PL122648B1 - Insecticide for hymenoptera control - Google Patents

Description

The subject of the invention is an agent against hymenopteran insects, containing as an active ingredient isothiourea derivatives of formula 1, in which R and Rx independently represent a C2-C10alkyl radical, preferably C5-C9alkyl, and especially C6-C8alkyl, a C2-C10alkoxyalkyl radical, preferably C5 -C9alkoxyalkyl, especially C6-C8alkoxyalkyl or phenyl radical, wherein R and R1 contain a total of 12 to 22 carbon atoms; R2 is a Cx-C14alkyl radical, preferably a C1-C6alkyl radical, especially a C1-(^alkyl radical, a C3-C10alkenyl radical, preferably a C3-C5+ alkenyl radical, a C3-C4alkynyl radical, a G2-C4 hydroxyalkyl radical, preferably C2 -C3-hydroxyalkyl, C2-C6alkylthioalkyl radical, preferably C2-C4alkylthioalkyl, C2-C6alkoxyalkyl radical, preferably C2-C4alkoxyalkyl, radical of the formula (CH2)nX (CH2)n)y3 in which n is 1 or 2, X means an oxygen or sulfur atom, and y means the number 1-4, preferably 1-2, or R2 means a radical with the formula -(CH2)nCOH, in which n means the number 1-10, preferably 1-5, and especially 1-3, or R2 is a phenyl radical or a phenethyl radical; and R3 is a carbalkoxyalkyl radical in which the alkyl moiety is a Cx-C4alkyl radical, preferably C1-C2alkyl, an alkylcarbonylalyl radical in which the alkyl moiety is a C1-C4alkyl radical, preferably C1-C2alkyl, a hydroxyalkenyl radical, in which the alkenyl moiety is a C3-C4alkenyl radical, a hydroxyalkyl radical in which the alkyl moiety is a C1-C6alkyl radical, preferably C1-C4kyl, especially Cx-C3alkyl, a formyl-hydroxymethyl radical, a hydroxyhaloethyl radical in which the halogen atom is chlorine, bromine or iodine, preferably chlorine or bromine, especially chlorine, a substituted phenoxyalkyl radical, in which the alkyl moiety is a C1-C2-kyl radical, preferably (^alkyl, and the substituents are p-methoxy, NO2 or CN or a chlorine atom; a radical of the formula 2, in which R1 is a -OH, -NH3 or Cj-C4 alkoxy group, preferably a methoxy group, a radical of the formula -CHOHCHOHNRCSRa(=NR1), in which R, Rx and R2 have the meanings given above, a group of the formula 3, in which R, R6 and R2 have the above-mentioned meanings, a group of the formula -P03 -B, -P (OH;Oa -B or -S03 -B, in which B is a basic cation, preferably a basic organic cation, especially a basic organic cation with the formula (CH3)3NH or formula 4, a group with the formula -CONR4Ri, in which R4 is -H, the radical Q-C22alkyl, preferably Cx-C12 alkyl, especially C± -C8alkyl, and especially Cx-C6alkyl, hydroxyethyl, naphthyl, phenyl, substituted phenyl radicals, the substituents of which are halogen atoms, preferably chlorine, C1-C5alkyl radical, preferably Cx-C2alkyl, C1-C5alkoxy group, preferably Ct- (^alkoxy, nitro, cyano or -CF3; a radical of the formula 5 in which R, Rx and R2 have the meanings given above, a radical of the formula - (CHa^NHCONRC (SR^)=NR*, 10 15 20 25 122 648122 648 3 wherein R, R4 and R2 has the meanings given above, the radical of the formula 6, 7, 8, 9, 10, 11 or 12, in which formulas R, Rx and R2 have the meanings given above, x is the number 1 to 8 and m is the number 2 or 3, a radical of formula 13, in which X is an oxygen or sulfur atom, an NU group or an NRlt group, Y is a hydrogen atom or a methyl radical, and R10 is a hydrogen atom, a C1-C18alkyl radical, preferably Ct-Cg*!- kelic, especially Cx-C2alkyl, C3-C4alkenyl radical, C3-C4alkynyl radical, C2-C6haloalkyl radical, preferably C2-G3haloalkyl radical, C3-C8cycloalkyl radical, C1-C6polycycloalkyl radical, radical C2-C16polyalkoxyalkyl, C2-Cfthydroxyalkyl radical, C3-C10alkoxy-kylkyl radical, -radical;C3-C8carboalkoxyalkyl radical, C4-C8cycloalkyl alkyl radical, C4-C8alkylcylalkyl radical, preferably C6-C8alkylcycloalkyl radical, k C4-C7cycloalkylimino , C2-C10alkyl imino radical, Cx-C3alkylamino radical, C4-C12dialkylaminoalkyl radical, C6-C10cycloalkenyl radical, phenyl radical, alkylphenyl radical in which the alkyl moiety is Cj-C4alkyl radical, parachloroalkylfeuyl radical in which the alkyl moiety is is a C1-(^alkyl radical, a naphthyl radical, an anthracenyl radical, a benzamidocycloalkyl radical, in which the alkyl moiety is a C1-C2alkyl radical, a pyranylmethyl radical, a tetrahydrofurfuryl radical, a thiophenemethyl radical, a benzhydryl radical, a halobenzhydryl radical, a polycyclic alcohol radical, and a substituted a phenyl radical whose substituents are a G1-C4alkyl radical, a halogen atom, a nitro group, a trifluoromethyl radical, a formyl group, a chloroacetyl group or a Cx-C4alkoxy group, a hydrogen atom, a benzyl, chlorobenzyl, phenethyl or substituted phenethyl radical, wherein the substituents are a C1-C4alkyl radical or a halogen atom; Rn is a Cx-C4alkyl, C3-C6alkoxyalkyl or C3-C4aikenyl radical; or R10 and Rn together constitute a heterocyclic radical, preferably an azepinyl, morpholinyl, piperidinyl or piperidinyl radical substituted with a C1-G3-alkyl radical; Y represents a hydrogen atom or a methyl radical, provided that when X represents an oxygen or sulfur atom, R10 is different from hydrogen; and a substituted phenyl radical in which the substituents are a halogen atom, a Cx-C4alkoxy, phenoxy, trifluoromethyl, C1-C6thioalkyl, nitro, isocyanate or C2-C4polyalkoxy group or a C3-C7-cycloalkyl or C3-C24carboalkoxyalkyl radical, preferably C3—G10carboalkoxyalkyl, CA—C8- haloalkyl radical, preferably C±—C4haloalkyl, C3—C12alkenyl radical, preferably C3—C4-alkenyl, C2—C6dialkylamino or phenylamino group, C±—G24 alkyl radical, preferably Cx— C4-alkyl radical, C3-C12hydroxyalkylamidoalkyl radical, C5-C10N3N-hydroxyalkylureidoalkyl radical, isocyanatoalkyl radical in which the alkyl moiety is C1-C5alkyl radical, C3-C12-alkylamidoalkyl radical, polyalkoxyamidoalkyl radical in which the polyalkoxy moiety is 3—6 repeating C2-C3alkoxy units, and the amidoalkyl fragment contains 4-12 carbon atoms, the **-SO2Cl group, the -SO2polyalkoxyamidoalkyl group, in which the polyalkoxy part contains 3-6 repeating C2-C3alkoxy units , and the amidoalkyl fragment contains 4-12 carbon atoms; R5 represents a hydrogen atom, a C1-C4alkyl, C3-C6alkoxyalkyl, C3-C4alkenyl, hydroxyethyl or phenyl radical; or R4 and R5 together constitute a heterocyclic radical, preferably an azepinyl, morpholinyl, piperidinyl or piperidinyl radical substituted with a Cx-C3 radical. lkyl; a group with the formula -COXnR6, where ¬ phenyl, where when n = 1, the substituents are the nitro group, the chlorine atom, the Gt-C2alkyl radical, ! 5 C4-C6 polyalkoxyalkyl, C3-C8 cycloalkyl, C3-C4alkenyl, C3-C6aLkoxyalkyl, C2-C6hydroxyalkyl, Cj-C3carboxyalkyl or C5-C8-trialkylammonium salts, and when n = 0, the substituents are chlorine atom, thiopotassium group , C1-C8alkyl radical, preferably C1-C12alkyl, especially C1-C4alkyl, benzyl radical, Cx-C2heteroalkyl, C2-C4chlorocarboxyalkyl, C4-C6polyalkoxyalkyl or acetyl; a group with the formula -COR7COYdZ, in which R? means the group — (CH2—)n, where n = 0—8, the group —CH= CH—, the group of formula 14, in which M is hydrogen or chlorine, the radical of formula 15, the group —CCI= CCI—, —CH2OCH2— or —OCH2 CH20—, and d is the number 0 or 1, and when d = 1, then Y is an oxygen or sulfur atom or the —NH group, Z is the radical CL—C16alkyl, preferably C±—C12alkyl, and especially Cx-C4alkyl, hydrogen atom, C4-C16polyalkoxyalkyl, C4-C8dialkylaminoalkyl, C3-C5alkynyl, phenyl, or substituted phenyl radical or organic or inorganic salts, and when d = 0, Z is a chlorine atom or group -NRC(SR2)=NR, where R, Rx and R2 have the meanings given above; group -PO(R8)2, where R8 is a Q-C10alkoxy radical, preferably C1-Csalkoxy, an amino group, a CL-C10alkoxyamino group, preferably a Ct-C5alkoxyamino group, a hydroxyl group and an organic base; a group with the formula -SOwR9, in which w = 0-2, and R9 is an amino group, C1-C10alkyl radical, preferably Ct-C5alkyl, Cx-C4haloalkyl radical, phenyl radical, CL-C10dialkylamino group, Ct-C10alkylamino group , C1-C10alkoxy, preferably Cx-C5alkoxy or a substituted phenyl radical whose substituents are a nitro group, a chlorine atom, a Cx-C4 radical or a methoxy group. ;o In the patent description St. United No. 3,969,511 and No. 4,062,892 disclose isothiurium compounds of the formula I, which are active against hymenopteran insects, in which R3 (or Rz) is hydrogen. The disadvantage of these compounds is their high phytotoxicity, therefore, although they protect crops against hymenopteran insects, they are harmful to the crops themselves. It has been found that replacing the active hydrogen in this type of isothiuronium and urea compounds with certain specific, relatively easily cleavable groups can reduce or eliminate the phytotoxic effect of the parent compound, while maintaining and, in some cases, increasing the activity against hymenoptera. . The preparation of isothioureas with an active hydrogen atom is well known. They are obtained by treating the isothiocyanate with a primary amine and the resulting thiourea with an alkyl halide. The reaction product is thiourea salt. An inert solvent may be used in both reaction steps. To accelerate both reactions, they are carried out at elevated temperatures. The course of the reaction for the preparation of isothiourea salts is presented in Scheme 1. The compounds constituting the active ingredient of the agent according to the invention are prepared by acting on the isothiourea base with isocyanate or acid chloride. The free base may be prepared by neutralizing the isothiourea salt with a cold aqueous solution of the base, such as dilute sodium hydroxide solution, extracting the free isothiourea with a water-insoluble solvent such as hexane, benzene, toluene, etc., drying over a dehydrating agent such as magnesium sulfate, filtration and evaporation under reduced pressure. In an alternative method, the isothiourea salt is dissolved in an inert solvent such as benzene or toluene, an equimolar amount of isocyanate and an equivalent amount of soluble tertiary base or acid chloride and two equivalents of soluble tertiary base are added. such as triethylamine, and the reaction is completed by stirring for several hours at room temperature or refluxing for a shorter time. A variation of the method using a base, such as triethylamine, is the treatment of the thiourea salt in a solvent. , such as benzene, in which triethylamine hydrohalide is almost completely insoluble, filtering off the triethylamine hydrohalide and treating the filtrate with isocyanate or acid chloride, completing the reaction as above. Solvents suitable for the condensation of isourea with isocyanate or acid chloride are solvents not reacting with any of the reagents. These include hexane, benzene, toluene, tetrahydrofuran, dioxane, methylene chloride, diethyl ether and the like. Depending on the reagents used, the reactions are carried out at -20 to 80°C for 0.5 to 24 hours. It has been found that in some cases the condensation of isothiourea with an isocyanate or an acid chloride can be accelerated by adding a catalyst such as triethylamine or dibutyltin dilaurate. The above-discussed reactions of thiourea base with isocyanate, isothiourea salt with base and isothiourea base with acid chloride are presented in Schemes 2, 3 and 4, respectively. Prior art isothiourea precursors can be obtained by the methods disclosed in United States Patent Nos. 3,969,511 and 4,062,892. The agents of the invention are useful in combating Hymenoptera (Lepidoptera) when used in effective amounts in their environment or in food. Some of the compounds constituting the active substance of the present invention also have phytotoxic activity, which makes them useful as herbicides and hymenoptera insecticides if combination of these activities is desired. Moreover, some of these compounds have fungicidal activity. By "an amount effective against hymenoptera" is meant an amount of an active compound which, when administered by any conventional method to the environment of these insects, to their food or to the insects themselves, will "control" them , killing or significantly damaging a significant part of them. The discussed compounds are useful in protecting food products, fibrous and feed crops, and ornamental plants against insects and larvae of the lepidopteran order. Examples of plants that can be protected by means of the invention are trees such as oak and pine, fruit trees such as peach, apple and walnut, vegetables such as tomatoes, other crops such as tobacco, cotton, lettuce, cabbage, corn and rice and any other plants constituting the food of hymenoptera. New compounds constituting the active ingredient of the agents 20 according to the invention can be prepared from the above precursors by the methods presented in the examples below. Example I. 1,3-diheptyl-2-ethyl-3-(0.0 -di-methylphosphorus)isothiourea. 25 To a 500 ml three-necked flask equipped with a stirrer, thermometer and dropping funnel, 6.0 g (0.02 mol) of 1,3-diheptyl-2-ethylisothiourea and 200 ml of methylene chloride were added. With stirring, the solution was cooled to 0°C and 2.0 g (0.02 mole) of triethylamine was added, followed by 3.0 g (0.02 mole) of phosphorus oxychloride dissolved in 25 ml of methylene chloride, with at such a rate to maintain a temperature of 0 to 5°C. After the addition was complete, the reaction mass was stirred for 30 minutes at 0°C. Then, over 15 minutes, a solution of 8.7 g (0.04 mol) of 25% sodium methylate in methanol with 25 ml of methylene chloride was added, maintaining the temperature at 0 to 5°C. The reaction mass was stirred for 30 minutes at 5 °C and then for 30 minutes at room temperature. The resulting mixture was washed with two 200 ml portions of water and the phases were separated. The methylene chloride phase was dried over anhydrous MgSO4, filtered and evaporated under reduced pressure, obtaining 7.4 g of the desired product - 1,3-diheptyl-2-ethyl-3-(0.0 - dimethylphosphorus)isothiourea with n^1, 4528. The structure of the product was confirmed by infrared (IR), proton resonance (NMR) and C13-NMR spectra. In table I the compound has the number 225. 50 Example II. 1,3- diheptyl-2-ethyl -3-N- (-4-methyl-3-(carbowax -350 -carbamyl)/phenylcarbamylisothiourea. The title compound was prepared as follows: Intermediate product a) Into a round-bottom flask of 55 volumes of 100 ml, 3.56 g (0.02 mol) of 2-methyl-5-nitrophenyl isocyanate, 7.0 g (0.02 mol) of carbowax 350, 2 drops of triethylamine, 1 drop of dilaurate were added dibutyltin and 25 ml of methylene chloride. After the exothermic reaction ceased, the solvent was stripped off under reduced pressure. The residue was dissolved in a 10:1 mixture of diethyl ether and toluene. The permanent white impurity was removed by filtration, and from the filtrate after evaporation under reduced pressure, 10.5 g of the desired compound was obtained - N-(2-methyl-5-nitrophenyl) carbamate 122 648 7 30 carbowax 350, nu 14810. The structure was confirmed by C13-NMR spectrometry. Intermediate product b) In a Parr glass pressure vessel, 7 g (0.013 mol) of intermediate product a) were dissolved in 200 ml of ethanol, 5-1 g of the palladium-on-carbon catalyst were added and the mixture was kept shaking. for 30 minutes under a hydrogen pressure of 3500 hPa. Then the reaction mass was filtered, and the filtrate was evaporated under reduced pressure, obtaining 6.0 g of the desired compound 10 - carbamate N-(2-methyl-5-aminophenyl)carbowax 350. The structure was confirmed by C13-NMR spectrometry. Intermediate product c ) In a three-necked flask with a capacity of 250 ml, equipped with condensers, stirrer L5 and gas supply tube, 5.8 g (0.0116 mol) of intermediate product b) were dissolved in 200 ml of toluene. While stirring, the solution was brought to 70 °C and saturated with HC1 gas. The mixture was then brought to reflux and phosgene was bubbled through it for 30 minutes. When the reaction mass became clear, N3 was bubbled through it to remove excess phosgene. The solvent was removed under reduced pressure to obtain 6.1 g of N-(2-methyl-5-isocyanophenyl) carbamate, bowax 350, n=1.5848. The structure was confirmed by C13-NMR spectrometry. 1,3- diheptyl -2-ethyl -3-N-(4-methyl -3- (carbowax 350-carbarnyl)/phenylcarbamylisothiourea. 2.0 g (0.004 mol) was added to a 100 ml round-bottom flask. intermediate product c), 12 g (0.004 mol) of 1,3-diheptyl -2-ethylisothiourea, 2 drops of triethylamine and 15 ml of methylene chloride. After the exothermic reaction stopped, the solvent was removed under reduced pressure, obtaining 3.3 g of the desired product - 1,3-diheptyl -2- ethyl -3- N- — /4-methyl -3- (carbowax 350-carbamyl)phenylcarbamylisothiourea. The structure was confirmed by C13-NMR spectrometry. The compound has no. 212 in table J. 40 Example Ul. 1,3-Diheptyl -2-ethyl-3-/N- — (3-tergitol (15-S-7)oxycarbamylphenyl)carbamyl/isothiourea. The title compound obtained as follows: Intermediate d) As in case 45 intermediate a) in Example II, 3.28 g (0.02 mol) of 3-nitrophenyl isocyanate, 10.1 g of teigitol (15-S-7), 2 drops of triethylamine and 25 ml of methylene chloride were mixed to obtain 13.2 g of the given compound - N-(3-nitrophenyl)tergitol carbamate (15-S-7). 5Q The structure was confirmed by IR spectra. Intermediate e) In the same manner as for intermediate b) in Example II, 11.2 g (0.0166 mol) of intermediate d) were reduced with Ha in ethanol, using 1 g of 55 as a catalyst. palladium on carbon. 9.3 g of the given compound were obtained - N-(3-aminophenyl)tergitol carbamate (15-S-7). The structure was confirmed by the IR spectrum. Intermediate product f) In the same manner as in the case of intermediate c) in Example II, 9.3 g 60 (0.0145 mol) of intermediate e) were treated with an excess of HCl gas and then with an excess of phosgene, obtaining 9.4 g of the given compound - N-(3-isocyanophenyl)tergitol carbamate (15-S-7). The structure was confirmed by the IR spectrum. 1-3-diheptyl-2-ethyl- 65 8 -3-/N-(3-tergitol (15-S-7)oxycarbamylphenyl)carbamyl/isothiourea. In the same way as in the case of the title compound from Example II, with 2 g (0.003 mol) of the intermediate compound f) 0.9 g of 1,3-diheptyl-2-ethylisothiourea, 2 drops of triethylamine and 10 ml of methylene chloride, 2.9 g of the desired product were obtained - 1,3-diheptyl -2-ethyl-3 -/N-(3-tergitol (15-S-7)oxycarbamylphenyl)-carbamyl/isothiourea, nD 1.5710. The structure was confirmed by the IR spectrum. The compound has number 215 in Table I. Example IV. 1,3-diheptyl -2-ethyl -3- (0.0- diethylphosphodithioylacetyl)isothiourea, Intermediate product g) To a three-necked flask with a capacity of 500 ml, equipped with a stirrer, thermometer and addition funnel, 30 g (0.1 mol) of 1,3-diheptyl-2-ethylisothiourea, 12.4 g (0.11 mol) of chloroacetyl chloride and 250 ml of toluene. To the solution cooled in a dry ice bath to -30°C, 11.1 g (0.11 mol) of triethylamine were added with stirring over a period of 30 minutes. After the addition was completed, the reaction bowl was brought to room temperature and stirring was continued. The reaction mass was then washed successively with two 200 ml portions of water, 100 ml of saturated sodium bicarbonate solution and two 200 ml portions of water. The toluene phase was dried over anhydrous MgSO4, filtered and evaporated under reduced pressure, obtaining 36.1 g of the desired compound - 1,3-diheptyl-2-ethyl-3-chloro-acetylisothiourea. The structure was confirmed by IR and NMR spectrometry. 1,3- diheptyl -2-ethyl -3- (0,0-diethylphosphorus-dithioylacetyl) isothiourea. 2.2 g (0.012 mol) of 0,0-diethyl dithiophosphoric acid were dissolved in 25 ml of acetone and 5 g of anhydrous potassium carbonate were added. After neutralization, the acetone phase was decanted into a 250 ml vessel containing a solution of 3.0 g (0.008 mol) of intermediate g) in 75 ml of acetone. The resulting mixture was stirred for 2 hours at room temperature and then poured into 200 ml of toluene. The resulting mixture was washed with two 220 ml portions of water. The toluene phase was dried over anhydrous MgSO4, filtered and evaporated under reduced pressure, obtaining 3.6 g of the desired product - 1,3-diheptyl-2-ethyl-3-(O,0-diethylphosphoride dithioylacetyl) isothiourea, 30 nD 1.5060 . The structure was confirmed by IR and NMR spectrometry. The compound is number 255 in Table I. Example V. N,N'-diheptyl -S- ethyl N- propanesulfonylisothiourea. 1.8 g (0.018 mole) of triethylamine was added to 4.5 g (0.015 mole) of N,N'-diheptyl-S-ethyl isothiourea in 50 ml of methylene chloride in a stirred round-bottom flask. To the above solution was added dropwise, at 0°C, a solution of propanesulfonyl chloride (0.018 mol. 2.6 g) in 8 ml of methylene chloride. The mixture was stirred for 1.5 hours at room temperature and then for 1.5 hours at 30-35°C. The cooled solution was washed twice with 20 ml of water, once with 25 ml of saturated sodium bicarbonate solution and twice with 20 ml of water. The organic phase was dried over magnesium sulfate and evaporated under reduced pressure to obtain the product as a yellow oil, n. 1.4805. Yield 5.2 g (85.4% of theoretical). Struk-122 648 9 rounds confirmed by IR spectrometry. The compound has number 201 in Table I. Example VI. N,N'-diheptyl -S-ethyl -N'-p-toluenesulfonylisothiourea. The reaction was carried out with 0.018 mol (3.4 g) of p-toluenesulfonyl chloride as in Example V above. The product had a value of, for example, 1.517. Yield 6.0 g (88% of theoretical). The structure was confirmed by IR, NMR and mass spectrometry. The compound has number 204 in Table I. Example VII. 1,3-di-n-heptyl -1-trichloro-methylthio-2-ethylisothiourea. To a round-bottomed flask containing 50 ml of tetrahydrofuran, chilled in an ice bath, 3 g (0.01 mol) of 1.3 was added with stirring. -di-n-heptyl-2-ethyl- isothiourea. Then 1.4 ml (0.01 mol) of triethylamine were added and stirred for 10 minutes. 1.1 ml (0.01 mol) of trichloromethylsulphenyl chloride were added dropwise over 2 minutes. A white precipitate formed. The mixture was stirred for an hour to bring to room temperature. The resulting reaction mixture was allowed to settle overnight. The white product was filtered off and washed with two 10 ml portions of fresh tetrahydrofuran. The filtrate was evaporated under reduced pressure to obtain 4.55 g of the title product, with a yield of 101.2%. The resulting liquid had a pH of 1*5084 and was identified by IR and mass spectrometry as the title compound. The compound has number 291 in Table I. Example VIII. 1,3-di-n-heptyl -1- (2*- -fluoro-l\r-2,,2'- tetrachloroethylthio-2- ethylisothiourea. 2.0 g (0.007 mol) 1,3-di -n-heptyl-2-ethylisothiourea was dissolved in 100 ml of tetrahydrofuran and added to a round-bottomed flask placed in an ice bath. While stirring, 0.7 g (0.0069 mol) of triethylamine was added and stirring was continued for 10 minutes. within about 15 minutes, 1.68 g (0.0068 mol) of 2-fluoro-1,1,2,2-tetrachloroethylsulfenyl chloride dissolved in 20 ml of tetrahydrofuran were added. While the mixture was stirring, it precipitated for 2 hours. precipitate. The mixture was filtered, and the residue on the filter was washed with two portions of 20 ml of tetrahydrofuran. The filtrate was evaporated under reduced pressure. 3.53 g of the title product 30 were obtained in the form of a liquid with an nD of 1.5091. The identity of the product was confirmed by IR and mass spectrometry. The compound is number 292 in Table I. Example 9. 1,3-di-n-heptyl-1-o-nitrophenylthio-2-ethylisothiourea. 1*9 g (0.01 mol) of 2-nitrobenzenesulfenyl chloride was dissolved in 50 ml tetrahydrofuran. To the mixture placed in a round-bottomed glass flask set in an ice bath, 3 g (0.01 mol) of 1,3-di- n-heptyl-2-ethylisourea in 30 ml of tetrahydrofuran were added. Then, within 10 minutes, 1.05 g (0.01 mol) of triethylamine in 10 ml of tetrahydrofuran were added. A white precipitate immediately formed. With stirring, the temperature was brought to room temperature for 3 hours, then the mixture was filtered and the filtrate was evaporated under reduced pressure! to obtain a light brown, sticky residue, which was dissolved in 100 ml of diethyl ether and filtered through magnesium sulfate and Dicalite 4200. The filtrate was evaporated under reduced pressure to obtain 4.2 g of liquid with nD 1.5463. The product was identified by IR spectrometry as the title compound. 5 The compound is number 294 in Table I. Example ) S-ethyl-1,3-diheptyl-2-isothiourea and 3 g 10 (0.03 mol) ethyl acrylate. After adding a catalytic amount of base (0.1 g NaH), the mixture was heated from 25 to 85 °C and kept at this temperature for 5 hours. The reaction mixture was then cooled and 150 ml of ether were added. The ether layer was washed with 100 ml of water, dried and evaporated to give 2 g of the title product. The structure was confirmed by IR and NMR spectrometry. The compound is number 197 in Table I. Example XI. S-ethyl-1,3-diheptyl-3-(3-ketobutyl)-2-isothiourea. The procedure was the same as in Example room temperature within 4 hours. 2 g of the title product was obtained, which was identified by IR and NMR spectrometry. Connections - 25 examples of table I no. 198. Example XII. N,N-di-n- heptyl -N'-ethyl- oxalyl-S-ethylisothiourea. In a 100 ml single-necked round-bottom flask, equipped with a magnetic stirrer and a stopper, 5.0 g (16.6 mmol) of S-ethyl - 1,3-dihcptyl-2-isothiourea and 1.8 g (18.3 mmol) triethylamine in 50 ml of methylene chloride. The clear, light yellow solution was cooled to 0°C in an ice bath. 2.50 g (18.3 mmol) of oxalyl chloride were added dropwise to the cooled solution while stirring, maintaining the temperature in the range of 5 to 15° C. Within a few seconds, a large amount of white precipitate formed. Stirring was continued for an hour at 0°C. The cooling bath was then removed and stirring was continued for 3 hours at room temperature. The precipitate was dissolved by adding 50 ml of water and the mixture was transferred to a separatory funnel containing 50 ml of methylene chloride. The layers were separated and the organic phase was washed once with 10 ml of saturated NaHCOa, three times with 10 ml of water, once with 10 ml of saturated sodium chloride and dried over NaaSO4. The dried, clear, yellow organic solution was filtered through Na2SO4 and the solvent was removed under reduced pressure, obtaining 6.63 g (yield 99.7%) of the title product as a yellow oil with nD 1.4757. The product was identified by IR, NMR and mass spectrometry as the title compound. The compound has number 555 in Table I. 55 Example XIII. Bis-N'-(N,N'-n-heptyl-S-ethylisothioureyl oxalate). The procedure was the same as in Example XII, except that instead of a 100 ml round-bottomed flask, a 50-200 ml round-bottomed flask was used, and instead of ethyloxalyl chloride, 1.16 g (9.13 mmol) of oxalyl chloride was used. A clear, yellow solution was obtained, which was stirred for one hour at 0°C and then for 20 hours at room temperature. The clear, yellow solution was transferred to a separatory funnel containing 50 ml of water and 50 ml of 122-11 methylene chloride. The layers were separated and the organic phase was washed once with 10 ml of 10% potassium carbonate, five times with 10 ml portions of water, once with 10 ml of saturated sodium chloride and dried over Na2SO4. The dried limiting solution was filtered and the solvent was stripped off as in Example XII to obtain 5.55 g (102.1% of theory) of an orange oil of M932. The product was identified by IR, NMR and mass spectrometry as the title compound. The compound has number 568 in Table I. Example XIV. N,N' -di- (l-heptyl)-N'- -(ethylmercaptocarbonyl)-S-ethylisothiourea. The procedure and device were the same as in Example XII, except that 5.0 g (16 .6 millimoles) N,N'-di- (l-heptyl)-S-ethylisothiourea, 1.85 g (18.3 millimoles) triethylamine and 50 ml methylene chloride, then 2.28 g (18.3 millimoles) 3 millimoles) of ethylthiochloroformate. The obtained product was subjected to phase separation, washed and dried as in Example XII. The solvent was removed under reduced pressure, obtaining 6.55 g (101.5% of theoretical yield) of a yellow oil with an nD of 1.4922. The product was identified by IR, NMR and mass spectroscopy as the title compound. The union has no. in table I. 294. Example XV. 1,3-diheptyl-2-ethyl-3- -\V (2" - ethoxyethoxycarbonylamino) - 4,-methylphenyl-aminocarbonyl/isothiourea. The title product was obtained as follows: Step a) 1,3-diheptyl-2-ethyl- 3-(3-isocyanate-4-methylphenylaminocarbonyl)isothiourea (intermediate product). 125 ml of methylene chloride were pipetted, under a flow of argon, into a 200 ml three-neck flask. While stirring, 15.1 g (0 .86 mol) of toluene-2,4-diisocyanate and, in turn, within 5 minutes, on cooling, 25.8 g (0.086 mol) of 1,3-diheptyl-2-ethylisothiourea. During the addition, the temperature increased from 20 to approximately 30°C. The mixture was brought to a reflux temperature (41°C) and maintained at this temperature for an hour. Then the obtained reaction mixture was evaporated in a rotary evaporator under high vacuum. 39.8 g of product with nD 1.5318, which was identified by IR and C13-NMR spectrometry as the title intermediate. Step b) I,3-diheptyl-2-ethyl-3-(3'-(2"-ethoxy-ethoxycarbonylamino)-4 ,-methylphenylaminocarbonyl/ 50 isothiourea. To the three-necked flask were added 4.74 g (0.010 mol) of the intermediate from step a), 0.95 g (0.0105 mol) 2-ethoxyethanol, 2 drops of triethylamine, 1 drop of 55 dibutyltin dilaurate and 25 ml of tetrahydrofuran dried over Linde 3A molecular sieves. The mixture was brought to reflux (67 to 68°C) and kept at reflux for 2 hours. The solvent was stripped off at a pressure of 0.3 mm or less 50, at a bath temperature of 80 to 90°C. 5.6 g of a viscous oil were obtained, which was identified as the title compound by IR and C13-NMR spectrometry. Example XVI. 1,3-diheptyl-2-ethyl-3-/3'- t5 648 12 - (3"-chloro-4"-methylphenylureido)-4'- methylphenyl-aminocarbonyl/isothiourea. The reaction and reagents were identical to Example XV b), except that instead of 2-ethoxyethanol, 1.49 g of 5 (0.0105 mol) 3-chloro-4-methylaniline was used. An insoluble by-product was formed, which was filtered off before evaporating the solvent. 3.5 g of product were obtained, which was identified as the title compound by IR and NMR spectrometry. 10 Example XVII. 1,3-Diheptyl-2-ethyl -3-(3'-propylureido-4'-methylphenylaminocarbonyl/isothiourea. 4.74 g (0.010 mol) of the intermediate prepared as in Example 15 were added to a three-necked flask. ) and 25 ml of dry tetrahydrofuran. Without cooling, 0.62 g (0.0105 mol) of propylamine was added at room temperature. The reaction was exothermic and the temperature rose from about 10 to 20°C. Without heat, the reaction was completed within an hour. The mixture was filtered off from a small amount of solid by-product and processed as in example 30 XV b). Otizymano 5.0 g of liquid with nD 1.5312, which IR and C13-NMR spectroscopy identified as the title compound. The compound has number 360 in Table I. Example XVIII. 1,3-diheptyl-2-ethyl-3- /3,-p-chlorobenzylthiocarbonylamino-4*-methylphenylaminocarbonyl/isothiourea. The reagents were the same as in Example XV b), except that instead of 2-ethoxyethanol 1.66 g (0.0105 mol) of 4-chlorobenzylmercaptan was used. 6.5 g of a viscous liquid were obtained, which was identified by IR and NMR spectroscopy as the title compound. Example 19. 1,3-Diheptyl-2-ethyl-3- (3'-phenoxycarbonylamino -4'-methylphenylaminocarbonyl)isothiourea. The reagents were the same as in Example XV b), except that instead of 2-ethoxyethanol 0, 99 g (0.0105 30 mol) phenol. 5.2 g of liquid obtained o no !» 5488, which NMR and IR spectroscopy identified as the title compound. The compound has number 374 in Table I. Example XX. 1-octyl-2-ethyl-3-Urz.heptyl-3-(3-(1-octyl-2-propyl-3-sec. heptyl-3-carbonylamino)-4-methylphenylcarbonylamino/ isothiourea. Step a ) 1-octyl-2-ethyl-3-IIr. heptyl-3-(3-isocyanate-4-methylphenylaminocarbonyl) isothiourea (intermediate product) The above intermediate was prepared as the intermediate from Example XV a), except that instead of thiourea from step XV a), 27 was used .2 g (0.086 mol) 1-octyl-2-ethyl-3-II heptylisothiourea. 41.5 g (98.8% of theoretical yield) of liquid with No. 1.5280 were obtained, which was identified by IR and C13-NMR spectroscopy as the title intermediate compound. Step b) 1-octyl-2-ethyl-3-IIrt. heptyl-3-(3-(1-octyl-2-propyl-3-sec. heptyl-3-carbonylamino)-4-methylphenylcarbonylamino/isothiourea. The title compound was prepared as in Example 15(b), except that 4.87 g (0.010 mol) of the intermediate compound from step XX a) and 3.29 g (0.010 mol) of 1-octyl-2-propyl-3-II row were used. heptyl isourea. 7.9 g (96.3% of theoretical yield) of liquid with nD 1.5185 were obtained, which was identified as the title compound by IR and C13-122 648 13 14 NMR spectrometry. The compound has number 448 in Table I. Example XXI. 1,3-bis-n-heptyl-1- (carbamylsulfonyl chloride)-2-S-ethylisothiourea. To a 200 ml flask equipped with a magnetic stirrer, thermometer and addition funnel, 50 ml of dry methylene chloride and 8, 49 g of chlorosulfonyl isocyanate (aldrich). Then, within 40-45 minutes, a solution of 18 g of 1,3-diheptyl-2-ethylisothiourea in 100 ml of dry methylene chloride was added dropwise. The reaction was slightly exothermic, so the flask was cooled with water to keep the temperature below 28 °C. The solution was stirred during overnight at about 25 °C. The solution was filtered and the filtrate was evaporated under reduced pressure. 26.2 g (99% of theoretical yield) of a thick liquid with an nD of 1.4833 were obtained. IR and NMR spectroscopy identified the product as the title compound. The compound has number 523 in Table I. Example XXII. 1,3-bis-n-heptyl-1-chlorocarbonyl-2-ethylisothiourea. 100 ml of dry CH2C12 were added to a 500 ml flask equipped with a thermometer and dropping funnel and cooled in an ice bath to 5° C A benzene solution of phosgene (170 g of a solution with a concentration of 17.5% by weight) was added, and then, within an hour, at 5°C, 10.1 g of triethylamine and 30 g of 1,3-diheptyl-2-ethylisothiourea were added dropwise. The mixture was stirred overnight at room temperature. The next morning the mixture was brought to 40° C. over 2 1/2 - 3 hours to ensure completion of the reaction. The solvent was then stripped off under reduced pressure. 100 ml of dry ether were added and filtered through a fritted glass. The solid product was washed with a small volume of ether and the combined filtrates were stripped of ether under reduced pressure. 38.6 g of liquid (106% of theoretical yield) with an nD of 1.4613 were obtained. Mass spectrography identified the product as the title compound. The compound has number 528 in Table 1. Example XXIII. 1,3-bis-n-heptyl-1-diethylcarbamyl-2-ethylisothiourea. 100 ml of dry benzene and 5.44 g of l,3-carbamyl chloride were added to a 200 ml flask, equipped with a thermometer and an addition funnel. diheptyl-2-ethylisothiourea. Within 10-12 minutes, a solution of 2.19 g of diethylamine in 12 ml of dry benzene was added dropwise. As a result of the exothermic reaction, the temperature increased to 21-30 °C. Then the mixture was kept at 45-50°C for 3 hours, cooled to 15°C and washed twice with 50 ml portions of cold water. The benzene phase was dried over MgSO4, filtered and the solvent was removed under reduced pressure. 5.75 g of liquid (96% of theoretical yield) with an nD of 1.4568 were obtained. Mass spectrometry revealed that the structure corresponds to the title compound. The compound has number 521 in Table I. Example XXIV. 1,3-bis-n-heptyl-1-(propargyloxycarbonyl)-2-ethylisothiourea. To a 200 ml flask equipped with a thermometer and an addition funnel, 50 ml of dry tetrahydrofuran and 0.36 g of NaH were added . Within 8-10 minutes, a solution of 0.84 g of propargyl alcohol in 10 ml of dry tetrahydrofuran was added dropwise. A slightly exothermic reaction occurred with evolution of hydrogen. To complete the reaction, stirring was continued for 3 hours. Over 10 minutes, a solution of 5.44 g of 1,3-diheptyl-2-ethylisothiourea carbamyl chloride in 15 ml of dry uranium tetrahydrogen was added dropwise. With stirring, the mixture was brought to 45 °C for 2 hours. Then the mixture was cooled and filtered through fritted glass. The solvent was removed under reduced pressure, obtaining 5.0 g of liquid (88% of theoretical yield) with an nD of 1.4553. NMR and mass spectroscopy revealed that the structure corresponds to the title compound. The compound has number 533 in Table I. Example XXV. Salt 1,3-bis (2-ethylhexyl)-l- (succinic anhydride adduct)-2- ethylisothiourea -Et3N. 200 ml of dry CH3C12, 32.8 g of 1.3 were added to a 500 ml flask. - (2-ethylhexyl)-2- ethyl isothiourea, 11 g of succinic anhydride and 11.1 g of Et3N. When mixing the ingredients, a slightly exothermic reaction occurred. The solution was left to rest overnight. The solvents were removed under reduced pressure, obtaining 47.3 g of liquid (89% of the theoretical yield) with an nD of 1.4899. IR and NMR spectrometry showed that the structure corresponds to the title compound. The compound has number 550 in Table I. Example XXVI. The reaction product of 2 moles of 1,3-di- (2'-ethylhexyl)-2-S-ethylisothiourea with toluene-2,4-diisocyanate. In a three-neck flask with a capacity of 200 ml, equipped with a magnetic stirrer, 3.28 g (0.01 mol) of 1,3-di- (2,-ethylhexyl-2-S-ethylisothiourea) were mixed with 20 ml of tetrahydrofuran. 0.87 g (0.005 mol) of toluene-2 was added to the solution The temperature was raised from 23 to 34°C. The mixture was left to rest overnight at room temperature and then evaporated under reduced pressure. Infrared analysis showed that no reaction had occurred. until the end, the mixture was dissolved in 30 ml of methylene chloride and 1 drop of dibutyltin dilaurate and 2 drops of triethylamine were added. The homogeneous solution was stirred for 1.5 hours at room temperature and evaporated again under reduced pressure. * 30 to obtain a yellow viscous liquid with nD 1.5201. Yield 4.3 g. IR and NMR analysis the product was identified as the title compound. The compound has number 83 in Table I. 50 Example XXVII. 1,3-di-n-heptyl-1-N-phenylcarbamyl-2-S-n-propylisothiourea. The device used was as in Example XXVI. 6.2 g (0.014 mol) of 1,3-di-n-heptyl-2-S-n-propylisothuronium hydroiodide was dissolved in 55 ml of tetrahydrofuran and, while cooling, 1.68 g (0.014 mol) of phenyl isocyanate was added, and then 1 .43 g (0.014 mol) triethylamine. The white product precipitated out. The mixture was stirred overnight at room temperature and then evaporated under reduced pressure to remove tetrahydrofuran. The residue was dissolved in chloroform and washed twice with 150 ml of water. The organic phase was dried over magnesium sulfate, filtered and evaporated under reduced pressure to remove the chloroform. 5.9 g (96.7%122 648 15 16 of theoretical yield) of a light yellow liquid with n3D 1*5188 were obtained. IR and NMR spectrometry identified the product as the title compound. The compound is number 10 in Table I. Example XXVIII. 1,3-di-n-heptyl-1-N-octadecylcarbamyl-2-S-ethylisothiourea. The device was the same as in Example XXVI. 4.5 g (0.015 mol) of 1,3-di-n-heptyl-2-S-ethylisothiourea were mixed with 40 ml of tetrahydrofuran and 4.43 g (0.015 mol) of N-octadecyl isocyanate were added. 3 drops were added triethylamine and the mixture was left to rest overnight. The mixture was then heated at 40°C for 20 minutes to complete the reaction. A small amount of solid product, which precipitated on cooling, was filtered off. The reaction mixture was then evaporated under reduced pressure, obtaining 8.9 g (100% of theoretical yield) of a clear liquid with n^} 1.4750. IR and NMR spectrometry identified the product as the title compound. The compound has number 28 in Table I. Example XXIX. 1,3-di-n-heptyl-1,N-4-methylthiophenylcarbamyl-2-S-ethylisothiourea. The device was the same as in Example XXVI. 3.0 g (0.01 mol) 1,3-di-n-heptyl-2-S-ethylisothio-urea was mixed with 25 ml of methylene chloride. 2 drops of triethylamine and 1 drop of dibutyltin dilaurate were added, followed by 1.65 g (0.01 mol) of 4-methylthiophenyl isocyanate. The temperature increased from 23 to 33 °C. The reaction mixture was evaporated under reduced pressure, after removing methylene chloride, to obtain 4.65 g (100% of theoretical yield) of a yellow liquid with n^sup 1.5340. The product solidified into a semi-solid upon standing. IR and NMR spectrometry identified the product as the title compound. The compound has plate I no. 46. Example XXX. 1,3-di-n-heptyl-1-N-2-chloroethylcarbamyl-2-S-ethylisothiourea. The procedure, apparatus and reagents were the same as in Example XXIX, except that instead of 4-methylthiolphenyl isocyanate, 4-methylthiolphenyl isocyanate was used. 1.06 g (0.01 mol) 2-chloroethyl isocyanate. 4.14 g (102% of theoretical yield) of a clear liquid with an nD of 1.4930 were obtained. IR and NMR spectrometry showed that the product is the title compound. The compound has number 47 in Table I. Example XXXI. l-II-heptyl-3-n-heptyl-2-S-ethylisothiourea (intermediate product). The device was the same as in Example XXVI. 11.5 g (0.1 mol) of 2-aminoheptane were mixed with 50 ml of ethanol and 15.7 g (0.1 mol) of N-heptyl isothiocyanate were added. As a result of the exothermic reaction, the temperature increased from 25 to 65 °C. The reaction mixture was kept at reflux for 1.5 hours on a steam bath. Then 17.16 g (0.11 mol) of ethyl iodide were added and the mixture was refluxed on a steam bath for 1.5 hours. The product was evaporated under reduced pressure to obtain 44.0 g of isothiuronium salt. The isothiuronium salt was dissolved in 200 ml of toluene and washed with 100 ml of 5% sodium hydroxide. The tolulene layer was washed with two 150 ml portions of water, dried over magnesium sulfate and evaporated under reduced pressure. After evaporation under high vacuum, 7.78 g (92.6% of theoretical yield) of a clear, yellow liquid with an nD of 1.4768 were obtained. By IR and NMR spectrometry the product was identified as the title compound. Example XXXII. 1-II-heptyl-3-n-hexyl-2-S-5-ethylisothiourea (intermediate product). The apparatus, procedure and reagents were the same as in Example 31, except that 10.01 g (0.07 mol) of n-hexyl isothiocyanate, 8.05 g (0.07 mol) of 2-aminoheptane, and 35 ml of ethanol, 11.7 g (0.075 mol) of ethyl iodide, 200 ml of toluene and 1% sodium hydroxide solution (0.08 mol). 19.6 g (98% of theoretical yield) was obtained. clear liquid with n^ 1.4765. By IR and NMR spectrometry the product was identified as the title compound 1. Example XXXIII. 1,3-di-n-heptyl-1-N-III butylcarbamyl-2-S-ethylisothiourea. The device was the same as in Example XXVI. 2Q 3.0 g (0.01 mol) of 1,3-di-n-heptyl-2-S-ethylisothiourea was mixed with 30 ml of methylene chloride. 2 drops of triethylamine and 1 drop of dibutyltin dilaurate were added, followed by 1.0 g (0.01 mol) of tert-butyl isocyanate. The temperature increased from 24 to 39°C. The reaction mixture was stirred overnight at room temperature and then heated for half an hour at 35 to 40°C to complete the reaction. The reaction mixture was evaporated under reduced pressure to give 3.83 g (96% of theoretical yield) of clear liquid with nD 1.4750. IR and NMR spectrometry the product was identified as the title compound. The compound has table I number 39. Example XXXIV. 1,3-di-n-heptyl-1-N-ethyl acetatecarbamyl-2-S-ethylisothiourea. The procedure, apparatus and reagents were the same as in Example XXXIII, except that instead of tert-butyl isocyanate, 1.29 g (0.01 mol) of ethyl isothiocyanatoacetate was used. 4.3 g (100% of theoretical yield) of a clear liquid number 1.4800 were obtained. 40 IR and NMR spectrometry the product was identified as the title compound. The compound has number 40 in table I. Example XXXV. 1,3-di-n-heptyl-3-hydroxyethylcarbamylmethylcarbamyl-2-S-ethylisothiourea. The apparatus was the same as in Example XXVI. 9.0 g (0.03 mol) of 1,3-di-n-heptyl-2-S-ethylisothiourea was mixed with 30 ml of methylene chloride to which 3.87 g (0.03 mol) of ethylcyanoacetate was added. Temperature increased from 23 to 45°C. The mixture was left to rest overnight and then 10 drops of isothiourea were added to react with the remaining isocyanate. Then, 1.83 g (0.03 mol) of 2-aminoethanol was added to the reaction mixture and the mixture was stirred overnight. The reaction mixture was evaporated under reduced pressure to remove methylene chloride, and 25 ml of ethanol were added to the residue. The reaction mixture was left to rest for 3 days. The obtained cloudy mixture was stirred overnight at room temperature and then evaporated under reduced pressure, obtaining 13.7 g of a yellow, cloudy liquid with an nD of 1.4800. IR and NMR spectrometry identified the product as the title compound. The compound has number 63 in table I 65. 45 50 55122 648 17 18 Example XXXVI. Reaction product of 2 moles of 1,3-di-n-III. -heptyl-2-S-ethylisothiourea with pp'-diphenylmethane diisocyanate. The apparatus was the same as in Example XXVI. 3.0 g (0.01 mol) of 1,3-di-II-heptyl-2-S-ethylisothiourea were mixed with 30 ml of toluene. 1.25 g (0.005 mol) pp'-diphenylmethane diisocyanate was added and the mixture was heated at 75 to 80 °C for 2 hours. The IR spectrum showed a weak isocyanate band. Therefore, 10 drops of isothiourea were added and heating was continued for 30 minutes. The reaction mixture was then stirred overnight at room temperature. It was then evaporated under reduced pressure, obtaining 4.5 g (104% of theoretical yield) of an amber-colored liquid with n3D 1.5310. IR and NMR spectroscopy the product was identified as the title compound. The compound has number 125 in Table I. Example XXXVII. The reaction product of 2 moles of 1-N-II-heptyl-3-N-n-hexyl-2-S-methylthiomethyl¬ isothiourea with toluene-2,4-diisocyanate. The procedure and device were the same as in Example XXVI, but 3, 8 g (0.01 mol) 1-sec-heptyl -3-N- n-hexyl-2-S-methylthiomethylisothiourea, 0.87 g (0.005 mol) toluene-2,4-diisocyanate and 25 ml of tetrahydrofuran. After the reaction was completed, 20 drops of isothiourea were added to react with the remaining isocyanate overnight at room temperature. The reaction mixture was evaporated under reduced pressure, obtaining 4.6 g of a red, viscous liquid with a nune of 1.5344. IR and NMR spectrometry identified the product as the title compound. The union has number 136 in table I. Example XXXVIII. 1-N-IIrt.heptyl-3-N-n-octyl-n-octadecylcarbamyl-2-S - allylisothiourea. The procedure and device were the same as in Example XXVI. 1.9 g (0.006 mol) of 1-II-heptyl-3- n-octyl-2-S-allylisothiourea was mixed with 25 ml of tetrahydrofuran, and 1.77 g (0.006 mol) of }-octadecyl isocyanate was added to the mixture. The whole was stirred overnight at room temperature and then evaporated under reduced pressure, obtaining 3.79 g (100% of theoretical yield) of a clear liquid with an nD of 1.4769. IR and NMR spectrometry identified the product as the title compound. The compound has number 142 in Table I. Example XXXIX. The reaction product of 2 moles of 1-phenyl-3-n-heptyl-2-S-ethylisothiourea with tolu-ene-2,4-diisocyanate. The apparatus was the same as in Example XXVI. 2.78 g (0.01 mol) of 1-phenyl-3-n-heptyl-2-S-ethyliso-urea in 35 ml of tetrahydrofuran were mixed with 0.87 g (0.005 mol) of toluene-2,4-diisocyanate. The reaction mixture was kept for an hour at reflux on a steam bath, then 15 drops of isothiourea were added and refluxing was continued for another hour to react all the isocyanate. The reaction mixture was evaporated under reduced pressure to obtain 4.1 g of a viscous, yellow liquid with an n = 1.5737. IR and NMR spectrometry identified the product as the title compound. The compound has number 149 in Table I. Example XL. N-(5-sila-5,5-dimethyl-1-heptyl)-N'-n-heptyl, n-octadecylcarbarnyl -2-S-ethylisothiourea. The apparatus was the same as in Example XXVI. 2.4 g (0.007 mol) of 1-(5,-sila-5,.5,-dimethyl-N-heptyl)-3-n-heptyl-2-S-ethylisothiourea in 25 ml of tetrahydrofuran were mixed with 2 .06 g (0.007 mol) of N-octadecyl isocyanate and stirring was continued for 2 hours at room temperature. The reaction mixture was evaporated under reduced pressure, obtaining 4.51 g (100% of theoretical yield) of a clear liquid with an nD of 1.4765. IR and NMR spectrometry identified the product as the title compound. The compound has number 182 in Table I. Example XLI. N-dichloroacetyl-N,N'-di-15-n-heptyl,S-ethylisothiourea. To a three-necked 200 ml flask equipped with a magnetic stirrer, 3.0 g (0.01 mol) l was added 3-di-n-heptyl-2-S-ethylisothiourea dissolved in 25 ml of methylene chloride. 1.1 g of triethylamine was added to the mixture, then the flask was placed in an ice bath and 1.5 g (0.01 mol) of dichloroacetyl chloride in 10 ml of methylene chloride were slowly added. The reaction mixture was brought to 40°C and held at this temperature within half an hour. The reaction product was washed with water, and the organic layer was dried over magnesium sulfate, filtered and evaporated under reduced pressure, obtaining 4.1 g of liquid - 14723. NMR spectrometry identified the product as the title compound. The compound has number 312 in Table I. Example XLII. Adduct of 1 mole of 1,3-di-n-heptyl-2-S-ethylisothiourea and 1 mole of diglycolic anhydride. The apparatus was the same as in Example XLI. 3.0 g (0.01 mole) of 1,3-di-n-heptyl-2-S-ethylisothiourea dissolved in 15 ml of glycol were mixed with 1.2 g (0.01 mole) of diglycolic anhydride dissolved in 10 ml of glycol. The reaction mixture was kept at reflux for 10 minutes and then evaporated under reduced pressure, obtaining 4.1 g of liquid at 1.4608. IR and NMR spectrometry identified the product as the title compound. The compound has number 306 in Table I. 45 Example XLIII. Adduct of 1 mole of 1,3-di-n-heptyl-2-S-ethylisothiourea and 1 mole of succinic anhydride. The apparatus, procedure and reagents were the same as in Example XLII, except that diglycolic anhydride was replaced with anhydride amber. 4.1 g of a semi-solid product were obtained, which was identified by NMR spectrometry as the title compound. Example XLIV. Adduct of 1 mole of 1,3-di-n-hep-55 tyl-2-S-ethylisothiourea and 1 mole of formaldehyde. The procedure, apparatus and reagents were the same as in Example XLII, except that instead of diglycolic anhydride, 1 .2 g of formaldehyde, as a 37% solution in water (0.01 mol + approximately 20% W in excess). 3.3 g of a semi-solid product were obtained, which was identified by NMR spectrometry as the title compound. Example XLV. 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Claims (9)

1. Patent claims 1. A preparation against hymenoptera, characterized in that it contains as an active ingredient a compound of formula 1, in which R and R are independently a C2-C10alkyl, C1-C10-alkoxyalkyl or phenyl radical, wherein R and Rx together contain 12 to 22 carbon atoms; R3 is a Cx-C14alkyl radical, C3-Cl0-alkenyl, C3-C4alkynyl, C1-C4hydroxyalkyl, C1-C6alkylthioalkyl, C1-C1alkoxyalkyl, a radical of the formula (CH2)n[X(CH2) Jy, where n is the number 1 or 2; R3 is a carboalkoxyalkyl radical in which the alkyl moiety is a Cx-^-alkyl radical, an alkylcarbonylalkyl radical in which the alkyl moiety is a Cx-C4alkyl radical, a hydroxy alkenyl radical in which the alkenyl moiety is a C3-C4alkenyl radical , a hydroxyalkyl radical in which the alkyl fragment is a Ct-C12alkyl radical, a formyl hydroxymethyl radical, a hydroxyhaloethyl radical in which the halogen atom i* is a chlorine, bromine or iodine atom, a substituted 122 648 81 82 phenoxyalkyl radical, in which the alkyl fragment is a C1-C2alkyl radical, and the substituents are a p-methoxy group, Cl, NO2 or CN, a radical of formula 2, in which R1 is -OH, -NH2 or a C1-C4alkoxy group; a group of the formula -CHOHCHOHNfcSR3 (=NRX), in which R, Rt and R3 have the meanings given above; a radical of the formula 3 in which R, fc* and fc3 have the meanings given above, a group of the formula -P03 B, -P(OH)O3 -B or -S03 B, in which B is a basic cation; a group of the formula -CONR^ in which R4 is a hydrogen atom, a Ct-(^alkyl, hydroxyethyl, naphthyl, phenylyl substituted phenyl radical, wherein the substituents are independently selected from the group consisting of halogen atoms, C1-C5-alkyl radicals, Ct groups -C5alkoxy, nitro group, cyano group and -CF3 group; a radical of the formula 5, in which R, Rj and R3 have the meanings given above; a radical of the formula -(CH^NHCONRCSR^NRi), in which R, Rt and R* have the meanings given above; a radical of the formula 6, in which R, Rx and Ra have the meanings given above; a radical of the formula 7, in which R, K% and Ra have the meanings given above; a radical of the formula 8, in wherein R, B1 and R3 have the above-mentioned attachments; a radical of the formula 9, wherein or 3, and R, Rx and Ra have the above-defined meanings; radical 9 of formula 11, wherein R, Rx and R3 have the above-defined meanings; radical of formula 12, wherein R, Rt and R' have the above-defined meanings; a radical of the formula 13, wherein C4-C4alkenyl radical, C3-C4alkynyl radical, C3-C4haloalkyl radical, C3-C3cycloalkyl radical, C1-C4pohcycloalkyl radical, C1-C**polyalkoxyalkyl radical, C3-C6hydroxyalkyl radical, Ca radical ^Cioalkoxyalkyl, C3-C1-carboalkoxyalkyl radical, C4-C8cycloalkylalkyl radical, C4-C12dialkylaminoalkyl radical, C4-Cycloalkylimino radical, Ct-C3alkylamino, C1^C10alkylimino radical, C6-C10cycloalkenyl radical , phenyl radical, an alkylphenyl radical in which the alkyl moiety is a Q-C4alkyl radical, a p-chloroalkylphenyl radical in which the alkyl moiety is a C1-C4alkyl radical, a naphthyl radical, anthracanyl radical, a benzamidocycloalkyl radical in which the alkyl moiety is a Cx radical —(^alkyl, pyranylmethyl, tetrahydrofurfuryl, thiophenomeyl, benzhydryl or halobenzhydryl radical, polycyclic alcohol and substituted phenyl radical, wherein the substituents are selected from the group consisting of C1-C4alkyl radical, halogen atoms, nitro group, trifluoromethyl radical, formyl radical, chloroacetyl, a C1-C4alkoxy group, a hydrogen atom, a benzyl, chlorobenzyl, fendtyl and substituted phenethyl radical, wherein the substituents are selected from the group consisting of a C1-C4alkyl radical and a halogen atom; and R 1 sulfur, then R10 is not hydrogen; and a substituted phenyl radical, wherein the substituents are selected from the group consisting of halogen atoms, a C1-C4alkoxy group, a phenoxy group, a trifluoromethyl radical, a Cx-C6thioalkyl radical, a nitro group, an isocyanate group , 5°2-C4polyalkoxy group, C3-C7cycloalkyl radical, C3-C6carboalkoxyalkyl, A-C,haloalkyl, C3-C3alkenyl radical, C3-C6dialkylpramino group, phenylamino group, Cx-C34alkyl radical, C3-C13hydroxyalkylamidoalkyl, C5-C10 10 N,N-hydroxyalkylureidoalkyl and alkyl isocyanate, where the alkyl fragment is a Cx-(^alkyl radical, an alkylamidoalkyl radical, a polyalkoxyamidoalkyl radical, where the polyalkoxy system contains 3-6 repeating C,-C3alkoxy units - j5, and the amidoalkyl fragment contains 4-12 carbon atoms; -SOaCl group and -SO3polyalkoxyalkyl group, where the polyalkoxy system contains 3-6 repeating C3-C3 alkoxy units and the amidoalkyl fragment contains 4-12 carbon atoms; R5 is selected from the group consisting of hydrogen, C3-C4alkyl radical, C3-C4alkoxyalkyl radical, C3-C4alkenyl radical, hydroxyethyl radical and phenyl radical; R* and R together form a heterocyclic radical; and the group -CC^R*, where n = 1, the substituents are selected from the group consisting of nitro, chlorine, C1-C3alkyl radical, C4-C6polyalkoxyalkyl radicals, C3-C4cycloalkyl, C1-C4alkenyl, C1-C6alkoxyalkyl, Ca-C *hydroxyalkyl, Cx-C6carboxyalkyl and Cs-C8trialkyl-amino salts, and when n = 0, the substituents are selected from the J5 group consisting of a chlorine atom, a thiopotassium group, a C1-C18alkyl, benzyl, C1-C3heteroalkyl radical, C3-C4chlorocarboxyalkyl, C4-C4polyalkoxyalkyl and acetyl; the group -CORjCOYdZ, where R7 is selected from the group consisting of the radical -(CH3-)n, 40 where n is a number from 0 to 8, the radical -CH =CH-, the radical of the formula 14, where M is H or Cl, the radical of the formula 15, radical —CCI=CCI—, —CH3OCH3— and —OCH3CH30; d is 0 or 1, and when d = 1, Y is selected from the group consisting of oxygen or sulfur and -NH, Z is selected from the group consisting of C1-C1Balkyl, hydrogen, C4- -ClFpolyalkoxyalkyl, C4-Cdialkylaminoalkyl, C3-C5alkynyl, phenyl and substituted phenyl, organic salts and inorganic salts, and when d « 0.50 then Z is a chlorine atom or the group -NRCSR(=NRt), where R, Rj and Rj have the meanings given above; the -POCR5 group, where R' is selected from the group consisting of -Cx-C10alkoxy, amino, C1-C10Xamino and hydroxyl groups and organic bases; 55 group -SOwR, where w is the number 0-2 and R» is selected from the group consisting of an amino group, a C1-C10alkyl radical, a C1-C4haloalkyl radical, a phenyl radical, a C1-C10dialkylamino group, a a Cx-C4alkylamino group, an alkoxy group and a substituted phenyl radical, wherein the substituents are selected from the group consisting of a nitro group, a chloro atom, a Ct-C4alkyl radical and a methoxy group; 05 and further an inert carrier. 122 648 832. The agent according to claim 1. 1, characterized in that it contains as an active ingredient a compound of formula 1, in which R and Rj independently represent a C5-C9alkyl radical, a C5-C9alkoxyalkyl radical or a phenyl radical, with R and R1 containing a total of 12 to 22 atoms. coal; and R2 is a C1-C6alkyl, C3-C5alkenyl, C3-C4alkynyl, C2-C3hydroxyalkyl, C2-C4alkylthioalkyl, C2-C4alkoxyalkyl radical, a radical of the formula (CH2)n-[X (CH2)n]y, where n is 1 or 2, X is oxygen or sulfur and y is 1 or 2; or R2 is a radical of the formula -(CH2)nC0OH, where n is a number from 1 to 5, or R2 is a phenyl radical or a phenethyl radical; and, moreover, an inert carrier. 3. The agent according to claim and, characterized in that it contains as an active ingredient a compound of formula 1, wherein R and Rt independently represent a C6-C8alkyl, C6-C8alkoxyalkyl or phenyl radical, wherein R and Rx together contain 12 to 22 carbon atoms; and R2 Denotes a C±-C13alkyl, G2-C3alkenyl, C3-C4alkynyl, C2-C3tiydroxyalkyl, G2-C4alkylthioalkyl, C2-C4alkoxyalkyl radical, a radical of the formula (CH2)n [X (CH2)J y where n is the number 1 or 2, X is oxygen or sulfur and y is 1 or 2; or R2 is a radical of the formula -(CH2)n-COOH, in which n is a number from 1 to 3, or R2 is a phenyl radical or a phenethyl radical and furthermore an inert carrier. 4. The agent according to claim 1 or 2 or 3, characterized in that it contains a compound of formula 1, in which R3 is a carboalkoxyalkyl radical, in which the alkyl fragment is a C1-C2ayl radical, an alkylcarbonylalpha radical, in which the alkyl fragment is a Cx-C2alkyl radical, hydroxyakenyl radical, in which the alkenyl fragment is a C3-C4alkenyl radical, hydroxyalkyl radical,. in which the alkyl moiety is a Q%-C6alkylyl radical, a formylhydroxymethyl radical, a hydroxyhaloethyl radical in which the halogen atom is a chlorine or bromine atom, a substituted phenoxyalkyl radical in which the alkyl moiety is a C1-alkyl radical and the substituents are p-methoxy group, 'Cl NO2.or CN; a radical of formula 2, in which R1 is -OH, -NH2 or a C1-C4alkoxy group; a group of the formula -CHOHCHOHNRCSR2(=NR1), wherein R, Rj and R2 are as defined above; a radical of the formula 3, in which R, R6 and R2 have the meanings given above, a group of the formula -P03-B, -P(OH)Q2 B or -SQ3-B, in which B is; basic cation; a group having the formula;—CONR4R5 in which R4 is a hydrogen atom, a C1-G12alkyl, hydroxyethyl, naphthyl, phenyl, substituted phenyl radical* where the substituents are independently selected from the group consisting of halogen atoms, C1-C5alkyl radicals, C1- C5alkoxy, nitro group, cyano group and; group -CF3; a radical of formula 5, in which ,Ra Ri. ¦ and *R2 have the above-mentioned meanings and the radical :# ^TOe.-(C.H2),NHCONRCSR2^ in which R, Rt and R2 have the above-described meanings; a radical of formula 6 in which R, Rx and R2 have the meanings given above; a radical of formula 7 in which R, R6 and R2 have the meanings given above; a radical of formula 8 in which R, RL and R2 have the meanings given above; a radical of formula 9, where x is 1 to 8 and R, R6 and R2 have the meanings given above; a radical of the formula 10, in which 84 m is 2 or 3 and R, RA and R2 have the meanings given above; a radical of formula 11 in which R, Rx and R2 have the meanings given above; a radical of formula 12 in which R, R6 and R2 have the meanings given above; 5 a radical of the formula 13, wherein C3-C4-Little, Ro- 10 C3- C4ALKINIL, RODZ C7- C20Policycloalkylkillekilkilo, radical C2- C16Polkoxyald or alkyl, radical C4-G12dialkylaminoalkyl, C4'-Ccycloalkylimino group, C1-C3alkylamino, C1-r-C10alkylimino, G6-C10cycloalkenyl radical, phenyl radical, alkylphenyl radical in which the alkyl moiety is C1-C4alkyl radical, p-chloroalkylphenyl radical, in which the alkyl fragment is a C1-C4alkyl radical, naphthyl radical, anthracene radical, benzamidocycloalkyl radical, in which the alkyl fragment is a C1-C6alkyl radical, pyranylmethyl radical, tetrahydrofurfuryl radical, thiophenemethyl radical, benzhydryl or halogenated benzhydryl, polycyclic alcohol and substituted phenyl radical, wherein the substituents are selected from the group consisting of C1-C4alkyl radical, halogen atoms, nitro group, trifluoromethyl, formyl, chloroacetyl radical, C1-C4alkoxy group, wo-f* atom hydrogen, benzyl, chlorobenzyl, phenethyl and substituted phenethyl, wherein the substituents are selected from the group consisting of C1-C4alkyl and halogen; and Ra is selected from the group consisting of G1-C4alkyl, C3-C6alkoxyalkyl and C3-C4alkenyl; and R10 and Rn together form a heterocyclic radical selected from the group consisting of azepine, morpholinyl, piperidinyl, piperidinyl radicals substituted with a C1-C3alkyl radical; provided that when X is an oxygen or sulfur atom, R10 is different from the r,v hydrogen atom; and a substituted phenyl radical, wherein the substituents are selected from the group consisting of halogen atoms, C1-C4alkoxy, phenoxy, trifluoromethyl, C1-C4thioalkyl, nitro, isocyanate, C2-G4polyalkoxy, C1-1Or cycloalkyl radical * C3-C10carboalkoxy, C1^C4haloalkyl, C3-C4alkenyl, dialkylamino group, phenylamino group, C±-C4alkyl radical, C3-C12hydroxyalkylamidoalkyl, Cs-C10-N,N-hydroxyalkylureidoalkyl, isocyanatoalkyl, ?° in which the alkyl fragment is the G^CsaL-kyl radical, the C3^-C12alkylamidoalkyl radical, the polyalkoxyamidoalkyl radical, in which the polyalkoxy fragment contains 3 to 6 repeating G2-C3alkoxy units, and the amidoalkyl fragment contains- {;f: contains 4-12 atoms coal; a ^S02C1 group and a rf^S02polyalkoxyamidoalkyl group, where the polyalkoxy moiety contains 3 to 6 repeating G2-^C3aikoxy units and the amidoalkyl moiety contains 4 to 12 carbon atoms; R* is/selected from the group consisting of hydrogen, C1-C4alkyl, C3-C6alkoxyalkyl, G3-C4alkenyl, ethyl hydroxyl and phenyl; R4 and R5 together form a heterocyclic radical selected from the group consisting of azepinyl, morpholinyl, piperidinyl and pipe-122 64S Wridinyl radicals substituted with a C1-C3alkyl radical; group -GOXnR6 where X is an oxygen or sulfur atom, n is the number 0 or 1, R6 is selected from the group consisting of the radical C±-CI3alkyl, C2-C6halo-alkyl, phenyl and substituted phenyl, when where n is the number 1, the substituents are selected from the group consisting of nitro, chlorine, Ct-C2-alkyl, G4-C6polyalkoxyalkyl, C3-C8cycloalkyl, C3-C4alkenyl, C3-C6alkoxyalkyl, C3-C6hydroxyalkyl, Cx-C3carboxyalkyl C5-C8trialkylammonium salts, and when n is 0, the substituents are selected from the group consisting of a chlorine atom, a thiopotassium group, a CL-C12alkyl, benzyl, C1-C3heteroalkyl, C2^C4chlorocarboxyalkyl, C4-(Vpolyalkoxyalkyl and acetyl; group of the formula -COR7COYdZ, where R7 is a radical selected from the group consisting of the radical - (CH2-)m where n = 0 to 8, -CH=CH-; a radical of the formula 14, where M is H or Gl; a radical of the formula 15 , radical —CC1=CG1—, —CH2OCH2—, —OCH2 CH20 and d = 0 or 1; when d = 1, Y is selected from the group consisting of oxygen and sulfur atoms and -—NH, and Z is selected from the group consisting of Ct-C12alkyl radical, hydrogen atom, C4-C16polyalkoxyalkyl* C4-C8dialkylaminoalkyl, C3-C5alkynyl, fanyl, and substituted phenyl radical and organic salts and inorganic salts, and when d = O, Z is Gl or a group of the formula -NRGSR^^NRO, where R, Rx and R2 are as defined above; the group -POCRg^, where R8 is selected from the group consisting of the groups Ct-C8-alkoxy, amine, Ct-C5-alkoxyamine, hydroxyl and organic base, the group -SOwR*y where w is 0-2 and R9 is selected from groups including amino, C1-C5alkyl, G1-C4haloalkyl, phenyl, C1-C10clw.u- alkylamino, C1-G10alkylamino, C1-C5alkoxy-Jpwa and substituted phenyl radical, wherein the substituents are selected from a group consisting of a nitro group, a chlorine atom, a Cx-C4alkyl radical and a methoxy group. 5. Agent according to claim. 1 or 2 or 3, characterized in that it contains a compound of the formula 1, in which R3 is a carboalxyalkyl radical, where the alkyl moiety is a C1-4Galkyl radical, nylalkyl, where the alkyl moiety is a C4-G2alkyl radical, hydroxyalkenyl, where the alkenyl fragment is a C3-C4alkenyl radical, hydroxyalkyl, where the alkyl fragment is a C1-C3alkyl radical,formylhydroxymethyl, hydroxyhaloethyl, where the halogen atom is a chlorine atom, substituted phenoxyalkyl, where the alkyl fragment is a C1-alkyl radical, and the substituents are p-methoxy group, Cl, NO2 or CN; a radical of formula 2 in which R1 is -OH, -NH2 or a methoxy group; a radical of the formula -CHOHCH-OHNRCSR2(=NR1), wherein R, J3 and R2 are as defined above; a radical of formula 3 in which R, Rj and R2 have the meanings given above; group -PÓ3 -B, -P (OH)O2 -B or -S03 -B, where B is an organic base selected from the group consisting of the cation (CH3)3 + NH and the cation of formula 4; a group of the formula -CONR4R5, wherein R4 is selected from the group consisting of hydrogen, C1-C8alkyl, hydroxyethyl, naphthyl phenyl or substituted phenyl, wherein the substituents are independently selected from the group consisting of chloro, C1-G2alkyl, C1 -C2-alkoxy, -nitro, cyano and CF3; a radical of formula 5 in which R, Rt and R2 have the meanings given above; the radical bwztf-Tze - (CH2)6NHCONRCSR^(=NR1) in which R, Rt and R2 have the above-mentioned meanings, the radical of Formula $ in which R, R4 and R2 have the above-described meanings; a radical of formula 7 in which R, Rt and R2 have the meanings given above; a radical of formula 8 in which R, Ri and R2 have the meanings given above; a radical of the formula 9, in which x is 1 to 8, and - R, Rt and R2 have the meanings given above; a radical of formula 10 in which m is 2 or 3 and R, Rt and R2 have the meanings given above; a radical of formula 11 in which R, Rx and Rj have the meanings given above; a radical of the formula 12 in which R, RL and R2 have the above-mentioned meanings; a radical of the formula 13, in which X is selected from the group consisting of oxygen and sulfur atoms and the NH and NRn groups, and Y is a hydrogen atom or a methyl radical! R10 is selected from the group consisting of hydrogen, C1-C2alkyl, C3-C4alkenyl, C3-C4alkynyl G2-G3haloalkyl, C3-^C8cycloalkyl, C7-*-C20polycycloalkyl, C2-C^polyalkoxyalkyl, C* - -G6-hydroxyalkyl, C3-G4alkoxyalkyl, C3-G8-carboalkylcycloalkyl, C4-<^8cycloalkylalkyl, Cft-Cstlkylcycloalkyl, group; C4-C1cycloalkyl- imine, G2-C10aBcno-imino or C1-C3alkuamine, C4-Claddualkylaminoalkyl radical, C1-C10-cycloalkenyl, phenyl, alkylphenyl, in which the alkyl moiety is a C1-C4alkyl radical, p-chloroalkylphenyl, in in which the alkyl moiety is a C1-C4alkyl radical, naphthite radical, 4m-tracenyl, benzamidocycloalkyl, in which the alkyl moiety is a C1-C2alkyl radical, pyranylmethyl, tetrahydrofurfurylY* thióphenomethyl, benzhydryl, halobenzhydryl, polycyclic alcohol and substituted phenyl radical wherein the substituents are selected from the group consisting of a C1-C4alkyl radical, a halogen atom, a nitro group, a trifluoromethyl, formyl or chloroacetyl radical, a C1-C4alkoxy group, a hydrogen atom, a benzyl, chlorobenzyl, phenethyl and subalkylcarbo substituted phenethyl radical. wherein the substituents are selected from the group consisting of C1-C4alkyl, halogen, and Rlt is selected from the group consisting of C1-C4alkyl, C3-C4alkoxyalkyl and C3-C4alkenyl:; R10 and Rn together form a heterocyclic radical, preferably selected from the group consisting of azepinyl, morpholinyl, piperidinyl and piperidinyl radicals substituted with a Ct-G3alkyl radical; and when X is oxygen or sulfur, R10 is other than hydrogen and substituted phenyl, wherein the substituents are selected from the group consisting of halogen atoms, CL-C4alkoxy, phenoxy, trifluoromethyl, Ct-C6thio - alkyl, nitro group, isocyanate group, C2-C4polyalkoxy group, C3-C7cycloalkyl radical, C3-Cl0carboalkoxyalkyl, C±-C4haloalkyl, C3-C4alkenyl, Ct-C4alkyl and C3-Cl2hydroxy- alkylamidoalkyl, C2-C6dialkylamino group and phenylamine, radical C5—C10hydroxyalkylureidoalkyl, isocyanatoalkyl radical, in which the alkyl fragment is C±—C5alkyl radical, C3—C12alkylamidoalkyl radical, polyalkoxy radical 10 15 20 25 30 .35 40 45 50 55 60122*48 87 amidoalkyl, in which fragment the polyalkoxy group contains 3-6 repeating C2-C3alkoxy units, and the amidoalkyl fragment contains 4-12 carbon atoms; -SOaCl group, -SO3polyalkoxyamidoalkyl group, where the polyalkoxy fragment contains 3-6 repeating alkoxy units and the amidoalkyl fragment contains 4-12 carbon atoms; Rs is selected from the group consisting of hydrogen, C1-C4-alkyl, C3-C4-alkoxyalkyl, C3-C4 alkyl, hydroxyethyl and phenyl; R4 and R5 together constitute a heterocyclic radical selected from the group consisting of azepinyl, morpholinyl, piperidinyl and piperidinyl radicals substituted with a C1-C3alkyl radical; -CO^R^ group where when n = 1, the substituents are selected from the group consisting of nitro, chloro, C3-(^alkyl, C4-C6polyalkoxyalkyl, Cj-C6cycloalkyl, C3^C4alkenyl, C3-C6 alkoxyalkyl, C1-Ohydroxyalkyl, C C3-C3carboxyalkyl and trialkylammonioalkyl salts, and when n = 0, the substituents are selected from the group consisting of chlorine, thiopotassium, C1-C4alkyl, benzyl, C1-C4heteroalkyl, C1-C4chlorocarboxyalkyl, C4-C4polyalkoxyalkyl and acetyl ; group *—GOR7COYdZ, where R7 is selected from the group consisting of the radical —(CH3—)n, where n is 0 to 8, the radical —CH=CH—, the radical of formula 14, where M is H or Cl, the radical o formula 15, the radical -CCI=CCI-, -CH2OCHa-, -OC^CHjO-, and is the number 0 or 1, gdg.d = 1, then Y is selected from the group consisting of oxygen and sulfur atoms and the group -NH, and Z is selected from the group consisting of Ct-C4alkyl radical, hydrogen atom, C4-C14polyalkoxyalkyl radical, C4-C8dualkylaminoalkyl, C3-Ccalkynyl, phenyl and substituted phenyl, organic salts, inorganic salts, and when d = 0 , then Z is Cl or a group of the formula -NRCSR(=NR1), where R, Rt and R, are as above; the group -PO(R,)3, where Rt is selected from the group consisting of Q-Csalkoxy, amino, Cx-Csalkoxyamino, hydroxyl and organic base; group -SOwR,3 where R* is selected from the group consisting of an amino group, a Ca-C5atkyl, C1-C4haloalkyl and phenyl radical, a C1-C10dialkylamino group, Q-C10alkylamino, Q-Csalkoxy, a substituted phenyl radical, where the substituents are selected from the group consisting of a nitro group, a chlorine atom, a CL-C4alkyl radical and a methoxy group. 6. Agent according to claim. 1, characterized in that the active substance contains a compound of formula 1, in which R is secondary -CjH3, Rt is -CjHu, R3 is -CjH, and R3 is -COCOO C,H5. 7. The agent according to claim 1, characterized in that it contains as an active ingredient a compound of formula 1, in which R is -II -CjH^Rt is -CgH17) R3 is -CH3 and R3 is -CONHCl8Hj7. 8. The agent according to claim 1, characterized in that it contains as an active ingredient a compound of formula 1, wherein R is -II -CyH,, Rt is -C8H17, R2 is -C25, and R3 is -CONHCjg-H37. 9. The agent according to claim 1, characterized in that it contains as an active ingredient a compound of formula 1, in which R is -II -CTH15J Ri is -CgHiT, R3 is -CjHs; and R3 is -COCOO-C,H'. R-NCS+H2N-R2 R'X RNHCNHR2 R-N=CNHR2 • HX Scheme 4 SR* SR2 R-N=CNHR1 + R3NC0 —R-N=CN-R1 0=CNHB3 Scheme Z122 648 SR2 R-N = CNHR1 HX+ Et3N -h R3NC0 SR2 R- rvl=CNR1 + E + 3 N • HX 0=CNHR3 Scheme 3 ^ 9 Et3N ^ RN-CNHR, + R3CCl —1— RN=CNRi+ Et,N • HCl 0 = CR3 Scheme 4 SR2 n RN=C-NRi -Ol R3 Ri Formula 1 Formula 2 OH SR2 a ohR Formula 3 Formula 4 CH3 0 SR2 C^-NHCN-C = NRi R Formula 5 0 SR2 , CH2NHCN-C = NR, chTch' R Formula 6122 648 O SR2 O SR2 £€H2^ -NHCN-C=NR1 .NHCN-C=NRi R -£ R Formula7 Formula 8 ¥ , V ^NHC-N-C-NR, NHC-0(CH2CH20)x-CNHhQ ^ tCH3 CÓ, O O SR2 MNf ? /NH(i-N-(:=NR1 ^CHHU3NNH (CH^m- NHCNH -Q ^ Formula 40 o n 2 ?R* NHC-O-^OCNH -O //XVCH3 - cfis W 0 SR* 9 ^ 9 ^nhC- n-c-nr, ,nhc-nh-0-nh(!!nh-0 ^ \=/~CH3 CH3 o "NHCXR,0 _/ •122 648 O -CMlQ-CH3 CH3-(CH2)n-CH3 NHC - OCH2CH2(OCH2CH2)6- O Ó Formula 16 CH3-(CH2)n-CH, 0 CH3 NHC-0CH2CH2(0CH2CH2)6-Ó U Formula 17 o o PL PL PL