Substituted quinolinones having herbicidal action

Abstract

Substituted quinolinones of the formula I

Description

This application claims priority under 35 U.S.C. §119 to European Patent Application No. 09174833.5, filed Nov. 3, 2009, the entire contents of which is hereby incorporated herein by reference.

The present invention relates to quinolinones of the formula I

in which the variables have the following meaning:

• R¹ is O—R^A, S(O)_n—R^A or O—S(O)_n—R^A;
  • R^A is hydrogen, C₁-C₄-alkyl, Z—C₃-C₆-cycloalkyl, C₁-C₄-haloalkyl, C₂-C₆-alkenyl, Z—C₃-C₆-cycloalkenyl, C₂-C₆-alkynyl, Z-(tri-C₁-C₄-alkyl)silyl, Z—C(═O)—R^a, —NRⁱ—C(O)—NRⁱRⁱⁱ, Z—P(═O)(R^a)₂, NRⁱRⁱⁱ, a 3- to 7-membered monocyclic or 9- or 10-membered bicyclic saturated, unsaturated or aromatic heterocycle which contains 1, 2, 3 or 4 heteroatoms selected from the group consisting of O, N and S, which may be partially or fully substituted by groups R^a and/or R^b,
    • R^a is hydrogen, OH, C₁-C₈-alkyl, C₁-C₄-haloalkyl, Z—C₃-C₆-cycloalkyl, C₂-C₈-alkenyl, Z—C₅-C₆-cycloalkenyl, C₂-C₈-alkynyl, Z—C₁-C₆-alkoxy, Z—C₁-C₄-haloalkoxy, Z—C₃-C₈-alkenyloxy, Z—C₃-C₈-alkynyloxy, NRⁱRⁱⁱ, C₁-C₆-alkylsulfonyl, Z-(tri-C₁-C₄-alkyl)silyl, Z-phenyl, Z-phenoxy, Z-phenylamino or a 5- or 6-membered monocyclic or 9- or 10-membered bicyclic heterocycle which contains 1, 2, 3 or 4 heteroatoms selected from the group consisting of O, N and S, where the cyclic groups are unsubstituted or substituted by 1, 2, 3, 4 or 5 groups R^b;
      • Rⁱ, Rⁱⁱ independently of one another are hydrogen, C₁-C₈-alkyl, C₁-C₄-haloalkyl, C₃-C₈-alkenyl, C₃-C₈-alkynyl, Z—C₃-C₆-cycloalkyl, Z—C₁-C₈-alkoxy, Z—C₁-C₈-haloalkoxy, Z—C(═O)—R^a, Z-phenyl, a 3- to 7-membered monocyclic or 9- or 10-membered bicyclic saturated, unsaturated or aromatic heterocycle which contains 1, 2, 3 or 4 heteroatoms selected from the group consisting of O, N and S and which is attached via Z;
      • Rⁱ and Rⁱⁱ together with the nitrogen atom to which they are attached may also form a 5- or 6-membered monocyclic or 9- or 10-membered bicyclic heterocycle which contains 1, 2, 3 or 4 heteroatoms selected from the group consisting of O, N and S;
    • Z is a covalent bond or C₁-C₄-alkylene;
  • n is 0, 1 or 2;
• R² is phenyl, naphthyl or a 5- or 6-membered monocyclic or 9- or 10-membered bicyclic aromatic heterocycle which contains 1, 2, 3 or 4 heteroatoms selected from the group consisting of O, N and S, where the cyclic groups are unsubstituted or substituted by 1, 2, 3 or 4 groups R^b;
  • R^b independently of one another are Z—CN, Z—OH, Z—NO₂, Z-halogen, C₁-C₈-alkyl, C₁-C₄-haloalkyl, C₂-C₈-alkenyl, C₂-C₈-alkynyl, Z—C₁-C₈-alkoxy, Z—C₁-C₈-haloalkoxy, Z—C₃-C₁₀-cycloalkyl, O—Z—C₃-C₁₀-cycloalkyl, Z—C(═O)—R^a, NRⁱRⁱⁱ, Z-(tri-C₁-C₄-alkyl)silyl, Z-phenyl and S(O)_nR^bb,
    • where R^bb is C₁-C₈-alkyl or C₁-C₆-haloalkyl and
    • n is 0, 1 or 2;
    • R^b together with the group R^b attached to the adjacent carbon atom may also form a five- or six-membered saturated or partially or fully unsaturated ring which, in addition to carbon atoms, may contain 1, 2 or 3 heteroatoms selected from the group consisting of O, N and S;
• X is O, S or N—R⁵;
  • R³, R⁴, R⁵ independently of one another are hydrogen, C₁-C₆-alkyl, C₁-C₄-haloalkyl, C₂-C₆-alkenyl, C₃-C₆-alkynyl, Z—C₃-C₁₀-cycloalkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl, C₁-C₆-cyanoalkyl, Z-phenyl, Z—C(═O)—R^a2 or tri-C₁-C₄-alkylsilyl;
    • R^a2 is C₁-C₆-alkyl, C₁-C₄-haloalkyl, Z—C₁-C₆-alkoxy, Z—C₁-C₄-haloalkoxy or NRⁱRⁱⁱ;
• A, E, G, M are N or C—R^b, at least one of these groups being N;
  • R^b is hydrogen or one of the groups mentioned for R^b;where in the groups R^A, R³, R⁴ and R⁵ and their substituents, the carbon chains and/or the cyclic groups may be partially or fully substituted by groups R^b,or a N-oxide or an agriculturally suitable salt thereof.

Moreover, the invention relates to processes and intermediates for preparing the quinolinones of the formula I and the N-oxides thereof, the agriculturally usable salts thereof, and also to active compound combinations comprising them, to compositions comprising them and to their use as herbicides, i.e. for controlling harmful plants, and also to a method for controlling unwanted vegetation which comprises allowing a herbicidally effective amount of at least one quinolinone of the formula I or of an agriculturally suitable salt of I to act on plants, their seed and/or their habitat.

Further embodiments of the present invention can be found in the claims, the description and the examples. It is to be understood that the features mentioned above and those still to be illustrated below of the subject matter of the invention can be applied not only in the respective given combination but also in other combinations without leaving the scope of the invention.

WO 2008/009908 and WO 2008/071918 describe herbicidal pyridopyrazines; however, their herbicidal action at low application rates and/or their compatibility with crop plants leave scope for improvement.

It is an object of the present invention to provide compounds having herbicidal action. To be provided are in particular active compounds having strong herbicidal action, in particular even at low application rates, whose compatibility with crop plants is sufficient for commercial application.

These and further objects are achieved by the compounds of the formula I defined at the outset and by their N-oxides and also their agriculturally suitable salts.

The quinolinones of the formula I according to the invention can be obtained analogously to known synthesis routes.

The reaction of the compounds of the formula II with hydroxylamine is usually carried out at temperatures of from −78° C. to 120° C., preferably from 0° C. to 50° C., in an inert organic solvent in the presence of a base [cf. lit. J. Med. Chem. 2008, 51, 392].

Suitable solvents are aliphatic hydrocarbons, aromatic hydrocarbons, such as toluene, o-, m- and p-xylene, halogenated hydrocarbons, ethers, nitriles, ketones, and also dimethyl sulfoxide, dimethylformamide and dimethylacetamide, particularly preferably toluene. 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, alkali metal and alkaline earth metal oxides, alkali metal and alkaline earth metal hydrides, alkali metal amides, alkali metal and alkaline earth metal carbonates, and also alkali metal bicarbonates, organometallic compounds, alkylmagnesium halides, and also alkali metal and alkaline earth metal alkoxides, 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 pyridine.

The bases are generally employed in catalytic amounts; however, they can also be used in equimolar amounts, in excess or, if appropriate, as solvents.

The starting materials of the formula II required for preparing the compounds I are known from the literature [J. Org. Chem., 1984, 49 (12), 2208] or can be prepared in accordance with the literature cited.

The reaction of the compounds of the formula III with formaldehyde is preferably carried out with an aqueous formaldehyde solution usually at temperatures of from −78° C. to 120° C., preferably from 0° C. to 50° C., in an inert organic solvent in the presence of an acid [cf. lit. J. Org. Chem. 2001, 66, 7666].

Suitable solvents are water, aliphatic hydrocarbons, aromatic hydrocarbons, halogenated hydrocarbons, ethers, nitriles, and also dimethyl sulfoxide, dimethylformamide and dimethylacetamide, particularly preferably water. It is also possible to use mixtures of the solvents mentioned.

Suitable acids and acid 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.

The acids are generally employed in catalytic amounts; however, they can also be used in equimolar amounts, in excess or, if appropriate, as solvents.

The reaction of the compounds of the formula IV with diazomethane compounds of the formula V is usually carried out at temperatures of from −78° C. to 120° C., preferably from 0° C. to 50° C., in an inert organic solvent [cf. Lit. Chem. Ber. 1969, 102, 2429].

Suitable solvents are aliphatic hydrocarbons, aromatic hydrocarbons, halogenated hydrocarbons, ethers, such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, dioxane, anisole and tetrahydrofuran, nitriles, ketones, and also dimethyl sulfoxide, dimethylformamide and dimethylacetamide, particularly preferably ethers. It is also possible to use mixtures of the solvents mentioned.

The starting materials are generally reacted with one another in equimolar amounts.

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, the purification can also be carried out by recrystallization or digestion.

If the synthesis yields mixtures of isomers, a separation is generally however not necessarily required since in some cases the individual isomers can be interconverted during work-up for use or during application (for example under the action of light, acids or bases). Such conversions may also take place after application, for example in the case of the treatment of plants in the treated plant or in the harmful plant to be controlled.

The organic moieties mentioned for the substituents of the compounds according to the invention are collective terms for individual enumerations of the individual group members. All hydrocarbon chains, such as alkyl, haloalkyl, alkenyl, alkynyl, and the alkyl moieties and alkenyl moieties in alkoxy, haloalkoxy, alkylamino, dialkylamino, N-alkylsulfonylamino, alkenyloxy, alkynyloxy, alkoxyamino, alkylaminosulfonylamino, dialkylaminosulfonylamino, alkenylamino, alkynylamino, N-(alkenyl)-N-(alkyl)amino, N-(alkynyl)-N-(alkyl)amino, N-(alkoxy)-N-(alkyl)amino, N-(alkenyl)-N-(alkoxy)amino or N-(alkynyl)-N-(alkoxy)amino can be straight-chain or branched.

The prefix C_n-C_m— indicates the respective number of carbons of the hydrocarbon unit. Unless indicated otherwise, halogenated substituents preferably carry one to five identical or different halogen atoms, in particular fluorine atoms or chlorine atoms.

The meaning halogen denotes in each case fluorine, chlorine, bromine or iodine.

Examples of other meanings are:

alkyl and the alkyl moieties for example in alkoxy, alkylamino, dialkylamino, N-alkylsulfonylamino, alkylaminosulfonylamino, dialkylaminosulfonylamino, N-(alkenyl)-N-(alkyl)amino, N-(alkynyl)-N-(alkyl)amino, N-(alkoxy)-N-(alkyl)amino: saturated straight-chain or branched hydrocarbon radicals having one or more carbon atoms, for example 1 or 2, 1 to 4 or 1 to 6 carbon atoms, for example C₁-C₆-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, hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 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, 1-ethyl-2-methylpropyl. In one embodiment according to the invention, alkyl denotes small alkyl groups, such as C₁-C₄-alkyl. In another embodiment according to the invention, alkyl denotes relatively large alkyl groups, such as C₅-C₆-alkyl.

Haloalkyl: an alkyl radical as mentioned above, some or all of whose hydrogen atoms are substituted by halogen atoms, such as fluorine, chlorine, bromine and/or iodine, for example chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 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, 2-fluoropropyl, 3-fluoropropyl, 2,2-difluoropropyl, 2,3-difluoropropyl, 2-chloropropyl, 3-chloropropyl, 2,3-dichloropropyl, 2-bromopropyl, 3-bromopropyl, 3,3,3-trifluoropropyl, 3,3,3-trichloropropyl, 2,2,3,3,3-pentafluoropropyl, heptafluoropropyl, 1-(fluoromethyl)-2-fluoroethyl, 1-(chloromethyl)-2-chloroethyl, 1-(bromomethyl)-2-bromoethyl, 4-fluorobutyl, 4-chlorobutyl, 4-bromobutyl and nonafluorobutyl.

Cycloalkyl and the cycloalkyl moieties for example in cycloalkoxy or cycloalkylcarbonyl: monocyclic saturated hydrocarbon groups having three or more carbon atoms, for example 3 to 6 carbon ring members, such as cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.

Alkenyl and the alkenyl moieties for example in alkenylamino, alkenyloxy, N-(alkenyl)-N-(alkyl)amino, N-(alkenyl)-N-(alkoxy)amino: monounsaturated straight-chain or branched hydrocarbon radicals having two or more carbon atoms, for example 2 to 4, 2 to 6 or 3 to 6 carbon atoms, and a double bond in any position, for example C₂-C₆-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, 1-ethyl-2-methyl-2-propenyl.

Cycloalkenyl: monocyclic monounsaturated hydrocarbon groups having 3 to 6, preferably 5 or 6, carbon ring members, such as cyclopenten-1-yl, cyclopenten-3-yl, cyclohexen-1-yl, cyclohexen-3-yl, cyclohexen-4-yl.

Alkynyl and the alkynyl moieties for example in alkynyloxy, alkynylamino, N-(alkynyl)-N-(alkyl)amino or N-(alkynyl)-N-(alkoxy)amino: straight-chain or branched hydrocarbon groups having two or more carbon atoms, for example 2 to 4, 2 to 6 or 3 to 6 carbon atoms, and a triple bond in any position, for example C₂-C₆-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, 1-ethyl-1-methyl-2-propynyl.

Alkoxy: alkyl as defined above which is attached via an oxygen atom, for example methoxy, ethoxy, n-propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy or 1,1-dimethylethoxy, pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy or 1-ethyl-2-methylpropoxy.

3- to 7-membered monocyclic or 9- or 10-membered bicyclic saturated, unsaturated or aromatic heterocycle which contains 1, 2, 3, or 4 heteroatoms selected from the group consisting of O, N and S and which can be attached via C or N. Preferred from among these are 5- or 6-membered heterocycles.

Saturated or unsaturated heterocyclic groups which are attached via N, such as: pyridazin-3-yl, pyridazin-4-yl, pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl, pyrazin-2-yl, 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, pyrazol-1-yl, pyrazol-3-yl, pyrazol-4-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, imidazol-1-yl, imidazol-2-yl, imidazol-4-yl, oxazol-2-yl, oxazol-4-yl, oxazol-5-yl, thiazol-2-yl, thiazol-4-yl and thiazol-5-yl.

Heteroaromatic groups which are attached via C, such as: pyrazol-3-yl, imidazol-5-yl, oxazol-2-yl, thiazol-2-yl, thiazol-4-yl, thiazol-5-yl, pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl, pyridazin-4-yl, pyrazin-2-yl, [1H]-tetrazol-5-yl and [2H]-tetrazol-5-yl.

The compounds of the formula I may, depending on the substitution pattern, contain one or more further centers of chirality. Accordingly, the compounds according to the invention can be present as pure enantiomers or diastereomers or as enantiomer or diastereomer mixtures. The invention provides both the pure enantiomers or diastereomers and their mixtures.

The compounds of the formula I may also be present in the form of the N-oxides and/or of their agriculturally useful salts, the type of salt generally not being important. Suitable salts are generally the salts of those cations or the acid addition salts of those acids whose cations and anions, respectively, have no adverse effect on the herbicidal activity of the compounds I.

Suitable cations are in particular ions of the alkali metals, preferably lithium, sodium or potassium, of the alkaline earth metals, preferably calcium or magnesium, and of the transition metals, preferably manganese, copper, zinc or iron. Another cation that may be used is ammonium, where, if desired, one to four hydrogen atoms may be replaced by C₁-C₄-alkyl, hydroxy-C₁-C₄-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, hydroxy-C₁-C₄-alkoxy-C₁-C₄-alkyl, phenyl or benzyl, preferably ammonium, dimethylammonium, diisopropylammonium, tetramethylammonium, tetrabutylammonium, 2-(2-hydroxyeth-1-oxy)eth-1-ylammonium, di(2-hydroxyeth-1-yl)ammonium, trimethylbenzylammonium. Another suitable ammonium cation is the pyridine nitrogen atom of the formula I quaternized by alkylation or arylation. Also suitable are phosphonium ions, sulfonium ions, preferably tri(C₁-C₄-alkyl)sulfonium, or sulfoxonium ions, preferably tri(C₁-C₄-alkyl)sulfoxonium.

Anions of suitable acid addition salts are primarily chloride, bromide, fluoride, hydrogensulfate, sulfate, dihydrogenphosphate, hydrogenphosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate and also the anions of C₁-C₄-alkanoic acids, preferably formate, acetate, propionate, butyrate or trifluoroacetate.

With respect to the variables, the particularly preferred embodiments of the intermediates correspond to those of the groups of the formula I.

In a particular embodiment, the variables of the compounds of the formula I have the following meanings, these meanings, both on their own and in combination with one another, being particular embodiments of the compounds of the formula I:

In one preferred embodiment of the compounds of the formula I, A is N and E, G and M are C—R^c. These compounds correspond to the formula I.1

in which the groups R³ and R⁴ are hydrogen and R^c1, R^c2 and R^c3 each correspond to a group R^c and preferably have the following meanings:

R^c1 is H, OH, CN, halogen, alkyl, alkoxy, haloalkyl, in particular H;

R^c2 is H, OH, CN, halogen, alkyl, alkoxy, haloalkyl, in particular H, Br, OH and OCH₃;

R^c3 is H, OH, CN, halogen, alkyl, alkoxy, haloalkyl, in particular H.

In a further embodiment of the compounds of the formula I, A, E and M are C—R^c and G is N. These compounds correspond to the formula I.2

in which the groups R³ and R⁴ are hydrogen and R^c1, R^c2 and R^c4 each correspond to a group R^c and preferably have the following meanings:

R^c1 is H, OH, CN, halogen, alkyl, alkoxy, haloalkyl, in particular H;

R^c2 is H, OH, CN, halogen, alkyl, alkoxy, haloalkyl, in particular H; and

R^c3 is H, OH, CN, halogen, alkyl, alkoxy, haloalkyl, in particular H, Br, OH and OCH₃.

In a further embodiment of the compounds of the formula I, A and G are N and E and M are C—R^c. These compounds correspond to the formula I.3

in which the groups R³ and R⁴ are hydrogen and R^c1 and R^c3 each correspond to a group R^c and preferably have the following meanings:

R^c1 is H, OH, CN, halogen, alkyl, alkoxy, haloalkyl, in particular H, Br, OH and OCH₃;

R^c2 is H, OH, CN, halogen, alkyl, alkoxy, haloalkyl, in particular H, Br, OH and OCH₃.

In a further embodiment of the compounds of the formula I, A and M are N and E and G are C—R^c. These compounds correspond to the formula I.4

in which the groups R³ and R⁴ are hydrogen and R^c2 and R^c3 each correspond to a group R^c and preferably have the following meanings:

R^c2 is H, OH, CN, halogen, alkyl, alkoxy, haloalkyl, in particular H;

R^c1 is H, OH, CN, halogen, alkyl, alkoxy, haloalkyl, in particular H, Br, OH and OCH₃.

In a further embodiment of the compounds of the formula I, A and E are N and G and M are C—R^c. These compounds correspond to the formula I.5,

in which the groups R³ and R⁴ are hydrogen and R^c3 and R^c4 each correspond to a group R^c and preferably have the following meanings:

R^c1 is H, OH, CN, halogen, alkyl, alkoxy, haloalkyl, in particular H, Br, OH and OCH₃;

R^c2 is H, OH, CN, halogen, alkyl, alkoxy, haloalkyl, in particular H.

Particularly preferred aspects of the compounds of the formula I relate to those of each of the formulae I.1 to I.5 in which the variables have the meanings preferred for formula I.

In a first preferred embodiment of the invention, R¹ is O—R^A.

In a further preferred embodiment of the invention, R¹ is S(O)_n—R^A where n is preferably 0 or 2, in particular 2.

In a further preferred embodiment, R¹ is O—S(O)_n—R^A, where n is preferably 0 or 2, in particular 2, such as, for example, OS(O)₂—CH₃, OS(O)₂—O₂H₅, OS(O)₂—C₃H₇, OS(O)₂—C₆H₅ or OS(O)₂-(4-CH₃—C₆H₄).

In a further preferred embodiment, R¹ is O—S(O), —NRⁱRⁱⁱ, which has in particular the groups NRⁱRⁱⁱ mentioned below as being preferred.

R^A is in particular H, C₁-C₆-alkylcarbonyl, such as C(O)CH₃, C(O)CH₂CH₃, C(O)CH(CH₃)₂ or C(O)C(CH₃)₃; C₁-C₆-cycloalkylcarbonyl, such as cyclopropylcarbonyl, cyclopentylcarbonyl or cyclohexylcarbonyl; C₂-C₆-alkenylcarbonyl, such as C(O)CH═CH₂ or C(O)CH₂CH═CH₂, optionally subst. benzoyl, such as C(O)C₆H₅, C(O)[2-CH₃—C₆H₄], C(O)[4-CH₃—C₆H₄], C(O)[2-F—C₆H₄], C(O)[4-F—C₆H₄], or optionally subst. heteroaryl, such as pyridine, which is attached via a carbonyl group. Particularly preferably, R^A is H or C₁-C₆-alkylcarbonyl.

More particularly preferably, R^A is selected from the group consisting of H, OCH₃, C(O)CH₃, C(O)CH₂CH₃, C(O)CH(CH₃)₂, C(O)C(CH₃)₃, C(O)-c-C₃H₅, C(O)—C₆H₅, C(O)—CH₂C₆H₅, C(O)CH₂Cl, C(O)CF₃, C(O)CH₂OCH₃, C(O)N(CH₃)₂ and C(O)OCH₂CH₃.

In a further preferred embodiment of the invention, R^A is NRⁱRⁱⁱ.

In a further preferred embodiment of the invention, R^A is Z—NRⁱ—C(O)—NRⁱRⁱⁱ, where Rⁱ and Rⁱⁱ are as defined at the outset and preferably as defined below. In further embodiments, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy and C₁-C₄-alkoxy-C₁-C₄-alkyl, in particular OCH₃, OC₂H₅, CH₂CH₂OCH₃ and CH₂CH₂Cl, may also be possible for Rⁱ and Rⁱⁱ, independently of one another.

Rⁱ and Rⁱⁱ are preferably C₁-C₈-alkyl, C₁-C₄-haloalkyl, Z—C₃-C₆-cycloalkyl, Z—C₁-C₈-alkoxy, Z—C₁-C₈-haloalkoxy, Z-phenyl, Z—C(═O)—R^a or Z-hetaryl. Here, preference is given to CH₃, C₂H₅, n-propyl, CH(CH₃)₂, butyl, 2-chloroethyl, cyclopentyl, cyclohexyl, 2-ethoxymethyl, 2-chloroethoxy, phenyl, pyrimidines or triazines whose rings are unsubstituted or substituted. Here, preferred substituents are C₁-C₄-alkylcarbonyl or C₁-C₄-haloalkylcarbonyl, in particular C(═O)—CH₃, C(═O)—C₂H₅, C(═O)—C₃H₇, C(═O)—CH(CH₃)₂, butylcarbonyl and C(═O)—CH₂Cl. Particularly preferred aspects of the group NRⁱRⁱⁱ are N(di-C₁-C₄-alkyl), in particular N(CH₃)—C₁-C₄-alkyl, such as N(CH₃)₂, N(CH₃)CH₂CH₃, N(CH₃)C₃H₇ and N(CH₃)CH(CH₃)₂.

Further particularly preferred aspects of NRⁱRⁱⁱ are NH-aryl, where aryl is preferably phenyl which is substituted—in particular in the 2- and 6-position—by one to three identical or different halogen, CH₃, halo-C₁-C₂-alkyl, halo-C₁-C₂-alkoxy and carboxyl groups, such as 2-C_1-6—COOH—C₆H₃, 2,6-Cl₂-C₆H₃, 2,6-Cl₂-C₆H₃, 2,6-Cl₂-3-C₆H₂, 2-CF₃, 6-CH₂CHF₂—C₆H₃, 2-CF₃-6-OCF₃—C₆H₃ and 2-CF₃-6-CH₂CHF₂—C₆H₃.

Further aspects of NRⁱRⁱⁱ are NH-heteroaryl, where heteroaryl is preferably one of the preferred heteroaromatic groups below, in particular triazinyl, pyrimidinyl or triazolopyrimidinyl, such as [1,2,4]triazolo[1,5-a]pyrimidin-2-yl, which groups may be substituted, in particular by C₁-C₄-alkoxy and/or halogen. Particular preference is given to 5,7-dimethoxy-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl, 5,7-diethoxy-[1,2,4]-triazolo[1,5-a]pyrimidin-2-yl, 5-fluoro-7-methoxy-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl and 5-fluoro-7-ethoxy-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl.

In particularly preferred embodiments of the compounds of the formula I and in particular those of the formula I.1, R¹ is selected from the group consisting of OH, OCH₃, OC(O)CH₃, OC(O)CH₂CH₃, OC(O)CH(CH₃)₂, OC(O)C(CH₃)₃, OC(O)-c-C₃H₅, OC(O)—C₆H₅, OC(O)—CH₂C₆H₅, OC(O)CH₂Cl, OC(O)—CF₃, OC(O)—CH₂OCH₃, OC(O)—N(CH₃)₂ and OC(O)—OCH₂CH₃.

In particularly preferred embodiments of the compounds of the formula I and in particular those of the formula I.1, R² is phenyl which is substituted by a group selected from the group consisting of 2-Br, 2-Cl, 2,4-Cl₂, 2-Cl-4-F, 2-Cl-5-F, 2-Cl-6-F, 2-Cl-4-CF₃, 2-Cl-5-CF₃, 2-Cl-6-CF₃, 2-Cl-3,6-F₂, 2-F, 2,4-F₂, 2,5-F₂, 2,6-F₂, 2-F-4-CF₃, 2-F-5-CF₃, 2-F-6-CF₃, 2,3,6-F₃, 2-NO₂, 2-NO₂-4-F, 2-NO₂-5-F, 2-NO₂-6-F, 2-NO₂-4-CF₃, 2-NO₂-5-CF₃, 2-NO₂-6-CF₃, 2-NO₂-3,6-F₂, 2-CN, 2-CH₃, 2-CH₃-4-F, 2-CH₃-5-F, 2-CH₃-6-F, 2-CH₃-4-CF₃, 2-CH₃-5-CF₃, 2-CH₃-6-CF₃, 2-CH₃-3,6-F₂, 2-OCH₃, 2-OCH₃-4-F, 2-OCH₃-5-F, 2-OCH₃-6-F, 2-OCH₃-4-CF₃, 2-OCH₃-5-CF₃, 2-OCH₃-6-CF₃, 2-OCH₃-3,6-F₂, 2-CH F₂, 2-CHF₂-4-F, 2-CHF₂-5-F, 2-CHF₂-6-F, 2-CHF₂-4-CF₃, 2-CHF₂-5-CF₃, 2-CH F₂-6-CF₃, 2-CHF₂-3,6-F₂, 2-CF₃, 2-CF₃-4-F, 2-CF₃-5-F, 2-CF₃-6-F, 2-CF₃-4-CF₃, 2-CF₃-5-CF₃, 2-CF₃-6-CF₃, 2-CF₃-3,6-F₂, 2-OCHF₂, 2-OCHF₂-4-F, 2-OCHF₂-5-F, 2-OCHF₂-6-F, 2-OCHF₂-4-CF₃, 2-OCHF₂-5-CF₃, 2-OCHF₂-6-CF₃, 2-OCHF₂-3,6-F₂, 2-OCF₃, 2-OCF₃-4-F, 2-OCF₃-5-F, 2-OCF₃-6-F, 2-OCF₃-4-CF₃, 2-OCF₃-5-CF₃, 2-OCF₃-6-CF₃ and 2-OCF₃-3,6-F₂.

In a further preferred embodiment of the invention, R^A is a 5- or 6-membered heterocycle optionally substituted by R^b as defined above, which preferably has either 1, 2, 3 or 4 nitrogen atoms or 1 oxygen or 1 sulfur atom and if appropriate 1 or 2 nitrogen atoms as ring members and which is unsubstituted or may have 1 or 2 substituents selected from R^b. Preference is given to saturated or unsaturated groups attached via nitrogen, such as, for example:

Heteroaromatic groups: pyridazin-3-yl, pyridazin-4-yl, pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl, pyrazin-2-yl, 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, pyrazol-1-yl, pyrazol-3-yl, pyrazol-4-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, imidazol-1-yl, imidazol-2-yl, imidazol-4-yl, oxazol-2-yl, oxazol-4-yl, oxazol-5-yl, thiazol-2-yl, thiazol-4-yl and thiazol-5-yl;

In another aspect, R^A is a heteroaromatic group attached via carbon, such as pyrazol-3-yl, imidazol-5-yl, oxazol-2-yl, thiazol-2-yl, thiazol-4-yl, thiazol-5-yl, pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl, pyridazin-4-yl, pyrazin-2-yl, [1H]-tetrazol-5-yl and [2H]-tetrazol-5-yl, where each of the heterocycles mentioned here in an exemplary manner may have 1 or 2 substituents selected from R^b. Preferred groups R^b are in particular F, Cl, CN, NO₂, CH₃, C₂H₅, OCH₃, OC₂H₅, OCHF₂, OCF₃ and CF₃.

In a further preferred aspect, R² is phenyl which is unsubstituted or partially or fully substituted by groups R^b. Particular preference is given to compounds in which a group R^b is located in the ortho-position. Such compounds of the formula I are described by the formula I.A:

In formula I.A, the index m is zero or an integer from one to four, preferably 0, 1 or 2, in particular 0 or 1. R⁶ and R⁷ are groups R^b as defined at the outset, preferably halogen, NO₂, C₁-C₄-alkyl, C₁-C₂-haloalkyl and C₁-C₄-alkoxy. One group R⁷ is preferably located in position 5. A group R⁷ in position 3 is a further preferred embodiment.

Particularly preferably, R⁶ is Br, F, NO₂, CN, CH₃, OCH₃, CF₃, OCF₃, CHF₂ or OCHF₂. R⁶ is particularly preferably halogen or halomethyl, such as Cl, F or CF₃. Especially preferably, (R⁷)_m is selected from the group consisting of 4-F, 5-F, 6-F, 4-CF₃, 5-CF₃ and 3,6-F₂.

The groups R³ and R⁴ are preferably hydrogen.

In a preferred embodiment, X is O.

In a further embodiment, X is S.

In a further embodiment, X is NR⁵.

R⁵ is preferably H, C₁-C₆-alkyl, such as CH₃, C₂H₅, n-C₃H₇, CH(CH₃)₂, n-C₃H₉, or C(CH₃)₃; C₃-C₆-cycloalkyl-C₁-C₄-alkyl, such as cyclopropylmethyl, C₃-C₆-alkenyl, such as CH₂CH═CH₂, CH₂C(CH₃)═CH₂, CH₂CH₂H═CH₂, CH₂CH₂C(CH₃)—CH₂, CH₂CH₂CH₂CH═CH₂, CH₂CH₂CH₂C(CH₃)═CH₂, or optionally subst. phenyl, such as C₆H₅, 4-CH₃—C₆H₄, 4-F—C₆H₄ or S(O)_n—R^N, where R^N is C₁-C₆-haloalkyl, such as CH₂CF₃, CH₂CHF₂.

A further embodiment relates to the N-oxides of the compounds of the formula I.

A further embodiment relates to salts of the compounds of the formula I, in particular those which are obtainable by quaternization of the pyridine nitrogen atom, which may preferably take place by alkylation or arylation of the compounds of the formula I. Preferred salts of the compounds are thus the N-alkyl salts, in particular the N-methyl salts, and the N-phenyl salts.

In particular with a view to their use, preference is given to the compounds of the formula I compiled in the tables below, which compounds correspond to the formulae I.1A*, I.2A*, I.3A*, I.4A* and I.5A*, respectively. The groups mentioned for a substituent in the tables are furthermore 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.1A*, in which X is oxygen, the index m in (R⁷)_m is zero and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 2

Compounds of the formula I.1A*, in which X is oxygen, (R⁷)_m is 4-Cl and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 3

Compounds of the formula I.1A*, in which X is oxygen, (R⁷)_m is 3-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 4

Compounds of the formula I.1A*, in which X is oxygen, (R⁷)_m is 4-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 5

Compounds of the formula I.1A*, in which X is oxygen, (R⁷)_m is 5-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 6

Compounds of the formula I.1A*, in which X is oxygen, (R⁷)_m is 6-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 7

Compounds of the formula I.1A*, in which X is oxygen, (R⁷)_m is 4-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 8

Compounds of the formula I.1A*, in which X is oxygen, (R⁷)_m is 5-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 9

Compounds of the formula I.1A*, in which X is oxygen, (R⁷)_m is 3,6-F₂ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 10

Compounds of the formula I.1A*, in which X is sulfur, the index m in (R⁷)_m is zero and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 11

Compounds of the formula I.1A*, in which X is sulfur, (R⁷)_m is 4-Cl and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 12

Compounds of the formula I.1A*, in which X is sulfur, (R⁷)_m is 3-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 13

Compounds of the formula I.1A*, in which X is sulfur, (R⁷)_m is 4-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 14

Compounds of the formula I.1A*, in which X is sulfur, (R⁷)_m is 5-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 15

Compounds of the formula I.1A*, in which X is sulfur, (R⁷)_m is 6-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 16

Compounds of the formula I.1A*, in which X is sulfur, (R⁷)_m is 4-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 17

Compounds of the formula I.1A*, in which X is sulfur, (R⁷)_m is 5-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 18

Compounds of the formula I.1A*, in which X is sulfur, (R⁷)_m is 3,6-F₂ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 19

Compounds of the formula I.1A*, in which X is sulfur, the index m in (R⁷)_m is zero and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 20

Compounds of the formula I.1A*, in which X is sulfur, (R⁷)_m is 4-Cl and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 21

Compounds of the formula I.1A*, in which X is sulfur, (R⁷)_m is 3-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 22

Compounds of the formula I.1A*, in which X is sulfur, (R⁷)_m is 4-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 23

Compounds of the formula I.1A*, in which X is sulfur, (R⁷)_m is 5-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 24

Compounds of the formula I.1A*, in which X is sulfur, (R⁷)_m is 6-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 25

Compounds of the formula I.1A*, in which X is sulfur, (R⁷)_m is 4-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 26

Compounds of the formula I.1A*, in which X is sulfur, (R⁷)_m is 5-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 27

Compounds of the formula I.1A*, in which X is sulfur, (R⁷)_m is 3,6-F₂ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 28

Compounds of the formula I.1A*, in which X is N—H, the index m in (R⁷)_m is zero and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 29

Compounds of the formula I.1A*, in which X is N—CH₃, the index m in (R⁷)_m is zero and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 30

Compounds of the formula I.1A*, in which X is N—C₂H₅, the index m in (R⁷)_m is zero and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 31

Compounds of the formula I.1A*, in which X is N-n-C₃H₇, the index m in (R⁷)_m is zero and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 32

Compounds of the formula I.1A*, in which X is N—CH(CH₃)₂, the index m in (R⁷)_m is zero and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 33

Compounds of the formula I.1A*, in which X is N-n-C₄H₉, the index m in (R⁷)_m is zero and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 34

Compounds of the formula I.1A*, in which X is N—CH₂CH═CH₂, the index m in (R⁷)_m is zero and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 35

Compounds of the formula I.1A*, in which X is N—CH₂C≡CH, the index m in (R⁷)_m is zero and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 36

Compounds of the formula I.1A*, in which X is N—CH₂CN, the index m in (R⁷)_m is zero and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 37

Compounds of the formula I.1A*, in which X is N—CH₂CF₃, the index m in (R⁷)_m is zero and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 38

Compounds of the formula I.1A*, in which X is N—CH₂C₆H₅, the index m in (R⁷)_m is zero and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 39

Compounds of the formula I.1A*, in which X is N—H, (R⁷)_m is 4-Cl and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 40

Compounds of the formula I.1A*, in which X is N—CH₃, (R⁷)_m is 4-Cl and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 41

Compounds of the formula I.1A*, in which X is N—C₂H₅, (R⁷)_m is 4-Cl and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 42

Compounds of the formula I.1A*, in which X is N-n-C₃H₇, (R⁷)_m is 4-Cl and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 43

Compounds of the formula I.1A*, in which X is N—CH(CH₃)₂, (R⁷)_m is 4-Cl and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 44

Compounds of the formula I.1A*, in which X is N-n-C₄H₉, (R⁷)_m is 4-Cl and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 45

Compounds of the formula I.1A*, in which X is N—CH₂CH═CH₂, (R⁷)_m is 4-Cl and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 46

Compounds of the formula I.1A*, in which X is N—CH₂C≡CH, (R⁷)_m is 4-Cl and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 47

Compounds of the formula I.1A*, in which X is N—CH₂CN, (R⁷)_m is 4-Cl and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 48

Compounds of the formula I.1A*, in which X is N—CH₂CF₃, (R⁷)_m is 4-Cl and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 49

Compounds of the formula I.1A*, in which X is N—CH₂C₆H₅, (R⁷)_m is 4-Cl and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 50

Compounds of the formula I.1A*, in which X is N—H, (R⁷)_m is 3-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 51

Compounds of the formula I.1A*, in which X is N—CH₃, (R⁷)_m is 3-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 52

Compounds of the formula I.1A*, in which X is N—C₂H₅, (R⁷)_m is 3-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 53

Compounds of the formula I.1A*, in which X is N-n-C₃H₇, (R⁷)_m is 3-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 54

Compounds of the formula I.1A*, in which X is N—CH(CH₃)₂, (R⁷)_m is 3-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 55

Compounds of the formula I.1A*, in which X is N-n-C₄H₉, (R⁷)_m is 3-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 56

Compounds of the formula I.1A*, in which X is N—CH₂CH═CH₂, (R⁷)_m is 3-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 57

Compounds of the formula I.1A*, in which X is N—CH₂C≡CH, (R⁷)_m is 3-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 58

Compounds of the formula I.1A*, in which X is N—CH₂CN, (R⁷)_m is 3-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 59

Compounds of the formula I.1A*, in which X is N—CH₂CF₃, (R⁷)_m is 3-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 60

Compounds of the formula I.1A*, in which X is N—CH₂C₆H₅, (R⁷)_m is 3-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 61

Compounds of the formula I.1A*, in which X is N—H, (R⁷)_m is 4-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 62

Compounds of the formula I.1A*, in which X is N—CH₃, (R⁷)_m is 4-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 63

Compounds of the formula I.1A*, in which X is N—C₂H₅, (R⁷)_m is 4-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 64

Compounds of the formula I.1A*, in which X is N-n-C₃H₇, (R⁷)_m is 4-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 65

Compounds of the formula I.1A*, in which X is N—CH(CH₃)₂, (R⁷)_m is 4-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 66

Compounds of the formula I.1A*, in which X is N-n-C₄H₉, (R⁷)_m is 4-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 67

Compounds of the formula I.1A*, in which X is N—CH₂CH═CH₂, (R⁷)_m is 4-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 68

Compounds of the formula I.1A*, in which X is N—CH₂C≡CH, (R⁷)_m is 4-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 69

Compounds of the formula I.1A*, in which X is N—CH₂CN, (R⁷)_m is 4-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 70

Compounds of the formula I.1A*, in which X is N—CH₂CF₃, (R⁷)_m is 4-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 71

Compounds of the formula I.1A*, in which X is N—CH₂C₆H₅, (R⁷)_m is 4-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 72

Compounds of the formula I.1A*, in which X is N—H, (R⁷)_m is 5-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 73

Compounds of the formula I.1A*, in which X is N—CH₃, (R⁷)_m is 5-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 74

Compounds of the formula I.1A*, in which X is N—C₂H₅, (R⁷)_m is 5-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 75

Compounds of the formula I.1A*, in which X is N-n-C₃H₇, (R⁷)_m is 5-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 76

Compounds of the formula I.1A*, in which X is N—CH(CH₃)₂, (R⁷)_m is 5-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 77

Compounds of the formula I.1A*, in which X is N-n-C₄H₉, (R⁷)_m is 5-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 78

Compounds of the formula I.1A*, in which X is N—CH₂CH═CH₂, (R⁷)_m is 5-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 79

Compounds of the formula I.1A*, in which X is N—CH₂C≡CH, (R⁷)_m is 5-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 80

Compounds of the formula I.1A*, in which X is N—CH₂CN, (R⁷)_m is 5-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 81

Compounds of the formula I.1A*, in which X is N—CH₂CF₃, (R⁷)_m is 5-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 82

Compounds of the formula I.1A*, in which X is N—CH₂C₆H₅, (R⁷)_m is 5-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 83

Compounds of the formula I.1A*, in which X is N—H, (R⁷)_m is 6-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 84

Compounds of the formula I.1A*, in which X is N—CH₃, (R⁷)_m is 6-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 85

Compounds of the formula I.1A*, in which X is N—C₂H₅, (R⁷)_m is 6-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 86

Compounds of the formula I.1A*, in which X is N-n-C₃H₇, (R⁷)_m is 6-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 87

Compounds of the formula I.1A*, in which X is N—CH(CH₃)₂, (R⁷)_m is 6-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 88

Compounds of the formula I.1A*, in which X is N-n-C₄H₉, (R⁷)_m is 6-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 89

Compounds of the formula I.1A*, in which X is N—CH₂CH═CH₂, (R⁷)_m is 6-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 90

Compounds of the formula I.1A*, in which X is N—CH₂C≡CH, (R⁷)_m is 6-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 91

Compounds of the formula I.1A*, in which X is N—CH₂CN, (R⁷)_m is 6-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 92

Compounds of the formula I.1A*, in which X is N—CH₂CF₃, (R⁷)_m is 6-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 93

Compounds of the formula I.1A*, in which X is N—CH₂C₆H₅, (R⁷)_m is 6-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 94

Compounds of the formula I.1A*, in which X is N—H, (R⁷)_m is 4-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 95

Compounds of the formula I.1A*, in which X is N—CH₃, (R⁷)_m is 4-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 96

Compounds of the formula I.1A*, in which X is N—C₂H₅, (R⁷)_m is 4-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 97

Compounds of the formula I.1A*, in which X is N-n-C₃H₇, (R⁷)_m is 4-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 98

Compounds of the formula I.1A*, in which X is N—CH(CH₃)₂, (R⁷)_m is 4-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 99

Compounds of the formula I.1A*, in which X is N-n-C₄H₉, (R⁷)_m is 4-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 100

Compounds of the formula I.1A*, in which X is N—CH₂CH═CH₂, (R⁷)_m is 4-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 101

Compounds of the formula I.1A*, in which X is N—CH₂C≡CH, (R⁷)_m is 4-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 102

Compounds of the formula I.1A*, in which X is N—CH₂CN, (R⁷)_m is 4-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 103

Compounds of the formula I.1A*, in which X is N—CH₂CF₃, (R⁷)_m is 4-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 104

Compounds of the formula I.1A*, in which X is N—CH₂C₆H₅, (R⁷)_m is 4-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 105

Compounds of the formula I.1A*, in which X is N—H, (R⁷)_m is 5-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 106

Compounds of the formula I.1A*, in which X is N—CH₃, (R⁷)_m is 5-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 107

Compounds of the formula I.1A*, in which X is N—C₂H₅, (R⁷)_m is 5-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 108

Compounds of the formula I.1A*, in which X is N-n-C₃H₇, (R⁷)_m is 5-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 109

Compounds of the formula I.1A*, in which X is N—CH(CH₃)₂, (R⁷)_m is 5-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 110

Compounds of the formula I.1A*, in which X is N-n-C₄H₉, (R⁷)_m is 5-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 111

Compounds of the formula I.1A*, in which X is N—CH₂CH═CH₂, (R⁷)_m is 5-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 112

Compounds of the formula I.1A*, in which X is N—CH₂C≡CH, (R⁷)_m is 5-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 113

Compounds of the formula I.1A*, in which X is N—CH₂CN, (R⁷)_m is 5-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 114

Compounds of the formula I.1A*, in which X is N—CH₂CF₃, (R⁷)_m is 5-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 115

Compounds of the formula I.1A*, in which X is N—CH₂C₆H₅, (R⁷)_m is 5-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 116

Compounds of the formula I.1A*, in which X is N—H, (R⁷)_m is 3,6-F₂ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 117

Compounds of the formula I.1A*, in which X is N—CH₃, (R⁷)_m is 3,6-F₂ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 118

Compounds of the formula I.1A*, in which X is N—C₂H₅, (R⁷)_m is 3,6-F₂ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 119

Compounds of the formula I.1A*, in which X is N-n-C₃H₇, (R⁷)_m is 3,6-F₂ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 120

Compounds of the formula I.1A*, in which X is N—CH(CH₃)₂, (R⁷)_m is 3,6-F₂ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 121

Compounds of the formula I.1A*, in which X is N-n-C₄H₉, (R⁷)_m is 3,6-F₂ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 122

Compounds of the formula I.1A*, in which X is N—CH₂CH═CH₂, (R⁷)_m is 3,6-F₂ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 123

Compounds of the formula I.1A*, in which X is N—CH₂C≡CH, (R⁷)_m is 3,6-F₂ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 124

Compounds of the formula I.1A*, in which X is N—CH₂CN, (R⁷)_m is 3,6-F₂ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 125

Compounds of the formula I.1A*, in which X is N—CH₂CF₃, (R⁷)_m is 3,6-F₂ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 126

Compounds of the formula I.1A*, in which X is N—CH₂C₆H₅, (R⁷)_m is 3,6-F₂ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 127

Compounds of the formula I.2A*, in which X is oxygen, the index m in (R⁷)_m is zero and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 128

Compounds of the formula I.2A*, in which X is oxygen, (R⁷)_m is 4-Cl and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 129

Compounds of the formula I.2A*, in which X is oxygen, (R⁷)_m is 3-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 130

Compounds of the formula I.2A*, in which X is oxygen, (R⁷)_m is 4-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 131

Compounds of the formula I.2A*, in which X is oxygen, (R⁷)_m is 5-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 132

Compounds of the formula I.2A*, in which X is oxygen, (R⁷)_m is 6-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 133

Compounds of the formula I.2A*, in which X is oxygen, (R⁷)_m is 4-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 134

Compounds of the formula I.2A*, in which X is oxygen, (R⁷)_m is 5-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 135

Compounds of the formula I.2A*, in which X is oxygen, (R⁷)_m is 3,6-F₂ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 136

Compounds of the formula I.2A*, in which X is sulfur, the index m in (R⁷)_m is zero and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 137

Compounds of the formula I.2A*, in which X is sulfur, (R⁷)_m is 4-Cl and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 138

Compounds of the formula I.2A*, in which X is sulfur, (R⁷)_m is 3-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 139

Compounds of the formula I.2A*, in which X is sulfur, (R⁷)_m is 4-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 140

Compounds of the formula I.2A*, in which X is sulfur, (R⁷)_m is 5-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 141

Compounds of the formula I.2A*, in which X is sulfur, (R⁷)_m is 6-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 142

Compounds of the formula I.2A*, in which X is sulfur, (R⁷)_m is 4-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 143

Compounds of the formula I.2A*, in which X is sulfur, (R⁷)_m is 5-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 144

Compounds of the formula I.2A*, in which X is sulfur, (R⁷)_m is 3,6-F₂ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 145

Compounds of the formula I.2A*, in which X is sulfur, the index m in (R⁷)_m is zero and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 146

Compounds of the formula I.2A*, in which X is sulfur, (R⁷)_m is 4-Cl and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 147

Compounds of the formula I.2A*, in which X is sulfur, (R⁷)_m is 3-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 148

Compounds of the formula I.2A*, in which X is sulfur, (R⁷)_m is 4-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 149

Compounds of the formula I.2A*, in which X is sulfur, (R⁷)_m is 5-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 150

Compounds of the formula I.2A*, in which X is sulfur, (R⁷)_m is 6-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 151

Compounds of the formula I.2A*, in which X is sulfur, (R⁷)_m is 4-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 152

Compounds of the formula I.2A*, in which X is sulfur, (R⁷)_m is 5-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 153

Compounds of the formula I.2A*, in which X is sulfur, (R⁷)_m is 3,6-F₂ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 154

Compounds of the formula I.2A*, in which X is N—H, the index m in (R⁷)_m is zero and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 155

Compounds of the formula I.2A*, in which X is N—CH₃, the index m in (R⁷)_m is zero and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 156

Compounds of the formula I.2A*, in which X is N—C₂H₅, the index m in (R⁷)_m is zero and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 157

Compounds of the formula I.2A*, in which X is N-n-C₃H₇, the index m in (R⁷)_m is zero and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 158

Compounds of the formula I.2A*, in which X is N—CH(CH₃)₂, the index m in (R⁷)_m is zero and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 159

Compounds of the formula I.2A*, in which X is N-n-C₄H₉, the index m in (R⁷)_m is zero and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 160

Compounds of the formula I.2A*, in which X is N—CH₂CH═CH₂, the index m in (R⁷)_m is zero and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 161

Compounds of the formula I.2A*, in which X is N—CH₂C≡CH, the index m in (R⁷)_m is zero and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 162

Compounds of the formula I.2A*, in which X is N—CH₂CN, the index m in (R⁷)_m is zero and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 163

Compounds of the formula I.2A*, in which X is N—CH₂CF₃, the index m in (R⁷)_m is zero and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 164

Compounds of the formula I.2A*, in which X is N—CH₂C₆H₅, the index m in (R⁷)_m is zero and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 165

Compounds of the formula I.2A*, in which X is N—H, (R⁷)_m is 4-Cl and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 166

Compounds of the formula I.2A*, in which X is N—CH₃, (R⁷)_m is 4-Cl and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 167

Compounds of the formula I.2A*, in which X is N—C₂H₅, (R⁷)_m is 4-Cl and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 168

Compounds of the formula I.2A*, in which X is N-n-C₃H₇, (R⁷)_m is 4-Cl and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 169

Compounds of the formula I.2A*, in which X is N—CH(CH₃)₂, (R⁷)_m is 4-Cl and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 170

Compounds of the formula I.2A*, in which X is N-n-C₄H₉, (R⁷)_m is 4-Cl and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 171

Compounds of the formula I.2A*, in which X is N—CH₂CH═CH₂, (R⁷)_m is 4-Cl and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 172

Compounds of the formula I.2A*, in which X is N—CH₂C≡CH, (R⁷)_m is 4-Cl and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 173

Compounds of the formula I.2A*, in which X is N—CH₂CN, (R⁷)_m is 4-Cl and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 174

Compounds of the formula I.2A*, in which X is N—CH₂CF₃, (R⁷)_m is 4-Cl and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 175

Compounds of the formula I.2A*, in which X is N—CH₂C₆H₅, (R⁷)_m is 4-Cl and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 176

Compounds of the formula I.2A*, in which X is N—H, (R⁷)_m is 3-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 177

Compounds of the formula I.2A*, in which X is N—CH₃, (R⁷)_m is 3-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 178

Compounds of the formula I.2A*, in which X is N—C₂H₅, (R⁷)_m is 3-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 179

Compounds of the formula I.2A*, in which X is N-n-C₃H₇, (R⁷)_m is 3-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 180

Compounds of the formula I.2A*, in which X is N—CH(CH₃)₂, (R⁷)_m is 3-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 181

Compounds of the formula I.2A*, in which X is N-n-C₄H₉, (R⁷)_m is 3-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 182

Compounds of the formula I.2A*, in which X is N—CH₂CH═CH₂, (R⁷)_m is 3-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 183

Compounds of the formula I.2A*, in which X is N—CH₂C≡CH, (R⁷)_m is 3-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 184

Compounds of the formula I.2A*, in which X is N—CH₂CN, (R⁷)_m is 3-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 185

Compounds of the formula I.2A*, in which X is N—CH₂CF₃, (R⁷)_m is 3-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 186

Compounds of the formula I.2A*, in which X is N—CH₂C₆H₅, (R⁷)_m is 3-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 187

Compounds of the formula I.2A*, in which X is N—H, (R⁷)_m is 4-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 188

Compounds of the formula I.2A*, in which X is N—CH₃, (R⁷)_m is 4-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 189

Compounds of the formula I.2A*, in which X is N—C₂H₅, (R⁷)_m is 4-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 190

Compounds of the formula I.2A*, in which X is N-n-C₃H₇, (R⁷)_m is 4-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 191

Compounds of the formula I.2A*, in which X is N—CH(CH₃)₂, (R⁷)_m is 4-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 192

Compounds of the formula I.2A*, in which X is N-n-C₄H₉, (R⁷)_m is 4-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 193

Compounds of the formula I.2A*, in which X is N—CH₂CH═CH₂, (R⁷)_m is 4-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 194

Compounds of the formula I.2A*, in which X is N—CH₂C≡CH, (R⁷)_m is 4-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 195

Compounds of the formula I.2A*, in which X is N—CH₂CN, (R⁷)_m is 4-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 196

Compounds of the formula I.2A*, in which X is N—CH₂CF₃, (R⁷)_m is 4-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 197

Compounds of the formula I.2A*, in which X is N—CH₂C₆H₅, (R⁷)_m is 4-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 198

Compounds of the formula I.2A*, in which X is N—H, (R⁷)_m is 5-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 199

Compounds of the formula I.2A*, in which X is N—CH₃, (R⁷)_m is 5-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 200

Compounds of the formula I.2A*, in which X is N—C₂H₅, (R⁷)_m is 5-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 201

Compounds of the formula I.2A*, in which X is N-n-C₃H₇, (R⁷)_m is 5-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 202

Compounds of the formula I.2A*, in which X is N—CH(CH₃)₂, (R⁷)_m is 5-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 203

Compounds of the formula I.2A*, in which X is N-n-C₄H₉, (R⁷)_m is 5-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 204

Compounds of the formula I.2A*, in which X is N—CH₂CH═CH₂, (R⁷)_m is 5-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 205

Compounds of the formula I.2A*, in which X is N—CH₂C≡CH, (R⁷)_m is 5-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 206

Compounds of the formula I.2A*, in which X is N—CH₂CN, (R⁷)_m is 5-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 207

Compounds of the formula I.2A*, in which X is N—CH₂CF₃, (R⁷)_m is 5-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 208

Compounds of the formula I.2A*, in which X is N—CH₂C₆H₅, (R⁷)_m is 5-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 209

Compounds of the formula I.2A*, in which X is N—H, (R⁷)_m is 6-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 210

Compounds of the formula I.2A*, in which X is N—CH₃, (R⁷)_m is 6-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 211

Compounds of the formula I.2A*, in which X is N—C₂H₅, (R⁷)_m is 6-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 212

Compounds of the formula I.2A*, in which X is N-n-C₃H₇, (R⁷)_m is 6-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 213

Compounds of the formula I.2A*, in which X is N—CH(CH₃)₂, (R⁷)_m is 6-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 214

Compounds of the formula I.2A*, in which X is N-n-C₄H₉, (R⁷)_m is 6-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 215

Compounds of the formula I.2A*, in which X is N—CH₂CH═CH₂, (R⁷)_m is 6-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 216

Compounds of the formula I.2A*, in which X is N—CH₂C≡CH, (R⁷)_m is 6-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 217

Compounds of the formula I.2A*, in which X is N—CH₂CN, (R⁷)_m is 6-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 218

Compounds of the formula I.2A*, in which X is N—CH₂CF₃, (R⁷)_m is 6-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 219

Compounds of the formula I.2A*, in which X is N—CH₂C₆H₅, (R⁷)_m is 6-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 220

Compounds of the formula I.2A*, in which X is N—H, (R⁷)_m is 4-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 221

Compounds of the formula I.2A*, in which X is N—CH₃, (R⁷)_m is 4-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 222

Compounds of the formula I.2A*, in which X is N—C₂H₅, (R⁷)_m is 4-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 223

Compounds of the formula I.2A*, in which X is N-n-C₃H₇, (R⁷)_m is 4-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 224

Compounds of the formula I.2A*, in which X is N—CH(CH₃)₂, (R⁷)_m is 4-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 225

Compounds of the formula I.2A*, in which X is N-n-C₄H₉, (R⁷)_m is 4-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 226

Compounds of the formula I.2A*, in which X is N—CH₂CH═CH₂, (R⁷)_m is 4-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 227

Compounds of the formula I.2A*, in which X is N—CH₂C≡CH, (R⁷)_m is 4-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 228

Compounds of the formula I.2A*, in which X is N—CH₂CN, (R⁷)_m is 4-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 229

Compounds of the formula I.2A*, in which X is N—CH₂CF₃, (R⁷)_m is 4-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 230

Compounds of the formula I.2A*, in which X is N—CH₂C₆H₅, (R⁷)_m is 4-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 231

Compounds of the formula I.2A*, in which X is N—H, (R⁷)_m is 5-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 232

Compounds of the formula I.2A*, in which X is N—CH₃, (R⁷)_m is 5-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 233

Compounds of the formula I.2A*, in which X is N—C₂H₅, (R⁷)_m is 5-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 234

Compounds of the formula I.2A*, in which X is N-n-C₃H₇, (R⁷)_m is 5-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 235

Compounds of the formula I.2A*, in which X is N—CH(CH₃)₂, (R⁷)_m is 5-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 236

Compounds of the formula I.2A*, in which X is N-n-C₄H₉, (R⁷)_m is 5-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 237

Compounds of the formula I.2A*, in which X is N—CH₂CH═CH₂, (R⁷)_m is 5-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 238

Compounds of the formula I.2A*, in which X is N—CH₂C≡CH, (R⁷)_m is 5-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 239

Compounds of the formula I.2A*, in which X is N—CH₂CN, (R⁷)_m is 5-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 240

Compounds of the formula I.2A*, in which X is N—CH₂CF₃, (R⁷)_m is 5-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 241

Compounds of the formula I.2A*, in which X is N—CH₂C₆H₅, (R⁷)_m is 5-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 242

Compounds of the formula I.2A*, in which X is N—H, (R⁷)_m is 3,6-F₂ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 243

Compounds of the formula I.2A*, in which X is N—CH₃, (R⁷)_m is 3,6-F₂ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 244

Compounds of the formula I.2A*, in which X is N—C₂H₅, (R⁷)_m is 3,6-F₂ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 245

Compounds of the formula I.2A*, in which X is N-n-C₃H₇, (R⁷)_m is 3,6-F₂ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 246

Compounds of the formula I.2A*, in which X is N—CH(CH₃)₂, (R⁷)_m is 3,6-F₂ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 247

Compounds of the formula I.2A*, in which X is N-n-C₄H₉, (R⁷)_m is 3,6-F₂ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 248

Compounds of the formula I.2A*, in which X is N—CH₂CH═CH₂, (R⁷)_m is 3,6-F₂ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 249

Compounds of the formula I.2A*, in which X is N—CH₂C≡CH, (R⁷)_m is 3,6-F₂ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 250

Compounds of the formula I.2A*, in which X is N—CH₂CN, (R⁷)_m is 3,6-F₂ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 251

Compounds of the formula I.2A*, in which X is N—CH₂CF₃, (R⁷)_m is 3,6-F₂ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 252

Compounds of the formula I.2A*, in which X is N—CH₂C₆H₅, (R⁷)_m is 3,6-F₂ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 253

Compounds of the formula I.3A*, in which X is oxygen, the index m in (R⁷)_m is zero and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 254

Compounds of the formula I.3A*, in which X is oxygen, (R⁷)_m is 4-Cl and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 255

Compounds of the formula I.3A*, in which X is oxygen, (R⁷)_m is 3-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 256

Compounds of the formula I.3A*, in which X is oxygen, (R⁷)_m is 4-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 257

Compounds of the formula I.3A*, in which X is oxygen, (R⁷)_m is 5-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 258

Compounds of the formula I.3A*, in which X is oxygen, (R⁷)_m is 6-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 259

Compounds of the formula I.3A*, in which X is oxygen, (R⁷)_m is 4-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 260

Compounds of the formula I.3A*, in which X is oxygen, (R⁷)_m is 5-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 261

Compounds of the formula I.3A*, in which X is oxygen, (R⁷)_m is 3,6-F₂ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 262

Compounds of the formula I.3A*, in which X is sulfur, the index m in (R⁷)_m is zero and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 263

Compounds of the formula I.3A*, in which X is sulfur, (R⁷)_m is 4-Cl and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 264

Compounds of the formula I.3A*, in which X is sulfur, (R⁷)_m is 3-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 265

Compounds of the formula I.3A*, in which X is sulfur, (R⁷)_m is 4-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 266

Compounds of the formula I.3A*, in which X is sulfur, (R⁷)_m is 5-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 267

Compounds of the formula I.3A*, in which X is sulfur, (R⁷)_m is 6-F and the combination of Wand R⁶ for a compound corresponds in each case to one row of Table A

Table 268

Compounds of the formula I.3A*, in which X is sulfur, (R⁷)_m is 4-CF₃ and the combination of Wand R⁶ for a compound corresponds in each case to one row of Table A

Table 269

Compounds of the formula I.3A*, in which X is sulfur, (R⁷)_m is 5-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 270

Compounds of the formula I.3A*, in which X is sulfur, (R⁷)_m is 3,6-F₂ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 271

Compounds of the formula I.3A*, in which X is sulfur, the index m in (R⁷)_m is zero and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 272

Compounds of the formula I.3A*, in which X is sulfur, (R⁷)_m is 4-Cl and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 273

Compounds of the formula I.3A*, in which X is sulfur, (R⁷)_m is 3-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 274

Compounds of the formula I.3A*, in which X is sulfur, (R⁷)_m is 4-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 275

Compounds of the formula I.3A*, in which X is sulfur, (R⁷)_m is 5-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 276

Compounds of the formula I.3A*, in which X is sulfur, (R⁷)_m is 6-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 277

Compounds of the formula I.3A*, in which X is sulfur, (R⁷)_m is 4-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 278

Compounds of the formula I.3A*, in which X is sulfur, (R⁷)_m is 5-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 279

Compounds of the formula I.3A*, in which X is sulfur, (R⁷)_m is 3,6-F₂ and the combination of Wand R⁶ for a compound corresponds in each case to one row of Table A

Table 280

Compounds of the formula I.3A*, in which X is N—H, the index m in (R⁷)_m is zero and the combination of Wand R⁶ for a compound corresponds in each case to one row of Table A

Table 281

Compounds of the formula I.3A*, in which X is N—CH₃, the index m in (R⁷)_m is zero and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 282

Compounds of the formula I.3A*, in which X is N—C₂H₅, the index m in (R⁷)_m is zero and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 283

Compounds of the formula I.3A*, in which X is N-n-C₃H₇, the index m in (R⁷)_m is zero and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 284

Compounds of the formula I.3A*, in which X is N—CH(CH₃)₂, the index m in (R⁷)_m is zero and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 285

Compounds of the formula I.3A*, in which X is N-n-C₄H₉, the index m in (R⁷)_m is zero and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 286

Compounds of the formula I.3A*, in which X is N—CH₂CH═CH₂, the index m in (R⁷)_m is zero and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 287

Compounds of the formula I.3A*, in which X is N—CH₂C≡CH, the index m in (R⁷)_m is zero and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 288

Compounds of the formula I.3A*, in which X is N—CH₂CN, the index m in (R⁷)_m is zero and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 289

Compounds of the formula I.3A*, in which X is N—CH₂CF₃, the index m in (R⁷)_m is zero and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 290

Compounds of the formula I.3A*, in which X is N—CH₂C₆H₅, the index m in (R⁷)_m is zero and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 291

Compounds of the formula I.3A*, in which X is N—H, (R⁷)_m is 4-Cl and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 292

Compounds of the formula I.3A*, in which X is N—CH₃, (R⁷)_m is 4-Cl and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 293

Compounds of the formula I.3A*, in which X is N—C₂H₅, (R⁷)_m is 4-Cl and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 294

Compounds of the formula I.3A*, in which X is N-n-C₃H₇, (R⁷)_m is 4-Cl and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 295

Compounds of the formula I.3A*, in which X is N—CH(CH₃)₂, (R⁷)_m is 4-Cl and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 296

Compounds of the formula I.3A*, in which X is N-n-C₄H₉, (R⁷)_m is 4-Cl and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 297

Compounds of the formula I.3A*, in which X is N—CH₂CH═CH₂, (R⁷)_m is 4-Cl and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 298

Compounds of the formula I.3A*, in which X is N—CH₂C≡CH, (R⁷)_m is 4-Cl and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 299

Compounds of the formula I.3A*, in which X is N—CH₂CN, (R⁷)_m is 4-Cl and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 300

Compounds of the formula I.3A*, in which X is N—CH₂CF₃, (R⁷)_m is 4-Cl and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 301

Compounds of the formula I.3A*, in which X is N—CH₂C₆H₅, (R⁷)_m is 4-Cl and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 302

Compounds of the formula I.3A*, in which X is N—H, (R⁷)_m is 3-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 303

Compounds of the formula I.3A*, in which X is N—CH₃, (R⁷)_m is 3-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 304

Compounds of the formula I.3A*, in which X is N—C₂H₅, (R⁷)_m is 3-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 305

Compounds of the formula I.3A*, in which X is N-n-C₃H₇, (R⁷)_m is 3-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 306

Compounds of the formula I.3A*, in which X is N—CH(CH₃)₂, (R⁷)_m is 3-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 307

Compounds of the formula I.3A*, in which X is N-n-C₄H₉, (R⁷)_m is 3-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 308

Compounds of the formula I.3A*, in which X is N—CH₂CH═CH₂, (R⁷)_m is 3-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 309

Compounds of the formula I.3A*, in which X is N—CH₂C≡CH, (R⁷)_m is 3-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 310

Compounds of the formula I.3A*, in which X is N—CH₂CN, (R⁷)_m is 3-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 311

Compounds of the formula I.3A*, in which X is N—CH₂CF₃, (R⁷)_m is 3-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 312

Compounds of the formula I.3A*, in which X is N—CH₂C₆H₅, (R⁷)_m is 3-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 313

Compounds of the formula I.3A*, in which X is N—H, (R⁷)_m is 4-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 314

Compounds of the formula I.3A*, in which X is N—CH₃, (R⁷)_m is 4-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 315

Compounds of the formula I.3A*, in which X is N—C₂H₅, (R⁷)_m is 4-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 316

Compounds of the formula I.3A*, in which X is N-n-C₃H₇, (R⁷)_m is 4-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 317

Compounds of the formula I.3A*, in which X is N—CH(CH₃)₂, (R⁷)_m is 4-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 318

Compounds of the formula I.3A*, in which X is N-n-C₄H₉, (R⁷)_m is 4-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 319

Compounds of the formula I.3A*, in which X is N—CH₂CH═CH₂, (R⁷)_m is 4-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 320

Compounds of the formula I.3A*, in which X is N—CH₂C≡CH, (R⁷)_m is 4-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 321

Compounds of the formula I.3A*, in which X is N—CH₂CN, (R⁷)_m is 4-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 322

Compounds of the formula I.3A*, in which X is N—CH₂CF₃, (RR⁷⁶)_m is 4-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 323

Compounds of the formula I.3A*, in which X is N—CH₂C₆H₅, (R⁷)_m is 4-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 324

Compounds of the formula I.3A*, in which X is N—H, (R⁷)_m is 5-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 325

Compounds of the formula I.3A*, in which X is N—CH₃, (R⁷)_m is 5-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 326

Compounds of the formula I.3A*, in which X is N—C₂H₅, (R⁷)_m is 5-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 327

Compounds of the formula I.3A*, in which X is N-n-C₃H₇, (R⁷)_m is 5-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 328

Compounds of the formula I.3A*, in which X is N—CH(CH₃)₂, (R⁷)_m is 5-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 329

Compounds of the formula I.3A*, in which X is N-n-C₄H₉, (R⁷)_m is 5-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 330

Compounds of the formula I.3A*, in which X is N—CH₂CH═CH₂, (R⁷)_m is 5-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 331

Compounds of the formula I.3A*, in which X is N—CH₂C≡CH, (R⁷)_m is 5-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 332

Compounds of the formula I.3A*, in which X is N—CH₂CN, (R⁷)_m is 5-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 333

Compounds of the formula I.3A*, in which X is N—CH₂CF₃, (R⁷)_m is 5-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 334

Compounds of the formula I.3A*, in which X is N—CH₂C₆H₅, (R⁷)_m is 5-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 335

Compounds of the formula I.3A*, in which X is N—H, (R⁷)_m is 6-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 336

Compounds of the formula I.3A*, in which X is N—CH₃, (R⁷)_m is 6-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 337

Compounds of the formula I.3A*, in which X is N—C₂H₅, (R⁷)_m is 6-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 338

Compounds of the formula I.3A*, in which X is N-n-C₃H₇, (R⁷)_m is 6-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 339

Compounds of the formula I.3A*, in which X is N—CH(CH₃)₂, (R⁷)_m is 6-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 340

Compounds of the formula I.3A*, in which X is N-n-C₄H₉, (R⁷)_m is 6-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 341

Compounds of the formula I.3A*, in which X is N—CH₂CH═CH₂, (R⁷)_m is 6-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 342

Compounds of the formula I.3A*, in which X is N—CH₂C≡CH, (R⁷)_m is 6-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 343

Compounds of the formula I.3A*, in which X is N—CH₂CN, (R⁷)_m is 6-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 344

Compounds of the formula I.3A*, in which X is N—CH₂CF₃, (R⁷)_m is 6-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 345

Compounds of the formula I.3A*, in which X is N—CH₂C₆H₅, (R⁷)_m is 6-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 346

Compounds of the formula I.3A*, in which X is N—H, (R⁷)_m is 4-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 347

Compounds of the formula I.3A*, in which X is N—CH₃, (R⁷)_m is 4-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 348

Compounds of the formula I.3A*, in which X is N—C₂H₅, (R⁷)_m is 4-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 349

Compounds of the formula I.3A*, in which X is N-n-C₃H₇, (R⁷)_m is 4-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 350

Compounds of the formula I.3A*, in which X is N—CH(CH₃)₂, (R⁷)_m is 4-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 351

Compounds of the formula I.3A*, in which X is N-n-C₄H₉, (R⁷)_m is 4-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 352

Compounds of the formula I.3A*, in which X is N—CH₂CH═CH₂, (R⁷)_m is 4-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 353

Compounds of the formula I.3A*, in which X is N—CH₂C≡CH, (R⁷)_m is 4-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 354

Compounds of the formula I.3A*, in which X is N—CH₂CN, (R⁷)_m is 4-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 355

Compounds of the formula I.3A*, in which X is N—CH₂CF₃, (R⁷)_m is 4-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 356

Compounds of the formula I.3A*, in which X is N—CH₂C₆H₅, (R⁷)_m is 4-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 357

Compounds of the formula I.3A*, in which X is N—H, (R⁷)_m is 5-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 358

Compounds of the formula I.3A*, in which X is N—CH₃, (R⁷)_m is 5-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 359

Compounds of the formula I.3A*, in which X is N—C₂H₅, (R⁷)_m is 5-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 360

Compounds of the formula I.3A*, in which X is N-n-C₃H₇, (R⁷)_m is 5-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 361

Compounds of the formula I.3A*, in which X is N—CH(CH₃)₂, (R⁷)_m is 5-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 362

Compounds of the formula I.3A*, in which X is N-n-C₄H₉, (R⁷)_m is 5-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 363

Compounds of the formula I.3A*, in which X is N—CH₂CH═CH₂, (R⁷)_m is 5-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 364

Compounds of the formula I.3A*, in which X is N—CH₂C≡CH, (R⁷)_m is 5-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 365

Compounds of the formula I.3A*, in which X is N—CH₂CN, (R⁷)_m is 5-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 366

Compounds of the formula I.3A*, in which X is N—CH₂CF₃, (R⁷)_m is 5-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 367

Compounds of the formula I.3A*, in which X is N—CH₂C₆H₅, (R⁷)_m is 5-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 368

Compounds of the formula I.3A*, in which X is N—H, (R⁷)_m is 3,6-F₂ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 369

Compounds of the formula I.3A*, in which X is N—CH₃, (R⁷)_m is 3,6-F₂ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 370

Compounds of the formula I.3A*, in which X is N—C₂H₅, (R⁷)_m is 3,6-F₂ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 371

Compounds of the formula I.3A*, in which X is N-n-C₃H₇, (R⁷)_m is 3,6-F₂ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 372

Compounds of the formula I.3A*, in which X is N—CH(CH₃)₂, (R⁷)_m is 3,6-F₂ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 373

Compounds of the formula I.3A*, in which X is N-n-C₄H₉, (R⁷)_m is 3,6-F₂ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 374

Compounds of the formula I.3A*, in which X is N—CH₂CH═CH₂, (R⁷)_m is 3,6-F₂ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 375

Compounds of the formula I.3A*, in which X is N—CH₂C≡CH, (R⁷)_m is 3,6-F₂ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 376

Compounds of the formula I.3A*, in which X is N—CH₂CN, (R⁷)_m is 3,6-F₂ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 377

Compounds of the formula I.3A*, in which X is N—CH₂CF₃, (R⁷)_m is 3,6-F₂ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 378

Compounds of the formula I.3A*, in which X is N—CH₂C₆H₅, (R⁷)_m is 3,6-F₂ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 379

Compounds of the formula I.4A*, in which X is oxygen, the index m in (R⁷)_m is zero and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 380

Compounds of the formula I.4A*, in which X is oxygen, (R⁷)_m is 4-Cl and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 381

Compounds of the formula I.4A*, in which X is oxygen, (R⁷)_m is 3-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 382

Compounds of the formula I.4A*, in which X is oxygen, (R⁷)_m is 4-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 383

Compounds of the formula I.4A*, in which X is oxygen, (R⁷)_m is 5-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 384

Compounds of the formula I.4A*, in which X is oxygen, (R⁷)_m is 6-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 385

Compounds of the formula I.4A*, in which X is oxygen, (R⁷)_m is 4-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 386

Compounds of the formula I.4A*, in which X is oxygen, (R⁷)_m is 5-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 387

Compounds of the formula I.4A*, in which X is oxygen, (R⁷)_m is 3,6-F₂ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 388

Compounds of the formula I.4A*, in which X is sulfur, the index m in (R⁷)_m is zero and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 389

Compounds of the formula I.4A*, in which X is sulfur, (R⁷)_m is 4-Cl and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 390

Compounds of the formula I.4A*, in which X is sulfur, (R⁷)_m is 3-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 391

Compounds of the formula I.4A*, in which X is sulfur, (R⁷)_m is 4-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 392

Compounds of the formula I.4A*, in which X is sulfur, (R⁷)_m is 5-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 393

Compounds of the formula I.4A*, in which X is sulfur, (R⁷)_m is 6-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 394

Compounds of the formula I.4A*, in which X is sulfur, (R⁷)_m is 4-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 395

Compounds of the formula I.4A*, in which X is sulfur, (R⁷)_m is 5-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 396

Compounds of the formula I.4A*, in which X is sulfur, (R⁷)_m is 3,6-F₂ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 397

Compounds of the formula I.4A*, in which X is sulfur, the index m in (R⁷)_m is zero and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 398

Compounds of the formula I.4A*, in which X is sulfur, (R⁷)_m is 4-Cl and the combination of Wand R⁶ for a compound corresponds in each case to one row of Table A

Table 399

Compounds of the formula I.4A*, in which X is sulfur, (R⁷)_m is 3-F and the combination of Wand R⁶ for a compound corresponds in each case to one row of Table A

Table 400

Compounds of the formula I.4A*, in which X is sulfur, (R⁷)_m is 4-F and the combination of Wand R⁶ for a compound corresponds in each case to one row of Table A

Table 401

Compounds of the formula I.4A*, in which X is sulfur, (R⁷)_m is 5-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 402

Compounds of the formula I.4A*, in which X is sulfur, (R⁷)_m is 6-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 403

Compounds of the formula I.4A*, in which X is sulfur, (R⁷)_m is 4-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 404

Compounds of the formula I.4A*, in which X is sulfur, (R⁷)_m is 5-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 405

Compounds of the formula I.4A*, in which X is sulfur, (R⁷)_m is 3,6-F₂ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 406

Compounds of the formula I.4A*, in which X is N—H, the index m in (R⁷)_m is zero and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 407

Compounds of the formula I.4A*, in which X is N—CH₃, the index m in (R⁷)_m is zero and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 408

Compounds of the formula I.4A*, in which X is N—C₂H₅, the index m in (R⁷)_m is zero and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 409

Compounds of the formula I.4A*, in which X is N-n-C₃H₇, the index m in (R⁷)_m is zero and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 410

Compounds of the formula I.4A*, in which X is N—CH(CH₃)₂, the index m in (R⁷)_m is zero and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 411

Compounds of the formula I.4A*, in which X is N-n-C₄H₉, the index m in (R⁷)_m is zero and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 412

Compounds of the formula I.4A*, in which X is N—CH₂CH═CH₂, the index m in (R⁷)_m is zero and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 413

Compounds of the formula I.4A*, in which X is N—CH₂C≡CH, the index m in (R⁷)_m is zero and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 414

Compounds of the formula I.4A*, in which X is N—CH₂CN, the index m in (R⁷)_m is zero and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 415

Compounds of the formula I.4A*, in which X is N—CH₂CF₃, the index m in (R⁷)_m is zero and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 416

Compounds of the formula I.4A*, in which X is N—CH₂C₆H₅, the index m in (R⁷)_m is zero and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 417

Compounds of the formula I.4A*, in which X is N—H, (R⁷)_m is 4-Cl and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 418

Compounds of the formula I.4A*, in which X is N—CH₃, (R⁷)_m is 4-Cl and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 419

Compounds of the formula I.4A*, in which X is N—C₂H₅, (R⁷)_m is 4-Cl and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 420

Compounds of the formula I.4A*, in which X is N-n-C₃H₇, (R⁷)_m is 4-Cl and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 421

Compounds of the formula I.4A*, in which X is N—CH(CH₃)₂, (R⁷)_m is 4-Cl and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 422

Compounds of the formula I.4A*, in which X is N-n-C₄H₉, (R⁷)_m is 4-Cl and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 423

Compounds of the formula I.4A*, in which X is N—CH₂CH═CH₂, (R⁷)_m is 4-Cl and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 424

Compounds of the formula I.4A*, in which X is N—CH₂C≡CH, (R⁷)_m is 4-Cl and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 425

Compounds of the formula I.4A*, in which X is N—CH₂CN, (R⁷)_m is 4-Cl and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 426

Compounds of the formula I.4A*, in which X is N—CH₂CF₃, (R⁷)_m is 4-Cl and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 427

Compounds of the formula I.4A*, in which X is N—CH₂C₆H₅, (R⁷)_m is 4-Cl and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 428

Compounds of the formula I.4A*, in which X is N—H, (R⁷)_m is 3-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 429

Compounds of the formula I.4A*, in which X is N—CH₃, (R⁷)_m is 3-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 430

Compounds of the formula I.4A*, in which X is N—C₂H₅, (R⁷)_m is 3-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 431

Compounds of the formula I.4A*, in which X is N-n-C₃H₇, (R⁷)_m is 3-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 432

Compounds of the formula I.4A*, in which X is N—CH(CH₃)₂, (R⁷)_m is 3-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 433

Compounds of the formula I.4A*, in which X is N-n-C₄H₉, (R⁷)_m is 3-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 434

Compounds of the formula I.4A*, in which X is N—CH₂CH═CH₂, (R⁷)_m is 3-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 435

Compounds of the formula I.4A*, in which X is N—CH₂C≡CH, (R⁷)_m is 3-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 436

Compounds of the formula I.4A*, in which X is N—CH₂CN, (R⁷)_m is 3-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 437

Compounds of the formula I.4A*, in which X is N—CH₂CF₃, (R⁷)_m is 3-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 438

Compounds of the formula I.4A*, in which X is N—CH₂C₆H₅, (R⁷)_m is 3-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 439

Compounds of the formula I.4A*, in which X is N—H, (R⁷)_m is 4-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 440

Compounds of the formula I.4A*, in which X is N—CH₃, (R⁷)_m is 4-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 441

Compounds of the formula I.4A*, in which X is N—C₂H₅, (R⁷)_m is 4-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 442

Compounds of the formula I.4A*, in which X is N-n-C₃H₇, (R⁷)_m is 4-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 443

Compounds of the formula I.4A*, in which X is N—CH(CH₃)₂, (R⁷)_m is 4-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 444

Compounds of the formula I.4A*, in which X is N-n-C₄H₉, (R⁷)_m is 4-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 445

Compounds of the formula I.4A*, in which X is N—CH₂CH═CH₂, (R⁷)_m is 4-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 446

Compounds of the formula I.4A*, in which X is N—CH₂C≡CH, (R⁷)_m is 4-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 447

Compounds of the formula I.4A*, in which X is N—CH₂CN, (R⁷)_m is 4-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 448

Compounds of the formula I.4A*, in which X is N—CH₂CF₃, (R⁷)_m is 4-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 449

Compounds of the formula I.4A*, in which X is N—CH₂C₆H₅, (R⁷)_m is 4-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 450

Compounds of the formula I.4A*, in which X is N—H, (R⁷)_m is 5-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 451

Compounds of the formula I.4A*, in which X is N—CH₃, (R⁷)_m is 5-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 452

Compounds of the formula I.4A*, in which X is N—C₂H₅, (R⁷)_m is 5-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 453

Compounds of the formula I.4A*, in which X is N-n-C₃H₇, (R⁷)_m is 5-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 454

Compounds of the formula I.4A*, in which X is N—CH(CH₃)₂, (R⁷)_m is 5-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 455

Compounds of the formula I.4A*, in which X is N-n-C₄H₉, (R⁷)_m is 5-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 456

Compounds of the formula I.4A*, in which X is N—CH₂CH═CH₂, (R⁷)_m is 5-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 457

Compounds of the formula I.4A*, in which X is N—CH₂C≡CH, (R⁷)_m is 5-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 458

Compounds of the formula I.4A*, in which X is N—CH₂CN, (R⁷)_m is 5-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 459

Compounds of the formula I.4A*, in which X is N—CH₂CF₃, (R⁷)_m is 5-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 460

Compounds of the formula I.4A*, in which X is N—CH₂C₆H₅, (R⁷)_m is 5-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 461

Compounds of the formula I.4A*, in which X is N—H, (R⁷)_m is 6-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 462

Compounds of the formula I.4A*, in which X is N—CH₃, (R⁷)_m is 6-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 463

Compounds of the formula I.4A*, in which X is N—C₂H₅, (R⁷)_m is 6-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 464

Compounds of the formula I.4A*, in which X is N-n-C₃H₇, (R⁷)_m is 6-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 465

Compounds of the formula I.4A*, in which X is N—CH(CH₃)₂, (R⁷)_m is 6-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 466

Compounds of the formula I.4A*, in which X is N-n-C₄H₉, (R⁷)_m is 6-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 467

Compounds of the formula I.4A*, in which X is N—CH₂CH═CH₂, (R⁷)_m is 6-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 468

Compounds of the formula I.4A*, in which X is N—CH₂C≡CH, (R⁷)_m is 6-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 469

Compounds of the formula I.4A*, in which X is N—CH₂CN, (R⁷)_m is 6-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 470

Compounds of the formula I.4A*, in which X is N—CH₂CF₃, (R⁷)_m is 6-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 471

Compounds of the formula I.4A*, in which X is N—CH₂C₆H₅, (R⁷)_m is 6-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 472

Compounds of the formula I.4A*, in which X is N—H, (R⁷)_m is 4-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 473

Compounds of the formula I.4A*, in which X is N—CH₃, (R⁷)_m is 4-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 474

Compounds of the formula I.4A*, in which X is N—C₂H₅, (R⁷)_m is 4-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 475

Compounds of the formula I.4A*, in which X is N-n-C₃H₇, (R⁷)_m is 4-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 476

Compounds of the formula I.4A*, in which X is N—CH(CH₃)₂, (R⁷)_m is 4-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 477

Compounds of the formula I.4A*, in which X is N-n-C₄H₉, (R⁷)_m is 4-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 478

Compounds of the formula I.4A*, in which X is N—CH₂CH═CH₂, (R⁷)_m is 4-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 479

Compounds of the formula I.4A*, in which X is N—CH₂C≡CH, (R⁷)_m is 4-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 480

Compounds of the formula I.4A*, in which X is N—CH₂CN, (R⁷)_m is 4-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 481

Compounds of the formula I.4A*, in which X is N—CH₂CF₃, (R⁷)_m is 4-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 482

Compounds of the formula I.4A*, in which X is N—CH₂C₆H₅, (R⁷)_m is 4-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 483

Compounds of the formula I.4A*, in which X is N—H, (R⁷)_m is 5-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 484

Compounds of the formula I.4A*, in which X is N—CH₃, (R⁷)_m is 5-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 485

Compounds of the formula I.4A*, in which X is N—C₂H₅, (R⁷)_m is 5-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 486

Compounds of the formula I.4A*, in which X is N-n-C₃H₇, (R⁷)_m is 5-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 487

Compounds of the formula I.4A*, in which X is N—CH(CH₃)₂, (R⁷)_m is 5-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 488

Compounds of the formula I.4A*, in which X is N-n-C₄H₉, (R⁷)_m is 5-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 489

Compounds of the formula I.4A*, in which X is N—CH₂CH═CH₂, (R⁷)_m is 5-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 490

Compounds of the formula I.4A*, in which X is N—CH₂C≡CH, (R⁷)_m is 5-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 491

Compounds of the formula I.4A*, in which X is N—CH₂CN, (R⁷)_m is 5-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 492

Compounds of the formula I.4A*, in which X is N—CH₂CF₃, (R⁷)_m is 5-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 493

Compounds of the formula I.4A*, in which X is N—CH₂C₆H₅, (R⁷)_m is 5-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 494

Compounds of the formula I.4A*, in which X is N—H, (R⁷)_m is 3,6-F₂ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 495

Compounds of the formula I.4A*, in which X is N—CH₃, (R⁷)_m is 3,6-F₂ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 496

Compounds of the formula I.4A*, in which X is N—C₂H₅, (R⁷)_m is 3,6-F₂ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 497

Compounds of the formula I.4A*, in which X is N-n-C₃H₇, (R⁷)_m is 3,6-F₂ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 498

Compounds of the formula I.4A*, in which X is N—CH(CH₃)₂, (R⁷)_m is 3,6-F₂ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 499

Compounds of the formula I.4A*, in which X is N-n-C₄H₉, (R⁷)_m is 3,6-F₂ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 500

Compounds of the formula I.4A*, in which X is N—CH₂CH═CH₂, (R⁷)_m is 3,6-F₂ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 501

Compounds of the formula I.4A*, in which X is N—CH₂C≡CH, (R⁷)_m is 3,6-F₂ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 502

Compounds of the formula I.4A*, in which X is N—CH₂CN, (R⁷)_m is 3,6-F₂ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 503

Compounds of the formula I.4A*, in which X is N—CH₂CF₃, (R⁷)_m is 3,6-F₂ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 504

Compounds of the formula I.4A*, in which X is N—CH₂C₆H₅, (R⁷)_m is 3,6-F₂ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 505

Compounds of the formula I.5A*, in which X is oxygen, the index m in (R⁷)_m is zero and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 506

Compounds of the formula I.5A*, in which X is oxygen, (R⁷)_m is 4-Cl and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 507

Compounds of the formula I.5A*, in which X is oxygen, (R⁷)_m is 3-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 508

Compounds of the formula I.5A*, in which X is oxygen, (R⁷)_m is 4-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 509

Compounds of the formula I.5A*, in which X is oxygen, (R⁷)_m is 5-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 510

Compounds of the formula I.5A*, in which X is oxygen, (R⁷)_m is 6-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 511

Compounds of the formula I.5A*, in which X is oxygen, (R⁷)_m is 4-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 512

Compounds of the formula I.5A*, in which X is oxygen, (R⁷)_m is 5-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 513

Compounds of the formula I.5A*, in which X is oxygen, (R⁷)_m is 3,6-F₂ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 514

Compounds of the formula I.5A*, in which X is sulfur, the index m in (R⁷)_m is zero and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 515

Compounds of the formula I.5A*, in which X is sulfur, (R⁷)_m is 4-Cl and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 516

Compounds of the formula I.5A*, in which X is sulfur, (R⁷)_m is 3-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 517

Compounds of the formula I.5A*, in which X is sulfur, (R⁷)_m is 4-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 518

Compounds of the formula I.5A*, in which X is sulfur, (R⁷)_m is 5-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 519

Compounds of the formula I.5A*, in which X is sulfur, (R⁷)_m is 6-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 520

Compounds of the formula I.5A*, in which X is sulfur, (R⁷)_m is 4-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 521

Compounds of the formula I.5A*, in which X is sulfur, (R⁷)_m is 5-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 522

Compounds of the formula I.5A*, in which X is sulfur, (R⁷)_m is 3,6-F₂ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 523

Compounds of the formula I.5A*, in which X is sulfur, the index m in (R⁷)_m is zero and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 524

Compounds of the formula I.5A*, in which X is sulfur, (R⁷)_m is 4-Cl and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 525

Compounds of the formula I.5A*, in which X is sulfur, (R⁷)_m is 3-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 526

Compounds of the formula I.5A*, in which X is sulfur, (R⁷)_m is 4-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 527

Compounds of the formula I.5A*, in which X is sulfur, (R⁷)_m is 5-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 528

Compounds of the formula I.5A*, in which X is sulfur, (R⁷)_m is 6-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 529

Compounds of the formula I.5A*, in which X is sulfur, (RR⁷⁶)_m is 4-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 530

Compounds of the formula I.5A*, in which X is sulfur, (R⁷)_m is 5-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 531

Compounds of the formula I.5A*, in which X is sulfur, (R⁷)_m is 3,6-F₂ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 532

Compounds of the formula I.5A*, in which X is N—H, the index m in (R⁷)_m is zero and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 533

Compounds of the formula I.5A*, in which X is N—CH₃, the index m in (R⁷)_m is zero and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 534

Compounds of the formula I.5A*, in which X is N—C₂H₅, the index m in (R⁷)_m is zero and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 535

Compounds of the formula I.5A*, in which X is N-n-C₃H₇, the index m in (R⁷)_m is zero and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 536

Compounds of the formula I.5A*, in which X is N—CH(CH₃)₂, the index m in (R⁷)_m is zero and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 537

Compounds of the formula I.5A*, in which X is N-n-C₄H₉, the index m in (R⁷)_m is zero and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 538

Compounds of the formula I.5A*, in which X is N—CH₂CH═CH₂, the index m in (R⁷)_m is zero and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 539

Compounds of the formula I.5A*, in which X is N—CH₂C≡CH, the index m in (R⁷)_m is zero and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 540

Compounds of the formula I.5A*, in which X is N—CH₂CN, the index m in (R⁷)_m is zero and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 541

Compounds of the formula I.5A*, in which X is N—CH₂CF₃, the index m in (R⁷)_m is zero and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 542

Compounds of the formula I.5A*, in which X is N—CH₂C₆H₅, the index m in (R⁷)_m is zero and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 543

Compounds of the formula I.5A*, in which X is N—H, (R⁷)_m is 4-Cl and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 544

Compounds of the formula I.5A*, in which X is N—CH₃, (R⁷)_m is 4-Cl and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 545

Compounds of the formula I.5A*, in which X is N—C₂H₅, (R⁷)_m is 4-Cl and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 546

Compounds of the formula I.5A*, in which X is N-n-C₃H₇, (R⁷)_m is 4-Cl and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 547

Compounds of the formula I.5A*, in which X is N—CH(CH₃)₂, (R⁷)_m is 4-Cl and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 548

Compounds of the formula I.5A*, in which X is N-n-C₄H₉, (R⁷)_m is 4-Cl and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 549

Compounds of the formula I.5A*, in which X is N—CH₂CH═CH₂, (R⁷)_m is 4-Cl and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 550

Compounds of the formula I.5A*, in which X is N—CH₂C≡CH, (R⁷)_m is 4-Cl and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 551

Compounds of the formula I.5A*, in which X is N—CH₂CN, (R⁷)_m is 4-Cl and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 552

Compounds of the formula I.5A*, in which X is N—CH₂CF₃, (R⁷)_m is 4-Cl and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 553

Compounds of the formula I.5A*, in which X is N—CH₂C₆H₅, (R⁷)_m is 4-Cl and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 554

Compounds of the formula I.5A*, in which X is N—H, (R⁷)_m is 3-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 555

Compounds of the formula I.5A*, in which X is N—CH₃, (R⁷)_m is 3-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 556

Compounds of the formula I.5A*, in which X is N—C₂H₅, (R⁷)_m is 3-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 557

Compounds of the formula I.5A*, in which X is N-n-C₃H₇, (R⁷)_m is 3-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 558

Compounds of the formula I.5A*, in which X is N—CH(CH₃)₂, (R⁷)_m is 3-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 559

Compounds of the formula I.5A*, in which X is N-n-C₄H₉, (R⁷)_m is 3-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 560

Compounds of the formula I.5A*, in which X is N—CH₂CH═CH₂, (R⁷)_m is 3-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 561

Compounds of the formula I.5A*, in which X is N—CH₂C≡CH, (R⁷)_m is 3-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 562

Compounds of the formula I.5A*, in which X is N—CH₂CN, (R⁷)_m is 3-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 563

Compounds of the formula I.5A*, in which X is N—CH₂CF₃, (R⁷)_m is 3-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 564

Compounds of the formula I.5A*, in which X is N—CH₂C₆H₅, (R⁷)_m is 3-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 565

Compounds of the formula I.5A*, in which X is N—H, (R⁷)_m is 4-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 566

Compounds of the formula I.5A*, in which X is N—CH₃, (R⁷)_m is 4-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 567

Compounds of the formula I.5A*, in which X is N—C₂H₅, (R⁷)_m is 4-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 568

Compounds of the formula I.5A*, in which X is N-n-C₃H₇, (R⁷)_m is 4-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 569

Compounds of the formula I.5A*, in which X is N—CH(CH₃)₂, (R⁷)_m is 4-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 570

Compounds of the formula I.5A*, in which X is N-n-C₄H₉, (R⁷)_m is 4-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 571

Compounds of the formula I.5A*, in which X is N—CH₂CH═CH₂, (R⁷)_m is 4-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 572

Compounds of the formula I.5A*, in which X is N—CH₂C≡CH, (R⁷)_m is 4-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 573

Compounds of the formula I.5A*, in which X is N—CH₂CN, (R⁷)_m is 4-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 574

Compounds of the formula I.5A*, in which X is N—CH₂CF₃, (R⁷)_m is 4-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 575

Compounds of the formula I.5A*, in which X is N—CH₂C₆H₅, (R⁷)_m is 4-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 576

Compounds of the formula I.5A*, in which X is N—H, (R⁷)_m is 5-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 577

Compounds of the formula I.5A*, in which X is N—CH₃, (R⁷)_m is 5-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 578

Compounds of the formula I.5A*, in which X is N—C₂H₅, (R⁷)_m is 5-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 579

Compounds of the formula I.5A*, in which X is N-n-C₃H₇, (R⁷)_m is 5-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 580

Compounds of the formula I.5A*, in which X is N—CH(CH₃)₂, (R⁷)_m is 5-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 581

Compounds of the formula I.5A*, in which X is N-n-C₄H₉, (R⁷)_m is 5-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 582

Compounds of the formula I.5A*, in which X is N—CH₂CH═CH₂, (R⁷)_m is 5-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 583

Compounds of the formula I.5A*, in which X is N—CH₂C≡CH, (R⁷)_m is 5-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 584

Compounds of the formula I.5A*, in which X is N—CH₂CN, (R⁷)_m is 5-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 585

Compounds of the formula I.5A*, in which X is N—CH₂CF₃, (R⁷)_m is 5-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 586

Compounds of the formula I.5A*, in which X is N—CH₂C₆H₅, (R⁷)_m is 5-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 587

Compounds of the formula I.5A*, in which X is N—H, (R⁷)_m is 6-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 588

Compounds of the formula I.5A*, in which X is N—CH₃, (R⁷)_m is 6-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 589

Compounds of the formula I.5A*, in which X is N—C₂H₅, (R⁷)_m is 6-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 590

Compounds of the formula I.5A*, in which X is N-n-C₃H₇, (R⁷)_m is 6-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 591

Compounds of the formula I.5A*, in which X is N—CH(CH₃)₂, (R⁷)_m is 6-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 592

Compounds of the formula I.5A*, in which X is N-n-C₄H₉, (R⁷)_m is 6-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 593

Compounds of the formula I.5A*, in which X is N—CH₂CH═CH₂, (R⁷)_m is 6-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 594

Compounds of the formula I.5A*, in which X is N—CH₂C≡CH, (R⁷)_m is 6-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 595

Compounds of the formula I.5A*, in which X is N—CH₂CN, (R⁷)_m is 6-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 596

Compounds of the formula I.5A*, in which X is N—CH₂CF₃, (R⁷)_m is 6-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 597

Compounds of the formula I.5A*, in which X is N—CH₂C₆H₅, (R⁷)_m is 6-F and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 598

Compounds of the formula I.5A*, in which X is N—H, (R⁷)_m is 4-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 599

Compounds of the formula I.5A*, in which X is N—CH₃, (R⁷)_m is 4-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 600

Compounds of the formula I.5A*, in which X is N—C₂H₅, (R⁷)_m is 4-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 601

Compounds of the formula I.5A*, in which X is N-n-C₃H₇, (R⁷)_m is 4-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 602

Compounds of the formula I.5A*, in which X is N—CH(CH₃)₂, (R⁷)_m is 4-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 603

Compounds of the formula I.5A*, in which X is N-n-C₄H₉, (R⁷)_m is 4-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 604

Compounds of the formula I.5A*, in which X is N—CH₂CH═CH₂, (R⁷)_m is 4-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 605

Compounds of the formula I.5A*, in which X is N—CH₂C≡CH, (R⁷)_m is 4-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 606

Compounds of the formula I.5A*, in which X is N—CH₂CN, (R⁷)_m is 4-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 607

Compounds of the formula I.5A*, in which X is N—CH₂CF₃, (R⁷)_m is 4-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 608

Compounds of the formula I.5A*, in which X is N—CH₂C₆H₅, (R⁷)_m is 4-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 609

Compounds of the formula I.5A*, in which X is N—H, (R⁷)_m is 5-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 610

Compounds of the formula I.5A*, in which X is N—CH₃, (R⁷)_m is 5-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 611

Compounds of the formula I.5A*, in which X is N—C₂H₅, (R⁷)_m is 5-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 612

Compounds of the formula I.5A*, in which X is N-n-C₃H₇, (R⁷)_m is 5-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 613

Compounds of the formula I.5A*, in which X is N—CH(CH₃)₂, (R⁷)_m is 5-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 614

Compounds of the formula I.5A*, in which X is N-n-C₄H₉, (R⁷)_m is 5-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 615

Compounds of the formula I.5A*, in which X is N—CH₂CH═CH₂, (R⁷)_m is 5-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 616

Compounds of the formula I.5A*, in which X is N—CH₂C≡CH, (R⁷)_m is 5-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 617

Compounds of the formula I.5A*, in which X is N—CH₂CN, (R⁷)_m is 5-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 618

Compounds of the formula I.5A*, in which X is N—CH₂CF₃, (R⁷)_m is 5-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 619

Compounds of the formula I.5A*, in which X is N—CH₂C₆H₅, (R⁷)_m is 5-CF₃ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 620

Compounds of the formula I.5A*, in which X is N—H, (R⁷)_m is 3,6-F₂ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 621

Compounds of the formula I.5A*, in which X is N—CH₃, (R⁷)_m is 3,6-F₂ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 622

Compounds of the formula I.5A*, in which X is N—C₂H₅, (R⁷)_m is 3,6-F₂ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 623

Compounds of the formula I.5A*, in which X is N-n-C₃H₇, (R⁷)_m is 3,6-F₂ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 624

Compounds of the formula I.5A*, in which X is N—CH(CH₃)₂, (R⁷)_m is 3,6-F₂ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 625

Compounds of the formula I.5A*, in which X is N-n-C₄H₉, (R⁷)_m is 3,6-F₂ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 626

Compounds of the formula I.5A*, in which X is N—CH₂CH═CH₂, (R⁷)_m is 3,6-F₂ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 627

Compounds of the formula I.5A*, in which X is N—CH₂C≡CH, (R⁷)_m is 3,6-F₂ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 628

Compounds of the formula I.5A*, in which X is N—CH₂CN, (R⁷)_m is 3,6-F₂ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 629

Compounds of the formula I.5A*, in which X is N—CH₂CF₃, (R⁷)_m is 3,6-F₂ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

Table 630

Compounds of the formula I.5A*, in which X is N—CH₂C₆H₅, (R⁷)_m is 3,6-F₂ and the combination of R¹ and R⁶ for a compound corresponds in each case to one row of Table A

	No.	R1	R6
	A-1	OH	Br
	A-2	OCH3	Br
	A-3	OC(O)CH3	Br
	A-4	OC(O)CH2CH3	Br
	A-5	OC(O)CH(CH3)2	Br
	A-6	OC(O)C(CH3)3	Br
	A-7	OC(O)-c-C3H5	Br
	A-8	OC(O)—C6H5	Br
	A-9	OC(O)—CH2C6H5	Br
	A-10	OC(O)CH2Cl	Br
	A-11	OC(O)—CF3	Br
	A-12	OC(O)—CH2OCH3	Br
	A-13	OC(O)—N(CH3)2	Br
	A-14	OC(O)—OCH2CH3	Br
	A-15	OS(O)2—CH3	Br
	A-16	OS(O)2—C2H5	Br
	A-17	OS(O)2—C3H7	Br
	A-18	OS(O)2—CH(CH3)2	Br
	A-19	OS(O)2—C6H5	Br
	A-20	OS(O)2—T1	Br
	A-21	OS(O)2—T2	Br
	A-22	OS(O)2—T3	Br
	A-23	OS(O)2—T4	Br
	A-24	OS(O)2—T5	Br
	A-25	OS(O)2—T6	Br
	A-26	OS(O)2—T7	Br
	A-27	OS(O)2—T8	Br
	A-28	OS(O)2—T9	Br
	A-29	OS(O)2—T10	Br
	A-30	OS(O)2—T11	Br
	A-31	OS(O)2—T12	Br
	A-32	OH	Cl
	A-33	OCH3	Cl
	A-34	OC(O)CH3	Cl
	A-35	OC(O)CH2CH3	Cl
	A-36	OC(O)CH(CH3)2	Cl
	A-37	OC(O)C(CH3)3	Cl
	A-38	OC(O)-c-C3H5	Cl
	A-39	OC(O)—C6H5	Cl
	A-40	OC(O)—CH2C6H5	Cl
	A-41	OC(O)CH2Cl	Cl
	A-42	OC(O)—CF3	Cl
	A-43	OC(O)—CH2OCH3	Cl
	A-44	OC(O)—N(CH3)2	Cl
	A-45	OC(O)—OCH2CH3	Cl
	A-46	OS(O)2—CH3	Cl
	A-47	OS(O)2—C2H5	Cl
	A-48	OS(O)2—C3H7	Cl
	A-49	OS(O)2—CH(CH3)2	Cl
	A-50	OS(O)2—C6H5	Cl
	A-51	OS(O)2—T1	Cl
	A-52	OS(O)2—T2	Cl
	A-53	OS(O)2—T3	Cl
	A-54	OS(O)2—T4	Cl
	A-55	OS(O)2—T5	Cl
	A-56	OS(O)2—T6	Cl
	A-57	OS(O)2—T7	Cl
	A-58	OS(O)2—T8	Cl
	A-59	OS(O)2—T9	Cl
	A-60	OS(O)2—T10	Cl
	A-61	OS(O)2—T11	Cl
	A-62	OS(O)2—T12	Cl
	A-63	OH	F
	A-64	OCH3	F
	A-65	OC(O)CH3	F
	A-66	OC(O)CH2CH3	F
	A-67	OC(O)CH(CH3)2	F
	A-68	OC(O)C(CH3)3	F
	A-69	OC(O)-c-C3H5	F
	A-70	OC(O)—C6H5	F
	A-71	OC(O)—CH2C6H5	F
	A-72	OC(O)CH2Cl	F
	A-73	OC(O)—CF3	F
	A-74	OC(O)—CH2OCH3	F
	A-75	OC(O)—N(CH3)2	F
	A-76	OC(O)—OCH2CH3	F
	A-77	OS(O)2—CH3	F
	A-78	OS(O)2—C2H5	F
	A-79	OS(O)2—C3H7	F
	A-80	OS(O)2—CH(CH3)2	F
	A-81	OS(O)2—C6H5	F
	A-82	OS(O)2—T1	F
	A-83	OS(O)2—T2	F
	A-84	OS(O)2—T3	F
	A-85	OS(O)2—T4	F
	A-86	OS(O)2—T5	F
	A-87	OS(O)2—T6	F
	A-88	OS(O)2—T7	F
	A-89	OS(O)2—T8	F
	A-90	OS(O)2—T9	F
	A-91	OS(O)2—T10	F
	A-92	OS(O)2—T11	F
	A-93	OS(O)2—T12	F
	A-94	OH	NO2
	A-95	OCH3	NO2
	A-96	OC(O)CH3	NO2
	A-97	OC(O)CH2CH3	NO2
	A-98	OC(O)CH(CH3)2	NO2
	A-99	OC(O)C(CH3)3	NO2
	A-100	OC(O)-c-C3H5	NO2
	A-101	OC(O)—C6H5	NO2
	A-102	OC(O)—CH2C6H5	NO2
	A-103	OC(O)CH2Cl	NO2
	A-104	OC(O)—CF3	NO2
	A-105	OC(O)—CH2OCH3	NO2
	A-106	OC(O)—N(CH3)2	NO2
	A-107	OC(O)—OCH2CH3	NO2
	A-108	OS(O)2—CH3	NO2
	A-109	OS(O)2—C2H5	NO2
	A-110	OS(O)2—C3H7	NO2
	A-111	OS(O)2—CH(CH3)2	NO2
	A-112	OS(O)2—C6H5	NO2
	A-113	OS(O)2—T1	NO2
	A-114	OS(O)2—T2	NO2
	A-115	OS(O)2—T3	NO2
	A-116	OS(O)2—T4	NO2
	A-117	OS(O)2—T5	NO2
	A-118	OS(O)2—T6	NO2
	A-119	OS(O)2—T7	NO2
	A-120	OS(O)2—T8	NO2
	A-121	OS(O)2—T9	NO2
	A-122	OS(O)2—T10	NO2
	A-123	OS(O)2—T11	NO2
	A-124	OS(O)2—T12	NO2
	A-125	OH	CN
	A-126	OCH3	CN
	A-127	OC(O)CH3	CN
	A-128	OC(O)CH2CH3	CN
	A-129	OC(O)CH(CH3)2	CN
	A-130	OC(O)C(CH3)3	CN
	A-131	OC(O)-c-C3H5	CN
	A-132	OC(O)—C6H5	CN
	A-133	OC(O)—CH2C6H5	CN
	A-134	OC(O)CH2Cl	CN
	A-135	OC(O)—CF3	CN
	A-136	OC(O)—CH2OCH3	CN
	A-137	OC(O)—N(CH3)2	CN
	A-138	OC(O)—OCH2CH3	CN
	A-139	OS(O)2—CH3	CN
	A-140	OS(O)2—C2H5	CN
	A-141	OS(O)2—C3H7	CN
	A-142	OS(O)2—CH(CH3)2	CN
	A-143	OS(O)2—C6H5	CN
	A-144	OS(O)2—T1	CN
	A-145	OS(O)2—T2	CN
	A-146	OS(O)2—T3	CN
	A-147	OS(O)2—T4	CN
	A-148	OS(O)2—T5	CN
	A-149	OS(O)2—T6	CN
	A-150	OS(O)2—T7	CN
	A-151	OS(O)2—T8	CN
	A-152	OS(O)2—T9	CN
	A-153	OS(O)2—T10	CN
	A-154	OS(O)2—T11	CN
	A-155	OS(O)2—T12	CN
	A-156	OH	CH3
	A-157	OCH3	CH3
	A-158	OC(O)CH3	CH3
	A-159	OC(O)CH2CH3	CH3
	A-160	OC(O)CH(CH3)2	CH3
	A-161	OC(O)C(CH3)3	CH3
	A-162	OC(O)-c-C3H5	CH3
	A-163	OC(O)—C6H5	CH3
	A-164	OC(O)—CH2C6H5	CH3
	A-165	OC(O)CH2Cl	CH3
	A-166	OC(O)—CF3	CH3
	A-167	OC(O)—CH2OCH3	CH3
	A-168	OC(O)—N(CH3)2	CH3
	A-169	OC(O)—OCH2CH3	CH3
	A-170	OS(O)2—CH3	CH3
	A-171	OS(O)2—C2H5	CH3
	A-172	OS(O)2—C3H7	CH3
	A-173	OS(O)2—CH(CH3)2	CH3
	A-174	OS(O)2—C6H5	CH3
	A-175	OS(O)2—T1	CH3
	A-176	OS(O)2—T2	CH3
	A-177	OS(O)2—T3	CH3
	A-178	OS(O)2—T4	CH3
	A-179	OS(O)2—T5	CH3
	A-180	OS(O)2—T6	CH3
	A-181	OS(O)2—T7	CH3
	A-182	OS(O)2—T8	CH3
	A-183	OS(O)2—T9	CH3
	A-184	OS(O)2—T10	CH3
	A-185	OS(O)2—T11	CH3
	A-186	OS(O)2—T12	CH3
	A-187	OH	OCH3
	A-188	OCH3	OCH3
	A-189	OC(O)CH3	OCH3
	A-190	OC(O)CH2CH3	OCH3
	A-191	OC(O)CH(CH3)2	OCH3
	A-192	OC(O)C(CH3)3	OCH3
	A-193	OC(O)-c-C3H5	OCH3
	A-194	OC(O)—C6H5	OCH3
	A-195	OC(O)—CH2C6H5	OCH3
	A-196	OC(O)CH2Cl	OCH3
	A-197	OC(O)—CF3	OCH3
	A-198	OC(O)—CH2OCH3	OCH3
	A-199	OC(O)—N(CH3)2	OCH3
	A-200	OC(O)—OCH2CH3	OCH3
	A-201	OS(O)2—CH3	OCH3
	A-202	OS(O)2—C2H5	OCH3
	A-203	OS(O)2—C3H7	OCH3
	A-204	OS(O)2—CH(CH3)2	OCH3
	A-205	OS(O)2—C6H5	OCH3
	A-206	OS(O)2—T1	OCH3
	A-207	OS(O)2—T2	OCH3
	A-208	OS(O)2—T3	OCH3
	A-209	OS(O)2—T4	OCH3
	A-210	OS(O)2—T5	OCH3
	A-211	OS(O)2—T6	OCH3
	A-212	OS(O)2—T7	OCH3
	A-213	OS(O)2—T8	OCH3
	A-214	OS(O)2—T9	OCH3
	A-215	OS(O)2—T10	OCH3
	A-216	OS(O)2—T11	OCH3
	A-217	OS(O)2—T12	OCH3
	A-218	OH	CHF2
	A-219	OCH3	CHF2
	A-220	OC(O)CH3	CHF2
	A-221	OC(O)CH2CH3	CHF2
	A-222	OC(O)CH(CH3)2	CHF2
	A-223	OC(O)C(CH3)3	CHF2
	A-224	OC(O)-c-C3H5	CHF2
	A-225	OC(O)—C6H5	CHF2
	A-226	OC(O)—CH2C6H5	CHF2
	A-227	OC(O)CH2Cl	CHF2
	A-228	OC(O)—CF3	CHF2
	A-229	OC(O)—CH2OCH3	CHF2
	A-230	OC(O)—N(CH3)2	CHF2
	A-231	OC(O)—OCH2CH3	CHF2
	A-232	OS(O)2—CH3	CHF2
	A-233	OS(O)2—C2H5	CHF2
	A-234	OS(O)2—C3H7	CHF2
	A-235	OS(O)2—CH(CH3)2	CHF2
	A-236	OS(O)2—C6H5	CHF2
	A-237	OS(O)2—T1	CHF2
	A-238	OS(O)2—T2	CHF2
	A-239	OS(O)2—T3	CHF2
	A-240	OS(O)2—T4	CHF2
	A-241	OS(O)2—T5	CHF2
	A-242	OS(O)2—T6	CHF2
	A-243	OS(O)2—T7	CHF2
	A-244	OS(O)2—T8	CHF2
	A-245	OS(O)2—T9	CHF2
	A-246	OS(O)2—T10	CHF2
	A-247	OS(O)2—T11	CHF2
	A-248	OS(O)2—T12	CHF2
	A-249	OH	CF3
	A-250	OCH3	CF3
	A-251	OC(O)CH3	CF3
	A-252	OC(O)CH2CH3	CF3
	A-253	OC(O)CH(CH3)2	CF3
	A-254	OC(O)C(CH3)3	CF3
	A-255	OC(O)-c-C3H5	CF3
	A-256	OC(O)—C6H5	CF3
	A-257	OC(O)—CH2C6H5	CF3
	A-258	OC(O)CH2Cl	CF3
	A-259	OC(O)—CF3	CF3
	A-260	OC(O)—CH2OCH3	CF3
	A-261	OC(O)—N(CH3)2	CF3
	A-262	OC(O)—OCH2CH3	CF3
	A-263	OS(O)2—CH3	CF3
	A-264	OS(O)2—C2H5	CF3
	A-265	OS(O)2—C3H7	CF3
	A-266	OS(O)2—CH(CH3)2	CF3
	A-267	OS(O)2—C6H5	CF3
	A-268	OS(O)2—T1	CF3
	A-269	OS(O)2—T2	CF3
	A-270	OS(O)2—T3	CF3
	A-271	OS(O)2—T4	CF3
	A-272	OS(O)2—T5	CF3
	A-273	OS(O)2—T6	CF3
	A-274	OS(O)2—T7	CF3
	A-275	OS(O)2—T8	CF3
	A-276	OS(O)2—T9	CF3
	A-277	OS(O)2—T10	CF3
	A-278	OS(O)2—T11	CF3
	A-279	OS(O)2—T12	CF3
	A-280	OH	OCHF2
	A-281	OCH3	OCHF2
	A-282	OC(O)CH3	OCHF2
	A-283	OC(O)CH2CH3	OCHF2
	A-284	OC(O)CH(CH3)2	OCHF2
	A-285	OC(O)C(CH3)3	OCHF2
	A-286	OC(O)-c-C3H5	OCHF2
	A-287	OC(O)—C6H5	OCHF2
	A-288	OC(O)—CH2C6H5	OCHF2
	A-289	OC(O)CH2Cl	OCHF2
	A-290	OC(O)—CF3	OCHF2
	A-291	OC(O)—CH2OCH3	OCHF2
	A-292	OC(O)—N(CH3)2	OCHF2
	A-293	OC(O)—OCH2CH3	OCHF2
	A-294	OS(O)2—CH3	OCHF2
	A-295	OS(O)2—C2H5	OCHF2
	A-296	OS(O)2—C3H7	OCHF2
	A-297	OS(O)2—CH(CH3)2	OCHF2
	A-298	OS(O)2—C6H5	OCHF2
	A-299	OS(O)2—T1	OCHF2
	A-300	OS(O)2—T2	OCHF2
	A-301	OS(O)2—T3	OCHF2
	A-302	OS(O)2—T4	OCHF2
	A-303	OS(O)2—T5	OCHF2
	A-304	OS(O)2—T6	OCHF2
	A-305	OS(O)2—T7	OCHF2
	A-306	OS(O)2—T8	OCHF2
	A-307	OS(O)2—T9	OCHF2
	A-308	OS(O)2—T10	OCHF2
	A-309	OS(O)2—T11	OCHF2
	A-310	OS(O)2—T12	OCHF2
	A-311	OH	OCF3
	A-312	OCH3	OCF3
	A-313	OC(O)CH3	OCF3
	A-314	OC(O)CH2CH3	OCF3
	A-315	OC(O)CH(CH3)2	OCF3
	A-316	OC(O)C(CH3)3	OCF3
	A-317	OC(O)-c-C3H5	OCF3
	A-318	OC(O)—C6H5	OCF3
	A-319	OC(O)—CH2C6H5	OCF3
	A-320	OC(O)CH2Cl	OCF3
	A-321	OC(O)—CF3	OCF3
	A-322	OC(O)—CH2OCH3	OCF3
	A-323	OC(O)—N(CH3)2	OCF3
	A-324	OC(O)—OCH2CH3	OCF3
	A-325	OS(O)2—CH3	OCF3
	A-326	OS(O)2—C2H5	OCF3
	A-327	OS(O)2—C3H7	OCF3
	A-328	OS(O)2—CH(CH3)2	OCF3
	A-329	OS(O)2—C6H5	OCF3
	A-330	OS(O)2—T1	OCF3
	A-331	OS(O)2—T2	OCF3
	A-332	OS(O)2—T3	OCF3
	A-333	OS(O)2—T4	OCF3
	A-334	OS(O)2—T5	OCF3
	A-335	OS(O)2—T6	OCF3
	A-336	OS(O)2—T7	OCF3
	A-337	OS(O)2—T8	OCF3
	A-338	OS(O)2—T9	OCF3
	A-339	OS(O)2—T10	OCF3
	A-340	OS(O)2—T11	OCF3
	A-341	OS(O)2—T12	OCF3
T1 = NH(4-CH3—C6H4)
T2 = N(CH3)2
T3 = N(CH3)CH2CH3
T4 = N(CH3)C3H7
T5 = N(CH3)CH(CH3)2
T6 = NH(2-Cl-6-COOH—C6H3)
T7 = NH(2,6-Cl2—C6H3)
T8 = NH(2,6-F2—C6H3)
T9 = NH(2,6-Cl2-3-CH3—C6H2)
T10 = NH(2-CF3-6-CH2CHF2—C6H3)
T11 = NH(2-CF3-6-OCF3—C6H3)
T12 = NH(2-CF3-6-OCH2CHF2—C6H3)

The compounds I and their agriculturally useful salts are suitable, both as isomer mixtures and in the form of the pure isomers, as herbicides. They are suitable as such or as an appropriately formulated composition. The herbicidal compositions comprising the compound I, in particular the preferred aspects thereof, control vegetation on non-crop areas very efficiently, especially at high rates of application. They act against broad-leaved weeds and weed grasses in crops such as wheat, rice, corn, soybeans and cotton without causing any significant damage to the crop plants. This effect is mainly observed at low rates of application.

Depending on the application method in question, the compounds I, in particular the preferred aspects thereof, or compositions comprising them can additionally be employed in a further number of crop plants for eliminating unwanted plants. Examples of suitable crops are the following:

Allium cepa, Ananas comosus, Arachis hypogaea, Asparagus officinalis, Avena sativa, Beta vulgaris spec. altissima, Beta vulgaris spec. rapa, Brassica napus var. napus, Brassica napus var. napobrassica, Brassica rapa var. silvestris, Brassica oleracea, Brassica nigra, Camellia sinensis, Carthamus tinctorius, Carya illinoinensis, Citrus limon, Citrus sinensis, Coffea arabica (Coffea canephora, Coffea liberica), Cucumis sativus, Cynodon dactylon, Daucus carota, Elaeis guineensis, Fragaria vesca, Glycine max, Gossypium hirsutum, (Gossypium arboreum, Gossypium herbaceum, Gossypium vitifolium), Helianthus annuus, Hevea brasiliensis, Hordeum vulgare, Humulus lupulus, Ipomoea batatas, Juglans regia, Lens culinaris, Linum usitatissimum, Lycopersicon lycopersicum, Malus spec., Manihot esculenta, Medicago sativa, Musa spec., Nicotiana tabacum (N. rustica), Olea europaea, Oryza sativa, Phaseolus lunatus, Phaseolus vulgaris, Picea abies, Pinus spec., Pistacia vera, Pisum sativum, Prunus avium, Prunus persica, Pyrus communis, Prunus armeniaca, Prunus cerasus, Prunus dulcis and Prunus domestica, Ribes sylvestre, Ricinus communis, Saccharum officinarum, Secale cereale, Sinapis alba, Solanum tuberosum, Sorghum bicolor (s. vulgare), Theobroma cacao, Trifolium pratense, Triticum aestivum, Triticale, Triticum durum, Vicia faba, Vitis vinifera, Zea mays.

The term “crop plants” also includes plants which have been modified by breeding, mutagenesis or genetic engineering. Genetically modified plants are plants whose genetic material has been modified in a manner which does not occur under natural conditions by crossing, mutations or natural recombination (i.e. reassembly of the genetic information). Here, in general, one or more genes are integrated into the genetic material of the plant to improve the properties of the plant.

Accordingly, the term “crop plants” also includes plants which, by breeding and genetic engineering, have acquired tolerance to certain classes of herbicides, such as hydroxyphenylpyruvate dioxygenase (HPPD) inhibitors, acetolactate synthase (ALS) inhibitors, such as, for example, sulfonylureas (EP-A 257 993, U.S. Pat. No. 5,013,659) or imidazolinones (see, for example, U.S. Pat. No. 6,222,100, WO 01/82685, WO 00/26390, WO 97/41218, WO 98/02526, WO 98/02527, WO 04/106529, WO 05/20673, WO 03/14357, WO 03/13225, WO 03/14356, WO 04/16073), enolpyruvylshikimate 3-phosphate synthase (EPSPS) inhibitors, such as, for example, glyphosate (see, for example, WO 92/00377), glutamine synthetase (GS) inhibitors, such as, for example, glufosinate (see, for example, EP-A 242 236, EP-A 242 246), or oxynil herbicides (see, for example, U.S. Pat. No. 5,559,024).

Numerous crop plants, for example Clearfield® oilseed rape, tolerant to imidazolinones, for example imazamox, have been generated with the aid of classic breeding methods (mutagenesis). Crop plants such as soybeans, cotton, corn, beet and oilseed rape, resistant to glyphosate or glufosinate, which are available under the tradenames RoundupReady® (glyphosate) and Liberty Link® (glufosinate) have been generated with the aid of genetic engineering methods.

Accordingly, the term “crop plants” also includes plants which, with the aid of genetic engineering, produce one or more toxins, for example those of the bacterial strain Bacillus ssp. Toxins which are produced by such genetically modified plants include, for example, insecticidal proteins of Bacillus spp., in particular B. thuringiensis, such as the endotoxins Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1, Cry9c, Cry34Ab1 or Cry35Ab1; or vegetative insecticidal proteins (VIPs), for example VIP1, VIP2, VIP3, or VIP3A; insecticidal proteins of nematode-colonizing bacteria, for example Photorhabdus spp. or Xenorhabdus spp.; toxins of animal organisms, for example wasp, spider or scorpion toxins; fungal toxins, for example from Streptomycetes; plant lectins, for example from peas or barley; agglutinins; proteinase inhibitors, for example trypsin inhibitors, serine protease inhibitors, patatin, cystatin or papain inhibitors, ribosome-inactivating proteins (RIPs), for example ricin, corn-RIP, abrin, luffin, saporin or bryodin; steroid-metabolizing enzymes, for example 3-hydroxysteroid oxidase, ecdysteroid-IDP glycosyl transferase, cholesterol oxidase, ecdysone inhibitors, or HMG-CoA reductase; ion channel blockers, for example inhibitors of sodium channels or calcium channels; juvenile hormone esterase; receptors of the diuretic hormone (helicokinin receptors); stilbene synthase, bibenzyl synthase, chitinases and glucanases. In the plants, these toxins may also be produced as pretoxins, hybrid proteins or truncated or otherwise modified proteins. Hybrid proteins are characterized by a novel combination of different protein domains (see, for example, WO 2002/015701). Further examples of such toxins or genetically modified plants which produce these toxins are disclosed in EP-A 374 753, WO 93/007278, WO 95/34656, EP-A 427 529, EP-A 451 878, WO 03/018810 and WO 03/052073. The methods for producing these genetically modified plants are known to the person skilled in the art and disclosed, for example, in the publications mentioned above. Numerous of the toxins mentioned above bestow, upon the plants by which they are produced, tolerance to pests from all taxonomic classes of arthropods, in particular to beetles (Coeleropta), dipterans (Diptera) and butterflies (Lepidoptera) and to nematodes (Nematoda).

Genetically modified plants which produce one or more genes coding for insecticidal toxins are described, for example, in the publications mentioned above, and some of them are commercially available, such as, for example, YieldGard® (corn varieties producing the toxin Cry1Ab), YieldGard® Plus (corn varieties which produce the toxins Cry1Ab and Cry3Bb1), Starlink® (corn varieties which produce the toxin Cry9c), Herculex® RW (corn varieties which produce the toxins Cry34Ab1, Cry35Ab1 and the enzyme phosphinothricin-N-acetyltransferase [PAT]); NuCOTN® 33B (cotton varieties which produce the toxin Cry1Ac), Bollgard® I (cotton varieties which produce the toxin Cry1Ac), Bollgard® II (cotton varieties which produce the toxins Cry1Ac and Cry2Ab2); VIPCOT® (cotton varieties which produce a VIP toxin); NewLeaf° (potato varieties which produce the toxin Cry3A); Bt-Xtra®, NatureGard®, KnockOut®, BiteGard®, Protecta®, Bt11 (for example Agrisure® CB) and Bt176 from Syngenta Seeds SAS, France (corn varieties which produce the toxin Cry1Ab and the PAT enzyme), MIR604 from Syngenta Seeds SAS, France (corn varieties which produce a modified version of the toxin Cry3A, see WO 03/018810), MON 863 from Monsanto Europe S.A., Belgium (corn varieties which produce the toxin Cry3Bb1), IPC 531 from Monsanto Europe S.A., Belgium (cotton varieties which produce a modified version of the toxin Cry1Ac) and 1507 from Pioneer Overseas Corporation, Belgium (corn varieties which produce the toxin Cry1F and the PAT enzyme).

Accordingly, the term “crop plants” also includes plants which, with the aid of genetic engineering, produce one or more proteins which are more robust or have increased resistance to bacterial, viral or fungal pathogens, such as, for example, pathogenesis-related proteins (PR proteins, see EP-A 0 392 225), resistance proteins (for example potato varieties producing two resistance genes against Phytophthora infestans from the wild Mexican potato Solanum bulbocastanum) or T4 lysozyme (for example potato cultivars which, by producing this protein, are resistant to bacteria such as Erwinia amylvora).

Accordingly, the term “crop plants” also includes plants whose productivity has been improved with the aid of genetic engineering methods, for example by enhancing the potential yield (for example biomass, grain yield, starch, oil or protein content), tolerance to drought, salt or other limiting environmental factors or resistance to pests and fungal, bacterial and viral pathogens.

The term “crop plants” also includes plants whose ingredients have been modified with the aid of genetic engineering methods in particular for improving human or animal diet, for example by oil plants producing health-promoting long-chain omega 3 fatty acids or monounsaturated omega 9 fatty acids (for example Nexera® oilseed rape).

The term “crop plants” also includes plants which have been modified with the aid of genetic engineering methods for improving the production of raw materials, for example by increasing the amylopectin content of potatoes (Amflora® potato).

Furthermore, it has been found that the compounds of the formula I are also suitable for the defoliation and/or desiccation of plant parts, for which crop plants such as cotton, potato, oilseed rape, sunflower, soybean or field beans, in particular cotton, are suitable. In this regard, there have been found compositions for the desiccation and/or defoliation of plants, processes for preparing these compositions and methods for desiccating and/or defoliating plants using the compounds of the formula I.

As desiccants, the compounds of the formula I are particularly suitable for desiccating the above-ground parts of crop plants such as potato, oilseed rape, sunflower and soybean, but also cereals. This makes possible the fully mechanical harvesting of these important crop plants.

Also of economic interest is to facilitate harvesting, which is made possible by concentrating within a certain period of time the dehiscence, or reduction of adhesion to the tree, in citrus fruit, olives and other species and varieties of pomaceous fruit, stone fruit and nuts. The same mechanism, i.e. the promotion of the development of abscission tissue between fruit part or leaf part and shoot part of the plants is also essential for the readily controllable defoliation of useful plants, in particular cotton.

Moreover, a shortening of the time interval in which the individual cotton plants mature leads to an increased fiber quality after harvesting.

The compounds I, or the herbicidal compositions comprising the compounds I, can be used, for example, in the form of ready-to-spray aqueous solutions, powders, suspensions, also highly concentrated aqueous, oily or other suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, materials for broadcasting, or granules, by means of spraying, atomizing, dusting, spreading, watering or treatment of the seed or mixing with the seed. The use forms depend on the intended purpose; in each case, they should ensure the finest possible distribution of the active ingredients according to the invention.

The herbicidal compositions comprise a herbicidally effective amount of at least one compound of the formula I or an agriculturally useful salt of I, and auxiliaries which are customary for the formulation of crop protection agents.

Examples of auxiliaries customary for the formulation of crop protection agents are inert auxiliaries, solid carriers, surfactants (such as dispersants, protective colloids, emulsifiers, wetting agents and tackifiers), organic and inorganic thickeners, bactericides, antifreeze agents, antifoams, if appropriate colorants and, for seed formulations, adhesives.

Examples of thickeners (i.e. compounds which impart to the formulation modified flow properties, i.e. high viscosity in the state of rest and low viscosity in motion) are polysaccharides, such as xanthan gum (Kelzan® from Kelco), Rhodopol® 23 (Rhone Poulenc) or Veegum® (from R.T. Vanderbilt), and also organic and inorganic sheet minerals, such as Attaclay® (from Engelhardt).

Examples of antifoams are silicone emulsions (such as, for example, Silikon® SRE, Wacker or Rhodorsil® from Rhodia), long-chain alcohols, fatty acids, salts of fatty acids, organofluorine compounds and mixtures thereof.

Bactericides can be added for stabilizing the aqueous herbicidal formulation. Examples of bactericides are bactericides based on dichlorophen and benzyl alcohol hemiformal (Proxel® from ICI or Acticide® RS from Thor Chemie and Kathon® MK from Rohm & Haas), and also isothiazolinone derivates, such as alkylisothiazolinones and benzisothiazolinones (Acticide MBS from Thor Chemie).

Examples of antifreeze agents are ethylene glycol, propylene glycol, urea or glycerol.

Examples of colorants are both sparingly water-soluble pigments and water-soluble dyes. Examples which may be mentioned are the dyes known under the names Rhodamin B, C.I. Pigment Red 112 and C.I. Solvent Red 1, and also pigment blue 15:4, pigment blue 15:3, pigment blue 15:2, pigment blue 15:1, pigment blue 80, pigment yellow 1, pigment yellow 13, pigment red 112, pigment red 48:2, pigment red 48:1, pigment red 57:1, pigment red 53:1, pigment orange 43, pigment orange 34, pigment orange 5, pigment green 36, pigment green 7, pigment white 6, pigment brown 25, basic violet 10, basic violet 49, acid red 51, acid red 52, acid red 14, acid blue 9, acid yellow 23, basic red 10, basic red 108.

Examples of adhesives are polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and tylose.

Suitable inert auxiliaries are, for example, the following:

mineral oil fractions of medium to high boiling point, such as kerosene and diesel oil, furthermore coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, for example paraffin, tetrahydronaphthalene, alkylated naphthalenes and their derivatives, alkylated benzenes and their derivatives, alcohols such as methanol, ethanol, propanol, butanol and cyclohexanol, ketones such as cyclohexanone or strongly polar solvents, for example amines such as N-methylpyrrolidone, and water.

Solid carriers are mineral earths such as silicas, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate and magnesium oxide, ground synthetic materials, fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate and ureas, and products of vegetable origin, such as cereal meal, tree bark meal, wood meal and nutshell meal, cellulose powders, or other solid carriers.

Suitable surfactants (adjuvants, wetting agents, tackifiers, dispersants and also emulsifiers) are the alkali metal salts, alkaline earth metal salts and ammonium salts of aromatic sulfonic acids, for example lignosulfonic acids (e.g. Borrespers-types, Borregaard), phenolsulfonic acids, naphthalenesulfonic acids (Morwet types, Akzo Nobel) and dibutylnaphthalenesulfonic acid (Nekal types, BASF SE), and of fatty acids, alkyl- and alkylarylsulfonates, alkyl sulfates, lauryl ether sulfates and fatty alcohol sulfates, and salts of sulfated hexa-, hepta- and octadecanols, and also of fatty alcohol glycol ethers, condensates of sulfonated naphthalene and its derivatives with formaldehyde, condensates of naphthalene or of the naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctyl-, octyl- or nonylphenol, alkylphenyl or tributylphenyl polyglycol ether, alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol/ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers or polyoxypropylene alkyl ethers, lauryl alcohol polyglycol ether acetate, sorbitol esters, lignosulfite waste liquors and proteins, denatured proteins, polysaccharides (e.g. methylcellulose), hydrophobically modified starches, polyvinyl alcohol (Mowiol types Clariant), polycarboxylates (BASF SE, Sokalan types), polyalkoxylates, polyvinylamine (BASF SE, Lupamine types), polyethyleneimine (BASF SE, Lupasol types), polyvinylpyrrolidone and copolymers thereof.

Powders, materials for broadcasting and dusts can be prepared by mixing or grinding the active ingredients together with a solid carrier.

Granules, for example coated granules, impregnated granules and homogeneous granules, can be prepared by binding the active ingredients to solid carriers.

Aqueous use forms can be prepared from emulsion concentrates, suspensions, pastes, wettable powders or water-dispersible granules by adding water. To prepare emulsions, pastes or oil dispersions, the compounds of the formula I or Ia, either as such or dissolved in an oil or solvent, can be homogenized in water by means of a wetting agent, tackifier, dispersant or emulsifier. Alternatively, it is also possible to prepare concentrates comprising active substance, wetting agent, tackifier, dispersant or emulsifier and, if desired, solvent or oil, which are suitable for dilution with water.

The concentrations of the compounds of the formula I in the ready-to-use preparations can be varied within wide ranges. In general, the formulations comprise from 0.001 to 98% by weight, preferably 0.01 to 95% by weight of at least one active compound. The active compounds are employed in a purity of from 90% to 100%, preferably 95% to 100% (according to NMR spectrum).

The compounds I of the invention can for example be formulated as follows:

1. Products for Dilution with Water

A Water-Soluble Concentrates

10 parts by weight of active compound are dissolved in 90 parts by weight of water or a water-soluble solvent. As an alternative, wetters or other adjuvants are added. The active compound dissolves upon dilution with water. This gives a formulation with an active compound content of 10% by weight.

B Dispersible Concentrates

20 parts by weight of active compound 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

15 parts by weight of active compound are dissolved in 75 parts by weight of an organic solvent (e.g. alkylaromatics) 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

25 parts by weight of active compound are dissolved in 35 parts by weight of an organic solvent (e.g. alkylaromatics) 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 emulsifier (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

In an agitated ball mill, 20 parts by weight of active compound are comminuted with addition of 10 parts by weight of dispersants and wetters 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

50 parts by weight of active compound are ground finely with addition of 50 parts by weight of dispersants and wetters and made into 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

75 parts by weight of active compound are ground in a rotor-stator mill with addition of 25 parts by weight of dispersants, wetters 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

In a ball mill, 20 parts by weight of active compound, 10 parts by weight of dispersant, 1 part by weight of gelling agent and 70 parts by weight of water or of an organic solvent are ground to give a fine suspension. Dilution with water gives a stable suspension with active compound content of 20% by weight.

2. Products to be Applied Undiluted

I Dusts

5 parts by weight of active compound are ground finely and mixed intimately with 95 parts by weight of finely divided kaolin. This gives a dusting powder with an active compound content of 5% by weight.

J Granules (GR, FG, GG, MG)

0.5 parts by weight of active compound are ground finely and associated with 99.5 parts by weight of carriers. Current methods here are extrusion, spray-drying or the fluidized bed. This gives granules to be applied undiluted with an active compound content of 0.5% by weight.

K ULV Solutions (UL)

10 parts by weight of active compound are dissolved in 90 parts by weight of an organic solvent, for example xylene. This gives a product to be applied undiluted with an active compound content of 10% by weight.

The compounds I or the herbicidal compositions comprising them can be applied pre- or post-emergence, or together with the seed of a crop plant. It is also possible to apply the herbicidal compositions or active compounds by applying seed, pretreated with the herbicidal compositions or active compounds, of a crop plant. If the active compounds are less well tolerated by certain crop plants, application techniques may be used in which the herbicidal compositions are sprayed, with the aid of the spraying equipment, in such a way that as far as possible they do not come into contact with the leaves of the sensitive crop plants, while the active compounds reach the leaves of undesirable plants growing underneath, or the bare soil surface (post-directed, lay-by).

In a further embodiment, the compounds of the formula I or the herbicidal compositions can be applied by treating seed.

The treatment of seed comprises essentially all procedures familiar to the person skilled in the art (seed dressing, seed coating, seed dusting, seed soaking, seed film coating, seed multilayer coating, seed encrusting, seed dripping and seed pelleting) based on the compounds of the formula I according to the invention or the compositions prepared therefrom. Here, the herbicidal compositions can be applied diluted or undiluted.

The term seed comprises seed of all types, such as, for example, corns, seeds, fruits, tubers, cuttings and similar forms. Here, preferably, the term seed describes corns and seeds.

The seed used can be seed of the useful plants mentioned above, but also the seed of transgenic plants or plants obtained by customary breeding methods.

The rates of application of active compound are from 0.001 to 3.0, preferably 0.01 to 1.0, kg/ha of active substance (a.s.), depending on the control target, the season, the target plants and the growth stage. To treat the seed, the compounds I are generally employed in amounts of from 0.001 to 10 kg per 100 kg of seed.

It may also be advantageous to use the compounds of the formula I in combination with safeners. Safeners are chemical compounds which prevent or reduce damage to useful plants without substantially affecting the herbicidal action of the compounds of the formula I on unwanted plants. They can be used both before sowing (for example in the treatment of seed, or on cuttings or seedlings) and before or after the emergence of the useful plant. The safeners and the compounds of the formula I can be used simultaneously or in succession. Suitable safeners are, for example, (quinolin-8-oxy)acetic acids, 1-phenyl-5-haloalkyl-1H-1,2,4-triazole-3-carboxylic acids, 1-phenyl-4,5-dihydro-5-alkyl-1H-pyrazole-3,5-dicarboxylic acids, 4,5-dihydro-5,5-diaryl-3-isoxazolecarboxylic acids, dichloroacetamides, alpha-oximinophenylacetonitriles, acetophenone oximes, 4,6-dihalo-2-phenylpyrimidines, N-[[4-(aminocarbonyl)phenyl]-sulfonyl]-2-benzamides, 1,8-naphthalic anhydride, 2-halo-4-(haloalkyl)-5-thiazolecarboxylic acids, phosphorothiolates and O-phenyl N-alkylcarbamates and their agriculturally useful salts and, provided that they have an acid function, their agriculturally useful derivatives, such as amides, esters and thioesters.

To broaden the activity spectrum and to obtain synergistic effects, the compounds of the formula I can be mixed and jointly applied with numerous representatives of other herbicidal or growth-regulating groups of active compounds or with safeners. Suitable mixing partners are, for example, 1,2,4-thiadiazoles, 1,3,4-thiadiazoles, amides, aminophosphoric acid and its derivatives, aminotriazoles, anilides, aryloxy/heteroaryloxyalkanoic acids and their derivatives, benzoic acid and its derivatives, benzothiadiazinones, 2-(hetaroyl/aroyl)-1,3-cyclohexanediones, heteroaryl aryl ketones, benzylisoxazolidinones, meta-CF₃-phenyl derivatives, carbamates, quinoline carboxylic acid and its derivatives, chloroacetanilides, cyclohexenone oxime ether derivates, diazines, dichloropropionic acid and its derivatives, dihydrobenzofurans, dihydrofuran-3-ones, dinitroanilines, dinitrophenols, diphenyl ethers, dipyridyls, halocarboxylic acids and their derivatives, ureas, 3-phenyluracils, imidazoles, imidazolinones, N-phenyl-3,4,5,6-tetrahydrophthalimides, oxadiazoles, oxiranes, phenols, aryloxy- and heteroaryloxyphenoxypropionic esters, phenylacetic acid and its derivatives, 2-phenylpropionic acid and its derivatives, pyrazoles, phenylpyrazoles, pyridazines, pyridinecarboxylic acid and its derivatives, pyrimidyl ethers, sulfonamides, sulfonylureas, triazines, triazinones, triazolinones, triazolecarboxamides, uracils and also phenylpyrazolines and isoxazolines and their derivatives.

Moreover, it may be useful to apply the compounds I alone or in combination with other herbicides or else also mixed with further crop protection agents, jointly, for example with compositions for controlling pests or phytopathogenic fungi or bacteria. Also of interest is the miscibility with mineral salt solutions which are employed for alleviating nutritional and trace element deficiencies. Other additives such as nonphytotoxic oils and oil concentrates may also be added.

Examples of herbicides which can be used in combination with the pyridine compounds of the formula I according to the present invention are:

b1) from the group of the lipid biosynthesis inhibitors:

alloxydim, alloxydim-sodium, butroxydim, clethodim, clodinafop, clodinafop-propargyl, cycloxydim, cyhalofop, cyhalofop-butyl, diclofop, diclofop-methyl, fenoxaprop, fenoxaprop-ethyl, fenoxaprop-P, fenoxaprop-P-ethyl, fluazifop, fluazifop-butyl, fluazifop-P, fluazifop-P-butyl, haloxyfop, haloxyfop-methyl, haloxyfop-P, haloxyfop-P-methyl, metamifop, pinoxaden, profoxydim, propaquizafop, quizalofop, quizalofop-ethyl, quizalofop-tefuryl, quizalofop-P, quizalofop-P-ethyl, quizalofop-P-tefuryl, sethoxydim, tepraloxydim, tralkoxydim, benfuresate, butylate, cycloate, dalapon, dimepiperate, EPTC, esprocarb, ethofumesate, flupropanate, molinate, orbencarb, pebulate, prosulfocarb, TCA, thiobencarb, tiocarbazil, triallate and vernolate;

b2) from the group of the ALS inhibitors:

amidosulfuron, azimsulfuron, bensulfuron, bensulfuron-methyl, bispyribac, bispyribac-sodium, chlorimuron, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cloransulam, cloransulam-methyl, cyclosulfamuron, diclosulam, ethametsulfuron, ethametsulfuron-methyl, ethoxysulfuron, flazasulfuron, florasulam, flucarbazone, flucarbazone-sodium, flucetosulfuron, flumetsulam, flupyrsulfuron, flupyrsulfuron-methyl-sodium, foramsulfuron, halosulfuron, halosulfuron-methyl, imazamethabenz, imazamethabenz-methyl, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, imazosulfuron, iodosulfuron, iodosulfuron-methyl-sodium, mesosulfuron, metosulam, metsulfuron, metsulfuron-methyl, nicosulfuron, orthosulfamuron, oxasulfuron, penoxsulam, primisulfuron, primisulfuron-methyl, propoxycarbazone, propoxycarbazone-sodium, prosulfuron, pyrazosulfuron, pyrazosulfuron-ethyl, pyribenzoxim, pyrimisulfan, pyriftalid, pyriminobac, pyriminobac-methyl, pyrithiobac, pyrithiobac-sodium, pyroxsulam, rimsulfuron, sulfometuron, sulfometuron-methyl, sulfosulfuron, thiencarbazone, thiencarbazone-methyl, thifensulfuron, thifensulfuron-methyl, triasulfuron, tribenuron, tribenuron-methyl, trifloxysulfuron, triflusulfuron, triflusulfuron-methyl and tritosulfuron;

b3) from the group of the photosynthesis inhibitors:

ametryn, amicarbazone, atrazine, bentazone, bentazone-sodium, bromacil, bromofenoxim, bromoxynil and its salts and esters, chlorobromuron, chloridazone, chlorotoluron, chloroxuron, cyanazine, desmedipham, desmetryn, dimefuron, dimethametryn, diquat, diquat-dibromide, diuron, fluometuron, hexazinone, ioxynil and its salts and esters, isoproturon, isouron, karbutilate, lenacil, linuron, metamitron, methabenzthiazuron, metobenzuron, metoxuron, metribuzin, monolinuron, neburon, paraquat, paraquat-dichloride, paraquat-dimetilsulfate, pentanochlor, phenmedipham, phenmedipham-ethyl, prometon, prometryn, propanil, propazine, pyridafol, pyridate, siduron, simazine, simetryn, tebuthiuron, terbacil, terbumeton, terbuthylazine, terbutryn, thidiazuron and trietazine;

b4) from the group of the protoporphyrinogen-IX oxidase inhibitors:

acifluorfen, acifluorfen-sodium, azafenidin, bencarbazone, benzfendizone, bifenox, butafenacil, carfentrazone, carfentrazone-ethyl, chlomethoxyfen, cinidon-ethyl, fluazolate, flufenpyr, flufenpyr-ethyl, flumiclorac, flumiclorac-pentyl, flumioxazin, fluoroglycofen, fluoroglycofen-ethyl, fluthiacet, fluthiacet-methyl, fomesafen, halosafen, lactofen, oxadiargyl, oxadiazon, oxyfluorfen, pentoxazone, profluazol, pyraclonil, pyraflufen, pyraflufen-ethyl, saflufenacil, sulfentrazone, thidiazimin, 2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluoro-N-[(isopropyl)-methylsulfamoyl]benzamide (H-1; CAS 372137-35-4), ethyl[3-[2-chloro-4-fluoro-5-(1-methyl-6-trifluoromethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-3-yl)phenoxy]-2-pyridyloxy]acetate (H-2; CAS 353292-31-6), N-ethyl-3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (H-3; CAS 452098-92-9), N-tetrahydrofurfuryl-3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (H-4; CAS 915396-43-9), N-ethyl-3-(2-chloro-6-fluoro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (H-5; CAS 452099-05-7) and N-tetrahydrofurfuryl-3-(2-chloro-6-fluoro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (H-6; CAS 45100-03-7);

b5) from the group of the bleacher herbicides:

aclonifen, amitrol, beflubutamid, benzobicyclon, benzolenap, clomazone, diflufenican, fluridone, fluorochloridone, flurtamone, isoxaflutole, mesotrione, norflurazon, picolinafen, pyrasulfutole, pyrazolynate, pyrazoxyfen, sulcotrione, tefuryltrione, tembotrione, topramezone, 4-hydroxy-3-[[2-[(2-methoxyethoxy)methyl]-6-(trifluoromethyl)-3-pyridyl]carbonyl]bicyclo[3.2.1]oct-3-en-2-one (H-7; CAS 352010-68-5) and 4-(3-trifluoromethylphenoxy)-2-(4-trifluoromethylphenyl)pyrimidine (H-8; CAS 180608-33-7);

b6) from the group of the EPSP synthase inhibitors:

glyphosate, glyphosate-isopropylammonium and glyphosate-trimesium (sulfosate);

b7) from the group of the glutamine synthase inhibitors:

bilanaphos (bialaphos), bilanaphos-sodium, glufosinate and glufosinate-ammonium;

b8) from the group of the DHP synthase inhibitors:

asulam;

b9) from the group of the mitose inhibitors:

amiprophos, amiprophos-methyl, benfluralin, butamiphos, butralin, carbetamide, chlorpropham, chlorthal, chlorthal-dimethyl, dinitramine, dithiopyr, ethalfluralin, fluchloralin, oryzalin, pendimethalin, prodiamine, propham, propyzamide, tebutam, thiazopyr and trifluralin;

b10) from the group of the VLCFA inhibitors:

acetochlor, alachlor, anilofos, butachlor, cafenstrole, dimethachlor, dimethanamid, dimethenamid-P, diphenamid, fentrazamide, flufenacet, mefenacet, metazachlor, metolachlor, metolachlor-S, naproanilide, napropamide, pethoxamid, piperophos, pretilachlor, propachlor, propisochlor, pyroxasulfone (KIH-485) and thenylchlor;

Compounds of the formula 2:

in which the variables have the following meanings:Y is phenyl or 5- or 6-membered heteroaryl as defined at the outset, which radicals may be substituted by one to three groups R^aa; R²¹, R²², R²³, R²⁴ are H, halogen or C₁-C₄-alkyl; X is O or NH; N is 0 or 1.

Compounds of the formula 2 have in particular the following meanings:

Y is

where # denotes the bond to the skeleton of the molecule; andR²¹, R²², R²³, R²⁴ are H, Cl, F or CH₃; R²⁵ is halogen, C₁-C₄-alkyl or C₁-C₄-haloalkyl; R²⁶ is C₁-C₄-alkyl; R²⁷ is halogen, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy; R²⁸ is H, halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl or C₁-C₄-haloalkoxy; M is 0, 1, 2 or 3; X is oxygen; N is 0 or 1.

Preferred compounds of the formula 2 have the following meanings:

Y

R²¹ is H; R²², R²³ are F; R²⁴ is H or F; X is oxygen; N is 0 or 1.

Particularly preferred compounds of the formula 2 are: 3-[5-(2,2-difluoroethoxy)-1-methyl-3-trifluoromethyl-1H-pyrazol-4-ylmethanesulfonyl]-4-fluoro-5,5-dimethyl-4,5-dihydroisoxazole (2-1); 3-{[5-(2,2-difluoroethoxy)-1-methyl-3-trifluoromethyl-1H-pyrazol-4-yl]fluoromethanesulfonyl}-5,5-dimethyl-4,5-dihydroisoxazole (2-2); 4-(4-fluoro-5,5-dimethyl-4,5-dihydroisoxazole-3-sulfonylmethyl)-2-methyl-5-trifluoromethyl-2H-[1,2,3]triazole (2-3); 4-[(5,5-dimethyl-4,5-dihydroisoxazole-3-sulfonyl)fluoromethyl]-2-methyl-5-trifluoromethyl-2H-[1,2,3]triazole (2-4); 4-(5,5-dimethyl-4,5-dihydroisoxazole-3-sulfonylmethyl)-2-methyl-5-trifluoromethyl-2H-[1,2,3]triazole (2-5); 3-{[5-(2,2-difluoroethoxy)-1-methyl-3-trifluoromethyl-1H-pyrazol-4-yl]difluoromethanesulfonyl}-5,5-dimethyl-4,5-dihydroisoxazole (2-6); 4-[(5,5-dimethyl-4,5-dihydroisoxazole-3-sulfonyl)difluoromethyl]-2-methyl-5-trifluoromethyl-2H-[1,2,3]triazole (2-7); 3-{[5-(2,2-difluoroethoxy)-1-methyl-3-trifluoromethyl-1H-pyrazol-4-yl]difluoromethanesulfonyl}-4-fluoro-5,5-dimethyl-4,5-dihydroisoxazole (2-8); 4-[difluoro-(4-fluoro-5,5-dimethyl-4,5-dihydroisoxazole-3-sulfonyl)methyl]-2-methyl-5-trifluoromethyl-2H-[1,2,3]triazole (2-9);

b11) from the group of the cellulose biosynthesis inhibitors:

chlorthiamid, dichlobenil, flupoxam and isoxaben;

b12) from the group of the decoupler herbicides:

dinoseb, dinoterb and DNOC and its salts;

b13) from the group of the auxin herbicides:

2,4-D and its salts and esters, 2,4-DB and its salts and esters, aminopyralid and its salts such as aminopyralid-tris(2-hydroxypropyl)ammonium and its esters, benazolin, benazolin-ethyl, chloramben and its salts and esters, clomeprop, clopyralid and its salts and esters, dicamba and its salts and esters, dichlorpropand its salts and esters, dichlorprop-P and its salts and esters, fluoroxypyr, fluoroxypyr-butomethyl, fluoroxypyr-meptyl, MCPA and its salts and esters, MCPA-thioethyl, MCPB and its salts and esters, mecopropand its salts and esters, mecoprop-P and its salts and esters, picloram and its salts and esters, quinclorac, quinmerac, TBA (2,3,6) and its salts and esters, triclopyr and its salts and esters, and 5,6-dichloro-2-cyclopropyl-4-pyrimidinecarboxylic acid (H-9; CAS 858956-08-8) and its salts and esters;

b14) from the group of the auxin transport inhibitors: diflufenzopyr, diflufenzopyr-sodium, naptalam and naptalam-sodium;

b15) from the group of the other herbicides: bromobutide, chlorflurenol, chlorflurenol-methyl, cinmethylin, cumyluron, dalapon, dazomet, difenzoquat, difenzoquat-metilsulfate, dimethipin, DSMA, dymron, endothal and its salts, etobenzanid, flamprop, flamprop-isopropyl, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl, flurenol, flurenol-butyl, flurprimidol, fosamine, fosamine-ammonium, indanofan, maleic hydrazide, mefluidide, metam, methyl azide, methyl bromide, methyl-dymron, methyl iodide, MSMA, oleic acid, oxaziclomefone, pelargonic acid, pyributicarb, quinoclamine, triaziflam, tridiphane and 6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinol (H-10; CAS 499223-49-3) and its salts and esters.

Examples of preferred safeners C are benoxacor, cloquintocet, cyometrinil, cyprosulfamide, dichlormid, dicyclonone, dietholate, fenchlorazole, fenclorim, flurazole, fluxofenim, furilazole, isoxadifen, mefenpyr, mephenate, naphthalic anhydride, oxabetrinil, 4-(dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane (H-11; MON4660, CAS 71526-07-3) and 2,2,5-trimethyl-3-(dichloroacetyl)-1,3-oxazolidine (H-12; R-29148, CAS 52836-31-4).

The active compounds of groups b1) to b15) and the safeners C are known herbicides and safeners, see, for example, The Compendium of Pesticide Common Names (http://www.alanwood.net/pesticides/); B. Hock, C. Fedtke, R. R. Schmidt, Herbizide [Herbicides], Georg Thieme Verlag, Stuttgart, 1995. Further herbicidally active compounds are known from WO 96/26202, WO 97/41116, WO 97/41117, WO 97/41118, WO 01/83459 and WO 2008/074991 and from W. Kramer et al. (ed.) “Modern Crop Protection Compounds”, Vol. 1, Wiley VCH, 2007 and the literature quoted therein.

The invention also relates to compositions in the form of a crop protection composition formulated as a 1-component composition comprising an active compound combination comprising at least one pyridine compound of the formula I and at least one further active compound, preferably selected from the active compounds of groups b1 to b15, and at least one solid or liquid carrier and/or one or more surfactants and, if desired, one or more further auxiliaries customary for crop protection compositions.

The invention also relates to compositions in the form of a crop protection composition formulated as a 2-component composition comprising a first component comprising at least one pyridine compound of the formula I, a solid or liquid carrier and/or one or more surfactants and a second component comprising at least one further active compound selected from the active compounds of groups b1 to b15, a solid or liquid carrier and/or one or more surfactants, where additionally both components may also comprise further auxiliaries customary for crop protection compositions.

In binary compositions comprising at least one compound of the formula I as component A and at least one herbicide B, the weight ratio of the active compounds A:B is generally in the range of from 1:1000 to 1000:1, preferably in the range of from 1:500 to 500:1, in particular in the range of from 1:250 to 250:1 and particularly preferably in the range of from 1:75 to 75:1.

In binary compositions comprising at least one compound of the formula I as component A and at least one safener C, the weight ratio of the active compounds A:C is generally in the range of from 1:1000 to 1000:1, preferably in the range of from 1:500 to 500:1, in particular in the range of from 1:250 to 250:1 and particularly preferably in the range of from 1:75 to 75:1.

In ternary compositions comprising both at least one compound of the formula I as component A, at least one herbicide B and at least one safener C, the relative parts by weight of the components A:B are generally in the range of from 1:1000 to 1000:1, preferably in the range of from 1:500 to 500:1, in particular in the range of from 1:250 to 250:1 and particularly preferably in the range of from 1:75 to 75:1; the weight ratio of the components A:C is generally in the range of from 1:1000 to 1000:1, preferably in the range of from 1:500 to 500:1, in particular in the range of from 1:250 to 250:1 and particularly preferably in the range of from 1:75 to 75:1; and the weight ratio of the components B:C is generally in the range of from 1:1000 to 1000:1, preferably in the range of from 1:500 to 500:1, in particular in the range of from 1:250 to 250:1 and particularly preferably in the range of from 1:75 to 75:1. Preferably, the weight ratio of the components A+B to the component C is in the range of from 1:500 to 500:1, in particular in the range of from 1:250 to 250:1 and particularly preferably in the range of from 1:75 to 75:1.

The active compounds in the compositions described are in each case preferably present in synergistically effective amounts.

The compounds I and the compositions according to the invention may also have a plant-strengthening action. Accordingly, they are suitable for mobilizing the defense system of the plants against attack by unwanted microorganisms, such as harmful fungi, but also viruses and bacteria. Plant-strengthening (resistance-inducing) substances are to be understood as meaning, in the present context, those substances which are capable of stimulating the defense system of treated plants in such a way that, when subsequently inoculated by unwanted microorganisms, the treated plants display a substantial degree of resistance to these microorganisms.

The compounds I can be employed for protecting plants against attack by unwanted microorganisms within a certain period of time after the treatment. The period of time within which their protection is effected generally extends from 1 to 28 days, preferably from 1 to 14 days, after the treatment of the plants with the compounds I, or, after treatment of the seed, for up to 9 months after sowing.

The compounds I and the compositions according to the invention are also suitable for increasing the harvest yield.

Moreover, they have reduced toxicity and are tolerated well by the plants.

Hereinbelow, the preparation of quinolinone compounds of the formula I is illustrated by way of examples, without limiting the subject matter of the present invention to the examples shown.

PREPARATION EXAMPLES

Preparation of 6,8-Dihydroxy-7-o-tolylquinoline

Step 1: 2-Iodo-1,3-dimethoxy-4-nitrobenzene

1,3-Difluoro-2-iodo-4-nitrobenzene (5.0 g, 17.5 mmol) was dissolved in 50 ml of methanol, and NaOMe (3.79 g, 70.1 mmol) was added. The solution was heated under reflux for 16 h. After concentration, the residue was chromatographed on silica gel using petroleum ether/ethyl acetate. This gave 2-iodo-1,3-dimethoxy-4-nitrobenzene (3 g) as a yellowish powder.

¹H-NMR (400 MHz, CDCl₃): 8.0 (d, 1H); 6.88 (d, 1H); 3.96 (s, 3H); 3.91 (s, 3H)

Step 2: 2,6-Dimethoxy-2′-methyl-3-nitrobiphenyl

2-Iodo-1,3-dimethoxy-4-nitrobenzene (0.5 g, 1.62 mmol) was dissolved in dioxane/acetonitrile/water (10 ml/2 ml/2 ml), and 2-tolylboronic acid was added. Pd(dppf)Cl₂ (0.11 mg, 0.16 mmol) and K₂CO₃ (0.33 g, 2.43 mmol) were added to this, and the mixture was stirred at 90° C. for 32 h. After concentration, the residue was chromatographed on silica gel using petroleum ether/ethyl acetate. This gave 2,6-dimethoxy-2′-methyl-3-nitrobiphenyl (0.2 g) as a colorless powder.

¹H-NMR (400 MHz, CDCl₃): 7.99 (d, 1H); 7.15-7.35 (m, 4H); 6.79 (d, 1H); 3.82 (s, 3H); 3.45 (s, 3H); 2.10 (s, 3H)

Step 3: 2,6-Dimethoxy-2′-methylbiphenyl-3-ylamine

Pd/C (0.1 g) was added to 2,6-dimethoxy-2′-methyl-3-nitrobiphenyl (0.2 g, 0.73 mmol) in methanol (20 ml), and under 1 atm of H₂, the mixture was heated at 50° C. for 2 h. Filtration and concentration gave 2,6-dimethoxy-2′-methylbiphenyl-3-ylamine (0.14 g) as a colorless oil, which was directly reacted further.

Step 4: 6,8-Dimethoxy-7-o-tolylquinoline

6-Dimethoxy-2′-methylbiphenyl-3-ylamine (0.14 g, 0.58 mmol), acrolein (100 mg, 1.8 mmol) and 1N HCl (4 ml) were heated at 90° C. for 2 h. After cooling, the mixture was diluted with ethyl acetate (10 ml) and neutralized with saturated NaHCO₃ solution, the aqueous phase was extracted 2× with ethyl acetate (3 ml) and the organic phase was dried with Na₂SO₄ and concentrated. The residue was chromatographed on silica gel using petroleum ether/ethyl acetate. This gave 6,8-dimethoxy-7-o-tolylquinoline (80 mg) as yellowish crystals.

¹H-NMR (400 MHz, CDCl₃): 8.83 (m, 1H); 8.10 (d, 1H); 7.2-7.4 (m, 5H); 6.95 (s, 1H); 3.85 (s, 3H); 3.77 (s, 3H); 2.13 (s, 3H)

Step 5: 6,8-Dihydroxy-7-o-tolylquinoline

At −78° C., 1N BBr₃ in CH₂Cl₂ (1.5 ml, 1.5 mmol) was added to 6,8-dimethoxy-7-o-tolylquinoline (0.10 g, 0.36 mmol) in CH₂Cl₂ (5 ml), and the mixture was warmed to room temperature and stirred for 6 h. The solution was poured into ice-water and neutralized with saturated NaHCO₃ solution. The mixture was extracted with ethyl acetate, and the organic phase was dried with Na₂SO₄. Purification of the residue by HPLC gave 6,8-dihydroxy-7-o-tolylquinoline (7 mg) as a white powder.

¹H-NMR (400 MHz, CDCl₃): 8.63 (d, 1H); 8.05 (d, 1H); 7.30-7.45 (m, 5H); 6.89 (s, 1H); 2.21 (s, 3H)

MS (M+H): 251.9

Use Examples

The herbicidal activity of the compound of the formula I is demonstrated by the following greenhouse experiments:

The culture containers used are plastic flowerpots containing loamy sand with approximately 3.0% of humus as the substrate. The seeds of the test plants are sown separately for each species.

For the pre-emergence treatment, the active ingredients, which have been suspended or emulsified in water, are applied directly after sowing by means of finely distributing nozzles. The containers are irrigated gently to promote germination and growth and subsequently covered with transparent plastic hoods until the plants have rooted. This cover causes uniform germination of the test plants, unless this has been impaired by the active ingredients.

For the post-emergence treatment, the test plants are first grown to a height of 3 to 15 cm, depending on the plant habit, and only then treated with the active ingredients which has been suspended or emulsified in water. For this purpose, the test plants are either sown directly and grown in the same containers, or they are first grown separately as seedlings and transplanted into the test containers a few days prior to treatment.

Depending on the species, the plants are kept at 10 to 25° C. or 20 to 35° C. The test period extends over 2 to 4 weeks. During this time, the plants are tended, and their response to the individual treatments is evaluated.

Evaluation is carried out using a scale from 0 to 100. 100 means no emergence of the plants, or complete destruction of at least the aerial moieties, and 0 means no damage, or normal course of growth. A good herbicidal activity is given at values of at least 70 and a very good herbicidal activity is given at values of at least 85.

Claims

1. A quinolinone compound of the formula I

2. The compound of the formula I according to claim 1 in which X is O.

3. The compound of the formula I according to claim 1 in which X is S.

4. The compound of the formula I according to claim 1 in which X is N—R5.

5. The compound of the formula I according to claim 1 in which R1 is O—RA or O—S(O)n—RA.

6. The compound of the formula I according to claim 1 which corresponds to the formula I.1

7. The compound of the formula I according to claim 1 which corresponds to the formula I.2

8. The compound of the formula I according to claim 1 which corresponds to the formula I.A

9. A composition comprising a herbicidally effective amount of at least one quinolinone of the formula I or an agriculturally suitable salt thereof according to claim 1 and auxiliaries customary for formulating crop protection agents.

10. The composition according to claim 9 which comprises at least one further active compound.

11. The composition according to claim 9 which comprises two further active compounds from the group of the herbicides and/or safeners.

12. A method for controlling unwanted vegetation which comprises allowing a herbicidally effective amount of at least one quinolinone of the formula I or of an agriculturally suitable salt thereof according to claim 1 to act on plants, their seed and/or their habitat.

13. The method of claim 12, wherein X is O.

14. The method of claim 12, wherein X is S.

15. The method of claim 12, wherein X is N—R5.

16. The method of claim 12, wherein R1 is O—RA or O—S(O)n—RA.

17. The method of claim 12, wherein the compound of formula I is I.1

18. The method of claim 12, wherein the compound of formula I is I.2

19. The method of claim 12, wherein the compound of formula I is I.A