PL98243B1 - Fungicide and insecticide - Google Patents

Description

The present invention relates to a fungicide and insecticide containing new 5-trifluoromethyl-1,3,4-thiadiazoles substituted in the 2-position as active substances. It is known that certain thio-5-trifluoromethyl-1,3,4-thiadiazoles substituted in the 2-position. On 2, they have fungicidal properties (patent specification of Sitanów Zied together of Aimeryki mir 3,562,284), but their action, especially when used in small amounts and concentrations, is not always completely satisfactory. The insecticidal properties of these 1,3,4-thiadiazoles are not known. It has been found that the new 5-trifluoromethyl-1,3,4-thiadiazoles substituted in the 2-position of the formula 1, where R is a substituted alkyl radical, a phenyl radical substituted with ortho or meta position, multisubstituted phenyl radical, substituted femylalkyl radical, optionally substituted phenylalkenyl radical, optionally substituted five or six ozone heterocyclic radical containing 1-4 heteroatoms (N, S), optionally substituted benzimidazoyl or benzothdazolyl radical, a naphthyl radical, a quinolyl radical, a cyano group or a group of formula 8, a group of formula 9 in which R1 and R2 together represent a tri-, four, or pentomethylene group, or a group of the formula where R 'and R "are radicals alkyl or together with nitrogen and optionally other (0, N) heteroatoms to form an optionally substituted 6 or 7 membered ring, and X is oxygen or sulfur, and n in formula 1 is the integer zero, I or 2, have strong fungicidal and insecticidal properties. The new 5-trifluoromethyl-1,3,4-thiadiazoles substituted in the position 2 of formula I are thus produced in such a way that a) 2 -halogen-5-trifluoromethyl-1,3,4-thiadiazole of formula II in which Y is chlorine or bromine is reacted with mercaptan of formula III in which R is as defined above, optionally in the presence of of a solvent and an acid-binding agent, and the resulting 2-substituted 5-trifluoromethyl-1,3,4-thiazole of formula IV, in which R is as defined above, is optionally subjected to the treatment of an oxidizing agent, receiving, depending on the oxidizing agent used, the compounds of formula I, in which n is the number 1 or 2, or b) 2-mercapto-5-triyluoromethyl-1,3,4-tiaddazole of formula 5a or 5b is subjected to reaction with a compound of formula 6, wherein R is as defined above and Z is chlorine, bromine or iodine, or a methane & ulfonylox group or tosulfonyloxy, optionally in the presence of a solvent and an acid-binding agent, and the resulting taso-5-trifluoro) -methyl-1-,4-lthiadiaBal substituted in the 2-position of formula IV is optionally subjected to treatment by by pouring the oxidizing agent and depending on the agent used, the compounds of formula I are obtained, in which n is the number 1 or 2, or c) 98 24398 243 3 in the case of the preparation of sulfonyl compounds (n in formula 1 is the number 2) React 2-halo-5-trifluoro-methyl-1,3,4-thiaddazo in the formula II with sulfinic acid of formula 7, wherein R is as defined above, in a solvent environment and in the presence of inorganic or organic bases, or by using the corresponding sulfinates in place of sulfinic acid and bases. Surprisingly, it has been found that the new 5-tri-fluoromethyl-1,3,4-thiadiazoles substituted in the 2-position exhibit stronger fungicidal and insecticidal activity, especially insecticidal activity. in the soil and inhibit the action The development of pests than the known, 2-substituted thio-5-trifluoromethyl-1,3,4-thiadiazoles, which are the most closely related compounds. The compounds of formula I are therefore an enrichment of the technology. If 2-bromo-5-trifluoromethyl-1,3,4-thiadiazole and 2-mercajpitobenzioic acid are used as starting products, the course of the reaction according to variant (a) is shown in Scheme 1. If 2-chloro-5-trifluoromethyl-1,3,4-thiadiazole and 2-mercaptopyrimidine and chlorine as the oxidizing agent are used as starting products, the reaction carried out according to variant (a) with oxidation proceeds according to Scheme 2. When 2-bromo-5-trifluoramethyl-1,3,4-tttadiazole and 3,5-dimethylthiophenol are used as starting products, and hydrogen peroxide as an oxidizing agent, the reaction according to variant ( a) with the oxidation according to the scheme 3. If 2-mercapto-5-1x6 j fl fl fl and 2-w-bromo-5-nitrothioiphene are used as the starting products, then the course of the process according to variant (b) can be represented by of scheme 4 If, according to variant (c), 2-bromo-5-trifluoromethyl-1,3,4-thiadiazole is subjected to reaction * with naphthalene-2Hsulfinic acid in the presence of sodium hydroxide, the reactions can be represented by scheme 5. Used in process variant (a) as a starting product 2-halo-5-trifluoromethyl-1,3,4-45-thiadiazole of formula 2 is a known compound [German Patent Specification DOS No. 2,162,575 and J. Het. Ghem. 11, 343-345 (1974)]. It is obtained by the method of Kanaok's band [Pharmaeeutical fiulletin 5, 385-389 (1957)] by diazotizing the appropriate 2-amino-thiadiazole {preparation J. Het. Chem. 3, 336-337 (1966)]. It was surprisingly found that the reaction described in this publication (Sandmeyer reaction) proceeds spontaneously with high yields, such that at a temperature of -5 ° C to 15 ° C and without the usual addition of copper salts. Otherwise, mercaptans used in variant (a) are generally defined by formula 3, in which R is preferably a straight or branched, monosubstituted or multisubstituted alkyl radical of 1 to 1 carbon atoms, the substituents 6a being preferably halogens, in particular fluorine, chlorine or gates, cyano, isothiocyanate groups. , phenyl, carboxyl, alkylcarbonyl groups having 1-2 carbon atoms in the alkyl radical, or phenylcarbonyl groups, optionally substituted with halogen or lower alkyl radicals. The R substituent also denotes a lenylalkenyl radical with 2 to 4 carbon atoms in the alkenyl radical, as well as a phenyl radical, preferably having one ortho or meta substituent, a phenyl radical having a greater number of identical or different substituents, and the radical phenylalkyl, in particular with 1 to 2 carbon atoms in the alkyl radical, containing one or more identical or different substituents, the phenyl radical in each case having preferably such substituents as alkyl radicals with 1 to 4 atoms carbon, haloalkyl, haloalkylthio and haloalkylsulfonyl radicals each containing 1-2 carbon atoms and 2-5 halogen atoms, especially fluorine, alkoxy groups, alkyl, cainbonyl and alkoxycaribonyl groups each containing 1-4 carbon atoms in hydroxyl radicals, alkyl groups, alkyl groups , cyano and thiocyanin. In addition, R is preferably the following five- and six-membered heterocyclic radicals: and imidazole, optionally substituted in the 1- and / or 4-position and / or 5 alkyl radicals having 1-2 carbon atoms, phenyl radicals which optionally contain chlorine atoms as substituents, or also with nitro groups, a thiazole radical optionally having in position 4 and / or as substituents: alkyl radicals with 1-2 carbon atoms, halogen atoms or nitro groups, 1,2,4-thiaddazole radical optionally substituted in the 3-position by an alkyl or alkylthio radical with 1-4 carbon atoms, 1,3,4-thiadiazole radical optionally substituted in the 2-position with an alkyl radical with 1 to 4 carbon atoms, amino, alphylcarbonyl, alkyldiaminic, dialkylamino, alkane-amino-methyleneimine or N, N * -dualkylurea radicals, the alkyl groups being in these groups each contain 1-2 carbon atoms, optionally chlorine-substituted phenyl radical, alkylthio or alkylsulfonyl group with 1-h2 carbon atoms in the alkyl radical, haloalkyl radical with 1-2 carbon atoms 1a and 2 to 5 halogen atoms or a nitro group, a tetrazole radical optionally substituted with an alkyl radical with 1 to 1 carbon atoms, a thiopera radical, optionally substituted with nitro gas or a halogen, optionally substituted with an alkyl radical with 1 to 2 carbon atoms, or a pyridine radical with a halogen, Pyridine N-oxide or pyrimidine N-oxide, optionally a methyl substituted thiazoline, tetrahydro-pyrimidine and tetrahydro-thiazine radical, R is also preferably an enziimidazolyl and benzothiazolyl radical, optionally substituted in a phenyl radical or a cM-halo pheoxy radical. - 2 carbon atoms, as well as R preferably represent groups of formulas 8, 9 or 10, where in formula 9 R1 and R2 are preferably together preferably a tri or ozteromethylene radical, in formula X is an oxygen or sulfur atom, and R 'and R "are preferably alkyl radicals with 1 to 2 carbon atoms, or preferably, together with the nitrogen atom, form a perhydrazepine ring. o-, morpholine- or piperazine-N-hydroxyethyl. Furthermore, R is preferably also a naityl radical substituted with a nitro group, a halogen or an alkyl radical of 1-2 carbon atoms, a quinolinyl radical, a quinoline N-oxide group or a cyano group. The mercaptans used for the reaction are partially known [see Houben-Weyl, vol 9, star. 7-48 (1955) and US Patent No. 3,798,229], or may be made by the methods described in these publications. For example, aromatic mercaptans are prepared by reacting sulfochlorides with zinc and sulfuric acid. In order to obtain aliphatic and araliphatic mercaptans, for example, the corresponding bromides are refluxed with ethanol thiourea and the resulting isothiuronium salts are broken down. an aqueous solution of an alkali metal hydroxide and the mercaptans are isolated by known methods. Examples of mercaptans of formula III are the following compounds: ethyl ester of 4-mercapovaleric acid, triphenylmethyl mercaptan, 2-chloroethyl mercaptan, mercaptan 3- (phenylallyl mercaptan) p-methylphenacyl, 2,6-dichlorophenyl mercaptan. - .. 2-mercaptoquinoline N-oxide, 4-chloro-3-methylenyl mercaptan, 1,4-bis-mercaptomethylbenzene, ethylene diamane bis-dithiocarbamate, 4-nitrobenzyl mercaptan , pentafluorophenyl mercaptan, 2-ethoxyphenyl mercaptan, 2-isopropylthio-5-mercaptan, pto-1,3,4-thiadiazole, 4-trifluoromethoxybenzyl mercaptan, -chloro-2Hnerkaptanaphthalene and 4-chloro-2-mercaptapyridine N-oxide,. f The starting material of the variant (b) Nmeirkapto-S-trifluoromethyl-13S-thiadiazole of the formula VI is a known compound (German Patent Specification No. 2,162,575). It is obtained by reacting 2-bromo-5-trifluoromethyl-1,3,4-thiadiazole of formula II with thiourea in boiling ethanol and subsequent treatment with concentrated sodium hydroxide solution. The second component of the reaction according to variant (b) is generally given by the formula 6 In this formula, R preferably represents those substituents as defined above. the preferred R substituents in the morcaptans of formula III. The compounds of formula VI used as starting compounds are known compounds in organic chemistry and can be prepared by simple, known methods. Examples of these compounds are: 2,4-two * trofluorobenz.en, 4 -chlorophenyltriuoromethylsulfone, 2-iodo-i-methyl-S ^ nitroimidazole, 1- (2-chloroethyl) -2-methyl-5-nitroimidazole, 2-bromo-5-niitro-1,3,4-tdadiazole, -chloro 3-Methylmercapto-1, 4-thiadiazole, N, N-Clumethytocarbamoyl chloride, 4-nifcrophenyleths bromide, chloromethyl isothiocyanate, 2-bromoacetone, chloroacetonitrile, 2,4-trichlorothiazole, 1,1,1-trifluOTo-2 -methanesulfonyloxy ethane, 4-chlorobenzyl chloride, 1,3-bis-toluenesulfonyloxypropane, and 3,4,5-trichloroniftrobenzene and 2-chloromethylpyridine. Sulfinic acids used as starting products in variant (c) are generally determined by formula 7 In this formula, R preferably represents those substituents which have been indicated above as the preferred R substituents in the imercaptans of formula 3 Sulfin acids. The compounds or sudinates which are hardly used in the reaction are compounds generally known in organic chemistry and can be prepared by simple, known methods, for example by reducing the corresponding suliochlorides with alkali metal sulphites in water, whereby more stable sulphonic acid salts can be continue without * singling out [Houben-Weyl, Methond der .organdschea Chemie vol. 9, 885-343 (1955), ed. Georg Tbieme Verlag Stuttgart]. Examples of these compounds are: Ninefluorobutaou sulfinate, 3,4-dimethylbenzide sulfinate, pyridine-3-sulfinate, thioteiUi-3-sulfinate; 3-bromotoenzene sulfinate, 3,4- ^^ ictorobenaene sulfindane, 85 3-bromo-4 ^ iitEottenzene sulfinate,: g-fluGrobenzemi sulfinate, 6-chloronaphthalene 2-sulfinate, 2,3-dich * orobenzene sulfinate, sulfinate bromomethyl, 49 2 * benzothiazole sulfinate, <RTI ID = 0.0> ix) </RTI> msiQ-butane-sulfinate,: sulfinate z-methylbenzenai, 3-methyl-4Htn-fluoromethyl) thiobenzene sulfinate, SAlMinate 2- <4-chk) ix) phenyl) - V-methyl 45 4-methyllnaphthalene 2-sulfinate &....,; 2,4-Divirniethoxybenzene sulfinate. :,. ¦; ¦¦ In the process according to variant (a), the solvents are preferably water and inert organic solvents. These preferably include cathones * such as diethyl ethyl ketone, in particular acetone and ethyl ethyl ketone, ni / triles such as propionitrile and in particular ascetonitrile, alcohols such as ethanol or isopropanol ethers such as ether / ofuran or diocfcan, lus hydrocarbons such as ligiroin, petroleum ether, benzene, toluene and xylene, chlorinated hydrocarbons such as elylform, tetrahydrocarbon and methylene chloride, as well as formamides, especially divomethylformaimide. 60 Reactions according to the variant (a. Are carried out in the presence of an acid binding agent. All the usual inorganic or organic acid binders can be used, such as alkali metal carbonates, e.g. sodium carbonate, potassium carbonate and sodium bicarbonate, or lower , tertiary alkylamines, cycloalkylamines or aralkylamines, e.g. triethylamine, dimethylbenzylamone and cyclohexylamine, or pyridines and diazaphoicyclooctane, as well as alkali metal alkoxides, e.g. sodium methoxide and potassium ethoxide or alkali metal hydroxides, e.g. The reaction according to variant (a) can be carried out at different temperatures, but the usual temperature is from about 0 ° C to about 120 ° C, preferably 20 to 100 ° C. If a solvent is used, it is preferable the reaction is carried out at its boiling point. The process according to variant (a) is carried out for 1 mole of the compound of formula II, preferably about 1 mole of mercaptan of the formula III and about 1 mole of the acid binding agent. In order to isolate the compound of formula 1, the reaction mixture is poured into ice-cold water, the remaining precipitate is filtered off, optionally washed and dried, or the reaction mixture is rinsed with water, the organic phase is separated, it is dried and the solvent is removed, or the precipitated salt (by-product) is filtered off and the reaction product is isolated from the filtrate. The products obtained can, if appropriate, be purified by conversion or distillation. According to variant (a), the compounds of formula IV obtained can be further oxidized. For this purpose, all customary and organic oxidizing agents, such as chlorine in water * peroxy acids, e.g. methachlonoperbenzoic acid, or hydrogen peroxide in glacial acetic acid or methanol, potassium permanganate and chromic acid. The oxidation process according to variant (a) can be carried out at different temperatures, but the temperature is usually around -30 ° C C to + 100 ° C, preferably -10 ° C to + 80 ° C. In the oxidation reaction according to variant a), about 1 to 4 moles of the oxidizing agent are used per 1 mode of the compound of formula IV. If 1 mole of an oxidizing agent, such as m-chioroperebenzoic acid in methylene chloride or hydrogen peroxide in acetic acid anhydride, is used at -10 ° C to + 0 ° C, the compounds of formula I are preferably obtained. where n = 1. In excess of the oxidizing agent and carrying out the reaction at higher temperatures (10- ^ 80 ° G), the compounds of formula I are preferably obtained where n = 2. In order to isolate the oxidation products, the reaction mixture is It is blown into ice water, the precipitate obtained is filtered off, optionally washed and dried, or the reaction solution is brought to a pH value of 7-8, extracted with an organic solvent, the extract is dried and the solvent is distilled off. In both cases, the reaction products can be purified by recrystallization or by column chromatography. In the process according to variant (b), preferably 8243 S water and polar organic solvents, preferably nitriles, for example acetonitrile, sulfoxide, e.g. dimethyl sulfottoide, formamides, v '»p. dimethylformamide, ketones e.g. acetone, ethers, nE. ethyl ether and tetrahydrofuran as well as • chlorohydrocarbons such as methylene chloride and chloroform. These reactions are carried out in the presence of an acid-binding agent, preferably using non-organic or organic acid-binding agents, mentioned above in the discussion of variant (a). The reactions according to variant (b) will be handled at temperatures (Added for variant (( a). For 1 mole of the compound of formula 5, approximately 1 mole of the halide of formula 6 and approximately 1 mole of the acid-binding agent are preferably used. The obtained compounds of formula 1 are prepared using the methods given in variant (a). in variant (b), oxidation reactions are also used, they are carried out similarly as described above for variant (a) (oxidizing agents, temperature and equilibration). In the process carried out according to variant (c), the diluents are preferably used as as stated above for variant (a) Reactions are carried out in the presence of a base All the usual inorganic and organic bases can be used, such as alkali metal hydroxides * e.g. sodium and potassium hydroxide, or lower tertiary aMriloamdny, e.g. triethylanine. The temperature during the process according to variant (c) corresponds to the temperature in variant (a). When carrying out the process according to variant (c), for 1 mole of the compound of formula 2, approximately 1 mole of sulfinic acid of formula 7 is used. In order to isolate the compounds of formula 1, the reaction mixture is poured into ice water, the precipitate formed is filtered off, dried it purifies it by recrystallization. The compounds of formula I have a strong fungicidal effect, and in the concentrations necessary for the control of fungi and bacteria, they do not harm the cultivated plants, and are also suitable as plant protection agents for combating fungi and bacteria. Fungicides are used in the protection of plants for the control of primary fungi (Airchimycetes), algae (Phycomycetes), Ascomycetes (Basidiomycetes) and non-perfect fungi (Fungi irnperfeoti). The active ingredients of the compositions according to the invention have a wide range of action and can be used against parasitic fungi and bacteria which attack the above-ground parts of plants and plants in the ground, as well as against seed-borne pathogens. They are particularly effective against pests of the genera Pythium, Phytophthora, Fusarium, Fusicdcladum and Botrytis and against Verticillium lubatrum, Coohliobolus miyabeanus 60 and Phialophora cinerescens. These compounds can also be used to combat cereal diseases such as the lightning effect of stone wheat. As plant protection agents, these compounds can be used to calibrate seeds and aerial parts ** of plants. 98 243 Compounds of formula 1 also show good insecticidal properties, especially they are highly insecticidal in soil. In addition, they strongly inhibit the development of insects and pre-venous insects, preventing their transformation into a pupa or a sexually mature individual. This effect occurs during moultment, which is only typical of arthropods, or is partly sustained also during many stages of development, and only occurs during initiation or hatching. These compounds can therefore be used effectively to combat harmful biting insects and flies. Insects with a mouth-sucking organ include, above all, aphids such as birch aphid (Myzus persicea), beetroot moth (Doralis fabae), June aphids, such as Aspidiotuis hederae, Lecanium hesperidum, and Pseudococcus maritimus, and bugs, such as beetroot moth (Piesma auadrata) and the house bug (Cime ~ x Slectularius). I For insects with mouth organ bites. Mainly there are caterpillars of butterflies such as Plutella maculipennis and Lymantria dispar, beetles such as the corn wolf (Sitophilus granarius), the Colorado potato beetle (Leptinotarsa decemlineata), as well as soil-living species such as Drutower (Agriotes sp. ) and cockroaches (Melolontha melolontha), as well as cockroaches such as German cockroach (Blattella germanica), orthoptera, such as house cricket (GryHas dome & ticus), such as Reti culitermes and sunflower, e.g. ants, include especially flies such as the moth (Drosophila melanogaster), the southern fruit fly (Ceratitis caopitata), the housefly (Musca domestica) and the long-afflicted fly, e.g. the mosquito (Aedes aegypti active substances). when used in appropriate amounts and concentrations, they also exhibit good herbicidal and microbostatic action. The compositions according to the invention may take the form of conventional formulations, such as solutions, emulsions, suspensions, powders, pastes and granular products. Such preparations are prepared by known methods, for example, by mixing the active ingredients with diluents such as liquid solvents, liquefied gases under pressure and / or solid carriers, possibly with the use of surfactants. namely emulsifying and / or dispersing and / or foaming agents. If water is used as the diluent, organic solvents, for example, can also be used as the auxiliary solvent. Aromatic hydrocarbons, such as xylene, toluene, benzene or alkylnitals, chlorinated aromatic hydrocarbons or chlorinated aliphatic hydrocarbons, such as pathhenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane, or paraffins, are mainly used as the diluents. , e.g. petroleum fractions as well as alcohols, e.g. butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylfermamide and sulfoxide dimethyl as well as water. "V" "By gaseous gaseous solvents or carriers are meant those liquids which, at normal temperature and pressure, are gases, for example gaseous and aerosol carriers, such as dichodubifluoromethane or trichlorofluoromethane. Solid supports are ground natural scales such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earths, and ground synthetic mineral products such as highly dispersed silica, gMn oxide and silicates. Nonionic and anionic emulsifiers, such as the condensation products of fatty acid esters with polyoxyethylene or polyoxyethylene ethers of fatty alcohols, for example alkylaryl ethers of polyglycol, alkylsulphonates, and alkyl sulphates are used as emulsifiers and / or formulators. arylsulfonates. Suitable dispersants are, for example, lignin, sulphite liquors and methylcellulose. The new active substances may be in the compositions of the invention mixed with other known active substances. The compositions according to the invention preferably contain 0.1-95%, preferably 0.5-90%, by weight of active ingredient. v: Active substances can be used alone, in concentrates or preparations made therefrom by further dilution, such as ready-to-use solutions, emulsions, suspensions, powders, pastes and granular products. It is used in the usual way, for example by pouring, spraying, fogging, dusting, scattering. dry, damp, wet or sludge or encrustation. The concentration of the active ingredient in the formulations These to be used can vary widely, but is typically, 0.0001- ^ 1OP / tikOffey-f 0.01-1%. For the treatment of seed, preferably 0.001-50 g, preferably 0.01-10 g, of active compound per kg of seed are used. The active compounds can also be used with good results in the ultra-low-volume method and Ultra-50 Low-Volume (ULV) y for which it is possible to use preparations containing up to 95P / r of the active substance, and even 100fAs is the active substance itself. Multiple possible uses of the invention wetflug 55 result from the examples given below. Example i. Trial with Fusiciadium, preventive on apple tree Solvent: 4.7 parts by weight of acetone 60 Emulsifier: 0.3 parts by weight of polyglycol allirylaryl ether Water: 95 parts by weight, Active substances in the amount necessary to obtain the desired concentration; in the apirifflation fluid, the mixture is mixed with the above-mentioned amount of solvent and the dilution concentrate is mixed with the above-mentioned amount of water, containing the mentioned additives. The resulting spray liquor is sprayed until the morning light on the young apple seedlings, which are at the 4-6 leaf stage, and the plants are left in the greenhouse at a temperature of 20 ° C and air with a relative humidity of 70%. After 24 hours, the plants are infected with an aqueous suspension of conidial embryos of apple scab (Fusicladiurn dendmtdcum) and cultivated for 18 hours in a humid chamber with a temperature of 18-20 ° C and a relative air humidity of 100%. The plants are then placed back in the greenhouse for a period of 14 days, and 15 days after the infection, the degree of attack of the seedlings is determined, converting the obtained values into the percentage of attack, where 0 * / * means no attack, and 100% means that the plants are not attacked. have been completely taken over by the pest. The active substances tested, their concentration and the test results are given in the following Table I. Table I Fusicdadium test (prophylactic against apple trees) 98 243 12 Active substance 1 • compound of formula 11] (known) compound of formula 12 1 (known) 1 compound formula 13 1 compound of formula 14 1 compound of formula 15 compound of formula 16 compound of formula 17 compound of formula 18 compound of formula 19 compound of formula 20 compound of formula 21 compound of formula 22 compound of formula 23 % with an active substance concentration of 0.00062% 16 66 0 0 0 6 2 1 7 1 0 0 2 Example II. Phyitopbthora test, preventive on tomato plants Solvent: 4.7 parts by weight of acetone Emulsifier: 0.3 parts by weight of polyglycol alkyl ether Water: 95 parts by weight Active substances in the amount necessary to obtain the desired concentration in the liquid to When spraying, mix with the amount of solvent specified above and the concentrate diluted with the amount of water specified above, containing the additives mentioned. The resulting spray liquor is sprayed until growing on young tomato plants at the 2 to 4 leaf stage and kept in a greenhouse at a temperature of 20 ° C. and a relative humidity of 70%. After 24 hours, the plants are blighted by the aqueous suspension of Phytophthora infestans, placed in a humid chamber with a relative air humidity of 40 45 50 100%, at a temperature of 18-20 ° C, and after 5 days the degree of attack of the plants is determined. The values obtained are converted into the percentage of attack, where 0% means no attack and 100% means complete attack of the plants. The active substances, their concentrations and the test results are given in the following Table II. Tab 1 ica II Test with Phytophthora (prophylactically on tomato plants) Active substance Compound of formula 11 (known compound of formula 12 (known) compound of formula 14 Compound of Formula 15 Compound of Formula 118 Compound of Formula 20 Compound of Formula 21 Compound of Formula 22 Compound of Formula 24 Compound of Formula 23 Degree of involvement in% of active substance concentration 0.00156% 91 27 16 22 17 14 4 Example III. Test of mycelium growth. Nutrient used - composition in parts by weight: parts of agar 200 parts of potato decoction parts of malt dextrose parts of peptone 2 parts of sodium dihydrogenphosphate 0.3 parts of calcium nitrate Ratio of the mixture of solvents to the quantity of nutrient: 2 parts by weight of the solvent mixture 100 parts by weight of nutrient agar The composition of the solvent mixture in parts by weight; 0.19 parts of diwiumeAyOofoo ^ iiaanidti or acetone 0.01 parts of emulsifier (polyalkylaryl ether) 1.80 parts of water 2 parts by weight of a mixture of solvents The active substances in the amount necessary to obtain the desired concentration of this substance in the culture medium are mixed with with the amount of solvent mixture given above, then the concentrate is thoroughly mixed in the above-mentioned ratio with liquid broth cooled to 42 ° C and poured into 9 cm diameter petri dishes. Control plates are also prepared without the addition of active ingredient. After cooling and solidifying, the media is inoculated with the types of fungi given in Table 3 and incubated at a temperature of about 21 ° C .; Evaluations were made depending on the growth rate of the fungi after 4-10 days, comparing the development of mycelium in the radial direction on the medium containing the test compounds with the growth of the mycelium on the medium in the controls. The results are expressed by the following indicators: 14 1 means no growth of the fungus up to 3 means a strong inhibition of growth up to 5 means an average inhibition of growth up to 7 means a slight inhibition of growth 9 means the condition as in the control sample. The active substances, their concentrations and results are given in Table III.T ab 1 and c a. III Mycelium growth test Concentration of active substance 10 ppm Active substance compound of formula 25 (known) compound of formula 26 (known) compound of formula 13 compound of formula 27 compound of formula 14 compound of formula 28 compound J 1 of formula 15 compound of formula 17 compound of formula 18 compound of formula 29 compound of formula 30 compound of formula 31 compound and formula 32 compound of formula 33 compound of formula 34 compound of formula 35 compound of formula 36 compound of formula 37 compound of formula 38 compound of formula 19 compound of formula 23 compound of formula 39 Test fungi Fusarium culmorum - 1 1 1 3 2 1 ... 1. 1 1 1 1 '1 1 1. 1 1 j 1 1 1 - • 1 Fusarium nivale 1 1 1 3 2 1 1 1 2 3 ¦1 1 3 1 1 1 3 .5. 2 Cochlio- bulus miyabe- anus 2 3 2 2 1 3 1 1 1 1 1 l 1 1 3 3 1 j Botrytis I cinerea 9 1 - 1 3 2 3 3 1 1 2 1 1 2 o Verti- j cillium oratrum 9 3 1 '3 1 1 1 1 3 -. 1 3 3 - - 1 3 Thialop- hora cinerescens 9 - 1 1 2 1 1 2 - - 1 j 1 Phytophthora cactorum - 2 - 1 and 3 1 3 I 1 1 1 3 1 1 1 "- - - 1 1 ] • "- I15 Example IV. Seed dressing test (wheat stone burn (fungal seed disease). In order to obtain a suitable dry dressing agent, the active ingredient is diluted with a mixture of equal parts by weight of talc and silica to obtain a finely powdered mixture of the desired active ingredient concentration. wheat is infected with 5 g of Tilletia caries chlamide spores per kg of seed. For dressing, the seed with dressing is shaken out in a sealed glass bottle, then placed on moist soil, covered with a layer of humus and 2 cm of soil with a compound It is kept in a refrigerator at 10 ° C for 10 days, in the direction most suitable for germination of the embryos. Then, using a microscope, the germination of spores on wheat grains is determined, each of which is attacked by about 100 000 spores. An active ingredient is more effective, the fewer spores that germinate. The nutrients, their concentration in the mortar, the amount of the mortar used and the number of sprouted spores in percentages are given in Table IV. Table IV Seed dressing test (wheat dying) 98 243 16 Example V. Limit concentration test (soil-living insects) Test insect: Tenebrio molitor - larvae in the bed Solvent: 3 parts by weight of acetone Emulsifier: 1 part by weight of polyglycol alkylaryl ether To obtain a preferred preparation of the active ingredient, 1 part by weight of the active ingredient is mixed with the amount of solvent indicated above ^ adds the specified amount of emulsifier and dilutes the concentrate with water to the desired concentration. The resulting preparation of the active substance is thoroughly mixed with the soil, but the concentration of the active substance in the preparation plays practically no role, because only the amount of active substance per unit of soil volume, expressed in ppm (mg / liter), is decisive. This soil fills the pots and leaves them at room temperature. After a drunken 24 hours, the test insects are introduced into the soil, and after a further 2 to 7 days, the degree of action of the active ingredient is determined by calculating the small and living insects. The degree of action is 100% when all insects are killed, and it is 0% when the number of insects remaining alive is the same as in the non-active compound test. Active substances, their amounts and obtained the results are given in Table V.] Active substance 1 No treatment 1 compound 1 of formula 11 I (known) 1 compound 1 of formula 12 j (known)] compound 1 of formula 34 1 compound 1 of formula 35 1 compound 1 of formula 40 1 compound of formula 41 1 compound of formula 14 | Compound Formula 42 Concentration of the active ingredient in the stabilizing agent in a weight ratio of ¦26 Amount of the stabilizing agent in g / kg of seed. t 1 1 1 1 iiiiii Seed germination ¬ników w! ° / o 10 0.5 10 0.05 0.05 0.0 0.0 0.0 0.05 0.05 0.05 40 45 50 65 Table V Insects living in the ground - Tenebrio molitor- larvae in the ground, Active substance, compound of formula 11 (known) compound of formula 12 (known) compound of formula 43, compound of formula 33, compound of formula 13, compound of formula 44, Active substance concentration in ppm Mortality rate in * / • 0 . 0 1 100 100 100 100 The following Examples VI and VII show the inhibitory effect of the compositions according to the invention on the development of arthropods, the range of action of the active compounds being tested is not limited to that stated in the tests. In these trials, the morphological changes in the overall development of the test animals were assessed, such as half-fledged animals, incompletely hatched larvae or caterpillars, damaged wings, semi-vascular epithelium in mature insects, and death. The sum of morphological distortions and mortality during the developmental process are determined as a percentage of the number of animals tested. Example VI * Growth inhibition (zeroing test) .98 17 Test animals: Plutella maculipennis (caterpillars, 4th stage) 20 Phadon cochleariae (larvae ) pieces Food plants: cabbage plants (Brassica oleracea) Solvent: 10 parts by weight of acetone Emulsifier: 2.5 parts by weight of polyglycol alkylaryl ether. 2 parts by weight of the active ingredient are mixed with the given ingredient to make a beneficial preparation of the active ingredient. more solvent, emulsifier and enough water to give a 1% mixture which is diluted to the desired concentration. The test animals feed on the leaves of the food plant, which are sprayed evenly with the mixture of the active substance of the given concentration, the test being carried out until the insects are fully developed. In the comparative test, leaves treated only with solvent and emulsifier were used as food. The results are given in Table VI. Table VI. Growth inhibitory effect (zero test) Active substance: compound of formula 45 (known) compound of formula 22, compound of formula 46, compound of formula 47 Inhibition of growth Test animals and concentration of active substance Plutella 0.01% 0 100 100 100 Phaedon 0.01 * / r 40 70 60 Example VII. Growth-inhibiting effect (Laphygma testing) Test animals: Laphygma exigua (caterpillars) Food: 3 cm diameter and 1 cm thick discs made of air-dried artificial bean grist, yeast, vitamin mixture, leaf powder, agar and Preservative Solvent: 10 parts by weight of acetone Emulsifier: 2.5 parts by weight of polyglycol alkylaryl ether. To obtain a preferred formulation of the active ingredient, 2 parts by weight of the active ingredient are mixed with the above-mentioned amount of solvent, emulsifier and added enough water to make a 1% mixture which is diluted with water to the desired concentration. One of the test animals is placed on a food disc moistened with 1.2 ml of the solution of the active substance of the given concentration and watched until the insect hatch. In the control test, one caterpillar is placed on a food disc moistened with 1.2 ml of a suitable concentration of solvent and emulsifier solution and observed until the hatching of a mature insect. The results are given in Table VII. 18 Table VII Growth inhibitory effect (test with Laphygma). Tested animal: Laphygma Active substance - compound of formula 45 (known) compound of formula 22 Growth inhibition in ° / t at the active substance concentration 0.1% '"40 100 o, oi »/ I | 60 The following examples explain the preparation of the active ingredient according to the invention. Example VIII (process variant (a)). For a solution of 98.1 g (0.66 mole) of 3j4-dichlorothiophenol and 57.6 g (0.66 mol) of triethylamine in 500 ml of ethanol were added dropwise 130.5 g (0.66 mol) of 2-gate-5-trifluoromethyl-1,3,4-thiadiazole. The mixture is kept under boiling for 2 hours, stirring under a gold cooler, and then concentrated to a half volume under reduced pressure, poured into 1 liter of ice-cold water, drained off the white-colored precipitate, dried over phosphorus pentoxide and crystallized with about 300 ml of petroleum ether. 147 g (7% of theory) of 2- (3 ', 4'-dichlorophenes) are obtained lotio) -5-trifluoromethyl-1,3,4-thiadiazole of formula 48; - The product melts at 46 ° C. The starting compounds are prepared as follows: a) In a solution 84 cooled to 5 ° C, 5 g (0.5 mol) of 2-amino-5-trifluoromethyl--1,3,4-thiadiazole in a mixture of 400 ml of 48% hydrogen and 100 ml of water are added dropwise with stirring during 1.5 1 hour a solution of 69 g (1.0 mol) of sodium nitrite in 150 ml of water, then stirred at 25 ° C (and for 1 hour) until the evolution of nitrous gases and nitrogen ceased. The product, which is separated in the form of a thick dark brown liquid, is extracted from the reaction mixture several times with methylene chloride in a total amount of 500 ml, then the extract is rinsed with 2 percent of 100 ml of water, dried over sodium sulphate, carefully distills off the solvent and under reduced pressure fralaonteje using a short column. 101 g (87% of theory) of 2-bromo-5-trifluoromethyl-1,3,4-thiadiazole of the formula 49 55, b.p. 55 [deg.] C. / 10 mm Hg, are obtained. b) To a mixture of 400 g of ice and 60 ml of concentrated sulfuric acid is added dropwise with stirring at 0 ° C. for 30 minutes. 37.5 g (0.15 mol) 3,4-dichlorobenzene sulfchloride. Then, 54.5 g (0.84 gram atom) of zinc in the form of a dust are added and the mixture is stirred for 1 hour at room temperature and for 6 hours under reflux, after which the thiophenol is distilled off from water vapor. , extracted with chloroform and pre-styled under reduced pressure. The yield is 13.1 g (47% of theory) of 3,4-dichlorothiophenol of the formula 50. The product has a boiling point of 114-115 ° C / 0.08 mm Hg. Example IX. (variant (a) of the oxidation process), 22.6 g (0.223 moles) of thriethylamine, 25 g (0.223 moles) of 2-mercaptopyrimidine and 52.2 g (0.223 moles) of 2-bromo-5-trifluoromethyl-1, The 3,4-thiazole is mixed with 250 ml of tetrahydrofuran, boiling the mixture under reflux for 3 hours, then concentrating to half its volume under reduced pressure and poured into 500 ml of ice water. The precipitate formed is filtered off, dried and recrystallized from petroleum ether with ethyl acetate (3: 1) to give 44.1 g (75% of theory) of 2-pyrimidyl- (2) -thio-5-trifluoromethyl-1. 3,4-thiadiazone, melting at 102 ° C. 31.9 g (0.121 mol) of the product obtained is mixed with 30 ml of water and chlorine is slowly introduced into the suspension at 0 ° -5 ° C until it is saturated. whereby a precipitate is formed. After 2 hours, enough potassium carbonate solution was added to the 0 ° C mixture to obtain a pH value of 8 (then the mixture was extracted with chloroform, evaporated and the residue recrystallized from ethyl acetate to give 17.4 g (51%). theoretical yield of (2-pyrimidyl- - (2) -aiqnyl-5-trifluoromethyl-1,3,4-thiad: azoleU of formula 51 and melting point 184 ° C. Example X (variant (a) of the process with oxidation 3.5 g (0.031 mol) 3,5-dimethylthiophenol, 6.2 g (0.061 mol) triethylamine and 14.3 g (0.061 mol) 2-b "romo-5-1y6 µl" oromethyl-1,3, The 4-thiadiazole in 150 ml of tetrahydrofuran is stirred under reflux for minutes. The separated salt (by-product) is filtered off and washed thoroughly with tetrahydrofuran. The solvent is distilled from the filter under reduced pressure and the residue is distilled to give colorless oily product 16.8 g (96% of theory) of 2- / 3 ', S, dimethylphenylthio is obtained. S-trifluoromethyl-and -thiadiazole, boiling point 107-108 ° C / 0.2 mm Hg. 22.8 g (0.201 mol) of 30% hydrogen peroxide in 100 ml of glacial acetic acid are added to the product obtained, and the mixture is stirred for 15 hours at 0 ° C. The reaction mixture was poured into ice-cold water, the precipitate was filtered off and recrystallized from ethanol to give 12.7 g (54% of theory) of 2- (8 ', 5'-divumety (Lophenylysullonyl) »5-trifluoromethyl-1 3T4-thiadiazole of the formula 18, melting at 110 ° C. Example 11 (process variant (b)) Mixing 18.6 g (0.1 mole) of 2-imercapto-5 * tr6 luonoime Tylyl-1,3,4-thiadiazole and 5.6 g (0.1 mole) of powdered potassium hydroxide in 100 ml of absolute dimethylformimide are stirred for minutes, then 20.8 g of ( 0.1 mole) of 2-broimino-5-niitrothiophene and stirred at 50 ° C. for 3 hours, then diluted with water, extracted with methylene chloride, dried over sodium sulfate and evaporated. under reduced pressure to obtain 24.4 g of crude product, boiling point 160 ° -10 ° C / 0.3 mm of Hg. The crude product is recrystallized from hexane with ethyl acetate (10: 1) and then from ether / ether. petroleum (4: 3), yielding 17.3 g (55% of theory) of pure 2- {5'-nitrosthiophen-2'-ylthio) -5-trifluoromethyl-1,3,4-thiadiazole of the formula 52 melting at 57 ° C. The starting compound is prepared as follows: 699 g (3 moles) of 2-ibromo-5-trifluoromethyl-1,3,4-thiadiazole and 248 g (3.3 moles) of thiourea and in a mixture of 600 ml of ethanol and 75 ml of water, the mixture is boiled under reflux for 2 hours, and then a solution of 223 g of potassium hydroxide in 2 liters of water is added dropwise to the still hot reaction solution and kept under reflux again. reflux cooler within 5 minutes. The solution is then cooled, adjusted to its pH value with dilute hydrochloric acid and repeatedly extracted with methylene chloride. The extract is dried, evaporated and the residue dissolved in a little petroleum ether. A further portion of the product is obtained from the mother liquor. The yield is 330 g (59% of theory) of 2-mercapto-5-trifluoromethyl-1,3,4-thiadiazoL of the formula 53, melting at 73 ° C. (variant (b) of the oxidation process). 9.3 g (0.05 mol) of 2-mercapto-5-trifluoromethyl-1,3,4-thiadiazole, 5.1 g (0.05 mol) of triethylamine and 8.1 g (0.05 moles) of o-Clorobenzyl chloride are stirred in 80 ml of absolute ethanol under nitrogen at 50 ° for 2 hours, then poured over ice, filtered off the precipitate and purified by low-temperature crystallization from petroleum ether. There are obtained 10 g (64% of theory) of 2 (o-chlorobenzyl-thio) -5-ft, horn-fluoromethyl-1,3,4-thiadiazole, mp 36-37 ° C. A solution of 9.8 g (0.048 mol) of 85% m-chloroperbenzoic acid in 85 ml of methylene chloride is added dropwise to 5 g (0.016 mol) of this compound in 10 ml of methylene chloride, and the mixture is stirred and refluxed under reflux. for 4.5 hours, then he treated successively with a solution of 6.4 g of sodium sulphite in a little amount of water and then with a solution of 2.7 g of sodium carbonate in a little amount of water and vigorously stirred for 15 minutes. The organic phase is evaporated and the residue is recrystallized from cyclohexane with ethyl acetate to give colorless crystals. 4.8 g (87% of theory) of 5o 2- (o-chloix) ienzylsulfonyl) -5-trifkioramethyl--1.3 are obtained. 4-thiadiazole of formula 54, melting at 103 ° C. Example Xiii. (process variant (c)). 75.6 g (0.6 mole) of sodium sulphite, pure for analysis, are dissolved in 300 ml of water in a beaker and pre-heated to 60-70 ° C, then added dropwise with stirring with a magnetic stirrer. 122.8 g (0.5 mole) of 3,5-dichlorobenzenesulfchloride and a solution of 40 g (1 mole) of sodium hydroxide in 200 ml of water using 2 dropping funnels such that the pH value of the reaction solution is measured by an electrode immersed in the solution , it grows constantly 7-9. A saturated solution containing 3,5-dichlorobenzene • tsulfinate salt (about 600 ml) is diluted with 1.8 liters of dimethylformimide and after adding 116.5 g (0.5 mol) of 2-tromo-5-trifluoromethyl-1, The 3,4-tliadiazol is stirred at 50 ° C. for 15 hours. The sulfone is completely destroyed by the addition of ice water, and after recrystallization from ethanol, 121 g (70% theoretical) of 2V3 ', 5'-dichlorophenylsq (foinyl) -5- t63fluoromethyl-1,3,4 are obtained. -thiadiazole of formula 38, melting at 1230 ° C. The starting sulfochloride is prepared as follows: 40.5 g (0.25 mol) of 3,5-dichloroaniline are dissolved in a mixture of 110 ml of glacial acetic acid and 135 ml of concentrated hydrochloric acid and a solution of 17.7 g (0.256 mol) of sodium nitrite in 35 ml of water is added to the obtained solution, while stirring, at a temperature of 0 ° "- 5 ° C below the surface, so that no nitrous gases are present. At the same time, a saturated solution of sulfur dioxide is prepared in 140 ml of glacial acetic acid and, together with 4 g of cuprous chloride, is placed in a 2-liter dropping funnel. The doubled solution is poured in portions (foaming!) And, after the evolution of nitrogen has ceased, diluted with 500 ml of ice water, then extracted twice methylene chloride, filter extract, dried over sodium sulphate, cool and distillate the sulphochloride under reduced pressure. 49.2 g (80% of theory) of 3,5-dichlorobenzene sulphchloride of formula 55, boiling point 83-84 ° C is obtained. / 0.1 mm Hg. Compounds of formula 1, listed in Table VIII, are prepared by methods analogous to those described in Examples VIII-XIII. Table VIII Compound code number 7 8 9 11 12 13 14 16 17 18 19 21 22 23 24 26 27 28 R pattern 56 pattern 57 pattern 58 pattern 59 pattern 60 pattern 61 pattern 62 pattern 63 pattern 64 pattern 65 pattern 66 pattern 67 pattern 68 pattern 69 • pattern 70 pattern 71 pattern 72 pattern 73 pattern 74 pattern 75 -CHaCOOH pattern 76 n 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 o The melting or boiling point of the product at ° C 102 92 49-50 139 133 190 137 135 91 188 88 135 210 92 140 107 119— 123 110 107 147 115 68 243 22 I Code number 1 union 29 I 31 I 32 33 34 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60 61 62 63 64 65 66 67 68 69 70 71 72 73 74 75 76 77 78 79 80 81 82 R pattern 77 pattern 78 pattern 79 pattern 80 pattern 81 pattern 82 pattern 83 pattern 84 pattern 85 -CS-N (CH) a) 8 pattern 86 pattern 87 pattern 88 pattern 89 pattern 90 -CH2CH2C4F9 pattern 91 pattern 92 pattern 93 pattern 94 pattern 95 -CH (C6H5 ^ pattern 96 -CN pattern 79 pattern 97 pattern 97 pattern 98 pattern 99 pattern 79 pattern 78 pattern 80 pattern 82 pattern 100 pattern, 101 pattern 102 pattern 103 pattern 104 pattern 105 pattern 106 pattern 81 pattern 107 pattern 108 pattern 109 pattern 110 pattern 111 pattern 112 pattern 113 pattern 114 -CH2OH2C4F9 pattern 94 pattern 95 pattern 115 -CHgjCl n 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1 1 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 The melting or boiling point of the product. 1 in? C. ¦ J? 152 128 (0.2 mm Hg) 109-112 (0.4 mm Hg) 1 56 116 126 151 127 74 r — 75 140 68 92 83 113 40 120 36—37 85 135—150 (0.2 mm Hg) 1 65 75 90 38 113 86 99—100 110 106 78 136 83 1 73 185 (xl / 2 dimethylformamide) 113 77 213 73 130 65 99 100 1117 100 74 120 93 125 174 97 131 142 148 6798 243 23 = \ = / '3 j2 st. 3 Cl PATTERN 27 N — N CL FC ^ S ^ SO.S \ \ / CL PATTERN 28 N — N \ c ^ c / ^ WZdR 31 F3 C ^ S ^ S ^ S ^ NO, WZdR 29 N — NN — NXXXJ F3 C ^ S ^ S ^ S ^ WZdR 30 N — NN ^ CH3 N — N c XX? r ^ F3C ^ sS / sS-Cf | p WZdR 32 F3 C ^ S ^ ShH WZdR 33 xxxi F3 C ^ S ^ S ^ S ^ CF3 WZdR 34 WZdR 35 N — NN — N Hi r, c ^ s ^ s ^ ntn ji CH, WZdR 36 N— ^ s F3 C ^^ S ^^ SCN: WZdR 37 .CH, ^ CH- N — N k, ~ r CL F3C / kS '/ kS02- ^ 3 Cl WZdR 38 XXX rs WZdR 39 N — N. /. N — NIX iTY ^ l X II F, C ^ S ^ sA ^ k ^ F3C / "S / ^ S0." WZdR 43 WZdR 47 F3C y — y ^ n — n cf3 0 WZdR 40 3 \ - / WZdR44 N— N XX CF3 ^ S ^ S / V-CL CL WZdR 48 N — NN — N F3 C ^ S ^ S ^ S ^ WZdR 41 NHCH.N — N F3C ^ "S ^ SO02 - ^^ N02 WZdR 45 N — NN —NXX WZdR 49 N — N CF.F3C ^ S ^ S02- ^ J WZdR 42 F3cA ^ S02-fCN HS- ^ CL 2W CN WZdR 46 Cl WZdR 50N — N j | jl n CE ^ S ^ SOnf 3 N ^ WZdR 51 08 243 CL a-S02-fi Cl WZdR 55 // NV-C6H5 ~ i X WZdR 59 N — NI fi— WZdR 52 ^ CF3 / "S /" S / ^ xN02 N — NH. 1 JL ¦ N — N CFT ^ ST "SH WZdR 53 / w N- WZdR 56 O ^ / WZdR 57 N — N 1 X ^ S ^ NHCH3 WZdR 60 xU ^ S ^ Nl '^ NHCH, ca WZdR 61 N — N Cl CF3 ^ S ^ SO02 -CH- ^ J - (WZdR 54 0C2H5 r ~ ^ N WZdR 63 N -Tl \ WZdR 64 NH WZdR 65 N ^ N 't WZdR 58 N — N / C6H5 CH ^ 3 WZdR 66 WZdR 67 N — N WZdR 68 WZdR 69 ^ S- ^ N = CH-N (CH3) S WZdR 70 N — NV WZdR 71 CH3 WZdR 72 WZdR 73 ^ S02CH3 WZdR 74 H WZdR 62 N— / I CH3 WZdR 75 £ H, N- WZdR 76 N / WZdR 77 CH30 P CH30 PATTERN 7898 243 CL V \ a PATTERN 79 / CF3 PATTERN 80 H00C PATTERN 83 ¦O-N0, N02 PATTERN 84 -CS-N PATTERN 87 ^ S ^ CF; STYLE 88 Jt, NO.V CH3 CK STYLE 91 -CH2-p CL MODEL 92 CF // \ VCL MODEL 81 -CS-N ^ Js] -CH2CH20H STYLE 85 XS ^ NO STYLE 89 IM- CH (CH3) 2, N STYLE 93 -CH, - ^ CL STYLE 95 -CS-N 0 STYLE 86 N_ / CH3 V f -CH2- / VCL Cl WZCSR 90 MODEL 99 STYLE 103 Cl STYLE 94 -CH2-C0 ^ VCL CL STYLE 96 COOH hQ-OH STYLE 100 C2H50 STYLE 104 CL // ^ -CL STYLE 97 CL CL STYLE 98 N02 STYLE 101 STYLE 102 f \ CK N02 STYLE 105 C0698 EXAMPLE 10 243 CL MODEL 107 FF MODEL 111 CN MODEL 112 ^ 0 N02 MODEL 109 CN MODEL 113 SCF3 MODEL 110 WZPR 114 MODEL 115 LZG Zd No 2 - 7tio / 78 100 e £ Z. forms. A-4 Price PLN 45 PL

Claims (2)

Claim 1. A fungicide and insecticide containing an active ingredient and a solid or liquid carrier, characterized in that the active ingredient is 2-substituted 5-trifluoromethyl-i-thiadiazoles of the general formula I, in which R is a substituted alkyl radical , an anto-or meta-substituted phenyl radical, a substituted phenyl-radical, a substituted phenylalkenyl radical, an optionally substituted phenylalkenyl radical, an optionally susceptible five-α-Jbo-hexagonal heterocyclone radical containing 1-4 heteroatoms (N, S), an optionally substituted benzimidazolyl or benzothiazole M radical, an optionally substituted naphthyl radical, a quinolyl radical, a cyano group, a group of the formula 8, a group of the formula 9, wherein R 1 and R 2 together represent a tri, four or pentiomyethylene, or the group of formula 10 where X is oxygen or sulfur and R 'and R "are alkyl radicals, or together with with the volume of nitrogen and optionally further heteroatoms (0, N) form an optionally substituted ring with 6 or 7 members, and n is an integer zero, 1 or 2. N — N 11 + CF3 ^ S ^ Br N — N cfAsas ^ COOH COOH -HBr * SCHEME 1 +; HS U jr \ IX CE / ^ S ^ CL k ^ N — N -HCl SCHEME 2 ¦W — N / CK CF ^ S ^ Br N — N rH CF3ASAS ^ CH3 ^ 2 ^ 2 / 'acetic acid cf / VSo2 ^ J ^ CH3 SCHEME 3 CK -HBr nt CE ^ S ^ SH Br ^ S ^ N02 -HBr N — N • N- / kCxA «c ^ CF ^ g, ^ ^ ^ N02 SCHEME 498 243 N ~ N HS ° 2 I + CF ^ S ^ Br N — N CF3- S SO2 SUMtlVIMI 3 ZR FORMULA 6 NaOH N — N CF3- ^ S ^ S (0) nR FORMULA1 R-SO2H FORMULA 7 V2 co F3C- N — N 2 \ _ PATTERN 11 N — N 1 X CF ^ S ^ Y PATTERN 2 RS- H PATTERN 3 N — N PATTERN 4 PATTERN 8 RK? 2 PATTERN 9 Z ** -CX- <N? "PATTERN 10 N — N F3C S ^ "SO2-CH-CH2-CH2-CH3 FORMULA 12 N — N Cl F, c ^ s ^ so0-f Ya \ / FORMULA 13 N — NIX CF / ^ S ^ SH FORMULA 5a N — NH I cf / -sr - s FORMULA 5b N — N Cl F3C ^ S ^ S02- ^ J FORMULA 1498 243 N — N ^ ^ y — N F3C ^ SAS02JUJ F3C ^ S ^ SO02 - ^ - CH3 FORMULA 15 N02 FORM 19 N — N FC ^ S ^ SO . * D o ^ - »'-s * -jy ^ j * ~ s Ti ^ T3 R.CA5XS0, - / VCI n'02 r» "^ ~ 2 W WZdR16 WZ (5R 2 ° N — NN — N Cl Xan ^ / \ F.cVsq, -CO ^ "^ Pattern 17 Cl Pattern 21 fl ^ PH3 NN f3c ^ VSo2- F cJ ^ sa-CH-CH-O CK N — N Cl WZdRB" 'JF ^ Ao-fYa WZ < 3R22 3 FORMULA 23 N — NN — NI '1 U 1 F3 C- ^ S ^ S ^ S ^ SCH, FORMULA 24 N — N F3C ^ S ^ S02 - ^ = yCl FORMULA 25 N — N F3C ^ S ^ SG ^ - ^ - NHCOCH, MODEL 2698 243 FrArSo2-fCL FC ^ SASASASO.-CH. F3cA ^ S ^ S ^ N02 JOL - N — NN — N * PL