CH643544A5 - Pesticide compounds, processes for their preparation, and their use - Google Patents

Description

The invention relates to imidazolines, processes for their preparation, their use as pesticides and pesticide preparations which contain these imidazoles.

45 It has been found that compounds of the formula I and their acid addition salts are active against arthropods, for example against members of the order Acarina.

These are compounds of the formula I:

CH-

N *

X-CH

wherein Y has the meaning given in claim 1, and then optionally converting the compound of formula (1) into an acid addition salt or the acid addition salt of formula (I) into the free base or another acid addition salt.

14. A pesticide preparation containing a compound of formula (1) according to claim 1 together with a carrier.

15. Preparation according to claim 14, characterized in that the carrier is a surface-active agent.

16. Preparation according to claim 14, characterized in that the carrier is a liquid.

60

and their acid addition salts, in which XO or NH and Y are bromine, fluorine, iodine, -N02, -OR, -C02R, -CONR'R2 or —S02NR'R2, and if X is NH, Y is also chlorine, CN 65 or Alkyl having 1 to 4 carbon atoms, where R is an alkyl group having 1 to 18 carbon atoms, preferably having 1 to 4 or 12 to 18 carbon atoms, and R1 and R2, which may be the same or different, for hydrogen or alkyl having 1

643 544

4th

up to 18 carbon atoms, preferably with 1 to 4 carbon atoms or 12 to 18 carbon atoms; in particular, either R1 or R2 is an alkyl radical having 12 to 18 carbon atoms. Preferred compounds of the formula I are those of the formula Ia:

X-CH

CH.

/ N \

: ^ 0

N-substituted carbamoyl compound) or by a substitution reaction with a compound of the formula III:

X -CO.NH

(in)

(Ia)

CO- NH-

and their acid addition salts, in which X has the meaning given above and Y1 is fluorine, bromine, —N02, CH30— or —C02C2Hs or X NH and Y1 are chlorine.

Individual compounds of formula I can exist in their solvated form.

Preferred compounds of formula I are: 1- [N- (4-methoxyphenyl) carbamoyl] -2- (2,3-dimethylphenoxymethyl) -2-imidazoline;

1- [N- (4-chlorophenyl) carbamoyl] -2- (2,3-dimethylanilinomethyl) -2-imidazoline;

1- [N- (4-bromophenyl) carbamoyl] -2- (2,3-dimethylphenoxymethyl) -2-imidazoline;

1- [N- (4-nitrophenyl) carbamoyl] -2- (2,3-dimethylphenoxymethyl) -2-imidazoline;

1- [N- (4-fluorophenyl) carbamoyl] -2- (2,3-dimethylphenoxymethyl) -2-imidazoline;

1- [N- (4-bromophenyl) carbamoyl) -2- (2,3-dimethylanilinomethyl) -2-imidazoline,

and their acid addition salts.

The compounds of formula I and their acid addition salts are active against arthropods. The compounds of formula I can be used to control pests, e.g. Rhipicephalus appendiculatus, Boophilus decoloratus, Boophilus microplus, Rhipicephalus evertsi, Amblyomma hebraeum, Psoroptes ovis and Hyalaoma species in animals and Tetranychus species in plants.

The compounds of formula I have improved stability in aqueous media compared to known imidazolines.

The compounds of the formula I can be prepared by known processes for the preparation of compounds of an analogous structure.

The compounds of the formula I are, according to one of the processes according to the invention, from imidazolines of the formula II substituted in the 2-position or their acid addition salts:

where Y has the meaning given above and X1 is a cleavable group, e.g. Halogen, acyl, alkoxy (for example carbamates) or sulfonyloxy is obtained.

For example, the reaction can be carried out either in water or in an organic solvent, e.g. Chloroform or methylene chloride, preferably in the presence of a base such as e.g. an alkali metal hydroxide, an alkali metal carbonate or a tertiary organic base such as e.g. Triethylamine, pyridine or substituted pyridines or piperidines, e.g. Pentamethylpiperidine or tetra-methylpiperidine and generally at temperatures from -70 to 120 ° C, preferably at -10 to 40 ° C.

Compounds of formula I, especially those in which the group

-C0NH-Ç _ ^ - Y

is not strongly electron-attracting, according to another process according to the invention, also by reacting ethylenediamine of the formula IV or one of its salts:

H2N.CH2CH2NH.CO.NI

// \\

(IV)

30th

where Y has the meaning given above with a suitable 2,3-dimethylphenoxyalkyl or 2,3-dimethylanilinoalkylcarbonic acid or a reactive functional derivative thereof, e.g. Imidate, thioimidate, imidohalide, ester, amidine, thioamide, nitrii or carboxyalkylthioamide. These reagents are represented by Formula V:

CH ^

(V)

X-CH2-Q

in which X has the meaning given above and Q represents a carboxyl group or one of its reactive functional derivatives which forms the imidazoline ring of the formula I when reacted with a compound of the formula IV.

Suitable derivatives are, for example:

NH

-C (imidate)

^ OAlk

OAlk

I.

—C — OAlk (Orthoester)

I.

OAlk

(II) 55 y

NH

—C (thioimidate)

^ SAlk

N

wherein X has the meaning given above, either by direct addition reaction with an isocyanate of the formula:

° = ° =

where Y has the meaning given above (to produce the

O

60

/

\

(Ester)

-C

-C

OAlk y

\ y

\

NH

Shark NH

'NH,

(Imidohalide)

(Amidine)

(Thioamide)

—C = N

(Nitrii)

NH,

5

643 544

-C

_ ^ (N-alkoxycarb- ^ onylthioamide)

NHC02Alk y \

(Thioester)

BAlk wherein Alk is an alkyl group with 1 to 6 carbon atoms and one of the radicals A and B is sulfur and the other is sulfur or oxygen.

The reaction conditions are of course dependent on the starting materials used. You can work in the presence or absence of a liquid medium. High or low temperatures and various pressures can be used.

If the functional carboxylic acid derivative is an imidate, it is preferably in the form of an acid addition salt, such as e.g. of the hydrogen halide salt is used and can be obtained, for example, from the nitrii and a suitable anhydrous alkanol, such as e.g. Ethanol or methanol, in the presence of dry diethyl ether or chloroform and hydrogen chloride at a low temperature. The reaction can be carried out, for example, within a temperature range from −20 ° C. to room temperature. The reaction with the ethylenediamine of formula IV can e.g. in an inert anhydrous medium, such as chloroform, methylene chloride or ether. The reaction components are preferably heated under reflux until the reaction is complete.

The thioimidate intermediates can be obtained, for example, from the corresponding nitriles by reaction with an alkyl mercapto and a hydrogen halide gas at low temperatures, e.g. at about 0 ° C, in the presence of dry diethyl ether in the form of the acid addition salt. The thioimidate can then be reacted with an ethylenediamine of the formula IV, preferably at the reflux temperature of the reaction mixture.

The ester intermediates can be in the form of the corresponding acid by known methods and the acid e.g. be prepared from the corresponding nitrii. They can be reacted with an ethylenediamine of the formula IV, preferably in the presence of a polar or apolar liquid medium. The reaction is preferably carried out at an elevated temperature.

The compounds of the formula I can be prepared from the imidohalide intermediates by reaction with an ethylenediamine of the formula IV, preferably under anhydrous conditions in the presence or absence of an acid acceptor and, if appropriate, at elevated temperature. The reaction mixture can contain a polar or apolar liquid medium, such as, for example, a lower alkanol or an ether.

The intermediate amidine in the form of the base or the acid addition salt is preferably converted into the compound of the formula I by heating under reflux with an ethylenediamine of the formula IV in the presence of a polar or apolar liquid medium, for example a lower alkanol, until ammonia no longer develops transferred. The amidine intermediates can be prepared by known processes, preferably from the corresponding imidates, by reaction with ammonia.

The thioamide and amide intermediates can be prepared, for example, from the corresponding nitriles or by other suitable methods and converted into the compounds of the formula I by heating with an ethylenediamine of the formula IV, for example at the reflux temperature or a higher temperature in the presence or absence of a polar or apolar solvent will. The reactions are preferably carried out in part under reduced pressure to remove ammonia and / or hydrogen sulfide from the reaction mixture.

The nitrile intermediates can be reacted in the presence or in the absence of a liquid medium with an ethylenediamine of the formula IV or one of its salts, which reaction can be carried out, for example, in the presence of hydrogen sulfide. A liquid medium, for example a lower alkanol, can be added to the reaction mixture, which is generally heated to reflux temperature or to a higher temperature, optionally in the presence of an inert gas, such as nitrogen, in a closed vessel.

If the intermediate product is the carboxylic acid, the ester or the thioamide, the acylethylenediamines of the formula VI can of course:

(VI)

CH2CH2täH2

CO.NH

are isolated, where X and Y have the meanings given above 25 and W is oxygen or sulfur. The invention further relates to the cyclization of a compound of the above formula VI. These compounds can be converted in situ to a compound of formula I, for example either by separate treatment with a dehydrating agent such as calcium oxide or by continuing the reaction until the reaction has ended under the original conditions, whereby a compound of formula I arises.

In a further process according to the invention, the compounds of the formula I are reacted by reacting a phenol or 35 amine of the formula VII or an O- or N-metal compound thereof: CH CH

J i 3

X-H

(VII)

wherein X has the meaning given above, with a compound of formula VIII:

N>

V- CH

(VIII)

CONH-

or one of their acid addition salts, in which Y has the meaning given above and V is a removable residue of an inorganic or organic acid. Suitable releasable radicals 60 are, for example, halogen, such as chlorine, iodine or bromine, alkylsulfonyloxy or arylsulfonyloxy, such as p-toluenesulfonyloxy.

The compounds of the formula VIII can be in the form of their bases or the acid addition salts. The reaction can be carried out, for example, in an inert liquid medium, preferably in a polar liquid such as acetonitrile or isopropanol or

Dimethyl sulfoxide, sulfolane, methyl ethyl ketone, dimethylformamide, acetone, dimethylacetamide, N-methyl-2-pyrrolidone or mixtures thereof. If V in formula VIII for chlorine

643 544

6

is preferably a small catalytic amount of an iodine salt, for example sodium iodide or a phase transfer catalyst, for example a quaternary ammonium salt such as benzyltrimethylammonium chloride, is added to the reaction mixture. The reagents can be heated to the reflux temperature of the mixture under an inert atmosphere, such as nitrogen.

According to a further process according to the invention, the compounds of the formula I are also obtained by reacting a compound of the formula IX:

CH, CH

-X-CH

, C

in which X has the meaning given above and P is a cleavable group, e.g. Halogen, acyl, alkoxy, alkylthio, S ~, SH, sulfonyloxy or carbalkoxy, with an active amine of the formula X:

Y

where Y has the meaning given above.

The compounds of formula I can be separated from the reaction mixture as a free base or in the form of an acid addition salt. The bases can be converted into their acid addition salts and the salts into the free bases or into other acid addition salts using a suitable acid.

The invention further relates to pesticidal preparations which contain a compound of formula I together with a carrier.

For use as pesticides, the compounds can be in the form of their acid addition salts or, preferably, the free bases. Suitable salts of the compounds of formula I are, for example, hydrohalide, sulfate, nitrate, phosphate, thio-cyanate, acetate, propionate, stearate, naphthenate, perchlorate, benzoate, methanesulfonate, ethanesulfonate, Tosylate and benzene sulfonate acid addition salts.

The compounds of formula I are used according to the invention for controlling arthropod pests; they can be used as pesticides for controlling insects, ticks, mites and other arthropods, including wild arthropods and the ectoparasites of plants, mammals and birds, alone or together with an additive which is in the form one or more of the known carriers, such as Wetting agents, diluents, stabilizers, thickeners, emulsifiers, dispersants or surface-active agents can be present, or other carrier components can be used.

The formulations can be used in the form of an aqueous solution of an acid addition salt of a compound of formula I or a suspension of a compound of formula I in water, alone or together with a suitable surfactant. The formulation can be applied alone or diluted with water to the pests or to their immediate environment by spraying or dipping.

The formulation may be in the form of a miscible oil containing a compound of formula I, in the form of its free base, or together with an equimolar amount of a suitable organic acid, e.g. Oleic acid or naphthenic acid, which form a salt which is soluble in organic solvents and which have emulsifiers and are applied as an emulsion by spraying or dipping.

The formulation can also be a non-aqueous solution or suspension of a compound of the formula I in a suitable organic solvent for direct application by the pour-on method. It can also be a wettable powder for dilution with water and use by dipping or spraying, other solid formulations for direct use without dilution such as dusts, powders or granules can also be used.

The formulation may also be a paste, an ointment or a gel containing a compound of formula I and a suitable carrier and can be applied by spreading over the infected area.

The pesticidal preparation preferably contains 5 to 80 wt .-%, in particular about 20 wt .-%, calculated as base, a compound of formula I in the form of an acid addition salt or a base. The concentration of the compound of the formula I, which is applied to the pests or to their immediate surroundings, is preferably 0.001 to 20% by weight, calculated as the base.

The invention relates to all new features described above, in particular:

a) new 2,3-dimethylphenoxyalkyl- or 2,3-dimethylanilinoal-kylimidazolines of the formula I and their acid addition salts;

b) a process for the preparation of the new compounds of formula I and their acid addition salts;

c) a method for controlling arthropod pests, in particular those of the order Acarina, by applying a compound of the formula I to the pests or to their surroundings, and d) pesticidal preparations containing a compound of the formula I and a carrier.

The following examples are intended to further illustrate the invention.

Example 1 :

1- [N- (4-Chlorophenyl) carbamoyl] -2- (2,3-dimethylanilino-methyl) -2-imidazoline

4.20 g (0.024 mol) of 2- (2,3-dimethylanilinomethyl) -2-imidazoline were stirred in 90 ml of methylene chloride, cooled to 0 ° C. and a solution of 3.66 g (0.024 mol) of 4-chlorophenyl isocyanate in 10 ml of methylene chloride added dropwise. A white precipitate quickly formed. After the addition, stirring was continued at 0 ° C for 2-3 hours, the temperature of the reaction mixture was allowed to rise to room temperature, and stirring was continued overnight. The reaction mixture was then evaporated to dryness under reduced pressure and the solid residue thus obtained was recrystallized from propan-2-ol, whereupon white crystals of

1- [N- (4-chlorophenyl) carbamoyl] -2- (2,3-dimethylanilinomethyl) -

2-imidazoline were obtained, melting point = mp 153 to 155 ° C.

Examples 2 to 6:

The compounds of Examples 2 to 6 were also prepared by processes analogous to those described in Example 1.

Example 2

1- [N- (4-bromophenyl) carbamoyl] -2- (2,3-dimethylphenoxymethyl) -2-imidazoline monohydrate, melting point = mp. 150 to 151 ° C (white powder).

Example 3:

1- [N- (4-methoxyphenyl) carbamoyl] -2- (2,3-dimethylphenoxymethyl) -2-imidazoline, melting point = mp. 126 to 127 "C (white powder).

5

10th

15

20th

25th

30th

35

40

45

50

55

60

65

7

643 544

Example 4:

1- [N- (4-nitrophenyl) carbamoyl] -2- (2,3-dimethylphenoxymethyl) -2-imidazoline monohydrate, melting point = mp. 182 to 185 ° C (light yellow powder).

Example 5:

1- [N- (4-Carbäthoxyphenyl) carbamoyl] -2- (2,3-dimethylphenoxymethyl) -2-imidazoline, melting point = mp. 153 ° C (white powder).

Example 6:

1- [N- (4-fluorophenyl) carbamoyl] -2- (2,3-dimethylphenoxymethyl) -2-imidazoline, melting point (impurity about 5%) = mp. 172 to 173 ° C.

Example 7:

A. Preparation of l- [N- (4-bromophenyl) carbamoyl] -2- (2,3-dimethylphenoxymethyl) -2-imidazoline

A solution of 20.4 g (1.0 mol) of 2- (2,3-dimethylphenoxy-methyl) -2-imidazoline in 300 ml of methylene chloride was cooled to -65 ° C. and a solution of 19.8 g for 30 minutes (1.0 mol) of 4-bromophenyl isocyanate in 300 ml of methylene chloride was added dropwise. The temperature of the reaction mixture was then allowed to rise to room temperature and the mixture was left for 2 hours, whereupon a precipitate formed. The reaction mixture was evaporated to dryness under reduced pressure, the residue was recrystallized from acetone and gave l- [N- (4-bromophenyl) carbamoyl] -2- (2,3-dimethylphenoxymethyl) -2-imidazoline monohydrate, melting point = mp. 150 to 151 ° C.

B. About the n-chlorocarbamoyl adduct of 2- (2,3-dimethylphenoxy-methyl) -2-imidazoline

A 17% solution of phosgene in toluene (3.2 g, containing 0.5521 g, 0.00549 mol COCl2) in 15 ml dry chloroform was slowly added to a solution of 2.40 g with stirring at 0 ° C ( 0.0115 mol) of 2- (2,3-dimethylphenoxymethyl) -2-imidazoline in 20 ml of dry chloroform was added. After the addition had ended, the reaction mixture was left to stand at room temperature for 2 h, diluted with an equal volume of dry diethyl ether and filtered quickly. The filtrate containing the N-chlorocarbamoyl adduct of 2- (2,3-dimethylphenoxymethyl) -2-imidazoline was treated with 1.22 g (0.00714 mol) of freshly distilled dry 4-bro-maniline and the mixture overnight Allow to stand at room temperature, whereupon the thin layer chromatogram showed that the main compound was the desired product. The mixture was evaporated to dryness in vacuo and the residue was taken up in a mixture of aqueous sodium carbonate and dichloromethane. The organic layer was washed with water, dried over magnesium sulfate and evaporated to dryness. A residue remained which, after purification, as described under A, gave l- [N- (4-bromophenyl) carbamoyl] -2- (2,3-dimethylphenoxymethyl) -2-imidazoline, which was identical to that described in A. .

Examples 8-10

The following compounds were prepared by processes analogous to those described in Example 1:

1- [N- (4-Methylphenyl) carbamoyl] -2- (2,3-dimethylanilino-methyl) -2-imidazoline, melting point = mp. 154 to 155 ° C; l- [N- (4-cyanophenyl) carbamoyl] -2- (2,3-dimethylanilinomethyl) -2-imidazoline, and l- [N- (4-bromophenyl) carbamoyl] -2- (2,3-dimethylanilinomethyl) -2-imidazoline, melting point = mp. 161.6 to 162.2 ° C.

Example 11:

Using the procedure of Example 1, except that no recrystallization step is used, l- [N- (4-dimethylsulfonamidophenyl) carbamoyl] -2- (2,3-dimethyl-

anilinomethyl) -2-imidazoline, melting point = mp. 151 to 153 ° C.

Example 12:

Soaked female ticks of the Biarra strain from Boophilus microplus are immersed in groups of 20 ticks per concentration in liquid preparations of a dilution series of the compound to be tested. The liquid is prepared immediately before the io test by diluting the compound to be tested with water. The ingredients can be in the form of miscible oil preparations or mesh powder. The concentration range desired for the experiment is obtained by further dilution of the stock solution or liquid.

15

The ticks are removed from the liquid after 10 minutes and the back is stuck on double-sided adhesive strips. They remain in this position for 14 days, after which the number of viable egg-laying ticks is determined. A regression line is drawn from this number (concentration against inhibition of egg production in percent) and the IR99 (concentration at which there is a 99% inhibition of egg production) is derived.

The results obtained are shown in Table 25 below:

table

30th

connection

Example No.

IR99 (%)

l- [N- (4-chlorophenyl) carbamoyl] -2-

(2,3-dimethylanilinomethyl) -2-

imidazoline

1

0.029

35

l- [N- (4-bromophenyl) carbamoyl] -2-

(2,3-dimethylphenoxymethyl) -2-

imidazoline

2nd

0.0095

1 - [N- (4-methoxyphenyl) carbamoy 1] -

2- (2,3-dimethylphenoxy) -2-imida-

40

zolin

3rd

0.0038

l- [N- (4-nitrophenyl) carbamoyl] -2-

(2,3-dimethylphenoxymethyl) -2-

imidazoline hydrate

4th

0.010

1 - [N- (4-Carbäthoxypheny l) carba-

45

moyl] -2- (2,3-dimethylphenoxyme-

thyl) -2-imidazoline

5

0.019

The following preparations are mentioned to show the way in which the pesticide compounds according to the invention can be applied to the pests or to the environment which is infested by the pests:

. Preparation 1:

Dust powder

Active ingredient talc

1.0 part by weight 99.0 parts by weight

60

20.0 parts by weight 80.0 parts by weight 100.0 parts by weight 100.0 parts by weight

Preparation 2:

Mesh powder

Active ingredient j sodium dicotyl sulfosuccinate dispersol ACA kaolin

25.0 parts by weight 1.0 part by weight 2.0 parts by weight 72.0 parts by weight 100.0 parts by weight

643 544

Preparation 3:

Aqueous dispersion active ingredient Keltrol

Sodium dioctyl sulfosuccinate water

Preparation 4: Infusion preparation active ingredient dimethylformamide castor oil

20.0 parts by weight '0.4 parts by weight 0.5 parts by weight

79.1 parts by weight 100.0 parts by weight

Preparation 5: fat

Active ingredient petroleum jelly

Preparation 6: 10 Miscible oil

5.0 parts by weight 85.0 parts by weight 10.0 parts by weight 100.0 parts by weight 15

Compound of Example 3 Aromasol H nonylphenol ethoxylate

6.0 parts by weight 94.0 parts by weight 100.0 parts by weight

10.0 parts by weight 70.0 parts by weight 20.0 parts by weight 100.0 parts by weight

stability

The compound of Example 1 had a half-life of greater than 6 months in an aqueous medium of pH 7, while that of 2- (2,3-dimethylphenoxy) -2-imidazoline was about 2 weeks.

Claims (25)

643 544 2nd PATENT CLAIMS 1. Compound of formula (I): X-CH CH ^ CH ^ (Ii) io or one of its acid addition salts, in which X has the meaning given in claim 1, with an isocyanate of the formula: 0 = C = N or one of their acid addition salts, wherein X is oxygen or NH, and Y is bromine, fluorine, iodine, —N02, —OR, —C02R, - CONR'R2 or - SC ^ NR ^ 2, or if X is NH, Y can also stand for Cl, CN or alkyl with 1 to 4 carbon atoms, R is an alkyl group having 1 to 18 carbon atoms, and R1 and R2, which may be the same or different, represent hydrogen or an alkyl group having 1 to 18 carbon atoms. 2. A compound according to claim 1, in which Y is —OR or —C02R is where R is an alkyl group of 1 to 4 or 12 to 18 carbon atoms. 3. A compound according to claim 1, wherein Y is - CONR'R2 or - SO2NR1R2, wherein R1 and R2, which may be the same or different, represent hydrogen or an alkyl group having 1 to 4 or 12 to 18 carbon atoms. 4. A compound according to claim 3, wherein either R1 or R2 represents an alkyl group having 12 to 18 carbon atoms. 5. A compound according to claim 1 of formula (Ia): CH3 ^ CH3 ^ A wherein Y has the meaning given in claim 1, or with a compound of the formula (III): X -CO.NH // \\ (in) 25 wherein Y has the meaning given in claim 1 and X1 is a cleavable group, and then optionally converting the compound of formula (I) into an acid addition salt or the acid addition salt of formula (I) into the free base or another acid addition salt. 10. A process for the preparation of a compound of formula (I) according to claim 1, characterized in that a compound of formula (IV): H2N.CH2CH2NH.CO, (IV) X-CH or one of its salts, in which Y has the meaning given in claim 1, with a compound of the formula (V): (Ia) (V) x-ch2-q CO-NH or one of their acid addition salts, wherein X is oxygen or NH and Y1 is fluorine, bromine, —N02, CH30— or - C02C2H5 or X NH and Y1 is chlorine. 6. One of the following compounds according to claim 1: 1- [N- (4-methoxyphenyl) carbamoyl] -2- (2,3-dimethylphenoxymeth-yl) -2-imidazoline, 1- [N- (4-chlorophenyl) carbamoyl ] -2- (2,3-dimethyl-anilinomethyl) -2-imidazoline, 1 - [N- (4-bromophenyl) carbamoyl] -2- (2,3-dimethylphenoxymethyl) -2-imidazoline, 1 - [N- (4-nitrophenyl) carbamoyl] -2- (2,3-dimethylphenoxymethyl) -2-imidazoline, l- [N- (4-fluorophenyl) carbamoyl] -2- (2,3-dimethylphenoxymethyl) -2-imide- azoline and l- [N- (4-bromophenyl) carbamoyl] -2- (2,3-dimethyl-anilinomethyl) -2-imidazoline or one of its acid addition salts. 7. l- [N- (4-chlorophenyl) carbamoyl] -2- (2,3-dimethylanilino-methyl) -2-imidazoline or one of its acid addition salts as a compound according to claim 1. 8. l- [N- (4-chlorophenyl) carbamoyl] -2- (2,3-dimethylanilino-methyl) -2-imidazoline as a compound according to claim 1. 9. A process for the preparation of a compound of formula (I) according to claim 1, characterized in that a compound of formula (II): wherein X has the meaning given in claim 1 and Q is a carboxyl group or one of its reactive functional derivatives, and then, if appropriate, the compound of the formula (I) in an acid addition salt or the acid addition salt of the formula so (I) in the free base or transferred other acid addition salt. 11. A process for the preparation of a compound of formula (I) according to claim 1, characterized in that a compound of formula (VI): (VI) CH2CH2NH2 CO.NH wherein X and Y have the meaning given in claim 1 and W is oxygen or sulfur, cyclized and then optionally 3rd 643 544 converting the compound of formula (I) into an acid addition salt or the acid addition salt of formula (I) into the free base or another acid addition salt. 12. A process for the preparation of a compound of formula (I) according to claim 1, characterized in that a phenol or amine of formula (VII): (VII) X-H or one of its O- or N-metal compounds, in which X has the meaning given in claim 1, with a compound of the formula (VIII): M V- CH (VIII), CONH- or one of its acid addition salts, in which Y has the meaning given in claim 1 and V represents a cleavable group based on an inorganic or organic acid, and then, if appropriate, the compound of the formula (I) in an acid addition salt or the acid addition salt of the formula (I) converted to the free base or another acid addition salt. 13. A process for the preparation of a compound of formula (I) according to claim 1, characterized in that a compound of formula (IX): 30th 17. Preparation according to claim 16, characterized in that the carrier is a suspending agent. 18. Preparation according to one of claims 14 to 17 in the form of an aqueous solution or suspension, a miscible oil, a non-aqueous solution or suspension, a paste, an ointment, a gel, a wettable powder, in the form of dust, Powder or granules. 19. Preparation according to one of claims 14 to 18, characterized in that it contains 5 to 80 wt .-%, calculated as the free base, of a compound of formula (I). 20. Preparation according to one of claims 14 to 19, characterized in that it contains l- [N- (4-chlorophenyl) carbamoyl] -2- (2,3-dimethylanilinomethyl) -2-imidazoline. 21. Preparation according to claim 20 in the form of a wettable powder. 22. Preparation according to claim 20 in the form of a miscible oil. 23. A method for controlling arthropod pests, characterized in that a compound according to any one of claims 1 to 8 is applied to the pests or their environment. 24. The method according to claim 23, characterized in that pests of the order Acarina are combated. 25. The method according to any one of claims 23 or 24, characterized in that ectoparasites are controlled in mammals or birds. 26. The method according to any one of claims 23 to 25, characterized in that the compound is applied by spraying, dusting or dipping. 27. The method according to any one of claims 23 to 26, characterized in that 0.001 to 20 wt .-%, calculated as the free base, of a compound of formula (I) is applied to the pests or to their environment. 28. The method according to any one of claims 23 to 27, characterized in that l- [N- (4-chlorophenyl) carbamoyl] -2- (2,3-dimethylanilinomethyl) -2-imidazoline is applied. X-CH 40 (IX) wherein X has the meaning given in claim 1 and P represents a cleavable group, with an amine of the formula (X):