SCHAEDLINGSBEKAEMPFUNGS AND PLANT GROWTH REGULATING AGENT

The invention refers to means for fighting against parasits and for adjusting plant growth, which as active substance a Sulfonanilid of the general formula R6 R-S SO=Rl I N-B-A __Ra R (D where RI B A alkyl, Thienyl, Morpholino or Dialkylamino is; Represents to alkyls or Alkenylen; a if necessary more alkyloder hydroxyalkyl-substituted Dithiolanyloder Dioxalanylgruppe, if necessary alkylated or acyliertes Hydroxyiminoalkyl, l, l-Dialkoxyalkyl, 011 i0 - COOH, - CEGB 9, - CENR i ù R l i _O_N=G/, - CN or - COR* 2 'R 9 means, whereby E and G are same or different and in each case oxygen or sulfur is; R and R9 same or different are and in each case hydrogen, alkyl, Cyclot5 alkyl or by Furanyl substituted alkyl represent; Bi° and Rll directly or differently are and in each case hydrogen, alkyl, if necessary thiocyanatsubstituiertes Phenyl, Amino, - NHCOO - alkyl or - CH=COO-Alkyl represent, and B 2 alkyl, if necessary acyliertes Hydroxyalky! , 1,1-Di (alkoxycarbonyl) - meant alkyl or a Morpholinoder Pyrazolyl group alkyl-substituted if necessary, how RA can be present if necessary in form of a Lactons, is, and R R R R5 and R6 same or different are and in each case hydrogen, alkyl, halogeneous-substituted alkyl, Hydroxy, Alkoxy, - SCN, Nitro, halogen, Phenylmercapto, Phenylsulfony! , Alkylsulfonyloxy or Phenyl is, or a salt hievon together with at least one material from the group of the carriers, surface-active means, other pesticides, other plant growth modulators, remedies and fertilizers contain. According to invention used the active substances are new. The new connections are received by the fact that one a) a sulfone amide of the formula SO=R1 I N-H R “R2 R-S R R (II) or a salt hievon with a halogen derivative of the formula X-R-A b) in which formulas X A, R, RI, RZ, R-S, R ", R-S and R6 converts, a Arylaminoderivat of the formula is halogen and the above meaning to have, H f N-R-A R “eJ R R-S R-S R (III) lo or a salt hievon with an acylation means of the formula RISOzZ or (BI SO2) zO, c) in which formulas Z halogen is and A, R, RI, RZ, R-S, R R-S and R “the above meaning aeyliert, if A - COOH meant, a Sulfonanilid of the formula (1) or a salt hievon, where A - COOR 9, - CONB i o R 11, - C-O-N=C R g or - CN d) e} meant, where R R-S, R hydrolyzes ° and R l the above meaning to have, if A - COOR° means, a Sulfonanilid of the formula (1) or a salt hievon, where A - COOH meant, with an alcohol of the formula R90H verestert, if A - CEGR means, an acyl halide of the formula 02R L N-R-CEY R (IV) f) g) with one Alcohol or Mercaptan of the formula R°GH, in which formulas Y halogen is and E, G, H, RI, R', RA, have R B5, H6 and B9 the above meaning, converts, if A - CONR*° R I means, the acyl halide of the formula (IV), where E oxygen is, with a Aminoderivat of the formula HNRI° R *, where RI° and R have the above meaning, converts, if A means, the acyl halide of the formula (IV), where E oxygen means, with a hydroxyl amine derivative of the formula HONE C R' = R9 h) where R' and R9 the above meaning to have, converts, if A - COR 2 means, a carbonic acid of the formula SO2R N-R-CD [COOH) RA R [v again. where D H R: z meant, decarhoxyliert, i) for the production of a salt of the Sulfonanilids the Sulfonanilid salted or j) for the production of the Sulfonanilids a salt of Sulfonanilid entsalzt. Some parent compounds with the production of the connections mentioned are likewise examples from usable according to invention active substances are: 2 “, 6” - Dimethyl l propansulfonanilid; 2 “, 6” - Dichlormethansulfon on [eyelid; 2 “- Chlor-6” - methylmethansulfonanilid; 2 ', 6 ' - Dimethy! - l-butansulfonanilid; 2 ', 6 ' - Dimethyläthansulfonanilid; 2 ' - Äthylmethansulfonanilid; 3 “, 4” - Dichlor-2-thiophensulfonanilid; 3 ' - Chlor-4 “- fluormethansulfonanilid; 3” - Chlor-4 “- - methylmethansulfonanilid; 2” - Methansulfonyloxymethansulfonanilid; 2 ', 6 “- Diisopropylmethansulfonanilid; 2” - Meth ansulfonyloxy-5 “- nitromethansulfonanilid; 2”, 6 “- Dimethyldimethylaminosulfon on [eyelid; 2” - - Chlor-6' methyldimethylaminosulfonanilid; 2 ', 3 ' - Dichlormethansulfonanilid; 3 ', 4 ' - Dimethylmethansulfon on [eyelid; 2 “, 6” - Dimethyl-2 “- propansulfonanilid; 3”, 4 “- Dichloräthoxycarbonylmethansulfon on [eyelid; 3”, 5 “- Dichlormethansulfonanilid; 2”, 6 “- D [methyl-4-morpholinsulfonanilid; 3”, 4 '- Dichlor-4-morpholinsulI0 fonanilid and their salts. New parent compounds of the formula (II) and their salts are manufactured thereby that one acyliert an aniline of the general formula NHz (VI) or a salt hievon with an acylation means of the formula R ISO=Z or (R tSOz) =O. The Sulfonanilid of the formula (I) can form salts. Such salts are Moral1, in particular alkali metal salts, like Natriumoder of potassium salts, and amine salts, e.g. Methylaminoder Kthanolaminsalze. The salts can formed from the Nichtsalzform (i.e. the Nichtsalzform can be led into a salt überZ0) by methods, which are usual for other salts, and transfer into the Nichtsalzform (i.e. entsalzt) by methods, which are usual for other salts. So a salt can be formed by shifting of the Nichtsalzform with a base, e.g. sodium hydroxide; a salt with a base can be e.g. transferred by shifting with an acid, hydrochloric acid, into the Nichtsalzform. The Carbonylderivate of A can be regarded by shifting with distance of a water molecule coming from the group of CO. The derivatives cover: Ketale, where A e.g. OCHs 1 /O-CH, - C-OCH3 or - C] C Hù O-CH CH3 is, Thioketale, where A e.g. SCHS I - C-SCH I @I3 or I CHs is, ex [ME, where A e.g. - C-CH s IL NOH is, Oximester, where A e.g. - C-CH 3 IL NOCOCH is, Oximäther, where A e.g. - C-CH3 is, II STILL 3 Oximcarbamate, where A e.g. - C-tert. Le II N-O-CNItCIt 3 II 0 is, Hydrazone, where A e.g. - C-CH 3 II NNH2 is, substituted Hydrazone, e.g. Methylhydrazone, where A e.g. - C-CH 3 II NNHCH 3 is, or Phenylhydrazone, where A e.g. - C-CH 2 II NNttPh is, and Semicarbazone, where A e.g. - C-CH2 II NNHOSNH is. The sulfone amide of the formula [II) or a salt hievon can by Acylieren of an aniline of the formula (VI) or a salt hievon with the acylation means of the formula (R*SO) 2 0 or R 'S02 Z to be preferably manufactured. Again Z is usually chlorine. The Aoylhalogenid of the formula (IV) can by shifting of a Sulfonanilids of the formula (I), where A - COOH or - means CSSH, or a salt hievon with Thionylhalogenid, Phosphorylhalogenid, Phosphorpentahalogenid or Oxalylhalogenid, in particular - chloride, preferably Thionylchlorid, to be manufactured. An alkyl group in the used symbols exhibits preferably 1 to 15, e.g. 1 to 8, in particular 1 to 6, C-atoms, e.g. methyl, ethyl, Propyl, Isopropyl, Butyl or Hexyl. Each halogen atom is preferably fluorine, chlorine or bromine, in particular however chlorine. Each alkoxy group exhibits preferably 1 to 6 C-atoms, e.g. 8thoxy. The group of alkyls for R can be straight or verzweigtkettig. Usually it contains of 1 to 6, preferably 1 to 3 C-atoms. B is particularly prefers Methylen. Preferred connections of the formula (I) are such, where R* alkyl with 1 to 15 C-atoms or Amino, disubstituiert by alkyl with 1 to 15 C-atoms means; where R* is alkyl with 1 to 4 C-atoms, Morpholino, Thi8nyl or Dialkylamino with 2 to 8 C-atoms, R alkyls with 1 to 3 C-flavours or Alkenylen with 3 C-flavours. A - COOH; - CENH; - CN; - CONHPh; Cycloalkyloxycarbonyl with 4 to 8 C-flavours; Morpholinocarbonyl; - CONHNH; - CONHCH2, COO AlkyI with 1 to 4 C-flavours; CH3 25-CONHNHCOOAIkyl with 1 to 4 C-atoms; - C-N A; - COOR.7 or - CON (R) 2, II O I CH3 whereby R* alkyl with 1 to 8 C-flavours is; - COCH3; - COCHzOH: : Ha - COOCH2/ ----- I \ o CH3 /0 CH CI-13 - COCH20COCH; - CONH BOO t SCN; - COC H; - C-CH s II COOÄt NOH; - COC (CH s) s; - Approx.-CHs; - Approx.-CHs or - C-CHs II II II STILL s STILL s NOCNHCH s II II O O /---I or B-The group %//O means; and three or four of the groups of R2, R-S, R, O R-S and RG hydrogen are alike or different in each case and the remaining are and in each case to alkyl with 1 to 3 C-flavours, halogen, Hydroxy, Phenylmercapto, - SCN, Nitro, Alkoxy with 1 to 6 C-atoms or tri fluorine methyl mean; where R* alkyl with 1 to 15 C-flavours or Dialkylamino means; R alkyls with I to ö C-flavours is, A - COOH, - CEGR9, CENR*°RI* or - CN represents, whereby E and G are same or different and in each case oxygen or means sulfur; H " alkyl with to 15 C-flavours is; I0 Bl° and R* same or different are and in each case hydrogen, alkyl with I to 15 C-atoms or Phenyl are; and R2, RA, R R-S and R6 directly or differently are and in each case hydrogen, alkyl with i to 15 C-flavours, if necessary more einoder several times replaced with halogen; Alkoxy with 1 to 6 C-atoms; - SCN; Nitro or halogen mean; and where RI alkyl with I to 15 C-atoms or Dialkylamino means; R alkyls or Alkenylen with i to 6 C-flavours represents; A - COR is, whereby R 2 alkyl with I to 15 C-flavours means; and R2, Bs, R ", R 5 and R6 directly or differently are and hydrogen in each case; Alkyl with 1 to 15 C-atoms, if necessary replaces more einoder several times with halogen; or disubstituiert by alkyl with 1 to 15 C-atoms, - SCN, Nitro; Is halogeneous or Mercaptophenyl, represent. Preferred specific connections, in particular as herbicides, are: N-Cyanomethyl-3', 4 ' - dichlormethansulfonanilid; N [l (Äthoxyearbonyl) - ethyl] -2 ', 6 ' - dimethyl - l-propansulfonanilid and n [l (Äthoxycarbonyl) - ethyl] -2 “, 6” - dimethyläthansulfonanilid. A further preferential specific connection, in particular than fungicide, for example for use on wine or potatoes, is N-I l (E4ethoxycarbenyl) - ethyl] -2 ', 6 ' - dimethylmethansulfonanilid. Finally a further preferential specific connection, in particular for use than fungicide, is N-2-Oxopropyl-2 “, 6” - dimethylmethansulfonanilid. The connections (I) are suitable as active substances in pesticides and Pflanzenwacbstumsregulatoren. The connections, where A - COOH, - CEGR “, - CENR *° R **, i O N C/B7…. R9 or - CN meant, are particularly effective on the plant physiology, as 3D affect them the Wachstnm of the plants, so that the connections can be used in herbicides or Pflanzenwaohstumsregulatoren. The connections (I), where A - COR*z means, it is also in particular in fungicides usable. The connections (I) are also in antibacterial-average as active substances usable. They are outstanding in means usable to fighting against mushrooms or weeds in arable crops. The connections can be used for example in means for the fight against Sternmiere [Stellaria media), white Gänsefuß (Chenopodium album), game oats (arena fatua), Binse (Alopecurus of myosuroides), chicken millet (Echinoehloa crus galli) or finger grass (Digitaria sanguinalls). - 8 - NR, 368358 the connections can in means for the fight against weeds for example in food fruits, how potatoes, wine, carrots or Cerealien, how rice, wheat, barley or corn, Sehmuckfrüchten or]? eldfrüchten, like cotton, to be used. For the use in fungicides the connections are used preferably for the fight against mushroom diseases against plants, in particular one of the evenly stated kinds. The connections can be used in means for the fight of different kinds of mushroom, e.g. Phythium, Phytophthora, Plasmopora or Pyricularia. The connections (I) erfindungsgemäfl in form ven compositions are used, which can be manufactured by mixing the components. Usually the Zusammeni0 setting is manufactured first in the form of concentrates, the e.g. 0.5 to 85% of the connection (I) contained, and these are usually diluted water, for the use, with water or a hydrocarbon, generally in such a manner that the concentration of the connection amounts to 0.05 to 5%, although with application in extremely low volume the concentration can be higher for example up to 20%. Percentages and parts in this description refer to the mass, if nothing else is indicated. The compositions usually contain an surface-active means and/or a carrier. The carrier can be a liquid, e.g. water (like the water, which is used for the dilution of a concentrate for the creation). If water is used as carrier in a Konz8ntrat, also an organic solvent can be present as carriers, although such is not used normally. Favourable way can be present a oberfläehenaktives means. The carrier can be another liquid than water, e.g. an organic solvent, like a solvent not misehbares with water, z, B. a hydrocarbon, which simmers within the range of 130 to 270°G, in which the connection is solved or is not suspended. A Konzentratù some solvent not mixable with water contains, contains appropriately also an surface-active means, so that the concentrate works as emulsive oil with mixing with water. The liquid can be a solvent, e.g. 2-Methoxyäthanol, methanol, propylene glycol, Diäthylenglykol, Diäthylenglykolmonoäthyläther, form amide or methyl form amide misehbares with water. The carrier can be a solid, which can be divided finely. Examples of suitable solids are limestone, clay/tone, sand, mica, chalk, Attapulgit, Diatomit, pearlite, Sepiolit, silicas, silicates, Lignosulfonate, peat and firm fertilizer. The carrier can be natural or synthetic origin or a modified natural material. Net-cash powders, which are in water soluble or dispersable, can be received by mixing the connection in Teilahenform with a teilehenförmigen carrier or Aufsprühen of the melted connection on the teilchenförmigen carrier, adding Netzund of dispersing agent and fine grinding of the entire Pulvermischnng. A Aerosolzusammensetzung can by mixing connection with a propellant, e.g. a polyhalogenierten alkane, like Dichlordifluormethan, and appropriately also with a solvent to be formed. A fluid suspension concentrate can, if the connection possesses a small Löslichkelt in water, by meals of the connection with water, a wetting agent and a suspending means be formed. A fluid suspension concentrate, where the carrier is a hydrocarbon with a boiling range from 130 to 270°C in place of water, can be formed. ISO can be for example firm the means according to invention (e.g. a dust or granulates) and a firm carrier contain, or it can be a liquid (e.g. a emulsifying shedding concentrate) and a liquid carrier, i.e. a hydrocarbon with a Siedebereieh from 130 to 270°C, contain. The expression T'oberflächenaktives means " is used in broad sense and covers materials, like emulsifying means, dispersing agents and wetting agents. Such center! are probably well-known. Nr.368358 the used surface-active means know anion-active surface-active means, e.g. Soaps, Monooder Diester of Phesphorsäure with Fettalkoholäthoxylaten or salts of such esters, fat alcohol sulfates, like Natriumdodecylsulfat, Natriumoctadecylsulfat or Natriumcetylsulrat, äthoxylierte fat alcohol sulfates, alkyl phenol sulfates, Ligninsulfonate, Petroleumsulfonate, äthoxylierte Alkylarylsulfonate, like alkylbenzenesulfonates or nied. Alkylnaphthalinsulfonate, e.g. Butylnaphthalinsulfonate, salts of sulfonierten Naphthalin formaldehyde condensates, salts of sulfonierten phenol formaldehyde condensates, or more complex Sulfonate, like the Amidsulfonate, e.g. the sulfonierte condensation product of oleic acid and N-Methyltaurin or the Uialkylsulfosuccinate, e.g. the Natriumsulfonat of Diectylsuccinat, its. The surface-active means can be also nichtionogene means, e.g. condensation products of fatty acid esters, Fettalkoholen, fatty acid amides or fat, more alkyloder alkenyl-substituted Phenolen with ethylen oxide, fat star of multi-valued alcohol ethers, e.g. Sorbitanfettsäureester, condensation products of such esters with ethylen oxide, e.g. Polyoxyäthylensorbitanfettsäureester, block copolymers of 21thylenoxyd and propylene oxide, acetylene glycols, like 2.4.7.9 - - Tetramethyl-5-decFn-4,7-diol, or äthoxylierte AcetFlenglykole. The surface-active means can be also cation-active means, e.g. alkylund/or aryl-substituted quaternäre ammonium compounds, like Cetyltrimethylammoniumbromid, or äthoxylierte tert. Fat amines. Preferential ones surface-active means are äthoxylierte fat alcohol sulfates, Ligninsulfonate, Alkylarylsulfonate, salts of sulfonierten Naphthalin Formaldehydkondensaten, salts of sulfonierten phenol formaldehyde condensates, Dialkylsulfosuccinate, Alkylphenoläthoxylate and Fettalkyläthoxylate. Nichtienogene surface-active means are preferred. The active connection can be e.g. mixed with another pesticide, herbicide, fungicide, insecticide or antibacterial means or with another plant growth regulating agent. Packing up preparations are possible, in which the connection (I) already with another pesticide or plant growth modulator mixed is, and also individual packing, which is intended for it to keep the connection (I) and another pesticide or another plant growth modulator in separate containers which are then mixed for example in a spraying container for use. Special one distributes with mixtures with another herbicide or fungicide is obtained. The means according to invention can be used successively with another pesticide or plant growth modulator, in particular with another herbicide or fungicide; e.g. a herbicide before planting or before accumulating a fruit is applied and the other one after accumulating the same. The other herbicide can be for example or several the following: phenoxyaliphatische acid, substituted urea, Triazin, phenol, nitrile, Bipyridyliumverbindung, substituted benzoic acid, halogenierte aliphatic acid, Carbämat, Thiocarbamat, Chloracetamid, Diazin or arsenic connections. B0 the relationship of the connection (I) to the other pesticide or plant growth modulator can vary over a wide range depending upon the special assigned connections and the intended Verwendungszweek. Generally amounts to the relationship of the connection (1) to the other pesticide or plant growth modulator I: 0,1 to I: The connections (I) can be in mixture with not-phytotoxic oils (e.g. Agri oil plus, Sun Oll IIE or Fyzol IIE). They can be in mixture with a remedy (a connection with the characteristic of the improvement of the selectivity of herbicides), e.g. N, N-Diallyl-2,2-dichloracetamid or 1,8-Naphthalinsäureanhydrid. The connections can be in mixture with fertilizers. When using the connections (I) in total herbicides usually high creation rates, e.g. at least I0 kg per ha, are like 10 to 25 kg per ha, which can be decreased connections necessarily, if they are not mixed with other herbicides, in which case the rate. When using the connections (I) in selective herbicides the application rate is usually substantially smaller and can amount to for example 0.5 to 10, e.g. 0.5 to 8 kg per ha, like 1 to 4 kg per ha. When using the connections in PflanzenwachstumsregulaLoren usually low AnwendungsraLen is necessary, like 0.1 to 4, e.g. 0.5 to 1 kg per ha. For use in fungicides, insecticides or antibacterial means the connections are used generally in a portion from 0,3 to 10, e.g. 1 to 6 kg per ha. For the use in fungicides the connections a plant growth medium, in particular a medium on basis of peat, in which plants are to grow, can be incorporated for example in a portion from 10 to 1000, preferably 50 to 500 g Verbindung/cm3. The connections can be used as seed fertilizers, whereby the expression “seed” is used in broad sense and tubers and bulb includes; for this use the connections in a portion of for example 0.1 to 1 g per kg seeds can be used; preferably they become in M [schung with a carrier begun, in order to facilitate the mixture with the seeds. The carrier can be a liquid, e.g. a Kohlenwass8rstoff, or a solid, e.g. a clay/tone or an Fuller earth. The means according to invention know the earth (including compost) on plants (including seeds), Landoder water surfaces or on liveless or stored materials, e.g. Textiles, paper, leathers or wood, which are exposed to mushroom attack, to be applied. Preferably they become as herbicides, in particular selective herbicides, or fungicide, in particular for application in a place, where an arable crop, in particular a Gerealienfrucht, like wheat, grows barley or corn, or, less preferentially, to grow is, applied. Thus the means before or after planting the fruit can be applied. They can be used to the Vorauflaufoder Nachauflaufverwendung. The means can be used for protecting plants against weeds and mushrooms. The following modes of production are to describe the production of active substances and/or raw materials used according to invention to their production. Mode of production 1: A solution of 25 ml 1-Propansulfcnylchlorid in 50 ml toluol was added during 15 min to an agitated solution by 55 ml 2,6-DimeLhylanilin in 400 ml Teluol. The mixture was agitated and for 20 h at the Rückf] uß was cooked, then cooled and filtered. The Toluoll6sung was washed three times with diluted hydrochloric acid and water, extracted then three times with diluted sodium hydroxide solution. The aqueous alkaline solution was acidified with diluted hydrochloric acid and the product by filtering was collected, washed and dried with water. By KrisLallisation from Toluol/60-80° petroleum ethers were received 2 ', 6 ' - DimeLhyl i - propansulfonanilid crystals to 28.0 brown in form g (55%), Fp. 72°G. Herstcllungsweise 2: A mixture of 28,0 g of the Sulfonanilids of mode of production l, 9.4 g water-free KaliumcarbnnaL, 17.6 ml Äthyl-2-brompropionat and 200 ml 1,2-DimeLhoxyäthan was agitated and 20 h at the return flow cooked, then cooled and filtered and the FilLrat was evaporated. A solution of the remaining oil in ethers was washed with diluted sodium hydroxide solution. The alkaline solution was acidified with diluted hydrochloric acid and the precipitated solid was collected by filtering. This material (13.3 g) were identified as not umgeseLztes Sulfoanilid. The ethereal solution was evaporated and a solution of the remaining oil in 100 ml Äthanol/10% sodium hydroxide solution (l: i) on 500C 2 h long heats up. Ethanol was evaporated, whereby an aqueous solution of the sodium salt of n (2,6-Dimethylphenyl} - n (1-propansulfonyl) - alanine remained. The solution was acidified with diluted hydrochloric acid. The received acid was extracted with chloroform, which chloroform solution dried and evaporated and the arrears from Toluol/60-80° petroleum ether crystallize, whereby 14.1 g (73% yield, related to not-won Sulfonanilid) brown crystals of n (2,6-Dimethylphenyl) - n (l-propansulfonyl) - - alanine was received. Mode of production 3: A solution of 6,5 g of the alanine derivative of mode of production 2 in i00 ml Tolunl was treated with 10 ml Thionylchlor Œ D, 1 h at the return flow was cooked and evaporated then. The remaining oil was again evaporated with toluol, in order to remove traces from Thionylchlorid to, and the arrears then 1 h long in 2-Propanol cooked and evaporated. A solution of this oily arrears in ethers was washed, dried with Natriumbicarbonatlösung and evaporated to a brown oil, which was perkoliert by a silica-gel column with chloroform. With evaporation of the Eluats the Isopropyläther SO= CH2 CH=CH3 was received • to Hs /CHs N-CHCOOCH CH 3 CHs ß jCHs as clear yellow oil. In similar way the following connections were received: : SO 2R 1 N-CH-A I Sub. Mode of production g 1 R18 substituent o l o n--\ O ME ME ME cooÄt COOMe coo t cooÄt 2,6-diMe 2,8-d£Me 2, B-diMe Fp. degrees of 1 3 - 144 62 108 ME 3, #-diC1 72 8 - CH2 COOH ME COOXt 3, #-diCl 52 modes of production 9 to 38: In similar way, as in the preceding described, the following connections were manufactured: Ester mode of production t7 acids Herstellungswe£se RST 1i 12 1# 18 tg 02Rz Rze I - CH-A E---Sub. G 1 He ME ME ME ME t ME e tear ME e ME e ME ne ne ME COOH COOß COOH COOH COOß COOH COOH substituent 2-Ät 2-C1-6 ME 2,8-diMe 2-OCH 2,6-diMe 2,6-diÄt 2, B-dLCl Fp. degrees i 131,212 g6 118,131,122 11B 12B ME 14 ME fuel element ME H ME ME R18 cooÄt cooÄt cooXt substituent 4-Ci 4-Ci 2,6-d£He Fp. AC ö [oil oil analysis, if the product is e£n oil analysis found computed C H CzzHzùC1N04S CzsMzöClNO S Cz3HzgNO S N ill ß, 7¢ 4.80 45.03 4.63 45.28 4.86 45.82 5.45 47.13 5.27 54.52 6.51 54” 72 6.71 56,0B, 7,2g 56.16 7.07 4,7B k, self-service 5.17 4.91 cooÄt 2,5-d£He oil Cz” BszNO” S 5.07 B, 6B ester Ilers el] ungsweise 21 22 23 24 26 27 29 31 32 33 34 8! 8 Te ME RH COOÄ 3-CF Subst£tuent Fp. degrees of analysis, if the product is an oil analysis found computes oil CL3 HIBF3 N04 8 45.84 5.00 4.37 46.01 4.75 4.13 ME H COOÄt 3-CF Öl2! time” FsNOùS 44.00 4.11 4.61 44.30 4.34 #, 31 ME It COOÄt 3, &-d£Cl oil C IH 3 Cl2 NO “S 40.78 3.96 4.59 BO, 50 4.02 4.29 COOL 2-isoPr oil C, ùH2 zNOùS 55, g9 7.38 4.96 55.15 7.07 4.58 ME ME COOÄt 3,4-dlCl OIL C2 11 L s612NO S 41.90 3.99 4.00 42.36 4.44 4.12 ME ME COOÄt 2-Ä oil C14 H21 t O4 S 55.94 5.89 4.80 56.18 7.07 4.68 ME ME COOÄt 2-Cl, 6Me Ö [C z3tl1 degrees] NO, S 48.52 5.43 4.33 48.82 5.57 4.38 ME ME COOÄt 2-061ts oil C sH10 NOsS 52.19 0.35 4.84 51.81 6.35 4.65 n-Pr ME COOÄt 2,6-diMe 44-46 c1 “HzsNO, S 58.28 7.77 4.11 58.69 7.70 4.28 ME ME COOÄt 2-Ci oil C zzH z “C1NO” S 47.05 5.60 4.60 47.14 5.27 4.58 Ät ME COOÄt 2,6-d£Me 702 NOùS 57.83 7.77 4.33 57.48 7.40 4.42 n-le ME COOÄt 2,6-diMe oil C z7H27NO, S 50.45 8.25 3.83 59.79 7.97 4.10 ME ME COOÄt 2,6-diCI 108 ME ME C80Me 2,5-d£Me oil C3 H, sNO, S 54.59 6.69 4.45 5#, 72 6.71 4.91 ME ME COOÄt 2,6-diÄt oil Cz6H2sNO S 59.00 7.35 4.59 58.69 7.70 4.28 - 14 - NR, 368358 esters Hersteilungsweise 36 3? 38 81 818 ME ME ME ME ME ME COOn Pr CDO (CHz) CH3 COOCHCH (! Cycles per second) CH3 Substltuent 2,6-diMe 2,8-d [ME 2,6-diMe Fp. °C oil oil oil analysis, if the product oil is found computes C/ùH23ri04S CzTHz N04S C=oHssNOùS 57.57 7, #9 57.48 7 0 59.66 8, [0 59.79 7.97 53.01 8.5 [62.63 8.67 4.41 B, 47 3, g8 4.10 3.70 3.65 mode of production 39: A solution of 5 g n (2,6-Dimethylphenyl) - N-methansulfonylalanin in 50 ml chloroform was treated with 5 ml Thionylchlorid and the solution i h at the bending river was cooked and evaporated then. The arrears were evaporated again with toluol, in order to remove traces from Thionylchlorid to. A chloroform solution of the bending conditions was left the mixture untouched 4 h treated with a satisfied solution of ammonia in chloroform, with Raumtemper&tur, added then water and evaporated the organic solvent. The suspended solid was filtered off, washed and dried with water. By recrystallizing from ethanol the amide became SO2CH3 ton of CH3 N - HCONH2 CHe I/CH3 in form of colorless crystals receive, Fp. 158°C. Modes of production 40 to 67: In similar way, as in manufacture example described 39, the following connections were manufactured: HersEellungswelse 42 43 44 46 47 48 49 51 52 OzR1 RzB I - CH-A [I1 ME ME ME ME ME ME ME ME ME e ME ME ME [iIß ME He ME ME ME ME A CONÄLz CONÄt 2 CONÄtz CONÄL 2 CONÄt2 CONHPh \ __/CONH2 CONH z CHs CHs eH3 - @o CHs CH3 J substituent 4-CI 3-CF3 3,4-d£Ci 2-ÄL 2-ÄE 2,6-diÄt 2-Ci, 6-Me 2-ÄL 2, B-diMe 2,6-dLÄL 2-Ät Fp. °C 76 76 108 54 90 156,120,134,158,126,124,135,103 mode of production 53 56 57 58 59 61 62 63 RI ME e ME ME le ME ME ME Rzs ME ME e e He 7 \ - II 0 7 \ - N 0 \ __/_N/m (L ö CH CHs - NN. _. CH3 - N 0 CH3/, 3 - N \ [/P CH3 Substltuent 2,6-diHe 2-Ät 2,6-d [He 2-Ät 2,6-diMe 2, “- diHe 3,4-dlC1 4-Me 2-Ät 4-Ät 2,6-disse Nr.368358 I Fp. °C 12k-126 93,138,168,110,156 IO “101 Fp. Herstellungswe [SE 64 66 67 R does not determine! ME ME e %Me NCH=C0 - H - N CH3 H - N H - N /- ' - _ substituent 2,6-diÄt 2, B-diMa B%He /-- \ l N NOCH2 - N 2,6-diHe Fp. degrees of 78 78 109,234 mode of production 68: A mixture of 7,0 g 3,4-Dichlormethansulfonanilid, 2.4 g water-free potassium carbonate, 2.2 ml chlorine acetonitrile and 100 ml 1,2-Dimethoxyäthan was agitated and for 6 h at the return flow was cooked. The dark reaction mixture was cooled down, filtered and evaporated. A solution of the remaining oil in chloroform was washed, getrooknet and evaporated well with water, whereby a black oil became to receive, which was perkoliert by a column by silica-gel with chloroform. With evaporation of the Eluats an oil was received, whose solution in ethanol solid separated a cream-colored, which was identified as N-Cyanomethyl-3,4-dichlormethansulfonanilid, I0 yield 3.8 g, Fp. 83°C, SO=CH, I N-CH2CN I c1 modes of production 69 to 72: In similar way, as in mode of production described 68, the following connections were manufactured: SO R * N-CH - A J Sub. Mode of production 69 71 72 RZ R=8 A substituent e e ME H H CN 4-CI CN 2,6-diMe CN 2-isoPr CN 3-CF 3 ME Fp. °C 102 84 99 61 mode of production 73: A slow hydrogen sulfide stream was blown by an agitated solution by 6,0 g N-Cyano methyl-3,4-diohlormethansulfomanilid in 75 ml Pyridin with a content by IL, 0 ml tri ethyl amine. The reaction was accomplished at ambient temperature during 4 h and the mixture was poured in 1500 ml ice/water. The precipitated brown Feststeff was collected by filtering, washed and dried with water. The product became as n (Thiocarbamoylmethyl) - 3,4-dichlormethansulfonanilid identifies, yield 6.0 g (89%), Fp. 1780C. I0 modes of production 74 to 77: In similar way, as in mode of production described 73, the following connections were manufactured: SO2R* R, 8 I N - CH - A Sub. Mode of production 74 76 77 RI ME ME ME ME R18 H H H S - CNH = S IL - CNH 2 S II - CNH2 S IL - CNH2 substituent 2-Isopropyl 4-Chlor 3-CF 3 2,6-Dimethyl Fp. °C 136,186,136,160 modes of production 78 to 80: In similar way, as in mode of production described 2, the following connections were manufactured: Rl ME n-le n-Pr mode of production 78 79 SO=R' Rle N - CH - A I Sub. R e A Ät COOH ME COOH ME COOH modes of production 81 to I08: Substituent 2,6-diMe 2,6-diMe 2,6-diMe Fp. °C 164 I12 143 in similar way, as in mode of production described 3, were manufactured the following connections of the formula indicated in the modes of production 78 to 80: Herstellun sweßse 81 82 83 8 8ö 87 B8 89 Ät ME NHez e NHe2 Me2 RI8 ME t e ME e ME ME cooh cooÄt cooÄt coo t coo coo t cooÄt coo t substituent 2,6-diHe 2-CI, 6He 2,6-d£Me 3, #-diCl #-OßO2He 3,4-diCl 2,6-d£Me 2,6-diMe Fp. °C oil oil oil oil 101 80-82 oil oil found computes Ct? Cycles per second N9 S Cz2HzeCINO S CzsHz NO S Cz3HzeC12NzO S C=vH2 NOB2 CzsH2 N204S C zùù2=c1ù2 oùs analysis, if the product is an oil analysis %C 60.02 59.79 46.79 #7,13 57.56 57.48 &2,70 42.28 50.01 55.56 55,0# 54.85 ME 2-CI, 6-Me oil 48.05 #6,20 oH N 7.61 7.97% 90 5.27 7.26 7, %0 B, 60 4.91 5.92 5.76 7” 00 7.37 5.68 B, 07 3.80 B, RST 4.37 4.58% 66 4.47 7.16 7,5g 3.58 3.81 8.36 8.53 7,9# 8.03 I I Z P CO Hertellun9swelse 90 gl 92 93 94 95 96 97 98 99 100 g 1 NHe2 ME ME ME ME NMe2 e NMe2 NMe RIB ME ME ME ME ME ME M8 COOHe CODÄt COOMe cooÄt CO0isoPr CO0isoPr cooÄt cOOHe cooÄt substituent Fp. °C found 2-C1,8-He 2-OS02Me 2,6-dlMe 4-OH computes 2, B-diMe 2-C1,8-He 2-C1,6-Me 3,4-d£C1 2, B-d£Me 3,4-diC1 {} 1 oil 108 64 76 78 öz I08 oil oil 4-01 analysis, if the product is an oil analysis I C H I I Cz3HzsC1N20ùS C13H19N07S2 Cz HzGC12N20ùS CzzRz4C12N204S Cz2Hz7CIN2O4S N 46.95 5.39 7, gl 46.63 5.72 8.37 42.76 5.34 3.60 42.73 5.24 3.83 42.88 4.54 7.85 42.51 4.39 7.63 39.01 4.00 8.81 38.72 4.14 8,2t 45.22 5.16 8.57 44.93 5.34 8.73 I I Z L CO ¢, o ol CO HersEel] ungsweise ioi 102,103,104,105,108,107,108 RI RK Ät e e e e RK nPr R18 ME ME for each Ät Ät cooisoPr - (CHz) 2-COO t - (CH2) 2-COOMe _, cù2, _c00il I CsH.2” COOffe cooÄt cooÄt substituent 2,6-diHe 2,6-d£Me 2,8-diHe 2,6-d ME 2,6-diMe 2-CFs, 4-SPh 2,6-diHe Fp. °C oil 92 oil oil oil oil oil found 5epechneE CzeH2sNO S C, sH23NO S Gz H2zNO S C =IH3 10.8 Cz “H, eFs O “S2 CxöHzsNOùS analysis, if the product eLn oil is analysis 59.02 58.69 57.14 57.48 55.81 56.15 63.80 63.44 49.72 B9,87 58.29 58,6g 2,6-diMe 51 7.95 7.70 7,1ö 7.40 6,9k 7.07 8.44 8.87 4.53 4.19 7.40 7.70 61 4.28 4.33 4.47 4.50 4.68 3.83 3.52 3.71 3.23 3.94 4.28 I I z L (33 CO mode of production I09: In similar way, like in Bromlactonausgangsmaterials, the Lacton IO was manufactured, Fp. 127°C. - 23 - Nr.36835B mode of production 2 described, however using a mode of production llO a III 112,113 towards the formula indicated in the examples 78 to 80 manufactured: Herste|lungswe£se llk 115,116,117,118 i19 120 RI ME ME ME ME nPr ME ME RIs ME CN CN CN CN CN CN CN Suhstltuent 2-CI, 8-Me 2,8-diMe 2-C1 3-el, k-ME 3,4-diCl 2,5-diC! 3-CI, #-f RZ R z8 A ME ME ME ME H CONÄL ME CONHCH2 COOÄt ME CONMNHCOOÄt H CH2 CH2 CONÄt2 modes of production 114 to 134: Substltuent 2-el, O-ME 2,8-diMe 2 - diMe 2 - diMe Fp. °C gg 178 oil analysis, if the product is an oil analysis found %C computes Cz, H20N20 S 5g, 88 5g, g7 H 8.64 8,2g %N 8, k0 8.23 in similar way, as in mode of production described 6B, became the following VerbindunFp, °C 88 80-82 88 112 II0 modes of production II0 to 113: In similar way, as in mode of production described 39, the following connections of the formula indicated in the examples 78 to 80 were manufactured: O = ME -- O CH3 I CH3 HersLellungswelse 121 R! ME H CN 122 ME H CN 98-99 123 RKs H CN 79-81 124 NHe2 H CN 125 ME H CN 86,126 ME H CN 64,127 ME H CN 118,128 ME H CN 114-116 129 ME H CN 88,130 NRe2 H CN 52,131 ME H C 192,132 ME H - (CH2) =CN 51,133 ME H - (CH2) =CN 78,134 ME H - (CHz) 2 CN 88 Substltuent 2,6-d£Ci 2-OS02Me 3,4-d£Ci 3 - diCl 2,3-d£Ci 3-C1 4-SCN 302,4-C1 2,4-dLCI 4-C1 3,4-diMe 2,6-d£He 3 - D c1 3,4-diMe modes of production 135 to 146: Nr.36835B Fp. °C B2 in similar way, as in mode of production described 73, towards the formula indicated in the modes of production 7B to 80 manufactured: became the following VerbindunHersLellungswelse RZ Rze A substituent Fp. °C 135 ME IL CSNHz 2-CI, 6-Me 52 J3 e S 2 3-CI, ¢-He 202,137 ME H CSNH 2-C1 172,138 ME H CSNH2 2,6-diC1 180 13g ME H CSNHz 2,5-dlC1 196,140 ME R CSNH2 3-C1 18,141 nPr H CSNh2 3,4-diC1 16B-170 142 Ät H CSNH2 3 - diCl 162-164 - 25 - NR, 368358 mode of production 143,144 I#5 148 R* RLa A substituent He He ME CSBH2 CSNH2 CSNH2 CSNH2 2,3-dlCl 3-C1,4-F 2,4-diC1 2-OS02Me ME Fp. °C 178,182,160,180 mode of production 147: S02Me l NHCH 2 COOÄt NCH2COOÄt MeSO2 CI Pyridin a solution of I0,0 g N-Phenylglycinäthylester in 50 ml Pyridin was treated with 4,3 ml methane sulphonyl chloride. The exotherms reaction it was let unchecked take place on which the mixture 2 1/2 h at the return flow was cooked and cooled then; subsequently, it was poured onto a rapidly agitated mixture from ice/water/hydrochloric acid. The precipitated, brown solid was collected dulch filtering, washed and getrecknet with water. Yield 7.0 g [49%). By recrystallizing from Æthylacetat/60-80°C petroleum ethers became colorless 1< ristalle with a RST Fp. receive from 66°C. Mode of production 148: SO, Ät O±Ät? H3 NCHCOOÄt I< 2 C03 /DMF a mixture of 6,0 g 2 ', 6 ' - Dimethyläthansulfonanilid, 2.1 g water-free Kaliumoarbonat, 3.65 ml Äthyl-2-brompropionat and 90 ml dimethylformamide (DMF) was agitated and heated up 7 1/2 h on 90°C. The mixture was cooled and filtered and washed the arrears at the filter with hot dimethylformamide and finally evaporated the filtrate. The received yellow oil was loosened in ethers and the solution was washed successively with 10%iger sodium hydroxide solution and water, then getrecknet (MgSO) and evaporated. The firm arrears were mixed into a paste with little ethanol and the crystals were also collected by filtering. Yield at N-I-Carboäthoxyäthyl-2',6' dimethyläthansulfonanilid 5.7 g (ö5%), Fp. 70°C. Mode of production 149: A mixture of ö8,5 g 2 ', 6 ' - Dimethyläthansulfonanilid, 24.5 g water-free potassium carbonate, 58.0 g Äthyl-2-brompropionat and 4Q0 ml 1,2-Dimethoxyäthan was agitated and cooked 66 h under return flow, cooled down and filtered then and evaporated the filtrate. A solution of the oily arrears in ethers was washed to 2 three times with I00 mI 10%iger sodium hydroxide solution and then with water, dried (MgSO) and evaporated, received wöbei to n (l-Carboäthoxyäthyl) - ', ö' dimethyläthansulfonanili as b eat-yellow oil with a purity from more than 99% (by gas liquid chromatography). The aqueous alkali washing liquids were combined and acidified with diluted HC1. The precipitated Feststeff (9.9 g) filtered off, with water one washed, one dried and one did not identify as urngesetztes Sulfonanilid. The Gesamtausbeute of the ester amounted to 84.5 g (98%, related to not won Sulfonanilid). Mode of production 150: SO2FAe SO2 ME OH3 ICH3 moùco ù ùcoo où, | où, cù, I cùo a solution of 5,6 g n [1 (2-Äthoxycarbonyl) - hydrazinocarbony]) - ethyl] -2 ', 6 ' - dimethylmethansulfonanilid in 75 ml Athannl plus 75 ml 10 iger NaOH Läsung was heated up 2 1/2 h on a Dampfbad and cooled then; afterwards ethanol was evaporated. The received aqueous solution was eye-acidified, 1 h Iang at the Dampfbad was heated up and filtered then. The filtrate was neutralized with diluted NaOH, satisfied with sodium chloride and extracted with chloroform. The chloroform solution was getrockuet and evaporated. The arrears resulted in 58%) nearly colorless crystals of n [1 (Hydrazinocarbonyl) - - ethyl] from a solution in Toluol/60-80°C petroleum ether 2.6 g (- 2 ', 6 ' - dimethylmethansnlfonanilid, Fp. 115 to 118°C. Mode of production 151: 2 “, 6” - Dimethyläthansulfonanilid 114.4 g ethane sulphonyl chloride were added slowly {during 15 min) to an agitated solution by llO ml 2,6-Dimethylanilin in 500 m] Pyridin. The exotherms reaction it was let unchecked take place (the temperature rose to 60°C), on which the reaction mixture 3 h at the Rückfluf3 cooked, cooled and into a fast agitated mixture (5 1) of water, ice and hydrochloric acid was eaten. The precipitated brown granulatförmige solid was collected by filtering, washed well with water and dried under vacuum with 50°C. The yield at raw 2 ', 6 ' - Dimethyläthansulfonanilid amounted to 152.0 g (80° “), Fp. 9O°C. The entire raw product was loosened in 100 ml 40%igerNatriumhydroxydlösung and the solution was diluted to approximately 2 1, warmed up with activated charcoal 30 min long and filtered then. The clear blaßge] fuel element filtrate was cooled down and poured slowly to a rapidly agitated mixture of ice, water and hydrochloric acid. The precipitated white solid was collected by filtering, washed with water and dried under vacuum with 5O°C. The yield at cleaned MaLerial amounted to 114.7 g (60B), Fp. 92°C. Production ways 152 to 167: In similar way, how in mode of production I besehrieben, the following Sulfonamide were manufactured: SO2R' I NH Sub. Hecstellungsweise 152,153 g 1 Methylen /4ethyl substituent 2,3-Dichloc 3 - Oi ethyl Fp. °C 102 92 Herstellungswelse 154,155 15@ 157 Fp. °C 102,104 94 158,159,160 13B 161 Iö2 163,164 g 1 Isopropyl - CH2COOÄt methyl methyl n-butyl methyl 2-Th£enyl methyl methyl methyl methyl methyl D£methylamino Dimethytamlno substituent 2, B-D£methyl 3,4-O chlorine 2,6-Dichlor 2-Chlor-6-methyl 2, ö-Dinethyl 2-Äthyl 3,4-D£chlor 3-Chlor-4-Fluor 3-Ch [or-4-methyl 2-Methansu1%nyloxy 2,6-Diisopropyl 2-MethansuiFonyloxy -5-nitro 2, ö-Dimethyl 2-Chlor-6-methyl 165,165,167,116 83 121-123 g3 178 Nr.368358 connection of mode of production 156,158,166,2.5 - 3.0, 3H, m (aromatic); 3,5, 1H, broad s (N-H); 6,7, 3H, s (OH3) 2.95, 3H, s (aromatic); 4,2, 1H, broad s (N-H); 6,67,0, 2H, m (S-CH=); 7,65, 6H, s (2,6-diCHa); 7,9 to 8.7, 4H, m (CH2 CH, CH, CIIa); 9,1, 3H, t (CH2 CH, CH2 CH3) 2.95, 3H, s (aromatic); 3,95, IH, broad s (N-H); 7,15, 6H, s, [N (CH3),]; 7,6, 6H, s (2,6-diCHs) (CDCla) the NMR spectra of the connections, for in the table no Fp. is indicated, are as follows: Connection of mode of production (CDCI 3) 167 2.75 - 3.0, 3B, m (aromatic); 3,8, IH, broad s (N-H); 7,2, 6H, s [N (CHa) 2]; 7,55, 3H, s (CHa) mode of production 168: N-2-Oxopropyl-4 “- ohlormethansulfonanilid a mixture of I0,0 g 4” - Chlormethansulfonanilid, 4.0 g water-free potassium carbonate, 4.8 ml chlorine acetone and 1,2-Dimethoxyäthan was agitated and cooked 24 h long at the Büokfluß and filtered then; the filtrate was evaporated. The oily arrears were solved in ethers and the solution was washed, dried with water (MgSO) and evaporated. The arrears resulted in nearly colorless crystals with a Fp from Aceton/40-60°C petroleum ether. of 168°C, yield 4.1 G. Modes of production 169 to 170: l0 in a similar way, as in mode of production described 168, were manufactured: N-2-Oxopropyl-2 “- ohlor-6” - methylmethansulfonanilid, Fp. 96 °C; N-2-Oxopropyl-2 “, 6” - dimethylmethansulfonanilid, Fp. 56 °C; N-2-Oxo-3,3-dimethylbutyl-2 “, 6” - dimethyläthansulfonanilid, analysis: Computed for C 6 H2 sNO S: C 61.70, H 8.09, N 4.50% found: C 61.75, H 8.26, N 4.62%; N-2-Oxopropyl-2', 6 ' - dimethyläthansulfonanilid, Fp. 68°C; N-2-Oxopropyl-2 “, 6” - dimethyl l propansulfona nilid, Fp. 104 o C; N-2-Oxopropyl-2', 6 ' - dimethyl Z thiophensulfonanilid, Fp. 127 to 128°C; N-2-Oxopropyl-2 “, 6” - diäthylmethansulfonanilid, Fp. 46 °C; N-2-Oxopropyl-2 “, 6” - dimethyl l butansulfon anilid, Fp. 69 °C; N-2-Oxopropyl-3 “, 4” - diohlormethansulfonanilid, Fp. 92 “C; N-2-Oxopropyl-3', 4 ' - diisopropylmethansulfonanilid, Fp. 134°C; N-2-Oxopropyl-2' methoxymethansulfonanilid, Fp. 126°C; and N-2-Oxopropyl-2',5' dichlormethansulfonanilid, Fp. 134°C. Mode of production 171: N (2,2-Dimethoxypropyl) - 2 “- chlor-6” - methylmethansulfonanilid to a solution of 5,7 g n (2-Oxopropyl) - 2 ' - ohlor-6' methylmethansulfonanilid in 80 ml methanol was added 0.2 g 4-Toluolsulfonsäure and afterwards 6.65 ml Trimethylorthoformiat. The mixture was agitated 24 h long at tree temperature and left untouched then 6 days long. The solution was poured into diluted Natriumbicarbonatlösung and the precipitated solid by filtration was collected, washed and dried with water, whereby 6.0 g of a nearly white solid became to receive, Fp. 84°C. Modes of production 172 and 173: In a similar way, how in mode of production 171 besohrieben, the following connections were manufactured: N (2,2-Dimethoxypropyl) - 4 ' - chlormethansulfonanilid, Fp. 850C; and n (2,2-Dimethoxypropyl) - 2 “, 6” - dimethylmethansulfonanilid, Fp. 82 °C. Mode of production 174: 4 ' - chlorine n [(2-methyl-i, 3-dithiolan-2-yl) - methyl] - methansulfonaniHd a solution of 3,2 g 4 ' - chlorine n (2,2-dimethoxypropyl) - methansulfonanilid in 50 ml acetic acid was treated with 0,96 ml Äthandithiol and the mixture slowly with application of a short Vigreux column 30 min was long distilled and the distillate was rejected. The remaining acetic acid solution was evaporated and the arrears again with toluol were evaporated, in order to remove acetic acid traces. A solution of the arrears in ethers separated pink crystals when leaving untouched. By recrystallizing from ethyl acetate/ether the product in form of nearly white crystals with a Fp became. receive from 114 to I17°C. Modes of production 175 and 176: In a similar way, as in mode of production described 174, the following connections were manufactured: N- [(2-Methyl-1,3-dithiol an-2-yl) - methyl] -2 “, 6” - dimethylmeth ansulfon anilid, Fp. 108 “C; and n [(2-Methyl-1,3-dithiolan-2-yl) - methyl] - 2 “- chlor-6” - methylmethansulfonanilid, Fp. 140°C. Mode of production 177: N [(2-Methyl-l, 3-dioxolan-2-yl) - methyl] - 4 ' - chlermethansulfonanilid a mixture of 6,0 g n (2-Oxopropyl) - 4 ' - chlormethansulfonanilid, i0 ml ethane l, 2-diol, 0.1 g 4-Toluolsulfonsäure and 75 ml toluol was agitated and cooked by means of a Dean strong device with water separation at the return flow. After 3 h the reaction mixture was cooled and poured in approximately 200 ml water, which some drops sodium hydroxide solution contained. The organic layer was separated, washed, dried with to water (MgSO} and evaporated to a i0 brown oil, which resulted in rehfarbene crystals from a solution in Toluol/80-1000C petroleum ether, yield 6.0 g (66%), Fp. 84 to 85 “C. Modes of production 178 to 179a: In a similar way, as in Herstellungswelse described 177, the following connections were manufactured: N- [(2-Methyl-4-hydroxymethy1-1,3-dioxolan-2-yl) - methyl] -4 “- chlormethansulfonanilid, Fp. IL 8 °; N [(2-Methyl-1,3-dioxolan-2-yl) - methyl] -2” - chlor-6 “- methylmethansulfonanilid, Fp. 84 " C; and n [(2-Methyl-i, 3-dioxolan-2-yl) - methyl] -2”, 6 '- dimethylmethansulfonanilid, Fp. 58 “C. Mode of production 180: N-2-Hydroxyiminopropyl-2 “, 6” - dimethylmethansulfonanilid a solution of 3,0 g n (2-Oxopropyl) - 2 ', 6 ' - dimethylmethansulfonanilid in 50 ml ethanol to a solution solved from 0,9 g hydroxyl amine hydrochloride and 1.1 g Natriumacetat, in the minimum portion water. added. The solution was cooked for 3 h long at the return flow, cooled down and evaporated then. A solution of the arrears in ethers was washed, dried with water (MgSO) and evaporated. The arrears were again evaporated with toluol, in order to remove acetic acid traces. Then the received product of one thylacetatlösung one crystallized, Fp. 122 to 124°C. Mode of production 181: 27,5 ml a 30%igen solution from sulfuric acid became drop by drop an agitated mixture of 0,1 ME! N (2-Oxepropyl) - 2 ', 6 ' - dimethylmethansulfonanilid, 6.2 g potassium cyanide and mI water added. The temperature was held with 15°C. The reaction mixture was long agitated 15 min and the Cyanohydrin of the Sulfonanilids was isolated. Mode of production 182: SO ME N-CHCOCH COOÄt GH jCHs SOzMe N-CHCOCHù BC H ù a mixture of 0,5 mol of n [3,3-Di (äthoxycarbonyl) - 2-oxo-l-methylpropyl] - 2 ', 6 ' - dimethylmethansulfonanilid, 1.5 mol sodium hydroxide, 500 ml ethanol and 500 ml water was heated up 2 1/2 h and cooled down then and evaporated ethanol. The received aqueous solution was acidified with hydrochloric acid and 1 h was long heated up and isolated then the product. Mode of production 183: A mixture of 12,5 g 2,6-Dimethylmethansulfonanilid, 14.2 g 2 ' - Chlor-4-thiocyanoacetanilid, 4.3 g potassium carbonate and 75 ml dimethylformamide was agitated and heated up 3 h long on 70 to 80oC and finally poured on ice/water. Precipitated viscose rayon the semisolid material was extracted in chloroform. The chloroform solution was then washed with 5% sodium hydroxide solution and with water, evaporated dried (MgSO) and to a brown oil. A solution of this oil in chloroform was perkoliert by a short silica-gel column. With evaporation of the Eluats a brown oil was received, which from a solution in ethyl acetate nearly colorless crystals of n {[(4-Thiocyanophenyl) - carbamoyl] - methyl} -2 ', 6, - dimethylmethansulfonanilid, Fp separated. 152°C. Mode of production 184: A solution of 2,8 g n (3-Hydroxy-2-oxopropyl) - 2 ', 6 ' - dimethylmethansulfonanilid in 5 ml Pyridin and 5 ml acetic anhydride was left untouched 20 h long at ambient temperature. Water was added, in order to decompose surplus anhydride, and the oily product was extracted in ethers. The ether solution was washed successively with diluted hydrochloric acid and NatriumbicarbonatlG solution, evaporated getroeknet (NgSO4) and to a yellow oil. A solution of this oil in chloroform was perkoliert by a short silica-gel column. With evaporation of the Eluats the product became, n (3-Acetoxy-2' - oxopropyl) - 2 “, 6” - dimethylmethansulfonanilid, when receive pale-yellow oil, yield 2.5 g [77%). Mode of production 185: A solution of 5,6 g n! - [2 (Äthoxycarbonyl) - hydrazincarbonyl) - ethyl] -2 ', 6 ' - dimethylmethansulfonanilid in 75 ml ethanol and 75 ml 10%iger sodium hydroxide solution 2 1/2 h was heated up long on a Dampfbad, on which ethanol was evaporated. The remaining aqueous solution was acidified with diluted hydrochloric acid, 1 h long on a Dampfbad was heated up and filtered then. The filtrate was neutralized with diluted sodium hydroxide solution, satisfied with sodium chloride and extracted with chloroform. The chloroform solution was dried and evaporated and the arrears resulted in from a solution in Toluol/60-80°C Petrcläther colorless crystals of n [(l-Hydr azinocarbonyl) - ethyl] -2 ', 6 ' - dimethylmethansulfonanilid in a yield of 2,6 g (58%), Fp. 115 to I18°C. Mode of production 186: A solution of 3,2 g of the hydrochloride salt of n [l (Hydrazinocarbonyl) - ethyl] - 2.6 ' - dimethylmethansulfonanilid and 1.0 ml acetylacetone in 25 ml Æthancl for simmering was heated up and left then during 2 h on ambient temperature cooling. The precipitated solid was collected by filtering and recrystallized from ethanol, whereby 1.5 g (43%) n [3 (3,5-Dimethyl-l-pyrazolyl) - l-methyl-2-oxoäthyl] -2 ', 6 ' - dimethylmethansulfonanilid, Fp were received. 168°C. Mode of production 187: 1,2 ml methyl isocyanate became an acetone solution of 2,7 g n (2-Hydroxyiminopropyl) - -2 ', 6 ' - dimethylmethansulfonanilid with a content vön 0.05 ml tri ethyl amine added. The mixture was left untouched over night at ambient temperature and evaporated then to a viscous oil, which solidified itself when leaving untouched slowly. By recrystallizing from ethyl acetate 60-80°C petroleum ethers became 3.0 g (of 91%) colorless crystals of n [2 (Methylearbamoyloxyimino) - propyl] - 2 ', 6 ' - dimethylmethansulfonanilid, Fp receive. 130 to 134°C. Mode of production 188: SO2 [Vie ùCH2 N CH2--/S02ble I N.Ctt2 CHs NOble CH a mixture of 2,7 g n (2-Hydroxyiminopropyl) - 2 ', 6 ' - dimethylmethansulfonanilid, 0.75 g potassium carbonate, 1.3 ml iodine methane and 50 ml acetone one agitated and one cooked 3 h long easily at the return flow. The reaction mixture was filtered and the filtrate to an oil was evaporated, which separated from a solution in Äther/40-60°G petroleum ether crystals, yield 0.6 g (21%), Fp. 126°C. Mode of production 189: 0,9 ml acetyl chloride became a solution of 2,6 g n (2-Hydroxyiminopropyl) - 2 ', 6 ' - dimethylmethansulfonanilid and 1.6 ml tri ethyl amine in 20 ml Dichlormethan added. The mixture was agitated and cooked 3 h long at the return flow, then and the filtrate filters to a clear yellow oil evaporated. A solution of this oil in chloroform was perkoliert by a short silica-gel column and the Eluat was evaporated, whereby 1.9 g analytically pure n [2 (Acetyloxyimino) - propyl] - 2 was received ', 6 ' - dimethylmethansulfonanilid (63%). Mode of production 190: A solution of Diäthyläthoxymagnesiummalonat was manufactured thereby that one kept, then with toluol evaporated a I0 mixture of 0,9 g magnesium, to 5.6 ml Diäthylmalonat, long 4.3 ml ethanol and 20 ml ethers 3 h at the return flow and replaced the solvent by dry ether. This solution drop by drop a ätherisohe solution of n (1-Chlorcarbonyläthyl) became - 2 ', 6 ' under agitating - dimethylmethansulfonanilid (made of 10 g acid and Thionylchlorid) added. After agitating over night with Raumtcmpcratur the received complex was decomposed by warming up with diluted sulfuric acid. The organic products were extracted in ethers and the solution was washed, dried with water (MgSO) and evaporated, whereby firm arrears became to receive. By recrystallizing from Äthylaoetat colorless crystals of n [3,3-Di (äthoxycarb0nyl) - 2-0x0-l-methylpr0pyl] became - 2 ', 6 ' - dimethylmethansulfonanilid, Fp. 125°C, receive. Mode of production 191: A solution of 7,5 g n (l-Äthoxycarbonyläthyl) -2 ' - trifluormeLhyl-4' phenylLhiomeLhansulfonanilid in 50 ml acetic acid was heated up under agitating for simmering and added 6 ml by 100 volumes hydrogen peroxide. Agitating and simmering at the return flow were long continued 3 h, on which the reaction mixture was poured in ice/water and extracted with chloroform. The chloroform solution was dried and evaporated to a yellow oil, which 6.6 g (of 83%) colorless crystals of n (l-Äthoxycarbonyläthyl) - 2 ' - trifluormethyl-4' resulted in phenylsulfonylmethansulfonanilid from an ethanol solution, yield 6.6 g (83%), Fp. 121°C. Mode of production 192: A solution of 7,2 g N-Carboxymethyl-2',6' dimeLhylmethansulfonanilid in 50 ml chloroform was treated with 5 ml Thionylchlorid and the mixture 1 1/2 h at the return flow was cooked and evaporated then. The arrears were solved with toluol again evaporated to remove (in order Thionylchloridspuren) and then in 10 ml dry tetrahydrofurane. 19.8 g and afterwards 3 drops tin (IV) trichloroethylene trimethylsilyloxyäthylen - chloride were added. The reaction mixture was left untouched 70 h long at ambient temperature, heated up then 2 h at the Dampfbad and poured into a mixture from same VolumsLeilen of diluted hydrochloric acid and tetrahydrofurane. This. Solution was heated up 1/2 h at the Dampfbad, satisfied with salt and extracted with ether. The united ether solution was washed, dried with Natriumbicarbenatlösung (MgSO) and evaporated, whereby 5.0 g n (3 - - Hydroxy-2-oxopropyl) - 2 ', 6 ' - dimethylmethansulfonanilid as clear yellow oil was received (66%) mode of production 193: In similar way, as in mode of production described 192, n (3-Hydroxy-2-oxo-1 - methylprepyl) became - 2 ', 6 ' - dimethylmethansulfonanilid manufactured, Fp. 125 to 126°C. Modes of production 194 and 195: In a similar way, as in the modes of production described 152 to 167, 2 became ', 8 ' - - Dimethyl-4-morpholinsulfonanilid, Fp. 124°C, and 3 ', 4 ' - Dichlor-4-morpholinosulfonanilid, Fp. 1220C, manufactured. 5 modes of production 196 to 198: In a similar way, as in mode of production described 3, the following esters of the formula indicated in the Hcrstellungsweisen 9 to 38 were manufactured: Mode of production 196 196a 197,198 g 1 n-Pf ME ME ME R18 ME ME ME COOCH2-- > CH=CHCOOÄt COOÄt COOMe substituent 2,6-diMe 2-CI, 6-Me 3,5-diCl 3,5-diCl Fp. °C oil 92 ii0 modes of production 199 and 200: In a similar way, as in mode of production described 39, the following connections of the formula indicated in the modes of production 40 to 67 were manufactured: Mode of production 199,200 g 1 e e g 1 e e A substituent 2,6-diMe 3,5-diCl Fp. °C 109,210 I0 mode of production 201: In a similar way, how in mode of production 168 besehrieben, n (2-Oxopropyl] became - 3 ', 5 ' - - dichlormethansulfonanilid, Fp. I06°C, manufactured. Mode of production 202: On similar-wise, as in mode of production 68 heschrieben, n (3-Cyanopropyl) became - 3 ', 5 ' - - diehlormethansulfonanilid, Fp. 82°C, manufactured. Mode of production 203: In a similar way, how in mode of production 109 beschriehen, the Lacton S02Me o c1 “CI was manufactured, Fp. 128 “C. Mode of production 204: In a similar way, as in mode of production described 73, n (Thiocarbamoylmethyl) became - -3 ', 5 ' - diohlormethansulfonanilid, Fp. 188 “C, manufactured. Ilerstellungsweise 205: In a similar way, as in mode of production described 168, n (2-Oxopropyl) became - 3 ', 4 ' - - dimethylmethansulfonanilid, Fp. 78°C, manufactured. The following examples are to describe the invention more near, without this is to be limited however on that. Examples 1 to 7: Seed in following indicated kinds into anodised aluminum pans, 19 cm long x 9.5 cm broad x 5 to deep, John senses I-Topfkompost contained, sown. They were then poured and into an area with controlled environment (22°C, 65 to 85% relative LuftfeuchI0 tigkeit; 14 h per day artificial lighting with 13000 lux) posed. 14 days after sowing became the seedlings below in the sheets with one that connections indicated, those as solution in aqueous acetone (I: 1 VOL.) formulated was sprayed. The concentration of the active component and the application volume corresponded to a portion of 11,2 kg/ha in 450! /ha. After 7 days growth in the area with controlled environment the plants were examined visually for herbicides or growth-adjusting reaction. All differences to untreated control were evaluated on the basis a scale, where 8 = does not mean effect and 100 = complete destruction. The results are shown in the following table. Example 1 2 3 4 5 6 7 connection of mode of production 20 27 3 2g 30 31 32 Species Oosierung kg/ha 11.2 11.2 11.2 11.2 11.2 11.2 11.2 peas (Pisum sativum) 5 5 5 20 5 5 mustard (Sinapis alba) go BO gg 100 BO 100,100 learning seeds Linum usltatissimu) go 30 30 gO 20 logs Raigras (Lolium perenne) 10 5 15 75 0 40 sugar beets (beta vulgarZs) gO BO 90 go 30 go 90 oats (Avena sativa) 5 5 5 30 20 40 beans (Phaseolus vulgarls) 70 BO BO i00 - examples 8 to 12: In following indicated connections were sand-deaf-formulated in each case as kaolin/and John the senses I-Topfkompost in a portion according to 26 TpM mass/volume an active component of earth incorporated and into anodised aluminum pans, 19 cm long × 9.5 cm broad × 5.0 cm deeply, brought in. This portion corresponds approximately to a creation on the Erdoberfläehe of ii, 2 kg of active Bestandteil/ha, cultivated up to a depth of 5 cm. Seeds in following indicated kinds were sown, poured into the treated earth and held in an area with controlled environment (22°C, 65 to 85% relative humidity, 14 h per day artificial lighting with 13000 lux) during 21 days. Then the plants were examined visually for growth-adjusting or herbicides of effects. All differences to untreated control were evaluated on the basis a scale from 0 to 100, whereby 0 does not mean effect and 1O0 vollstänB0 dige destruction. The results are shown in the following table. Rank-race examples 13 to 17: Example 8 g 10 11 12 connection of Herstellungsueise 20 68 27 3 2g Specles Oosierung (TpN) 26 26 26 26 26 peas. (Plsum sat vum) 0 0 0 0 0 mustard (Sinapls alba) 100 kO 100 go tO0 flax seed (Linus usitatlssimum) 70 20 100 20 100 of shark (Zea May) of 50 5 50 20 bar ones (arena sat va) 20 60 50 20 (Logium perenne) 100 5 go go 100 seeds in following indicated kinds was sown in Jehn Innes l-Topfkempcst in aluminum pans, 19 cm long × 9.5 cm broad × 5.0 cm highly, u.zw a kind per pan. The earth's surface became then with one in following indicated connections, those as solution in aqueous acetone (1: 1 VOL.) was formulated, with exception of the connection of mode of production 68, those as aqueous suspension with a content of I000 TpM of the wetting agent Lissapo! NX ONE (Nonylphenol/ethylen oxide condensate) formulated was sprayed. Each connection was applied in a portion of 2, B kg of active Bestandteil/ha in 450 1 Sprühflüssigkeit/ha. Then I0 were poured the pans and 21 days long into an area with controlled environment (22°C, relative humidity 65 to 85 14 h daily artificial lighting with 17000 lux) were placed. Whereupon the plants were examined visually for growth-adjusting or herbicides of effects. All differences to untreated control were evaluated on the basis a scale from 0 to I00, whereby 0 does not mean effect and 100 complete destruction. The results are shown in the following table: Sen£ cotton tomato 13 14 8 ispiel connection of mode of production Species Oosierung kg/ha 2.8 2, B 2.8 Sternmiere (position air medla) 30 - {Sinapls alba) 10 - go (Gnssyp£um frame) 0 0 {Lycopersicon esculentum) 20 - kO white Gänsefuß (Chenopod£um album) 68 27 lO0 - lO0 Karette (Daunus carota) 0 0 RST 2.8 17 29 2.8 fuel element [splel connection of mode of production Species wheat barley game oats Binse chicken millet (Echinochloa crusgalli) finger grass (D gltaria sanguinalls) rice (Orysae sativa) dosage kg/ha (rrltlcum aestlvum) (Hordeum vulgäre) (arena fatua) (Alopecurus my0 sur0 ßde5) 13 process cards ö8 2.8,2,8 0 0 tO0 0 0 CO 27,2.8 0 kO go 16 17 29 i00 gO 100 gO 100 example 18: Seeds following kinds indicated by Monocotyledonen in were sown into anodised aluminum pans, 19 cm long × 9.5 cm broad × 5.0 cm deeply, which contained John senses I-Topfkompost. They were then poured and placed in an area with controlled environment (20QC, to 85% relative humidity, 14 h daily artificial lighting with 17000 lux). 14 days after sowing were sprayed the seedlings with the connection by mode of production 68, which as aqueous suspension as well as 2000 TpM of a wetting agent (Lissapol NX ONE) was formuIiert, at the BIättern. The dosage portion was stopped to 2,8 kg an active component in 450 I/ha. I0 after further 14 days in the area with controlled environment were examined visually the PfIanzen for growth-adjusting or herbicides effects. All differences to untreated control were evaluated on the basis a scale from 0 to I00, whereby no effect and I00 complete destruction meant 0. The results come out from the following table: Species dosage kg/ha 2.8 ù, wheat (Triticum aestivum) 0 barley (Hordeum vulgare) 0 chicken millet (Echinochloa crusgalli) of 100 examples 19 to 35: In following indicated connections were tested in accordance with the procedure of the examples 8 to 12, however in a portion of 130 TpM mass/volume of the active component to earth. This portion corresponds for instance to an earth's surface creation cultivated by 56 kg active Bestandteil/ha, up to a depth of 5 cm. The results are shown in the following. 8eispiel connection of mode of production Species peas (Pisun sativum) mustard (SlnapZs alba) flax seed (Linum usltatisslmum) rank-race (Lolium perenne) to oats (Avena sat£va) corn (Zea ays) 19 gO 21 12 0 22 14 23 17? CO2 19 lOO go 22 0 go 26 23 27 I00 28 31 100 I00 lOO IOO lOO IOO 2g 32 IOO lOO 1oo 100,100 o 1oo 31 41 xoo 32 69 IOO go 33,100 gO 34 71 I0 I00 so IO 72 lOO IOO go I I z CO CO ù, example 36: Aqueous acetone suspensions with a content of 2000 mg of the connection of mode of production 20/1 and 125 mg wetting agent (Nonylphenol/Äthylenoxydkondensat = Lissapol NX ONE) /I were applied on those the roots and sheets by cucumber plants with two sheets surrounding earth fully attained full growth. The treated plants as well as controls alone treated with the wetting agent were angeimpft 24 h after the chemical treatment with spores of the disease organism cucumber flour rope (Erysiphe cichoracearum). Then the plants were brought into a Flaum with controlled environment (18°C, 80 to 90% relative humidity); after 14 days the extent of the illness was measured, whereby it was found that the treatment with the active connection had resulted in a 82%ige mushroom fight, while with controls a fight against less than 5% was evident. Example 37: With a standard test on insecticides effectiveness showed the connection n [2 (Methylcarbamyloxyimino) - propyl] -2 ', 6 ' - dimethylmethansulfonanilid with 100-mikromolarer concentration a 30%ige inhibition of acetylcholinesterase. Example 38: A one percent suspension/solution of the product of mode of production 143 in Polyäthylenglykel (Carbowax 400) was added to a Dextrosenährbrühe in a concentration of 1000 TpM mass/volume medium. Then a Verdfinnung was accomplished in test pipes, in order to obtain a concentration of 200 TpM mass/volume medium. To 8 ml-portions of Brühe 0.2 was added ml to a close Brfihenkultur of the bacterium Xanthomonas malvacearum, which strikes in particular cotton. After 8 days Bebrütung with 25°C all Brühenproben for signs by bacteria growth were examined. No growth arose, which proves that the connection is highly bakteriostatisch against this organism. Examples 39 to 41: A 1 week old corn flour/Sandkultur of the falling down disease organism Pythium ultimum was mixed by hand out thoroughly with pure sterile John senses Nr.l Topfkompost in the relationship 3 kg of culture to 12 1 earth. The infected earth was then left untouched before the use about 18 h long. Everyone in following indicated connections became together with a wetting agent (Tween 20; 1% of the final volume) husbands, until a solution or a fine suspension was formed, which was then diluted with distilled water, in order for 160 ml solution with a content from 15O0, 500, 150 or 50 TpM an active component to receive. 15 ml aliquot of parts of this solution was added to 75 g-portions of the earth, which was contained in small plastic containers (60 mm in diameter, 55 mm highly), infected with Pythium ultimum. 15 Kohl seeds, Varietät Flower OF jump. into elne circular recess in the treated infected earth were brought, covered and locked the whole with a plastic cover. The containers became then into a Flaum with constant temperature (25°C + I°C) brought in. Four repetitions per treatment with an additional treatment were accomplished, whereby seeds in earth were sown, which had been only chemically treated, i.e. it was not infection accomplished. Latter treatment was accomplished, in order to measure the direct effect of the chemical compound on the Auskeimen of the seeds. After 6 days the containers on the area with controlled temperature were removed and examined for the extent of mushroom growth at the earth's surface and the percentage at seed accumulating. The results of these two investigations are expressed on the basis the following scale: 0 i 2 3 4 6 7 8 < 20% inhibition 20-34% inhibition 35-44% inhibition 45-54% inhibition 55-64% inhibition 65-74% inhibition 75-84% inhibition ß5 94% inhibition > 94% inhibition and in the following Tabe! le indicated: Example 39 connection of mode of production dose TpM Mycelbekämpfung Bewortung 14,300,100 0 0 0 Auskeimen evaluation 1 29 100 0 0 I 31 0 0 0 300,100 41 4 4 3 untreatedly - - 0 0 Nr.368358 of examples 42 to 50: Aqueous acetone solution œ n or suspensions with a content the following Verbindungen/l as well as 125 mg of the Netzmittels/l, indicated by 2000 or 500 mg in, applied up: A] those the roots and sheets of rice plants with two sheets surrounding earth, B) the sheets of wine plants with five sheets fully attained full growth, I0 C) those, fully attained full growth, the roots of potato plants with seven sheets surrounding earth, D) the sheets of potato plants with seven sheets fully attained full growth, E) those, fully attained full growth, the roots and sheets of barley plants with a sheet surrounding earth or F) those fully attained full growth the roots and sheets of cucumber plants with two sheets surrounding earth fully attained full growth. The treated plants as well as controls, which had been alone treated with the wetting agent, were angeimpft 24 h after the chemical treatment: in case of A) with an aqueous Sperensuspension of the disease organism rice fire Pyricularia oryzae, in case of B) Sperangien of the disease organism wine flour rope Plasmopara ven with an aqueous suspension viticola, in case of C) and D) by spraying with an aqueous suspension of Sporangien of the disease organism Kartoffelfäule Phytophthora infestans, in case of E) by vibrating with spores of the disease organism barley flour rope Erysiphe graminis or in case of F) by vibrating with spores of the disease organism cucumber flour rope Erysiphe eichoracearum. Then the plants were placed in case of A) into an atmosphere with 80 to 100% humidity with 28°C placed, whereby the occurrence of the illness was measured 7 days later, in case of B) into an atmosphere with 80 to 100% humidity with 14 to 18°C placed, whereby the occurrence of the illness was measured 12 days later, in case of C) and D) into an atmosphere with 100% humidity during 24 h and brought then into an area with controlled environment (18°C and 80 to 90% of relative humidity), whereby the occurrence of the illness was measured 5 days later, in case of E) into an area with controlled environment (18°C and 80 to 00% relative humidity} brought in, whereby the occurrence of the illness after 10 days was measured, or in case of F) into an area with controlled environment (18°C and 80 to 90% relative humidity} brought in, whereby the occurrence of the illness was measured after 14 days. It was found that in the comparison with less than 5% in the case of controls the chemical treatments resulted in the prozentuelle fight shown in the following table. Beispie! 42 43 44 46 47 48 49 example 51: Connection of mode of production! 27 34 34 46 118,118,134,133,132,109,109 Bate TpM 2000 2000 500 2000 2000 500 2000 2000 2000 2000 2000 illness rice fire wine flour rope wine flour rope Kartoffelfäule Kartoffelfäule Kartoffelfäule barley flour rope barley flour rope barley flour rope barley flour rope cucumber flour rope % fight 84 98 90 93 76 59 89 96 92 95 92 the product against mode of production f13 became in accordance with the procedure of the examples! to 7 geteI0 constantly. The following results were received: Species peas mustard Leinsamsn Raigras sugar beets oats fire beans of examples 52 to 58: Effect! 00 10O 100 in following indicated connections became in accordance with the procedure ven example! 8 tested, whereby however rice (Oryza sativa) as additional Testspeeies was included: Example wheat connection of mode of production 73 I17 123,136,142 barley chicken millet rice 52 0 0 90 0 53 5 I0 90 0 54 0 0 80 0 0 0 80 flat steel bars 56 0 flat steel bars 90 0 example 57: The product of mode of production 83 was tested in accordance with the procedure examples 8 to 12, however in a portion of 130 and 26 TpM mass/volume. The results were as follows; Spocies dose TpM 130 28 peas mustard flax seed corn oats Raigras lfl0 lfl0 i00 of 100 90 0 0 90 examples 58 to 63: Everyone in following connections mentioned formulated as: (1) kaolin/sand-deaf and John senses I-Topfkompost incorporated in a portion according to 6.5 and 3.25 TpM mass/volume of the active component of earth and into anodised aluminum pans, 19 cm long × 9.5 cm broad × 5.0 cm highly, brought in. This corresponds approximately to a surface creation cultivated by 2,8 and 1,4 kg of active Bestandteil/he, up to a depth of 5 cm. Seeds that nachstend indicated kind were sown into the treated earth, poured u.zw a kind per pan, and placed into an area with controlled environment (22°C, 65 to 85% relative humidity and 14 h artificial lighting with 17000 lux) 21 days long. (IL) An aqueous Suspensien as well as i000 TpM wetting agent (Lissapol NX ONE). The surfaces of a further set of pans with seeds already sown were then sprayed with 2,8 or 1,4 kg/ha in 450 I/ha and the pans in the tree with controlled environment were kept 21 days long. Then the plants were examined visually for growth-adjusting or herbicides of effects. All differences to untreated control were evaluated on the basis a scale from 0 to 100, whereby 0 does not mean effect and 100 complete suppression. The results are shown in the following table, where I incorporation in earth and IL 2S surface spraying mean. Species i cotton Ooslerun9 TpM 142 I i Ver61edun9 von Herstellungswels.e 123 I 117 73 II IIII IIl11 I 136 II I I 0 0 5.5 3.25 5.5 3.25 5.5 3.25 6.5 3.25 6.5 3.25 6.5 3.25 6.5 3.25 6.5,5.5,6.5 0 0 0 0 0 0 o o o o o o i o o o o 0 i o o o o o I go I 90 o o o o o o I 83 I I II 0 0 0 0 0 0 0 0 i tomatoes 0 0 0 0 0 0 0 0 90 0 0 0 0 0 0 0 0 wheat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 barley 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 HUhnerh [rse go 100 60 100 70 80 go 100 - 80 60 90 50 60 90 90 - rice 0 0 0 0 0 0 0 0 I 0 0 0 0 0 0 0 0 carrots 0 0 0 0 0 0 0 0 0 I 0 0 Miere go mustard 50! Gäesefuß i00 of examples 64 to 65: A 1 week old corn flour/Sandkultur of the falling down disease organism Pythium ultimum was mixed by hand out thoroughly with clean sterile John Innes Nr.l Topfkompost in the relationship of 3 kg of culture to 12 1 earth. This infected earth was then left untouched before the use about 18 h long. The connections stated in the following table became in each case with a wetting agent (Tween 20; 1% of the final volume) husbands, until a solution or a fine suspension became to receive, which was then diluted with distilled water, in order to 160 ml solution with a content from 1500 or 500 TpM an active component to receive. 15 ml aliquot of portions of this solution was added to 75 g-portions of the earth infected with Pythium ultimum, which was contained in small plastic containers (60 mm in diameter, 55 mm highly). Kohl seed, Varietät Flower OF jump, into a circular recess in the treated infected earth were put, covered and the whole with a plastic cover locked. Then the containers became into an area with constant temperature (25 - + 1°C) placed. It four repetitions per treatment made with an additional treatment, whereby seeds in earth were sown, which had been only chemically treated, i.e. were not infected. This latter treatment was taken up, in order to measure the direct effect of the chemical compound on the Auskeimen of the seeds. After 6 days the containers were removed from the cream with controlled temperature and on the extent of mushroom growth on the earth's surface and prozentuelle accumulating of the seedlings to examine. The results of these two investigations are expressed on the basis a scale by i0 0 to 8: 0 1 2 3 4 6 7 8 < 20% inhibition 20-84% inhibition 35-44% inhibition 45-54% inhibition 55-64% inhibition 65-74 inhibition 75-84% inhibition 85-94% inhibition > 94% inhibition and in the following table aforementioned. Each Phytotoxizität, which was alone induced by the chemical compound, came from the treatment only with the chemical compound alone. Connection dose TpM Mycelbekämpfung Auskeimung evaluation evaluation n [(2-Me hyl l, 3-d [oxolan-2-y))- - methy)]- 4 ' - chlormethansulfonanilid n (2,2-Oimethoxypropyl) - -2 ' - chlor-6' methylmethansulfonanilld untreatedly 300,300 lO0 4 3 1 1 Phytotox zlt t evaluation o o of examples 66 and 67: Aqueous acetone solutions of everyone of the connections with a content, stated in the following table, by 2000 TpM, sheets surrounding earth fully attained full growth together with 125 TpM of a suitable wetting agent, were applied on those the roots and sheets of wine plants with five. The treated plants as well as controls alone treated with the wetting agent were angeimpft 24 h after the chemical treatment with an aqueous suspension by Sporangien of the disease organism wine flour rope, Plasmopara viLicola. Then the plants were brought into an atmosphere with 100% Feuchtigkeit/80% humidity with 14 to 18°C and the occurrence of the illness was measured 12 days later, whereby it was found that the treatments had resulted in the following mushroom fight in the comparison with less than 5% at controls. Connection n (2,2-Dimethoxypropyl) - 2 “- chlorine -6” - methylmeth ansulfonanilid n [(2-Methyl-i, 3-dioxolan-2-yl) - - methyl] -2 “- chlor-6” - methylmethansulfonanilid I % fight against wine flour rope of 94 examples 68 to 7@: Aqueous acetone solutions of everyone in following aforementioned connections with a content net with rock suitable of 2000, 500 or 125 TpM mass/volume as well as 125 TpM were applied on those the roots and sheets by potato plants with seven sheets surrounding earth fully attained full growth. The treated plants as well as only controls treated with the wetting agent 24 h after the chemical treatment with an aqueous suspension of Sporangien as Kartoffelfäule admitted disease organism Phytophthora infestans angeimpft. Then the plants were long brought into an atmosphere with 100% Feuchtigkeit/80% humidity 24 h and placed afterwards into a tree with controlled environment (18°C and 80 to 00% relative humidity); the occurrence of the illness was measured after 5 days. It was found that the treatments in the comparison with less than 5% at controls had resulted in the extent at mushroom fight, shown in the following table. I0 connection dose TpM N-2-Oxoprop l-2 “, 6” - dimethylmethansulfonanilid n (2,2-Dimethoxypropyl) - 2 “, 6” - dimethylmethansulfon anilld n [(2-Methyi-I, 3-dioxolan-2-yl) - - methyl] -2 ', 6 '- dimethylmethansulfonanilid 2000 5O0 125 2000 500 2000% fight potato rot 00 94 90 98 98 example 71: Aqueous acetone solutions of a wetting agent suitable by N-2-Oxo-3,3-dimethylbutyl-2',6' dimethyläthansulfonanilid with a content of 2000 TpM mass/volume as well as 125 TpM were applied on those the roots and sheets by rice plants with two sheets surrounding earth fully attained full growth. The treated plants as well as only alone controls treated with the wetting agent 24 h after the chemical treatment with an aqueous suspension of spores as rice fire admitted disease organism Piricularia oryzae angeimpft. Then the plants were placed into an atmosphere with 100% Feuchtlgkelt/80% humidity with 28°C; the occurrence of the illness was measured 7 days later. It was found that the treatment in the comparison with less than 5% at controls had resulted in a 80%ige mushroom fight. Example 72: N (2-Oxopropyl) - 2 ' - chlor-6' methylmethansulfonanilid, formulated as kaolin/sand-deaf, was incorporated John Innes I-Topfkompost in a portion according to 130 TpM mass/volume of the active component to earth and brought in into anodised aluminum pans (19 cm long x 9.5 cm broad x 5.0 cm deeply). These portions corresponded approximately to an earth's surface creation cultivated by 56 kg an active component per ha, up to a depth of 5 cm. Seeds of peas, mustard, flax seed, corn, oats and Raigras were sown, watered into the treated earth and placed into an area with controlled environment (22 “C, 65 to 85% relative humidity, 14 h artificial lighting with 13000 lux) 21 days long. Then the plants were examined visually for growth-adjusting or herbicides of effects. All differences to untreated control were evaluated on the basis a scale from 0 to 100, whereby 0 does not mean effect and 100 complete suppression. The results come out from the following table: RST Species dosage (TpM) 130 Nr.368358 peas (Pisum sativum) mustard (Sinapis alba) flax seed Linum usitatissimum) corn (Zea May} oats (Avena sativa) Raigras (Lolium perenne) 100 example 73: A 40%-Masse/Vol. emulsive Kenzentrat was manufactured by preparing a xylene solution of the following components: N- [l (thoxycarbonyl) - ethyl] - 2 “, 6” - dimethyl - l - propansulfonanilid Kalziumdodeeylbenzolsulfonat 70% in butanol (Arylan APPROX.) castor-oil thylenoxyd condensate (Ethylan C40AH) xylene (on I i) for instance 40O g g g 600 ml example 74: A 25%-Masse/Vol. emulsive concentrate was manufactured by preparing a xylene solution of the following components: N [1 (Äth0xycarb0nyi) - ethyl] - 2 ', 6 ' - dimethyläthansulfonanilid Kalziumdodecylbenzolsulfonat 70% in butanol (Arylan APPROX.) castor-oil thylenoxyd condensate (Ethylan C40AH) xylene (on 1 I) about 250 g g g 740 ml example 75: N (2-Oxopropyl) - 3 ', 4 ' - dimethylmethansulfonanilid in a portion of 300 TpM in the test described in the examples 64 and 65 one examined. It resulted in a Mycelbekämpfungsbewertung of 0 and a Auskeimungsbewertung of 3, while the untreated samples for both resulted in a value 0. Examples 76 to 78: In following indicated connections were examined in the examples 42 to descriptive test. The results are as follows: Example 76 77 connection Antei! Illness fight “; pM Produk% of mode of production 70 2000 N (2-Oxopropyl) - 3=, 4=-dlmethyl2000 ethansuifonaniiid 56 67 example 77 78 connection n (2-Oxopropyl) - 3r, 4 ' - dlnethylmethansulfonan ID n (2-Oxopropyi) - 3 ', M-dimethylmethansu [Fonanilid product of Herstellumgswe Œ SE 188 product of mode of production 188 portion of TpM 2000 2000 5OO 500 illness barley flour rope Ka Kartoffelfäule Kartoffelfäule rice fire fight gg 62 74 66