiypropylene-polyethylene oxide adducts, tributylphenoxypolyethoxyethanol, polyethylene glycol and octylphenoxypolyethoxyethanol mentioned. Fatty acid esters of polyoxyethylene sorbitan, such as polyoxyethylene sorbitan trioleate, are also suitable.

The cationic surfactants are primarily quaternary ammonium salts which have at least one alkyl radical having 8 to 22 carbon atoms as substituents and low, optionally halogenated, alkyl, benzyl or lower hydroxyalkyl radicals as further substituents. The salts are preferably in the form of halides, methyl sulfates or ethyl sulfates. Examples are the stearyl trimethyl ammonium chloride and the benzyl di (2-chloroethyl) ethyl ammonium bromide.

Suitable anionic surfactants can be both water-soluble soaps and water-soluble synthetic surface-active compounds. Suitable soaps are the alkali metal, alkaline earth metal and optionally substituted ammonium salts of higher fatty acids (C10-C22), such as the sodium or potassium salts of oleic or stearic acid, or of natural fatty acid mixtures, for example from coconut or Tall oil can be extracted; the fatty acid methyl taurine salts should also be mentioned. However, synthetic surfactants are used more frequently, in particular fatty sulfonates, fatty sulfates, sulfonated benzimidazole derivatives or alkylarylsulfonates. The fatty sulfonates and sulfates are generally present as alkali, alkaline earth or optionally substituted ammonium salts and generally have an alkyl radical having 8 to 22 carbon atoms, alkyl also including the alkyl part of acyl radicals; Examples include the sodium or calcium salt of lignosulfonic acid, do-decylsulfuric acid ester or a fatty alcohol sulfate mixture made from natural fatty acids. This subheading also includes the salts of sulfuric acid esters and sulphonic acids from fatty alcohol-ethylene oxide adducts. The sulfonated benzimidazole derivatives preferably contain 2 sulfonic acid groups and a fatty acid residue with about 8 to 22 carbon atoms. Examples of alkylarylsulfonates are the sodium, calcium or triethanolammonium salts of dodecylbenzenesulfonic acid, dibutylnaphthalenesulfonic acid or a naphthalenesulfonic acid / formaldehyde condensation product. Corresponding phosphates, such as salts of the phosphoric acid ester of a p-nonylphenol (4-14) ethylene oxide adduct or phospholipids, are also suitable.

The agents generally contain 0.1 to 99%, in particular 0.1 to 95%, active ingredient and 1 to 99.9%, in particular 5 to 99.9%, - at least - of a solid or liquid auxiliary, in which Rule 0 to 25%, in particular 0.1 to 20%, of the agent can be surfactants (% means weight percent in each case). While concentrated agents are preferred as a commercial product, the end user generally uses diluted agents which have significantly lower active substance concentrations. Preferred agents are composed in particular as follows (% = weight percent);

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Emulsifiable concentrates:

Active substance:

Surfactant:

Solvent:

1 to 90%, 1 to 30%, 5 to 98%,

preferably preferably preferably

5 to 20% 10 to 20% 70 to 85%

Dusts:

Active substance:

solid carrier:

0.1 to 10%, 99.9 to 90%,

preferably preferably

0.1 to 1% 99.9 to 99%

Suspension concentrates:

Active substance:

Water:

Surfactant:

5 to 75%, 94 to 24%, 1 to 40%,

preferably preferably preferably

10 to 50% 88 to 30% 2 to 30%

Wettable powders:

Active substance:

Surfactant:

solid carrier:

0.5 to 90%, 0.5 to 20%, 5 to 99%,

preferably preferably preferably

1 to 80% 1 to 15% 15 to 98%

Granules:

Active substance:

solid carrier:

0.5 to 30%, 99.5 to 70%,

preferably preferably

3 to 15% 97 to 85%

The action of the agents according to the invention can be broadened considerably by adding other insecticidal active ingredients and adapted to the given circumstances. The active ingredient additives are e.g. Representatives of the following classes of active substance are considered: organic phosphorus compounds, nitrophenols and derivatives, formamidines, ureas, carbamates, pyrethroids, chlorinated hydrocarbons and Bacillus thuringiensis preparations. The agents according to the invention can also contain other solid or liquid auxiliaries, such as stabilizers, e.g. optionally epoxidized vegetable oils (e.g. epoxidized coconut oil, rapeseed oil or soybean oil), defoamers, e.g. Silicone oil, preservatives, viscosity regulators, binders and / or adhesives, as well as fertilizers or other active ingredients to achieve special effects, e.g. Bactericides, fungicides, nematicides, molluscicides or selective herbicides.

The agents according to the invention are produced in a known manner, e.g. by intimately mixing and / or grinding the active ingredient or mixture of active ingredients with the auxiliary (s). These processes for the preparation of the compositions according to the invention and the use of the compounds I for the production of these compositions likewise form a subject of the invention.

The application methods for the agents, i.e. the methods for controlling pests of the type mentioned, such as, depending on the desired objectives and given circumstances, to be selected, spraying, atomizing, dusting, brushing, pickling, scattering or pouring, and the use of the agents for controlling pests of the type mentioned are further objects of the invention. Typical application concentrations are between 0.1 and 1000 ppm, preferably between 0.1 and 500 ppm, of active ingredient. In particular, spray liquors with active ingredient concentrations of 50, 100, 150 or 200 ppm are used. The application rates per hectare are generally 1 to 2000 g of active ingredient per hectare, in particular 10 to 1000 g / ha, preferably 20 to 600 g / ha. Application rates of 300, 400 or 450 g of active ingredient per hectare are preferred. Application rates of 0.25, 0.75, 1.0 or 2.0 g of active ingredient per tree are preferred.

A preferred application method in the field of crop protection is application to the foliage of the plants (foliar application), the frequency of application and application rate being able to be adjusted to the infestation pressure of the respective pest. The active ingredient can also get into the plants through the root system (systemic effect) by soaking the location of the plants with a liquid agent or the active ingredient in solid form in the location of the plants, e.g. in the ground, e.g. in the form of granules (floor application).

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The following examples serve to illustrate the invention. They do not limit the invention. Temperatures are given in degrees Celsius.

Formulation examples (% = weight percent)

Example F1: Emulsion concentrates a)

b)

c)

Active ingredient

25%

40%

50%

Ca dodecylbenzenesulfonate

5%

8th%

6%

Castor oil polyethylene glycol ether (36 mol EO)

5%

-

-

Tributylphenol polyethylene glycol ether (30 mol EO)

-

12%

4%

Cyclohexanone

-

15%

20%

Xylene mixture

65%

25%

20%

Emulsions of any desired concentration can be prepared from such concentrates by dilution with water.

Example F2: Solutions a

b)

c)

d)

Active ingredient

80%

10%

5%

95%

Ethylene glycol monomethyl ether

20%

-

-

-

Polyethylene glycol MG 400

-

70%

-

-

N-methyl-2-pyrrolidone

-

20%

-

-

Epoxidized coconut oil

-

-

1%

5%

Petrol (boiling limits 160-190 °)

-

-

94%

-

Solutions are suitable for use in the form of tiny drops.

Example F3: Granules a)

b)

c)

d)

Active ingredient

5%

10%

8th%

21%

kaolin

94%

-

79%

54%

Fumed silica

1%

-

13%

7%

Attapulgite

-

90%

-

18%

The active ingredient is dissolved in dichloromethane, sprayed onto the carrier and the solvent is then evaporated off in vacuo.

Example F4: dusts a)

b)

Active ingredient

Fumed silica

talc

kaolin

2% 1% 97%

5% 5%

90%

tel.

Ready-to-use dust particles are obtained by intimately mixing the carrier substances with the active ingredient.

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Example F5: wettable powder a) b) c)

Active ingredient

25%

50%

75%

Na lignin sulfonate

5%

5%

-

Na lauryl sulfate

3%

-

5%

Na diisobutylnaphthalenesulfonate

-

6%

10%

Octylphenol polyethylene glycol ether (7-8 mol EO)

-

2%

-

Fumed silica

5%

10%

10%

kaolin

62%

27%

-

The active ingredient is mixed with the additives and ground well in a suitable grinder. Spray powder is obtained which can be diluted with water to form suspensions of any desired concentration.

Example F6: Emulsion concentrate

Active ingredient 10%

Octylphenol polyethylene glycol ether (4-5 mol EO) 3%

Ca-dodecylbenzenesulfonate 3%

Castor oil polyglycol ether (36 mol EO) 4%

Cyclohexanone 30%

Xylene mixture 50%

Emulsions of any desired concentration can be prepared from this concentrate by dilution with water.

Example F7: dusts a)

b)

Active ingredient

5%

8th%

talc

95%

-

kaolin

-

92%

Ready-to-use dusts are obtained by mixing the active ingredient with the carrier and grinding it in a suitable mill.

Example F8: Extruder granules

Active ingredient 10%

Na lignin sulfonate 2%

Carboxymethyl cellulose 1%

Kaolin 87%

The active ingredient is mixed with the additives, ground and moistened with water. This mixture is extruded, granulated and then dried in a stream of air.

Example F9: coated granules

Active ingredient 3%

Polyethylene glycol (MG 200) 3%

Kaolin 94%

The finely ground active ingredient is applied evenly in a mixer to the kaolin moistened with polyethylene glycol. In this way, dust-free coating granules are obtained.

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Example F10: Suspension concentrate

Active ingredient ethylene glycol

Nonylphenol polyethylene glycol ether (15 mol EO)

Na lignin sulfonate

Carboxymethyl cellulose

37% aqueous formaldehyde solution

Silicone oil in the form of a 75% aqueous emulsion

water

40%

10%

6%

10%

1%

0.2%

0.8%

32%

The finely ground active ingredient is intimately mixed with the additives. This gives a suspension concentrate from which suspensions of any desired concentration can be prepared by dilution with water.

Biological examples

(% = Weight percent, unless otherwise stated)

Example B1:

Effect against Adoxophyes reticulana (ovizidi

Eggs from Adoxophyes reticulana deposited on filter paper are briefly immersed in an acetone-aqueous test solution containing 400 ppm of active ingredient. After the test solution has dried on, the eggs are incubated in petri dishes. After 6 days, the percentage hatching of the eggs is evaluated compared to untreated control batches (% hatching reduction). Compounds of the formula I show good activity in this test. In particular, the compound of formula I, wherein R is ethyl, shows an activity of more than 80%.

Example B2:

Effect against Aonidiella aurantii

Potato tubers are populated with Aonidiella aurantii migrating larvae (“crawlers”). After about 2 weeks, the potatoes are immersed in an aqueous emulsion or suspension spray liquor which contains 400 ppm of active ingredient. After the tubers have dried, they are incubated in a plastic container. For evaluation, the survival rate of the migrating larvae of the first subsequent generation of the treated population is compared with that of untreated control batches 10 to 12 weeks later. Compounds of the formula I show good activity in this test. In particular, the compound of formula I, wherein R is ethyl, shows an activity of more than 80%.

Example B3

Effect against Aonidiella aurantii

Citrus trifoliata cuttings are colonized with Aonidiella aurantii migrating larvae. After about 2 weeks, the cuttings are sprayed to runoff point with an aqueous emulsion spray mixture which contains 50 ppm of active ingredient. For evaluation, the survival rate of the migrating larvae of the first subsequent generation of the treated population is compared with that of untreated control batches 10 to 12 weeks later. Compounds of the formula I show good activity in this test. In particular, the compound of formula I, wherein R is ethyl, shows an activity of more than 80%.

Example B4

Effect geoen Bemisia tabaci

Bush bean plants are placed in gauze cages and populated with Bemisia tabaci adults. After the eggs have been laid, all adults are removed. 10 days later, the plants with the nymphs on them are sprayed with an aqueous emulsion spray mixture which contains 400 ppm of active ingredient. After a further 14 days, the percentage hatching of the eggs is evaluated in comparison to untreated control batches. Compounds of the formula I show good activity in this test. In particular, the compound of formula I, wherein R is ethyl, shows an activity of more than 80%.

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Example B5

Effect against Bemisia tabaci

Bush bean plants are placed in gauze cages and populated with Bemisia tabaci adults. After the eggs have been laid, all adults are removed. 2 days later, the plants with the nymphs on them are sprayed with an aqueous emulsion spray mixture which contains 400 ppm of active ingredient. After a further 10 days, the percentage hatching of the eggs is evaluated in comparison to untreated control batches. Compounds of the formula I show good activity in this test. In particular, the compound of formula I, wherein R is ethyl, shows an activity of more than 80%.

Example B6

Effect against Cvdia pomonella fovizid)

Eggs of Cydia pomonella deposited on filter paper are briefly immersed in an acetone-aqueous test solution containing 400 ppm of active ingredient. After the test solution has dried on, the eggs are incubated in petri dishes. After 6 days, the percentage hatching of the eggs is evaluated compared to untreated control batches (% hatching reduction). Compounds of the formula I show good activity in this test. In particular, the compound of formula I, wherein R is ethyl, shows an activity of more than 80%.

Claims (14)

Claims 1. Method for controlling insects belonging to the order Homoptera, families Aleyrodidae, Cicadellidae, Coccidae, Margarodidae and Psyllidae, of insects of the genera Aonidiella, Aspidiotus, Aulacaspis, Chrysomphalus, Lepidosaphes, Parlatoria, Pseudaulididiotaspus, Selraspaspaspas, Quadr , belonging to the order Homoptera, family Diaspididae, from insects of the genus Planococcus from the, belonging to the order Homoptera, family Pseu-dococcidae and from insects belonging to the order Lepidoptera, families Gracilariidae, Lyo-netiidae, Olethreutidae, Psychidae and Tortricida which an "insecticidal agent is applied to the insects or their habitat, characterized in that the agent contains at least one compound of the formula in which R is ethyl or propyl, as active ingredient and at least one auxiliary substance, the proviso that (2R, 4S ) -2-ethyl-4- (4-phenoxy) phenoxymethyl-1,3-dioxolane in complete e nantiomerically pure form and in essentially enantiomerically pure form is excluded from the scope of the active substances contained in the composition. 2. The method according to claim 1, characterized in that in the compound of formula I R is ethyl. 3. The method according to claim 1 for controlling insects from the Coccidae family, in particular the genera Ceroplastes, Pulvinaria and Saissetia, preferably the species Ceroplastes floridensis, Ceroplastes sinensis, Pulvinaria psidii and Saissetia olea, in particular the species Ceroplastes floridensis, Ceroplastes sinensis and Saissetia olea. 4. The method according to claim 1 for combating insects of the genera Aonidiella, Lepidosaphes, Parlatoria, Chrysomphalus, Aulacaspis, Aspidiotus, Selenaspidus, Pseudaulacaspis, Quadraspidiotus and Unaspis, preferably of the types Aonidiella aurantii, Lepidosaphes beckatoria, Perpidia, lepidia, Lepidia Parlatoria Ziziphi, Chrysomphalus aonidum, Aulacaspis tubercu-laris, hederae Aspidiotus, Selenaspidus articulatus, Pseudaulacaspis pentagona, Quadraspidiotus perniciosus, Unaspis citri and Unaspis yanonensis, particularly of the species Aonidiella aurantii, Lepidosaphes beckii, Parlatoria pergandei, Pseudaulacaspis pentagona, Quadraspidiotus perniciosus, Unaspis citri and Unaspis yanonensis, from the Diaspididae family. 5. The method according to claim 1 for controlling insects of the Margarodidae family, in particular the genus Icerya, preferably the species Icerya purchasi. 6. The method according to claim 1 for controlling insects of the genus Planococcus from the family Pseudococcidae, the genus Psy-Ila from the family Psyllidae and the genera Trialeurodes and Bemisia from the family Aleyrodidae, preferably of the species Planococcus ficus, Planococcus citri, Psylla pyri, Psylla pyricola, Trialeurodes vaporariorum and Bemisia tabaci, in particular of the species Psylla pyricola. (I), 10th 5 10th 15 20th 25th 30th 35 40 45 50 55 60 65 CH 685 090 A5 7. The method according to claim 1 for controlling insects of the family Olethreutidae, in particular the genera Cydia and Laspeyresia, preferably the species Cydia pomonella, Laspeyresia molesta and Laspeyresia funebrana, in particular the species Laspeyresia molesta. 8. The method according to claim 1 for controlling insects from the Tortricidae family, in particular the genera Adoxophyes, Pandemis, Cacoecia and Eulia, preferably the species Adoxophyes reticulana, Pandemis heparana, Cacoecia costana, Cacoecia pronubana and Eulia sphaleropa, in particular the species Adoxophyes reticulana, Pandemis heparana and Cacoecia pronubana. 9. The method according to claim 1 for controlling insects of the family Lyonetiidae, in particular the genera Leucoptera and Lyonetia, preferably the species Leucoptera scitella and Lyonetia clerkella, in particular the species Leucoptera scitella. 10. The method according to claim 1 for controlling insects of the Gracilariidae family, in particular the genus Lithocolletis; preferred of the species Lithocolletis blancardella and Lithocolletis corylifoliel-la, in particular of the species Lithocolletis blancardella. 11. Insect control agent for carrying out the method described in claims 1 to 10, characterized in that the agent contains at least one compound of the formula in which R is ethyl or propyl as an active ingredient and at least one auxiliary substance, the proviso that (2R, 4S ) -2-Ethyl-4- (4-phenoxy) phenoxymethyl-1,3-dioxolane in completely enantiomerically pure form and in essentially enantiomerically pure form is excluded from the scope of the active substances contained in the agent. 12. A process for the preparation of the agent described in claim 11, characterized in that the active ingredient is intimately mixed and / or ground with the auxiliary (s). 13. Use of a compound of the formula in which R is ethyl or propyl, with the proviso that the compound of the formula I is derived from (2R, 4S) -2-ethyl-4- (4-phenoxy) phenoxymethyl-1,3-dioxolane in completely enantiomerically pure form and in essentially enantiomerically pure form is different for the preparation of the agent described in claim 11. 14. Use of the agent described in claim 11 for performing the method described in claims 1 to 10. O (D O 11