DD149012A5 - SOIL INSECTICIDES MEDIUM - Google Patents

Abstract

The invention relates to agents against soil insects for use in horticulture and in agriculture and forestry. According to the invention, substituted cyclopropanecarboxylic acid esters of the formula I are used as active ingredient. In the formula: R CH & ind3 !, Cl, Br, F; X Cl, Br, J; Y is Cl or F and m and n are integers from 0 to 5, provided that m and n can not be 0 at the same time.

Description

215614-4-

Field of application of the invention

The present invention relates to the use of partially known Cyclopropancarbonsäureester ala soil insecticides.

Characteristic of the known technical solutions

It has already been disclosed in E3 that esters of 2,2-dimethyl- (3-substituted vinyl-1-cyclopropanecarboxylic acids with substituted benzyl alcohols have insecticidal properties (Peetic, Sci., 1975, pp. 537-542, Agr. Biol. Chem. Pp. 247-249 (1976), FR-PS 2 290 415, FR-PS 2 271 196, DE-OS 2 658 074).

Of the interesting pyrethroids that have been studied in detail, it has become known that they are not suitable as soil insecticides (Pestic. 1977 , p.241, Pestic., 1977. S, 267, Proceedings 1977 Brit. Crop. Protect. Conf 2, Si 647 and 655). It was concluded that pyrethroids are generally unsuitable as soil insecticides (Pestic Sc, 1977, p 267, Nachr. Chem. Techn. Lab. 26 (1978) No. 3 p.

Aim of the invention

The aim of the invention is the provision of new agents which are suitable for controlling soil insects.

Explanation of the essence of the invention

The invention is based on the object, new compounds

in particular to find new cyclopropanecarboxylic esters which are suitable as active ingredient in soil insecticidal agents.

: 20. 6. 1980

AP A 01 H / 215 614

56 135 12

It has now been found that the substituted cyclopropanecarboxylic acid esters of the general formula I

CH

COOCH,

in which

R is CH ₃ , Cl, Br, P and

X for Cl, "Br, J and

Y stands for Cl, F and

m and η can be integers from 0 to 5, provided that m and η can not be 0 at the same time,

are highly effective soil insecticides.

This surprising finding, which according to previous knowledge could not be expected, thus represents a valuable asset to the art.

The substituted cyclopropanecarboxylic acid esters of the formula I Bind are known in part from V§E-OS 26 58 074 and FR-PS 22 71 and FR-PS 22 90 415.

The substituted cyclopropanecarboxylic acid esters of the formula I, in which

R has the meaning given above and X is Br, J and

Y for Cl, F and

m is an integer from 1 to 3 and η is an integer from 0 to 4,

are new.

; 20. 6. 1980

AP A 01 U / 215

56 135 12

215614-3-

They are prepared by reacting a) an acid chloride of the formula II

CH ₃ CH ₃ R Δ Π.

_{R /} > - ^x coci

in which

R has the meaning given above,

with an alcohol of formula III

III,

in which

X, Y, m and η are as defined above,

at temperatures between 20 and 100 ⁰ C optionally in the presence of a diluent or an acid scavenger, or by reacting

b) a salt of general formula IV

CH ₃ , ) / ^CH 3 M ⁺ IV, / \ Λ R ' COO "

20. 6. 1980

AP A 01 H / 215 614

56 135 12

215614 -4-

in which

R has the abovementioned meaning and IA ⁺ denotes an alkali or alkaline earth cation or a primary, secondary or tertiary ammonium ion,

with a benzyl halide of the general formula V

in which

Shark stands for Cl, Br and

X ₁ Y, m and η have the abovementioned meaning,

reacted in a polar solvent at temperatures between 20 and 120 ⁰ C.

The substances which can be used according to the invention are generally defined by the formula I. In this formula, R is preferably identical or different and is methyl, F or chlorine or bromine, in particular chlorine or bromine, m is preferably integers from 0 to 51, η is preferably integers from 0 to 5.

The compounds are in the form of their stereoisomers. The substituents am'Cyclopropanring can be ice or trans each other. The carbon atoms C. and C.sub.1 can each have the R and / or S configuration and thus lead to optically active or racemic cis and / or trans isomers.

20, 6, 1980

AP A 01 N / 215

, '56 135

21 5 61 4,. _5. "

Examples of the substances which can be used according to the invention are:

2ι2-dimethyl-3-dichloiTrinylcyclopropancarbonsäure-pentafluorbenzylester

2 _f 2-Di-ethyl-3-dichlorovinylcyclopropanecarboxylic acid, tetrafluoro-2-chloro-benzyl ester

2,2-dimethyl-3-dichlorovinyl-tetrafluoro-3-cnlor benzyl ester

2,2-dimethyl-3-dichlorovinyl-tetrafluoro-4-chloro-benzyl ester

2,2-dimethyl-3-dichlorovinyl-tetrafluoro-3-bromo-benzyl ester

2,2-dimethyl-3-dichlorvinylcyclopropancarbonsäuren, 4,6-trifluoro-dichloro-benzyl ester

2 1 2-Dimethyl-3-dichlorovinylcyclopropanecarboxylic acid-2,3> 6-trifluoro-dichloro-benzyl ester

2,2-dimethyl-3-dichlorovinyl-2,4,5-trifluoro-dichloro-benzyl ester

2ι2-dimethyl-3-dichlorovinyl-3,4,5-trifluoro-dichloro-benzyl ester

2,2-dimethyl-3-dichlorovinyl-2,4,6-trifluoro-dibromo-benzyl ester

2,2-dimethyl-3-dichlorovinyl 2,4,6-trichloro-difluoro-benzyl ester

•. 2,2-dimethyl-3-dichlorovinyl 2,3,6-trichloro-difluoro-benzyl ester

2,2-Dimethyl-3-dichlorovinylcyclopropanecarboxylic acid 2,4> 5-trichloro-difluoro-benzyl ester

2,2-dimethyl-3-dichlorvinylcyclopropancarbonsäuren, 4,5-trichloro-difluoro-benzyl ester

20. 6. 1980

AP A 01 N / 215 614

56 135 12

215 614-6-

2 f 2-Dimethyl-3-dichlorovinylcyclopropanecarboxylic acid tetrachloro-2-fluoro-benzyl ester

2,2-dimethyl-3 ~ dicta.lorvinylcyclopropancarbonsäure tetra-chloro-3-fluoro-benzyl ester

2,2-Dimetb ^ l-3-dichlorovinyl-tetrachloro-4-fluoro-benzyl ester

2,2-dimethyl-3-'dichlorvinylcyclopropancarbonBäure-2,315,6-tetrafluorbenzylestcr

2,2-dimethyl-3-dichlorovinyl ~ 2.3 "4.5-tetrafluorbenzylester

2,2-Diraeth.yl-3-dichlorovinylcyclopropanecarboxylic acid 2,3, 5,6-tetrachlorobenzyl ester

212 ~ dimethyl-3-dichlorovinyl-2,314,5-tetrachlorbenzylester

2,2-D: ünethyl-3- & ichlorvinylcyclopropancarbonsäure-2,4 »6-trifluorbenzylester

2,2-Dimethyl-3-dichloro-ylcyclopropanecarboxylic acid-2,3,6-trifluorobenzyl ester

2f 2-Dimethyl-3-dichlorovinylcyclopropanecarboxylic acid 2,4,5-trifluorobenzyl ester

2,2-dimethyl-3-dichlorovinyl 3,4,5-trifluorbenzylester

2,2-Dimethyl-3-dichlorovinylcyclopropanecarboxylic acids, 4,6-trichlorobenzyl ester

2,2-dimethyl-3-dichlorovinyl 2,3,6-trichlorbenzylester

2,2-dimethyl-3-dichlorovinyl 2,4,5-trichlorbenzylester

: 20. 6. 1980

AP A 01 N / 215

56 135

215614 -7-

2,2-Dimethyl-3-dichlorovinylcyclopropanecarboxylic acids, 415-trichlorobenzyl ester

2,2-dimethyl-3-dichlorovinyl 2,4,6-trichloro-3-brombenzylester

2,2-dimethyl-3 ~ dichlorovinyl 2,4,6-trichloro-3-jodbenzylester

2 _{t of} 2-dimethyl-3-dichlorovinylcyclopropanecarboxylic acid 2,4-dichloro-6-bromobenzyl ester

2 _f 2-Dimethyl-3-dichloro-3-cyclopropanecarboxylic acid 3,5-dichloro-4-bromobenzyl ester

2ι2-dimethyl-3- <lichlorvinylcyclopropancarbonsäure-2,4-dichloro-5-jodbenzylester

2,2-dimethyl-3-dichlorovinyl-2,4-dichlorobenzyl

2,2-Dimethyl-3-dichlorovinylcyclopropanecarbonic acid 3,4-dichlorobenzyl ester

2t2-dimethyl-3-dichlorvinylcyclopropancarbonsä ^ lre-3,5-dichlorobenzyl

2,2-dimethyl-3-dichlorovinyl 2,4,6-tribrombenzylester

2,2-dimethyl-3-dichlorvinylcyclopropancarbonsäuren, 4,5-tribrombenzylester

2 | 2-dimethyl-3-dichlorovinyl-2,4-dibromo-6-chlorobenzyl

2,2-dimethyl-3-dichlorovinyl-2,4-dlbrom benzyl ester

2,2-dimethyl-3-dichlorovinyl-3,4-dibromo-benzyl ester

2,2-dimethyl-3-dichlorovinyl-3,5-dibromo-benzyl ester

20. 6. 1980

AP A 01 N / 215

56 135

215614 - β -

2,2-Dimetllyl-3-dichlorovinyl-2,6-dibromo-benzyl ester

2,2-dimethyl-3-d.ichlorvinylcyclopropancarbonsäure-2,4-difluoro-benzyl ester

2,2-dimethyl-3-dichlorvinylcyclopropancarbonsäuren »5-difluoro-benzyl ester

2 _ϊ 2-Dimethyl-3-dichlorovinylcyclopropanecarboxylic acid 2-fluoro-3-iodo-benzyl ester

2 _f 2-Dimethyl-3-dichlorovinylcyclopropanecarboxylic acid 4-fluoro-3-iodo-benzyl ester

2,2 ~ dimethyl-3-dichlorv: iJiylcyclopropancarbonsäure ~ 4-chloro-2-iodo-benzyl ester

212-Dimethyl-3-difluorocyclopropanecarboxylic acid> 2> 4-difluoro-3-chloro-5-oodobenzyl ester

2-Dimethyl-3-dichloro-2-cyclopropanecarboxylic acid 2-bromo-4-dod-benzyl ester

2,2-dimethyl-3-dichlorovinyl-3-

2 _{t of} 2-dimethyl-3-diallyl-vinylcyclopropanecarboxylic acid 3-bromo-benzyl ester

212-dimethyl-3-dichlorovinyl-3-iodo-4-chloro ~ benzyl ester

2,2 ~ dimethyl-3-dichlorovinyl-3-iodo-4-fluoro-benzyl ester

2,2-dimethyl-3-dichlorovinyl-3-iodo-benzyl ester

and the corresponding 2,2-dimethyl-3- (2-methylbutene-1-yD-cyclopropanecarboxylic acids and the like

2,2 ~ dimethyl-3-dibromvinylcyclopropancarbonsäureester.

20. 6. 1980

AP A 01 N / 215 614

56 135 12

215614 -9-

The esters listed include both the racemic and the optically active and the cis and / or trans isomers.

If, as the acid chloride of the formula II, 2,2-dimethyl-3-dichlorovinylcyclopropanecarboxylic acid chloride and, as alcohol of the formula III, 3-iodobenzyl alcohol, the course of the reaction in process a can be represented by the following formula scheme:

+ HO-CH ₀ -. , - ^ -ν- / χ COCl ^ά \ sJ ni ^ COO-CH ₂

The compounds of general formula II are known (DE-OS 2,439,177).

The alcohols of general formula III are known in some cases (Beilstein, 5th main volume, p. 446, 447).

New alcohols of the formula III can be prepared by known processes, for example by reduction of the corresponding carbonyl compounds of the general formula VIII

VIII,

in which

X ₁ Y, m and η have the abovementioned meaning and

Z is hydroxy, alkoxy, chloro-fluoro or

Hydrogen is associated with complex metal hydrides

20. 6. 1980 AP A 01 N / 215

215614.ίο.

The carbonyl compounds of the formula VIII required for the reduction are known (Beilstein, 9th main volume, Syst. Hiv 938, pp. 355-368; 9 * main volume, 3rd supplementary volume, Syst. No. 938, p. 1378, 1427-1431); Pp. 1452-1456).

Specific examples of the alcohols of the formula III are:

2-, 3- or 4-iodobenzyl alcohol 2-, 3-resp. 4-bromobenzyl alcohol 4-chloro-3-dodobenzyl alcohol 4-chloro-3-ylbenzyl alcohol 4 ~ bromo-3-oxybenzylalkobol Dichlorobromobenzyl alcohol Dichloro-iodobenzyl alcohol Diiodochlorobenzyl alcohol Dibromo-chlorobenzyl alcohol Dibroin-benzyl alcohol Di-iodobenzyl alcohol.

If sodium 2,2-dimethyl-3-dichlorovinylcyclopropane-1-carboxylate is used as the salt of the general formula IV and 3,5-dibromobenzyl chloride is the benzyl halide of the general formula V, the course of the reaction in process b can be represented by the following formula scheme:

, + ClCH 00 "Na ⁺ "

20. 6. 1980

, ., .. AP A 01 K / 215 614

  , 56 135 12

215614 _β11 _

The salts of the formula IV which can be used as starting materials in the performance of the process b) are known (German Offenlegungsschrift No. 2,436,178). The benzyl halides of the formula V required as reactants are known in some cases (Beilstein, 5th main volume, 3rd supplementary volume, Syst. No. 466, pages 717-720, S, 726-727).

New benzyl chlorides of the general formula V can be prepared in a manner known per se by halogenation of the corresponding toluene (Beilstein, 5th main volume, 3 # Supplementary tape Syst. Br. 466, p. 719-720, pp. 725-728). As an example of the benzyl chlorides which can be used according to the invention, mention may be made of 3t5-dibromobenzyl chloride.

The process according to b) is carried out in polar organic diluents such as ketones (z, B. acetone), nitriles (eg acetonitrile), acid amides (eg DIJF, hexamethylphosphoric triamide) or their mixtures with water. It is worked at temperatures between 20 and 100 ⁰ C.

Eb is worked in the presence or absence of suitable catalysts. Such catalysts are peralkylated polyamines, such as pentamethyldiethylenetriamine. The reaction is carried out as described in Synthesis 1975 p. 805.

The active compounds are suitable for controlling animal pests, in particular insects, which live in the soil. They are effective against normally sensitive and resistant species as well as against all or individual stages of development.

: 20. 6. 1980 AP A 01 H / 215 614

215614 _ ₁₂ "

The active ingredients are suitable for good plant tolerance and favorable toxicity to warm-blooded animals for controlling animal pests, in particular insects that occur in agriculture. They are effective against normally sensitive and resistant species as well as against all or individual stages of development. The above mentioned pests include:

From the order of Isopoda z. B. Oniscus esellus, Armadillidium vulgaris, Porcellio scaber.

From the order of Diplopoda z, B. Blaniulus guttulatus.

From the order of Chilopoda z, B, Geophilus carpophaus, Scutigera spec.

From the order of Symphyla z, B, Scutigerella immaculata.

From the order of Collembola z, B, Onychiurus arinatus.

From the order of Orthoptera z. B, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus differentialis, Schistocerca gregaria.

From the order of Dermaptera z, B, Porficula auricularis.

From the order of Isoptera z, B. Reticulitermes spp.

From the order of Anoplura z. B, Phylloxera vastatrix, Pemphigus spp., Linognathus spp.

From the order of Lepidoptera z. Agrotis spp., Euxoa spp., Peltia spp. Earias insulana, Prodenia litura, Spodoptera spp., Chilo spp., Pyrausta nubilalis.

From the order of Coleoptera z. B. Diabrotica spp., Psylliodes chrysocephala, Atomaria spp., Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites sordidus, Ceuthorrhynchus assimilis, Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha, Amphimallon solstitialis, Costelytra zealandica.

20. 6. 1980

AP A 01 N / 215 614

_ *, "56 135 12

215614. ₁₃ _

From the order of Diptera z. B, Bibio hortulanus, Oscinella frit, Phorbia spp., Pegomyia hyoscyami, Tipula paludcsa.

The active compounds can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, soluble powders, granules, IC emulsion suspension concentrates, seed powders, active ingredient-impregnated ITatur and synthetic substances, Peinstverkapselungen in polymeric materials and in enveloping materials for seeds. \

These formulations are prepared in a known manner, by mixing the active compounds with extenders, ie liquid solvents, liquefied gases under pressure and / or solid carriers, optionally with the use of surface-active agents, ie emulsifiers and / or dispersants and / or or foaming agents. In the case of using water as an extender z. As well as organic solvents can be used as auxiliary solvent. Suitable liquid solvents are essentially: aromatics, v / ie xylene, toluene, the Alky! Naphthalenes, chlorinated aromatic or chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, eg. As petroleum fractions, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water; with liquefied gas

20. 6. 1980

AP A 01 Ν / 215

56 135

21561 4 - ¹ 4-

shaped extenders or carriers are meant liquids which are gaseous at normal temperature and under normal pressure, eg aerosol propellants, such as halogenated hydrocarbons as well as butane, propane, nitrogen and carbon dioxide; suitable solid carriers are: z * B, ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as finely divided silica, alumina and silicates; as solid carriers for granules are: z, B. broken and fractionated natural rocks, such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules of inorganic and organic flours and granules of organic material, such as sawdust, coconut shells, corncobs and tobacco stalks; as emulsifying and / or foam-producing agents are in question: z. Nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. B. Alkylarylpolyglykol ether, alkyl sulfonates, alkyl sulfates, arylsulfonates and protein hydrolysates; suitable dispersants are: z, B. Lignin-sulphite liquors and methylcellulose.

Adhesives such as carboxymethylcellulose, natural and synthetic powdery, granular or latex-type polymers may be used in the formulations, such as gum arabic, polyvinyl alcohol, polyvinyl acetate.

Dyes such as inorganic pigments, e.g., iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azole-metallophthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc may be used ,

AP A Ol N / 215 614 56 135 12

215614

- 15 -

The formulations generally contain between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90 JB.

The application of the active compounds according to the invention takes place in the form of their commercially available formulations and / or the forms of use prepared for these formulations.

The active ingredient content of the formulations prepared from the commercial formulations may vary widely. The active ingredient concentration of the use forms may be from 0.0000001 to 100% by weight of active ingredient, preferably between 0.01 and 10% by weight.

The application is carried out in a customary manner adapted to the application forms, as a rule by spraying, scattering or dusting on or into the soil or else by administration in baits which are spread out when pests appear.

embodiment

The invention will be explained in more detail below with reference to some embodiments.

- 16 -

Π for

20. 6. 1980

AP A 01 H / 215 614

56 135 12

21 561 4 -ie

Example A

Limit concentration test / soil insects

Test insect: Tenebrio molitor larvae in the soil Solvent: 3 parts by weight of acetone Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To prepare a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration,

The preparation of active compound is intimately mixed with the soil. In this case, the concentration of the active substance in the preparation plays virtually no role, the only decisive factor is the amount of active substance per unit volume of soil, which is stated in ppm (= mg / l). The soil is poured into pots and allowed to stand at room temperature.

After 24 hours, the test animals are placed in the treated soil and after a further 2 to 7 days the efficacy of the active ingredient is determined by counting the dead and living test insects in % . The efficiency is 100 %, if all test insects have been killed, it is 0 % _t if there are just as many test insects live as in the untreated control.

Active ingredients, application rates and results are shown in the following table:

215614

20. 6. 1980

AP A 01 K / 215 614

56 135 12

table

Soil insecticides Tenebrio molitor larvae in soil

Active ingredient (constitution) Degree of destruction in % at active substance concentration in ppm

2.5 ppm

known

permethrin

₃ C

CO-O-CH

Cl Cl

Sumicidin

CH

Oil

Cl Cl 100

CH

CH. CH,

V ³

P P

100

215614

^: 20. 6. 1980

AP A 01 Bf / 215 614

56 135

- 18 -

0? a b e 1 1 e

Soil insecticides Tenebrio molitor larvae in soil

Active ingredient (constitution) Degree of destruction in % at active substance concentration in ppm

2.5 ppm

₃ C

P F

Cl

Cl

COOCH ₂ -

Cl 100

CH ₃ CH ₃

P P

Cl Cl

COOCH,

(1) trans-isomer

100

^CH 3V ^CH 3

P P

COOCH,

= U ice

P P 100

CH ₃ CH 3V

Cl Cl

OOCH

100

21 5 614 - ₁₉ _.

table

Soil insecticides Tenebrio molitor larvae in soil

20. 6. 1980 AP A 01 N / 215 614 56 135 12

Active ingredient (constitution) Abbb'tungsgrad in % at drug concentration in ppm

2.5 ppm

^CH 3y ^CH 3

P P

Cl Cl (-) trans

100

CH ^ .X3H.

Cl Cl

> A

_C1

OOCH,

P 'C 100

06/20/1980

• - * AP A 01 N / 215 614

56 135 12

215 614 - so -

Example B

Limit concentration test / soil insects

Test Insect: Agrotis segeturn larvae in soil Solvent: 3 parts by weight of acetone Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To prepare a suitable preparation of active compound, 1 part by weight Y / irkstoff mixed with the stated amount of solvent, the indicated amount of emulsifier and dilute the concentrate with water to the desired concentration.

The preparation of active compound is intimately mixed with the soil. In this case, the concentration of the active substance in the preparation plays virtually no role, the only decisive factor is the amount of active substance per unit volume of soil, which is stated in ppm (= mg / l). The soil is poured into pots and allowed to stand at room temperature.

After 24 hours, the test animals are placed in the treated soil and after a further 2 to 7 days the efficacy of the active ingredient is determined by counting the dead and living test insects in % . The efficiency is 100%, if all test insects have been killed, it is 0 %, if there are just as many test insects live as in the untreated control.

Active ingredients, application rates and results are shown in the following table:

2 15614 CN C-OOCCHra ΛΤΤ / ΊΤΤ ν / Xl ^ vll , - 21 - Table : 20. 6. 1980 AP A 01 K / 215 614 56 135 12 Agrotis Ground insecticidal segeturn larvae in the ground Active ingredient (constitution) Degree of killing in % at concentration of active compound in ppm 0.5 ppm known ere Sumieidin 3 0 %

CH

P P

100 %

P P

P Cl

100 %

^CH

100 %

20. 6. 1980

AP A 01 N / 215 614

56 135 12

- 22 -

table

Soil insecticides Agrotis se / yetura larvae in soil

Active ingredient (constitution)

Degree of kill in % at drug concentration in ppm 0.5 ppm

^CH3 / ^CH3

Cl Cl

/ == COOCH,

P P

P 'P

100

P Cl

OOCH,

P P

100

/ ο

OOCH

\ -

100

20. 6. 1980

AP A 01 N / 215 614

56 135 12

215614 -23-

example 1

2,2 ~ dimethyl-3-dichlorovinyl cyclopropane carboxylic acid 3-jodbenzylester

0.01 mol of 2,2-dimethyl-3-dichlorovinylcyclopropanecarboxylic acid chloride and 0.02 mol of 3-iodobenzyl alcohol were heated together to 100 ⁰ C until the evolution of HCl. The residual oil was then distilled on the Kugelrohr at 160 ⁰ C and 0.1 Torr.

IR: 2950, 1790, 1630, 1610, 1580, 1460, 1420, 1390, 1350, 1290, 1270, 1230, 1180, 1170, 1140, 1120, 1090, 1060, 1000, 930, 890, 870, 810, 785, 735, 700 cm " ¹

Example 2

Analogously, the 3-bromo-benzyl ester was prepared:

IR: 2950, 1720, 1610, 1580, 1450, 1410, 1390, 1350, 1270, 1230, 1180, 1110, 1090, 1060, 1000, 970, 930, 890, 860, 785, 700, 690 cm ^-1 .

Claims (4)

2156t 4 Erf induncjsans pruc-h 1 »Soil insecticidal agent, characterized by a content of substituted Cyclopropancarbon3äureestern the general formula I. CH COOCH in which R for CH ₃ , Cl ₁ Br, F and X for Cl, Br, O and Y stands for Cl, F and m and η for all Z _a choose of O can stand to 5, η is not with the proviso that m and can be O at the same time
in addition to extenders and / or surface-active agents, 2, use of substituted cyclopropane carboxylic acid esters of the formula I, characterized in that they are used for controlling soil insects. 3, Method of controlling soil insects, characterized in that substituted cyclopropanecarboxylic esters of the formula I are allowed to act on soil insects and / or their habitat. - 25 - AP A Ol N / 215 614 56 135 12 215614 - 25 - 4. Process for the preparation of soil insecticidal agents, characterized in that substituted cyclopropanecarboxylic acid esters of the formula I are mixed with extenders and / or surface-active agents.