PL122155B1 - Method for manufacturing novel derivatives of benzamidine and fungicidegicid - Google Patents

Description

The subject of the invention is a method for preparing new derivatives of benzantidine and a fungicide. As fungicides, many different organomercury compounds, arsenic compounds, copper compounds, etc. have been used in agriculture. However, it was found that these compounds have a number of unfavorable features, such as residual soil poisoning and toxicity and residual toxicity to humans and animals, and therefore their use has been limited. Moreover, recently among the pests of various crop plants many fungi and bacteria resistant to the used products have appeared. This phenomenon occurs especially among fungi causing mildew, gray mold, sclerotia and pyrifculariosis. Therefore, the effect of chemical compounds that have been used for years on these plant pests has weakened For this reason, there is a need to select the type of fungicides intended for pest control. As a result of intensive research, it was found that the compounds produced according to the invention, i.e. new derivatives, have excellent fungicidal activity against various pests causing plant diseases. benzamidines of formula 1, in which alkyl groups, alkenyl groups, cycloalkyl groups or phenyl groups, or together with the nitrogen atom to which they are bonded, form a 5-7-membered saturated alicyclic ring, which may contain an oxygen atom as one of the members or may be substituted with one methyl group or two methyl groups, and R3 represents a hydrogen atom, a prostochain or branched alkyl, alkenyl or allkynyl group, a benzyl group, optionally substituted with chlorine atoms, a gypsy group, a cyanoalkyl group, an alkoxycaribonylimeityl group, a tanalkoxycarbonylethyl group, an alkoxymethyl group, a bis group /alkoxyxaribonylmethyl or phenoxyethyl group, optionally substituted alkyl group or alkoxy group, or R3 is a group of the formula an alkoxyalyl group, a lower alkenyl group, a lower alkylthiomethyl group, a furyl group, a thienyl group, a lower alkylthio group, a phenylthiomethyl group, a phenoxy group, an optionally substituted methyl group or a phenyl group, optionally substituted with a halogen atom, a methyl group, a methoxy group or a nitro group, or R3 denotes a group of formula 3, in which R5 and Rfl are the same or different and represent hydrogen atoms, lower alkyl groups, cyclohexyl groups, anilinocarbonyl groups, optionally substituted by an atom halogen and phenyl groups, optionally substituted with a halogen atom or a methyl group, or R3 is a group of the formula 4, in which R7 is a lower alkyl group, a cyclohexyl group, a benzyl group, a lower alkoxycarbonyl group The phenoxycarbonyl group, or R3, represents a group of the formula -SOa-R8, in which R8 represents a lower alkyl group, a trifluoroirmethyl group, a chloromethyl group or a phenyl group, optionally substituted with a halogen atom or a methyl group, as well as salts of these compounds of formula 5 in which Y is an acid, m is the number of equivalents of acid needed to obtain the salt, and X, n, R1, R2 and R3 have the meanings given above. Examples of lower alkyl groups constituting the substituent X are e.g. alkyl groups with 1-2 carbon aphthoms, there are methyl and ethyl groups.' Examples of alkyl groups constituting the substituents R1 and R2 are, for example, alkyl groups with 1-5 carbon atoms, such as methyl, ethyl, propyl, butyl and pentyl groups. Examples of alkenide groups constituting the substituent R1 and R2 are, for example, alkenyl groups with 3-4 carbon atoms, such as the allyl and 2-butenyl groups. Examples of cycloalkyl groups constituting substituents of R1 and R2 are, for example, cycloalkyl groups with 5-6 carbon atoms, such as the cyclopentyl group and cyclohexyl. Examples of 5-7 membered saturated alicyclic groups formed by the substituents R1 and R2 together with the nitrogen atom to which they are bonded are, for example, groups such as 1-pyrrolMynyl, 1-piperidyl, 2-methyl- 1-piperidyl, 2,6-dimatyl-1-piperidyl and hexahydroazepinyl. Examples of straight-chain or branched alkyl groups constituting the R3 substituent are, for example, alkyl groups with 1-13 carbon atoms, such as methyl, ethyl , isopropyl, butyl, penthyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl and tridecyl. Examples of straight-chain or branched aikenyl groups constituting the R3 substituent are, for example, alkenyl groups with 3-4 carbon atoms, such as allyl or 2-butenyl group. Examples of straight-chain or branched alkynyl groups constituting the R3 substituent are, for example, alkynyl groups with 3-4 carbon atoms, such as propyl and butynyl groups. Examples of benisyl groups substituted with chlorine atoms constituting the R3 substituent are e.g. chlorobenzyl and dichlorobenzyl groups. Examples of cyanoalkali groups constituting the R3 substituent are, for example, cyanoalkyl groups with 2-3 carbon atoms, such as cyanomethyl and cyanoethyl groups. Examples of aikoxycarbonylmethyl groups constituting the R3 substituent are, for example, alkoxycarbonylmethyl groups with 3-6 carbon atoms, such as methoxycarbonylmethyl, ethoxycarbonylmethyl, isopropoxycarbonylmethyl, α-ipropoxycarbonylmethyl and butoxycarbonylmethyl ignups. Examples of analkaxycarbonylmethyl groups constituting the R3 substituent are, for example, α-alkoxycarbonyl ethyl groups with 4^6 carbon atoms, such as as a-methoxycarbonylethyl group, \ α-ethoxycarbonylethyl, α-isopropoxycarbonylethyl, α-n-propoxycarbonylethyl and α-butoxycarfoonylethyl. 10 Examples of alkoxymethyl groups constituting the substituent R3 are, for example, alkoxymethyl groups with 2-5 carbon atoms, such as methoxymethyl, ethoxymethyl, propoxymethyl and butoxymethyl groups. 15 Examples of bis(alkoxycarbonyl/methyl) groups constituting the substituent R3 are, for example, bis(alkoxycarbonyl/methyl) groups with 5-11 carbon atoms, such as the bis/metaxycarbonylphaiethyl group, bis/ethoxycarbonyl/methyl group, bis/propoxycarbonyl group methyl and bis(buitoxylcarbonyl)methyl. Examples of substituted phenoxyethyl groups constituting the R3 substituent are, for example, substituted phenoxyethyl groups with 9-10 carbon atoms, such as methylphenoxyethyl, ethylphenoxyethyl, methoxyphenylethyl and ethoxyphenylmethyl. nyioethyl group. Examples of groups of formula 2 constituting the R3 substituent are, for example, the Formyl group, lower alkanoyl groups with 2-4 carbon atoms, such as the acetyl, propionyl, n-butyryl and isobutyryl groups, and the acetyl group substituted with carbon atoms. halogen groups, such as chloroacetyl, dichloroacetyl, trichloroacetyl, bromoacetyl and iodoacetyl, lower alkoxycarbonyl groups with 2-6 carbon atoms, such as methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl, n -butoxycarbonyl, isobutoxycarbonyl, tertiary butoxycarbonyl and tertiary butoxycarbonyl, lower alkoxyalkanoyl groups with 3-6 carbon atoms, such as rnetoxymethylcarbonyl, ethoxymethylcarbonyl and ethoxyethiocarbonyl groups, lower alkanoyl groups with 3-5 carbon atoms, such as acryloyl, crotonoyl, methacrylic, 3,3-dimethylaMyioyl and tert-2,3-dimethylacryloyl groups, lower alMlorbiomethylcarbonyl groups with 3-6 carbon atoms, such as the methylthioacetyyl group , ethylthioacetyl, propylthioacetyl, isopropylthioacetyl and butylthioacetyl, furolyl group, thienoyl group, smaller alMlothiocarbonyl groups with 2-5 carbon atoms, such as methylthiocarbonyl group, propylthiocarbonyl group, isopropylthiocarbonyl group and butylthiocarbonyl group, phenyl group iomethylcarboine- 55 Iowa , a phenoxycarbonyl group, halophenylcarbonyl groups such as p-chlorophenylcarbonyl group and 2,4-dimethylphenylcarbonyl group, methylphenylcarbonyl group, methoxyphenylcarbonyl group and nitrophenylcarbonyl group. 60 Examples of groups of formula 3 constituting the substituent R3 are, for example, the carbamoyl group, smaller alkylcarhamoyl groups with 2-5 carbon atoms, such as the methylcanbamoyl group, ethylcanbamoyl group, n-propylcarbamoyl group, isopropylcarbamoyl group, n^ butylcarbamoyl, isobutylcarbamoyl-5 122 155 6 wa, tertiary butylcarbamoyl and tert.butylcarbamoyl, lower dialkylcarbamoyl groups with 3-9 carbon atoms, such as divimethylcarbamoyl, diethylcarbamoyl, di-n-propylcarbamoyl groups ilowa , diisopropylcarbamoyl, dioxyfutylcarbamoyl, di-second-butylcarbamoyl and di-tertiary-butylcarbamoyl, cyMohexylcarbamoyl group, dicyclohexylcanbamoyl group, andilinocarbonylcarbamoyl group, cMoroanilineicarbonylcarbamoyl groups, such as 4-cMoixaniinocarbonylcarbamoyl group, phenylcarbamoyl group , halogen-phanylcarbamoyl groups, such as the 2-chlorophenylcarbamoyl group, the 3,4-dichloiphenylcarbamoyl group and the methylphenylcarbamoyl group. Examples of groups of the formula 4 constituting the substituent R3 are, for example, the lower α-Mlothiocarbamoyl groups of 2-5 carbon atoms, such as the meltylthiocarbamoyl group d atylthiocarbamoyl group, the cy-Mohexylthiocarbamoyl group, the benzylthiocarbamoyl group, lower alkoxycarbonylthiocarbamoyl groups with 3-6 carbon atoms, such as the methoxycarbonylthiocarbymoyl group, ethoxycanbonyl-thiocarbamoyl group, n-propoxycarbonylothiocarbamoyl, isopropooxycarbonyl liocaribamoyl , n--ibu(toxycar,bonyldiacarbamoylofwa, isobuitoxycarbonylthiocarbamoylofwa, II-n. butoxycadoonyiothiocarbamodyl and IH-rt. butoxycarbonyldocarbamoyl group and phenoxycarbonylthiocarbamoyl group. Examples of groups with the formula —SO2—R8 constituting a substituent R3 are, for example, lower alkanesulfonyl groups with 1^-2 carbon atoms, such as the methanesulfonyl group, the atanesulfonyl group, the trifluoromethanesulfonyl group, a chromomethanesulfonyl group, a benzenesulfonyl group, halobenzenesulfonyl groups, such as the 4hciMorobenesulfonyl group, 4-bromobenzenesulfonyl group and 2,5-diohloylbenzenesulfonyl group, and the toluenesulfonyl group. Thus, the method according to the invention towards wylt/wa- rza are new ibenzamidine derivatives of formula 1, and the feature of this method is that the nitrile of formula 6, in which X and n have the meanings given above, is reacted with II-row. an amine of the formula RXR2 NH, in which R1 and R2 have the meanings given above, in the presence of aluminum chloride, then the resulting complex is decomposed with water or an inorganic acid, and then treated with a strong alkaline agent, to obtain a benzamidine derivative of the formula 1, in which R3 is hydrogen and except for the hydrogen atom, and X, n, R1 and R2 have the meanings given above, a benzamidine derivative of formula 1, in which R3 is hydrogen, is reacted with a compound of the formula R3-Z, in which R3 is the given meanings with the exception of the hydrogen atom, and Z denotes a halogen atom, an isocyanate group or an isothiocyanate group, and then the compound of formula 1 is optionally converted into a salt by reaction with an acid. Thus, according to the invention, the new bemzamidine derivatives - of formula 1 can be prepared by the reaction shown in the scheme. The reactions are carried out at temperatures ranging from room temperature to 60°C, optionally in an organic solvent. The solvents that can be used are benzene, toluene, xylene, chlorobenzene, tetraline, nitrobenzene, chloroform, carbon tetrachloride, dixane, ethers, etc. The resulting complex of aluminum chloride and ibenzamidine is decomposed with water or an inorganic acid, and then the action of a strongly alkaline agent, obtaining a compound of formula 1, in which R3 is a hydrogen atom, and XJ n, R1 and R2 have the meanings given above. Hydrochloric acid, sulfuric acid, nitric acid, etc. can be used as the nondeongandic acid. The decomposition reaction is preferably carried out at a temperature ranging from room temperature to 50°C. As a strongly alkaline agent, sodium hydroxide, potassium hydroxide, etc. can be used, and the treatment with this agent is preferably carried out at room temperature or lower. Benzamidine derivatives with formula 1 in which R3 is hydrogen can also be prepared by reacting a Grignard reagent and II-row. amine in a solvent medium, and then treating with nitrile using heat and decomposing the product with ammonium chloride, and then treating with a strong alkaline agent. Benzamidine derivatives of formula 1, in which R3 has the above-mentioned meaning with the exception of the hydrogen atom, and - 40 hydrogen atoms, and Z is a halogen atom, such as chlorine or bromine, an isocyanate group or an isothiocyanate group. These reactions can be carried out without a solvent or in a solvent such as ether, benzene, acetone , tetrahydraBuran, dioxane, etc., optionally in the presence of a base such as potassium carbonate, sodium carbonate, pyridine, triethylamine, sodium hydroxide, potassium hydroxide, etc., at a temperature from room temperature to 50-250°C. the ibenzamidine derivative of formula I is reacted with an acid to give the product a salt of formula 5, in which X, n, R1, R2, R8 Y and mcg have the meanings given above. As the acid in this reaction, hydrochloric acid, ibromic acid, hydroiodic acid, perchloric acid, nitric acid, myalonic acid, oxalic acid, pdcrinic acid, tartaric acid, benzenesulfonic acid, tereiphthaic acid, adipic acid, salicylic acid, formic acid, acetylsalicylic acid, Icid cyclohexane carboxylic acid, propionic acid, acrylic acid, ifthalic acid, isophthalic acid, diglyco-65 acid, citric acid, alkylbenzenesulfonic acid, aminobenzenesilphonic acid, deihydroacetic acid, etc. Thus, Y in formula 5 means one of such acids. The acid treatment can be carried out by dissolving the acid in a solvent such as water, ethers, dioxane, dimethylsulfate, dimethylphoimamide, benzene, acetone, hexane, ethanol, methanol, isopropanol, tetrahydrororturane, etc., and then adding the compound to the solution of formula 1 at temperatures up to 100°C. Examples of new benzairnidine derivatives of formula 1 prepared according to the invention, as well as melting point (mp) or boiling point (p.p.) at a given pressure or refractive index (n) The dHa of these compounds is given in Table 1. Compound No. 1 1 1 2 / 1 3 4 5 « 7 e 0 10 ii Table 1 1 Meaning of substituents in formula 5 Substituent of formula 6 1 2 formula 8 formula 8 formula 8 pattern 8 pattern 8 pattern 8 pattern 8 pattern 8 pattern 12 and pattern 12 pattern 12 R1 1 3 i n-CsHy n-C4Hg —CH*CH= =CH,— iy 1 4 C2H5 n-C3H7 11-C4H9 —CH2CH= =CH^- I formula 9 formula 10 formula 11 CH, CHS CtH, n-CaHT formula 8 CH, , C2H5 n-CjH7 R8 5 H H H H H H H H H H H /Y/m 6 — — — — — — — — — " Melting point Md boiling point Hiub refractive index 7 t,w. 109—112°C/ 799.8 Pa /86°C/399.9 Pa t.b. 95—98°C/ 399.9 Pa b.p. 117-119°C/ 399.9 Pa | i.e. 98-101°C/ 399.9 Pa | i.e. 111-112°C/ 399.9 Pa | i.e. 141-147°C/ 533.2 Pa | i.e. | 145-146°C/ 799.8 Pa | i.e. 135—137°C/ 533.2Pa mp. 83—85°C b.b. 65-68°C/ 533.2 Pa | i.e. 97-106°C/ 533.2 Pa | i.e. 105—107°C/ 399.9 Pa |122 155 9 10 italblica 1 (continued) 12 1 12 13 14 15 | 16 17 18 19 20 21 1 22 23 24 " ** 26 27 26 29 pattern 12 pattern 12 pattern 12 pattern 12 pattern 12 pattern 12 pattern 12 pattern 12 pattern 12 pattern 12 pattern 12 pattern 12 pattern 17 pattern 18 pattern 18 pattern 19 pattern 19 formula 19 3 IZO-C3H7 11-C4H9 iso-CfHf 11-C5H11 1ZO-C5H11 11-C3H7 formula 13 n-CgHis n-C^H^ 4 5 iso-CsHr 11-C4H9 iso-CA n-C5Hii iso-C5Hii 11- C5H11 pattern 13 n-C6H13 n-C»Hi7 pattern 14 pattern 15 pattern 16 11-C3H7 C2H6 111-C3H7 11-C3H7 11-C4H9 iso-CsHn 11-C3H7 C,H, II-C3H7 II-C3H7 II-C4H0 iso-C5Hu H H H H H H H H H H H H H H H H mass 150—155°C/ 399.9 Pa | mass 130—134°C/ 133.3 Pa | mass 129—134°C/ 266.6 Pa | ng 1.5430 mass 156—163°C/ 133 .3 Pa 1 ng 1.4970 p.p. 119—121°C/ 533.2 Pa | m.p. 129—134°C/ 399.9 Pa 1 U. 61—63°C p. 117—1190CV 533.2 Pa p. 105—108°C/ 533.2 Ba | p. 115—122° CV 266.6 Pa | p. 117—120°C/ 133.3 Pa p. 130—134°C/ 133.3 Pa | p. 145— 150°C/ 133.3 Pa122 155 11 12 table 1 (continued) 1 30 31 32 33 34 35 36 37 38 39 1 40 ! 41 and 42 43 44 | 45 46 2 pattern 20 /formula 21 pattern 22 pattern 22 pattern 12 pattern 12 pattern 12 pattern 17 pattern 18 pattern 23 pattern 24 pattern 24 pattern 25 pattern 25 pattern 25 pattern 25 pattern 26 3 n-C3H7 n-C4H9 11-C3H7 iso- C5Hn C2H5 n-C3H7 11-C4H9 n-CaHy C2H5 n-C3H7 n-C3H7 iso-CgHii CH3 C2H5 n-CsH7 11-C4H9 C2H, 4 n-C3H7 n-C4H9 n-C3H7 iso-C5Hn C2H5 n-C3H7 H1- C4H9 n-C3H7 C2H5 n-C3H7 n-C3H7 iso-C5Hn CH3 C2H5 in-C3H7 n-C4H9 C2H, 5 H H H H H H H H H H H H H H H H 6 — — — — — — — — — — — — — — — 7 t.w. 113—119°C/ 266.6 Pa July 1.5160 mp. 114—117°C/ 133.3Pa t.b. 139—143°C/ 133.3Pa t.p. 111—118°CV 266.6Pa t.p. 124—130°C/ 133.3Pa t.p. 132—143°C/ 133.3Pa t.p. 123aC/ 133.3 Pa Lw. 123—126°C/ 399.9 Pa b.p. 134—139°C/ 266.6Pa t.p. 134-149°C/ 133.3 Pa | it.W. 167-170°C/ 133.3Pa t.p. 129—134°C/ 133.3Pa t.p. 99—103°C/ 133.3 Pa b.p. 123—12'6°C/ 133.3 Pa b.b. 138—144°C/ 133.3Pa t.p. 114—120°C/ 399.9 Pa |122 155 13 14 table 1 (continued) 1 47 48 49 50 51 52 53 54 55 56 57 58 59 60 61 62 63 2 1 pattern 26 pattern 27 pattern 27 pattern 28 pattern 28 pattern 29 pattern 30 pattern 30 pattern 31 pattern 31 pattern 32 pattern 33 pattern 3^ pattern 35 iwizóir 36 pattern 37 pattern 37 | 3 | 4 11-C4H9 C2H5 111-C3H7 C2H5 n-C3H7 C2H5 C2H5 n-C3H7 C^Hg 11-C3H7 CiHb QH5 C2H5 C2H5 C2H5 n-C3H7 C2H5 11-C4H9 C2H5 in-C3H7 C2H5 n-C3H7 C2H5 C2H5 n -C3H7 C2H5 n -C3H7 C2H5 C2H5 C2H5 C2H5 C2H5 n-C3H7 1 C2H5 1 5 H H H H H H H H H H H H ^ H H H H H 6 — — — — | — — — — — — — 7 t.p. 141—143°C/ 133.3Pa t.b. 112—117°C/ 399.9 Pa b.p. 127—133°C/ 133.3Pa t.b. 123-129°C/ 266.6 Pa | (b.p. 135—143°C/ 266.6 Pa | b.p. 138—147°C/ 399.9 Pa b.p. 130—136°C/ 266.6 Pa b.b. 127—134°C/ 266.6 Pa | lt.W 122—127°C/ 266.6 Pa i.t. 130—135°C/ 133.3 Pa 1 p.i. 115—120°C/ 266.6 Pa i.p. 105—108°C/ 799.8 Pa i.p. 119—123°C/ 133.3 Pa po 146—153°C/ 399.9 Pa po 138—146°C/ 266.6 Pa po 137—148°CV 166.6 Pa po 126—133°C/ 266 .6 Pa |122155 15 16 talMdica 1 (continued) . 1 64 65 66 67 68 69 \ 70 , Tl 72 73 74 75 76 77 78 79 80 81,, 82 63 94 85 86 87 88 89 90 91 92. 93 94 95 , 96 97 98 99 2 pattern 8 pattern 8 pattern 8 . pattern 8 i pattern 8 pattern 8 pattern jB pattern 8 pattern 8 pattern 8 pattern 8 pattern 8 pattern 8 pattern 8 pattern 8 Pattern 8 pattern 8 pattern 8 pattern 8 pattern 8 Pattern 18 pattern 12 pattern 12 pattern 17 pattern 17 pattern 8 pattern 23 pattern 8 pattern 8 pattern 8 pattern 8 pattern 8 pattern 8 pattern 8 pattern 8 pattern 8 3 C*H9 CaH5 C2H3 C»H, CH, CH, C2H5 C»h« Crfl, QH, C*H, C*H, C»H5 CjH5 CiH, Crfl, Crfl, n-CsHr —CIfcCH= 11-C4H, CjHj CH, 4 CjH, C2H5 C2H5 C2H5 CaH|CaH, C2H7 C2H5 C2H5 C2H5 C2H5 C2H5 C2H5 CjH5 C2H5 C2H6 C2H5 n-C3H7 ^CHjCH= n-C4H, CA CHj formula 14 11-C3H7 CiHb CHj C,Hg C2H5 CH, CH, CH, C2H5 C2H5 CjHj C2H5 C2H5 | n-C3HT CjHj formula 7 C*H5 CjHs C2H8 C2H5 C,H5 CjH, C,H5 CjH, C2H, C2H5 6 H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H 6 HO HBr HJ HNO3 HCIO4 HCOOH .[( COOHCH/ /OH)h CHf (COOH) ), ( CHi)4 (COOH), formula 38 formula 39 formula 40 formula 41 .formula 42 formula 43 formula 44 Ha HO Ha Ha Ha Ha Ha Ha Ha HCl^HjO CHsCH, COOH —0(CH, COOH), CH»= CHCOOH formula 45 pattern 46 pattern 47 pattern 48 pattern 49 pattern 50 7 m.p. 143—146°C U. 165—169°C mp. 177—178°C t,mp. 95—97QC mp. 143—146°C mp. 89-91°C mp. 168—169°C ¦t-t 129—130°C | mp 107—109°C mp. 119—121aC U. 61—63°C mp. 107—109oC mp. 117—119aC mp. 119-120°C mp. 202—203*C ' mp. 131-132°C mp. 158—160°C L.L. 181—185°C mp. 137-141°C mp. 169-171°C mp. 205—207°C mp. 253-254°C mp. 267-268°C mp. 171-172°C mp. 232-233°C mp. 234^235°C t-t 170—173°C | n£ 1.5190 njj1 1.5330 n}.1 1.5443 t.p. 180°C n?? 1.5645 m.p. 124—126°C n* 1.5211 ng 1.5104 U. 224—226°C122 155 17 18 table 1 (continued) 1 1 100 | 101 | 102 | 103 104 | 105 106 107 108 1 109 110 | 111 112 113 114 115 1)16 117 118 119 120 1 2 pattern 8 L pattern 8 pattern 8 pattern 8 pattern 8 pattern 8 pattern 8 pattern 8 pattern 8 pattern 8 pattern 8 pattern 8 pattern 8 pattern 8 pattern 8 pattern 8 pattern 8 pattern 8 pattern 8 pattern 8 pattern 8 3 C2H5 | C2H5 | C2H5 C2H5 C2H5 C2H5 C2H5 C2H5 C2H5 C2H5 C2H5 C2H5 C2H5 C2H6 C2H5 C2H5 C2H5 C2H5 C2H5 C2H5 C*H5 4 C2H5 C,H5 C2H5 C2H5 C2H5 C2H5 C*H5 C2H5 C2H6 C2H5 C2H6 C2 H5 C2H5 C2H5 C2H5 C2H5 C2H5 C2H6 C2H5 C2H5 C2H6 5 H CH3 C*H5 11-C3H7 iso-CjH7 11-C4H9 in-CjHn pattern 52 djzo-C5Hn pattern 18 —CHiCOOCjH, —CHiCHfCN —CHA^DOCjH^a —/CH2/10—CHj —/CHJu-CH3 —/CH2/12 —CH9 formula 52 formula 53 formula 54 —CH2CN —CHjOCHs 6 formula 51 HJ HJ HJ N HJ — — — Ha — — — — — — — — — — 7 n*® 1.5452 mp. 139—142°C U. 155^158°C mp. 122^124°C mp. 98—104aC/ 666.5Pa mp. 10&—111°C itJW. 128—132°C/ 666.5Pa t.p. 172—177°C/ 133.3Pa t.b. 126^133°C/ 799.8 Pa mp. 154—15 €°C b.p. 130—137°C/ 3&9.9Pa t.b. 161-165°C | ng 1.5023 p.p. 159°C/59.9Pa t.p. 155^159°C/ 33.3Pa t.b. 164^169°C/ 33.3 Pa | i.e. 156-161°C/ 33.3 Pa | it,w. 152—155°CV 33.3 Pa 1 p.p. 164-171°C/ 46.7 Pa | i.e. 157-164°C/ 133.3 Pa | i.e. 1 119—123°C/ 799.8 Pa ' |122 155 19 20 table 1 {continued) 1 1 | 121 1 122 123 124 125 1126 127 128 129 130 131 1 132 133 134 135 136 137 138 139 140 141 142 143 144 145 1 2 1 'pattern 8 pattern 8 pattern 8 pattern 12 pattern 12 pattern 12 pattern 12 pattern 12 pattern 12 pattern 12 pattern 12 pattern 12 pattern 12 pattern 12 pattern 12 pattern 12 pattern 8 pattern 8 pattern 8 pattern 8 pattern 8 pattern 8 pattern 8 pattern 8 pattern 8 | 3. | 4 | 5 C2H5 n-C3H7 11-C3H7 H-C3H7 n-C3H7 n-C3H7 11-C4H9 n-C3H7 n-CsH7 n-C3H7 n-C3H7 n-C3H7 n-C3H7 n-C3H7 n-C3H7 iso-CgHn C2H5 C2H5 C2H5 C2H5 C2H5 C2H5 C2H5 C2H5 C2H5 C2H5 J1-C3H7 in-C3H7 in-C3H7 ¦n-C3H7 n-C3H7 11-C4H9 n-C3H7 n-C3H7 ,n-C3H7 ,n-C3H7 ,n-C3H7 n-C3H7 ,n- C3H7 n-C3H7 iso-C5Hn C2H5 C2H5 C2H5 C2H5 C2H5 C2H5 C2H5 C2H5 C2H5 | —CN | CH3 CH3 C2H5 11-C3H7 H-C3H7 11-C3H7 H1-C4H9 —i^CHa/eCHs n-C5Hn formula 55 formula 56 iso-C3H7 iso-CgHn C2H5 11-C3H7 —CHigGH^CH2 —CH2C=CH —CH/CH3 /—COOC^H —CH/COO-iso-C3HT/2 —CH2COOCH3 —CH*COO-! Lz! 0-C3H7 —c/o/cn —CTD/CHACHa pattern 57 6 — HJ — — HJ — HJ — — HJ HBr HBr HJ — HJ HJ — — — — — — — — — : 7 mp. 84-85°C mp. 124—126°C ng 1.5152 ng 1.5290 mp. 158—159°C ng 1.5054 mp. 131-133°C mp. 89-94°C b.b. 154—163°C/ 399.9Pa mp. 63—67°C mp. 136-137°C mp. 145—147°C mp. 152—156°C mp. 139°C/399.9 Pa | m.p. 157-158°C decomposition at 124-126°C mp. 122°C/799.8 Pa | i.e. 132—133°C/ 799.8Pa t.b. 133-136°C/ 399.9 Pa | ng 1.4830 p.p. 144-153°C/ 933.1 Pa | i.e. 117-134°C/ 399.9 Pa b.b. 130—134°C/ 133.3 Pa b.b. 136-138°C/ 133.3 Pa | m.p. 68—70°C122 155 21 22 /table 1 (continued) 1 | 2 '146 147 148 .149. 150 151 152 ; 153 154 155 156 157 1j58 1(59 160 161 162 163 164 165 166 167 168 169 170 pattern 8 pattern 8 pattern 8 pattern 8 pattern 8 pattern 8 pattern 8 pattern 8 pattern 8 pattern 8 pattern 8 pattern 8 pattern 8 pattern 8 pattern 8 pattern 8 pattern 8 pattern 8 pattern 8 pattern 12 pattern 12 pattern 8 pattern 8 pattern 8 pattern 8 3 C2H5 C2H5 C2H5 C2H5 C2H5 C2H5 C2H5 C2H5 C2H5 C2H5t C2H5 C2H5 C2H5 C2H5 C2H5 C2H5 C2H5 N C2H5 C2H5 11-C 3H7 C3H7 C2H5 C2H5 C2H5 C2H5 4 C2H5 C2H5 C2H5 C2H.5 C2H5 C2H5 C2H5 C2H5 C2H5 C2H5 C2H5 C2H5 C2H5 C2H5 C2H5 C2H5 C2H5 C2H5 C2H5 n-C3H7 C3H7 C2H5 C2H5 C2H5 C2H5 5 pattern 58 pattern 59 pattern 60 —C/O/CHj GL —C/O/CH2SCH3 —C /0/CH2S-iso-CaH7 formula 61 formula 62 formula 63 —C/0/CH=C/CH3/2 —C/0/C/CH3/=CVH/CHf —C/O/CHsPCaHg —C/O/ CHzOCHs —C/O/CHjjCHjOCjHb —C/0/CHQt —C/O/CCl, ^C/0/CH2Br —C/O/CH2J —CHO formula 58 formula 64 —C/O/—O—CHj —C/ O/—OC2H5 —C/0/0-n-C3H7 —C/O/O-iizo-CaH?6 — — — — — — — — — — — — — — — — — — — — j_ — — — — — 7 t, mp 150—152°C mp 140—141°C mp 75—77°C ng 1.5540 ng 1.5640 n^ 1.5521 n£ 1.6066 1 ng 1.5830 ng 1.5946 og 1.5508 ng 1.5495 ng 1.5240 ,r£° 1.5400 ng 1.5052 ng 1.5580 m.p. 73—74°C ng 1.5624 ng 1.5920 vol., vol. 79—82°C ng 1.5805 mp. 115—116°C mp. 132—133°C/ 119.9Pa t.b. 148—149°C/ 266.6Pa t.b. 142—14*5°C/ 99.9Pa t.p. 113—122°C/ 0.33 Pa122 155 23 24 table 1 (continued) 1 1 171 172 173 174 \175 176 177 | 178 | 170 | 160 101 132 | 183 | 184 | 185 186 187 | 188 189 190 ldl ' 192 193 104 195 | 196 | 197 | 198 199 | 2 pattern 8 pattern 8 IWZÓGT 8 pattern 8 pattern 8 pattern 8 pattern 8 pattern 8 pattern 8 pattern 8 pattern 8 pattern 8 pattern 8 pattern 8 pattern 8 pattern 8 pattern 8 pattern 8 pattern 8 pattern 8 pattern 8 and pattern 8 pattern 8 pattern 8 pattern 8 pattern 8 pattern 8 pattern 8 pattern 8 3 1 C2H5 C2H5 C2H5 CjHs C2H5 C,HS C*H5 C*H5 C*H5 C*H5 CjH5 CjHj CXH5 C,HS C,H5 C2H5 C*HS C*H, C *H, C2HS _ CtHs C2H5 C*H5 C*H5 C*H, C*H5 C,H5 CtH5 C,HB | 1 4 CsH, 1 CaH, CjH» C,H„ CjH, CjH,- C2HS C,H« CjH, CjHj CrfJ, e,H, C2H5 CjH, C,H, C,H, C,H, CjH, C2H5 ,CiH, CjH, C,H, CjH, . C2H, CjH, CjH5 | C,U« C2H5 C2H9 | 5 —C/O/O-n-CA —C/O/SCH/CH3/, —C/O/SCjHs formula 57 formula 65 —CyO/N/CHa/, ^cyo/N/c^Hj/, —CVO/ N/-ai-CjH7/j —C/O/NHCH3 —CyO/NHCjHs —Cto/NH-n-CsHT —C/O/NH-n-C^ formula 66 formula 67 formula 68 formula 69 formula 70 formula 71 —C/ S/NHCH3 —C/S/NH-iso-C3H7 formula 72 formula 73 formula 74 -S03CH3 SO&Jis formula 75 formula 6r 76 formula 77 formula 78 6 — — — — — — — — — — — — — — — — — — — — — — — — — — — — — ...)... . ^—.,„,,,,.,„,J 7 t.w. 141—144°C/ 59.9 Pa n£ 1.5543 n£ 1.5670 n£ 1.5763' ng 1.5675 1 p.p. 142^144°C/ 106.6Pa t.b. 140°G/79.9 Pa | i.e. 144-147°C/ 66.7 Pa | m.p. 72-74°C | U. 69—70°C nj* 1.5418 mp. 66-68°C | m.p. 164-165°C | , m.p. 148-150°C | m.p. 105-107°C | n^ 1.6016 n£ 1.5982 U. 57—60°C | n£ 1.6101 ng 1.5888 m.p. 87-89°C | U. 152^153°C | n£ 1.6200 n£ 1.5533 t.p. 76-77°C | m.p. 53—54°C ' 1 mp. 99-102°C mp. 119-121°C | m.p. 143—145°C122 155 25 26 table 1 (continued) 1 200 201 202 203 204 205 206 2 pattern 8 pattern 8 pattern 8 pattern 8 pattern 8 pattern 8 pattern 8 3 C*H5 C2H5 C,H5 C*H5 C* H5 C2H5 C2H< 4 C*H5 C2H5 C2H5 C2H5 C2H5 C2H5 C2H5 6 —S02CF, —SO2CH2CI —C/S/NHC/O/CH3 —C/S/NHCYO/OCtHa .—CyS/NHC/O/O-n- -C3H7 ^C/S/NHC/O/O-iso- -C3H7 formula 70 6 — — — ¦ _ — — — 7 mp. 102-103°C mp. 89-91°C mp. 138-139°C mp. 112-113°C, mp 93-95°C, mp 113-115°C, decomposition temperature 145-146°C. The above-mentioned drugs and excipients can be used individually or in mixtures, depending on the purpose and type of preparation. rat, method of application and other factors. Dusts generally contain, for example, 1-25 parts by weight of the active substance, and the remaining part of the preparation constitutes a solid carrier. Wettable powders usually contain, for example, 25-90 parts by weight of the active substance, and, in addition, a solid carrier, a dispersant and a wetter, and, if necessary, a protective colloid, a thixotropic agent, an antifoam agent, etc. The granulates generally contain 1-35 parts by weight of the active substance and a solid carrier as the main component of the remaining part of the preparation. The active substance is mixed with the carrier to obtain a homogeneous mixture or it is deposited on the carrier or adsorbed on its surface, the size of the granules being approximately 0.2-1.5 mm. Emulsifiable concentrates usually contain, for example, 5-50 parts by weight of the active substance and about 5-20 parts by weight of the emulsifier, and the remaining part of the preparation constitutes a liquid carrier and, if necessary, a corrosion inhibitor. In order to effectively combat diseases, The fungicides according to the invention, which can be given in the form of various preparations, can be applied to flooded or untreated fields at a dose of 1-6000 g of active substance, preferably 10-1000 g of active substance per 0.1 ha, applying the treatment before - dressing the plants or treating the leaves after the plants have emerged, or introducing them into the soil or water. By disinfecting or covering the seeds with the agents according to the invention, it is also possible to effectively combat diseases transmitted by soil or infected seeds. For this purpose, the seeds are covered with the agent in an amount of 0.1-2 micrograms, preferably 0.2-0.5 thousand of the active substance per seed weight. The fungicides according to the invention in vetches have excellent effectiveness in combating powdery mildew in crops. different field plants, even when using lower doses than with commercially available fungicides. 65 Thanks to the use of the agents according to the invention, the subject of the invention is also a fungicide containing an inert carrier and an active substance acceptable in agriculture, and the feature of this agent is that it contains as an active substance a new benzamidine derivative of the formula 1 or its salt. The compounds are preferably used as the active substances of the agents according to the invention are salts of the formula 5, in which each of the substituents R1 and R represents an alkyl group, especially an ethyl group, R3 represents a hydrogen alt, an alkyl group, such as an isopropyl group, an alkoxycarbonylmethyl group, a α-alkoxycarbonyl ethyl group, alkoxymethyl group, bistooxycarbonyl/methyl group, formyl group or lower alkoxycarbonylthiocaryltamoyl group, and , adipic acid, salicylic acid, tartaric acid and hydrochloric acid. To use the compound of formula 1 or its derivative as a fungicide, it can be given in the form of preparations commonly used for fungicides, e.g. in the form of dust, granules, wettable powder, concentrate for emulsification, water-soluble powder, milk, etc., by mixing with an inert carrier. As inert carriers may be used solid, liquid or gaseous carriers usually used for the preparation of herbicidal preparations, e.g. talc, clay, kaolin, diatomaceous earth, white coal, calcium carbonate, potassium chlorate, potassium nitrate, wood flour, starch, sodium cellulose, apnabian gum, vinyl chloride, carbon dioxide, Fleon, propane, butane, etc. The fungicides of the invention can also be used contain auxiliary substances such as spraying agents, dispersants, emulsifiers, etc. Moreover, fungicides according to the invention can be mixed with herbicides, insecticides, other chemical substances used in agriculture, fertilizers, such as urea, ammonium sulfate, ammonium phosphate and potassium fertilizers, soil care agents, etc.122 155 17 28, very good effectiveness is achieved in combating gray mold, anthracnose, piriculariosis, helmintosporia, bacterial leaf rot, hardwood rot wild boar and bark damping off (Valsa mali). Moreover, the agents according to the invention have minimal toxicity towards cultivated plants, as well as towards humans and animals. The method according to the invention and the fungicides according to the invention are illustrated by the following examples. Example I. Preparation of N,N-diethylbenzamidine ( compound no. 1). To a cooled and stirred mixture of 10 g (0.097 mol) of benzonitrile and 9.5 g (0.128 mol) of diethylamine, 14.3 g (0.1 mol) of powdered (anhydrous aluminum chloride) are gradually added, and the mixture is heated for 1.5 hours at a temperature of about 50°C. After pouring the reaction mixture into 200 ml of ice water containing 4 ml of concentrated Hd, a solution prepared by dissolving 40 g (1 mole) of caustic soda in 150 ml of water is added to obtain a strong reaction. alkaline. The mixture was stirred for 30 minutes and extracted with ether, and the extract was dried over anhydrous sodium sulfate and distilled to obtain 15.7 g of N,N-diethyl-benzimidine in the form of a light yellow liquid. Example II. Preparation of N,N-diethylbenzamidine oxalate (compound No. 71) 2.1 g of oxalic acid are dissolved in 30 ml of ethyl alcohol, and then 3.0 g of N,N-diethylbenzamidine obtained as in the example are added dropwise to the cooled solution I. The reaction mixture is allowed to stand overnight and then the ethyl alcohol is removed, obtaining crystals which are recrystallized from a mixture of ethyl alcohol and ether. 4.0 g of N,N-diethylbenzamidine oxalate are obtained in the form of colorless crystals. Example III. Preparation of N,N-di-n-propyl-4-methylbenzamidine (compound of formula 26). 11.7 g (0.1 mole) of p-cyanotoluene and 12 g (0.12 mole) of di-n-propylamine are dissolved in 50 ml of benzene and 16 g (0.11 mole) are gradually added to the resulting solution. powdered anhydrous aluminum chloride. The resulting mixture is stirred for 3 hours at a temperature not higher than 60°C, then poured into 200 ml of ice water and a 20% aqueous solution of caustic soda is gradually added to the mixture to obtain a strongly alkaline. The mixture is stirred for 30 minutes and then extracted with two 100 ml portions of benzene. The benzene layer is dried over anhydrous sodium sulfate, and then the benzene is distilled off. The residue is distilled under reduced pressure to obtain 16.5 g of the desired product in the form of a light yellow liquid. Example IV. Preparation of N,N-diethylbenzamidine adiptimiate (compound no. 73). 8.3 g (0.056 mol) of adipidic acid are dissolved in 150 ml of ethanol, and then 10 g (0.056 mol) of N,N-diethylbenzamidine obtained as in Example I. The reaction mixture is left in the refrigerator for 3 days, and then the precipitated crystals are filtered off and recrystallized from a mixture of ethanol and ether, obtaining 12.5 g of the desired product in the form of colorless crystals. 5 Example V. Preparation of N,'N-diethyl-N'-isopropylibenzamidine (compound No. 104). A mixture of 3 g (0.017 mol) of N,'N-diethylbenzamidine obtained as in Example I and 8.7 g (0.051 mol) of iodide isopropyl is heated at 80°C for 1 hour, then left to cool and strongly alkalinized with a 25% aqueous solution of caustic soda. After extraction with ether, the organic layer is dried over anhydrous sodium sulfate and then distilled, obtaining 1.3 g of N-diethyl-N-isopropylphoenzamidine in the form of a colorless liquid. Example VI. Preparation of NjN-diethyl-N'-ethoxycanbonylmethylbenizamadine (compound no. 110). 20 5.3 g (0.03 mol) of N,N-diethyiobenzamidine obtained as in Example 1 are dissolved in 50 ml of ether, and then added dropwise to the resulting solution with stirring and at a room temperature of 5 .h g (0.03 mol) of ethyl bromoacetate. The mixture, which turns cloudy quickly and whose temperature rises slightly, is stirred for 2 hours, heating it to reflux temperature. The mixture is left to cool. ¬ and in order to make it strongly alkaline, 30 concentrated aqueous sodium hydroxide solution is added. The resulting mixture is extracted with ether, the ether layer is dried over anhydrous magnesium sulfate, and then the solvent is distilled off under reduced pressure. The residue is distilled under reduced pressure. pressure, obtaining 4.9 g of the desired product in the form of a light yellow liquid. Example 7. Preparation of NjN-diethylD-N'-methoxymethylbenzamidine (compound No. 120). 5.3 g (0.3 g) are dissolved in 50 ml of benzene. 03 mol) of N,N-methylenebenzamidine obtained as in Example 1, and then 2.5 g (0.032 mol) of methoxymethyl chloride are gradually added with stirring, as a result of which the mixture becomes rapidly messy. The mixture is stirred at room temperature for 1 hour, then heated to reflux for 10 minutes, left to cool and made basic with a highly concentrated aqueous solution of 5t sodium hydroxide. After extraction with benzene, the benzene layer is It is stirred over anhydrous magnesium sulfate and the solvent is distilled off under reduced pressure. The residue is distilled under reduced pressure, obtaining 1 g of the edible product in the form of a colorless liquid. Example VIII. Preparation of N,N-diethide-N-3-allylbenzanridine (compound no. 137). A mixture of 5.0 g (0.0248 mol) of iN^N^diethylbenzamidine obtained as in Example 1 and 5.2 g (0.0425 mol) of allyl bromide is heated at reflux temperature for 1.5 hours, left to cool, made strongly alkaline with 250% aqueous sodium hydroxide solution and extracted with ether. The ether layer was dried over anhydrous sodium sulfate and distilled under reduced pressure to obtain 2.1 g of the desired product in the form of a colorless liquid. Example 9. Preparation of N,N-diethyl-N-blis(isopylcartoonyl)methylbenzamadine (compound of formula 140). To 100 ml of acetone are added 5.3 g (0.03 mole) of N,N-diethylbenzamidine obtained as in Example 1, 8 g (0.03 mole) of isopropyl brommallotate and 4 g (0.03 mole) of anhydrous carbonate. calcium, then the mixture is refluxed for 3 hours and allowed to cool. After filtering off the insoluble solids, acetone is distilled off under reduced pressure, and the residue is dissolved in benzene and washed with brine solution. The benzene layer is dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The concentrated benzene solution and solution were chromatographed on a column filled with silica gel, using first benzene as the eluent, and then a mixture of benzene and ethyl acetate (4:1). 2.1 g of the desired compound are obtained in the form of a light yellow liquid. Example X. Preparation of N,N-diethyl-N'-methoxycarbonylbenzamidine (compound no. 167). 5.0 g (0.028 mol) of N,N-diethylbenzamidine obtained as in Example 1 and 3.9 g (0.028 mol) of potassium carbonate are added to 200 ml of acetone, and then 5.3 g (0.028 mol) of potassium carbonate are added dropwise to the resulting mixture cooled with ice. g (0.057 mol) of methyl chloroformate. The ice-cooled mixture was stirred for 2 hours, left overnight, and then filtered. The filtrate is concentrated and extracted with benzene, and then the benzene layer is washed successively with dilute aqueous sodium hydroxide solution, dilute hydrochloric acid and water, and then distilled to obtain 2.4 g of NjNncVuethyl-N^methoxycarbonylbenzaimaidine in the form of a yellow liquid. Example XI. Preparation of N,N-diethyl-N'-phenylcarbamoyl-benzanikine (compound no. 185). To 80 ml of benzene, 5.3 g (0.03 mol) of N,N-diethylbenzanidine obtained as in Example 1 and 3.7 g (0.03 mol) of phenyl isocyanate are added, and the mixture is stirred at room temperature. ¬ January within 3 hours. After the reaction is completed, the reaction mixture is concentrated under reduced pressure to a volume of approximately 40 ml and n-hexane is gradually added to it to obtain crude crystals, which are re-formalized from a mixture of benzene and n-hexane to obtain 4.8 g N,N-diethyl-N-phenyl caribaimoyl benzamidine in the form of fine-grained crystals. Example XII. Preparation of N,N-diethyl-N,-methylcarbamoylbenzamidine (compound no. 189). 5 g (0.0284 mol) of N,N-diethylbenziamidine obtained as in Example 1 were dissolved in anhydrous benzene, and then 2.1 g (0.02 (84 mol) of methyl isothiocyanate were added dropwise while cooling with ice. After addition, the mixture is stirred for 30 minutes at room temperature, and then heated in a water bath at 40° C. for 1 hour. The mixture is left overnight, then the benzene is distilled off, and the residue is chromatographed on a precipitation column. filled with silica gel, obtaining 5.2 g of the desired product in the form of a yellow viscous liquid. Example 13. Preparation of N,N-diethyl-N-trifluoromethanesulfonylbenzamidine {compound No. 200). io To 50 ml of acetone, 5.3 g (0.03 mol) of N,N-diethylbenzamidine obtained as in Example 1 and 4.3 g (0.03 mol) of anhydrous potassium carbonate are added. A solution of 5 g (0.03 mol) of trifluoromethanesulfonyl chloride in a small amount of acetone was gradually added dropwise to the stirred and ice-cooled mixture, and the mixture was stirred while cooling with ice for 1 hour. The mixture is allowed to warm to room temperature and stirred overnight. After filtration, the insoluble substances are removed from the filtrate under reduced pressure and acetone, and the residue is dissolved in benzene. The benzene solution is washed with water and dried over anhydrous magnesium sulfate, and then the solvent is distilled off under reduced pressure. The residue is recrystallized from a mixture of benzene and n-hexane to obtain 3 g of the desired product in the form of granular colorless crystals. 30 Example XIV. Preparation of N,NHdiethyl-N'-(e1xoxycaribonylthio1carbamoyl)-ibenzamdine (compound no. 203). 6.3 g (0.062 mol) of potassium thiocyanate are dissolved in 100 ml of anhydrous acetone, then 6.2 g (0.057 mol) of ethyl chlorocarbonate are added at room temperature and the mixture is heated for 30 minutes. Then, while cooling the mixture with ice, N,NHdiethylbenzamiidine obtained as in Example 1 is added and the mixture is stirred at room temperature for 4 hours. After pouring the mixture into 300 ml of ice water and recrystallizing the precipitated crystals from ethanol, 9.5 g of the desired compound are obtained in the form of light yellow crystals. 45 Example XV. Emulsifiable concentrates. 20 parts of N,N-diethylbenzimidine (compound No. 1), 5 parts of Toxanone (surfactant produced by Sanyo Kasei Kogyo K.K.) and 75 parts of xylene are mixed to obtain 100 parts of monomogenous emulsifiable concentrate. Example XVI. Wetted powders. 20 parts N,N-two-! n-ibutyl-2,5-dimethylbenzamidine (compound no. 28), 1 part of powdered Demol EP (surfactant produced by 55 Kao-Atlas Co., Ltd.), 20 parts of white carbon and 59 parts of talc are mixed to obtain a homogeneous mixture, after pulverization, 100 parts of wettable powder are obtained. Example XVII. Dust. 60 2 parts of N,N-diethyl-pHOchlorobenzamldine (pipe compound 48) and 98 parts of talc are mixed until 100 parts of homogeneous dust are obtained. Example 18. Granules or tablets. 10 parts of N,N-tetraniethyylene-2-methyliobenzamidine-65 (compound No. 86), 15 parts of starch, 2 parts of ben-31 122155 tomite and 3 parts of sodium lauryl sulfate are mixed until a homogeneous mixture is obtained, which is powdered to obtain 100 parts of granules or tablets. Example XIX. Effect on cucumber mildew. Petiole seedlings (Sagamihanijiro-fushinari varieties) were planted one in plastic pots with a diameter of 6 cm, and after 17 days they were used as host plants. Each plant was treated a diluted emulsifiable concentrate prepared as in Example 15 and containing 1,000 parts per million (ppm) of the active substance in question. The concentrates were applied by spraying at a dose of 20 ml per pot. Each plant was air-dried and infected by uniform spraying with a suspension of Sphaeroitheca Fuligiinea spores. A spore suspension was prepared by shaking spores from already infected cucumber leaves onto a Petri dish using a soft brush and diluting the conidia with water to such a concentration that 10 conidia could be observed in the preparation under a 150x magnifying microscope. The infected plants were kept in the greenhouse for 11 days, after which the number of disease outbreaks on the first leaf was calculated. The percentage effectiveness of each compound was calculated using the following equation. < / effectiveness = Average number of disease outbreaks v in groups of treated plants \ 1 | 26 28 35 37 30 42. 43 45 46 47 48 Efficacy (? /a) 2 U0O 96 100 100 100 80 82 98 80 93 97 80 95 100 100 99 100 90 100 Phytotoxicity 3 | none none none birak none none none none none none birak ibrak none none none none ibrak none ibrak | 10 15 20 25 30 35 45 55 60 1 50 51 52 53 54 55 57 58 59 60 61 63 64 65 66 6* 68 69 70 71 72 73 74 75 76 77 78 79 80 81 83 8 4 85 87 88 89 90 91 92 93 94 95 96 97 98 99 100 101 102 103 104 105 106 107 108 1109 110 112 114 115 116 117 118 2 100 85 100 87 92 96 94 aoo 100 10 0 100 100 100 100 100 100 100 100 100 100 aoo 100 aoo aoo 100 aoo 100 100 aoo aoo 98 98 100 100 100 80 100 100 aoo 100 100 100 100 100 100 100 100 95 99 100 100 94 100 100 100 85 100 100 98 96 92 100 100 3 none inone none none none none none none 'none none none none ' none none none none none none none none none none none 1 none none none none none none none ' none none none none none none none none none none none none none ( none ( none and none 1 none none none none none none none none none ( none ibrak none none Ibrak ibrak Ibrak ibrak Ibrak none33 122 155 table 2 (continued) 34 table 2 (continued) 1 l ' 120 122 123 124 126 127 128 129 130 131 132 ¦ 133 134 135 136 143 144 145 146 147 148 149 150 151 152 153 154 155 156 157 158 159 160 161 162 163 | 164 165 166 167 168 169 170 171 172 173 174 176 1177 178 179 180 181 183 184 185 186 188 189 190 191 192 2 89 85 80 91 82 1 00 95 100 . 90 87 100 84 89 80 100 100 88 72 92 ttOO 100 100 81 84 75 100 94 87 85 100 100 94 100 100 92 83 100 86 89 92 80 86 96 90 100 100 100 82 80 85 78 80 84 96 100 100 94 82 86 95 1O0 100 3 (none Ibrak ibrak ibrak none none none ibrak none (none Ibrak none ibrak none none none none ibrak none none none none ibrak none none none none 'none ibrake ibrak none none none (none none none none none none none none none none none none none none none none none none none none none none none none none none none none none none | nipropylbenzamidine N-n-isopropylbenzardine and N-n-otatyl-benzamidine N-decyl- -^Hokytyl-isobutaneamidine N-benzyl- -N'-okityl- isobuitano- | aimLdyina 1 2 93 100 100 75 100 98 95 90 89 12 7 0 0 75 81 3 none none none none none none none none none none none none the leaves turn brown none and none | *) Commercially available powder containing 25% of bicarbonate S,S-imei;yikohi- 35 noksalimodiiyQ/u-2.3. Example XX. Effect on petiole powdery mildew at low concentrations of the active substance. The experiment was carried out as in Example XIX, except that groups of plants containing 10 seedlings were sprayed with 40 ml of diluted conicitrait for emulsification prepared as in Example XV and containing 50.25 or 12.5 ppm of the active substance. The results are presented in table 3. Table 3 Number of the tested compound 1 1 43 67 Concentration of the active substance ((ppm) 2 50 25 12.5 50 25 12.5 50 25 12.5 Effectiveness 3 100 99 95 100 95 87 97 93 90 Phytotoxicity 4 none none none none none none none none none35 122 155 table 3 (continued) table 4 (continued) 1 l 1 2 78 164 172 Morestan 50 25 12.5 50 25 12.5 50 25 12.5 50 25 12.5 3 1.00 95 94 100 93 87 76 76 61 69 54 32 4 III none none none ml none none none Example XXI. Effect on real tobacco maozindak. Tobacco seedlings (MC-1 varieties) were planted in one row of unwatered pots with a diameter of 12 cm and after two months they were used as host plants. Each plant was infected by spraying with a spore suspension of ErySiphe quiet-racearum using a small hand-held sprayer. The spore suspension was prepared by diluting the comidia with distilled water so that With a 150x magnifying scope, it was possible to observe 10 conidia in the preparation. After 2 or 5 days after infection, the leaves of each plant were sprayed with an evenly diluted emulsifying concentrate as in Example 15 and containing the desired concentration of the active substance. The plants were kept in air-conditioned greenhouse at 25°C until signs of the disease appear. Then the number of disease outbreaks on the leaves was counted and the percentage effectiveness was determined using the equation given in Example 19. The average number of disease outbreaks in the group of control plants was 522. The results of the experiment are listed in table 4. Number of the tested compound 1 1 1 46 67 Ta Concentration of the active substance 2 200 100 50 300 100 50 200 100 50 blica 4 Efficacy (%) 2 days after treatment 3 100 97 96 100 100 95 100 98 74 5 days after treatment 4 100 95 87 100 97 89 100 98 71 Phytotoxicity 5 | none none ¦ none none none none none none none none 10 15 20 25 35 50 55 60 | 1 | 2 78 1 164 172 Topsin- M*) 200 100 50 200 100 50 200 100 50 200 1100 50 3 100 89 83 100 91 89 100 95 92 100 75 45 4 100 90 76 IWO 86 79 100 91 89 99 69 30 5 | 'no no no no no no no no no no no no no no no *) A commercially available wettable powder containing 50% by weight of 1,2-bW3-methoxycarbonyl-2-thioureido/beinzen. Example XXII. Effect on gray mold of cucumbers. Cucumber seedlings (Saga-mihanjiro-fushinari varieties) were planted one at a time in plastic pots with a diameter of 6 cm and after 17 days were used as host plants. Each plant was sprayed with diluted moistened nyni with a powder prepared as in Example 16 and containing 1000 ppm of a given active substance. The application dose was 20 ml per pot. After the plants were air-dried, they were infected by spraying with a Botrytis cinerea suspension. The suspension was prepared by shock culturing the microorganism for 3 days in a yeast-glucose medium, then powdering it in a homogenizer and diluting it to such a concentration that the absorption measured with a spectrophotometer at 610 m is approximately 1.1. The host plants were kept for three days in the inoculation chamber at a temperature of 20°C, and the number of diseased plants to various degrees (nj-n7) was assessed using the following indicators. 0: no disease symptoms 1: small number of subsurface disease outbreaks 2: large number of subsurface disease outbreaks, no large disease outbreaks large disease outbreaks in less than about 1715 leaf surface areas large disease outbreaks in approximately 1/2— 1/4 of the leaf surface, large disease lesions, approximately 1/2-1/4 podia of the leaf surface, large disease lesions, over approximately 1/2 of the leaf surface. The percentage effectiveness of individual compounds was calculated from the following equation: 3: 5: 6 (number of plants: ni) (number of plants: n2) (number of plants: m) (number of plants: n4) (number of plants: n^) (number of plants: nj (number of plants: n7)skuteez- = { nosc 1 — $7 treated groups (0x11! +1xn2+2xn,+3xn +4xnB+5xng-|-6xn7) 122 155 'control groups (0xn! + + Ixni+3xnj+3ixn4+4xn5 +Qxns+6xn7) } Xioo The experimental results are presented in Table 5. Table 5 Number of the tested compound 1 3 4 8 10 12 14 28 90 165 166 174 175 186 194 195 Difoiatan *) Efficacy m 100 95 60 85 98 100 85 93 1010 89 92 85 78 90 75 86 76 Phytotoxicity none none none none none none none none none none none br, as none none none none none | *) A commercially available powder containing 80% of N-iM,1,2,2-tetrahydroflorhydrate. Example XXIII. Effect on cucumber anthracosis. Cucumber seedlings (Sagamihanjiro-fushinari varieties) were planted one at a time in plastic pots with a diameter of 6 mm and after 16 days were used as host plants. Each plant was sprayed with a diluted emulsifying concentrate. obtained as in Example 15 and containing 1000 ppm of the given active substance or diluted with a flexible powder obtained as in Example 16 and also containing 1000 ppm of the active substance. The application dose was 20 ml per pot. The plants were air-dried and they were infected by uniform spraying with a spore suspension of Colletotrichum lagenarium. The spore suspension was prepared by cultivating the spores on a medium and sweetened corn, and then diluting them so that 200 spores could be observed in the preparation under a 150x magnifying microscope. The plants were left in a humidification chamber at a temperature of 27°C and a humidity of 100°/©, and after 1 day they were transferred to the greenhouse, where after 4 days the number of disease outbreaks on the first leaf was counted. Using the equation from Example 19, the percent effectiveness was calculated. The experimental results are presented in Table 6. 10 15 25 30 35 40 50 60 38 Table 6 Number of the tested compound *. t 1 3 10 16 56 85 86 90 101 .102 103 104 137 136 139 140 Maneb Dithane**) Efficacy Wd) 2 100 100 90 95 100 95 100 96 92 98 100 93 60 90 85 93 Phytotoxicity 1 3 none none none .no none none none none none none none none none none andno none none | *) Emulsifiable concentrates containing compounds Nos. 3, 10, 16, 56, 85, 86 and 90, respectively; regenerable powders containing compounds Nos. 101-404 and 137-140, respectively. **) Commercially available wettable powder containing 70% manganese ethylenebisdithiocarbamium. Example XXIV. Effect on bacterial browning of leaves of rice plants. Rice seedlings (Ndihonbare varieties) were planted in groups of 5 in plastic pots with a capacity of 6 cm and grown in a glass greenhouse until the stage of 5.5-6.5 leaves. The granulate prepared as in Example 18 was applied subsurface at a dose of 15 mg per pot. After the treatment, the plants were placed in a glass greenhouse so that the active substance could be absorbed from the parts of the soil under the air within 2 days. Each plant was infected with Xanithomonas oryizae by means of two injections into the upper two leaves, avoiding the innervation. . The microorganisms were previously cultured in a shock culture at a temperature of 28°C and in Suwa's liquid medium, and then its concentration was brought to 107-a/lmil. The infected plants were kept in a glass greenhouse for 2 weeks, and then the length of the disease outbreaks on the leaves was measured to calculate the number of leaves (ni—n^ with different degrees of disease according to the following indices: 0: 1: 2: 5: no infection, weak infection, disease outbreaks with a length of less than 1 cm, disease outbreaks with a length of less than 2 cm disease outbreaks with a length of less than 5 cm disease outbreaks with a length of less than 10 cm (number of leaves: ni) (number of leaves: mj (number of leaves: n$) (number of leaves: ni) {number of leaves: n^) (number of leaves: ne)122 155 39 6: disease lesions with a length of more than 10 cm 40 (number of leaves: n7) The percentage effectiveness of a given active substance was calculated on the basis of the following equation: (0xni+1x112+ groups subjected to -+2xn3 + 3xn4 ne treatment +4xri5+5xn6 + 6xn7) effectiveness 1- control groups (0xni+lxn£-h +2xn3+ 3xin4 +4xn5+5xn6 + 6xn7) Xioo The experimental results are presented in Table 7. Table 7 Number 1 of the tested compound and 31 47 66 85 86 87 ' 88 89 90 101 102 103 105 111 112 116 117 119 121 157 161 162 163 167 168 .169 171 172 175 179 180 iai 182 183 184 190 194 1 95 198 199 | Phenazine * Efficacy m 2 76 . 73 78 75 100 100 96 83 87 74 82 100 87 69 95 79 83 72 76 100 70 96 95 85 89 100 79 82 100 75 68 86 79 . 75 83 96 98 1 100 88 92 76 Phytotoxicity 3 none none none 'none no no no no no no .no no no no no no no no no no no no (no no no no no | -no no no no no .no no no ' none none none none none none none ; none none none none none none | 10 15 20 30 35 40 45 50 55 Example XXV. Action against bacterial wet rot of Chinese cabbage. Chinese cabbage seedlings (Nozaki No. 2 varieties) grown in pots plastics with a diameter of 6 cm in an air-conditioned greenhouse at a temperature of 25°C were used as host plants 18 days after sowing. Each plant was treated with a diluted wettable powder prepared as in Example 16 and containing 1000 ppm of a given substance. active substance. The application dose for spraying was 20 ml per pot. The plants were then infected by spraying them with Erwinia aroideae E-7105. The microorganisms were previously cultured in a shock culture at a temperature of 28°C in liquid Suwa medium for 24 hours, and then the diluted nutrient solution with the concentration of microorganisms to ensure proper infection of the plants was mixed with carborindium (300 mesh) before spraying. The infected plants were placed in an inoculum chamber at a temperature of 28°C, and after 3 days the degree of disease was assessed to determine disease indicators. Assessment of the degree of disease Disease index no infection 0 weak infection 1 small infected area 2 infected area corresponding to giving approximately 1/4 of the total area 3 infected area corresponding to approximately 1/3 of the total area 4 infected area corresponding to approximately 1/2 of the total area 5 whole infected plant 6 The percentage effectiveness of a given active substance was calculated using the following equation. effect- = \ part 1- Degree of disease in groups treated disease indicators in 10 series for 60, as each trial was carried out in 10 series. The experimental results are given in Table 8. Table 8 11 55 Efficacy 2 75 82 Phytotoxicity 3 none none ¦ ¦ 122 155 41 42 Rice seedlings (Nihombare varieties) were planted in groups of 10 in a plastic pot with a diameter of 6 ohm and grown to the stage 4.0 - 4.6 leaves, and then each host plant was sprayed with a diluted wettable powder prepared as in Example XVI or a diluted concentrated concentrate prepared as in Example XV, each containing 500 ppm of a given active substance. io The application rate was 20 ml per pot. The plants were air-dried and infected with Cochliobolus irtiyadeanus. The microorganisms were previously cultured at a temperature of 28°C for 10 days, using rice straw extract as a medium, and then the concentration was selected so that 10-15 conidia could be observed under a 150x magnifying microscope. The infected plants were placed in a chamber inoculation at a temperature of 27°C, at which the relative humidity was over 05°C/ou. After 2 days, the disease foci were counted on the upper two leaves, and then the percentage effectiveness of the individual active substances was calculated as in the case. clade XIX. The results are presented in table 10. 25 Table 10 table 8 (continued) 1 57 65 65 68 00 Agirept *) 2 00 65 76 03 /100 75 3 none none none none none ¦ none | *) Condensable powder containing 25% of isftreptomycin sulfate (20% as streptomycin). Example XXVI. Action against rice pyriculariosis. Rice seedlings (variety Nohrin No. 20) were planted in pots with a diameter of 6 cm and grown until they reached 50°/4 of the 4-leaf stage. The leaves were sprayed (20 ml per pot) with a diluted wettable powder prepared as in Example 16 and containing 1000 ppm of the active substance in question. The plants were air-dried and infected by spraying them evenly with a suspension of Piricularia oryzae spores. Spraying was carried out in an inoculation chamber. The microorganism was previously cultured at a temperature of 27°C for 7-10 days on rice husk medium (3 g of rice husk, 0.01 g of powdered malt extract, 0.2 g of glucose, 0.05 g of soluble starch and 5 mL of water). The host plants were maintained at a temperature of 27°C and a relative humidity of over 05°C for 2 days and then placed in a greenhouse for 4 days. The number of disease outbreaks and the percentage effectiveness of the given active substances were calculated using the method as in Example 19. The experimental results are presented in Table 9. Table 0 Number of the tested compound 103 107 113 114 115 125 127 128 120 133 134 161 163 165 193 197 198 100 200 201 Effectiveness f/d) 100 0 6 93 86 88 100 100 93 96 100 06 95 100 86 89 96 ¦100 72 80 75 Phytotoxicity none | none none none none none none none none ¦ none none ' none none none none none none none none btrak . 'none J Example XXVII. Effect against blight on rice plants. Number of tested compound *) 1 113 114 115 116 137 138 130 140 145 152 158 1161 162 163 164 172 173 174 180 100 103 Efficacy «°/«) 2 100 93 97 90 85 77 87 80 86 82 100 80 93 100 05 80 01 87 89 82 100 Phytotoxicity 3 none none none none none none none none none none none none none none none none none none none none none . | *) The wettable powders contained compounds Nos. 113-116 and 137--140, respectively; emulsifiable concentrates contained compounds Nos. 145, 152, 158, 161-164, 172-174, 189, 100 and 103, respectively. Example XXVIII. Action against rice plant pox. Rice seedlings (Nihonbare varieties) were planted in 10 pots with a diameter of 6 cm and grown until the 7-8 leaf stage, after which the host plants were sprayed with diluted avilal powder 65 prepared as in Example XVI, and containing - 10 15 20 25 30 35 40 45 50 55 60122 155 43 44 -500 ppm of the active substance. The application rate was 20 ml per pot. The plants were air-dried and infected with Pellicularia sasakii by placing the microorganisms on the soil in the pot, and the pots were then placed in an inoculation chamber in the greenhouse. The microorganisms were previously cultured on rice bran medium for 14 days. After 7-10 days after infection, the length of disease outbreaks appearing on plant stems was measured and disease indicators were determined. Assessment of infection: no infection, weak infection, disease outbreaks with a length below 1 cm disease outbreaks with a length of less than 2 cm disease outbreaks with a length of less than 5 cm disease outbreaks with a length of less than 10 cm disease outbreaks with a length of more than 10 cm Disease indicator 0 (number of plants: ni) 1 (number of plants: n2) 2 (number of plants : n3) 3 (number of plants: ru) 4 (number of plants: n5) 5 (number of plants: ri6) 6 (number of plants: n7) Based on the observations, the percentage effectiveness of individual active substances was calculated using the equation given in Example XX The experimental results are presented in Table 11. Table 11 Number of the tested compound 145 146 147 161 162 163 164 Efficacy (%) 99 94 85 91 80 33 95 Phytotoxicity: no him barley. Barley seedlings (Kuromugi variety) were planted in 10 groups in unwatered pots with a diameter of 15 cm and cultivated until the first leaf was sufficiently developed in a glass greenhouse at a temperature of 20-25°C for 7 days. Emulsifiable concentrates containing N,N-diethylbenzamirine (compound No. 1) obtained in Example 1 were diluted to the appropriate concentration and sprayed on the leaves of host plants at a dose of 20 ml per pot. After the plants were air-dried, the first leaves of these plants were infected by spraying with Erisiphe graminus H-14 spores. The infected plants were placed in a glass greenhouse at a temperature of 20-25°C, and after 7 days the degree of the disease was determined. The results are given in Table 12. Example XXX. Action against the crown grass of oats. 15 20 25 30 35 40 45 50 55 60 65 Oat seedlings (Zenshin varieties) were planted in 20 groups in unwatered pots (15 cm in diameter) and grown in a glass greenhouse at a temperature of 20-25°C until the 2nd leaf stage. The cultivation lasted 7 days. The emulsifiable concentrate containing N,N-diethylbenzamidine (compound No. 1) obtained as in Example I was diluted with water to the required concentration, and then the plant leaves were sprayed at a dose of 20 ml per pot. (The host plants were dried). in the air and prohibited by spraying a suspension of Puccinia coronata spores, and then placed in a humidification chamber at a temperature of 23°C. After 24 hours, the plants were placed in a glass greenhouse at a temperature of 20-25°C, and (after 20 days after infection, disease outbreaks were counted and the degree of disease was calculated. The results are given in table 12. Example XXXI. Action against chrysanthemum rust. Chrysanthemums (Ryuzanshiimpu varieties) were planted in unwatered pots with a diameter of 15 cm and were used as plants - breadwinners. The emulsifiable concentrate containing N,N-diethylbenzimidene (compound No. 1) was diluted with water to the desired concentration and sprayed on the plants at a dose of 50 ml per pot, and then the spraying was repeated twice more, at seven-day intervals. The plants were naturally infected by placing chrysanthemum plants infected with Puccinia chrysanithemi around them. After 1 month, the degree of the disease was assessed. The results are given in Table 12. Table 12 Concentration of the active substance (ppm) 1000 500 200 control groups Degree of disease Example XXIX 0 0 P 100 Example XXX 1.6 4.7 36.0 100 Example XXXI 0 11.4 26.7 100 Reservations patent 1. Method for preparing new benzamidine derivatives of formula 1, in which the same or different and denote alkyl groups, alkenyl groups, cycloalkyl groups or phenyl groups, or together with the nitrogen atom to which they are bound, they form a 5-7 member saturated aMcyclic ring, which may contain an atom as one of the members. oxygen or which may be substituted by one methyl group or two methyl groups, and R3 represents a hydrogen atom, as well as salts of compounds of the formula 1, characterized in that the nitrile of the formula 6, in which X and n have the meanings given above, gives reaction network with Il-rz. amine with formula R1R2! NH,45 122 155 46 wherein R1 and R2 have the above-mentioned meanings, in the presence of aluminum chloride, and then the resulting chlorplex compound is decomposed with the help of an inorganic acid, and then treated with a salt-alkaline agent, after which the compound with visoin <1 is optionally converted into a salt by reaction with an acid. 2. Method according to instructions. 1, characterized in that the reactions of nitrile of formula 6 and Il-riz. amines of the formula R^^H are carried out at temperatures ranging from room temperature to 60°C, optionally in an organic solvent. 3. The method according to claim 1, characterized in that the complex compound is decomposed with hydrochloric acid, sulfuric acid or nitric acid at a temperature ranging from room temperature to 50°C, and soda or potash is used as a strongly alkaline agent to precipitate ¬ pouring this agent at a temperature lower than room temperature. 4. A fungicide containing an agriculturally acceptable inert carrier and an active substance, characterized in that the active substance contains a new benzamidine derivative of formula 1, in which 1, 2 or 3, R1 and R2 are the same or different and denote alkyl groups, alkenyl groups, cycloalkyl groups or phenyl groups, or together with the nitrogen atom to which they are bound, they form a 5-7-membered saturated alicyclic ring, which as one of the members may contain an oxygen atom or which may be substituted with one methyl group or two methyl groups, and R3 is a hydrogen atom or a salt of the compound of formula 1. 5. A fungicide according to claim 1. 4, characterized in that it contains as active substance a salt of the compound of formula 1 and terephthalic acid, adipic acid, salicylic acid, tartaric acid or hydrochloric acid. 6. A fungicide according to claim 1. 4, characterized in that the active substance contains N,N-diethylbenzamidine, N,N-diethylbenzamidine salicylate, N,N-diethylbenzamidine adipate or N,N-diethyl-o-ohlorabenzamiidine. 7. A method for preparing new benzamidine derivatives of formula 1, wherein Alkyl, alkenyl or aikinyl group, benzyl group, possibly found by chlorine atoms, cyanoalkil group, a group of alcohoxicarbonylometile group, group of a-alkoxarboniumleetia, group aicoxician group, group bis/alcoholkony/metyl because a pheneonian group, possibly a substituted alkyl group or an alkoxy group, as well as salts of compounds of formula 1, characterized in that the nitrile of formula 6, in which where R1 and R2 have the meaning given above, in the presence of aluminum chloride, and then the resulting compact compound is decomposed with water or an inorganic acid, and then treated with a strong alkaline agent to obtain a benzamidine derivative of formula 1, wherein R3 is hydrogen and X, u; R15 and R2 have the meanings given above, and then, in order to prepare the benzamidine derivative of formula I, in which R3 has the meanings given above except for the hydrogen atom, and X, n, R1 and R2 have the meanings given above, the derivative is benzamidine of the formula I, in which R3 is hydrogen, reacting with a compound of the formula R3-Z, in which R3 has the above-mentioned meaning with the exception of the hydrogen atom, and Z is a halogen atom, an isocyanate group or a isothiocyanate, and then the compound of formula 1 is optionally converted into a salt by reaction with an acid. 8. The method according to claim 7, characterized in that the reactions iiiitryjliu with vision 6 and Il-irz. amines of the formula RWNH are carried out at a temperature from room temperature to 60°C, optionally in an organic solvent. 9. The method according to claim 7, characterized in that the complex compound is decomposed with hydrochloric acid, sulfuric acid or nitric acid, at a temperature ranging from room temperature to 50°C, and the strongly alkaline agent used is caustic soda or caustic potassium, carrying out the treatment with this agent at a temperature lower than room temperature. 30 10. The method according to claim 30. 7, characterized in that the benzamidine derivative of the formula 1, in which R3 is hydrogen and X, n, R1 and R2 have the meanings given above, is reacted with a compound of the formula R3-Z, wherein R3 has the meanings given above. with the exception of the hydrogen atom and Z has the meaning given above, in the presence of a base and at a temperature from room temperature to 250°C. 11. A fungicide containing an agriculturally acceptable inert carrier and an active substance, characterized in that the active substance is a new benzamidine derivative of the formula 1, in which X is a lower alkyl group, n is zero or 1, R1 and R2 are the same or different and denote alkyl groups or alkenyl groups, 45 and R3 denotes a straight-chain or branched alkyl, alkenyl or alkyinyl group, a benzyl group, optionally substituted with cMo atoms, a cyano group, a cyanoalkyl group, an alkoxycarbonylmethyl group, an α-adkoxycarbo- nylethyl group, an alkoxymethyl group, a bis(-alkoxycarbonylmethyl) group or a phenoxyethyl group, an optionally substituted alkyl group or an alkoxy group, or a salt of the compound of formula 1. 12. A fungicide according to claim 1. 1:1, characterized in that it contains as the active substance a salt of the compound of formula 1 and terephthalic acid, adipic acid, salicylic acid, tartaric acid or hydrochloric acid. 13. Fungicide according to assibrz. lii, characterized in that it contains as the active substance N,N-diethyl-N-formylbenzamidine or N,N-diethyl-N-ethoxycarbonylmethylbenzamidine. 14. A method for preparing new benzalmidine derivatives of formula 1, wherein wherein R4 is either a hydrogen group, a lower alkyl group, a c-morylmethyl group, a lower alkoxy group, a lower alkyl-alkyl group, a lower alkenyl group, a lower alkylthiomethyl group, a furyl group, a thienyl group, a lower allkyl group, a phenylthiomethyl group, a phenoxy group, optionally a substituted mephthyl group or a phenyl group, optionally substituted with a Moro atom, a methyl group, a methyl group or a nitro group, or R3 is a group of the formula 3, in which R5 and R* are the same or different and denote hydrogen atoms* lower alkyl groups, cyclohexyl groups, anyldinoicarbonyl groups, optionally substituted with a halogen atom or phenyl groups, optionally substituted with a halogen atom or a methyl group, or R3 represents a group of formula 4, in which R7 is a lower alkyl group, a cycloheixyl group, a benzyl group, a lower alkoxycarbonyl group or a phenoxycarbonyl group, or R3 is a group of the formula -SO*-R8, in which R8 is a lower alkyl group, a triphylluoromethyl group, a chloromethyl group or a group phenyl, optionally substituted with a halogen atom or a methyl group, as well as salts of compounds of the formula 1, characterized in that the nitrile of the formula 6, in which X and n have the meanings indicated above, is reacted with II. amine with the formula RWNH, in which R1 and R2 have the meanings given above, in the presence of aluminum chloride, then the resulting complex compound is decomposed with water (or an inorganic acid, and then treated with a strong alkaline agent to obtain the derivative benzamidine derivatives of formula I, wherein R3 is hydrogen and X, n, R1 and R2 are as defined above, then to prepare a benzamidine derivative of formula I, wherein R3 is as defined above except hydrogen atom, and X, n, R1 and Ra have the meanings given above, a benzamidine derivative of the formula 1, in which R3 is a hydrogen atom, is reacted with a compound of the formula R3-Z, in which R3 has the above-given meanings. meaning except for the hydrogen atom, and Z is a halogen atom, an isocyanate group or an isothiocyanate group, and then the compound of formula 1 is optionally converted into a salt by reaction with an acid. 15. The method according to claim 14, characterized in that the nitrile reaction of formula 6 and second-row amines of formula R^^NH are carried out at temperatures ranging from room temperature to 60°C, optionally in an organic spray. 16. The method according to claim 14, characterized in that the complex compound is decomposed with hydrochloric acid, sulfuric acid or nitric acid at a temperature ranging from room temperature to 50°C, and caustic soda or potash is used as the alkaline salt agent. turn off by treating it with this agent at a temperature lower than room temperature. . 17. The method according to claim 14, characterized in that the benzamidine derivative of formula 1, in which R3 is hydrogen and X, m, R1, and R* are as defined above, is reacted with a compound of formula R3-Z, wherein R3 is ¬ has the meaning given above except for the hydrogen atom and Z has the meaning given above, in the presence of a base and at a temperature from room temperature to 250°C. 18. A fungicide containing an agriculturally acceptable inert carrier and an active substance, characterized in that the active substance is a new benzimidine derivative of the formula 1, wherein alkoxy, lower alkoxyalkyl, lower alkenyl, lower alkylthiomethyl, furyl, thienyl, lower alkylthio, phenylthiomethyl, phenoxy, optionally substituted methyl or phenyl, optionally substituted halogen , a methyl group, a methoxy group or a nitro group, or R3 represents a group of formula 3, in which R5 and R* are the same or different and represent hydrogen atoms, lower alkyl groups, cyclohexyl groups, anilinocarbonyl groups, optionally substituted with a halogen atom or phenyl groups, optionally substituted with a halogen atom or a methyl group, or R3 is a group of the formula 4, in which R7 is a lower alkyl group, a cyclohexyl group, a benzyl group, a lower alkoxycarbonyl group or a phenoxycarbonyl group, or R3 is a group of the formula -S02-R8, in which R8 is a lower alkyl group, a trifluoromethyl group, a chloromethyl group or a phenyl group, optionally substituted with a chloro atom or a methyl group, or a salt of the compound of formula 1. 19. A fungicide according to claim . 18, characterized in that the active ingredient is a salt of the compound of formula 1 and terephthalic acid, adipic acid, salicylic acid, tartaric acid or hydrochloric acid. 20. A fungicide according to claim 1. 18, characterized in that it contains as an active substance N,N-diethyl-N'-ethoxycarbonylthiocarba-moylbenzamidine. 21. A method for preparing new benzamidine derivatives of the formula I, in which alkyl groups, alkenyl groups, cycloalkyl groups or phenyl groups, or together with the nitrogen atom to which they are bound, form a 5-7 membered saturated alicyclicine ring, which may contain an oxygen atom as one of its members or may be a base. ¬ bounded by one methyl group or two methyl groups, and R3 represents a hydrogen atom, a straight-chain or branched alkyl, aikenyl or alkynyl group, a benzyl group, optionally substituted with chlorine atoms, a cyano group, a cyanoalkyl group, an alkoxycarbonylmethyl group, analkoxycarbonylethyl group 10 15 20 25 30 35 40 45 50 55 60122155 49 50 Iowa, alkoxymelyl group, bdsMkoxycarbonyl/methyl group or femoxyethyl group, optionally substituted alkyl group or alkoxy group, or R3 denotes the group p of formula 2, v wherein R4 is hydrogen, lower alkyl group, e-Moroomethyl group, lower alkoxy group, lower aikoxy-alkyl group, lower alkenyl group, lower alkylthiomethyl group, furyl group, thienyl group, lower alkylthio group, phenylthiomethyl group, phenoxy, an optionally substituted methyl group or a phenyl group, optionally substituted with a halogen atom, a methyl group, a methoxy group or a nitro group, or R3 is a group of the formula 3, in which R5 and R9 are the same or different and represent hydrogen atoms, lower groups alkyl groups, cyMophoexyl groups, anilinocaribonyl groups, optionally substituted with a chloro atom or phenyl groups, optionally substituted with a halogen atom or a methyl group, or R3 denotes a group of the formula 4, in which R7 is a lower alkyl group, a cyclohexyl group, a benzyl group, a lower alkoxycarbonyl group or a phenoxycarbonyl group, or R3 is a group with the formula -SO2-R8, in which R8 is a lower alkyl group, a trifluoromethyl group, a chloromethyl group or a phenyl group, optionally substituted with a halogen atom or a methyl group, except where X is a lower alkyl group, a halogen atom, a methoxy group or a dimethylimino group, n is zero, 1, 2 or 3, R1 and Ra are the same or different and represent alkyl groups, groups Alikenyl dusts, cycloalkyl groups or phenyl groups, or together with the nitrogen atom to which they are bound, form a 5-7 membered saturated alicyclic ring, which may contain an oxygen atom as one of its members or may be substituted with one methyl group. or two methyl groups, and R3 is hydrogen, and except where X is an alkyl group, n is zero or 1, R1 and R2 are the same or different and represent alkyl groups or alkenyl groups, and R1 represents a straight-chain or branched alkyl, alkenyl or alkymyl group, a benzyl group, optionally substituted with chlorine atoms, a cyano group, a cyanalkyl group, an ad-koxymethyl group, an alkoxymethyl group, an alkoxymethyl group, an alkoxyimethyl group, a group pe b5s/afltaoJoxycartoonyl/methyl group or group phenoxyethyl, an optionally substituted alkyl group or an alkoxy group, and except where wherein R4 is a hydrogen atom, lower alkyl group, halocornethyl group, lower alkoxy group, lower alkoxyalkyl group, lower alkenyl group, lower alphatrialthiomethyl group, furyl group, thienyl group, lower alkylthio group, phenylthiomethyl group, gru a phenoxy group, an optionally substituted methyl group or a phenyl group, an optionally substituted halogen atom, a methyl group, a methoxy group or a nitro group, or R8 is a group of formula 3 in which R5 and R* are the same or different and denote hydrogen atoms, lower alkyl groups, cyclohexyl groups, anoliinocarbonyl groups, optionally substituted with a halogen atom or phenyl groups, optionally substituted with a halogen atom or a methyl group, or R3 denotes a group of the formula 4, in which R7 denotes a lower alkyl group, a cyclohexyl group, a benzyl group, a lower allkoxycarbonyl group or a tephenoxycarbonyl group, or R8 denotes a group of the formula ^S02^RB, in which R8 denotes a lower alkyl group, a trifluoromethyl group, a chloromethyl group or a phenyl group, optionally a sub-alkyl group. halogenated or methyl group, as well as salts of compounds of formula 1, characterized in that the nitrile of formula 6, in which X and n have the meanings given above, is reacted with II-row. amine with the formula R^OT, in which R1 and R2 have the meanings given above, in the presence of aluminum chloride, then the resulting complex compound is decomposed with water or an inorganic acid, and then treated with a strongly alkaline agent, obtaining a phoenzanlidine derivative of the formula I, wherein R3 is hydrogen and except for the hydrogen atom, and X, n, R1 and R2 have the meanings given above, the benzamdidine derivative of formula I, in which R3 is hydrogen, reacts with a compound of the formula R3-Z, in which R3 has the meaning given above. except for the hydrogen atom, and Z is a halogen atom, an isocyanate group or an isothiocyanate group, and then the compound of formula I is optionally converted into a salt by reaction with an acid. 22. The method according to claim 21, characterized in that the ni/solid reactions of formula c and II-row amines of the formula RJR2NH are carried out at a temperature from room temperature to 60°C, optionally in an organic solvent. 23. The method according to claim 21, characterized in that the complex compound is decomposed with hydrochloric acid, sulfuric acid or nitric acid at a temperature from room temperature to 50°C, and as a strongly alkaline agent, soda or potash is used to precipitate treatment with this agent at a temperature lower than room temperature. ' 24. The method according to claim 2il, characterized in that the benzamidine derivative of the formula 1, in which R3 is hydrogen and X, m, R1 and R2 have the meanings given above, is reacted with a compound of the formula R3^Z, in which R3 has the above the meanings given with the exception of the hydrogen atom and Z have the meanings given above, in the presence of a base and at a temperature from room temperature to 250°C. 25. A fungicide containing an agriculturally acceptable inert carrier and an active substance, characterized in that as active substances it contains a new benzene derivative of the formula 1, in wherein phenyl, or together with the nitrogen atom to which they are bound, form a 5-7-membered saturated alicyclic ring, which may contain an oxygen atom as one of its members, or which may be substituted with one methyl group or two methyl groups, and R3 is an atom hydrogen, a pyrosto-chain or branched alkyl, alkenyl or alkynyl group, a benzyl group, optionally substituted with chlorine atoms, a cyam group, a cyanoalikyl group, a group of alkoxycarbonylmethyl, an α-alkoxytearbylethyl group, a group of aikoxymethyl, a bL group s/ an alkoxycarbonyl/methyl group or a phenoxymethyl group, an optionally substituted alkyl group or an alkoxy group, or R3 represents a group of the formula 2, in which R4 represents a hydrogen atom, a lower alkyl group, a halomethyl group, a lower alkoxy group, a lower alkoxyalkyl group, lower alkenyl group, lower alkylthiomethyl group, furyl group, thienyl group, lower alkylthio group, phenylthiomethyl group, phenoxy group, optionally substituted methyl group or phenyl group, optionally substituted with halogen atom, methyl group, group methoxy or nitro group, or R3 denotes a group of formula 3, in which R5 and R6 are the same or different and represent hydrogen atoms, lower alkyl groups, cyclohexyl groups, anilinecarbonyl groups, optionally substituted halogenated latomeim or phenyl groups , optionally substituted with a halogen atom or a methyl group, or R3 represents a group of formula 4 in which R7 represents a lower alkyl group, a cyclohexyl group, a benzyl group, a lower alkoxycarbonyl group or a phenoxycarbonyl group, or R3 represents a group of the formula -SO2-R8, wherein R8 is a lower alkyl group, a trifluoromethyl group, a chloromethyl group or a phenyl group, optionally substituted with a halogen atom or a methyl group, except in the case where X is a lower alkyl group, halogen atom, methoxy group or dimethylamino group, n is zero, 1, 2 or 3, R1 and R2 are the same or different and denote alkyl groups, alkenyl groups, cycloalkyl groups or phenyl groups, or together with with the nitrogen atom to which they are bonded, they form a 5-7-membered saturated alicyclic ring, which as one of the members may contain an oxygen atom, or which may be substituted with one methyl group or two methyl groups, and R3 is a hydrogen atom and except where X is a lower alkyl group, n is zero or 1, R1 and R2 are the same or different and are alkyl or alkenyl groups, and R3 is a straight-chain or branched alkyl group, an alkenyl or alkynyl group, a benzyl group, optionally substituted with chlorine atoms, a cyano group, a cyanoalkyl group, an alkoxycarbonylmethyl group, an α-alkoxycarbonylethyl group, an alkoxymethyl group, a bis/alkoxycarbonyl/methyl group or a phenoxyethyl group, optionally substituted alkyl or alkoxy group, and except where X is a lower alkyl group, n is zero or 1, R1 and R2 are alkyl groups, and R3 is a group of formula 2, wherein R4 is an atom hydrogen, lower alkyl group, halomethyl group, lower alkoxy group, lower alkoxyalkyl group, lower alkenyl group, lower alkylthiomethyl group, furyl group, thienyl group, lower alkylthio group, tphenylthiomethyl group, phenoxy group, optionally substituted me group ¬ a back or phenyl group, optionally substituted with a halogen atom, a methyl group, a methoxy group or a nitro group, or R3 is a group of formula 3, in which R5 and R* are the same or different and represent hydrogen atoms, lower alkyl groups, cyclohexyl groups, anilinecarbonyl groups, optionally substituted with a halogen atom, or phenyl groups, optionally substituted with a halogen atom, or a methyl group, or R3 is a group of formula 4, in which R7 is a lower alkyl group, a cyclohexyl group, a benzyl group, a lower group alkoxycarbonyl or phenoxycarbonyl group, or R3 is a group with the formula -S02-1-R8, in which R8 is a lower alkyl group, a trifluoroniethyl group, a chloromethyl group or a phenyl group, optionally substituted with a halogen atom or a methyl group ¬ wa or a salt of the compound of formula 1. 26. A fungicide according to claim 1. 25, characterized in that it contains as active substance a salt of the compound of formula I and terephthalic acid, adipic acid, salicylic acid, tartaric acid or hydrochloric acid. 27. The fungicide according to claim 1. 25, characterized in that the active substance is N,N-diethyl-N'-bisethoxycarbonylmethylbenzamidine or N,N-di-n-propyl-N'-methyl-o-methylbenzamidine. 10 15 20 25 30 35 40 45 50122 155 x"^nJ /R' iphysór 1 O /Yztf/-3 -C-R 4 O -C-NH-R7 u S Formula 4 Xn N-R* R1 v ^C-N<"-(Y)m <* VCN Formula 6 Xn -o Wa*- w O- Formula / \ Formula n -rP\ n^C/- P C? -® Pattern 12 ¦N Pattern /3 Pattern W CH, CH CK /VZ<&- /5 CH, ~CKh(J WZ0/- Pattern W Pattern I' /CH3 CH3 ^^ # /CH3 Qj. ".CH" '2n5 W^a i^ / \X Wzór23122 155 CHp CHp/ (^ Cl^ Cl CL Formula 24 V \ =r ci- ttcór 27 Formula 25 ,ci ^l Formula 30 Br O Formula 32 CH CH, 3\ N // W Formula 35 Formula 28 \ci Formula 2S Cl Formula 29 flFormula 33 Formula 31 Formula 34 Formula 36 Formula 37 /OH Formula 40 (TTy-COOH fiyCOOH Formula 38 Formula 39 Formula 44 /OCOCH3 ^J^COOH Formula 41 Formula 43 COOH COOH Formula or 45 ocC00H V^COOH Formula 46 CH r% 3 \= Formula 47 S03H122 155 C*H„-Q-SAH WLOr 48 0-SO3H c Yizór 50 CH2COOH HO-C-COOH CH2COOH Yizór 49 OH ^ ^ a CH Yizór 51 Yizór 52 CC2H5 -CHjOtfK 7 CH3 -CH2CH£M^J Yizór 53 Yizór 54 cHrO Yizór 55 -CH2-^Q^Cl Pattern 56 o Y\'Z0r 57 o Yizór 59 -? Oa o Pattern i8 OCH3 0 cchlshQ 0 Yizór 61 - c II o ^y /^zc)r & Wafr 63 -co II o II ° o OH3 A CH3 Chip 65 Ol N02 -c-t5 -CNHCNH-O 0 O122 155 -CNHCNH-^^ ii li O O Formula 67 -C -NH^ o ci Formula 69 -CNH-/ XX Formula GQ ¦c^^3 O ^CH, Formula 70 -CNH^CH3 -CNH^H) 0 ,., '.O Formula 71 -cnh^h) s Formula 73 Formula 75 Formula 72 CNHCH2-^3 Formula 74 S02-C^CH3 -SOj^^Cl MzOr 77 Formula 76 -S02^Q^Br Formula 78 - CNHCO -4~S ¦ li li \=/ s o Formula 79 CN R \ Pattern 6 R 1/ NH

Claims (27)

1. Patent claims 1. Method for preparing new benzamidine derivatives of formula 1, in which X is a lower alkyl group, a halogen atom, a methoxy group or a dimethylamino group, n is the number zero, 1, 2 or 3, R1 and Ra are the same or different and denote alkyl groups, alkenyl groups, cycloalkyl groups or phenyl groups, or together with the nitrogen atom to which they are bound, they form a 5-7 member saturated aMcyclic ring, which, as one of the members may contain an oxygen atom or which may be substituted with one methyl group or two methyl groups, and R3 is a hydrogen atom, as well as salts of compounds of formula 1, characterized in that nitrile of formula 6, in which X and n have the meanings given above, undergoes reaction with II-row. amine of the formula R1R2!NH,45 122 155 46 in which R1 and R2 have the above-mentioned meanings, in the presence of aluminum chloride, and then the resulting cyanplex compound is decomposed with the help of an inorganic acid and then treated with a salt-alkaline agent , then the compound with a visoin <1 is optionally converted into a salt by reaction with an acid. 2. Method according to instructions. 1, characterized in that the reactions of nitrile of formula 6 and Il-riz. amines of the formula R^^H are carried out at temperatures ranging from room temperature to 60°C, optionally in an organic solvent. 3. The method according to claim 1, characterized in that the complex compound is decomposed with hydrochloric acid, sulfuric acid or nitric acid at a temperature ranging from room temperature to 50°C, and soda or potash is used as a strongly alkaline agent to precipitate ¬ pouring this agent at a temperature lower than room temperature. 4. A fungicide containing an agriculturally acceptable inert carrier and an active substance, characterized in that the active substance contains a new benzamidine derivative of formula 1, in which 1, 2 or 3, R1 and R2 are the same or different and denote alkyl groups, alkenyl groups, cycloalkyl groups or phenyl groups, or together with the nitrogen atom to which they are bound, they form a 5-7-membered saturated alicyclic ring, which as one of the members may contain an oxygen atom or which may be substituted with one methyl group or two methyl groups, and R3 is a hydrogen atom or a salt of the compound of formula 1. 5. Fungicide according to claim. 4, characterized in that it contains as active substance a salt of the compound of formula 1 and terephthalic acid, adipic acid, salicylic acid, tartaric acid or hydrochloric acid. 6. A fungicide according to claim 1. 4, characterized in that the active substance contains N,N-diethylbenzamidine, N,N-diethylbenzamidine salicylate, N,N-diethylbenzamidine adipate or N,N-diethyl-o-ohlorabenzamiidine. 7. A method for preparing new benzamidine derivatives of formula 1, wherein Alkyl, alkenyl or aikinyl group, benzyl group, possibly found by chlorine atoms, cyanoalkil group, a group of alcohoxicarbonylometile group, group of a-alkoxarboniumleetia, group aicoxician group, group bis/alcoholkony/metyl because a pheneonian group, possibly a substituted alkyl group or an alkoxy group, as well as salts of compounds of formula 1, characterized in that the nitrile of formula 6, in which where R1 and R2 have the meaning given above, in the presence of aluminum chloride, and then the resulting compact compound is decomposed with water or an inorganic acid, and then treated with a strong alkaline agent to obtain a benzamidine derivative of formula 1, wherein R3 is hydrogen and X, u; R15 and R2 have the meanings given above, and then, in order to prepare the benzamidine derivative of formula I, in which R3 has the meanings given above except for the hydrogen atom, and X, n, R1 and R2 have the meanings given above, the derivative is benzamidine of the formula I, in which R3 is hydrogen, reacting with a compound of the formula R3-Z, in which R3 has the above-mentioned meaning with the exception of the hydrogen atom, and Z is a halogen atom, an isocyanate group or a isothiocyanate, and then the compound of formula 1 is optionally converted into a salt by reaction with an acid. 8. The method according to claim 7, characterized in that the reactions iiiitryjliu with vision 6 and Il-irz. amines of the formula RWNH are carried out at a temperature from room temperature to 60°C, optionally in an organic solvent. 9. The method according to claim 7, characterized in that the complex compound is decomposed with hydrochloric acid, sulfuric acid or nitric acid, at a temperature ranging from room temperature to 50°C, and the strongly alkaline agent used is caustic soda or caustic potassium, carrying out the treatment with this agent at a temperature lower than room temperature. 3010. 10. The method according to claim 7, characterized in that the benzamidine derivative of the formula 1, in which R3 is hydrogen and X, n, R1 and R2 have the meanings given above, is reacted with a compound of the formula R3-Z, wherein R3 has the meanings given above. with the exception of the hydrogen atom and Z has the meaning given above, in the presence of a base and at a temperature from room temperature to 250°C. 11. A fungicide containing an agriculturally acceptable inert carrier and an active substance, characterized in that the active substance is a new benzamidine derivative of the formula 1, in which X is a lower alkyl group, n is zero or 1, R1 and R2 are the same or different and denote alkyl groups or alkenyl groups, and R3 denotes a straight-chain or branched alkyl, alkenyl or alkenyl group, a benzyl group, optionally substituted with cMo atoms, a cyano group, a cyanoalkyl group, an alkoxycarbonylmethyl group, an α-adkoxycarbo- nylethyl group, an alkoxymethyl group, a bis(-alkoxycarbonylmethyl) group or a phenoxyethyl group, an optionally substituted alkyl group or an alkoxy group, or a salt of the compound of formula I. 12. A fungicide according to claim 1. 1:1, characterized in that it contains as the active substance a salt of the compound of formula 1 and terephthalic acid, adipic acid, salicylic acid, tartaric acid or hydrochloric acid. 13. Fungicide according to assibrz. lii, characterized in that it contains as the active substance N1-N-diethyl-N-formylbenzamidine or N,N-diethyl-N-ethoxycarbonylmethylbenzamidine. 14. A method for preparing new benzalmidine derivatives of formula 1, wherein wherein R4 is either a hydrogen group, a lower alkyl group, a c-morylmethyl group, a lower alkoxy group, a lower alkyl-alkyl group, a lower alkenyl group, a lower alkylthiomethyl group, a furyl group, a thienyl group, a lower allkyl group, a phenylthiomethyl group, a phenoxy group, optionally a substituted mephthyl group or a phenyl group, optionally substituted with a Moro atom, a methyl group, a methyl group or a nitro group, or R3 is a group of the formula 3, in which R5 and R* are the same or different and denote hydrogen atoms* lower alkyl groups, cyclohexyl groups, anyldinoicarbonyl groups, optionally substituted with a halogen atom or phenyl groups, optionally substituted with a halogen atom or a methyl group, or R3 represents a group of formula 4, in which R7 is a lower alkyl group, a cycloheixyl group, a benzyl group, a lower alkoxycarbonyl group or a phenoxycarbonyl group, or R3 is a group of the formula -SO*-R8, in which R8 is a lower alkyl group, a triphylluoromethyl group, a chloromethyl group or a group phenyl, optionally substituted with a halogen atom or a methyl group, as well as salts of compounds of the formula 1, characterized in that the nitrile of the formula 6, in which X and n have the meanings indicated above, is reacted with II. amine with the formula RWNH, in which R1 and R2 have the meanings given above, in the presence of aluminum chloride, then the resulting complex compound is decomposed with water (or an inorganic acid, and then treated with a strong alkaline agent to obtain the derivative benzamidine derivatives of formula I, wherein R3 is hydrogen and X, n, R1 and R2 are as defined above, then to prepare a benzamidine derivative of formula I, wherein R3 is as defined above except hydrogen atom, and X, n, R1 and Ra have the meanings given above, a benzamidine derivative of the formula 1, in which R3 is a hydrogen atom, is reacted with a compound of the formula R3-Z, in which R3 has the above-given meanings. meaning except for the hydrogen atom, and Z represents a halogen atom, an isocyanate group or an isothiocyanate group, and the compound of formula 1 is optionally converted into a salt by reaction with an acid. 15. The method according to claim 14, characterized in that the reactions of the nitrile of formula 6 and II-row amines of the formula R^^NH are prepared at a temperature ranging from room temperature to 60°C, optionally in an organic spray. 16. The method according to claim 14, characterized in that the complex compound is decomposed with hydrochloric acid, sulfuric acid or nitric acid at a temperature ranging from room temperature to 50°C, and caustic soda or potash is used as the alkaline salt agent. turn off by treating it with this agent at a temperature lower than room temperature. 17. . 17. The method according to claim 14, characterized in that the benzamidine derivative of formula 1, in which R3 is hydrogen and X, m, R1, and R* are as defined above, is reacted with a compound of formula R3-Z, wherein R3 is ¬ has the meaning given above except for the hydrogen atom and Z has the meaning given above, in the presence of a base and at a temperature from room temperature to 250°C. 18. A fungicide containing an agriculturally acceptable inert carrier and an active substance, characterized in that the active substance is a new benzimidine derivative of the formula 1, wherein alkoxy, lower alkoxyalkyl, lower alkenyl, lower alkylthiomethyl, furyl, thienyl, lower alkylthio, phenylthiomethyl, phenoxy, optionally substituted methyl or phenyl, optionally substituted halogen , a methyl group, a methoxy group or a nitro group, or R3 represents a group of formula 3, in which R5 and R* are the same or different and represent hydrogen atoms, lower alkyl groups, cyclohexyl groups, anilinocarbonyl groups, optionally substituted with a halogen atom or phenyl groups, optionally substituted with a halogen atom or a methyl group, or R3 is a group of the formula 4, in which R7 is a lower alkyl group, a cyclohexyl group, a benzyl group, a lower alkoxycarbonyl group or a phenoxycarbonyl group, or R3 is a group of the formula -S02-R8, in which R8 is a lower alkyl group, a trifluoromethyl group, a chloromethyl group or a phenyl group, optionally substituted with a chloro atom or a methyl group, or a salt of the compound of formula 1. 19. A fungicide according to claim 1. 18, characterized in that the active ingredient is a salt of the compound of formula 1 and terephthalic acid, adipic acid, salicylic acid, tartaric acid or hydrochloric acid. 20. A fungicide according to claim 1. 18, characterized in that it contains as an active substance N,N-diethyl-N'-ethoxycarbonylthiocarba-moylbenzamidine. 21. Process for the preparation of new benzamidine derivatives of the formula I, in which and denote alkyl groups, alkenyl groups, cycloalkyl groups or phenyl groups, or together with the nitrogen atom to which they are bound, they form a 5-7 membered saturated alicyclicine ring, which may contain an oxygen atom as one of its members, or which may be substituted by one methyl group or two methyl groups, and R3 represents a hydrogen atom, a straight-chain or branched alkyl, aikenyl or alkynyl group, a benzyl group, optionally substituted with chlorine atoms, a cyano group, a cyanoalkyl group, an alkoxy- carbonylmethyl, analkoxycarbonylethyl group, 10 15 20 25 30 35 40 45 50 55 60122155 49 50 Iowa, alkoxymelyl group, bdsMkoxycarbonyl/methyl group or femoxyethyl group, optionally substituted alkyl group or alkoxy group, or R3 denotes the p group of formula 2 , in which R4 is a hydrogen atom, lower alkyl group, eMoroomethyl group, lower alkoxy group, lower aikoxy-alkyl group, lower alkenyl group, lower alkylthiomethyl group, furyl group, thienyl group, lower alkylthio group, phenylthiomethyl group , a phenoxy group, an optionally substituted methyl group or a phenyl group, optionally substituted with a halogen atom, a methyl group, a methoxy group or a nitro group, or R3 is a group of the formula 3, in which R5 and R9 are the same or different and represent hydrogen atoms, lower alkyl groups, cyMophoexyl groups, anilinocaribonyl groups, optionally substituted with a halogen atom or phenyl groups, optionally substituted with a halogen atom or a methyl group, or R3 denotes a group of formula 4, in which R7 denotes a lower alkyl group, a group a cyclohexyl group, a benzyl group, a lower alkoxycarbonyl group or a phenoxycarbonyl group, or R3 is a group with the formula -SO2-R8, in which R8 is a lower alkyl group, a trifluoromethyl group, a chloromethyl group or a phenyl group, optionally substituted with a halogen atom or a methyl group. halogen, except where X is a lower alkyl group, a halogen atom, a methoxy group or a dimethylimino group, n is zero, 1, 2 or 3, R1 and Ra are the same or different and represent alkyl groups, alkyl groups, cycloalkyl groups or phenyl groups, or together with the nitrogen atom to which they are bound, form a 5-7 membered saturated alicyclic ring, which may contain an oxygen atom as one of the members or may be substituted with one a methyl group or two methyl groups, and R3 is a hydrogen atom, and except where X is an alkyl group, n is zero or 1, R1 and R2 are the same or different and represent alkyl groups or alkenyl groups and R1 is a straight-chain or branched alkyl, alkenyl or alkyl group, a benzyl group, optionally substituted with chlorine, a cyano group, a cyanalkyl group, an ad-koxy ionyl methyl group, a halkoxy teribonyl ethyl group, an alkoxy methyl group. , b5s/afltaoJoxycartoonyl/methyl group or a phenoxyethyl group, an optionally substituted alkyl group or an alkoxy group, and except where 2, wherein R4 is a hydrogen atom, lower alkyl group, halocornethyl group, lower alkoxy group, lower alkoxyalkyl group, lower alkenyl group, lower altrialthiomethyl group, furyl group, thienyl group, lower alkylthio group, phenylthiomethyl group , a phenoxy group, an optionally substituted methyl group or a phenyl group, an optionally substituted halogen atom, a methyl group, a methoxy group or a nitro group, or R8 is a group of formula 3 in which R5 and R* are the same or . different and denote hydrogen atoms, lower alkyl groups, cyclohexyl groups, anoliinocarbonyl groups, optionally substituted with a halogen atom or phenyl groups, optionally substituted with a halogen atom or a methyl group, or R3 denotes a group of the formula 4, in which R7 denotes a lower group an alkyl group, a cyclohexyl group, a benzyl group, a lower allkoxycarbonyl group or a tephenoxycarbonyl group, or R8 represents a group of the formula ^S02^RB, in which R8 represents a lower alkyl group, a trifluoromethyl group, a chloromethyl group or a phenyl group, optionally halogen-substituted methyl group, as well as salts of compounds of formula 1, characterized in that the nitrile of formula 6, in which X and n have the meanings given above, is reacted with II-row. amine with the formula R^OT, in which R1 and R2 have the meanings given above, in the presence of aluminum chloride, then the resulting complex compound is decomposed with water or an inorganic acid, and then treated with a strongly alkaline agent, obtaining a phoenzanlidine derivative of the formula I, wherein R3 is hydrogen and except for the hydrogen atom, and X, n, R1 and R2 have the meanings given above, the benzamdidine derivative of formula I, in which R3 is hydrogen, reacts with a compound of the formula R3-Z, in which R3 has the meaning given above. except for the hydrogen atom, and Z is a halogen atom, an isocyanate group or an isothiocyanate group, and then the compound of formula I is optionally converted into a salt by reaction with an acid. 22. The method according to claim 21, characterized in that the ni/solid reactions of formula c and II-row amines of the formula RJR2NH are carried out at a temperature from room temperature to 60°C, optionally in an organic solvent. 23. The method according to claim 21, characterized in that the complex compound is decomposed with hydrochloric acid, sulfuric acid or nitric acid at a temperature from room temperature to 50°C, and as a strongly alkaline agent, soda or potash is used to precipitate treatment with this agent at a temperature lower than room temperature. ' 24. The method according to claim 2il, characterized in that the benzamidine derivative of the formula 1, in which R3 is hydrogen and X, m, R1 and R2 have the meanings given above, is reacted with a compound of the formula R3^Z, in which R3 has the above the meanings given with the exception of the hydrogen atom and Z have the meanings given above, in the presence of a base and at a temperature from room temperature to 250°C. 25. A fungicide containing an agriculturally acceptable inert carrier and an active substance, characterized in that as active substances it contains a new benzene derivative of the formula 1, in wherein phenyl, or together with the nitrogen atom to which they are bound, form a 5-7-membered saturated alicyclic ring, which may contain an oxygen atom as one of its members, or which may be substituted with one methyl group or two methyl groups, and R3 is an atom hydrogen, a pyrosto-chain or branched alkyl, alkenyl or alkynyl group, a benzyl group, optionally substituted with chlorine atoms, a cyam group, a cyanoalikyl group, a group of alkoxycarbonylmethyl, an α-alkoxytearbylethyl group, a group of aikoxymethyl, a bL group s/ an alkoxycarbonyl/methyl group or a phenoxymethyl group, an optionally substituted alkyl group or an alkoxy group, or R3 represents a group of the formula 2, in which R4 represents a hydrogen atom, a lower alkyl group, a halomethyl group, a lower alkoxy group, a lower alkoxyalkyl group, lower alkenyl group, lower alkylthiomethyl group, furyl group, thienyl group, lower alkylthio group, phenylthiomethyl group, phenoxy group, optionally substituted methyl group or phenyl group, optionally substituted with halogen atom, methyl group, group methoxy or nitro group, or R3 denotes a group of formula 3, in which R5 and R6 are the same or different and represent hydrogen atoms, lower alkyl groups, cyclohexyl groups, anilinecarbonyl groups, optionally substituted halogenated latomeim or phenyl groups , optionally substituted with a halogen atom or a methyl group, or R3 represents a group of formula 4 in which R7 represents a lower alkyl group, a cyclohexyl group, a benzyl group, a lower alkoxycarbonyl group or a phenoxycarbonyl group, or R3 represents a group of the formula -SO2-R8, wherein R8 is a lower alkyl group, a trifluoromethyl group, a chloromethyl group or a phenyl group, optionally substituted with a halogen atom or a methyl group, except in the case where X is a lower alkyl group, halogen atom, methoxy group or dimethylamino group, n is zero, 1, 2 or 3, R1 and R2 are the same or different and denote alkyl groups, alkenyl groups, cycloalkyl groups or phenyl groups, or together with with the nitrogen atom to which they are bonded, they form a 5-7-membered saturated alicyclic ring, which as one of the members may contain an oxygen atom, or which may be substituted with one methyl group or two methyl groups, and R3 is a hydrogen atom and except where X is a lower alkyl group, n is zero or 1, R1 and R2 are the same or different and are alkyl or alkenyl groups, and R3 is a straight-chain or branched alkyl group, an alkenyl or alkynyl group, a benzyl group, optionally substituted with chlorine atoms, a cyano group, a cyanoalkyl group, an alkoxycarbonylmethyl group, an α-alkoxycarbonylethyl group, an alkoxymethyl group, a bis/alkoxycarbonyl/methyl group or a phenoxyethyl group, optionally substituted alkyl or alkoxy group, and except where X is a lower alkyl group, n is zero or 1, R1 and R2 are alkyl groups, and R3 is a group of formula 2, wherein R4 is an atom hydrogen, lower alkyl group, halomethyl group, lower alkoxy group, lower alkoxyalkyl group, lower alkenyl group, lower alkylthiomethyl group, furyl group, thienyl group, lower alkylthio group, tphenylthiomethyl group, phenoxy group, optionally substituted me group ¬ a back or phenyl group, optionally substituted with a halogen atom, a methyl group, a methoxy group or a nitro group, or R3 is a group of formula 3, in which R5 and R* are the same or different and represent hydrogen atoms, lower alkyl groups, cyclohexyl groups, anilinecarbonyl groups, optionally substituted with a halogen atom, or phenyl groups, optionally substituted with a halogen atom, or a methyl group, or R3 is a group of formula 4, in which R7 is a lower alkyl group, a cyclohexyl group, a benzyl group, a lower group alkoxycarbonyl or phenoxycarbonyl group, or R3 is a group with the formula -S02-1-R8, in which R8 is a lower alkyl group, a trifluoroniethyl group, a chloromethyl group or a phenyl group, optionally substituted with a halogen atom or a methyl group ¬ water or a salt of the compound of formula 1. 26. The fungicide according to claim 1. 25, characterized in that it contains as active substance a salt of the compound of formula I and terephthalic acid, adipic acid, salicylic acid, tartaric acid or hydrochloric acid. 27. The fungicide according to claim 1. 25, characterized in that the active substance is N,N-diethyl-N'-bisethoxycarbonylmethylbenzamidine or N,N-di-n-propyl-N'-methyl-o-methylbenzamidine. 10 15 20 25 30 35 40 45 50122 155 x"^nJ /R' iphysór 1 O /Yztf/-3 -C-R 4 O -C-NH-R7 u S Formula 4 Xn N-R* R1 v ^C-N<"-(Y)m <* VCN Formula 6 Xn -o Wa*- w O- Formula / \ Formula n -rP\ n^C/- P •C? -® Pattern 12 ¦N Pattern /3 Pattern W CH, CH CK /VZ<&- /5 CH, ~CKh(J WZ0/- Pattern W Pattern I' /CH3 CH3 ^^ # /CH3 Qj.„.CH" '2n5 W^a i^ / \X Wzór23122 155 CHp CHp/ (^ Cl^ Cl CL Formula 24 V \ =r ci- ttcór 27 Formula 25 ,ci ^l Formula 30 Br O Formula 32 CH CH, 3\ N // W Formula 35 Formula 28 \ci Formula 2S Cl Formula 29 flFormula 33 Formula 31 Formula 34 Formula 36 Formula 37 /OH Formula 40 (TTy-COOH fiyCOOH Formula 38 Formula 39 Formula 44 /OCOCH3 ^J^COOH Formula 41 Formula 43 COOH COOH Formula or 45 ocC00H V^COOH Formula 46 CH r% 3 \= Formula 47 S03H122 155 C*H„-Q-SAH WLOr 48 0-SO3H c Yizór 50 CH2COOH HO-C-COOH CH2COOH Yizór 49 OH ^ ^ a CH Yizór 51 Yizór 52 CC2H5 -CHjOtfK 7 CH3 -CH2CH£M^J Yizór 53 Yizór 54 cHrO Yizór 55 -CH2-^Q^Cl Pattern 56 o Y\'Z0r 57 o Yizór 59 -?Oa o Pattern i8 OCH3 0 cchlshQ 0 Yizór 61 - c II o ^y /^zc)r & Wafr 63 -co II o II ° o OH3 A CH3 Chip 65 Ol N02 -c-t5 -CNHCNH-O 0 O122 155 -CNHCNH-^^ ii li O O Formula 67 -C -NH^ o ci Formula 69 -CNH-/ XX Formula GQ ¦c^^3 O ^CH, Formula 70 -CNH^CH3 -CNH^H) 0 ,., '. O Formula 71 -cnh^h) s Formula 73 Formula 75 Formula 72 CNHCH2-^3 Formula 74 S02-C^CH3 -SOj^^Cl MzOr 77 Formula 76 -S02^Q^Br Formula 78 - CNHCO -4~S ¦ li li \=/ s o Formula 79 CN R \ Pattern 6 R 1/ NH