MXPA00011363A - Composition for keeping away vermin - Google Patents

Abstract

The invention describes essentially a non-therapeutical process for deterring vermin, which is based on the usage of the largely known compounds of formula (I), as defined herein. Furthermore, it describes the corresponding vermin-deterring compositions which contain these substances as the active ingredient, compounds of formula (I) for the preparation of vermin-deterring compositions, and the use of compounds of formula (I) in the defence against vermin. Thus, the invention describes how and in which form the compounds of formula (I) or their acid addition salts are used to deter vermin from materials, places or warm-blooded animals.

Description

COMPOSITION TO REMOVE PANINIAN ANIMALS The present invention essentially relates to a non-therapeutic process for driving away harmful animals, which is based on the use of the largely known compounds of formula (I) shown below. In addition, it relates to the remote compositions of corresponding harmful animals which contain these substances as the active ingredient, to compounds of the formula (I) for the preparation of compositions remote from the harmful animals, and to the use of the compounds of the formula (I) in the defense against harmful animals. Surprisingly, it has been found that the compounds of the following formula (I): or their acid addition salts, wherein: R is hydrogen, alkyl of 1 to 20 carbon atoms, or -C (0) -R8, wherein R8 is alkyl of 1 to 20 carbon atoms, alkoxy of 1 to 20 carbon atoms, unsubstituted phenyl, or phenyl which is one or many times substituted by alkyl of 1 to 3 carbon atoms, haloalkyl of 1 to 3 carbon atoms, haloalkoxy of 1 to 3 carbon atoms, halogen, cyano, hydroxyl, alkoxy, amino, or nitro; Ri is hydrogen, alkyl of 1 to 20 carbon atoms, -C (0) -R3, -C (S) -R, C (0) -0-R5- -C (0) -NH-R6 or -C (S) -NH-R; wherein R.sub.3, R., R.sub.5, Re and R.sub.7 independently of each other, mean alkyl of 1 to 10 carbon atoms, acetoxy, haloalkyl of 1 to 10 carbon atoms, alkoxy of 1 to 10 carbon atoms, or haloalkoxy of 1 to 10 carbon atoms, or independently of one another denote unsubstituted phenyl, or phenyl which is substituted one or many times by alkyl of 1 to 3 carbon atoms, haloalkyl of 1 to 3 carbon atoms, haloalkoxy of 1 to 3 atoms carbon, halogen, cyano, hydroxyl, alkoxy of 1 to 3 carbon atoms, amino, CHO, or nitro; R2 and R3, independently of one another, are hydrogen, alkyl of 1 to 3 carbon atoms, haloalkyl of 1 to 3 carbon atoms, haloalkoxy of 1 to 3 carbon atoms, halogen, cyano, hydroxyl, amino, aryl, or nitro; Ra denotes hydrogen, alkyl of 1 to 20 unsubstituted carbon atoms, or alkyl of 1 to 20 carbon atoms which is substituted one or many times by halogen, cyano, hydroxyloxy, alkoxy, nitro, phenyl, biphenyl, benzyloxy, or phenoxyphenyl, wherein each phenyl, biphenyl, benzyloxy, or phenoxyphenyl is in turn unsubstituted or substituted one or many times by alkyl of 1 to 3 carbon atoms, haloalkyl of 1 to 3 carbon atoms, haloalkoxy of 1 to 3 carbon atoms, carbon, alkoxy of 1 to 3 carbon atoms, halogen, cyano, hydroxyl, amino, or nitro; or denotes cycloalkyl of 3 to 8 carbon atoms, phenyl, biphenyl, phenoxyphenyl, or heterocyclyl, wherein each of these cyclic radicals is unsubstituted or substituted one or many times by alkyl of 1 to 3 carbon atoms, alkenyl of 2 to 6 carbon atoms, haloalkyl of 1 to 3 carbon atoms, haloalkoxy of 1 to 3 carbon atoms, alkoxy of 1 to 3 carbon atoms, halogen, cyano, hydroxyl, amino, (alkyl of 1 to 3 carbon atoms) 2N, acetyl or nitro; or denotes alkylenearyl of 1 to 6 carbon atoms, wherein the aryl radical is unsubstituted or substituted one or many times by alkyl of 1 to 3 carbon atoms, haloalkyl of 1 to 3 carbon atoms, haloalkoxy of 1 to 3 atoms carbon, halogen, cyano, hydroxyl, or nitro; or denotes alkyl of 1 to 20 carbon atoms which, depending on the number of carbon atoms, is interrupted by oxygen in one or more positions; and Rb means hydrogen, alkyl of 1 to 20 carbon atoms, heterocyclyl, or aryl, wherein each of the cyclic radicals is unsubstituted or substituted one or many times by alkyl of 1 to 3 carbon atoms, haloalkyl of 1 to 3 carbon atoms, haloalkoxy of 1 to 3 carbon atoms, alkenyl of 2 to 6 carbon atoms, halogen, cyano, hydroxyl, alkoxy of 1 to 3 carbon atoms, amino, (alkyl of 1 to 3 carbon atoms) 2N , or nitro; they are eminently suitable for keeping animals away harmful. Through the use according to the invention, of the above compounds, the most varied harmful animals can be kept away from humans, animals, objects, or from certain places, where numerous compounds within the scope of the formula (I) they are notorious for their particularly long duration of effectiveness. The compounds of the formula (I), which have at least one basic center, can form, for example, acid addition salts. These are formed, for example, with strong inorganic acids, such as mineral acids, for example perchloric acid, sulfuric acid, nitric acid, nitrous acid, a phosphoric acid or a hydrohalic acid, with strong organic carboxylic acids, typically alkancarboxylic acids of 1 to 4 carbon atoms substituted, where appropriate, for example, by halogen, for example acetic acid, such as dicarboxylic acids which are unsaturated, where appropriate, for example, oxalic, malonic, succinic, maleic, fumaric, or phthalic, normally hydroxycarboxylic acids, for example ascorbic, lactic, malic, tartaric, or citric acid, or benzoic acid, or with organic sulfonic acids, usually 1 to 4 carbon atoms or substituted aryl sulfonic acid, where suitable, for example, by halogen, for example methanesulfonic or p-toluenesulfonic acid. Of the salts, a particular preference is given to those formed with strong acids, especially with acids minerals, in particular with the halohydric acids of HCl and HBr. All multiple substitutions must be interpreted in such a way that identical or different substituents can be presented in a simultaneous manner. The alkyl groups present in the definitions of the substituents can be straight or branched chain, depending on the number of carbon atoms, and can be, for example, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl , decyl, undecyl, dodecyl, tetradecyl, hexadecyl, octadecyl, or eicosyl, as well as their branched isomers, for example isopropyl, isobutyl, secondary butyl, tertiary butyl, isopentyl, neopentyl, or isohexyl. The alkoxy, haloalkyl, and haloalkoxy radicals are derived from these alkyl groups. Halo denotes halogen, and usually means fluorine, chlorine, bromine, or iodine, preferably fluorine or chlorine, especially chlorine, wherein the corresponding substituent may contain one or more identical or different halogen atoms. Carbon-containing groups substituted by halogen, such as haloalkyl or haloalkoxy, may be partially halogenated or perhalogenated, wherein, in the case of multiple halogenation, the halogen substituents may be identical or different. Examples of haloalkyl-like a group by itself, and as a structural element of other groups and compounds, such as haloalkoxy - are methyl which is mono- to trisubstituted by fluorine, chlorine, and / or bromine, such as CHF2 or CF3; ethyl which is mono- to pentasubstituted by fluorine, chlorine, and / or bromine, such as CH2CF3, CF2CF3, CF2CC13, CF2CHC12, CF2CHF2, CF2CFCI2, CFCHBr2 CF2CHCIF, CF2CHBrF or CC1FCHC1F; propyl or isopropyl, mono- to heptasubstituted by fluorine, chlorine, and / or bromine, such as CH2CHBrCH2Br, CF2CHFCF3, CH2CF2CF3 or CH. { CF3) 2; and butyl or one of its isomers, mono- to non-substituted by fluorine, chlorine, and / or bromine, such as CF (CF3) CHFCF3 or CH2 (CF2) 2CF3. Alkenyl - as a group by itself and as a structural element of other groups and compounds, such as alkenoxyl, haloalkenyl, or haloalkenoxyl - is, in each case giving due consideration to the specific number of carbon atoms in the group or compound in subject, whether straight chain, for example vinyl, 1-methylvinyl, allyl, 1-butenyl, or 2-hexenyl, or branched, for example isopropenyl. Suitable cycloalkyl substituents contain from 3 to 8 carbon atoms and are, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, or cyclooctyl. The corresponding cycloalkenyl substituents can be mono- or also repeatedly unsaturated, for example, cyclopentadienyl or cyclo-octatetraenyl. Cyclopentyl and cyclohexyl are preferred.

In the context of the present invention, it is understood that aryl is phenyl or naphthyl, especially phenyl. These aryl groups are unsubstituted or are substituted one or many times by alkyl of 1 to 3 carbon atoms, haloalkyl of 1 to 3 carbon atoms, alkoxy of 1 to 3 carbon atoms, haloalkoxy of 1 to 3 carbon atoms, halogen , cyano, hydroxyl, amino, or nitro, wherein each multiple substitution is not limited to identical substituents; instead, mixed substituents can appear. In the context of the present invention, it is understood that heterocyclyl means aliphatic or aromatic cyclic radicals, and furthermore also benzo-condensates, containing at least one oxygen, sulfur, or nitrogen atom. The 5- and 6-membered heterocycles are preferred. Heterocyclyl typically includes substituents such as dioxolanyl, pyrrolidinyl, piperidinyl, morpholinyl, pyridyl, pyrryl, furyl, thienyl, imidazolyl, tetrahydrofuryl, tetrahidropirri-lo, tetrahydropyranyl, dihydrofuryl, dihydropyranyl, benzofu-rilo, benzothienyl, isoxazolyl, oxazolyl, thiazolyl, oxazolinyl, oxazolidinyl, indolyl, imidazolinyl, imidazolidinyl, and dioxanyl. Preference is given especially to those which are unsubstituted, or which have 1 or 2 halogen atoms, denoting halogen in this case, fluorine, chlorine, or bromine, but especially chlorine. Of these heterocyclyl radicals, pyrrolidinyl are especially noteworthy, pipepdynyl, pyridyl, pirp, furyl, thienyl, tetrahydrofuryl, benzofuryl, and benzothienyl. A preferred subgroup in the context of formula (I) is formed by the compounds wherein: R is hydrogen or alkyl of 1 to 6 carbon atoms; Ri is hydrogen, alkyl of 1 to 6 carbon atoms, -C (0) -R3 or -C (S) -R4; wherein R3 and R_, independently of one another, are alkyl of 1 to 3 carbon atoms, acetoxy, haloalkyl of 1 to 3 carbon atoms, or independently of each other, are unsubstituted phenyl, or phenyl which is substituted one or many sometimes by alkyl of 1 to 3 carbon atoms, haloalkyl of 1 to 3 carbon atoms, or halogen; R2 and R3, independently of one another, are hydrogen or alkyl of 1 to 3 carbon atoms; Ra is hydrogen, alkyl of 5 to 20 carbon atoms, cycloalkyl of 3 to 8 carbon atoms, or phenyl, wherein each of the cyclic radicals is unsubstituted or is substituted one or many times by alkyl of 1 to 3 carbon atoms. carbon, haloalkyl of 1 to 3 carbon atoms, alkoxy of 1 to 3 carbon atoms, halogen, amino, (alkyl of 1 to 3 carbon atoms) 2N, or acetyl; and Rb is hydrogen, unsubstituted phenyl or phenyl which is one or many times substituted by alkyl of 1 to 3 carbon atoms, haloalkyl of 1 to 3 carbon atoms, alkoxy of 1 to 3 carbon atoms, halogen, amino, or ( alkyl of 1 to 3 atoms carbon) 2N; including its acid addition salts. In the context of formula (I), the compounds which are especially preferred are those in which R is hydrogen, and the remaining substituents are defined as in formula (I), as well as their acid addition salts. A further subgroup, which is preferred due to its notorious activity, is formed by the compounds of the formula I, wherein i is -C (0) -R3, wherein R3 represents unsubstituted phenyl, or phenyl which is substituted one or many sometimes by alkyl of 1 to 3 carbon atoms, especially by methyl, ethyl, or isopropyl, and the remaining substituents are defined as in formula (I), as well as their acid addition salts. Also of interest are compounds of the formula (I), wherein R 2 and R 3, independently of one another, are hydrogen or methyl, and the remaining substituents are defined as in the formula (I), as well as their addition salts of acid. Of the aforementioned compounds of the formula (I), a particular preference is given to those in which Ra is alkyl of 5 to 20 carbon atoms, benzoyloxymethyl, 2,3-dihydrobenzo (b) furryl-2, phenyl unsubstituted , or phenyl which is substituted one or many times by alkyl of 1 to 3 carbon atoms, methoxy, or chlorine; including its acid addition salts, and in particular the representatives in which Ra is a straight chain alkyl of 7 to 20 carbon atoms; including its acid addition salts. The free active ingredients are clearly preferred over r üBÜffr ^ t _____________ l_? the acid addition salts Each representative of the group of individual substances mentioned below is especially preferred due to its notorious activity, the new asterisk being marked, and representing a constituent of the present invention 2- [n- (1-h? drox? hex? l)] piperidma *, 2- [n- (1-h? drox? hep-tyl)] piperidine *, 2- [n- (1-h? drox? oct? l)] -pipepdma * , 2- [n- (l-hydroxmonyl) Jpiperi ina, 2- [n- (1-h? Drox? Dec? L)] piperidine, 2- [n- (1-h? Drox? Undec? L)] piperidma, 2- [n- (1-hydrox? dodec? l)] pipe-pdma, 2- [n- (1-h? drox? tdec? l)] piperidine, 2 [n (1-h? drox? -tetradecil)] pipepdma, 2- [n- (1-h? drox? pentadec? l)] piperidma, 2- [n- (1-h? drox? hexadec? l) piperidma, 2- [n- (1-H? Drox? Heptadec? L)] piperidma, 2- [n- (1-h? Drox? Octadec? L)] pipe idma, 2- [n- (l-hydroxmonadecyl)] piperidine, 2- [ n- (1-hydrox? cos? l)] pipep-dyna, 2- [n- (1-hydrox? ene? l)] pipepdma, 2- [(1-c? clopent (l) (1-h? drox?) methyl] piperidine, 2 - [(l-phen? l) (lh? drox?) met? l] -4-terbutilpip eridin, 2- [(1-phen? l) (1-h? drox?) methyl] pipepdma, N-met? l-2- [(1-phen? l) (l?? drox?) met? l] piperidma, 2- [(1-d? phen? l) (1-hydroxy) methyl] pipepdma, 2 - [(l-phen? l) (1- [2, 3-d? h? drobenzo (b) furpl? ] (1-h? Drox?) Methyl] pipepdine, N-met? L-2- [(1- [4-met? Lfe-nil]) (l?? Drox?) Met? L] p? Per? Dma , 2- [(1- [4-met? Lfen? L]) (1-h? -drox?) Me? L] pipepdine, 2- [(1- [4-isopropylphenyl]) (1-h? Drox ?) useful] pipe idma, N-met? l-2- [(1- [4-isopropyl-phenyl]) (lh? drox?) useful] piperidma, 2- [(1- [4-methox? fen? l]) (1-h? drox?) met? l? p? per? -dine, 2- [(1- [benzyloxymethyl]) (1-hydrox?) methyl] pipepdma, 2 - [( l- thienyl) (1-hydroxy) methyl] piperidine, 6,6-dimethyl-2 - [(1- [4-chlorophenyl]) (1-hydroxy) methyl] piperidine, N-acetyl-2- [(1 - hydroxy) (1-undecyl)] piperidine *, or N-ethoxycarbonyl-2- [(1-hydroxy) (1-undecyl)] piperidine *. Chemical Abstracts, Volume 107, Number 23, December 7, 1987, Columbus, Ohio, US; Excerpt No. 215128 discloses, among other compounds, deoxynojirimycin as a finer that exhibits slight activity against certain insects that damage plants. British Patent Number GB-A-2,071,653 discloses compounds that are structurally related to the compounds of formula I of the present invention. They can be used in marine environments and fresh water, particularly to reduce the growth of algae, barnacles, or fungi. European Patent Number EP-A-0,281,908 and European Patent Number EP-A-0, 289, 842, disclose the use of certain a,? -aminoalcohol derivatives, for example, some piperidines, as insect repellents and ticks In the context of the present invention, it is understood that the damaging animals are in particular insects, mites, and ticks. These include insects of the orders of: Lepidoptera, Coleoptera, Homoptera, Heteroptera, Diptera, Thysanoptera, Orthoptera, Anoplura, Siphonaptera, Malophagous, Thysanura, Isoptera, Psocoptera and fimimenoptera. However, the harmful animals that can be mentioned in particular are those that they give problems to humans or animals, and carry pathogens, for example flies, such as Musca domestica, Musca vetustissima, Musca autumnalis, Fannia canicularis, Sarcophaga carnaria, Lucilia cuprina, Hypoderma bovis, Hypoderma lineatum, Chryso yia chloropyga, Der atobia hominis , Cochliomyia hominivo-rax, Gasterophilus intestinalis, Oestrus ovis, Sto oxys calci -trans, Haematobia irri tans and moths (Nematocera), such as Culicidae, Simuliidae, Psychodidae, but also blood-sucking harmful animals, for example fleas, such as Ctenocephalides felis and Ctenocephalides canis (fleas of cats and dogs), Xenopsylla cheopis, Pulex irritans, Dermatophilus penetrans, lice, such as Damalina ovis, Pediculus hu anis, flies bites and horse flies (Tabanidae), Haematopota spp. such as Haematopota pluvialis, Tahanidea spp. such as Tabanus nigrovi ttatus, Chrysopsinae spp. such as Chrysops caecutiens, tsetse flies, such as Glossinia species, biting insects, particularly cockroaches, such as Germanic philately, Blatta orientalis, American Periplaneta, mites, such as Dermanyssus gallinae, Sarcoptes scabiei, Psoroptes ovis and Psorergates spp. and finally, but not at least, ticks. The last belong to the order of Acariña. The known representatives of ticks are, for example, Boophilus, Amblyomma, Anocentor, Dermacentor, Haemaphysalis, Hyalomma, Ixodes, Rhipicentor, Margaropus, Rhipiceps, Argas, Otobius and Orni thodoros and the like, which Preference infest warm-blooded animals, including farm animals, such as cattle, pigs, sheep and goats, poultry, such as chickens, turkeys, and geese, fur animals, such as mink, foxes, chinchillas, rabbits , and the like, as well as domestic animals such as cats and dogs, but also humans. Ticks can be divided into hard and soft ticks, and are characterized by infesting one, two, or three host animals. They join a host animal that passes, and they suck blood or bodily fluids. Fully satiated female ticks fall from the host animal, and place large numbers of eggs (2,000 to 3,000) in a suitable crack in the floor, or in any other protected site where the larvae hatch. These in turn seek a host animal, in order to suck blood from it. The larvae of ticks that only infest a host animal, change twice, and therefore, they become nymphs, and finally adult ticks, without leaving the host they have selected. The larvae of the ticks that infest two or three host animals leave the animal after feeding on the blood, move in the local environment, and look for a second or third host as nymphs or as adult ticks, in order to suck their blood. Ticks are responsible throughout the world for the transmission and spread of many human and animal diseases. them. Due to its economic influence, the most important ticks are Boophilus, Rhipicepe, Ixodes, Hyalom a, Amblyomma and Dermacentor. They are carriers of bacterial, viral, and protozoal diseases, and cause tick paralysis and ticks toxicosis. Even a single tick can cause paralysis, when its saliva penetrates the host animal during ingestion. Diseases caused by ticks are usually transmitted by ticks, which infest several host animals. These diseases, for example babesiosis, anaplasmosis, teileriasis, and water heart disease, are responsible for the death or damage of a large number of domestic and farm animals worldwide. In many temperate countries, Ixodide ticks transmit the chronically damaging agent of Lyme disease from wild animals to humans. Apart from the transmission of diseases, ticks are responsible for large economic losses in livestock production. The losses are not confined to the death of the host animals, but also include damage to the skins, loss of growth, a reduction in milk production, and a reduced value of the meat. Although the harmful effects of a tick infestation on animals have been known for years, and enormous progress has been made using tick control programs, no methods have been found so far. _J -__-__ «i ___-_-. completely satisfactory to control or eliminate these parasites, and in addition, ticks have often developed resistance to active chemical ingredients. The infestation of fleas on domestic animals and pets in the same way still represents for the owner a problem that has not been satisfactorily resolved, or that can only be solved at a considerable expense. As with ticks, fleas are not only problematic, but are carriers of diseases, and transmit different fungal diseases from a host animal to another host animal and to the animal's caretaker, particularly in hot and humid climatic areas, for example in the Mediterranean, in the southern part of the USA, and so on. Those at risk in particular are people with a weakened immune system, or children whose immune systems have not yet fully developed. Due to its complex life cycle, none of the known methods for flea control is completely satisfactory, especially since most of the known methods are basically directed towards the control of adult fleas in the hair, and leave completely untouched. different juvenile stages of fleas, which exist not only in the hair of the animal, but also in the floor, in the carpets, in the bed of the animal, in the chairs, in the garden, and in all other places with which contact the infested animal. The treatment of fleas is usually costly, and it has to continue for long periods of time. Success usually depends on the treatment not only of the infested animal, for example the dog or the cat, but at the same time all the places that the infested animal frequents are treated. This complicated procedure is unnecessary with the present compounds of the formula (I), because a particular advantage of the compounds of the formula (I) under discussion, is that they are extremely effective, and at the same time of very low toxicity, both for white parasites as for warm-blooded animals. This is because their activity is based not on the death of the white parasite, but on its remote defense before it attacks, bites, bites, or otherwise harms the host organism. The presence of the compounds of the formula (I) which are discussed herein seems to alter the parasites in such a way that they suddenly leave the treated environment without biting or stinging, or even do not infest a treated host animal at all. What is surprising is that the effect is established when the parasite comes in contact with the active ingredient for a short time. After contact for a short time, the parasite avoids any other contact with the active ingredient. An additional advantage is in the long-term action, for example, compared with DEET (N, N-diethyl-m-toluamide), which, although very effective, quickly volatilizes, and consequently, it has to be reapplied after approximately 2 hours, and therefore, is not appropriate for the long-term treatment of the animals. The use of the present active ingredients is also pleasant, because they are almost odorless. Although the present active ingredients, of course, can be mixed with other substances having the same sphere of activity, or with parasiticides or with other activity-enhancing substances, to achieve an enhanced or lasting additional action, and then they can be applied, in contrast to many prior art compounds, this is totally unnecessary, because they combine all the convenient properties. If the parasite is not only going to keep away, but is also going to be annihilated, of course, this can be achieved by the addition of appropriate insecticides and / or acaricides. However, in practice this is not necessary in most cases. The present active ingredients are preferably used in a dilute form. Typically, they are brought to the final application form by the use of suitable formulation excipients, and then contain between 0.1 and 95 weight percent, preferably 0.5 to 90 weight percent of the active ingredient. Because the active ingredients are applied in many cases to warm-blooded animals, and of course, come into contact with the skin, the suitable formulating excipients are the excipients and the administration forms that are known in cosmetics. They can be administered in the form of solutions, emulsions, ointments, creams, pastes, powders, sprays, et cetera. To be administered to farm animals or to pets, such as cows, horses, oxen, camels, dogs, cats, poultry, sheep, goats, etc., formulations called "pouring" or "application" are especially suitable; these liquid or semi-liquid formulations have the advantage that they only have to be applied to a small area of hair or plumage, and thanks to the proportion of extension oils or other extender additives, they are dispersed over all the hair or plumage, without having to do anything else, and become active over the entire area. Of course, inanimate materials, for example clothes or baskets of dogs and cats, stables, carpets, curtains, rooms, conservators, etc., can be treated with these formulations, and thus protect themselves from the infestation of parasites . To control cockroaches, you can spray or sprinkle their locus, usually cracks in the walls, furniture, and so on. Because the cockroaches are extremely vigorous, and it is almost impossible to remove them completely, recommends that, when the present active ingredients are used, insecticides having activity against cockroaches are additionally used. To apply to humans, a pleasant-smelling essence, for example a perfume, can be added to make the application more attractive. The following examples of preparation and use of the active ingredients according to the invention serve to illustrate the invention without restricting it. In particular, the preferred formulations are made as follows: Formulation Example 1 A remote composition of harmful animals is prepared in the form of a lotion to be applied to the skin, by mixing 30 parts of one of the active ingredients according to the invention, of Table 1, 1.5 parts of perfume, and 68.5 parts of isopropanol, where the latter can be replaced by ethanol.

Formulation Example 2 A remote composition of harmful animals in the form of an aerosol spray is prepared on the hair of a pet by formulating a 50 percent active ingredient solution consisting of 30 parts of one. of the active ingredients according to the invention, from Table 1, 1 parts of perfume, and 68 parts of isopropanol with 50% Frigen 11/12 (a halogenated hydrocarbon) as a propellant gas in an aerosol can Formulation Example 3 A remote composition of harmful animals is prepared in the form of an aerosol spray on the skin, by the formulation of a 40 percent active ingredient solution, consisting of 20 parts of one of the active ingredients. according to the invention, a perfume part 79 parts isopropanol, with 60 percent propane / butane (at a ratio of 15 85) as propellant gas in an aerosol can. By way of example, the following tables reproduce a few of the compounds included in the formula (I), which may be used according to the invention, but is not claimed to be a total list The substances shown in italics are new and are part of the present invention The remaining substances, including their preparation processes, are known from the literature The following example of preparation merely serves to exemplify, and refers to a particularly preferred substance May of these known substances are used in human medicine for different diseases, for example as bronchodilators, agents antiallergics, analgesics, diuretics, antidepressants, dopamine antagonists, and so on. Some are attributed a herbicidal or fungicidal activity. The new representatives within the scope of formula (I), shown in italics in Table 1 below, can be prepared in a manner analogous to known substances. In the "R" column, representatives having the acid in parentheses, are the corresponding acid addition salts.

Preparation Example: Preparation of 2 (n-decylhydroxy) iperidine according to the following reaction scheme: A mixture of bromomagnesium-decane (0.31 mol) in 350 milliliters of dry diethyl ether is mixed by dripping at 25 ° C with a solution of 2-cyanopyridine (0.3 mol) in 250 milliliters of dry ethyl ether. The reaction mixture is heated at reflux for 2 hours, then cooled to 10 ° C, and mixed with aqueous sulfuric acid (70 milliliters of water / 200 milliliters of 5N H2SO4). The product of the reaction is extracted with diethyl ether. The The ether phase is repeatedly washed with a saturated solution of sodium chloride, dried over magnesium sulfate, filtered, and concentrated in vacuo. 72.5 grams of compound B (yield 97.7 percent) are obtained as an oil, which is used for the next stage without further purification. In this step, a mixture of 4.6 grams of compound B, and 0.25 grams of Pt02 in 45 milliliters of acetic acid, is mixed with elemental hydrogen for hydrogenation at room temperature. After 17 hours, all the solid constituents are filtered, and the liquid phase is mixed with a 2-normal caustic soda solution. Then the extraction with dichloroethane follows. The organic phase is repeatedly washed with a saturated solution of sodium chloride, dried over magnesium sulfate, filtered, and concentrated in vacuo. The residue is mixed with methanol, whereby the title compound is precipitated as an amorphous powder. After filtration and drying under vacuum, 2.8 grams (62% yield) of the title substance are obtained with a m.p. 61-63 ° C. In the following Table, Ac is acetyl, AcO is acetyloxy, Me is methyl, MeO is methoxy, Et is ethyl, EtO is ethoxy, P is propyl, PO is propoxyl, nP is normal propyl, iP is isopropyl, B is butyl, nB is normal butyl, iB is isobutyl, sB is secondary butyl, tB is tertiary butyl, Ph is phenyl; Bz is benzyl, cPro is cyclopropyl, cBu is cyclobutyl, cPen is cyclopentyl, cHex is cyclohexyl, cHep is cycloheptyl, cOc is cyclooctyl, and methylene is me. Table 1: Compounds of the formula (I) Biological Examples: Field test method to test substances that remove harmful animals This method is done on titration plates that have 6 wells with a cross section of 5 centimeters each, using a computer supported video system. Each cavity of the titration plate is coated with a circular filter paper or other suitable carrier material. The substance of the formula I to be tested is dissolved in methanol, acetonitrile, or other suitable solvent, using ultrasound treatment and heating for the poorly soluble substances. In an amount of 1 to 100 micrograms / square centimeter, the dissolved test substance is placed in the center of the filter paper on a quadrant or circular area of approximately 2 square centimeters of radius. 4 of the 6 wells are filled with different test substances, or with the same test substance in different dilutions (for example, 1, 3.2, 5, 10, and 20 micrograms / square centimeter). The fifth well is treated with DEET (N, N-diethyl-m-toluamide) as the standard substance. The sixth well is filled with pure solvent, and serves as a control. 60 to 100 larvae, or 25 to 50 nymphs, or 10 to 25 adults, of the parasite to be tested, for example ticks, are added to each filter paper, and the system is covered with a glass plate, and it is placed under a video camera. ig ^ • "• ** - • - At 5-second intervals, the video camera takes individual images of the six wells. For a qualitative evaluation, these images are observed in a period of time as a continuous film, following optically the movements of the parasites on the filter paper, and comparing them with the movements in the control well Number 6, or with the standard of the fifth water well. In this way, a qualitative observation is made as to whether the test parasites move uniformly over the entire surface of the filter paper and ignore the test substance, or if and on what period they avoid the treated area, and what influence the dilution of the test Test substance on the behavior of the test parasites. In this way, the neutral and remote substances are determined. At the same time, the duration of activity of the test substance is determined, and compared with that of the standard. By plotting all the images for each individual well on top of each other, different areas of density are obtained. This represents the frequency at which parasites visit certain places. This frequency is evaluated statistically, and therefore, quantitatively, by means of the Willcoxon method, in a comparison with the control and with the standard. The compounds of Table 1, for example Nos. 1.22 to 1.41, 1.44, 1.45, 1.59 1.87, 1.89, 1.95, 1.96, 1.97, 1.101, 1.137, 1.138 and 1.139 exhibit excellent activity.

Field test in vi tro against Amblvomma hebraeum or variecratum (nymphs) The test is carried out as described above, adding approximately 25 to 50 nymphs per well. 10 milligrams of the dissolved test substance are applied to an area of 2.4 square centimeters in radius. An evaluation of the video images shows that the compounds of the formula I exhibit a noticeable remote action against the nymphs of Amblyomma, which lasts considerably longer than that of DEET. For example, a particularly noticeable long-term activity is shown with compounds numbers 1.26, 1.36, 1.40, 1.45, 1.47, 1.95, 1.96, 1.97, 1.137, and 1.139, even up to a dilution of 3.2 micrograms / square centimeter.

In vitro field test against BoopAilus microOlus Biarra (larvae) The test is performed as described above, adding approximately 60 to 100 larvae per well. 10 milligrams of the dissolved test substance are applied to an area of 2.4 square centimeters in radius. An evaluation of the video images shows that the compounds of the formula I exhibit a noticeable remote action against the larvae of Boophilus, which lasts considerably longer than that of DEET. A particularly noticeable long-term activity is shown, for example, with compounds numbers 1.26, to 1.36, 1 40, 1.45, 1 47, 1 95, 1 96, 1"97, 1137, 1139, 1140, 1141, 1142 and 1143 inclusive up to a dilution of 10 micrograms / square centimeter.

Field test against Rhipicetihalus sanauineus (nymphs) A test is performed in a manner analogous to Example B, using approximately 40 to 50 nymphs. An evaluation of the video images shows that the compounds according to the invention exhibit a good off-setting action. In particular, the compounds are notorious for their almost complete removal action, which lasts considerably longer than that of DEET. Long-term activity is shown. particularly noticeable period with compounds numbers 1.27, 1.29, 1.32, 1.34, 1.36, 1.40, 1.45, 1.59, 1.96, 1 137, and 1139 inclusive up to a dilution of 10 micrograms / square centimeter. In analogous field tests, the same test substances are tested to determine their attractive activity to different fly species, such as Musca domestica. It is shown that the aforementioned substances exhibit a strong action away, even with these models tested.

Claims (13)

1. A non-therapeutic process for removing harmful animals from warm-blooded animals, by which a compound of the formula (I): or one of its acid addition salts, wherein: R is hydrogen, alkyl of 1 to 20 carbon atoms, or -C (0) -Ra, wherein R 8 is alkyl of 1 to 20 carbon atoms, alkoxy 1 to 20 carbon atoms, more substituted phenyl, or phenyl which is substituted one or many times by alkyl of 1 to 3 carbon atoms, haloalkyl of 1 to 3 carbon atoms, haloalkoxy of 1 to 3 carbon atoms, halogen, cyano , hydroxyl, alkoxy, amino, or nitro; Ri is hydrogen, alkyl of 1 to 20 carbon atoms, -C (0) -R3, -C (S) -R4, C (0) -0-R5- -C (0) -NH-R6 or -C (S) -NH-R,; wherein R3, R4, R5, R6 and R7 independently of one another, mean alkyl of 1 to 10 carbon atoms, acetoxy, haloalkyl of 1 to 10 carbon atoms, alkoxy of 1 to 10 carbon atoms, or haloalkoxy of 1 to 10 carbon atoms, or independently of one another denote unsubstituted phenyl, or phenyl which is substituted one or many times by alkyl of 1 to 3 carbon atoms. carbon, haloalkyl of 1 to 3 carbon atoms, haloalkoxy of 1 to 3 carbon atoms, halogen, cyano, hydroxyl, alkoxy of 1 to 3 carbon atoms, amino, CHO, or nitro; R2 and R3, independently of one another, are hydrogen, alkyl of 1 to 3 carbon atoms, haloalkyl of 1 to 3 carbon atoms, haloalkoxy of 1 to 3 carbon atoms, halogen, cyano, hydroxyl, amino, aryl, or nitro; Ra denotes hydrogen, alkyl of 1 to 20 unsubstituted carbon atoms, or alkyl of 1 to 20 carbon atoms which is substituted one or many times by halogen, cyano, hydroxyl, alkoxy, nitro, phenyl, biphenyl, benzyloxy, or phenoxyphenyl, wherein each phenyl, biphenyl, benzyloxy, or phenoxyphenyl in turn is unsubstituted or substituted one or many times by alkyl of 1 to 3 carbon atoms, haloalkyl of 1 to 3 carbon atoms, haloalkoxy of 1 to 3 carbon atoms, alkoxy of 1 to 3 carbon atoms, halogen, cyano, hydroxyl, amino, or nitro; or denotes cycloalkyl of 3 to 8 carbon atoms, phenyl, biphenyl, phenoxyphenyl, or heterocyclyl, wherein each of these cyclic radicals is unsubstituted or substituted one or many times by alkyl of 1 to 3 carbon atoms, alkenyl of 2 to 6 carbon atoms, haloalkyl of 1 to 3 carbon atoms, haloalkoxy of 1 to 3 carbon atoms, alkoxy of 1 to 3 carbon atoms, halogen, cyano, hydroxyl, amino, (alkyl of 1 to 3 carbon atoms) carbon) 2N, acetyl or nitro; or denotes alkylenearyl of 1 to 6 carbon atoms, wherein the aryl radical is unsubstituted or substituted one or many times by alkyl of 1 to 3 carbon atoms, haloalkyl of 1 to 3 carbon atoms, haloalkoxy of 1 to 3 atoms carbon, halogen, cyano, hydroxyl, or nitro; or denotes alkyl of 1 to 20 carbon atoms which, depending on the number of carbon atoms, is interrupted by oxygen in one or several positions; and Rb means hydrogen, alkyl of 1 to 20 carbon atoms, heterocyclyl, or aryl, wherein each of the cyclic radicals is unsubstituted or substituted one or many times by alkyl of 1 to 3 carbon atoms, haloalkyl of 1 to 3 carbon atoms, haloalkoxy of 1 to 3 carbon atoms, alkenyl of 2 to 6 carbon atoms, halogen, cyano, hydroxyl, alkoxy of 1 to 3 carbon atoms, amino, (alkyl of 1 to 3 carbon atoms) 2N , or nitro; it is applied topically, together with an extender additive, to the skin, hair, or plumage of the warm-blooded animal.

2. A process according to claim 1, wherein a compound of the formula (I), or one of its acid addition salts, is applied, wherein: R is hydrogen or alkyl of 1 to 6 carbon atoms; carbon; Ri is hydrogen, alkyl of 1 to 6 carbon atoms, -C (0) -R3 or -C (S) -R; wherein R3 and R, independently of one another, are alkyl of 1 to 3 carbon atoms, acetoxy, haloalkyl, of 1 to 3 carbon atoms, or independently of one another, are unsubstituted phenyl, or phenyl which is one or many times substituted by alkyl of 1 to 3 carbon atoms, haloalkyl of 1 to 3 carbon atoms, or halogen; R2 and R3, independently of one another, are hydrogen 0 alkyl of 1 to 3 carbon atoms; Ra is hydrogen, alkyl of 5 to 20 carbon atoms, cycloalkyl of 3 to 8 carbon atoms, or phenyl, wherein each of the cyclic radicals is unsubstituted or is substituted one or many times by alkyl of 1 to 3 carbon atoms. carbon, haloalkyl of 1 to 3 carbon atoms, alkoxy of 1 to 3 carbon atoms, halogen, amino, (alkyl of 1 to 3 carbon atoms) 2N, or acetyl; and Rb is hydrogen, unsubstituted phenyl, or phenyl which is one or many times substituted by alkyl of 1 to 3 carbon atoms, haloalkyl of 1 to 3 carbon atoms, alkoxy 1 to 3 carbon atoms, halogen, amino, or (alkyl of 1 to 3 carbon atoms) 2N; including its acid addition salts.

3. A process according to one of claims 1 or 2, by which a compound of the formula (I) or one of its acid addition salts is applied, wherein R is hydrogen, and the remaining substituents are defined as the formula (I).

4. The process according to one of claims 1 to 3, whereby a compound of the formula (I), or one of its acid addition salts, wherein Ri is -C (0) -R3, wherein R3 represents unsubstituted phenyl, or phenyl which is substituted one or many times by alkyl of 1 to 3 atoms of carbon, especially methyl, ethyl, or isopropyl, and the remaining substituents are defined as in formula (I).

A process according to one of claims 1 to 4, by which a compound of the formula (I), or one of its acid addition salts, is applied, wherein R2 and R3, independently of one another , they are hydrogen or methyl, and the remaining substituents are defined as in formula (I).

The process according to one of claims 1 to 5, by which a compound of the formula (I) or one of its acid addition salts is applied, wherein Ra is alkyl of 5 to 20 carbon atoms , benzoyloxymethyl-2, 3-dihydrobenzo (b) furryl-2, unsubstituted phenyl, or phenyl which is one or many times substituted by alkyl of 1 to 3 carbon atoms, methoxy, or chloro.

The process according to one of claims 1 to 6, by which a compound of the formula (I), or one of its acid addition salts, is applied, wherein Ra is straight chain alkyl of 7 to 20 carbon atoms.

8. The process according to claim 1, wherein the active ingredient employed is one of the following substances mentioned, or one of its acid addition salts: 2- [n- (1-hydroxyhexyl)] piperidine, 2- [n- (1-hydroxyheptyl)] piperidine, 2- [n- (1-hydroxylethyl)] -piperidine, 2- [n - (l-hydroxynonyl)] piperidine, 2 [n- (1-hydroxydecyl)] piperidine, 2- [n- (1-hydroxyundecyl)] piperidine, 2- [n- (1-hydroxydecyl)] piperidine, 2 - [n- (1-hydroxytridecyl) piperidine, 2- [n- (1-hydroxytetrade-cyl)] piperidine, 2- [n- (1-hydroxypentadecyl)] piperidine, 2- [n- (1-hydroxyhexadecyl)] piperidine, 2- [n- (1-hydroxyheptadecyl)] piperidine, 2- [n- (1-hydroxyoctadecyl)] piperidine, 2- [n- (1-hydroxynadedecyl)] piperidine, 2- [n- (1 -hydroxyeicosyl)] piperidine, 2- [n- (1-hydroxy-sonicosyl)] iperidine, 2- [(1-cyclopentyl) (1-hydroxy-xi) methyl] piperidine, 2 - [(1-phenyl) (1-hydroxy ) methyl] -4-tert-butyl-piperidine, 2- [(1-phenyl) (1-hydroxy) methyl] piperidine, N-methyl-2 - [(1-phenyl) (1-hydroxy) methyl] piperidine, 2- [(1-difnyl) (1-hydroxy-xi) methyl] piperidine, 2 - [(1-phenyl) -1- [2, 3-dihydro-benzo (b) fu-rryl] (1-hydroxy) methyl] piperidine, N-methyl-2- [( 1- [4-methylphene]] (1-hydroxy) methyl] piperidine, 2- [(1- [4-methylphenyl]) (1-hydroxy) methyl] piperidine, 2- [(1- [4-isopropylphenyl] ]) (1-hydroxy) methyl] piperidine, N-methyl-2- [(1- [4-isopropylphenyl]) (1-hydroxy) methyl] piperidine, 2- [(1- [4-methoxyphenyl]) (1 -hydroxy) methyl] pipe-ridine, 2- [(1- [benzyloxymethyl]) (1-hydroxy) methyl] piperidine, 2- [(1-thienyl) (1-hydroxy) methyl] iperidine, 6,6-dimethyl -2- [(1- [4-chlorophenyl]) (l-hydroxy) methyl] piperidine, N-acetyl-2- [(1-hydroxy) (1-undecyl)] piperidine, or N-ethoxycarbonyl-2- [ (1-hydroxy) (1-undecyl)] iperidine.

9. The process according to one of the i claims 1 to 8, by which the compound of the formula (I) is applied, in the form of a poured or applied formulation.

10. A process for removing harmful animals from places or materials where they are not wanted, by means of which an effective amount of a compound of the formula (I) according to one of claims 1 to 8 is applied to the place or to the material from which you want to move the insect away.

11. A composition for removing harmful animals, which contains a compound of the formula (I) according to one of claims 1 to 8, and an extender additive.

12. A process for the preparation of a composition for removing harmful animals, wherein a compound of the formula (I) according to one of claims 1 to 8, is mixed with an extender additive.

13. A compound of the formula (I) selected from the group consisting of: 2- [n- (1-hydroxyhexyl)] piperidine, 2- [n- (1-hydroxyheptyl)] piperidine, 2- [ n- (1-hydroxyoctyl)] -piperidine, N-acetyl-2- [(1-hydroxy) (1-undecyl)] piperidine, and N-ethoxycarbonyl-2- [(1-hydroxy) (1-undecyl)] piperidine. - "- '' - H > - r ^ & ..-