MXPA99005160A - 3-thiocarbamoylpyrazole derivatives as pesticides - Google Patents

Abstract

This invention concerns new 3-thiocarbamoylpyrazole derivatives of formula (I) which Ar stands for substituted phenyl or pyridyl, R1 stands for H2N-CS- and R2 and R3 have the meaning given in the description, several processes for their production, and their use as pesticides.

Description

DERIVATIVES OF 3-TIOCARBAMOI PI? ZOL AS PESTICIDES. Field of the invention. The invention relates to novel 3-thiocarba-moilpyrazole derivatives, to various processes for their preparation and to their use as pesticidal agents. Description of the prior art. It is already known that certain substituted l-arylpyrazoles, such as for example 5-amino-l- [2,6-di-chloro-4- (trifluoromethyl) -phenyl] -3-cyano-4- [(trifluoromethyl) ) -sulfinyl] -lH-pyrazole have good activity against pests (see, for example, EP-A 295 117 and EP-A 352 944). In addition, a large number of substituted 1-aryl-pyrazoles have been described, which can be used for the control of pests (see for example EP-A 01 852, EP-A 418 016 or EP-A 0 659 745). However, the level of activity or duration of activity of the previously known compounds, and especially in the case of certain insects or at low application concentrations, are not always completely satisfactory in all fields of application. Detailed description of the invention. We have now found new 3-thiocarbamoylpyrazole derivatives of the general formula (I), REF .: 30241 Ar wherein R1 signifies H2N-CS, R2 means haloalkyl, haloalkenyl or halogenalkynyl, R3 means hydrogen, amino or means one of the following groupings: -NHR ' where R 4 signifies alkyl, haloalkyl or alkoxyalkyl or means phenyl or pyridyl substituted respectively where appropriate, R 5 signifies hydrogen or alkyl, R 6 signifies hydrogen, alkyl or means phenyl or pyridyl substituted respectively, and R7 is alkyl, alkenyl, alkynyl, formyl, alkylcarbonyl, haloalkylcarbonyl or alkoxycarbonyl; Ar means substituted phenyl or pyridyl, respectively, and n means a number 0, 1 or 2. It has also been found that the novel 3-thiocarbamoylpyrazole derivatives of the formula (I) are obtained if: -cyanopyrazole of the formula (II) Ar wherein Ar, R2, R3 and n have the meaning indicated above, with hydrogen sulphide, if appropriate in the presence of an auxiliary agent of the reaction; and, if applicable, in the presence of a diluent; b) 3-thiocarbamoylpyrazole derivatives of the formula (III) are reacted where Ar has the meaning indicated above and R3 1 means one of the following groupings: O R = N R "N N N H N ^ R6 -NHR where R4, R5, R6 and R7 have the meaning indicated above, with sulfenyl halides of the formula (IV) Hal-S-R2 (IV) in which R2 has the meaning indicated above and Hal means halogen, especially chlorine or bromine , if appropriate in the presence of a diluent and, if appropriate, in the presence of a reaction auxiliary agent; or c) the 2-thiocarbamoylpyrazole derivatives obtainable according to processes (a) or (b) of the formula (a) are oxidized. wherein Ar, R2 and R3 have the meaning indicated above, with oxidizing agents if appropriate in the presence of a diluent and, if appropriate, in the presence of a catalyst. Finally, it has been found that the new 3-thiocarbamoylpyrazole derivatives of the formula (I) have strongly marked biological properties and above all are suitable for the control against animal pests, especially against insects, arachnids and nematodes, which occur in agriculture. , in forestry, in the protection of stored products and materials as well as in the hygiene sector. The compounds according to the invention are generally defined by the formula (I). The substituents or the preferred ranges of the residues indicated in the above formulas and which will be cited below, are explained below. R1 means H2N-CS-. Preferably R2 means haloalkyl- (with 1 to 6 carbon atoms), with 1 to 12 halogen atoms, haloalkenyl- (with 2 to 6 carbon atoms) with 1 to 8 halogen atoms or halogenoalkynyl (with 2 to 6 carbon atoms) ) with 1 to 6 halogen atoms. Preferably * R3 means hydrogen, amino, or means one of the following groupings: where R 4 signifies alkyl- (with 1 to 6 carbon atoms), halogenalkyl- (with 1 to 6 carbon atoms) with 1 to 3 halogen atoms, alkoxy- ( with 1 to 6 carbon atoms) -alkyl- (with 1 to 6 carbon atoms) or means phenyl or pyridyl substituted, if appropriate, one to three times, in the same or different forms by cyano, by nitro, by halogen, for alkyl having 1 to 6 carbon atoms, for alkoxy with 1 to 6 carbon atoms, for alkylthio with 1 to 6 carbon atoms, for halogenalkyl with 1 to 4 carbon atoms, for halogenalkoxy with 1 to 4 carbon atoms; carbon or by haloalkylthio with 1 to 4 carbon atoms with respectively 1 to 5 halogen atoms, R5 means hydrogen or alkyl- (with 1 to 6 carbon atoms), R6 means hydrogen, alkyl- (with 1 to 6 carbon atoms) - bonus) or means phenyl substituted, if appropriate, one to three times, in the same way or different forms by cyano, by nitro, by halogen, by alkyl with 1 to 6 carbon atoms, by alkoxy with 1 to 6 carbon atoms, by alkylthio with 1 to 6 carbon atoms, by haloalkyl with 1 to 4 carbon atoms - bono, by halogenalkoxy with 1 to 4 carbon atoms or by halogenalkylthio with 1 to 4 carbon atoms with respectively 1 to 5 halogen atoms or by hydroxy, or means pyridyl substituted by cyano, by nitro, by halogen, by alkyl with 1 to 6 carbon atoms, for alkoxy with 1 to 6 carbon atoms, for alkylthio with 1 to 6 carbon atoms, for halogenalkyl with 1 to 4 carbon atoms, for halogenalkoxy with 1 to 4 carbon atoms or for halogenalkylthio with 1 to 4 carbon atoms with respectively 1 to 5 halogen atoms and R7 means alkyl- (with 1 to 6 carbon atoms), alkenyl- (with 2 to 6 carbon atoms), alkynyl- (with 2 to 6 carbon atoms) carbon), formyl, alkylcarbonyl- (with 1 to 6 carbon atoms) , haloalkylcarbonyl- (with 1 to 6 carbon atoms), with 1 to 6 halogen atoms or alkoxycarbonyl- (with 1 6 carbon atoms). Preferably, Ar means phenyl or pyridyl substituted, where appropriate, one to three times, in the same or different ways by halogen, by halogen-alkyl (with 1 to 6 carbon atoms), by halogen-al - quiltium (with 1 to 6 carbon atoms), for halogenoalkoxy (with 1 to 6 carbon atoms), for alkoxy (with 1 to 6 carbon atoms), for hydrazine, for dialkylhydrazino- (with 1 to 6 atoms) carbon), by amino, by alkylamino (with 1 to 6 carbon atoms), by di- (with 1 to 6 carbon atoms) -alkylamino, by alkylimino (with 1 to 6 carbon atoms), by cyano, by alkylthio (with 1 to 6 carbon atoms) or by grouping where R8 and R9 are the same or different and mean hydrogen or alkyl- (with 1 to 6 carbon atoms). Preferably n means a number 0, 1 or 2. R1 means H2N-CS-. Especially preferably. R2 means haloalkyl- (with 1 to 4 carbon atoms) with 1 to 9 halogen atoms equal or different from the group consisting of fluorine, chlorine and bromine, halogenalkenyl- (with 2 to 4 carbon atoms) with 1 to 5 Halogen atoms which are the same or different from the group consisting of fluorine, chlorine and bromine and halogenoalkynyl- (with 2 to 4 carbon atoms) with 1 to 5 halogen atoms which are the same or different from the group formed by fluorine, chlorine and bromine.

Especially preferably. R3 means hydrogen, amino or means one of the following groupings O R 5 R 3 \. R N R "N N N ^ R6 c -NHR H where R 4 means alkoyl- (with 1 to 4 carbon atoms), halogenoalkyl- (with 1 to 4 carbon atoms) with 1 to 3 halogen atoms, alkoxy- (with 1 to 4 carbon atoms) -alkyl- (with 1 to 2 carbon atoms) or phenyl, optionally substituted one to three times, in the same or different manner by hydroxy, or cyano, by nitro, by halogen, by alkyl with 1 to 4 carbon atoms, C 1 -C 4 -alkoxy, C 1 -C 2 haloalkyl, halogen-C 1 -C 2 -alkoxy or halogen-1-C 2 -alkyl with 1 to 3 halogen atoms, R 5 denotes hydrogen or alkyl- (with 1 to 4 carbon atoms), R6 signifies hydrogen, alkyl- (with 1 to 4 carbon atoms) or means phenyl optionally substituted once or twice, in the same or in different forms, by hydroxy , by cyano, by nitro, by halogen, by alkyl with 1 to 4 carbon atoms, by alkoxy with 1 to 4 carbon atoms, for halogenalkyl with 1 to 2 carbon atoms, for halogenalkoxy with 1 to 2 carbon atoms or for halogenalkylthio with 1 to 2 carbon atoms with respectively 1 to 3 halogen atoms, especially means 4-hydroxy -3-methoxy-phenyl and R7 means alkyl- (with 1 to 4 carbon atoms), alkenyl- (with 2 to 4 carbon atoms), alkynyl- (with 2 to 4 carbon atoms), formyl, alkyl- ( with 1 to 4 carbon atoms) -carbonyl, haloalkyl- (1 to 4 carbon atoms) -carbonyl with 1 to 5 halogen atoms equal or different from the group consisting of fluorine, chlorine or bromine or alkoxycarbonyl- (with 1 to 4 carbon atoms). Particularly preferably, Ar means phenyl or pyridyl, each optionally substituted one to three times, in the same or different ways by fluorine, chlorine, trifluoromethyl, trifluoromethylthio, trifluoromethoxy, methoxy, hydrazine, dimethylhydrazino, by amino, by methylamino, by dimethylamino, by iminomethyl, by cyano, by methylthio or by the group R ° / • N where R8 and R9 are the same or different and mean hydrogen, or alkyl- (with 1 to 4) carbon atoms). Especially preferably. n means a number 0, 1 or 2. R1 means H2N-CS-, very particularly preferably, R2 means one of the residues: -CF, -CI? F, -CF2-CH3, -CF3-CHF2, -CF2 -CHFC1, -CH2-CF3, -CH2-CF2C1, -CH -CF2 ~ CHF, -CF2-CFC1-CF3, -C (C1) (CF3) -CF2C1, -C (C1) (CF3) -CHC1-CF3 , -C (CF3) = CC12, very particularly preferably, R3 means hydrogen, amino or one of the groupings -NH-C0-CH3, -NH-CO-C2H5 -N = CH-NH2, -N = C ( CH3) -NH2, -N = CH-N (CH3) 2, -N = C (CH3) -N (CH3) 2, -NHC2H5 or -NH-CH2-CH = CH2, Very particularly preferably, Ar means (1) phenyl substituted two or three times, in the same or in different forms, being in the 2-position fluorine or chlorine, in the position 4 trifluoromethyl and in the 6-position fluorine, chlorine, cyano, methoxy, methylthio, trifluoromethyl, trifluoromethoxy, trifluoromethylthio or hydrazino; or (2) a 2-pyridyl radical, which is substituted in the 4-position by trifluoromethyl and in the 6-position by fluorine or chlorine. Very particularly preferably, n means one of the integers 0, 1 or 2. The definitions of the residues or the explanations indicated above or indicated in the preferred ranges are valid for the final products and, correspondingly, for the starting products and for the intermediate products. These definitions of the remains can be combined arbitrarily with each other, that is to say even between the respective preferred ranges. According to the invention, the compounds of the formula (I) are preferred, in which a combination of the meanings indicated above, preferably (or preferably), is present.

Particularly preferred according to the invention are compounds of the formula (I), in which a combination of the meanings indicated above and, more preferably, is present. According to the invention, the compounds of the formula (I) are very particularly preferred, in which a combination of the meanings indicated above is very particularly preferably present. In the definitions of the residues indicated above and which will be indicated below, the hydrocarbon radicals, such as alkyl or alkenyl - even in combination with heteroatoms such as alkoxy or alkylthio - will, respectively, be straight chain or branched chain as long as possible . Preference is given to the compounds of the formula (IA) where Ar, R2 and n have the meaning indicated above. Examples of the new 3-thiocarba-moylpyrazole derivatives have been indicated in Tables 1 to 60: Table 1.

Compounds of table 1 corresponding to the general formula (IB), in which R3 = NH. n = the number 0 R2 = as listed below. "2 -CF, -CF -CH- -CF3-CHF2 -CF2-CHFC1 -CH2-CF3 -CH2-CF2C1 -CF2-CFC1-CF3, -C (C1) (CF3) -CF2C1 -C (C1) (CF3) -CHC1-CF3 -C (CF3) = CC12. Table 2. Table 2 contains compounds of the general formula (IB), in which R2, R3 and n = as listed in Table 1. Table 3. Table 3 contains compounds of the general formula (IB), in which R2, R3 and n = as listed in Table 1. Table 4. Table 4 contains compounds of the general formula (IB), in which R2, R3 and n = as listed in table 1.

Tables 5 to 8. Tables 5 to 8 contain compounds of the general formula (IB), wherein R3 = H Ar, R2 and n = as listed in Tables 1 to 4. Tables 9 to 12. Tables 9 to 12 contain compounds of the general formula (IB) in which - -O Ar, R2 and n = as listed in Tables 1 to 4. Tables 13 to 16. Tables 13 to 16 contain compounds of the general formula (IB), in which Ar, R, and n = as listed in Tables 1 to 4. Tables 17 to 20. Tables 17 to 20 contain compounds of the general formula (IB), in which Ar, R and n = as listed in Tables 1 to 4. Tables 21 to 40. Tables 21 to 40 contain compounds of the general formula (IB), wherein n = the number 1 Ar, R2 and R3 = as listed in Tables 1 to 20. Tables 41 to 60. Tables 41 to 60 contain compounds of the general formula (IB), wherein n = the number 2 Ar, R2 and R3 = as listed in Tables 1 to 20. If used, for example, 5-amino-3-cyano-4- (1,1-difluoroethylthio) -1- (2,6-dichloro-4-trifluoromethylphene-nyl) -pyrazole and Hydrogen sulphide as starting compounds, the development of the reaction of process (a) according to the invention can be represented by means of the following formula scheme: If, for example, l- (2,6-dichloro-4-) is used. trifluoromethylphenyl) -3-thiocarbamoyl-5- (pyrrol-1-yl) -pyrazole and 1,1-difluoromethyl sulfenyl chloride as starting compounds, the development of the reaction of process (b) according to the invention may be represented r means of the following formula schema: If, for example, 5- (pyrrol-1-yl) -3-thiocarbamoyl-4- (1, 1-difluoroethylthio) -l- (2,6-dichloro-4-trifluoromethyl-phenyl) -pyrazole and Hydrogen sulphide or starting compounds, the development of the reaction of process (c) according to the invention can be represented by means of the following formula scheme: The 3-cyanopyrazole derivatives to be used as starting materials in carrying out the process ( a) according to the invention, of the formula (II) are known (see for example EP-A 0 295 117 and EP-A 0 659 745) and / or can be prepared in analogy with the known processes. The 3-thiocarbamoylpyrazole derivatives, to be used as starting materials in carrying out the process (b) according to the invention, of the formula (III) are new and also constitute an object of the invention. The compounds of the formula (III) can be obtained by reacting 2-cyanopyrazoles of the form-mule (V) N wherein Ar and R3-1 have the meaning indicated above, according to process (a) of the invention, with hydrogen sulphide, if appropriate in the presence of an auxiliary agent of the reaction and, if appropriate, in the presence of a diluent. The 3-cyanopyrazoles of the formula (V) are known and / or can be prepared in a known manner, if the corresponding 5-amino-3-cyano-pyrazoles of the formula (VI) are derivatized, for example. in which Ar has the meaning indicated above, in the usual manner and manner, in the amino group (see, for example, EP-A 0 659 745). The compounds of the formula (III) can also be obtained by derivatizing 5-amino-3-thiocarbamoylpi-razoles of the formula (VII) wherein Ar has the meaning indicated above, in a manner and manner customary in the amino group (see, for example, EP-A 0 659 745). The 5-amino-3-thiocarbamoylpyrazoles of the formula (VII) are new and also constitute an object of the invention. These are obtained if 5-amino-3-cyanopyrazoles of the formula (VI) are reacted according to the process (a) according to the invention with hydrogen sulphide, if appropriate in the presence of a diluent (see also the preparation examples). The sulfenyl halides of the formula (IV) to be further used as the starting compounds for the process (b) according to the invention are generally known compounds of organic chemistry. The 3-thiocarbamoylpyrazole derivatives to be used as starting materials for the process (c) according to the invention of the formula (la) are compounds according to the invention. The process (a) according to the invention is preferably carried out using a diluent. Suitable diluents are virtually all inert organic solvents. These preferably include aliphatic and aromatic hydrocarbons, if appropriate halogenated, such as pentane, hexane, heptane, cyclohexane, petroleum ether, benzine, ligroin, benzene, toluene, xylene, methylene chloride, ethylene chloride, chloroform, tetrachloride carbon, chlorobenzene and o-dichlorobenzene, ethers such as diethyl- and dibutyl ether, glycol dimethyl ether and diglycoldimethyl ether, tetrahydrofuran and dioxane, ketones such as acetone, methyl-ethyl-, methyl-isopropyl- or methyl-isobutyl-ketone, esters such as methyl or ethyl, nitriles such as for example acetonitrile or propionitrile, amides such as for example dimethylformamide, dimethylacetamide and N-methylpyrrolidone, as well as dimethylsulfoxide, tetraethylenesulfone or hexamethylphosphorotriamide. As the auxiliary agents of the reaction, in the process (a) according to the invention, all bases which are usually usable for this type of reaction can be used. Preference is given to basic nitrogenous compounds, such as trimethylamine, triethylamine, tripropylamine, tributylamine, diisobutyl amine, dicyclohexylamine, ethyldiisopropylamine, ethyldicyclohexylamine, N, N-dimethylbenzylamine, N, N-dimethylaniline, pyridine, 2- methyl-, 3-methyl-, 4-methyl-, 2, 4-dimethyl-, 2,6-dimethyl-, 2-ethyl-, 4-ethyl- 5-ethyl-2-methyl-pyridine, l, 5- diazabicyclo [4.3.0] -on-5-ene (DBN), 1,8-diazabicyclo- [5,4,0] -undec-7-ene (DBU) or 1,4-diazabicyclo [2.2 , 2] -octane (DABCO). It is also possible to use an excess of the auxiliary agent of the reaction used as a diluent. The temperatures of the reaction in process (a) according to the invention can vary within wide limits. In general, temperatures are between 0 ° C and 100 ° C, preferably at temperatures between 10 ° C and 80 ° C. The process (a) according to the invention is generally carried out under normal pressure. However, it is also possible to work under higher pressure or at a lower pressure. for carrying out the process (a) according to the invention, hydrogen sulphide is generally used in excess. The reactions will generally be carried out in a suitable diluent in the presence of a basic nitrogenous compound. The preparation is carried out according to customary methods (see the exemplary embodiments). Suitable diluents for carrying out process (b) according to the invention are inert organic solvents. These include aliphatic hydrocarbons, alicyclic or aromatic, if appropriate halogenated, such as for example benzine, benzene, toluene, xylene, chlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform, carbon tetrachloride, ethers, such as diethyl ether, dioxane, tetrahydrofuran or ethylene glycololdi-methyl- or -diethylether, ketones such as acetone or butane, nitriles, such as acetonitrile or propionitrile, amides, such as dimethylformamide, dimethylacetamide, N-ethylformanilide, N-methylpyrrolidone or hexamethylphosphorotriamide, esters such as ethyl acetate, sulfoxides such as dimethyl sulfoxide or acids, such as acetic acid. The process (b) according to the invention can be carried out, if appropriate, in the presence of a reaction auxiliary agent. As such, all usual inorganic or organic bases are considered. These include, for example, alkali metal hydroxides, such as sodium hydroxide or potassium hydroxide, carbonates or bicarbonates of alkali metals, such as sodium carbonate, potassium carbonate or sodium bicarbonate, as well as tertiary amines, such as triethylamine, N, N-dimethylaniline, pyridine, N, N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyclonone (DBN) or diazabicycloundecene (DBU). The reaction temperatures in carrying out the process (b) according to the invention can vary within wide limits. In general, work is carried out at temperatures between -20 ° C and + 120 ° C, preferably at temperatures between 0 ° C and + 50 ° C. For carrying out process (b) according to the invention, per mol of 1-arylpyrazole substi- tuted at the 4-position, of the formula (III), generally from 1.0 to 2.5 mol, preferably from 1, are used. 0 to 1.5 moles of sulfenyl halide of the formula (IV), and optionally 1.0 to 2.5 moles, preferably 1.0 to 1.5 moles of reaction aid. The conduct of the reaction, the preparation and the isolation of the reaction products is carried out according to usual methods in general. Oxidizing agents for carrying out process (c) according to the invention are all auxiliary agents which are usually usable for the oxidation of sulfur. Particularly suitable are hydrogen peroxide, organic peracids, such as, for example, peracetic acid, m-chloroperbenzoic acid, p-nitroperbenzoic acid or oxygen from the air. Suitable diluents for carrying out process (c) according to the invention are inert organic solvents. Preference is given to using hydrocarbons, such as benzine, benzene, toluene, hexane or petroleum ether, chlorinated hydrocarbons such as dichloromethane, 1,2-dichloroethane, chloroform, carbon tetrachloride or chlorobenzene, ethers, such as diethyl ether, dioxane or tetrahydrofuran. , carboxylic acids, such as acetic acid or propionic acid, or dipolar aprotic solvents, such as acetonitrile, acetone, ethyl acetate or dimethylformamide. The process (c) according to the invention can be carried out, if appropriate, in the presence of an acid-binding agent. Suitable as such are all the organic and inorganic acid acceptor agents usually usable. Preference is given to using alkaline earth metal or alkali metal hydroxides, acetates or carbonates, such as, for example, calcium hydroxide, sodium hydroxide, sodium acetate or sodium carbonate. The process (c) according to the invention can be carried out, if appropriate, in the presence of a suitable catalyst. As such, all conventional metal salt catalysts suitable for this type of oxidation of sulfur are suitable. By way of example, mention may be made of ammonium molybdate and sodium tungstate. The reaction temperatures in the process (c) according to the invention can vary within wide limits. In general, work is carried out at temperatures between -20 ° C and + 70 ° C, preferably at temperatures between 0 ° C and + 50 ° C. For carrying out the process (c) according to the invention, per mole of the form-mule compound (la), in general from 0.8 to 1.2 moles, preferably equimolar amounts of the oxidizing agent, are used at any time interrupting the oxidation of sulfur to the sulfoxide level. For the oxidation at the sulfone level, per mole of the compound of the formula (la), generally from 1.8 to 3.0 moles, preferably twice molar quantities of oxidizing agent are used. The conduction of the reaction, the elaboration and the isolation of the final products was carried out according to usual procedures. The active compounds according to the invention are suitable, with a good compatibility for plants and a suitable toxicity for warm-blooded animals, for the control of animal pests, preferably against insects, arachnids and nematodes, which occur in agriculture, in forestry, for the protection of stored products and materials as well as in the field of hygiene. They are active against normally sensitive and resistant species as well as against all or some of the stages of development. The pests mentioned above belong: From the order of the isopods, for example, Oniscus asellus Armadillidium vulgare and Porcellio scaber. From the order of the diplópodos, for example, Blaniulus guttulatus. From the order of the chilopoda, for example, Geo-philus carpophagus and Scutigera spec ..

From the order of the sinfilos, for example, Scuti-gerella immaculata. From the order of the tisane, for example, Lepisma saccharina. From the order of springtails, for example, Ony-chiurus armatus. From the order of the orthoptera, for example, Blat-ta orientalis, Periplaneta americana, Leucophaea ade-rae, Germanic Blattella; Acheta do esticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus dif-ferentialis and Schistocerca gregaria. From the order of dermápteros, for example, Forfícula auricularia. From the order of the isoptera, for example, Reti-culitermes spp .. From the order of the anopplides, for example, Pedi-culus humanus corporis, Haematopinus spp. , and Linognathus spp. From the order of the malophagous, for example, Tri-chodectes spp. and Damalinea spp. From the order of the Thysanoptera, for example, Hercinothrips femoralis and Thrips tabaci. From the order of the heteroptera, for example, Eurygaster spp. , Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodnius prolixus and Triatoma spp ..

From the order of the Homoptera, for example, Aleu-rodes brassicae, Bemisia tabaci, Trialeurodes vaporario-rum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Aphis pomi, Eriosoma lanigerum, Hya-lopterus arundinis, Phylloxera vastatrix, Pemphigus spp. . , Macrosiphum avenae, Myzus spp., Phorodon humuli, Rhopalo-siphum padi, Empoasca spp., Euscelis bilobatus, Nephotet-tix cincticeps, Lecanium corni, Saissetia oleae, Laodel-phax striatellus, Nilaparvata lugens; Aonidiella auran-tii, Aspidiotus hederae, Pseudococcus spp., Psylla spp. From the order of the Lepidoptera, for example, Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brumata, 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., Spodoptera exigua, Mamestra brassicae, Panolis flammea, Spodoptera litura, Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo spp. Pyrausta nubilalis, Ephestia kuehniella, Galleria mellonella, Tineola bisselliella, Tinea pellionella, Hofmannophila pseudospretella, Ca-coecia podana. Capua retícula, Choristoneura fumiferana, Clysia ambiguella, Homona magnánima and Tortrix viridana. From the order of Coleoptera, for example, Ano-bium punctatum, Rhizopertha dominica, Bruchidius obtectus, Acanthoscelides obtectus, Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedon co-chleariae, Diabrotica spp. , Psylliodes chrysocephala, Epilachna varivestis, Atomaria spp., Oryzaephilus suri-namensis, Anthonomus spp. , Sitophilus spp. , Otiorrhyn-chus sulcatus, Cosmopolites sordidus, Ceuthorrhynchus assimilis, Hypera postica, Dermestes spp., Trogoderma spp. , Anthrenus spp. , Attagenus spp. , Lyctus spp. , Me-ligethes aeneus, Ptinus spp., Niptus hololeucus, Gibbium psylloides, Tribolium spp. , Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha, Amphimallon solstitialis and Costelytra zealandica. From the order of Hymenoptera, for example, Di-prion spp. , Hoplocampa spp. , Lasius spp. , Monomorium pha-raonis and 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. , Gastrophi-lus spp. , Hyppobosca spp. , Stomoxys spp. , Oestrus spp. , Hypoderma spp. , Tabanus spp. , Tannia spp. , Bibio hortula-nus, Oscinella frit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae and Tipula paludosa. From the order of the siphonoptera, for example, Xe-nopsylla cheopis, Ceratophyllus spp. From the order of the arachnids, for example Scorpio maurus, Latrodectus mactans. From the order of mites, for example Acarus si-ro, Argas spp., Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp., Rhipicephalus spp., Amblyom a spp., Hyalomma spp., Ixodes spp., Psoroptes spp., Chorioptes spp., Sarcoptes spp., Tarsonemus spp. , Bryobia praetiosa, Panonychus spp. , Tetranychus spp. Plant parasitic nematodes belong, for example, to Pratylenchus spp. , Radopholus similis, Ditylenchus dipsaci, Tylenchulus semipenetrans, Heterodera spp., Globodera spp., Meloidogyne spp., Aphe-lenchoides spp., Longidorus spp., Xiphinema spp., Tricho-dorus spp. The compounds according to the invention of the formula (I) are characterized especially by a high insecticidal activity with partially systemic properties in the roots. They can be used with an especially good success in the fight against insects harmful to plants, such as, for example, against the larvae of the horseradish leaf beetle (Phaedon cochlae-riae), the caterpillars of the cabbage moth. (Plutella macu-lipennis), the green rice cicada (Nephotettix cinc-triceps), the caterpillars of the nocturnal moth (Spodoptera frugiperda), the louse of the leaf of the peach tree (Mycus persicae) or to fight the larvae of the cucumber beetle (Diabrotica bateata). The active compounds according to the invention can be converted into customary formulations, such as solutions, emulsions, sprayable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension-emulsion concentrates, natural and synthetic materials impregnated with the active product, as well as microencapsulated in polymer materials. These formulations are prepared in known form, for example by mixing the active compounds with extenders, ie with liquid solvents and / or solid excipients, optionally with the use of surfactants, ie emulsifiers and / or dispersants. and / or foam generating means. When water is used as an extender, organic solvents can be used, for example, as auxiliary solvents. Preferred liquid solvents are: aromatic hydrocarbons, such as xylene, toluene or alkylnaphthalenes, chlorinated aromatic hydrocarbons and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example petroleum fractions, alcohols such as butanol or glycol, as well as their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, or strongly polar solvents, such as dimethylformamide and dimethyl sulfoxide as well as water. Suitable solid excipients are, for example, ammonium salts and ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic molten minerals, such as highly silicic acid. dispersed, aluminum oxide and silicates, as solid excipients for granulates come into consideration: for example broken and fractionated natural minerals, such as calcite, marble, pumice, sepiolite and dolomite, as well as synthetic granules of inorganic and organic flours and granulates of organic material, such as sawdust, coconut husks, corn ears and tobacco stems; as emulsifiers and / or foamers they come into consideration: for example, non-ionogenic and anionic emulsifiers, such as polyoxyethylenated esters of fatty acids, polyoxyethylenated ethers of fatty alcohols, for example, alkylaryl polyglycol ether, alkylsulfonates, the alkyl sulphates, the arylsulpho-nates, as well as the albumin hydrolysates; Dispersants are suitable as dispersants: for example, sulphite lignin liquors and methylcellulose. In the formulations, adhesives such as carboxymethylcellulose, natural and synthetic polymers that are pulverulent, granulable or in the form of latex, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, as well as natural phospholipids such as cephalin and lecithin, and synthetic phospholipids can be used. Other additives can be mineral and vegetable oils. Dyes, such as inorganic pigments, for example, iron oxide, titanium oxide, Prussian blue and organic dyes, such as metallic alizarin, azo and phthalocyanine dyes as well as trace nutrients, such as iron salts, manganese, may be employed. , boron, copper, cobalt, molybdenum and zinc. The formulations contain, in general, between 0.1 and 95% by weight, preferably between 0.5 and 90% of active product. The active compounds according to the invention can be present in their commercially available formulations as well as in the application forms prepared from these formulations, in admixture with other active ingredients, such as insecticides, baits, sterilizers, acaricides, nematicides, fungicides, growth regulating products or herbicides. Insecticides include, for example, esters of phosphoric acid, carbamates, esters of carbonic acid, chlorinated hydrocarbons, phenylureas, products prepared by means of micro-organisms and the like. Particularly convenient components of the mixture are, for example, the following: Fungicides: 2-Aminobutane; 2-anilino-4-methyl-6-cyclopropylpyrimidine; 2 ', 6'-dibromo-2-methyl-4'-trifluoromethoxy-4'-trifluoromethyl-1,3-thiazole-5-carboxanilide; 2,6-dichloro-N- (4-trifluoromethylbenzyl) benzaide; (E) -2-methoxyimino-N-methyl-2- (2-phenoxyphenyl) acetamide; 8-hydroxyquinolinesulfate; methyl- (E) -2-. { 2- [6- (2-Cyanophenoxy) pyrimidin-4-yloxy] phenyl} -3-methoxyacrylate; methyl- (E) -methoxyimino [alpha- (o-tolyloxy) -o-tolyl] acetate; 2-Phenylphenol (OPP), Aldimorph, Am-propylfos, Anilazin, Azaconazole, Benalaxyl, Benodanil, Benomyl, Binapacryl, Biphenyl, Bitertanol, Blasticidin-S, Bromuconazole, Bupirimate, Bu-thiobate, calcium polysulfide, Captafol, Captan, Carbendazim , Carboxin, Chinomethionat (Quinómethionat), Chloroneb, Chloropicrin, Chlorothalonil, Chlozolinat, Cufraneb, Cymoxanil, Cyproconazole, Cyprofuram, Dichlorophen, Diclobutrazol, Diclofuanid, Diclomezin, Dicloran, Diethofencarb, Difenoconazole, Dimethirimol, Dimethomorph, Diniconazole, Dinocap, Diphenylamin, Dipy- rithion, Ditalimfos, Dithianon, Dodine, Drazoxolon, Edifenphos, Epoxyconazole, Ethyrimol, Etridiazole, Fenarimol, Fenbuconazole, Fenfuram, Fenitropan, Fenpi-clonil, Fenpropidin, Fenpropimorf, Fentinacetat, Fen-tinhydroxyd, Ferbam, Ferimzone, Fluazinam, Fludioxonil, Fluoromide, Fluquinconazole, Flusilazole, Flusulfamide, Flutolanil, Flutriafol, Folpet, Fosetyl-Aluminum, Ftha-lide, Fuberidazole, Furalaxil, Furmecyclox, Guazatine, Hexachlorobenzene , Hexaconazole, Hymexazole, Imazalil, Imibenconazole, Iminoctadin, Iprobenfos (IBP), Iprodion, Isoprothiolan, Kasugamycin, copper compositions, such as; copper hydroxide, copper naphthenate, copper oxychloride, copper sulfate, copper oxime and mixture of Bordeux, Mancopper, Mancozeb, Maneb Mepanipyrim, Mepronil, Me-talaxyl, Metconazole, Methasulfocarb, Methfuroxam, Metiram, Metsulfovax, Myclobutanil, Nickel dimethyldithiocarbamate, Nitrothal-isopropyl, Nuarimol, Ofurace, Oxadixyl, Oxamocarb, Oxycarboxin, Perfurazoat, Penconazole, Pencycuron, Phosdiphen, Phtha-lid, Pimaricin, Piperalin, Polycarbamate, Polyoxin, Pro-Benazole, Prochloraz, Procymidon, Propamocarb, Propiconazole, Propineb, Pyrazophos, Pyrifenox, Pyrimethanil, Py-Roquilon, Quintozen (PCNB), Sulfur and Sulfur Compositions, Tebuconazole, Teclofta-lam, Tecnazen, Tetraconazole, Thiabendazole, Thicyofen, Thiophanat-methyl, Thira, Tolclophos-methyl, Tolylfluanid, Triadimefon, Triadimenol, Triazoxid, Trichlamid, Tricyclazole, Tridemorph, Triflumizol, Triforin, Tritico-nazole, Validamycin A, Vinclozolin, Zineb, Ziram. Bactericides: Bronopol, Dichlorophen, Nitrapyrin, nickel dimethyldithiocarbamate, Kasugamycin, Octhilinon, furancarboxylic acid, Oxytetracyclin, Probenazol, Streptomycin, Teclof-talam, copper sulfate and other copper preparations. Insecticides / Acaricides / Ne Aicides: Abamectin, AC 303 630, Acephat, Acrinathrin, Alanycarb, Aldicarb, Alphamethrin, Amitraz, Avermectin, AZ 60541, Azadirachtin, Azinphos, A, Azinphos M, Azocyclotin, Bacillus thuringiensis, Bendiocarb, Benfuracarb, Bensul- tap, Betacyfluthrin, Bifenthrin, BPMC, Brofenprox, Bromophos A, Bufencarb, Buprofezin, Butocarboxin, Butylpyride-ben, Cadusafos, Carbaryl, Carbofuran, Carbophenothion, Carbosulfan, Cartap, CGA 157 419, CGA 184699, Chloethocarb, Chlorethoxyphos, Chlorfenvinphos, Chlorfluazuron, Chlor-mephos, Chlorpyrifos, Chlorpyrifos M, Cis-Resmethrin, Clocythrin, Clofentezin, Cyanophos, Cycloprothrin, Cy-fluthrin, Cyhalothrin, Cyhexatin, Cypermethrin, Cyroma-zin, Deltamethrin, Demeton M, Demeton S, Demeton-S-methyl, Diafenthiuron , Diazinon, Dichlofenthion, Dichlorvos, Dicliphos, Dicrotophos, Diethion, Diflubenzuron, Dimet-hoat, Dymethylvinphos, Dioxathion, Disulfoton, Edifenphos, Emamectin, Esfenvalerat, Ethiophencarb, Ethion, Ethofenprox, Ethopropho s, Etrimphos, Fenamiphos, Fenazaquin, Fenbutatinoxid, Fenitrothion, Fenobucarb, Fenothiocarb, Fenoxycarb, Fenpropathrin, Fenpyrad, Fenpyroximat, Fenthion, Fenvalerate, Fipronil, Fluazinam, Flucycloxuron, Flucythrinat, Flufenoxuron, Flufenprox, Fluvalinate, Fonophos, Formothion, Fosthiazat, Fubfenprox, Furathiocarb, HCH, Heptenophos, Hexaflumuron, Hexythiazox, Imidacloprid, Iprobenfos, Isazophos, Isofenphos, Isoprocarb, Isoxathion, Ivermectin, Lamda-cyhalothrin, Lufenuron, Malathion, Mecarbam, Mervinphos, Mesulfenphos, Metalde-hyd, Methacrifos, Methamidophos, Methidathion, Methio- carb, Methomyl, Metolcarb, Milbemectin, Monocrotophos, Moxidectin, Naled, NC 184, NI 25, Nitenpyram Omethoat, Oxamyl, Oxydemethon M, Oxydeprofos, Parathion A, Parathion M, Permethrin, Phenthoat, Phorat, Phosalon, Phosmet, Phosphamidon, Phoxi, Pirimicarb, Pirimiphos M. Pirimiphos A, Profenofos, Promecarb, Propap-hos, Propoxur, Prothiophos, Prothoat, Pymetrozin, Pyra-chlophos, Pyradaphenthion, Pyresmethrin, Pyr ethrum, Pyridaben, Pyrimidifen, Pyriproxifen, Quinalphos. RH 5992. Salithion, Sebufos, Silafluofen, Sulfotep, Sulprofos, Tebufenozid, Tebufenpyrad, Tebupirimphos, Teflubenzuron, Tefluthrin, Temephos, Terbam, Terbufos, Tetrachlorvin-phos, Thiafenox, Thiodicarb, Thiofanox, Thiomethon, Thio-nazin, Thuringiensin, Tralomethrin, Triarathen , Triazop-hos, Triazuron, Trichlorfon, Triflumuron, Trimethacarb, Vamidothion, XMC, Xylylcarb, Yl 5301/5302, Zetamethrin. It is also possible to mix with other active pro-ducts, such as herbicides or with fertilizers and growth regulators. The active compounds according to the invention can also be present in their customary formulations in commerce as well as in the application forms prepared from these formulations in a mixture with synergists. The synergists are compounds through which the effect of the active products is increased without the synergistic aggregate having to be active in itself. The active ingredient content of the application forms prepared from the commercially available formulations can vary within wide limits. The concentration in active product of the application forms can be from 0.0000001 to 95% by weight of active product, preferably between 0, 0001 and 1% by weight. The application is carried out in a form adapted to the forms of application. When used against health pests and stored products, the active products are characterized by the outstanding residual effect on wood and clay as well as good alkali stability on whitewashed substrates. The active compounds according to the invention not only act against plant pests, hygiene and stored products, but also in the veterinary sector against animal parasites (ectoparasites) such as hard ticks, soft ticks, mites of the scabies, migratory mites, flies (choppers and suckers), larvae of parasitic flies, lice, hair nits, nits of feathers and fleas. These parasites belong to: From the order of the anopplides for example Haematopinus spp., Linognathus spp., Pediculus, Pthirus spp., Solenopotes spp. From the order of the Mallofagos and the suborders of the amblycerins as well as the ischinocerines, for example , Trimenopon spp. , Menopon spp. , Trinoton spp. , Bovicola spp., Erneckiella spp., Lepikentron spp., Dama-lina spp. , Trichodectes spp. , Felicola spp. From the order of the dipterans and the suborders of the nematocerins as well as the brachykeri, for example, Aedes spp., Anopheles spp., Culex spp., Simulium spp. , Eusimulium spp. , Phlebotomus spp. , Lutzomyia spp. , Culicoides spp., Chrysops spp., Hybomitra spp., Atylotus spp. , Tabanus spp. , Haematopota spp. , Philipomyia spp. , Braula spp. , Musca spp. , Hydrotaea spp. , Stomoxys spp. , Haematobia spp., Morellia spp, Fannia spp., Glossina spp. , calliphora spp. , Lucilia spp. , Chrysomyia spp. , ohlfahrtia spp., Sarcophaga spp., Oestrus spp., Hypoderma spp., Gasterophilus spp., Hippobosca spp., Lipoptena spp. , Melophagus spp. From the order of the siphonoptera, for example Ctenocephalides spp., Xenopsylla spp., Ceratophyllus spp.; From the order of heteropterids, for example Cimex spp., Triatoma spp., Rhodnius spp., Panstrongylus spp. From the order of the blatarids, for example Blatta orientals, Periplaneta americana, Germanic Blattela, Supelia spp .. From the subclass of the mites (Acarida) and the suborder of the meta- as well as mesostigmat, for example Argas spp. , Ornithodorus spp. , Otobius spp. , Ixodes spp. , Amblyomma spp., Boophilus spp., Dermacentor spp., Haemo-physalis spp. , Hyalomma spp. , Rhipicephalus spp. , Derma-nyssus spp., Raillietia spp., Pneumonyssus spp., Sternos-toma spp. , Varroa spp .. From the order of actinedides (Prostigmata) and acaridids (Astigmata), for example Acarapis spp., Cheyletieella spp., Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Listro. -phorus spp., Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoe-dres spp. , Knemidocoptes spp. , Cytodites spp. , Lamino-sioptes spp .. In an exemplary way, they have a good effect against flies (Musca domestica), an inhibitory effect of development against larvae of the Lucilla cu-prina fly, as well as a good effect against cockroaches (Periplaneta americana) and against ticks (Boophilus micro-plus), even in the form of an inhibition of egg laying. The active compounds of the formula (I) according to the invention are also suitable for the control of arthropods, which attack animals useful in agriculture, such as, for example, cows, lambs, goats, horses, pigs, donkeys, camels, hippos, hen, chickens, ducks, turkeys, geese, bees, other domestic animals such as, for example, dogs, cats, game birds, aquarium fish as well as so-called test animals such as, for example, hamsters , guinea pigs, rats and mice. Through the fight against these arthropods deaths and decreases in productivity (in meat, milk, wool, skins, eggs, honey, etc.) are avoided, so that, by using the active products according to the invention, a more economical maintenance is possible and simple of the animals.

The application of the active compounds according to the invention is carried out, in the veterinary field, in a known manner by enteral administration in the form, for example, of tablets, capsules, beverages, dragees, pastes, boli, by means of the process by means of I think "feed-through", suppositories, by parenteral administration, such as for example by injection (intramuscular, subcutaneous, intravenous, intraperitoneal and similar), implants, by nasal application, by dermal application in the form of for example immersion or bathing (Dippen ), sprayed (Spray), irrigated (Pour-on and Spot-on), washed, powdered as well as with the aid of molded bodies containing the active product such as collars, ear tags, tails for the tail, bands for limbs, halters, marking devices etc. When used for livestock, poultry, domestic animals, the active compounds of the formula (I) can be used as formulations (for example powders, emulsions, spreadable agents), containing the active compounds in amounts of 1 to 80% by weight. weight, directly or after a dilution of 100 up to . 000 times or can be applied in the form of a chemical bath. Furthermore, it has been found that the compounds of the formula I show a high insecticidal effect against the insects that destroy industrial materials. In an exemplary and preferred way - however without limitation - the following insects can be mentioned: Beetles, such as Hylotrupes bajulus, Chlorophorus pilosis, Anobium punctatum, Xestobium rufovillosum, Ptilinus pecticornis, Dendrobium pertinex, Ernobius mollis, Priobium carpini, Lyctus brunneus , Lyctus africanus, Lyctus planicollis, Lyctus linearis, Lyctus pubescens, Trogoxylon aequale, Minthes rugicollis; Xyleborus spec. , Tryptodendron spec. , Apate monachus, Bostrychus capucins, Heterobostrychus brunneus, Sinoxylon spec., Dinoderus minutus. Hymenoptera, such as Sirex juvencus, Urocerus gigas, Urocerus gigas taignus, Urocerus augur. Termites, such as Kalotermes flavicollis, Cryptotermes brevis, Heterotermes indicala, Reticulitermes flavipes, Reticulitermes santo-nensis, Reticulitermes lucifugus, Mastotermes darwinien-sis, Zootermopsis nevadensis, Coptotermes formosanus. Thysanides, such as Lepisma saccarina. By industrial materials it will be understood in the present context non-living materials, such as, preferably, synthetic materials, glues, glues, paper and cardboard, leather, wood and products of wood processing and paints. In a very special way, the materials to be protected against attack by insects are made of wood and wood products. For wood and wood processing products, which can be protected by means of the agents according to the invention or of the mixtures containing them, it should be understood, for example: construction wood, wooden beams, railway sleepers, parts for bridges, boat ribs, wooden vehicles, boxes, pallets, containers, telephone poles, wooden girders, wooden windows and doors, wooden plywood, plywood slabs, carpentry works or wood products, which are found application, in a very general way, at home or in the construction industry. The active compounds can be used as such, in the form of concentrates or customary formulations in general, such as powders, granules, solutions, suspensions, emulsions or pastes. Said formulations can be prepared in a manner known per se, for example by mixing the active ingredients with at least one solvent or diluent, emulsifier, dispersants and / or binder or binding agent, water repellent, optionally drying agents and stabilizers. against UV and, if necessary, colorants and pigments as well as other processing aids. Insecticidal agents or concentrates to be used for the protection of wood and wood materials, contain the active compound according to the invention in a concentration of 0.0001 to 95% by weight, in particular of 0.001 to 60% by weight. The amounts of the agents or concentrates used depend on the type and origin of the insects and the environment. The optimum application quantities can be determined respectively by means of series of tests prior to the application. In general, however, it is sufficient to employ from 0.0001 to 20% by weight, preferably from 0.001 to 10% by weight of the active product, based on the material to be protected. A solvent or a mixture of organochemical solvents and / or a solvent or mixture of organo-chemical, oleaginous or oil-like solvents, which are not readily volatile and / or a solvent or mixture of organochemical solvents, is used as solvent and / or diluent. -res and / or water and, if appropriate, an emulsifier and / or humectant. As organochemical solvents, oleaginous or olea-ginous solvents are preferably used, with an evaporation value above 35 and a flame point above 30 ° C, preferably above 45 ° C. . By way of such water-insoluble, oil-soluble or oleaginous-type solvents which are difficult to volatile, corresponding mineral oils or their aromatic fractions or mixtures of solvents containing mineral oils, preferably benzine for tests, petroleum and / or alkylbenzene, will be used. Advantageously, mineral oils with a boiling range of 170 to 220 ° C, benzine for tests with a boiling range of 170 to 220 ° C, spindle oil with a boiling range of 250 to 350 ° C, petroleum or aromatic hydrocarbons with a boiling range of 160 to 280 ° C, terpene oil and the like. In a preferred embodiment, liquid aliphatic hydrocarbons having a boiling range of 180 to 210 ° C or a high-boiling mixture of aromatic and aliphatic hydrocarbons having a boiling range of 180 to 220 ° C and / or spindle oil and / or monochloronaphthalene, preferably α-monochloronaphthalene. The organic solvents, which are hardly soluble, oleaginous or oil-based, are an evaporation index located above 35 and with a flame point situated po-. above 30 ° C, preferably above 45 ° C, can be partially replaced by light or medium volatility organochemical solvents, provided that the solvent mixture has an evaporation index above 35 and a point of flame located above 30 ° C, preferably above 45 ° C, and that the insecticidal-fungicidal mixture is soluble or emulsifiable in this mixture of solvents. According to a preferred embodiment, a part of the solvent or mixture of organochemical solvents or a solvent or mixture of aliphatic, polar organochemical solvents will be substituted. Preference is given to using aliphatic organochemical solvents containing hydroxyl and / or ester and / or ether groups, such as, for example, glycol ether, esters or the like. As organic-chemical binders, synthetic resins and / or setting drying oils, which are dilutable, are water and / or soluble or dispersible or emulsifiable in organic solvents, will be used within the scope of the present invention. employed substances, especially binders consisting of or containing acrylic resin, a vinyl resin, for example polyvinyl acetate, polyester resin, polycondensation or polyaddition resin, polyurethane resin, alkyd resin or modified alkyd resin, phenolic resin, hydrocarbon resin such as indeno-coumaron resin, silicone resin, vegetable drying and / or drying oils and / or physical drying binders based on a natural and / or synthetic resin. The synthetic resin, used as a binder, it can be used in the form of an emulsion, dispersion or solution. Binders or bituminous substances up to 10% by weight can also be used as binders. In a complementary manner, dyes, pigments, water-repelling agents, odor correctors and inhibitors or anticorrosive agents known per se and the like can be used. It is preferred to use at least one alkyd resin or a modified alkyd resin and / or a drying vegetable oil in the medium or concentrate according to the invention as an organochemical binder. Preferably, according to the invention, alkylamino resins having an oil content of greater than 45% by weight, preferably from 50 to 68% by weight, are used. The aforementioned binder can be partially or totally replaced by a fixing agent (mixture) or by a (a) plasticizer (mixture). These additives should avoid a volatilization of the active products as well as a crystallization or precipitation. They preferably replace 0.01 to 30% of the binder (based on 100% of the binder used). The plasticizers are from the Quimisa slase of esters of phthalic acid such somo dibutylphthalate, of diostilo or bensilbutilo, esters of phosphoric ASID, such as tributyl phosphate, adipic esters such somo adipate di- ( 2-ethylhexyl), stearates such as butyl stearate or amyl stearate, oleates such as butyl oleate, glycerol ethers or higher molecular weight glycol ethers, glycerol esters and esters of p-toluenesulfonic acid. Fixative agents are chemically based on polyvalkyl ethers such as polyv methyl ether or ketones such as benzophenone, ethylenebenzophenone. As the solvent or diluent, water, optionally in admixture with one or more of the above-mentioned solvents or diluents, emulsifier and organo-chemical dispersants, is particularly suitable. Specially effective wood preservation is carried out by the impregnation processes on an industrial scale, for example vacuum, double vacuum or pressure processes. Ready-for-application agents can be supplied with other insecticides and, if necessary, one or more other fungicides. As adisionales somponentes of mezsla are, preferably the insecticides and fungicides mentioned in WO 94/29 268. The compounds mentioned in that document are expressly part of the present solisitud part. As very preferred somespecifiers of mezsla come into unsightly consideration, such as Chlorpyriphos, Phoxim, Silafluofin, Alphamethrin, Cyfluthrin, Cypermethrin, Deltamethrin, Permethrin, Imidacloprid, NI-25, Flufenoxuron, Hexaflumuron and Tri-flumuron, as well as fungicides such somo Epoxisonazole , Hexasonazole, Azasonazole, Propiconazole, Tebuconazole, Cyproconazole, Metconazole, Imazalil, Dichlorfluanid, tolylfluanid, 3-iodo-2-propynyl butylcarbamate, N-octyl-isothiazolin-3-one and 4,5-dichloro-N-ostilisotiazolin-3 -one The obtention and use of the active products according to the invention follows from the following examples. Examples of obtaining. Example 1 11 g (0.024 mol) of 5-amino-3-cyano-4- (1, 1-difluoroethyl sulfonyl) -1- (2,6-dichloro-4-trifluoromethylphenyl) -pyrazole are dissolved in 80 ml of pyridine and 10 ml of triethylamine. Then hydrogen sulfide is passed through at room temperature for about 3 hours. The reaction solution is then combined with water and extracted several times with dichloromethane. After drying over magnesium sulfate, the mixture is concentrated by evaporation in vacuo by removal of the solvent by distillation, the oily residue is stirred with diethyl ether and filtered off with suction. 8 g (68% of theory) of 5-amino-4- (1,1-difluoroethyl sulfonyl) -1- (2,6-dichloro-4-trifluoromethylphenyl) -3-thiocarbamoyl-pyrazole are obtained with a melting point of 228-29 ° C. In a manner analogous to that of Example 1, or according to the general indisasions for the obtention, the formulations (I) given in the following A are prepared: Table A: Ar Obtaining the new starting products of the formula (VII). Example (VII-l) 3.8 g (0.012 mol) of 5-amino-3-cyano-1- (2,6-dichloro-4-trifluoromethylphenyl) -pyrazol are dissolved in 50 ml of pyridine and 5 ml of triethylamine. After this, hydrogen sulphide is passed through at room temperature for about 2 hours, followed by stirring for another 10 minutes at 50 ° C. The solution of the reaction is sonsentra by evaporation in vasío. The remaining residue is denoted by water and is dichloromethane. It is extracted several times with dichloromethane, the combined dichloromethane phases are dried over magnesium sulfate and evaporated in vacuo. 3.4 g (81% of theory) of 5-amino-1- (2,6-dichloro-4-trifluoromethylphenyl) -3-thiocarbamoyl-pyrazole are obtained. - '• H-NMR (in DMSO with TMS as internal standard, S in ppm): 9.49 (ÍH); 9.08 (ÍH); 8.21 (2H); 5.96 (ÍH); 5.69 (2H).

Obtaining the new starting products of the formula (III). Example (III-l) Example (III-1) is obtained, starting from 3-siane-1- (2,6-disloro-4-trifluoromethylphenyl) -5- (pyrrol-1-yl) -pyrazole, analogously to that of the example (VII-1). 1 H-NMR (in DMSO are TMS as internal standard, 5 in ppm): 9.95 (1H); 9.58 (ÍH); 8.30 (2H); 7.19 (ÍH); 6.20 (2H); 6.13 (2H). Application Examples In the following application examples, somatic substances are used for the purpose of sontinuation: (TO) CF, (All compounds are conosidos by EP-A 0 659 745) Example A Test with Phaedon larvae. Solvent: 7 parts by weight of dimethylformamide. Emulsifier: 1 Part by weight of alkylaryl polyglycol ether. To obtain a preparative preparation of astive product, 1 part by weight of asthmatic prodrug is mixed with the indicated amount of solvent and is the sanitized index of emulsifier and the concentrate is diluted with water to the desired concentration. Cabbage leaves (Brassica olerácea) are treated by immersion in the active preparation of the desired concentration and covered with larvae of the horseradish leaf beetle (Phaedon co-chleariae), while the leaves are still moist. After the desired time the detrussion in% is determined. In this 100% saso it means that all the beetle larvae were destroyed; 0% means that no beetle larvae were destroyed. In this test they caused, at an exemplary concentration of astusto produsto of 0.00001%, for example the compounds according to the obtaining examples 1 and 2 a destrussión of 100% respestivamente to the flavor of 3 days, whereas the compound conosido (A) It showed only 25% destruction. Example B Test with Plutella. Solvent: 7 parts by weight of dimethylformamide. Emulsifier: 1 Part by weight of alkylaryl polyglycol ether. For the preparation of a preparative preparation of astive product, 1 part by weight of the active compound is mixed with the indicated amount of solvent and with the indicated amount of emulsifier and the concentrate is diluted with water to the desired concentration. Sun leaves (Brassica olearacea) are treated by immersion in the preparation of astivo product of the desired soncentration and subtracted are caterpillars of the cabbage moth (Plutella aculipennis)while the leaves are still wet. After the desired time the destruction is determined in%. In this case 100% means that all caterpillars were destroyed; 0% means that no caterpillar was destroyed. In this test, he proved, to an exemplary analysis of 0.0001% astivo prodrug, for example the compound according to the obtaining example 1 a 75% destruction and the one of the obtaining example 2 a 100% destrussión 3 days, whereas the conoside compound (A) showed only 15% destruction. Example C Assay with Spodoptera frugiperda. Solvent: 7 parts by weight of dimethylformamide. Emulsifier: 1 Part by weight of alkylaryl polyglycol ether.

In order to obtain a suitable active preparation, 1 part by weight of the asthmatic product is mixed and the indicated amount of the solvent and with the indicated amount of the emulsifier and the solution diluted are water to the desired concentration. Sun leaves (Brassica olerácea) are treated by immersion in the preparation of active compound of the desired concentration and are covered with caterpillars of the nocturnal moth (Spodoptera frugiperda), while the leaves are still moist. The destruction in% is determined by the taste of the desired time. In this case 100% means that all caterpillars were destroyed; 0% means that no caterpillar was destroyed. In this test, they caused, to an exemplary constellation of astute produst of 0.01%, for example the blanks according to the examples of obtention 1, 2 and 4 a 100% detrustion respectively to the 7 days savor, while the somatic ones. (B) showed only 10% destruction and (C) showed no destruction. Example D Test with Nephotettix. Solvent: 20 parts by weight of dimethylformamide. Emulsifier: 1 Part by weight of alkylaryl polyglycol ether. To obtain a suitable preparation of astivo product, 1 part by weight of asthmatic prodrug is mixed, the indicated sanctity of solvent and with the indicated amount of emulsifier and the diluted concentrate are water until the desired sonsension. Rice seedlings (Oryza sativa) are treated by immersion in the preparation of active product of the desired consension and are subtended to be larvae of green greens of rice (Nephotettix sinstiseps), while the seedlings are still moist. After the desired time the destruction is determined in%. In this case 100% means that all the sigarras were destroyed; 0% means no cicada was destroyed. In this test they gave, at an exemplary concentration of active compound of 0.1%, for example, the compounds according to Preparation Examples 2 and 4, a 100% extrusion and the compound of Example 5 a detrussion of 80%. , respec- tively to the 6-day flavor, while the known compounds (A) showed only a 10% detrussion and (D) showed no detrussion.

Example E Test with Myzus Solvent: 7 parts by weight of dimethylformamide. Emulsifier: 1 Part by weight of alkylaryl polyglycol ether. In order to obtain a suitable preparation of active compound, 1 part by weight of the asthmatic product is mixed in the sanity index of the solvent and with the indicated amount of emulsifier and the concentrate is diluted with water to the desired concentration. Cabbage leaves (Brassica olerácea), which are attacked by the green louse of the peach leaf (Myzus persicae), are treated by immersion, in the preparation of the active product at the consension de-seada. The destrussión in porsentaje is determined by the desired time. In this saso 100% it means that all the lice of the leaves were destroyed; 0% means no leaf louse was destroyed. In this test, they caused, at an exemplary concentration of astute produst of 0.1%, for example the compounds according to the following preparation examples, the following destructions: 1 = 80%, 2 = 98% and 4 = 100%, respectively after 6 days, while the sonoside compounds (C) showed only a 50% destruction and (B) showed no efesto. Example F. Test of boundary concentration / soil insects. Test insects: Larvae on the ground of Diabrotica balteata. Solvent: 4 parts by weight of acetone. Emulsifier: 1 Part by weight of alkylaryl polyglycol ether. For the preparation of a suitable preparation of active compound, 1 part by weight of active compound is mixed with the indicated amount of solvent, the indicated amount of emulsifier is added and the concentration is diluted with water until the desired sonsension. In this case, the concentration of astute produsto in the preparation does not generate practically any paper, being decisive only the amount of active product by weight per unit of soil volume, which is indicated in ppm (mg / l). The soil is loaded in pots of 0.5 liters and these are allowed to stand at 20 ° C. Immediately after loading, 5 grains of corn, previously germinated in each pot, are placed. After 1 day, the test insects are placed on the treated land. After 7 days, the degree of astivity of the active produst is determined by counting the dead and live test insects in%. The degree of astivity is 100%, if all the test insects have failed, it will be 0% when exactly the same number of test insects are alive as in the untreated controls. In this test, they caused, at an exemplifying concentration of the active product of 0.002%, for example the compounds of the preparation examples 2, 4 and 5, a destruction of 100%. Example G. Test of limit concentration / systemic effect on the roots. Test insects: Larvae of Phaedon cochleariae. Solvent: 4 parts by weight of acetone. Emulsifier: 1 Part by weight of alkylaryl polyglycol ether. To obtain a suitable preparation of the active compound, 1 part by weight of the active compound is mixed with the indicated solvent, the sanitized index of the emulsifier is added and the water is diluted until the desired sonication is obtained. the preparation of the active produsto is intimately mixed with the soil. In this case practically no role plays the concentration of the active produst in the preparation, being decisive only the amount by weight of the active product per unit of volume of the soil, which is indicated in ppm (= mg / l) ). The treated areas are sown in pots and planted these are sun (Brassica olerácea). The active product can be absorbed in this way from the ground by the roots of the plants and transported to the leaves. To demonstrate the systemic effect of the roots are covered, after 7 days, the leaves are the test animals previously placed. At the taste of another 2 days the evaluation is carried out by sonating or evaluating the dead animals. From the number of failures the systemic efesto of the roots of the active product was used. This is 100% when all test animals have died and will be 0% when they live exactly the same number of test animals as in the untreated controls. In this test, they caused, at an exemplary consentration of the active product of 0.002%, for example the compounds of Examples 1, 4 and 5 a distribution of 100%. Example H. Test with flies (Musca domestica). - Test animals: Musca domestica, adults, Reichswald family (OP, SP), resistant to carbamate).

Solvents: 35 parts by weight of ethylene glycol monomethyl ether, 35 parts by weight of nonylphenol polyglycol ether. In order to prepare a suitable formulation, 3 parts by weight of active compound are 7 parts by weight of the solvent-emulsifier mixture indicated above and the concentrated emulsion, obtained in this way, is diluted with water, up to -centralization desired in sada saso. 2 ml of this active prodrug preparation are pipetted onto filter paper discs (9.5 cm), which are found in petri dishes of sorresponding size. After the screening of the filter paper disks, 25 test animals are transferred to the Petri dishes and subnetted. At the taste of 1, 3, 5 and 24 hours the astivity of the preparation of the active product is determined. In this case 100% means that all the flies were destroyed; 0% means that no fly was destroyed. In this test they showed, for example, the compounds of the seeds of preparation 1, 2, 4 and 5, at an exemplary consentration of the astive product of 100 ppm, a degree of astivity of 100%.

Example I. Test with fly larvae / developmental inhibitor effect. Test animals: All larval stages of Lusili suppress (OP-resistant). [pupae and adults (no contact with the astivo product] Solvent: 35 parts by weight of ethyleneglisol monomethyl ether 35 parts by weight of nonylphenol polyglycol ether In order to prepare a suitable formulation, 3 parts by weight of the produsto astivo are mixed 7 parts by weight of the emulsifier-emulsifier mixture previously indicated and diluted in emulsion, obtained in this way, are water up to the desired concentration in each case 30-50 larvae are available, per each consension, on sarne. of saballo that is ensued in glass tubes (1 cm3), on which 500 μl of the dilution to be tested has been pipetted.The glass tubes are arranged in plastic cups, whose bottom is covered with sand. sea, and stored in an air-conditioned enclosure (26 ° C ± 1.5 ° C, relative humidity 70% ± 10%). The test of astivity is verified at the 24-hour and 48-hour flavors (lard-like efesto). After the migration of larvae (approximately 72 hours) the glass tubes are removed and perforated caps of synthetic material are placed on the glasses. At the time of development equal to 1% of the time, (control flies are slashed), the fringed flies and the pupae / pupal pods are counted. As a criterion for the assassination, the appearance of death is taken in the larvae treated at 48-hour flavor (larvicidal ephesus) or the inhibition of the eslosion of the adults from the pupae or the inhibition of the formation of Pupae As a criterion for the in vitro effect of a substance serves the inhibition of the development of fleas, or a stoppage of development before reaching the adult stage. In this case, a 100% larvicidal effect means that all the larvae died after 48 hours. An inhibitor of 100% development signifies that no adult fly was found. In this test, for example, the compounds according to Preparation Examples 1, 2, 4 and 5 showed an exemplary consension of the active ingredient of 100 ppm, a 100% effect.

Example J. Assay with resistant Boophilus microplus / Parkhurst SP-resistant family. Test animals: Adult females. Solvent: 35 Parts by weight of ethylene glycol monomethyl ether. 35 Parts by weight of nonylphenol polyglycol ether. To obtain a suitable formulation, 3 parts by weight of the asthmatic prodrug are mixed with 7 parts of the solvent-emulsifier mixture indicated above and the concentrate is diluted in emulsion, obtained in this way with water to the desired concentration in each case. 120 Booophilus microplus adults are immersed in the preparation of active product to be tested for 1 minute. After the transfer to plastic cups and maintenance in a slimatized segment the degree of destruction is determined. In this case 100% means that all the ticks were destroyed; 0% means that no ticks were destroyed. In this test, for example, the compounds of Preparation Examples 2, 4 and 5 showed an exemplary sonsension of the active compound in 100 ppm, an effect of 100%. Example K. Assay with resistant Boophilus micropolus / Parkhurs SP-resistant family. Test animals: Adult females. Solvent: Dimethylsulfoxide. 20 mg of the active compound are dissolved in 1 ml of dimethylsulfoxide, with lower concentrations being prepared by dilution in the same solvent. The test is carried out in 5 determinations. 1 μl of the solutions are injected into the abdomen, the animals are transferred to sapsules and kept in an air-conditioned room. The effect is determined through the inhibition of egg laying. In this case 100% means that no tick has laid eggs. In this test, for example, the compounds of Preparation Examples 1, 3, 4 and 5 show an exemplary constraction of the active compound of 20 μg / animal, an effect of 100%. Example L. Test with cockroaches. Test animals: American Periplaneta. Solvent: 35 Parts by weight of ethylene glycol monomethyl ether. 35 Parts by weight of nonylphenol polyglycol ether. In order to obtain a suitable formulation, 3 parts by weight of the active compound are mixed with 7 parts of the aforementioned solvent / emulsifier mixture and the emulsion concentrate obtained in this way is diluted with water to the desired concentration. in each saso. 2 ml of this asthma prodrug preparation are pipetted onto filter paper discs (09.5 cm), which are found in petri dishes of sorresponding size. After the screening of the filter paper disks, 5 Periplaneta americana test animals are transferred and covered. After 3 days the activity of the preparation of the astivo product is determined. In this 100% saso it means that all the cockroaches had been destroyed; 0% means that no cockroach was destroyed. In this test, for example, the compounds of Preparation Examples 1 and 2 showed an exemplary consension of the astute prodrug of 100 ppm, a 100% effect. It is made to sound that they are relasion to this fesha, the best method sonosido by the solisitante to take to the prástisa the sitada invensión, is the one that slaro of the present dessripsión of the invention.

Claims (9)

2. Having described the invention as above, the property contained in the following claims is claimed as property: 1. Compounds of the general formula (I) i Ar characterized in that: R1 signifies H2N-CS, R2 signifies haloalkyl, haloalkenyl or halogenalkynyl, R3 signifies hydrogen, amino or means one of. The following groupings: where R 4 signifies alkyl, halogenoalkyl or alkoxyalkyl or means substituted phenyl or pyridyl, if appropriate, R 5 signifies hydrogen or alkyl, R 6 signifies hydrogen, alkyl or signifies phenyl or pyridyl substituted respectively, and R 7 signifies alkyl, alkenyl, alkynyl, formyl, alkylcarbonyl, haloalkylcarbonyl or also isakaromyl nyl; Ar signifisa phenyl or pyridyl substituted respec- tively if given and n means a number 0, 1 or 2. 2. - Proseeding for the obtention of compounds of the formula (I) according to claim 1, because a) has been derivatized derivatives of 3-siapyrazole of the formula (II)
3. Ar wherein Ar, R2, R3 and n have the meaning indicated above, with hydrogen side, if appropriate in the presence of a reactive auxiliary agent; and in given saso, in pre-sensia of a diluent; or b) 3-thiosarbamoylpyrazole derivatives of the formula (III) have been reached.
4. (III) where Ar has the previously unidentified meaning and > 3-l means one of the following groupings: where R 4, R 5, R 6 and R 7 have the meaning previously unsubstantiated, are sulfenyl halides of the formula (IV) Hal-S-R 2 (IV) in which R 2 has the meaning previously unsubdued and Hal signifisa halogen, especially chlorine or bromine , if appropriate in the presence of a diluent and, if appropriate, in the presence of a reaction auxiliary agent; c) the 2-thiosarbamoylpyrazole derivatives obtainable according to the processes (a) or (b) of the formula (la) are oxidized wherein Ar, R2 and R3 have the meaning indicated above, with oxidizing agents if appropriate in the presence of a diluent and, in a given case, in the presence of a satallizer. 3.- Compounds of the formula (III)
5. Ar characterized because Ar has the previously unnamed meaning and R 3-1 means one of the groupings where R4, R5, R6 and R7 have the meaning given in claim 1. 4.- Compounds of the formula (VII) characterized because Ar has the previously unnamed meaning. 5. - Sarasterized pestisid agents because they have a content in at least one compound of the formula (I) according to claim 1.
6. 6.- Use of the compounds of the formula (I) according to claim 1, characterized in that it is for the fight against pests.
7. 7. Process for the control of pests characterized in that compounds of the formula (I) according to claim 1 are allowed to act on the pests and / or on their environment.
8. 8. - Process for obtaining pesticidal agents, characterized in that compounds of the formula (I) according to claim 1 are mixed, are extenders and / or surfactants.
9. 9. Use of the compounds of the formula (I) according to claim 1, characterized in that it is for the preparation of pesticide agents