JPS61275251A - Esters of cyclopropanecarboxylic acids and diacetylene alcohols, manufacture, vermifugal use and compositions - Google Patents

Abstract

(57) [Summary] This bulletin contains application data before electronic filing, so abstract data is not recorded.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to new esters of cyclopropanecarboxylic acid and diacetylene alcohol, their preparation, their use in combating parasites and compositions containing them.

The subject of the invention is therefore the following general formula CI) C=CR
□ (R1 and R2 may be the same or different and represent a hydrogen atom or an alkyl group containing 1 to 8 carbon atoms, Rs is the following formula (the configuration of the double bond is E or Z, R4 is a hydrogen atom,
represents a fluorine, chlorine or bromine atom, or an alkyl or alkoxyl group containing 1 to 8 carbon atoms, Z represents an oxygen or sulfur atom, and R represents (a) one or more of the same or different functional groups; a saturated or unsaturated linear, branched or cyclic alkyl group containing from 1 to 18 carbon atoms optionally substituted with (b) one or more of the same or different functional groups; or (C) a heterocyclic group optionally substituted with one or more of the same or different functional groups. or R5 is of the formula linear, branched or cyclic saturated or unsaturated alkyl groups, which chain may be interrupted by one or more heteroatoms and/or substituted by one or more halogen atoms; ) or R3 represents an aryl or aralkyl group containing up to 18 carbon atoms; or R3 represents a group of the formula (wherein Hat represents a halogen atom); K corresponds to a compound in all possible stereoisomeric forms and in the form of a mixture of all possible stereoisomers.

Compounds of formula (I) can exist in many stereoisomeric forms. In fact, they have 2 in the 1 and 3 positions of the cyclopropane.
It has asymmetric carbon atoms. They can also have other asymmetric centers or axes in the R3 group.

When R1 or R2 represents an alkyl group, it is preferably a methyl, ethyl, n-propyl or isopropyl group.

When R3 represents a group of the following formula, it means that R represents a group of the following formula:
A group representing one of the preferred meanings of R in No. 86, No. 0050554, No. 0077721, and No. 0108679 is preferred.

When R4 or R5 represents an alkyl group, it is preferably methyl, ethyl, n-propyl, isopropyl, or optionally substituted with bromine or bromine atoms.

When R4 represents an alkoxy group, it is preferably a methoxy or ethoxy group.

When R5 represents an aryl or aralkyl group, it is preferably a phenyl or benzyl group.

When R5 represents a group of the following formula, the preferred meaning of Hal is fluorine,
They are chlorine and bromine.

A subject of the invention is in particular the compounds of the formula (I) in which R1 and R2 represent hydrogen atoms.

Among the preferred compounds of the present invention, in particular, R3 is of the following formula (where the double bond configuration is E or 2, R and R4
has the above-mentioned meaning). Among these compounds, those in which R represents a linear or branched alkyl group containing 1 to 8 carbon atoms, such as a methyl, ethyl, isopropyl or t-butyl group; or R represents one or more Examples include compounds representing an alkyl group containing 1 to 8 carbon atoms substituted with a halogen atom, for example one or more fluorine atoms. Therefore, as the R group, -CH2C
F, groups can be mentioned.

More specifically, the present invention provides that R5 is of the following formula (where R4
represents a hydrogen atom, the configuration of the double bond is Z, and the structure of the cyclopropane moiety is I R.

cis) Subject is a compound of formula (I) representing a radical.

Among the preferred compounds of the present invention, R1 is also represented by the following formula (where R4 represents a fluorine, chlorine or bromine atom, the configuration of the double bond is E, and the structure of the cyclopropane moiety is I R, cis). Compounds of formula (I) representing a group of

In particular, the subject of the invention is the abovementioned compounds in which R4 represents a fluorine atom.

Among the preferred compounds of the invention are those whose preparation is shown in the experimental section below.

Further, the present invention provides that, per k for producing the compound of formula (I), an acid of the following formula (n) (wherein R3 has the above-mentioned meaning) or a functional derivative of this acid of the following formula <m> ( Here R
1 and R2 have the meanings given above) or a functional derivative of this alcohol to form the corresponding formula (
The subject matter is a process for the preparation of a compound of formula (I), characterized in that a compound of formula (I) is obtained.

According to a preferred embodiment of the production method of the invention, the formula (ff
) is esterified with an alcohol of formula (III) in the presence of dicyclohexylcarbodiimide and 4-dimethylaminopyridine.

Compounds of formula CI) can also be prepared according to variants of the above-mentioned methods. Therefore, when it is desired to produce a compound of formula (I) in which R5 represents a group of the following formula, that is, when it is desired to produce the following formula, first, an acid of the following formula is left behind,
This is then esterified according to conventional methods to give the formula (I
) can be obtained.

Acids of formula (n) are known compounds, for example European Patent Application Nos. 0038271 and 0041021.
No. 0048186, No. 0050534, No. 00
No. 7721, No. 0108679 and French Patent No. 2536389.

In addition, alcohol of formula (III) is also a known compound, and 13u
ll.

Soc, Chim, 6.947-9 (1939) or by Jones et al., J.C.
hem.

Soc, (1960), 3483-9.

The compounds of formula (I) exhibit beneficial properties that make it possible to use them for combating parasites. For example, this includes the control of plant parasites, house parasites and warm-blooded animal parasites. Therefore, the compounds of the present invention can be used for the control of pests, nematodes and mites which are parasites of plants and animals.

The subject of the invention is therefore the use of the compounds of formula (I) as defined above for the control of plant parasites, house parasites and warm-blooded animal parasites.

The compounds of formula (I) can therefore be used, in particular, for the control of pests in the agricultural field, such as larvae of the Aphids, Lepidoptera and Coleoptera. They are used in dosages between 101 and 500 I per hectare of active substance.

The compound of formula (I) can also be used to combat pests in houses, especially flies.
It can be used to control mosquitoes and cockroaches, as well as animal parasitic pests such as cattle, sheep and urea lice.

The compounds of formula (I) can also be used to exterminate plant parasites such as mites and nematodes.

The compound of formula (I) can also be used to exterminate parasitic mites on animals,
For example, ticks (tiek L, especially boophilus (B)
oophilus) 11 ticks, Hif o Muni 7
(Hyalomnia) mites, Amblyomnia species mites, phipicephalus 17M mites, or all kinds of arcoptic mites, especially Sarcoptic mites.
e), psoropti
c m1te) and Cryoptych Mite (c
horioptic mlte).

The subject of the invention is therefore the general formula (I
) A composition for exterminating warm-blooded animal parasites, house parasites, and plant parasites, characterized by containing at least one compound of the following.

In particular, the subject of the invention is at least 111! of the compounds of general formula (1) as defined above! 1 as an active ingredient.

The present invention also provides an acaricidal composition containing at least one compound of formula (I) as an active ingredient, and a nematicidal composition containing at least one compound of formula (I) as an active ingredient. Take objects as subjects.

The present invention also provides a method for controlling parasitic mites of warm-blooded animals, in particular ticks and mites, using a small amount of the compound of general formula (I) as an active ingredient. The subject matter is an acaricide composition comprising:

Among the preferred pesticide compositions of the invention, mention may be made in particular of compositions containing the compounds described in the Examples.

These compositions of the invention are manufactured according to conventional methods in the agricultural and chemical industry. One or more other besticides can be added to them. These compositions can be provided in the form of powders, granules, suspensions, emulsions, solutions, aerosol solutions, combustible strips, baits or other formulations commonly used for the application of compounds of this class.

In addition to the active ingredients, these compositions generally contain, among other things:
Contains a vinyl and/or nonionic surfactant that enables uniform dispersion of the components that make up the mixture.

The vehicles used may be water, alcohols, hydrocarbons or other organic solvents, liquids such as mineral oil, animal or vegetable oils, powders such as Merck, clay, silicates or diatomaceous earth, or combustible solids. It's fine.

The insecticide composition according to the invention preferably has a
Contains 0% active substance by weight.

For domestic use, in a useful embodiment the compositions of the invention are used in the form of smokable compositions.

Thus, the composition according to the invention may consist of a combustible insecticide coil or a non-combustible fibrous substrate for the non-active part. In the latter case, the smoke agent obtained after compounding the active substance is placed on a heating device.

When insecticide coils are used, inert carriers can be used, for example, pyrethrum lees, machilusthu powder, etc.
mbergil (7) leaf powder), pyrethrum stem powder, cedar needle powder, wood powder (pine sawdust)
, starch and coconut shell powder.

In that case, the dosage of the active substance is, for example, Q, 03-25
Weight%.

If a non-combustible fibrous carrier is used, the dosage of active substance may be, for example, α03-25% by weight.

The compositions of the invention for domestic use can also be obtained by preparing a spray oil based on the active ingredient and impregnating a lamp wick with this oil, which is then combusted.

The concentration of active ingredient incorporated into this oil is preferably 0.03 to 25% by weight.

Acaricides and nematocides are provided in particular in the form of powders, granules, suspensions, emulsions or solutions.

For acaricide applications, preferably foliar spray wettable powders containing 1-80% active ingredient, or 1-5oog
A foliar spray solution containing 7i active ingredient is used.

Foliar powders containing α05-3X active substances can also be used.

As a nematicide, a soil treatment solution containing 300 to 500 g/J of active ingredient is used.

The acaricidal and nematocidal compounds according to the invention are used in dosages of 1 to 100 1 active substance per hectare.

When the control of parasitic mites on animals is a problem, the compounds of the invention can be incorporated into feeding compositions in combination with nutrient mixtures for animal fattening. The nutrient mixture can vary depending on the species of animal. It's grains, sugars
It can contain S-shell grains, soybean cake, peanut cake, sunflower cake, animal-based powders, such as fish meal, synthetic amino acids, inorganic salts, vitamins, antioxidants, and the like.

The subject of the present invention is therefore a composition for animal breeding which contains as active ingredient at least one compound of the general formula (I) as defined above.

For combating parasitic mites on animals, the composition of the invention can be applied externally, by transpiration, by shampooing, by bathing,
Alternatively, it can be administered by application onto the spine using the "pour-on" method.

The subject of the invention also provides as active substance on the one hand the general formula (
I) and, on the other hand, a dilute acid and arethrolone, 44 to 6-titrahydro7talimidomethyl alcohol, 5-benzyl-3-furylmethyl alcohol, 3-phenoxybenzyl alcohol and α-
Each ester with cyano-3-phenoxybenzyl alcohol: 2゜2-dimethyl-3-(2-oxo-3-tetrahydrothiophenylidenemethyl)cyclopropane-1
-Ester of carboxylic acid and 5-benzyl-3-furylmethyl alcohol; 2,2-dimethyl-3-(z2-dichlorovinylcyclopropane-1-carboxylic acid and 3-phenoxybenzyl alcohol, IL/:ff- and each ester with α-cyano-3-phenoxybenzyl alcohol;
2.2-dimethyl-5-(2゜2-dibromviny/L/
) α-cyano-3- of cyclopropane-1-carboxylic acid
Ester with phenoxybenzyl alcohol; 2-1
)-ester of chlorphenyl-2-inglobyl acetic acid and 3-phenoxybenzyl alcohol; 2,2-dimethyl-3-(1,2,2,2-tetrahaloethyl)cyclopropane-1-carboxylic acid (wherein hap represents a fluorine, chlorine or bromine atom) and arethrolone, & 4.5
゜6-Titrahydrophthalimidomethyl alcohol, 5
-Contains at least one pyrethrinoid ester selected from the group consisting of benzyl-3-furyl methyl alcohol, 3-phenoxybenzyl alcohol, and each ester with α-cyano-3-phenoxybenzyl alcohol (here, the formula The compound (I) and the above-mentioned pyrethrinoid esters have an insecticidal, acaricidal or nematicidal activity characterized in that the acid and alcohol linkages of the pyrethrinoid esters are in all possible stereoisomeric forms thereof. The composition is endowed with

In order to increase the biological activity of the compounds of the invention, standard synergists used in analogous cases, such as 1-(2
,5,8-)rioxadodecyl)-2-propyl-4,
5-methylenedioxybenzene (piperonyl butoxide), or N-(2-ethylheptyl)bicyclo[2,2
, 1:1-5-hebutene-containing 3-dicarboxamide, or biperonyl bis-2-(2'-n-butoxyethoxy)ethyl acetal (trobital) can be added.

The invention therefore also subjects compositions as described above, characterized in that they additionally contain a synergist for pyrethrinoids.

The following examples are illustrative of the invention and do not limit the invention in any way.

Example 1: (IR,C15tE)-2,2-dimethyl-
3α7II penta-1,4-diyn-3-ol, t
oa, y's (IRpct' + E) -2,
2-dimethyl-5-(2-fluoro-3-oxo-3-
mixing methoxypropenylcocyclopropane-1-cardanoic acid (prepared as described in Preparation Example 4 of French Patent No. 2,536,389) and 15ee of methylene chloride;
Cool to 0°C, add 50 μ of 4-dimethylaminopyridine, then add ta3. A solution of dicyclohexylcarbodiimide (y) dissolved in 5 cc of methylene chloride is added. The whole was stirred at 20° C. for 2 hours, the resulting precipitate was separated, and the F solution was concentrated by vacuum distillation to obtain the crude desired product of t9p. This is chromatographed on silica, eluting with a mixture of hexane and ethyl acetate (9-1). 1 g of the expected compound was obtained.

[α]D=+56”: k 2-50 (C= CL 4
Xchloroform).

2.5Ii of penta-14-diyn-3-ol, 6.
89 (IR, cis, E)-2,2-dimethy/L/3
-[2-fluoro-3-oxo-3-t-butoxypropenylcocyclopropanecarboxylic acid (prepared as described in the preparation example of FR 2536389) and 2
After mixing 5 cc of methylene chloride, introducing 100 m9 of dimethylaminopyridine and cooling to 0° C., 5.4.
A solution of dicyclohexylcarbodiimide (No. 9) dissolved in 10 cc of methylene chloride is added. After stirring at 20° C. for 16 hours, the resulting precipitate is separated and the solution F is concentrated by vacuum distillation. 113 g of crude desired compound were obtained,
This is chromatographed on silica, eluting with a mixture of hexane and ethyl acetate (95/5).

The desired compound of 6.ii was obtained.

[α]D=+515°±1°(c=2X chlorotetraform)
.

-3-yl4.8JF') (IRecis*Z)-2,2-dimef
k-3-(3-oxo-3-t-butoxyp-benyl)
Mix 1,2 g of cyclopropanecarboxylic acid penta-Ia-diyn-3-ol (prepared as described in Preparation Example 8 of European Patent No. 0041021) and 30 cc of methylene chloride and introduce 50w9 of dimethylaminopyridine. Then, a solution of 405 g of dicyclohexylcarbodiimide dissolved in 10 cc of methylene chloride was added, and the mixture was stirred at 20° C. for 16 hours. The resulting precipitate was separated and the filtrate was concentrated to dryness by distillation under reduced pressure to obtain a crude desired compound of 7.51i. This is chromatographed on silica, eluting with a mixture of hexane and ethyl acetate (9-1). 4.5 g of the expected compound was obtained. mp91℃.

(α)D=+75°±1°(C=1% era form)
.

xsy (IR, cls, E)-2,2-dimethyl-s
-[2-Fluoro-3-oxo-3-ethoxybutetrabenyl]cyclopropanecarboxylic acid (French Patent No. 24
91060), tsIi penta-14-diyn-3-ol and 25 cc of methylene chloride were mixed together, cooled to 0° C., and 351/19 dimethylaminopyridine was added. A solution of dicyclohexylcarbodiimide 31 dissolved in 10 cc of methylene chloride is then added. After stirring at 20℃ for 3 hours,
The resulting precipitate was separated, and the r solution was concentrated to dryness by distillation under reduced pressure to obtain a crude desired product of 5.9Ii. This was chromatographed on silica, eluting with a mixture of hexane and ethyl acetate (9-1) to give the desired compound of 'Lql.

[α]D=+45°±15°(c=t 2% a
ctform).

One Il 3! ! (IR, cis, Z)-2,2-dimethyl-3
-1:3-Methoxy-5-oxopropenylcocyclopropanecarboxylic acid (Venter 14 of Manufacturer 15I as described in Preparation Example 1 of French Patent No. 2480748)
- Diyn-3-ol and 508e of methylene chloride are mixed, cooled to 0°C, then 30 μ of dimethylaminopyridine is introduced, followed by a solution of 3 g of dicyclohexylcarbodiimide dissolved in 15 cc of methylene chloride. will be introduced. After stirring at 20°C for 3 hours, add 15 cc of acetic acid and 0,000 sec of ethanol, and stir for an additional 15 minutes. The resulting precipitate was separated and the PK was concentrated by vacuum distillation to obtain 5.71 of the crude desired compound. This is chromatographed on silica, eluting with a mixture of hexane and ethyl acetate (9-1). 3.11 of the expected product was obtained.

[αID=+645°±2.5°(C=16
Xchloroform).

-3-yl 5g of (11,cis,E)-2,2-dimethyl-3-
[2-Fluoro-5-t-butyloxy-3-oxopropenylcocyclopropanecarboxylic acid penta-1,4-
A toluene solution of diyn-3-yl, 500 μl of p-toluenesulfonic acid, and hiscocc was combined and refluxed until the evolution of isobutylene ceased (about 20 minutes). After cooling,
The toluene solution was washed with water and then concentrated to dryness by vacuum distillation to yield 41.90 of the desired product.

1705 Absorption of tx-', attributed to C=O of acid 1757
Absorption of am-', C=Ok ascription of ester 1653c
Absorption of IrL, attributed to C=C in E configuration 33ooi' and 213o,y', attributed to C3CH - 2g of compound prepared in step A, 15g of 2.2°2-
Trifluoroethanol and 15 cc of methylene chloride are mixed, cooled to 0° C. and 100 η of dimethylaminopyridine are introduced. After cooling to 0° C., a solution of 1.56 g of dicyclohexylcarbodiimide dissolved in 5 CC of methylene chloride is added and stirred at 20° C. for 3 hours.

The resulting precipitate was separated and the solution F was concentrated to dryness by distillation under reduced pressure to obtain 4.39 of the crude desired compound. This is purified on silica and eluted with a mixture of hexane and isopropyl ether (9-1). The desired compound of t9p was obtained.

[α]D=+35°±2° (c=14X chloroform).

2I (IR-ci'*E)-2,2-dimethyl-5-
(2-fluoro-2-carboxyethynylcocyclopropanecarboxylic acid venter i, 4-diyn-3-yl, 1
g of Improper Tool, 20 cc of methylene chloride and 1
Mix 00Tn9 of dimethylaminopyridine and cool to 0°C. A solution of 156 g of dicyclohexylcarbodiimide dissolved in 5 cc of methylene chloride is introduced,
Stir at 20° C. for 3 hours, then filter the resulting insoluble matter. The p-liquid was concentrated by vacuum distillation to obtain 3.2 g of the crude desired compound, which was chromatographed on silica and treated with a mixture of hexane and inglovir ether (9-1
). 17 g of the expected compound were obtained.

[α]D=+45°±1°(C=1X chloroform)
.

zy(1R,cis,Z)-zz-dimethyl-3-
(3-oxo-3-t-ptoxygropenyl)cyclopropanecarboxylic acid venter-14-diyn-5-yl, 2
001R9 p-toluenesulfonic acid and 20 cc of toluene are mixed and the reaction mixture is heated to reflux at 150° C. (external temperature) until inbutylene evolution ceases (approximately 15 minutes). After cooling, washing with water, drying and concentration to dryness by vacuum distillation, the expected product 169 was obtained. mp 110℃
.

'L6g of the compound produced in step A, 2g of 2.2゜2
- Mix trifluoroethanol and 15 cc of methylene chloride and cool to 0<0>C. 50 η of dimethylaminopyridine are introduced, followed by a solution of t59 dicyclohexylcarbodiimide dissolved in 5 cc of methylene chloride. Stirring was continued at 20°C for 16 hours, then the resulting precipitate was separated, and the F solution was concentrated to dryness by vacuum distillation.
4 g of crude desired compound was obtained which was chromatographed on silica and chromatographed on a mixture of hexane and ethyl acetate (9-
Elute with 1). 8 g of the expected compound was obtained.

[α”ID=+47°±t5° (c=iX chloroform).

Insecticidal activity of compounds of the invention The insects tested were female house flies 4 days after emergence.

The experiments were carried out by direct spraying in a Kerr 7-March chamber using a mixture of acetone (5%) and Isopar #L (petroleum-based solvent) as the solvent at a concentration of 1/1 or 119/no (use of solvents). amount: 21R1/sec).

Fifty animals were used per treatment. Testing is done every minute for up to 10 minutes.
This was then carried out at 15 minutes, and the KT50 was determined in the usual manner.

The experimental results obtained are summarized in the table below.

1 t5 1.9 5 5.1 1, fir4
5 2I1.1g 5 5 8 1fi 7 4.8 Q, IF8 2
．． 4 111 Example 9: Preparation of Soluble Concentrate A homogeneous mixture consisting of the following components was prepared.

Compound of Example 4 D, 25.9 piperonyl butoxide to og Tween 80
Q, 25. l10 dopanol AQ
, 1g water 9&
41 The following ingredients were mixed intimately.

Compound of Example 4 n, oosg piperonyl butoxide o, os9 Dopanol A
(111 tween 80
55g xylene?
6.345. pThe following ingredients were mixed intimately.

Compound of Example 7 109 Tween 80
15g Dopanol A
α5I xylene 74
．． 5.9 A homogeneous mixture was prepared consisting of the following ingredients.

Claims (21)

[Claims] (1) The following general formula (I) ▲Mathematical formulas, chemical formulas, tables, etc.▼(I) [R_1 and R_2 may be the same or different and contain a hydrogen atom or 1 to 8 carbon atoms Represents an alkyl group, R_3 is the following formula ▲ Numerical formula, chemical formula, table, etc. represents an alkyl or alkoxyl group containing carbon atoms of saturated or unsaturated linear, branched or cyclic alkyl groups containing atoms or (b) containing from 6 to 14 carbon atoms optionally substituted with one or more identical or different functional groups; or (c) a heterocyclic group optionally substituted with one or more of the same or different functional groups), or R_3 represents the following formula ▲ mathematical formula, chemical formula, table etc.▼ (Here, the configuration of the double bond is E or Z, A represents an oxygen or sulfur atom, a sulfoxide group or a sulfone group, and R_5 is a linear or branched bond containing up to 18 carbon atoms. or represents a cyclic saturated or unsaturated alkyl group, the chain optionally being interrupted by one or more heteroatoms and/or substituted by one or more halogen atoms, or R_5 represents an aryl or aralkyl group containing up to 18 carbon atoms), or R_3 represents a group of the following formula ▲There is a mathematical formula, chemical formula, table, etc.▼ (where Hal represents a halogen atom) represents a group] in all possible stereoisomeric forms and in the form of mixtures of all possible stereoisomers. (2) A compound of formula (I) according to claim 1, wherein R_1 and R_2 represent hydrogen atoms. (3) R_3 is the following formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (Here, the configuration of the double bond is E or Z, and R and R_
4 has the above-mentioned meaning) as defined in claim 1 or 2,
I) Compound. (4) The formula according to claim 3, wherein R represents a linear or branched alkyl group containing 1 to 8 carbon atoms (
I) Compound. (5) A compound of formula (I) according to claim 4, wherein R represents a methyl, ethyl, isopropyl or t-butyl group. (6) 1-8 in which R is substituted with one or more halogen atoms
5. A compound of formula (I) according to claim 4, which represents an alkyl group containing 5 carbon atoms. (7) A compound of formula (I) according to claim 6, wherein R is a group substituted with one or more fluorine atoms. (8) A compound of formula (I) according to claim 7, wherein R represents a -CH_2CF_3 group. (9) R_4 represents a hydrogen atom, and the double bond configuration is Z
and the structure of the cyclopropane moiety is 1R, cis, the formula according to any one of claims 3 to 8 (
I) Compound. (10) R_4 represents a fluorine, chlorine or bromine atom,
9. The compound of formula (I) according to any one of claims 3 to 8, wherein the configuration of the double bond is E and the structure of the cyclopropane moiety is 1R, cis. (11) A compound of formula (I) according to claim 10, wherein R_4 represents a fluorine atom. (12) In producing the compound of formula (I) according to any one of claims 1 to 11, the following formula (II)
▲There are mathematical formulas, chemical formulas, tables, etc. ▼ (II) (where R_3 has the meaning above) The acid or the functional derivative of this acid has the following formula (III) ▲ Mathematical formula,
There are chemical formulas, tables, etc. ▼(III) (where R_1 and R_2 have the meanings given above) or a functional derivative of this alcohol is reacted to obtain the corresponding compound of formula (I). A method for producing a compound of formula (I). (13) A method of using the compound of formula (I) according to any one of claims 1 to 11 for exterminating plant parasites, house parasites, and warm-blooded animal parasites. (14) Plant parasites, house parasites, and warm-blooded animal parasites, characterized by containing at least one compound according to any one of claims 1 to 11 as an active ingredient. Disinfecting composition. (15) An insecticide composition containing at least one compound described in any one of claims 1 to 11 as an active ingredient. (16) An acaricide composition containing at least one compound described in any one of claims 1 to 11 as an active ingredient. (17) A nematicide composition containing at least one compound described in any one of claims 1 to 11 as an active ingredient. (18) Parasites of warm-blooded animals, especially mites and other mites, characterized in that they contain as an active ingredient at least one of the compounds according to any one of claims 1 to 11. Acaricide composition for exterminating type (mite). (19) An animal breeding composition containing at least one of the compounds described in any one of claims 1 to 11 as an active ingredient. (20) on the one hand at least one compound of the general formula (I) as active substance and on the other hand chrysanthemum acid and arethrolone, 3,4,5,6-tetrahydrophthalimidomethyl alcohol, 5-benzyl-3-furyl Each ester with methyl alcohol, 3-phenoxybenzyl alcohol and α-cyano-3-phenoxybenzyl alcohol;
Ester of 2,2-dimethyl-3-(2-oxo-3-tetrahydrothiophenylidenemethyl)cyclopropane-1-carboxylic acid and 5-benzyl-3-furylmethyl alcohol; 2,2-dimethyl-3- (esters of 2,2-dichlorovinylcyclopropane-1-carboxylic acid and 3-phenoxybenzyl alcohol and α-cyano-3-phenoxybenzyl alcohol; 2,2-dimethyl-3-(2,2-dibromvinyl ) Cyclopropane
Esters of 1-carboxylic acid with α-cyano-3-phenoxybenzyl alcohol; 2-p-chlorophenyl-2
-Ester of isopropylacetic acid and 3-phenoxybenzyl alcohol; 2,2-dimethyl-3-(1,2,2
, 2-tetrahaloethyl) cyclopropane-1-carboxylic acid (where halo represents a fluorine, chlorine or bromine atom) and arethrolone, 3,4,5,6-tetrahydrophthalimidomethyl alcohol, 5-benzyl-3 - Contains at least one pyrethrinoid ester selected from the group consisting of esters with furyl methyl alcohol, 3-phenoxybenzyl alcohol, and α-cyano-3-phenoxybenzyl alcohol (wherein the formula (
I) and the acid and alcohol bonding moieties of the above-mentioned pyrethrinoid esters are in all possible stereoisomeric forms). composition. (21) The composition according to any one of claims 14 to 20, which also contains a pyrethrinoid synergist.