Patent Publication Number: US-2010130359-A1

Title: Fungicidal Pyridazines, Processes for Their Preparation and Their Use for Controlling Harmful Fungi, and Compositions Comprising Them

Description:
The present invention relates to pyridazines of the formula I 
     
       
         
         
             
             
         
       
     
     in which the substituents have the following meaning:
     R 1 , R 4  independently of one another are halogen, cyano, C 1 -C 8 -alkyl or C 1 -C 8 -alkoxy;   R 2  is C 1 -C 12 -alkyl, C 1 -C 10 -haloalkyl, C 2 -C 10 -alkenyl, C 2 -C 10 -haloalkenyl, C 2 -C 10 -alkynyl, C 2 -C 10 -haloalkynyl, C 3 -C 6 -cycloalkyl, C 3 -C 8 -cycloalkenyl, C 3 -C 12 -cycloalkenyl, C 3 -C 6 -halocycloalkyl, C 3 -C 12 -halocycloalkenyl, aryl or aromatic heterocycle which, in addition to carbon atoms, contains one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or oxygen atom as ring members, where the aromatic groups are five-, six-, seven-, eight-, nine- or ten-membered ring systems; and R 2  may contain one, two, three or four identical or different groups R a  independently of one another selected from the group consisting of:
       R a  is cyano, nitro, hydroxyl, carboxyl, C 1 -C 6 -alkyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cyclo-alkyl, C 3 -C 8 -cycloalkenyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyloxy, C 3 -C 6 -alkynyloxy, C 3 -C 6 -cycloalkoxy, C 3 -C 6 -cycloalkenyloxy, C(O)R π , C(O)OR π , C(S)OR π , C(O)SR π , C(S)SR π , OC(O)OR π , C 1 -C 6 -alkylthio, amino, C 1 -C 6 -alkylamino, di-C 1 -C 6 -alkylamino, C 1 -C 6 -alkylene, oxy-C 1 -C 4 -alkylene, oxy-C 1 -C 3 -alkyleneoxy, where divalent groups may be attached to the same atom or to adjacent atoms, phenyl, naphthyl, a five-, six-, seven-, eight-, nine- or ten-membered saturated, partially unsaturated or aromatic heterocycle which, in addition to carbon atoms, contains one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or oxygen atom as ring members;
           R π  is C 1 -C 8 -alkyl, C 3 -C 8 -alkenyl, C 3 -C 8 -alkynyl, C 3 -C 6 -cycloalkyl or C 3 -C 6 -cycloalkenyl;
               where the aliphatic, alicyclic or aromatic groups in groups R a  and R π  mentioned above for their part may be partially or fully halogenated and/or may carry one, two or three groups R b :   
               R b  is halogen, cyano, nitro, hydroxyl, mercapto, amino, carboxyl, alkyl, haloalkyl, alkenyl, alkoxy, haloalkoxy, alkenyloxy, alkynyloxy, alkylthio, alkylamino, dialkylamino, formyl, alkylcarbonyl, alkylsulfonyl, alkylsulfoxyl, alkoxycarbonyl, alkylcarbonyloxy, alkoxycarbonyloxy, aminocarbonyl, aminothiocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkylaminothiocarbonyl, dialkylaminothiocarbonyl, where the alkyl groups in these groups contain 1 to 6 carbon atoms and the alkenyl or alkynyl groups mentioned in these groups contain 2 to 8 carbon atoms; cycloalkyl, cycloalkoxy, heterocyclyl, heterocyclyloxy, where the cyclic systems contain 3 to 10 ring members; aryl, aryloxy, arylthio, aryl-C 1 -C 6 -alkoxy, aryl-C 1 -C 6 -alkyl, hetaryl, hetaryloxy, hetarylthio, where the aryl radicals preferably contain 6 to 10 ring members and the hetaryl radicals 5 or 6 ring members, where the cyclic systems may be partially or fully halogenated and/or substituted by alkyl or haloalkyl groups;   
           
       R 3  is phenyl or a 5- or 6-membered heteroaromatic group which, in addition to carbon atoms, contains 1, 2, 3 or 4 heteroatoms selected from the group consisting of O, S and N as ring members, where phenyl or the heteroaromatic group carries one substituents L 1  and optionally substituents L m ;
       L 1  is a group of the formulae —Y 1 —Y 2 -T, C(R i )═C(R ii )—Y 1 —Y 2 -T or C≡C—Y 1 —Y 2 -T, in which
           Y 1  is CR h R i , C(O)O, C(O)NR h , O, NR h  or S(O) r ;   Y 2  is C 1 -C 8 -alkylene, C 2 -C 8 -alkenylene or C 2 -C 8 -alkynylene, where r may be interrupted by one, two, three or four heteroatoms from the group consisting of NR h , O and S(O) r  and/or may contain one, two, three or four identical or different groups R a ;
               r is 0, 1 or 2;   
               T is OR h , NR h R i , C(O)OR h , C(O)NR h R i , C(NOR h )R i  or T 1 -C(=T 2 )-T 3 , where   T 1  is O or NR h ;   T 2  is O, S or NR h ;   T 3  is R h , OR h , SR h  or NR h R i ;
               independently, each R h  is hydrogen or has one of the meanings mentioned for R π ; and   
               
           R i , R ii  independently of one another are one of the groups mentioned for R a ; L independently of one another are halogen, hydroxyl, mercapto (SH), cyanato (OCN), cyano, nitro, C 1 -C 8 -alkyl, C 2 -C 10 -alkenyl, C 2 -C 10 -haloalkenyl, C 2 -C 10 -alkynyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halocycloalkyl, C 3 -C 6 -cycloalkenyl, C 1 -C 8 -alkoxy, C 1 -C 8 -haloalkoxy, C 2 -C 10 -alkenyloxy, C 2 -C 10 -alkynyloxy, C 3 -C 6 -cycloalkyloxy, C 3 -C 6 -cycloalkenyloxy, amino, C 1 -C 4 -alkylamino, di-(C 1 -C 4 )-alkylamino, C(O)—R Φ , C(S)—R Φ , S(O) n —R Φ ; C 1 -C 8 -alkoxyimino-(C 1 -C 8 )-alkyl, C 2 -C 10 -alkenyloxyimino-(C 1 -C 8 )-alkyl, C 2 -C 10 -alkynyloxyimino-(C 1 -C 8 )-alkyl, C 2 -C 10 -alkynylcarbonyl, C 3 -C 6 -cycloalkylcarbonyl, or a five-, six-, seven-, eight-, nine- or ten-membered saturated, partially unsaturated or aromatic heterocycle which contains one, two, three or four heteroatoms from the group consisting of O, N and S;
           R Φ  is hydrogen, C 1 -C 4 -alkyl, C 1 -C 2 -haloalkyl, C 1 -C 4 -alkoxy, C 2 -C 4 -alkenyloxy, C 2 -C 4 -alkynyloxy; where the groups R Φ  may be substituted by one, two or three identical or different groups R b , as defined above;   n is zero, 1 or 2;   
           m is 1, 2, 3 or 4;   
       

     and agriculturally acceptable salts thereof. 
     Moreover, the invention relates to processes and intermediates for preparing these compounds, to compositions comprising them and also to their use for controlling phytopathogenic harmful fungi. Moreover, the invention provides the use of the pyridazines for preparing a medicament for treating cancer. 
     WO 2005/121104 and WO 2006/045192 disclose 3,6-dimethyl-4,5-diphenylpyridazines and 3-chloro-6-methyl-4,5-diphenylpyridazines, respectively, having fungicidal action. Individual 3,6-dichloro-4,5-diphenylpyridazines and 3,6-dichloro-4-methyl-5-phenylpyridazines are disclosed in WO 2005/063762, J. Org. Chem. Vol. 29, pp. 2128-35 (1964), J. Chem. Soc., p. 1316 (1970). 
     In many cases, in particular at low application rates, the fungicidal action of the known compounds is unsatisfactory. Accordingly, it is an object of the present invention to provide compounds having improved action and/or a broader activity spectrum. 
     Accordingly, we have found the compounds defined at the outset. Furthermore, we have found processes and intermediates for their preparation, compositions comprising them and also methods for controlling harmful fungi using the compounds I. 
     The compounds of the formula I according to the invention can be obtained by different routes. 
     Pyridazines of the formula I in which both groups R 1  and R 4  are halogen, in particular chlorine, are advantageously accessible by halogenation of the compounds of the formula II with a halogenating agent [HAL] by the route below. They correspond to the formula I.1, in which Hal is halogen, preferably bromine or chlorine, in particular chlorine. 
     
       
         
         
             
             
         
       
     
     This reaction is usually carried out at temperatures of from 0 to 150° C. or preferably from 80 to 125° C., in the absence of a solvent or in an inert organic solvent [cf. Bioorg Med Chem Lett, 2003, 13, 1581; J Chem Soc, 1970, 1316]. Preferred halogenating agents are chlorinating or brominating agents, such as phosphorus oxybromide, phosphorus oxychloride, thionyl chloride, thionyl bromide or sulfuryl chloride, in particular phosphorus oxychloride. The reaction can be carried out in the absence of a solvent or in the presence of a solvent. 
     The halogenating agent is generally employed in equimolar amounts. It may also be used in excess or as solvent. 
     Suitable solvents are aliphatic hydrocarbons, such as pentane, hexane, cyclohexane and petroleum ether, aromatic hydrocarbons, such as toluene, o-, m- and p-xylene, halogenated hydrocarbons, such as methylene chloride, chloroform and chlorobenzene, ethers, such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, dioxane, anisole and tetrahydrofuran, nitriles, such as acetonitrile and propionitrile, ketones, such as acetone, methyl ethyl ketone, diethyl ketone and tert-butyl methyl ketone, alcohols, such as methanol, ethanol, n-propanol, isopropanol, n-butanol and tert-butanol, and also dimethyl sulfoxide, dimethylformamide and dimethylacetamide. It is also possible to use mixtures of the solvents mentioned. 
     The 3,6-dihydroxypyridazines of the formula II are preferably obtained by reacting furandiones of the formula III with hydrazine or hydrazine hydrate. 
     
       
         
         
             
             
         
       
     
     This reaction is usually carried out at temperatures of from −30° C. to 150° C., preferably from 50° C. to 120° C., in an inert organic solvent or in suitable inorganic or organic acids and also water [cf. Eur J Org Chem, 2004, 2797-2804; J Chem Soc, 1970, 1316; WO 2006/032518; Heteroatom Chem, 16(4), 298-307, 2005; Hely Chim Acta, 85 (7), 2195-2213, 2002]. 
     Suitable solvents are ethers, such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, dioxane, anisole and tetrahydrofuran, alcohols, such as methanol, ethanol, n-propanol, isopropanol, n-butanol and tert-butanol. It is also possible to use mixtures of the solvents mentioned. 
     Suitable for use as acids are inorganic acids, such as hydrofluoric acid, hydrochloric acid, hydrobromic acid, sulfuric acid and perchloric acid, and also organic acids, such as formic acid, acetic acid, propionic acid, oxalic acid, toluenesulfonic acid, benzenesulfonic acid, camphorsulfonic acid, citric acid and trifluoroacetic acid. 
     The starting materials are generally reacted with one another in equimolar amounts. In terms of yield, it may be advantageous to employ the hydrazine or hydrazine hydrate in an excess of up to 5 molar equivalents, based on III. 
     The furandiones of the formula III are advantageously obtained by oxidative cyclization of esters of the formula IV. 
     
       
         
         
             
             
         
       
     
     This reaction is usually carried out at temperatures of from ±30° C. to +100° C., preferably from +10° C. to +50° C., in an inert organic solvent in the presence of a base [cf. Synlett, 2002, (6), 947-951; Bioorg Med Chem Lett, 2003, 13, 1195]. A suitable oxidizing agent is, for example, oxygen. 
     Suitable solvents are aliphatic hydrocarbons, such as pentane, hexane, cyclohexane and petroleum ether, aromatic hydrocarbons, such as toluene, o-, m- and p-xylene, halogenated hydrocarbons, such as methylene chloride, chloroform and chlorobenzene, ethers, such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, dioxane, anisole and tetrahydrofuran, nitriles, such as acetonitrile and propionitrile, ketones, such as acetone, methyl ethyl ketone, diethyl ketone and tert-butyl methyl ketone, alcohols, such as methanol, ethanol, n-propanol, isopropanol, n-butanol and tert-butanol, and also dimethyl sulfoxide, dimethylformamide and dimethylacetamide, particularly preferably nitriles, such as acetonitrile and propionitrile. It is also possible to use mixtures of the solvents mentioned. 
     Suitable bases are, in general, inorganic compounds, such as alkali metal and alkaline earth metal hydroxides, such as lithium hydroxide, sodium hydroxide, potassium hydroxide and calcium hydroxide, alkali metal and alkaline earth metal oxides, such as lithium oxide, sodium oxide, calcium oxide and magnesium oxide, alkali metal and alkaline earth metal hydrides, such as lithium hydride, sodium hydride, potassium hydride and calcium hydride, alkali metal amides, such as lithium amide, sodium amide and potassium amide, alkali metal and alkaline earth metal carbonates, such as lithium carbonate, potassium carbonate and calcium carbonate, and also alkali metal bicarbonates, such as sodium bicarbonate, organometallic compounds, in particular alkali metal alkyls, such as methyllithium, butyllithium and phenyllithium, alkylmagnesium halides, such as methylmagnesium chloride, and also alkali metal and alkaline earth metal alkoxides, such as sodium methoxide, sodium ethoxide, potassium ethoxide, potassium tert-butoxide and dimethoxymagnesium, moreover organic bases, for example tertiary amines, such as trimethylamine, triethylamine, diisopropylethylamine and N-methylpiperidine, pyridine, substituted pyridines, such as collidine, lutidine and 4-dimethylaminopyridine, and also bicyclic amines, such as 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU). Particular preference is given to DBU. The bases are generally employed in catalytic amounts; however, they can also be employed in equimolar amounts, in excess or, if appropriate, as solvent. 
     The starting materials are generally reacted with one another in equimolar amounts. In terms of yield, it may be advantageous to employ about 3 molar equivalents of the base, based on IV. 
     The esters of the formula IV can be obtained by condensation of carboxylic acids of the formula V or sodium or potassium salts thereof with halides of the formula VI in which X is a halogen, such as iodine, chlorine or bromine, preferably chlorine or bromine. 
     
       
         
         
             
             
         
       
     
     This reaction is usually carried out at temperatures of from −50° C. to 100° C., preferably from 25° C. to 100° C., in an inert organic solvent in the presence or absence of a base [cf. Bioorg Med Chem Lett, 2003, 13, 1195; Synth. Commun., 25(12), 1681-1686, 2005, Org Prep and Proc Int, 20(5), 527-532, 1988; Synth Commun, 16 (14), 1777-1780, 1986]. 
     Suitable solvents are water, aliphatic hydrocarbons, such as pentane, hexane, cyclohexane and petroleum ether, aromatic hydrocarbons, such as toluene, o-, m- and p-xylene, halogenated hydrocarbons, such as methylene chloride, chloroform and chlorobenzene, ethers, such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, dioxane, anisole and tetrahydrofuran, nitriles, such as acetonitrile and propionitrile, ketones, such as acetone, methyl ethyl ketone, diethyl ketone and tert-butyl methyl ketone, alcohols, such as methanol, ethanol, n-propanol, isopropanol, n-butanol and tert-butanol, and also dimethyl sulfoxide, dimethylformamide and dimethylacetamide, particularly preferably acetonitrile. It is also possible to use mixtures of the solvents mentioned. 
     Suitable bases are, in general, inorganic compounds, such as alkali metal and alkaline earth metal hydroxides, such as lithium hydroxide, sodium hydroxide, potassium hydroxide and calcium hydroxide, alkali metal and alkaline earth metal oxides, such as lithium oxide, sodium oxide, calcium oxide and magnesium oxide, alkali metal and alkaline earth metal hydrides, such as lithium hydride, sodium hydride, potassium hydride and calcium hydride, alkali metal amides, such as lithium amide, sodium amide and potassium amide, alkali metal and alkaline earth metal carbonates, such as lithium carbonate, potassium carbonate and calcium carbonate, and also alkali metal bicarbonates, such as sodium bicarbonate, organometallic compounds, in particular alkali metal alkyls, such as methyllithium, butyllithium and phenyllithium, alkylmagnesium halides, such as methylmagnesium chloride, and also alkali metal and alkaline earth metal alkoxides, such as sodium methoxide, sodium ethoxide, potassium ethoxide, potassium tert-butoxide and dimethoxymagnesium, moreover organic bases, for example tertiary amines, such as trimethylamine, triethylamine, diisopropylethylamine, trisdioxaheptylamine (TDA) and N-methylpiperidine, pyridine, substituted pyridines, such as collidine, lutidine and 4-dimethylaminopyridine, and also bicyclic amines. Particular preference is given to bases, such as potassium carbonate and TDA. 
     The bases are generally employed in catalytic amounts; however, they can also be employed in equimolar amounts, in excess or, if appropriate, as solvent. 
     Halides of the formula VI in which X is a halogen, such as iodine, bromine or chlorine, in particular chlorine or bromine, can be obtained by halogenation of ketones of the formula VII. 
     
       
         
         
             
             
         
       
     
     This reaction is usually carried out at temperatures of from −78° C. to 100° C., preferably from 25° C. to 80° C., in an inert organic solvent or in an acid [cf. JACS, 1997, 119, 2453-2463; Synthesis (2), 143-146, 1980; JACS, 1208 (8), 2558-2570, 2006]. Preferred halogenating agents are elemental halogen, such as chlorine or bromine, in particular bromine, or other customary halogenating agents, such as N-bromosuccinimide, thionyl chloride, sulfuryl chloride, Cu(2) bromide or benzyltrimethylammonium tribromide. 
     Suitable solvents are ethers, such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, dioxane, anisole and tetrahydrofuran (THF), particularly preferably THF, or halogenated hydrocarbons, such as methylene chloride, chloroform and carbon tetrachloride, but also other solvents, such as, for example, ethyl acetate. 
     Suitable acids are organic acids, such as formic acid, acetic acid, propionic acid, oxalic acid, toluenesulfonic acid, benzenesulfonic acid, camphorsulfonic acid, citric acid and trifluoroacetic acid. It is also possible to use mixtures of the solvents mentioned. 
     Compounds of the formula I in which both groups R 1  and R 4  are halogen, in particular chlorine, and R 2  is an aliphatic group, can alternatively be obtained from furandiones of the formula III, which can be obtained by reacting α-ketocarboxylic acids or activated derivatives thereof, such as, for example, esters of the formula VIII in which R is C 1 -C 4 -alkyl, such as methyl or ethyl, with carboxylic anhydrides of the formula IX. 
     
       
         
         
             
             
         
       
     
     This reaction is usually carried out at temperatures of from 0° C. to 150° C., preferably from 0° C. to 50° C., in an inert organic solvent in the presence of a base and also a catalyst [cf. Tetrahedron Lett, 47 (2006), 2107-2109]. 
     Suitable solvents are aliphatic hydrocarbons, such as pentane, hexane, cyclohexane and petroleum ether, aromatic hydrocarbons, such as toluene, o-, m- and p-xylene, halogenated hydrocarbons, such as methylene chloride, 1,2-dichloroethane, chloroform and chlorobenzene, ethers, such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, dioxane, anisole and tetrahydrofuran, nitriles, such as acetonitrile and propionitrile, ketones, such as acetone, methyl ethyl ketone, diethyl ketone and tert-butyl methyl ketone, alcohols, such as methanol, ethanol, n-propanol, isopropanol, n-butanol and tert-butanol, and also dimethyl sulfoxide, dimethylformamide and dimethylacetamide, particularly preferably dichloromethane. It is also possible to use mixtures of the solvents mentioned. 
     Suitable bases are, in general, inorganic compounds, such as alkali metal and alkaline earth metal hydroxides, such as lithium hydroxide, sodium hydroxide, potassium hydroxide and calcium hydroxide, alkali metal and alkaline earth metal oxides, such as lithium oxide, sodium oxide, calcium oxide and magnesium oxide, alkali metal and alkaline earth metal hydrides, such as lithium hydride, sodium hydride, potassium hydride and calcium hydride, alkali metal amides, such as lithium amide, sodium amide and potassium amide, alkali metal and alkaline earth metal carbonates, such as lithium carbonate, potassium carbonate and calcium carbonate, and also alkali metal bicarbonates, such as sodium bicarbonate, organometallic compounds, in particular alkali metal alkyls, such as methyllithium, butyllithium and phenyllithium, alkylmagnesium halides, such as methylmagnesium chloride, and also alkali metal and alkaline earth metal alkoxides, such as sodium methoxide, sodium ethoxide, potassium ethoxide, potassium tert-butoxide and dimethoxymagnesium, moreover organic bases, for example tertiary amines, such as trimethylamine, triethylamine, tributylamine, diisopropylethylamine and N-methylpiperidine, pyridine, substituted pyridines, such as collidine, lutidine and 4-dimethylaminopyridine, and also bicyclic amines. Particular preference is given to tributylamine. The bases are generally employed in catalytic amounts; however, they can also be employed in equimolar amounts, in excess or, if appropriate, as solvent. 
     Suitable acids and acidic catalysts are Lewis acids, such as boron trifluoride, aluminum trichloride, iron(III) chloride, tin(IV) chloride, titanium(IV) chloride and zinc(II) chloride, preferably titanium(IV) chloride. 
     α-Ketocarboxylic esters of the formula VIII can preferably be obtained under Grignard conditions from the appropriate (hetero)aryl halides, in particular (hetero)aryl bromides, of the formula R 3 —X in which X is halogen, such as chlorine or bromine, in particular bromine, and the appropriate dialkyl oxalates of the formula XI, in particular diethyl oxalate. 
     
       
         
         
             
             
         
       
     
     This reaction is in the first step usually carried out at temperatures of from −100° C. to 0° C., preferably from −80° C. to −20° C., in the absence of a solvent or in an inert organic solvent in the presence of a Grignard reagent or in the presence of magnesium [cf. lit. Synlett, (6), 885-887, 2003; J Med Chem, 49 (4), 1271-1281, 2006]. Suitable Grignard salts are, preferably, C 1 -C 4 -alkylmagnesium chlorides, in particular isopropylmagnesium chloride. 
     Suitable solvents are the dialkyl oxalate of the formula XI, aliphatic hydrocarbons, such as pentane, hexane, cyclohexane and petroleum ether, aromatic hydrocarbons, such as toluene, o-, m- and p-xylene, halogenated hydrocarbons, such as methylene chloride, chloroform and chlorobenzene, ethers, such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, dioxane, anisole and tetrahydrofuran (THF), nitriles, such as acetonitrile and propionitrile, ketones, such as acetone, methyl ethyl ketone, diethyl ketone and tert-butyl methyl ketone, alcohols, such as methanol, ethanol, n-propanol, isopropanol, n-butanol and tert-butanol, and also dimethyl sulfoxide, dimethylformamide and dimethylacetamide, particularly preferably ethers, such as diethyl ether or THF. It is also possible to use mixtures of the solvents mentioned. 
     The reaction of the Grignard reagent, formed in the first step, with the oxalic esters is usually carried out at temperatures of from −78° C. to +100° C., preferably from +10° C. to +50° C., in an inert organic solvent [cf. lit. J Med Chem, 49, (4), 1271-1281, 2006; JOC, 68 (10), 3990-3998, 2003]. 
     Suitable solvents are aliphatic hydrocarbons, such as pentane, hexane, cyclohexane and petroleum ether, aromatic hydrocarbons, such as toluene, o-, m- and p-xylene, halogenated hydrocarbons, such as methylene chloride, chloroform and chlorobenzene, ethers, such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, dioxane, anisole and tetrahydrofuran, nitriles, such as acetonitrile and propionitrile, ketones, such as acetone, methyl ethyl ketone, diethyl ketone and tert-butyl methyl ketone, alcohols, such as methanol, ethanol, n-propanol, isopropanol, n-butanol and tert-butanol, and also dimethyl sulfoxide, dimethylformamide and dimethylacetamide, particularly preferably ethers, such as diethyl ether or THF and aliphatic hydrocarbons, such as, for example, hexane. It is also possible to use mixtures of the solvents mentioned. 
     Furthermore, the α-ketocarboxylic esters of the formula VIII can be prepared directly from oxalic esters of the formula XI and the appropriate aryl halides of the formula X in the presence of a base [cf. JACS, 125 (30), 9032-9034, 2003; Synthesis, 9, 1241-1242, 1998] 
     Suitable bases are, in general, inorganic compounds, such as alkali metal and alkaline earth metal hydroxides, such as lithium hydroxide, sodium hydroxide, potassium hydroxide and calcium hydroxide, alkali metal and alkaline earth metal oxides, such as lithium oxide, sodium oxide, calcium oxide and magnesium oxide, alkali metal and alkaline earth metal hydrides, such as lithium hydride, sodium hydride, potassium hydride and calcium hydride, alkali metal amides, such as lithium amide, sodium amide and potassium amide, alkali metal and alkaline earth metal carbonates, such as lithium carbonate, potassium carbonate and calcium carbonate, and also alkali metal bicarbonates, such as sodium bicarbonate, organometallic compounds, in particular alkali metal alkyls, such as methyllithium, butyllithium and phenyllithium, particularly preferably butyllithium, alkylmagnesium halides, such as methylmagnesium chloride, and also alkali metal and alkaline earth metal alkoxides, such as sodium methoxide, sodium ethoxide, potassium ethoxide, potassium tert-butoxide and dimethoxymagnesium, moreover organic bases, for example tertiary amines, such as trimethylamine, triethylamine, tributylamine, diisopropylethylamine and N-methylpiperidine, pyridine, substituted pyridines, such as collidine, lutidine and 4-dimethylaminopyridine, and also bicyclic amines. The bases are generally employed in catalytic amounts; however, they can also be employed in equimolar amounts, in excess or, if appropriate, as solvent. 
     Compounds of the formula I in which one of the groups R 1  and R 4  is alkoxy and the respective other group is halogen, in particular chlorine, correspond to the formulae I.2 and I.3, respectively. They can be obtained by reacting the compounds of the formula I.1 with the appropriate alkoxide [Y − — − M + ]. 
     
       
         
         
             
             
         
       
     
     This reaction is usually carried out at temperatures of from 0° C. to 120° C., preferably from 25° C. to 100° C., in an inert organic solvent [cf. Tetrahedron, 60(36), 7983-7994, 2004; Synthesis, (7), 1163-1168, 1999]. 
     Suitable solvents are aliphatic hydrocarbons, such as pentane, hexane, cyclohexane and petroleum ether, aromatic hydrocarbons, such as toluene, o-, m- and p-xylene, ketones, such as acetone, methyl ethyl ketone, diethyl ketone and tert-butyl methyl ketone, alcohols, such as methanol, ethanol, n-propanol, isopropanol, n-butanol and tert-butanol, and also dimethyl sulfoxide, dimethylformamide and dimethylacetamide, particularly preferably alcohols, such as methanol, ethanol, n-propanol, isopropanol, n-butanol and tert-butanol, in particular methanol. It is also possible to use mixtures of the solvents mentioned. 
     The starting materials are generally reacted with one another in equimolar amounts. In terms of yield, it may be advantageous to employ an excess of Y+M − , based on I.1. 
     Compounds of the formula I in which both groups R 1  and R 4  are alkoxy correspond to the formula I.4. They can be obtained by reacting the compounds of the formula I.1 with the appropriate alkoxide [Y + M − ], where M is a cation, usually an alkali metal or alkaline earth metal cation. 
     
       
         
         
             
             
         
       
     
     This reaction is usually carried out at temperatures of from 0° C. to 120° C., preferably from 25° C. to 100° C., in an inert organic solvent [cf. Helv. Chim. Acta, 37, 121-33; 1954; Chem. &amp; Pharm. Bull., 13(5), 586-93; 1965]. 
     Suitable solvents are aliphatic hydrocarbons, such as pentane, hexane, cyclohexane and petroleum ether, aromatic hydrocarbons, such as toluene, o-, m- and p-xylene, ketones, such as acetone, methyl ethyl ketone, diethyl ketone and tert-butyl methyl ketone, alcohols, such as methanol, ethanol, n-propanol, isopropanol, n-butanol and tert-butanol, and also dimethyl sulfoxide, dimethylformamide and dimethylacetamide, particularly preferably alcohols, such as methanol, ethanol, n-propanol, isopropanol, n-butanol and tert-butanol, in particular methanol. It is also possible to use mixtures of the solvents mentioned. 
     The starting materials are generally reacted with one another in equimolar amounts. In terms of yield, it may be advantageous to employ an excess of Y + M − , based on I.1. 
     Compounds of the formula I in which one of the groups R 1  and R 4  is cyano and the respective other group is halogen, in particular chlorine, or where both groups R 1  and R 4  are cyano, correspond to the formulae I.5, I.6 and I.7, respectively. Depending on the chosen parameters, they can be obtained from compounds of the formula I.1 by reaction with cyanides. 
     
       
         
         
             
             
         
       
     
     This reaction is usually carried out at temperatures of from 50° C. to 150° C., preferably from 80° C. to 100° C., in an inert organic solvent, if appropriate in the presence of a catalyst, such as p-toluenesulfonic acid sodium salt [cf. Heterocycles, 39(1), 345-56; 1994]. Usually, use is made of alkali metal or alkaline earth metal cyanides, preferably potassium cyanide. 
     Suitable solvents are aliphatic hydrocarbons, such as pentane, hexane, cyclohexane and petroleum ether, aromatic hydrocarbons, such as toluene, o-, m- and p-xylene, halogenated hydrocarbons, such as methylene chloride, chloroform and chlorobenzene, ethers, such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, dioxane, anisole and tetrahydrofuran, nitriles, such as acetonitrile and propionitrile, ketones, such as acetone, methyl ethyl ketone, diethyl ketone and tert-butyl methyl ketone, alcohols, such as methanol, ethanol, n-propanol, isopropanol, n-butanol and tert-butanol, and also dimethyl sulfoxide, dimethylformamide and dimethylacetamide, particularly preferably dimethylformamide. It is also possible to use mixtures of the solvents mentioned. 
     The starting materials are generally reacted with one another in equimolar amounts. In terms of yield, it may be advantageous to employ an excess of the cyanide, based on I.1 
     Alternatively, the compounds of the formula I can be obtained by oxidation of 4,5-dihydropyridazines of the formula XII. 
     
       
         
         
             
             
         
       
     
     The oxidation is usually carried out at temperatures of from 20° C. to 100° C., preferably from 40° C. to 80° C., in an inert organic solvent in the presence of an oxidizing agent and/or a catalyst, such as, preferably, Pt or Pd, or oxides or peroxides, such as H 2 O 2  [lit.: Comprehensive Organic Reactions, R. C. Larock, Chapter 5.1 Aromatization—Dehydrogenation, page 93, VCH, 1989; J Het, Chem, 26 (3), 717-719, 1989]. 
     Reaction times are usually from 1 to 48 hours. Suitable solvents are aliphatic hydrocarbons, such as pentane, hexane, cyclohexane and petroleum ether, aromatic hydrocarbons, such as toluene, o-, m- and p-xylene, halogenated hydrocarbons, such as methylene chloride, chloroform and chlorobenzene, ethers, such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, dioxane, anisole and tetrahydrofuran, nitriles, such as acetonitrile and propionitrile, ketones, such as acetone, methyl ethyl ketone, diethyl ketone and tert-butyl methyl ketone, alcohols, such as methanol, ethanol, n-propanol, isopropanol, n-butanol and tert-butanol, and also dimethyl sulfoxide, dimethylformamide and dimethylacetamide. It is also possible to use mixtures of the solvents mentioned. 
     The oxidizing agent is usually employed in equimolar amounts, based on the compound of the formula XII. In terms of yield, it may be advantageous to employ the oxidizing agent in equimolar amounts or in an excess of up to 5 molar equivalents, based on XII. 
     Furthermore, dihydropyridazines may be obtained by chlorination or bromination and subsequent elimination of HCl or HBr. This reaction is usually carried out at temperatures of from −30° C. to 100° C., preferably from 0° C. to 80° C., in an inert organic solvent or in organic acids such as acetic acid [cf. lit. Synthesis, 1995, (10), 240-242; Syn Comm, 23(21), 2957-2964, 1993]. 
     4,5-Dihydropyridazines of the formula XII can be obtained in an advantageous manner from 1,2-diketones of the formula XIII by reaction with hydrazine or hydrazine hydrate. 
     
       
         
         
             
             
         
       
     
     This reaction is usually carried out at temperatures of from −30° C. to 100° C., preferably from 0° C. to 80° C., in an inert organic solvent [cf. lit. Syn Comm, 31 (5), 645-651, 2001; Heterocycles, 57 (1), 39-46, 2002]. 
     Suitable solvents are ethers, such as diethyl ether, diisopropyl ether, dimethoxyethane, tert-butyl methyl ether, dioxane, anisole and tetrahydrofuran, alcohols, such as methanol, ethanol, n-propanol, isopropanol, n-butanol and tert-butanol, particularly preferably alcohols. It is also possible to use mixtures of the solvents mentioned. 
     The starting materials are generally reacted with one another in equimolar amounts. In terms of yield, it may be advantageous to employ the hydrazine or hydrazine hydrate in an excess of up to 5 molar equivalents, based on XIII. 
     Diketones of the formula XIII can be obtained by reacting compounds of the formulae XIV and V, via intermediate XIIIa. 
     
       
         
         
             
             
         
       
     
     The reaction of the compounds XIV and XV is usually carried out at temperatures of from −30° C. to 100° C., preferably from 20° C. to 40° C., in the absence of a solvent or in an inert organic solvent [cf. lit. Tetrahedron, 45 (17), 5667-5678, 1989]. 
     The reaction is preferably carried out in the absence of a solvent. 
     The reaction of the intermediate XIIIa is usually carried out at temperatures of from −30° C. to 80° C., preferably from 0° C. to 30° C., in an aqueous organic solvent, in an acidic medium, preferably at a pH of about 2 [cf. lit. Tetrahedron, 45 (17), 5667-5678, 1989; Tetrahedron, 45 (7), 2099-2108, 1989. 
     Suitable solvents are water and ethers, such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, dioxane, anisole and tetrahydrofuran, alcohols, such as methanol, ethanol, n-propanol, isopropanol, n-butanol and tert-butanol, particularly preferably ethanol. It is also possible to use mixtures of the solvents mentioned. 
     Suitable for use as acids and acidic catalysts are inorganic acids, such as hydrofluoric acid, hydrochloric acid, hydrobromic acid, sulfuric acid and perchloric acid, Lewis acids, such as boron trifluoride, aluminum trichloride, iron(III) chloride, tin(IV) chloride, titanium(IV) chloride and zinc(II) chloride, and also organic acids, such as formic acid, acetic acid, propionic acid, oxalic acid, toluenesulfonic acid, benzenesulfonic acid, camphorsulfonic acid, citric acid and trifluoroacetic acid, preferably hydrochloric acid. 
     The acids are generally employed in catalytic amounts; however, they can also be employed in equimolar amounts, in excess or, if appropriate, as solvent. 
     Alternatively, the compounds of the formula I can be obtained from substituted hydrazonoketones of the formula XVI. 
     
       
         
         
             
             
         
       
     
     This reaction is usually carried out at temperatures of from 0° C. to 120° C., preferably from 50° C. to 100° C., in an inert organic solvent in the presence of a base [cf. lit. J Chem Res, 3, 187-189, 2005]. 
     Suitable solvents are ethers, such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, dimethoxyethane, dioxane, anisole and tetrahydrofuran, alcohols, such as methanol, ethanol, n-propanol, isopropanol, n-butanol and tert-butanol, particularly preferably ethanol. It is also possible to use mixtures of the solvents mentioned. 
     Suitable bases are, in general, inorganic compounds, such as alkali metal and alkaline earth metal hydroxides, such as lithium hydroxide, sodium hydroxide, potassium hydroxide and calcium hydroxide, alkali metal and alkaline earth metal oxides, such as lithium oxide, sodium oxide, calcium oxide and magnesium oxide, alkali metal and alkaline earth metal hydrides, such as lithium hydride, sodium hydride, potassium hydride and calcium hydride, alkali metal amides, such as lithium amide, sodium amide and potassium amide, alkali metal and alkaline earth metal carbonates, such as lithium carbonate, potassium carbonate and calcium carbonate, and also alkali metal bicarbonates, such as sodium bicarbonate, organometallic compounds, in particular alkali metal alkyls, such as methyllithium, butyllithium and phenyllithium, alkylmagnesium halides, such as methylmagnesium chloride, and also alkali metal and alkaline earth metal alkoxides, such as sodium methoxide, sodium ethoxide, potassium ethoxide, potassium tert-butoxide and dimethoxymagnesium, moreover organic bases, for example tertiary amines, such as trimethylamine, triethylamine, diisopropylethylamine and N-methylpiperidine, pyridine, substituted pyridines, such as collidine, lutidine and 4-dimethylaminopyridine, and also bicyclic amines. Particular preference is given to tertiary amines, such as, for example, triethylamine. 
     The bases are generally employed in catalytic amounts; however, they can also be employed in equimolar amounts, in excess, preferably up to 2 molar equivalents, or, if appropriate, as solvent. 
     The hydrazonoketones of the formula XVI can be obtained by reacting compounds of the formulae XVII and XVIII. 
     
       
         
         
             
             
         
       
     
     This reaction is usually carried out at temperatures of from 0° C. to 150° C., preferably from 20° C. to 120° C., in an inert organic solvent in the presence or absence of a base or an acidic catalyst [cf. lit. J für Prakt Chem, 328 (4), 551-557, 1986; J für Prakt Chem, 327 (1), 109-116, 1985; Synthesis, (5), 691-694, 2003]. 
     Suitable solvents are aliphatic hydrocarbons, such as pentane, hexane, cyclohexane and petroleum ether, aromatic hydrocarbons, such as toluene, o-, m- and p-xylene, benzene, particularly preferably benzene, halogenated hydrocarbons, such as methylene chloride, chloroform and chlorobenzene, particularly preferably dichloromethane, ethers, such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, dioxane, anisole and tetrahydrofuran, particularly preferably dioxane, nitriles, such as acetonitrile and propionitrile, ketones, such as acetone, methyl ethyl ketone, diethyl ketone and tert-butyl methyl ketone, alcohols, such as methanol, ethanol, n-propanol, isopropanol, n-butanol and tert-butanol, and also dimethyl sulfoxide, dimethylformamide and dimethylacetamide, particularly preferably dimethylformamide. It is also possible to use mixtures of the solvents mentioned. 
     Suitable for use as acids and acidic catalysts are inorganic acids, such as hydrofluoric acid, hydrochloric acid, hydrobromic acid, sulfuric acid and perchloric acid, Lewis acids, such as boron trifluoride, aluminum trichloride, iron(III) chloride, tin(IV) chloride, titanium(IV) chloride and zinc(II) chloride, and also organic acids, such as formic acid, acetic acid, propionic acid, oxalic acid, citric acid, trifluoroacetic acid and sulfonic acids, such as toluenesulfonic acid, benzenesulfonic acid, camphorsulfonic acid, particularly preferably p-toluenesulfonic acid. The acids are generally employed in catalytic amounts, preferably from 0.001 to 0.05 molar equivalents, based on XVIII; however, they can also be employed in equimolar amounts, in excess or, if appropriate, as solvent. 
     Suitable bases are, in general, inorganic compounds, such as alkali metal and alkaline earth metal hydroxides, such as lithium hydroxide, sodium hydroxide, potassium hydroxide and calcium hydroxide, alkali metal and alkaline earth metal oxides, such as lithium oxide, sodium oxide, calcium oxide and magnesium oxide, alkali metal and alkaline earth metal hydrides, such as lithium hydride, sodium hydride, potassium hydride and calcium hydride, alkali metal amides, such as lithium amide, sodium amide and potassium amide, alkali metal and alkaline earth metal carbonates, such as lithium carbonate, potassium carbonate and calcium carbonate, and also alkali metal bicarbonates, such as sodium bicarbonate, organometallic compounds, in particular alkali metal alkyls, such as methyllithium, butyllithium and phenyllithium, alkylmagnesium halides, such as methylmagnesium chloride, and also alkali metal and alkaline earth metal alkoxides, such as sodium methoxide, sodium ethoxide, potassium ethoxide, potassium tert-butoxide and dimethoxymagnesium, moreover organic bases, for example tertiary amines, such as trimethylamine, triethylamine, diisopropylethylamine and N-methylpiperidine, pyridine, substituted pyridines, such as collidine, lutidine and 4-dimethylaminopyridine, and also bicyclic amines. Particular preference is given to alkali metal bicarbonates, such as sodium bicarbonate. 
     The bases are generally employed in catalytic amounts; however, they can also be employed in equimolar amounts, in excess, preferably up to 2 molar equivalents, or, if appropriate, as solvent. 
     The starting materials are generally reacted with one another in equimolar amounts. In terms of yield, it may be advantageous to employ about 0.8 to 1.3 molar equivalents of XVII, based on XVIII. 
     The hydrazonoketones of the formula XVIII can be obtained by reacting diketones of the formula XIX with hydrazine or hydrazine hydrate. 
     
       
         
         
             
             
         
       
     
     This reaction is usually carried out at temperatures of from −30° C. to 120° C., preferably from 0° C. to 80° C., in an inert organic solvent [cf. lit. J Med Chem, 48 (22), 6843-6854, 2005]. 
     Suitable solvents are inter alia alcohols, such as methanol, ethanol, n-propanol, isopropanol, n-butanol and tert-butanol, particularly preferably ethanol. It is also possible to use mixtures of the solvents mentioned. 
     The starting materials are generally reacted with one another in equimolar amounts. In terms of yield, it may be advantageous to employ the hydrazine or hydrazine hydrate in a molar ratio of from 0.8 to 1.3, based on XIX. 
     Compounds of the formula I in which R 1  and/or R 4  is/are alkyl can be obtained from the compounds I.1, preferably from the compounds I.1 in which both “Hal” are chlorine. Depending on the nature of the groups R 2  and R 3  and the chosen reaction conditions and molar ratios of the reactants, the compounds I.8, I.9 and I.10 can be obtained with various selectivity by the following routes. In the formulae I.8, I.9 and I.10, R 1′  and R 4′  are alkyl, in particular methyl. Compounds of the formulae I.8, I.9 and I.10 can be obtained by reacting the compounds of the formula I.1 with alkylmagnesium halides. 
     
       
         
         
             
             
         
       
     
     This reaction is usually carried out at temperatures of from −30° C. to 25° C., preferably from 0° C. to 20° C., in an inert organic solvent in the presence of a catalyst [cf. JACS, 124 (46), 13856-13863]. 
     Suitable solvents are ethers, such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, dioxane, anisole and tetrahydrofuran, and also N-methylpyrrolidone (NMP), particularly preferably THF and NMP. 
     Advantageous for use as catalyst are Fe (acac) 3  or Fe(salen)Cl in catalytic amounts, such as, for example, 5 mol %. 
     The starting materials are generally reacted with one another in equimolar amounts. In terms of yield, it may be advantageous to employ a slight excess of alkylmagnesium halide, based on the pyridazine. 
     Alternatively, the compounds of the formulae I.8, I.9 and I.10 can also be obtained by reacting the compounds of the formula I.1 with alkylzinc halides at temperatures of from 0° C. to 120° C., preferably from 20° C. to 60° C., in an inert organic solvent in the presence of a catalyst [cf. Tetrahedron Letters, 46 (8), 1303-1305 (2005)]. 
     Suitable solvents are ethers, such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, dioxane, anisole and tetrahydrofuran. 
     The catalyst used is advantageously a Pd(0) catalyst, particularly preferably Pd(PPh 3 ) 4 , in an amount of about 5 mol %. 
     The starting materials are generally reacted with one another in equimolar amounts in order to obtain the monosubstituted products. If the zinc reagent is employed in larger amounts (1.6 eq.), some disubstituted product is obtained as byproduct. If the reaction temperature is increased from 20° to 60° C., mainly disubstituted product is obtained. 
     Alternatively, the group L 1  may be introduced at the stage of pyridazines of the formula XIX by nucleophilic substitution according to the synthesis shown below. 
     
       
         
         
             
             
         
       
     
     In formula XIX, the variables have the meanings mentioned above, LG 1  is a nucleophilically replaceable group, such as halogen, for example fluorine, and   is phenyl or a 5- or 6-membered heteroaromatic group which contains 1, 2, 3 or 4 heteroatoms selected from the group consisting of O, S and N as ring members. 
     The reaction of XIX with H-L 1  is carried out, for example, according to the method described in WO 2005/030775 and is advantageously carried out in the presence of strong bases. Suitable bases are, for example, alkali metal hydroxides, such as sodium hydroxide or potassium hydroxide, alkali metal carbonates, such as sodium carbonate or potassium carbonate, alkaline earth metal carbonates, such as calcium carbonate or magnesium carbonate, or alkali metal hydrides, such as lithium hydride or sodium hydride. The reaction can be carried out in the presence of a solvent. Suitable solvents are aprotic solvents, for example N,N-disubstituted amides, such as N,N-dimethylformamide, N,N-dimethylacetamide or N-methylpyrrolidone, sulfoxides, such as dimethyl sulfoxide, or ethers, such as diethyl ether, diisopropyl ether, tert-butyl ether, 1,2-dimethoxyethane, tetrahydrofuran, dioxane or anisole. The reaction is usually carried out at temperatures in the range of from 0° C. to the boiling point of the solvent. 
     If T in group L 1  is OH or a primary or secondary amino group, it is advantageous to protect the hydroxyl group or the amino group. A suitable protective group for the hydroxyl group is, for example, the benzyl group, which optionally carries a methoxy group in the 4-position of the phenyl ring. The protective group for the hydroxyl group can be removed, for example, by catalytic hydrogenolysis or with the aid of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ). A suitable protective group for primary and secondary amino groups is, for example, the tert-butoxycarbonyl group (Boc), which is usually removed using trifluoroacetic acid or p-toluenesulfonic acid. 
     Pyridazines of the formula XIX can be prepared analogously to the synthesis routes above by modifying the precursors with respect to the nature of R 3 . 
     Compounds H-L 1  are generally commercially available or can be prepared by processes known from the literature. 
     Alternatively, compounds of the formula I in which L 1  is a group attached via oxygen can be obtained according to the process described below. 
     
       
         
         
             
             
         
       
     
     In the formulae XX and XXa, the variables and   have the meanings mentioned above. 
     In a first step, the compound XX is reacted with a Lewis acid, such as aluminum trichloride or iron(III) chloride, giving the phenolic compound XXa. Usually, the ether cleavage is carried out in an organic solvent, for example in an aromatic hydrocarbon, such as benzene, toluene or xylene. The introduction of the group L 1  is carried out by nucleophilic substitution of the hydroxyl group under basic conditions, as described above. 
     Pyridazines of the formula XX can be prepared analogously to the synthesis routes above by modifying the precursors with respect to the nature of R 3 . 
     Compounds of the formula I in which L 1  is a group attached via carbon can advantageously be prepared from compounds XXa. Initially, the hydroxyl compound XXa is reacted with trifluoromethanesulfonic anhydride giving a trifluoromethanesulfonate XXb, which is then treated with an aminoalkylboronic acid) XXI; 
     
       
         
         
             
             
         
       
     
     In the formulae XXb and XXI, the variables and   have the meanings mentioned above. 
     Compounds of the formula I in which L 1  is a group attached via nitrogen can advantageously be prepared from precursors in which group   carries an amino group, which, if appropriate, can be obtained from the corresponding nitro-substituted compounds by reduction. 
     The required starting materials are known from the literature or can be prepared in accordance with the literature cited. 
     The reaction mixtures are worked up in a customary manner, for example by mixing with water, separating the phases and, if appropriate, chromatographic purification of the crude products. Some of the intermediates and end products are obtained in the form of colorless or slightly brownish viscous oils which are purified or freed from volatile components under reduced pressure and at moderately elevated temperature. If the intermediates and end products are obtained as solids, purification can also be carried out by recrystallization or digestion. 
     If individual compounds of the formula I can not be obtained by the routes described above, they can be prepared by derivatization of other compounds I. 
     If the synthesis yields mixtures of isomers, a separation is generally not necessarily required since in some cases the individual isomers can be interconverted during preparation for application or during application (for example under the action of light, acid or bases). Such conversions may also take place after application, for example in the case of the treatment of plants in the treated plants or in the harmful fungus to be controlled. 
     In the definitions of the symbols given in the above formulae, collective terms were used which are generally representative for the following substituents: 
     halogen: fluorine, chlorine, bromine and iodine; 
     alkyl: saturated straight-chain or branched hydrocarbon radicals having 1 to 4, 6 or 8 carbon atoms, for example C 1 -C 6 -alkyl, such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl and 1-ethyl-2-methylpropyl; 
     haloalkyl: straight-chain or branched alkyl groups having 1 to 2, 4 or 6 carbon atoms (as mentioned above), where some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as mentioned above: in particular C 1 -C 2 -haloalkyl, such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl or 1,1,1-trifluoroprop-2-yl; 
     alkenyl: unsaturated straight-chain or branched hydrocarbon radicals having 2 to 4, 6 or 8 carbon atoms and one or two double bonds in any position, for example C 2 -C 6 -alkenyl, such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-1-propenyl and 1-ethyl-2-methyl-2-propenyl; 
     alkynyl: straight-chain or branched hydrocarbon groups having 2 to 4, 6 or 8 carbon atoms and one or two triple bonds in any position, for example C 2 -C 6 -alkynyl, such as ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-1-pentynyl, 3-methyl-4-pentynyl, 4-methyl-1-pentynyl, 4-methyl-2-pentynyl, 1,1-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl-1-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl and 1-ethyl-1-methyl-2-propynyl; 
     cycloalkyl: mono- or bicyclic saturated hydrocarbon groups having 3 to 6 or 8 carbon ring members, for example C 3 -C 8 -cycloalkyl, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl; 
     aryl: a mono-, bi- or tricyclic aromatic hydrocarbon group which contains 6, 8, 10, 12 or 14 ring members, such as phenyl, naphthyl or anthracenyl, preferably phenyl or naphthyl, in particular phenyl; 
     a five- or six-membered saturated, partially unsaturated or aromatic heterocycle which contains one, two, three or four heteroatoms from the group consisting of O, N and S:
         non-aromatic saturated or partially unsaturated 5- or 6-membered heterocyclyl which contains one to three nitrogen atoms and/or one oxygen or sulfur atom or one or two oxygen and/or sulfur atoms, for example 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazolidinyl, 4-isoxazolidinyl, 5-isoxazolidinyl, 3-isothiazolidinyl, 4-isothiazolidinyl, 5-isothiazolidinyl, 3-pyrazolidinyl, 4-pyrazolidinyl, 5-pyrazolidinyl, 2-oxazolidinyl, 4-oxazolidinyl, 5-oxazolidinyl, 2-thiazolidinyl, 4-thiazolidinyl, 5-thiazolidinyl, 2-imidazolidinyl, 4-imidazolidinyl, 2-pyrrolin-2-yl, 2-pyrrolin-3-yl, 3-pyrrolin-2-yl, 3-pyrrolin-3-yl, 2-piperidinyl, 3-piperidinyl, 4-piperidinyl, 1,3-dioxan-5-yl, 2-tetrahydropyranyl, 4-tetrahydropyranyl, 2-tetrahydrothienyl, 3-hexahydropyridazinyl, 4-hexahydropyridazinyl, 2-hexahydropyrimidinyl, 4-hexahydropyrimidinyl, 5-hexahydropyrimidinyl and 2-piperazinyl;   5-membered heteroaryl which contains one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or oxygen atom: 5-membered heteroaryl groups which, in addition to carbon atoms, may contain one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or oxygen atom as ring members, for example 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyrrolyl, 3-pyrrolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 2-imidazolyl, 4-imidazolyl, and 1,3,4-triazol-2-yl;   6-membered heteroaryl which contains one to three or one to four nitrogen atoms: 6-membered heteroaryl groups which, in addition to carbon atoms, may contain one to three or one to four nitrogen atoms as ring members, for example 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl and 2-pyrazinyl;       

     alkylene: divalent unbranched chains of 2 to 8 CH 2  groups, for example CH 2 CH 2 , CH 2 CH 2 CH 2 , CH 2 CH 2 CH 2 CH 2 , CH 2 CH 2 CH 2 CH 2 CH 2 , CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 , CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2  and CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 ; 
     oxyalkylene: divalent unbranched chains of 2 to 4 CH 2  groups where one valency is attached via an oxygen atom to the skeleton, for example OCH 2 CH 2 , OCH 2 CH 2 CH 2  and OCH 2 CH 2 CH 2 CH 2 ; 
     oxyalkyleneoxy: divalent unbranched chains of 1 to 3 CH 2  groups where both valencies are attached via an oxygen atom to the skeleton, for example OCH 2 O, OCH 2 CH 2 O and OCH 2 CH 2 CH 2 O. 
     In accordance with the present invention, agriculturally acceptable salts are in particular the salts of those cations and the acid addition salts of those acids whose cations and anions, respectively, have no adverse effect on the pesticidal action of the pyrimidines according to the invention. 
     Agriculturally useful salts include in particular the salts of those cations or the acid addition salts of those acids whose cations and anions, respectively, have no adverse effect on the fungicidal action of the compounds I. Thus, suitable cations are in particular the ions of the alkali metals, preferably sodium and potassium, of the alkaline earth metals, preferably calcium, magnesium and barium, and of the transition metals, preferably manganese, copper, zinc and iron, and also the ammonium ion which, if desired, may carry from one to four (C 1 -C 4 )-alkyl substituents and/or one phenyl or benzyl substituent, preferably diisopropylammonium, tetramethylammonium, tetrabutylammonium, trimethylbenzylammonium, and also phosphonium ions, sulfonium ions, preferably tri(C 1 -C 4 )-alkylsulfonium, and sulfoxonium ions, preferably tri(C 1 -C 4 )-alkylsulfoxonium. 
     Anions of useful acid addition salts are, primarily, chloride, bromide, fluoride, hydrogensulfate, sulfate, dihydrogenphosphate, hydrogenphosphate, phosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and also the anions of (C 1 -C 4 )-alkanoic acids, preferably formate, acetate, propionate and butyrate. They can be formed by reacting I with an acid of the corresponding anion, preferably hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid. 
     Suitable pharmaceutically acceptable salts are especially physiologically tolerated salts of the compound I, in particular the acid addition salts with physiologically acceptable acids. Examples of suitable organic and inorganic acids are hydrochloric acid, hydrobromic acid, phosphoric acid, sulfuric acid, C 1 -C 4 -alkylsulfonic acids, such as methanesulfonic acid, aromatic sulfonic acids, such as benzenesulfonic acid and toluenesulfonic acid, oxalic acid, maleic acid, fumaric acid, lactic acid, tartaric acid, adipic acid and benzoic acid. Further suitable acids are described, for example, in Fortschritte der Arzneimittelforschung, Volume 10, pages 224 ff., Birkhäuser Verlag, Basle and Stuttgart, 1966, the entire contents of which is expressly incorporated herein by way of reference. 
     The scope of the present invention includes the (R)- and (S)-isomers and the racemates of compounds of the formula I having chiral centers. 
     As a result of hindered rotation of asymmetrically substituted groups, atrope isomers of compounds of the formula I may be present. They also form part of the subject matter of the invention. 
     The embodiments of the intermediates with respect to the variables correspond to those of the formula I. 
     With a view to the intended use of the pyridazines of the formula I, particular preference is given to the following meanings of the substituents, in each case on their own or in combination: 
     One aspect relates to compounds I in which R 1  and R 4  are halogen, in particular chlorine. These compounds correspond to the formula I.1. 
     
       
         
         
             
             
         
       
     
     A further aspect relates to compounds I in which R 1  is halogen, in particular chlorine, and R 4  is C 1 -C 5 -alkoxy, such as methoxy, ethoxy, n-propoxy, isopropoxy, in particular methoxy. These compounds correspond to the formula I.2. 
     
       
         
         
             
             
         
       
     
     A further aspect relates to compounds I in which R 1  is C 1 -C 6 -alkoxy, such as methoxy, ethoxy, n-propoxy, isopropoxy, in particular methoxy, and R 4  is halogen, in particular chlorine. These compounds correspond to the formula I.3. 
     
       
         
         
             
             
         
       
     
     A further aspect relates to compounds I in which R 1  and R 4  are C 1 -C 6 -alkoxy, such as methoxy, ethoxy, n-propoxy, isopropoxy, in particular methoxy. These compounds correspond to the formula I.4. 
     
       
         
         
             
             
         
       
     
     A further aspect relates to compounds I in which R 1  is halogen, in particular chlorine, and R 4  is cyano. These compounds correspond to the formula I.5. 
     
       
         
         
             
             
         
       
     
     A further aspect relates to compounds I in which R 1  is cyano and R 4  is halogen, in particular chlorine. These compounds correspond to the formula I.6. 
     
       
         
         
             
             
         
       
     
     A further aspect relates to compounds I in which R 1  and R 4  are cyano. These compounds correspond to the formula I.7. 
     
       
         
         
             
             
         
       
     
     A further aspect relates to compounds I in which R 1  is halogen, in particular chlorine, and R 4  is alkyl, in particular methyl. These compounds correspond to the formula I.8 in which R 4′  has the meaning given above. 
     
       
         
         
             
             
         
       
     
     A further aspect relates to compounds I in which R 1  is alkyl, in particular methyl, and R 4  is halogen, in particular chlorine. These compounds correspond to the formula I.9, in which R 1′  has the meaning given above. 
     
       
         
         
             
             
         
       
     
     A further aspect relates to compounds I in which R 1  and R 4  are alkyl, in particular methyl. These compounds correspond to the formula I.10 in which R 1′  and R 4′  have the meaning given above. 
     
       
         
         
             
             
         
       
     
     In the compounds according to the invention, R 2  is preferably C 1 -C 10 -alkyl, C 1 -C 10 -haloalkyl, C 2 -C 10 -alkenyl, C 2 -C 10 -haloalkenyl, C 2 -C 10 -alkynyl, C 2 -C 10 -haloalkynyl, C 3 -C 12 -cycloalkyl (including in particular C 3 -C 5 -cycloalkyl and/or C 9 -C 12 -cycloalkyl), C 3 -C 12 -halocycloalkyl, C 3 -C 12 -cycloalkenyl, C 3 -C 12 -halocycloalkenyl, naphthyl or halonaphthyl or a five-, six-, seven-, eight-, nine- or ten-membered saturated, partially unsaturated or aromatic heterocycle which is attached via carbon and contains one, two, three or four heteroatoms from the group consisting of oxygen, nitrogen and sulfur, more preferably C 1 -C 10 -alkyl, C 1 -C 10 -haloalkyl, C 2 -C 10 -alkenyl, C 2 -C 10 -haloalkenyl, C 2 -C 10 -alkynyl, C 2 -C 10 -haloalkynyl, C 3 -C 12 -cycloalkyl, C 3 -C 12 -halocycloalkyl, C 3 -C 12 -cycloalkenyl or C 3 -C 12 -halocycloalkenyl or a five-, six-, seven-, eight-, nine- or ten-membered saturated, partially unsaturated or aromatic heterocycle which is attached via carbon and contains one, two, three or four heteroatoms from the group consisting of oxygen, nitrogen and sulfur; where R 2  may contain one, two, three or four identical or different groups R a , as defined herein. 
     One aspect relates to compounds I in which R 2  is an aliphatic group which is unsubstituted or substituted by R a , as defined at the outset. These compounds correspond to formula I.a. 
     One aspect of the compounds I.a relates to those compounds in which R 2  is C 1 -C 10 -alkyl, C 1 -C 10 -haloalkyl, C 2 -C 10 -alkenyl, C 2 -C 10 -haloalkenyl, C 2 -C 10 -alkynyl, C 2 -C 10 -haloalkynyl, C 3 -C 12 -cycloalkyl, C 3 -C 12 -halocycloalkyl, C 3 -C 12 -cycloalkenyl, C 3 -C 12 -halocycloalkenyl. 
     One aspect relates to compounds I.a in which R 2  is C 1 -C 8 -alkyl, in particular branched C 3 -C 8 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 8 -alkenyl, in particular branched C 3 -C 5 -alkenyl, C 3 -C 6 -cycloalkyl which may have a C 1 -C 4 -alkyl group, or C 5 -C 6 -cycloalkenyl which may have a C 1 -C 4 -alkyl group. 
     A further aspect relates to compounds I.a in which R 2  is C 3 -C 12 -cycloalkyl, in particular C 6 -C 8 -cycloalkyl. 
     A further aspect relates to compounds I.a in which R 2  is C 1 -C 10 -alkyl, in particular C 3 -C 8 -alkyl, which is optionally substituted by one, two or three R a . Here, R a  is preferably selected from the group consisting of halogen, cyano, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkoximino, C 2 -C 6 -alkenyloximino, C 2 -C 6 -alkynyloximino, C 3 -C 6 -cycloalkyl or C 5 -C 6 -cycloalkenyl, where the aliphatic and/or alicyclic groups for their part may be substituted by one, two or three groups R b . Here, each R b  is preferably independently halogen, cyano, C 1 -C 8 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonyl or C 1 -C 6 -haloalkylcarbonyl. 
     According to one aspect of this embodiment, R 2  is C 1 -C 10 -haloalkyl, in particular C 3 -C 8 -haloalkyl. 
     A further aspect relates to compounds I.a in which R 2  is C 2 -C 10 -alkenyl, in particular C 3 -C 8 -alkenyl, which is optionally substituted by one, two or three R a , as defined herein. 
     A further aspect relates to compounds I.a in which R 2  is C 2 -C 10 -alkynyl, in particular C 3 -C 8 -alkynyl, which is optionally substituted by one, two or three R a , as defined herein. 
     A further aspect relates to compounds I.a in which R 2  is C 3 -C 12 -cycloalkenyl, in particular C 8 -C 10 -cycloalkenyl, especially C 5 - or C 6 -cycloalkenyl, which is optionally substituted by one, two or three R a , as defined herein. According to one aspect of this embodiment according to the invention, the cycloalkenyl group is mono-, di- or trisubstituted by C 1 -C 4 -alkyl, such as, for example, methyl and/or ethyl. 
     One aspect relates to compounds I in which R 2  is a five-, six-, seven-, eight-, nine- or ten-membered saturated, partially unsaturated or aromatic heterocycle which is attached via carbon to the pyridazine skeleton and which contains one, two, three or four heteroatoms from the group consisting of oxygen, nitrogen and sulfur, where the heterocycle is unsubstituted or substituted by one, two, three or four identical or different substituents R a , as defined herein. These compounds correspond to the formula I.B. According to a preferred aspect of this embodiment, R 2  is an optionally substituted five- or six-membered saturated or aromatic heterocycle which is attached via carbon to the pyridazine skeleton. 
     If R 2  carries one, two, three or four, preferably one, two or three, identical or different groups R a , then R a  is preferably selected from the group consisting of halogen, cyano, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkoximino, C 2 -C 6 -alkenyloximino, C 2 -C 6 -alkynyloximino, C 3 -C 6 -cycloalkyl, C 5 -C 6 -cycloalkenyl, where the aliphatic or alicyclic groups for their part may be partially or fully halogenated or may carry one, two or three groups R b . 
     If R a  carries at least one group R b , then R b  is preferably selected from the group consisting of halogen, cyano, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkylcarbonyl and C 1 -C 6 -alkoxy. 
     According to a preferred embodiment of the invention, R 2  is C 1 -C 10 -alkyl, in particular C 3 -C 5 -alkyl, which is optionally substituted by one, two or three R a . Here, R a  is preferably selected from the group consisting of halogen, cyano, C 1 -C 8 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkoximino, C 2 -C 6 -alkenyloximino, C 2 -C 6 -alkynyloximino, C 3 -C 6 -cycloalkyl and C 5 -C 6 -cycloalkenyl, where the aliphatic and/or alicyclic groups for their part may be substituted by one, two or three groups R b . Here, each R b  is preferably independently chosen from the group consisting of halogen, cyano, C 1 -C 8 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonyl and C 1 -C 6 -haloalkylcarbonyl. According to one aspect of this embodiment, R 2  is C 1 -C 10 -haloalkyl, in particular C 3 -C 8 -haloalkyl. 
     A further aspect relates to compounds I in which R 2  is an aryl group which is unsubstituted or substituted by R a , as defined at the outset, such as phenyl or naphthyl, in particular a phenyl group. These compounds correspond to formula I.b. Preferred compounds of the formula I.b have a group selected from the group consisting of phenyl, 3-fluorophenyl, 4-fluorophenyl, 3-chlorophenyl, 4-chlorophenyl, 3-methoxyphenyl, 4-methoxyphenyl, 3-hydroxyphenyl, 4-hydroxyphenyl, 3-tolyl and 4-tolyl in position R 2    
     A further aspect relates to compounds I in which R 2  is a heteroaryl group which is attached via carbon and which is unsubstituted or substituted by R a , as defined at the outset. These compounds correspond to formula I.c. Preferred compounds of the formula I.c have a group selected from the group consisting of pyridin-3-yl and pyridin-4-yl in position R 2 . 
     A further aspect relates to compounds I in which R 2  is a heteroaryl group which is attached via nitrogen and which is unsubstituted or substituted by R a , as defined at the outset. These compounds correspond to formula I.d. 
     According to one embodiment, R 2  is not optionally substituted phenyl. 
     According to a further embodiment, R 2  is not C 6 -C 8 -cycloalkyl, more preferably not C 3 -C 12 -cycloalkyl. Preferably, R 2  is not C 6 -C 8 -cycloalkyl, more preferably not C 3 -C 12 -cycloalkyl. 
     According to a further preferred embodiment of the invention, R 2  is C 2 -C 10 -alkenyl, in particular C 3 -C 8 -alkenyl, which is optionally substituted by one, two or three R a , as defined herein. 
     According to a further preferred embodiment of the invention, R 2  is C 2 -C 10 -alkynyl, in particular C 3 -C 8 -alkynyl, which is optionally substituted by one, two or three R a , as defined herein. 
     According to a further preferred embodiment of the invention, R 2  is C 3 -C 12 -cycloalkenyl, in particular C 5 -C 10 -cycloalkenyl, especially C 5 - or C 6 -cycloalkenyl, which is optionally substituted by one, two or three R a , as defined herein. According to one aspect of this embodiment according to the invention, the cycloalkenyl group is mono-, di- or trisubstituted by C 1 -C 4 -alkyl, such as, for example, methyl and/or ethyl. 
     According to a further preferred embodiment of the invention, R 2  is a five-, six-, seven-, eight-, nine- or ten-membered saturated, partially unsaturated or aromatic heterocycle which is attached via carbon to the pyridazine skeleton and which contains one, two, three or four heteroatoms from the group consisting of oxygen, nitrogen and sulfur, where the heterocycle is unsubstituted or substituted by one, two, three or four identical or different substituents R a , as defined herein. 
     A further aspect relates to compounds I in which R 3  is an aryl group which is unsubstituted or substituted by R a  as defined at the outset, such as phenyl or naphthyl, in particular a phenyl group. These compounds correspond to formula I.A. 
     In one aspect of the compounds I.A, R 3  is phenyl which, in addition to a group L 1  in the ortho-position to the bond to the pyridazine skeleton, carries at least one further group L m . 
     In a further aspect of the compounds I.A, R 3  is phenyl which is substituted only by one group L 1  in the ortho-position to the bond to the pyridazine skeleton. 
     In a further aspect of the compounds I.A, R 3  is phenyl which, in addition to two groups L 1  in the two ortho-positions to the bond to the pyridazine skeleton, carries at least one further group L m . 
     In a further aspect of the compounds I.A, R 3  is phenyl which is substituted only by two groups L 1  in the two ortho-positions to the bond to the pyridazine skeleton. 
     A further aspect relates to compounds I in which R 3  is a heteroaryl group which is attached via carbon and which is unsubstituted or, as defined at the outset, substituted by R a . These compounds correspond to formula I.B. 
     A further aspect relates to compounds I in which R 3  is a heteroaryl group which is attached via nitrogen and which is unsubstituted or, as defined at the outset, substituted by R a . These compounds correspond to formula I.C. 
     In a further preferred embodiment of the invention, R 3  is phenyl, pyridinyl, for example 2-, 3- or 4-pyridinyl, pyrimidinyl, for example 2-, 4- or 5-pyrimidinyl, pyrazinyl, for example 2-pyrazinyl, pyridazinyl, for example 3- or 4-pyridazinyl, triazinyl, furyl, for example 2- or 3-furyl, thienyl, for example 2- or 3-thienyl, pyrrolyl, for example 2- or 3-pyrrolyl, pyrazolyl, for example 1-, 3-, 4- or 5-pyrazolyl, imidazolyl, for example 1-, 2-, 4- or 5-imidazolyl, oxazolyl, for example 2-, 4- or 5-oxazolyl, isoxazolyl, for example 3-, 4- or 5-isoxazolyl, thiazolyl, for example 2-, 4- or 5-thiazolyl, isothiazolyl, for example 3-, 4- or 5-isothiazolyl, triazolyl, for example 1-, 4- or 5-[1,2,3]-1H-triazolyl, 2-, 4- or 5-[1,2,3]-2H-triazolyl, 1-, 3- or 5-[1,2,4]-1H-triazolyl or 3-, 4- or 5-[1,2,4′-4H-triazolyl, oxadiazolyl, for example 4- or 5-[1,2,3]-oxadiazolyl, 3- or 5-[1,2,4]-oxadiazolyl or 2- or 5-[1,3,4]-oxadiazolyl, thiadiazolyl, for example 4- or 5-[1,2,3]-thiadiazolyl, 3- or 5-[1,2,4]-thiadiazolyl or 2- or 5-[1,3,4]-thiadiazolyl, or tetrazolyl, for example 1-, 2- or 5-[1,2,3,4]tetrazolyl, which carries one substituent L 1  and 0, 1, 2, 3 or 4, preferably 0, 1 or 2, substituents L, where L 1  and L 2  are defined as described above or preferably as described below. 
     Particularly preferably, R 3  is phenyl, pyridinyl, for example 2-, 3- or 4-pyridinyl, pyrimidinyl, especially 4- or 5-pyrimidinyl, pyrazinyl, for example 2-pyrazinyl, pyridazinyl, for example 3- or 4-pyridazinyl, furyl, for example 2- or 3-furyl, thienyl, for example 2- or 3-thienyl, pyrazolyl, especially 1- or 5-pyrazolyl, imidazolyl, especially 1-, 2- or 5-imidazolyl, oxazolyl, for example 2-, 4- or 5-oxazolyl, isoxazolyl, for example 3-, 4- or 5-isoxazolyl, thiazolyl, for example 2-, 4- or 5-thiazolyl, isothiazolyl, for example 3-, 4- or 5-isothiazolyl, or triazolyl, especially 1-[1,2,4]-1H-triazolyl which carries one substituent L 1  and 0, 1, 2, 3 or 4, preferably 0, 1 or 2, in particular 1 or 2, substituents L, where L 1  and L are as defined above or preferably as described below. 
     In a preferred embodiment of the invention, R 3  is phenyl which is substituted by a group L 1  and 0, 1, 2, 3 or 4 radicals L. 
     Suitable groups L are in particular the following groups: halogen, such as fluorine or chlorine; cyano; nitro; alkoxycarbonyl; aminocarbonyl; C 1 -C 4 -alkyl, such as methyl; C 1 -C 4 -haloalkyl, such as trifluoromethyl; C 1 -C 4 -alkoxy, such as methoxy. 
     
       
         
         
             
             
         
       
     
     Aspects of R 3  relate in particular to phenyl groups which, in addition to the group L 1 , may have the following substituents: 
     position 2: fluorine, chlorine, methyl; position 3: hydrogen, fluorine, methoxy; position 4: hydrogen, fluorine, chlorine, methyl, methoxy, cyano, nitro, alkoxycarbonyl, aminocarbonyl, haloalkyl, particularly preferably fluorine, chlorine, methyl, methoxy, cyano; position 5: hydrogen, fluorine, chlorine, methyl; particularly preferably hydrogen, fluorine; position 6: hydrogen, fluorine, chlorine, methyl; particularly preferably hydrogen, fluorine. 
     The group L 1  is preferably located in position 3, 4 or 5. 
     In a preferred embodiment of the invention, R 3  is one of the groups A1 or A2 (m=0, 1, 2, 3, 4). 
     
       
         
         
             
             
         
       
     
     Here, L m  is preferably one of the substituent combinations below: 
     2-Cl; 2-F; 2-CH 3 ; 2,6-F 2 ; 2,6-Cl 2 ; 2-F, 6-CH 3 ; 2,4,6-F 3 ; 2,6-F 2 -4-OCH 3 ; 2-Cl-4-OCH 3 ; 2-CH 3 -4-F; 2-CF 3 ; 2-OCH 3 ,6-F; 2,4-F2; 2-F-4-Cl; 2-F-6-Cl; 2-Cl,4-F; 2-Cl,5-F; 2,3-F 2 ; 2,5-F 2 ; 2,3,4-F 3 ; 2-CH 3 ; 2,4-(CH 3 ) 2 ; 2-CH 3 -4-Cl; 2-CH 3 ,5-F; 2-F,4-CH 3 ; 2,6-(CH 3 ) 2 ; 2,4,6-(CH 3 ) 3 ; 2,6-F2,4-CH 3 . Particularly preferably, L m  is one of the substituent combinations below: 2-F; 2-Cl; 2-CH 3 ; 2,6-F 2 ; 2-F,6-Cl; 2-F,6-CH 3 . 
     The compounds of the formula I which carry group A1 or A2 correspond to the formulae I.A1 and I.A2, respectively (m=0, 1, 2, 3, 4). 
     
       
         
         
             
             
         
       
     
     In a further embodiment of the invention, R 3  is a 5-membered heteroaryl which is substituted by L 1  and, if appropriate, by 1, 2 or 3 groups L. Here, the 5-membered heteroaryl ring is preferably selected from the group consisting of thienyl, for example 2- or 3-thienyl, pyrazolyl, for example 1-, 3-, 4- or 5-pyrazolyl, and thiazolyl, for example 2-, 4- or 5-thiazolyl. 
     In a further embodiment of the invention, R 3  is a 6-membered heteroaryl which is substituted by a group L 1  and, if appropriate, by 1, 2 or 3 groups L and which contains one to three nitrogen atoms. Here, the 6-membered heteroaryl ring is preferably selected from the group consisting of pyridinyl, for example 2-, 3- or 4-pyridinyl, pyrimidinyl, for example 2-, 4- or 5-pyrimidinyl, pyrazinyl, for example 2-pyrazinyl and pyridazinyl, for example 3- or 4-pyridazinyl. 
     In a preferred embodiment of the invention, R 3  is pyridyl which is attached in the 2-, 3- or 4-position to the pyridazine ring and which may carry 1, 2 or 3 identical or different substituents L, which are preferably selected from the group consisting of fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, methoxy, methylthio, hydroximinomethyl, hydroximinoethyl, methoximinomethyl, methoximinoethyl and trifluoromethyl. A preferred aspect of such compounds are those of the formulae I.B1 and I.B2 (m=0, 1, 2, 3). 
     
       
         
         
             
             
         
       
     
     In an alternative preferred embodiment of the invention, R 3  is pyrimidyl which is attached in the 2- or 4-position to the pyridazine ring and which may carry 1 or 2 identical or different substituents L, which are preferably selected from the group consisting of fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, methoxy, methylthio, hydroximinomethyl, hydroximinoethyl, methoximinomethyl, methoximinoethyl and trifluoromethyl. A preferred aspect of such compounds are those of the formulae I.B3 and I.B4 (m=0, 1, 2). 
     
       
         
         
             
             
         
       
     
     In an alternative preferred embodiment of the invention, R 3  is thienyl which is attached in the 2- or 3-position to the pyridazine ring and which may carry 1 or 2 identical or different substituents L, which are preferably selected from the group consisting of fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, methoxy, methylthio, hydroximinomethyl, hydroximinoethyl, methoximinomethyl, methoximinoethyl and trifluoromethyl. A preferred aspect of such compounds are those of the formulae I.B5 and I.B6 (m=0, 1, 2). 
     
       
         
         
             
             
         
       
     
     In an alternative preferred embodiment of the invention, R 3  is thiazolyl which is attached in the 2-, 4- or 5-position to the pyridazine ring and which may carry one substituent L, which is preferably selected from the group consisting of fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, methoxy, methylthio, hydroximinomethyl, hydroximinoethyl, methoximinomethyl, methoximinoethyl and trifluoromethyl. A preferred aspect of such compounds are those of the formulae I.B7 and I.B8 (m=0, 1). 
     
       
         
         
             
             
         
       
     
     In an alternative preferred embodiment of the invention, R 3  is imidazolyl which is attached in the 4- or 5-position to the pyridazine ring and which may carry 1 or 2 identical or different substituents L, which are preferably selected from the group consisting of fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, methoxy, methylthio, hydroximinomethyl, hydroximinoethyl, methoximinomethyl, methoximinoethyl and trifluoromethyl. A preferred aspect of such compounds are those of the formulae I.B9 and I.B10 (m=0, 1). 
     
       
         
         
             
             
         
       
     
     In an alternative preferred embodiment of the invention, R 3  is pyrazolyl which is attached in the 1-, 3-, 4- or 5-position to the pyridazine ring and which may carry 1 or 2 identical or different substituents L, which are preferably selected from the group consisting of fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, methoxy, methylthio, hydroximinomethyl, hydroximinoethyl, methoximinomethyl, methoximinoethyl and trifluoromethyl. A preferred aspect of such compounds are those of the formulae I.B11, I.B12 and I.B13 (m=0, 1). 
     
       
         
         
             
             
         
       
     
     In an alternative preferred embodiment of the invention, R 3  is oxazolyl which is attached in the 2-, 3- or 4-position to the pyridazine ring and which may carry one substituent L, which is preferably selected from the group consisting of fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, methoxy, methylthio, hydroximinomethyl, hydroximinoethyl, methoximinomethyl, methoximinoethyl and trifluoromethyl. A preferred aspect of such compounds are those of the formulae I.B14 and I.B15 (m=0, 1) 
     
       
         
         
             
             
         
       
     
     In one aspect of the compounds I.C, R 3  is pyrazol-1-yl. 
     One aspect relates to compounds I.C in which R 3  is pyrazol-1-yl which may be mono- to trisubstituted in the 3-, 4- or 5-position by identical or different L 1  and optionally by L m , which here is preferably chlorine, bromine and/or methyl. Aspects of the compounds of the formula I relate to those of the formulae I.C1 and I.C2 (m=0, 1, 2). 
     
       
         
         
             
             
         
       
     
     In a preferred aspect of the compounds I, in particular of the formulae I.A1 to I.B15, at least one group L is located ortho to the point of attachment of group R 3  to the pyridazine skeleton, in particular chlorine, fluorine or methyl. 
     In a further preferred aspect, a heteroatom of the heteroaromatic R 3  is located ortho to the point of attachment. 
     The index m is, if structurally possible, preferably 1 to 4, where the groups L may be identical of different. If the heteroaromatic groups R 3  carry further substituents L in addition to a group L 1 , these substituents L are preferably selected from the group consisting of: fluorine, chlorine, methyl, methoxy, cyano, nitro, alkoxycarbonyl, aminocarbonyl and haloalkyl. In a further aspect, the optional substituents L are selected from the group consisting of fluorine, chlorine, methyl and methoxy. In a further aspect, the optional substituents L are selected from the group consisting of chlorine, methyl and methoxy. A further aspect relates to heteroaromatic groups R 3  which, in addition to a group L 1 , are also substituted by chlorine. 
     R 3  is in particular phenyl or pyridinyl, where these groups carry a substituent L 1  and 0, 1, 2, 3 or 4, preferably 0, 1 or 2, in particular 1 or 2, substituents L, where L 1  and L are defined as described above or below. 
     If R 3  is phenyl or 2-pyridinyl, these rings carry the substituents L 1  preferably in the 3- or in particular the 4-position (based on the 1-position of the bond to the pyridazine ring; i.e. L 1  is particularly preferably located in the meta- or in particular para-position to this point of attachment). The phenyl or the 2-pyridinyl ring has optionally also 1 or 2 further substituents L. These are preferably attached in the 2- and/or 6-position of the phenyl ring (based on the 1-position of the bond to the pyridazine ring), i.e. located ortho to the point of attachment to the pyridazine ring, and in the case of the 2-pyridine ring preferably in the 6-position (based on the 1-position of the bond to the pyridazine ring). 
     In a preferred embodiment of the invention, the substituent L 1  of group R 3  is a group L 11  of the formula 
       —Y α1 A α —Y α2 ] a -A α -T α   
     where 
     A α  is C 1 -C 4 -alkylene;
 
Y α2  independently of one another are O, S or NR hα ;
 
     T α  is OR hα , SR hα  or NR hα R jα ; 
     each R hα  and R jα  is independently hydrogen or C 1 -C 4 -alkyl; and
 
a is 1, 2, 3 or 4.
 
     C 1 -C 4 -alkylene in A α  is preferably methylene, 1,2-ethylene, 1,2- or 1,3-propylene or 1,4-n-butylene. 
     A α  is preferably methylene, 1,2-ethylene, 1,2-propylene or 1,3-propylene and in particular methylene or 1,2-ethylene. 
     Y α1  and Y α2  independently of one another are preferably O or NR hα , If Y α1  is O, Y α2  is also preferably O. Moreover, in this case T α  is preferably OR hα . If Y α1  is NR hα R hα  and Y α2  is simultaneously O, T α  is in this case preferably OR hα . 
     T α  is preferably OR hα  or NR hα R jα . 
     R hα  and R jα  independently of one another are preferably H, methyl or ethyl. 
     a is preferably 1, 2 or 3. 
     In another preferred embodiment of the invention, the substituent L 1  of group R 3  is a group L 12  of the formula 
       Y β -A β -T β   
     where 
     Y β  is CH 2 , O, S or NR hβ R β ; 
     A β  is C 1 -C 8 -alkylene; 
     T β  is OR hβ , NR hβ R jβ  or OC(═O)-T 3β ; 
     T 3β  is R hβ , OR hβ  or NR hβ R jβ ; and 
     each R hβ  and R jβ  is independently H or C 1 -C 4 -alkyl. 
     Y β  is preferably CH 2  or O and especially O. 
     A β  is preferably C 1 -C 6 -alkylene, in particular C 1 -C 4 -alkylene. 
     T β  is preferably OR hβ  or NR hβ R jβ . 
     R hβ  and R jβ  independently of one another are preferably hydrogen, methyl or ethyl. 
     In another preferred embodiment of the invention, the substituent L 1  of group R 3  is a group L 13  of the formula 
       —Y 1γ -A γ -T γ   
     where 
     Y 1γ  is —CONR hγ  or —COO; 
     A γ  is C 2 -C 6 -alkylene; 
     T γ  is OR hγ , NR hγ R jγ  or OC(═O)-T 3γ ; 
     T 3γ  is R hγ , OR hγ  or NR hγ R jγ ; and 
     each R hγ  and R jγ  is independently H or C 1 -C 4 -alkyl. 
     In another preferred embodiment of the invention, the substituent L 1  of group R 3  is a group L 14  of the formula 
       C(R i )═C(R ii )—Y δ1 A δ -Y δ2 ] a -A δ -T δ   
     where
 
R i , R ii  is hydrogen;
 
A δ  is C 1 -C 4 -alkylene;
 
Y δ1 , Y δ2  independently of one another are O, S or NR hδ ;
 
     T δ  is OR hδ , SR hδ  or NR hδ R jδ ; 
     each R hδ  and R jδ  is independently hydrogen or C 1 -C 4 -alkyl; and
 
a is 1, 2, 3 or 4.
 
C 1 -C 4 -Alkylene in A δ  is preferably methylene, 1,2-ethylene, 1,2- or 1,3-propylene or 1,4-n-butylene.
 
A δ  is preferably methylene, 1,2-ethylene, 1,2-propylene or 1,3-propylene and in particular methylene or 1,2-ethylene.
 
Y δ1  and Y δ2  independently of one another are preferably O or NR hδ . If Y δ1  is O, Y δ2  is also preferably O. Moreover, in this case T δ  is preferably OR hδ . If Y δ1  is NR hδ R jδ  and Y δ2  is simultaneously O, T δ  is in this case preferably OR hδ .
 
T δ  is preferably OR hδ  or NR hδ R jδ .
 
R hδ  and R jδ  independently of one another are preferably H, methyl or ethyl.
 
a is preferably 1, 2 or 3.
 
     In another preferred embodiment of the invention, the substituent L 1  of group R 3  is a group L 15  of the formula 
       C≡C—Y ε1 A ε -Y ε2 ] a -A ε -T ε   
     where
 
A ε  is C 1 -C 4 -alkylene;
 
A ε1 , Y ε2  independently of one another are O, S or NR hε ;
 
     T ε  is OR hε , SR hε  or NR hε R iε ; 
     each R hε  and R iε  is independently hydrogen or C 1 -C 4 -alkyl; and
 
a is 1, 2, 3 or 4.
 
C 1 -C 4 -Alkylene in A δ  is preferably methylene, 1,2-ethylene, 1,2- or 1,3-propylene or 1,4-n-butylene.
 
A ε  is preferably methylene, 1,2-ethylene, 1,2-propylene or 1,3-propylene and in particular methylene or 1,2-ethylene.
 
Y ε1  and Y ε2  independently of one another are preferably O or NR hε . If Y ε1  is O, Y ε2  is also preferably O. Moreover, in this case T ε  is preferably OR hε . If Y ε1  is NR hε R iε  and Y ε2  is simultaneously O, T ε  is in this case preferably OR hε .
 
T ε  is preferably OR hε  or NR hε R iε .
 
R hε  and R iε  independently of one another are preferably H, methyl or ethyl.
 
a is preferably 1, 2 or 3.
 
     The substituent L 1  of group R 3  is particularly preferably a group L 11  or L 12 . 
     L m  is preferably in each case independently selected from the preferred meanings given herein for L m , where it may furthermore be preferred for L to be selected from the group consisting of halogen, nitro, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, in particular C 1 -C 2 -fluoroalkyl, C 1 -C 4 -alkoxy and C 1 -C 4 -alkoxycarbonyl, more preferably selected from the group consisting of nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, isopropyl, trifluoromethyl, fluoromethyl, methoxy and methoxycarbonyl. Preferred L in the ortho position are fluorine, chlorine, bromine, C 1 -C 4 -alkyl, in particular methyl or ethyl, C 1 -C 2 -fluoroalkyl, such as trifluoromethyl, and C 1 -C 4 -alkoxy, in particular methoxy or ethoxy. 
     Furthermore preferably, the substituents L which are attached to R 3 =heteroaryl, such as illustrated below, or R 3 =phenyl, are independently of one another:
         halogen, cyano, nitro, amino, hydroxyl, formyl, carboxy, carbamoyl, thiocarbamoyl;   in each case straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl having in each case 1 to 6 carbon atoms;   in each case straight-chain or branched alkenyl or alkenyloxy having in each case 2 to 6 carbon atoms;   in each case straight-chain or branched haloalkyl, haloalkoxy, haloalkylthio, haloalkylsulfinyl or haloalkylsulfonyl having in each case 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms;   in each case straight-chain or branched haloalkenyl or haloalkenyloxy having in each case 2 to 6 carbon atoms and 1 to 13 identical or different halogen atoms;   in each case straight-chain or branched haloalkenyl or haloalkenyloxy having in each case 2 to 6 carbon atoms and 1 to 11 identical or different halogen atoms;   in each case straight-chain or branched alkylamino, dialkylamino, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkylsulfonyloxy, hydroximinoalkyl or alkoximinoalkyl having in each case 1 to 6 carbon atoms in the individual alkyl moieties;   cycloalkyl having 3 to 6 carbon atoms,   2,3-attached 1,3-propanediyl, 1,4-butanediyl, methylenedioxy   (—O—CH 2 —O—) or 1,2-ethylenedioxy (—O—CH 2 —CH 2 —O—), where these groups may be mono- or polysubstituted by identical or different substituents from the group consisting of halogen, alkyl having 1 to 4 carbon atoms and/or haloalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms.       

     Suitable L m  are in particular the following groups: halogen, such as fluorine or chlorine; cyano; nitro; alkoxycarbonyl; C 1 -C 4 -alkyl, such as methyl; C 1 -C 4 -haloalkyl, such as trifluoromethyl; C 1 -C 4 -alkoxy, such as methoxy. 
     Examples of preferred compounds the general formula I are those of the formulae I.a and I.b 
     
       
         
         
             
             
         
       
     
     where the variables R 1 , R 2  and R 4  and L 1  have the general or preferred meanings given above and L′ and L″ are hydrogen or have one of the general or preferred meanings given for L. 
     In particular with a view to their use, preference is given to the compounds I compiled in the tables below. Moreover, the groups mentioned for a substituent in the tables are per se, independently of the combination in which they are mentioned, a particularly preferred aspect of the substituent in question. 
     Table 1 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ and L″ are H, L 1  is —(OCH 2 ) 2 —OH and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 2 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ and L″ are H, L 1  is —(OCH 2 ) 2 —OCH 3  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 3 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ and L″ are H, L 1  is —(OCH 2 ) 2 —OC 2 H 5  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 4 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ and L″ are H, L 1  is —(OCH 2 ) 3 —OH and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 5 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ and L″ are H, L 1  is —(OCH 2 ) 3 —OCH 3  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 6 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ and L″ are H, L 1  is —(OCH 2 ) 3 —OC 2 H 5  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 7 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ and L″ are H, L 1  is —O—CH 2 CH 2 —OH and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 8 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ and L″ are H, L 1  is —O—CH 2 CH 2 —OCH 3  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 9 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ and L″ are H, L 1  is —O—CH 2 CH 2 —OC 2 H 5  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 10 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ and L″ are H, L 1  is —(O—CH 2 CH 2 ) 2 —OH and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 11 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ and L″ are H, L 1  is —(O—CH 2 CH 2 ) 2 —OCH 3  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 12 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ and L″ are H, L 1  is —(O—CH 2 CH 2 ) 2 —OC 2 H 5  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 13 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ and L″ are H, L 1  is —O—CH 2 CH 2 —NHCH 3  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 14 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ and L″ are H, L 1  is —O—CH 2 CH 2 —N(CH 3 ) 2  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 15 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ and L″ are H, L 1  is —O—CH 2 CH 2 —NHC 2 H 5  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 16 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ and L″ are H, L 1  is —O—CH 2 CH 2 —N(C 2 H 5 ) 2  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 17 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ and L″ are H, L 1  is —O—CH 2 CH 2 CH 2 —NHCH 3  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 18 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ and L″ are H, L 1  is —O—CH 2 CH 2 CH 2 —N(CH 3 ) 2  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 19 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ and L″ are H, L 1  is —O—CH 2 CH 2 CH 2 —NHC 2 H 5  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 20 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ and L″ are H, L 1  is —O—CH 2 CH 2 CH 2 —N(C 2 H 5 ) 2  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 21 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ and L″ are H, L 1  is —O—CH 2 CH 2 CH 2 CH 2 —NHCH 3  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 22 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ and L″ are H, L 1  is —O—CH 2 CH 2 CH 2 CH 2 —N(CH 3 ) 2  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 23 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ and L″ are H, L 1  is —O—CH 2 CH 2 CH 2 CH 2 —NHC 2 H 5  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 24 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ and L″ are H, L 1  is —O—CH 2 CH 2 CH 2 CH 2 —N(C 2 H 5 ) 2  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 25 
     
         
         
           
             Compounds of the formula I.a in which R 1 , R 4  and L′ are Cl, L″ is H, L 1  is —(OCH 2 ) 2 —OH and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 26 
     
         
         
           
             Compounds of the formula I.a in which R 1 , R 4  and L′ are Cl, L″ is H, L 1  is —(OCH 2 ) 2 —OCH 3  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 27 
     
         
         
           
             Compounds of the formula I.a in which R 1 , R 4  and L′ are Cl, L″ is H, L 1  is —(OCH 2 ) 2 —OC 2 H 5  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 28 
     
         
         
           
             Compounds of the formula I.a in which R 1 , R 4  and L′ are Cl, L″ is H, L 1  is —(OCH 2 ) 3 —OH and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 29 
     
         
         
           
             Compounds of the formula I.a in which R 1 , R 4  and L′ are Cl, L″ is H, L 1  is —(OCH 2 ) 3 —OCH 3  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 30 
     
         
         
           
             Compounds of the formula I.a in which R 1 , R 4  and L′ are Cl, L″ is H, L 1  is —(OCH 2 ) 3 —OC 2 H 5  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 31 
     
         
         
           
             Compounds of the formula I.a in which R 1 , R 4  and L′ are Cl, L″ is H, L 1  is —O—CH 2 CH 2 —OH and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 32 
     
         
         
           
             Compounds of the formula I.a in which R 1 , R 4  and L′ are Cl, L″ is H, L 1  is —O—CH 2 CH 2 —OCH 3  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 33 
     
         
         
           
             Compounds of the formula I.a in which R 1 , R 4  and L′ are Cl, L″ is H, L 1  is —O—CH 2 CH 2 —OC 2 H 5  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 34 
     
         
         
           
             Compounds of the formula I.a in which R 1 , R 4  and L′ are Cl, L″ is H, L 1  is —(O—CH 2 CH 2 ) 2 —OH and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 35 
     
         
         
           
             Compounds of the formula I.a in which R 1 , R 4  and L′ are Cl, L″ is H, L 1  is —(O—CH 2 CH 2 ) 2 —OCH 3  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 36 
     
         
         
           
             Compounds of the formula I.a in which R 1 , R 4  and L′ are Cl, L″ is H, L 1  is —(O—CH 2 CH 2 ) 2 —OC 2 H 5  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 37 
     
         
         
           
             Compounds of the formula I.a in which R 1 , R 4  and L′ are Cl, L″ is H, L 1  is —O—CH 2 CH 2 —NHCH 3  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 38 
     
         
         
           
             Compounds of the formula I.a in which R 1 , R 4  and L′ are Cl, L″ is H, L 1  is —O—CH 2 CH 2 —N(CH 3 ) 2  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 39 
     
         
         
           
             Compounds of the formula I.a in which R 1 , R 4  and L′ are Cl, L″ is H, L 1  is —O—CH 2 CH 2 —NHC 2 H 5  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 40 
     
         
         
           
             Compounds of the formula I.a in which R 1 , R 4  and L′ are Cl, L″ is H, L 1  is —O—CH 2 CH 2 —N(C 2 H 5 ) 2  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 41 
     
         
         
           
             Compounds of the formula I.a in which R 1 , R 4  and L′ are Cl, L″ is H, L 1  is —O—CH 2 CH 2 CH 2 —NHCH 3  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 42 
     
         
         
           
             Compounds of the formula I.a in which R 1 , R 4  and L′ are Cl, L″ is H, L 1  is —O—CH 2 CH 2 CH 2 —N(CH 3 ) 2  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 43 
     
         
         
           
             Compounds of the formula I.a in which R 1 , R 4  and L′ are Cl, L″ is H, L 1  is —O—CH 2 CH 2 CH 2 —NHC 2 H 5  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 44 
     
         
         
           
             Compounds of the formula I.a in which R 1 , R 4  and L′ are Cl, L″ is H, L 1  is —O—CH 2 CH 2 CH 2 —N(C 2 H 5 ) 2  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 45 
     
         
         
           
             Compounds of the formula I.a in which R 1 , R 4  and L′ are Cl, L″ is H, L 1  is —O—CH 2 CH 2 CH 2 CH 2 —NHCH 3  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 46 
     
         
         
           
             Compounds of the formula I.a in which R 1 , R 4  and L′ are Cl, L″ is H, L 1  is —O—CH 2 CH 2 CH 2 CH 2 —N(CH 3 ) 2  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 47 
     
         
         
           
             Compounds of the formula I.a in which R 1 , R 4  and L′ are Cl, L″ is H, L 1  is —O—CH 2 CH 2 CH 2 CH 2 —NHC 2 H 5  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 48 
     
         
         
           
             Compounds of the formula I.a in which R 1 , R 4  and L′ are Cl, L″ is H, L 1  is —O—CH 2 CH 2 CH 2 CH 2 —N(C 2 H 5 ) 2  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 49 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ is F, L″ is H, L 1  is —(OCH 2 ) 2 —OH and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 50 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ is F, L″ is H, L 1  is —(OCH 2 ) 2 —OCH 3  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 51 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ is F, L″ is H, L 1  is —(OCH 2 ) 2 —OC 2 H 5  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 52 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ is F, L″ is H, L 1  is —(OCH 2 ) 3 —OH and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 53 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ is F, L″ is H, L 1  is —(OCH 2 ) 3 —OCH 3  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 54 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ is F, L″ is H, L 1  is —(OCH 2 ) 3 —OC 2 H 5  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 55 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ is F, L″ is H, L 1  is —O—CH 2 CH 2 —OH and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 56 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ is F, L″ is H, L 1  is —O—CH 2 CH 2 —OCH 3  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 57 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ is F, L″ is H, L 1  is —O—CH 2 CH 2 —OC 2 H 5  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 58 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ is F, L″ is H, L 1  is —(O—CH 2 CH 2 ) 2 —OH and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 59 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ is F, L″ is H, L 1  is —(O—CH 2 CH 2 ) 2 —OCH 3  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 60 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ is F, L″ is H, L 1  is —(O—CH 2 CH 2 ) 2 —OC 2 H 5  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 61 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ is F, L″ is H, L 1  is —O—CH 2 CH 2 —NHCH 3  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 62 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ is F, L″ is H, L 1  is —O—CH 2 CH 2 —N(CH 3 ) 2  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 63 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ is F, L″ is H, L 1  is —O—CH 2 CH 2 —NHC 2 H 5  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 64 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ is F, L″ is H, L 1  is —O—CH 2 CH 2 —N(C 2 H 5 ) 2  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 65 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ is F, L″ is H, L 1  is —O—CH 2 CH 2 CH 2 —NHCH 3  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 66 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ is F, L″ is H, L 1  is —O—CH 2 CH 2 CH 2 —N(CH 3 ) 2  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 67 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ is F, L″ is H, L 1  is —O—CH 2 CH 2 CH 2 —NHC 2 H 5  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 68 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ is F, L″ is H, L 1  is —O—CH 2 CH 2 CH 2 —N(C 2 H 5 ) 2  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 69 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ is F, L″ is H, L 1  is —O—CH 2 CH 2 CH 2 CH 2 —NHCH 3  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 70 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ is F, L″ is H, L 1  is —O—CH 2 CH 2 CH 2 CH 2 —N(CH 3 ) 2  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 71 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ is F, L″ is H, L 1  is —O—CH 2 CH 2 CH 2 CH 2 —NHC 2 H 5  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 72 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ is F, L″ is H, L 1  is —O—CH 2 CH 2 CH 2 CH 2 —N(C 2 H 5 ) 2  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 73 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ is CH 3 , L″ is H, L 1  is —(OCH 2 ) 2 —OH and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 74 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ is CH 3 , L″ is H, L 1  is —(OCH 2 ) 2 —OCH 3  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 75 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ is CH 3 , L″ is H, L 1  is —(OCH 2 ) 2 —OC 2 H 5  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 76 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ is CH 3 , L″ is H, L 1  is —(OCH 2 ) 3 —OH and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 77 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ is CH 3 , L″ is H, L 1  is —(OCH 2 ) 3 —OCH 3  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 78 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ is CH 3 , L″ is H, L 1  is —(OCH 2 ) 3 —OC 2 H 5  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 79 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ is CH 3 , L″ is H, L 1  is —O—CH 2 CH 2 —OH and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 80 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ is CH 3 , L″ is H, L 1  is —O—CH 2 CH 2 —OCH 3  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 81 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ is CH 3 , L″ is H, L 1  is —O—CH 2 CH 2 —OC 2 H 5  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 82 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ is CH 3 , L″ is H, L 1  is —(O—CH 2 CH 2 ) 2 —OH and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 83 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ is CH 3 , L″ is H, L 1  is —(O—CH 2 CH 2 ) 2 —OCH 3  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 84 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ is CH 3 , L″ is H, L 1  is —(O—CH 2 CH 2 ) 2 —OC 2 H 5  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 85 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ is CH 3 , L″ is H, L 1  is —O—CH 2 CH 2 —NHCH 3  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 86 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ is CH 3 , L″ is H, L 1  is —O—CH 2 CH 2 —N(CH 3 ) 2  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 87 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ is CH 3 , L″ is H, L 1  is —O—CH 2 CH 2 —NHC 2 H 5  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 88 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ is CH 3 , L″ is H, L 1  is —O—CH 2 CH 2 —N(C 2 H 5 ) 2  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 89 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ is CH 3 , L″ is H, L 1  is —O—CH 2 CH 2 CH 2 —NHCH 3  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 90 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ is CH 3 , L″ is H, L 1  is —O—CH 2 CH 2 CH 2 —N(CH 3 ) 2  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 91 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ is CH 3 , L″ is H, L 1  is —O—CH 2 CH 2 CH 2 —NHC 2 H 5  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 92 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ is CH 3 , L″ is H, L 1  is —O—CH 2 CH 2 CH 2 —N(C 2 H 5 ) 2  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 93 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ is CH 3 , L″ is H, L 1  is —O—CH 2 CH 2 CH 2 CH 2 —NHCH 3  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 94 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ is CH 3 , L″ is H, L 1  is —O—CH 2 CH 2 CH 2 CH 2 —N(CH 3 ) 2  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 95 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ is CH 3 , L″ is H, L 1  is —O—CH 2 CH 2 CH 2 CH 2 —NHC 2 H 5  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 96 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ is CH 3 , L″ is H, L 1  is —O—CH 2 CH 2 CH 2 CH 2 —N(C 2 H 5 ) 2  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 97 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ and L″ are F, L 1  is —(OCH 2 ) 2 —OH and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 98 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ and L″ are F, L 1  is —(OCH 2 ) 2 —OCH 3  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 99 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ and L″ are F, L 1  is —(OCH 2 ) 2 —OC 2 H 5  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 100 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ and L″ are F, L 1  is —(OCH 2 ) 3 —OH and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 101 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ and L″ are F, L 1  is —(OCH 2 ) 3 —OCH 3  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 102 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ and L″ are F, L 1  is —(OCH 2 ) 3 —OC 2 H 5  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 103 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ and L″ are F, L 1  is —O—CH 2 CH 2 —OH and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 104 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ and L″ are F, L 1  is —O—CH 2 CH 2 —OCH 3  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 105 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ and L″ are F, L 1  is —O—CH 2 CH 2 —OC 2 H 5  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 106 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ and L″ are F, L 1  is —(O—CH 2 CH 2 ) 2 —OH and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 107 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ and L″ are F, L 1  is —(O—CH 2 CH 2 ) 2 —OCH 3  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 108 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ and L″ are F, L 1  is —(O—CH 2 CH 2 ) 2 —OC 2 H 5  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 109 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ and L″ are F, L 1  is —O—CH 2 CH 2 —NHCH 3  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 110 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ and L″ are F, L 1  is —O—CH 2 CH 2 —N(CH 3 ) 2  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 111 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ and L″ are F, L 1  is —O—CH 2 CH 2 —NHC 2 H 5  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 112 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ and L″ are F, L 1  is —O—CH 2 CH 2 —N(C 2 H 5 ) 2  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 113 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ and L″ are F, L 1  is —O—CH 2 CH 2 CH 2 —NHCH 3  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 114 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ and L″ are F, L 1  is —O—CH 2 CH 2 CH 2 —N(CH 3 ) 2  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 115 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ and L″ are F, L 1  is —O—CH 2 CH 2 CH 2 —NHC 2 H 5  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 116 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ and L″ are F, L 1  is —O—CH 2 CH 2 CH 2 —N(C 2 H 5 ) 2  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 117 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ and L″ are F, L 1  is —O—CH 2 CH 2 CH 2 CH 2 —NHCH 3  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 118 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ and L″ are F, L 1  is —O—CH 2 CH 2 CH 2 CH 2 —N(CH 3 ) 2  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 119 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ and L″ are F, L 1  is —O—CH 2 CH 2 CH 2 CH 2 —NHC 2 H 5  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 120 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ and L″ are F, L 1  is —O—CH 2 CH 2 CH 2 CH 2 —N(C 2 H 5 ) 2  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 121 
     
         
         
           
             Compounds of the formula I.a in which R 1 , R 4  and L′ are Cl and L″ is F, L 1  is —(OCH 2 ) 2 —OH and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 122 
     
         
         
           
             Compounds of the formula I.a in which R 1 , R 4  and L′ are Cl and L″ is F, L 1  is —(OCH 2 ) 2 —OCH 3  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 123 
     
         
         
           
             Compounds of the formula I.a in which R 1 , R 4  and L′ are Cl and L″ is F, L 1  is —(OCH 2 ) 2 —OC 2 H 5  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 124 
     
         
         
           
             Compounds of the formula I.a in which R 1 , R 4  and L′ are Cl and L″ is F, L 1  is —(OCH 2 ) 3 —OH and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 125 
     
         
         
           
             Compounds of the formula I.a in which R 1 , R 4  and L′ are Cl and L″ is F, L 1  is —(OCH 2 ) 3 —OCH 3  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 126 
     
         
         
           
             Compounds of the formula I.a in which R 1 , R 4  and L′ are Cl and L″ is F, L 1  is —(OCH 2 ) 3 —OC 2 H 5  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 127 
     
         
         
           
             Compounds of the formula I.a in which R 1 , R 4  and L′ are Cl and L″ is F, L 1  is —O—CH 2 CH 2 —OH and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 128 
     
         
         
           
             Compounds of the formula I.a in which R 1 , R 4  and L′ are Cl and L″ is F, L 1  is —O—CH 2 CH 2 —OCH 3  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 129 
     
         
         
           
             Compounds of the formula I.a in which R 1 , R 4  and L′ are Cl and L″ is F, L 1  is —O—CH 2 CH 2 —OC 2 H 5  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 130 
     
         
         
           
             Compounds of the formula I.a in which R 1 , R 4  and L′ are Cl and L″ is F, L 1  is —(O—CH 2 CH 2 ) 2 —OH and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 131 
     
         
         
           
             Compounds of the formula I.a in which R 1 , R 4  and L′ are Cl and L″ is F, L 1  is —(O—CH 2 CH 2 ) 2 —OCH 3  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 132 
     
         
         
           
             Compounds of the formula I.a in which R 1 , R 4  and L′ are Cl and L″ is F, L 1  is —(O—CH 2 CH 2 ) 2 —OC 2 H 5  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 133 
     
         
         
           
             Compounds of the formula I.a in which R 1 , R 4  and L′ are Cl and L″ is F, L 1  is —O—CH 2 CH 2 —NHCH 3  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 134 
     
         
         
           
             Compounds of the formula I.a in which R 1 , R 4  and L′ are Cl and L″ is F, L 1  is —O—CH 2 CH 2 —N(CH 3 ) 2  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 135 
     
         
         
           
             Compounds of the formula I.a in which R 1 , R 4  and L′ are Cl and L″ is F, L 1  is —O—CH 2 CH 2 —NHC 2 H 5  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 136 
     
         
         
           
             Compounds of the formula I.a in which R 1 , R 4  and L′ are Cl and L″ is F, L 1  is —O—CH 2 CH 2 —N(C 2 H 5 ) 2  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 137 
     
         
         
           
             Compounds of the formula I.a in which R 1 , R 4  and L′ are Cl and L″ is F, L 1  is —O—CH 2 CH 2 CH 2 —NHCH 3  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 138 
     
         
         
           
             Compounds of the formula I.a in which R 1 , R 4  and L′ are Cl and L″ is F, L 1  is —O—CH 2 CH 2 CH 2 —N(CH 3 ) 2  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 139 
     
         
         
           
             Compounds of the formula I.a in which R 1 , R 4  and L′ are Cl and L″ is F, L 1  is —O—CH 2 CH 2 CH 2 —NHC 2 H 5  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 140 
     
         
         
           
             Compounds of the formula I.a in which R 1 , R 4  and L′ are Cl and L″ is F, L 1  is —O—CH 2 CH 2 CH 2 —N(C 2 H 5 ) 2  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 141 
     
         
         
           
             Compounds of the formula I.a in which R 1 , R 4  and L′ are Cl and L″ is F, L 1  is —O—CH 2 CH 2 CH 2 CH 2 —NHCH 3  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 142 
     
         
         
           
             Compounds of the formula I.a in which R 1 , R 4  and L′ are Cl and L″ is F, L 1  is —O—CH 2 CH 2 CH 2 CH 2 —N(CH 3 ) 2  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 143 
     
         
         
           
             Compounds of the formula I.a in which R 1 , R 4  and L′ are Cl and L″ is F, L 1  is —O—CH 2 CH 2 CH 2 CH 2 —NHC 2 H 5  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 144 
     
         
         
           
             Compounds of the formula I.a in which R 1 , R 4  and L′ are Cl and L″ is F, L 1  is —O—CH 2 CH 2 CH 2 CH 2 —N(C 2 H 5 ) 2  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 145 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ is CH 3 , L″ is F, L 1  is —(OCH 2 ) 2 —OH and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 146 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ is CH 3 , L″ is F, L 1  is —(OCH 2 ) 2 —OCH 3  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 147 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ is CH 3 , L″ is F, L 1  is —(OCH 2 ) 2 —OC 2 H 5  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 148 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ is CH 3 , L″ is F, L 1  is —(OCH 2 ) 3 —OH and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 149 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ is CH 3 , L″ is F, L 1  is —(OCH 2 ) 3 —OCH 3  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 150 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ is CH 3 , L″ is F, L 1  is —(OCH 2 ) 3 —OC 2 H 5  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 151 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ is CH 3 , L″ is F, L 1  is —O—CH 2 CH 2 —OH and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 152 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ is CH 3 , L″ is F, L 1  is —O—CH 2 CH 2 —OCH 3  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 153 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ is CH 3 , L″ is F, L 1  is —O—CH 2 CH 2 —OC 2 H 5  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 154 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ is CH 3 , L″ is F, L 1  is —(O—CH 2 CH 2 ) 2 —OH and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 155 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ is CH 3 , L″ is F, L 1  is —(O—CH 2 CH 2 ) 2 —OCH 3  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 156 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ is CH 3 , L″ is F, L 1  is —(O—CH 2 CH 2 ) 2 —OC 2 H 5  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 157 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ is CH 3 , L″ is F, L 1  is —O—CH 2 CH 2 —NHCH 3  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 158 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ is CH 3 , L″ is F, L 1  is —O—CH 2 CH 2 —N(CH 3 ) 2  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 159 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ is CH 3 , L″ is F, L 1  is —O—CH 2 CH 2 —NHC 2 H 5  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 160 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ is CH 3 , L″ is F, L 1  is —O—CH 2 CH 2 —N(C 2 H 5 ) 2  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 161 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ is CH 3 , L″ is F, L 1  is —O—CH 2 CH 2 CH 2 —NHCH 3  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 162 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ is CH 3 , L″ is F, L 1  is —O—CH 2 CH 2 CH 2 —N(CH 3 ) 2  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 163 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ is CH 3 , L″ is F, L 1  is —O—CH 2 CH 2 CH 2 —NHC 2 H 5  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 164 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ is CH 3 , L″ is F, L 1  is —O—CH 2 CH 2 CH 2 —N(C 2 H 5 ) 2  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 165 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ is CH 3 , L″ is F, L 1  is —O—CH 2 CH 2 CH 2 CH 2 —NHCH 3  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 166 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ is CH 3 , L″ is F, L 1  is —O—CH 2 CH 2 CH 2 CH 2 —N(CH 3 ) 2  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 167 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ is CH 3 , L″ is F, L 1  is —O—CH 2 CH 2 CH 2 CH 2 —NHC 2 H 5  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 168 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ is CH 3 , L″ is F, L 1  is —O—CH 2 CH 2 CH 2 CH 2 —N(C 2 H 5 ) 2  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 169 
     
         
         
           
             Compounds of the formula I.a in which R 1 , R 4 , L′ and L″ are Cl, L 1  is —(OCH 2 ) 2 —OH and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 170 
     
         
         
           
             Compounds of the formula I.a in which R 1 , R 4 , L′ and L″ are Cl, L 1  is —(OCH 2 ) 2 —OCH 3  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 171 
     
         
         
           
             Compounds of the formula I.a in which R 1 , R 4 , L′ and L″ are Cl, L 1  is —(OCH 2 ) 2 —OC 2 H 5  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 172 
     
         
         
           
             Compounds of the formula I.a in which R 1 , R 4 , L′ and L″ are Cl, L 1  is —(OCH 2 ) 3 —OH and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 173 
     
         
         
           
             Compounds of the formula I.a in which R 1 , R 4 , L′ and L″ are Cl, L 1  is —(OCH 2 ) 3 —OCH 3  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 174 
     
         
         
           
             Compounds of the formula I.a in which R 1 , R 4 , L′ and L″ are Cl, L 1  is —(OCH 2 ) 3 —OC 2 H 5  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 175 
     
         
         
           
             Compounds of the formula I.a in which R 1 , R 4 , L′ and L″ are Cl, L 1  is —O—CH 2 CH 2 —OH and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 176 
     
         
         
           
             Compounds of the formula I.a in which R 1 , R 4 , L′ and L″ are Cl, L 1  is —O—CH 2 CH 2 —OCH 3  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 177 
     
         
         
           
             Compounds of the formula I.a in which R 1 , R 4 , L′ and L″ are Cl, L 1  is —O—CH 2 CH 2 —OC 2 H 5  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 178 
     
         
         
           
             Compounds of the formula I.a in which R 1 , R 4 , L′ and L″ are Cl, L 1  is —(O—CH 2 CH 2 ) 2 —OH and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 179 
     
         
         
           
             Compounds of the formula I.a in which R 1 , R 4 , L′ and L″ are Cl, L 1  is —(O—CH 2 CH 2 ) 2 —OCH 3  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 180 
     
         
         
           
             Compounds of the formula I.a in which R 1 , R 4 , L′ and L″ are Cl, L 1  is —(O—CH 2 CH 2 ) 2 —OC 2 H 5  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 181 
     
         
         
           
             Compounds of the formula I.a in which R 1 , R 4 , L′ and L″ are Cl, L 1  is —O—CH 2 CH 2 —NHCH 3  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 182 
     
         
         
           
             Compounds of the formula I.a in which R 1 , R 4 , L′ and L″ are Cl, L 1  is —O—CH 2 CH 2 —N(CH 3 ) 2  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 183 
     
         
         
           
             Compounds of the formula I.a in which R 1 , R 4 , L′ and L″ are Cl, L 1  is —O—CH 2 CH 2 —NHC 2 H 5  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 184 
     
         
         
           
             Compounds of the formula I.a in which R 1 , R 4 , L′ and L″ are Cl, L 1  is —O—CH 2 CH 2 —N(C 2 H 5 ) 2  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 185 
     
         
         
           
             Compounds of the formula I.a in which R 1 , R 4 , L′ and L″ are Cl, L 1  is —O—CH 2 CH 2 CH 2 —NHCH 3  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 186 
     
         
         
           
             Compounds of the formula I.a in which R 1 , R 4 , L′ and L″ are Cl, L 1  is —O—CH 2 CH 2 CH 2 —N(CH 3 ) 2  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 187 
     
         
         
           
             Compounds of the formula I.a in which R 1 , R 4 , L′ and L″ are Cl, L 1  is —O—CH 2 CH 2 CH 2 —NHC 2 H 5  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 188 
     
         
         
           
             Compounds of the formula I.a in which R 1 , R 4 , L′ and L″ are Cl, L 1  is —O—CH 2 CH 2 CH 2 —N(C 2 H 5 ) 2  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 189 
     
         
         
           
             Compounds of the formula I.a in which R 1 , R 4 , L′ and L″ are Cl, L 1  is —O—CH 2 CH 2 CH 2 CH 2 —NHCH 3  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 190 
     
         
         
           
             Compounds of the formula I.a in which R 1 , R 4 , L′ and L″ are Cl, L 1  is —O—CH 2 CH 2 CH 2 CH 2 —N(CH 3 ) 2  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 191 
     
         
         
           
             Compounds of the formula I.a in which R 1 , R 4 , L′ and L″ are Cl, L 1  is —O—CH 2 CH 2 CH 2 CH 2 —NHC 2 H 5  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 192 
     
         
         
           
             Compounds of the formula I.a in which R 1 , R 4 , L′ and L″ are Cl, L 1  is —O—CH 2 CH 2 CH 2 CH 2 —N(C 2 H 5 ) 2  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 193 
     
         
         
           
             Compounds of the formula I.a in which R 1 , R 4  and L′ are Cl, L″ is CH 3 , L 1  is —(OCH 2 ) 2 —OH and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 194 
     
         
         
           
             Compounds of the formula I.a in which R 1 , R 4  and L′ are Cl, L″ is CH 3 , L 1  is —(OCH 2 ) 2 —OCH 3  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 195 
     
         
         
           
             Compounds of the formula I.a in which R 1 , R 4  and L′ are Cl, L″ is CH 3 , L 1  is —(OCH 2 ) 2 —OC 2 H 5  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 196 
     
         
         
           
             Compounds of the formula I.a in which R 1 , R 4  and L′ are Cl, L″ is CH 3 , L 1  is —(OCH 2 ) 3 —OH and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 197 
     
         
         
           
             Compounds of the formula I.a in which R 1 , R 4  and L′ are Cl, L″ is CH 3 , L 1  is —(OCH 2 ) 3 —OCH 3  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 198 
     
         
         
           
             Compounds of the formula I.a in which R 1 , R 4  and L′ are Cl, L″ is CH 3 , L 1  is —(OCH 2 ) 3 —OC 2 H 5  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 199 
     
         
         
           
             Compounds of the formula I.a in which R 1 , R 4  and L′ are Cl, L″ is CH 3 , L 1  is —O—CH 2 CH 2 —OH and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 200 
     
         
         
           
             Compounds of the formula I.a in which R 1 , R 4  and L′ are Cl, L″ is CH 3 , L 1  is —O—CH 2 CH 2 —OCH 3  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 201 
     
         
         
           
             Compounds of the formula I.a in which R 1 , R 4  and L′ are Cl, L″ is CH 3 , L 1  is —O—CH 2 CH 2 —OC 2 H 5  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 202 
     
         
         
           
             Compounds of the formula I.a in which R 1 , R 4  and L′ are Cl, L″ is CH 3 , L 1  is —(O—CH 2 CH 2 ) 2 —OH and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 203 
     
         
         
           
             Compounds of the formula I.a in which R 1 , R 4  and L′ are Cl, L″ is CH 3 , L 1  is —(O—CH 2 CH 2 ) 2 —OCH 3  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 204 
     
         
         
           
             Compounds of the formula I.a in which R 1 , R 4  and L′ are Cl, L″ is CH 3 , L 1  is —(O—CH 2 CH 2 ) 2 —OC 2 H 5  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 205 
     
         
         
           
             Compounds of the formula I.a in which R 1 , R 4  and L′ are Cl, L″ is CH 3 , L 1  is —O—CH 2 CH 2 —NHCH 3  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 206 
     
         
         
           
             Compounds of the formula I.a in which R 1 , R 4  and L′ are Cl, L″ is CH 3 , L 1  is —O—CH 2 CH 2 —N(CH 3 ) 2  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 207 
     
         
         
           
             Compounds of the formula I.a in which R 1 , R 4  and L′ are Cl, L″ is CH 3 , L 1  is —O—CH 2 CH 2 —NHC 2 H 5  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 208 
     
         
         
           
             Compounds of the formula I.a in which R 1 , R 4  and L′ are Cl, L″ is CH 3 , L 1  is —O—CH 2 CH 2 —N(C 2 H 5 ) 2  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 209 
     
         
         
           
             Compounds of the formula I.a in which R 1 , R 4  and L′ are Cl, L″ is CH 3 , L 1  is —O—CH 2 CH 2 CH 2 —NHCH 3  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 210 
     
         
         
           
             Compounds of the formula I.a in which R 1 , R 4  and L′ are Cl, L″ is CH 3 , L 1  is —O—CH 2 CH 2 CH 2 —N(CH 3 ) 2  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 211 
     
         
         
           
             Compounds of the formula I.a in which R 1 , R 4  and L′ are Cl, L″ is CH 3 , L 1  is —O—CH 2 CH 2 CH 2 —NHC 2 H 5  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 212 
     
         
         
           
             Compounds of the formula I.a in which R 1 , R 4  and L′ are Cl, L″ is CH 3 , L 1  is —O—CH 2 CH 2 CH 2 —N(C 2 H 5 ) 2  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 213 
     
         
         
           
             Compounds of the formula I.a in which R 1 , R 4  and L′ are Cl, L″ is CH 3 , L 1  is —O—CH 2 CH 2 CH 2 CH 2 —NHCH 3  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 214 
     
         
         
           
             Compounds of the formula I.a in which R 1 , R 4  and L′ are Cl, L″ is CH 3 , L 1  is —O—CH 2 CH 2 CH 2 CH 2 —N(CH 3 ) 2  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 215 
     
         
         
           
             Compounds of the formula I.a in which R 1 , R 4  and L′ are Cl, L″ is CH 3 , L 1  is —O—CH 2 CH 2 CH 2 CH 2 —NHC 2 H 5  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 216 
     
         
         
           
             Compounds of the formula I.a in which R 1 , R 4  and L′ are Cl, L″ is CH 3 , L 1  is —O—CH 2 CH 2 CH 2 CH 2 —N(C 2 H 5 ) 2  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 217 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ and L″ are CH 3 , L 1  is —(OCH 2 ) 2 —OH and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 218 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ and L″ are CH 3 , L 1  is —(OCH 2 ) 2 —OCH 3  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 219 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ and L″ are CH 3 , L 1  is —(OCH 2 ) 2 —OC 2 H 5  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 220 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ and L″ are CH 3 , L 1  is —(OCH 2 ) 3 —OH and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 221 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ and L″ are CH 3 , L 1  is —(OCH 2 ) 3 —OCH 3  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 222 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ and L″ are CH 3 , L 1  is —(OCH 2 ) 3 —OC 2 H 5  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 223 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ and L″ are CH 3 , L 1  is —O—CH 2 CH 2 —OH and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 224 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ and L″ are CH 3 , L 1  is —O—CH 2 CH 2 —OCH 3  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 225 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ and L″ are CH 3 , L 1  is —O—CH 2 CH 2 —OC 2 H 5  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 226 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ and L″ are CH 3 , L 1  is —(O—CH 2 CH 2 ) 2 —OH and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 227 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ and L″ are CH 3 , L 1  is —(O—CH 2 CH 2 ) 2 —OCH 3  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 228 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ and L″ are CH 3 , L 1  is —(O—CH 2 CH 2 ) 2 —OC 2 H 5  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 229 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ and L″ are CH 3 , L 1  is —O—CH 2 CH 2 —NHCH 3  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 230 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ and L″ are CH 3 , L 1  is —O—CH 2 CH 2 —N(CH 3 ) 2  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 231 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ and L″ are CH 3 , L 1  is —O—CH 2 CH 2 —NHC 2 H 5  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 232 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ and L″ are CH 3 , L 1  is —O—CH 2 CH 2 —N(C 2 H 5 ) 2  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 233 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ and L″ are CH 3 , L 1  is —O—CH 2 CH 2 CH 2 —NHCH 3  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 234 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ and L″ are CH 3 , L 1  is —O—CH 2 CH 2 CH 2 —N(CH 3 ) 2  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 235 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ and L″ are CH 3 , L 1  is —O—CH 2 CH 2 CH 2 —NHC 2 H 5  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 236 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ and L″ are CH 3 , L 1  is —O—CH 2 CH 2 CH 2 —N(C 2 H 5 ) 2  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 237 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ and L″ are CH 3 , L 1  is —O—CH 2 CH 2 CH 2 CH 2 —NHCH 3  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 238 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ and L″ are CH 3 , L 1  is —O—CH 2 CH 2 CH 2 CH 2 —N(CH 3 ) 2  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 239 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ and L″ are CH 3 , L 1  is —O—CH 2 CH 2 CH 2 CH 2 —NHC 2 H 5  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 240 
     
         
         
           
             Compounds of the formula I.a in which R 1  and R 4  are Cl, L′ and L″ are CH 3 , L 1  is —O—CH 2 CH 2 CH 2 CH 2 —N(C 2 H 5 ) 2  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 241 
     
         
         
           
             Compounds of the formula I.b in which R 1  and R 4  are Cl, L′ is H, L 1  is —(OCH 2 ) 2 —OH and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 242 
     
         
         
           
             Compounds of the formula I.b in which R 1  and R 4  are Cl, L′ is H, L 1  is —(OCH 2 ) 2 —OCH 3  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 243 
     
         
         
           
             Compounds of the formula I.b in which R 1  and R 4  are Cl, L′ is H, L 1  is —(OCH 2 ) 2 —OC 2 H 5  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 244 
     
         
         
           
             Compounds of the formula I.b in which R 1  and R 4  are Cl, L′ is H, L 1  is —(OCH 2 ) 3 —OH and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 245 
     
         
         
           
             Compounds of the formula I.b in which R 1  and R 4  are Cl, L′ is H, L 1  is —(OCH 2 ) 3 —OCH 3  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 246 
     
         
         
           
             Compounds of the formula I.b in which R 1  and R 4  are Cl, L′ is H, L 1  is —(OCH 2 ) 3 —OC 2 H 5  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 247 
     
         
         
           
             Compounds of the formula I.b in which R 1  and R 4  are Cl, L′ is H, L 1  is —O—CH 2 CH 2 —OH and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 248 
     
         
         
           
             Compounds of the formula I.b in which R 1  and R 4  are Cl, L′ is H, L 1  is —O—CH 2 CH 2 —OCH 3  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 249 
     
         
         
           
             Compounds of the formula I.b in which R 1  and R 4  are Cl, L′ is H, L 1  is —O—CH 2 CH 2 —OC 2 H 5  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 250 
     
         
         
           
             Compounds of the formula I.b in which R 1  and R 4  are Cl, L′ is H, L 1  is —(O—CH 2 CH 2 ) 2 —OH and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 251 
     
         
         
           
             Compounds of the formula I.b in which R 1  and R 4  are Cl, L′ is H, L 1  is —(O—CH 2 CH 2 ) 2 —OCH 3  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 252 
     
         
         
           
             Compounds of the formula I.b in which R 1  and R 4  are Cl, L′ is H, L 1  is —(O—CH 2 CH 2 ) 2 —OC 2 H 5  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 253 
     
         
         
           
             Compounds of the formula I.b in which R 1  and R 4  are Cl, L′ is H, L 1  is —O—CH 2 CH 2 —NHCH 3  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 254 
     
         
         
           
             Compounds of the formula I.b in which R 1  and R 4  are Cl, L′ is H, L 1  is —O—CH 2 CH 2 —N(CH 3 ) 2  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 255 
     
         
         
           
             Compounds of the formula I.b in which R 1  and R 4  are Cl, L′ is H, L 1  is —O—CH 2 CH 2 —NHC 2 H 5  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 256 
     
         
         
           
             Compounds of the formula I.b in which R 1  and R 4  are Cl, L′ is H, L 1  is —O—CH 2 CH 2 —N(C 2 H 5 ) 2  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 257 
     
         
         
           
             Compounds of the formula I.b in which R 1  and R 4  are Cl, L′ is H, L 1  is —O—CH 2 CH 2 CH 2 —NHCH 3  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 258 
     
         
         
           
             Compounds of the formula I.b in which R 1  and R 4  are Cl, L′ is H, L 1  is —O—CH 2 CH 2 CH 2 —N(CH 3 ) 2  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 259 
     
         
         
           
             Compounds of the formula I.b in which R 1  and R 4  are Cl, L′ is H, L 1  is —O—CH 2 CH 2 CH 2 —NHC 2 H 5  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 260 
     
         
         
           
             Compounds of the formula I.b in which R 1  and R 4  are Cl, L′ is H, L 1  is —O—CH 2 CH 2 CH 2 —N(C 2 H 5 ) 2  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 261 
     
         
         
           
             Compounds of the formula I.b in which R 1  and R 4  are Cl, L′ is H, L 1  is —O—CH 2 CH 2 CH 2 CH 2 —NHCH 3  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 262 
     
         
         
           
             Compounds of the formula I.b in which R 1  and R 4  are Cl, L′ is H, L 1  is —O—CH 2 CH 2 CH 2 CH 2 —N(CH 3 ) 2  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 263 
     
         
         
           
             Compounds of the formula I.b in which R 1  and R 4  are Cl, L′ is H, L 1  is —O—CH 2 CH 2 CH 2 CH 2 —NHC 2 H 5  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 264 
     
         
         
           
             Compounds of the formula I.b in which R 1  and R 4  are Cl, L′ is H, L 1  is —O—CH 2 CH 2 CH 2 CH 2 —N(C 2 H 5 ) 2  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 265 
     
         
         
           
             Compounds of the formula I.b in which R 1 , R 4  and L′ are Cl, L 1  is —(OCH 2 ) 2 —OH and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 266 
     
         
         
           
             Compounds of the formula I.b in which R 1 , R 4  and L′ are Cl, L 1  is —(OCH 2 ) 2 —OCH 3  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 267 
     
         
         
           
             Compounds of the formula I.b in which R 1 , R 4  and L′ are Cl, L 1  is —(OCH 2 ) 2 —OC 2 H 5  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 268 
     
         
         
           
             Compounds of the formula I.b in which R 1 , R 4  and L′ are Cl, L 1  is —(OCH 2 ) 3 —OH and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 269 
     
         
         
           
             Compounds of the formula I.b in which R 1 , R 4  and L′ are Cl, L 1  is —(OCH 2 ) 3 —OCH 3  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 270 
     
         
         
           
             Compounds of the formula I.b in which R 1 , R 4  and L′ are Cl, L 1  is —(OCH 2 ) 3 —OC 2 H 5  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 271 
     
         
         
           
             Compounds of the formula I.b in which R 1 , R 4  and L′ are Cl, L 1  is —O—CH 2 CH 2 —OH and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 272 
     
         
         
           
             Compounds of the formula I.b in which R 1 , R 4  and L′ are Cl, L 1  is —O—CH 2 CH 2 —OCH 3  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 273 
     
         
         
           
             Compounds of the formula I.b in which R 1 , R 4  and L′ are Cl, L 1  is —O—CH 2 CH 2 —OC 2 H 5  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 274 
     
         
         
           
             Compounds of the formula I.b in which R 1 , R 4  and L′ are Cl, L 1  is —(O—CH 2 CH 2 ) 2 —OH and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 275 
     
         
         
           
             Compounds of the formula I.b in which R 1 , R 4  and L′ are Cl, L 1  is —(O—CH 2 CH 2 ) 2 —OCH 3  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 276 
     
         
         
           
             Compounds of the formula I.b in which R 1 , R 4  and L′ are Cl, L 1  is —(O—CH 2 CH 2 ) 2 —OC 2 H 5  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 277 
     
         
         
           
             Compounds of the formula I.b in which R 1 , R 4  and L′ are Cl, L 1  is —O—CH 2 CH 2 —NHCH 3  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 278 
     
         
         
           
             Compounds of the formula I.b in which R 1 , R 4  and L′ are Cl, L 1  is —O—CH 2 CH 2 —N(CH 3 ) 2  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 279 
     
         
         
           
             Compounds of the formula I.b in which R 1 , R 4  and L′ are Cl, L 1  is —O—CH 2 CH 2 —NHC 2 H 5  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 280 
     
         
         
           
             Compounds of the formula I.b in which R 1 , R 4  and L′ are Cl, L 1  is —O—CH 2 CH 2 —N(C 2 H 5 ) 2  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 281 
     
         
         
           
             Compounds of the formula I.b in which R 1 , R 4  and L′ are Cl, L 1  is —O—CH 2 CH 2 CH 2 —NHCH 3  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 282 
     
         
         
           
             Compounds of the formula I.b in which R 1 , R 4  and L′ are Cl, L 1  is —O—CH 2 CH 2 CH 2 —N(CH 3 ) 2  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 283 
     
         
         
           
             Compounds of the formula I.b in which R 1 , R 4  and L′ are Cl, L 1  is —O—CH 2 CH 2 CH 2 —NHC 2 H 5  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 284 
     
         
         
           
             Compounds of the formula I.b in which R 1 , R 4  and L′ are Cl, L 1  is —O—CH 2 CH 2 CH 2 —N(C 2 H 5 ) 2  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 285 
     
         
         
           
             Compounds of the formula I.b in which R 1 , R 4  and L′ are Cl, L 1  is —O—CH 2 CH 2 CH 2 CH 2 —NHCH 3  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 286 
     
         
         
           
             Compounds of the formula I.b in which R 1 , R 4  and L′ are Cl, L 1  is —O—CH 2 CH 2 CH 2 CH 2 —N(CH 3 ) 2  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 287 
     
         
         
           
             Compounds of the formula I.b in which R 1 , R 4  and L′ are Cl, L 1  is —O—CH 2 CH 2 CH 2 CH 2 —NHC 2 H 5  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 288 
     
         
         
           
             Compounds of the formula I.b in which R 1 , R 4  and L′ are Cl, L 1  is —O—CH 2 CH 2 CH 2 CH 2 —N(C 2 H 5 ) 2  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 289 
     
         
         
           
             Compounds of the formula I.b in which R 1  and R 4  are Cl, L′ is F, L 1  is —(OCH 2 ) 2 —OH and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 290 
     
         
         
           
             Compounds of the formula I.b in which R 1  and R 4  are Cl, L′ is F, L 1  is —(OCH 2 ) 2 —OCH 3  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 291 
     
         
         
           
             Compounds of the formula I.b in which R 1  and R 4  are Cl, L′ is F, L 1  is —(OCH 2 ) 2 —OC 2 H 5  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 292 
     
         
         
           
             Compounds of the formula I.b in which R 1  and R 4  are Cl, L′ is F, L 1  is —(OCH 2 ) 3 —OH and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 293 
     
         
         
           
             Compounds of the formula I.b in which R 1  and R 4  are Cl, L′ is F, L 1  is —(OCH 2 ) 3 —OCH 3  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 294 
     
         
         
           
             Compounds of the formula I.b in which R 1  and R 4  are Cl, L′ is F, L 1  is —(OCH 2 ) 3 —OC 2 H 5  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 295 
     
         
         
           
             Compounds of the formula I.b in which R 1  and R 4  are Cl, L′ is F, L 1  is —O—CH 2 CH 2 —OH and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 296 
     
         
         
           
             Compounds of the formula I.b in which R 1  and R 4  are Cl, L′ is F, L 1  is —O—CH 2 CH 2 —OCH 3  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 297 
     
         
         
           
             Compounds of the formula I.b in which R 1  and R 4  are Cl, L′ is F, L 1  is —O—CH 2 CH 2 —OC 2 H 5  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 298 
     
         
         
           
             Compounds of the formula I.b in which R 1  and R 4  are Cl, L′ is F, L 1  is —(O—CH 2 CH 2 ) 2 —OH and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 299 
     
         
         
           
             Compounds of the formula I.b in which R 1  and R 4  are Cl, L′ is F, L 1  is —(O—CH 2 CH 2 ) 2 —OCH 3  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 300 
     
         
         
           
             Compounds of the formula I.b in which R 1  and R 4  are Cl, L′ is F, L 1  is —(O—CH 2 CH 2 ) 2 —OC 2 H 5  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 301 
     
         
         
           
             Compounds of the formula I.b in which R 1  and R 4  are Cl, L′ is F, L 1  is —O—CH 2 CH 2 —NHCH 3  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 302 
     
         
         
           
             Compounds of the formula I.b in which R 1  and R 4  are Cl, L′ is F, L 1  is —O—CH 2 CH 2 —N(CH 3 ) 2  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 303 
     
         
         
           
             Compounds of the formula I.b in which R 1  and R 4  are Cl, L′ is F, L 1  is —O—CH 2 CH 2 —NHC 2 H 5  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 304 
     
         
         
           
             Compounds of the formula I.b in which R 1  and R 4  are Cl, L′ is F, L 1  is —O—CH 2 CH 2 —N(C 2 H 5 ) 2  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 305 
     
         
         
           
             Compounds of the formula I.b in which R 1  and R 4  are Cl, L′ is F, L 1  is —O—CH 2 CH 2 CH 2 —NHCH 3  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 306 
     
         
         
           
             Compounds of the formula I.b in which R 1  and R 4  are Cl, L′ is F, L 1  is —O—CH 2 CH 2 CH 2 —N(CH 3 ) 2  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 307 
     
         
         
           
             Compounds of the formula I.b in which R 1  and R 4  are Cl, L′ is F, L 1  is —O—CH 2 CH 2 CH 2 —NHC 2 H 5  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 308 
     
         
         
           
             Compounds of the formula I.b in which R 1  and R 4  are Cl, L′ is F, L 1  is —O—CH 2 CH 2 CH 2 —N(C 2 H 5 ) 2  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 309 
     
         
         
           
             Compounds of the formula I.b in which R 1  and R 4  are Cl, L′ is F, L 1  is —O—CH 2 CH 2 CH 2 CH 2 —NHCH 3  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 310 
     
         
         
           
             Compounds of the formula I.b in which R 1  and R 4  are Cl, L′ is F, L 1  is —O—CH 2 CH 2 CH 2 CH 2 —N(CH 3 ) 2  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 311 
     
         
         
           
             Compounds of the formula I.b in which R 1  and R 4  are Cl, L′ is F, L 1  is —O—CH 2 CH 2 CH 2 CH 2 —NHC 2 H 5  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 312 
     
         
         
           
             Compounds of the formula I.b in which R 1  and R 4  are Cl, L′ is F, L 1  is —O—CH 2 CH 2 CH 2 CH 2 —N(C 2 H 5 ) 2  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 313 
     
         
         
           
             Compounds of the formula I.b in which R 1  and R 4  are Cl, L′ is CH 3 , L 1  is —(OCH 2 ) 2 —OH and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 314 
     
         
         
           
             Compounds of the formula I.b in which R 1  and R 4  are Cl, L′ is CH 3 , L 1  is —(OCH 2 ) 2 —OCH 3  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 315 
     
         
         
           
             Compounds of the formula I.b in which R 1  and R 4  are Cl, L′ is CH 3 , L 1  is —(OCH 2 ) 2 —OC 2 H 5  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 316 
     
         
         
           
             Compounds of the formula I.b in which R 1  and R 4  are Cl, L′ is CH 3 , L 1  is —(OCH 2 ) 3 —OH and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 317 
     
         
         
           
             Compounds of the formula I.b in which R 1  and R 4  are Cl, L′ is CH 3 , L 1  is —(OCH 2 ) 3 —OCH 3  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 318 
     
         
         
           
             Compounds of the formula I.b in which R 1  and R 4  are Cl, L′ is CH 3 , L 1  is —(OCH 2 ) 3 —OC 2 H 5  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 319 
     
         
         
           
             Compounds of the formula I.b in which R 1  and R 4  are Cl, L′ is CH 3 , L 1  is —O—CH 2 CH 2 —OH and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 320 
     
         
         
           
             Compounds of the formula I.b in which R 1  and R 4  are Cl, L′ is CH 3 , L 1  is —O—CH 2 CH 2 —OCH 3  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 321 
     
         
         
           
             Compounds of the formula I.b in which R 1  and R 4  are Cl, L′ is CH 3 , L 1  is —O—CH 2 CH 2 —OC 2 H 5  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 322 
     
         
         
           
             Compounds of the formula I.b in which R 1  and R 4  are Cl, L′ is CH 3 , L 1  is —(O—CH 2 CH 2 ) 2 —OH and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 323 
     
         
         
           
             Compounds of the formula I.b in which R 1  and R 4  are Cl, L′ is CH 3 , L 1  is —(O—CH 2 CH 2 ) 2 —OCH 3  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 324 
     
         
         
           
             Compounds of the formula I.b in which R 1  and R 4  are Cl, L′ is CH 3 , L 1  is —(O—CH 2 CH 2 ) 2 —OC 2 H 5  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 325 
     
         
         
           
             Compounds of the formula I.b in which R 1  and R 4  are Cl, L′ is CH 3 , L 1  is —O—CH 2 CH 2 —NHCH 3  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 326 
     
         
         
           
             Compounds of the formula I.b in which R 1  and R 4  are Cl, L′ is CH 3 , L 1  is —O—CH 2 CH 2 —N(CH 3 ) 2  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 327 
     
         
         
           
             Compounds of the formula I.b in which R 1  and R 4  are Cl, L′ is CH 3 , L 1  is —O—CH 2 CH 2 —NHC 2 H 5  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 328 
     
         
         
           
             Compounds of the formula I.b in which R 1  and R 4  are Cl, L′ is CH 3 , L 1  is —O—CH 2 CH 2 —N(C 2 H 5 ) 2  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 329 
     
         
         
           
             Compounds of the formula I.b in which R 1  and R 4  are Cl, L′ is CH 3 , L 1  is —O—CH 2 CH 2 CH 2 —NHCH 3  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 330 
     
         
         
           
             Compounds of the formula I.b in which R 1  and R 4  are Cl, L′ is CH 3 , L 1  is —O—CH 2 CH 2 CH 2 —N(CH 3 ) 2  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 331 
     
         
         
           
             Compounds of the formula I.b in which R 1  and R 4  are Cl, L′ is CH 3 , L 1  is —O—CH 2 CH 2 CH 2 —NHC 2 H 5  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 332 
     
         
         
           
             Compounds of the formula I.b in which R 1  and R 4  are Cl, L′ is CH 3 , L 1  is —O—CH 2 CH 2 CH 2 —N(C 2 H 5 ) 2  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 333 
     
         
         
           
             Compounds of the formula I.b in which R 1  and R 4  are Cl, L′ is CH 3 , L 1  is —O—CH 2 CH 2 CH 2 CH 2 —NHCH 3  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 334 
     
         
         
           
             Compounds of the formula I.b in which R 1  and R 4  are Cl, L′ is CH 3 , L 1  is —O—CH 2 CH 2 CH 2 CH 2 —N(CH 3 ) 2  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 335 
     
         
         
           
             Compounds of the formula I.b in which R 1  and R 4  are Cl, L′ is CH 3 , L 1  is —O—CH 2 CH 2 CH 2 CH 2 —NHC 2 H 5  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     Table 336 
     
         
         
           
             Compounds of the formula I.b in which R 1  and R 4  are Cl, L′ is CH 3 , L 1  is —O—CH 2 CH 2 CH 2 CH 2 —N(C 2 H 5 ) 2  and R 2  for a compound corresponds in each case to one row of Table A 
           
         
       
    
     
       
         
           
               
               
               
             
               
                   
                 TABLE A 
               
               
                   
                   
               
               
                   
                 No. 
                 R 2   
               
               
                   
                   
               
             
            
               
                   
                 A-1 
                 CH 3   
               
               
                   
                 A-2 
                 CH 2 CH 3   
               
               
                   
                 A-3 
                 CH 2 CH 2 CH 3   
               
               
                   
                 A-4 
                 CH(CH 3 ) 2   
               
               
                   
                 A-5 
                 CH 2 CH(CH 3 ) 2   
               
               
                   
                 A-6 
                 (±) CH(CH 3 )CH 2 CH 3   
               
               
                   
                 A-7 
                 (S) CH(CH 3 )CH 2 CH 3   
               
               
                   
                 A-8 
                 (R) CH(CH 3 )CH 2 CH 3   
               
               
                   
                 A-9 
                 (CH 2 ) 3 CH 3   
               
               
                   
                 A-10 
                 C(CH 3 ) 3   
               
               
                   
                 A-11 
                 (CH 2 ) 4 CH 3   
               
               
                   
                 A-12 
                 CH(CH 2 CH 3 ) 2   
               
               
                   
                 A-13 
                 CH 2 CH 2 CH(CH 3 ) 2   
               
               
                   
                 A-14 
                 (±) CH(CH 3 )(CH 2 ) 2 CH 3   
               
               
                   
                 A-15 
                 (S) CH(CH 3 )(CH 2 ) 2 CH 3   
               
               
                   
                 A-16 
                 (R) CH(CH 3 )(CH 2 ) 2 CH 3   
               
               
                   
                 A-17 
                 (±) CH 2 CH(CH 3 )CH 2 CH 3   
               
               
                   
                 A-18 
                 (S) CH 2 CH(CH 3 )CH 2 CH 3   
               
               
                   
                 A-19 
                 (R) CH 2 CH(CH 3 )CH 2 CH 3   
               
               
                   
                 A-20 
                 (±) CH(CH 3 )CH(CH 3 ) 2   
               
               
                   
                 A-21 
                 (S) CH(CH 3 )CH(CH 3 ) 2   
               
               
                   
                 A-22 
                 (R) CH(CH 3 )CH(CH 3 ) 2   
               
               
                   
                 A-23 
                 (CH 2 ) 5 CH 3   
               
               
                   
                 A-24 
                 (±,±) CH(CH 3 )CH(CH 3 )CH 2 CH 3   
               
               
                   
                 A-25 
                 (±,S) CH(CH 3 )CH(CH 3 )CH 2 CH 3   
               
               
                   
                 A-26 
                 (±,R) CH(CH 3 )CH(CH 3 )CH 2 CH 3   
               
               
                   
                 A-27 
                 (±) CH 2 CH(CH 3 )CF 3   
               
               
                   
                 A-28 
                 (S) CH 2 CH(CH 3 )CF 3   
               
               
                   
                 A-29 
                 (R) CH 2 CH(CH 3 )CF 3   
               
               
                   
                 A-30 
                 (±) CH 2 CH(CF 3 )CH 2 CH 3   
               
               
                   
                 A-31 
                 (S) CH 2 CH(CF 3 )CH 2 CH 3   
               
               
                   
                 A-32 
                 (R) CH 2 CH(CF 3 )CH 2 CH 3   
               
               
                   
                 A-33 
                 (±,±) CH(CH 3 )CH(CH 3 )CF 3   
               
               
                   
                 A-34 
                 (±,S) CH(CH 3 )CH(CH 3 )CF 3   
               
               
                   
                 A-35 
                 (±,R) CH(CH 3 )CH(CH 3 )CF 3   
               
               
                   
                 A-36 
                 (±,±) CH(CH 3 )CH(CF 3 )CH 2 CH 3   
               
               
                   
                 A-37 
                 (±,R) CH(CH 3 )CH(CF 3 )CH 2 CH 3   
               
               
                   
                 A-38 
                 (±,S) CH(CH 3 )CH(CF 3 )CH 2 CH 3   
               
               
                   
                 A-39 
                 CF 3   
               
               
                   
                 A-40 
                 CF 2 CF 3   
               
               
                   
                 A-41 
                 CF 2 CF 2 CF 3   
               
               
                   
                 A-42 
                 cyclo-C 3 H 5   
               
               
                   
                 A-43 
                 (1-CH 3 )-cyclo-C 3 H 4   
               
               
                   
                 A-44 
                 cyclo-C 5 H 9   
               
               
                   
                 A-45 
                 cyclo-C 6 H 11   
               
               
                   
                 A-46 
                 (4-CH 3 )-cyclo-C 6 H 10   
               
               
                   
                 A-47 
                 CH 2 C(CH 3 )═CH 2   
               
               
                   
                 A-48 
                 CH 2 CH 2 C(CH 3 )═CH 2   
               
               
                   
                 A-49 
                 CH 2 C(CH 3 ) 3   
               
               
                   
                 A-50 
                 CH 2 Si(CH 3 ) 3   
               
               
                   
                 A-51 
                 n-C 6 H 13   
               
               
                   
                 A-52 
                 (CH 2 ) 3 CH(CH 3 ) 2   
               
               
                   
                 A-53 
                 (CH 2 ) 2 CH(CH 3 )C 2 H 5   
               
               
                   
                 A-54 
                 CH 2 CH(CH 3 )-n-C 3 H 7   
               
               
                   
                 A-55 
                 CH(CH 3 )-n-C 4 H 9   
               
               
                   
                 A-56 
                 CH 2 CH(C 2 H 5 ) 2   
               
               
                   
                 A-57 
                 CH(C 2 H 5 )-n-C 3 H 7   
               
               
                   
                 A-58 
                 CH 2 -cyclo-C 5 H 9   
               
               
                   
                 A-59 
                 CH 2 CH(CH 3 )CH(CH 3 ) 2   
               
               
                   
                 A-60 
                 CH(CH 3 )CH 2 CH(CH 3 ) 2   
               
               
                   
                 A-61 
                 CH(CH 3 )CH(CH 3 )C 2 H 5   
               
               
                   
                 A-62 
                 CH(CH 3 )C(CH 3 ) 3   
               
               
                   
                 A-63 
                 (CH 2 ) 2 C(CH 3 ) 3   
               
               
                   
                 A-64 
                 CH 2 —C(CH 3 ) 2 C 2 H 5   
               
               
                   
                 A-65 
                 2-CH 3 -cyclo-C 5 H 8   
               
               
                   
                 A-66 
                 3-CH 3 -cyclo-C 5 H 8   
               
               
                   
                 A-67 
                 C(CH 3 ) 2 -n-C 3 H 7   
               
               
                   
                 A-68 
                 (CH 2 ) 6 CH 3   
               
               
                   
                 A-69 
                 (CH 2 ) 4 CH(CH 3 ) 2   
               
               
                   
                 A-70 
                 (CH 2 ) 3 CH(CH 3 )C 2 H 5   
               
               
                   
                 A-71 
                 (CH 2 ) 2 CH(CH 3 )-n-C 3 H 7   
               
               
                   
                 A-72 
                 CH 2 CH(CH 3 )-n-C 4 H 9   
               
               
                   
                 A-73 
                 CH(CH 3 )-n-C 5 H 11   
               
               
                   
                 A-74 
                 (CH 2 ) 3 C(CH 3 ) 3   
               
               
                   
                 A-75 
                 (CH 2 ) 2 CH(CH 3 )CH(CH 3 ) 2   
               
               
                   
                 A-76 
                 (CH 2 )CH(CH 3 )CH 2 CH(CH 3 ) 2   
               
               
                   
                 A-77 
                 CH(CH 3 )(CH 2 ) 2 CH(CH 3 ) 2   
               
               
                   
                 A-78 
                 (CH 2 ) 2 C(CH 3 ) 2 C 2 H 5   
               
               
                   
                 A-79 
                 CH 2 CH(CH 3 )CH(CH 3 )C 2 H 5   
               
               
                   
                 A-80 
                 CH(CH 3 )CH 2 CH(CH 3 )C 2 H 5   
               
               
                   
                 A-81 
                 CH 2 C(CH 3 ) 2 -n-C 3 H 7   
               
               
                   
                 A-82 
                 CH(CH 3 )CH(CH 3 )-n-C 3 H 7   
               
               
                   
                 A-83 
                 C(CH 3 ) 2 -n-C 4 H 9   
               
               
                   
                 A-84 
                 (CH 2 ) 2 CH(C 2 H 5 ) 2   
               
               
                   
                 A-85 
                 CH 2 CH(C 2 H 5 )-n-C 3 H 7   
               
               
                   
                 A-86 
                 CH(C 2 H 5 )-n-C 4 H 9   
               
               
                   
                 A-87 
                 CH 2 CH(CH 3 )C(CH 3 ) 3   
               
               
                   
                 A-88 
                 CH(CH 3 )CH 2 C(CH 3 ) 3   
               
               
                   
                 A-89 
                 CH 2 C(CH 3 ) 2 CH(CH 3 ) 2   
               
               
                   
                 A-90 
                 CH 2 CH(C 2 H 5 )CH(CH 3 ) 2   
               
               
                   
                 A-91 
                 CH(CH 3 )CH(CH 3 )CH(CH 3 ) 2   
               
               
                   
                 A-92 
                 C(CH 3 ) 2 CH 2 CH(CH 3 ) 2   
               
               
                   
                 A-93 
                 CH(C 2 H 5 )CH 2 CH(CH 3 ) 2   
               
               
                   
                 A-94 
                 CH(CH 3 )C(CH 3 ) 2 C 2 H 5   
               
               
                   
                 A-95 
                 CH(CH 3 )CH(C 2 H 5 ) 2   
               
               
                   
                 A-96 
                 C(CH 3 ) 2 CH(CH 3 )C 2 H 5   
               
               
                   
                 A-97 
                 CH(C 2 H 5 )CH(CH 3 )C 2 H 5   
               
               
                   
                 A-98 
                 C(CH 3 )(C 2 H 5 )-n-C 3 H 7   
               
               
                   
                 A-99 
                 CH-(n-C 3 H 7 ) 2   
               
               
                   
                 A-100 
                 CH(n-C 3 H 7 )CH(CH 3 ) 2   
               
               
                   
                 A-101 
                 C(CH 3 ) 2 C(CH 3 ) 3   
               
               
                   
                 A-102 
                 C(CH 3 )(C 2 H 5 )CH(CH 3 ) 2   
               
               
                   
                 A-103 
                 C(C 2 H 5 ) 3   
               
               
                   
                 A-104 
                 (3-CH 3 )-cyclo-C 6 H 10   
               
               
                   
                 A-105 
                 (2-CH 3 )-cyclo-C 6 H 10   
               
               
                   
                 A-106 
                 n-C 8 H 17   
               
               
                   
                 A-107 
                 CH 2 C(═NO—CH 3 )CH 3   
               
               
                   
                 A-108 
                 CH 2 C(═NO—C 2 H 5 )CH 3   
               
               
                   
                 A-109 
                 CH 2 C(═NO-n-C 3 H 7 )CH 3   
               
               
                   
                 A-110 
                 CH 2 C(═NO-i-C 3 H 7 )CH 3   
               
               
                   
                 A-111 
                 CH(CH 3 )C(═NOCH 3 )CH 3   
               
               
                   
                 A-112 
                 CH(CH 3 )C(═NOC 2 H 5 )CH 3   
               
               
                   
                 A-113 
                 CH(CH 3 )C(═NO-n-C 3 H 7 )CH 3   
               
               
                   
                 A-114 
                 CH(CH 3 )C(═NO-i-C 3 H 7 )CH 3   
               
               
                   
                 A-115 
                 C(═NOCH 3 )C(═NOCH 3 )CH 3   
               
               
                   
                 A-116 
                 C(═NOCH 3 )C(═NOC 2 H 5 )CH 3   
               
               
                   
                 A-117 
                 C(═NOCH 3 )C(═NO-n-C 3 H 7 )CH 3   
               
               
                   
                 A-118 
                 C(═NOCH 3 )C(═NO-i-C 3 H 7 )CH 3   
               
               
                   
                 A-119 
                 C(═NOC 2 H 5 )C(═NOCH 3 )CH 3   
               
               
                   
                 A-120 
                 C(═NOC 2 H 5 )C(═NOC 2 H 5 )CH 3   
               
               
                   
                 A-121 
                 C(═NOC 2 H 5 )C(═NO-n-C 3 H 7 )CH 3   
               
               
                   
                 A-122 
                 C(═NOC 2 H 5 )C(═NO-i-C 3 H 7 )CH 3   
               
               
                   
                 A-123 
                 CH 2 C(═NO—CH 3 )C 2 H 5   
               
               
                   
                 A-124 
                 CH 2 C(═NO—C 2 H 5 )C 2 H 5   
               
               
                   
                 A-125 
                 CH 2 C(═NO-n-C 3 H 7 )C 2 H 5   
               
               
                   
                 A-126 
                 CH 2 C(═NO-i-C 3 H 7 )C 2 H 5   
               
               
                   
                 A-127 
                 CH(CH 3 )C(═NOCH 3 )C 2 H 5   
               
               
                   
                 A-128 
                 CH(CH 3 )C(═NOC 2 H 5 )C 2 H 5   
               
               
                   
                 A-129 
                 CH(CH 3 )C(═NO-n-C 3 H 7 )C 2 H 5   
               
               
                   
                 A-130 
                 CH(CH 3 )C(═NO-i-C 3 H 7 )C 2 H 5   
               
               
                   
                 A-131 
                 C(═NOCH 3 )C(═NOCH 3 )C 2 H 5   
               
               
                   
                 A-132 
                 C(═NOCH 3 )C(═NOC 2 H 5 )C 2 H 5   
               
               
                   
                 A-133 
                 C(═NOCH 3 )C(═NO-n-C 3 H 7 )C 2 H 5   
               
               
                   
                 A-134 
                 C(═NOCH 3 )C(═NO-i-C 3 H 7 )C 2 H 5   
               
               
                   
                 A-135 
                 C(═NOC 2 H 5 )C(═NOCH 3 )C 2 H 5   
               
               
                   
                 A-136 
                 C(═NOC 2 H 5 )C(═NOC 2 H 5 )C 2 H 5   
               
               
                   
                 A-137 
                 C(═NOC 2 H 5 )C(═NO-n-C 3 H 7 )C 2 H 5   
               
               
                   
                 A-138 
                 C(═NOC 2 H 5 )C(═NO-i-C 3 H 7 )C 2 H 5   
               
               
                   
                 A-139 
                 CH═CHCH 2 CH 3   
               
               
                   
                 A-140 
                 CH 2 CH═CHCH 3   
               
               
                   
                 A-141 
                 CH 2 CH 2 CH═CH 2   
               
               
                   
                 A-142 
                 C(CH 3 ) 2 CH 2 CH 3   
               
               
                   
                 A-143 
                 CH═C(CH 3 ) 2   
               
               
                   
                 A-144 
                 C(═CH 2 )CH 2 CH 3   
               
               
                   
                 A-145 
                 C(CH 3 )═CHCH 3   
               
               
                   
                 A-146 
                 CH(CH 3 )CH═CH 2   
               
               
                   
                 A-147 
                 CH═CH-n-C 3 H 7   
               
               
                   
                 A-148 
                 CH 2 —CH═CHC 2 H 5   
               
               
                   
                 A-149 
                 (CH 2 ) 2 CH═CH—CH 3   
               
               
                   
                 A-150 
                 (CH 2 ) 3 CH═CH 2   
               
               
                   
                 A-151 
                 CH═CHCH(CH 3 ) 2   
               
               
                   
                 A-152 
                 CH 2 CH═C(CH 3 ) 2   
               
               
                   
                 A-153 
                 (CH 2 ) 2 C(CH 3 )═CH 2   
               
               
                   
                 A-154 
                 CH═C(CH 3 )C 2 H 5   
               
               
                   
                 A-155 
                 (CH 2 )C(═CH 2 )C 2 H 5   
               
               
                   
                 A-156 
                 (CH 2 )C(CH 3 )═CHCH 3   
               
               
                   
                 A-157 
                 CH 2 CH(CH 3 )CH═CH 2   
               
               
                   
                 A-158 
                 C(═CH 2 )CH 2 (CH 2 )CH 3   
               
               
                   
                 A-159 
                 C(CH 3 )═CHCH 2 CH 3   
               
               
                   
                 A-160 
                 C(CH 3 )CH═CHCH 3   
               
               
                   
                 A-161 
                 C(CH 3 )CH 2 CH═CH 2   
               
               
                   
                 A-162 
                 C(═CH 2 )CH(CH 3 ) 2   
               
               
                   
                 A-163 
                 C(CH 3 )═C(CH 3 ) 2   
               
               
                   
                 A-164 
                 CH(CH 3 )C(═CH 2 )CH 3   
               
               
                   
                 A-165 
                 C(CH 3 ) 2 CH═CH 2   
               
               
                   
                 A-166 
                 C(C 2 H 5 )═CHCH 3   
               
               
                   
                 A-167 
                 C(C 2 H 5 )CH═CH 2   
               
               
                   
                 A-168 
                 CH═CHCH 2 CH 2 CH 2 CH 3   
               
               
                   
                 A-169 
                 CH 2 CH═CHCH 2 CH 2 CH 3   
               
               
                   
                 A-170 
                 CH 2 CH 2 CH═CHCH 2 CH 3   
               
               
                   
                 A-171 
                 CH 2 CH 2 CH 2 CH═CHCH 3   
               
               
                   
                 A-172 
                 CH 2 CH 2 CH 2 CH 2 CH═CH 2   
               
               
                   
                 A-173 
                 CH═CHCH 2 CH(CH 3 )CH 3   
               
               
                   
                 A-174 
                 CH 2 CH═CHCH(CH 3 )CH 3   
               
               
                   
                 A-175 
                 CH 2 CH 2 CH═C(CH 3 )CH 3   
               
               
                   
                 A-176 
                 CH 2 CH 2 CH 2 C(CH 3 )═CH 2   
               
               
                   
                 A-177 
                 CH═CHCH(CH 3 )CH 2 CH 3   
               
               
                   
                 A-178 
                 CH 2 CH═C(CH 3 )CH 2 CH 3   
               
               
                   
                 A-179 
                 CH 2 CH 2 C(═CH 2 )CH 2 CH 3   
               
               
                   
                 A-180 
                 CH 2 CH 2 C(CH 3 )═CHCH 3   
               
               
                   
                 A-181 
                 CH 2 CH 2 CH(CH 3 )CH═CH 2   
               
               
                   
                 A-182 
                 CH═C(CH 3 )CH 2 CH 2 CH 3   
               
               
                   
                 A-183 
                 CH 2 C(═CH 2 )CH 2 CH 2 CH 3   
               
               
                   
                 A-184 
                 CH 2 C(CH 3 )═CHCH 2 CH 3   
               
               
                   
                 A-185 
                 CH 2 CH(CH 3 )CH═CHCH 3   
               
               
                   
                 A-186 
                 CH 2 CH(CH 3 )CH 2 CH═CH 2   
               
               
                   
                 A-187 
                 C(═CH 2 )CH 2 CH 2 CH 2 CH 3   
               
               
                   
                 A-188 
                 C(CH 3 )═CH—CH 2 CH 2 CH 3   
               
               
                   
                 A-189 
                 CH(CH 3 )CH═CHCH 2 CH 3   
               
               
                   
                 A-190 
                 CH(CH 3 )CH 2 CH═CHCH 3   
               
               
                   
                 A-191 
                 CH(CH 3 )CH 2 CH 2 CH═CH 2   
               
               
                   
                 A-192 
                 CH═CHC(CH 3 ) 3   
               
               
                   
                 A-193 
                 CH═C(CH 3 )CH(CH 3 )CH 3   
               
               
                   
                 A-194 
                 CH 2 C(═CH 2 )CH(CH 3 )CH 3   
               
               
                   
                 A-195 
                 CH 2 C(CH 3 )═C(CH 3 )CH 3   
               
               
                   
                 A-196 
                 CH 2 CH(CH 3 )C(═CH 2 )CH 3   
               
               
                   
                 A-197 
                 C(═CH 2 )CH 2 CH(CH 3 )CH 3   
               
               
                   
                 A-198 
                 C(CH 3 )═CHCH(CH 3 )CH 3   
               
               
                   
                 A-199 
                 CH(CH 3 )CH═C(CH 3 )CH 3   
               
               
                   
                 A-200 
                 CH(CH 3 )CH 2 C(═CH 2 )CH 3   
               
               
                   
                 A-201 
                 CH═C(CH 2 CH 3 )CH 2 CH 3   
               
               
                   
                 A-202 
                 CH 2 C(═CHCH 3 )CH 2 CH 3   
               
               
                   
                 A-203 
                 CH 2 CH(CH═CH 2 )CH 2 CH 3   
               
               
                   
                 A-204 
                 C(═CH—CH 3 )—CH 2 CH 2 CH 3   
               
               
                   
                 A-205 
                 CH(CH═CH 2 )CH 2 CH 2 CH 3   
               
               
                   
                 A-206 
                 C(CH 2 CH 3 )═CHCH 2 CH 3   
               
               
                   
                 A-207 
                 CH(CH 2 CH 3 )CH═CHCH 3   
               
               
                   
                 A-208 
                 CH(CH 2 CH 3 )CH 2 CH═CH 2   
               
               
                   
                 A-209 
                 CH 2 C(CH 3 ) 2 CH═CH 2   
               
               
                   
                 A-210 
                 C(═CH 2 )CH(CH 3 )CH 2 CH 3   
               
               
                   
                 A-211 
                 C(CH 3 )═C(CH 3 )CH 2 CH 3   
               
               
                   
                 A-212 
                 CH(CH 3 )C(═CH 2 )CH 2 CH 3   
               
               
                   
                 A-213 
                 CH(CH 3 )C(CH 3 )═CHCH 3   
               
               
                   
                 A-214 
                 CH(CH 3 )CH(CH 3 )CH═CH 2   
               
               
                   
                 A-215 
                 C(CH 3 ) 2 CH═CHCH 3   
               
               
                   
                 A-216 
                 C(CH 3 ) 2 CH 2 CH═CH 2   
               
               
                   
                 A-217 
                 C(═CH 2 )C(CH 3 ) 3   
               
               
                   
                 A-218 
                 C(═CHCH 3 )CH(CH 3 )CH 3   
               
               
                   
                 A-219 
                 CH(CH═CH 2 )CH(CH 3 )CH 3   
               
               
                   
                 A-220 
                 C(CH 2 CH 3 )═C(CH 3 )CH 3   
               
               
                   
                 A-221 
                 CH(CH 2 CH 3 )C(═CH 2 )CH 3   
               
               
                   
                 A-222 
                 C(CH 3 ) 2 C(═CH 2 )CH 3   
               
               
                   
                 A-223 
                 C(CH 3 )(CH═CH 2 )CH 2 CH 3   
               
               
                   
                 A-224 
                 C(CH 3 )(CH 2 CH 3 )CH 2 CH 2 CH 3   
               
               
                   
                 A-225 
                 CH(CH 2 CH 3 )CH(CH 3 )CH 2 CH 3   
               
               
                   
                 A-226 
                 CH(CH 2 CH 3 )CH 2 CH(CH 3 )CH 3   
               
               
                   
                 A-227 
                 C(CH 3 ) 2 C(CH 3 ) 3   
               
               
                   
                 A-228 
                 C(CH 2 CH 3 ) 2 C(CH 3 ) 3   
               
               
                   
                 A-229 
                 C(CH 2 CH 3 )(CH 3 )CH(CH 3 ) 2   
               
               
                   
                 A-230 
                 CH(CH(CH 3 ) 2 )CH(CH 3 ) 2   
               
               
                   
                 A-231 
                 CH═CHCH 2 CH 2 CH 2 CH 2 CH 3   
               
               
                   
                 A-232 
                 CH 2 CH═CHCH 2 CH 2 CH 2 CH 3   
               
               
                   
                 A-233 
                 CH 2 CH 2 CH═CHCH 2 CH 2 CH 3   
               
               
                   
                 A-234 
                 CH 2 CH 2 CH 2 CH═CHCH 2 CH 3   
               
               
                   
                 A-235 
                 CH 2 CH 2 CH 2 CH 2 CH═CH—CH 3   
               
               
                   
                 A-236 
                 CH 2 CH 2 CH 2 CH 2 CH 2 CH═CH 2   
               
               
                   
                 A-237 
                 CH═CHCH 2 CH 2 CH(CH 3 )CH 3   
               
               
                   
                 A-238 
                 CH 2 CH═CHCH 2 CH(CH 3 )CH 3   
               
               
                   
                 A-239 
                 CH 2 CH 2 CH═CHCH(CH 3 )CH 3   
               
               
                   
                 A-240 
                 CH 2 CH 2 CH 2 CH═C(CH 3 )CH 3   
               
               
                   
                 A-241 
                 CH 2 CH 2 CH 2 CH 2 C(═CH 2 )CH 3   
               
               
                   
                 A-242 
                 CH═CHCH 2 CH(CH 3 )CH 2 CH 3   
               
               
                   
                 A-243 
                 CH 2 CH═CHCH(CH 3 )CH 2 CH 3   
               
               
                   
                 A-244 
                 CH 2 CH 2 CH═C(CH 3 )CH 2 CH 3   
               
               
                   
                 A-245 
                 CH 2 CH 2 CH 2 C(═CH 2 )CH 2 CH 3   
               
               
                   
                 A-246 
                 CH 2 CH 2 CH 2 C(CH 3 )═CHCH 3   
               
               
                   
                 A-247 
                 CH 2 CH 2 CH 2 CH(CH 3 )CH═CH 2   
               
               
                   
                 A-248 
                 CH═CHCH(CH 3 )CH 2 CH 2 CH 3   
               
               
                   
                 A-249 
                 CH 2 CH═C(CH 3 )CH 2 CH 2 CH 3   
               
               
                   
                 A-250 
                 CH 2 CH 2 C(═CH 2 )CH 2 CH 2 CH 3   
               
               
                   
                 A-251 
                 CH 2 CH 2 C(CH 3 )═CHCH 2 CH 3   
               
               
                   
                 A-252 
                 CH 2 CH 2 CH(CH 3 )CH═CHCH 3   
               
               
                   
                 A-253 
                 CH 2 CH 2 CH(CH 3 )CH 2 CH═CH 2   
               
               
                   
                 A-254 
                 CH═C(CH 3 )CH 2 CH 2 CH 2 CH 3   
               
               
                   
                 A-255 
                 CH 2 C(═CH 2 )CH 2 CH 2 CH 2 CH 3   
               
               
                   
                 A-256 
                 CH 2 C(CH 3 )═CHCH 2 CH 2 CH 3   
               
               
                   
                 A-257 
                 CH 2 CH(CH 3 )CH═CHCH 2 CH 3   
               
               
                   
                 A-258 
                 CH 2 CH(CH 3 )CH 2 CH═CHCH 3   
               
               
                   
                 A-259 
                 CH 2 CH(CH 3 )CH 2 CH 2 CH═CH 2   
               
               
                   
                 A-260 
                 C(═CH 2 )CH 2 CH 2 CH 2 CH 2 CH 3   
               
               
                   
                 A-261 
                 C(CH 3 )═CHCH 2 CH 2 CH 2 CH 3   
               
               
                   
                 A-262 
                 CH(CH 3 )CH═CHCH 2 CH 2 CH 3   
               
               
                   
                 A-263 
                 CH(CH 3 )CH 2 CH═CHCH 2 CH 3   
               
               
                   
                 A-264 
                 CH(CH 3 )CH 2 CH 2 CH═CHCH 3   
               
               
                   
                 A-265 
                 CH(CH 3 )CH 2 CH 2 CH 2 CH═CH 2   
               
               
                   
                 A-266 
                 CH═CHCH 2 C(CH 3 ) 3   
               
               
                   
                 A-267 
                 CH 2 CH═CHC(CH 3 ) 3   
               
               
                   
                 A-268 
                 CH═CHCH(CH 3 )CH(CH 3 ) 2   
               
               
                   
                 A-269 
                 CH 2 CH═C(CH 3 )CH(CH 3 ) 2   
               
               
                   
                 A-270 
                 CH 2 CH 2 C(═CH 2 )CH(CH 3 ) 2   
               
               
                   
                 A-271 
                 CH 2 CH 2 C(CH 3 )═C(CH 3 ) 2   
               
               
                   
                 A-272 
                 CH 2 CH 2 CH(CH 3 )C(═CH 2 )(CH 3 ) 
               
               
                   
                 A-273 
                 CH═C(CH 3 )CH 2 CH(CH 3 ) 2   
               
               
                   
                 A-274 
                 CH 2 C(═CH 2 )CH 2 CH(CH 3 ) 2   
               
               
                   
                 A-275 
                 CH 2 C(CH 3 )═CHCH(CH 3 ) 2   
               
               
                   
                 A-276 
                 CH 2 CH(CH 3 )CH═C(CH 3 ) 2   
               
               
                   
                 A-277 
                 CH 2 CH(CH 3 )CH 2 C(═CH 2 )CH 3   
               
               
                   
                 A-278 
                 C(═CH 2 )CH 2 CH 2 CH(CH 3 ) 2   
               
               
                   
                 A-279 
                 C(CH 3 )═CHCH 2 CH(CH 3 ) 2   
               
               
                   
                 A-280 
                 CH(CH 3 )CH═CHCH(CH 3 ) 2   
               
               
                   
                 A-281 
                 CH(CH 3 )CH 2 CH═C(CH 3 ) 2   
               
               
                   
                 A-282 
                 CH(CH 3 )CH 2 CH 2 C(═CH 2 )CH 3   
               
               
                   
                 A-283 
                 CH═CHC(CH 3 ) 2 CH 2 CH 3   
               
               
                   
                 A-284 
                 CH 2 CH 2 C(CH 3 ) 2 CH═CH 2   
               
               
                   
                 A-285 
                 CH═C(CH 3 )CH(CH 3 )CH 2 CH 3   
               
               
                   
                 A-286 
                 CH 2 C(═CH 2 )CH(CH 3 )CH 2 CH 3   
               
               
                   
                 A-287 
                 CH 2 C(CH 3 )═C(CH 3 )CH 2 CH 3   
               
               
                   
                 A-288 
                 CH 2 CH(CH 3 )C(═CH 2 )CH 2 CH 3   
               
               
                   
                 A-289 
                 CH 2 CH(CH 3 )C(CH 3 )═CHCH 3   
               
               
                   
                 A-290 
                 CH 2 CH(CH 3 )CH(CH 3 )CH═CH 2   
               
               
                   
                 A-291 
                 C(═CH 2 )CH 2 CH(CH 3 )CH 2 CH 3   
               
               
                   
                 A-292 
                 C(CH 3 )═CHCH(CH 3 )CH 2 CH 3   
               
               
                   
                 A-293 
                 CH(CH 3 )CH═C(CH 3 )CH 2 CH 3   
               
               
                   
                 A-294 
                 CH(CH 3 )CH 2 C(═CH 2 )CH 2 CH 3   
               
               
                   
                 A-295 
                 CH(CH 3 )CH 2 C(CH 3 )═CHCH 3   
               
               
                   
                 A-296 
                 CH(CH 3 )CH 2 CH(CH 3 )CH═CH 2   
               
               
                   
                 A-297 
                 CH 2 C(CH 3 ) 2 CH═CHCH 3   
               
               
                   
                 A-298 
                 CH 2 C(CH 3 ) 2 CH 2 CH═CH 2   
               
               
                   
                 A-299 
                 C(═CH 2 )CH(CH 3 )CH 2 CH 2 CH 3   
               
               
                   
                 A-300 
                 C(CH 3 )═C(CH 3 )CH 2 CH 2 CH 3   
               
               
                   
                 A-301 
                 CH(CH 3 )C(═CH 2 )CH 2 CH 2 CH 3   
               
               
                   
                 A-302 
                 CH(CH 3 )C(CH 3 )═CHCH 2 CH 3   
               
               
                   
                 A-303 
                 CH(CH 3 )CH(CH 3 )CH═CHCH 3   
               
               
                   
                 A-304 
                 CH(CH 3 )CH(CH 3 )CH 2 CH═CH 2   
               
               
                   
                 A-305 
                 C(CH 3 ) 2 CH═CHCH 2 CH 3   
               
               
                   
                 A-306 
                 C(CH 3 ) 2 CH 2 CH═CHCH 3   
               
               
                   
                 A-307 
                 C(CH 3 ) 2 CH 2 CH 2 CH═CH 2   
               
               
                   
                 A-308 
                 CH═CHCH(CH 2 CH 3 )CH 2 CH 3   
               
               
                   
                 A-309 
                 CH 2 CH═C(CH 2 CH 3 )CH 2 CH 3   
               
               
                   
                 A-310 
                 CH 2 CH 2 C(═CHCH 3 )CH 2 CH 3   
               
               
                   
                 A-311 
                 CH 2 CH 2 CH(CH═CH 2 )CH 2 CH 3   
               
               
                   
                 A-312 
                 CH═C(CH 2 CH 3 )CH 2 CH 2 CH 3   
               
               
                   
                 A-313 
                 CH 2 C(═CHCH 3 )CH 2 CH 2 CH 3   
               
               
                   
                 A-314 
                 CH 2 CH(CH═CH 2 )CH 2 CH 2 CH 3   
               
               
                   
                 A-315 
                 CH 2 C(CH 2 CH 3 )═CHCH 2 CH 3   
               
               
                   
                 A-316 
                 CH 2 CH(CH 2 CH 3 )CH═CHCH 3   
               
               
                   
                 A-317 
                 CH 2 CH(CH 2 CH 3 )CHCH═CH 2   
               
               
                   
                 A-318 
                 C(═CHCH 3 )CH 2 CH 2 CH 2 CH 3   
               
               
                   
                 A-319 
                 CH(CH═CH 2 )CH 2 CH 2 CH 2 CH 3   
               
               
                   
                 A-320 
                 C(CH 2 CH 3 )═CHCH 2 CH 2 CH 3   
               
               
                   
                 A-321 
                 CH(CH 2 CH 3 )CH═CHCH 2 CH 3   
               
               
                   
                 A-322 
                 CH(CH 2 CH 3 )CH 2 CH═CHCH 3   
               
               
                   
                 A-323 
                 CH(CH 2 CH 3 )CH 2 CH 2 CH═CH 2   
               
               
                   
                 A-324 
                 C(═CHCH 2 CH 3 )CH 2 CH 2 CH 3   
               
               
                   
                 A-325 
                 CH(CH═CHCH 3 )CH 2 CH 2 CH 3   
               
               
                   
                 A-326 
                 CH(CH 2 CH═CH 2 )CH 2 CH 2 CH 3   
               
               
                   
                 A-327 
                 CH═C(CH 3 )C(CH 3 ) 3   
               
               
                   
                 A-328 
                 CH 2 C(═CH 2 )C(CH 3 ) 3   
               
               
                   
                 A-329 
                 CH 2 C(CH 3 ) 2 CH(═CH 2 )CH 3   
               
               
                   
                 A-330 
                 C(═CH 2 )CH(CH 3 )CH(CH 3 )CH 3   
               
               
                   
                 A-331 
                 C(CH 3 )═C(CH 3 )CH(CH 3 )CH 3   
               
               
                   
                 A-332 
                 CH(CH 3 )C(═CH 2 )CH(CH 3 )CH 3   
               
               
                   
                 A-333 
                 CH(CH 3 )C(CH 3 )═C(CH 3 )CH 3   
               
               
                   
                 A-334 
                 CH(CH 3 )CH(CH 3 )C(═CH 2 )CH 3   
               
               
                   
                 A-335 
                 C(CH 3 ) 2 CH═C(CH 3 )CH 3   
               
               
                   
                 A-336 
                 C(CH 3 ) 2 CH 2 C(═CH 2 )CH 3   
               
               
                   
                 A-337 
                 C(CH 3 ) 2 C(═CH 2 )CH 2 CH 3   
               
               
                   
                 A-338 
                 C(CH 3 ) 2 C(CH 3 )═CHCH 3   
               
               
                   
                 A-339 
                 C(CH 3 ) 2 CH(CH 3 )CH═CH 2   
               
               
                   
                 A-340 
                 CH(CH 2 CH 3 )CH 2 CH(CH 3 )CH 3   
               
               
                   
                 A-341 
                 CH(CH 2 CH 3 )CH(CH 3 )CH 2 CH 3   
               
               
                   
                 A-342 
                 C(CH 3 )(CH 2 CH 3 )CH 2 CH 2 CH 3   
               
               
                   
                 A-343 
                 CH(i-C 3 H 7 )CH 2 CH 2 CH 3   
               
               
                   
                 A-344 
                 CH═C(CH 2 CH 3 )CH(CH 3 )CH 3   
               
               
                   
                 A-345 
                 CH 2 C(═CHCH 3 )CH(CH 3 )CH 3   
               
               
                   
                 A-346 
                 CH 2 CH(CH═CH 2 )CH(CH 3 )CH 3   
               
               
                   
                 A-347 
                 CH 2 C(CH 2 CH 3 )═C(CH 3 )CH 3   
               
               
                   
                 A-348 
                 CH 2 CH(CH 2 CH 3 )C(═CH 2 )CH 3   
               
               
                   
                 A-349 
                 CH 2 C(CH 3 )(CH═CH 2 )CH 2 CH 3   
               
               
                   
                 A-350 
                 C(═CH 2 )CH(CH 2 CH 3 )CH 2 CH 3   
               
               
                   
                 A-351 
                 C(CH 3 )═C(CH 2 CH 3 )CH 2 CH 3   
               
               
                   
                 A-352 
                 CH(CH 3 )C(═CHCH 3 )CH 2 CH 3   
               
               
                   
                 A-353 
                 CH(CH 3 )CH(CH═CH 2 )CH 2 CH 3   
               
               
                   
                 A-354 
                 CH═C(CH 2 CH 3 )CH(CH 3 )CH 3   
               
               
                   
                 A-355 
                 CH 2 C(═CHCH 3 )CH(CH 3 )CH 3   
               
               
                   
                 A-356 
                 CH 2 CH(CH═CH 2 )CH(CH 3 )CH 3   
               
               
                   
                 A-357 
                 CH 2 C(CH 2 CH 3 )═(CH 3 )CH 3   
               
               
                   
                 A-358 
                 CH 2 CH(CH 2 CH 3 )C(═CH 2 )CH 3   
               
               
                   
                 A-359 
                 C(═CHCH 3 )CH 2 CH(CH 3 )CH 3   
               
               
                   
                 A-360 
                 CH(CH═CH 2 )CH 2 CH(CH 3 )CH 3   
               
               
                   
                 A-361 
                 C(CH 2 CH 3 )═CHCH(CH 3 )CH 3   
               
               
                   
                 A-362 
                 CH(CH 2 CH 3 )CH═C(CH 3 )CH 3   
               
               
                   
                 A-363 
                 CH(CH 2 CH 3 )CH 2 C(═CH 2 )CH 3   
               
               
                   
                 A-364 
                 C(═CHCH 3 )CH(CH 3 )CH 2 CH 3   
               
               
                   
                 A-365 
                 CH(CH═CH 2 )CH(CH 3 )CH 2 CH 3   
               
               
                   
                 A-366 
                 C(CH 2 CH 3 )═C(CH 3 )CH 2 CH 3   
               
               
                   
                 A-367 
                 CH(CH 2 CH 3 )C(═CH 2 )CH 2 CH 3   
               
               
                   
                 A-368 
                 CH(CH 2 CH 3 )C(CH 3 )═CHCH 3   
               
               
                   
                 A-369 
                 CH(CH 2 CH 3 )CH(CH 3 )CH═CH 2   
               
               
                   
                 A-370 
                 C(CH 3 )(CH═CH 2 )CH 2 CH 2 CH 3   
               
               
                   
                 A-371 
                 C(CH 3 )(CH 2 CH 3 )CH═CHCH 3   
               
               
                   
                 A-372 
                 C(CH 3 )(CH 2 CH 3 )CH 2 CH═CH 2   
               
               
                   
                 A-373 
                 C[═C(CH 3 )CH 3 ]CH 2 CH 2 CH 3   
               
               
                   
                 A-374 
                 CH[C(═CH 2 )CH 3 ]CH 2 CH 2 CH 3   
               
               
                   
                 A-375 
                 C(i-C 3 H 7 )═CHCH 2 CH 3   
               
               
                   
                 A-376 
                 CH(i-C 3 H 7 )CH═CHCH 3   
               
               
                   
                 A-377 
                 CH(i-C 3 H 7 )CH 2 CH═CH 2   
               
               
                   
                 A-378 
                 C(═CHCH 3 )C(CH 3 ) 3   
               
               
                   
                 A-379 
                 CH(CH═CH 2 )C(CH 3 ) 3   
               
               
                   
                 A-380 
                 C(CH 3 )(CH═CH 2 )CH(CH 3 )CH 3   
               
               
                   
                 A-381 
                 C(CH 3 )(CH 2 CH 3 )C(═CH 2 )CH 3   
               
               
                   
                 A-382 
                 2-CH 3 -cyclohex-1-enyl 
               
               
                   
                 A-383 
                 [2-(═CH 2 )]-cyclo-C 6 H 9   
               
               
                   
                 A-384 
                 2-CH 3 -cyclohex-2-enyl 
               
               
                   
                 A-385 
                 2-CH 3 -cyclohex-3-enyl 
               
               
                   
                 A-386 
                 2-CH 3 -cyclohex-4-enyl 
               
               
                   
                 A-387 
                 2-CH 3 -cyclohex-5-enyl 
               
               
                   
                 A-388 
                 2-CH 3 -cyclohex-6-enyl 
               
               
                   
                 A-389 
                 3-CH 3 -cyclohex-1-enyl 
               
               
                   
                 A-390 
                 3-CH 3 -cyclohex-2-enyl 
               
               
                   
                 A-391 
                 [3-(═CH 2 )]-cyclo-C 6 H 9   
               
               
                   
                 A-392 
                 3-CH 3 -cyclohex-3-enyl 
               
               
                   
                 A-393 
                 3-CH 3 -cyclohex-4-enyl 
               
               
                   
                 A-394 
                 3-CH 3 -cyclohex-5-enyl 
               
               
                   
                 A-395 
                 3-CH 3 -cyclohex-6-enyl 
               
               
                   
                 A-396 
                 4-CH 3 -cyclohex-1-enyl 
               
               
                   
                 A-397 
                 4-CH 3 -cyclohex-2-enyl 
               
               
                   
                 A-398 
                 4-CH 3 -cyclohex-3-enyl 
               
               
                   
                 A-399 
                 [4-(═CH 2 )]-cyclo-C 6 H 9   
               
               
                   
                 A-400 
                 C 6 H 5   
               
               
                   
                 A-401 
                 4-CH 3 —C 6 H 4   
               
               
                   
                 A-402 
                 3-CH 3 —C 6 H 4   
               
               
                   
                 A-403 
                 2-CH 3 —C 6 H 4   
               
               
                   
                 A-404 
                 4-C 2 H 5 —C 6 H 4   
               
               
                   
                 A-405 
                 4-(CH 2 ) 2 CH 3 —C 6 H 4   
               
               
                   
                 A-406 
                 4-CH(CH 3 ) 2 —C 6 H 4   
               
               
                   
                 A-407 
                 4-(CH 2 ) 3 CH 3 —C 6 H 4   
               
               
                   
                 A-408 
                 4-CH(CH 3 )C 2 H 5 —C 6 H 4   
               
               
                   
                 A-409 
                 4-CH 2 CH(CH 3 ) 2 —C 6 H 4   
               
               
                   
                 A-410 
                 4-C(CH 3 ) 3 —C 6 H 4   
               
               
                   
                 A-411 
                 2,3-(CH 3 ) 2 —C 6 H 3   
               
               
                   
                 A-412 
                 2,4-(CH 3 ) 2 —C 6 H 3   
               
               
                   
                 A-413 
                 2,5-(CH 3 ) 2 —C 6 H 3   
               
               
                   
                 A-414 
                 3,4-(CH 3 ) 2 —C 6 H 3   
               
               
                   
                 A-415 
                 3,5-(CH 3 ) 2 —C 6 H 3   
               
               
                   
                 A-416 
                 4-C 6 H 5 —C 6 H 4   
               
               
                   
                 A-417 
                 3-C 6 H 5 —C 6 H 4   
               
               
                   
                 A-418 
                 4-Cl—C 6 H 4   
               
               
                   
                 A-419 
                 3-Cl—C 6 H 4   
               
               
                   
                 A-420 
                 2-Cl—C 6 H 4   
               
               
                   
                 A-421 
                 4-F—C 6 H 4   
               
               
                   
                 A-422 
                 3-F—C 6 H 4   
               
               
                   
                 A-423 
                 2-F—C 6 H 4   
               
               
                   
                 A-424 
                 2,3-Cl 2 —C 6 H 3   
               
               
                   
                 A-425 
                 2,4-Cl 2 —C 6 H 3   
               
               
                   
                 A-426 
                 2,5-Cl 2 —C 6 H 3   
               
               
                   
                 A-427 
                 3,4-Cl 2 —C 6 H 3   
               
               
                   
                 A-428 
                 3,5-Cl 2 —C 6 H 3   
               
               
                   
                 A-429 
                 2,3-F 2 —C 6 H 3   
               
               
                   
                 A-430 
                 2,4-F 2 —C 6 H 3   
               
               
                   
                 A-431 
                 2,5-F 2 —C 6 H 3   
               
               
                   
                 A-432 
                 3,4-F 2 —C 6 H 3   
               
               
                   
                 A-433 
                 3,5-F 2 —C 6 H 3   
               
               
                   
                 A-434 
                 2-Cl,4-F—C 6 H 3   
               
               
                   
                 A-435 
                 4-CF 3 —C 6 H 4   
               
               
                   
                 A-436 
                 3-CF 3 —C 6 H 4   
               
               
                   
                 A-437 
                 2-CF 3 —C 6 H 4   
               
               
                   
                 A-438 
                 3,5-(CF 3 ) 2 —C 6 H 3   
               
               
                   
                 A-439 
                 4-OCH 3 —C 6 H 4   
               
               
                   
                 A-440 
                 3-OCH 3 —C 6 H 4   
               
               
                   
                 A-441 
                 2-OCH 3 —C 6 H 4   
               
               
                   
                 A-442 
                 2,3-(OCH 3 ) 2 —C 6 H 3   
               
               
                   
                 A-443 
                 2,4-(OCH 3 ) 2 —C 6 H 3   
               
               
                   
                 A-444 
                 2,5-(OCH 3 ) 2 —C 6 H 3   
               
               
                   
                 A-445 
                 3,4-(OCH 3 )—C 6 H 3   
               
               
                   
                 A-446 
                 3,5-(OCH 3 ) 2 —C 6 H 3   
               
               
                   
                 A-447 
                 2,3,4-(OCH 3 ) 3 —C 6 H 2   
               
               
                   
                 A-448 
                 3,4,5-(OCH 3 ) 3 —C 6 H 2   
               
               
                   
                 A-449 
                 4-OC 2 H 5 —C 6 H 4   
               
               
                   
                 A-450 
                 3-OC 2 H 5 —C 6 H 4   
               
               
                   
                 A-451 
                 2-OC 2 H 5 —C 6 H 4   
               
               
                   
                 A-452 
                 4-SCH 3 —C 6 H 4   
               
               
                   
                 A-453 
                 3-SCH 3 —C 6 H 4   
               
               
                   
                 A-454 
                 2-SCH 3 —C 6 H 4   
               
               
                   
                 A-455 
                 4-SC 2 H 5 —C 6 H 4   
               
               
                   
                 A-456 
                 4-OCF 3 —C 6 H 4   
               
               
                   
                 A-457 
                 3-OCF 3 —C 6 H 4   
               
               
                   
                 A-458 
                 2-OCF 3 —C 6 H 4   
               
               
                   
                 A-459 
                 4-CN—C 6 H 4   
               
               
                   
                 A-460 
                 3-CN—C 6 H 4   
               
               
                   
                 A-461 
                 2-CN—C 6 H 4   
               
               
                   
                 A-462 
                 4-CHO—C 6 H 4   
               
               
                   
                 A-463 
                 3-CHO—C 6 H 4   
               
               
                   
                 A-464 
                 2-CHO—C 6 H 4   
               
               
                   
                 A-465 
                 4-COCH 3 —C 6 H 4   
               
               
                   
                 A-466 
                 3-COCH 3 —C 6 H 4   
               
               
                   
                 A-467 
                 2-COCH 3 —C 6 H 4   
               
               
                   
                 A-468 
                 4-COOCH 3 —C 6 H 4   
               
               
                   
                 A-469 
                 4-COOC 2 H 5 —C 6 H 4   
               
               
                   
                 A-470 
                 4-COOCH(CH 3 ) 2 —C 6 H 4   
               
               
                   
                 A-471 
                 4-CH 3 ,4-F—C 6 H 3   
               
               
                   
                 A-472 
                 4-OH—C 6 H 4   
               
               
                   
                 A-473 
                 3-OH—C 6 H 4   
               
               
                   
                 A-474 
                 2-OH—C 6 H 4   
               
               
                   
                 A-475 
                 pyridin-2-yl 
               
               
                   
                 A-476 
                 pyridin-3-yl 
               
               
                   
                 A-477 
                 pyridin-4-yl 
               
               
                   
                   
               
            
           
         
       
     
     In addition to the compounds individually listed in Tables 1 to 336, the invention also provides the corresponding derivatives in which R 1  and R 4  are cyano. 
     In addition to the compounds individually listed in Tables 1 to 336, the invention also provides the corresponding derivatives in which R 1  and R 4  are methoxy. 
     In addition to the compounds individually listed in Tables 1 to 336, the invention also provides the corresponding derivatives in which R 1  and R 4  are methyl. 
     The compounds I are suitable as fungicides. They are distinguished by an excellent activity against a broad spectrum of phytopathogenic fungi from the class of the Ascomycetes, Deuteromycetes, Basidiomycetes and Peronosporomycetes (syn. Oomycetes). Some of them are systemically effective and can be used in crop protection as foliar fungicides, as fungicides for seed dressing and as soil fungicides. 
     They are particularly important in the control of a multitude of fungi on various cultivated plants, such as wheat, rye, barley, oats, rice, corn, grass, bananas, cotton, soybeans, coffee, sugar cane, vines, fruit and ornamental plants, and vegetables, such as cucumbers, beans, tomatoes, potatoes and cucurbits, and on the seeds of these plants. They may also be used in crops which are tolerant to attack by insects or fungi owing to breeding, including genetic engineering methods. Furthermore, they are suitable for controlling  Botryosphaeria  species,  Cylindrocarpon  species,  Eutypa lata, Neonectria lifiodendri  and  Stereum hirsutum , which inter alia attack the wood or the roots of grapevines. 
     They are especially suitable for controlling the following plant diseases: 
       Alternaria  species on vegetables, oilseed rape, sugar beet, fruit, rice, soybeans, and also on potatoes (for example  A. solani  or  A. alternata ) and tomatoes (for example  A. solani  or  A. alternata ) and  Alternaria  ssp. (black point) on wheat, 
       Aphanomyces  species on sugar beet and vegetables, 
       Ascochyta  species on cereals and vegetables, for example  Ascochyta tritici  (leaf spot) on wheat, 
       Bipolaris  and  Drechslera  species on corn (for example  D. maydis ), cereals, rice and lawn, 
       Blumeria graminis  (powdery mildew) on cereals (for example wheat or barley), 
       Botrytis cinerea  (gray mold) on strawberries, vegetables, flowers, grapevines and wheat (ear mold), 
       Bremia lactucae  on lettuce, 
       Cercospora  species on corn, rice, sugar beet and, for example,  Cercospora sojina  (leaf blotch) or  Cercospora kikuchii  (leaf blotch) on soybeans, 
       Cladosporium herbarum  (black mold) on wheat, 
       Cochliobolus  species on corn, cereals (for example  Cochliobolus sativus ) and rice (for example  Cochliobolus miyabeanus ), 
       Colletotricum  species on cotton and, for example,  Colletotrichum truncatum  (antracnose) on soybeans, 
       Corynespora cassficola  (leaf blotch) on soybeans, 
       Dematophora necatrix  (root/stem rot) on soybeans, 
       Diaporthe phaseolorum  (stem disease) on soybeans, 
       Drechslera species, Pyrenophora  species on corn, cereals, rice and lawn, on barley (for example  D. teres ) and on wheat (for example  D. tritici - repentis ), 
       Esca  on grapevines, caused by  Phaeoacremonium chlamydosporium, Ph. Aleophilum , and  Formitipora punctata  (syn.  Phellinus punctatus ), 
       Elsinoe ampelina  on grapevines, 
       Epicoccum  spp. (black head) on wheat, 
       Exserohlium  species on corn, 
       Erysiphe cichoracearum  and  Sphaerotheca fuliginea  on cucumbers, 
       Fusarium  and  Verticillium  species on various plants: for example  F. graminearum  or  F. culmorum  (foot rot) on cereals (for example wheat or barley) or, for example,  F. oxysporum  on tomatoes and  Fusarium solani  (stem disease) on soybeans, 
     Gaeumanomyces graminis (take-all) on cereals (for example wheat or barley), 
       Gibberella  species on cereals and rice (for example  Gibberella fujikuroi ), 
       Glomerella cingulata  on grapevines and other plants, 
     Grainstaining complex on rice, 
       Guignardia budwelli  on grapevines, 
       Helminthosporium  species on corn and rice, 
       Isariopsis clavispora  on grapevines, 
       Macrophomina phaseolina  (root/stem rot) on soybeans, 
       Michrodochium nivale  (pink snow mold) on cereals (for example wheat or barley), 
       Microsphaera diffusa  (powdery mildew) on soybeans, 
       Mycosphaerella  species on cereals, bananas and peanuts, such as, for example,  M. graminicola  on wheat or  M. fijiensis  on bananas, 
       Peronospora  species on cabbage (for example  P. brassicae ), bulbous plants (for example  P. destructor ) and, for example,  Peronospora manshurica  (downy mildew) on soybeans, 
       Phakopsara pachyrhizi  (soybean rust) and  Phakopsara meibomiae  (soybean rust) on soybeans, 
       Phialophora gregata  (stem disease) on soybeans, 
       Phomopsis  species on sunflowers, grapevines (for example  P. viticola ) and soybeans (for example  Phomopsis phaseoli ), 
       Phytophthora  species on various plants, for example  P. capsici  on bell peppers, 
       Phytophthora megasperma  (leaf/stem rot) on soybeans,  Phytophthora infestans  on potatoes and tomatoes, 
       Plasmopara viticola  on grapevines, 
       Podosphaera leucotricha  on apples, 
       Pseudocercosporella herpotrichoides  (strawbreaker) on cereals (wheat or barley), 
       Pseudoperonospora  on various plants, for example  P. cubensis  on cucumbers or  P. humili  on hops, 
       Pseudopezicula tracheiphllai  on grapevines, 
       Puccima  species on various plants, for example  P. triticina, P. striformins, P. hordei  or  P. graminis  on cereals (for example wheat or barley) or on asparagus (for example  P. asparagi ), 
       Pyriculana oryzae, Corticium sasakii, Sarocladium oryzae, S. attenuatum, Pyrenophora tritici - repentis  (leaf spot) on wheat or  Pyrenophora teres  (net blotch) on barley, 
       Entyloma oryzae  on rice, 
       Pyricularia grisea  on lawn and cereals, 
       Pythium  spp. on lawn, rice, corn, wheat, cotton, oilseed rape, sunflowers, sugar beet, vegetables and other plants (for example  P. ultimum  or  P. aphanidermatum ), 
       Ramularia collo - cygni  (physiological leaf spots) on barley, 
       Rhizoctonia  species on cotton, rice, potatoes, lawn, corn, oilseed rape, potatoes, sugar beet, vegetables and on various other plants, for example  Rhizoctonia solani  (root/stem rot) on soybeans or  Rhizoctonia cerealis  (yellow patch) on wheat or barley, 
       Rhynchosporium secalis  on barley (scald), rye and triticale, 
       Sclerotinia  species on oilseed rape, sunflowers and, for example,  Sclerotinia scierotiorum  (stem disease) or  Sclerotinuia rolfsii  (stem disease) on soybeans, 
       Septoria glycines  (brown spot) on soybeans, 
       Septoria tritici  (leaf spot) and  Stagonospora nodorum  on wheat, 
       Erysiphe  (syn.  Uncinula )  necator  on grapevines, 
       Setospaena  species on corn and lawn, 
       Sphacelotheca reilinia  on corn, 
       Stagonospora nodorum  (glume blotch) on wheat, 
       Thievaliopsis  species on soybeans and cotton, 
       Tilletia  species on cereals, 
       Typhula incarnata  (snow mold) on wheat or barley, 
       Ustilago  species on cereals, corn (for example  U. maydis ) and sugar cane, 
       Venturia  species (scab) on apples (for example  V. inaequalis ) and pears. 
     The compounds I are furthermore suitable for controlling harmful fungi in the protection of materials (for example wood, paper, paint dispersions, fibers or fabrics) and in the protection of stored products. In the protection of wood, particular attention is paid to the following harmful fungi: Ascomycetes, such as  Ophiostoma  spp.,  Ceratocystis  spp.,  Aureobasidium pullulans, Sclerophoma  spp.,  Chaetomium  spp.,  Humicola  spp.,  Petriella  spp.,  Trichurus  spp.; Basidiomycetes, such as  Coniophora  spp.,  Coriolus  spp.,  Gloeophyllum  spp.,  Lentinus  spp.,  Pleurotus  spp.,  Poria  spp.,  Serpula  spp. and  Tyromyces  spp., Deuteromycetes, such as  Aspergillus  spp.,  Cladosporium  spp.,  Penicillium  spp.,  Trichoderma  spp.,  Alternaria  spp.,  Paecilomyces  spp. and Zygomycetes, such as  Mucor  spp., additionally in the protection of materials the following yeasts:  Candida  spp. and  Saccharomyces cerevisae.    
     The compounds I are employed by treating the fungi or the plants, seeds or materials to be protected against fungal attack or the soil with a fungicidally effective amount of the active compounds. Application can be both before and after the infection of the materials, plants or seeds by the fungi. 
     The fungicidal compositions generally comprise between 0.1 and 95% by weight, preferably between 0.5 and 90% by weight, of active compound. 
     When employed in crop protection, the application rates are, depending on the kind of effect desired, between 0.01 and 2.0 kg of active compound per ha. 
     In seed treatment, the amounts of active compound required are generally from 1 to 1000 g/100 kg of seed, preferably from 5 to 100 g/100 kg of seed. 
     When used in the protection of materials or stored products, the active compound application rate depends on the kind of application area and on the desired effect. Amounts typically applied in the protection of materials are, for example, from 0.001 g to 2 kg, preferably from 0.005 g to 1 kg, of active compound per cubic meter of treated material. 
     The compounds of the formula I can be present in different crystal modifications which may differ in their biological activity. They are likewise subject matter of the present invention. 
     The compounds I can be converted into the customary formulations, for example solutions, emulsions, suspensions, dusts, powders, pastes or granules. The use form depends on the particular intended purpose; in each case, it should ensure a fine and even distribution of the compound according to the invention. 
     The formulations are prepared in a known manner, for example by extending the active compounds with solvents and carriers or solvents or carriers, if desired using further auxiliaries such as emulsifiers and dispersants. Here, individual compounds may also have various functions. Solvents, carriers and auxiliaries suitable for this purpose are essentially:
         water, aromatic solvents (for example Solvesso® products, xylene), paraffins (for example mineral oil fractions), alcohols (for example methanol, butanol, pentanol, benzyl alcohol), ketones (for example cyclohexanone, gamma-butyrolactone), pyrrolidones (NMP, NOP), acetates (glycol diacetate), glycols, fatty acid dimethylamides, fatty acids and fatty acid esters. In principle, solvent mixtures may also be used.   carriers such as ground natural minerals (for example kaolins, clays, talc, chalk) and ground synthetic minerals (for example highly disperse silica, silicates);       

     emulsifiers such as nonionogenic and anionic emulsifiers (for example polyoxyethylene fatty alcohol ethers, alkylsulfonates and arylsulfonates) and dispersants such as lignosulfite waste liquors and methylcellulose. 
     The compositions according to the invention can be formulated in solid form or in liquid form. Depending on the embodiment, the compositions according to the invention may also comprise auxiliaries and/or carriers customary in crop protection compositions or in compositions for the protection of materials. The auxiliaries include in particular conventional surface-active substances and other additives and carriers customary in crop protection and in the protection of materials, which compounds may be solid or liquid. The surface-active substances include in particular surfactants, especially those having wetting agent properties. The other auxiliaries (additives) include in particular thickeners, antifoams, preservatives, antifreeze agents, stabilizers, anticaking agents or powder-flow aids and buffers. 
     Conventional surface-active substances which are usable in principle are anionic, nonionic and amphoteric surfactants including polymer surfactants, and the molecular weight of the surfactants will typically not exceed a value of 2000 Dalton and in particular 1000 Dalton (number-average). 
     The anionic surfactants include, for example, carboxylates, in particular alkali metal, alkaline earth metal, and ammonium salts of fatty acids, for example potassium stearate, which are usually also referred to as soaps; acyl glutamates; sarcosinates, for example sodium lauroyl sarcosinate; taurates; methylcelluloses; alkyl phosphates, in particular alkyl esters of mono- and diphosphoric acid; sulfates, in particular alkyl sulfates and alkyl ether sulfates; sulfonates, further alkyl sulfonates and alkylaryl sulfonates, in particular alkali metal, alkaline earth metal and ammonium salts of arylsulfonic acids and of alkyl-substituted arylsulfonic acids, alkylbenzenesulfonic acids, such as, for example, lignol and phenolsulfonic acid, naphthalene- and dibutylnaphthalenesulfonic acids, or dodecylbenzenesulfonates, alkylnaphthalene-sulfonates, alkyl methyl ester sulfonates, condensates of sulfonated naphthalene and derivatives thereof with formaldehyde, condensates of naphthalene sulfonic acids, phenol- and/or phenolsulfonic acids with formaldehyde or with formaldehyde and urea, mono- or dialkyl sulfosuccinates; and also protein hydrolysates and lignosulfite waste liquors. The abovementioned sulfonic acids are advantageously used in the form of their neutral or, if appropriate, basic salts. 
     The nonionic surfactants include, for example:
         fatty alcohol alkoxylates and oxoalcohol alkoxylates, in particular ethoxylates and propoxylates having degrees of alkoxylation of usually from 2 to 100 and in particular from 3 to 50, for example alkoxylates of C 8 -C 30 -alkanols or alk(adi)enols, for example of isotridecyl alcohol, lauryl alcohol, oleyl alcohol or stearyl alcohol, and their C 1 -C 4 -alkyl ethers and C 1 -C 4 -alkyl esters, for example their acetates;   alkoxylated animal and/or vegetable fats and/or oils, for example corn oil ethoxylates, castor oil ethoxylates, tallow fat ethoxylates,   glycerol esters, such as, for example, glycerol monostearate,   alkylphenol alkoxylates, such as, for example, ethoxylated isooctylphenol, octylphenol or nonylphenol, tributylphenol polyoxyethylene ether,   fatty amine alkoxylates, fatty acid amide alkoxylates and fatty acid diethanolamide alkoxylates, in particular their ethoxylates,   sugar surfactants, sorbitol esters, such as, for example, sorbitan fatty acid esters (sorbitan monooleate, sorbitan tristearate), polyoxyethylene sorbitan fatty acid esters, alkyl polyglycosides, N-alkylgluconamides,   alkyl methyl sulfoxides,   alkyldimethylphosphine oxides, such as, for example, tetradecyldimethylphosphine oxide.       

     The amphoteric surfactants include, for example, sulfobetaines, carboxybetaines and alkyldimethylamine oxides, for example tetradecyldimethylamine oxide. 
     Other surfactants which may be mentioned here by way of example are perfluoro surfactants, silicone surfactants, phospholipids, such as, for example, lecithin or chemically modified lecithins, amino acid surfactants, for example N-lauroylglutamate. 
     Suitable for the preparation of directly sprayable solutions, emulsions, pastes or oil dispersions are mineral oil fractions of medium to high boiling point, such as kerosene or diesel oil, furthermore coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, for example toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, methanol, ethanol, propanol, butanol, cyclohexanol, cyclohexanone, isophorone, strongly polar solvents, for example dimethyl sulfoxide, N-methylpyrrolidone and water. 
     Powders, materials for spreading and dustable products can be prepared by mixing or concomitantly grinding the active components A and B and, if present further actives with at least one solid carrier. 
     Granules, for example coated granules, impregnated granules and homogeneous granules, can be prepared by binding the active compounds to at least one solid carrier. Examples of solid carriers are mineral earths such as silica gels, silicates, talc, kaolin, attaclay, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, ground synthetic materials, fertilizers, such as, for example, ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas, and products of vegetable origin, such as cereal meal, tree bark meal, wood meal and nutshell meal, cellulose powders and other solid carriers. 
     The formulations of the compounds according to the invention generally comprise from 0.01 to 95% by weight, preferably from 0.1 to 90% by weight, of the compounds I and II. Here, the active compounds are preferably employed in a purity of from 90% to 100%, preferably from 95% to 100%. 
     For the treatment of seed, the formulations in question give, after two- to tenfold dilution, active compound concentrations of from 0.01 to 60% by weight, preferably from 0.1 to 40% by weight, in the ready-to-use preparations. 
     In general, the formulations comprise from 0.01 to 95% by weight, preferably from 0.1 to 90% by weight, of the active compound. The active compounds are employed in a purity of from 90% to 100%, preferably 95% to 100% (according to NMR spectrum). 
     The following are examples of formulations: 1. Products for dilution with water 
     A Water-Soluble Concentrates (SL, LS) 
     10 parts by weight of the active compounds are dissolved in 90 parts by weight of water or in a water-soluble solvent. As an alternative, wetting agents or other auxiliaries are added. The active compound dissolves upon dilution with water. In this way, a formulation having a content of 10% by weight of active compound is obtained. 
     B Dispersible Concentrates (DC) 
     20 parts by weight of the active compounds are dissolved in 70 parts by weight of cyclohexanone with addition of 10 parts by weight of a dispersant, for example polyvinylpyrrolidone. Dilution with water gives a dispersion. The active compound content is 20% by weight 
     C Emulsifiable Concentrates (EC) 
     15 parts by weight of the active compounds are dissolved in 75 parts by weight of xylene with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight). Dilution with water gives an emulsion. The formulation has an active compound content of 15% by weight. 
     D Emulsions (EW, EO, ES) 
     25 parts by weight of the active compounds are dissolved in 35 parts by weight of xylene with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight). This mixture is introduced into 30 parts by weight of water by means of an emulsifying machine (e.g. Ultraturrax) and made into a homogeneous emulsion. Dilution with water gives an emulsion. The formulation has an active compound content of 25% by weight. 
     E Suspensions (SC, OD, FS) 
     In an agitated ball mill, 20 parts by weight of the active compounds are comminuted with addition of 10 parts by weight of dispersants and wetting agents and 70 parts by weight of water or an organic solvent to give a fine active compound suspension. Dilution with water gives a stable suspension of the active compound. The active compound content in the formulation is 20% by weight. 
     F Water-Dispersible Granules and Water-Soluble Granules (WG, SG) 
     50 parts by weight of the active compounds are ground finely with addition of 50 parts by weight of dispersants and wetting agents and prepared as water-dispersible or water-soluble granules by means of technical appliances (for example extrusion, spray tower, fluidized bed). Dilution with water gives a stable dispersion or solution of the active compound. The formulation has an active compound content of 50% by weight. 
     G Water-Dispersible Powders and Water-Soluble Powders (WP, SP, SS, WS) 
     75 parts by weight of the active compounds are ground in a rotor-stator mill with addition of 25 parts by weight of dispersants, wetting agents and silica gel. Dilution with water gives a stable dispersion or solution of the active compound. The active compound content of the formulation is 75% by weight. 
     H Gel Formulations (GF) 
     In a ball mill, 20 parts by weight of the active compounds, 10 parts by weight of dispersant, 1 part by weight of gelling agent and 70 parts by weight of water or an organic solvent are ground to give a fine suspension. On dilution with water, a stable suspension having an active compound content of 20% by weight is obtained. 
     2. Products to be Applied Undiluted 
     I Dustable Powders (DP, DS) 
     5 parts by weight of the active compounds are ground finely and mixed intimately with 95 parts by weight of finely divided kaolin. This gives a dustable product having an active compound content of 5% by weight. 
     J Granules (GR, FG, GG, MG) 
     0.5 part by weight of the active compounds is ground finely and associated with 99.5 parts by weight of carriers. Current methods are extrusion, spray-drying and the fluidized bed. This gives granules to be applied undiluted having an active compound content of 0.5% by weight. 
     K ULV Solutions (UL) 
     10 parts by weight of the active compounds are dissolved in 90 parts by weight of an organic solvent, for example xylene. This gives a product to be applied undiluted having an active compound content of 10% by weight. 
     For seed treatment, use is usually made of water-soluble concentrates (LS), suspensions (FS), dustable powders (DS), water-dispersible and water-soluble powders (WS, SS), emulsions (ES), emulsifiable concentrates (EC) and gel formulations (GF). These formulations can be applied to the seed in undiluted form or, preferably, diluted. Application can be carried out prior to sowing. 
     The active compounds can be used as such, in the form of their formulations or of the use forms prepared therefrom, e.g. in the form of directly sprayable solutions, powders, suspensions or dispersions, emulsions, oil dispersions, pastes, dustable products, materials for broadcasting or granules, by means of spraying, atomizing, dusting, broadcasting or watering. The use forms depend entirely on the intended purposes; they should always ensure the finest possible distribution of the active compounds according to the invention. 
     Aqueous use forms can be prepared from emulsifiable concentrates, pastes or wettable powders (spray powders, oil dispersions) by addition of water. To prepare emulsions, pastes or oil dispersions, the substances can be homogenized in water, as such or dissolved in an oil or solvent, by means of wetting agents, tackifiers, dispersants or emulsifiers. However, it is also possible to prepare concentrates comprising active substance, wetting agent, tackifier, dispersant or emulsifier and possibly solvent or oil which are suitable for dilution with water. 
     The concentrations of active compound in the ready-for-use preparations can be varied within relatively wide ranges. In general, they are between 0.0001 and 10%, preferably between 0.01 and 1%. 
     The active compounds can also be used with great success in the ultra-low volume (ULV) process, it being possible to apply formulations with more than 95% by weight of active compound or even the active compound without additives. 
     Oils of various types, wetting agents, adjuvants, herbicides, fungicides, other pesticides and bactericides can be added to the active compounds, if appropriate also not until immediately before use (tank mix). These agents can be added to the compositions according to the invention in a weight ratio of 1:100 to 100:1, preferably of 1:10 to 10:1. 
     The following are particularly suitable as adjuvants in this context: organically modified polysiloxanes, for example Break Thru S 240®; alcohol alkoxylates, for example Atplus 245®, Atplus MBA 1303®, Plurafac LF 300® and Lutensol ON 30®; EO-PO block polymers, for example Pluronic RPE 2035® and Genapol B®; alcohol ethoxylates, for example Lutensol XP 80®; and sodium dioctylsulfosuccinate, for example Leophen RA®. 
     The compositions according to the invention in the application form as fungicides can also be present together with other active compounds, for example with herbicides, insecticides, growth regulators, fungicides or else with fertilizers. When mixing the compounds (I) or the compositions comprising them with one or more further active compounds, in particular fungicides, it is in many cases possible, for example, to widen the activity spectrum or to prevent the development of resistance. In many cases, synergistic effects are obtained. The fungicides are preferably selected from the following groups. Preferred representatives of these groups are listed in Table B. 
     Strobilurins, carboxamides, such as carboxanilides, carboxylic acid morpholides, benzamides, other carboxamides, azoles, such as triazoles, imidazoles, benzimidazoles, others, nitrogenous heterocyclyl compounds, such as pyridines, pyrimidines, pyrroles, morpholines, dicarboximides, other nitrogenous heterocyclyl compounds, thio- and dithiocarbamates, carbamates, guanidines, antibiotics, nitrophenyl derivatives, organometal compounds, sulfur-containing heterocyclyl compounds, organophosphorus compounds, organochlorine compounds, inorganic active compounds, other fungicides. 
     The present invention further relates, accordingly, to the compositions that are listed in Table B, each line of Table B corresponding to a fungicidal composition comprising a compound of the formula I (component 1), which is preferably one of the compounds described herein as being preferred, and comprising the further active compound indicated in each case in the row in question (component 2). According to one embodiment of the invention, component 1 in each row of Table B is in each case one of the compounds of the formula I that are specifically individualized in Tables 1 to 336. 
     
       
         
           
               
               
               
             
               
                 TABLE B 
               
               
                   
               
               
                 Row 
                 Component 1 
                 Component 2 
               
               
                   
               
             
            
               
                 B-1 
                 a compound of the formula I 
                 azoxystrobin 
               
               
                 B-2 
                 a compound of the formula I 
                 dimoxystrobin 
               
               
                 B-3 
                 a compound of the formula I 
                 enestroburin 
               
               
                 B-4 
                 a compound of the formula I 
                 fluoxastrobin 
               
               
                 B-5 
                 a compound of the formula I 
                 kresoxim-methyl 
               
               
                 B-6 
                 a compound of the formula I 
                 metominostrobin 
               
               
                 B-7 
                 a compound of the formula I 
                 orysastrobin 
               
               
                 B-8 
                 a compound of the formula I 
                 picoxystrobin 
               
               
                 B-9 
                 a compound of the formula I 
                 pyraclostrobin 
               
               
                 B-10 
                 a compound of the formula I 
                 pyribencarb 
               
               
                 B-11 
                 a compound of the formula I 
                 trifloxystrobin 
               
               
                 B-12 
                 a compound of the formula I 
                 2-(2-(6-(3-chloro-2-methylphenoxy)-5-fluoropyrimidin- 
               
               
                   
                   
                 4-yloxy)phenyl)-2-methoxyimino-N-methylacetamide 
               
               
                 B-13 
                 a compound of the formula I 
                 methyl 2-(ortho-((2,5-dimethylphenyloxy- 
               
               
                   
                   
                 methylene)phenyl)-3-methoxyacrylate 
               
               
                 B-14 
                 a compound of the formula I 
                 methyl 3-methoxy-2-(2-(N-(4-methoxyphenyl)- 
               
               
                   
                   
                 cyclopropanecarboximidoylsulfanyl- 
               
               
                   
                   
                 methyl)phenyl)acrylate 
               
               
                 B-15 
                 a compound of the formula I 
                 benalaxyl 
               
               
                 B-16 
                 a compound of the formula I 
                 benalaxyl-M 
               
               
                 B-17 
                 a compound of the formula I 
                 benodanil 
               
               
                 B-18 
                 a compound of the formula I 
                 bixafen 
               
               
                 B-19 
                 a compound of the formula I 
                 boscalid 
               
               
                 B-20 
                 a compound of the formula I 
                 carboxin 
               
               
                 B-21 
                 a compound of the formula I 
                 fenfuram 
               
               
                 B-22 
                 a compound of the formula I 
                 fenhexamid 
               
               
                 B-23 
                 a compound of the formula I 
                 flutolanil 
               
               
                 B-24 
                 a compound of the formula I 
                 furametpyr 
               
               
                 B-25 
                 a compound of the formula I 
                 isotianil 
               
               
                 B-26 
                 a compound of the formula I 
                 kiralaxyl 
               
               
                 B-27 
                 a compound of the formula I 
                 mepronil 
               
               
                 B-28 
                 a compound of the formula I 
                 metalaxyl 
               
               
                 B-29 
                 a compound of the formula I 
                 ofurace 
               
               
                 B-30 
                 a compound of the formula I 
                 oxadixyl 
               
               
                 B-31 
                 a compound of the formula I 
                 oxycarboxin 
               
               
                 B-32 
                 a compound of the formula I 
                 penthiopyrad 
               
               
                 B-33 
                 a compound of the formula I 
                 thifluzamide 
               
               
                 B-34 
                 a compound of the formula I 
                 tecloftalam 
               
               
                 B-35 
                 a compound of the formula I 
                 tiadinil 
               
               
                 B-36 
                 a compound of the formula I 
                 2-amino-4-methylthiazole-5-carboxanilide 
               
               
                 B-37 
                 a compound of the formula I 
                 2-chloro-N-(1,1,3-trimethylindan-4-yl)-nicotinamide 
               
               
                 B-38 
                 a compound of the formula I 
                 N-(3′,4′-dichloro-5-fluorobiphenyl-2-yl)- 
               
               
                   
                   
                 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide 
               
               
                 B-39 
                 a compound of the formula I 
                 5-fluoro-1,3-dimethyl-1H-pyrazole- 
               
               
                   
                   
                 4-carboxylic acid [2-(1,3-dimethylbutyl)- 
               
               
                   
                   
                 phenyl]amide 
               
               
                 B-40 
                 a compound of the formula I 
                 N-(4′-chloro-3′,5-difluorobiphenyl-2-yl)- 
               
               
                   
                   
                 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide 
               
               
                 B-41 
                 a compound of the formula I 
                 N-(4′-chloro-3′,5-difluorobiphenyl-2-yl)- 
               
               
                   
                   
                 3-trifluoromethyl-1-methyl-1H-pyrazole-4-carboxamide 
               
               
                 B-42 
                 a compound of the formula I 
                 N-(3′,4′-dichloro-5-fluorobiphenyl-2-yl)- 
               
               
                   
                   
                 3-trifluoromethyl-1-methyl-1H-pyrazole-4-carboxamide 
               
               
                 B-43 
                 a compound of the formula I 
                 N-(3′,5-difluoro-4′-methylbiphenyl-2-yl)- 
               
               
                   
                   
                 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide 
               
               
                 B-44 
                 a compound of the formula I 
                 N-(3′,5-difluoro-4′-methylbiphenyl-2-yl)- 
               
               
                   
                   
                 3-trifluoromethyl-1-methyl-1H-pyrazole-4-carboxamide 
               
               
                 B-45 
                 a compound of the formula I 
                 N-(2-bicyclopropyl-2-ylphenyl)-3-difluoro- 
               
               
                   
                   
                 methyl-1-methyl-1H-pyrazole-4-carboxamide 
               
               
                 B-46 
                 a compound of the formula I 
                 N-(cis-2-bicyclopropyl-2-ylphenyl)- 
               
               
                   
                   
                 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide 
               
               
                 B-47 
                 a compound of the formula I 
                 N-(trans-2-bicyclopropyl-2-ylphenyl)-3- 
               
               
                   
                   
                 difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide 
               
               
                 B-48 
                 a compound of the formula I 
                 dimethomorph 
               
               
                 B-49 
                 a compound of the formula I 
                 flumorph 
               
               
                 B-50 
                 a compound of the formula I 
                 flumetover 
               
               
                 B-51 
                 a compound of the formula I 
                 fluopicolide (picobenzamid) 
               
               
                 B-52 
                 a compound of the formula I 
                 fluopyram 
               
               
                 B-53 
                 a compound of the formula I 
                 zoxamide 
               
               
                 B-54 
                 a compound of the formula I 
                 N-(3-ethyl-3,5,5-trimethylcyclohexyl)- 
               
               
                   
                   
                 3-formylamino-2-hydroxybenzamide 
               
               
                 B-55 
                 a compound of the formula I 
                 carpropamid 
               
               
                 B-56 
                 a compound of the formula I 
                 diclocymet 
               
               
                 B-57 
                 a compound of the formula I 
                 mandipropamid 
               
               
                 B-58 
                 a compound of the formula I 
                 oxytetracyclin 
               
               
                 B-59 
                 a compound of the formula I 
                 silthiofam 
               
               
                 B-60 
                 a compound of the formula I 
                 N-(6-methoxypyridin-3-yl)cyclopropane-carboxamide 
               
               
                 B-61 
                 a compound of the formula I 
                 azaconazole 
               
               
                 B-62 
                 a compound of the formula I 
                 bitertanol 
               
               
                 B-63 
                 a compound of the formula I 
                 bromuconazole 
               
               
                 B-64 
                 a compound of the formula I 
                 cyproconazole 
               
               
                 B-65 
                 a compound of the formula I 
                 difenoconazole 
               
               
                 B-66 
                 a compound of the formula I 
                 diniconazole 
               
               
                 B-67 
                 a compound of the formula I 
                 diniconazole-M 
               
               
                 B-68 
                 a compound of the formula I 
                 enilconazole 
               
               
                 B-69 
                 a compound of the formula I 
                 epoxiconazole 
               
               
                 B-70 
                 a compound of the formula I 
                 fenbuconazole 
               
               
                 B-71 
                 a compound of the formula I 
                 flusilazole 
               
               
                 B-72 
                 a compound of the formula I 
                 fluquinconazole 
               
               
                 B-73 
                 a compound of the formula I 
                 flutriafol 
               
               
                 B-74 
                 a compound of the formula I 
                 hexaconazole 
               
               
                 B-75 
                 a compound of the formula I 
                 imibenconazole 
               
               
                 B-76 
                 a compound of the formula I 
                 ipconazole 
               
               
                 B-77 
                 a compound of the formula I 
                 metconazole 
               
               
                 B-78 
                 a compound of the formula I 
                 myclobutanil 
               
               
                 B-79 
                 a compound of the formula I 
                 oxpoconazole 
               
               
                 B-80 
                 a compound of the formula I 
                 paclobutrazole 
               
               
                 B-81 
                 a compound of the formula I 
                 penconazole 
               
               
                 B-82 
                 a compound of the formula I 
                 propiconazole 
               
               
                 B-83 
                 a compound of the formula I 
                 prothioconazole 
               
               
                 B-84 
                 a compound of the formula I 
                 simeconazole 
               
               
                 B-85 
                 a compound of the formula I 
                 tebuconazole 
               
               
                 B-86 
                 a compound of the formula I 
                 tetraconazole 
               
               
                 B-87 
                 a compound of the formula I 
                 triadimenol 
               
               
                 B-88 
                 a compound of the formula I 
                 triadimefon 
               
               
                 B-89 
                 a compound of the formula I 
                 triticonazole 
               
               
                 B-90 
                 a compound of the formula I 
                 uniconazole 
               
               
                 B-91 
                 a compound of the formula I 
                 1-(4-chlorophenyl)-2-([1,2,4]triazol-1-yl)- 
               
               
                   
                   
                 cycloheptanol 
               
               
                 B-92 
                 a compound of the formula I 
                 cyazofamid 
               
               
                 B-93 
                 a compound of the formula I 
                 imazalil 
               
               
                 B-94 
                 a compound of the formula I 
                 imazalil sulfate 
               
               
                 B-95 
                 a compound of the formula I 
                 pefurazoate 
               
               
                 B-96 
                 a compound of the formula I 
                 prochloraz 
               
               
                 B-97 
                 a compound of the formula I 
                 triflumizole 
               
               
                 B-98 
                 a compound of the formula I 
                 benomyl 
               
               
                 B-99 
                 a compound of the formula I 
                 carbendazim 
               
               
                 B-100 
                 a compound of the formula I 
                 fuberidazole 
               
               
                 B-101 
                 a compound of the formula I 
                 thiabendazole 
               
               
                 B-102 
                 a compound of the formula I 
                 ethaboxam 
               
               
                 B-103 
                 a compound of the formula I 
                 etridiazole 
               
               
                 B-104 
                 a compound of the formula I 
                 hymexazole 
               
               
                 B-105 
                 a compound of the formula I 
                 fluazinam 
               
               
                 B-106 
                 a compound of the formula I 
                 pyrifenox 
               
               
                 B-107 
                 a compound of the formula I 
                 1-(4-chlorophenyl)-1-(propyn-2-yloxy)-3-(4-(3,4- 
               
               
                   
                   
                 dimethoxyphenyl)isoxazol-5-yl)-propan-2-one 
               
               
                 B-108 
                 a compound of the formula I 
                 3-[5-(4-chlorophenyl)-2,3-dimethyl- 
               
               
                   
                   
                 isoxazolidin-3-yl]pyridine 
               
               
                 B-109 
                 a compound of the formula I 
                 2,3,5,6-tetrachloro-4-methanesulfonyl-pyridine 
               
               
                 B-110 
                 a compound of the formula I 
                 3,4,5-trichloropyridine-2,6-dicarbonitrile 
               
               
                 B-111 
                 a compound of the formula I 
                 N-(1-(5-bromo-3-chloropyridin-2-yl)ethyl)- 
               
               
                   
                   
                 2,4-dichloronicotinamide 
               
               
                 B-112 
                 a compound of the formula I 
                 N-((5-bromo-3-chloropyridin-2-yl)methyl)- 
               
               
                   
                   
                 2,4-dichloronicotinamide 
               
               
                 B-113 
                 a compound of the formula I 
                 bupirimate 
               
               
                 B-114 
                 a compound of the formula I 
                 cyprodinil 
               
               
                 B-115 
                 a compound of the formula I 
                 diflumetorim 
               
               
                 B-116 
                 a compound of the formula I 
                 ferimzone 
               
               
                 B-117 
                 a compound of the formula I 
                 fenarimol 
               
               
                 B-118 
                 a compound of the formula I 
                 mepanipyrim 
               
               
                 B-119 
                 a compound of the formula I 
                 nitrapyrin 
               
               
                 B-120 
                 a compound of the formula I 
                 nuarimol 
               
               
                 B-121 
                 a compound of the formula I 
                 pyrimethanil 
               
               
                 B-122 
                 a compound of the formula I 
                 fludioxonil 
               
               
                 B-123 
                 a compound of the formula I 
                 fenpiclonil 
               
               
                 B-124 
                 a compound of the formula I 
                 aldimorph 
               
               
                 B-125 
                 a compound of the formula I 
                 dodemorph 
               
               
                 B-126 
                 a compound of the formula I 
                 dodemorph acetate 
               
               
                 B-127 
                 a compound of the formula I 
                 fenpropimorph 
               
               
                 B-128 
                 a compound of the formula I 
                 tridemorph 
               
               
                 B-129 
                 a compound of the formula I 
                 fluoroimide 
               
               
                 B-130 
                 a compound of the formula I 
                 iprodione 
               
               
                 B-131 
                 a compound of the formula I 
                 procymidone 
               
               
                 B-132 
                 a compound of the formula I 
                 vinclozolin 
               
               
                 B-133 
                 a compound of the formula I 
                 acibenzolar-S-methyl 
               
               
                 B-134 
                 a compound of the formula I 
                 amisulbrom 
               
               
                 B-135 
                 a compound of the formula I 
                 anilazine 
               
               
                 B-136 
                 a compound of the formula I 
                 blasticidin-S 
               
               
                 B-137 
                 a compound of the formula I 
                 captan 
               
               
                 B-138 
                 a compound of the formula I 
                 captafol 
               
               
                 B-139 
                 a compound of the formula I 
                 chinomethionat 
               
               
                 B-140 
                 a compound of the formula I 
                 dazomet 
               
               
                 B-141 
                 a compound of the formula I 
                 debacarb 
               
               
                 B-142 
                 a compound of the formula I 
                 diclomezine 
               
               
                 B-143 
                 a compound of the formula I 
                 difenzoquat 
               
               
                 B-144 
                 a compound of the formula I 
                 difenzoquat methylsulfate 
               
               
                 B-145 
                 a compound of the formula I 
                 famoxadone 
               
               
                 B-146 
                 a compound of the formula I 
                 fenamidone 
               
               
                 B-147 
                 a compound of the formula I 
                 fenoxanil 
               
               
                 B-148 
                 a compound of the formula I 
                 fenpropidin 
               
               
                 B-149 
                 a compound of the formula I 
                 folpet 
               
               
                 B-150 
                 a compound of the formula I 
                 octhilinone 
               
               
                 B-151 
                 a compound of the formula I 
                 oxolinic acid 
               
               
                 B-152 
                 a compound of the formula I 
                 piperalin 
               
               
                 B-153 
                 a compound of the formula I 
                 probenazole 
               
               
                 B-154 
                 a compound of the formula I 
                 proquinazid 
               
               
                 B-155 
                 a compound of the formula I 
                 pyroquilon 
               
               
                 B-156 
                 a compound of the formula I 
                 quinoxyfen 
               
               
                 B-157 
                 a compound of the formula I 
                 triazoxide 
               
               
                 B-158 
                 a compound of the formula I 
                 tricyclazole 
               
               
                 B-159 
                 a compound of the formula I 
                 triforine 
               
               
                 B-160 
                 a compound of the formula I 
                 5-chloro-7-(4-methylpiperidin-1-yl)- 
               
               
                   
                   
                 6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo- 
               
               
                   
                   
                 [1,5-a]pyrimidine 
               
               
                 B-161 
                 a compound of the formula I 
                 2-butoxy-6-iodo-3-propylchromen-4-one 
               
               
                 B-162 
                 a compound of the formula I 
                 ferbam 
               
               
                 B-163 
                 a compound of the formula I 
                 mancozeb 
               
               
                 B-164 
                 a compound of the formula I 
                 maneb 
               
               
                 B-165 
                 a compound of the formula I 
                 metiram 
               
               
                 B-166 
                 a compound of the formula I 
                 metam 
               
               
                 B-167 
                 a compound of the formula I 
                 methasulfocarb 
               
               
                 B-168 
                 a compound of the formula I 
                 propineb 
               
               
                 B-169 
                 a compound of the formula I 
                 thiram 
               
               
                 B-170 
                 a compound of the formula I 
                 zineb 
               
               
                 B-171 
                 a compound of the formula I 
                 ziram 
               
               
                 B-172 
                 a compound of the formula I 
                 diethofencarb 
               
               
                 B-173 
                 a compound of the formula I 
                 flubenthiavalicarb 
               
               
                 B-174 
                 a compound of the formula I 
                 iprovalicarb 
               
               
                 B-175 
                 a compound of the formula I 
                 propamocarb 
               
               
                 B-176 
                 a compound of the formula I 
                 propamocarb hydrochloride 
               
               
                 B-177 
                 a compound of the formula I 
                 methyl 3-(4-chlorophenyl)-3-(2-isopropoxy- 
               
               
                   
                   
                 carbonylamino-3-methylbutyrylamino)-propionate 
               
               
                 B-178 
                 a compound of the formula I 
                 valiphenal 
               
               
                 B-179 
                 a compound of the formula I 
                 4-fluorophenyl N-(1-(1-(4-cyanophenyl)- 
               
               
                   
                   
                 ethanesulfonyl)but-2-yl)carbamate 
               
               
                 B-180 
                 a compound of the formula I 
                 dodine 
               
               
                 B-181 
                 a compound of the formula I 
                 dodine free base 
               
               
                 B-182 
                 a compound of the formula I 
                 iminoctadine 
               
               
                 B-183 
                 a compound of the formula I 
                 iminoctadine triacetate 
               
               
                 B-184 
                 a compound of the formula I 
                 iminoctadine tris(albesilate) 
               
               
                 B-185 
                 a compound of the formula I 
                 guazatine 
               
               
                 B-186 
                 a compound of the formula I 
                 guazatine acetate 
               
               
                 B-187 
                 a compound of the formula I 
                 kasugamycin 
               
               
                 B-188 
                 a compound of the formula I 
                 kasugamycin hydrochloride hydrate 
               
               
                 B-189 
                 a compound of the formula I 
                 polyoxine 
               
               
                 B-190 
                 a compound of the formula I 
                 streptomycin 
               
               
                 B-191 
                 a compound of the formula I 
                 validamycin A 
               
               
                 B-192 
                 a compound of the formula I 
                 binapacryl 
               
               
                 B-193 
                 a compound of the formula I 
                 dicloran 
               
               
                 B-194 
                 a compound of the formula I 
                 dinobuton 
               
               
                 B-195 
                 a compound of the formula I 
                 dinocap 
               
               
                 B-196 
                 a compound of the formula I 
                 nitrothal-isopropyl 
               
               
                 B-197 
                 a compound of the formula I 
                 tecnazen 
               
               
                 B-198 
                 a compound of the formula I 
                 fentin acetate 
               
               
                 B-199 
                 a compound of the formula I 
                 fentin chloride 
               
               
                 B-200 
                 a compound of the formula I 
                 fentin hydroxide 
               
               
                 B-201 
                 a compound of the formula I 
                 isoprothiolane 
               
               
                 B-202 
                 a compound of the formula I 
                 dithianon 
               
               
                 B-203 
                 a compound of the formula I 
                 edifenphos 
               
               
                 B-204 
                 a compound of the formula I 
                 fosetyl 
               
               
                 B-205 
                 a compound of the formula I 
                 fosetyl aluminum 
               
               
                 B-206 
                 a compound of the formula I 
                 iprobenfos 
               
               
                 B-207 
                 a compound of the formula I 
                 pyrazophos 
               
               
                 B-208 
                 a compound of the formula I 
                 tolclofos-methyl 
               
               
                 B-209 
                 a compound of the formula I 
                 chlorothalonil 
               
               
                 B-210 
                 a compound of the formula I 
                 dichlofluanid 
               
               
                 B-211 
                 a compound of the formula I 
                 dichlorophen 
               
               
                 B-212 
                 a compound of the formula I 
                 flusulfamide 
               
               
                 B-213 
                 a compound of the formula I 
                 hexachlorobenzene 
               
               
                 B-214 
                 a compound of the formula I 
                 pencycuron 
               
               
                 B-215 
                 a compound of the formula I 
                 pentachlorophenol and salts thereof 
               
               
                 B-216 
                 a compound of the formula I 
                 phthalide 
               
               
                 B-217 
                 a compound of the formula I 
                 quintozene 
               
               
                 B-218 
                 a compound of the formula I 
                 thiophanate methyl 
               
               
                 B-219 
                 a compound of the formula I 
                 tolylfluanid 
               
               
                 B-220 
                 a compound of the formula I 
                 N-(4-chloro-2-nitrophenyl)-N-ethyl- 
               
               
                   
                   
                 4-methylbenzenesulfonamide 
               
               
                 B-221 
                 a compound of the formula I 
                 phosphorous acid and salts thereof 
               
               
                 B-222 
                 a compound of the formula I 
                 sulfur 
               
               
                 B-223 
                 a compound of the formula I 
                 Bordeaux mixture 
               
               
                 B-224 
                 a compound of the formula I 
                 copper acetate 
               
               
                 B-225 
                 a compound of the formula I 
                 copper hydroxide 
               
               
                 B-226 
                 a compound of the formula I 
                 copper oxychloride 
               
               
                 B-227 
                 a compound of the formula I 
                 basic copper sulfate 
               
               
                 B-228 
                 a compound of the formula I 
                 biphenyl 
               
               
                 B-229 
                 a compound of the formula I 
                 bronopol 
               
               
                 B-230 
                 a compound of the formula I 
                 cyflufenamid 
               
               
                 B-231 
                 a compound of the formula I 
                 cymoxanil 
               
               
                 B-232 
                 a compound of the formula I 
                 diphenylamine 
               
               
                 B-233 
                 a compound of the formula I 
                 metrafenone 
               
               
                 B-234 
                 a compound of the formula I 
                 mildiomycin 
               
               
                 B-235 
                 a compound of the formula I 
                 oxine-copper 
               
               
                 B-236 
                 a compound of the formula I 
                 prohexadione-calcium 
               
               
                 B-237 
                 a compound of the formula I 
                 spiroxamine 
               
               
                 B-238 
                 a compound of the formula I 
                 tolylfluanid 
               
               
                 B-239 
                 a compound of the formula I 
                 N-(cyclopropylmethoxyimino-(6-difluoro- 
               
               
                   
                   
                 methoxy-2,3-difluorophenyl)methyl)-2-phenylacetamide 
               
               
                 B-240 
                 a compound of the formula I 
                 N′-(4-(4-chloro-3-trifluoromethylphenoxy)- 
               
               
                   
                   
                 2,5-dimethylphenyl)-N-ethyl-N-methyl-formamidine 
               
               
                 B-241 
                 a compound of the formula I 
                 N′-(4-(4-fluoro-3-trifluoromethylphenoxy)- 
               
               
                   
                   
                 2,5-dimethylphenyl)-N-ethyl-N-methyl-formamidine 
               
               
                 B-242 
                 a compound of the formula I 
                 N′-(2-methyl-5-trifluoromethyl-4-(3-tri- 
               
               
                   
                   
                 methylsilanylpropoxy)phenyl)-N-ethyl-N-methylformamidine 
               
               
                 B-243 
                 a compound of the formula I 
                 N′-(5-difluoromethyl-2-methyl-4-(3-tri- 
               
               
                   
                   
                 methylsilanylpropoxy)phenyl)-N-ethyl-N-methylformamidine 
               
               
                   
               
            
           
         
       
     
     The active compounds II, mentioned above as component 2, their preparation and their action against harmful fungi are generally known (cf.: http://www.hclrss.demon.co.uk/index.html); they are commercially available. The compounds named according to IUPAC, their preparation and their fungicidal action are likewise known [cf. EP-A 226 917; EP-A 10 28 125; EP-A 10 35 122; EP-A 12 01 648; WO 98/46608; WO 99/24413; WO 03/14103; WO 03/053145; WO 03/066609; WO 04/049804]. 
     The present invention furthermore relates to a pharmaceutical composition comprising at least one pyridazine according to the invention and/or a pharmaceutically acceptable salt thereof and, if appropriate, at least one pharmaceutically acceptable carrier. The invention also relates to the pharmaceutical use of the pyridazines of the formula I according to the invention, in particular the pyridazines of the formula I described in the above description as being preferred, and/or their pharmaceutically acceptable salts, in particular their use for preparing a medicament for the treatment of cancer. 
     The pyridazines of the formula I according to the invention, in particular the pyridazines of the formula I according to the invention described in the above description as being preferred, and/or their pharmaceutically acceptable salts effectively inhibit the growth and/or the propagation of tumor cells, as can be demonstrated in standard tests with tumor cell lines, such as HeLa, MCF-7 and COLO 205. In particular, the pyrimidines of the formula I according to the invention generally have IC 50  values of &lt;10 −6  mol/l (i.e. &lt;1 μM), preferably IC 50  values of &lt;10 −7  mol/l (i.e. &lt;100 nM), for cell cycle inhibition in HeLa cells. 
     The pyridazines of the formula I according to the invention, in particular the pyridazines of the formula I according to the invention described in the above description as being preferred, and/or their pharmaceutically acceptable salts are suitable for the treatment, inhibiton or control of growth and/or propagation of tumor cells and the disorders associated therewith. Accordingly, they are suitable for cancer therapy in warm-blooded vertebrates, for example mammals and birds, in particular man, but also other mammals, in particular useful and domestic animals, such as dogs, cats, pigs, ruminants (cattle, sheep, goats, bison, etc.), horses and birds, such as chicken, turkey, ducks, geese, guineafowl and the like. 
     The pyridazines of the formula I according to the invention, especially the pyridazines of the formula I according to the invention described in the above description as being preferred, and/or their pharmaceutically acceptable salts are particularly suitable for the therapy of cancer or cancerous disorders of the following organs: breast, lung, intestine, prostate, skin (melanoma), kidney, bladder, mouth, larynx, esophagus, stomach, ovaries, pancreas, liver and brain. 
     In addition to the pyridazine I according to the invention and/or its pharmaceutically acceptable salt, the pharmaceutical compositions according to the invention comprise at least optionally a suitable carrier. Suitable carriers are, for example, the solvents, carriers, excipients, binders and the like customarily used for pharmaceutical formulations, which are described below in an exemplary manner for individual types of administration. 
     The compounds I according to the invention can be administered in a customary manner, for example orally, intravenously, intramuscularly or subcutaneously. For oral administration, the active compound can be mixed, for example, with an inert diluent or with an edible carrier; it can be embedded into a hard or soft gelatin capsule, it can be compressed to tablets or it can be mixed directly with the food/feed. The active compound can be mixed with excipients and administered in the form of indigestible tablets, buccal tablets, pastilles, pills, capsules, suspensions, potions, syrups and the like. Such preparations should contain at least 0.1% of active compound. The composition of the preparation may, of course, vary. It usually comprises from 2 to 60% by weight of active compound, based on the total weight of the preparation in question (dosage unit). Preferred preparations of the compound I according to the invention comprise from 10 to 1000 mg of active compound per oral dosage unit. 
     The tablets, pastilles, pills, capsules and the like may furthermore comprise the following components: binders, such as traganth, gum arabic, corn starch or gelatin, excipients, such as dicalcium phosphate, disintegrants, such as corn starch, potato starch, alginic acid and the like, glidants, such as magnesium stearate, sweeteners, such as sucrose, lactose or saccharin, and/or flavors, such as peppermint, vanilla and the like. The capsules may furthermore comprise a liquid carrier. Other substances which modify the properties of the dosage unit may also be used. For example, tablets, pills and capsules may be coated with shellac, sugar or mixtures thereof. In addition to the active compound, syrups or potions may also comprise sugar (or other sweeteners), methyl- or propylparaben as preservative, a colorant and/or a flavor. The components of the active compound preparations must, of course, be pharmaceutically pure and nontoxic at the quantities employed. Furthermore, the active compounds can be formulated as preparations with a controlled release of active compound, for example as delayed-release preparations. 
     The active compounds can also be administered parenterally or intraperitoneally. Solutions or suspensions of the active compounds or their salts can be prepared with water using suitable wetting agents, such as hydroxypropylcellulose. Dispersions can also be prepared using glycerol, liquid polyethylene glycols and mixtures thereof in oils. Frequently, these preparations furthermore comprise a preservative to prevent the growth of microorganisms. 
     Preparations intended for injections comprise sterile aqueous solutions and dispersions and also sterile powders for preparing sterile solutions and dispersions. The preparation has to be sufficiently liquid for injection. It has to be stable under the preparation and storage conditions and it has to be protected against contamination by microorganisms. The carrier may be a solvent or a dispersion medium, for example, water, ethanol, a polyol (for example glycerol, propylene glycol or liquid polyethylene glycol), a mixture thereof and/or a vegetable oil. 
    
    
     SYNTHESIS EXAMPLES 
     With appropriate modification of the starting materials, the procedures given in the synthesis examples below were used to obtain further compounds I. The compounds produced in this manner are listed in the table below, together with physical data. 
     The HPLC retention times (RT) in the following examples were determined using the RP-18 column Chromolith Speed ROD (Merck KgaA, Germany), with the eluent acetonitrile+0.1% trifluoroacetic acid (TFA)/water+0.1% TFA in a gradient of from 5:95 to 95:5 in 5 minutes at 40° C. Mass spectrometry was effected using quadropole electrospray ionization, 80 V (positive mode) 
     Example 1 
     Preparation of (3-{-4-[3-chloro-5-(4-chlorophenyl)-6-methylpyridazin-4-yl]-3,5-difluorophenoxy}propyl)dimethylamine [I-1] 
     Step 1: 4-[3-Chloro-5-(4-chlorophenyl)-6-methylpyridazin-4-yl)-3,5-difluorophenol 
     0.2 g of 3-chloro-5-(4-chlorophenyl)-4-(2,6-difluoro-4-methoxyphenyl)-6-methylpyridazine (cf. WO 2005/121104) and 1 ml of 1M BBr 3  solution in methylene chloride were stirred at 20 to 25° C. for about 6 hours. The reaction mixture was then hydrolyzed with water, and the aqueous phase was extracted with ethyl acetate. The combined organic phases were dried and freed from the solvent. This gave 0.2 g of the title compound as a lightly colored crystalline material. 
       1 H-NMR (CDCl 3 , δ in ppm): 7.35 (d, 2H); 7.1 (s, br, 1H); 7.05 (d, 2H); 6.4 (d, 2H); 2.55 (s, 3H) 
     Step 2: (3-{-4-[3-Chloro-5-(4-chlorophenyl)-6-methylpyridazin-4-yl]-3,5-difluorophenoxy}propyl)dimethylamine 
     0.2 g of diethyl azodicarboxylate was added to 0.2 g of 4-[3-chloro-5-(4-chlorophenyl)-6-methylpyridazin-4-yl)-3,5-difluorophenol (from step 1), 0.1 g of dimethylaminopropanol and 0.3 g of triphenylphosphine in 5 ml of tetrahydrofuran, and the mixture was stirred at from 20 to 25° C. for about 1 hour. The reaction mixture was concentrated and the residue was purified by MPLC on silica gel using cyclohexane/ethyl acetate mixtures. The residue obtained after concentration of the eluate crystallized and was digested with hexane/diisopropyl ether. This gave 0.13 g of the title compound as a colorless crystalline material of m.p. 112-113° C. 
       1 H-NMR (CDCl 3 , δ in ppm): 7.3 (d, 2H); 7.0 (d, 2H); 6.4 (d, 2H); 3.95 (t, 2H); 2.55 (s, 3H); 2.4 (t, 2H); 2.25 (s, 6H); 1.9 (m, 2H) 
     
       
         
           
               
             
               
                 TABLE I 
               
             
            
               
                   
               
               
                 Compounds of the formula I.A1 
               
            
           
           
               
               
               
               
               
               
               
            
               
                   
                   
                   
                   
                   
                   
                 Phys. data; (m.p. [° C.]; 
               
               
                 No. 
                 R 1   
                 R 2   
                 L m   
                 L 1   
                 R 4   
                 HPLC/MS RT [min]/MS [m/z]) 
               
               
                   
               
               
                 I-1  
                 CH 3   
                 4-Cl—C 6 H 4   
                 2,6-F 2   
                 —O—CH 2 CH 2 CH 2 N(CH 3 ) 2   
                 Cl 
                   
               
               
                 I-2  
                 CH 3   
                 C 6 H 5   
                 2,6-F 2   
                 —O—CH 2 CH 2 CH 2 N(CH 3 ) 2   
                 Cl 
               
               
                 I-3  
                 CH 3   
                 C 6 H 5   
                 2,6-F 2   
                 —O—CH 2 CH 2 CH 2 OH 
                 Cl 
               
               
                 I-4  
                 CH 3   
                 4-F—C 6 H 4   
                 2,6-F 2   
                 —O—CH 2 CH 2 CH 2 N(CH 3 ) 2   
                 Cl 
               
               
                 I-5  
                 CH 3   
                 4-F—C 6 H 4   
                 2,6-F 2   
                 —O—CH 2 CH 2 CH 2 OH 
                 Cl 
               
               
                 I-6  
                 CH 3   
                 4-CH 3 —C 6 H 4   
                 2,6-F 2   
                 —O—CH 2 CH 2 CH 2 N(CH 3 ) 2   
                 Cl 
               
               
                 I-7  
                 CH 3   
                 4-CH 3 —C 6 H 4   
                 2,6-F 2   
                 —O—CH 2 CH 2 CH 2 OH 
                 Cl 
               
               
                 I-8  
                 CH 3   
                 4-Cl—C 6 H 4   
                 2,6-F 2   
                 —O—CH 2 CH 2 CH 2 NHCH 3   
                 Cl 
                 2.669/437.7 
               
               
                 I-9  
                 CH 3   
                 4-Cl—C 6 H 4   
                 2,6-F 2   
                 —O—CH 2 CH 2 CH 2 OH 
                 Cl 
                 47-66 
               
               
                 I-10 
                 CH 3   
                 4-Cl—C 6 H 4   
                 2,6-F 2   
                 —O—CH 2 CH 2 OH 
                 Cl 
                 3.092/410.6 
               
               
                 I-11 
                 CH 3   
                 4-Cl—C 6 H 4   
                 2,6-F 2   
                 —O—CH 2 CH 2 NHC(O)NH 2   
                 Cl 
               
               
                 I-12 
                 CH 3   
                 4-Cl—C 6 H 4   
                 2,6-F 2   
                 —O—CH 2 CH 2 CH 2 NHC(O)NH 2   
                 Cl 
                 158-164 
               
               
                 I-13 
                 CH 3   
                 4-Cl—C 6 H 4   
                 2,6-F 2   
                 —O—CH 2 CH 2 CH 2 OC(O)NH 2   
                 Cl 
               
               
                 I-14 
                 CH 3   
                 4-Cl—C 6 H 4   
                 2,6-F 2   
                 —O—CH 2 CH 2 CH 2 NHC(O)OCH 3   
                 Cl 
                 169-173 
               
               
                 I-15 
                 CH 3   
                 4-Cl—C 6 H 4   
                 2,6-F 2   
                 —O—CH 2 CH 2 CH 2 NHCHO 
                 Cl 
               
               
                 I-16 
                 CH 3   
                 4-Cl—C 6 H 4   
                 2,6-F 2   
                 —O—CH 2 CH 2 CH 2 N(CH 3 )CHO 
                 Cl 
                 3.289/465.6 
               
               
                 I-17 
                 CH 3   
                 4-Cl—C 6 H 4   
                 2,6-F 2   
                 —O—CH 2 CH 2 CH 2 NHC(O)CH 3   
                 Cl 
                 65-70 
               
               
                   
               
               
                 1-18 
                 CH 3   
                 4-Cl—C 6 H 4   
                 2,6-F 2   
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 Cl 
                 203-206 
               
               
                   
               
            
           
         
       
     
     Examples of the Action Against Harmful Fungi 
     The fungicidal action of the compounds of the formula I was demonstrated by the following experiments: 
     The active compounds were prepared as a stock solution comprising 25 mg of active compound which was made up to 10 ml using a mixture of acetone and/or DMSO and the emulsifier Uniperol® EL (wetting agent having emulsifying and dispersing action based on ethoxylated alkylphenols) in a volume ratio of solvent/emulsifier of 99/1. The mixture was then made up to 100 ml with water. This stock solution was diluted with the solvent/emulsifier/water mixture described to the concentration of active compounds stated below. Alternatively, the active compounds were used as a commercial finished formulation and diluted with water to the stated active compound concentration. 
     Use Example 1 
     Activity Against Late Blight on Tomatoes Caused by  Phytophthora infestans , Protective Treatment 
     Leaves of potted tomato plants were sprayed to runoff point with an aqueous suspension having the active compound concentration stated below. The next day, the leaves were infected with an aqueous sporangia suspension of  Phytophthora infestans . The plants were then placed in a water vapor-saturated chamber at temperatures between 18 and 20° C. After 6 days, the late blight on the untreated but infected control plants had developed to such an extent that the infection could be determined visually in %. 
     In this test, the plants treated with 250 ppm of the active compound I-1 showed no infection, whereas the untreated plants were 80% infected. 
     Use Example 2 
     Protective Activity Against  Septoria  Leaf Blotch of Wheat Caused by  Septoria tritici    
     Leaves of potted wheat seedlings were inoculated with a spore suspension of the leaf blotch disease  Septoria tritici . The test plants were then placed in a greenhouse at temperatures between 20 and 22° C. and a relative atmospheric humidity of close to 100% and then at temperatures between 16 and 18° C. and an atmospheric humidity of about 70% for 4 days. Six days after the inoculation, the plants were sprayed to runoff point with an aqueous active compound solution having the concentration stated below. After the spray coating had dried on, the plants were returned. After 14 days, the extent of the development of the disease was determined visually in % infection of the entire leaf area. 
     In this test, the plants which had been treated with 250 ppm of the active compound I-1 showed an infection of 10%, whereas the untreated plants were 90% infected. The active compounds were formulated separately as a stock solution having a concentration of 10 000 ppm in DMSO. 
     Use Example 3 
     Activity Against the  Septoria  Leaf Blotch Pathogen  Septoria tritici  the Microtiter Test 
     The stock solution is pipetted into a microtiter plate (MTP) and diluted with an aqueous malt-based fungus nutrient medium to the stated active compound concentration. An aqueous spore suspension of  Septoria tritici  was then added. The plates were placed in a water vapor-saturated chamber at temperatures of 18° C. Using an absorption photometer, the MTPs were measured at 405 nm on day 7 after the inoculation. 
     The measured parameters were compared to the growth of the active compound-free control variant (100%) and the fungus- and active compound-free blank value to determine the relative growth in % of the pathogens in the individual active compounds. 
     Use Example 4 
     Activity Against the Gray Mold Pathogen  Botrytis cinerea  in the Microtiter Test 
     The stock solution is pipetted into a microtiter plate (Mtp) and diluted with an aqueous malt-based fungus nutrient medium to the stated active compound concentration. An aqueous spore suspension of  Botrytis cinerea  was then added. The plates were placed in a water vapor-saturated chamber at temperatures of 18° C. Using an absorption photometer, the MTPs were measured at 405 nm on day 7 after the inoculation. 
     The measured parameters were compared to the growth of the active compound-free control variant and the fungus- and active compound-free blank value to determine the relative growth in % of the pathogens in the individual active compounds.