CA1109787A - Imidazoline derivatives and their pesticidal use - Google Patents

Abstract

ABSTRACT OF THE DISCLOSURE

Ectoparasiticidal compositions are disclosed containing as active ingredient 2-(2'-methyl-3'-chlorophenylaminomethyl)-2-imidazoline or an acid addition salt thereof, particularly the hydrochloride. The compositions are effective against ectoparasites, such as ticks and mites.

Description

The presen~ inven~ion relates to cornpositions for comba~ing eetoparasi~es and microorganisms, and also to the use o~ these compositions for combating ectoparasites and microorganisms.
The compositions according to the invention contain as active ingredient at least one compound of the formula I

~ ~ ~ Cl)2-N _ ~ R5 (I) wherein .
Rl represents hydrogen or al~yl having 1 to 10 carbon atoms, R2 represents hydrogen, alkyl having 1 to 10 carbon atoms, or phenyl optionally substituted by alkyl having 1 to 5 carboL. atoms, alkoxy having 1 to 5 carbon atoms, thioalkyl having 1 to 5 carbon atoms, hy~roxyl, halogen, nitro, cyano or the trifluoromethyl group, -~R3, R4 and R~ independently of one another represent hydrogen, alkyl having 1 to 5 carbon atoms, alkoxy having 1 to 5 carbon atoms, alkylthio having 1 to 5 carbon atoms, hydroxyl, halogen, nitro, cyano or the trifluoromethyl group, or R3 and R4 in neighboring position together represent the 1,4-butadienyl group, whilst R5 has one of the given meanings, or at least one acid addition salt of the compounds of the for~ula I. 2 -~

. ~ , ' 0~7 B~ alliyl gro~lps or by alkyl as part o~ another group aremeant, depending on the number o~ the given carbon atoms~
both straight-chain and branched-chain alkyl groups. These include tlne methyL group and ethyl group, and also the isomers of the propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl and decyl groups.
Halogen denotes according to the formula I fluorine, chlorine, bromine and iodine.
The compounds of the formula I can be converted by methods known per se into their acid addition salts, and in this respect the hydrochlorides are to be considered as being preferred.
Besides hydrochloric acid~ suitable acids for forming salts are, for example, hydrobromic acid, hydriodic acid, sulphuric acid, phosphoric acid, nitric acid, ~cetic acid, propionic acid, butyric acid, valeric acid, oxalic acid, malonic acid, succinic acid, malic acid, maleic acid, fumaric acid, lactic acid, tartaric acid, citric acid, benzoic acid, phthalic acid, cinnamic acid and salicylic acid.
Some of the compounds embraced by the general formula I are novel, some are known; those which are known have been described hitherto as being pharmacologically effective in the spheL-e of the cardiovascular system (see ~nglish Pa~ent Specification No.
1,i74,349). The novel compounds of the formula I are likewise part of the invention.

. i )97~7 Tl~e compounds of the fol~mula 1 can be ~roduced by methods kno~n peL- se. Tlley can lie produced, for e~sample, by the metl~ods of synthesis whicll are shown below in schematic form:

a) 4~ NH-R2 + Cl-CH2--~ ~ . HCl R3 ~'1 5~ N-CH2 4 R3 . Rl R5 ~ ~ R2 ~NH . HCl b) 4 ~ N-C~2-C \ ~ ~H2- ~2~CH2 hHP`l C) ~ CH2'-C ~ + N

( I) , - ; ~ . . :
' .:

~1~9787 d) 5 ~ X2 R4 ~\~ ~ N_cll2_c N ~12 C1l2 C}~2-~l~l ~ C1~3-C~l4-So31 , ( I) Rl to R5 have the meanings given under the formula I.
The process is performed at a temperature of between 40 and 180C and in the presence of anhydrous solvents, or al~erna-tively without solvents. Exar.lples of suitable solvents are alcohols, aliphatic and aromatic hydrocarbon~, chlorina~ed ,, ,. , .~ ~.. ....
hydrocarbons, ethers such as ~ioxane, '~-F, or ~etones such as acetone and rnethyl ethyl ketone.
The syntheses referred to ~re kno~n from the li~era~ure and are described in: US~ Patent Specification No. 2,252,723;
Helv. Chimica Acta 33, 1386 (1~50); USA Patent Specification No.

~:" ~ . .

2,252,721; and British ~atent Specification No. 1,174,349.
The individual starting rnaterials and production thereof are ~nown from:

. . .

Cl-CH2 ~ ¦ . HCl Helv. Chimica Acta 27, 1762 (1944) I - Swiss Patent Spec. No. 229,606 H

,~

:

C112 -C-N Helv . Chimica Acl:a 3 7, R4~ 166 (1954) R5 NH . HCl C112-C ~ and R4~ NH-CH2-G ~ USA ]'atent Spec. No. Z,252,721 n ' ..

' ' ., .
, :, :
' ~

g~

The following Ex~nples serve to illustrate the production of the compounds of the formula I;
E~ample 1 (Method a) Production of 2-(4'-clllorophenylaminomethyl)-2-imidazoline hydrochloride (Compound ~o. 1.1) 31 g of 2-chloromethyl-2-imidazoline hydrochloride is refluxed with 51 g of 4-chloroaniline in 65 ml of abs. ethanol for 3 hours. After cooling, the substance which has crystallised out is filtered off with suction and recrystallised from water.
to yield 39 g (79% of theory) of the final product, m.p. 198-199C.

Example 2 (Method a) 2-(2',3'-Dimethylphenylaminomethyl)-2-imidazoline hydrochloride (Compound No. 2.6) .
31.0 g of 2-chloromethyl-2-imidazoline hydrochloride is refluxed wi~h 48.4 g of 2,3-dimethylaniline in 65 ml of abs.
ethanol for 5 hours. After cooling, the substance which has crystallised out is filtered off with suction and recrystallised from water. There is obtained 36.0 g (= 77% yield) of the final product, m.p.: 242C.

Example 3 (Method d) 2-~2'~3'-Dimethylphenylam omethyl)-2-imidazoline (Comp. No. 2.26) 26.4 g of 2,3-dimethylphenyl-aminoacetonitrile and 39.4 g of ethyl~nediamine toluenesulphonate are placed together and heated at 140C until the evolution of a~nonia has ceased.
To the oily reaction product is added 15Q ml of 15% aqueous sodium hydroxide solution, and extraction is perforr.led three times with 100 ml of methylene chloride each time. The combined methylene chloride extracts are washed with water, dried with sodium sulphate and filtered off, and the solvent is distilled off. The dark oil remaining behind is distilled in vacuo to yield 13.6 g (39.4% of theory) of 2-(2',3'-dimethylphenylamino-methyl)-2-imidazoline in the form of oil, b.p. 154-160C/
0.2 Torr, which solidifies on standing to form crystals having a melting point of 80 - 82C.

11~7 T~e follo~ing comp~unds, divided into Group I (known compounds) and Gl-oup II (novel compounds), are produced analogously to the illustrative Examples or analogously to the other processes given.

Rl 3 Group I
No. Rl K2 K3 R4 R5 Salt Melting point in C
, . . .

1.1 H H H H 4-Cl HCl l98-199 1.2 H 11 2-Cl H H HCl 263 1.3 H H 2-C113 H 4-Cl HCl 257 1.4 H H H 3-Cl H HCl 203 1.5~ H H 2-CH3 H H HCl 230 1.6 H H 2 -Cl H 4-Cl HCl 285 1.7 H H 2-Cl H 6-Cl HCl 276-280 1.8 H H H H 4-CH3 HCl 162 1.9 H H H 3-CH3 H HCl 202 1.10 H H H H 4-OC~3 HC1 165 1.11 H H 2 -OCH3 H H HCl 202 1.12 H H 2-CH3 H 4-CH3 HCl 23C~-232 1.13.H .__.___ 2-CH3 H 5-CH3 HCl 211-213 1.14 H H H 4 -N2 HCl . 230 1.15 H H 2~No2 H H HCl 210 -220 1 .16H H 2-CH3 3-Cl H HCl 263-264 1.17~1 ~l . 2 -CH3 H 5-Cl HCl 241-243 1.18 H H H 3-Cl 4 -CH3 HCl 207-209 1.19 H H H H ' H HCl 180-182 1.20 ~ c~3 H _ ~ ~Cl 225-22?

11~g7~7 Group Il No. Rl R2 R3 4 R5 Salt point C
_ .. _ ~ _ . .. _ ~ . __ 2.1 H H 2 -CH3 H 6 -CI~3 HC 1 2 35 -242 2.2 ~.~ H 2-F H H HC1 246 2.3 H H 2-Br H H HC1 245 2.4 H H H H 4-Br HC 1 2]6-217 2,5 H H H H 4-F HC1 l85 2 . 6 H H 2 -CH3 3 -CH3 H HC1 242 2.7~ H H 2-Cl H 5-Cl HCl 282 2.8 H H 2-Cl 3 -Cl ~ HCl 260 2.9 H H H 3 C 1 5 -C 1 HC 1 240 2.10 H H H 3-C1 4-C1 HC1 230 2.11 H H H 3-CF3 H HC1 2.12 H H H 3~CH3 5-CH3 HCl220 2.13 H H H 3-CH3 4-CH3 HCl 195 2.14 H H H 3-F H HC1203 2.15 H H 3-Br ~ IIC1205 2.16 H H 2~C1 4-C1 5;C1 HCl~ 250 2.17 ~1 H 2-~r }I 4-Br H C l 24 0 2 . 18 H H 2 -CH3 - 3 -CH3 6 -CIi3 HC 1215 ':' . . . .
2 . 1 9 CH 3 H 2 -CH 3 3~- -CH3 H IIC l 1 90 - 1 92 2 . 20 CH3 CH3 . 2-CII~ 3-CH3 H ~ICl183 - 184 2 . 21 CH3 H 2 -Cl ~ 3-Cl H ~Cl226 - 227 2 . 22 CH3 CH3 2-C1 3-Cl H llCl l9C-l91 2.23 CH 3 H 2 -CH 3 3-C1 H HC l 2 12 - 2 14 2 . 24 CH3 CH3 2 -CH3 3 Cl H . HC1 2.25 lI CH3 2-CH3 3-C}13 H }-IC1 182 - 183 2 . 26 H H 2-C~I3 3-CH3 H _ ~;0-~2 .

; N~. Rl R2 R3 4 ~5 sal t ~le 1 t ~n~C

2.27 H H H ~ CF3 H HCl 2.28 H H 2-Cl 4-Cl 6-Cl HCl 2.29 H H 2-~r H 4-Br HCl 2.30 H H 2-CH3 4-CH3 6-CH~ HCl 2.31 CH3 H 2-CH3 4-CH3 H HCl 2.32 CH3 CH3 2-CH3 4-CH3 H HCl 2.33 CH3 H 2-Cl 4-Cl H HCl 2.34 CH3 CH3 2-Cl 4-Cl H HCl 2.35 CH3 H 2-CH3 4-Cl H HCl 2.36 CH3 CH3 2-CH3 4-Cl H HCl 2.37 H CH3 2-CH3 4~CH3 H HCl 2.38 H H 2-CH3 4-CH3 H _ 2.39 CH3 H H H 4-Cl HCl ` 2.40 CH3 CH3 H H 4-Cl HCl 2.41 H H H H 4-Cl _ . 2.42 H H 3-NO2 4-F H HCl 2.43 H H 3-NO2 H H HCl 2.44 H H H H 4-J HCl 2.45 H H 3-J H H HCl 2.46 H H 3-OCH3 H H HCl 2.47 H CH3 2-CH3 4-Cl H HCl 2.48 H H 2-SCH3 H H HCl 2.49 H H 2-01-1 H H ~Cl 2.5~ H H 3-CN H H HCl 2.51 C5Hll H H H 4-Cl HCl 2.52 HC4Hg(n H ~ H 4-Cl HCl 2.53 H Cl ~ H H 4-Cl HCl 2.54 H Cl ~ - H H 4-Cl HCl ' - 11 - .

l~g7~

No. ~2 ¦ 1~3 4 ¦ Rs Salt ¦ polnt gC
~ __ _. j . .
2 ~ 5~ C~3 H 2-CH3 4~Cl H HCl 2 ~ 5~ ~13 ~,H3 2-CH3 4-Cl H HCl 2. 60 11 C}~3 2-CH3 4-Cl H ~ICl 2 . 61 . }~ H 2-SCH3 H H HCl 2. 62 H H 2~0H H H HCl 2. 63 H H 3-CN H ~ HCl 2 . 64 c5H 1 ] H H H 4 -C l HC l 2. 65 H ¦ C4H9(n) 11 H 4-Cl HCl 2 . 66 ~ ~C l_~_ H H 4 -C 1 HC 1 2.67 ~ 'Cl~ ~ 4-Cl I I~Cl , : , . .
.

;

... .
- .. .... . .

It has been discovered that the compounds of the formula I
as such or as constituents of the compositions according to the invention surprisingly have valuable ectoparacitic properties.
They are suitable in particular for combating mites (Acarina), but preferably for combating parasitic ticks (Ixodidae). This applies to all stages of monoxenous and heteroxenous species of ticks, as ~ell as to the inhibition of oviposition, both with respect to normally sensitive strains and to strains that are resistant to compounds such as phosphoric acid esters and carbamates and to other already known pesticides for combating ticks. Furthermore, these compounds have a marked detaching effect, which is of speclal importance for the treatment of host animals already infested (e.g. cattle or rabbits). The detaching effect co~nences immediately after application of the active substance, as a consequence of which the ticks are prevented from continuing the absorption of their food, namely the extraction of blood. They detach themselves in the course of treatment from the host animal, the end effect of which is the complete removal of the pests from the treated animal.
Species of tic~s which can be thus combated include, f~r example, Amblyomma, Rhipicephalus and Boophilus.
Compounds to be mentioned as having a particularly marked 2ctoparasitic action are those of the formula Ia 2 ~ ~ R5 Rl R3 4 wherein Rl, R2, R3 and R4 have the meanings given under the formula I, and R5 represents hydrogen.
The ~ollowing compounds are characterised by having an outstanding acaricidal action:
2-(2',3'-dimethylphenylaminomethyl)-2-imidazoline hydrochloride, 2-(2',3'-dichlorophenylaminomethyl)-2-imidazoline hydrochloride, 2-(2'-methyl-3'-chlorophenylaminomethyl)-2-imidazoline hydro-chloride.
In addition, the compounds of the formula I and the compositions containing them have been recognised as being effective against lice.
Example 4 Test to determine the effect on ticks: inhibition of oviposition The test insects used are females of the cattle tick Boophilus microplus which have sucked themselves full. There are treated with each concentration 10 ~icks o~ a resistant strain and 10 ticlcs of a normally sensitive strain. The ticlcs are immersed for a short time in aqueous emulsions or aqueous solutions of the salts of the compounds to be examined. They are fixed on plates covered with double adhesive tape and kept , -- .

" :

in an air-con~;tioned chamber under constant conditions. An evaluation is made after three weelcs, and the overall inhibi.tion of the oviposition of fertile eggs is determined.
The inhibitory effect of the substances is expressed in terms of the minimum su~stance concentration in ppm to produce a 100% effect against normally sensitive adult fernale ticks and resistant adult female ticks, respectively.

. .

` Results ...... ___ ___ ., .
~inimum concentration in ppm for 100% inl~ibitory - Compound effect sensitive ~ resistant .~ _ __ __ .__ l) 2-(2',3'-dimethylphenylaminomethyl)-2-imidazoline hyd~ochloride 50 50 2) 2-(2',3'-dichlorophellylaminomethyl)-2-imidazoline hydrochloride 50 50

3) 2-(2'-methyl-3'-chlorophenylamino-methyl)-2-imidazoline hydrochloride 100 100

4) 2-(2'-chlorophenylaminomethyl)-2-imidazoline hydrochloride -50 50

5) 2-(2'-fluorophenylaminomethyl)-2-imidazoline hydrochloride 50 50

6) 2-(3'-methylphenylaminomethyl)-2-imidazoline hydrochloride 100 100 Comparison _ _ . _ 2-(3,4-dicllorophenylimino)-N-n-butyl-pyrrolidine ('`Bimarit")1000 1000 .~ 2-(3,4-dichlorophenylimino)-3-methyl-thiazoline (Swiss Patent Specification No. 439,858) ~1000 ~ ~lO00 ~; 2-(3,4-dichlorophenylimino)-3-methyl-thiazo]ine-HCl (S~iss Patent Specification ~o. 4~9,85~) > 1000 ~ lO00 2-(4-chlorophenylimino)-3-methyl-thiazoline-HCl (Swiss Patent Specification No. 439,858) > 1000 ~ 1000 l-naphthyl-N-methylcarbamate ("Sevin"; U.S. Pat.Spec.No. 2,903,478) 1000 ~1000 .~ empir CloHloC18 (`'Toxaphen`'; U.S. Pat.Spec.1000 1000 No. 2,565,~71) _ _ ~ 7 ~ 7 Example 5 Test t:o deter)nine the effect on ticks: destroyin~ action at vari_ls sta~es of development As test objects are used larvae (in each case about 50), nymphs (in each case about 25) and imagines (in each case about 10) of the tick species Amblyomma hebraeum and Rhipice~halus bursa. The test insects are immersed for a short time in aqueous emulsions or solutions of the salts of the substances to be examined at a specific concentration. The emulsions or solutions in small test tubes are absorbed with cotton wool and the wetted test insects are then left in the contaminated test tubes. An evaluation with respect to larvae is made after 3 days, and with respect to nymphs and imagines after 14 days.
There is determined the minimum substance concentration ~hich effects a 100% destruc~ion (LCloo~, expressed in ppm of active ;~ substance relative to the total amount of emulsion or solution.

'

7~ 9 7 8 7 Resul~s ;

. _ CompoundA. hellraeum R. bursa Nymphs Larvae Imagines Larvae _ . _ ~ _ 1) 2-(2',3'-dimethyl-phen~771aminomethyl)-2-imidazoline hydro-chloride 1 1 50 2) 2-(2',3'-dichloro-phenylaminomethyl)-2-imidazoline 7nydro-chloride 1 1 100 1 . 3) 2-(2'-methyl-3'-: chlorophenylamino-s methyl)-2-imidazol-ine hydrochloride 1 1 0.1 0.1 -, .
' ~ Comparison ~ ~ . . _ . 2-(3,4-dichlorophenyl-., imino)-N-n-butylpyrro- ~
idine ("Bimarit") 100 100 100 10 l-naphthyl-N-methyl-~ arbanate 10 S 100 10 .. ("Sevin": US.PS 2,903,478) _ .
', :

,~

;

:

11~19787 The co~pounds of the formula I for ectopaL-asitic application are used on their own or together with suit~ble earriers and/or carL-iers and additives. Suitable/additives can be solid or liquid and they correspond to the substances common in formulation prac,ice sueh as natural or regenerated substances, solvents, dispersing agents, wetting agents, adhesives, thickeners and binders.
For application, the eompounds of the formula I can be processed in~o the form of dusts, emulsion concentrates, granulates, dispersions, sprays or solutions, the forrrlulation of these preparations being effeeted in a manner eommonly known in the art. The compositions according to the invention are produced in a manner known per se by the intimate mixing and/or grinding of the active substances of the formula I with suitable carriers, optionally with the addition of dispersing agents ~r solvents which are inert to the active substanees. The aetive substances ean be obtained and used in the following forms:
solid preparations: dusts, seattering agents, granules (coated /, ~" granules~ impregnated granules and homogeneous granules~;
liquid preparations:

a) water-dispersible concentrates of active substance:
- wettable powders, pastes or emulsions;
b) solutions: "pour-on".

The content of active substance in the described compositions is between 1 and 80%.

l~g78 7 Examl)le 6 Emulsion concentrate 20 parts by weight o active substance are dissolved in 70 parts by weigh, of xylene, and to the solution are added 10 parts by weight of an emulsifying agent consisting of a mixture of an arylphenyl polyglycol ether and the calcium salt of dodecylbenzenesulphonic acid. A milky emulsion is formed by adding water to the emulsion concentrate in the desired proportion.
Example 7 Emulsion concentrate . _ .
5 to a maximum of 30 parts by weight of active substance are dissolved at room temperature, with stirring, in 30 parts by weight of dibutylphthalate, 10 parts by weight of Solvent 200 ~low-viscous, highly aromatic petxoleum distillate) and 15 to 35 parts by l~eight of Dutrex 238 FC (viscous,~highly aromatic petroleum distillate; and to this solution are added 10 parts by weight o~ an emulsifier mixture consisting of castor oil polyglycol ether and the calcium salt of dodecylbenzene sulphonic acid. The emulsion concentrate thus obtained gives milky emulsions in water.
Example 8 Wettable J~o~der 5 to 30 parts by weight of ~he active substance are thoroughly ;

:
mi~ed, in a Mixing apparatus, with 5 parts by weigllt of an absorbent carrier (silicic acid K 320 or Wessalon S) and 55 to 80 parts by weight of a carrer (bolus alba or Kaolin B 24) and a dispersing agent mixture consisting of 5 parts by ~eigh~
o~ an Na-lauryl-sulphonate and 5 parts by weight of an alkyl-aryl polyglycol ether. This mixture is ground in a dowelled disc mill or in an air-jet mill to 5 - 15 ~m. The wettable powder obtained in this manner gives a good suspension in water.
Exar,tple 9 :
~ust 5 parts by weight of finely ground active substance are thoroughly mixed with 2 parts by weight of a precipitated silicic acid and 93 parts by welght of talcum.
.:~
`' Exam~le 10 ~ Pour-on so]ution .. ...
~ active subs.ance 30,0 g ; . .~
sodium dioctylsulphQsuccinate 3.0 g benzyl alcohol 4~.0 g peanut oil 19.8 g 100.8 g The active substance is dissolved in the benzyl alcohol with stirring and if necessary also with slight heating. To the solution are added the sodium dioctylsulphosuccinate and the peanut oil, and dissolved with heating and vigorous mixing.

mple 11 Pour-ollL sol.ution active substnnce 30.03 g sodium dioctylsulphosuccinate3.00 g benzyl alcohol 35.46 g ; ethylene glycol monomethyl ether 35.46 g 103.92 g = 100 ml The active substance is dissolved in the major part of the mixture of the two solvents with vigorous stirring. The sodium dioctylsulphosuccinate is subsequently dissolved, if necessary with heating, and the amount is made up with the remainder of the solvent mixture.

The compounds of the formula I and the compositions cont~ining them possess moreover for practical requirements a very favourable microbicidal spectrum for the protection of cultivated plants. Examples of cultivated plants which may be mentioned are: fruit trees, ornamental plants, grape vines, cucumber plants, solanaceae such as potatoes, particularly however peanuts, sugar-beet, banai~as, cotton and vegetables.
It is possible with the active substances of the formula I
or with the compositions containing them to check or destroy on plants or on parts of plants (fruits, blossom, foliage, stalks, tubers or roots) in these crops and in related crops of cultivated plants the f~ngi occurring, with p~rts of plants subseyuently growing also remaining protected from such fungi.

` 11~9~78~

The ~c~ive su~stances are effective against the phytopathogenic fungi belonginv to the following classes: Phycomycetes such as Plasmopara, Basidiomycetes such as Puccinia, Ascomycetes such as ~rysiphe, Venturia and Fusarium, particularly however Fungi ilr.perfecti such as Cercospora and Verticillium. Further-; more, the compounds of ~he formula I and the compositions containing them have a systemic action. They can also be used as dressing agents for the treatn7ent or seed (fruits, tubers or grain) and plant cuttings for protection against fungus infections and against phytopathogenic fungi occurring in the soil.

- Example 12 .
Action against Cercospora arachidicola on peanut plants ~Arachis hypogaea) Residual protective action Peanut plants 10 - 15 cm in height are sprayed with a spray liquor produced from wettable powder of the ac~ive substance (0.02% of active substance), and 48 hours later are infested witl~ a conidiospore suspension of the fungus. The infested plants are incubated for 24 hours at about 21C with high relative humidity, and subsequently placed in a greenhouse until appearance of the typical leaf spots. An assessment of the fungicidal action is made 12 days af~er infestation on the basis of the number and size of the spots occurring.
With the use ~f comp~unds of the formula I, inter alia ;

~1~9787 compoull~s Nos. 1.1, 1.3, 1.6, 2.3 and 2.~, infestation is reduced to less than 20~/~ of that occurring on untreated but infes~ed control plan~s.

E~amPl e 13 Action against Verticillium albo-atrum on cot-ton plants (Gossypium hirsutum) __ After 4 weeks' cultivation, cotton plants are damaged at the roots and infested witll a spore suspenslon of the wilt pathogen. After 24 hours, the infested plants are sprayed with a spray liquor prepared from wet-~àble po~der of the active substance (0.18~/~ of active substance). An evaluation is made after 14 days' incubation in a greenhouse at about 22C of the degree of wilt of the infested cotton plants.
l~lth the use of compounds of the formula I, e.g. compound 1.1, infestation is reduced to less than 20% of that occurring on untreated but infested control plants.

The compo~lnds of the formula I for microbicidai application are used on their own or together with suitable carriers and/or additives. Suitable additives can be solid or liquid and they correspond to the s~bstances common in formula practice, SUCIl as nat-lral or regenerated substances, solvents~ dispersing agen~s, wetting agents, adhesives, thickeners, binders or fertilisers.
The content of active substance in compositions for use con~mercially is between 0.1 and 90%.
For application~ the compounds of the formula I can be --`` llU9787 in the ~ollo~7i~g forms (the weight percentage figures in braclcets denote advantageous amounts o~ active substance):

solid prepar~tion~s: dusts and scat~ering agents (up to 10%);
granu]es (coated granules, impre~nated granules and llomogeneous granules) and pellets (1 to 80%) liquid preparations:
a) ~ater-dispersible concentra~es o~ active substance:-wettable-powders and pastes (25-90% in commercial package, 0.01 to 15% in ready-for-use solution); emulsion concentrates and solution concentrates (10 to 50%; 0.01 to 15% in ready-for-use solution);
b) solutions (0.1 to 20%); aerosols.

The ac~ive substances of the formula I of the present invention can be formulated for example as follo~s:

Example 14 The ~ollowing substances are used to produce a) a 5% dust and b) a 2% dust: --a) 5 parts of active substance, parts of talcum;
b) 2 parts oi active substance, 1 part of highl~ dispersed silicic acid, 97 parts o~ talcum.
The active substances are mixed and ground with the carriers and can be dusted on in this form.

E~
`
` ~ran~ ?~
-Tl~e follo~ing ingredlents are used to produce a 5% granulate:
parts of active substance, 0.25 part of epichlorollydrin, 0.25 part of cetyl polyglycol ether, 3.50 parts of polyethylene glycol, 91 parts of kaolin (particle size 0.3 - 0.~ mm).
The active su'~stance is mixed with epichlorohydrin and dissolved in 6 parts of acetone, and the polyetl~ylene glycol and cetyl polyglycol ether are ~hen added. The solution obtained is sprayed onto kaolin and the acetone is subsequently evaporated off in vacuo. A microgranulate of this kind is advantageously used for ccmbating soil fungi.

Example 16 ~ettable powder The follo~ing constituents are used to produce a) a 70%, b) a 40%, c) and d) a 25%, and e) a 10% ~et~able po~ider:
a) 70 parts of active substance, parts of sodium dibutylnaphthylsulphonate, 3 parts of naphthalenesulphonic acid/phenolsulphonlc acid/formaldehyde condensate 3:2:1, parts of kaolin, 12 parts of Champa~ne chalk;

~) 40 par~s of activ~ sul~stance, S parts of sodium lignin sulphona~e, 1 part o~ sodium dibutylnaphthalenesulphonate, 54 parts of silicic acid;
c) 25 parts o~ active substance, 4.5 parts of calcium lignin sulphona~e, 1.9 parts of Champagne chalk/hydroxyethylcellulose mixture (1:1), 1.5 parts of sodium dibutylnaphthalenesulpllonate, 19.5 parts of silicic acid, l9.S parts of Champagne chalk, 28.1 parts of kaolin;
d) 25 parts of active substance, 2.5 parts of isooctylphenoxy-polyoxyethylene-ethanol, 1.7 parts of Champagne chalk/hydroxyetl~ylcellulose mixture (1;1),

8.3 parts of sodium aluminium silicate, 16.5 parts o~ kieselguhr, 46 parts of kaolin;
e) 10 parts of active substance, 3 parts of a mixture of the sodium salts of saturated fatty alcohol sulphàtes, - S parts of naphthaLenesulphonic acid/formaldehyde condensate, 82 parts of kaolin.

The active su~stances are intimately mixed in suitable mixers ;

wl~h tl~e adclitives~ and the mixture ;s then ~round in the appropriate mills antl rolleL-s ~o ol~aln ~A~ettable powders which have e~cellen~ wetting and suspension prop2r~ies, which can be diluted with wa~er to give suspensions of the desired concentration and which can be used in particular for leaf application.

E~ample 17 Emu]siflable concentrate The following substances are used to procluce a 25%
emulsifiable concen~rate:
parts of active sub~tance, 2.5 parts of èpoxidised vegetable oil, parts of an alkylarylsulphona~e/fatty alcohol polyglycol ether mixture, parts of dimethylformamide, 57.5 parts of xylene.
Emulsions of the required concentration can be prepared from such concentrates by dilution with water, and these emulsions are particularly suitable for leaf app]ication.

For the broadening of the sphere of action of such compo-sitions, the compounds of the formula I can be used with other suitable pesticides or with active substances promoting plant grow~h.

Claims (6)

THE EMBODIMENTS OF THE INVENTION IN WHICH AN EXCLUSIVE
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:

1. Ectoparasiticidal composition containing as active ingredient 2-(2'-methyl-3'-chlorophenylaminomethyl)-2-imidazoline or an acid addition salt thereof with an inorganic or organic acid, together with a liquid or solid carrier or additive or a mixture thereof.

2. Ectoparasiticidal composition according to claim 1 wherein the carrier or additive is selected from the group consisting of natural or regenerated substances, solvents, emulsifying agents, dispersing agents, wetting agents, adhesives, thickeners and binders or mixtures thereof.

3. Ectoparasiticidal composition according to claim 1 or 2, wherein the active compound is 2-(2'-methyl-3'-chlorophenylaminomethyl)-2-imidazoline hydrochloride.

4. A method of combating ectoparasitic organisms which comprises ap-plying thereto an ectoparasiticidally effective amount of 2-(2'-methyl-3'-chlorophenylaminomethyl)-2-imidazoline or an acid addition salt thereof.

5. The method according to claim 4 of combating mites and ticks which comprises applying thereto an effective amount of 2-(2'-methyl-3'-chloro-phenylaminomethyl)-2-imidazoline or an acid addition salt thereof.

6. The method according to claim 5 which comprises applying to mites and ticks an effective amount of 2-(2'-methyl-3'-chlorophenylaminomethyl)-2-imidazoline hydrochloride.