DE2639748A1 - (N)-Aryl-(N')-alkyl-thiourea derivs. - useful as ectoparasiticides, insecticides, fungicides, acaricides - Google Patents

Abstract

N-Aryl-N'-(cyclo)alkyl-thioureas of formula (I) and their acid-addn. salts are new: (where R1 is 1-6C alkul or 3-7C cycloalkyl; R2 is 2-6C alkyl or 3-7C cycloalkyl; R3 is 1-6C alkyl, 3-6C alkenyl, 3-7C cycloalkyl, 5-7C cycloalkenyl or halogen; n = 0-2; R7 is opt. substd. 3-10C cycloalkyl, opt. substd. 5-10C cycloalkenyl, or CR4R5R5; R4 is H, 1-6C alkyl or 3-7C cycloalkyl; R5 and R6 alkyl or 3-7C cycloalkyl). They are esp. active against phosphate-resistant Boophilus ticks and other animal ectoparasites. A typical cpd. is N-(2,6-di-s-butulphenyl)-N'-butyl-thiourea. In an example, this is prepd. from 2,6-di-s-butylphenyl isothiocyanate and t-butylamine.

Description

New N-aryl-N'-alkyl-thioureas, method too

their production and their use as a means of combating of animal and vegetable pests The present invention relates to new ones N-Aryl-N'-alkylthioureas, processes for their preparation and their use as a means of combating animal and vegetable pests, in particular as ectoparasiticides, insecticides and acaricides.

It is already known that N-aryl-N ', N'-dialkyl-thioureas as ectoparasiticides, in particular as tickicides against ticks of the genus boophilus, are effective (see DT-OS 2 337 122).

Show towards the known and chemically related compounds the N-aryl-N'-alkylthioureas according to the invention have a better effect against phosphoric ester-resistant Ticks of the genus boqphilus as well a distinctly pronounced insecticidal Side effect that the comparative products from DT-OS 2 337 122 lack. They are also Effective in agriculture against insects which are harmful to plants and against mites.

It has been found that the new N-aryl-N'-alkyl-thioureas of the general formula (I) in which R1 and R2 can be identical or different and are alkyl (C1-C6) or cycloalkyl (C4-C7), R3 is alkyl (C1-C6) or halogen, n is an integer from 0-2 and R4 stands for hydrogen, alkyl (C1-C6) or cycloalkyl (c4-c7) and R5 and R6 can be the same or different and stand for alkyl (C1-C6 or cycloalkyl (C4-C7)), a strong one Have an effect on animal and plant pests, in particular an ectoparasiticidal, insecticidal and acaricidal effect.

It has also been found that the new N-aryl-N'-alkyl-thioureas of the formula (I) are obtained if a) aryl isothiocyanates of the formula with alkylamines of the formula or alternatively b) alkyl isothiocyanates of the formula with arylamines of the formula reacted, where R1, R2, R3, R4, R5, R6 and n each have the meaning given above.

The novel N-aryl-N'-alkyl-thioureas according to the invention surprisingly show a more pronounced ectoparasiticidal effect than the chemically closely related ones N-aryl-N ', N'-dialkyl-thioureas from DT-OS 2 337 122 as well as an additional insecticidal Effect as well as an effect against mites, which corresponds to the compounds from DT-OS 2 337 122 are missing.

The compounds according to the invention are thus an enrichment of technology.

If, according to variant a), 2,6-di-sec-butylphenyl isothiocyanate and tert-butylamine are used as starting materials, the course of the reaction can be represented by the following equation: (Reaction equation A) If, according to variant b), tert-butyl isothiocyanate and 2,6-diisopropyl phenyl isothiocyanate are used as starting materials, the course of the reaction can be represented by the following equation: (Reaction equation B) In formula (I), the radicals R1, R2, R4, R5 and R6 are preferably alkyl (C1-C6) and cycloalkyl (C4-C7). Examples include: methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, iso-butyl, tert-butyl, pentyl (2), pentyl (3), tert-pentyl, cyclopentyl, hexyl ( 2), hexyl- (3), cyclohexyl.

The radical R3 is preferably alkyl (C1-C4), for example Methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, iso-butyl, tert-butyl or for halogen, preferably for chlorine or bromine.

The aryl isothiocyanates used as starting compounds of the general Formula (II) and alkyl isothiocyanates of the general formula (IV) are known or are known can be prepared by known methods, for example by reaction of arylamines of the general formula (V) or alkylamines of the general formula (III) with thiophosgene, by reacting N-aryl or N-alkyl dithiocarboxylic acids Salts with phosgene or oxidizing agents or from alkyl halides and alkali thiocyanates or from olefins and hydrogen rhodanic acid (see Houben-Weyl, "Methods of organic Chemie ", Vol. IX, pages 867-878).

As starting compounds for the according to reaction equation A to be used Aryl isothiocyanates of the general formula (II) may be mentioned, for example: 2, 6-dimethyl-phenyl isothiocyanate, 2-methyl-6-ethyl-phenyl isothiocyanate, 2,6-diethyl-phenyl isothiocyanate 2-ethyl-6-isopropyl-phenyl-isothiocyanate, 2,6-diisopropyl-phenyl-isothiocyanate, 2,6-di-sec-butyl-phenyl isothiocyanate 2-methyl-6-sec-butyl-phenyl isothiocyanate, 2-ethyl-6-sec-butyl-phenyl isothiocyanate 2-isopropyl-6-sec-butyl-phenyl isothiocyanate, 2-methyl-6-isopropyl-phenyl isothiocyanate 2-methyl-6-cyclopentyl-phenyl isothiocyanate, 2-ethyl-6-cyclopentyl-phenyl isothiocyanate 2-isopropyl-6-cyclopentyl-phenyl isothiocyanate, 2,6-di-cyclopentyl-phenyl isothiocyanate 2-methyl-6-tert-butyl-phenyl isothiocyanate, 2-ethyl-6-tert-butyl-phenyl isothiocyanate 2-methyl-6-cyclohexyl-phenyl isothiocyanate, 2-ethyl-6-cyclopentyl-phenyl isothiocyanate 2,4-dimethyl-6-ethyl-phenyl isothiocyanate 2,4-dimethyl-6-isopropyl-phenyl isothiocyanate 2,4-dimethyl-6-sec-butyl-phenyl isothiocyanate 2,4-dimethyl-6-tert-butyl-phenyl isothiocyanate 2,4,6-trimethyl-phenyl-isothiocyanate, 2,6-diethyl-4-methyl-phenyl-isothiocyanate, 2,6-diisopropyl-4-methyl-phenyl-isothiocyanate 2,6-dimethyl-2,6-diethyl phenyl isothiocyanate, 3-methyl-2,6-diethyl phenyl isothiocyanate 3-chloro-2,6-diethil-phenyl isothiocyanate The aforementioned aryl isothiocyanates underlying - arylamines of the general formula V can alternatively be used for the Manufacturing of the compounds of the general formula I according to reaction equation B can be used.

Examples of alkyl isothiocyanates of the general formula IV are called: isopropyl isothiocyanate sec-butyl isothiocyanate pentyl (2) isothione cyanate Hexyl (2) isothiocyanate octyl (2) isothiocyanate 3-methyl butyl (2) isothiocyanate 3-methyl pentyl (2) isothiocyanate 4-methyl pentyl (2) isothiocyanate pentyl (3) isothiocyanate 2-methylpentyl (3) isothiocyanate 2,4-dimethylpentyl (3) isothiocyanate hexyl (3) isothiocyanate 2-methyl-hexyl- (3) -isothiocyanate 3,3-dimethyl-butyl- (2) -isothiocyanate 2,2-dimethyl-pentyl- (3) -isothiocyanate 1-Cyclopentyl ethyl isothiocyanate, tert-butyl isothiocyanate, tert-pentyl isothiocyanate 3-methyl-pentyl- (3) -isothiocyanate 3-ethyl-pentyl- (3) -isothiocyanate 2-methylpentyl (2) isothiocyanate 2-methyl-hexyl- (2) -isothiocyanate 3-methyl-hexyl- (3) -isothiocyanate 2-methyl-octyl- (2) isothiocyanate The alkylamines on which the aforementioned alkyl isothiocyanates are based of the general formula (III) can alternatively be used for the preparation of compounds of the general formula (I) can be used in analogy to reaction equation A.

According to the invention, as already mentioned above, a) the substituted Aryl isothiocyanates of the general formula (II) with the alkylamines of the general formula Formula (III) or alternatively b) alkyl isothiocyanates of the general formula (IV) reacted with arylamines of the general formula (V).

The conversion takes place in molar or approximately molar ratios, the more volatile or less valuable component being used in excess can be, for example with 5-50% excess. However, it is in a preferred one Embodiment also possible, for example the alkylamines of the general formula (III) in a large excess, namely 2-20 moles, based on 1 mole of aryl isothiocyanate II to use. They thus also serve as a solvent for the resulting Thioureas of the general formula (I) and can after implementation Distillation can be largely recovered.

When carrying out the implementation according to equation A or B can tertiary organic bases are added to accelerate the reaction. One works for example at temperatures from 10 to 1200C, in particular from 20 to 600C. The implementation of the substituted aryl isothiocyanates of the general formula (II) with the alkylamines of the general formula III or, alternatively, the alkyl isothiocyanates IV with the arylamines of the formula V can be in the melt or without a solvent take place with the addition of a solvent and diluent. As such, for example are used: hydrocarbons or halogenated hydrocarbons such as petroleum ether, Benzene, ligroin, cyclohexane, benzene, toluene, chlorobenzene, methylene chloride, Chloroform, carbon tetrachloride, water-soluble solvents such as methanol, methanol, Acetone, acetonitrile, dimethylformamide, if necessary, can continue the approaches inorganic or, as already mentioned above, organic bases as accelerators be added, for example triethylamine, 1,4-diazablcyclo- / 2,2,27-octane (DABCO) 1,5-Diaza-bicyclo- [4,3,0] -nonen- (5) (DBN) 1, -Diaza-bicyclo-C5 ß5,4, Q -ndecen- (7) (DBU), potassium hydroxide, sodium hydroxide, sodium hydride, sodium oxide.

Depending on the starting compounds, the reactions can be exothermic and depending on the size and presence of diluent by cooling under Control must be kept, or the reactions must be effected by heating, for example be accelerated to temperatures of 40-1500C, preferably 50-1000C. The implementation conditions are therefore individually different and depend on the type and amount of used Starting materials and the solvent used.

Working up is carried out either by distilling off solvents and recrystallizing the reaction product or by pouring it into water or dilute aqueous mineral acids, filtration and drying.

As new N-aryl-N'-alkyl-thioureas of the general formula (I) the following compounds are listed: N- (2,6-diisopropyl-phenyl) -N'-tert-butyl-thiourea F: 135-13700 N- (2,6-diisopropyl-phenyl) -N'-tert-pentyl-thiourea F: 134 - 135 ° C N- (2,6-Diisopropyl-phenyl) -N '- (1,1,2,2-tetramethyl-propyl thiourea F: 161-16200 N- (2,6-diethylphenyl) -n'-tert-butyl-thiourea F: 98-10,000 N- (2,6-diethyl-phenyl) -N'-tert-pentyl-thiourea F: 85 - 8700 N- (2,6-di.sec.-butyl-phenyl) -N'-tert.-pentyl-triourea F: 116 - 118 ° C N- (2,6-Dissek-butyl-phenSl) -Nt-tert-butyl-thiourea F: 115 - 117 ° C N- (2,6-diethyl-phenyl) -N'-isopropyl- triourea F: 108 - 11000 N- (2,6-diethyl-phenyl) -N'-sec-butyl-triourea F: 78 - 80 ° C N- (2,6-di-sec-butyl-phenyl) - Nt-isopropyl thiourea F: 108 - 11100 N- (2,6-di-sec-butyl-phenyl) -N-sec-butyl-thiourea F: 103 - 105 ° C N- (2,4-dimethyl-6-ethyl-phenyl) -N'-tert-butyl-triourea F: 130-13,200 N- (2,4-Dimethyl-6-ethyl-phenyl) -N'-tert-butyl-triourea F: 105-1070c N- (4-methyl-2,6-diethyl-phenyl) ° N'-tert-butyl-thiourea F: 121-1230C N- (4-methyl-2,6-diethyl-phenyl) -N'-tert-pentyl-thiourea F: 98-101% N- (2-methyl-6-ethyl-phenyl) -N'-tert-butyl-triourea F: 94-96 ° C N- (2-methyl-6-ethyl-phenyl) -N '-tert. -pentyl-thiourea F: 78 - 81 ° C N- (2,4,6-trimethylphenyl) -N'-tert-pentyl-thiourea N- (2,6-diethyl) -methyl-phenyl) -N-tert-butyl-thiourea N- (2,6-diethyl-3,5-dimethyl-phenyl) -N'-tert-butyl-triourea N- (2,6-Diethyl-3,5-dimethyl-phenyl) -N'-tert-pentyl- (2) -triourea N- (2,6-di-isopropyl-phenyl) -N '- [3 -methyl-butyl- (2)] - triourea N- (2,6-di-sec-butyl-phenyl) -N '- [pentyl- (2)] -triourea N- (2,6-di-sec, -butyl-phenyl) -N' {hexyl - (22-thiourea N- (2,6-di-sec-butyl-phenyl) -N | pentyl- (3g-thiourea N- (2,6-di-sec-butyl-phenyl) -N '- [4-methyl-pentyl- (2)] - triourine substance N- (2,6-di-sec-butyl-phenyl) -N '- [2-methyl-pentyl- (3)] -triourea N- (2,6-diisopropyl-phenyl) -N' {pentyl - (22-thiourine N- (2,6-Diisopropyl-phenyl) -N '+ hexyl- (2) 3-thiourea N- (2,6-Diisopropyl-phenyl) -N' - [3-methyl-pentyl- (2)] - triourea N- (2,6-Diisopropyl-phenyl) -N'ientyl- (32-thiourea N- (2,6-diisopropyl-phenyl) -N-22,2-dimethyl-pentyl- (3) -thiourea N- (2-Ethyl-6-sec-butyl-phenyl) -N'-tert-butyl-triourea F: 96-99 ° C N- (2-isopropyl-6-sel-butyl-phenyl) -N '-tert-butyl triourea F: 121-123 C N- (2-isopropyl-6-sec-butyl-phenyl) -N'-tert-butyl-triourea F: 51-530C N- (2,6-Diisopropyl-phenyl) -N '- [1-cyclopentyl-ethyl] -triourea N- (2,6-di-sec-butyl-phenyl) -N '- [2-methyl-penthyl- (2)] - triourea N- (2,6-di-sec-butyl-phenyl) - N '- [2-ethyl-penthyl- (2)] - triourea N- (2,6-di-sec-butyl-phenyl) -N '- [2-methyl-heyl- (2)] - triourea N- (2,6-diethyl-phenyl) -N' - [2 -methyl-octyl- (2)] - triourea N- (2,6-diisopropyl-phenyl) -N '- [2-methyl-penthyl- (2)] - triourea N- (2,6-diisopropyl-phenyl) -N' - [2-ethyl-penthyl- (2)] - triourea N- (2,6-diethyl-3-chloro-phenyl) -N'-tert.-butyl-triourea N- (2-ethyl-6-sec-butyl-phenyl) -N'-tert.-pentyl- thiourea F: 74 - 76 ° C N- (2,6-Di-cyclopenthyl-phenyl) -N'-tert-butyl-triourea N- (2-ethyl-4-methyl-6-sec-butyl-phenyl) -N2-tert-butyl-thiourea N- (2,4-Dimethyl-6-tert-butyl-phenyl) -N'-tert-pentyl-thiourea N- [2,6-di-pentyl- (2) -phenyl] -N'-tert .-butyl triourea N-2,4-Dimethyl-6-cyclohexyl-phenyl) -N'-tert-butyl-triourea N- (2,6-diisopropyl-4-chlorophenyl) -N'-tert-butyl-triourea N- (2,5-dimethyl-6-ethyl-phenyl) -N'-tert-pentyl-thiourea N- (2,5-dimethyl-6-isopropyl-phenyl) -N'-tert-pentyl-triourea N- (2,6-diethyl-phenyl) -N '- [2-methyl-pentyl- (2)] -triourea N- (2,6-diethyl-phenyl) -N' - [2-ethyl-pentyl- (2)] - triourea N- (2,6-diethyl-phenyl) -N '- [2-methyl-hexyl- (2)] - triourea N- (2,6-diethyl-phenyl) -N'- Rdecyl- (5 µg -thiourea N- (2,6-diethyl-phenyl) -N '- [1,1,2,2-tetramethyl-propyl] -triourea N- (2,6-diethyl-phenyl) -N '- [2,4-dimethyl-hexyl- (3)] - triourea N- (2,6-dimethyl-phenyl) -N' - [2,2- dimethyl-hexyl- (3)] -triourea the Active ingredients are suitable if they are well tolerated by plants and have favorable toxicity to warm-blooded animals to control animal pests, especially insects and arachnids, those in veterinary medicine, in agriculture, in forests, in storage and Material protection as well as in the hygiene sector. You are sensitive to normal and resistant species and effective against all or individual stages of development.

The pests mentioned above include: From the order of the Isopoda z. B. Oniscus asellus, Armadillidium vulgare, Porcellio scaber.

From the order of the Diplopoda, for. B. Blaniulus guttulatus.

From the order of the Chilopoda, for. B. Geophilus carpophagus, Scutigera spec.

From the order of the Symphyla z. B. Scutigerella immaculata.

From the order of the Thysanura z. B. Lepisma saccharina.

From the order of the Collembola, for. B. Onychiurus armatus.

From the order of the Orthoptera z. B. Blatta orientalis, Periplaneta americana, Leucophaea maderae, Blattella germanica, Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus differentialis, Schistocerca gregaria.

From the order of the Dermaptera, for. B. Forficula auricularia.

From the order of the Isoptera, for. B. Reticulitermes spp ..

From the order of the Anoplura, e.g. B. Phylloxera vastatrix, Pemphigus spp., Pediculus humanus corporis, Haematopinus spp., Linognathus spp.

From the order of the Mallophaga, for example Trichodectes spp., Damalinea spp.

From the order of the Thysanoptera, e.g. Hercinothrips femoralis, Thrips tabaci.

From the order of the Heteroptera, e.g. Eurygaster spp., Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodnius prolixus, Triatoma spp.

From the order of the Homoptera, e.g. Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Doralis fabae, Doralis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Macrosiphum avenae, Myzus spp., Phorodon humuli, Rhopalosiphum padi, Empoasca spp., Euscelis bilobatus, Nephotettix cincticepsS Lecanium corni, Saissetia oleat Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp.

Psylla spp ..

From the order of the Lepidoptera, for. B. Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brumataw Lithocolletis blancardella, Hyponomeuta padella, Plutella maculipennis, Malacosoma neustria, Euproctis chrysorrhoea, Lymantria spp., Bucculatrix thurberiella, Phyllocnistis citrella, Agrotis spp., Euxoa spp., Feltia spp., Earias insulana, Heliothis spp., Laphygma exigua, Mamestra brassicae, Panolis flammea, Prodenia litura, Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Galleria mellonella, Cacoecia podana, Capua reticulans, Choristoneura fumiferana, Clysia ambiguella, Homona magnanima, Tortrix viridana.

From the order of the Coleoptera, for. B. Anobium punctatum, Rhizopertha dominica, Bruchidjus obtectus, Acanthoscelides obtectus, Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedon cochleariae, Diabrotica spp., Psylliodes chrysocephala, Epilachna varivestis, Atomaria spp., Oryzaephilus surinamensis, Anthonomus spp., Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites sordidus, Ceuthorrhynchuæ assimilis, Hypera postica, Dermestes spp., Trogoderma spp., Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus, Ptinus spp., Niptus hololecus, Gibbium psylloides, Tribolium spp., Tenebrio molitor, Agriotes spp., Conoderus spp.

Melolontha melolontha, Amphimallon solstitialis, Coatelytra zealandica.

From the order of the Hymenoptera, for. B. Diprion spp., Hoplooampa spp., Lasius spp., Monomorium pharaonis, Vespa spp.

From the order of the Diptera, for example, Aedes spp., Anopheles spp., Culex spp., Drosophila melanogaster, Musca spp., Fannia spp., Calliphora erythrocephala, Lucilia spp., - Chrysomyia spp., Cuterebra spp., Gastrophilus spp., Hyppobosca spp., Stomoxys spp., Oestrus spp., Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinella frit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae, Tipula paludosa.

From the order of the Siphonaptera, e.g. Xenopsylla cheopis, Ceratophyllus spp.

From the order of the Arachnida, e.g. Scorpio maurus, Latrodectus mactans From the order of the Acarina, e.g. Acarus siro, Argas spp., Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalomma spp., Ixodes sppO, Psoroptes spp., Chorioptes spp., Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp ..

The active compounds according to the invention are used in the form of them commercial formulations and / or those prepared from these formulations Application forms.

The active ingredient content of the prepared from the commercially available formulations Application forms can vary within wide ranges.

The active ingredient concentration of the use forms can range from 0.0000001 up to 100% by weight of active ingredient, preferably between 0.01 and 10% by weight.

They are used in a customary manner adapted to the use forms Way.

The active compounds according to the invention are used in the veterinary sector in a known manner, such as by oral use in the form of, for example, tablets, Capsules, potions, granules, through dermal application in the form of, for example, the Dipping (dipping), spraying (spraying), pour-on and spot-on and des Powdering as well as through. parenteral use in the form of, for example, injection.

The active ingredients can be stirred into the usual formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, foams, Pastes, soluble powders, granulates, aerosols, suspension emulsion concentrates, Seed powder, natural and synthetic substances impregnated with active ingredients, ultra-fine encapsulation in polymeric substances and in coating compounds for seeds, also in formulations with Burning sets, such as incense cartridges, cans, spirals, etc. as well as ULV cold and warm mist formulations.

These formulations are prepared in a known manner, e.g. by mixing the active ingredients with extenders, i.e. liquid solvents, liquefied gases under pressure and / or solid carriers, if appropriate using surface-active agents, i.e. emulsifying agents uld / or Dispersants and / or foam-generating agents.

In the case of using water as an extender, e.g.

organic solvents can also be used as auxiliary solvents. The main liquid solvents that can be used are: aromatics, such as xylene, Toluene, or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffin, e.g. petroleum fractions, alcohols such as butanol or Glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strong pole solvents such as dimethylformamide and dimethyl sulfide, as well as water; with liquefied gaseous extenders or carriers such liquids are meant which are at normal temperature and under normal pressure are gaseous, e.g. aerosol propellants such as halogenated hydrocarbons as Butane, propane, nitrogen and carbon dioxide; as solid carriers: natural rock flour, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic barley in flours, such as fumed silica, alumina and Silicates; as solid carriers for granules: broken and fractionated natural Rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granulates made from inorganic and organic flours and granulates made from organic material such as sawdust, wokosnut shells, corn on the cob and tobacco stalks; as an emulsifier and / or Foaming agents: non-ionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, Polyoxyethylene fatty alcohol ethers, e.g. alkylaryl polyglycol ethers, alkyl sulfonates, Alkyl sulfates, aryl sulfonates and protein hydrolysates; as a dispersant: e.g. Lignin, sulphite waste liquors and methyl cellulose.

Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-like polymers are used such as gum arabic, polyvinyl alcohol, polyvinyl acetate There can be dyes such as inorganic pigments such as iron oxide, titanium oxide, ferrocyan blue and organic Dyes such as alizarin, azo metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.

The formulations generally contain between 0.1 and 95 percent by weight Active ingredient, preferably between 0.5 and 90%.

Example In vivo tick test on Boophilus microplus 3 parts of active ingredient are with 7 parts of a mixture of equal parts by weight of ethylene glycol monomethyl ether and nonylphenyl polyglycol ether mixed. The emulsicin concentrate thus obtained is diluted with water to the desired application concentration.

Cattle are sprayed with the active ingredient preparation obtained in this way, those with resistant tick larvae of the species Boophilus mleroplus, Biarra strain, several times (Infection 12 times with an interval of 2 days) have been infected.

The effect of the active ingredient preparation is determined by determination the number of adult females developing on the treated cattle Ticks. This number is compared to the number of adult female ticks that develop on untreated cattle. A connection is all the more effective the fewer female ticks develop after treatment.

The number of adult females used in treated and untreated animals in the the last three days before the time of treatment to develop.

in vivo Number of ticks with fertile clutches Active ingredient concentration days days after treatment effect tration and forward in% Active ingredient Beh. # -2 # 0 + 1-3 4-6 7-9 10-18 13-15 16-18 19-21 + 1-21 known from DT-OS 2 337 122: CH3 S # # Cl - # - NH-CN-CH3 # CH3 1,000 ppm 1910 132 37 35 54 15 0 0 273 97.63 according to the invention: CH3CH2 CH3 # # CH S CH3 # # # # -NH-C-NH-C-CH3 # # CH CH3 # # CH3CH2 CH3 250 ppm 1244 21 12 10 10 2 0 0 55 98.5 C2H5 S CH3 # # # # -NH-C-NH-C-CH3 # # C2H5 CH3 250 ppm 595 21 0 27 8 0 0 0 56 96.5 Tick test solvent: 35 parts by weight of ethylene glycol Imonome thylacther 35 parts by weight of nonylphenol polycola ether To prepare a suitable formulation, mix three parts by weight of active ingredient with seven parts of the above solvent-emulsifier mixture and dilute the resulting emulsion concentrate with water to the desired concentration.

Adult female ticks are suckled into these active ingredient preparations of the species Boophilus microplus (sensitive or resistant) immersed for one minute. After diving from Je lo female specimens of the various tick species transferred they are placed in Petri dishes, the bottom of which is covered with a correspondingly large filter disk is occupied.

After 10 days, the effectiveness of the active ingredient preparation is determined by determining the inhibition of oviposition compared to untreated control ticks. The effect is expressed in percent, where loo ffi means that there are no more eggs and 0 ffi means that the ticks laid eggs in normal quantities.

The active ingredient investigated, the concentration tested, the parasites tested and the results obtained are shown in the following table. Active ingredient concentration killing effect according to the invention in% Active ingredient tration in ppm Boophilus miaroplus res. 5 CH $ 3CH3 S 1 3 10,000 100 NH-C-NH-C CH3 1,000> 50 CH3 CH3 CH3 CH CH'CH3 S CH3 10,000 100 (/ \ 9NH-C-NH-C C2H5 1 1,000 100 CH CH3 3 C2H5 CH3 10,000 100 <NH-C-NH-c -CH3 1.OC0> 50 - 1 3 1,000> 50 2H5 CH L3 C2H5 2H5 S CH3 10,000 100 NH-C-NHC C2H5 1,000> 50 - 1 C2H5 CH3 CH CHoC2H5 S CH3 10,000 100 II 1 3 NHC-NHC -C2H5 1,000> 50 CH H CH3 CH 2 5 3 CfI'c2H5 5 CEr3 10,000 100 NH-C-NH-C 1,000 1st (X) 100 CH cH3 H 3 CH? C2H5 3 S CH3 10,000 100 NHC-NH-CH 1,000 <50 C5 C2H5 C2H5 10,000 100 CH NH-C-NH-C 100 H3 S 1 3 10030> C2H5 CH3 CH5511 S, 10,000 100 Jjr s. CI3 3 <g C2H5 1,000> 50 rmT C2H5 CH3 For comparison: Active substance-killing effect in ffi Active ingredient concentration Boophilus microplus in ppm res. known pears CH, 3 s 1,000 <50 bl U -NH-CN-CH3 100 O CH3 Test with parasitic fly larvae Solvent: 35 parts by weight of ethylene polyglycol monomethyl ether 35 parts by weight of nonylphenol polyglycol ether To produce an appropriate preparation of the active ingredient, 30 parts by weight of the active substance in question are mixed with the specified amount of solvent which contains the above-mentioned proportion of emulsifier and then diluted thus obtained concentrate with water to the desired concentration.

About 20 fly larvae (Lucilia cuprina) are placed in a test tube which contains approx. 2 cm3 horse muscles. 0.5 ml of the active compound preparation are placed on this horse meat. The degree of destruction is determined in% after 24 hours. 100% means that all larvae have been killed and 0% that none of the larvae have been killed. Active ingredient active ingredient concentration from killing effect in% tration in ppm Lucilia cuprina res. CH3 / \ CHCH3 S CH3 1,000 100 NHC-NHC CtI 300 100 - w 3 CH-CH CH3 CH CH3 \ CHC2H5 S CH3 1,000 100 <NH-C-NH-C -C2H5 CH, C2H5 CH3 CH CH H 2 5 "1.0C0 100 > NH-C-NH-C-NH 300 NH 3 300 100 CH-C2H5 CH3 100> 50 CH3 C2H5 S 3 1,000 100 NHC "-NHC -CH H3 1 'CH3 3 C2H5 CH3 Active ingredient active ingredient concentration killing effect in% tration in ppn Psoroptes cuniculi CH3 / CH3 G CH S CH3 1,000 100 NHC-NHC CH 300 100 3 / CF CH3 100 100 CH3 I.ooo CH 3 3 CH3 \ / CH3 1,000 100 5 o CH3 S CM NH $ '- NH-C' 3 100 100 - C2H5 CH3 cH3 CH3 3 CH3 \ / cH3 CH 5 CH3 CM 1,000 100 II NH-C-NH-C 1 - I 3 100 100 J 10 100 CM CH3 CH3 3 3 3 CM CH 3 3 z 2H5 S CH3 1,000 100 {NH-C-NH-C-CH3 100 100 <, 3 100 100 C2H5 CH3 10 100 1 100 1C2HSS11 CH3 1,000 100 NHC-NHC C2Hg 100 100 <, 2 5 100 100 C2H5 CH3 10 100 1> 50 CH3 / C2H5 CM 5 CH3 1,000 100 II -C, pa, 1 -C-NH-C -C2H5 100 100 io ioo CH3 3 XC2H5 1 100 ~ ~. Active ingredient active ingredient concentration killing effect in% tration in ppm Psoroptes cuniculi. CH3 / C2H5 5 CH CH II CH3 1,000 100 t NH-C-NH-C 3 100 100 / CH CH3 10 100 CH XC H 1 50 CH 5 S CIH, 1,000 100 II " 100 \ <-C-NH-CH 100 2Hg C2H5 C2H5 cH3 / C2H5 1,000 100 vCH S CH / I NH-C- 1 3 100 100 z NH-CH <1 10 100 / CH CH3 3 CH3 \ C2H5 25th CH \ / C2H S CH3 1,000 100 -NH-NH-CH NH-C-NH-CH 100 100 10 100 CH C2H5 CH3 \ CH 25th (313 1,000 100 / H3 100 e 1 sCH3 100 100 - NH-C-NH-C 13 C2H5 CH3 5 S CH3 1,000 100 NH-N, 2 H 100 100 - 25th C2H5 CH3 C2H5 3 Active ingredient active ingredient concentration killing effect in% tration in ppn Psoroptes cunicul CH3 S CH3 3 5 CH II 1 3 \ t-N1 -NH-C CH3 1,000 100 C2H5 CH3 100 100 C2H5 5 cH3 CH3 NH-C-NH-C -CH3 1,000 100 CH 100 100 C2H5 CH3 100 100 C2H5 S CH3 CH3CMHC -C2H, 1,000 100 C2H5 CH3 L3 HSCH, S CH, -JH-C-NH-C C2H, 1,000 100 2 5 CH3 Example Tetranychus test (resistant) Solvent: 3 parts by weight of dimethylformamide emulsifier: 1 part by weight of alkylaryl polyglycol ether To produce an appropriate preparation of active ingredient, 1 part by weight of active ingredient is mixed with the specified amount of solvent and the specified amount of emulsifier and the concentrate is diluted with water to the desired concentration.

Bean plants (Phaseolus vulgaris), which strongly differ from all stages of development of the common spider mite or bean spider mite (Tetranychus urticae) are infected, sprayed dripping wet.

After the specified times, the destruction in 96 is determined.

100 9 'means that all spider mites have been killed; 0 96 means that no spider mites have been killed.

Active ingredients, active ingredient concentrations 9 Evaluation times and results are shown in the following table: Table (plant-damaging mites) Tetranychus test (resistant) Active ingredients active ingredient killing degree centering in% in% 2 days CH Cl- Q -NH-CS-Ns 0.1 60 CH3 0.01 0 CH3 known Active ingredients according to the invention: CH3 / C2H5 CH CH M -NH-CS-NH-CH 0.1 100 - \ CH3 0.01 100 / CH 3 CH3 CH3 CH3 / C2H5 2 / CH3 (NH-CS-NH-CH 0.1 100 9 H \ C2H5 0.01 100 CH3 \ C2H5 3 25 CH3 \ / CH3 CH CH J β -NH-CS-NH-C 0.1 0.1 100 0.01 100 / CH \ CH3 CH3 CH3 CH3u / C2H5 CH CH3 4 -NH-CS-NH-C-CH3 0.1 100 CH 0.07 70 / CHX 3 CH3 C2H5 Table (plant-damaging mites) Tetranychus test (resistant) Active ingredients active ingredient killing degree centering in% in% 2 days C2H5 H H3C- (J. H3C-X-NH-CS-NH-C -C2H5 0.1 100 C2H5 CH3 0.01 99 CH3 \ / cH3 CII CII 3 Q -NH-CS-NH-C 0.1 0.01 100 -; 1H 0.01 99 CIT CM CH / \ CH3 3 CH3 / C2H5 / CH 3 ß NH-CS-NH-C --C2H5 0.1 100 H 0.01 100 CII CH3 3 CH3 C2H5 Example Plutella test Solvent: 3 parts by weight of dimethylformamide emulsifier: 1 part by weight of alkylaryl polyglycol ether To produce an appropriate preparation of active ingredient, 1 part by weight of active ingredient is mixed with the stated amount of solvent and the stated amount of emulsifier and the concentrate is diluted with water to the desired concentration.

Cabbage leaves (Brassica oleracea) are sprayed with the preparation of the active compound dewy and populated with caterpillars of the cabbage moth (Plutella maculipennis).

After the specified times, the destruction in 96 is determined.

100% means that all the caterpillars have been killed; 0% means that no caterpillars were killed.

Active ingredients, active ingredient concentrations, evaluation times and results are shown in the table below: Table (insects which are harmful to plants) Plutella test Active ingredients hirkstoffxo.n- Abtst scvad centering in E r -> - 3 T.- ai Cl-O, 1 3 0.1 83 3 »3 0.01 0 = i3 ErfL sgmevZe active ingredients: Gj / C2H5 CH z a.-CSt CH3 0.1 100 CH 0.01 100 3 C-l3 CS5 Gl3 \, eC2H5 CH. "2H5 NH at 0.1 100 N 0.01 CH ½ 3 0.01 100 C2H5 3 1. X CS-E C -CH3 0.1 0.1 103 C = CX3 0.01 95 "5 CTi3 -cH3 0.1 100 . \ 90 Cw J3 0.01 D. Table (plant damaging insects) Plutella test Active ingredients active ingredient killing degree centering in% in% 3 days f3 \ / CH3 CH3 CH CH3 -NH-CS-NH-C CH 0.1 100 63 = (1 3 0.01 100 CH CH CH3 3 / C2H5 CH CH 13th IJ - CH7 -CH3 0.1 100 0.01 100 CH3 CH CH 25th C2H5 CH H3C- 4 -NH-CS-NH-C -C2H5 0.1 100 0.01 100 C2H5 CH CI3 CH3 \ / CH3 CH CH I. \) - JH-CS-NH-C c2Hs 0.1 100 Cm 0.01 100 CH CH3 CH \ CH3 CH3 / C2H5 CH CH 3 4 NH-CS-NH-C -C2H5 0.1 100 \ 'O.01 100 ha, 0.01 CH3 CH3 C2H5 Table (plant damaging insects) Plutella test Active ingredients active ingredient killing degree centering in% in% naca 3 days CH3 \ CH3 CH CH CH 3.3 \\) - NH-CS-MI- 0.1 100 - HZ 3 0.01 100 ZCH3 \ C 3 C 3 CH3 CH3 3 3 Example 1 N- (2,6-di-sec-butyl-phenyl) -N'-tert-butyl-thiourea 20.0 g of 2,6-di-sec-butyl-phenyl isothiocyanate are added in 20.0 g Dissolved tert-butylamine and the batch was stored at 20 ° C. for 12 hours. It is then poured into dilute hydrochloric acid, the reaction product is filtered off, washed neutral and dried.

Yield 25.0 g; 96% d. Th. F: 115-117 ° C is obtained analogously from 2,6-di-sec-butyl-phenyl isothiocyanate and tert-pentylamine N- (2,6-di-sec-butyl-phenyl) -N'-tert-pentyl-thiourea from F: 116 - 11800.

The 2,6-di-sec used as the starting material. butyl phenyl isothiocyanate can be prepared as follows: 100 g of 2,6-di-sec-butyl-aniline in 200 ml Methylene chloride are mixed at 0 - 5 ° with stirring to a mixture of 300 ml of water, 500 ml of methylene chloride, 100 g of calcium carbonate and 68 g of thiophosgene were added dropwise. Thereafter the mixture is heated under reflux until the evolution of gas has ceased. After cooling down is filtered off from the solids, the methylene chloride layer is separated over Calcium chloride dried and fractionated: bp 117-1200C / 1.0 Torr; Yield 112 G; 93% d. Th.

The following are prepared in analogy to Example 1: From 2-ethyl-6-sec-butylphenyl isothiocyanate and tert-butylamine the compound N- (2-ethyl-6-sec-butyl-phenyl) -N'-tert-butyl-thiourea from melting point 96-990C; from 2-ethyl-6-sec-butyl-phenylisothiocyanate and tert. Pentylamine the compound N- (2-ethyl-6-sec-butyl-phenyl) -N'-tert-pentyl-thiourea from melting point 74-760C; from 2-isopropyl-6-sec-butyl-phenyl isothiocyanate and tert-butylamine the compound N- (2-isopropy ', - 6-sec-butyl-phenyl) -N'-tert-butyl-thiourea from melting point 121 - 123oC; from 2-isopropyl-6-sec. -butyl-phenyl) -isothiocyanate and tert. Pentylamine the compound N- (2,6-isopropyl-6-sec-butyl-phenyl) -N'-tert-pentyl-thiourea from melting point 51-530C.

Example 2 N- (2,6-Diisopropyl-phenyl) -N'-tert-butylthiourine peat 15 g of 2,6-diisopropyl-phenyl isothiocyanate are tert in 25 g. -Butylamine registered and kept at 200 for 12 hours. It is then poured into dilute hydrochloric acid, filtered, washes and dries.

Yield 17 g, melting point 135-137 °.

The same connection can also be obtained in the following way: 50 g of 2,6-diisopropyl-phenyl isothiocyanate and 19.0 g of tert-butylamine are in 250 ml of benzene and 20 ml of triethylamine for 5 hours. Heated under reflux. Then distilled the solvent is removed and the residue is crystallized with petroleum ether.

Yield 34g, F: 135-1370.

The 2,6-diisopropylphenyl isothiocyanate used as the starting compound can be prepared as follows: 100 g of 2,6-diisopropyl phenyl isothiocyanate in 200 ml of methylene chloride at 0 - 50 with stirring to a mixture of 300 ml of water, 500 ml of methylene chloride, 120 g of calcium carbonate and 78 g of thiophosgene were added dropwise. The mixture is then heated under reflux until the evolution of CO 2 has ended. After this Cooling is filtered, the methylene chloride layer is separated off over calcium chloride dried and fractionated.

Yield 110 g; 144-1480C / ll Torr.

Example 3 N- (2e6-Diisopropyl-phenyl) -N'-tert-pentyl-thiourea 11.0 g of 2,6-diisopropyl phenyl isothiocyanate and 10 g of tert-pentylamine are with 5 ml of triethylamine heated to 1000 for 10 minutes. After standing for 12 hours it will partially crystallized mixture stirred with petroleum ether, cooled to -100C, filtered off and dried.

Yield 14.0 g; F: 134-13500.

By reacting 15.0 g of 2,6-diisopropylphenyl isothiocyanate with 9.0 g of 1,1,2,2-tetramethyl-propylamine in 10 ml of triethylamine, as described above, the N- (2,6-diisopropyl-phenyl) -N '- (1,1,2,2-tetramethyl-propyl) -thiourea, F: 161-162 ° C.

Example 4 N- (2,6-Diethyl-phenyl) -N '-tert. -butyl thiourea 20 g of 2,6-diethyl phenyl isothiocyanate are introduced into 20 g of tert-butyl amine. It is cooled in such a way that 40.degree. C. is not exceeded. After 3 hours it is diluted with Stirred hydrochloric acid, suction filtered the crystalline reaction product, washed neutral and dried.

Yield 28.0 g; F-: 98-1000C.

In the above example, if the tert-butylamine is replaced by the the same amount of tert-pentylamine and if the procedure is as indicated, N- (2,6-diethyl-phenyl) -N'-tert-pentyl-thiourea is obtained; F: 85-870C.

2,6-Diethyl-phenylisothiocyanate can be prepared as follows: 100 g of 2,6-diethylaniline in 200 ml of methylene chloride are stirred at 0-50 to a mixture of 500 ml of methylene chloride, 300 ml of water, 120 g calcium carbonate and 92 g thiophosgene were added dropwise. Then it is heated to reflux, until the C02 development has ended. The cooled batch is filtered, the methylene chloride layer separated, dried with calcium chloride and fractionated.

Yield 112 g; Bp 101-1030C / 1.4 Torr.

Example 5 N- (2,6-Di-sec-butyl-phenyl) -N'-isopropyl-thiourea 15.0 g of 2,6-di-sec-butyl-phenyl isothiocyanate are cooled in 20 g of a 65% strength aqueous solution of isopropylamine entered. After stirring for 3 hours at 200 the batch is stirred into dilute hydrochloric acid, the precipitated crystalline The reaction product is sucked off, washed neutral, the paste is triturated with 50% methanol, vacuumed again and dried.

Yield 17.0 g; Q: 108 - 1110 If this is replaced in the example above Isopropylamine by 15.0 g sec. -Butylamine and works as indicated, so receives the N- (2,6-di-sec-butyl-phenyl) -N'-sec-butyl-thiourea F: 103-105 ° C By reacting 2,6-diethyl phenyl isothiocyanate with isopropylamine according to the above The process given gives N- (2,6-diethylphenyl) -N'-isopropylthiourea from F: 108 to 1100; with sec-butylamine the N- (2,6-diethyl-phenyl) -N'-sec-butyl-thiourea from F: 78 80 ° C.

Example 6 N- (2-methyl-6-ethyl-phenyl) -N '-tert. pentyl thioureas 15.0 g of 2-methyl-6-ethyl-phenyl isothiocyanate are tert with cooling in 20.0 g. -Pentylamine registered. After 2 hours the batch is stirred into dilute hydrochloric acid, the reaction product sucked off, triturated with 50 show methanol, sucked off and dried.

Yield 19.0g; F: 78-810C.

If in the above example the tert. -Pentylamine by the same Replaced the amount of tert-butylamine, the N- (2-methyl-6-ethyl-phenyl) -N'-tert-butyl-thiourea is obtained; F: 94-960C.

2-Methyl-6-ethyl-phenyl isothiocyanate can be prepared as follows be: 100 g of 2-methyl-6-ethyl-aniline in 200 ml of methylene chloride at 0 - 50 to a mixture of 500 ml of methylene chloride, 300 ml of water, 120 g of calcium carbonate and 103 g of thiophosgene were added dropwise.

The mixture is then refluxed until the evolution of CO 2 has ended is. Then solids are filtered off, the methylene chloride layer is separated off, dries over calcium chloride and fractionates.

Yield 121 g; Bp: 88-910C / 1.0 Torr.

Example 7 N- (4-methyl-2,6-diethyl-phenyl) -N'-tert-butyl-thiourea 15.0 g of 4-methyl-2,6-diethyl-phenyl-isothiocyanate are cooled in 20.0 g tert-butylamine entered. The mixture is stirred for 2 hours, poured into dilute hydrochloric acid, filtered, washed and dried.

Yield 18.0 g; F: 121-1230C.

If the tert-butylamine is replaced by the same in the above example Amount of tert-pentylamine and works as indicated, one obtains the N- (4-methyl-2,6-diethyl-phenyl) -N'-tert-pentyl-thiourea, F: 98-1010C is obtained analogously from 2,4-dimethyl-6-ethyl-phenyl isothiocyanate and tert-butylamine N- (2,4-dimethyl-6-ethyl-phenyl) -N'-tert-butyl-thiourea, F: 130 - 132 ° C, and from the same subst.

Phenylsothiocyanate and tert-pentylamine N- (4,2-dimethyl-6-ethyl-phenyl) -N'-tert-butyl-thiourea, F: 105-107 ° C.

The 4-methyl-2,6-diethylphenyl isothiocyanate used as the starting compound above can be prepared according to the following procedure: 100 g of 2,4-dimethyl-6-ethylaniline in 200 ml of methylene chloride at 0 - 5 ° C to a mixture of 500 ml of methylene chloride, 300 ml of water, 120 g of calcium carbonate and 92 g of thiophosgene were added dropwise with stirring. The mixture is then heated to reflux until the evolution of CO 2 has ended. To After cooling, the batch is filtered off from solids, the methylene chloride layer separated, dried over calcium chloride and fractionated; Yield 118 g, b.p. 101-104 ° C / 1.5 Torr.

Using the same procedure, 4-methyl-2,6-diethylaniline is obtained and thiophosgene 4-methyl-2,6-diethyl-phenyl isothiocyanate, boiling point 113-116 ° C / 1.2 Torr.

Claims (9)

Claims N-aryl-N'-alkyl-thioureas of the formula in which R1 and R2 can be identical or different and are alkyl (C1-C6) or cycloalkyl (C4-C7), R3 is alkyl (C1-C6) or halogen, n is an integer from 0 to 2 , R4 represents hydrogen, alkyl (C1-C6) or cycloalkyl (C4-C7) and R5 and R6 can be identical or different and represent alkyl (C1-C6) or cycloalkyl (C4-C7). 2) Process for the preparation of N-aryl-N'-alkyl-thioureas of the formula in which R1 and R² are identical or different and are alkyl (C1-C6) or cycloalkyl (C4-C7), R3 is alkyl (C1-C6) or halogen, n is an integer from 0 to 2, R4 stands for hydrogen, alkyl (C1-C6) or cycloalkyl (C4-C7) and R5 and R6 can be identical or different and stand for alkyl (C1-C6) or cycloalkyl (C4-C7), characterized that either a) aryl isothiocyanates of the formula in which R7, R2, R3 and n have the meaning given above, with alkylamines of the formula in which R4, R5 and R6 have the meaning given above, optionally in the presence of inert solvents, to react, or by b) alkyl isothiocyanates of the formula in which R4, R5 and R6 have the meaning given above, with arylamines of the formula in which R1, R2, R3 and n are as defined above, optionally in the presence of inert solvents. 3) Method according to claim 2, characterized in that at variant a) works with an excess of alkylamine. 4) Method according to claim 3, characterized in that the Reaction in the presence of tertiary organic bases at temperatures from 10 to 120 C, preferably 20 to 600C. 5) Ectoparasiticidal agents, characterized by a content of N-aryl-N'-alkylthioureas according to claim 1. 6) Agents effective against insects and acarids, characterized by a content of N-aryl-N'-alkylthioureas according to claim 1. 7) Process for the preparation of ectoparasiticidal agents, thereby characterized in that N-aryl-N'-alkylthioureas according to claim 1 with inert, mixed with non-toxic diluents or carriers. 8) Process for the production of agents which against insects and Acarides are effective, characterized in that one N-aryl-NI-alkylthioureas according to claim 1 mixed with suitable diluents or carriers. 9) method for combating ectoparasites, characterized in that that one infected by ectoparasites animals with N-aryl-N'-alkylthioureas according to Claim 1 treated.