Imidazole and Triazole Compounds, Their Use and Agents Containing the Same

Abstract
The present invention relates to compounds of the formula I
Description

The present invention relates to imidazole and triazole compounds of the formula I




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in which the variables have the following meanings:

    • X is CH or N;
    • Z is a saturated hydrocarbon chain having three carbon atoms which may contain one, two, three, four, five or six substituents Rz, where Rz is as defined below:
      • Rz is halogen, cyano, nitro, cyanato (OCN), C1-C8-alkyl, C1-C8-haloalkyl, C2-C8-alkenyl, C2-C8-haloalkenyl, C2-C8-alkynyl, C3-C8-haloalkynyl, C1-C8-alkoxy, C1-C8-haloalkoxy, C1-C8-alkylcarbonyloxy, C1-C8-alkylsulfonyloxy, C2-C8-alkenyloxy, C2-C8-haloalkenyloxy, C2-C8-alkynyloxy, C3-C8-haloalkynyloxy, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C3-C8-cycloalkenyl, C3-C8-halocycloalkenyl, C3-C8-cycloalkoxy, C3-C6-cycloalkenyloxy, C1-C6-alkylene, oxy-C2-C4-alkylene, oxy-C1-C3-alkyleneoxy, phenoxy, phenyl, heteroaryloxy, heterocyclyloxy, heteroaryl, heterocyclyl, where in the groups mentioned above the heteroaryl is an aromatic five-, six- or seven-membered heterocycle and the heterocyclyl is a saturated or partially unsaturated five-, six- or seven-membered heterocycle, each of which contains one, two, three or four heteroatoms from the group consisting of O, N and S, or is NA3A4, where A3, A4 are as defined below, where two radicals Rz attached to the same carbon atom, together with the carbon atom to which they are attached, may also form C3-C10-cycloalkyl, C3-C10-cycloalkenyl or a saturated or partially unsaturated heterocycle having one, two or three heteroatoms selected from the group consisting of O, S and N, where the cycloalkyl, cycloalkenyl and the heterocycle are unsubstituted or substituted by one, two or three independently selected groups L;
    • R1 is C3-C10-cycloalkyl, C3-C10-halocycloalkyl, C3-C10-cycloalkenyl, C3-C10-halocycloalkenyl, where the carbocycles mentioned above are unsubstituted or, contain one, two, three, four or five substituents independently selected from the group consisting of halogen, hydroxyl, C1-C8-alkyl, C1-C8-haloalkyl, C2-C8-alkenyl, C2-C8-haloalkenyl, C2-C8-alkynyl and C3-C8-haloalkynyl, or is 6- to 10-membered aryl which contains one, two, three, four or five substituents L selected independently, where L is as defined below:
      • L is halogen, cyano, nitro, hydroxyl, cyanato (OCN), C1-C8-alkyl, C1-C8-haloalkyl, C2-C8-alkenyl, C2-C8-haloalkenyl, C2-C8-alkynyl, C3-C8-haloalkynyl, C4-C10-alkadienyl, C4-C10-haloalkadienyl, C1-C8-alkoxy, C1-C8-haloalkoxy, C1-C8-alkylcarbonyloxy, C1-C8-alkylsulfonyloxy, C2-C8-alkenyloxy, C2-C8-haloalkenyloxy, C2-C8-alkynyloxy, C3-C8-haloalkynyloxy, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C3-C8-cycloalkenyl, C3-C8-halocycloalkenyl, C3-C8-cycloalkoxy, C3-C6-cycloalkenyloxy, hydroxyimino-C1-C8-alkyl, C1-C6-alkylene, oxy-C2-C4-alkylene, oxy-C1-C3-alkyleneoxy, C1-C8-alkoximino-C1-C8-alkyl, C2-C8-alkenyloximino-C1-C8-alkyl, C2-C8-alkynyloximino-C1-C8-alkyl, S(═O)nA1, C(═O)A2, C(═S)A2, NA3A4, phenoxy, phenyl, heteroaryloxy, heterocyclyloxy, heteroaryl, heterocyclyl, where in the groups mentioned above the heteroaryl is an aromatic five-, six- or seven-membered heterocycle and the heterocyclyl is a saturated or partially unsaturated five-, six- or seven-membered heterocycle, each of which contains one, two, three or four heteroatoms from the group consisting of O, N and S; where n, A1, A2, A3, A4 are as defined below:
        • n is 0, 1 or 2;
        • A1 is hydrogen, hydroxyl, C1-C8-alkyl, C1-C8-haloalkyl, amino, C1-C8-alkylamino, di-C1-C8-alkylamino, phenyl, phenylamino or phenyl-C1-C8-alkylamino;
        • A2 is one of the groups mentioned for A1 or is C2-C8-alkenyl, C2-C8-haloalkenyl, C2-C8-alkynyl, C3-C8-haloalkynyl, C1-C8-alkoxy, C1-C8-haloalkoxy, C2-C8-alkenyloxy, C2-C8-haloalkenyloxy, C2-C8-alkynyloxy, C3-C8-haloalkynyloxy, C3-C8-cycloalkyl, C3-C8-halocyclo-alkyl, C3-C8-cycloalkoxy or C3-C8-halocycloalkoxy;
        • A3,A4 independently of one another are hydrogen, C1-C8-alkyl, C1-C8-haloalkyl, C2-C8-alkenyl, C2-C8-haloalkenyl, C2-C8-alkynyl, C3-C8-haloalkynyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C3-C8-cycloalkenyl or C3-C8-halocycloalkenyl, phenyl or 5- or six-membered heteroaryl having one, two, three or four heteroatoms from the group consisting of O, N and S in the heterocycle;


          the aliphatic and/or alicyclic and/or aromatic groups of the radical definitions of L for their part may carry one, two, three or four identical or different groups RL:
        • RL is halogen, hydroxyl, cyano, nitro, C1-C8-alkyl, C1-C8-haloalkyl, C1-C8-alkoxy, C1-C8-haloalkoxy, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C3-C8-cycloalkenyl, C3-C8-cycloalkoxy, C3-C8-halocycloalkoxy, C1-C6-alkylene, oxy-C2-C4-alkylene, oxy-C1-C3-alkyleneoxy, C1-C8-alkylcarbonyl, C1-C8-alkylcarbonyloxy, C1-C8-alkoxycarbonyl, amino, C1-C8-alkylamino, di-C1-C8-alkylamino;
      • R2 is hydrogen, C1-C10-alkyl, C1-C10-haloalkyl, C4-C10-alkenyl, C2-C10-haloalkenyl, C2-C10-alkynyl, C3-C10-haloalkynyl, C4-C10-alkadienyl, C4-C10-haloalkadienyl, C3-C10-cycloalkyl, C3-C10-halocycloalkyl, C3-C10-cycloalkenyl, C3-C10-halocycloalkenyl;
      • R3 is hydrogen, C1-C10-alkyl, C1-C10-haloalkyl, C2-C10-alkenyl, C2-C10-haloalkenyl, C2-C10-alkynyl, C3-C10-haloalkynyl, C4-C10-alkadienyl, C4-C10-haloalkadienyl, C3-C10-cycloalkyl, C3-C10-halocycloalkyl, C3-C10-cycloalkenyl, C3-C10-halocycloalkenyl, carboxyl, formyl, Si(A5A6A7), C(O)Rπ, C(O)ORπ, C(S)ORπ, C(O)SRπ, C(S)SRπ, C(NRA)SRπ, C(S)Rπ, C(NRπ)N—NA3A4, C(NRπ)RA, C(NRπ)ORA, C(O)NA3A4, C(S)NA3A4 or S(═O)nA1; where
        • Rπ is C1-C8-alkyl, C3-C8-alkenyl, C3-C8-alkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkenyl or phenyl;
        • RA is hydrogen, C2-alkenyl, C2-alkynyl or one of the groups mentioned for Rπ;
        • A5, A6, A7 independently of one another are C1-C10-alkyl, C3-C8-alkenyl, C3-C8-alkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkenyl or phenyl;
        • where Rπ, RA, A5, A6 and A7 are, unless indicated otherwise, independently of one another unsubstituted or substituted by one, two, three, four or five L, as defined above;
      • R4 is hydrogen, C1-C10-alkyl, C1-C10-haloalkyl, C2-C10-alkenyl, C2-C10-haloalkenyl, C2-C10-alkynyl, C3-C10-haloalkynyl, C4-C10-alkadienyl, C4-C10-haloalkadienyl, C3-C10-cycloalkyl, C3-C10-halocycloalkyl, C3-C10-cycloalkenyl, C3-C10-halocycloalkenyl;
        • R2, R3 and R4 are, unless indicated otherwise, independently of one another unsubstituted or substituted by one, two, three, four or five L, as defined above;
    • with the proviso that R1 is not 4-chlorophenyl, 4-bromophenyl, 4-fluorophenyl or 4-methylphenyl if Z is an unsubstituted hydrocarbon chain and R2, R3 and R4 are hydrogen; and that R1 is not 4-chlorophenyl, 2-fluorophenyl, 4-fluorophenyl, 4-methylphenyl, 4-t-butylphenyl, 4-methoxyphenyl or 2,4-dichlorophenyl if Z is CH2CH(CH3)CH2 and R2, R3 and R4 are hydrogen;
    • and agriculturally acceptable salts thereof.


The invention furthermore relates to the preparation of the compounds I, to the intermediates for preparing the compounds I and to their preparation, and also to the use of the compounds according to the invention for controlling phytopathogenic fungi, and to compositions comprising them.


Triazole compounds are known, for example, from EP 0 129 186.


However, in particular at low application rates, the fungicidal action of the compounds known from the prior art is sometimes unsatisfactory. Accordingly, it was an object of the present invention to provide novel compounds which preferably have improved properties, such as improved fungicidal action and/or better toxicological properties. Surprisingly, this object was achieved with the compounds of the formula I described herein.


Owing to the basic character of their nitrogen atoms, the compounds I are capable of forming salts or adducts with inorganic or organic acids or with metal ions . This also applies to most of the precursors described herein of compounds I, the salts and adducts of which are also provided by the present invention.


Examples of inorganic acids are hydrohalic acids, such as hydrogen fluoride, hydrogen chloride, hydrogen bromide and hydrogen iodide, carbonic acid, sulfuric acid, phosphoric acid and nitric acid.


Suitable organic acids are, for example, formic acid and alkanoic acids, such as acetic acid, trifluoroacetic acid, trichloroacetic acid and propionic acid, and also glycolic acid, thiocyanic acid, lactic acid, succinic acid, citric acid, benzoic acid, cinnamic acid, oxalic acid, alkylsulfonic acids (sulfonic acids having straight-chain or branched alkyl radicals of 1 to 20 carbon atoms), arylsulfonic acids or aryldisulfonic acids (aromatic radicals, such as phenyl and naphthyl, which carry one or two sulfonic acid groups), alkylphosphonic acids (phosphonic acids having straight-chain or branched alkyl radicals with 1 to 20 carbon atoms), arylphosphonic acids or aryldiphosphonic acids (aromatic radicals, such as phenyl and naphthyl, which carry one or two phosphoric acid radicals), where the alkyl or aryl radicals may carry further substituents, for example p-toluenesulfonic acid, salicylic acid, p-aminosalicylic acid, 2-phenoxybenzoic acid, 2-acetoxybenzoic acid etc.


Suitable metal ions are in particular the ions of the elements of the second main group, in particular calcium and magnesium, of the third and fourth main groups, in particular aluminum, tin and lead and also of the elements of transition groups one to eight, in particular chromium, manganese, iron, cobalt, nickel, copper, zinc and others. Particular preference is given to the metal ions of the elements of transition groups of the fourth period. The metals can be present in the various valencies that they can assume.


The compounds I according to the invention can be prepared by different routes analogously to processes known per se of the prior art (see, for example, the prior art cited at the outset). The compounds according to the invention can be prepared, for example, according to the syntheses shown in the schemes below.


Thus, a compound of the formula I in which R2, R3 and R4 are hydrogen (compounds I-1)




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where X, Z and R1 are as defined or as preferably defined for formula I can be prepared from compounds II-1 by reducing the keto group




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The reduction of the OH group may be carried out according to the literature below: DE 3321023, DE 3019049 or analogously to DE 3209431; Chem Ber 121(6), 1988, 1059 ff Tetrahedron, 63 (19), 4027-4038; 2007 ff.


The present invention furthermore provides compounds of the formula II-1




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in which X, Z and R1 are as defined as described herein for formula I.


Compounds of the formula II-1 can be obtained by alkylation reactions, for example by reacting a compound of the formula III




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with a compound IV





R1—Z-LG   (IV)


and a base, where LG is a leaving group such as, for example, halogen, in particular Cl, Br and I, or mesylate, tosylate, or another suitable leaving group known to the person skilled in the art. R1, X and Z have the meanings or preferred meanings as defined for formula I. Suitable bases are alkali metal or alkaline earth metal hydrides, alkali metal amides or alkoxides.


Processes for preparing compounds of type IV are known to the person skilled in the art.


Processes for preparing compounds of type III are likewise known to the person skilled in the art.


Compounds II-1 can also be obtained from alkylboranes of type V:




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in which X and Z are as defined or as preferably defined for formula I and A is in each case independently a C1-C6-alkyl group, C3-C6-cycloalkoxy group or OH by reaction with a compound VI





R1-LG   VI


in which R1 is as defined or as preferably defined for formula I and LG is a leaving group. Suitable leaving groups LG are halogen, preferably chlorine, bromine or iodine, alkyl carbonylate, benzoate, alkylsulfonate, haloalkylsulfonate or arylsulfonate, particularly preferably chlorine and bromine. The reaction is usually carried out in the presence of a base and a catalyst, in particular in the presence of a palladium catalyst, as described, for example, in: Synth. Commun. Vol. 11, p. 513 (1981); Acc. Chem. Res. Vol. 15, pp. 178-184 (1982); Chem. Rev. Vol. 95, pp. 2457-2483 (1995); Organic Letters Vol. 6 (16), p. 2808 (2004); “Metal catalyzed cross coupling reactions”, 2nd Edition, Wiley, V C H 2005 (Eds. De Meijere, Diederich); “Handbook of organopalladium chemistry for organic synthesis” (Eds Negishi), Wiley, Interscience, New York, 2002; “Handbook of functionalized organometallics”, (Ed. P. Knochel), Wiley, V C H, 2005.


Suitable catalysts are tetrakis(triphenylphosphine)palladium(0); bis(triphenylphosphine)palladium(II) chloride; bis(acetonitrile)palladium(II) chloride; [1,1′-bis(diphenylphosphino)ferrocene]palladium(II) chloride/methylene chloride (1:1) complex; bis[bis-(1,2-diphenylphosphino)ethane]palladium(0); bis[bis-(1,2-diphenyl-phosphino)butane]palladium(II) chloride; palladium(II) acetate; palladium(II) chloride; palladium(II) acetate/tri-o-tolylphosphine complex or mixtures of phosphines and Pd salts or phosphines and Pd complexes, for example dibenzylideneacetonepalladium and tri-tert-butylphosphine (or the corresponding tetrafluoroborate), tricyclohexyl-phosphines or a polymer-bound Pd/triphenylphosphine catalyst system.


Suitable bases are, for example, inorganic bases, such as alkali metal or alkaline earth metal oxides, such as lithium oxide, sodium oxide, calcium oxide and magnesium oxide, alkali metal or alkaline earth metal carbonates, such as lithium carbonate, sodium carbonate, potassium carbonate, cesium carbonate and calcium carbonate. Also suitable are alkali metal bicarbonates, such as sodium bicarbonate, and alkali metal or alkaline earth metal alkoxides, such as, for example, sodium methoxide, sodium ethoxide, potassium ethoxide or potassium tert-butoxide. Suitable are furthermore amine bases, in particular tertiary amines, such as trimethylamine, triethylamine, diisopropylethylamine and N-methylpiperidine, or aromatic bases, such as pyridines, substituted pyridines, such as, for example, collidine, lutidine and 4-dimethylaminopyridine. Particularly advantageous are frequently bases such as sodium carbonate, potassium carbonate, cesium carbonate, triethylamine and sodium bicarbonate.


The base is usually employed in a molar ratio of from 1:1 to 1:10, preferably in a molar ratio of from 1:1.5 to 1:5, based on R1-LG. The boron compound is employed in a molar ratio of from 1:1 to 1:5, preferably from 1:1 to 1:2.5, based on R1-LG. Here, R1 is preferably substituted phenyl.


The reaction is usually carried out in an inert organic solvent. Suitable solvents are aliphatic hydrocarbons, such as, for example, pentane, hexane, cyclohexane and petroleum ether, aromatic hydrocarbons, such as toluene, o-, m- or p-xylene, ethers, such as, for example, diisopropyl ether, methyl tert-butyl ether, dioxane, anisole, tetrahydrofuran and dimethoxyethane. Suitable are furthermore ketones, such as acetone, ethyl methyl ketone, diethyl ketone and methyl tert-butyl ketone. Also suitable are solvents such as dimethyl sulfoxide, dimethylformamide and dimethylacetamide. Suitable are in particular ethers such as tetrahydrofuran, dioxane and dimethoxyethane. Preferably, the solvents mentioned above may also be used as mixtures with one another or as a mixture with water.


The coupling reaction is usually carried out at temperatures between 20 and 180° C., preferably between 40 and 120° C.


After the reaction has ended, the coupling products can be isolated according to standard methods. It is also possible to use a scavenger to remove byproducts or remaining starting material. Further details and references for this subject can be found, for example, in “Synthesis and purification catalog”, Argonaut, 2003.


According to a further process, compounds I (where R3=hydrogen) can be obtained by reacting an oxirane of the formula VIII




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in which Z, R1, R2 and R4 are as defined or as preferably defined for formula I, with imidazole or triazole in the presence of a base with opening of the epoxide to form the target products. Such processes are described, for example, in EP 0 236 884.


The oxirane VIII can be obtained by reacting the corresponding olefin IX




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with a peracid or an equivalent reagent (such as, for example, dimethyldioxirane or other peroxides, see also EP 0 236 884).


The olefin IX can be prepared by a Wittig reaction from




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(see also EP 0 236 884).


Alternatively, olefins IX can be prepared via the corresponding alcohol XII




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which, in an elimination reaction familiar to the person skilled in the art, is converted into the olefin (see also EP 0 236 884). The preparation of the alcohols XII is described, for example, in DE 3400829. The double bond may optionally be isomerized to obtain the desired configuration of the oxirane. Processes for achieving this will be familiar to the person skilled in the art.


To prepare compounds of the formula I in which R2≠hydrogen (compounds I-2) from compounds I-1,




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for example, the appropriate ketone of the formula II (see above) is reacted, for example, with NaH in DMF at RT and with addition of the appropriate halide R2-Hal at 0-5° C.


Compounds of type I-2 can furthermore also be obtained by reacting a halide of the formula IV (see above, LG is in particular Cl or Br) analogously with NaH in DMF and a compound IIIa.




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To obtain, starting with compounds of the formula I-1, compounds I where R3≠hydrogen (compounds I-3),




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methods, known to the person skilled in the art, for alkylating, esterifying etc. alcohols may be employed (see in this regard also DE 3321422, DE 3019049).


To prepare compounds of the formula I in which R4≠hydrogen (compounds I-4),




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a procedure analogous to the processes described in DE 3126022, DE 3049542 may be adopted, and the corresponding ketone of the formula II-1 (see above) can be converted with a Grignard reagent (R4—Mg-Hal) into the corresponding tertiary alcohol.


In a corresponding manner, it is also possible to prepare compounds I in which two or three substituents of R2, R3 and R4 are not hydrogen from compounds I-1 by combining the processes mentioned with one another.


In some of the definitions of the symbols in the formulae given herein, collective terms are used which are generally representative of the following substituents:


halogen: fluorine, chlorine, bromine and iodine;


alkyl and the alkyl moieties of composite groups such as, for example, alkylamino: saturated straight-chain or branched hydrocarbon radicals having 1 to 4, 6, 8 or 12 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-dimethyl-propyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methyl-pentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl and 1-ethyl-2-methylpropyl;


haloalkyl: alkyl as mentioned above, where some or all of the hydrogen atoms in these groups are replaced by halogen atoms as mentioned above; in particular C1-C2-haloalkyl, such as chloromethyl, bromomethyl, dichioromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl or 1,1,1-trifluoroprop-2-yl;


alkenyl and also the alkenyl moieties in composite groups, such as alkenyloxy: unsaturated straight-chain or branched hydrocarbon radicals having 2 to 4, 2 to 6 or 2 to 8 carbon atoms and one double bond in any position. According to the invention, it may be preferred to use small alkenyl groups, such as (C2-C4)-alkenyl; on the other hand, it may also be preferred to employ larger alkenyl groups, such as (C5-C8)-alkenyl. Examples of alkenyl groups are, 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 and 1-ethyl-2-methyl-2-propenyl;


haloalkenyl: alkenyl as defined above, where some or all of the hydrogen atoms in these groups are replaced by halogen atoms as described above under haloalkyl, in particular by fluorine, chlorine or bromine;


alkadienyl: unsaturated straight-chain or branched hydrocarbon radicals having 4 to 6 or 4 to 8 carbon atoms and two double bonds in any position;


alkynyl and the alkynyl moieties in composite groups: straight-chain or branched hydrocarbon groups having 2 to 4, 2 to 6 or 2 to 8 carbon atoms and one or two triple bonds 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 and 1-ethyl-1-methyl-2-propynyl;


haloalkynyl: alkoxy as defined above, where some or all of the hydrogen atoms in these groups are replaced by halogen atoms as described above under haloalkyl, in particular by fluorine, chlorine or bromine;


cycloalkyl and also the cycloalkyl moieties in composite groups: mono- or bicyclic saturated hydrocarbon groups having 3 to 8, in particular 3 to 6, carbon ring members, for example C3-C6-cycloalkyl, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl;


halocycloalkyl: cycloalkyl as defined above, where some or all of the hydrogen atoms in these groups are replaced by halogen atoms as described above under haloalkyl, in particular by fluorine, chlorine or bromine;


cycloalkenyl: monocyclic monounsaturated hydrocarbon groups having preferably 3 to 8 or 4 to 6, in particular 5 to 6, carbon ring members, such as cyclopenten-1-yl, cyclopenten-3-yl, cyclohexen-1-yl, cyclohexen-3-yl, cyclohexen-4-yl and the like;


halocycloalkenyl: cycloalkenyl as defined above, where some or all of the hydrogen atoms in these groups are replaced by halogen atoms as described above under haloalkyl, in particular by fluorine, chlorine or bromine;


alkoxy: an alkyl group as defined above which is attached via an oxygen, preferably having 1 to 8, more preferably 2 to 6, carbon atoms. Examples are: methoxy, ethoxy, n-propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy or 1,1-dimethylethoxy, and also, for example, 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;


haloalkoxy: alkoxy as defined above, where some or all of the hydrogen atoms in these groups are replaced by halogen atoms as described above under haloalkyl, in particular by fluorine, chlorine or bromine. Examples are OCH2F, OCHF2, OCF3, OCH2Cl, OCHCl2, OCCl3, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoro-methoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2-difluoro-ethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, OC2F5, 2-fluoropropoxy, 3-fluoro-propoxy, 2,2-difluoropropoxy, 2,3-difluoropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2,3-dichloropropoxy, 2-bromopropoxy, 3-bromopropoxy, 3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy, OCH2—C2F5, OCF2—C2F5, 1-(CH2F)-2-fluoroethoxy, 1-(CH2Cl)-2-chloroethoxy, 1-(CH2Br)-2-bromoethoxy, 4-fluorobutoxy, 4-chiorobutoxy, 4-bromo-butoxy or nonafluorobutoxy; and also 5-fluoropentoxy, 5-chloropentoxy, 5-bromo-pentoxy, 5-iodopentoxy, undecafluoropentoxy, 6-fluorohexoxy, 6-chlorohexoxy, 6-bromohexoxy, 6-iodohexoxy or dodecafluorohexoxy.


alkylene: divalent unbranched chains of CH2 groups. Preference is given to (C1-C6)-alkylene, more preference to (C2-C4)-alkylene; furthermore, it may be preferred to use (C1-C3)-alkylene groups. Examples of preferred alkylene radicals are CH2, CH2CH2, CH2CH2CH2, CH2(CH2)2CH2, CH2(CH2)3CH2 and CH2(CH2)4CH2;


6- to 10-membered aryl: an aromatic hydrocarbon cycle having 6, 7, 8, 9 or 10 carbon atoms in the ring. In particular phenyl or naphthyl.


a 3-, 4-, 5-, 6-, 7-, 8-, 9- or 10-membered saturated or partially unsaturated heterocycle which contains 1, 2, 3 or 4 heteroatoms from the group consisting of O, N and S, where the heterocycle in question may be attached via a carbon atom or, if present, via a nitrogen atom. According to the invention, it may be preferred for the heterocycle in question to be attached via carbon; on the other hand, it may also be preferred for the heterocycle to be attached via nitrogen. In particular:

    • a three- or four-membered saturated heterocycle (hereinbelow also referred to as heterocyclyl) which contains one or two heteroatoms from the group consisting of O, N and S as ring members;
    • a five- or six-membered saturated or partially unsaturated heterocycle which contains one, two, three or four heteroatoms from the group consisting of O, N and S as ring members: for example monocyclic saturated or partially unsaturated heterocycles which, in addition to carbon ring members, contain one, two or three nitrogen atoms and/or one oxygen or sulfur atom or one or two oxygen and/or sulfur atoms, for example 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazolidinyl, 4-isoxazolidinyl, 5-isoxazolidinyl, 3-isothiazolidinyl, 4-isothiazolidinyl, 5-isothiazolidinyl, 3-pyrazolidinyl, 4-pyrazolidinyl, 5-pyrazolidinyl, 2-oxazolidinyl, 4-oxazolidinyl, 5-oxazolidinyl, 2-thiazolidinyl, 4-thiazolidinyl, 5-thiazolidinyl, 2-imidazolidinyl, 4-imidazolidinyl, 1,2,4-oxadiazolidin-3-yl, 1,2,4-oxadiazolidin-5-yl, 1,2,4-thiadiazolidin-3-yl, 1,2,4-thiadiazolidin-5-yl, 1,2,4-triazolidin-3-yl, 1,3,4-oxadiazolidin-2-yl, 1,3,4-thiadiazolidin-2-yl, 1,3,4-triazolidin-2-yl, 2,3-dihydrofur-2-yl, 2,3-dihydrofur-3-yl, 2,4-dihydrofur-2-yl, 2,4-dihydrofur-3-yl, 2,3-dihydrothien-2-yl, 2,3-dihydrothien-3-yl, 2,4-dihydrothien-2-yl, 2,4-dihydrothien-3-yl, 2-pyrrolin-2-yl, 2-pyrrolin-3-yl, 3-pyrrolin-2-yl, 3-pyrrolin-3-yl, 2-isoxazolin-3-yl, 3-isoxazolin-3-yl, 4-isoxazolin-3-yl, 2-isoxazolin-4-yl, 3-isoxazolin-4-yl, 4-isoxazolin-4-yl, 2-isoxazolin-5-yl, 3-isoxazolin-5-yl, 4-isoxazolin-5-yl, 2-isothiazolin-3-yl, 3-isothiazolin-3-yl, 4-isothiazolin-3-yl, 2-isothiazolin-4-yl, 3-isothiazolin-4-yl, 4-isothiazolin-4-yl, 2-isothiazolin-5-yl, 3-isothiazolin-5-yl, 4-isothiazolin-5-yl, 2,3-dihydropyrazol-1-yl, 2,3-dihydropyrazol-2-yl, 2,3-dihydropyrazol-3-yl, 2,3-dihydropyrazol-4-yl, 2,3-dihydropyrazol-5-yl, 3,4-dihydropyrazol-1-yl, 3,4-dihydropyrazol-3-yl, 3,4-dihydropyrazol-4-yl, 3,4-dihydropyrazol-5-yl, 4,5-dihydropyrazol-1-yl, 4,5-dihydropyrazol-3-yl, 4,5-dihydropyrazol-4-yl, 4,5-dihydropyrazol-5-yl, 2,3-dihydrooxazol-2-yl, 2,3-dihydrooxazol-3-yl, 2,3-dihydrooxazol-4-yl, 2,3-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, 3,4-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, 2-piperidinyl, 3-piperidinyl, 4-piperidinyl, 1,3-dioxan-5-yl, 2-tetrahydropyranyl, 4-tetrahydropyranyl, 2-tetrahydrothienyl, 3-hexahydropyridazinyl, 4-hexahydropyridazinyl, 2-hexahydropyrimidinyl, 4-hexahydropyrimidinyl, 5-hexahydropyrimidinyl, 2-piperazinyl, 1,3,5-hexahydrotriazin-2-yl and 1,2,4-hexahydrotriazin-3-yl and also the corresponding -ylidene radicals;
    • a seven-membered saturated or partially unsaturated heterocycle which contains one, two, three or four heteroatoms from the group consisting of O, N and S as ring members: for example mono- and bicyclic heterocycles having 7 ring members which, in addition to carbon ring members, contain one, two or three nitrogen atoms and/or one oxygen or sulfur atom or one or two oxygen and/or sulfur atoms, for example tetra- and hexahydroazepinyl, such as 2,3,4,5-tetrahydro[1H]azepin-1-, -2-, -3-, -4-, -5-, -6- or -7-yl, 3,4,5,6-tetrahydro[2H]azepin-2-, -3-, -4-, -5-, -6- or -7-yl, 2,3,4,7-tetrahydro[1H]azepin-1-, -2-, -3-, -4-, -5-, -6- or -7-yl, 2,3,6,7-tetrahydro[1H]azepin-1-, -2-, -3-, -4-, -5-, -6- or -7-yl, hexahydroazepin-1-, -2-, -3- or -4-yl, tetra- and hexahydrooxepinyl such as 2,3,4,5-tetrahydro[1H]oxepin-2-, -3-, -4-, -5-, -6- or -7-yl, 2,3,4,7-tetrahydro[1H]oxepin-2-, -3-, -4-, -5-, -6- or -7-yl, 2,3,6,7-tetrahydro[1H]oxepin-2-, -3-, -4-, -5-, -6- or -7-yl, hexahydroazepin-1-, -2-, -3- or -4-yl, tetra- and hexahydro-1,3-diazepinyl, tetra- and hexahydro-1,4-diazepinyl, tetra- and hexahydro-1,3-oxazepinyl, tetra- and hexahydro-1,4-oxazepinyl, tetra- and hexahydro-1,3-dioxepinyl, tetra- and hexahydro-1,4-dioxepinyl and the corresponding -ylidene radicals;


      a 5-, 6-, 7-, 8-, 9- or 10-membered aromatic heterocycle which contains 1, 2, 3 or 4 heteroatoms from the group consisting of O, N and S: in particular a five- or six-membered aromatic mono- or bicyclic heterocycle which contains one, two, three or four heteroatoms from the group consisting of O, N and S: the heterocycle in question may be attached via a carbon atom or, if present, via a nitrogen atom. According to the invention, it may be preferred for the heterocycle in question to be attached via carbon; on the other hand, it may also be preferred for the heterocycle to be attached via nitrogen. The heterocycle is in particular:
    • 5-membered heteroaryl which contains one, two, three or four nitrogen atoms or one, two or three nitrogen atoms and/or one sulfur or oxygen atom, where the heteroaryl may be attached via carbon or nitrogen, if present: 5-membered heteroaryl groups which, in addition to carbon atoms, may contain one to four nitrogen atoms or one, two or three nitrogen atoms and/or one sulfur or oxygen atom as ring members, for example furyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl (1,2,3-; 1,2,4-triazolyl), tetrazolyl, oxazolyl, isoxazolyl, 1,3,4-oxadiazolyl, thiazolyl, isothiazolyl and thiadiazolyl, in particular 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyrrolyl, 3-pyrrolyl, 3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 2-imidazolyl, 4-imidazolyl, 1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl, 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl, 1,2,4-triazol-3-yl, 1,3,4-oxadiazol-2-yl, 1,3,4-thiadiazol-2-yl and 1,3,4-triazol-2-yl;
    • 6-membered heteroaryl which contains one, two, three or four, preferably one, two or three, nitrogen atoms, where the heteroaryl may be attached via carbon or nitrogen, if present: 6-membered heteroaryl groups which, in addition to carbon atoms, may contain one to four or one, two or three nitrogen atoms as ring members, for example pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, 1,2,3-triazinyl, 1,2,4-triazinyl, 1,3,5-triazinyl, in particular 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrazinyl, 1,3,5-triazin-2-yl and 1,2,4-triazin-3-yl.


The novel compounds according to the invention comprise chiral centers and are generally obtained in the form of racemates or as diastereomer mixtures of erythro and threo forms. The erythro and threo diastereomers of the compounds according to the invention can be separated and isolated in pure form, for example, on the basis of their different solubilities or by column chromatography. Using known methods, such uniform pairs of diastereomers can be used to obtain uniform enantiomers. Suitable for use as antimicrobial agents are both the uniform diastereomers or enantiomers and mixtures thereof obtained in the synthesis. This applies correspondingly to the fungicidal compositions.


Accordingly, the invention provides both the pure enantiomers or diastereomers and mixtures thereof. This applies to the compounds according to the invention of the formula I and optionally correspondingly to their precursors. The scope of the present invention includes in particular the (R) and (S) isomers and the racemates of the compounds according to the invention, in particular of the formula I, which have centers of chirality. Suitable compounds according to the invention, in particular of the formula I, also comprise all possible stereoisomers (cis/trans isomers) and mixtures thereof.


The compounds according to the invention, in particular of the formula I, may be present in various crystal modifications which may differ in their biological activity. They are likewise provided by the present invention.


In the compounds I according to the invention, particular preference is given to the following meanings of the substituents, in each case on their own or in combination.


According to one embodiment, X is N (triazole compounds of the formula I.A).


According to a further embodiment, X═CH (imidazole compounds of the formula I.B).


Z in the compounds according to the invention is a saturated hydrocarbon chain having three carbon atoms which may contain one, two, three, four, five or six substituents Rz. According to one embodiment, Z is unsubstituted. According to a further embodiment, Z contains at least one substituent Rz, as defined herein or as defined as being preferred.


According to one embodiment of the invention, Z is a group Z1:




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in which # are the points of attachment, n and m are each 0, 1 or 2, where n+m=2, and Rz1 and Rz2 are in each case independently of one another selected from the group consisting of hydrogen and Rz, as defined or as defined as being preferred herein.


According to one aspect, n=0 and m is 2.


According to a further aspect, n=2 and m is 0.


According to yet a further aspect, n and m are each 1.


According to one embodiment, Rz1 is hydrogen and Rz2 is selected from Rz, as defined herein, where Rz2 is in particular selected from the group consisting of halogen, C1-C4-alkyl and C3-C6-cycloalkyl. In a specific aspect, Rz2 is selected from the group consisting of F and Cl. In a further specific aspect, Rz2 is selected from the group consisting of methyl and ethyl and n-propyl.


According to a further embodiment, Rz1 and Rz2 together with the carbon to which they are attached form a C3-C6-cycloalkyl ring, in particular a cyclopropyl ring.


In a specific embodiment of the invention, Rz1 and Rz2 in Z1 are hydrogen.


The substituent(s) Rz at Z or in group Z1, Z2 and Z3 is/are, unless indicated otherwise, in each case selected from the group consisting of halogen, cyano, nitro, cyanato (OCN), C1-C8-alkyl, C1-C8-haloalkyl, C2-C8-alkenyl, C2-C8-haloalkenyl, C2-C8-alkynyl, C3-C8-haloalkynyl, C1-C8-alkoxy, C1-C8-haloalkoxy, C1-C8-alkylcarbonyloxy, C1-C8-alkylsulfonyloxy, C2-C8-alkenyloxy, C2-C8-haloalkenyloxy, C2-C8-alkynyloxy, C3-C8-haloalkynyloxy, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C3-C8-cycloalkenyl, C3-C8-halocycloalkenyl, C3-C8-cycloalkoxy, C3-C6-cycloalkenyloxy, C1-C6-alkylene, oxy-C2-C4-alkylene, oxy-C1-C3-alkyleneoxy, phenoxy, phenyl, heteroaryloxy, heterocyclyloxy, heteroaryl, heterocyclyl, where in the groups mentioned above the heteroaryl is an aromatic five-, six- or seven-membered heterocycle and the heterocyclyl is a saturated or partially unsaturated five-, six- or seven-membered heterocycle, each of which contains one, two, three or four heteroatoms from the group consisting of O, N and S, or is NA3A4, where two radicals Rz attached to the same carbon atom, together with the carbon atom to which they are attached, may also form C3-C10-cycloalkyl, C3-C10-cycloalkenyl or a saturated or partially unsaturated heterocycle having one, two or three heteroatoms selected from the group consisting of O, S and N, where the cycloalkyl, cycloalkenyl and the heterocycle are unsubstituted or substituted by one, two or three independently selected groups L; where A3, A4 are as defined below;


According to one embodiment, Rz is in each case independently halogen, cyano, nitro, cyanato (OCN), C1-C8-alkyl, C1-C8-haloalkyl, C2-C8-alkenyl, C2-C8-haloalkenyl, C2-C8-alkynyl, C3-C8-haloalkynyl, C1-C8-alkoxy, C1-C8-haloalkoxy, C1-C8-alkylcarbonyloxy, C1-C8-alkylsulfonyloxy, C2-C8-alkenyloxy, C2-C8-haloalkenyloxy, C2-C8-alkynyloxy, C3-C8-haloalkynyloxy, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C3-C8-cycloalkenyl, C3-C8-halocycloalkenyl, C6-C8-cycloalkynyl, C6-C8-halocycloalkynyl, C3-C8-cycloalkoxy, C3-C6-cycloalkenyloxy, or NA3A4.


According to a further embodiment, Rz is in each case independently Cl, F, Br, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C3-C6-cycloalkyl or C3-C6-halocycloalkyl, in particular methyl, ethyl, trifluoromethyl, methoxy, ethoxy or cyclopropyl.


According to a further embodiment, at least one Rz is halogen, in particular Cl or F.


According to a further embodiment, at least one Rz is C1-C4-alkyl, in particular methyl or ethyl.


According to a further embodiment, at least one Rz is C1-C4-haloalkyl.


According to a further embodiment, two radicals Rz attached to the same carbon atom form, together with the carbon atom to which they are attached, a C3-C6-cycloalkyl ring.


R1 in the compounds according to the invention is C3-C10-cycloalkyl, C3-C10-halocyclo-alkyl, C3-C10-cycloalkenyl, C3-C10-halocycloalkenyl, where the carbocycles mentioned above are unsubstituted or contain one, two, three, four or five substituents independently of one another selected from the group consisting of halogen, hydroxyl, C1-C8-alkyl, C1-C8-haloalkyl, C2-C8-alkenyl, C2-C8-haloalkenyl, C2-C8-alkynyl and C3-C8-haloalkynyl; or is 6- to 10-membered aryl which contains one, two, three, four or five independently selected substituents L, where L is as defined herein, with the proviso that R1 is not 4-chlorophenyl, 4-bromophenyl, 4-fluorophenyl or 4-methylphenyl if Z is an unsubstituted hydrocarbon chain and R2, R3 and R4 are hydrogen; and that R1 is not 4-chlorophenyl, 2-fluorophenyl, 4-fluorophenyl, 4-methylphenyl, 4-t-butylphenyl, 4-methoxyphenyl or 2,4-dichlorophenyl if Z is CH2CH(CH3)CH2 and R2, R3 and R4 are hydrogen.


According to one embodiment of the invention, R1 is substituted phenyl which contains one, two, three, four or five substituents L, as defined herein or as defined as being preferred, with the proviso mentioned.


According to a further embodiment, R1 is phenyl which contains exactly one substituent L1. According to one aspect, L1 is selected from the group consisting of Br, cyano, ethyl, isopropyl, C1-C4-haloalkyl, ethoxy, C1-C4-haloalkoxy, C3-C6-cycloalkyl and C3-C6-halocycloalkyl, in particular 2-Br, 3-Br, 4-Br, 2-CN, 3-CN, 4-CN, 2-ethyl, 3-ethyl, 4-ethyl, 2-isopropyl, 3-isopropyl, 4-isopropyl, 2-ethoxy, 3-ethoxy, 4-ethoxy, 2-trifluoromethoxy, 3-trifluoromethoxy, 4-trifluoromethoxy, 2-trifluoromethyl, 3-trifluoromethyl, 4-trifluoromethyl, 2-difluoromethyl, 3-difluoromethyl and 4-difluoromethyl. According to a specific aspect, L1 is selected from the group consisting of Br, trifluoromethyl and difluoromethyl.


According to a further embodiment, R1 is phenyl which contains exactly one substituent L1, where L1 is selected from the group consisting of 2-methyl, 3-methyl, 2-methoxy, 3-methoxy, 2-Cl, 3-Cl, 3-F, 2-t-butyl and 3-t-butyl.


According to a further embodiment, R1 is phenyl which contains two, three, four or five independently selected substituents L, with the proviso that R1 is not 2,4-dichlorophenyl. According to a further embodiment R1 is phenyl which contains one substituent L1 and one substituent L2 and may additionally contain one, two or three independently selected substituents L, where L, L1 and L2 are defined like L, with the proviso that L2 is not chlorine if L1 is chlorine. According to one aspect, R2 is simultaneously hydrogen.


According to a further embodiment, R1 is phenyl which contains two, three, four or five substituents L, with the proviso that at most one L is chlorine.


According to a further embodiment, R1 is phenyl which contains one substituent L1 and one substituent L2 and may additionally contain another one, two or three independently selected substituents L, where L1 is selected from the group consisting of Cl, F, Br, cyano, nitro, hydroxyl, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy and L2 is selected from the group consisting of F, Br, cyano, nitro, hydroxyl, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy, and the further one, two or three substituents L optionally present are independently of one another selected from L, as defined herein or as defined as being preferred. According to a specific aspect thereof, L1 is selected from the group consisting of Cl, F, C1-C4-alkyl and C1-C4-haloalkyl, in particular from the group consisting of Cl, F, Br, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, methoxy, ethoxy and trifluoromethoxy, and L2 is selected from the group consisting of Cl, F, C1-C4-alkyl and C1-C4-haloalkyl, in particular from the group consisting of F, Br, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, methoxy, ethoxy and trifluoromethoxy. According to a further aspect, R1 is phenyl which contains exactly two substituents L1 and L2, as just defined or defined as being preferred.


According to a further aspect, the phenyl group is substituted by Cl and contains exactly one further substituent L2, with the proviso that R1 is not 2,4-dichlorophenyl. In particular, L2 is selected here from the group consisting of F, Br, cyano, nitro, hydroxyl, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy. According to one aspect, the phenyl group is 2,3-disubstituted. According to a further aspect, the phenyl group is 2,4-disubstituted, with the proviso mentioned. According to yet a further aspect, the phenyl group is 2,5-disubstituted. According to yet a further aspect, the phenyl group is 2,6-disubstituted.


According to a further aspect, the phenyl group is substituted by Cl and contains exactly two further substituents, L2 and L3. According to one aspect, R2 is simultaneously hydrogen.


According to a further embodiment, R1 is phenyl which may contain a substituent L1 which is F and may additionally also contain one, two, three or four substituents L selected independently of one another, where the radicals L are in each case independently as defined herein. According to one aspect thereof, the phenyl group is substituted by F in the 2-position. According to a further aspect, the phenyl group of this embodiment is substituted by F in the 3-position. According to yet a further aspect, the phenyl group of this embodiment is substituted by F in the 4-position.


According to a further aspect, the phenyl group is substituted by F and contains exactly one further substituent L2. According to one aspect, the phenyl group is 2,3-disubstituted. According to a further aspect, the phenyl group is 2,4-disubstituted. According to yet a further aspect, the phenyl group is 2,5-disubstituted. According to yet a further aspect, the phenyl group is 2,6-disubstituted. Preferably, F is in each case in the 2-position. Furthermore preferably, the second substituent L2 is selected from the group consisting of F, Cl, Br, methyl and methoxy. According to a specific embodiment, the phenyl group is 2,3-, 2,4-, 2,5- or 2,6-difluoro-substituted. According to a further specific embodiment, the phenyl group is 2-fluoro-3-chloro-, 2-fluoro-4-chloro-, 2-fluoro-5-chloro- or 2-fluoro-6-chloro-substituted.


According to a further aspect, the phenyl group is substituted by F and contains exactly two further substituents, L2 and L3.


According to a further embodiment, R1 is phenyl which may contain a substituent L1 which is methyl and additionally also one, two, three or four independently selected substituents L, where L is in each case independently as defined herein. According to one aspect, the phenyl group is substituted by methyl in the 2-position. According to a further aspect, the phenyl group of this embodiment is substituted by methyl in the 3-position. According to yet a further aspect, the phenyl group of this embodiment is substituted by methyl in the 4-position.


According to a further aspect, the phenyl group is substituted by methyl (=L1) and contains exactly one further substituent L2. According to one aspect, the phenyl group is 2,3-disubstituted. According to a further aspect, the phenyl group is 2,4-disubstituted. According to yet a further aspect, the phenyl group is 2,5-disubstituted. According to yet a further aspect, the phenyl group is 2,6-disubstituted.


According to a further aspect, the phenyl group is substituted by methyl (=L1) and contains exactly two further substituents, L2 and L3.


According to a further embodiment, R1 is phenyl which may contain one substituent L1 which is methoxy and additionally also one, two, three or four independently selected substituents L, where L is in each case independently as defined herein. According to one aspect, the phenyl group is substituted by methoxy in the 2-position. According to a further aspect, the phenyl group of this embodiment is substituted by methoxy in the 3-position. According to yet a further aspect, the phenyl group of this embodiment is substituted by methoxy in the 4-position.


According to a further aspect, the phenyl group is substituted by methoxy (=L1) and contains exactly one further substituent L2. According to one aspect, the phenyl group is 2,3-disubstituted. According to a further aspect, the phenyl group is 2,4-disubstituted. According to yet a further aspect, the phenyl group is 2,5-disubstituted. According to yet a further aspect, the phenyl group is 2,6-disubstituted.


According to a further aspect, the phenyl group is substituted by methoxy (=L1) and contains exactly two further substituents, L2 and L3.


According to a further embodiment, R1 is phenyl which contains three, four or five substituents L, where L is independently as defined herein or as defined as being preferred.


According to a further embodiment of the invention, R1 is a 2,3,5-trisubstituted phenyl ring. According to a further embodiment, R1 is a 2,3,4-trisubstituted phenyl ring. According to yet a further embodiment, R1 is a 2,4,5-trisubstituted phenyl ring. According to yet a further embodiment, R1 is a 2,4,6-trisubstituted phenyl ring. According to a specific aspect, R1 is a 2,4,6-trisubstituted phenyl ring and R2 is simultaneously hydrogen. According to yet a further embodiment, R1 is a 2,3,6-trisubstituted phenyl ring. According to one aspect, at least one of the three substituents is Cl. According to a further aspect, exactly one or exactly two of the three substituents are Cl. According to one aspect, at least one of the three substituents is F. According to a further aspect, at least one of the three substituents is methyl. According to yet a further aspect, at least one of the three substituents is methoxy.


According to a further embodiment, R1 is C3-C10-cycloalkyl or C3-C10-halocycloalkyl. According to one aspect, R1 is C3-C7-cycloalkyl, in particular cyclopropyl (c-C3H5), cyclopentyl (c-C5H9), cyclohexyl (c-C6H11) or cycloheptyl (c-C7H13), each of which may optionally be substituted. Specific examples of R1 are 1-chlorocyclopropyl, 1-methylcyclopropyl, 1-chlorocyclopentyl, 1-methylcyclopentyl and 1-methylcyclohexyl.


According to a further embodiment, R1 is C3-C10-cycloalkenyl or C3-C10-halocycloalkenyl.


According to the present invention, R2 is hydrogen, F, C1-C10-alkyl, C1-C10-haloalkyl, C4-C10-alkenyl, C2-C10-haloalkenyl, C2-C10-alkynyl, C3-C10-haloalkynyl, C4-C10-alkadienyl, C4-C10-haloalkadienyl, C3-C10-cycloalkyl, C3-C10-halocycloalkyl, C3-C10-cycloalkenyl or C3-C10-halocycloalkenyl, in particular hydrogen, C1-C10-alkyl, C1-C10-haloalkyl, C3-C10-cycloalkyl, C3-C10-halocycloalkyl, C3-C10-cycloalkenyl or C3-C10-halocycloalkenyl, where R2 may in each case contain one, two, three, four or five substituents L, as defined herein.


According to one embodiment, R2 is hydrogen, C1-C10-alkyl, C1-C10-haloalkyl, C4-C10-alkenyl, C2-C10-haloalkenyl, C2-C10-alkynyl, C3-C10-haloalkynyl, C4-C10-alkadienyl, C4-C10-haloalkadienyl, C3-C10-cycloalkyl, C3-C10-halocycloalkyl, C3-C10-cycloalkenyl or C3-C10-halocycloalkenyl, in particular hydrogen, C1-C10-alkyl, C1-C10-haloalkyl, C3-C10-cycloalkyl, C3-C10-halocycloalkyl, C3-C10-cycloalkenyl or C3-C10-halocycloalkenyl, where R2 may in each case contain one, two, three, four or five substituents L, as defined herein.


According to a preferred embodiment, R2 is hydrogen.


According to a further embodiment, R2 is C1-C10-alkyl, C1-C10-haloalkyl, phenyl-C1-C4-alkyl, C4-C10-alkenyl, C4-C10-haloalkenyl, C2-C10-alkynyl, C3-C10-haloalkynyl, C4-C10-alkadienyl, C4-C10-haloalkadienyl, C3-C10-cycloalkyl, C3-C10-halocycloalkyl, C3-C10-cycloalkenyl or C3-C10-halocycloalkenyl, in particular C1-C4-alkyl, C3-C4-alkynyl or phenyl-C1-C4-alkyl. Specific examples of R2 are methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, 3-propargyl, 4-but-2-ynyl and benzyl.


According to the present invention, R3 is hydrogen, C1-C10-alkyl, C1-C10-haloalkyl, C2-C10-alkenyl, C2-C10-haloalkenyl, C2-C10-alkynyl, C3-C10-haloalkynyl, C4-C10-alkadienyl, C4-C10-haloalkadienyl, C3-C10-cycloalkyl, C3-C10-halocycloalkyl, C3-C10-cycloalkenyl, C3-C10-halocycloalkenyl, carboxyl, formyl, Si(A5A6A7), C(O)Rπ, C(O)Rπ, C(S)ORπ, C(O)SRπ, C(S)SRπ, C(NRA)SRπ, C(S)Rπ, C(NRπ)N NA3A4, C(NRπ)RA, C(NRπ)ORA, C(O)NA3A4, C(S)NA3A4 or S(═O)nA1; where

    • A1 is hydrogen, hydroxyl, C1-C8-alkyl, C1-C8-haloalkyl, amino, C1-C8-alkylamino, di-C1-C8-alkylamino, phenyl, phenylamino or phenyl-C1-C8-alkylamino;
    • Rπ is C1-C8-alkyl, C3-C8-alkenyl, C3-C8-alkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkenyl or phenyl;
    • RA is hydrogen, C2-alkenyl, C2-alkynyl or one of the groups mentioned for Rπ;
    • A5, A6, A7 independently of one another are C1-C10-alkyl, C3-C8-alkenyl, C3-C8-alkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkenyl or phenyl,


      where Rπ, RA, A5, A6 and A7 are, unless indicated otherwise, independently of one another unsubstituted or substituted by one, two, three, four or five L, as defined above.


R3 may contain one, two, three, four or five substituents L, as defined herein.


According to a preferred embodiment, R3 is hydrogen.


According to a further embodiment, R3 is C1-C10-alkyl, C1-C10-haloalkyl, phenyl-C1-C10-alkyl, C2-C10-alkenyl, C2-C10-haloalkenyl, C2-C10-alkynyl, C3-C10-haloalkynyl, C4-C10-alkadienyl, C4-C10-haloalkadienyl, C3-C10-cycloalkyl, C3-C10-halocycloalkyl, C3-C10-cycloalkenyl, C3-C10-halocycloalkenyl, carboxyl, formyl, Si(A5A6A7), C(O)Rπ, C(O)Rπ, C(S)ORπ, C(O)SRπ, C(S)SRπ, C(NRA)SRπ, C(S)Rπ, C(NRπ)N NA3A4, C(NRπ)RA, C(NRπ)ORA, C(O)NA3A4, C(S)NA3A4 or S(═O)nA1, in particular C1-C4-alkyl, phenyl-C1-C4-alkyl, halophenyl-C1-C4-alkyl, C2-C4-alkenyl, C3-C4-alkynyl, tri-C1-C4-alkylsilyl, C(O)Rπ or S(═O)2A1, where

    • A1 is hydroxyl, C1-C4-alkyl, phenyl or C1-C4-alkylphenyl;
    • Rπ is C1-C4-alkyl, carboxy-C1-C4-alkyl or carboxyphenyl;
    • RA is hydrogen, C2-alkenyl, C2-alkynyl or one of the groups mentioned for Rπ, preferably C1-C4-alkyl, C3-C6-cycloalkyl or phenyl;


A5, A6, A7 independently of one another are C1-C4-alkyl or phenyl, where the phenyl ring is unsubstituted or substituted by one, two, three, four or five L, as defined herein.


Specific examples of R3 are trimethylsilyl, Si(CH3)2(CH2)3CH3, Si(CH3)2(C6H5), methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, 2-vinyl, 3-allyl, 3-propargyl, 4-but-2-ynyl, C(═O)CH3, C(═O)CH2CH3, C(═O)CH2CH2CH3, C(═O)(CH2)2COOH, C(═O)(CH2)3COOH, C(═O)(2-COOH—C6H4), SO2OH, SO2CH3, SO2C6H5, SO2(4-methyl-C6H4), benzyl and 4-chlorobenzyl.


According to the present invention, R4 is hydrogen, C1-C10-alkyl, C1-C10-haloalkyl, C2-C10-alkenyl, C2-C10-haloalkenyl, C2-C10-alkynyl, C3-C10-haloalkynyl, C4-C10-alkadienyl, C4-C10-haloalkadienyl, C3-C10-cycloalkyl, C3-C10-halocycloalkyl, C3-C10-cycloalkenyl or C3-C10-halocycloalkenyl, where R4 may contain one, two, three, four or five substituents L, as defined herein.


According to a preferred embodiment, R4 is hydrogen.


According to a further embodiment, R4 is C1-C10-alkyl, C1-C10-haloalkyl, phenyl-C1-C4-alkyl, C2-C10-alkenyl, C2-C10-haloalkenyl, C2-C10-alkynyl, C3-C10-haloalkynyl, C4-C10-alkadienyl, C4-C10-haloalkadienyl, C3-C10-cycloalkyl, C3-C10-halocycloalkyl, C3-C10-cycloalkenyl or C3-C10-halocycloalkenyl, in particular C1-C4-alkyl, C2-C4-alkenyl, C3-C4-alkynyl or phenyl-C1-C4-alkyl. Specific examples of R4 are methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, 2-vinyl, 3-allyl, 3-propargyl, 4-but-2-ynyl and benzyl.


According to a further embodiment of the compounds according to the invention, R1 is phenyl which contains one, two, three, four or five independently selected substituents L, as defined herein or as defined as being preferred, and at least one of the substituents R2, R3 and R4 is not hydrogen. According to one aspect, R2 is not hydrogen. According to a further aspect, R3 is not hydrogen. According to one aspect, R4 is not hydrogen.


Independently, L has the meanings or preferred meanings mentioned herein and in the claims for L. Unless indicated otherwise, L is preferably independently selected from the group consisting of halogen, cyano, nitro, cyanato (OCN), C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, S-A1, C(═O)A2, C(═S)A2, NA3A; where A1, A2, A3, A4 are as defined below:

    • A1 is hydrogen, hydroxyl, C1-C4-alkyl, C1-C4-haloalkyl;
    • A2 is one of the groups mentioned for A1 or C1-C4-alkoxy, C1-C4-haloalkoxy, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C3-C6-cycloalkoxy or C3-C6-halocycloalkoxy;
    • A3,A4 independently of one another are hydrogen, C1-C4-alkyl, C1-C4-haloalkyl;
    • where the aliphatic and/or alicyclic and/or aromatic groups of the radical definitions of L for their part may carry one, two, three or four identical or different groups RL:
    • RL is halogen, cyano, nitro, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, amino, C1-C8-alkylamino, di-C1-C8-alkylamino.


Furthermore preferably, L is independently selected from the group consisting of halogen, NO2, amino, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-haloalkyl, C1-C4-haloalkoxy, C1-C4-alkylamino, C1-C4-dialkylamino, thio and C1-C4-alkylthio.


Furthermore preferably, L is independently selected from the group consisting of halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy and C1-C4-haloalkylthio.


According to a further preferred embodiment, L is independently selected from the group consisting of F, Cl, Br, CH3, C2H5, i-C3H7, t-C4H9, OCH3, OC2H5, CF3, CCl3, CHF2, CClF2, OCF3, OCHF2 and SCF3, in particular selected from the group consisting of F, Cl, CH3, C2H5, OCH3, OC2H5, CF3, CHF2, OCF3, OCHF2 and SCF3. According to one aspect, L is independently selected from the group consisting of F, Cl, CH3, OCH3, CF3, OCF3 and OCHF2. It may be preferred for L to be independently F or Cl.


According to a further embodiment, L, in particular if L is a substituent at R1=phenyl, is independently selected from the group consisting of F, Br, CH3, C2H5, i-C3H7, t-C4H9, OC2H5, CF3, CCl3, CHF2, CClF2, OCF3, OCHF2 and SCF3.


According to yet a further embodiment, L is independently selected from the group consisting of F, Cl, Br, methyl and methoxy.


The meanings described above of the variables X, Z, R1, R2, R3 and R4 and L for compounds I apply correspondingly to the precursors of the compounds according to the invention.


In particular with a view to their use, preference is given to the compounds I according to the invention compiled in Tables 1a to 308a below, taking into account the provisos stated herein. 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 1a

    • Compounds I in which X is N, Z is CH2CH2CH2, R4 is H, R3 is H and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.1aA-1 to I.1aA-1554)


Table 2a

    • Compounds I in which X is N, Z is CH2CH(CH3)CH2, R4 is H, R3 is H and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.2aA-1 to I.2aA-1554)


Table 3a

    • Compounds I in which X is N, Z is CH2CH2CH(CH3), R4 is H, R3 is H and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.3aA-1 to I.3aA-1554)


Table 4a

    • Compounds I in which X is N, Z is CH2C(CH3)2CH2, R4 is H, R3 is H and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.4aA-1 to I.4aA-1554)


Table 5a

    • Compounds I in which X is N, Z is CH(CH3)CH2CH2, R4 is H, R3 is H and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.5aA-1 to I.5aA-1554)


Table 6a

    • Compounds I in which X is N, Z is CH2C(CH2CH2)CH2, R4 is H, R3 is H and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.6aA-1 to I.6aA-1554)


Table 7a

    • Compounds I in which X is N, Z is C(CH2CH2)CH2CH2, R4 is H, R3 is H and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.7aA-1 to I.7aA-1554)


Table 8a

    • Compounds I in which X is N, Z is CH2CH2CH2, R4 is H, R3 is CH2CH═CH2 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.8aA-1 to I.8aA-1554)


Table 9a

    • Compounds I in which X is N, Z is CH2CH(CH3)CH2, R4 is H, R3 is CH2CH═CH2 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.9aA-1 to I.9aA-1554)


Table 10a

    • Compounds I in which X is N, Z is CH2CH2CH(CH3), R4 is H, R3 is CH2CH═CH2 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.10aA-1 to I.10aA-1554)


Table 11a

    • Compounds I in which X is N, Z is CH2C(CH3)2CH2, R4 is H, R3 is CH2CH═CH2 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.11aA-1 to I.11aA-1554)


Table 12a

    • Compounds I in which X is N, Z is CH(CH3)CH2CH2, R4 is H, R3 is CH2CH═CH2 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.12aA-1 to I.12aA-1554)


Table 13a

    • Compounds I in which X is N, Z is CH2C(CH2CH2)CH2, R4 is H, R3 is CH2CH═CH2 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.13aA-1 to I.13aA-1554)


Table 14a

    • Compounds I in which X is N, Z is C(CH2CH2)CH2CH2, R4 is H, R3 is CH2CH═CH2 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.14aA-1 to I.14aA-1554)


Table 15a

    • Compounds I in which X is N, Z is CH2CH2CH2, R4 is H, R3 is CH3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.15aA-1 to I.15aA-1554)


Table 16a

    • Compounds I in which X is N, Z is CH2CH(CH3)CH2, R4 is H, R3 is CH3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.16aA-1 to I.16aA-1554)


Table 17a

    • Compounds I in which X is N, Z is CH2CH2CH(CH3), R4 is H, R3 is CH3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.17aA-1 to I.17aA-1554)


Table 18a

    • Compounds I in which X is N, Z is CH2C(CH3)2CH2, R4 is H, R3 is CH3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.18aA-1 to I.18aA-1554)


Table 19a

    • Compounds I in which X is N, Z is CH(CH3)CH2CH2, R4 is H, R3 is CH3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.19aA-1 to I.19aA-1554)


Table 20a

    • Compounds I in which X is N, Z is CH2C(CH2CH2)CH2, R4 is H, R3 is CH3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.20aA-1 to I.20aA-1554)


Table 21a

    • Compounds I in which X is N, Z is C(CH2CH2)CH2CH2, R4 is H, R3 is CH3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.21aA-1 to I.21aA-1554)


Table 22a

    • Compounds I in which X is N, Z is CH2CH2CH2, R4 is H, R3 is CH2C≡CH and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.22aA-1 to I.22aA-1554)


Table 23a

    • Compounds I in which X is N, Z is CH2CH(CH3)CH2, R4 is H, R3 is CH2C≡CH and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.23aA-1 to I.23aA-1554)


Table 24a

    • Compounds I in which X is N, Z is CH2CH2CH(CH3), R4 is H, R3 is CH2C≡CH and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.24aA-1 to I.24aA-1554)


Table 25a

    • Compounds I in which X is N, Z is CH2C(CH3)2CH2, R4 is H, R3 is CH2C≡CH and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.25aA-1 to I.25aA-1554)


Table 26a

    • Compounds I in which X is N, Z is CH(CH3)CH2CH2, R4 is H, R3 is CH2C≡CH and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.26aA-1 to I.26aA-1554)


Table 27a

    • Compounds I in which X is N, Z is CH2C(CH2CH2)CH2, R4 is H, R3 is CH2C≡CH and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.27aA-1 to I.27aA-1554)


Table 28a

    • Compounds I in which X is N, Z is C(CH2CH2)CH2CH2, R4 is H, R3 is CH2C≡CH and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.28aA-1 to I.28aA-1554)


Table 29a

    • Compounds I in which X is N, Z is CH2CH2CH2, R4 is H, R3 is C(═O)CH3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.29aA-1 to I.29aA-1554)


Table 30a

    • Compounds I in which X is N, Z is CH2CH(CH3)CH2, R4 is H, R3 is C(═O)CH3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.30aA-1 to I.30aA-1554)


Table 31a

    • Compounds I in which X is N, Z is CH2CH2CH(CH3), R4 is H, R3 is C(═O)CH3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.31aA-1 to I.31aA-1554)


Table 32a

    • Compounds I in which X is N, Z is CH2C(CH3)2CH2, R4 is H, R3 is C(═O)CH3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.32aA-1 to I.32aA-1554)


Table 33a

    • Compounds I in which X is N, Z is CH(CH3)CH2CH2, R4 is H, R3 is C(═O)CH3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.33aA-1 to I.33aA-1554)


Table 34a

    • Compounds I in which X is N, Z is CH2C(CH2CH2)CH2, R4 is H, R3 is C(═O)CH3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.34aA-1 to I.34aA-1554)


Table 35a

    • Compounds I in which X is N, Z is C(CH2CH2)CH2CH2, R4 is H, R3 is C(═O)CH3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.35aA-1 to I.35aA-1554)


Table 36a

    • Compounds I in which X is N, Z is CH2CH2CH2, R4 is CH3, R3 is H and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.36aA-1 to I.36aA-1554)


Table 37a

    • Compounds I in which X is N, Z is CH2CH(CH3)CH2, R4 is CH3, R3 is H and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.37aA-1 to I.37aA-1554)


Table 38a

    • Compounds I in which X is N, Z is CH2CH2CH(CH3), R4 is CH3, R3 is H and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.38aA-1 to I.38aA-1554)


Table 39a

    • Compounds I in which X is N, Z is CH2C(CH3)2CH2, R4 is CH3, R3 is H and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.39aA-1 to I.39aA-1554)


Table 40a

    • Compounds I in which X is N, Z is CH(CH3)CH2CH2, R4 is CH3, R3 is H and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.40aA-1 to I.40aA-1554)


Table 41a

    • Compounds I in which X is N, Z is CH2C(CH2CH2)CH2, R4 is CH3, R3 is H and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.41aA-1 to I.41aA-1554)


Table 42a

    • Compounds I in which X is N, Z is C(CH2CH2)CH2CH2, R4 is CH3, R3 is H and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.42aA-1 to I.42aA-1554)


Table 43a

    • Compounds I in which X is N, Z is CH2CH2CH2, R4 is CH3, R3 is CH2CH═CH2 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.43aA-1 to I.43aA-1554)


Table 44a

    • Compounds I in which X is N, Z is CH2CH(CH3)CH2, R4 is CH3, R3 is CH2CH═CH2 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.44aA-1 to I.44aA-1554)


Table 45a

    • Compounds I in which X is N, Z is CH2CH2CH(CH3), R4 is CH3, R3 is CH2CH═CH2 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.45aA-1 to I.45aA-1554)


Table 46a

    • Compounds I in which X is N, Z is CH2C(CH3)2CH2, R4 is CH3, R3 is CH2CH═CH2 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.46aA-1 to I.46aA-1554)


Table 47a

    • Compounds I in which X is N, Z is CH(CH3)CH2CH2, R4 is CH3, R3 is CH2CH═CH2 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.47aA-1 to I.47aA-1554)


Table 48a

    • Compounds I in which X is N, Z is CH2C(CH2CH2)CH2, R4 is CH3, R3 is CH2CH═CH2 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.48aA-1 to I.48aA-1554)


Table 49a

    • Compounds I in which X is N, Z is C(CH2CH2)CH2CH2, R4 is CH3, R3 is CH2CH═CH2 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.49aA-1 to I.49aA-1554)


Table 50a

    • Compounds I in which X is N, Z is CH2CH2CH2, R4 is CH3, R3 is CH3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.50aA-1 to I.50aA-1554)


Table 51a

    • Compounds I in which X is N, Z is CH2CH(CH3)CH2, R4 is CH3, R3 is CH3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.51aA-1 to I.51aA-1554)


Table 52a

    • Compounds I in which X is N, Z is CH2CH2CH(CH3), R4 is CH3, R3 is CH3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.52aA-1 to I.52aA-1554)


Table 53a

    • Compounds I in which X is N, Z is CH2C(CH3)2CH2, R4 is CH3, R3 is CH3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.53aA-1 to I.53aA-1554)


Table 54a

    • Compounds I in which X is N, Z is CH(CH3)CH2CH2, R4 is CH3, R3 is CH3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.54aA-1 to I.54aA-1554)


Table 55a

    • Compounds I in which X is N, Z is CH2C(CH2CH2)CH2, R4 is CH3, R3 is CH3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.55aA-1 to I.55aA-1554)


Table 56a

    • Compounds I in which X is N, Z is C(CH2CH2)CH2CH2, R4 is CH3, R3 is CH3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.56aA-1 to I.56aA-1554)


Table 57a

    • Compounds I in which X is N, Z is CH2CH2CH2, R4 is CH3, R3 is CH2C≡CH and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.57aA-1 to I.57aA-1554)


Table 58a

    • Compounds I in which X is N, Z is CH2CH(CH3)CH2, R4 is CH3, R3 is CH2C≡CH and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.58aA-1 to I.58aA-1554)


Table 59a

    • Compounds I in which X is N, Z is CH2CH2CH(CH3), R4 is CH3, R3 is CH2C≡CH and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.59aA-1 to I.59aA-1554)


Table 60a

    • Compounds I in which X is N, Z is CH2C(CH3)2CH2, R4 is CH3, R3 is CH2C≡CH and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.60aA-1 to I.60aA-1554)


Table 61a

    • Compounds I in which X is N, Z is CH(CH3)CH2CH2, R4 is CH3, R3 is CH2C≡CH and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.61aA-1 to I.61aA-1554)


Table 62a

    • Compounds I in which X is N, Z is CH2C(CH2CH2)CH2, R4 is CH3, R3 is CH2C≡CH and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.62aA-1 to I.62aA-1554)


Table 63a

    • Compounds I in which X is N, Z is C(CH2CH2)CH2CH2, R4 is CH3, R3 is CH2C≡CH and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.63aA-1 to I.63aA-1554)


Table 64a

    • Compounds I in which X is N, Z is CH2CH2CH2, R4 is CH3, R3 is C(═O)CH3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.64aA-1 to I.64aA-1554)


Table 65a

    • Compounds I in which X is N, Z is CH2CH(CH3)CH2, R4 is CH3, R3 is C(═O)CH3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.65aA-1 to I.65aA-1554)


Table 66a

    • Compounds I in which X is N, Z is CH2CH2CH(CH3), R4 is CH3, R3 is C(═O)CH3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.66aA-1 to I.66aA-1554)


Table 67a

    • Compounds I in which X is N, Z is CH2C(CH3)2CH2, R4 is CH3, R3 is C(═O)CH3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.67aA-1 to I.67aA-1554)


Table 68a

    • Compounds I in which X is N, Z is CH(CH3)CH2CH2, R4 is CH3, R3 is C(═O)CH3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.68aA-1 to I.68aA-1554)


Table 69a

    • Compounds I in which X is N, Z is CH2C(CH2CH2)CH2, R4 is CH3, R3 is C(═O)CH3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.69aA-1 to I.69aA-1554)


Table 70a

    • Compounds I in which X is N, Z is C(CH2CH2)CH2CH2, R4 is CH3, R3 is C(═O)CH3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.70aA-1 to I.70aA-1554)


Table 71a

    • Compounds I in which X is N, Z is CH2CH2CH2, R4 is CH═CH2, R3 is H and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.71aA-1 to I.71aA-1554)


Table 72a

    • Compounds I in which X is N, Z is CH2CH(CH3)CH2, R4 is CH═CH2, R3 is H and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.72aA-1 to I.72aA-1554)


Table 73a

    • Compounds I in which X is N, Z is CH2CH2CH(CH3), R4 is CH═CH2, R3 is H and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.73aA-1 to I.73aA-1554)


Table 74a

    • Compounds I in which X is N, Z is CH2C(CH3)2CH2, R4 is CH═CH2, R3 is H and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.74aA-1 to I.74aA-1554)


Table 75a

    • Compounds I in which X is N, Z is CH(CH3)CH2CH2, R4 is CH═CH2, R3 is H and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.75aA-1 to I.75aA-1554)


Table 76a

    • Compounds I in which X is N, Z is CH2C(CH2CH2)CH2, R4 is CH═CH2, R3 is H and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.76aA-1 to I.76aA-1554)


Table 77a

    • Compounds I in which X is N, Z is C(CH2CH2)CH2CH2, R4 is CH═CH2, R3 is H and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.77aA-1 to I.77aA-1554)


Table 78a

    • Compounds I in which X is N, Z is CH2CH2CH2, R4 is CH═CH2, R3 is CH2CH═CH2 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.78aA-1 to I.78aA-1554)


Table 79a

    • Compounds I in which X is N, Z is CH2CH(CH3)CH2, R4 is CH═CH2, R3 is CH2CH═CH2 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.79aA-1 to I.79aA-1554)


Table 80a

    • Compounds I in which X is N, Z is CH2CH2CH(CH3), R4 is CH═CH2, R3 is CH2CH═CH2 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.80aA-1 to I.80aA-1554)


Table 81a

    • Compounds I in which X is N, Z is CH2C(CH3)2CH2, R4 is CH═CH2, R3 is CH2CH═CH2 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.81aA-1 to I.81aA-1554)


Table 82a

    • Compounds I in which X is N, Z is CH(CH3)CH2CH2, R4 is CH═CH2, R3 is CH2CH═CH2 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.82aA-1 to I.82aA-1554)


Table 83a

    • Compounds I in which X is N, Z is CH2C(CH2CH2)CH2, R4 is CH═CH2, R3 is CH2CH═CH2 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.83aA-1 to I.83aA-1554)


Table 84a

    • Compounds I in which X is N, Z is C(CH2CH2)CH2CH2, R4 is CH═CH2, R3 is CH2CH═CH2 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.84aA-1 to I.84aA-1554)


Table 85a

    • Compounds I in which X is N, Z is CH2CH2CH2, R4 is CH═CH2, R3 is CH3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.85aA-1 to I.85aA-1554)


Table 86a

    • Compounds I in which X is N, Z is CH2CH(CH3)CH2, R4 is CH═CH2, R3 is CH3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.86aA-1 to I.86aA-1554)


Table 87a

    • Compounds I in which X is N, Z is CH2CH2CH(CH3), R4 is CH═CH2, R3 is CH3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.87aA-1 to I.87aA-1554)


Table 88a

    • Compounds I in which X is N, Z is CH2C(CH3)2CH2, R4 is CH═CH2, R3 is CH3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.88aA-1 to I.88aA-1554)


Table 89a

    • Compounds I in which X is N, Z is CH(CH3)CH2CH2, R4 is CH═CH2, R3 is CH3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.89aA-1 to I.89aA-1554)


Table 90a

    • Compounds I in which X is N, Z is CH2C(CH2CH2)CH2, R4 is CH═CH2, R3 is CH3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.90aA-1 to I.90aA-1554)


Table 91a

    • Compounds I in which X is N, Z is C(CH2CH2)CH2CH2, R4 is CH═CH2, R3 is CH3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.91aA-1 to I.91aA-1554)


Table 92a

    • Compounds I in which X is N, Z is CH2CH2CH2, R4 is CH═CH2, R3 is CH2C≡CH and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.92aA-1 to I.92aA-1554)


Table 93a

    • Compounds I in which X is N, Z is CH2CH(CH3)CH2, R4 is CH═CH2, R3 is CH2C≡CH and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.93aA-1 to I.93aA-1554)


Table 94a

    • Compounds I in which X is N, Z is CH2CH2CH(CH3), R4 is CH═CH2, R3 is CH2C≡CH and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.94aA-1 to I.94aA-1554)


Table 95a

    • Compounds I in which X is N, Z is CH2C(CH3)2CH2, R4 is CH═CH2, R3 is CH2C≡CH and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.95aA-1 to I.95aA-1554)


Table 96a

    • Compounds I in which X is N, Z is CH(CH3)CH2CH2, R4 is CH═CH2, R3 is CH2C≡CH and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.96aA-1 to I.96aA-1554)


Table 97a

    • Compounds I in which X is N, Z is CH2C(CH2CH2)CH2, R4 is CH═CH2, R3 is CH2C≡CH and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.97aA-1 to I.97aA-1554)


Table 98a

    • Compounds I in which X is N, Z is C(CH2CH2)CH2CH2, R4 is CH═CH2, R3 is CH2C≡CH and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.98aA-1 to I.98aA-1554)


Table 99a

    • Compounds I in which X is N, Z is CH2CH2CH2, R4 is CH═CH2, R3 is C(═O)CH3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.99aA-1 to I.99aA-1554)


Table 100a

    • Compounds I in which X is N, Z is CH2CH(CH3)CH2, R4 is CH═CH2, R3 is C(═O)CH3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.100aA-1 to I.100aA-1554)


Table 101a

    • Compounds I in which X is N, Z is CH2CH2CH(CH3), R4 is CH═CH2, R3 is C(═O)CH3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.101aA-1 to I.101aA-1554)


Table 102a

    • Compounds I in which X is N, Z is CH2C(CH3)2CH2, R4 is CH═CH2, R3 is C(═O)CH3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.102aA-1 to I.102aA-1554)


Table 103a

    • Compounds I in which X is N, Z is CH(CH3)CH2CH2, R4 is CH═CH2, R3 is C(═O)CH3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.103aA-1 to I.103aA-1554)


Table 104a

    • Compounds I in which X is N, Z is CH2C(CH2CH2)CH2, R4 is CH═CH2, R3 is C(═O)CH3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.104aA-1 to I.104aA-1554)


Table 105a

    • Compounds I in which X is N, Z is C(CH2CH2)CH2CH2, R4 is CH═CH2, R3 is C(═O)CH3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.105aA-1 to I.105aA-1554)


Table 106a

    • Compounds I in which X is N, Z is CH2CH2CH2, R4 is CH2C≡CH, R3 is H and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.106aA-1 to I.106aA-1554)


Table 107a

    • Compounds I in which X is N, Z is CH2CH(CH3)CH2, R4 is CH2C≡CH, R3 is H and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.107aA-1 to I.107aA-1554)


Table 108a

    • Compounds I in which X is N, Z is CH2CH2CH(CH3), R4 is CH2C≡CH, R3 is H and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.108aA-1 to I.108aA-1554)


Table 109a

    • Compounds I in which X is N, Z is CH2C(CH3)2CH2, R4 is CH2C≡CH, R3 is H and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.109aA-1 to I.109aA-1554)


Table 110a

    • Compounds I in which X is N, Z is CH(CH3)CH2CH2, R4 is CH2C≡CH, R3 is H and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.110aA-1 to I.110aA-1554)


Table 111a

    • Compounds I in which X is N, Z is CH2C(CH2CH2)CH2, R4 is CH2C≡CH, R3 is H and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.111aA-1 to I.111aA-1554)


Table 112a

    • Compounds I in which X is N, Z is C(CH2CH2)CH2CH2, R4 is CH2C≡CH, R3 is H and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.112aA-1 to I.112aA-1554)


Table 113a

    • Compounds I in which X is N, Z is CH2CH2CH2, R4 is CH2C≡CH, R3 is CH2CH═CH2 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.113aA-1 to I.113aA-1554)


Table 114a

    • Compounds I in which X is N, Z is CH2CH(CH3)CH2, R4 is CH2C≡CH, R3 is CH2CH═CH2 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.114aA-1 to I.114aA-1554)


Table 115a

    • Compounds I in which X is N, Z is CH2CH2CH(CH3), R4 is CH2C≡CH, R3 is CH2CH═CH2 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.115aA-1 to I.115aA-1554)


Table 116a

    • Compounds I in which X is N, Z is CH2C(CH3)2CH2, R4 is CH2C≡CH, R3 is CH2CH═CH2 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.116aA-1 to I.116aA-1554)


Table 117a

    • Compounds I in which X is N, Z is CH(CH3)CH2CH2, R4 is CH2C≡CH, R3 is CH2CH═CH2 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.117aA-1 to I.117aA-1554)


Table 118a

    • Compounds I in which X is N, Z is CH2C(CH2CH2)CH2, R4 is CH2C≡CH, R3 is CH2CH═CH2 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.118aA-1 to I.118aA-1554)


Table 119a

    • Compounds I in which X is N, Z is C(CH2CH2)CH2CH2, R4 is CH2C≡CH, R3 is CH2CH═CH2 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.119aA-1 to I.119aA-1554)


Table 120a

    • Compounds I in which X is N, Z is CH2CH2CH2, R4 is CH2C≡CH, R3 is CH3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.120aA-1 to I.120aA-1554)


Table 121a

    • Compounds I in which X is N, Z is CH2CH(CH3)CH2, R4 is CH2C≡CH, R3 is CH3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.121aA-1 to I.121aA-1554)


Table 122a

    • Compounds I in which X is N, Z is CH2CH2CH(CH3), R4 is CH2C≡CH, R3 is CH3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.122aA-1 to I.122aA-1554)


Table 123a

    • Compounds I in which X is N, Z is CH2C(CH3)2CH2, R4 is CH2C≡CH, R3 is CH3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.123aA-1 to I.123aA-1554)


Table 124a

    • Compounds I in which X is N, Z is CH(CH3)CH2CH2, R4 is CH2C≡CH, R3 is CH3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.124aA-1 to I.124aA-1554)


Table 125a

    • Compounds I in which X is N, Z is CH2C(CH2CH2)CH2, R4 is CH2C≡CH, R3 is CH3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.125aA-1 to I.125aA-1554)


Table 126a

    • Compounds I in which X is N, Z is C(CH2CH2)CH2CH2, R4 is CH2C≡CH, R3 is CH3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.126aA-1 to I.126aA-1554)


Table 127a

    • Compounds I in which X is N, Z is CH2CH2CH2, R4 is CH2C≡CH, R3 is CH2C≡CH and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.127aA-1 to I.127aA-1554)


Table 128a

    • Compounds I in which X is N, Z is CH2CH(CH3)CH2, R4 is CH2C≡CH, R3 is CH2C≡CH and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.128aA-1 to I.128aA-1554)


Table 129a

    • Compounds I in which X is N, Z is CH2CH2CH(CH3), R4 is CH2C≡CH, R3 is CH2C≡CH and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.129aA-1 to I.129aA-1554)


Table 130a

    • Compounds I in which X is N, Z is CH2C(CH3)2CH2, R4 is CH2C≡CH, R3 is CH2C≡CH and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.130aA-1 to I.130aA-1554)


Table 131a

    • Compounds I in which X is N, Z is CH(CH3)CH2CH2, R4 is CH2C≡CH, R3 is CH2C≡CH and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.131aA-1 to I.131aA-1554)


Table 132a

    • Compounds I in which X is N, Z is CH2C(CH2CH2)CH2, R4 is CH2C≡CH, R3 is CH2C≡CH and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.132aA-1 to I.132aA-1554)


Table 133a

    • Compounds I in which X is N, Z is C(CH2CH2)CH2CH2, R4 is CH2C≡CH, R3 is CH2C≡CH and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.133aA-1 to I.133aA-1554)


Table 134a

    • Compounds I in which X is N, Z is CH2CH2CH2, R4 is CH2C≡CH, R3 is C(═O)CH3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.134aA-1 to I.134aA-1554)


Table 135a

    • Compounds I in which X is N, Z is CH2CH(CH3)CH2, R4 is CH2C≡CH, R3 is C(═O)CH3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.135aA-1 to I.135aA-1554)


Table 136a

    • Compounds I in which X is N, Z is CH2CH2CH(CH3), R4 is CH2C≡CH, R3 is C(═O)CH3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.136aA-1 to I.136aA-1554)


Table 137a

    • Compounds I in which X is N, Z is CH2C(CH3)2CH2, R4 is CH2C≡CH, R3 is C(═O)CH3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.137aA-1 to I.137aA-1554)


Table 138a

    • Compounds I in which X is N, Z is CH(CH3)CH2CH2, R4 is CH2C≡CH, R3 is C(═O)CH3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.138aA-1 to I.138aA-1554)


Table 139a

    • Compounds I in which X is N, Z is CH2C(CH2CH2)CH2, R4 is CH2C≡CH, R3 is C(═O)CH3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.139aA-1 to I.139aA-1554)


Table 140a

    • Compounds I in which X is N, Z is C(CH2CH2)CH2CH2, R4 is CH2C≡CH, R3 is C(═O)CH3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.140aA-1 to I.140aA-1554)


Table 141a

    • Compounds I in which X is CH, Z is CH2CH2CH2, R4 is H, R3 is H and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.141aA-1 to I.141aA-1554)


Table 142a

    • Compounds I in which X is CH, Z is CH2CH(CH3)CH2, R4 is H, R3 is H and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.142aA-1 to I.142aA-1554)


Table 143a

    • Compounds I in which X is CH, Z is CH2CH2CH(CH3), R4 is H, R3 is H and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.143aA-1 to I.143aA-1554)


Table 144a

    • Compounds I in which X is CH, Z is CH2C(CH3)2CH2, R4 is H, R3 is H and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.144aA-1 to I.144aA-1554)


Table 145a

    • Compounds I in which X is CH, Z is CH(CH3)CH2CH2, R4 is H, R3 is H and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.145aA-1 to I.145aA-1554)


Table 146a

    • Compounds I in which X is CH, Z is CH2C(CH2CH2)CH2, R4 is H, R3 is H and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.146aA-1 to I.146aA-1554)


Table 147a

    • Compounds I in which X is CH, Z is C(CH2CH2)CH2CH2, R4 is H, R3 is H and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.147aA-1 to I.147aA-1554)


Table 148a

    • Compounds I in which X is CH, Z is CH2CH2CH2, R4 is H, R3 is CH2CH═CH2 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.148aA-1 to I.148aA-1554)


Table 149a

    • Compounds I in which X is CH, Z is CH2CH(CH3)CH2, R4 is H, R3 is CH2CH═CH2 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.149aA-1 to I.149aA-1554)


Table 150a

    • Compounds I in which X is CH, Z is CH2CH2CH(CH3), R4 is H, R3 is CH2CH═CH2 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.150aA-1 to I.150aA-1554)


Table 151a

    • Compounds I in which X is CH, Z is CH2C(CH3)2CH2, R4 is H, R3 is CH2CH═CH2 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.151aA-1 to I.151aA-1554)


Table 152a

    • Compounds I in which X is CH, Z is CH(CH3)CH2CH2, R4 is H, R3 is CH2CH═CH2 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.152aA-1 to I.152aA-1554)


Table 153a

    • Compounds I in which X is CH, Z is CH2C(CH2CH2)CH2, R4 is H, R3 is CH2CH═CH2 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.153aA-1 to I.153aA-1554)


Table 154a

    • Compounds I in which X is CH, Z is C(CH2CH2)CH2CH2, R4 is H, R3 is CH2CH═CH2 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.154aA-1 to I.154aA-1554)


Table 155a

    • Compounds I in which X is CH, Z is CH2CH2CH2, R4 is H, R3 is CH3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.155aA-1 to I.155aA-1554)


Table 156a

    • Compounds I in which X is CH, Z is CH2CH(CH3)CH2, R4 is H, R3 is CH3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.156aA-1 to I.156aA-1554)


Table 157a

    • Compounds I in which X is CH, Z is CH2CH2CH(CH3), R4 is H, R3 is CH3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.157aA-1 to I.157aA-1554)


Table 158a

    • Compounds I in which X is CH, Z is CH2C(CH3)2CH2, R4 is H, R3 is CH3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.158aA-1 to I.158aA-1554)


Table 159a

    • Compounds I in which X is CH, Z is CH(CH3)CH2CH2, R4 is H, R3 is CH3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.159aA-1 to I.159aA-1554)


Table 160a

    • Compounds I in which X is CH, Z is CH2C(CH2CH2)CH2, R4 is H, R3 is CH3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.160aA-1 to I.160aA-1554)


Table 161a

    • Compounds I in which X is CH, Z is C(CH2CH2)CH2CH2, R4 is H, R3 is CH3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.161aA-1 to I.161aA-1554)


Table 162a

    • Compounds I in which X is CH, Z is CH2CH2CH2, R4 is H, R3 is CH2C≡CH and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.162aA-1 to I.162aA-1554)


Table 163a

    • Compounds I in which X is CH, Z is CH2CH(CH3)CH2, R4 is H, R3 is CH2C≡CH and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.163aA-1 to I.163aA-1554)


Table 164a

    • Compounds I in which X is CH, Z is CH2CH2CH(CH3), R4 is H, R3 is CH2C≡CH and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.164aA-1 to I.164aA-1554)


Table 165a

    • Compounds I in which X is CH, Z is CH2C(CH3)2CH2, R4 is H, R3 is CH2C≡CH and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.165aA-1 to I.165aA-1554)


Table 166a

    • Compounds I in which X is CH, Z is CH(CH3)CH2CH2, R4 is H, R3 is CH2C≡CH and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.166aA-1 to I.166aA-1554)


Table 167a

    • Compounds I in which X is CH, Z is CH2C(CH2CH2)CH2, R4 is H, R3 is CH2C≡CH and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.167aA-1 to I.167aA-1554)


Table 168a

    • Compounds I in which X is CH, Z is C(CH2CH2)CH2CH2, R4 is H, R3 is CH2C≡CH and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.168aA-1 to I.168aA-1554)


Table 169a

    • Compounds I in which X is CH, Z is CH2CH2CH2, R4 is H, R3 is C(═O)CH3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.169aA-1 to I.169aA-1554)


Table 170a

    • Compounds I in which X is CH, Z is CH2CH(CH3)CH2, R4 is H, R3 is C(═O)CH3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.170aA-1 to I.170aA-1554)


Table 171a

    • Compounds I in which X is CH, Z is CH2CH2CH(CH3), R4 is H, R3 is C(═O)CH3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.171aA-1 to I.171aA-1554)


Table 172a

    • Compounds I in which X is CH, Z is CH2C(CH3)2CH2, R4 is H, R3 is C(═O)CH3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.172aA-1 to I.172aA-1554)


Table 173a

    • Compounds I in which X is CH, Z is CH(CH3)CH2CH2, R4 is H, R3 is C(═O)CH3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.173aA-1 to I.173aA-1554)


Table 174a

    • Compounds I in which X is CH, Z is CH2C(CH2CH2)CH2, R4 is H, R3 is C(═O)CH3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.174aA-1 to I.174aA-1554)


Table 175a

    • Compounds I in which X is CH, Z is C(CH2CH2)CH2CH2, R4 is H, R3 is C(═O)CH3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.175aA-1 to I.175aA-1554)


Table 176a

    • Compounds I in which X is CH, Z is CH2CH2CH2, R4 is CH3, R3 is H and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.176aA-1 to I.176aA-1554)


Table 177a

    • Compounds I in which X is CH, Z is CH2CH(CH3)CH2, R4 is CH3, R3 is H and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.177aA-1 to I.177aA-1554)


Table 178a

    • Compounds I in which X is CH, Z is CH2CH2CH(CH3), R4 is CH3, R3 is H and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.178aA-1 to I.178aA-1554)


Table 179a

    • Compounds I in which X is CH, Z is CH2C(CH3)2CH2, R4 is CH3, R3 is H and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.179aA-1 to I.179aA-1554)


Table 180a

    • Compounds I in which X is CH, Z is CH(CH3)CH2CH2, R4 is CH3, R3 is H and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.180aA-1 to I.180aA-1554)


Table 181a

    • Compounds I in which X is CH, Z is CH2C(CH2CH2)CH2, R4 is CH3, R3 is H and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.181aA-1 to I.181aA-1554)


Table 182a

    • Compounds I in which X is CH, Z is C(CH2CH2)CH2CH2, R4 is CH3, R3 is H and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.182aA-1 to I.182aA-1554)


Table 183a

    • Compounds I in which X is CH, Z is CH2CH2CH2, R4 is CH3, R3is CH2CH═CH2 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.183aA-1 to I.183aA-1554)


Table 184a

    • Compounds I in which X is CH, Z is CH2CH(CH3)CH2, R4 is CH3, R3 is CH2CH═CH2 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.184aA-1 to I.184aA-1554)


Table 185a

    • Compounds I in which X is CH, Z is CH2CH2CH(CH3), R4 is CH3, R3 is CH2CH═CH2 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.185aA-1 to I.185aA-1554)


Table 186a

    • Compounds I in which X is CH, Z is CH2C(CH3)2CH2, R4 is CH3, R3 is CH2CH═CH2 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.186aA-1 to I.186aA-1554)


Table 187a

    • Compounds I in which X is CH, Z is CH(CH3)CH2CH2, R4 is CH3, R3 is CH2CH═CH2 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.187aA-1 to I.187aA-1554)


Table 188a

    • Compounds I in which X is CH, Z is CH2C(CH2CH2)CH2, R4 is CH3, R3 is CH2CH═CH2 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.188aA-1 to I.188aA-1554)


Table 189a

    • Compounds I in which X is CH, Z is C(CH2CH2)CH2CH2, R4 is CH3, R3 is CH2CH═CH2 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.189aA-1 to I.189aA-1554)


Table 190a

    • Compounds I in which X is CH, Z is CH2CH2CH2, R4 is CH3, R3 is CH3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.190aA-1 to I.190aA-1554)


Table 191a

    • Compounds I in which X is CH, Z is CH2CH(CH3)CH2, R4 is CH3, R3 is CH3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.191aA-1 to I.191aA-1554)


Table 192a

    • Compounds I in which X is CH, Z is CH2CH2CH(CH3), R4 is CH3, R3 is CH3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.192aA-1 to I.192aA-1554)


Table 193a

    • Compounds I in which X is CH, Z is CH2C(CH3)2CH2, R4 is CH3, R3 is CH3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.193aA-1 to I.193aA-1554)


Table 194a

    • Compounds I in which X is CH, Z is CH(CH3)CH2CH2, R4 is CH3, R3 is CH3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.194aA-1 to I.194aA-1554)


Table 195a

    • Compounds I in which X is CH, Z is CH2C(CH2CH2)CH2, R4 is CH3, R3 is CH3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.195aA-1 to I.195aA-1554)


Table 196a

    • Compounds I in which X is CH, Z is C(CH2CH2)CH2CH2, R4 is CH3, R3 is CH3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.196aA-1 to I.196aA-1554)


Table 197a

    • Compounds I in which X is CH, Z is CH2CH2CH2, R4 is CH3, R3 is CH2C≡CH and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.197aA-1 to I.197aA-1554)


Table 198a

    • Compounds I in which X is CH, Z is CH2CH(CH3)CH2, R4 is CH3, R3 is CH2C≡CH and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.198aA-1 to I.198aA-1554)


Table 199a

    • Compounds I in which X is CH, Z is CH2CH2CH(CH3), R4 is CH3, R3 is CH2C≡CH and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.199aA-1 to I.199aA-1554)


Table 200a

    • Compounds I in which X is CH, Z is CH2C(CH3)2CH2, R4 is CH3, R3 is CH2C≡CH and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.200aA-1 to I.200aA-1554)


Table 201a

    • Compounds I in which X is CH, Z is CH(CH3)CH2CH2, R4 is CH3, R3 is CH2C≡CH and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.201aA-1 to I.201aA-1554)


Table 202a

    • Compounds I in which X is CH, Z is CH2C(CH2CH2)CH2, R4 is CH3, R3 is CH2C≡CH and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.202aA-1 to I.202aA-1554)


Table 203a

    • Compounds I in which X is CH, Z is C(CH2CH2)CH2CH2, R4 is CH3, R3 is CH2C≡CH and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.203aA-1 to I.203aA-1554)


Table 204a

    • Compounds I in which X is CH, Z is CH2CH2CH2, R4 is CH3, R3 is C(═O)CH3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.204aA-1 to I.204aA-1554)


Table 205a

    • Compounds I in which X is CH, Z is CH2CH(CH3)CH2, R4 is CH3, R3 is C(═O)CH3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.205aA-1 to I.205aA-1554)


Table 206a

    • Compounds I in which X is CH, Z is CH2CH2CH(CH3), R4 is CH3, R3 is C(═O)CH3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.206aA-1 to I.206aA-1554)


Table 207a

    • Compounds I in which X is CH, Z is CH2C(CH3)2CH2, R4 is CH3, R3 is C(═O)CH3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.207aA-1 to I.207aA-1554)


Table 208a

    • Compounds I in which X is CH, Z is CH(CH3)CH2CH2, R4 is CH3, R3 is C(═O)CH3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.208aA-1 to I.208aA-1554)


Table 209a

    • Compounds I in which X is CH, Z is CH2C(CH2CH2)CH2, R4 is CH3, R3 is C(═O)CH3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.209aA-1 to I.209aA-1554)


Table 210a

    • Compounds I in which X is CH, Z is C(CH2CH2)CH2CH2, R4 is CH3, R3 is C(═O)CH3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.210aA-1 to I.210aA-1554)


Table 211a

    • Compounds I in which X is CH, Z is CH2CH2CH2, R4 is CH═CH2, R3 is H and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.211aA-1 to I.211aA-1554)


Table 212a

    • Compounds I in which X is CH, Z is CH2CH(CH3)CH2, R4 is CH═CH2, R3 is H and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.212aA-1 to I.212aA-1554)


Table 213a

    • Compounds I in which X is CH, Z is CH2CH2CH(CH3), R4 is CH═CH2, R3 is H and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.213aA-1 to I.213aA-1554)


Table 214a

    • Compounds I in which X is CH, Z is CH2C(CH3)2CH2, R4 is CH═CH2, R3 is H and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.214aA-1 to I.214aA-1554)


Table 215a

    • Compounds I in which X is CH, Z is CH(CH3)CH2CH2, R4 is CH═CH2, R3 is H and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.215aA-1 to I.215aA-1554)


Table 216a

    • Compounds I in which X is CH, Z is CH2C(CH2CH2)CH2, R4 is CH═CH2, R3 is H and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.216aA-1 to I.216aA-1554)


Table 217a

    • Compounds I in which X is CH, Z is C(CH2CH2)CH2CH2, R4 is CH═CH2, R3 is H and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.217aA-1 to I.217aA-1554)


Table 218a

    • Compounds I in which X is CH, Z is CH2CH2CH2, R4 is CH═CH2, R3 is CH2CH═CH2 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.218aA-1 to I.218aA-1554)


Table 219a

    • Compounds I in which X is CH, Z is CH2CH(CH3)CH2, R4 is CH═CH2, R3 is CH2CH═CH2 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.219aA-1 to I.219aA-1554)


Table 220a

    • Compounds I in which X is CH, Z is CH2CH2CH(CH3), R4 is CH═CH2, R3 is CH2CH═CH2 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.220aA-1 to I.220aA-1554)


Table 221a

    • Compounds I in which X is CH, Z is CH2C(CH3)2CH2, R4 is CH═CH2, R3 is CH2CH═CH2 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.221aA-1 to I.221aA-1554)


Table 222a

    • Compounds I in which X is CH, Z is CH(CH3)CH2CH2, R4 is CH═CH2, R3 is CH2CH═CH2 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.222aA-1 to I.222aA-1554)


Table 223a

    • Compounds I in which X is CH, Z is CH2C(CH2CH2)CH2, R4 is CH═CH2, R3 is CH2CH═CH2 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.223aA-1 to I.223aA-1554)


Table 224a

    • Compounds I in which X is CH, Z is C(CH2CH2)CH2CH2, R4 is CH═CH2, R3 is CH2CH═CH2 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.224aA-1 to I.224aA-1554)


Table 225a

    • Compounds I in which X is CH, Z is CH2CH2CH2, R4 is CH═CH2, R3 is CH3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.225aA-1 to I.225aA-1554)


Table 226a

    • Compounds I in which X is CH, Z is CH2CH(CH3)CH2, R4 is CH═CH2, R3 is CH3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.226aA-1 to I.226aA-1554)


Table 227a

    • Compounds I in which X is CH, Z is CH2CH2CH(CH3), R4 is CH═CH2, R3 is CH3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.227aA-1 to I.227aA-1554)


Table 228a

    • Compounds I in which X is CH, Z is CH2C(CH3)2CH2, R4 is CH═CH2, R3 is CH3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.228aA-1 to I.228aA-1554)


Table 229a

    • Compounds I in which X is CH, Z is CH(CH3)CH2CH2, R4 is CH═CH2, R3 is CH3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.229aA-1 to I.229aA-1554)


Table 230a

    • Compounds I in which X is CH, Z is CH2C(CH2CH2)CH2, R4 is CH═CH2, R3 is CH3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.230aA-1 to I.230aA-1554)


Table 231a

    • Compounds I in which X is CH, Z is C(CH2CH2)CH2CH2, R4 is CH═CH2, R3 is CH3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.231 aA-1 to I.231aA-1554)


Table 232a

    • Compounds I in which X is CH, Z is CH2CH2CH2, R4 is CH═CH2, R3 is CH2C≡CH and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.232aA-1 to I.232aA-1554)


Table 233a

    • Compounds I in which X is CH, Z is CH2CH(CH3)CH2, R4 is CH═CH2, R3 is CH2C≡CH and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.233aA-1 to I.233aA-1554)


Table 234a

    • Compounds I in which X is CH, Z is CH2CH2CH(CH3), R4 is CH═CH2, R3 is CH2C≡CH and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.234aA-1 to I.234aA-1554)


Table 235a

    • Compounds I in which X is CH, Z is CH2C(CH3)2CH2, R4 is CH═CH2, R3 is CH2C≡CH and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.235aA-1 to I.235aA-1554)


Table 236a

    • Compounds I in which X is CH, Z is CH(CH3)CH2CH2, R4 is CH═CH2, R3 is CH2C≡CH and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.236aA-1 to I.236aA-1554)


Table 237a

    • Compounds I in which X is CH, Z is CH2C(CH2CH2)CH2, R4 is CH═CH2, R3 is CH2C≡CH and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.237aA-1 to I.237aA-1554)


Table 238a

    • Compounds I in which X is CH, Z is C(CH2CH2)CH2CH2, R4 is CH═CH2, R3 is CH2C≡CH and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.238aA-1 to I.238aA-1554)


Table 239a

    • Compounds I in which X is CH, Z is CH2CH2CH2, R4 is CH═CH2, R3 is C(═O)CH3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.239aA-1 to I.239aA-1554)


Table 240a

    • Compounds I in which X is CH, Z is CH2CH(CH3)CH2, R4 is CH═CH2, R3 is C(═O)CH3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.240aA-1 to I.240aA-1554)


Table 241a

    • Compounds I in which X is CH, Z is CH2CH2CH(CH3), R4 is CH═CH2, R3 is C(═O)CH3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.241aA-1 to I.241aA-1554)


Table 242a

    • Compounds I in which X is CH, Z is CH2C(CH3)2CH2, R4 is CH═CH2, R3 is C(═O)CH3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.242aA-1 to I.242aA-1554)


Table 243a

    • Compounds I in which X is CH, Z is CH(CH3)CH2CH2, R4 is CH═CH2, R3 is C(═O)CH3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.243aA-1 to I.243aA-1554)


Table 244a

    • Compounds I in which X is CH, Z is CH2C(CH2CH2)CH2, R4 is CH═CH2, R3 is C(═O)CH3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.244aA-1 to I.244aA-1554)


Table 245a

    • Compounds I in which X is CH, Z is C(CH2CH2)CH2CH2, R4 is CH═CH2, R3 is C(═O)CH3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.245aA-1 to I.245aA-1554)


Table 246a

    • Compounds I in which X is CH, Z is CH2CH2CH2, R4 is CH2C≡CH, R3 is H and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.246aA-1 to I.246aA-1554)


Table 247a

    • Compounds I in which X is CH, Z is CH2CH(CH3)CH2, R4 is CH2C≡CH, R3 is H and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.247aA-1 to I.247aA-1554)


Table 248a

    • Compounds I in which X is CH, Z is CH2CH2CH(CH3), R4 is CH2C≡CH, R3 is H and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.248aA-1 to I.248aA-1554)


Table 249a

    • Compounds I in which X is CH, Z is CH2C(CH3)2CH2, R4 is CH2C≡CH, R3 is H and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.249aA-1 to I.249aA-1554)


Table 250a

    • Compounds I in which X is CH, Z is CH(CH3)CH2CH2, R4 is CH2C≡CH, R3 is H and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.250aA-1 to I.250aA-1554)


Table 251a

    • Compounds I in which X is CH, Z is CH2C(CH2CH2)CH2, R4 is CH2C≡CH, R3 is H and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.251aA-1 to I.251aA-1554)


Table 252a

    • Compounds I in which X is CH, Z is C(CH2CH2)CH2CH2, R4 is CH2C≡CH, R3 is H and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.252aA-1 to I.252aA-1554)


Table 253a

    • Compounds I in which X is CH, Z is CH2CH2CH2, R4 is CH2C≡CH, R3 is CH2CH═CH2 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.253aA-1 to I.253aA-1554)


Table 254a

    • Compounds I in which X is CH, Z is CH2CH(CH3)CH2, R4 is CH2C≡CH, R3 is CH2CH═CH2 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.254aA-1 to I.254aA-1554)


Table 255a

    • Compounds I in which X is CH, Z is CH2CH2CH(CH3), R4 is CH2C≡CH, R3 is CH2CH═CH2 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.255aA-1 to I.255aA-1554)


Table 256a

    • Compounds I in which X is CH, Z is CH2C(CH3)2CH2, R4 is CH2C≡CH, R3 is CH2CH═CH2 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.256aA-1 to I.256aA-1554)


Table 257a

    • Compounds I in which X is CH, Z is CH(CH3)CH2CH2, R4 is CH2C≡CH, R3 is CH2CH═CH2 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.257aA-1 to I.257aA-1554)


Table 258a

    • Compounds I in which X is CH, Z is CH2C(CH2CH2)CH2, R4 is CH2C≡CH, R3 is CH2CH═CH2 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.258aA-1 to I.258aA-1554)


Table 259a

    • Compounds I in which X is CH, Z is C(CH2CH2)CH2CH2, R4 is CH2C≡CH, R3 is CH2CH═CH2 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.259aA-1 to I.259aA-1554)


Table 260a

    • Compounds I in which X is CH, Z is CH2CH2CH2, R4 is CH2C≡CH, R3 is CH3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.260aA-1 to I.260aA-1554)


Table 261a

    • Compounds I in which X is CH, Z is CH2CH(CH3)CH2, R4 is CH2C≡CH, R3 is CH3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.261 aA-1 to I.261aA-1554)


Table 262a

    • Compounds I in which X is CH, Z is CH2CH2CH(CH3), R4 is CH2C≡CH, R3 is CH3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.262aA-1 to I.262aA-1554)


Table 263a

    • Compounds I in which X is CH, Z is CH2C(CH3)2CH2, R4 is CH2C≡CH, R3 is CH3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.263aA-1 to I.263aA-1554)


Table 264a

    • Compounds I in which X is CH, Z is CH(CH3)CH2CH2, R4 is CH2C≡CH, R3 is CH3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.264aA-1 to I.264aA-1554)


Table 265a

    • Compounds I in which X is CH, Z is CH2C(CH2CH2)CH2, R4 is CH2C≡CH, R3 is CH3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.265aA-1 to I.265aA-1554)


Table 266a

    • Compounds I in which X is CH, Z is C(CH2CH2)CH2CH2, R4 is CH2C≡CH, R3 is CH3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.266aA-1 to I.266aA-1554)


Table 267a

    • Compounds I in which X is CH, Z is CH2CH2CH2, R4 is CH2C≡CH, R3 is CH2C≡CH and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.267aA-1 to I.267aA-1554)


Table 268a

    • Compounds I in which X is CH, Z is CH2CH(CH3)CH2, R4 is CH2C≡CH, R3 is CH2C≡CH and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.268aA-1 to I.268aA-1554)


Table 269a

    • Compounds I in which X is CH, Z is CH2CH2CH(CH3), R4 is CH2C≡CH, R3 is CH2C≡CH and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.269aA-1 to I.269aA-1554)


Table 270a

    • Compounds I in which X is CH, Z is CH2C(CH3)2CH2, R4 is CH2C≡CH, R3 is CH2C≡CH and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.270aA-1 to I.270aA-1554)


Table 271a

    • Compounds I in which X is CH, Z is CH(CH3)CH2CH2, R4 is CH2C≡CH, R3 is CH2C≡CH and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.271aA-1 to I.271aA-1554)


Table 272a

    • Compounds I in which X is CH, Z is CH2C(CH2CH2)CH2, R4 is CH2C≡CH, R3 is CH2C≡CH and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.272aA-1 to I.272aA-1554)


Table 273a

    • Compounds I in which X is CH, Z is C(CH2CH2)CH2CH2, R4 is CH2C≡CH, R3 is CH2C≡CH and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.273aA-1 to I.273aA-1554)


Table 274a

    • Compounds I in which X is CH, Z is CH2CH2CH2, R4 is CH2C≡CH, R3 is C(═O)CH3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.274aA-1 to I.274aA-1554)


Table 275a

    • Compounds I in which X is CH, Z is CH2CH(CH3)CH2, R4 is CH2C≡CH, R3 is C(═O)CH3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.275aA-1 to I.275aA-1554)


Table 276a

    • Compounds I in which X is CH, Z is CH2CH2CH(CH3), R4 is CH2C≡CH, R3 is C(═O)CH3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.276aA-1 to I.276aA-1554)


Table 277a

    • Compounds I in which X is CH, Z is CH2C(CH3)2CH2, R4 is CH2C≡CH, R3 is C(═O)CH3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.277aA-1 to I.277aA-1554)


Table 278a

    • Compounds I in which X is CH, Z is CH(CH3)CH2CH2, R4 is CH2C≡CH, R3 is C(═O)CH3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.278aA-1 to I.278aA-1554)


Table 279a

    • Compounds I in which X is CH, Z is CH2C(CH2CH2)CH2, R4 is CH2C≡CH, R3 is C(═O)CH3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.279aA-1 to I.279aA-1554)


Table 280a

    • Compounds I in which X is CH, Z is C(CH2CH2)CH2CH2, R4 is CH2C≡CH, R3 is C(═O)CH3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.280aA-1 to I.280aA-1554)


Table 281a

    • Compounds I in which X is N, Z is CH2CH2CH2, R4 is H, R3 is Si(CH3)3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.281aA-1 to I.281aA-1554)


Table 282a

    • Compounds I in which X is N, Z is CH2CH(CH3)CH2, R4 is H, R3 is Si(CH3)3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.282aA-1 to I.282aA-1554)


Table 283a

    • Compounds I in which X is N, Z is CH2CH2CH(CH3), R4 is H, R3 is Si(CH3)3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.283aA-1 to I.283aA-1554)


Table 284a

    • Compounds I in which X is N, Z is CH2C(CH3)2CH2, R4 is H, R3 is Si(CH3)3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.284aA-1 to I.284aA-1554)


Table 285a

    • Compounds I in which X is N, Z is CH(CH3)CH2CH2, R4 is H, R3 is Si(CH3)3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.285aA-1 to I.285aA-1554)


Table 286a

    • Compounds I in which X is N, Z is CH2C(CH2CH2)CH2, R4 is H, R3 is Si(CH3)3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.286aA-1 to I.286aA-1554)


Table 287a

    • Compounds I in which X is N, Z is C(CH2CH2)CH2CH2, R4 is H, R3 is Si(CH3)3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.287aA-1 to I.287aA-1554)


Table 288a

    • Compounds I in which X is N, Z is CH2CH2CH2, R4 is CH3, R3 is Si(CH3)3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.288aA-1 to I.288aA-1554)


Table 289a

    • Compounds I in which X is N, Z is CH2CH(CH3)CH2, R4 is CH3, R3 is Si(CH3)3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.289aA-1 to I.289aA-1554)


Table 290a

    • Compounds I in which X is N, Z is CH2CH2CH(CH3), R4 is CH3, R3 is Si(CH3)3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.290aA-1 to I.290aA-1554)


Table 291a

    • Compounds I in which X is N, Z is CH2C(CH3)2CH2, R4 is CH3, R3 is Si(CH3)3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.291aA-1 to I.291aA-1554)


Table 292a

    • Compounds I in which X is N, Z is CH(CH3)CH2CH2, R4 is CH3, R3 is Si(CH3)3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.292aA-1 to I.292aA-1554)


Table 293a

    • Compounds I in which X is N, Z is CH2C(CH2CH2)CH2, R4 is CH3, R3 is Si(CH3)3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.293aA-1 to I.293aA-1554)


Table 294a

    • Compounds I in which X is N, Z is C(CH2CH2)CH2CH2, R4 is CH3, R3 is Si(CH3)3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.294aA-1 to I.294aA-1554)


Table 295a

    • Compounds I in which X is N, Z is CH2CH2CH2, R4 is CH═CH2, R3 is Si(CH3)3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.295aA-1 to I.295aA-1554)


Table 296a

    • Compounds I in which X is N, Z is CH2CH(CH3)CH2, R4 is CH═CH2, R3 is Si(CH3)3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.296aA-1 to I.296aA-1554)


Table 297a

    • Compounds I in which X is N, Z is CH2CH2CH(CH3), R4 is CH═CH2, R3 is Si(CH3)3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.297aA-1 to I.297aA-1554)


Table 298a

    • Compounds I in which X is N, Z is CH2C(CH3)2CH2, R4 is CH═CH2, R3 is Si(CH3)3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.298aA-1 to I.298aA-1554)


Table 299a

    • Compounds I in which X is N, Z is CH(CH3)CH2CH2, R4 is CH═CH2, R3 is Si(CH3)3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.299aA-1 to I.299aA-1554)


Table 300a

    • Compounds I in which X is N, Z is CH2C(CH2CH2)CH2, R4 is CH═CH2, R3 is Si(CH3)3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.300aA-1 to I.300aA-1554)


Table 301a

    • Compounds I in which X is N, Z is C(CH2CH2)CH2CH2, R4 is CH═CH2, R3 is Si(CH3)3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.301aA-1 to I.301aA-1554)


Table 302a

    • Compounds I in which X is N, Z is CH2CH2CH2, R4 is CH2C≡CH, R3 is Si(CH3)3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.302aA-1 to I.302aA-1554)


Table 303a

    • Compounds I in which X is N, Z is CH2CH2CH(CH3), R4 is CH2C≡CH, R3 is Si(CH3)3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.303aA-1 to I.303aA-1554)


Table 304a

    • Compounds I in which X is N, Z is CH2CH2CH(CH3), R4 is CH2C≡CH, R3 is Si(CH3)3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.304aA-1 to I.304aA-1554)


Table 305a

    • Compounds I in which X is N, Z is CH2C(CH3)2CH2, R4 is CH2C≡CH, R3 is Si(CH3)3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.305aA-1 to I.305aA-1554)


Table 306a

    • Compounds I in which X is N, Z is CH(CH3)CH2CH2, R4 is CH2C≡CH, R3 is Si(CH3)3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.306aA-1 to I.306aA-1554)


Table 307a

    • Compounds I in which X is N, Z is CH2C(CH2CH2)CH2, R4 is CH2C≡CH, R3 is Si(CH3)3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.307aA-1 to I.307aA-1554)


Table 308a

    • Compounds I in which X is N, Z is C(CH2CH2)CH2CH2, R4 is CH2C≡CH, R3 is Si(CH3)3 and the combination of R1 and R2 corresponds in each case to one row of Table A (compounds I.308aA-1 to I.308aA-1554)













TABLE A







Row
R1
R2









A-1
C6H5
H



A-2
[2-Cl]—C6H4
H



A-3
[3-Cl]—C6H4
H



A-4
[4-Cl]—C6H4
H



A-5
[2-F]—C6H4
H



A-6
[3-F]—C6H4
H



A-7
[4-F]—C6H4
H



A-8
[2-CN]—C6H4
H



A-9
[3-CN]—C6H4
H



A-10
[4-CN]—C6H4
H



A-11
[2-CH3]—C6H4
H



A-12
[3-CH3]—C6H4
H



A-13
[4-CH3]—C6H4
H



A-14
[2-C2H5]—C6H4
H



A-15
[3-C2H5]—C6H4
H



A-16
[4-C2H5]—C6H4
H



A-17
[2-iso-C3H7]—C6H4
H



A-18
[3-iso-C3H7]—C6H4
H



A-19
[4-iso-C3H7]—C6H4
H



A-20
[2-(C(CH3)3)]—C6H4
H



A-21
[3-(C(CH3)3)]—C6H4
H



A-22
[4-(C(CH3)3)]—C6H4
H



A-23
[2-OCH3]—C6H4
H



A-24
[3-OCH3]—C6H4
H



A-25
[4-OCH3]—C6H4
H



A-26
[2-OC2H5]—C6H4
H



A-27
[3-OC2H5]—C6H4
H



A-28
[4-OC2H5]—C6H4
H



A-29
[2-CF3]—C6H4
H



A-30
[3-CF3]—C6H4
H



A-31
[4-CF3]—C6H4
H



A-32
[2-OCF]—C6H43
H



A-33
[3-OCF3]—C6H4
H



A-34
[4-OCF3]—C6H4
H



A-35
[2-CHF2]—C6H4
H



A-36
[3-CHF2]—C6H4
H



A-37
[4-CHF2]—C6H4
H



A-38
[2,3-(Cl)2]—C6H3
H



A-39
[2,4-(Cl)2]—C6H3
H



A-40
[2,5-(Cl)2]—C6H3
H



A-41
[2,6-(Cl)2]—C6H3
H



A-42
[3,4-(Cl)2]—C6H3
H



A-43
[3,5-(Cl)2]—C6H3
H



A-44
[2,3,4-(Cl)3]—C6H2
H



A-45
[2,3,5-(Cl)3]—C6H2
H



A-46
[2,3,6-(Cl)3]—C6H2
H



A-47
[2,4,5-(Cl)3]—C6H2
H



A-48
[2,4,6-(Cl)3]—C6H2
H



A-49
[3,4,5-(Cl)3]—C6H2
H



A-50
[2,3,4,5-(Cl)4]—C6H
H



A-51
[2,3,4,6-(Cl)4]—C6H
H



A-52
[2,3,5,6-(Cl)4]—C6H
H



A-53
[2,3,4,5,6-(Cl)5]—C6
H



A-54
[3,4-(Cl)2-2-F]—C6H2
H



A-55
[3,5-(Cl)2-2-F]—C6H2
H



A-56
[3,6-(Cl)2-2-F]—C6H2
H



A-57
[4,5-(Cl)2-2-F]—C6H2
H



A-58
[2,3-(Cl)2-6-F]—C6H2
H



A-59
[3,4-(Cl)2-5-F]—C6H2
H



A-60
[2,4-(Cl)2-3-F]—C6H2
H



A-61
[2,5-(Cl)2-3-F]—C6H2
H



A-62
[2,6-(Cl)2-3-F]—C6H2
H



A-63
[2,3-(Cl)2-4-F]—C6H2
H



A-64
[2,5-(Cl)2-4-F]—C6H2
H



A-65
[2,6-(Cl)2-4-F]—C6H2
H



A-66
[4,6-(Cl)2-2,3-(F)2]—C6H
H



A-67
[2,3-(Cl)2-5,6-(F)2]—C6H
H



A-68
[2,5-(Cl)2-4,6-(F)2]—C6H
H



A-69
[3,5-(Cl)2-2,4-(F)2]—C6H
H



A-70
[2,3-(Cl)2-4,6-(F)2]—C6H
H



A-71
[2,4-(Cl)2-3,6-(F)2]—C6H
H



A-72
[2,5-(Cl)2-3,6-(F)2]—C6H
H



A-73
[3,4-(Cl)2-2,5-(F)2]—C6H
H



A-74
[3,4-(Cl)2-2,6-(F)2]—C6H
H



A-75
[3,5-(Cl)2-2,6-(F)2]—C6H
H



A-76
[3,4,6-(Cl)3-2-F]—C6H
H



A-77
[2,3,5-(Cl)3-6-F]—C6H
H



A-78
[2,3,4-(Cl)3-6-F]—C6H
H



A-79
[3,4,5-(Cl)3-2-F]—C6H
H



A-80
[2,4,6-(Cl)3-3-F]—C6H
H



A-81
[2,4,5-(Cl)3-3-F]—C6H
H



A-82
[2,3,4-(Cl)3-5-F]—C6H
H



A-83
[2,3,5-(Cl)3-4-F]—C6H
H



A-84
[2,3,6-(Cl)3-4-F]—C6H
H



A-85
[2,3,4,5-(Cl)4-6-F]—C6
H



A-86
[2,3,4,6-(Cl)4-5-F]—C6
H



A-87
[2,3,5,6-(Cl)4-4-F]—C6
H



A-88
[2,3,4-(Cl)3-5,6-(F)2]—C6
H



A-89
[2,3,5-(Cl)3-4,6-(F)2]—C6
H



A-90
[2,4,5-(Cl)3-3,6-(F)2]—C6
H



A-91
[3,4,5-(Cl)3-2,6-(F)2]—C6
H



A-92
[2,3-(Cl)2-4,5,6-(F)3]—C6
H



A-93
[2,4-(Cl)2-3,5,6-(F)3]—C6
H



A-94
[3,4-(Cl)2-2,5,6-(F)3]—C6
H



A-95
[2,5-(Cl)2-3,4,6-(F)3]—C6
H



A-96
[2,6-(Cl)2-3,4,5-(F)3]—C6
H



A-97
[2,3-(F)2]—C6H3
H



A-98
[2,4-(F)2]—C6H3
H



A-99
[2,5-(F)2]—C6H3
H



A-100
[2,6-(F)2]—C6H3
H



A-101
[2,3,4-(F)3]—C6H2
H



A-102
[2,3,5-(F)3]—C6H2
H



A-103
[2,4,6-(F)3]—C6H2
H



A-104
[2,3,6-(F)3]—C6H2
H



A-105
[3,4,5-(F)3]—C6H2
H



A-106
[3,4,6-(F)3]—C6H2
H



A-107
[3-Cl-2-F]—C6H3
H



A-108
[4-Cl-2-F]—C6H3
H



A-109
[5-Cl-2-F]—C6H3
H



A-110
[2-Cl-6-F]—C6H3
H



A-111
[4-Cl-2,6-(F)2]—C6H2
H



A-112
[4-Cl-2,3-(F)2]—C6H2
H



A-113
[5-Cl-2,3-(F)2]—C6H2
H



A-114
[6-Cl-2,3-(F)2]—C6H2
H



A-115
[3-Cl-2,6-(F)2]—C6H2
H



A-116
[3-Cl-2,4-(F)2]—C6H2
H



A-117
[5-Cl-2,4-(F)2]—C6H2
H



A-118
[2-Cl-4,6-(F)2]—C6H2
H



A-119
[3-Cl-2,5-(F)2]—C6H2
H



A-120
[4-Cl-2,5-(F)2]—C6H2
H



A-121
[2-Cl-3,6-(F)2]—C6H2
H



A-122
[2,4-(CH3)2]—C6H3
H



A-123
[2-(CH3)-3-Cl]—C6H3
H



A-124
[2-(CH3)-4-F]—C6H3
H



A-125
[2-(CH3)-3-F]—C6H3
H



A-126
[2-(CH3)-4-Cl]—C6H3
H



A-127
[2-(CH3)-5-Cl]—C6H3
H



A-128
[2-(CH3)-5-F]—C6H3
H



A-129
[2-(CH3)-6-F]—C6H3
H



A-130
[2-(CH3)-6-Cl]—C6H3
H



A-131
[4-(CH3)-3-Cl]—C6H3
H



A-132
[4-(CH3)-2-F]—C6H3
H



A-133
[4-(CH3)-3-F]—C6H3
H



A-134
[4-(CH3)-2-Cl]—C6H3
H



A-135
[4-(CH3)-5-Cl]—C6H3
H



A-136
[4-(CH3)-5-F]—C6H3
H



A-137
[4-(CH3)-6-F]—C6H3
H



A-138
[4-(CH3)-6-Cl]—C6H3
H



A-139
[3-(CH3)-2-Cl]—C6H3
H



A-140
[3-(CH3)-4-F]—C6H3
H



A-141
[3-(CH3)-2-F]—C6H3
H



A-142
[3-(CH3)-4-Cl]—C6H3
H



A-143
[3-(CH3)-5-Cl]—C6H3
H



A-144
[3-(CH3)-5-F]—C6H3
H



A-145
[3-(CH3)-6-F]—C6H3
H



A-146
[3-(CH3)-6-Cl]—C6H3
H



A-147
[2,4-(OCH3)2]—C6H3
H



A-148
[3,5-(OCH3)2]—C6H3
H



A-149
[2-(OCH3)-3-Cl]—C6H3
H



A-150
[2-(OCH3)-4-F]—C6H3
H



A-151
[2-(OCH3)-3-F]—C6H3
H



A-152
[2-(OCH3)-4-Cl]—C6H3
H



A-153
[2-(OCH3)-5-Cl]—C6H3
H



A-154
[2-(OCH3)-5-F]—C6H3
H



A-155
[2-(OCH3)-6-F]—C6H3
H



A-156
[2-(OCH3)-6-Cl]—C6H3
H



A-157
[4-(OCH3)-3-Cl]—C6H3
H



A-158
[4-(OCH3)-2-F]—C6H3
H



A-159
[4-(OCH3)-3-F]—C6H3
H



A-160
[4-(OCH3)-2-Cl]—C6H3
H



A-161
[4-(OCH3)-5-Cl]—C6H3
H



A-162
[4-(OCH3)-5-F]—C6H3
H



A-163
[4-(OCH3)-6-F]—C6H3
H



A-164
[4-(OCH3)-6-Cl]—C6H3
H



A-165
[3-(OCH3)-2-Cl]—C6H3
H



A-166
[3-(OCH3)-4-F]—C6H3
H



A-167
[3-(OCH3)-2-F]—C6H3
H



A-168
[3-(OCH3)-4-Cl]—C6H3
H



A-169
[3-(OCH3)-5-Cl]—C6H3
H



A-170
[3-(OCH3)-5-F]—C6H3
H



A-171
[3-(OCH3)-6-F]—C6H3
H



A-172
[3-(OCH3)-6-Cl]—C6H3
H



A-173
[2,4-(CF3)2]—C6H3
H



A-174
[2-(CF3)-3-Cl]—C6H3
H



A-175
[2-(CF3)-4-F]—C6H3
H



A-176
[2-(CF3)-3-F]—C6H3
H



A-177
[2-(CF3)-4-Cl]—C6H3
H



A-178
[2-(CF3)-5-Cl]—C6H3
H



A-179
[2-(CF3)-5-F]—C6H3
H



A-180
[2-(CF3)-6-F]—C6H3
H



A-181
[2-(CF3)-6-Cl]—C6H3
H



A-182
[4-(CF3)-3-Cl]—C6H3
H



A-183
[4-(CF3)-2-F]—C6H3
H



A-184
[4-(CF3)-3-F]—C6H3
H



A-185
[4-(CF3)-2-Cl]—C6H3
H



A-186
[4-(CF3)-5-Cl]—C6H3
H



A-187
[4-(CF3)-5-F]—C6H3
H



A-188
[4-(CF3)-6-F]—C6H3
H



A-189
[4-(CF3)-6-Cl]—C6H3
H



A-190
[3-(CF3)-2-Cl]—C6H3
H



A-191
[3-(CF3)-4-F]—C6H3
H



A-192
[3-(CF3)-2-F]—C6H3
H



A-193
[3-(CF3)-4-Cl]—C6H3
H



A-194
[3-(CF3)-5-Cl]—C6H3
H



A-195
[3-(CF3)-5-F]—C6H3
H



A-196
[3-(CF3)-6-F]—C6H3
H



A-197
[3-(CF3)-6-Cl]—C6H3
H



A-198
[2,4-(Br)2]—C6H3
H



A-199
[2-Br-3-Cl]—C6H3
H



A-200
[2-Br-4-F]—C6H3
H



A-201
[2-Br-3-F]—C6H3
H



A-202
[2-Br-4-Cl]—C6H3
H



A-203
[2-Br-5-Cl]—C6H3
H



A-204
[2-Br-5-F]—C6H3
H



A-205
[2-Br-6-F]—C6H3
H



A-206
[2-Br-6-Cl]—C6H3
H



A-207
[4-Br-3-Cl]—C6H3
H



A-208
[4-Br-2-F]—C6H3
H



A-209
[4-Br-3-F]—C6H3
H



A-210
[4-Br-2-Cl]—C6H3
H



A-211
[4-Br-5-Cl]—C6H3
H



A-212
[4-Br-5-F]—C6H3
H



A-213
[4-Br-6-F]—C6H3
H



A-214
[4-Br-6-Cl]—C6H3
H



A-215
[3-Br-2-Cl]—C6H3
H



A-216
[3-Br-4-F]—C6H3
H



A-217
[3-Br-2-F]—C6H3
H



A-218
[3-Br-4-Cl]—C6H3
H



A-219
[3-Br-5-Cl]—C6H3
H



A-220
[3-Br-5-F]—C6H3
H



A-221
[3-Br-6-F]—C6H3
H



A-222
[3-Br-6-Cl]—C6H3
H



A-223
C6H5
CH3



A-224
[2-Cl]—C6H4
CH3



A-225
[3-Cl]—C6H4
CH3



A-226
[4-Cl]—C6H4
CH3



A-227
[2-F]—C6H4
CH3



A-228
[3-F]—C6H4
CH3



A-229
[4-F]—C6H4
CH3



A-230
[2-CN]—C6H4
CH3



A-231
[3-CN]—C6H4
CH3



A-232
[4-CN]—C6H4
CH3



A-233
[2-CH3]—C6H4
CH3



A-234
[3-CH3]—C6H4
CH3



A-235
[4-CH3]—C6H4
CH3



A-236
[2-C2H5]—C6H4
CH3



A-237
[3-C2H5]—C6H4
CH3



A-238
[4-C2H5]—C6H4
CH3



A-239
[2-iso-C3H7]—C6H4
CH3



A-240
[3-iso-C3H7]—C6H4
CH3



A-241
[4-iso-C3H7]—C6H4
CH3



A-242
[2-(C(CH3)3)]—C6H4
CH3



A-243
[3-(C(CH3)3)]—C6H4
CH3



A-244
[4-(C(CH3)3)]—C6H4
CH3



A-245
[2-OCH3]—C6H4
CH3



A-246
[3-OCH3]—C6H4
CH3



A-247
[4-OCH3]—C6H4
CH3



A-248
[2-OC2H5]—C6H4
CH3



A-249
[3-OC2H5]—C6H4
CH3



A-250
[4-OC2H5]—C6H4
CH3



A-251
[2-CF3]—C6H4
CH3



A-252
[3-CF3]—C6H4
CH3



A-253
[4-CF3]—C6H4
CH3



A-254
[2-OCF]—C6H43
CH3



A-255
[3-OCF3]—C6H4
CH3



A-256
[4-OCF3]—C6H4
CH3



A-257
[2-CHF2]—C6H4
CH3



A-258
[3-CHF2]—C6H4
CH3



A-259
[4-CHF2]—C6H4
CH3



A-260
[2,3-(Cl)2]—C6H3
CH3



A-261
[2,4-(Cl)2]—C6H3
CH3



A-262
[2,5-(Cl)2]—C6H3
CH3



A-263
[2,6-(Cl)2]—C6H3
CH3



A-264
[3,4-(Cl)2]—C6H3
CH3



A-265
[3,5-(Cl)2]—C6H3
CH3



A-266
[2,3,4-(Cl)3]—C6H2
CH3



A-267
[2,3,5-(Cl)3]—C6H2
CH3



A-268
[2,3,6-(Cl)3]—C6H2
CH3



A-269
[2,4,5-(Cl)3]—C6H2
CH3



A-270
[2,4,6-(Cl)3]—C6H2
CH3



A-271
[3,4,5-(Cl)3]—C6H2
CH3



A-272
[2,3,4,5-(Cl)4]—C6H
CH3



A-273
[2,3,4,6-(Cl)4]—C6H
CH3



A-274
[2,3,5,6-(Cl)4]—C6H
CH3



A-275
[2,3,4,5,6-(Cl)5]—C6
CH3



A-276
[3,4-(Cl)2-2-F]—C6H2
CH3



A-277
[3,5-(Cl)2-2-F]—C6H2
CH3



A-278
[3,6-(Cl)2-2-F]—C6H2
CH3



A-279
[4,5-(Cl)2-2-F]—C6H2
CH3



A-280
[2,3-(Cl)2-6-F]—C6H2
CH3



A-281
[3,4-(Cl)2-5-F]—C6H2
CH3



A-282
[2,4-(Cl)2-3-F]—C6H2
CH3



A-283
[2,5-(Cl)2-3-F]—C6H2
CH3



A-284
[2,6-(Cl)2-3-F]—C6H2
CH3



A-285
[2,3-(Cl)2-4-F]—C6H2
CH3



A-286
[2,5-(Cl)2-4-F]—C6H2
CH3



A-287
[2,6-(Cl)2-4-F]—C6H2
CH3



A-288
[4,6-(Cl)2-2,3-(F)2]—C6H
CH3



A-289
[2,3-(Cl)2-5,6-(F)2]—C6H
CH3



A-290
[2,5-(Cl)2-4,6-(F)2]—C6H
CH3



A-291
[3,5-(Cl)2-2,4-(F)2]—C6H
CH3



A-292
[2,3-(Cl)2-4,6-(F)2]—C6H
CH3



A-293
[2,4-(Cl)2-3,6-(F)2]—C6H
CH3



A-294
[2,5-(Cl)2-3,6-(F)2]—C6H
CH3



A-295
[3,4-(Cl)2-2,5-(F)2]—C6H
CH3



A-296
[3,4-(Cl)2-2,6-(F)2]—C6H
CH3



A-297
[3,5-(Cl)2-2,6-(F)2]—C6H
CH3



A-298
[3,4,6-(Cl)3-2-F]—C6H
CH3



A-299
[2,3,5-(Cl)3-6-F]—C6H
CH3



A-300
[2,3,4-(Cl)3-6-F]—C6H
CH3



A-301
[3,4,5-(Cl)3-2-F]—C6H
CH3



A-302
[2,4,6-(Cl)3-3-F]—C6H
CH3



A-303
[2,4,5-(Cl)3-3-F]—C6H
CH3



A-304
[2,3,4-(Cl)3-5-F]—C6H
CH3



A-305
[2,3,5-(Cl)3-4-F]—C6H
CH3



A-306
[2,3,6-(Cl)3-4-F]—C6H
CH3



A-307
[2,3,4,5-(Cl)4-6-F]—C6
CH3



A-308
[2,3,4,6-(Cl)4-5-F]—C6
CH3



A-309
[2,3,5,6-(Cl)4-4-F]—C6
CH3



A-310
[2,3,4-(Cl)3-5,6-(F)2]—C6
CH3



A-311
[2,3,5-(Cl)3-4,6-(F)2]—C6
CH3



A-312
[2,4,5-(Cl)3-3,6-(F)2]—C6
CH3



A-313
[3,4,5-(Cl)3-2,6-(F)2]—C6
CH3



A-314
[2,3-(Cl)2-4,5,6-(F)3]—C6
CH3



A-315
[2,4-(Cl)2-3,5,6-(F)3]—C6
CH3



A-316
[3,4-(Cl)2-2,5,6-(F)3]—C6
CH3



A-317
[2,5-(Cl)2-3,4,6-(F)3]—C6
CH3



A-318
[2,6-(Cl)2-3,4,5-(F)3]—C6
CH3



A-319
[2,3-(F)2]—C6H3
CH3



A-320
[2,4-(F)2]—C6H3
CH3



A-321
[2,5-(F)2]—C6H3
CH3



A-322
[2,6-(F)2]—C6H3
CH3



A-323
[2,3,4-(F)3]—C6H2
CH3



A-324
[2,3,5-(F)3]—C6H2
CH3



A-325
[2,4,6-(F)3]—C6H2
CH3



A-326
[2,3,6-(F)3]—C6H2
CH3



A-327
[3,4,5-(F)3]—C6H2
CH3



A-328
[3,4,6-(F)3]—C6H2
CH3



A-329
[3-Cl-2-F]—C6H3
CH3



A-330
[4-Cl-2-F]—C6H3
CH3



A-331
[5-Cl-2-F]—C6H3
CH3



A-332
[2-Cl-6-F]—C6H3
CH3



A-333
[4-Cl-2,6-(F)2]—C6H2
CH3



A-334
[4-Cl-2,3-(F)2]—C6H2
CH3



A-335
[5-Cl-2,3-(F)2]—C6H2
CH3



A-336
[6-Cl-2,3-(F)2]—C6H2
CH3



A-337
[3-Cl-2,6-(F)2]—C6H2
CH3



A-338
[3-Cl-2,4-(F)2]—C6H2
CH3



A-339
[5-Cl-2,4-(F)2]—C6H2
CH3



A-340
[2-Cl-4,6-(F)2]—C6H2
CH3



A-341
[3-Cl-2,5-(F)2]—C6H2
CH3



A-342
[4-Cl-2,5-(F)2]—C6H2
CH3



A-343
[2-Cl-3,6-(F)2]—C6H2
CH3



A-344
[2,4-(CH3)2]—C6H3
CH3



A-345
[2-(CH3)-3-Cl]—C6H3
CH3



A-346
[2-(CH3)-4-F]—C6H3
CH3



A-347
[2-(CH3)-3-F]—C6H3
CH3



A-348
[2-(CH3)-4-Cl]—C6H3
CH3



A-349
[2-(CH3)-5-Cl]—C6H3
CH3



A-350
[2-(CH3)-5-F]—C6H3
CH3



A-351
[2-(CH3)-6-F]—C6H3
CH3



A-352
[2-(CH3)-6-Cl]—C6H3
CH3



A-353
[4-(CH3)-3-Cl]—C6H3
CH3



A-354
[4-(CH3)-2-F]—C6H3
CH3



A-355
[4-(CH3)-3-F]—C6H3
CH3



A-356
[4-(CH3)-2-Cl]—C6H3
CH3



A-357
[4-(CH3)-5-Cl]—C6H3
CH3



A-358
[4-(CH3)-5-F]—C6H3
CH3



A-359
[4-(CH3)-6-F]—C6H3
CH3



A-360
[4-(CH3)-6-Cl]—C6H3
CH3



A-361
[3-(CH3)-2-Cl]—C6H3
CH3



A-362
[3-(CH3)-4-F]—C6H3
CH3



A-363
[3-(CH3)-2-F]—C6H3
CH3



A-364
[3-(CH3)-4-Cl]—C6H3
CH3



A-365
[3-(CH3)-5-Cl]—C6H3
CH3



A-366
[3-(CH3)-5-F]—C6H3
CH3



A-367
[3-(CH3)-6-F]—C6H3
CH3



A-368
[3-(CH3)-6-Cl]—C6H3
CH3



A-369
[2,4-(OCH3)2]—C6H3
CH3



A-370
[3,5-(OCH3)2]—C6H3
CH3



A-371
[2-(OCH3)-3-Cl]—C6H3
CH3



A-372
[2-(OCH3)-4-F]—C6H3
CH3



A-373
[2-(OCH3)-3-F]—C6H3
CH3



A-374
[2-(OCH3)-4-Cl]—C6H3
CH3



A-375
[2-(OCH3)-5-Cl]—C6H3
CH3



A-376
[2-(OCH3)-5-F]—C6H3
CH3



A-377
[2-(OCH3)-6-F]—C6H3
CH3



A-378
[2-(OCH3)-6-Cl]—C6H3
CH3



A-379
[4-(OCH3)-3-Cl]—C6H3
CH3



A-380
[4-(OCH3)-2-F]—C6H3
CH3



A-381
[4-(OCH3)-3-F]—C6H3
CH3



A-382
[4-(OCH3)-2-Cl]—C6H3
CH3



A-383
[4-(OCH3)-5-Cl]—C6H3
CH3



A-384
[4-(OCH3)-5-F]—C6H3
CH3



A-385
[4-(OCH3)-6-F]—C6H3
CH3



A-386
[4-(OCH3)-6-Cl]—C6H3
CH3



A-387
[3-(OCH3)-2-Cl]—C6H3
CH3



A-388
[3-(OCH3)-4-F]—C6H3
CH3



A-389
[3-(OCH3)-2-F]—C6H3
CH3



A-390
[3-(OCH3)-4-Cl]—C6H3
CH3



A-391
[3-(OCH3)-5-Cl]—C6H3
CH3



A-392
[3-(OCH3)-5-F]—C6H3
CH3



A-393
[3-(OCH3)-6-F]—C6H3
CH3



A-394
[3-(OCH3)-6-Cl]—C6H3
CH3



A-395
[2,4-(CF3)2]—C6H3
CH3



A-396
[2-(CF3)-3-Cl]—C6H3
CH3



A-397
[2-(CF3)-4-F]—C6H3
CH3



A-398
[2-(CF3)-3-F]—C6H3
CH3



A-399
[2-(CF3)-4-Cl]—C6H3
CH3



A-400
[2-(CF3)-5-Cl]—C6H3
CH3



A-401
[2-(CF3)-5-F]—C6H3
CH3



A-402
[2-(CF3)-6-F]—C6H3
CH3



A-403
[2-(CF3)-6-Cl]—C6H3
CH3



A-404
[4-(CF3)-3-Cl]—C6H3
CH3



A-405
[4-(CF3)-2-F]—C6H3
CH3



A-406
[4-(CF3)-3-F]—C6H3
CH3



A-407
[4-(CF3)-2-Cl]—C6H3
CH3



A-408
[4-(CF3)-5-Cl]—C6H3
CH3



A-409
[4-(CF3)-5-F]—C6H3
CH3



A-410
[4-(CF3)-6-F]—C6H3
CH3



A-411
[4-(CF3)-6-Cl]—C6H3
CH3



A-412
[3-(CF3)-2-Cl]—C6H3
CH3



A-413
[3-(CF3)-4-F]—C6H3
CH3



A-414
[3-(CF3)-2-F]—C6H3
CH3



A-415
[3-(CF3)-4-Cl]—C6H3
CH3



A-416
[3-(CF3)-5-Cl]—C6H3
CH3



A-417
[3-(CF3)-5-F]—C6H3
CH3



A-418
[3-(CF3)-6-F]—C6H3
CH3



A-419
[3-(CF3)-6-Cl]—C6H3
CH3



A-420
[2,4-(Br)2]—C6H3
CH3



A-421
[2-Br-3-Cl]—C6H3
CH3



A-422
[2-Br-4-F]—C6H3
CH3



A-423
[2-Br-3-F]—C6H3
CH3



A-424
[2-Br-4-Cl]—C6H3
CH3



A-425
[2-Br-5-Cl]—C6H3
CH3



A-426
[2-Br-5-F]—C6H3
CH3



A-427
[2-Br-6-F]—C6H3
CH3



A-428
[2-Br-6-Cl]—C6H3
CH3



A-429
[4-Br-3-Cl]—C6H3
CH3



A-430
[4-Br-2-F]—C6H3
CH3



A-431
[4-Br-3-F]—C6H3
CH3



A-432
[4-Br-2-Cl]—C6H3
CH3



A-433
[4-Br-5-Cl]—C6H3
CH3



A-434
[4-Br-5-F]—C6H3
CH3



A-435
[4-Br-6-F]—C6H3
CH3



A-436
[4-Br-6-Cl]—C6H3
CH3



A-437
[3-Br-2-Cl]—C6H3
CH3



A-438
[3-Br-4-F]—C6H3
CH3



A-439
[3-Br-2-F]—C6H3
CH3



A-440
[3-Br-4-Cl]—C6H3
CH3



A-441
[3-Br-5-Cl]—C6H3
CH3



A-442
[3-Br-5-F]—C6H3
CH3



A-443
[3-Br-6-F]—C6H3
CH3



A-444
[3-Br-6-Cl]—C6H3
CH3



A-445
C6H5
CH2CH═CH2



A-446
[2-Cl]—C6H4
CH2CH═CH2



A-447
[3-Cl]—C6H4
CH2CH═CH2



A-448
[4-Cl]—C6H4
CH2CH═CH2



A-449
[2-F]—C6H4
CH2CH═CH2



A-450
[3-F]—C6H4
CH2CH═CH2



A-451
[4-F]—C6H4
CH2CH═CH2



A-452
[2-CN]—C6H4
CH2CH═CH2



A-453
[3-CN]—C6H4
CH2CH═CH2



A-454
[4-CN]—C6H4
CH2CH═CH2



A-455
[2-CH3]—C6H4
CH2CH═CH2



A-456
[3-CH3]—C6H4
CH2CH═CH2



A-457
[4-CH3]—C6H4
CH2CH═CH2



A-458
[2-C2H5]—C6H4
CH2CH═CH2



A-459
[3-C2H5]—C6H4
CH2CH═CH2



A-460
[4-C2H5]—C6H4
CH2CH═CH2



A-461
[2-iso-C3H7]—C6H4
CH2CH═CH2



A-462
[3-iso-C3H7]—C6H4
CH2CH═CH2



A-463
[4-iso-C3H7]—C6H4
CH2CH═CH2



A-464
[2-(C(CH3)3)]—C6H4
CH2CH═CH2



A-465
[3-(C(CH3)3)]—C6H4
CH2CH═CH2



A-466
[4-(C(CH3)3)]—C6H4
CH2CH═CH2



A-467
[2-OCH3]—C6H4
CH2CH═CH2



A-468
[3-OCH3]—C6H4
CH2CH═CH2



A-469
[4-OCH3]—C6H4
CH2CH═CH2



A-470
[2-OC2H5]—C6H4
CH2CH═CH2



A-471
[3-OC2H5]—C6H4
CH2CH═CH2



A-472
[4-OC2H5]—C6H4
CH2CH═CH2



A-473
[2-CF3]—C6H4
CH2CH═CH2



A-474
[3-CF3]—C6H4
CH2CH═CH2



A-475
[4-CF3]—C6H4
CH2CH═CH2



A-476
[2-OCF]—C6H43
CH2CH═CH2



A-477
[3-OCF3]—C6H4
CH2CH═CH2



A-478
[4-OCF3]—C6H4
CH2CH═CH2



A-479
[2-CHF2]—C6H4
CH2CH═CH2



A-480
[3-CHF2]—C6H4
CH2CH═CH2



A-481
[4-CHF2]—C6H4
CH2CH═CH2



A-482
[2,3-(Cl)2]—C6H3
CH2CH═CH2



A-483
[2,4-(Cl)2]—C6H3
CH2CH═CH2



A-484
[2,5-(Cl)2]—C6H3
CH2CH═CH2



A-485
[2,6-(Cl)2]—C6H3
CH2CH═CH2



A-486
[3,4-(Cl)2]—C6H3
CH2CH═CH2



A-487
[3,5-(Cl)2]—C6H3
CH2CH═CH2



A-488
[2,3,4-(Cl)3]—C6H2
CH2CH═CH2



A-489
[2,3,5-(Cl)3]—C6H2
CH2CH═CH2



A-490
[2,3,6-(Cl)3]—C6H2
CH2CH═CH2



A-491
[2,4,5-(Cl)3]—C6H2
CH2CH═CH2



A-492
[2,4,6-(Cl)3]—C6H2
CH2CH═CH2



A-493
[3,4,5-(Cl)3]—C6H2
CH2CH═CH2



A-494
[2,3,4,5-(Cl)4]—C6H
CH2CH═CH2



A-495
[2,3,4,6-(Cl)4]—C6H
CH2CH═CH2



A-496
[2,3,5,6-(Cl)4]—C6H
CH2CH═CH2



A-497
[2,3,4,5,6-(Cl)5]—C6
CH2CH═CH2



A-498
[3,4-(Cl)2-2-F]—C6H2
CH2CH═CH2



A-499
[3,5-(Cl)2-2-F]—C6H2
CH2CH═CH2



A-500
[3,6-(Cl)2-2-F]—C6H2
CH2CH═CH2



A-501
[4,5-(Cl)2-2-F]—C6H2
CH2CH═CH2



A-502
[2,3-(Cl)2-6-F]—C6H2
CH2CH═CH2



A-503
[3,4-(Cl)2-5-F]—C6H2
CH2CH═CH2



A-504
[2,4-(Cl)2-3-F]—C6H2
CH2CH═CH2



A-505
[2,5-(Cl)2-3-F]—C6H2
CH2CH═CH2



A-506
[2,6-(Cl)2-3-F]—C6H2
CH2CH═CH2



A-507
[2,3-(Cl)2-4-F]—C6H2
CH2CH═CH2



A-508
[2,5-(Cl)2-4-F]—C6H2
CH2CH═CH2



A-509
[2,6-(Cl)2-4-F]—C6H2
CH2CH═CH2



A-510
[4,6-(Cl)2-2,3-(F)2]—C6H
CH2CH═CH2



A-511
[2,3-(Cl)2-5,6-(F)2]—C6H
CH2CH═CH2



A-512
[2,5-(Cl)2-4,6-(F)2]—C6H
CH2CH═CH2



A-513
[3,5-(Cl)2-2,4-(F)2]—C6H
CH2CH═CH2



A-514
[2,3-(Cl)2-4,6-(F)2]—C6H
CH2CH═CH2



A-515
[2,4-(Cl)2-3,6-(F)2]—C6H
CH2CH═CH2



A-516
[2,5-(Cl)2-3,6-(F)2]—C6H
CH2CH═CH2



A-517
[3,4-(Cl)2-2,5-(F)2]—C6H
CH2CH═CH2



A-518
[3,4-(Cl)2-2,6-(F)2]—C6H
CH2CH═CH2



A-519
[3,5-(Cl)2-2,6-(F)2]—C6H
CH2CH═CH2



A-520
[3,4,6-(Cl)3-2-F]—C6H
CH2CH═CH2



A-521
[2,3,5-(Cl)3-6-F]—C6H
CH2CH═CH2



A-522
[2,3,4-(Cl)3-6-F]—C6H
CH2CH═CH2



A-523
[3,4,5-(Cl)3-2-F]—C6H
CH2CH═CH2



A-524
[2,4,6-(Cl)3-3-F]—C6H
CH2CH═CH2



A-525
[2,4,5-(Cl)3-3-F]—C6H
CH2CH═CH2



A-526
[2,3,4-(Cl)3-5-F]—C6H
CH2CH═CH2



A-527
[2,3,5-(Cl)3-4-F]—C6H
CH2CH═CH2



A-528
[2,3,6-(Cl)3-4-F]—C6H
CH2CH═CH2



A-529
[2,3,4,5-(Cl)4-6-F]—C6
CH2CH═CH2



A-530
[2,3,4,6-(Cl)4-5-F]—C6
CH2CH═CH2



A-531
[2,3,5,6-(Cl)4-4-F]—C6
CH2CH═CH2



A-532
[2,3,4-(Cl)3-5,6-(F)2]—C6
CH2CH═CH2



A-533
[2,3,5-(Cl)3-4,6-(F)2]—C6
CH2CH═CH2



A-534
[2,4,5-(Cl)3-3,6-(F)2]—C6
CH2CH═CH2



A-535
[3,4,5-(Cl)3-2,6-(F)2]—C6
CH2CH═CH2



A-536
[2,3-(Cl)2-4,5,6-(F)3]—C6
CH2CH═CH2



A-537
[2,4-(Cl)2-3,5,6-(F)3]—C6
CH2CH═CH2



A-538
[3,4-(Cl)2-2,5,6-(F)3]—C6
CH2CH═CH2



A-539
[2,5-(Cl)2-3,4,6-(F)3]—C6
CH2CH═CH2



A-540
[2,6-(Cl)2-3,4,5-(F)3]—C6
CH2CH═CH2



A-541
[2,3-(F)2]—C6H3
CH2CH═CH2



A-542
[2,4-(F)2]—C6H3
CH2CH═CH2



A-543
[2,5-(F)2]—C6H3
CH2CH═CH2



A-544
[2,6-(F)2]—C6H3
CH2CH═CH2



A-545
[2,3,4-(F)3]—C6H2
CH2CH═CH2



A-546
[2,3,5-(F)3]—C6H2
CH2CH═CH2



A-547
[2,4,6-(F)3]—C6H2
CH2CH═CH2



A-548
[2,3,6-(F)3]—C6H2
CH2CH═CH2



A-549
[3,4,5-(F)3]—C6H2
CH2CH═CH2



A-550
[3,4,6-(F)3]—C6H2
CH2CH═CH2



A-551
[3-Cl-2-F]—C6H3
CH2CH═CH2



A-552
[4-Cl-2-F]—C6H3
CH2CH═CH2



A-553
[5-Cl-2-F]—C6H3
CH2CH═CH2



A-554
[2-Cl-6-F]—C6H3
CH2CH═CH2



A-555
[4-Cl-2,6-(F)2]—C6H2
CH2CH═CH2



A-556
[4-Cl-2,3-(F)2]—C6H2
CH2CH═CH2



A-557
[5-Cl-2,3-(F)2]—C6H2
CH2CH═CH2



A-558
[6-Cl-2,3-(F)2]—C6H2
CH2CH═CH2



A-559
[3-Cl-2,6-(F)2]—C6H2
CH2CH═CH2



A-560
[3-Cl-2,4-(F)2]—C6H2
CH2CH═CH2



A-561
[5-Cl-2,4-(F)2]—C6H2
CH2CH═CH2



A-562
[2-Cl-4,6-(F)2]—C6H2
CH2CH═CH2



A-563
[3-Cl-2,5-(F)2]—C6H2
CH2CH═CH2



A-564
[4-Cl-2,5-(F)2]—C6H2
CH2CH═CH2



A-565
[2-Cl-3,6-(F)2]—C6H2
CH2CH═CH2



A-566
[2,4-(CH3)2]—C6H3
CH2CH═CH2



A-567
[2-(CH3)-3-Cl]—C6H3
CH2CH═CH2



A-568
[2-(CH3)-4-F]—C6H3
CH2CH═CH2



A-569
[2-(CH3)-3-F]—C6H3
CH2CH═CH2



A-570
[2-(CH3)-4-Cl]—C6H3
CH2CH═CH2



A-571
[2-(CH3)-5-Cl]—C6H3
CH2CH═CH2



A-572
[2-(CH3)-5-F]—C6H3
CH2CH═CH2



A-573
[2-(CH3)-6-F]—C6H3
CH2CH═CH2



A-574
[2-(CH3)-6-Cl]—C6H3
CH2CH═CH2



A-575
[4-(CH3)-3-Cl]—C6H3
CH2CH═CH2



A-576
[4-(CH3)-2-F]—C6H3
CH2CH═CH2



A-577
[4-(CH3)-3-F]—C6H3
CH2CH═CH2



A-578
[4-(CH3)-2-Cl]—C6H3
CH2CH═CH2



A-579
[4-(CH3)-5-Cl]—C6H3
CH2CH═CH2



A-580
[4-(CH3)-5-F]—C6H3
CH2CH═CH2



A-581
[4-(CH3)-6-F]—C6H3
CH2CH═CH2



A-582
[4-(CH3)-6-Cl]—C6H3
CH2CH═CH2



A-583
[3-(CH3)-2-Cl]—C6H3
CH2CH═CH2



A-584
[3-(CH3)-4-F]—C6H3
CH2CH═CH2



A-585
[3-(CH3)-2-F]—C6H3
CH2CH═CH2



A-586
[3-(CH3)-4-Cl]—C6H3
CH2CH═CH2



A-587
[3-(CH3)-5-Cl]—C6H3
CH2CH═CH2



A-588
[3-(CH3)-5-F]—C6H3
CH2CH═CH2



A-589
[3-(CH3)-6-F]—C6H3
CH2CH═CH2



A-590
[3-(CH3)-6-Cl]—C6H3
CH2CH═CH2



A-591
[2,4-(OCH3)2]—C6H3
CH2CH═CH2



A-592
[3,5-(OCH3)2]—C6H3
CH2CH═CH2



A-593
[2-(OCH3)-3-Cl]—C6H3
CH2CH═CH2



A-594
[2-(OCH3)-4-F]—C6H3
CH2CH═CH2



A-595
[2-(OCH3)-3-F]—C6H3
CH2CH═CH2



A-596
[2-(OCH3)-4-Cl]—C6H3
CH2CH═CH2



A-597
[2-(OCH3)-5-Cl]—C6H3
CH2CH═CH2



A-598
[2-(OCH3)-5-F]—C6H3
CH2CH═CH2



A-599
[2-(OCH3)-6-F]—C6H3
CH2CH═CH2



A-600
[2-(OCH3)-6-Cl]—C6H3
CH2CH═CH2



A-601
[4-(OCH3)-3-Cl]—C6H3
CH2CH═CH2



A-602
[4-(OCH3)-2-F]—C6H3
CH2CH═CH2



A-603
[4-(OCH3)-3-F]—C6H3
CH2CH═CH2



A-604
[4-(OCH3)-2-Cl]—C6H3
CH2CH═CH2



A-605
[4-(OCH3)-5-Cl]—C6H3
CH2CH═CH2



A-606
[4-(OCH3)-5-F]—C6H3
CH2CH═CH2



A-607
[4-(OCH3)-6-F]—C6H3
CH2CH═CH2



A-608
[4-(OCH3)-6-Cl]—C6H3
CH2CH═CH2



A-609
[3-(OCH3)-2-Cl]—C6H3
CH2CH═CH2



A-610
[3-(OCH3)-4-F]—C6H3
CH2CH═CH2



A-611
[3-(OCH3)-2-F]—C6H3
CH2CH═CH2



A-612
[3-(OCH3)-4-Cl]—C6H3
CH2CH═CH2



A-613
[3-(OCH3)-5-Cl]—C6H3
CH2CH═CH2



A-614
[3-(OCH3)-5-F]—C6H3
CH2CH═CH2



A-615
[3-(OCH3)-6-F]—C6H3
CH2CH═CH2



A-616
[3-(OCH3)-6-Cl]—C6H3
CH2CH═CH2



A-617
[2,4-(CF3)2]—C6H3
CH2CH═CH2



A-618
[2-(CF3)-3-Cl]—C6H3
CH2CH═CH2



A-619
[2-(CF3)-4-F]—C6H3
CH2CH═CH2



A-620
[2-(CF3)-3-F]—C6H3
CH2CH═CH2



A-621
[2-(CF3)-4-Cl]—C6H3
CH2CH═CH2



A-622
[2-(CF3)-5-Cl]—C6H3
CH2CH═CH2



A-623
[2-(CF3)-5-F]—C6H3
CH2CH═CH2



A-624
[2-(CF3)-6-F]—C6H3
CH2CH═CH2



A-625
[2-(CF3)-6-Cl]—C6H3
CH2CH═CH2



A-626
[4-(CF3)-3-Cl]—C6H3
CH2CH═CH2



A-627
[4-(CF3)-2-F]—C6H3
CH2CH═CH2



A-628
[4-(CF3)-3-F]—C6H3
CH2CH═CH2



A-629
[4-(CF3)-2-Cl]—C6H3
CH2CH═CH2



A-630
[4-(CF3)-5-Cl]—C6H3
CH2CH═CH2



A-631
[4-(CF3)-5-F]—C6H3
CH2CH═CH2



A-632
[4-(CF3)-6-F]—C6H3
CH2CH═CH2



A-633
[4-(CF3)-6-Cl]—C6H3
CH2CH═CH2



A-634
[3-(CF3)-2-Cl]—C6H3
CH2CH═CH2



A-635
[3-(CF3)-4-F]—C6H3
CH2CH═CH2



A-636
[3-(CF3)-2-F]—C6H3
CH2CH═CH2



A-637
[3-(CF3)-4-Cl]—C6H3
CH2CH═CH2



A-638
[3-(CF3)-5-Cl]—C6H3
CH2CH═CH2



A-639
[3-(CF3)-5-F]—C6H3
CH2CH═CH2



A-640
[3-(CF3)-6-F]—C6H3
CH2CH═CH2



A-641
[3-(CF3)-6-Cl]—C6H3
CH2CH═CH2



A-642
[2,4-(Br)2]—C6H3
CH2CH═CH2



A-643
[2-Br-3-Cl]—C6H3
CH2CH═CH2



A-644
[2-Br-4-F]—C6H3
CH2CH═CH2



A-645
[2-Br-3-F]—C6H3
CH2CH═CH2



A-646
[2-Br-4-Cl]—C6H3
CH2CH═CH2



A-647
[2-Br-5-Cl]—C6H3
CH2CH═CH2



A-648
[2-Br-5-F]—C6H3
CH2CH═CH2



A-649
[2-Br-6-F]—C6H3
CH2CH═CH2



A-650
[2-Br-6-Cl]—C6H3
CH2CH═CH2



A-651
[4-Br-3-Cl]—C6H3
CH2CH═CH2



A-652
[4-Br-2-F]—C6H3
CH2CH═CH2



A-653
[4-Br-3-F]—C6H3
CH2CH═CH2



A-654
[4-Br-2-Cl]—C6H3
CH2CH═CH2



A-655
[4-Br-5-Cl]—C6H3
CH2CH═CH2



A-656
[4-Br-5-F]—C6H3
CH2CH═CH2



A-657
[4-Br-6-F]—C6H3
CH2CH═CH2



A-658
[4-Br-6-Cl]—C6H3
CH2CH═CH2



A-659
[3-Br-2-Cl]—C6H3
CH2CH═CH2



A-660
[3-Br-4-F]—C6H3
CH2CH═CH2



A-661
[3-Br-2-F]—C6H3
CH2CH═CH2



A-662
[3-Br-4-Cl]—C6H3
CH2CH═CH2



A-663
[3-Br-5-Cl]—C6H3
CH2CH═CH2



A-664
[3-Br-5-F]—C6H3
CH2CH═CH2



A-665
[3-Br-6-F]—C6H3
CH2CH═CH2



A-666
[3-Br-6-Cl]—C6H3
CH2CH═CH2



A-667
C6H5
CH2C≡CH



A-668
[2-Cl]—C6H4
CH2C≡CH



A-669
[3-Cl]—C6H4
CH2C≡CH



A-670
[4-Cl]—C6H4
CH2C≡CH



A-671
[2-F]—C6H4
CH2C≡CH



A-672
[3-F]—C6H4
CH2C≡CH



A-673
[4-F]—C6H4
CH2C≡CH



A-674
[2-CN]—C6H4
CH2C≡CH



A-675
[3-CN]—C6H4
CH2C≡CH



A-676
[4-CN]—C6H4
CH2C≡CH



A-677
[2-CH3]—C6H4
CH2C≡CH



A-678
[3-CH3]—C6H4
CH2C≡CH



A-679
[4-CH3]—C6H4
CH2C≡CH



A-680
[2-C2H5]—C6H4
CH2C≡CH



A-681
[3-C2H5]—C6H4
CH2C≡CH



A-682
[4-C2H5]—C6H4
CH2C≡CH



A-683
[2-iso-C3H7]—C6H4
CH2C≡CH



A-684
[3-iso-C3H7]—C6H4
CH2C≡CH



A-685
[4-iso-C3H7]—C6H4
CH2C≡CH



A-686
[2-(C(CH3)3)]—C6H4
CH2C≡CH



A-687
[3-(C(CH3)3)]—C6H4
CH2C≡CH



A-688
[4-(C(CH3)3)]—C6H4
CH2C≡CH



A-689
[2-OCH3]—C6H4
CH2C≡CH



A-690
[3-OCH3]—C6H4
CH2C≡CH



A-691
[4-OCH3]—C6H4
CH2C≡CH



A-692
[2-OC2H5]—C6H4
CH2C≡CH



A-693
[3-OC2H5]—C6H4
CH2C≡CH



A-694
[4-OC2H5]—C6H4
CH2C≡CH



A-695
[2-CF3]—C6H4
CH2C≡CH



A-696
[3-CF3]—C6H4
CH2C≡CH



A-697
[4-CF3]—C6H4
CH2C≡CH



A-698
[2-OCF]—C6H43
CH2C≡CH



A-699
[3-OCF3]—C6H4
CH2C≡CH



A-700
[4-OCF3]—C6H4
CH2C≡CH



A-701
[2-CHF2]—C6H4
CH2C≡CH



A-702
[3-CHF2]—C6H4
CH2C≡CH



A-703
[4-CHF2]—C6H4
CH2C≡CH



A-704
[2,3-(Cl)2]—C6H3
CH2C≡CH



A-705
[2,4-(Cl)2]—C6H3
CH2C≡CH



A-706
[2,5-(Cl)2]—C6H3
CH2C≡CH



A-707
[2,6-(Cl)2]—C6H3
CH2C≡CH



A-708
[3,4-(Cl)2]—C6H3
CH2C≡CH



A-709
[3,5-(Cl)2]—C6H3
CH2C≡CH



A-710
[2,3,4-(Cl)3]—C6H2
CH2C≡CH



A-711
[2,3,5-(Cl)3]—C6H2
CH2C≡CH



A-712
[2,3,6-(Cl)3]—C6H2
CH2C≡CH



A-713
[2,4,5-(Cl)3]—C6H2
CH2C≡CH



A-714
[2,4,6-(Cl)3]—C6H2
CH2C≡CH



A-715
[3,4,5-(Cl)3]—C6H2
CH2C≡CH



A-716
[2,3,4,5-(Cl)4]—C6H
CH2C≡CH



A-717
[2,3,4,6-(Cl)4]—C6H
CH2C≡CH



A-718
[2,3,5,6-(Cl)4]—C6H
CH2C≡CH



A-719
[2,3,4,5,6-(Cl)5]—C6
CH2C≡CH



A-720
[3,4-(Cl)2-2-F]—C6H2
CH2C≡CH



A-721
[3,5-(Cl)2-2-F]—C6H2
CH2C≡CH



A-722
[3,6-(Cl)2-2-F]—C6H2
CH2C≡CH



A-723
[4,5-(Cl)2-2-F]—C6H2
CH2C≡CH



A-724
[2,3-(Cl)2-6-F]—C6H2
CH2C≡CH



A-725
[3,4-(Cl)2-5-F]—C6H2
CH2C≡CH



A-726
[2,4-(Cl)2-3-F]—C6H2
CH2C≡CH



A-727
[2,5-(Cl)2-3-F]—C6H2
CH2C≡CH



A-728
[2,6-(Cl)2-3-F]—C6H2
CH2C≡CH



A-729
[2,3-(Cl)2-4-F]—C6H2
CH2C≡CH



A-730
[2,5-(Cl)2-4-F]—C6H2
CH2C≡CH



A-731
[2,6-(Cl)2-4-F]—C6H2
CH2C≡CH



A-732
[4,6-(Cl)2-2,3-(F)2]—C6H
CH2C≡CH



A-733
[2,3-(Cl)2-5,6-(F)2]—C6H
CH2C≡CH



A-734
[2,5-(Cl)2-4,6-(F)2]—C6H
CH2C≡CH



A-735
[3,5-(Cl)2-2,4-(F)2]—C6H
CH2C≡CH



A-736
[2,3-(Cl)2-4,6-(F)2]—C6H
CH2C≡CH



A-737
[2,4-(Cl)2-3,6-(F)2]—C6H
CH2C≡CH



A-738
[2,5-(Cl)2-3,6-(F)2]—C6H
CH2C≡CH



A-739
[3,4-(Cl)2-2,5-(F)2]—C6H
CH2C≡CH



A-740
[3,4-(Cl)2-2,6-(F)2]—C6H
CH2C≡CH



A-741
[3,5-(Cl)2-2,6-(F)2]—C6H
CH2C≡CH



A-742
[3,4,6-(Cl)3-2-F]—C6H
CH2C≡CH



A-743
[2,3,5-(Cl)3-6-F]—C6H
CH2C≡CH



A-744
[2,3,4-(Cl)3-6-F]—C6H
CH2C≡CH



A-745
[3,4,5-(Cl)3-2-F]—C6H
CH2C≡CH



A-746
[2,4,6-(Cl)3-3-F]—C6H
CH2C≡CH



A-747
[2,4,5-(Cl)3-3-F]—C6H
CH2C≡CH



A-748
[2,3,4-(Cl)3-5-F]—C6H
CH2C≡CH



A-749
[2,3,5-(Cl)3-4-F]—C6H
CH2C≡CH



A-750
[2,3,6-(Cl)3-4-F]—C6H
CH2C≡CH



A-751
[2,3,4,5-(Cl)4-6-F]—C6
CH2C≡CH



A-752
[2,3,4,6-(Cl)4-5-F]—C6
CH2C≡CH



A-753
[2,3,5,6-(Cl)4-4-F]—C6
CH2C≡CH



A-754
[2,3,4-(Cl)3-5,6-(F)2]—C6
CH2C≡CH



A-755
[2,3,5-(Cl)3-4,6-(F)2]—C6
CH2C≡CH



A-756
[2,4,5-(Cl)3-3,6-(F)2]—C6
CH2C≡CH



A-757
[3,4,5-(Cl)3-2,6-(F)2]—C6
CH2C≡CH



A-758
[2,3-(Cl)2-4,5,6-(F)3]—C6
CH2C≡CH



A-759
[2,4-(Cl)2-3,5,6-(F)3]—C6
CH2C≡CH



A-760
[3,4-(Cl)2-2,5,6-(F)3]—C6
CH2C≡CH



A-761
[2,5-(Cl)2-3,4,6-(F)3]—C6
CH2C≡CH



A-762
[2,6-(Cl)2-3,4,5-(F)3]—C6
CH2C≡CH



A-763
[2,3-(F)2]—C6H3
CH2C≡CH



A-764
[2,4-(F)2]—C6H3
CH2C≡CH



A-765
[2,5-(F)2]—C6H3
CH2C≡CH



A-766
[2,6-(F)2]—C6H3
CH2C≡CH



A-767
[2,3,4-(F)3]—C6H2
CH2C≡CH



A-768
[2,3,5-(F)3]—C6H2
CH2C≡CH



A-769
[2,4,6-(F)3]—C6H2
CH2C≡CH



A-770
[2,3,6-(F)3]—C6H2
CH2C≡CH



A-771
[3,4,5-(F)3]—C6H2
CH2C≡CH



A-772
[3,4,6-(F)3]—C6H2
CH2C≡CH



A-773
[3-Cl-2-F]—C6H3
CH2C≡CH



A-774
[4-Cl-2-F]—C6H3
CH2C≡CH



A-775
[5-Cl-2-F]—C6H3
CH2C≡CH



A-776
[2-Cl-6-F]—C6H3
CH2C≡CH



A-777
[4-Cl-2,6-(F)2]—C6H2
CH2C≡CH



A-778
[4-Cl-2,3-(F)2]—C6H2
CH2C≡CH



A-779
[5-Cl-2,3-(F)2]—C6H2
CH2C≡CH



A-780
[6-Cl-2,3-(F)2]—C6H2
CH2C≡CH



A-781
[3-Cl-2,6-(F)2]—C6H2
CH2C≡CH



A-782
[3-Cl-2,4-(F)2]—C6H2
CH2C≡CH



A-783
[5-Cl-2,4-(F)2]—C6H2
CH2C≡CH



A-784
[2-Cl-4,6-(F)2]—C6H2
CH2C≡CH



A-785
[3-Cl-2,5-(F)2]—C6H2
CH2C≡CH



A-786
[4-Cl-2,5-(F)2]—C6H2
CH2C≡CH



A-787
[2-Cl-3,6-(F)2]—C6H2
CH2C≡CH



A-788
[2,4-(CH3)2]—C6H3
CH2C≡CH



A-789
[2-(CH3)-3-Cl]—C6H3
CH2C≡CH



A-790
[2-(CH3)-4-F]—C6H3
CH2C≡CH



A-791
[2-(CH3)-3-F]—C6H3
CH2C≡CH



A-792
[2-(CH3)-4-Cl]—C6H3
CH2C≡CH



A-793
[2-(CH3)-5-Cl]—C6H3
CH2C≡CH



A-794
[2-(CH3)-5-F]—C6H3
CH2C≡CH



A-795
[2-(CH3)-6-F]—C6H3
CH2C≡CH



A-796
[2-(CH3)-6-Cl]—C6H3
CH2C≡CH



A-797
[4-(CH3)-3-Cl]—C6H3
CH2C≡CH



A-798
[4-(CH3)-2-F]—C6H3
CH2C≡CH



A-799
[4-(CH3)-3-F]—C6H3
CH2C≡CH



A-800
[4-(CH3)-2-Cl]—C6H3
CH2C≡CH



A-801
[4-(CH3)-5-Cl]—C6H3
CH2C≡CH



A-802
[4-(CH3)-5-F]—C6H3
CH2C≡CH



A-803
[4-(CH3)-6-F]—C6H3
CH2C≡CH



A-804
[4-(CH3)-6-Cl]—C6H3
CH2C≡CH



A-805
[3-(CH3)-2-Cl]—C6H3
CH2C≡CH



A-806
[3-(CH3)-4-F]—C6H3
CH2C≡CH



A-807
[3-(CH3)-2-F]—C6H3
CH2C≡CH



A-808
[3-(CH3)-4-Cl]—C6H3
CH2C≡CH



A-809
[3-(CH3)-5-Cl]—C6H3
CH2C≡CH



A-810
[3-(CH3)-5-F]—C6H3
CH2C≡CH



A-811
[3-(CH3)-6-F]—C6H3
CH2C≡CH



A-812
[3-(CH3)-6-Cl]—C6H3
CH2C≡CH



A-813
[2,4-(OCH3)2]—C6H3
CH2C≡CH



A-814
[3,5-(OCH3)2]—C6H3
CH2C≡CH



A-815
[2-(OCH3)-3-Cl]—C6H3
CH2C≡CH



A-816
[2-(OCH3)-4-F]—C6H3
CH2C≡CH



A-817
[2-(OCH3)-3-F]—C6H3
CH2C≡CH



A-818
[2-(OCH3)-4-Cl]—C6H3
CH2C≡CH



A-819
[2-(OCH3)-5-Cl]—C6H3
CH2C≡CH



A-820
[2-(OCH3)-5-F]—C6H3
CH2C≡CH



A-821
[2-(OCH3)-6-F]—C6H3
CH2C≡CH



A-822
[2-(OCH3)-6-Cl]—C6H3
CH2C≡CH



A-823
[4-(OCH3)-3-Cl]—C6H3
CH2C≡CH



A-824
[4-(OCH3)-2-F]—C6H3
CH2C≡CH



A-825
[4-(OCH3)-3-F]—C6H3
CH2C≡CH



A-826
[4-(OCH3)-2-Cl]—C6H3
CH2C≡CH



A-827
[4-(OCH3)-5-Cl]—C6H3
CH2C≡CH



A-828
[4-(OCH3)-5-F]—C6H3
CH2C≡CH



A-829
[4-(OCH3)-6-F]—C6H3
CH2C≡CH



A-830
[4-(OCH3)-6-Cl]—C6H3
CH2C≡CH



A-831
[3-(OCH3)-2-Cl]—C6H3
CH2C≡CH



A-832
[3-(OCH3)-4-F]—C6H3
CH2C≡CH



A-833
[3-(OCH3)-2-F]—C6H3
CH2C≡CH



A-834
[3-(OCH3)-4-Cl]—C6H3
CH2C≡CH



A-835
[3-(OCH3)-5-Cl]—C6H3
CH2C≡CH



A-836
[3-(OCH3)-5-F]—C6H3
CH2C≡CH



A-837
[3-(OCH3)-6-F]—C6H3
CH2C≡CH



A-838
[3-(OCH3)-6-Cl]—C6H3
CH2C≡CH



A-839
[2,4-(CF3)2]—C6H3
CH2C≡CH



A-840
[2-(CF3)-3-Cl]—C6H3
CH2C≡CH



A-841
[2-(CF3)-4-F]—C6H3
CH2C≡CH



A-842
[2-(CF3)-3-F]—C6H3
CH2C≡CH



A-843
[2-(CF3)-4-Cl]—C6H3
CH2C≡CH



A-844
[2-(CF3)-5-Cl]—C6H3
CH2C≡CH



A-845
[2-(CF3)-5-F]—C6H3
CH2C≡CH



A-846
[2-(CF3)-6-F]—C6H3
CH2C≡CH



A-847
[2-(CF3)-6-Cl]—C6H3
CH2C≡CH



A-848
[4-(CF3)-3-Cl]—C6H3
CH2C≡CH



A-849
[4-(CF3)-2-F]—C6H3
CH2C≡CH



A-850
[4-(CF3)-3-F]—C6H3
CH2C≡CH



A-851
[4-(CF3)-2-Cl]—C6H3
CH2C≡CH



A-852
[4-(CF3)-5-Cl]—C6H3
CH2C≡CH



A-853
[4-(CF3)-5-F]—C6H3
CH2C≡CH



A-854
[4-(CF3)-6-F]—C6H3
CH2C≡CH



A-855
[4-(CF3)-6-Cl]—C6H3
CH2C≡CH



A-856
[3-(CF3)-2-Cl]—C6H3
CH2C≡CH



A-857
[3-(CF3)-4-F]—C6H3
CH2C≡CH



A-858
[3-(CF3)-2-F]—C6H3
CH2C≡CH



A-859
[3-(CF3)-4-Cl]—C6H3
CH2C≡CH



A-860
[3-(CF3)-5-Cl]—C6H3
CH2C≡CH



A-861
[3-(CF3)-5-F]—C6H3
CH2C≡CH



A-862
[3-(CF3)-6-F]—C6H3
CH2C≡CH



A-863
[3-(CF3)-6-Cl]—C6H3
CH2C≡CH



A-864
[2,4-(Br)2]—C6H3
CH2C≡CH



A-865
[2-Br-3-Cl]—C6H3
CH2C≡CH



A-866
[2-Br-4-F]—C6H3
CH2C≡CH



A-867
[2-Br-3-F]—C6H3
CH2C≡CH



A-868
[2-Br-4-Cl]—C6H3
CH2C≡CH



A-869
[2-Br-5-Cl]—C6H3
CH2C≡CH



A-870
[2-Br-5-F]—C6H3
CH2C≡CH



A-871
[2-Br-6-F]—C6H3
CH2C≡CH



A-872
[2-Br-6-Cl]—C6H3
CH2C≡CH



A-873
[4-Br-3-Cl]—C6H3
CH2C≡CH



A-874
[4-Br-2-F]—C6H3
CH2C≡CH



A-875
[4-Br-3-F]—C6H3
CH2C≡CH



A-876
[4-Br-2-Cl]—C6H3
CH2C≡CH



A-877
[4-Br-5-Cl]—C6H3
CH2C≡CH



A-878
[4-Br-5-F]—C6H3
CH2C≡CH



A-879
[4-Br-6-F]—C6H3
CH2C≡CH



A-880
[4-Br-6-Cl]—C6H3
CH2C≡CH



A-881
[3-Br-2-Cl]—C6H3
CH2C≡CH



A-882
[3-Br-4-F]—C6H3
CH2C≡CH



A-883
[3-Br-2-F]—C6H3
CH2C≡CH



A-884
[3-Br-4-Cl]—C6H3
CH2C≡CH



A-885
[3-Br-5-Cl]—C6H3
CH2C≡CH



A-886
[3-Br-5-F]—C6H3
CH2C≡CH



A-887
[3-Br-6-F]—C6H3
CH2C≡CH



A-888
[3-Br-6-Cl]—C6H3
CH2C≡CH



A-889
C6H5
CH2C≡CCH3



A-890
[2-Cl]—C6H4
CH2C≡CCH3



A-891
[3-Cl]—C6H4
CH2C≡CCH3



A-892
[4-Cl]—C6H4
CH2C≡CCH3



A-893
[2-F]—C6H4
CH2C≡CCH3



A-894
[3-F]—C6H4
CH2C≡CCH3



A-895
[4-F]—C6H4
CH2C≡CCH3



A-896
[2-CN]—C6H4
CH2C≡CCH3



A-897
[3-CN]—C6H4
CH2C≡CCH3



A-898
[4-CN]—C6H4
CH2C≡CCH3



A-899
[2-CH3]—C6H4
CH2C≡CCH3



A-900
[3-CH3]—C6H4
CH2C≡CCH3



A-901
[4-CH3]—C6H4
CH2C≡CCH3



A-902
[2-C2H5]—C6H4
CH2C≡CCH3



A-903
[3-C2H5]—C6H4
CH2C≡CCH3



A-904
[4-C2H5]—C6H4
CH2C≡CCH3



A-905
[2-iso-C3H7]—C6H4
CH2C≡CCH3



A-906
[3-iso-C3H7]—C6H4
CH2C≡CCH3



A-907
[4-iso-C3H7]—C6H4
CH2C≡CCH3



A-908
[2-(C(CH3)3)]—C6H4
CH2C≡CCH3



A-909
[3-(C(CH3)3)]—C6H4
CH2C≡CCH3



A-910
[4-(C(CH3)3)]—C6H4
CH2C≡CCH3



A-911
[2-OCH3]—C6H4
CH2C≡CCH3



A-912
[3-OCH3]—C6H4
CH2C≡CCH3



A-913
[4-OCH3]—C6H4
CH2C≡CCH3



A-914
[2-OC2H5]—C6H4
CH2C≡CCH3



A-915
[3-OC2H5]—C6H4
CH2C≡CCH3



A-916
[4-OC2H5]—C6H4
CH2C≡CCH3



A-917
[2-CF3]—C6H4
CH2C≡CCH3



A-918
[3-CF3]—C6H4
CH2C≡CCH3



A-919
[4-CF3]—C6H4
CH2C≡CCH3



A-920
[2-OCF]—C6H43
CH2C≡CCH3



A-921
[3-OCF3]—C6H4
CH2C≡CCH3



A-922
[4-OCF3]—C6H4
CH2C≡CCH3



A-923
[2-CHF2]—C6H4
CH2C≡CCH3



A-924
[3-CHF2]—C6H4
CH2C≡CCH3



A-925
[4-CHF2]—C6H4
CH2C≡CCH3



A-926
[2,3-(Cl)2]—C6H3
CH2C≡CCH3



A-927
[2,4-(Cl)2]—C6H3
CH2C≡CCH3



A-928
[2,5-(Cl)2]—C6H3
CH2C≡CCH3



A-929
[2,6-(Cl)2]—C6H3
CH2C≡CCH3



A-930
[3,4-(Cl)2]—C6H3
CH2C≡CCH3



A-931
[3,5-(Cl)2]—C6H3
CH2C≡CCH3



A-932
[2,3,4-(Cl)3]—C6H2
CH2C≡CCH3



A-933
[2,3,5-(Cl)3]—C6H2
CH2C≡CCH3



A-934
[2,3,6-(Cl)3]—C6H2
CH2C≡CCH3



A-935
[2,4,5-(Cl)3]—C6H2
CH2C≡CCH3



A-936
[2,4,6-(Cl)3]—C6H2
CH2C≡CCH3



A-937
[3,4,5-(Cl)3]—C6H2
CH2C≡CCH3



A-938
[2,3,4,5-(Cl)4]—C6H
CH2C≡CCH3



A-939
[2,3,4,6-(Cl)4]—C6H
CH2C≡CCH3



A-940
[2,3,5,6-(Cl)4]—C6H
CH2C≡CCH3



A-941
[2,3,4,5,6-(Cl)5]—C6
CH2C≡CCH3



A-942
[3,4-(Cl)2-2-F]—C6H2
CH2C≡CCH3



A-943
[3,5-(Cl)2-2-F]—C6H2
CH2C≡CCH3



A-944
[3,6-(Cl)2-2-F]—C6H2
CH2C≡CCH3



A-945
[4,5-(Cl)2-2-F]—C6H2
CH2C≡CCH3



A-946
[2,3-(Cl)2-6-F]—C6H2
CH2C≡CCH3



A-947
[3,4-(Cl)2-5-F]—C6H2
CH2C≡CCH3



A-948
[2,4-(Cl)2-3-F]—C6H2
CH2C≡CCH3



A-949
[2,5-(Cl)2-3-F]—C6H2
CH2C≡CCH3



A-950
[2,6-(Cl)2-3-F]—C6H2
CH2C≡CCH3



A-951
[2,3-(Cl)2-4-F]—C6H2
CH2C≡CCH3



A-952
[2,5-(Cl)2-4-F]—C6H2
CH2C≡CCH3



A-953
[2,6-(Cl)2-4-F]—C6H2
CH2C≡CCH3



A-954
[4,6-(Cl)2-2,3-(F)2]—C6H
CH2C≡CCH3



A-955
[2,3-(Cl)2-5,6-(F)2]—C6H
CH2C≡CCH3



A-956
[2,5-(Cl)2-4,6-(F)2]—C6H
CH2C≡CCH3



A-957
[3,5-(Cl)2-2,4-(F)2]—C6H
CH2C≡CCH3



A-958
[2,3-(Cl)2-4,6-(F)2]—C6H
CH2C≡CCH3



A-959
[2,4-(Cl)2-3,6-(F)2]—C6H
CH2C≡CCH3



A-960
[2,5-(Cl)2-3,6-(F)2]—C6H
CH2C≡CCH3



A-961
[3,4-(Cl)2-2,5-(F)2]—C6H
CH2C≡CCH3



A-962
[3,4-(Cl)2-2,6-(F)2]—C6H
CH2C≡CCH3



A-963
[3,5-(Cl)2-2,6-(F)2]—C6H
CH2C≡CCH3



A-964
[3,4,6-(Cl)3-2-F]—C6H
CH2C≡CCH3



A-965
[2,3,5-(Cl)3-6-F]—C6H
CH2C≡CCH3



A-966
[2,3,4-(Cl)3-6-F]—C6H
CH2C≡CCH3



A-967
[3,4,5-(Cl)3-2-F]—C6H
CH2C≡CCH3



A-968
[2,4,6-(Cl)3-3-F]—C6H
CH2C≡CCH3



A-969
[2,4,5-(Cl)3-3-F]—C6H
CH2C≡CCH3



A-970
[2,3,4-(Cl)3-5-F]—C6H
CH2C≡CCH3



A-971
[2,3,5-(Cl)3-4-F]—C6H
CH2C≡CCH3



A-972
[2,3,6-(Cl)3-4-F]—C6H
CH2C≡CCH3



A-973
[2,3,4,5-(Cl)4-6-F]—C6
CH2C≡CCH3



A-974
[2,3,4,6-(Cl)4-5-F]—C6
CH2C≡CCH3



A-975
[2,3,5,6-(Cl)4-4-F]—C6
CH2C≡CCH3



A-976
[2,3,4-(Cl)3-5,6-(F)2]—C6
CH2C≡CCH3



A-977
[2,3,5-(Cl)3-4,6-(F)2]—C6
CH2C≡CCH3



A-978
[2,4,5-(Cl)3-3,6-(F)2]—C6
CH2C≡CCH3



A-979
[3,4,5-(Cl)3-2,6-(F)2]—C6
CH2C≡CCH3



A-980
[2,3-(Cl)2-4,5,6-(F)3]—C6
CH2C≡CCH3



A-981
[2,4-(Cl)2-3,5,6-(F)3]—C6
CH2C≡CCH3



A-982
[3,4-(Cl)2-2,5,6-(F)3]—C6
CH2C≡CCH3



A-983
[2,5-(Cl)2-3,4,6-(F)3]—C6
CH2C≡CCH3



A-984
[2,6-(Cl)2-3,4,5-(F)3]—C6
CH2C≡CCH3



A-985
[2,3-(F)2]—C6H3
CH2C≡CCH3



A-986
[2,4-(F)2]—C6H3
CH2C≡CCH3



A-987
[2,5-(F)2]—C6H3
CH2C≡CCH3



A-988
[2,6-(F)2]—C6H3
CH2C≡CCH3



A-989
[2,3,4-(F)3]—C6H2
CH2C≡CCH3



A-990
[2,3,5-(F)3]—C6H2
CH2C≡CCH3



A-991
[2,4,6-(F)3]—C6H2
CH2C≡CCH3



A-992
[2,3,6-(F)3]—C6H2
CH2C≡CCH3



A-993
[3,4,5-(F)3]—C6H2
CH2C≡CCH3



A-994
[3,4,6-(F)3]—C6H2
CH2C≡CCH3



A-995
[3-Cl-2-F]—C6H3
CH2C≡CCH3



A-996
[4-Cl-2-F]—C6H3
CH2C≡CCH3



A-997
[5-Cl-2-F]—C6H3
CH2C≡CCH3



A-998
[2-Cl-6-F]—C6H3
CH2C≡CCH3



A-999
[4-Cl-2,6-(F)2]—C6H2
CH2C≡CCH3



A-1000
[4-Cl-2,3-(F)2]—C6H2
CH2C≡CCH3



A-1001
[5-Cl-2,3-(F)2]—C6H2
CH2C≡CCH3



A-1002
[6-Cl-2,3-(F)2]—C6H2
CH2C≡CCH3



A-1003
[3-Cl-2,6-(F)2]—C6H2
CH2C≡CCH3



A-1004
[3-Cl-2,4-(F)2]—C6H2
CH2C≡CCH3



A-1005
[5-Cl-2,4-(F)2]—C6H2
CH2C≡CCH3



A-1006
[2-Cl-4,6-(F)2]—C6H2
CH2C≡CCH3



A-1007
[3-Cl-2,5-(F)2]—C6H2
CH2C≡CCH3



A-1008
[4-Cl-2,5-(F)2]—C6H2
CH2C≡CCH3



A-1009
[2-Cl-3,6-(F)2]—C6H2
CH2C≡CCH3



A-1010
[2,4-(CH3)2]—C6H3
CH2C≡CCH3



A-1011
[2-(CH3)-3-Cl]—C6H3
CH2C≡CCH3



A-1012
[2-(CH3)-4-F]—C6H3
CH2C≡CCH3



A-1013
[2-(CH3)-3-F]—C6H3
CH2C≡CCH3



A-1014
[2-(CH3)-4-Cl]—C6H3
CH2C≡CCH3



A-1015
[2-(CH3)-5-Cl]—C6H3
CH2C≡CCH3



A-1016
[2-(CH3)-5-F]—C6H3
CH2C≡CCH3



A-1017
[2-(CH3)-6-F]—C6H3
CH2C≡CCH3



A-1018
[2-(CH3)-6-Cl]—C6H3
CH2C≡CCH3



A-1019
[4-(CH3)-3-Cl]—C6H3
CH2C≡CCH3



A-1020
[4-(CH3)-2-F]—C6H3
CH2C≡CCH3



A-1021
[4-(CH3)-3-F]—C6H3
CH2C≡CCH3



A-1022
[4-(CH3)-2-Cl]—C6H3
CH2C≡CCH3



A-1023
[4-(CH3)-5-Cl]—C6H3
CH2C≡CCH3



A-1024
[4-(CH3)-5-F]—C6H3
CH2C≡CCH3



A-1025
[4-(CH3)-6-F]—C6H3
CH2C≡CCH3



A-1026
[4-(CH3)-6-Cl]—C6H3
CH2C≡CCH3



A-1027
[3-(CH3)-2-Cl]—C6H3
CH2C≡CCH3



A-1028
[3-(CH3)-4-F]—C6H3
CH2C≡CCH3



A-1029
[3-(CH3)-2-F]—C6H3
CH2C≡CCH3



A-1030
[3-(CH3)-4-Cl]—C6H3
CH2C≡CCH3



A-1031
[3-(CH3)-5-Cl]—C6H3
CH2C≡CCH3



A-1032
[3-(CH3)-5-F]—C6H3
CH2C≡CCH3



A-1033
[3-(CH3)-6-F]—C6H3
CH2C≡CCH3



A-1034
[3-(CH3)-6-Cl]—C6H3
CH2C≡CCH3



A-1035
[2,4-(OCH3)2]—C6H3
CH2C≡CCH3



A-1036
[3,5-(OCH3)2]—C6H3
CH2C≡CCH3



A-1037
[2-(OCH3)-3-Cl]—C6H3
CH2C≡CCH3



A-1038
[2-(OCH3)-4-F]—C6H3
CH2C≡CCH3



A-1039
[2-(OCH3)-3-F]—C6H3
CH2C≡CCH3



A-1040
[2-(OCH3)-4-Cl]—C6H3
CH2C≡CCH3



A-1041
[2-(OCH3)-5-Cl]—C6H3
CH2C≡CCH3



A-1042
[2-(OCH3)-5-F]—C6H3
CH2C≡CCH3



A-1043
[2-(OCH3)-6-F]—C6H3
CH2C≡CCH3



A-1044
[2-(OCH3)-6-Cl]—C6H3
CH2C≡CCH3



A-1045
[4-(OCH3)-3-Cl]—C6H3
CH2C≡CCH3



A-1046
[4-(OCH3)-2-F]—C6H3
CH2C≡CCH3



A-1047
[4-(OCH3)-3-F]—C6H3
CH2C≡CCH3



A-1048
[4-(OCH3)-2-Cl]—C6H3
CH2C≡CCH3



A-1049
[4-(OCH3)-5-Cl]—C6H3
CH2C≡CCH3



A-1050
[4-(OCH3)-5-F]—C6H3
CH2C≡CCH3



A-1051
[4-(OCH3)-6-F]—C6H3
CH2C≡CCH3



A-1052
[4-(OCH3)-6-Cl]—C6H3
CH2C≡CCH3



A-1053
[3-(OCH3)-2-Cl]—C6H3
CH2C≡CCH3



A-1054
[3-(OCH3)-4-F]—C6H3
CH2C≡CCH3



A-1055
[3-(OCH3)-2-F]—C6H3
CH2C≡CCH3



A-1056
[3-(OCH3)-4-Cl]—C6H3
CH2C≡CCH3



A-1057
[3-(OCH3)-5-Cl]—C6H3
CH2C≡CCH3



A-1058
[3-(OCH3)-5-F]—C6H3
CH2C≡CCH3



A-1059
[3-(OCH3)-6-F]—C6H3
CH2C≡CCH3



A-1060
[3-(OCH3)-6-Cl]—C6H3
CH2C≡CCH3



A-1061
[2,4-(CF3)2]—C6H3
CH2C≡CCH3



A-1062
[2-(CF3)-3-Cl]—C6H3
CH2C≡CCH3



A-1063
[2-(CF3)-4-F]—C6H3
CH2C≡CCH3



A-1064
[2-(CF3)-3-F]—C6H3
CH2C≡CCH3



A-1065
[2-(CF3)-4-Cl]—C6H3
CH2C≡CCH3



A-1066
[2-(CF3)-5-Cl]—C6H3
CH2C≡CCH3



A-1067
[2-(CF3)-5-F]—C6H3
CH2C≡CCH3



A-1068
[2-(CF3)-6-F]—C6H3
CH2C≡CCH3



A-1069
[2-(CF3)-6-Cl]—C6H3
CH2C≡CCH3



A-1070
[4-(CF3)-3-Cl]—C6H3
CH2C≡CCH3



A-1071
[4-(CF3)-2-F]—C6H3
CH2C≡CCH3



A-1072
[4-(CF3)-3-F]—C6H3
CH2C≡CCH3



A-1073
[4-(CF3)-2-Cl]—C6H3
CH2C≡CCH3



A-1074
[4-(CF3)-5-Cl]—C6H3
CH2C≡CCH3



A-1075
[4-(CF3)-5-F]—C6H3
CH2C≡CCH3



A-1076
[4-(CF3)-6-F]—C6H3
CH2C≡CCH3



A-1077
[4-(CF3)-6-Cl]—C6H3
CH2C≡CCH3



A-1078
[3-(CF3)-2-Cl]—C6H3
CH2C≡CCH3



A-1079
[3-(CF3)-4-F]—C6H3
CH2C≡CCH3



A-1080
[3-(CF3)-2-F]—C6H3
CH2C≡CCH3



A-1081
[3-(CF3)-4-Cl]—C6H3
CH2C≡CCH3



A-1082
[3-(CF3)-5-Cl]—C6H3
CH2C≡CCH3



A-1083
[3-(CF3)-5-F]—C6H3
CH2C≡CCH3



A-1084
[3-(CF3)-6-F]—C6H3
CH2C≡CCH3



A-1085
[3-(CF3)-6-Cl]—C6H3
CH2C≡CCH3



A-1086
[2,4-(Br)2]—C6H3
CH2C≡CCH3



A-1087
[2-Br-3-Cl]—C6H3
CH2C≡CCH3



A-1088
[2-Br-4-F]—C6H3
CH2C≡CCH3



A-1089
[2-Br-3-F]—C6H3
CH2C≡CCH3



A-1090
[2-Br-4-Cl]—C6H3
CH2C≡CCH3



A-1091
[2-Br-5-Cl]—C6H3
CH2C≡CCH3



A-1092
[2-Br-5-F]—C6H3
CH2C≡CCH3



A-1093
[2-Br-6-F]—C6H3
CH2C≡CCH3



A-1094
[2-Br-6-Cl]—C6H3
CH2C≡CCH3



A-1095
[4-Br-3-Cl]—C6H3
CH2C≡CCH3



A-1096
[4-Br-2-F]—C6H3
CH2C≡CCH3



A-1097
[4-Br-3-F]—C6H3
CH2C≡CCH3



A-1098
[4-Br-2-Cl]—C6H3
CH2C≡CCH3



A-1099
[4-Br-5-Cl]—C6H3
CH2C≡CCH3



A-1100
[4-Br-5-F]—C6H3
CH2C≡CCH3



A-1101
[4-Br-6-F]—C6H3
CH2C≡CCH3



A-1102
[4-Br-6-Cl]—C6H3
CH2C≡CCH3



A-1103
[3-Br-2-Cl]—C6H3
CH2C≡CCH3



A-1104
[3-Br-4-F]—C6H3
CH2C≡CCH3



A-1105
[3-Br-2-F]—C6H3
CH2C≡CCH3



A-1106
[3-Br-4-Cl]—C6H3
CH2C≡CCH3



A-1107
[3-Br-5-Cl]—C6H3
CH2C≡CCH3



A-1108
[3-Br-5-F]—C6H3
CH2C≡CCH3



A-1109
[3-Br-6-F]—C6H3
CH2C≡CCH3



A-1110
[3-Br-6-Cl]—C6H3
CH2C≡CCH3



A-1111
C6H5
CH2C6H5



A-1112
[2-Cl]—C6H4
CH2C6H5



A-1113
[3-Cl]—C6H4
CH2C6H5



A-1114
[4-Cl]—C6H4
CH2C6H5



A-1115
[2-F]—C6H4
CH2C6H5



A-1116
[3-F]—C6H4
CH2C6H5



A-1117
[4-F]—C6H4
CH2C6H5



A-1118
[2-CN]—C6H4
CH2C6H5



A-1119
[3-CN]—C6H4
CH2C6H5



A-1120
[4-CN]—C6H4
CH2C6H5



A-1121
[2-CH3]—C6H4
CH2C6H5



A-1122
[3-CH3]—C6H4
CH2C6H5



A-1123
[4-CH3]—C6H4
CH2C6H5



A-1124
[2-C2H5]—C6H4
CH2C6H5



A-1125
[3-C2H5]—C6H4
CH2C6H5



A-1126
[4-C2H5]—C6H4
CH2C6H5



A-1127
[2-iso-C3H7]—C6H4
CH2C6H5



A-1128
[3-iso-C3H7]—C6H4
CH2C6H5



A-1129
[4-iso-C3H7]—C6H4
CH2C6H5



A-1130
[2-(C(CH3)3)]—C6H4
CH2C6H5



A-1131
[3-(C(CH3)3)]—C6H4
CH2C6H5



A-1132
[4-(C(CH3)3)]—C6H4
CH2C6H5



A-1133
[2-OCH3]—C6H4
CH2C6H5



A-1134
[3-OCH3]—C6H4
CH2C6H5



A-1135
[4-OCH3]—C6H4
CH2C6H5



A-1136
[2-OC2H5]—C6H4
CH2C6H5



A-1137
[3-OC2H5]—C6H4
CH2C6H5



A-1138
[4-OC2H5]—C6H4
CH2C6H5



A-1139
[2-CF3]—C6H4
CH2C6H5



A-1140
[3-CF3]—C6H4
CH2C6H5



A-1141
[4-CF3]—C6H4
CH2C6H5



A-1142
[2-OCF]—C6H43
CH2C6H5



A-1143
[3-OCF3]—C6H4
CH2C6H5



A-1144
[4-OCF3]—C6H4
CH2C6H5



A-1145
[2-CHF2]—C6H4
CH2C6H5



A-1146
[3-CHF2]—C6H4
CH2C6H5



A-1147
[4-CHF2]—C6H4
CH2C6H5



A-1148
[2,3-(Cl)2]—C6H3
CH2C6H5



A-1149
[2,4-(Cl)2]—C6H3
CH2C6H5



A-1150
[2,5-(Cl)2]—C6H3
CH2C6H5



A-1151
[2,6-(Cl)2]—C6H3
CH2C6H5



A-1152
[3,4-(Cl)2]—C6H3
CH2C6H5



A-1153
[3,5-(Cl)2]—C6H3
CH2C6H5



A-1154
[2,3,4-(Cl)3]—C6H2
CH2C6H5



A-1155
[2,3,5-(Cl)3]—C6H2
CH2C6H5



A-1156
[2,3,6-(Cl)3]—C6H2
CH2C6H5



A-1157
[2,4,5-(Cl)3]—C6H2
CH2C6H5



A-1158
[2,4,6-(Cl)3]—C6H2
CH2C6H5



A-1159
[3,4,5-(Cl)3]—C6H2
CH2C6H5



A-1160
[2,3,4,5-(Cl)4]—C6H
CH2C6H5



A-1161
[2,3,4,6-(Cl)4]—C6H
CH2C6H5



A-1162
[2,3,5,6-(Cl)4]—C6H
CH2C6H5



A-1163
[2,3,4,5,6-(Cl)5]—C6
CH2C6H5



A-1164
[3,4-(Cl)2-2-F]—C6H2
CH2C6H5



A-1165
[3,5-(Cl)2-2-F]—C6H2
CH2C6H5



A-1166
[3,6-(Cl)2-2-F]—C6H2
CH2C6H5



A-1167
[4,5-(Cl)2-2-F]—C6H2
CH2C6H5



A-1168
[2,3-(Cl)2-6-F]—C6H2
CH2C6H5



A-1169
[3,4-(Cl)2-5-F]—C6H2
CH2C6H5



A-1170
[2,4-(Cl)2-3-F]—C6H2
CH2C6H5



A-1171
[2,5-(Cl)2-3-F]—C6H2
CH2C6H5



A-1172
[2,6-(Cl)2-3-F]—C6H2
CH2C6H5



A-1173
[2,3-(Cl)2-4-F]—C6H2
CH2C6H5



A-1174
[2,5-(Cl)2-4-F]—C6H2
CH2C6H5



A-1175
[2,6-(Cl)2-4-F]—C6H2
CH2C6H5



A-1176
[4,6-(Cl)2-2,3-(F)2]—C6H
CH2C6H5



A-1177
[2,3-(Cl)2-5,6-(F)2]—C6H
CH2C6H5



A-1178
[2,5-(Cl)2-4,6-(F)2]—C6H
CH2C6H5



A-1179
[3,5-(Cl)2-2,4-(F)2]—C6H
CH2C6H5



A-1180
[2,3-(Cl)2-4,6-(F)2]—C6H
CH2C6H5



A-1181
[2,4-(Cl)2-3,6-(F)2]—C6H
CH2C6H5



A-1182
[2,5-(Cl)2-3,6-(F)2]—C6H
CH2C6H5



A-1183
[3,4-(Cl)2-2,5-(F)2]—C6H
CH2C6H5



A-1184
[3,4-(Cl)2-2,6-(F)2]—C6H
CH2C6H5



A-1185
[3,5-(Cl)2-2,6-(F)2]—C6H
CH2C6H5



A-1186
[3,4,6-(Cl)3-2-F]—C6H
CH2C6H5



A-1187
[2,3,5-(Cl)3-6-F]—C6H
CH2C6H5



A-1188
[2,3,4-(Cl)3-6-F]—C6H
CH2C6H5



A-1189
[3,4,5-(Cl)3-2-F]—C6H
CH2C6H5



A-1190
[2,4,6-(Cl)3-3-F]—C6H
CH2C6H5



A-1191
[2,4,5-(Cl)3-3-F]—C6H
CH2C6H5



A-1192
[2,3,4-(Cl)3-5-F]—C6H
CH2C6H5



A-1193
[2,3,5-(Cl)3-4-F]—C6H
CH2C6H5



A-1194
[2,3,6-(Cl)3-4-F]—C6H
CH2C6H5



A-1195
[2,3,4,5-(Cl)4-6-F]—C6
CH2C6H5



A-1196
[2,3,4,6-(Cl)4-5-F]—C6
CH2C6H5



A-1197
[2,3,5,6-(Cl)4-4-F]—C6
CH2C6H5



A-1198
[2,3,4-(Cl)3-5,6-(F)2]—C6
CH2C6H5



A-1199
[2,3,5-(Cl)3-4,6-(F)2]—C6
CH2C6H5



A-1200
[2,4,5-(Cl)3-3,6-(F)2]—C6
CH2C6H5



A-1201
[3,4,5-(Cl)3-2,6-(F)2]—C6
CH2C6H5



A-1202
[2,3-(Cl)2-4,5,6-(F)3]—C6
CH2C6H5



A-1203
[2,4-(Cl)2-3,5,6-(F)3]—C6
CH2C6H5



A-1204
[3,4-(Cl)2-2,5,6-(F)3]—C6
CH2C6H5



A-1205
[2,5-(Cl)2-3,4,6-(F)3]—C6
CH2C6H5



A-1206
[2,6-(Cl)2-3,4,5-(F)3]—C6
CH2C6H5



A-1207
[2,3-(F)2]—C6H3
CH2C6H5



A-1208
[2,4-(F)2]—C6H3
CH2C6H5



A-1209
[2,5-(F)2]—C6H3
CH2C6H5



A-1210
[2,6-(F)2]—C6H3
CH2C6H5



A-1211
[2,3,4-(F)3]—C6H2
CH2C6H5



A-1212
[2,3,5-(F)3]—C6H2
CH2C6H5



A-1213
[2,4,6-(F)3]—C6H2
CH2C6H5



A-1214
[2,3,6-(F)3]—C6H2
CH2C6H5



A-1215
[3,4,5-(F)3]—C6H2
CH2C6H5



A-1216
[3,4,6-(F)3]—C6H2
CH2C6H5



A-1217
[3-Cl-2-F]—C6H3
CH2C6H5



A-1218
[4-Cl-2-F]—C6H3
CH2C6H5



A-1219
[5-Cl-2-F]—C6H3
CH2C6H5



A-1220
[2-Cl-6-F]—C6H3
CH2C6H5



A-1221
[4-Cl-2,6-(F)2]—C6H2
CH2C6H5



A-1222
[4-Cl-2,3-(F)2]—C6H2
CH2C6H5



A-1223
[5-Cl-2,3-(F)2]—C6H2
CH2C6H5



A-1224
[6-Cl-2,3-(F)2]—C6H2
CH2C6H5



A-1225
[3-Cl-2,6-(F)2]—C6H2
CH2C6H5



A-1226
[3-Cl-2,4-(F)2]—C6H2
CH2C6H5



A-1227
[5-Cl-2,4-(F)2]—C6H2
CH2C6H5



A-1228
[2-Cl-4,6-(F)2]—C6H2
CH2C6H5



A-1229
[3-Cl-2,5-(F)2]—C6H2
CH2C6H5



A-1230
[4-Cl-2,5-(F)2]—C6H2
CH2C6H5



A-1231
[2-Cl-3,6-(F)2]—C6H2
CH2C6H5



A-1232
[2,4-(CH3)2]—C6H3
CH2C6H5



A-1233
[2-(CH3)-3-Cl]—C6H3
CH2C6H5



A-1234
[2-(CH3)-4-F]—C6H3
CH2C6H5



A-1235
[2-(CH3)-3-F]—C6H3
CH2C6H5



A-1236
[2-(CH3)-4-Cl]—C6H3
CH2C6H5



A-1237
[2-(CH3)-5-Cl]—C6H3
CH2C6H5



A-1238
[2-(CH3)-5-F]—C6H3
CH2C6H5



A-1239
[2-(CH3)-6-F]—C6H3
CH2C6H5



A-1240
[2-(CH3)-6-Cl]—C6H3
CH2C6H5



A-1241
[4-(CH3)-3-Cl]—C6H3
CH2C6H5



A-1242
[4-(CH3)-2-F]—C6H3
CH2C6H5



A-1243
[4-(CH3)-3-F]—C6H3
CH2C6H5



A-1244
[4-(CH3)-2-Cl]—C6H3
CH2C6H5



A-1245
[4-(CH3)-5-Cl]—C6H3
CH2C6H5



A-1246
[4-(CH3)-5-F]—C6H3
CH2C6H5



A-1247
[4-(CH3)-6-F]—C6H3
CH2C6H5



A-1248
[4-(CH3)-6-Cl]—C6H3
CH2C6H5



A-1249
[3-(CH3)-2-Cl]—C6H3
CH2C6H5



A-1250
[3-(CH3)-4-F]—C6H3
CH2C6H5



A-1251
[3-(CH3)-2-F]—C6H3
CH2C6H5



A-1252
[3-(CH3)-4-Cl]—C6H3
CH2C6H5



A-1253
[3-(CH3)-5-Cl]—C6H3
CH2C6H5



A-1254
[3-(CH3)-5-F]—C6H3
CH2C6H5



A-1255
[3-(CH3)-6-F]—C6H3
CH2C6H5



A-1256
[3-(CH3)-6-Cl]—C6H3
CH2C6H5



A-1257
[2,4-(OCH3)2]—C6H3
CH2C6H5



A-1258
[3,5-(OCH3)2]—C6H3
CH2C6H5



A-1259
[2-(OCH3)-3-Cl]—C6H3
CH2C6H5



A-1260
[2-(OCH3)-4-F]—C6H3
CH2C6H5



A-1261
[2-(OCH3)-3-F]—C6H3
CH2C6H5



A-1262
[2-(OCH3)-4-Cl]—C6H3
CH2C6H5



A-1263
[2-(OCH3)-5-Cl]—C6H3
CH2C6H5



A-1264
[2-(OCH3)-5-F]—C6H3
CH2C6H5



A-1265
[2-(OCH3)-6-F]—C6H3
CH2C6H5



A-1266
[2-(OCH3)-6-Cl]—C6H3
CH2C6H5



A-1267
[4-(OCH3)-3-Cl]—C6H3
CH2C6H5



A-1268
[4-(OCH3)-2-F]—C6H3
CH2C6H5



A-1269
[4-(OCH3)-3-F]—C6H3
CH2C6H5



A-1270
[4-(OCH3)-2-Cl]—C6H3
CH2C6H5



A-1271
[4-(OCH3)-5-Cl]—C6H3
CH2C6H5



A-1272
[4-(OCH3)-5-F]—C6H3
CH2C6H5



A-1273
[4-(OCH3)-6-F]—C6H3
CH2C6H5



A-1274
[4-(OCH3)-6-Cl]—C6H3
CH2C6H5



A-1275
[3-(OCH3)-2-Cl]—C6H3
CH2C6H5



A-1276
[3-(OCH3)-4-F]—C6H3
CH2C6H5



A-1277
[3-(OCH3)-2-F]—C6H3
CH2C6H5



A-1278
[3-(OCH3)-4-Cl]—C6H3
CH2C6H5



A-1279
[3-(OCH3)-5-Cl]—C6H3
CH2C6H5



A-1280
[3-(OCH3)-5-F]—C6H3
CH2C6H5



A-1281
[3-(OCH3)-6-F]—C6H3
CH2C6H5



A-1282
[3-(OCH3)-6-Cl]—C6H3
CH2C6H5



A-1283
[2,4-(CF3)2]—C6H3
CH2C6H5



A-1284
[2-(CF3)-3-Cl]—C6H3
CH2C6H5



A-1285
[2-(CF3)-4-F]—C6H3
CH2C6H5



A-1286
[2-(CF3)-3-F]—C6H3
CH2C6H5



A-1287
[2-(CF3)-4-Cl]—C6H3
CH2C6H5



A-1288
[2-(CF3)-5-Cl]—C6H3
CH2C6H5



A-1289
[2-(CF3)-5-F]—C6H3
CH2C6H5



A-1290
[2-(CF3)-6-F]—C6H3
CH2C6H5



A-1291
[2-(CF3)-6-Cl]—C6H3
CH2C6H5



A-1292
[4-(CF3)-3-Cl]—C6H3
CH2C6H5



A-1293
[4-(CF3)-2-F]—C6H3
CH2C6H5



A-1294
[4-(CF3)-3-F]—C6H3
CH2C6H5



A-1295
[4-(CF3)-2-Cl]—C6H3
CH2C6H5



A-1296
[4-(CF3)-5-Cl]—C6H3
CH2C6H5



A-1297
[4-(CF3)-5-F]—C6H3
CH2C6H5



A-1298
[4-(CF3)-6-F]—C6H3
CH2C6H5



A-1299
[4-(CF3)-6-Cl]—C6H3
CH2C6H5



A-1300
[3-(CF3)-2-Cl]—C6H3
CH2C6H5



A-1301
[3-(CF3)-4-F]—C6H3
CH2C6H5



A-1302
[3-(CF3)-2-F]—C6H3
CH2C6H5



A-1303
[3-(CF3)-4-Cl]—C6H3
CH2C6H5



A-1304
[3-(CF3)-5-Cl]—C6H3
CH2C6H5



A-1305
[3-(CF3)-5-F]—C6H3
CH2C6H5



A-1306
[3-(CF3)-6-F]—C6H3
CH2C6H5



A-1307
[3-(CF3)-6-Cl]—C6H3
CH2C6H5



A-1308
[2,4-(Br)2]—C6H3
CH2C6H5



A-1309
[2-Br-3-Cl]—C6H3
CH2C6H5



A-1310
[2-Br-4-F]—C6H3
CH2C6H5



A-1311
[2-Br-3-F]—C6H3
CH2C6H5



A-1312
[2-Br-4-Cl]—C6H3
CH2C6H5



A-1313
[2-Br-5-Cl]—C6H3
CH2C6H5



A-1314
[2-Br-5-F]—C6H3
CH2C6H5



A-1315
[2-Br-6-F]—C6H3
CH2C6H5



A-1316
[2-Br-6-Cl]—C6H3
CH2C6H5



A-1317
[4-Br-3-Cl]—C6H3
CH2C6H5



A-1318
[4-Br-2-F]—C6H3
CH2C6H5



A-1319
[4-Br-3-F]—C6H3
CH2C6H5



A-1320
[4-Br-2-Cl]—C6H3
CH2C6H5



A-1321
[4-Br-5-Cl]—C6H3
CH2C6H5



A-1322
[4-Br-5-F]—C6H3
CH2C6H5



A-1323
[4-Br-6-F]—C6H3
CH2C6H5



A-1324
[4-Br-6-Cl]—C6H3
CH2C6H5



A-1325
[3-Br-2-Cl]—C6H3
CH2C6H5



A-1326
[3-Br-4-F]—C6H3
CH2C6H5



A-1327
[3-Br-2-F]—C6H3
CH2C6H5



A-1328
[3-Br-4-Cl]—C6H3
CH2C6H5



A-1329
[3-Br-5-Cl]—C6H3
CH2C6H5



A-1330
[3-Br-5-F]—C6H3
CH2C6H5



A-1331
[3-Br-6-F]—C6H3
CH2C6H5



A-1332
[3-Br-6-Cl]—C6H3
CH2C6H5



A-1333
C6H5
CH═CH2



A-1334
[2-Cl]—C6H4
CH═CH2



A-1335
[3-Cl]—C6H4
CH═CH2



A-1336
[4-Cl]—C6H4
CH═CH2



A-1337
[2-F]—C6H4
CH═CH2



A-1338
[3-F]—C6H4
CH═CH2



A-1339
[4-F]—C6H4
CH═CH2



A-1340
[2-CN]—C6H4
CH═CH2



A-1341
[3-CN]—C6H4
CH═CH2



A-1342
[4-CN]—C6H4
CH═CH2



A-1343
[2-CH3]—C6H4
CH═CH2



A-1344
[3-CH3]—C6H4
CH═CH2



A-1345
[4-CH3]—C6H4
CH═CH2



A-1346
[2-C2H5]—C6H4
CH═CH2



A-1347
[3-C2H5]—C6H4
CH═CH2



A-1348
[4-C2H5]—C6H4
CH═CH2



A-1349
[2-iso-C3H7]—C6H4
CH═CH2



A-1350
[3-iso-C3H7]—C6H4
CH═CH2



A-1351
[4-iso-C3H7]—C6H4
CH═CH2



A-1352
[2-(C(CH3)3)]—C6H4
CH═CH2



A-1353
[3-(C(CH3)3)]—C6H4
CH═CH2



A-1354
[4-(C(CH3)3)]—C6H4
CH═CH2



A-1355
[2-OCH3]—C6H4
CH═CH2



A-1356
[3-OCH3]—C6H4
CH═CH2



A-1357
[4-OCH3]—C6H4
CH═CH2



A-1358
[2-OC2H5]—C6H4
CH═CH2



A-1359
[3-OC2H5]—C6H4
CH═CH2



A-1360
[4-OC2H5]—C6H4
CH═CH2



A-1361
[2-CF3]—C6H4
CH═CH2



A-1362
[3-CF3]—C6H4
CH═CH2



A-1363
[4-CF3]—C6H4
CH═CH2



A-1364
[2-OCF]—C6H43
CH═CH2



A-1365
[3-OCF3]—C6H4
CH═CH2



A-1366
[4-OCF3]—C6H4
CH═CH2



A-1367
[2-CHF2]—C6H4
CH═CH2



A-1368
[3-CHF2]—C6H4
CH═CH2



A-1369
[4-CHF2]—C6H4
CH═CH2



A-1370
[2,3-(Cl)2]—C6H3
CH═CH2



A-1371
[2,4-(Cl)2]—C6H3
CH═CH2



A-1372
[2,5-(Cl)2]—C6H3
CH═CH2



A-1373
[2,6-(Cl)2]—C6H3
CH═CH2



A-1374
[3,4-(Cl)2]—C6H3
CH═CH2



A-1375
[3,5-(Cl)2]—C6H3
CH═CH2



A-1376
[2,3,4-(Cl)3]—C6H2
CH═CH2



A-1377
[2,3,5-(Cl)3]—C6H2
CH═CH2



A-1378
[2,3,6-(Cl)3]—C6H2
CH═CH2



A-1379
[2,4,5-(Cl)3]—C6H2
CH═CH2



A-1380
[2,4,6-(Cl)3]—C6H2
CH═CH2



A-1381
[3,4,5-(Cl)3]—C6H2
CH═CH2



A-1382
[2,3,4,5-(Cl)4]—C6H
CH═CH2



A-1383
[2,3,4,6-(Cl)4]—C6H
CH═CH2



A-1384
[2,3,5,6-(Cl)4]—C6H
CH═CH2



A-1385
[2,3,4,5,6-(Cl)5]—C6
CH═CH2



A-1386
[3,4-(Cl)2-2-F]—C6H2
CH═CH2



A-1387
[3,5-(Cl)2-2-F]—C6H2
CH═CH2



A-1388
[3,6-(Cl)2-2-F]—C6H2
CH═CH2



A-1389
[4,5-(Cl)2-2-F]—C6H2
CH═CH2



A-1390
[2,3-(Cl)2-6-F]—C6H2
CH═CH2



A-1391
[3,4-(Cl)2-5-F]—C6H2
CH═CH2



A-1392
[2,4-(Cl)2-3-F]—C6H2
CH═CH2



A-1393
[2,5-(Cl)2-3-F]—C6H2
CH═CH2



A-1394
[2,6-(Cl)2-3-F]—C6H2
CH═CH2



A-1395
[2,3-(Cl)2-4-F]—C6H2
CH═CH2



A-1396
[2,5-(Cl)2-4-F]—C6H2
CH═CH2



A-1397
[2,6-(Cl)2-4-F]—C6H2
CH═CH2



A-1398
[4,6-(Cl)2-2,3-(F)2]—C6H
CH═CH2



A-1399
[2,3-(Cl)2-5,6-(F)2]—C6H
CH═CH2



A-1400
[2,5-(Cl)2-4,6-(F)2]—C6H
CH═CH2



A-1401
[3,5-(Cl)2-2,4-(F)2]—C6H
CH═CH2



A-1402
[2,3-(Cl)2-4,6-(F)2]—C6H
CH═CH2



A-1403
[2,4-(Cl)2-3,6-(F)2]—C6H
CH═CH2



A-1404
[2,5-(Cl)2-3,6-(F)2]—C6H
CH═CH2



A-1405
[3,4-(Cl)2-2,5-(F)2]—C6H
CH═CH2



A-1406
[3,4-(Cl)2-2,6-(F)2]—C6H
CH═CH2



A-1407
[3,5-(Cl)2-2,6-(F)2]—C6H
CH═CH2



A-1408
[3,4,6-(Cl)3-2-F]—C6H
CH═CH2



A-1409
[2,3,5-(Cl)3-6-F]—C6H
CH═CH2



A-1410
[2,3,4-(Cl)3-6-F]—C6H
CH═CH2



A-1411
[3,4,5-(Cl)3-2-F]—C6H
CH═CH2



A-1412
[2,4,6-(Cl)3-3-F]—C6H
CH═CH2



A-1413
[2,4,5-(Cl)3-3-F]—C6H
CH═CH2



A-1414
[2,3,4-(Cl)3-5-F]—C6H
CH═CH2



A-1415
[2,3,5-(Cl)3-4-F]—C6H
CH═CH2



A-1416
[2,3,6-(Cl)3-4-F]—C6H
CH═CH2



A-1417
[2,3,4,5-(Cl)4-6-F]—C6
CH═CH2



A-1418
[2,3,4,6-(Cl)4-5-F]—C6
CH═CH2



A-1419
[2,3,5,6-(Cl)4-4-F]—C6
CH═CH2



A-1420
[2,3,4-(Cl)3-5,6-(F)2]—C6
CH═CH2



A-1421
[2,3,5-(Cl)3-4,6-(F)2]—C6
CH═CH2



A-1422
[2,4,5-(Cl)3-3,6-(F)2]—C6
CH═CH2



A-1423
[3,4,5-(Cl)3-2,6-(F)2]—C6
CH═CH2



A-1424
[2,3-(Cl)2-4,5,6-(F)3]—C6
CH═CH2



A-1425
[2,4-(Cl)2-3,5,6-(F)3]—C6
CH═CH2



A-1426
[3,4-(Cl)2-2,5,6-(F)3]—C6
CH═CH2



A-1427
[2,5-(Cl)2-3,4,6-(F)3]—C6
CH═CH2



A-1428
[2,6-(Cl)2-3,4,5-(F)3]—C6
CH═CH2



A-1429
[2,3-(F)2]—C6H3
CH═CH2



A-1430
[2,4-(F)2]—C6H3
CH═CH2



A-1431
[2,5-(F)2]—C6H3
CH═CH2



A-1432
[2,6-(F)2]—C6H3
CH═CH2



A-1433
[2,3,4-(F)3]—C6H2
CH═CH2



A-1434
[2,3,5-(F)3]—C6H2
CH═CH2



A-1435
[2,4,6-(F)3]—C6H2
CH═CH2



A-1436
[2,3,6-(F)3]—C6H2
CH═CH2



A-1437
[3,4,5-(F)3]—C6H2
CH═CH2



A-1438
[3,4,6-(F)3]—C6H2
CH═CH2



A-1439
[3-Cl-2-F]—C6H3
CH═CH2



A-1440
[4-Cl-2-F]—C6H3
CH═CH2



A-1441
[5-Cl-2-F]—C6H3
CH═CH2



A-1442
[2-Cl-6-F]—C6H3
CH═CH2



A-1443
[4-Cl-2,6-(F)2]—C6H2
CH═CH2



A-1444
[4-Cl-2,3-(F)2]—C6H2
CH═CH2



A-1445
[5-Cl-2,3-(F)2]—C6H2
CH═CH2



A-1446
[6-Cl-2,3-(F)2]—C6H2
CH═CH2



A-1447
[3-Cl-2,6-(F)2]—C6H2
CH═CH2



A-1448
[3-Cl-2,4-(F)2]—C6H2
CH═CH2



A-1449
[5-Cl-2,4-(F)2]—C6H2
CH═CH2



A-1450
[2-Cl-4,6-(F)2]—C6H2
CH═CH2



A-1451
[3-Cl-2,5-(F)2]—C6H2
CH═CH2



A-1452
[4-Cl-2,5-(F)2]—C6H2
CH═CH2



A-1453
[2-Cl-3,6-(F)2]—C6H2
CH═CH2



A-1454
[2,4-(CH3)2]—C6H3
CH═CH2



A-1455
[2-(CH3)-3-Cl]—C6H3
CH═CH2



A-1456
[2-(CH3)-4-F]—C6H3
CH═CH2



A-1457
[2-(CH3)-3-F]—C6H3
CH═CH2



A-1458
[2-(CH3)-4-Cl]—C6H3
CH═CH2



A-1459
[2-(CH3)-5-Cl]—C6H3
CH═CH2



A-1460
[2-(CH3)-5-F]—C6H3
CH═CH2



A-1461
[2-(CH3)-6-F]—C6H3
CH═CH2



A-1462
[2-(CH3)-6-Cl]—C6H3
CH═CH2



A-1463
[4-(CH3)-3-Cl]—C6H3
CH═CH2



A-1464
[4-(CH3)-2-F]—C6H3
CH═CH2



A-1465
[4-(CH3)-3-F]—C6H3
CH═CH2



A-1466
[4-(CH3)-2-Cl]—C6H3
CH═CH2



A-1467
[4-(CH3)-5-Cl]—C6H3
CH═CH2



A-1468
[4-(CH3)-5-F]—C6H3
CH═CH2



A-1469
[4-(CH3)-6-F]—C6H3
CH═CH2



A-1470
[4-(CH3)-6-Cl]—C6H3
CH═CH2



A-1471
[3-(CH3)-2-Cl]—C6H3
CH═CH2



A-1472
[3-(CH3)-4-F]—C6H3
CH═CH2



A-1473
[3-(CH3)-2-F]—C6H3
CH═CH2



A-1474
[3-(CH3)-4-Cl]—C6H3
CH═CH2



A-1475
[3-(CH3)-5-Cl]—C6H3
CH═CH2



A-1476
[3-(CH3)-5-F]—C6H3
CH═CH2



A-1477
[3-(CH3)-6-F]—C6H3
CH═CH2



A-1478
[3-(CH3)-6-Cl]—C6H3
CH═CH2



A-1479
[2,4-(OCH3)2]—C6H3
CH═CH2



A-1480
[3,5-(OCH3)2]—C6H3
CH═CH2



A-1481
[2-(OCH3)-3-Cl]—C6H3
CH═CH2



A-1482
[2-(OCH3)-4-F]—C6H3
CH═CH2



A-1483
[2-(OCH3)-3-F]—C6H3
CH═CH2



A-1484
[2-(OCH3)-4-Cl]—C6H3
CH═CH2



A-1485
[2-(OCH3)-5-Cl]—C6H3
CH═CH2



A-1486
[2-(OCH3)-5-F]—C6H3
CH═CH2



A-1487
[2-(OCH3)-6-F]—C6H3
CH═CH2



A-1488
[2-(OCH3)-6-Cl]—C6H3
CH═CH2



A-1489
[4-(OCH3)-3-Cl]—C6H3
CH═CH2



A-1490
[4-(OCH3)-2-F]—C6H3
CH═CH2



A-1491
[4-(OCH3)-3-F]—C6H3
CH═CH2



A-1492
[4-(OCH3)-2-Cl]—C6H3
CH═CH2



A-1493
[4-(OCH3)-5-Cl]—C6H3
CH═CH2



A-1494
[4-(OCH3)-5-F]—C6H3
CH═CH2



A-1495
[4-(OCH3)-6-F]—C6H3
CH═CH2



A-1496
[4-(OCH3)-6-Cl]—C6H3
CH═CH2



A-1497
[3-(OCH3)-2-Cl]—C6H3
CH═CH2



A-1498
[3-(OCH3)-4-F]—C6H3
CH═CH2



A-1499
[3-(OCH3)-2-F]—C6H3
CH═CH2



A-1500
[3-(OCH3)-4-Cl]—C6H3
CH═CH2



A-1501
[3-(OCH3)-5-Cl]—C6H3
CH═CH2



A-1502
[3-(OCH3)-5-F]—C6H3
CH═CH2



A-1503
[3-(OCH3)-6-F]—C6H3
CH═CH2



A-1504
[3-(OCH3)-6-Cl]—C6H3
CH═CH2



A-1505
[2,4-(CF3)2]—C6H3
CH═CH2



A-1506
[2-(CF3)-3-Cl]—C6H3
CH═CH2



A-1507
[2-(CF3)-4-F]—C6H3
CH═CH2



A-1508
[2-(CF3)-3-F]—C6H3
CH═CH2



A-1509
[2-(CF3)-4-Cl]—C6H3
CH═CH2



A-1510
[2-(CF3)-5-Cl]—C6H3
CH═CH2



A-1511
[2-(CF3)-5-F]—C6H3
CH═CH2



A-1512
[2-(CF3)-6-F]—C6H3
CH═CH2



A-1513
[2-(CF3)-6-Cl]—C6H3
CH═CH2



A-1514
[4-(CF3)-3-Cl]—C6H3
CH═CH2



A-1515
[4-(CF3)-2-F]—C6H3
CH═CH2



A-1516
[4-(CF3)-3-F]—C6H3
CH═CH2



A-1517
[4-(CF3)-2-Cl]—C6H3
CH═CH2



A-1518
[4-(CF3)-5-Cl]—C6H3
CH═CH2



A-1519
[4-(CF3)-5-F]—C6H3
CH═CH2



A-1520
[4-(CF3)-6-F]—C6H3
CH═CH2



A-1521
[4-(CF3)-6-Cl]—C6H3
CH═CH2



A-1522
[3-(CF3)-2-Cl]—C6H3
CH═CH2



A-1523
[3-(CF3)-4-F]—C6H3
CH═CH2



A-1524
[3-(CF3)-2-F]—C6H3
CH═CH2



A-1525
[3-(CF3)-4-Cl]—C6H3
CH═CH2



A-1526
[3-(CF3)-5-Cl]—C6H3
CH═CH2



A-1527
[3-(CF3)-5-F]—C6H3
CH═CH2



A-1528
[3-(CF3)-6-F]—C6H3
CH═CH2



A-1529
[3-(CF3)-6-Cl]—C6H3
CH═CH2



A-1530
[2,4-(Br)2]—C6H3
CH═CH2



A-1531
[2-Br-3-Cl]—C6H3
CH═CH2



A-1532
[2-Br-4-F]—C6H3
CH═CH2



A-1533
[2-Br-3-F]—C6H3
CH═CH2



A-1534
[2-Br-4-Cl]—C6H3
CH═CH2



A-1535
[2-Br-5-Cl]—C6H3
CH═CH2



A-1536
[2-Br-5-F]—C6H3
CH═CH2



A-1537
[2-Br-6-F]—C6H3
CH═CH2



A-1538
[2-Br-6-Cl]—C6H3
CH═CH2



A-1539
[4-Br-3-Cl]—C6H3
CH═CH2



A-1540
[4-Br-2-F]—C6H3
CH═CH2



A-1541
[4-Br-3-F]—C6H3
CH═CH2



A-1542
[4-Br-2-Cl]—C6H3
CH═CH2



A-1543
[4-Br-5-Cl]—C6H3
CH═CH2



A-1544
[4-Br-5-F]—C6H3
CH═CH2



A-1545
[4-Br-6-F]—C6H3
CH═CH2



A-1546
[4-Br-6-Cl]—C6H3
CH═CH2



A-1547
[3-Br-2-Cl]—C6H3
CH═CH2



A-1548
[3-Br-4-F]—C6H3
CH═CH2



A-1549
[3-Br-2-F]—C6H3
CH═CH2



A-1550
[3-Br-4-Cl]—C6H3
CH═CH2



A-1551
[3-Br-5-Cl]—C6H3
CH═CH2



A-1552
[3-Br-5-F]—C6H3
CH═CH2



A-1553
[3-Br-6-F]—C6H3
CH═CH2



A-1554
[3-Br-6-Cl]—C6H3
CH═CH2











From the tables above, the compound names for the individual compounds are derived as follows: The “compound I.3aA-10” (emphasis added), for example, is the compound of the formula I according to the invention in which X is N, Z is CH2CH2CH(CH3), R4 is hydrogen, R3 is hydrogen (as stated in Table 3a) and R1 is 4-cyanophenyl and R2 is hydrogen (as stated in row 10 of Table A).


The compounds of the formula I and the compositions according to the invention are suitable as fungicides for controlling harmful fungi. They are distinguished by excellent activity against a broad spectrum of phytopathogenic fungi including soilborne pathogens which originate in particular from the classes of the Plasmodiophoromycetes, Peronosporomycetes (syn. Oomycetes), Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes (syn. Fungi imperfecti). Some of them are systemically active and can be used in crop protection as foliar fungicides, fungicides for seed dressing and soil fungicides. In addition, they are suitable for controlling fungi which, inter alia, attack the wood or the roots of plants.


The compounds I and the compositions according to the invention are of particular importance for the control of a large number of pathogenic fungi on various crop plants such as cereals, for example wheat, rye, barley, triticale, oats or rice; beets, for example sugar beets or fodder beets; pomaceous fruits, stone fruits and soft fruits, for example apples, pears, plums, peaches, almonds, cherries, strawberries, raspberries, currants or gooseberries; leguminous plants, for example beans, lentils, peas, lucerne or soybeans; oil plants, for example oilseed rape, mustard, olives, sunflowers, coconut, cocoa, castor beans, oil palms, peanuts or soybeans; cucurbits, for example pumpkins, cucumbers or melons; fiber plants, for example cotton, flax, hemp or jute; citrus fruits, for example oranges, lemons, grapefruits or mandarins; vegetable plants, for example spinach, lettuce, asparagus, cabbage plants, carrots, onions, tomatoes, potatoes, pumpkins or bell peppers; laurel plants, for example avocados, cinnamon or camphor; energy and raw material plants, for example corn, soybeans, wheat, oilseed rape, sugar cane or oil palms; corn; tobacco; nuts; coffee; tea; bananas; grapevines (grapes for eating and grapes for wine making); hops; grass, for example lawns; rubber plants; ornamental and forest plants, for example flowers, shrubs, deciduous trees and coniferous trees, and also on the propagation material, for example seeds, and on the harvested material of these plants.


Preferably, the compounds I and the compositions according to the invention are used for controlling a large number of fungal pathogens in agricultural crops, for example potatoes, sugar beets, tobacco, wheat, rye, barley, oats, rice, corn, cotton, soybeans, oilseed rape, leguminous plants, sunflowers, coffee or sugar cane; fruit plants, grapevines and ornamental plants and vegetables, for example cucumbers, tomatoes, beans and pumpkins and also on the propagation material, for example seeds, and the harvested products of these plants.


The term plant propagation materials comprises all generative parts of the plant, for example seeds, and vegetative plant parts, such as seedlings and tubers (for example potatoes) which can be utilized for propagating a plant. These include seeds, roots, fruits, tubers, bulbs, rhizomes, shoots and other plant parts including seedlings and young plants which are transplanted after germination or after emergence. The young plants can be protected by partial or complete treatment, for example by immersion or watering, against harmful fungi.


The treatment of plant propagation materials with compounds I or with the compositions according to the invention is used for controlling a large number of fungal pathogens in cereal crops, for example wheat, rye, barley or oats; rice, corn, cotton and soybeans.


The term crop plants also includes those plants which have been modified by breeding, mutagenesis or genetic engineering methods including the biotechnological agricultural products which are on the market or under development (see, for example, http://www.bio.org/speeches/pubs/er/agri_products.asp). 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 by natural recombination (that is to say, a recombination of the genetic information). In general, one or more genes are integrated into the genetic material of the plant in order to improve the properties of the plant. Such modifications by genetic engineering include post-translational modifications of proteins, oligopeptides or polypeptides, for example by glycosylation or attachment of polymers such as, for example, prenylated, acetylated or farnesylated radicals or PEG radicals.


By way of example, mention may be made of 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 (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). Clearfield® oilseed rape (BASF SE, Germany), for example, which is tolerant to imidazolinones, for example imazamox, was generated by breeding and mutagenesis. With the aid of genetic engineering methods, crop plants such as soybeans, cotton, corn, beets and oilseed rape were generated which are resistant to glyphosate or glufosinate, and which are obtainable under the trade names RoundupReady® (glyphosate-resistant, Monsanto, U.S.A.) and Liberty Link® (glufosinate-resistant, Bayer CropScience, Germany).


Also included are plants which, owing to interventions by genetic engineering, produce one or more toxins, for example those of the bacterial strain Bacillus. 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, ecdyson 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 93/07278, WO 95/34656, EP-A 427 529, EP-A 451 878, WO 03/18810 and WO 03/52073. 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. Many 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 which produce 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).


Also included are plants which, with the aid of genetic engineering, produce one or more proteins which 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 varieties which, by producing this protein, are resistant to bacteria such as Erwinia amylvora).


Also included are 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.


Also included are 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, DOW Agro Sciences, Canada).


Also included are 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, BASF SE, Germany).


Specifically, the compounds I and, respectively, the compositions according to the invention are suitable for controlling the following plant diseases:



Albugo spp. (white rust) on ornamental plants, vegetable crops (for example A. candida) and sunflowers (for example A. tragopogonis);



Alternaria spp. (black spot disease, black blotch) on vegetables, oilseed rape (for example A. brassicola or A. brassicae), sugar beet (for example A. tenuis), fruit, rice, soybeans and also on potatoes (for example A. solani or A. alternata) and tomatoes (for example A. solani or A. alternata) and Alternaria spp. (black head) on wheat; Aphanomyces spp. on sugar beet and vegetables;



Ascochyta spp. on cereals and vegetables, for example A. tritici (Ascochyta leaf blight) on wheat and A. hordei on barley;



Bipolaris and Drechslera spp. (teleomorph: Cochliobolus spp.) for example leaf spot diseases (D. maydis and B. zeicola) on corn, for example glume blotch (B. sorokinlana) on cereals and for example B. oryzae on rice and on lawn;



Blumeria (old name: Erysiphe) graminis (powdery mildew) on cereals (for example wheat or barley);



Botryosphaeria spp. (‘Black Dead Arm Disease’) on grapevines (for example B. obtusa);



Botrytis cinerea (teleomorph: Botryotinia fuckeliana: gray mold, gray rot) on soft fruit and pome fruit (inter alia strawberries), vegetables (inter alia lettuce, carrots, celeriac and cabbage), oilseed rape, flowers, grapevines, forest crops and wheat (ear mold);



Bremia lactucae (downy mildew) on lettuce;



Ceratocystis (syn. Ophiostoma) spp. (blue stain fungus) on deciduous trees and coniferous trees, for example C. ulmi (Dutch elm disease) on elms;



Cercospora spp. (Cercospora leaf spot) on corn (for example C. zeae-maydis), rice, sugar beet (for example C. beticola), sugar cane, vegetables, coffee, soybeans (for example C. sojina or C. kikuchii) and rice;



Cladosporium spp. on tomato (for example C. fulvum: tomato leaf mold) and cereals, for example C. herbarum (ear rot) on wheat;



Claviceps purpurea (ergot) on cereals;



Cochliobolus (anamorph: Helminthosporium or Bipolaris) spp. (leaf spot) on corn (for example C. carbonum), cereals (for example C. sativus, anamorph: B. sorokiniana: glume blotch) and rice (for example C. miyabeanus, anamorph: H. oryzae);



Colletotrichum (teleomorph: Glomerella) spp. (anthracnosis) on cotton (for example C. gossypii), corn (for example C. graminicola: stem rot and anthracnosis), soft fruit, potatoes (for example C. coccodes: wilt disease), beans (for example C. lindemuthianum) and soybeans (for example C. truncatum);



Corticium spp., for example C. sasakii (sheath blight) on rice;



Corynespora cassiicola (leaf spot) on soybeans and ornamental plants;



Cycloconium spp., for example C. oleaginum on olive; Cylindrocarpon spp. (for example fruit tree cancer or black foot disease of grapevine, teleomorph: Nectria or Neonectria spp.) on fruit trees, grapevines (for example C. liriodendri, teleomorph: Neonectria liriodendri, black foot disease) and many ornamental trees;



Dematophora (teleomorph: Rosellinia) necatrix (root/stem rot) on soybeans;



Diaporthe spp. for example D. phaseolorum (stem disease) on soybeans;



Drechslera (syn. Helminthosporium, teleomorph: Pyrenophora) spp. on corn, cereals, such as barley (for example D. teres, net blotch) and on wheat (for example D. tritici-repentis: DTR leaf spot), rice and lawn;


Esca disease (dieback of grapevine, apoplexia) on grapevines, caused by Formitiporia (syn. Phellinus) punctata, F. mediterranea, Phaeomoniella chlamydospora (old name Phaeoacremonium chlamydosporum), Phaeoacremonium aleophilum and/or Botryosphaeria obtusa; Elsinoe spp. on pome fruit (E. pyri) and soft fruit (E. veneta: anthracnosis) and also grapevines (E. ampelina: anthracnosis);



Entyloma oryzae (leaf smut) on rice;



Epicoccum spp. (black head) on wheat; Erysiphe spp. (powdery mildew) on sugar beet (E. betae), vegetables (for example E. pisi), such as cucumber species (for example E. cichoracearum) and cabbage species, such as oilseed rape (for example E. cruciferarum);



Eutypa lata (Eutypa cancer or dieback, anamorph: Cytosporina lata, syn. Libertella blepharis) on fruit trees, grapevines and many ornamental trees;



Exserohilum (syn. Helminthosporium) spp. on corn (for example E. turcicum);



Fusarium (teleomorph: Gibberella) spp. (wilt disease, root and stem rot) on various plants, such as for example F. graminearum or F. culmorum (root rot and silver-top) on cereals (for example wheat or barley), F. oxysporum on tomatoes, F. solani on soybeans and F. verticillioides on corn;



Gaeumannomyces graminis (take-all) on cereals (for example wheat or barley) and corn; Gibberella spp. on cereals (for example G. zeae) and rice (for example G. fujikuroi: bakanae disease);



Glomerella cingulata on grapevines, pome fruit and other plants and G. gossypii on cotton; Grainstaining complex on rice;



Guignardia bewellii (black rot) on grapevines;



Gymnosporangium spp. on Rosaceae and juniper, for example G. sabinae (pear rust) on pears;



Helminthosporium spp. (syn. Drechslera, teleomorph: Cochliobolus) on corn, cereals and rice; Hemileia spp., for example H. vastatrix (coffee leaf rust) on coffee;



Isariopsis clavispora (syn. Cladosporium vitis) on grapevines;



Macrophomina phaseolina (syn. phaseoli) (root/stem rot) on soybeans and cotton; Microdochium (syn. Fusarium) nivale (pink snow mold) on cereals (for example wheat or barley);



Microsphaera diffusa (powdery mildew) on soybeans;



Monilinia spp., for example M. laxa, M. fructicola and M. fructigena (blossom and twig blight) on stone fruit and other Rosaceae; Mycosphaerella spp. on cereals, bananas, soft fruit and peanuts, such as for example M. graminicola (anamorph: Septoria tritici, Septoria leaf blotch) on wheat or M. fijiensis (sigatoka disease) on bananas;



Peronospora spp. (downy mildew) on cabbage (for example P. brassicae), oilseed rape (for example P. parasitica), bulbous plants (for example P. destructor), tobacco (P. tabacina) and soybeans (for example P. manshurica);



Phakopsora pachyrhizi and P. meibomiae (soybean rust) on soybeans;



Phialophora spp. for example on grapevines (for example P. tracheiphila and P. tetraspora) and soybeans (for example P. gregata: stem disease);



Phoma lingam (root and stem rot) on oilseed rape and cabbage and P. betae (leaf spot) on sugar beet;



Phomopsis spp. on sunflowers, grapevines (for example P. viticola: dead-arm disease) and soybeans (for example stem canker/stem blight: P. phaseoli, teleomorph: Diaporthe phaseolorum);



Physoderma maydis (brown spot) on corn;



Phytophthora spp. (wilt disease, root, leaf, stem and fruit rot) on various plants, such as on bell peppers and cucumber species (for example P. capsici), soybeans (for example P. megasperma, syn. P. sojae), potatoes and tomatoes (for example P. infestans: late blight and brown rot) and deciduous trees (for example P. ramorum: sudden oak death);



Plasmodiophora brassicae (club-root) on cabbage, oilseed rape, radish and other plants;



Plasmopara spp., for example P. viticola (peronospora of grapevines, downy mildew) on grapevines and P. halstedii on sunflowers; Podosphaera spp. (powdery mildew) on Rosaceae, hops, pome fruit and soft fruit, for example P. leucotricha on apple;



Polymyxa spp., for example on cereals, such as barley and wheat (P. graminis) and sugar beet (P. betae) and the viral diseases transmitted thereby;



Pseudocercosporella herpotrichoides (eyespot/stem break, teleomorph: Tapesia yallundae) on cereals, for example wheat or barley;



Pseudoperonospora (downy mildew) on various plants, for example P. cubensis on cucumber species or P. humili hops;



Pseudopezicula tracheiphila (angular leaf scorch, anamorph: Phialophora) on grapevines;



Puccinia spp. (rust disease) on various plants, for example P. triticina (brown rust of wheat), P. striiformis (yellow rust), P. hordei (dwarf leaf rust), P. graminis (black rust) or P. recondita (brown rust of rye) on cereals, such as for example wheat, barley or rye, and on asparagus (for example P. asparagi);



Pyrenophora (anamorph: Drechslera) tritici-repentis (speckled leaf blotch) on wheat or P. teres (net blotch) on barley;



Pyricularia spp., for example P. oryzae (teleomorph: Magnaporthe grisea, rice blast) on rice and P. grisea on lawn and cereals;



Pythium spp. (damping-off disease) on lawn, rice, corn, wheat, cotton, oilseed rape, sunflowers, sugar beet, vegetables and other plants (for example P. ultimum or P. aphanidermatum);



Ramularia spp., for example R. collo-cygni (Ramularia leaf and lawn spot/physiological leaf spot) on barley and R. beticola on sugar beet;



Rhizoctonia spp. on cotton, rice, potatoes, lawn, corn, oilseed rape, potatoes, sugar beet, vegetables and on various other plants, for example R. solani (root and stem rot) on soybeans, R. solani (sheath blight) on rice or R. cerealis (sharp eyespot) on wheat or barley;



Rhizopus stolonifer (soft rot) on strawberries, carrots, cabbage, grapevines and tomato; Rhynchosporium secalis (leaf spot) on barley, rye and triticale;



Sarocladium oryzae and S. attenuatum (sheath rot) on rice;



Sclerotinia spp. (stem or white rot) on vegetable and field crops, such as oilseed rape, sunflowers (for example Sclerotinia sclerotiorum) and soybeans (for example S. rolfsii);



Septoria spp. on various plants, for example S. glycines (leaf spot) on soybeans, S. tritici (Septoria leaf blotch) on wheat and S. (syn. Stagonospora) nodorum (leaf blotch and glume blotch) on cereals;



Uncinula (syn. Eysiphe) necator (powdery mildew, anamorph: Oidium tuckeri) on grapevines;



Setospaeria spp. (leaf spot) on corn (for example S. turcicum, syn. Helminthosporium turcicum) and lawn;



Sphacelotheca spp. (head smut) on corn, (for example S. reiliana: kernel smut), millet and sugar cane;



Sphaerotheca fuliginea (powdery mildew) on cucumber species;



Spongospora subterranea (powdery scab) on potatoes and the viral diseases transmitted thereby;



Stagonospora spp. on cereals, for example S. nodorum (leaf blotch and glume blotch, teleomorph: Leptosphaeria [syn. Phaeosphaeria] nodorum) on wheat;



Synchytrium endobioticum on potatoes (potato wart disease);



Taphrina spp., for example T. deformans (curly-leaf disease) on peach and T. pruni (plum-pocket disease) on plums;



Thielaviopsis spp. (black root rot) on tobacco, pome fruit, vegetable crops, soybeans and cotton, for example T. basicola (syn. Chalara elegans); Tilletia spp. (bunt or stinking smut) on cereals, such as for example T. tritici (syn. T. caries, wheat bunt) and T. controversa (dwarf bunt) on wheat;



Typhula incarnata (gray snow mold) on barley or wheat;



Urocystis spp., for example U. occulta (flag smut) on rye;



Uromyces spp. (rust) on vegetable plants, such as beans (for example U. appendiculatus, syn. U. phaseoli) and sugar beet (for example U. betae);



Ustilago spp. (loose smut) on cereals (for example U. nuda and U. avaenae), corn (for example U. maydis: corn smut) and sugar cane;



Venturia spp. (scab) on apples (for example V. inaequalis) and pears and



Verticillium spp. (leaf and shoot wilt) on various plants, such as fruit trees and ornamental trees, grapevines, soft fruit, vegetable and field crops, such as for example V. dahliae on strawberries, oilseed rape, potatoes and tomatoes.


Moreover, the compounds I and the compositions according to the invention are suitable for controlling harmful fungi in the protection of stored products (also of harvested products) and in the protection of materials and buildings. The term “protection of materials and buildings” encompasses the protection of industrial and non-living materials such as, for example, adhesives, glues, wood, paper and cardboard, textiles, leather, paint dispersions, plastic, cooling lubricants, fibers and tissues, against attack and destruction by unwanted microorganisms such as fungi and bacteria. In the protection of wood and materials, particular attention is paid to the following harmful fungi: Ascomycetes, such as Ophiostoma spp., Ceratocystis spp., Aureobasidium pullulans, Sclerophoma spp., Chaetomium spp., Humicola spp., Petriella spp., Trichurus spp.; Basidiomycetes such as Coniophora spp., Coriolus spp., Gloeophyllum spp., Lentinus spp., Pleurotus spp., Poria spp., Serpula spp. and Tyromyces spp., Deuteromycetes such as Aspergillus spp., Cladosporium spp., Penicillium spp., Trichoderma spp., Alternaria spp., Paecilomyces spp. and Zygomycetes such as Mucor spp., and in addition in the protection of materials to the following yeast fungi: Candida spp. and Saccharomyces cerevisae.


The compounds of the formula I may be present in various crystal modifications which may differ in their biological activity. These are included in the scope of the present invention.


The compounds I and the compositions according to the invention are suitable for improving plant health. Moreover, the invention relates to a method for improving plant health by treating the plants, the plant propagation material and/or the site at which the plants grow or are intended to grow with an effective amount of the compounds I or the compositions according to the invention.


The term “plant health” comprises those states of a plant and/or its harvested material which are determined by various indicators individually or in combination, such as, for example, yield (for example increased biomass and/or increased content of utilizable ingredients), plant vitality (for example increased plant growth and/or greener leaves (“greening effect”)), quality (for example increased content or composition of certain ingredients) and tolerance to biotic and/or abiotic stress. The indicators mentioned here for a state of plant health may occur independently of one another or may influence each other.


The compounds I are employed as such or in the form of a composition by treating the harmful fungi, their habitat or the plants or plant propagation materials, for example seed materials, to be protected from fungal attack, the soil, areas, materials or spaces with a fungicidally effective amount of the compounds I. The application can be carried out both before and after the infection of the plants, plant propagation materials, for example seed materials, the soil, the areas, materials or spaces by the fungi.


Plant propagation materials can be treated prophylactically during or even before sowing or during or even before transplanting with compounds I as such or with a composition comprising at least one compound I.


The invention furthermore relates to agrochemical compositions comprising a solvent or solid carrier and at least one compound I, and also to their use for controlling harmful fungi.


An agrochemical composition comprises a fungicidally effective amount of a compound I. The term “effective amount” refers to an amount of the agrochemical composition or of the compound I which is sufficient for controlling harmful fungi on crop plants or in the protection of materials and buildings and does not cause any significant damage to the treated crop plants. Such an amount may vary within a wide range and is influenced by numerous factors, such as, for example, the harmful fungus to be controlled, the respective crop plant or materials treated, the climatic conditions and compounds.


The compounds I, their N-oxides and their salts can be converted into the types customary for agrochemical compositions, for example solutions, emulsions, suspensions, dusts, powders, pastes and granules. The type of composition depends on the respective intended purpose; in each case, it should ensure a fine and even distribution of the compound according to the invention.


Here, examples of types of compositions are suspensions (SC, OD, FS), emulsifiable concentrates (EC), emulsions (EW, EO, ES), pastes, pastilles, wettable powders or dusts (WP, SP, SS, WS, DP, DS) or granules (GR, FG, GG, MG) which may either be water-soluble or dispersible (wettable), and also gels for treating plant propagation materials such as seed (GF).


In general, the composition types (for example EC, SC, OD, FS, WG, SG, WP, SP, SS, WS, GF) are used in diluted form. Composition types such as DP, DS, GR, FG, GG and MG are generally employed in undiluted form.


The agrochemical compositions are prepared in a known manner (see, for example, U.S. Pat. No. 3,060,084, EP-A 707 445 (for liquid concentrates), Browning, “Agglomeration”, Chemical Engineering, Dec. 4, 1967, 147-48, Perry's Chemical Engineer's Handbook, 4th edition, McGraw-Hill, New York, 1963, 8-57 and ff., WO 91/13546, U.S. Pat. No. 4,172,714, U.S. Pat. No. 4,144,050, U.S. Pat. No. 3,920,442, U.S. Pat. No. 5,180,587, U.S. Pat. No. 5,232,701, U.S. Pat. No. 5,208,030, GB 2,095,558, U.S. Pat. No. 3,299,566, Klingman: Weed Control as a Science (John Wiley & Sons, New York, 1961), Hance et al.: Weed Control Handbook (8th Ed., Blackwell Scientific Publications, Oxford, 1989) und Mollet, H. und Grubemann, A.: Formulation technology (Wiley VCH Verlag, Weinheim, 2001).


The agrochemical compositions may furthermore also comprise auxiliaries customary for crop protection compositions, the selection of the auxiliaries depending on the use form or the active compound in question.


Examples of suitable auxiliaries are solvents, solid carriers, surfactants (such as further solubilizers, protective colloids, wetting agents and tackifiers), organic and inorganic thickeners, bactericides, antifreeze agents, antifoams, optionally colorants and adhesives (for example for the treatment of seed).


Suitable solvents are water, organic solvents, such as mineral oil fractions having a medium to high boiling point, such as kerosene and diesel oil, furthermore coal tar oils, and also oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, for example paraffins, tetrahydronaphthalene, alkylated naphthalenes and derivatives thereof, alkylated benzenes and derivatives thereof, alcohols, such as methanol, ethanol, propanol, butanol and cyclohexanol, glycols, ketones, such as cyclohexanone, gamma-butyrolactone, dimethyl fatty amides, fatty acids and fatty acid esters and strongly polar solvents, for example amines, such as N-methylpyrrolidone. In principle, it is also possible to use solvent mixtures, and also mixtures of the solvents mentioned above and water.


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


Suitable surfactants (adjuvants, wetting agents, tackifiers, dispersants or emulsifiers) are the alkali metal, alkaline earth metal and ammonium salts of aromatic sulfonic acids, for example of lignosulfonic acid (Borresperse® types, Borregaard, Norway), phenolsulfonic acid, naphthalenesulfonic acid (Morwet® types, Akzo Nobel, USA) and dibutylnaphthalenesulfonic acid (Nekal® types, BASF, Germany), and also of fatty acids, alkyl- and alkylarylsulfonates, alkyl, lauryl ether and fatty alcohol sulfates, and also 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 octyl phenol ether, ethoxylated isooctylphenol, octylphenol or nonylphenol, alkylphenyl polyglycol ether, 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 also proteins, denatured proteins, polysaccharides (for example methylcellulose), hydrophobically modified starches, polyvinyl alcohol (Mowiol® types, Clariant, Switzerland), polycarboxylates (Sokalan® types, BASF, Germany), polyalkoxylates, polyvinylamine (Lupamin® types, BASF, Germany), polyethyleneimine (Lupasol® types, BASF, Germany), polyvinylpyrrolidone and copolymers thereof.


Examples of thickeners (i.e. compounds which impart modified flow properties to the composition, i.e. high viscosity in the state of rest and low viscosity in motion) are polysaccharides and also organic and inorganic sheet minerals, such as xanthan gum (Kelzan®, CP Kelco, USA), Rhodopol® 23 (Rhodia, France) or Veegum® (R.T. Vanderbilt, USA) or Attaclay® (Engelhard Corp., NJ, USA).


Bactericides can be added for stabilizing the composition. 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 derivatives, such as alkylisothiazolinones and benzisothiazolinones (Acticide® MBS from Thor Chemie).


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


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


Examples of colorants are both sparingly water-soluble pigments and water-soluble dyes. Examples which may be mentioned are the dyes and pigments known under the names Rhodamin B, C. I. Pigment Red 112 and C. I. Solvent Red 1, 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 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 cellulose ether (Tylose®, Shin-Etsu, Japan).


Suitable for the preparation of directly sprayable solutions, emulsions, pastes or oil dispersions are mineral oil fractions of medium to high boiling point, such as kerosene or diesel oil, furthermore coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, for example toluene, xylene, paraffin, tetrahydro-naphthalene, alkylated naphthalenes or their derivatives, methanol, ethanol, propanol, butanol, cyclohexanol, cyclohexanone, isophorone, strongly polar solvents, for example dimethyl sulfoxide, N-methylpyrrolidone and water.


Powders, materials for spreading and dustable products can be prepared by mixing or concomitantly grinding the compounds I and, if present, further active compounds with at least one solid carrier.


Granules, for example coated granules, impregnated granules and homogeneous granules, can be prepared by binding the active compounds to at least one solid carrier. Solid carriers are, for example, mineral earths, such as silica gels, silicates, talc, kaolin, attaclay, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate and magnesium sulfate, magnesium oxide, ground synthetic substances, fertilizers, such as ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas and vegetable products, such as cereal meal, tree bark meal, sawdust and nutshell meal, cellulose powder or other solid carriers.


The following are examples of types of composition:


1. Types of Composition for Dilution with Water


i) Water-Soluble Concentrates (SL, LS)


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


ii) Dispersible Concentrates (DC)


20 parts by weight of the active compounds are dissolved in 70 parts by weight of cyclohexanone with addition of 10 parts by weight of a dispersant, for example polyvinylpyrrolidone. Dilution with water gives a dispersion. The active compound content is 20% by weight.


iii) Emulsifiable Concentrates (EC)


15 parts by weight of the active compounds are dissolved in 75 parts by weight of xylene with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight). Dilution with water gives an emulsion. The composition has an active compound content of 15% by weight.


iv) Emulsions (EW, EO, ES)


25 parts by weight of the active compounds are dissolved in 35 parts by weight of xylene with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight). This mixture is added to 30 parts by weight of water by means of an emulsifying machine (e.g. Ultraturrax) and made into a homogeneous emulsion. Dilution with water gives an emulsion. The composition has an active compound content of 25% by weight.


v) Suspensions (SC, OD, FS)


In an agitated ball mill, 20 parts by weight of the active compounds are comminuted with addition of 10 parts by weight of dispersants and 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 composition is 20% by weight.


vi) Water-Dispersible Granules and Water-Soluble Granules (WG, SG)


50 parts by weight of the active compounds are ground finely with addition of 50 parts by weight of dispersants and 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 composition has an active compound content of 50% by weight.


vii) Water-Dispersible Powders and Water-Soluble Powders (WP, SP, SS, WS)


75 parts by weight of the active compounds are ground in a rotor-stator mill with addition of 25 parts by weight of dispersants, wetters and silica gel. Dilution with water gives a stable dispersion or solution of the active compound. The active compound content of the composition is 75% by weight.


viii) Gels (GF)


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


2. Types of Composition to be Applied Undiluted

ix) Dusts (DP, DS)


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


x) Granules (GR, FG, GG, MG)


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


xi) ULV Solutions (UL)


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


In general, the compositions of the compounds according to the invention comprise from 0.01 to 95% by weight, preferably from 0.1 to 90% by weight, of the compounds I. The compounds are preferably employed in a purity of from 90% to 100%, preferably 95% to 100%.


Water-soluble concentrates (LS), suspensions (FS), dusts (DS), water-dispersible and water-soluble powders (WS, SS), emulsions (ES), emulsifiable concentrates (EC) and gels (GF) are usually used for the treatment of plant propagation materials, in particular seed. These compositions can be applied to the propagation materials, in particular seed, in undiluted or, preferably, diluted form. In this case, the corresponding composition can be diluted 2 to 10 times so that in the compositions used for the seed dressing from 0.01 to 60% by weight, preferably from 0.1 to 40% by weight of active compound are present. The application can be carried out before or during sowing. The treatment of plant propagation material, in particular the treatment of seed, is known to the person skilled in the art and is carried out by dusting, coating, pelleting, dipping or drenching the plant propagation material, the treatment preferably being carried out by pelleting, coating and dusting or by furrow treatment, such that, for example, premature germination of the seed is prevented.


For seed treatment, preference is given to using suspensions. Such compositions usually comprise from 1 to 800 g of active compound/I, from 1 to 200 g of surfactants/I, from 0 to 200 g of antifreeze agents/I, from 0 to 400 g of binders/I, from 0 to 200 g of colorants/I and solvents, preferably water.


The compounds can be used as such or in the form of their compositions, for example in the form of directly sprayable solutions, powders, suspensions, dispersions, emulsions, oil dispersions, pastes, dustable products, materials for spreading or granules, by means of spraying, atomizing, dusting, spreading, raking in, immersing or pouring. The types of composition depend entirely on the intended purposes; the intention is to ensure in each case the finest possible distribution of the active compounds according to the invention.


Aqueous use forms can be prepared from emulsion concentrates, pastes or wettable powders (sprayable powders, oil dispersions) by adding water. To prepare emulsions, pastes or oil dispersions, the substances, as such or dissolved in an oil or solvent, can be homogenized in water by means of a wetter, tackifier, dispersant or emulsifier. Alternatively, it is also possible to prepare concentrates composed of active substance, wetter, tackifier, dispersant or emulsifier and, if appropriate, solvent or oil, and such concentrates are suitable for dilution with water.


The active compound concentrations in the ready-to-use preparations can be varied within relatively wide ranges. In general, they are from 0.0001 to 10%, preferably from 0.01 to 1%.


The active compounds may also be used successfully in the ultra-low-volume process (ULV), by which it is possible to apply compositions comprising over 95% by weight of active compound, or even to apply the active compound without additives.


When used in crop protection, the application rates are from 0.001 to 2.0 kg of active compound per ha, preferably from 0.005 to 2 kg per ha, particularly preferably from 0.05 to 0.9 kg per ha, especially from 0.1 to 0.75 kg per ha, depending on the nature of the desired effect.


In the treatment of plant propagation materials, for example seed, the amounts of active compound used are generally from 0.1 to 1000 g/100 kg of propagation material or seed, preferably from 1 to 1000 g/100 kg, particularly preferably from 1 to 100 g/100 kg, especially from 5 to 100 g/100 kg.


When used in the protection of materials or stored products, the active compound application rate depends on the kind of application area and on the desired effect. Amounts typically applied in the protection of materials are, for example, from 0.001 g to 2 kg, preferably from 0.005 g to 1 kg, of active compound per cubic meter of treated material.


Various types of oils, wetters, adjuvants, herbicides, bactericides, other fungicides and/or pesticides may be added to the active compounds or the compositions comprising them, optionally not until immediately prior to use (tank mix). These compositions can be admixed with the compositions according to the invention in a weight ratio of from 1:100 to 100:1, preferably from 1:10 to 10:1.


The following are particularly suitable as adjuvants in this context: organically modified polysiloxanes, for example Break Thru S 240®; alcohol alkoxylates, for example Atplus® 245, Atplus® MBA 1303, Plurafac® LF 300 and Lutensol® ON 30; EO-PO block polymers, for example Pluronic® RPE 2035 and Genapol® B; alcohol ethoxylates, for example Lutensol® XP 80; and sodium dioctylsulfosuccinate, for example Leophen® RA.


The compositions according to the invention in the application form as fungicides can also be present together with other active compounds, for example with herbicides, insecticides, growth regulators, fungicides or else with fertilizers, as premix or optionally also only immediately prior to use (tank mix).


When mixing the compounds I or the compositions comprising them with one or more further active compounds, in particular fungicides, it is in many cases possible, for example, to widen the activity spectrum or to prevent the development of resistance. In many cases, synergistic effects are obtained.


The following list of active compounds with which the compounds according to the invention can be applied together is meant to illustrate the possible combinations, but not to limit them:

  • A) strobilurins:
    • azoxystrobin, dimoxystrobin, enestroburin, fluoxastrobin, kresoxim-methyl, metominostrobin, orysastrobin, picoxystrobin, pyraclostrobin, pyribencarb, trifloxystrobin, 2-(2-(6-(3-chloro-2-methylphenoxy)-5-fluoropyrimidin-4-yloxy)phenyl)-2-methoxyimino-N-methylacetamide, methyl 2-(ortho-((2,5-dimethylphenyloxymethylene)phenyl)-3-methoxyacrylate, methyl 3-methoxy-2-(2-(N-(4-methoxyphenyl)cyclopropanecarlooximidoylsulfanylmethyl)phenyl)acrylate, 2-(2-(3-(2,6-dichlorophenyl)-1-methylallylideneaminooxymethyl)phenyl)-2-methoxyimino-N-methylacetamide;
  • B) carboxamides:
    • carboxanilides: benalaxyl, benalaxyl-M, benodanil, bixafen, boscalid, carboxin, fenfuram, fenhexamid, flutolanil, furametpyr, isopyrazam, isotianil, kiralaxyl, mepronil, metalaxyl, metalaxyl-M (mefenoxam), ofurace, oxadixyl, oxycarboxin, penflufen (N-(2-(1,3-dimethylbutyl)phenyl)-1,3-dimethyl-5-fluoro-1H-pyrazol-4-carboxamide), penthiopyrad, sedaxane, tecloftalam, thifluzamide, tiadinil, 2-amino-4-methylthiazol-5-carboxanilide, 2-chloro-N-(1,1,3-trimethyl-indan-4-yl)nicotinamide, N-(3′,4′,5′-trifluorobiphenyl-2-yl)-3-difluoromethyl-1-methyl-1H-pyrazol-4-carboxamide, N-(4′-trifluoromethylthiobiphenyl-2-yl)-3-difluoromethyl-1-methyl-1H-pyrazol-4-carboxamide, N-(2-(1,3,3-trimethylbutyl)phenyl)-1,3-dimethyl-5-fluoro-1H-pyrazol-4-carboxamide;
    • carboxylic acid morpholides: dimethomorph, flumorph, pyrimorph;
    • benzamides: flumetover, fluopicolide, fluopyram, zoxamide, N-(3-ethyl-3,5,5-trimethylcyclohexyl)-3-formylamino-2-hydroxybenzamide;
    • other carboxamides: carpropamid, diclocymet, mandipropamid, oxytetracyclin, silthiofam, N-(6-methoxypyridin-3-yl)cyclopropanecarboxamide;
  • C) azoles:
    • triazoles: azaconazole, bitertanol, bromuconazole, cyproconazole, difenoconazole, diniconazole, diniconazole-M, epoxiconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil, oxpoconazole, paclobutrazole, penconazole, propiconazole, prothioconazole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triticonazole, uniconazole, 1-(4-chlorophenyl)-2-([1,2,4]triazol-1-yl)cycloheptanol;
    • imidazoles: cyazofamid, imazalil, imazalil sulfate, pefurazoate, prochloraz, triflumizole;
    • benzimidazoles: benomyl, carbendazim, fuberidazole, thiabendazole;
    • others: ethaboxam, etridiazole, hymexazole, 2-(4-chlorophenyl)-N-[4-(3,4-dimethoxyphenyl)isoxazol-5-yl]-2-prop-2-ynyloxyacetamide;
  • D) nitrogenous heterocyclyl compounds
    • pyridines: fluazinam, pyrifenox, 3-[5-(4-chlorophenyl)-2,3-dimethylisoxazolidin-3-yl]pyridine, 3-[5-(4-methylphenyl)-2,3-dimethylisoxazolidin-3-yl]pyridine, 2,3,5,6-tetrachloro-4-methanesulfonylpyridine, 3,4,5-trichloropyridine-2,6-dicarbonitrile, N-(1-(5-bromo-3-chloropyridin-2-yl)ethyl)-2,4-dichloronicotinamide, N-((5-bromo-3-chloropyridin-2-yl)methyl)-2,4-dichloronicotinamide;
    • pyrimidines: bupirimate, cyprodinil, diflumetorim, fenarimol, ferimzone, mepanipyrim, nitrapyrin, nuarimol, pyrimethanil;
    • piperazines: triforine;
    • pyrroles: fludioxonil, fenpiclonil;
    • morpholines: aldimorph, dodemorph, dodemorph acetate, fenpropimorph, tridemorph;
    • piperidines: fenpropidin;
    • dicarboximides: fluoroimide, iprodione, procymidone, vinclozolin;
    • nonaromatic 5-membered heterocycles: famoxadone, fenamidone, flutianil, octhilinone, probenazole, S-allyl 5-amino-2-isopropyl-3-oxo-4-ortho-tolyl-2,3-dihydropyrazole-1-thiocarboxylate;
    • others: acibenzolar-S-methyl, amisulbrom, anilazine, blasticidin-S, captafol, captan, chinomethionat, dazomet, debacarb, diclomezine, difenzoquat, difenzoquat methylsulfate, fenoxanil, folpet, oxolinic acid, piperalin, proquinazid, pyroquilon, quinoxyfen, triazoxide, tricyclazole, 2-butoxy-6-iodo-3-propylchromen-4-one, 5-chloro-1-(4,6-dimethoxypyrimidin-2-yl)-2-methyl-1H-benzimidazole, 5-chloro-7-(4-methylpiperidin-1-yl)-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine, 5-ethyl-6-octyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-ylamine;
  • E) carbamates and dithiocarbamates
    • thio- and dithiocarbamates: ferbam, mancozeb, maneb, metam, methasulfocarb, metiram, propineb, thiram, zineb, ziram;
    • carbamates: diethofencarb, benthiavalicarb, iprovalicarb, propamocarb, propamocarb hydrochloride, valiphenal, 4-fluorophenyl N-(1-(1-(4-cyanophenyl)ethanesulfonyl)but-2-yl)carbamate;
  • F) other fungicides
    • guanidines: dodine, dodine free base, guazatine, guazatine acetate, iminoctadine, iminoctadine triacetate, iminoctadine tris(albesilate);
    • antibiotics: kasugamycin, kasugamycin hydrochloride hydrate, polyoxins, streptomycin, validamycin A;
    • nitrophenyl derivatives: binapacryl, dicloran, dinobuton, dinocap, nitrothal isopropyl, tecnazene;
    • organometallic compounds: fentin salts, such as, for example, fentin acetate, fentin chloride, fentin hydroxide;
    • sulfur-containing heterocyclyl compounds: dithianon, isoprothiolane;
    • organophosphorus compounds: edifenphos, fosetyl, fosetyl aluminum, iprobenfos, phosphorus acid and its salts, pyrazophos, tolclofos-methyl;
    • organochlorine compounds: chlorothalonil, dichlofluanid, dichlorophen, flusulfamide, hexachlorobenzene, pencycuron, pentachlorophenol and its salts, phthalide, quintozene, thiophanate methyl, tolylfluanid, N-(4-chloro-2-nitrophenyl)-N-ethyl-4-methylbenzenesulfonamide;
    • inorganic active compounds: phosphorus acid and its salts, Bordeaux mixture, copper salts, such as, for example, copper acetate, copper hydroxide, copper oxychloride, basic copper sulfate, sulfur;
    • others: biphenyl, bronopol, cyflufenamid, cymoxanil, diphenylamine, metrafenone, mildiomycin, oxine-copper, prohexadione-calcium, spiroxamine, tolylfluanid, N-(cyclopropylmethoxyimino-(6-difluoromethoxy-2,3-difluorophenyl)methyl)-2-phenylacetamide, N′-(4-(4-chloro-3-trifluoromethylphenoxy)-2,5-dimethylphenyl)-N-ethyl-N-methylformamidine, N′-(4-(4-fluoro-3-trifluoromethylphenoxy)-2,5-dimethylphenyl)-N-ethyl-N-methylformamidine, N′-(2-methyl-5-trifluoromethyl-4-(3-trimethylsilanylpropoxy)phenyl)-N-ethyl-N-methylformamidine, N′-(5-difluoromethyl-2-methyl-4-(3-trimethylsilanylpropoxy)phenyl)-N-ethyl-N-methylformamidine, methyl N-(1,2,3,4-tetrahydronaphthalen-1-yl)-2-{1-[2-(5-methyl-3-trifluoromethylpyrazol-1-yl)acetyl]piperidin-4-yl}thiazole-4-carboxamide, methyl (R)-N-(1,2,3,4-tetrahydronaphthalen-1-yl)-2-{1-[2-(5-methyl-3-trifluoromethylpyrazol-1-yl)acetyl]piperidin-4-yl}thiazole-4-carboxamide, 6-tert-butyl-8-fluoro-2,3-dimethylquinolin-4-ylacetate, 6-tert-butyl-8-fluoro-2,3-dimethylquinolin-4-ylmethoxyacetate, N-methyl-2-{1-[2-(5-methyl-3-trifluoromethyl-1H-pyrazol-1-yl)acetyl]piperidin-4-yl}-N-[(1R)-1,2,3,4-tetrahydronaphthalen-1-yl]-4-thiazolcarboxamide;
  • G) growth regulators
    • abscisic acid, amidochlor, ancymidol, 6-benzylaminopurine, brassinolide, butralin, chlormequat (chlormequat chloride), choline chloride, cyclanilide, daminozide, dikegulac, dimethipin, 2,6-dimethylpuridine, ethephon, flumetralin, flurprimidol, fluthiacet, forchlorfenuron, gibberellic acid, inabenfid, indole-3-acetic acid, maleic hydrazide, mefluidide, mepiquat (mepiquat chloride), metconazole, naphthalene acetic acid, N-6-benzyladenine, paclobutrazole, prohexadione (prohexadione-calcium), prohydrojasmon, thidiazuron, triapenthenol, tributyl phosphorotrithioate, 2,3,5-triiodobenzoic acid, trinexapac-ethyl and uniconazole;
  • H) herbicides
    • acetamides: acetochlor, alachlor, butachlor, dimethachlor, dimethenamid, flufenacet, mefenacet, metolachlor, metazachlor, napropamide, naproanilide, pethoxamid, pretilachlor, propachlor, thenylchlor;
    • amino acid analogs: bilanafos, glyphosate, glufosinate, sulfosate;
    • aryloxyphenoxypropionates: clodinafop, cyhalofop-butyl, fenoxaprop, fluazifop, haloxyfop, metamifop, propaquizafop, quizalofop, quizalofop-p-tefuryl;
    • bipyridyls: diquat, paraquat;
    • carbamates and thiocarbamates: asulam, butylate, carbetamide, desmedipham, dimepiperate, eptam (EPTC), esprocarb, molinate, orbencarb, phenmedipham, prosulfocarb, pyributicarb, thiobencarb, triallate;
    • cyclohexanediones: butroxydim, clethodim, cycloxydim, profoxydim, sethoxydim, tepraloxydim, tralkoxydim;
    • dinitroanilines: benfluralin, ethalfluralin, oryzalin, pendimethalin, prodiamine, trifluralin;
    • diphenyl ethers: acifluorfen, aclonifen, bifenox, diclofop, ethoxyfen, fomesafen, lactofen, oxyfluorfen;
    • hydroxybenzonitriles: bromoxynil, dichlobenil, ioxynil;
    • imidazolinones: imazamethabenz, imazamox, imazapic, imazapyr, imazaquin, imazethapyr;
    • phenoxyacetic acids: clomeprop, 2,4-dichlorophenoxyacetic acid (2,4-D), 2,4-DB, dichlorprop, MCPA, MCPA-thioethyl, MCPB, mecoprop;
    • pyrazines: chioridazon, flufenpyr-ethyl, fluthiacet, norflurazone, pyridate;
    • pyridines: aminopyralid, clopyralid, diflufenican, dithiopyr, fluridone, fluroxypyr, picloram, picolinafen, thiazopyr;
    • sulfonylureas: amidosulfuron, azimsulfuron, bensulfuron, chlorimuron-ethyl, chiorsulfuron, cinosulfuron, cyclosulfamuron, ethoxysulfuron, flazasulfuron, flucetosulfuron, flupyrsulfuron, foramsulfuron, halosulfuron, imazosulfuron, iodosulfuron, mesosulfuron, metsulfuron-methyl, nicosulfuron, oxasulfuron, primisulfuron, prosulfuron, pyrazosulfuron, rimsulfuron, sulfometuron, sulfosulfuron, thifensulfuron, triasulfuron, tribenuron, trifloxysulfuron, triflusulfuron, tritosulfuron, 1-((2-chloro-6-propylimidazo[1,2-b]pyridazin-3-yl)sulfonyl)-3-(4,6-dimethoxypyrimidin-2-yl)urea;
    • triazines: ametryn, atrazine, cyanazine, dimethametryn, ethiozine, hexazinone, metamitron, metribuzin, prometryn, simazine, terbuthylazine, terbutryn, triaziflam;
    • ureas: chlorotoluron, daimuron, diuron, fluometuron, isoproturon, linuron, methabenzthiazuron, tebuthiuron;
    • other inhibitors of acetolactate synthase: bispyribac-sodium, cloransulam-methyl, diclosulam, florasulam, flucarbazone, flumetsulam, metosulam, ortho-sulfamuron, penoxsulam, propoxycarbazone, pyribambenz-propyl, pyribenzoxim, pyriftalid, pyriminobac-methyl, pyrimisulfan, pyrithiobac, pyroxasulfone, pyroxsulam;
    • others: amicarbazone, aminotriazole, anilofos, beflubutamid, benazolin, bencarbazone, benfluresate, benzofenap, bentazone, benzobicyclon, bromacil, bromobutide, butafenacil, butamifos, cafenstrole, carfentrazone, cinidon-ethlyl, chlorthal, cinmethylin, clomazone, cumyluron, cyprosulfamide, dicamba, difenzoquat, diflufenzopyr, Drechslera monoceras, endothal, ethofumesate, etobenzanid, fentrazamide, flumiclorac-pentyl, flumioxazin, flupoxam, fluorochloridone, flurtamone, indanofan, isoxaben, isoxaflutole, lenacil, propanil, propyzamide, quinclorac, quinmerac, mesotrione, methylarsenic acid, naptalam, oxadiargyl, oxadiazon, oxaziclomefone, pentoxazone, pinoxaden, pyraclonil, pyraflufen-ethyl, pyrasulfotol, pyrazoxyfen, pyrazolynate, quinoclamine, saflufenacil, sulcotrione, sulfentrazone, terbacil, tefuryltrione, tembotrione, thiencarbazone, topramezone, 4-hydroxy-3-[2-(2-methoxyethoxymethyl)-6-trifluoromethylpyridine-3-carbonyl]bicyclo[3.2.1]oct-3-en-2-one, ethyl(3-[2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-2H-pyrimidin-1-yl)phenoxy]pyridin-2-yloxy)acetate, methyl 6-amino-5-chloro-2-cyclopropylpyrimidine-4-carboxylate, 6-chloro-3-(2-cyclopropyl-6-methylphenoxy)pyridazin-4-ol, 4-amino-3-chloro-6-(4-chlorophenyl)-5-fluoropyridine-2-carboxylic acid, methyl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylate and methyl 4-amino-3-chloro-6-(4-chloro-3-dimethylamino-2-fluorophenyl)pyridine-2-carboxylate;
  • I) insecticides
    • organo(thio)phosphates: acephate, azamethiphos, azinphos-methyl, chlorpyrifos, chlorpyrifos-methyl, chlorfenvinphos, diazinon, dichlorvos, dicrotophos, dimethoate, disulfoton, ethion, fenitrothion, fenthion, isoxathion, malathion, methamidophos, methidathion, methyl-parathion, mevinphos, monocrotophos, oxydemeton-methyl, paraoxon, parathion, phenthoate, phosalone, phosmet, phosphamidon, phorate, phoxim, pirimiphos-methyl, profenofos, prothiofos, sulprophos, tetrachlorvinphos, terbufos, triazophos, trichlorfon;
    • carbamates: alanycarb, aldicarb, bendiocarb, benfuracarb, carbaryl, carbofuran, carbosulfan, fenoxycarb, furathiocarb, methiocarb, methomyl, oxamyl, pirimicarb, propoxur, thiodicarb, triazamate;
    • pyrethroids: allethrin, bifenthrin, cyfluthrin, cyhalothrin, cyphenothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, zeta-cypermethrin, deltamethrin, esfenvalerate, etofenprox, fenpropathrin, fenvalerate, imiprothrin, lambda-cyhalothrin, permethrin, prallethrin, pyrethrin I and II, resmethrin, silafluofen, tau-fluvalinate, tefluthrin, tetramethrin, tralomethrin, transfluthrin, profluthrin, dimefluthrin,
    • inhibitors of insect growth: a) chitin synthesis inhibitors: benzoylureas: chlorfluazuron, cyromazine, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, teflubenzuron, triflumuron; buprofezin, diofenolan, hexythiazox, etoxazole, clofentazin; b) ecdysone antagonists: halofenozide, methoxyfenozide, tebufenozide, azadirachtin; c) juvenoids: pyriproxyfen, methoprene, fenoxycarb; d) lipid biosynthesis inhibitors: spirodiclofen, spiromesifen, spirotetramate;
    • nicotine receptor agonists/antagonists: clothianidin, dinotefuran, imidacloprid, thiamethoxam, nitenpyram, acetamiprid, thiacloprid, 1-(2-chlorothiazol-5-ylmethyl)-2-nitrimino-3,5-dimethyl-[1,3,5]triazinane;
    • GABA antagonists: endosulfan, ethiprol, fipronil, vaniliprol, pyrafluprol, pyriprol, 5-amino-1-(2,6-dichloro-4-methylphenyl)-4-sulfinamoyl-1H-pyrazole-3-thiocarboxamide;
    • macrocyclic lactones: abamectin, emamectin, milbemectin, lepimectin, spinosad, spinetoram;
    • mitochondrial electron transport chain inhibitor (METI) I acaricides: fenazaquin, pyridaben, tebufenpyrad, tolfenpyrad, flufenerim;
    • METI II and III substances: acequinocyl, fluacyprim, hydramethylnon;
    • decouplers: chlorfenapyr;
    • inhibitors of oxidative phosphorylation: cyhexatin, diafenthiuron, fenbutatin oxide, propargite;
    • insect molting inhibitors: cryomazine;
    • mixed function oxidase inhibitors: piperonyl butoxide;
    • sodium channel blockers: indoxacarb, metaflumizone;
    • others: benclothiaz, bifenazate, cartap, flonicamid, pyridalyl, pymetrozine, sulfur, thiocyclam, flubendiamid, chlorantraniliprol, cyazypyr (HGW86); cyenopyrafen, flupyrazofos, cyflumetofen, amidoflumet, imicyafos, bistrifluron, and pyrifluquinazon.


The present invention relates in particular also to fungicidal compositions which comprise at least one compound of the general formula I and at least one further crop protection active compound, in particular at least one fungicidal active compound, for example one or more, for example 1 or 2, active compounds of groups A) to F) mentioned above and optionally one or more agriculturally suitable carriers. With a view to reducing the application rates, these mixtures are of interest, since many show, at a reduced total amount of active compounds applied, an improved activity against harmful fungi, in particular for certain indications. By simultaneous, joint or separate application of compound(s) I with at least one active compound of groups A) to I), the fungicidal activity can be increased in a superadditive manner.


In the sense of the present application, joint application means that the at least one compound I and the at least one further active compound are present simultaneously at the site of action (i.e. the plant-damaging fungi to be controlled and their habitat, such as infected plants, plant propagation materials, in particular seed, soils, materials or spaces and also the plants, plant propagation materials, in particular seed, soils, materials or spaces to be protected against fungal attack) in an amount sufficient for an effective control of fungal growth. This can be achieved by applying the compounds I and at least one further active compound jointly in a joint active compound preparation or in at least two separate active compound preparations simultaneously, or by applying the active compounds successively to the site of action, the interval between the individual active compound applications being chosen such that the active compound applied first is, at the time of application of the further active compound(s), present at the site of action in a sufficient amount. The order in which the active compounds are applied is of minor importance.


In binary mixtures, i.e. compositions according to the invention comprising a compound I and a further active compound, for example an active compound from groups A) to I), the weight ratio of compound I to the 1st further active compound depends on the properties of the respective active compounds; usually, it is in the range of from 1:100 to 100:1, frequently in the range of from 1:50 to 50:1, preferably in the range of from 1:20 to 20:1, particularly preferably in the range of from 1:10 to 10:1, especially in the range of from 1:3 to 3:1.


In ternary mixtures, i.e. compositions according to the invention comprising an active compound I and a 1st further active compound and a 2nd further active compound, for example two different active compounds from groups A) to I), the weight ratio of compound I to the 1st further active compound depends on the properties of the respective active compounds; preferably, it is in the range of from 1:50 to 50:1 and in particular in the range of from 1:10 to 10:1. The weight ratio of compound I to the 2nd further active compound is preferably in the range of from 1:50 to 50:1, in particular in the range of from 1:10 to 10:1. The weight ratio of 1st further active compound to 2nd further active compound is preferably in the range of from 1:50 to 50:1, in particular in the range of from 1:10 to 10:1.


The components of the composition according to the invention can be packaged and used individually or as a ready-mix or as a kit of parts.


In one embodiment of the invention, the kits may comprise one or more, and even all, components which may be used for preparing an agrochemical composition according to the invention. For example, these kits may comprise one or more fungicide components and/or an adjuvant component and/or an insecticide component and/or a growth regulator component and/or a herbicide. One or more components may be present combined or preformulated with one another. In the embodiments where more than two components are provided in a kit, the components can be present combined with one another and packaged in a single container, such as a vessel, a bottle, a tin, a bag, a sack or a canister. In other embodiments, two or more components of a kit may be packaged separately, i.e. not preformulated or mixed. Kits may comprise one or more separate containers, such as vessels, bottles, tins, bags, sacks or canisters, each container comprising a separate component of the agrochemical composition. The components of the composition according to the invention can be packaged and used individually or as a ready-mix or as a kit of parts. In both forms, a component may be used separately or together with the other components or as a part of a kit of parts according to the invention for preparing the mixture according to the invention.


The user uses the composition according to the invention usually for use in a predosage device, a knapsack sprayer, a spray tank or a spray plane. Here, the agrochemical composition is diluted with water and/or buffer to the desired application concentration, with further auxiliaries being added, if required, thus giving the ready-to-use spray liquor or the agrochemical composition according to the invention. Usually, from 50 to 500 liters of the ready-to-use spray liquor are applied per hectare of agricultural utilized area, preferably from 100 to 400 liters.


According to one embodiment, the user may himself mix individual components, such as, for example, parts of a kit or a two- or three-component mixture of the composition according to the invention in a spray tank and, if required, add further auxiliaries (tank mix).


In a further embodiment, the user may mix both individual components of the composition according to the invention and partially pre-mixed components, for example components comprising compounds I and/or active compounds from groups A) to I), in a spray tank and, if required, add further auxiliaries (tank mix).


In a further embodiment, the user may use both individual components of the composition according to the invention and partially pre-mixed components, for example components comprising compounds I and/or active compounds from groups A) to I), jointly (for example as a tank mix) or in succession.


Preference is given to compositions of a compound I (component 1) with at least one active compound from group A) (component 2) of the strobilurins and in particular selected from the group consisting of azoxystrobin, dimoxystrobin, fluoxastrobin, kresoxim-methyl, orysastrobin, picoxystrobin, pyraclostrobin and trifloxystrobin.


Preference is also given to compositions of a compound I (component 1) with at least one active compound selected from group B) (component 2) of the carboxamides and in particular selected from the group consisting of bixafen, boscalid, isopyrazam, fluopyram, penflufen, penthiopyrad, sedaxane, fenhexamid, metalaxyl, mefenoxam, ofurace, dimethomorph, flumorph, fluopicolide (picobenzamid), zoxamide, carpropamid, mandipropamid and N-(3′,4′,5′-trifluorobiphenyl-2-yl)-3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide.


Preference is also given to compositions of a compound I (component 1) with at least one active compound selected from group C) (component 2) of the azoles and in particular selected from the group consisting of cyproconazole, difenoconazole, epoxiconazole, fluquinconazole, flusilazole, flutriafol, metconazole, myclobutanil, penconazole, propiconazole, prothioconazole, triadimefon, triadimenol, tebuconazole, tetraconazole, triticonazole, prochloraz, cyazofamid, benomyl, carbendazim and ethaboxam.


Preference is also given to compositions of a compound I (component 1) with at least one active compound selected from group D) (component 2) of the nitrogenous heterocyclyl compounds and in particular selected from the group consisting of fluazinam, cyprodinil, fenarimol, mepanipyrim, pyrimethanil, triforin, fludioxonil, fodemorph, fenpropimorph, tridemorph, fenpropidin, iprodione, vinclozolin, famoxadone, fenamidone, probenazole, proquinazid, acibenzolar-S-methyl, captafol, folpet, fenoxanil, quinoxyfen and 5-ethyl-6-octyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-ylamine.


Preference is also given to compositions of a compound I (component 1) with at least one active compound selected from group E) (component 2) of the carbamates and in particular selected from the group consisting of mancozeb, metiram, propineb, thiram, iprovalicarb, benthiavalicarb and propamocarb.


Preference is also given to compositions of a compound I (component 1) with at least one active compound selected from the fungicides of group F) (component 2) and in particular selected from the group consisting of dithianon, fentin salts, such as fentin acetate, fosetyl, fosetyl-aluminum, H3PO3 and salts thereof, chlorothalonil, dichlofluanid, thiophanate-methyl, copper acetate, copper hydroxide, copper oxychloride, copper sulfate, sulfur, cymoxanil, metrafenone, spiroxamine and N-methyl-2-{1-[(5-methyl-3-trifluoromethyl-1H-pyrazol-1-yl)acetyl]piperidin-4-yl}-N-[(1R)-1,2,3,4-tetrahydronaphthalen-1-yl]-4-thiazolcarboxamide.


Accordingly, the present invention furthermore relates to compositions of a compound I (component 1) with a further active compound (component 2), the latter being selected from rows B-1 to B-347 in the column “component 2” of Table B.


A further embodiment of the invention relates to the compositions B-1 to B-347 listed in Table B, where a row of Table B corresponds in each case to an agrochemical composition comprising one of the compounds of the formula I individualized in the present description (component 1) and the respective further active compound from the groups A) to I) (component 2) stated in the row in question. According to one embodiment, the component 1 corresponds to one of the compounds I individualized in Tables 1a to 308a. The active compounds in the described compositions are in each case preferably present in synergistically active amounts.









TABLE B







Active compound composition comprising an individualized compound I and a


further active compound from groups A) to I)









Row
Component 1
Component 2





B-1
an individualized compound I
azoxystrobin


B-2
an individualized compound I
dimoxystrobin


B-3
an individualized compound I
enestroburin


B-4
an individualized compound I
fluoxastrobin


B-5
an individualized compound I
kresoxim-methyl


B-6
an individualized compound I
metominostrobin


B-7
an individualized compound I
orysastrobin


B-8
an individualized compound I
picoxystrobin


B-9
an individualized compound I
pyraclostrobin


B-10
an individualized compound I
pyribencarb


B-11
an individualized compound I
trifloxystrobin


B-12
an individualized compound I
2-(2-(6-(3-chloro-2-methylphenoxy)-




5-fluoropyrimidin-4-yloxy)phenyl)-




2-methoxyimino-N-methylacetamide


B-13
an individualized compound I
2-(ortho-((2,5-dimethylphenyloxy-




methylene)phenyl)-3-methoxyacrylic acid




methyl ester


B-14
an individualized compound I
3-methoxy-2-(2-(N-(4-methoxyphenyl)-




cyclopropanecarboximidoylsulfanyl-




methyl)phenyl)acrylic acid methyl ester


B-15
an individualized compound I
2-(2-(3-(2,6-dichlorophenyl)-1-




methylallylideneaminooxymethyl)phenyl)-




2-methoxyimino-N-methylacetamide


B-16
an individualized compound I
benalaxyl


B-17
an individualized compound I
benalaxyl-M


B-18
an individualized compound I
benodanil


B-19
an individualized compound I
bixafen


B-20
an individualized compound I
boscalid


B-21
an individualized compound I
carboxin


B-22
an individualized compound I
fenfuram


B-23
an individualized compound I
fenhexamid


B-24
an individualized compound I
flutolanil


B-25
an individualized compound I
furametpyr


B-26
an individualized compound I
isopyrazam


B-27
an individualized compound I
isotianil


B-28
an individualized compound I
kiralaxyl


B-29
an individualized compound I
mepronil


B-30
an individualized compound I
metalaxyl


B-31
an individualized compound I
metalaxyl-M


B-32
an individualized compound I
ofurace


B-33
an individualized compound I
oxadixyl


B-34
an individualized compound I
oxycarboxin


B-35
an individualized compound I
penflufen


B-36
an individualized compound I
penthiopyrad


B-37
an individualized compound I
sedaxane


B-38
an individualized compound I
tecloftalam


B-39
an individualized compound I
thifluzamide


B-40
an individualized compound I
tiadinil


B-41
an individualized compound I
2-amino-4-methylthiazole-5-carboxanilide


B-42
an individualized compound I
2-chloro-N-(1,1,3-trimethylindan-4-yl)-




nicotinamide


B-43
an individualized compound I
N-(3′,4′,5′-trifluorobiphenyl-2-yl)-3-




difluoromethyl-1-methyl-1H-pyrazole-4-




carboxamide


B-44
an individualized compound I
N-(4′-trifluoromethylthiobiphenyl-2-yl)-3-




difluoromethyl-1-methyl-1H-pyrazole-4-




carboxamide


B-45
an individualized compound I
N-(2-(1,3,3-trimethylbutyl)phenyl)-1,3-




dimethyl-5-fluoro-1H-pyrazole-4-




carboxamide


B-46
an individualized compound I
dimethomorph


B-47
an individualized compound I
flumorph


B-48
an individualized compound I
pyrimorph


B-49
an individualized compound I
flumetover


B-50
an individualized compound I
fluopicolide


B-51
an individualized compound I
fluopyram


B-52
an individualized compound I
zoxamide


B-53
an individualized compound I
N-(3-ethyl-3,5,5-trimethylcyclohexyl)-




3-formylamino-2-hydroxybenzamide


B-54
an individualized compound I
carpropamid


B-55
an individualized compound I
diclocymet


B-56
an individualized compound I
mandipropamid


B-57
an individualized compound I
oxytetracyclin


B-58
an individualized compound I
silthiofam


B-59
an individualized compound I
N-(6-methoxypyridin-3-yl)cyclopropane-




carboxamide


B-60
an individualized compound I
azaconazole


B-61
an individualized compound I
bitertanol


B-62
an individualized compound I
bromuconazole


B-63
an individualized compound I
cyproconazole


B-64
an individualized compound I
difenoconazole


B-65
an individualized compound I
diniconazole


B-66
an individualized compound I
diniconazole-M


B-67
an individualized compound I
epoxiconazole


B-68
an individualized compound I
fenbuconazole


B-69
an individualized compound I
fluquinconazole


B-70
an individualized compound I
flusilazole


B-71
an individualized compound I
flutriafol


B-72
an individualized compound I
hexaconazole


B-73
an individualized compound I
imibenconazole


B-74
an individualized compound I
ipconazole


B-75
an individualized compound I
metconazole


B-76
an individualized compound I
myclobutanil


B-77
an individualized compound I
oxpoconazole


B-78
an individualized compound I
paclobutrazole


B-79
an individualized compound I
penconazole


B-80
an individualized compound I
propiconazole


B-81
an individualized compound I
prothioconazole


B-82
an individualized compound I
simeconazole


B-83
an individualized compound I
tebuconazole


B-84
an individualized compound I
tetraconazole


B-85
an individualized compound I
triadimefon


B-86
an individualized compound I
triadimenol


B-87
an individualized compound I
triticonazole


B-88
an individualized compound I
uniconazole


B-89
an individualized compound I
1-(4-chlorophenyl)-2-([1,2,4]triazol-1-yl)-




cycloheptanol


B-90
an individualized compound I
cyazofamid


B-91
an individualized compound I
imazalil


B-92
an individualized compound I
imazalil-sulfate


B-93
an individualized compound I
pefurazoate


B-94
an individualized compound I
prochloraz


B-95
an individualized compound I
triflumizole


B-96
an individualized compound I
benomyl


B-97
an individualized compound I
carbendazim


B-98
an individualized compound I
fuberidazole


B-99
an individualized compound I
thiabendazole


B-100
an individualized compound I
ethaboxam


B-101
an individualized compound I
etridiazole


B-102
an individualized compound I
hymexazole


B-103
an individualized compound I
2-(4-chlorophenyl)-N-[4-(3,4-




dimethoxyphenyl)isoxazol-5-yl]-2-prop-2-




ynyloxyacetamide


B-104
an individualized compound I
fluazinam


B-105
an individualized compound I
pyrifenox


B-106
an individualized compound I
3-[5-(4-chlorophenyl)-2,3-dimethyl-




isoxazolidin-3-yl]pyridine


B-107
an individualized compound I
3-[5-(4-methylphenyl)-2,3-




dimethylisoxazolidin-3-yl]pyridine


B-108
an individualized compound I
2,3,5,6-tetrachloro-4-methanesulfonyl-




pyridine


B-109
an individualized compound I
3,4,5-trichloropyridine-2,6-dicarbonitrile


B-110
an individualized compound I
N-(1-(5-bromo-3-chloropyridin-2-yl)ethyl)-




2,4-dichloronicotinamide


B-111
an individualized compound I
N-((5-bromo-3-chloropyridin-2-yl)methyl)-




2,4-dichloronicotinamide


B-112
an individualized compound I
bupirimate


B-113
an individualized compound I
cyprodinil


B-114
an individualized compound I
diflumetorim


B-115
an individualized compound I
fenarimol


B-116
an individualized compound I
ferimzone


B-117
an individualized compound I
mepanipyrim


B-118
an individualized compound I
nitrapyrin


B-119
an individualized compound I
nuarimol


B-120
an individualized compound I
pyrimethanil


B-121
an individualized compound I
triforine


B-122
an individualized compound I
fenpiclonil


B-123
an individualized compound I
fludioxonil


B-124
an individualized compound I
aldimorph


B-125
an individualized compound I
dodemorph


B-126
an individualized compound I
dodemorph acetate


B-127
an individualized compound I
fenpropimorph


B-128
an individualized compound I
tridemorph


B-129
an individualized compound I
fenpropidin


B-130
an individualized compound I
fluoroimide


B-131
an individualized compound I
iprodione


B-132
an individualized compound I
procymidone


B-133
an individualized compound I
vinclozolin


B-134
an individualized compound I
famoxadone


B-135
an individualized compound I
fenamidone


B-136
an individualized compound I
flutianil


B-137
an individualized compound I
octhilinone


B-138
an individualized compound I
probenazole


B-139
an individualized compound I
S-allyl 5-amino-2-isopropyl-4-




orthotolylpyrazol-3-one-1-thiocarboxylate


B-140
an individualized compound I
acibenzolar-S-methyl


B-141
an individualized compound I
amisulbrom


B-142
an individualized compound I
anilazine


B-143
an individualized compound I
blasticidin-S


B-144
an individualized compound I
captafol


B-145
an individualized compound I
captan


B-146
an individualized compound I
chinomethionate


B-147
an individualized compound I
dazomet


B-148
an individualized compound I
debacarb


B-149
an individualized compound I
diclomezine


B-150
an individualized compound I
difenzoquat


B-151
an individualized compound I
difenzoquat methylsulfate


B-152
an individualized compound I
fenoxanil


B-153
an individualized compound I
folpet


B-154
an individualized compound I
oxolinic acid


B-155
an individualized compound I
piperalin


B-156
an individualized compound I
proquinazid


B-157
an individualized compound I
pyroquilon


B-158
an individualized compound I
quinoxyfen


B-159
an individualized compound I
triazoxide


B-160
an individualized compound I
tricyclazole


B-161
an individualized compound I
2-butoxy-6-iodo-3-propylchromen-4-one


B-162
an individualized compound I
5-chloro-1-(4,6-dimethoxypyrimidin-2-yl)-




2-methyl-1H-benzimidazole


B-163
an individualized compound I
5-chloro-7-(4-methylpiperidin-1-yl)-




6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo-




[1,5-a]pyrimidine


B-164
an individualized compound I
5-ethyl-6-octyl-[1,2,4]triazolo[1,5-




a]pyrimidin-7-ylamine


B-165
an individualized compound I
ferbam


B-166
an individualized compound I
mancozeb


B-167
an individualized compound I
maneb


B-168
an individualized compound I
metam


B-169
an individualized compound I
methasulfocarb


B-170
an individualized compound I
metiram


B-171
an individualized compound I
propineb


B-172
an individualized compound I
thiram


B-173
an individualized compound I
zineb


B-174
an individualized compound I
ziram


B-175
an individualized compound I
diethofencarb


B-176
an individualized compound I
benthiavalicarb


B-177
an individualized compound I
iprovalicarb


B-178
an individualized compound I
propamocarb


B-179
an individualized compound I
propamocarb hydrochloride


B-180
an individualized compound I
valiphenal


B-181
an individualized compound I
4-fluorophenyl N-(1-(1-(4-cyanophenyl)-




ethanesulfonyl)but-2-yl)carbamate


B-182
an individualized compound I
dodine


B-183
an individualized compound I
dodine free base


B-184
an individualized compound I
guazatine


B-185
an individualized compound I
guazatine acetate


B-186
an individualized compound I
iminoctadine


B-187
an individualized compound I
iminoctadine triacetate


B-188
an individualized compound I
iminoctadine tris(albesilate)


B-189
an individualized compound I
kasugamycin


B-190
an individualized compound I
kasugamycin hydrochloride hydrate


B-191
an individualized compound I
polyoxin


B-192
an individualized compound I
streptomycin


B-193
an individualized compound I
validamycin A


B-194
an individualized compound I
binapacryl


B-195
an individualized compound I
dicloran


B-196
an individualized compound I
dinobuton


B-197
an individualized compound I
dinocap


B-198
an individualized compound I
nitrothal-isopropyl


B-199
an individualized compound I
tecnazene


B-200
an individualized compound I
fentin salts


B-201
an individualized compound I
dithianon


B-202
an individualized compound I
isoprothiolane


B-203
an individualized compound I
edifenphos


B-204
an individualized compound I
fosetyl, fosetyl aluminum


B-205
an individualized compound I
iprobenfos


B-206
an individualized compound I
phosphorous acid and derivatives


B-207
an individualized compound I
pyrazophos


B-208
an individualized compound I
tolclofos-methyl


B-209
an individualized compound I
chlorothalonil


B-210
an individualized compound I
dichlofluanid


B-211
an individualized compound I
dichlorophen


B-212
an individualized compound I
flusulfamide


B-213
an individualized compound I
hexachlorobenzene


B-214
an individualized compound I
pencycuron


B-215
an individualized compound I
pentachlorophenol and salts


B-216
an individualized compound I
phthalide


B-217
an individualized compound I
quintozene


B-218
an individualized compound I
thiophanate-methyl


B-219
an individualized compound I
tolylfluanid


B-220
an individualized compound I
N-(4-chloro-2-nitrophenyl)-N-ethyl-




4-methylbenzenesulfonamide


B-221
an individualized compound I
Bordeaux mixture


B-222
an individualized compound I
copper acetate


B-223
an individualized compound I
copper hydroxide


B-224
an individualized compound I
copper oxychloride


B-225
an individualized compound I
basic copper sulfate


B-226
an individualized compound I
sulfur


B-227
an individualized compound I
biphenyl


B-228
an individualized compound I
bronopol


B-229
an individualized compound I
cyflufenamid


B-230
an individualized compound I
cymoxanil


B-231
an individualized compound I
diphenylamine


B-232
an individualized compound I
metrafenone


B-233
an individualized compound I
mildiomycin


B-234
an individualized compound I
oxine-copper


B-235
an individualized compound I
prohexadione-calcium


B-236
an individualized compound I
spiroxamine


B-237
an individualized compound I
tolylfluanid


B-238
an individualized compound I
N-(cyclopropylmethoxyimino-(6-difluoro-




methoxy-2,3-difluorophenyl)methyl)-




2-phenylacetamide


B-239
an individualized compound I
N′-(4-(4-chloro-3-trifluoromethylphenoxy)-




2,5-dimethylphenyl)-N-ethyl-N-methyl-




formamidine


B-240
an individualized compound I
N′-(4-(4-fluoro-3-trifluoromethylphenoxy)-




2,5-dimethylphenyl)-N-ethyl-N-methyl-




formamidine


B-241
an individualized compound I
N′-(2-methyl-5-trifluoromethyl-4-(3-tri-




methylsilanylpropoxy)phenyl)-N-ethyl-




N-methylformamidine


B-242
an individualized compound I
N′-(5-difluoromethyl-2-methyl-4-(3-tri-




methylsilanylpropoxy)phenyl)-N-ethyl-




N-methylformamidine


B-243
an individualized compound I
methyl N-(1,2,3,4-tetrahydronaphthalen-




1-yl)-2-{1-[2-(5-methyl-3-trifluoromethyl-




pyrazol-1-yl)acetyl]piperidin-4-yl}thiazole-




4-carboxamide


B-244
an individualized compound I
methyl N—(R)-(1,2,3,4-tetrahydro-




naphthalen-1-yl)-2-{1-[2-(5-methyl-3-




trifluoromethylpyrazol-1-yl)acetyl]-




piperidin-4-yl}thiazole-4-carboxamide


B-245
an individualized compound I
6-tert-butyl-8-fluoro-2,3-dimethylquinolin-




4-yl acetate


B-246
an individualized compound I
6-tert-butyl-8-fluoro-2,3-dimethylquinolin-




4-yl methoxyacetate


B-247
an individualized compound I
N-methyl-2-{1-[(5-methyl-3-




trifluoromethyl-1H-pyrazol-1-yl)-




acetyl]piperidin-4-yl}-N-[(1R)-1,2,3,4-




tetrahydronaphthalen-1-yl)-4-




thiazolecarboxamide


B-248
an individualized compound I
carbaryl


B-249
an individualized compound I
carbofuran


B-250
an individualized compound I
carbosulfan


B-251
an individualized compound I
methomylthiodicarb


B-252
an individualized compound I
bifenthrin


B-253
an individualized compound I
cyfluthrin


B-254
an individualized compound I
cypermethrin


B-255
an individualized compound I
alpha-cypermethrin


B-256
an individualized compound I
zeta-cypermethrin


B-257
an individualized compound I
deltamethrin


B-258
an individualized compound I
esfenvalerate


B-259
an individualized compound I
lambda-cyhalothrin


B-260
an individualized compound I
permethrin


B-261
an individualized compound I
tefluthrin


B-262
an individualized compound I
diflubenzuron


B-263
an individualized compound I
flufenoxuron


B-264
an individualized compound I
lufenuron


B-265
an individualized compound I
teflubenzuron


B-266
an individualized compound I
spirotetramate


B-267
an individualized compound I
clothianidin


B-268
an individualized compound I
dinotefuran


B-269
an individualized compound I
imidacloprid


B-270
an individualized compound I
thiamethoxam


B-271
an individualized compound I
acetamiprid


B-272
an individualized compound I
thiacloprid


B-273
an individualized compound I
endosulfan


B-274
an individualized compound I
fipronil


B-275
an individualized compound I
abamectin


B-276
an individualized compound I
emamectin


B-277
an individualized compound I
spinosad


B-278
an individualized compound I
spinetoram


B-279
an individualized compound I
hydramethylnon


B-280
an individualized compound I
chlorfenapyr


B-281
an individualized compound I
fenbutatin oxide


B-282
an individualized compound I
indoxacarb


B-283
an individualized compound I
metaflumizone


B-284
an individualized compound I
flonicamid


B-285
an individualized compound I
lubendiamid


B-286
an individualized compound I
chlorantraniliprol


B-287
an individualized compound I
cyazypyr (HGW86)


B-288
an individualized compound I
cyflumetofen


B-289
an individualized compound I
acetochlor


B-290
an individualized compound I
dimethenamid


B-291
an individualized compound I
metolachlor


B-292
an individualized compound I
metazachlor


B-293
an individualized compound I
glyphosate


B-294
an individualized compound I
glufosinate


B-295
an individualized compound I
sulfosate


B-296
an individualized compound I
clodinafop


B-297
an individualized compound I
fenoxaprop


B-298
an individualized compound I
fluazifop


B-299
an individualized compound I
haloxyfop


B-300
an individualized compound I
paraquat


B-301
an individualized compound I
phenmedipham


B-302
an individualized compound I
clethodim


B-303
an individualized compound I
cycloxydim


B-304
an individualized compound I
profoxydim


B-305
an individualized compound I
sethoxydim


B-306
an individualized compound I
tepraloxydim


B-307
an individualized compound I
pendimethalin


B-308
an individualized compound I
prodiamine


B-309
an individualized compound I
trifluralin


B-310
an individualized compound I
acifluorfen


B-311
an individualized compound I
bromoxynil


B-312
an individualized compound I
imazamethabenz


B-313
an individualized compound I
imazamox


B-314
an individualized compound I
imazapic


B-315
an individualized compound I
imazapyr


B-316
an individualized compound I
imazaquin


B-317
an individualized compound I
imazethapyr


B-318
an individualized compound I
2,4-dichlorophenoxyacetic acid (2,4-D)


B-319
an individualized compound I
chloridazon


B-320
an individualized compound I
clopyralid


B-321
an individualized compound I
fluroxypyr


B-322
an individualized compound I
picloram


B-323
an individualized compound I
picolinafen


B-324
an individualized compound I
bensulfuron


B-325
an individualized compound I
chlorimuron-ethyl


B-326
an individualized compound I
cyclosulfamuron


B-327
an individualized compound I
iodosulfuron


B-328
an individualized compound I
mesosulfuron


B-329
an individualized compound I
metsulfuron-methyl


B-330
an individualized compound I
nicosulfuron


B-331
an individualized compound I
rimsulfuron


B-332
an individualized compound I
triflusulfuron


B-333
an individualized compound I
atrazine


B-334
an individualized compound I
hexazinone


B-335
an individualized compound I
diuron


B-336
an individualized compound I
florasulam


B-337
an individualized compound I
pyroxasulfone


B-338
an individualized compound I
bentazone


B-339
an individualized compound I
cinidon-ethyl


B-340
an individualized compound I
cinmethylin


B-341
an individualized compound I
dicamba


B-342
an individualized compound I
diflufenzopyr


B-343
an individualized compound I
quinclorac


B-344
an individualized compound I
quinmerac


B-345
an individualized compound I
mesotrione


B-346
an individualized compound I
saflufenacil


B-347
an individualized compound I
topramezone









The active compounds specified above as component 2, their preparation, and their action against harmful fungi are known (cf.: http://www.alanwood.net/pesticides/); they are available commercially. The compounds with IUPAC nomenclature, their preparation, and their fungicidal activity are likewise known (cf. Can. J. Plant Sci. 48(6), 587-94, 1968; EP-A 141 317; EP-A 152 031; EP-A 226 917; EP-A 243 970; EP-A 256 503; EP-A 428 941; EP-A 532 022; EP-A 1 028 125; EP-A 1 035 122; EP-A 1 201 648; EP-A 1 122 244, JP 2002316902; DE 19650197; DE 10021412; DE 102005009458; U.S. Pat. No. 3,296,272; U.S. Pat. No. 3,325,503; WO 98/46608; WO 99/14187; WO 99/24413; WO 99/27783; WO 00/29404; WO 00/46148; WO 00/65913; WO 01/54501; WO 01/56358; WO 02/22583; WO 02/40431; WO 03/10149; WO 03/11853; WO 03/14103; WO 03/16286; WO 03/53145; WO 03/61388; WO 03/66609; WO 03/74491; WO 04/49804; WO 05/120234; WO 05/123689; WO 05/123690; WO 05/63721; WO 05/87772; WO 05/87773; WO 06/15866; WO 06/87325; WO 06/87343; WO 07/82098; WO 07/90624).


The compositions for mixtures of active compounds are prepared in a known manner in the form of compositions comprising, in addition to the active compounds, a solvent or solid carrier, for example in the manner stated for compositions of the compounds I.


With respect to the customary ingredients of such compositions, reference is made to what was said about the compositions comprising the compounds I. The compositions for mixtures of active compounds are suitable as fungicides for controlling harmful fungi. They are distinguished by excellent activity against a broad spectrum of phytopathogenic fungi including soilborne pathogens which originate in particular from the classes of the Plasmodiophoromycetes, Peronosporomycetes (syn. Oomycetes), Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes (syn. Fungi imperfecti). Furthermore, reference is made to what was said about the activity of the compounds I and the compositions comprising the compounds I.


The present invention furthermore provides the use of compounds I and their pharmaceutically acceptable salts for treating diseases, in particular the use of the compounds I as antimycotics. Thus, one embodiment of the invention relates to a medicament comprising at least one compound of the formula I and/or a pharmaceutically acceptable salt thereof. A further embodiment relates to the use of a compound I and/or of a pharmaceutically effective salt thereof for preparing an antimycotic.


The present invention also provides the use of compounds I and their pharmaceutically acceptable salts for treating tumors in mammals such as, for example, humans. Thus, one embodiment of the invention relates to the use of a compound I and/or a pharmaceutically acceptable salt thereof for preparing a composition which inhibits the growth of tumors and cancer in mammals. “Cancer” means in particular a malignant tumor, for example breast cancer, cancer of the prostate, lung cancer, cancer of the CNS, melanocarcinomas, ovarial carcinomas or renal cancer, in particular in humans.


The present invention also provides the use of compounds I and their pharmaceutically acceptable salts for treating virus infections, in particular virus infections leading to diseases in warmblooded animals. Thus, one embodiment of the invention relates to the use of a compound I and/or a pharmaceutically acceptable salt thereof for preparing a composition for treating virus infections. The virus diseases to be treated include retrovirus diseases such as, for example: HIV and HTLV, influenza virus, rhinovirus diseases, herpes and the like.







SYNTHESIS EXAMPLES

With appropriate modification of the starting materials, the procedures given in the synthesis examples below were used to obtain further compounds of the formula I or the precursors thereof, for example for preparing the compounds according to the invention listed in Table E.


Example 1
Synthesis of 7-(2,3-dichlorophenyl)-2,2,6-trimethyl-4-[1,2,4]triazol-1-ylheptan-3-ol (Compound I.A29a, (RR/SS) Stereoisomer)

0.6 g of 7-(2,3-dichlorophenyl)-2,2,6-trimethyl-4-[1,2,4]triazol-1-ylheptan-3-one were dissolved in 10 ml of MeOH. At 0° C., 0.06 g of NaBH4 was then added a little at a time. The mixture was stirred at RT for 12 hours and then added to ammonium chloride solution, and the aqueous phase was extracted three times with EtOAc. The organic phase was washed with water, dried and concentrated. The crude product was purified by column chromatography on silica gel. This gave 0.4 g (66% of theory) of the desired product.


Example 2
Synthesis of 7-(2,4-difluorophenyl)-2,2,6-trimethyl-4-[1,2,4]triazol-1-ylheptan-3-ol ((RS/SR) Stereoisomer)
2.1 Synthesis of 7-(2,4-difluorophenyl)-2,2,6-trimethyl-4-[1,2,4]triazol-1-ylheptan-3-one

A mixture of 7.5 g of 3,3-dimethyl-1-[1,2,4]triazol-1-ylbutan-2-one, 10 g of 1-(3-bromo-2-methylpropyl)-2,4-difluorobenzene, 5 g of finely powdered potassium hydroxide and 1 g of PEG-600 in 120 ml of acetonitrile was heated at 60° C. for two hours. The reaction mixture was then filtered, and the filtrate was concentrated and water and EtOAc were added. The aqueous phase was extracted two more times with EtOAc, and the combined organic phases were washed with saturated sodium chloride solution, dried and concentrated. The crude product was purified by column chromatography on silica gel. This gave 5.3 g (35% of theory) of the desired product.


2.2 Synthesis of 7-(2,4-difluorophenyl)-2,2,6-trimethyl-4-[1,2,4]triazol-1-ylheptan-3-ol ((RS/SR) Stereoisomer)

At −60° C., 0.68 g of a 1 M solution of TiCl4 in CH2Cl2 were added dropwise to a solution of 1 g of 7-(2,4-difluorophenyl)-2,2,6-trimethyl-4-[1,2,4]triazol-1-ylheptan-3-one from step 2.1 in 30 ml of CH2Cl2. The mixture was warmed to RT and stirred at this temperature for 30 minutes. The mixture was then once more cooled to −60° C., and a solution of 0.39 g of tetra-n-butylammonium hydride in 3 ml of CH2Cl2 was added. The mixture was stirred at −60° C. for 4 hours, then carefully hydrolyzed with saturated NH4Cl solution and extracted twice with Ch2Cl2. The organic phase was washed with water, dried and concentrated. The crude product was purified by column chromatography on silica gel. This gave 0.7 g (70% of theory) of the desired product.


Biological Experiments


A) Greenhouse


Active Compound Preparation


The active compounds were prepared separately as a stock solution with 25 mg of active compound, which was made up to 10 ml with a mixture of acetone and/or DMSO and the emulsifier Uniperol® EL (wetting agent with emulsifying and dispersing action based on ethoxylated alkylphenols) in the volume ratio solvent/emulsifier of from 99 to 1. Subsequently, it was made up to 100 ml with water. This stock solution was diluted with the described solvent/emulsifier/water mixture to the active compound concentration indicated below. Alternatively, the active compounds were used as a commercially available ready-to-use solution and diluted with water to the active compound concentration indicated.


Example G1
Activity Against Gray Mold on Bell Pepper Leaves Caused by Botrytis Cinerea, 1 Day Protective Application

Bell pepper seedlings were, after 2-3 leaves were well developed, sprayed to run off point with an aqueous suspension having the active compound concentration stated below. The next day, the treated plants were inoculated with a spore suspension of Botrytis cinerea in a 2% biomalt solution. The test plants were then placed in a dark acclimatized chamber at 22 to 24° C. and high atmospheric humidity. After 5 days, the extent of the fungal infection on the leaves could be determined visually in %. The plants which had been treated with an aqueous active compound preparation comprising 600 ppm of the active compounds I.A30a, I.A26b, I.A30b, I.A25b, I.A28b, I.A27b, I.A29a, I.A28a, I.A27a or I.A24b of Table E showed an infection of at most 15%, whereas the untreated plants were 90% infected.


Example G2
Curative Activity Against Soybean Rust Caused by Phakopsora Pachyrhizi

Leaves of soybean seedlings grown in pots were inoculated with a spore suspension of soybean rust (Phakpsora pachyrhizi). The pots were then placed in a chamber of high atmospheric humidity (90 to 95%) and 23 to 27° C. for 24 hours. During this time, the spores germinated and the germ tubes penetrated into the leaf tissue. The infected plants were then cultivated further in a greenhouse at temperatures between 23 and 27° C. and 60 to 80% relative atmospheric humidity. After two days, the plants were sprayed to run off point with the active compound solution described above at the active compound concentration indicated below. After the spray coating had dried on, the test plants were cultivated in a greenhouse at temperatures between 23 and 27° C. and 60 to 80% relative atmospheric humidity for a further 10 days. The extent of the rust fungus development on the leaves was then determined visually in % infection. The plants which had been treated with an aqueous active compound preparation comprising 600 ppm of the active compounds I.A30a, I.A26b, I.A30b, I.A36b, I.A39a, I.A25b or I.A24b of Table E showed no infection (0%), whereas the untreated plants were 100% infected.


Micro Test


The active compounds were formulated separately as a stock solution having a concentration of 10 000 ppm in DMSO.


Example M1
Activity Against the Septoria Leaf Spot Pathogen Septoria Tritici in the Microtiter Test

The stock solution was pipetted into a microtiter plate (MTP) and diluted with water to the stated active compound concentration. An aqueous malt-based spore suspension of Septoria tritici was then added. The plates were placed in a water vapor-saturated chamber at temperatures of 18° C. Using an absorption photometer, the MTPs were measured at 405 nm on day 7 after the inoculation. The measured parameters were compared to the growth of the active compound-free control variant (100%) and the fungus- and active compound-free blank value to determine the relative growth in % of the pathogens in the individual active compounds. At an active compound concentration of 31 ppm, the active compounds I.A6a/b (mixture), I.A7a/b (mixture), I.A8, I.A14a, I.A10, I.A12a, I.A14b, I.A14a, I.A15a, I.A16a, I.A17a, I.A11b, I.A18b, I.A17b, I.A16b, I.A15b, I.A19a, I.A20a, I.A21a, I.A22a, I.A23a, I.A24a, I.A25a, I.A19b, I.A20b, I.A22b, I.A23b, I.A21b, I.A26a, I.A31a, I.A31b, I.A32, I.A34, I.A37a, I.A9 and I.A38 of Table E led to a growth of at most 14%.


Example M2
Activity Against the Gray Mold Pathogen Botrytis Cinerea in the Microtiter Test

The stock solution was pipetted into a microtiter plate (MTP) and diluted with water to the stated active compound concentration. An aqueous malt-based spore suspension of Botrytis cinerea was then added. The plates were placed in a water vapor-saturated chamber at temperatures of 18° C. Using an absorption photometer, the MTPs were measured at 405 nm on day 7 after the inoculation. The measured parameters were compared to the growth of the active compound-free control variant and the fungus- and active compound-free blank value to determine the relative growth in % of the pathogens in the individual active compounds. At an active compound concentration of 31 ppm, the active compounds I.A6a/b (mixture), I.A14a, I.A10, I.A12a, I.A14b, I.A14a, I.A15a, I.A16a, I.A17a, I.A12b, I.A18b, I.A16b, I.A15b, I.A20a, I.A21a, I.A22a, I.A23a, I.A24a, I.A25a, I.A19b, I.A20b, I.A22b, I.A23b, I.A26a, I.A31a, I.A31b, I.A32, I.A33, I.A34, I.A35a, I.A36a, I.A9 and I.A38 of Table E led to a growth of at most 14%.


Example M3
Activity Against the Rice Blast Pathogen Pyricularia Oryzae in the Microtiter Test

The stock solution was pipetted into a microtiter plate (MTP) and diluted with water to the stated active compound concentration. An aqueous malt-based spore suspension of Pyricularia oryzae was then added. The plates were placed in a water vapor-saturated chamber at temperatures of 18° C. Using an absorption photometer, the MTPs were measured at 405 nm on day 7 after the inoculation. The measured parameters were compared to the growth of the active compound-free control variant (=100%) and the fungus- and active compound-free blank value to determine the relative growth in % of the pathogens in the individual active compounds. At an active compound concentration of 31 ppm, the active compounds I.A5, I.A7a/b (mixture), I.A8, I.A19a, I.A33, I.A35a and I.A36a of Table E led to a growth of at most 13%.


Comparison with the Prior Art


Greenhouse


Active Compound Preparation


The active compounds were prepared separately as a stock solution with 25 mg of active compound, which was made up to 10 ml with a mixture of acetone and/or DMSO and the emulsifier Uniperol® EL (wetting agent with emulsifying and dispersing action based on ethoxylated alkylphenols) in the volume ratio solvent/emulsifier of from 99 to 1. Subsequently, it was made up to 100 ml with water. This stock solution was diluted with the described solvent/emulsifier/water mixture to the active compound concentration indicated below. Alternatively, the active compounds were used as a commercially available ready-to-use solution and diluted with water to the active compound concentration indicated.


C1 Activity Against Late Blight on Tomatoes Caused by Phytophthora Infestans, Protective Treatment

Leaves of potted tomato plants were sprayed to run off point with an aqueous suspension having the active compound concentration stated below. The next day, the leaves were inoculated with an aqueous sporangia suspension of Phytophthora infestans. The plants were then placed in a water vapor-saturated chamber at temperatures between 18 and 20° C. After 6 days, the late blight on the untreated but infected control plants had developed to such an extent that the infection could be determined visually in %.


C2 Activity Against Gray Mold on Bell Pepper Leaves Caused by Botrytis Cinerea, 1 Day Protective Application

Bell pepper seedlings were, after 2-3 leaves were well developed, sprayed to run off point with an aqueous suspension having the active compound concentration stated below. The next day, the treated plants were inoculated with a spore suspension of Botrytis cinerea in a 2% biomalt solution. The test plants were then placed in a dark acclimatized chamber at 22 to 24° C. and high atmospheric humidity. After 5 days, the extent of the fungal infection on the leaves could be determined visually in %.

















Infection (%) at 600 ppm



Structure
C1





















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7









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90







untreated control
90










The tests show that the prior art compound in which R1 is 2,4-dichlorophenyl and Z is CH2CH(CH3)CH2 leads to a considerably higher infection (90%) than the compounds according to the invention in which Z is an unsubstituted alkyl chain, with identical R1 (7%). The result with the prior art compound thus corresponds to the result of the untreated control.

















Infection (%) at 600 ppm



Structure
C2





















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7









embedded image


15









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10









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70







untreated control
100










The tests show that the prior art compound in which R1 is a 4-chlorophenyl leads to a considerably higher infection (70%) than the compounds according to the invention in which R1 is likewise a mono-chloro-substituted phenyl ring, but is 2-chloro- or 3-chlorophenyl (7%, 15% and 10%, respectively).









TABLE E







I.A




embedded image
























Stereochemistry


No.
R1
Z [****]
R2
R3
R4
physical data
















I.A1
4-tert-butylphenyl
CH2CH2CH2
H
H
H
RR/SS








3.928 [**]


I.A2
2-methylphenyl
CH2CH(CH3)CH2
H
H
H
RR/SS








3.705 [**]


I.A3
2-chlorophenyl
CH2CH(CH3)CH2
H
H
H
RR/SS








3.511 [**]


I.A4
2,4-dichlorophenyl
CH2CH(CH2CH3)CH2
H
H
H
RR/SS


I.A5
2,4-dichlorophenyl
CH2CH[(CH2)3CH3]CH2
H
H
H
RR/SS-RS/SR mixture 1:1








4.398 (broad) [**]


I.A6
3,4-dichlorophenyl
CH2CH(CH3)CH2
H
H
H
a) RR/SS








3.782 [**]








b) RS/SR








3.840 [**]








MP 86-88 [***]


I.A7
3,5-dichlorophenyl
CH2CH(CH3)CH2
H
H
H
a) RR/SS








3.846 [**]








b)RS/SR








3.923 [**]


I.A8
4-iso-propylphenyl
CH2CH(CH3)CH2
H
H
H
RR/SS-RS/SR-mixture (1:1)


I.A9
4-iso-propylphenyl
CH(CH3)CH2CH2
H
H
H
RR/SS








3.914 (broad) [**]


I.A10
2,6-difluorphenyl
CH2CH2CH2
H
H
H
RR/SS








3.256 [**]


I.A11
2,4-dichlorophenyl
CH2CH2CH2
H
H
H
a) RR/SS








3.700 [**]








b) RS/SR








3.528 [**]


I.A12
2-fluorphenyl
CH2CH2CH2
H
H
H
a) RR/SS








3.208 [**]








b) RS/SR








3.044 [**]


I.A13
2,4-dichlorophenyl
CH2CH(CH3)CH2
F
H
H
RR/SS


I.A14
2-chlorophenyl
CH2CH2CH2
H
H
H
a) RR/SS








3.378 [**]








b) RS/SR








3.160 [**]


I.A15
2-methylphenyl
CH2CH2CH2
H
H
H
a) RS/SR








3.068 [**]








b) RR/SS








3.210 [**]


I.A16
3-methylphenyl
CH2CH2CH2
H
H
H
a) RS/SR








3.312 [**]








b) RR/SS








3.273 [**]


I.A17
4-methoxyphenyl
CH2CH2CH2
H
H
H
a) RS/SR








3.069 [**]








b) RR/SS








3.005 [**]


I.A18
3-chlorophenyl
CH2CH2CH2
H
H
H
a) RS/SR








3.156 [**]








b) RR/SS








3.265 [**]


I.A19
3,4-difluorphenyl
CH2CH2CH2
H
H
H
a) RR/SS








8.2 (s, 1H), 7.9 (s, 1H), 7.1-6.8 (m,








3H), 4.4 (m, 1H), 3.8 (br s, 1H), 3.4 (s,








1H), 2.5 (m, 2H), 2.2 (m, 1H), 1.8 (m,








1H), 1.5 (m, 1H), 1.3 (m, 1H), 0.7 (s,








9H) [*]








b) RS/SR








3.260 [**]


I.A20
3,5-difluorphenyl
CH2CH2CH2
H
H
H
a) RR/SS








8.2 (s, 1H), 8.0 (s, 1H), 6.5 (m, 3H), 4.5








(m, 1H), 3.6 (br s, 1H), 3.4 (s, 1H), 2.5








(m, 2H), 2.2 (m, 1H), 1.9 (m, 1H), 1.5








(m, 1H), 1.2 (m, 1H), 0.7 (s, 9H) [*]








b) RS/SR








3.228 [**]


I.A21
5-chloro-2-fluorphenyl
CH2CH2CH2
H
H
H
a) RR/SS








3.406 [**]








b) RS/SR








3.517 [**]


I.A22
4-chloro-2-fluorphenyl
CH2CH2CH2
H
H
H
a) RR/SS








3.467 [**]








b) RS/SR








3.571 [**]


I.A23
2,3-dichlorophenyl
CH2CH2CH2
H
H
H
a) RR/SS








3.554 [**]








b) RS/SR








3.660 [**]


I.A24
2,5-difluorphenyl
CH2CH2CH2
H
H
H
a) RR/SS








3.206 [**]








b) RS/SR








3.155 [**]


I.A25
2,3-difluorphenyl
CH2CH2CH2
H
H
H
a) RR/SS








3.230 [**]








b) RS/SR








3.171 [**]


I.A26
2,5-difluorphenyl
CH2CH(CH3)CH2
H
H
H
a) RR/SS








3.392 [**]








b) RS/SR








3.279 [**]


I.A27
3,4-difluorphenyl
CH2CH(CH3)CH2
H
H
H
a) RR/SS








3.356 [**]








b) RS/SR








3.384 [**]


I.A28
3-chloro-5-fluorphenyl
CH2CH(CH3)CH2
H
H
H
a) RR/SS








3.675 [**]








b) RS/SR








3.638 [**]


I.A29
2,3-dichlorophenyl
CH2CH(CH3)CH2
H
H
H
a) RR/SS








3.643 [**]








b) RS/SR








3.685 [**]


I.A30
2,4-difluorphenyl
CH2CH(CH3)CH2
H
H
H
a) RR/SS








3.388 [**]








b) RS/SR








3.319 [**]


I.A31
2-chloro-6-fluorophenyl
CH2CH(CH3)CH2
H
H
H
a)RR/SS








3.415 [**]








b) RS/SR








3.439 [**]


I.A32
3-methylphenyl
CH2CH(CH3)CH2
H
H
H
RS/SR








3.437 [**]


I.A33
4-chlorophenyl
C(CH3)2CH2CH2
H
H
H
RR/SS








3.580 [**]


I.A34
4-fluorophenyl
C(CH3)2CH2CH2
H
H
H
RR/SS








3.378 [**]


I.A35
2,4-difluorophenyl
CH(CH3)CH2CH2
H
H
H
a) RR/SS








3.336 [**]








b) RS/SR








3.310 [**]


I.A36
2-fluorophenyl
CH(CH3)CH2CH2
H
H
H
a) RR/SS








3.236 [**]








b) RS/SR








95 [***]


I.A37
3-chlorophenyl
C(CH3)2CH2CH2
H
H
H
a) RR/SS








3.548 [**]








b) RS/SR








3.548 [**]


I.A38
2-chloro-4-fluorophenyl
CH2CH(CH3)CH2
H
H
H
RR/SS








3.513 [**]


I.A39
3-chlorophenyl
CH2CH(CH3)CH2
H
H
H
a) RR/SS








3.461 [**]








b) RS/SR








3.455 [**]


I.A40
4-chloro-2-fluorophenyl
CH2CH(CH3)CH2
H
H
H
RR/SS








3.551 [**]


I.A41
4-tert-butylcyclohexyl
CH2CH(CH3)CH2
H
H
H
a) RR/SS








4.570 [**]








b) RS/SR








4.590 [**]


I.A42
cyclohexyl
CH2CH2CH2
H
H
H
a) RR/SS-RS/SR mixture








3.689 & 4.402 [**]








b) RR/SS








3.689 [**]


I.A43
4-methylcyclohexyl
CH2CH(CH3)CH2
H
H
H
RR/SS








4.052 [**]


I.A44
cyclohexyl
CH2CH2CH2
H
H
CH3
a) RR/SS








3.724 [**]








b) RS/SR








3.723 [**]


I.A45
cyclohexyl
CH2CH(CH3)CH2
H
H
H
RR/SS








3.853 [**]


I.A46
2-fluorophenyl
CH2CH(CH3)CH2
H
H
H
a) RR/SS








3.278 [**]








b) RS/SR








3.248 [**]


I.A47
2,4-dichlorophenyl
CH2CH(CH3)CH2
H
H
H
RR/SS








107-108 [***]





[*] 1H-NMR (CDCl3)


[**] retention time in min. (HPLC-MS)/m/z (High Performance Liquid Chromatography Mass Spectrometry) HPLC column: RP-18 column (Chromolith Speed ROD from Merck KgaA, Germany) mobile phase: acetonitrile + 0.1% trifluorooacetic acid (TFA)/water + 0.1% TFA in a gradient of from 5:95 to 95:5 over the course of 5 minutes at 40° C. MS: quadrupole electrospray ionization, 80 V (positive mode)


[***] melting point (MP) ° C.


[****] if the chain Z is asymmetrically branched, an analytical separation of the resulting diastereomers is not possible





Claims
  • 1-13. (canceled)
  • 14. A compound of the formula I
  • 15. The compound of claim 14, wherein R2 is hydrogen and R1 is phenyl which contains one substituent L1 and one substituent L2 and may additionally contain one, two or three independently selected substituents L, where L, L1 and L2 are defined as in claim 14, with the proviso that L2 is not chlorine if L1 is chlorine.
  • 16. The compound of claim 14, wherein R1 is phenyl which contains one substituent L1 which is F and one substituent L2 and may additionally contain one, two or three independently selected substituents L, where L2 and L are defined like L in claim 14.
  • 17. The compound of claim 14, wherein R1 is phenyl which contains two, three, four or five substituents L, with the proviso that at most one L is chlorine.
  • 18. The compound of claim 14, wherein R2, R3 and R4 are hydrogen.
  • 19. The compound of claim 14, wherein Z is a group Z1
  • 20. The compound of claim 14, wherein X is N.
  • 21. An active compound composition comprising at least one compound of the formula I as defined in claim 14, and/or a salt thereof and at least one further fungicidally, insecticidally and/or herbicidally active compound.
  • 22. The active compound composition of claim 21, further comprising at least one solid or liquid carrier.
  • 23. A seed treated at least one compound of claim 14, and/or an agriculturally acceptable salt thereof.
  • 24. A method for controlling phytopathogenic fungi wherein the fungi or the materials, plants, the soil or seed to be protected from fungal attack are treated with an effective amount of the compound of claim 14, or an agriculturally acceptable salt thereof.
  • 25. The method of claim 24, wherein R2 is hydrogen and R1 is phenyl which contains one substituent L1 and one substituent L2 and may additionally contain one, two or three independently selected substituents L, where L, L1 and L2 are defined as in claim 14, with the proviso that L2 is not chlorine if L1 is chlorine.
  • 26. The method of claim 24, wherein R1 is phenyl which contains one substituent L1 which is F and one substituent L2 and may additionally contain one, two or three independently selected substituents L, where L2 and L are defined like L in claim 14.
  • 27. The method of claim 24, wherein R1 is phenyl which contains two, three, four or five substituents L, with the proviso that at most one L is chlorine.
  • 28. The method of claim 24, wherein R2, R3 and R4 are hydrogen.
  • 29. The method of claim 24, wherein Z is a group Z1
  • 30. The method of claim 24, wherein X is N.
  • 31. The seed of claim 23, wherein R2 is hydrogen and R1 is phenyl which contains one substituent L1 and one substituent L2 and may additionally contain one, two or three independently selected substituents L, where L, L1 and L2 are defined as in claim 14, with the proviso that L2 is not chlorine if L1 is chlorine.
  • 32. The seed of claim 23, wherein R1 is phenyl which contains one substituent L1 which is F and one substituent L2 and may additionally contain one, two or three independently selected substituents L, where L2 and L are defined like L in claim 14.
  • 33. The seed of claim 23, wherein R1 is phenyl which contains two, three, four or five substituents L, with the proviso that at most one L is chlorine.
Priority Claims (1)
Number Date Country Kind
08164777.8 Sep 2008 EP regional
PCT Information
Filing Document Filing Date Country Kind 371c Date
PCT/EP2009/062129 9/18/2009 WO 00 3/21/2011