DE1617414A1 - Wormer - Google Patents

Description

"Worming agent" Priority: S. September 1966, Jepan Registration Wr .: 41/48918 The subject of the invention is a worming agent for wern- or cold-blooded vertebrates, which is @ekennseichnet by an active ingredient content of an inidasole derivative of the general @@@ nen formula in which R1 is a hydrogen atom, a lower alkenyl, aralkyl, an alkyl radical optionally substituted in the # -position with a hydroxyl, cyano, amino or carbalkoxy group, or a radical of the general formula is, in which @ denotes a lower alkylene chain or a copper atom and where in both formulas R2 is a hydrogen atom, an alkyl or a phenyl radical optionally substituted with a nitro group, R3 is a hydrogen atom, a lower alkyl radical or an iitro group, R4 is a hydrogen atom or an Eitro group and Y is a ring nitrogen atom or a group of the general formula is, in which R3 represents a hydrogen atom, a lower alkonyl, aralkyl, phenyl, nitrophenyl or alkyl radical, which can optionally carry a hydroxyl group or carbalkuky group as a substituent in the # -position, and in which X represents an organic or inorganic acid radical .

The wormers according to the invention, which as an active ingredient one or more Compounds of the general formula I contain or consist thereof, can for Deworming of parasitic worms, e.g. B. trematodes, cestodes or nematodes infested warm-blooded animals, e.g. humans, domestic animals such as cats, dogs, pigs, Cattle, goats, Sohafen, horses, lifes, ruminants, poultry, laboratory animals, such as mice or rats, as well as of cold-blooded vertebrates, e.g. farmed fish, be used. The warming agents according to the invention can, however, also be used prophylactically be applied to warm-blooded or cold-blooded vertebrates from infestation with to protect parasitic worms by periodically treating the animals with the invention Anthelmintics treated.

Trematodes against which the wormers according to the invention are effective are, for example, are Clonorchis sinensis or amines heterocerca, are cestodes e.g. Diphyllobothrium erinacei, Reillietina tetragona or Dipylidium caninum. Nematodes, against which the wormer compositions according to the invention are effective are e.g.

Syphacia obvalata, Ancylostome tubaeforme, Enterobius vermioularis, Ancylostoma eaaainum and Dirofilaria initis.

Although because of the urgent need for effective wormers Numerous compounds have already been tested for anthelmintic effectiveness, It was hitherto unknown that compounds rom the type in the inventive Imidazole derivatives contained as active ingredients anthelmintic efficacy own.

The dosage of the wormers according to the invention depends of course of the compound used in each case as active ingredient and of how they each are administered, but it is generally inferior when administered orally 100 mg / kg. Table I below lists numerous active ingredients according to the invention Imidazole derivatives of formula 1 suitable for anthelmintics are listed.

Table I. Connecting application no. R1 R2 R3 R4 #Y R5 X- Snp. ° C 1 CH2- C1123- H- N- 5 - c} 13so11 197 - 198 2 C17H35-1? VI 3 Hoc2c2- dm23- II : = = II II = 3'3 '119 - 120 5 OC112cF½- C11H23 VI II? 1 IV IV 68 - 69.5 T able I (continued) pp ev II CC co: tr. .., O 3 00 rl rt 10 CH2 OH3- II fl II C12H25- - "- 109.8 11 'H0CH2CH2- II II 1? II 1? If 62 - 63 CH2 cu - H- H- VI CH? II 210-211 ii 'IV C11H23 IV II 1? 1? tI 150 - 151 II II 208 - 208> 5 T able I (continued) Connecting Application No. R1 R2 R3 R4 #Y R5 X- m.p. ° C II 125 - 126 21 H2 -'- C-CR2- II IV II 1? fl II 106-107 22 NC-CH2CH'2- IV? V VI IV Vf 59 - 62 23 II- II? I ft VI II viscous 1 'liquid' [mj¼ {% {\ OH2- T able I (continued) Connecting Application No. R1 R2 R3 R4 #Y R5 X- m.p. ° C 28 O2F; S00CH.? II / ½; ½50'cH2cH2 {U ~~~~~~~ il9 - 55 91-92 II 1? 1il2 - 1il3.5 tI IV 60 - 61 32 cH3c09cH 2CH2-017H35 II fl N ~~~~~~~~~~~ ~~~~~~~~~~~~~ 121 - 122 33 H- ~~~~~~~~~~~~ ~~~~~~~~~~~~~ 1113 - iLlil 311 H- ~~~~~~~~~~~ 127 - 128 ---- OH3- II II + R5 H- ----'--- HS04 36 H2N-CH2CH2CH2 IV II II II VI HC02C02 '198 - 199 T able I (continued) Connecting dung rr. n - nil #Y 'n5 Srip. --- C - ~~~~~~~~~~~~~ 19il - 195 39 1 $ OH 3- II H- 1eimarti HC02C02 <U N ~ ~ ~~~~~~~~~~~ ~ ~ ~~~~~~~~~~~~~ 127 111 II - II I II \ 5! H- 01 y½3-o 62 - 65, - 88> 5 C2H5-OH3- - 012H25- ci, .waxarti 115 OH2- OH3- IV, I - VI, - 207 - 208 St'p. OC r (, - n S OO 1 1 - CU 5 83 - .90. II -----; - 83 - 90, tk O2H5- Br I : - ----? 1 O2H5S011 ---- RI Ln - 136 V - -D -a105 - 105> 7 i '. II 1? 105 - 105>'7 290-2911; ~~~~~~~~~~ 290 - 291 2115 - 2118 ~~~~~~~~~ ~~~~~~~~~~~~ 2115 - 2118 L f OH '- ci 189-190 i115i116,3L \\ 'IV H0CH2CH2- IV 1115 .1116s3 T able I (continued) Connecting dung flr. R1 n2 R5 - 0 55 OH3? H2cH'2 oH - ~~~~ ~~~~~~~~~~~ 79 - 80 C11H c3. 02H580il »2.005-201, - -. , .-- ---- - 57 II CH3S03 l, 33 1311 j -I H- 'II, 11f1'& ssig #x IR # X 92-93 66 s C2 VI OH3- H'M / \ s03 92 - 93, 61 H0CH2OH2- OH3- NO2- VI N ~~~~~~~~~ ~~~~~~~~~~~ 129 - 130 R ~~~~~~~~~~~~~. 157 - 158 Ln 2 & 7 - 2118 T able I (continued) Connecting application no. Ln R2 R3 R11 - n5 Sn.p. 0 611 H30, O 00H2OH2- II II II - II ~~~~~~~~~ ~~~~~~~~~~~ 1110 - 1111 65 CH2: CH- OH3- H- H- '1? ~~~~~~ R HP0 66 - II V IV Vf -1111 - 115 67 OH2- 010H, 21-? I 1? VI a2l11 170 - 171 U fl 'C12H25- IV II VI II IV' i116-i118 69 IV O10H21- VI IV IV CH3CH / 903 1111-115 31, X- M OH32 II VI IV IV c3o- - 201 - 202 OioH2l 17 IV IV OH 3- 106 - VI IV II CH2- cl 105 - Table I (continued) Verb in-1? y - 0 v; rr. n1 E2 nil - 5 .rp. C. .--- I - 73 0112 C12H25- II VI VI OH 3 - OH3S011 191 - 192 o - ~ -. 711 22 0111123 VI VI IV O12H25- cl 89D5 - 90.5 cr5 O12H25 VI II VI VI OH 3 cH3s0) I ,, 82 76 VI CH3 Ms03i252'l26 77 Compounds No. 1 to 12, 14, 15, 17, 19, 20, 22 to 32, 35 to 39, 41 to 50, 52 to 64, 66 and 67 are new.

The imidazole derivatives contained in the worming agents according to the invention can be prepared in accordance with the examples given below in the form of reaction equations (1) H2NO112CH2NE2 + C11R23CN ~ IN HNv - vvN 11h} C11823 2 CK2Cl aH N you23 e2) c7 tctra N2NCB2OllNK2 + cN fj D.iwdrenni im CD CH, PCHN -CH2CN2- mr "lss w XOcHaCKr ß The active ingredients of the wormers according to the invention can be used pure or in a mixture with a liquid, solid or gaseous carrier or diluent in the form of powders, granules, tablets, capsules, injection solutions or suspensions or as a syrup. They can also be administered to animals mixed with the feed. For the treatment of fish, wormer compositions according to the invention can not only be administered orally, but can also be used in the form of a Madisin bath.

Preferred carrier or diluent is a potassium carbonate, kaolin, Starch, lactose and alcohol. Are the active ingredients of the wormers according to the invention in combination with a surface active agent, an anti-diarrheal agent or used with antibiotics, an increased effect is to be expected.

The invention is further illustrated by the following experimental examples explains the anthelmintic effectiveness of the worming agents according to the invention show compounds contained as active ingredients. The numbering of the connections corresponds to that of Table 1.

Experimental Example 1 Efficacy against the mouse nematode, Syphaoia obvelata.

1. Test animals and methods: The test animals were 6 weeks used old male mice that were naturally infected with Syphaoia obvelata was. The mice were housed in aluminum cages. Per kg body weight 15-100 mg of the compound to be tested for effectiveness were administered orally. The worming of the nose to be examined was started 2 days before the wormer administration Checked daily up to 5 days after the application of the worming agent by the worm removed from the anus using cellophane tape. The ones with these Strips of isolated worm eggs were oweils identified under a microscope and counted. 5 days after the administration of the worm medium, the number of survivors was determined Worms found in the host cocoon by autopsy.

2. Results: Table II shows the effectiveness of the various tested connections.

In this table: +++ means that the number of those eliminated Worm eggs decreased to 0 1 to 2 days after the administration of the worming agent, and this value remained at this value until the end of the experiment, ++ that the number of excreted Worm eggs decreased to 0 and 3 to 5 days after the worming agent was administered + that the number of excreted worm eggs 5 days after administration of the Wurmittelas to less al. 10% of the number of worm eggs excreted before administration went back.

Link decrease in number No. of eggs 2 ++ 4 +++ 5 ++ 6 ++ 7 + 8 + 9 ++ 10 11 + 12 + 13 14 +++ F 15 + 16 17 ++ 18 ++ 19 ++ 20 + 23 + 24 + 25 + 26 + 28 + 29 ++ 30 + 31 + 32 + 33 + 34 + 35 + 37 ++ connection decrease the number No. of beers 38 + 39 + 40 ++ 42 ++ 43 + 44 ++ 46 + 47 ++ 49 + 51 + 52 + 53 + 54 + 55 + 56 + 57 + 58 + 59 + 60 + 61 + 62 +++ 63 + 64 + 65 + 66 + 67 ++ 68 + 69 + 70 + 71 + 72 + 73 + Of the anthelmintics examined are the compounds Nos. 1, 4, 10, 13, 14, 16 and 62 are particularly effective. The exact numerical values of the experiments with these compounds are listed in Table IIX.

Table III Connection Dose Number of eggs boiled out dung, mg / kg before administration / after administration No. 2 1 1 2 3 4 5 Days days 1 30 63 51 0 20 11 27 167 4 15 177 276 110 17 0 0 0 10 100 43 15 1 2 0 0 0 13 100 744 271 116 1 0 0 0 14 100 183 78 0 0 0 0 0 16 100 56 63 1 5 0 0 0 62 100 953 1533 545 5 0 0 0 When trying compound no. 62, autopsy did not find any adult or immature worms in the Coocum.

Test Example 2 Activity against Manson's tapeworm, Diphyllobothrium erinacei (in vitro) 1. Test material and method: Adult worms before Dogs infected naturally with the cestodes were immersed in Tyrode's solutions for 24 hours kept the 0.01 and 0.001 96 of the compound to be tested for effectiveness contained. D The motility of the treated tapeworms was tested and recorded.

2. Results: In Table IV are the efficacies of the various Veroindungen against adult specimens of Manson's tapeworm listed.

Table IV Connection concentration 0.01% 0.001% 14 + ~ 27 + 48 + ~ 50 + - means that the whole body was actively moving ..

+ means that the proglattids respond indefinitely to physical stimuli reacted wisely, while the Scolex showed no reaction.

+ means that the entire body including the Scolex does not have any Showed reaction to physical travel.

Experimental example 3 Efficacy against the cat liver gel, Clonorchis sinensis.

1. Test material and method: The test animals were 4 on natural Wise used for cats infected with Clonorchis sinensis. One of the cats became for comparison not treated, while the other 3 cats received compounds no. 14, 27 and 48 were administered.

The test animals were per kg of body weight on three consecutive Days administered 30 mg of the test compound. the The number of eggs excreted with the peces was recorded before and after the administration of the wormer remedy determined and recorded daily. 8 days after administration The wormer tested was the number of surviving liver fluke in all cats found in the bile ducts and gallbladder by autopsy.

2. Results: The number of the untreated cat changed of the excreted eggs practically not during the trial period, while the Number of excreted eggs in cats that were wormers according to the invention were administered, decreased extremely sharply after the administration.

The autopsy showed that di. untreated cat numerous normal Flukes contained no normal parasites, while no normal parasites were found in any of the treated cats were found.

Trial beisDiel 4 Efficacy against Manson's tapeworm, Diphylobothrium erinacei, and cat hookworm, Ancylostoma tubasforne.

1. Test material and method: As test animals 3 were natural Wise double-lit Manson tapeworm and cat hookworm infected katsen are used, One of these cats was used for comparison and was not treated. From the others both cats became one per kg. Body weight 30 mg of compound no.14 and 15 mg of compound no. 4 in the form of a prepared according to embodiment no capsule administered. The third cats were made in the form of buckets in an analogous manner Capsule per kg of body weight 10 mg of compound No. 1 and 20 mg of the compound No. 48 administered. and the number of eggs excreted was determined.

2. Results: Treated with the two worm remedies not according to the invention cats, the number of excreted eggs fell extremely sharply. In particular the cat treated with active ingredients no. 14 and no. 4 did not divorce any ' Eggs with the feces out more. The number of people excreted in faeces per day Eggs changed practically in the untreated cat during the duration of the experiment not. All test animals were sacrificed 7 days after the administration of the anthelmintics and autopsied. in the case of the compounds Xr. 14 and no. X dealt with Katse no living parasites were found in which the compounds no and No. 48 treated cat became @ur a Manson tapeworm and two cat hookworms found 12 Manson's tapeworms and 16 cat hookworms in the untreated cat were taken.

Experimental example 5 Efficacy against the dog hookworm, anoylostoma @aninum.

As a test animal, a naturally occurring dog chakworm was used infected dog used. The pro ka body weight was 5 from the compound No. 4 in the form of an injection solution prepared according to embodiment No. 3 administered subouten.

The test animal was then monitored for two weeks, whereby determined was that the number of excreted here decrease 2 days after the injection started and 4 days after injection down to 0 aboutc. From then on, until sun No more eggs excreted at the end of the experiment.

The number of beers eliminated was determined after the Flotation method using saturated saline solution.

Experimental example 6 6 puppies were used for this Versuoh, the Thrown in isolated and extremely clean kennels and up to the after 28 days of weaning. Woke up weaning g * -feeds the puppies with apesial puppy diet. Three of the pups all became two Weeks per kg of body weight 15 mg of compound no. 4 orally in tom of wafers a powder provided according to Example 1 is administered. The others 3 dogs were not treated.

During a 3 month observation period from birth no worm eggs were found in the faeces of the treated dogs, while in The excretions of the untreated dogs numerous Hunderundwur @ - @nd Hundehakenwurmeier were found.

Test example Testing the effectiveness against the bird tapeworm, Reillietina tetragona (in vitro) Normally shaped tapeworms that occur in the Autoprio naturally intended Broken poultry were removed as Experimental animals used. The tapeworms were washed completely with Tyrode's solution and then stored in 50 ml of Tyrode's solution. the 0.001 and 0.01% of the compounds, respectively Nos. 14, 27 and 48, respectively.

The movement of the tapeworms at room temperature was observed. The results of these experiments are listed in Table V.

Table V @Concentration @the connection state of the worms (%) No. 14 were 0.01% 9 hours after treatment all worms dead. No. 14 were 0.001% 24 hours after treatment all worms dead. No. 27 were 0.01% 14 hours after treatment all worms dead. No. 27 were 0.001% 36 hours after treatment all worms dead. No. 48 were 0.01% 14 hours after treatment all worms dead. No. 48 was 0.001% 20 hours after treatment all worms dead. - All worms moved during 48 Hours active.

Test Example 8 Testing of the effectiveness against Axine heterocerca.

1. Test material and method: 30 young, Yellowtails naturally infected with Axine heterocerca are used. the Yellowtails were divided into two groups, which were kept in 2 baton pans. One group was served with minced fish meat for 4 days os the compound No. 14 administered in an amount of 0.2 g / kg body weight / day. The other group was not treated.

7 days after the last administration, all fish were killed.

The gills were removed and examined for parasites.

2. Results: In the fish of the untreated group were 105 to 231 parasites were found in each case, while in those with the worming agent according to the invention treated fish 'no parasites were present.

Experimental Example 9 Testing of the effectiveness against infective larvae of the Cat hookworm, Ancylostoma tubaeforme.

1. Test material and method t The test animals were 8 to 14 Days aite used infective larvae that had been cultured according to the Sasa method was.

The larvae were kept for 24 hours in solutions containing 0.02, 0, 1 and 0.2 ffi of the compounds to be examined for their effectiveness. 24 hours after contacting with the connection under test the activity he observed larvae under a weak microscope.

2. Results: As can be seen from the values in Table VI, show all tested compounds have larvicidal activity.

Table VI Active ingredient No. 0.2% 0.1% 0.02% 19 +++ 20 +++ 10 + - - 18 + + - 6 + + - + No surviving larvae in the sample tube.

@ The number of surviving larvae is about the same as that Number of larvae before the treatment. Experimental example 10 Testing the effectiveness against the dog heartworm, Dirofilaria immitis.

1. Material and method used: Mature dog heartworms became isolated from dogs at autopsy u. The worms were in divided into several groups of 3 pieces each.

The worms were kept in Tyrode's solutions for 24 hours 0.1 @ 0.01 or 0.001% of the compound to be tested.

The worms thus treated were then placed in pure Tyrode's solution and stored in it for 7 days.

All the while the activity was the. Warmer carefully observed.

2. Results: EB was found that compounds no. 10, 19, 18, 2, 9, 76, 77, 54, 74, 75 and 68 are effective against Dirofilaria immitis.

Test Example 11 Testing the effectiveness against Manson's tapeworm, Diphyllobothrium erinacei.

1. Test material and method: The test animals were 2 on natural Used away cats infected with Manson's tapeworm. One of the two cats 30 mg of Compound No. 68 per kg of body weight was orally administered while the other was not treated.

2. Result: It was found that the number of excreted Eggs in the treated cat declined extraordinarily, while such a cat There was no decrease in the untreated cat.

At autopsy, 7 days after compound administration No. 68 were made when the untreated cat numerous tapeworms were found in the small intestine while the cat that with the compound 68 had been treated was tapeworm free. During the pre-search period there was no side effect to be noticed.

Experimental Example 12 Testing of the effectiveness against Dipylidium caninum.

1. Test material and method: Three naturally with tapeworms Infigured dogs were used as test animals. Became the first of these dogs per kg of body weight, 20 mg of Compound No. 70 administered orally to the second dog 15 ing per kg of body weight of Compound No. 77 were orally administered while the third of the dogs was not treated. The number of those excreted in the faeces proglottids were determined and recorded.

2. Results: In those treated with worms according to the invention In dogs, the number of proglottids secreted decreased considerably during the course of the experiment back, while a large number of proglottids were constantly present in the untreated dog was eliminated.

At a 7 day after the administration of the vermicelli according to the invention performed autopsy, numerous tapeworms were identified while no tapeworms were found in the dog treated with Compound No. 70 and in the dog treated with compound no. 77 only 2. During the duration of the experiment no side effects were observed.

Experimental example 13 Testing the effectiveness against Dirofilaria immitis.

Test material and method: There were 15 two to three year olds dogs infected with Dirofilaria immitis were used as experimental animals.

The worming of the test animals was confirmed by the finding of Dirofilariae detected in peripheral venous blood.

The test animals were divided into 5 groups of 3 dogs each. The animals of the first group were each given 1.5 mg of the compound per kg of body weight No. 18 administered intravenously; the animals of the second group were per kg of body weight 15 mg of compound no. 9 administered orally three times each time; the animals of the third group were administered orally three times per 10 ag of compound No. 2 per kg of body weight; The children of the fourth group were instead assigned compound no. 18 in the same way Administered wisely, while the animals of the fifth group for comparison purposes did not were treated.

One week after treatment, all dogs were counted Surviving worms in the heart determined by autopsy.

2. Results: Found in the hearts of the three untreated dogs 17, 12 and 14 stormers.

The hearts of the rest of the dogs were free of worms.

Few side effects were to be noticed during the duration of the experiment.

Test Example 14 Testing of the effectiveness against the pinworm, Enterobius vermincularis, 1. Experimental material and method: The environment of the age of 54 male children were tested using the "Scotch tape" method (= "Scotch swab" method) examined. The examination lasted 3 days showed that 15 of these Kin'd'er were infected with the pinworm. These 15 children were used as test subjects. They were divided into 9 groups of 5 children each. The children of the first group 25 mg of compound no. 14 were administered orally per kg of body weight; the children of the second group were given 7 mg of compound no. 1 and the children of the last group were given compound no. 62 in administered orally in an amount of 25 ag per kg of body weight.

2. Results: 2 weeks after administration of the The anus of the children was treated with worms on 5 consecutive days the scotch tape method. One of the three groups became worm eggs found around the anus.

There were no side effects.

Experimental Example 15 Testing of the acute toxicity of the compounds used as active ingredients in the worming agents according to the invention @ Table VII Connection LD50 on the mouse No orally intravenous 14 122 + 11.1 mg / kg 19 157 + 10.4 4 49 + 10.9 1 183 + 10.8 20 518 + 11.4 16 127 + 10.6 10 226.5 + 27.4 9.44 + 1.77 13 176 + 22.6 75 453.7 + 21.6 74 1038 + 27.1 17.26 + 1.77 62> 1600 18 210.9 + 23t9 8.15 + ~ 0.6 I 16 Two 8-month-old goats were used as test animals for the experiments. One of the two goats was given compound No. 4 in an amount of 10 mg / kg body weight and the other goat was given compound No. 20 in an amount of 15 mg / kg body weight, each orally. Then the general clinical symptoms were examined, such as a blood test and a urine test. This examination did not reveal any abnormal symptoms, such as diarrhea or interruption of rumination.

The examples illustrate the invention. Example 1 It becomes a powdery Wu, rmmittel manufactured by adding 5 parts by weight of 1-dodecyl-2-phenyl-3-methylimidasolium-p-toluenesulfonate (Compound No. 4) and 95 parts by weight of lactose mixed together and pulverized.

Example 2 By mixing, kneading and drying 45 parts by weight of 1-dodecyl -2-phenyl-3-methylimidazolium iodide (compound no. 50), 90 parts by weight of lactose, 13.5 parts by weight of corn starch and 1 part by weight of 8% starch paste become granules made from the talc tablets with the addition of one part by weight which each contain 150 mg of active ingredient.

Example 3 By dissolving 50 mg of 1,3-dibenzyl-2-methylimidazolium chloride (Compound No. 130 in 1 ml of saline is made into a solution for injection.

Example 4 By mixing 50 mg of 1-benzyl-2-undecyl-3-methylinidasolium methyl sulfate (Compound No. 1) and 450 mg of lactose, a capsule filling is made.

Example 5 By intimately mixing 30 mg of 1,3- @ ibenzyl-2-undecylimidazolium chloride (Compound No. 14), mg of 1-dodecyl-2-phenyl-3-methylimidazolium p-toluenesulfonate (Compound No. 4) 200 mg of calcium carbonate and 255 mg of lactose becomes one capsule filling manufactured.

Example 6 From 0.1 part by weight of 1-Doe cyl-2-hepf ade cyl-3-ethoxy-carbonylmethylimidazolium chloride (Compound No. 27), 44.9 parts by weight of nais starch, 44.0 parts by weight of soybean residue, 5.0 parts by weight of soybean oil, 4.0 parts by weight of minerals and 2.0 parts by weight Vitamins are made into a cattle feed additive by intimately mixing them.

Example 7 10 parts by weight of 1,3-dibenzyl-2-undecyl-imidazolium chloride (Compound No. 14), 40 parts by weight of yeast and 50 parts by weight of corn starch become one Mixed powder, which can be used as an additive for cattle feed, e.g. as an additive to minced fish meat, disnt.

Example 8 2d g of 1-dodecyl-2-phenyl-3-ethylimidazolium ethyl sulfate (compound No. 48) 300 g soybean residue, 500 g yeast, 880 g fish meal and 600 g corn meal are mixed. The mix is a chick feed additive that may be added Vitamins and minerals can be added.

Claims

Claims (7)

P a t e n t a n 5 rü c h e 1. Wormers for cold-blooded goods Vertebrates, indicated by an active ingredient content of a. Imidazole derivative of the general formula in which R1 is a hydrogen atom, a lower alkenyl, aralkyl or an alkyl radical optionally substituted in the # -position by a hydroxyl, cyano, amino or carboalkoxy group, or a radical of the general formula in which Z denotes a lower alkylene chain or a copper atom and where in both formulas R2 denotes a hydrogen atom, an alkyl or a phenyl group optionally substituted by a nitro group, R7 denotes a hydrogen atom, a lower alkyl group or a nitro group, R4 denotes a hydrogen atom or a nitro group and Y is a ring nitrogen atom or a group of the general formula is, in which R5 is a hydrogen atom, a lower alkenyl, aralkyl, phenyl, nitrophenyl or alkyl radical, which can optionally carry a hydroxyl group or carboalkoxy group as a substituent in the # -position and in which X is an organic or inorganic acid radical. 2. wormer according to claim 1, characterized by an active ingredient content of an imidazole derivative of the general formula in which R1 'is an aralkyl radical or an alkyl radical optionally substituted in the # -position by a hydroxyl, cyano, amino or carboalkoxy group, or a radical of the general formula in which Z 'is a lower alkylene chain, and where in both formulas R2' represents a Waeaeratoffatom, an alkyl, phenyl or nitrophenyl radical, R3 'and R4' each represent a hydrogen atom or a nitro group, R51 a hydrogen atom, a phenyl, Nitrophenyl or an alkyl radical optionally substituted in the # -position with a hydroxyl or carboalkoxy group and X 'denotes an organic or inorganic acid radical, 3. wormer according to claim 1, g e k e n n ß e i c h n e t due to a content of 1,3-dibenzyl-2-undecylimidazolium chloride as active ingredient. 4. wormer according to claim 2, g e k e n n z e i c h n e t by a Content of 1-benzyl-2-ethyl-3-dodecylimidezolium chloride as active ingredient. 5. wormer according to claim 2, g e k e fl n z e i c h n e t through a content of 1-benzyl-2-methyl-3-hexadecylimidazolium chloride as an active ingredient. 6. wormer according to claim 1, g e k e n n z e i c h n e $ by a Content of 1,3-dibenzyl-2-dodecylimidazolium chloride as active ingredient. 7. wormer according to claim 1, g e k e n n n z e i o h n e t by a Content of 1-ß-hydroxyethyl-2-methyl-4-nitroimidazolium-p-toluenesulfonate as active ingredient.