TREA

2-Substituted Hydroxylaminopyrimidine, Method for the Production and the Use Thereof in the Form of Pesticides

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  • Patent Application
  • 20090076047
  • Publication Number
    20090076047
  • Date Filed
    September 21, 2006
    18 years ago
  • Date Published
    March 19, 2009
    15 years ago
Information
Abstract
2-Substituted pyrimidines of the formula I,
Description

The present invention relates to 2-substituted pyrimidines of the formula I







where the indices and substituents are as defined below:

  • R1, R11 independently of one another are hydrogen, C1-C8-alkyl, C1-C8-haloalkyl, C2-C8-alkenyl, C2-C8-haloalkenyl, C2-C8-alkynyl, C2-C8-haloalkynyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl; C4-C6-cycloalkenyl or C4-C6-halocycloalkenyl;
    • R1 and R11 together with the atoms to which they are attached may also form a five-, six- or seven-membered saturated or unsaturated heterocycle which may contain a further heteroatom from the group consisting of O, N and S as ring member, where
    • R1 and/or R11 or a heterocycle formed by R1 and R11 may carry one, two, three or four identical or different substituents R2 and/or two substituents attached to adjacent ring atoms may be C1-C6-alkylene, oxy-C2-C4-alkylene or oxy-C1-C3-alkyleneoxy; where R2 is:
    • R2 halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C4-C6-cycloalkenyl, hydroxyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C8-alkenyloxy, C2-C8-alkynyloxy, C3-C6-cycloalkyloxy, C4-C6-cycloalkenyloxy, C1-C6-alkylthio, ═CH2, ═CH(C1-C4-alkyl), ═C(C1-C4-alkyl)2, —C(═O)-A, —C(═O)—O-A, —C(═O)—N(A′)A, C(A′)(═N—OA), N(A′)A, N(A′)-C(═O)-A, N(A″)—C(═O)—N(A′)A, S(═O)m-A, S(═O)m—O-A, S(═O)m—N(A′)A, —Si(C1-C6-alkyl)3 or phenyl, where the phenyl moiety may carry one, two or three radicals independently of one another selected from the group consisting of: halogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C1-C6-haloalkyl, C1-C6-alkoxy, cyano, nitro, —C(═O)-A, —C(═O)—O-A, —C(═O)—N(A′)A, C(A′)(═N—OA), N(A′)A; where m, A, A′ and A″ are:
      • m 0, 1 or 2;
      • A, A′, A″ independently of one another hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C8-cycloalkyl, C3-C8-cycloalkenyl, phenyl, where the organic radicals may be partially or fully halogenated and/or may be mono- or polysubstituted by nitro, cyanato, cyano, C1-C4-alkoxy; A and A′ together with the atoms to which they are attached may also be a five- or six-membered saturated, partially unsaturated or aromatic heterocycle which contains one, two, three or four heteroatoms from the group consisting of O, N and S;
  • R3 is halogen, cyano, azido, C1-C4-alkyl, C1-C4-haloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl, C2-C4-haloalkynyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C1-C4-alkoxy, C3-C4-alkenyloxy, C3-C4-alkynyloxy, C1-C6-alkylthio, di-(C1-C6-alkyl)amino or C1-C6-alkylamino, where the aliphatic and alicyclic groups of the radical definitions of R3 for their part may contain one, two, three or four substituents independently of one another selected from the group consisting of halogen, cyano, nitro, C1-C2-alkoxy and C1-C4-alkoxycarbonyl;
  • R4 is a five- or six-membered saturated, partially unsaturated or aromatic heterocycle which contains one, two, three or four heteroatoms from the group consisting of O, N and S, where R4 may be partially or fully halogenated and/or may carry one, two, three or four identical or different groups Ru:
    • Ru is halogen, cyano, C1-C8-alkyl, C1-C8-haloalkyl, C2-C8-alkenyl, C2-C8-haloalkenyl, C2-C8-alkynyl, C2-C8-haloalkynyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C2-C8-alkenyloxy, C2-C8-alkynyloxy, C4-C6-cycloalkenyl, C3-C6-cycloalkyloxy, C4-C6-cycloalkenyloxy, —C(═O)-A, —C(═O)—O-A, —C(═O)—N(A′)A, C(A′)(═N—OA), N(A′)A, N(A′)-C(═O)-A, N(A″)—C(═O)—N(A′)A, S(═O)m-A, S(═O)m—O-A or S(═O)m—N(A′)A; where m, A, A′, A″ are as defined above;
      • R4 may furthermore be:
      • cyano, C1-C8-alkoxy, (=Z)ORa, C(=Z)NRzRb, C(=Z)NRa—NRzRb,
      • C(=Z)Ra,
      • CRaRb—ORz, CRaRb—NRzRc,
      • ON(═CRaRb), O—C(=Z)Ra,
      • NRaRb′, NRa(C(=Z)Rb), NRa(C(=Z)ORb), NRa(C(=Z)-NRzRb),
      • NRa(N═CRCRb), NRa—NRzRb, NRz—ORa; where
      • Z is O, S, NRd, NORd or N—NRzRc;
    • Rb′ is C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl or C4-C6-cycloalkenyl;
    • Ra, Rb, Rc, Rd independently of one another are hydrogen or have one of the meanings mentioned for Rb′;
    • Rz has the same meanings as Ra and may additionally be —CO—Rd or —COO—Rd;
    • where die aliphatic and alicyclic groups of the radical definitions of Ra, Rb, Rc, Rd, Rb′ and Rz for their part may be partially or fully halogenated and/or may carry one, two, three or four identical or different groups Rw:
    • Rw is halogen, cyano, C1-C8-alkyl, C2-C10-alkenyl, C2-C10-alkynyl, C1-C6-alkoxy, C2-C10-alkenyloxy, C2-C10-alkynyloxy, C3-C6-cycloalkyl, C3-C6-cycloalkenyl, C3-C6-cycloalkoxy, C3-C6-cycloalkenyloxy;
    • and where two of the radicals Ra, Rb, Rc, Rz together with the atoms to which they are attached may form a five- or six-membered saturated, partially unsaturated or aromatic heterocycle which may contain one, two, three or four heteroatoms from the group consisting of O, N and S;







is five- or six-membered heteroaryl which contains one, two, three or four heteroatoms selected from the group consisting of O, N and S, or is phenyl;

  • L is halogen, cyano, cyanato (OCN), C1-C8-alkyl, C1-C8-haloalkyl, C2-C8-alkenyl, C2-C8-haloalkenyl, C2-C8-alkynyl, C2-C8-haloalkynyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C8-alkenyloxy, C2-C8-alkynyloxy, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C4-C6-cycloalkenyl, C3-C6-cycloalkyloxy, C4-C6-cycloalkenyloxy, nitro, —C(═O)-A, —C(═O)—O-A, —C(═O)—N(A′)A, —C(═S)—N(A′)A, C(A′)(═N—OA), N(A′)A, N(A′)-C(═O)-A, N(A″)—C(═O)—N(A′)A, S(═O)m-A, S(═O)m—O-A or S(═O)m—N(A′)A; where m, A, A′, A″ are as defined above;
    • where the aliphatic and alicyclic groups of the radical definitions of L may carry one, two, three or four groups RL:
    • RL is halogen, cyano, C1-C6-alkoxy, C3-C6-cycloalkyl, C2-C8-alkenyloxy, C2-C8-alkynyloxy, C4-C6-cycloalkenyl, C3-C6-cycloalkyloxy, C4-C6-cycloalkenyloxy, —C(═O)-A, —C(═O)—O-A, —C(═O)—N(A′)A, C(A′)(═N—OA), N(A′)A, N(A′)-C(═O)-A, N(A″)—C(═O)—N(A′)A, S(═O)m-A, S(═O)m—O-A or S(═O)m—N(A′)A; where m, A, A′, A″ are as defined above;
  • and
  • n is 1, 2, 3, 4 or 5;


    and agriculturally acceptable salts of the compounds I.


Furthermore, the present invention relates to compositions comprising at least one of the compounds according to the invention, to processes for preparing these compounds, to intermediates for preparing these compounds and to the agriculturally acceptable salts thereof, to the preparation of the intermediates and to the use of the compounds according to the invention for controlling phytopathogenic fungi and for controlling animal pests.


Depending on the substitution pattern, the compounds according to the invention may have one or more centers of chirality, in which case they are present as enantiomer or diastereomer mixtures. The invention provides both the pure enantiomers or diastereomers or rotamers and mixtures thereof. Suitable compounds of the formula (I) also include all possible stereoisomers (cis/trans isomers) and mixtures thereof. The compounds according to the invention can be present in different crystal modifications, which may differ in their biological activity. They also form part of the subject matter of the present invention.


2-substituted pyrimidines having fungicidal action are known from the literature (WO 01/096314, WO 02/074753, WO 03/043993, WO 04/103978).


However, in many cases the action of the abovementioned pyrimidines is not entirely satisfactory. Accordingly, it was an object of the present invention to provide further compounds having fungicidal activity.


Surprisingly, this object is achieved by the 2-substituted pyrimidines according to the invention. Also provided in the context of the present invention are processes for their preparation and compositions comprising them, their use for controlling phytopathogenic fungi and their use for controlling animal pests.


According to the present invention, agriculturally acceptable salts include in particular the salts of those cations and the acid addition salts of those acids whose cations and anions, respectively, have no adverse effect on the pesticidal action of the compounds according to the invention.


Thus, suitable cations are in particular the ions of the alkali metals, preferably sodium and potassium, of the alkaline earth metals, preferably calcium, magnesium and barium, and of the transition metals, preferably manganese, copper, zinc and iron, and also the ammonium ion which, if desired, may bear from one to four (C1-C4)-alkyl substituents and/or one phenyl or benzyl substituent, preferably diisopropylammonium, tetramethylammonium, tetrabutylammonium, trimethylbenzylammonium, and also phosphonium ions, sulfonium ions, preferably tri(C1-C4-alkyl)sulfonium, and sulfoxonium ions, preferably tri(C1-C4-alkyl)sulfoxonium.


Anions of useful acid addition salts are for example chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogenphosphate, hydrogenphosphate, phosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and also the anions of (C1-C4)-alkanoic acids, preferably formate, acetate, propionate and butyrate. They can be formed by reacting the compounds according to the invention with an acid of the corresponding anion, preferably hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.


The compounds according to the invention can be obtained by various routes.


The compounds according to the invention can be prepared, for example, from correspondingly substituted phenylmalonates 2. These are known or obtainable analogously to the known substances.










Using thiourea (3) and a methylating agent or using S-methylisothiourea, phenylmalonates 2 can be converted into the dihydroxypyrimidine derivatives 4 (see Scheme 1). Suitable methylating agents are, for example, methyl iodide, methyl bromide or dimethyl sulfate.


Here, preference is given to using a solvent which is inert under the reaction conditions and in which the reactants are sufficiently soluble. The reaction temperature is preferably between −20° C. and 150° C., with preference between 0° C. and 100° C.


The dihydroxypyrimidines 4 obtainable in this manner can then be halogenated by customary methods, for example chlorinated to give the dichloropyrimidines 5, as illustrated in Scheme 1. For the chlorination, it has been found to be particularly suitable to use phosphorus oxychloride, if appropriate with addition of an amine such as diethylaniline, an amine hydrochloride such as trimethylammonium chloride, or dimethylformamide. It may be advantageous to carry out the reaction at elevated temperature, for example under reflux of the phosphorus oxychloride, to increase the conversion. Bromination may be carried out by known methods using, for example, POBr3.


The dihalopyrimidines formed, such as, for example, dichloropyrimidines 5 (Scheme 1) can then be substituted further by various routes. Here, it has been found that the regioselectivity often depends unexpectedly strongly on the chosen reaction partners and conditions. In the route shown in Scheme 1, the hydroxylamine is attached nucleophilically in the 4-position. Here, it is possible to use both monoalkylated (H—NH—O—R11, as shown in Scheme 1) and dialkylated hydroxylamines (R1—NH—O—R11). Since the latter are frequently not commercially available, it has been found to be expedient to alkylate the compounds 6, if appropriate, to 6a (as shown in Scheme 1). Frequently, it is possible to avoid this by the separate synthesis of the corresponding disubstituted hydroxylamine. A further advantage of the subsequent introduction of the alkyl group is that the pyrimidine radical replaces the protective group which is otherwise in most cases required at the hydroxylamine, so that the synthesis is shortened by this procedure.


The thiolate group (C1-C6-alkylthio, in Scheme 1 shown in an exemplary manner as a methyl group) in the 2-position of the compound 6a is oxidized to the C1-C6-alkylsulfonyl (C1-C6-alkylS[═O]2—) group of the compound 7 and thus converted into a leaving group for further exchange reactions. Hydrogen peroxide or peracids of organic carboxylic acids have been found to be particularly suitable oxidizing agents. However, the oxidation can also be carried out using, for example, selenium dioxide.


For introducing a heterocyclic radical R4 into the 2-position of the compound 7, it may be possible, depending on the nucleophilicity, to use the heterocycle directly (such as, for example, pyrazole, triazole). In these cases, an auxiliary base is generally employed. Heterocyclic substituents can also be introduced via palladium- or nickel-catalysed reactions. Here, the heterocycle carries a suitable organometallic leaving group.


In this manner it is possible, according to Scheme 2, to introduce cyanides (nitriles) into the 2-position of the compound 7, which cyanides can then be converted further by known methods, for example into amides, amidoximes, amidines. Amidoximes 11 or 12, for example, can be prepared from the nitriles 10 and hydroxylamine or O-alkylated hydroxylamines, as shown in an exemplary manner in Scheme.







What was said above also applies to the preparation of compounds in which R3 is an alkyl group. An alkyl group (R3) can be introduced via organometallic compounds of the formula (R3)n-M, where M is, for example, magnesium, zinc or lithium, for example at the stage of the compound 5 (see Scheme 1). Here, it is frequently advantageous to use a transition metal catalyst. Particularly successful here was the use of palladium alkyl- and aryl-phosphine complexes. If R3 is a cyano group or an alkoxy substituent, the radical R3 can be introduced by reaction with alkali metal cyanides or alkali metal alkoxides.


An alternative to the preparation of the compounds 6a is the reaction of a dichloropyrimidine with a hydroxylamine derivative 13 and the subsequent halogenation, for example to the iodine derivative 15 (Scheme 3). The iodination can be carried out with the customary reagents such as, for example, iodosuccinimide. Also suitable is I—Cl. Instead of the iodine atom, it is frequently also possible to use bromine for the subsequent reaction. This is then followed by reaction with a benzene derivative 16 where MT is one of the leaving groups customary for transition metal-catalysed C—C bond formations, such as, for example, boron, zinc, tin or magnesium. Here, the free valencies of these metals are preferably taken up by halogen, in the case of boron preferably by hydroxyl or alkoxy. Suitable catalysts are in particular palladium compounds which may carry mono- or bidentate phosphine ligands.







The present invention furthermore provides intermediates for compounds of the formula I according to the invention, in particular intermediates of the formulae 6a′ and 7′







in which Hal is chlorine or bromine and R1, R11 and Ln have the meanings defined for the compounds of the formula I.


In the definitions of the symbols given for the compounds according to the invention, collective terms were 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, alkoxy, alkylamino, alkoxycarbonyl: saturated straight-chain or branched hydrocarbon radicals having 1 to 4, 6 or 8 carbon atoms, for example C1-C6-alkyl, such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl and 1-ethyl-2-methylpropyl;


haloalkyl: straight-chain or branched alkyl groups having 1 to 2, 4, 6 or 8 carbon atoms (as mentioned above), where some or all of the hydrogen atoms in these groups are replaced by halogen atoms as mentioned above. In one embodiment, the alkyl groups are substituted at least once or completely by a particular halogen atom, preferably fluorine, chlorine or bromine. In a further embodiment, the alkyl groups are partially or fully halogenated by different halogen atoms; in the case of mixed halogen substitutions, the combination of chlorine and fluorine is preferred. Particular preference is given to (C1-C3)-haloalkyl, more preferably (C1-C2)-haloalkyl, such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl or 1,1,1-trifluoroprop-2-yl;


hydroxyalkyl: straight-chain or branched alkyl groups having 1 to 2, 4, 6 or 8 carbon atoms (as mentioned above), where one or more hydrogen atoms are replaced by hydroxyl (OH) groups;


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 furthermore 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 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: alkynyl 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 fluorine, chlorine or bromine;


cycloalkyl and also the cycloalkyl moieties in composite groups: mono- or bicyclic saturated hydrocarbon groups having 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 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 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. According to the invention it may be preferred to use small alkoxy groups, such as (C1-C4)-alkoxy, on the other hand, it may also be preferred to use larger alkoxy groups, such as (C5-C8)-alkoxy. Examples of preferred alkoxy groups are: methoxy, ethoxy, n-propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy or 1,1-dimethylethoxy, pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy or 1-ethyl-2-methylpropoxy;


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 fluorine, chlorine or bromine.


According to the invention it may be preferred to use short-chain haloalkoxy groups, such as (C1-C4)-haloalkoxy, on the other hand, it may also be preferred to use relatively long-chain haloalkoxy groups, such as (C5-C8)-haloalkoxy.


Examples of preferred haloalkoxy radicals are OCH2F, OCHF2, OCF3, OCH2Cl, OCHCl2, OCCl3, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 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-fluoropropoxy, 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-chlorobutoxy, 4-bromobutoxy or nonafluorobutoxy; and also 5-fluoropentoxy, 5-chloropentoxy, 5-bromopentoxy, 5-iodopentoxy, undecafluoropentoxy, 6-fluorohexoxy, 6-chlorohexoxy, 6-bromohexoxy, 6-iodohexoxy or dodecafluorohexoxy;


alkenyloxy: alkenyl as defined above which is attached via an oxygen atom. Preference is given to (C2-C8)-alkenyloxy, more preference to (C3-C6)-alkenyloxy. According to the invention, it may be preferred to use short-chain alkenyloxy radicals, such as (C2-C4)-alkenyloxy, on the other hand, it may also be preferred to use relatively long-chain alkenyloxy groups, such as (C5-C8)-alkenyloxy;


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;


oxyalkylene: alkylene as defined above, preferably with 2 to 4 CH2 groups, where one valency is attached to the skeleton via an oxygen atom. Examples of preferred oxyalkylene radicals are OCH2, OCH2CH2, OCH2CH2CH2 and OCH2(CH2)2CH2;


oxyalkyleneoxy: alkylene as defined above, preferably with 1 to 3 CH2 groups, where both valencies are attached to the skeleton via an oxygen atom. Examples of preferred oxyalkyleneoxy radicals are OCH2O, OCH2CH2O and OCH2CH2CH2O.


Alkylthio: alkyl as defined above which is attached via an S atom.


Alkylsulfinyl: alkyl as defined above which is attached via an SO group.


Alkylsulfonyl: alkyl as defined above which is attached via an S(O)2 group.


Five- or six-membered saturated, partially unsaturated or 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 via a nitrogen atom, if present. 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- or 6-membered saturated or partially unsaturated heterocyclyl which contains one, two or three nitrogen atoms and/or one oxygen or sulfur atom or one or two oxygen and/or sulfur atoms, where the heterocyclyl may be attached via C or N;
    • 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 which may be attached via C or N; or
    • 6-membered heteroaryl which contains one, two, three or four, preferably one, two or three, nitrogen atoms which may be attached via C or N;


5- or 6-membered saturated or partially unsaturated heterocyclyl, which contains one, two or three nitrogen atoms and/or one oxygen or sulfur atom or one or two oxygen and/or sulfur atoms, where the heterocyclyl may be attached via C or N, if present: 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;


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 C or N, if present: 5-membered heteroaryl groups which, in addition to carbon atoms, may carry one to four nitrogen atoms or one to 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 C or N, if present: 6-membered heteroaryl groups which, in addition to carbon atoms, may contain one to four or one to 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 scope of the present invention embraces the (R) and (S) isomers or rotamers and the racemates of compounds according to the invention having chiral centers. The compounds according to the invention may be present in various crystal modifications which may differ in their biological activity. They are likewise provided by the present invention.


With a view to the intended use of the 2-substituted pyrimidines according to the invention, particular preference is given to the following meanings of the substituents, in each case on their own or in combination. The preferred substituents or preferred combinations of substituents apply correspondingly to the precursors of the compounds according to the invention.


Preference is given to compounds according to the invention in which R1 and R11 independently of one another are hydrogen, C1-C8-alkyl, C1-C8-haloalkyl, C2-C8-alkenyl, C2-C8-haloalkenyl, C2-C8-alkynyl, C2-C8-haloalkynyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl; C4-C6-cycloalkenyl or C4-C6-halocycloalkenyl, where R1 and/or R11 may carry one, two, three or four identical or different substituents R2, where R2 is as defined above.


Here, R2 is advantageously halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C4-C6-cycloalkenyl, hydroxyl, C1-C6-alkoxy, C2-C8-alkenyloxy, C3-C6-cycloalkyloxy, —C(═O)-A, —C(═O)—O-A, —C(═O)—N(A′)A, C(A′)(═N—OA), N(A′)A, N(A′)-C(═O)-A, N(A″)—C(═O)—N(A′)A, or phenyl, where the phenyl moiety may carry one, two or three radicals independently of one another selected from the group consisting of: halogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C1-C6-haloalkyl, C1-C6-alkoxy, cyano, nitro, —C(═O)-A, —C(═O)—O-A, —C(═O)—N(A′)A, C(A′)(═N—OA), N(A′)A; where A, A′ and A″ are as defined above and are preferably hydrogen, C1-C6-alkyl, C2-C6-alkenyl or phenyl, where the organic radicals may be partially or fully halogenated and/or substituted by C1-C4-alkoxy; A and A′ together with the atoms to which they are attached may also be a five- or six-membered saturated heterocycle which contains one or two heteroatoms from the group consisting of O, N and S.


More preferably, R1 and R11 independently of one another are C1-C6-alkyl, C1-C6-40 haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C3-C6-cycloalkyl or C3-C6-halocycloalkyl, where R1 and/or R11 may carry one, two, three or four identical or different substituents R2 as defined above.


Also preferably, R1 and R11 independently of one another are C1-C6-alkyl, C3-C6-cycloalkyl, C1-C4-alkyl-C3-C6-cycloalkyl, C3-C6-cycloalkyl-C1-C6-alkyl, di-C1-C4-alkyl-C3-C6-cycloalkyl, C1-C4-alkoxy-C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl or C2-C6-haloalkynyl, where R1 and/or R11 may carry one, two, three or four identical or different substituents R2 as defined above.


Furthermore preferably, R1 and R11 independently of one another are C1-C6-alkyl, C3-C6-cycloalkyl, (C1-C4-alkyl)-C3-C6-cycloalkyl, (C3-C6-cycloalkyl)-C1-C6-alkyl, di-(C1-C4-alkyl)-C3-C6-cycloalkyl, (C1-C4-alkoxy)-C1-C6-alkyl, C2-C6-alkenyl, C1-C6-haloalkyl, C1-C6-hydroxyalkyl or C2-C6-haloalkenyl. More preferably, R1 and R11 independently of one another are C1-C6-alkyl, C3-C6-cycloalkyl, (C1-C4-alkyl)-C3-C6-cycloalkyl, (C3-C6-cycloalkyl)-C1-C6-alkyl, di-(C1-C4-alkyl)-C3-C6-cycloalkyl, (C1-C4-alkoxy)-C1-C6-alkyl, C2-C6-alkenyl, C1-C6-haloalkyl or C2-C6-haloalkenyl. Preference is furthermore given to compounds according to the invention in which R1 and R11 independently of one another are cyclopropylmethyl, cyclopentylmethyl, methyl, ethyl, propyl, isopropyl, 1,2-dimethylpropyl, 1,2,2-trimethylpropyl, 1-methyl-2,2,2-trifluoroethyl or 2,2,2-trifluoroethyl.


Also preferably, R1 and R11 independently of one another are C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl or C3-C6-cycloalkyl.


Especially preferred are compounds according to the invention in which R1 and R11 independently of one another are C1-C6-haloalkyl, C2-C6-alkenyl or C1-C6-alkyl, branched in the a-position. In addition, preference is given to compounds according to the invention in which R1 or R11 is C1-C4-haloalkyl or C3-C6-cycloalkyl-C1-C4-alkyl.


In one embodiment of the present invention, R1 and R11 independently of one another are C1-C4-haloalkyl or C3-C6-cycloalkyl-C1-C4-alkyl or R1 and R11 together form a five-, six- or seven-membered saturated heterocycle which is optionally substituted by one to four R2.


In a further preferred embodiment of the invention, R1 and R11 together form an optionally substituted five-, six- or seven-membered saturated or unsaturated heterocycle which may contain a further heteroatom from the group consisting of O, N and S as ring member. In one embodiment of the invention, the heterocycle contains no further heteroatoms as ring members.


If an unsaturated heterocycle is formed, this is preferably only partially unsaturated. Particularly preferably, R1 and R11 form an optionally substituted saturated five-, six- or seven-membered heterocycle, more preferably an optionally substituted saturated five- or six-membered heterocycle.


If the heterocycle formed by R1 and R11, in particular in the preferred embodiments listed above, is substituted, it contains one, two or three or one, two, three or four independently selected substituents R2, as defined above. Here, particularly preferred substituents R2 are halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C4-C6-cycloalkenyl, hydroxyl, C1-C6-alkoxy, C2-C8-alkenyloxy, C3-C6-cycloalkyloxy, —C(═O)-A, —C(═O)—O-A, —C(═O)—N(A′)A, C(A′)(═N—OA), N(A′)A, N(A′)—C(═O)-A, N(A″)—C(═O)—N(A′)A, or phenyl, where the phenyl moiety may carry one, two or three radicals independently of one another selected from the group consisting of: halogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C1-C6-haloalkyl, C1-C6-alkoxy, cyano, nitro, —C(═O)-A, —C(═O)—O-A, —C(═O)—N(A′)A, C(A′)(═N—OA), N(A′)A; where A, A′ and A″ are as defined above and are preferably independently of one another hydrogen, C1-C6-alkyl, C2-C6-alkenyl or phenyl, where the organic radicals may be partially or fully halogenated and/or substituted by C1-C4-alkoxy; A and A′ together with the atoms to which they are attached may also be a five- or six-membered saturated heterocycle which contains one or two heteroatoms from the group consisting of O, N and S. Particularly preferably, R2 is C1-C6-alkyl or C1-C6-haloalkyl.


Preference is furthermore given to compounds according to the invention in which R3 is halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy, preferably halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy or halomethoxy. Also preferably, R3 is halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl or C1-C4-alkoxy. With particular preference, R3 is C1-C4-alkyl or C1-C4-haloalkyl. Furthermore preferably, R3 is halogen, cyano, C1-C4-alkyl or C1-C4-alkoxy, in particular methyl, cyano, methoxy or halogen, particularly preferably chlorine.


In a preferred embodiment, R4 is a five- or six-membered saturated, partially unsaturated or aromatic heterocycle which contains one, two, three or four heteroatoms from the group consisting of O, N and S, where R4 may be partially or fully halogenated and/or may carry one, two, three or four identical or different groups Ru. Here, the heterocycle may be attached via C or N.


In a further embodiment of the invention, R4 is a five- or six-membered saturated, partially unsaturated or aromatic heterocycle which is attached via nitrogen and which contains one, two, three or four heteroatoms from the group consisting of O, N and S, where R4 may be partially or fully halogenated and/or may carry one, two, three or four identical or different groups Ru or R4 is NRaRb′, NRa(C(=Z)Rb), NRa(C(=Z)ORb), NRa(C(=Z)-NRzRb), NRa(N═CRCRb), NRe—NRzRb or NRz—ORa.


In a further preferred embodiment of the invention, R4 is a five- or six-membered saturated, partially unsaturated or aromatic heterocycle which is attached via carbon and which contains one, two, three or four heteroatoms from the group consisting of O, N and S, where R4 may be partially or fully halogenated and/or may carry one, two, three or four identical or different groups Ru or R4 is cyano, C(=Z)ORa, C(=Z)NRzRb, C(=Z)NRa—NRzRb, C(=Z)Ra, CRaRb—ORz or CRaRb—NRzRc.


In a further preferred embodiment of the invention, R4 is a five- or six-membered saturated, partially unsaturated or aromatic heterocycle which is attached via nitrogen and which contains one, two, three or four heteroatoms from the group consisting of O, N and S, where R4 may be partially or fully halogenated and/or may carry one, two, three or four identical or different groups Ru or R4 is cyano, C(=Z)ORa, C(=Z)NRzRb, C(=Z)NRa—NRzRb, C(=Z)Ra, CRaRb—ORz or CRaRb—NRzRc.


In a further preferred embodiment of the invention, R4 is a five- or six-membered saturated or partially unsaturated heterocycle, which may be partially or fully halogenated and/or may carry one, two, three or four identical or different groups Ru and may be attached via C or N.


In an even further preferred embodiment of the invention, R4 is a five- or six-membered aromatic heterocycle which may be partially or fully halogenated and/or may carry one, two, three or four identical or different groups Ru and may be attached via C or N. Here, R4 is, according to one embodiment of the invention, an optionally substituted five-membered aromatic heterocycle and according to a further embodiment of the invention, an optionally substituted six-membered aromatic heterocycle, each of which may be attached via C or N.


Preference is furthermore given in particular to compounds according to the invention in which R4 is pyrrolyl, pyrazolyl, imidazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, tetrazolyl, oxazolyl, isoxazolyl, 1,3,4-oxadiazolyl, furyl, thienyl, thiazolyl, isothiazolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, 1,2,3-triazinyl, 1,2,4-triazinyl, 1-pyridin(1,2-dihydro)-2-onyl or 1-pyrrolidone. Furthermore preferably, R4 is 1-pyrrolidone, imidazolidinone, isoxazolidinone or oxazolidinone, in particular 2-pyrrolidon-1-yl, imidazolidinon-1-yl, isoxazolidin-3-on-2-yl or oxazolin-2-on-3-yl. Here, the heterocycle may in each case be attached to the pyrimidine ring via C or N and is unsubstituted or substituted by one, two or three substituents Ru. This preference gives both in combination with the broad definition of Ru given in claim 1 and with the following narrower definition of Ru compounds which are preferred according to the invention: halogen, cyano, C1-C8-alkyl, C1-C8-haloalkyl, C1-C6-alkoxy, —C(═O)-A, —C(═O)—O-A, —C(═O)—N(A′)A, C(A′)(═N—OA), N(A′)A, N(A′)-C(═O)-A.


Particular preference is given to compounds I in which R4 is 1-pyrazolyl, 1-[1,2,4]triazolyl, 2-thiazolyl, 2-pyridinyl, 2-pyrimidinyl, 3-pyridazinyl, 1-pyridin(1,2-dihydro)-2-onyl or 1-pyrrolidonyl, where the heterocycle is unsubstituted or substituted by one, two or three substituents Ru. This preference gives both in combination with the broad definition of Ru given in claim 1 and with the following narrower definition of Ru: halogen, cyano, C1-C8-alkyl, C1-C8-haloalkyl, C1-C6-alkoxy, —C(═O)-A, —C(═O)—O-A, —C(═O)—N(A′)A, C(A′)(═N—OA), N(A′)A, N(A′)-C(═O)-A compounds which are preferred according to the invention.


Preference is furthermore given to compounds according to the invention in which R4 is 2-pyridinyl, 3-pyridazinyl, 1-pyridin(1,2-dihydro)-2-onyl or 2-pyrrolidon-1-yl, which radicals are unsubstituted or substituted by one, two or three substituents Ru, as defined above, where Ru is preferably halogen, cyano, C1-C8-alkyl or C1-C8-haloalkyl.


Preference is furthermore given to compounds according to the invention in which R4 is pyrazolyl or [1,2,4]triazolyl, which radicals are unsubstituted or substituted by one, two or three substituents Ru, as defined above, where Ru is preferably halogen, cyano, C1-C8-alkyl or C1-C8-haloalkyl.


Especially preferred are compounds according to the invention in which R4 is 2-pyrimidinyl which is unsubstituted or substituted by one, two or three substituents Ru, as defined above. This preference gives both in combination with the broad definition of Ru given in claim 1 and with the following narrower definition of Ru: halogen, cyano, C1-C8-alkyl, C1-C8-haloalkyl, C1-C6-alkoxy, —C(═O)-A, —C(═O)—O-A, —C(═O)—N(A′)A, C(A′)(═N—OA), N(A′)A, N(A′)-C(═O)-A compounds which are preferred according to the invention, where Ru is furthermore preferably halogen, cyano, C1-C8-alkyl or C1-C8-haloalkyl.


In a further preferred embodiment of the invention, R4 is cyano, C(=Z)ORa, C(=Z)NRzRb, C(=Z)NRa—NRzRb, C(=Z)Ra, CRaRb—ORz, CRaRb—NRzRc, ON(═CRaRb), O—C(=Z)Ra, NRaRb′, NRa(C(=Z)Rb), NRa(C(=Z)ORb), NRa(C(=Z)-NRzRb), NRa(N═CRCRb), NRaNRzRb, NRz—ORa.


In a further preferred embodiment of the invention, R4 is cyano, C(=Z)ORa, C(=Z)NRzRb, C(=Z)NRa—NRzRb, C(=Z)Ra, CRaRb—ORz, CRaRb—NRzRc, ON(═CRaRb) or O—C(=Z)Ra, more preferably cyano, C(=Z)ORa, C(=Z)NRzRb, C(=Z)NRa—NRzRb, C(=Z)Ra, CRaRb—ORz or CRaRb—NRzRc.


Preference is furthermore given to compounds according to the invention in which R4 is cyano, C(═O)NRzRb, C(═NORa)NRzRb, C(═NORb)Ra, C(═N—NRzRb)Ra or CRaRb—NRzRc, ON(═CRaRb), NRa(C(═O)Rb), NRa(C(═O)ORb), NRa(N═CRcRb) or NRz—ORa.


Moreover, preference is given to compounds according to the invention in which R4 is C(=Z)ORa, C(=Z)NRzRb or C(=Z)Ra, where Z is O, NRd or NORd.


Especially preferred are compounds according to the invention in which R4 is C(═O)NH2 or C(═N—OCH3)NH2.


Preference is furthermore given to compounds according to the invention in which R4 is C(═NH)NRzRb and Rz is a substituent —CO—Rd or —COO—Rd.


In the compounds according to the invention,







is five- or six-membered heteroaryl which contains 1, 2, 3 or 4, preferably 1, 2 or 3, heteroatoms selected from the group consisting of O, N and S, or phenyl. In one embodiment, the heteroaryl is attached via C, in a further embodiment via N.


In one embodiment,







is five- or six-membered heteroaryl which contains 1, 2 or 3 heteroatoms selected from the group consisting of O, N and S, particularly preferably

    • 5-membered heteroaryl which contains one, two or three nitrogen atoms or one or two nitrogen atoms and/or a sulfur or oxygen atom, where the heteroaryl may be attached via C or N: 5-membered heteroaryl groups which, in addition to carbon atoms, may contain one to three nitrogen atoms or one or two nitrogen atoms and/or a sulfur or oxygen atom as ring members, for example furyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl (1,2,3-; 1,2,4-triazolyl), 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 or three nitrogen atoms: 6-membered heteroaryl groups which, in addition to carbon atoms, may contain one to three nitrogen atoms as ring members, where the heteroaryl may be attached via C or N: for example pyridine, pyrimidine, pyrazine, pyridazine, 1,2,3-triazine, 1,2,4-triazine, 1,3,5-triazine, 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.


In a further preferred embodiment,







is five-membered heteroaryl which contains 1, 2 or 3 heteroatoms selected from the group consisting of O, N and S. Particular preference is given to pyrazolyl.


In a further preferred embodiment,







is six-membered heteroaryl which contains 1, 2 or 3 nitrogen atoms. Particular preference is given to pyridyl.


According to a further preferred embodiment,







is five-membered heteroaryl which contains 1, 2 or 3 heteroatoms selected from the group consisting of O, N and S, or phenyl, in particular pyrazolyl, pyridyl or phenyl.


In a further preferred embodiment of the invention,







is phenyl.


Especially preferred are 2-substituted pyrimidines according to the invention in which the substituents L (L1 bis L5) independently of one another are as defined below:

  • L is halogen, cyano, methyl, methoxy, —C(═O)—O-A, —C(═O)—N(A′)A, C(A′)(═N—OA), N(A′)A, N(A′)-C(═O)-A,
    • A,A′ independently of one another are hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, phenyl, where the organic radicals may be partially or fully halogenated or may be substituted by C1-C4-alkoxy, or A and A′ together with the atoms to which they are attached are a five- or six-membered saturated heterocycle which contains one or two heteroatoms from the group consisting of O, N and S;


Moreover, preference is given to pyrimidines according to the invention in which group B substituted by Ln is phenyl and is represented by







where # is the point of attachment to the pyridine skeleton and

    • L1 is fluorine, chlorine, CH3 or CF3;
    • L2, L4 independently of one another are hydrogen, CH3 or fluorine;
    • L3 is hydrogen, fluorine, chlorine, bromine, cyano, CH3, SCH3, OCH3, SO2CH3, CO—NH2, CO—NHCH3, CO—NHC2H5, CO—N(CH3)2, NH—C(═O)CH3, N(CH3)—C(═O)CH3 or COOCH3 and
    • L5 is hydrogen, fluorine, chlorine or CH3.


Preference is furthermore given to 2-substituted pyrimidines of the formula I′,







where the indices and substituents are as defined below:

  • R1, R11 independently of one another are C1-C6-alkyl, C3-C6-cycloalkyl, C1-C4-alkyl-C3-C6-cycloalkyl, C3-C6-cycloalkyl-C1-C6-alkyl, di-C1-C4-alkyl-C3-C6-cycloalkyl, C1-C4-alkoxy-C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl or C2-C6-haloalkynyl, where R1 and R11 together may also form a five-, six- or seven-membered saturated or unsaturated heterocycle; where
    • R1 and/or R11 or a heterocycle formed by R1 and R11 may carry one, two, three or four identical or different substituents R2, where R2 is:
    • R2 halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C4-C6-cycloalkenyl, hydroxyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C8-alkenyloxy, C3-C6-cycloalkyloxy, —O(═O)-A, —C(═O)—O-A, —C(═O)—N(A′)A, C(A′)(═N—OA), N(A′)A, N(A′)-C(═O)-A, N(A″)—C(═O)—N(A′)A, or phenyl, where the phenyl moiety may carry one, two or three radicals independently of one another selected from the group consisting of: halogen, C1-C6-alkyl, C2-C6-alkenyl, C3-C6-cycloalkyl, C1-C6-haloalkyl, C1-C6-alkoxy, cyano, nitro, —C(═O)-A, —C(═O)—O-A, —C(═O)—N(A′)A, C(A′)(═N—OA), N(A′)A; where A, A′ and A″ are:
    • A, A′, A″ independently of one another hydrogen, C1-C6-alkyl, C2-C6-alkenyl, phenyl, where the organic radicals may be partially of fully halogenated and/or may be substituted by C1-C4-alkoxy; A and A′ together with the atoms to which they are attached may also be a five- or six-membered saturated heterocycle which contains one or two heteroatoms from the group consisting of C, N and S;
  • R3 is halogen, cyano, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-haloalkoxy or C1-C4-haloalkyl, preferably halogen, cyano, C1-C4-alkyl, C1-C4-alkoxy or C1-C4-haloalkyl;
  • R4 is pyrrolyl, pyrazolyl, imidazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, tetrazolyl, oxazolyl, isoxazolyl, 1,3,4-oxadiazolyl, furyl, thienyl, thiazolyl, isothiazolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, 1,2,3-triazinyl, 1,2,4-triazinyl, 1-pyridin(1,2-dihydro)-2-onyl or 1-pyrrolidonyl, where R4 is unsubstituted or substituted by one, two or three substituents Ru:
    • Ru is halogen, cyano, C1-C8-alkyl, C1-C6-alkoxy, —C(═O)-A, —C(═O)—O-A, —C(═O)—N(A′)A, C(A′)(═N—OA), N(A′)A, N(A′)-C(═O)-A; where A,A′ are as defined above;
    • or
      • cyano, C(═O)NRzRb, C(═O)ORa, C(═NORa)NRzRb, C(═NORb)Ra, C(═N—NRzRb)Ra or CRaRb—NRzRc, ON(═CRaRb), NRa(C(═O)Rb), NRa(C(═O)ORb), NRa(N═CRCRb) or NRz—ORa;
  • L is halogen, cyano, methyl, methoxy, —C(═O)—O-A, —C(═O)—N(A′)A, —C(═S)—N(A′)A, C(A′)(═N—OA), N(A′)A, N(A′)-C(═O)-A; where the aliphatic groups of the radical definitions of L for their part may be partially or fully halogenated;
  • and
  • n is 1, 2 or 3, where at least one substituent L on the phenyl ring is located in the ortho-position to the point of attachment to the pyrimidine skeleton.


Preference is also given to 2-substituted pyrimidines of the formula I′ in which the indices and substituents are as defined below:

  • R1, R11 independently of one another are C1-C6-alkyl, C3-C6-cycloalkyl, C1-C4-alkyl-C3-C6-cycloalkyl, C3-C6-cycloalkyl-C1-C6-alkyl, di-C1-C4-alkyl-C3-C6-cycloalkyl, C1-C4-alkoxy-C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl or C2-C6-haloalkynyl, where R1 and R11 together may also form a five-, six- or seven-membered saturated or unsaturated heterocycle; where
    • R1 and/or R11 or a heterocycle formed by R1 and R11 may carry one, two, three or four identical or different substituents R2, where R2 is:
    • R2 halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C4-C6-cycloalkenyl, hydroxyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C8-alkenyloxy, C3-C6-cycloalkyloxy, —C(═O)-A, —C(═O)—O-A, —C(═O)—N(A′)A, C(A′)(═N—OA), N(A′)A, N(A′)-C(═O)-A, N(A″)—C(═O)—N(A′)A, or phenyl, where the phenyl moiety may carry one, two or three radicals independently of one another selected from the group consisting of: halogen, C1-C6-alkyl, C2-C6-alkenyl, C3-C6-cycloalkyl, C1-C6-haloalkyl, C1-C6-alkoxy, cyano, nitro, —C(═O)-A, —C(═O)—O-A, —C(═O)—N(A′)A, C(A′)(═N—OA), N(A′)A; where A, A′ and A″ are:
    • A, A′, A″ independently of one another hydrogen or C1-C6-alkyl which may be partially or fully halogenated and/or may be substituted by C1-C4-alkoxy;
  • R3 is halogen, cyano, C1-C4-alkyl, C1-C4-alkoxy, halogenmethoxy or C1-C4-haloalkyl;
  • R4 is pyrazolyl, 1,2,3-triazolyl or 1,2,4-triazolyl, where R4 is attached to the pyrimidine ring via N and is unsubstituted or substituted by one or two substituents Ru:
    • Ru is halogen, cyano, C1-C4-alkyl, C1-C4-alkoxy, —C(═O)—O-A, —C(═O)—N(A′)A, C(A′)(═N—OA), N(A′)A, N(A′)-C(═O)-A; where A,A′ are as defined above;
  • R4 may furthermore be:
    • C(═O)NRzRb, C(═O)ORa, C(═NORa)NH2, C(═NORb)Ra or NRa(C(═O)ORb); where
      • Ra, Rb, Rc, Rd independently of one another are hydrogen, C1-C6-alkyl, or C3-C6-cycloalkyl;
      • Rz has the same meanings as Ra and may additionally be —CO—Rd or —COO—Rd
  • L is halogen, cyano, methyl, methoxy, —C(═O)—O-A, —C(═O)—N(A′)A, —C(═S)—N(A′)A, C(A′)(═N—OA), N(A′)A, N(A′)-C(═O)-A; where A and A′ are as defined above;
  • and
  • n is 1, 2 or 3, where at least one substituent L on the phenyl ring is located in the ortho-position to the point of attachment to the pyrimidine skeleton.


Preference is also given to 2-substituted pyrimidines of the formula I′







in which the indices and substituents are as defined below:

  • R1, R11 independently of one another are hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, where only one of the two radicals may be hydrogen and R1 and R11 together may also form a five-, six- or seven-membered saturated heterocycle;
  • R3 is halogen, cyano, C1-C4-alkyl, C1-C4-alkoxy or C1-C4-haloalkyl;
  • R4 is pyrrolyl, pyrazolyl, imidazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, tetrazolyl, oxazolyl, isoxazolyl, 1,3,4-oxadiazolyl, furyl, thienyl, thiazolyl, isothiazolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, 1,2,3-triazinyl, 1,2,4-triazinyl, 1-pyridin(1,2-dihydro)-2-onyl or 1-pyrrolidonyl (in particular 2-pyrrolidon-1-yl), where R4 is unsubstituted or substituted by one, two or three identical or different substituents Ru:
    • Ru is halogen, cyano, C1-C8-alkyl, C1-C6-alkoxy, —C(═O)-A, —C(═O)—O-A, —C(═O)—N(A′)A, C(A′)(═N—OA), N(A′)A, N(A′)-C(═O)-A,
    • R4 may furthermore be:
    • cyano, C(═O)NRzRb, C(═NORa)NRzRb, C(═NORb)Ra, C(═N—NRzRb)Ra or CRaRb—NRzRc, ON(═CRaRb), NRa(C(═O)Rb), NRa(C(═O)ORb), NRa(N═CRCRb) or NRz—ORa;
  • L is halogen, cyano, methyl, methoxy, —C(═O)—O-A, —C(═O)—N(A′)A, C(A′)(═N—OA), N(A′)A, N(A′)-C(═O)-A, where
    • A,A′ independently of one another are hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, phenyl, where the organic radicals may be partially or fully halogenated and/or substituted by C1-C4-alkoxy; A and A′ together with the atoms to which they are attached may also be a five- or six-membered saturated heterocycle which contains one or two heteroatoms from the group consisting of O, N and S;
    • where the aliphatic groups of the radical definitions of L for their part may be partially or fully halogenated;
  • n is 1, 2 or 3, where at least one substituent L on the phenyl ring is located in the ortho-position to the point of attachment to the pyrimidine skeleton.


Particular preference is also given to 2-substituted pyrimidines of the formula I″







where the substituents are as defined below:

  • R1, R11 independently of one another are C1-C6-alkyl, C3-C6-cycloalkyl-C1-C4-alkyl or C1-C6-haloalkyl; R1 and R11 together may also form a five-, six- or seven-membered saturated heterocycle; where the heterocycle may carry one, two, three or four identical or different substituents R2, as defined above;
  • R3 is halogen;
  • R4 is pyrazolyl, 1,2,4-triazolyl, C(═N—OCH3)NH2 or CONH2;
  • L1 is chlorine or fluorine;
  • L3 is fluorine;
  • L5 is hydrogen or fluorine;


    especially preferred are compounds of the formula I″ in which the substituents are as defined below:
  • R1, R11 independently of one another are ethyl, propyl, isopropyl, 1,2-dimethylpropyl, 1,2,2-trimethylpropyl, 1-methyl-2,2,2-trifluorethyl or 2,2,2-trifluorethyl;
  • R3 is fluorine or chlorine;
  • R4 is pyrazolyl, 1,2,4-triazolyl, C(═N—OCH3)NH2 or CONH2;
  • L1 is chlorine or fluorine;
  • L2 is fluorine;
  • L5 is hydrogen or fluorine


In particular with respect to their use, particular preference is given to the compounds, shown below, of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix where the substituents R1, R11, R3 and Ln have the meanings defined further above for compounds of the formulae I, I′ and/or I″. Especially preferred here are those compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix according to the invention in which the substituents R1, R11, R3 and/or Ln have the preferred meanings given for compounds of the formulae I, I′ and/or I″.


Especially preferred compounds in accordance with the present invention are the compounds I compiled in the tables below (Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix). Here, the groups mentioned in the tables for a substituent are furthermore, independently of the combination in which they are mentioned, a particularly preferred embodiment of the substituent in question.
















Table 1

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2-fluoro,6-chloro, R3 is methyl and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 2

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2,6-difluoro, R3 is methyl and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 3

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2,6-dichloro, R3 is methyl and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 4

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2-fluoro,6-methyl, R3 is methyl and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 5

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2,4,6-trifluoro, R3 is methyl and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 6

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2-methyl,4-fluoro, R3 is methyl and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 7

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2-fluoro,4-methoxycarbonyl, R3 is methyl and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 8

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2-fluoro,4-CN, R3 is methyl and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 9

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2,4,5-trifluoro, R3 is methyl and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 10

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2,4-dichloro, R3 is methyl and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 11

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2-chloro, R3 is methyl and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 12

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2-fluoro, R3 is methyl and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 13

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2,4-difluoro, R3 is methyl and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 14

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2-fluoro-4-chloro, R3 is methyl and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 15

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2-chloro-4-fluoro, R3 is methyl and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 16

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2-chloro-5-fluoro, R3 is methyl and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 17

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2,3-difluoro, R3 is methyl and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 18

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2,5-difluoro, R3 is methyl and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 19

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2,3,4-trifluoro, R3 is methyl and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 20

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2-methyl, R3 is methyl and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 21

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2,4-dimethyl, R3 is methyl and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 22

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and ix in which Ln is 2-methyl-4-chloro, R3 is methyl and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 23

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2-fluoro-4-methyl, R3 is methyl and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 24

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2,6-dimethyl, R3 is methyl and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 25

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2,4,6-trimethyl, R3 is methyl and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 26

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2,6-difluoro-4-cyano, R3 is methyl and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 27

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2,6-difluoro-4-methyl, R3 is methyl and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 28

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2,6-difluoro-4-methoxycarbonyl, R3 is methyl and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 29

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2-chloro,4-methoxy, R3 is methyl and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 30

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2-chloro,4-methyl, R3 is methyl and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 31

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2-chloro,4-methoxycarbonyl, R3 is methyl and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 32

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2-chloro,4-bromo, R3 is methyl and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 33

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2-chloro,4-cyano, R3 is methyl and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 34

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2,6-difluoro,4-methoxy, R3 is methyl and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 35

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2-fluoro,3-methyl, R3 is methyl and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 36

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2,5-dimethyl, R3 is methyl and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 37

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2-methyl,4-cyano, R3 is methyl and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 38

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2-methyl,4-bromo, R3 is methyl and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 39

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2-methyl,5-fluoro, R3 is methyl and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 40

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2-methyl,4-methoxy, R3 is methyl and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 41

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2-methyl,4-methoxycarbonyl, R3 is methyl and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 42

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2,5-dimethyl,4-bromo, R3 is methyl and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 43

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2-fluoro,4-bromo, R3 is methyl and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 44

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2-fluoro,4-methoxy, R3 is methyl and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 45

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2-fluoro,5-methyl, R3 is methyl and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 46

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is pentafluoro, R3 is methyl and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 47

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2-fluoro,6-chloro, R3 is chlorine and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 48

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2,6-difluoro, R3 is chlorine and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 49

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2,6-dichloro, R3 is chlorine and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 50

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2-fluoro,6-methyl, R3 is chlorine and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 51

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2,4,6-trifluoro, R3 is chlorine and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 52

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2-methyl,4-fluoro, R3 is chlorine and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 53

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2-fluoro,4-methoxycarbonyl, R3 is chlorine and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 54

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2-fluoro,4-CN, R3 is chlorine and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 55

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2,4,5-trifluoro, R3 is chlorine and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 56

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2,4-dichloro, R3 is chlorine and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 57

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2-chloro, R3 is chlorine and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 58

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2-fluoro, R3 is chlorine and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 59

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2,4-difluoro, R3 is chlorine and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 60

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2-fluoro-4-chloro, R3 is chlorine and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 61

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2-chloro-4-fluoro, R3 is chlorine and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 62

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2-chloro-5-fluoro, R3 is chlorine and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 63

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2,3-difluoro, R3 is chlorine and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 64

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2,5-difluoro, R3 is chlorine and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 65

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2,3,4-trifluoro, R3 is chlorine and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 66

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2-methyl, R3 is chlorine and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 67

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2,4-dimethyl, R3 is chlorine and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 68

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2-methyl-4-chloro, R3 is chlorine and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 69

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2-fluoro-4-methyl, R3 is chlorine and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 70

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2,6-dimethyl, R3 is chlorine and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 71

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2,4,6-trimethyl, R3 is chlorine and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 72

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2,6-difluoro-4-cyano, R3 is chlorine and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 73

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2,6-difluoro-4-methyl, R3 is chlorine and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 74

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2,6-difluoro-4-methoxycarbonyl, R3 is chlorine and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 75

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2-chloro,4-methoxy, R3 is chlorine and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 76

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2-chloro,4-methyl, R3 is chlorine and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 77

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2-chloro,4-methoxycarbonyl, R3 is chlorine and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 78

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2-chloro,4-bromo, R3 is chlorine and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 79

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2-chloro,4-cyano, R3 is chlorine and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 80

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2,6-difluoro,4-methoxy, R3 is chlorine and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 81

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2-fluoro,3-methyl, R3 is chlorine and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 82

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2,5-dimethyl, R3 is chlorine and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 83

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2-methyl,4-cyano, R3 is chlorine and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 84

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2-methyl,4-bromo, R3 is chlorine and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 85

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2-methyl,5-fluoro, R3 is chlorine and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 86

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2-methyl,4-methoxy, R3 is chlorine and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 87

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2-methyl,4-methoxycarbonyl, R3 is chlorine and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 88

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2,5-dimethyl,4-bromo, R3 is chlorine and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 89

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2-fluoro,4-bromo, R3 is chlorine and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 90

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2-fluoro,4-methoxy, R3 is chlorine and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 91

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2-fluoro,5-methyl, R3 is chlorine and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 92

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is pentafluoro, R3 is chlorine and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 93

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2-fluoro,6-chloro, R3 is methoxy and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 94

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2,6-difluoro, R3 is methoxy and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 95

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2,6-dichloro, R3 is methoxy and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 96

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2-fluoro,6-methyl, R3 is methoxy and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 97

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2,4,6-trifluoro, R3 is methoxy and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 98

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2-methyl,4-fluoro, R3 is methoxy and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 99

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2-fluoro,4-methoxycarbonyl, R3 is methoxy and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 100

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2-fluoro,4-CN, R3 is methoxy and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 101

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2,4,5-trifluoro, R3 is methoxy and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 102

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and ix in which Ln is 2,4-dichloro, R3 is methoxy and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 103

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2-chloro, R3 is methoxy and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 104

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2-fluoro, R3 is methoxy and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 105

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2,4-difluoro, R3 is methoxy and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 106

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2-fluoro-4-chloro, R3 is methoxy and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 107

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2-chloro-4-fluoro, R3 is methoxy and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 108

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2-chloro-5-fluoro, R3 is methoxy and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 109

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2,3-difluoro, R3 is methoxy and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 110

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2,5-difluoro, R3 is methoxy and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 111

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2,3,4-trifluoro, R3 is methoxy and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 112

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2-methyl, R3 is methoxy and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 113

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2,4-dimethyl, R3 is methoxy and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 114

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2-methyl-4-chloro, R3 is methoxy and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 115

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2-fluoro-4-methyl, R3 is methoxy and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 116

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2,6-dimethyl, R3 is methoxy and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 117

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2,4,6-trimethyl, R3 is methoxy and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 118

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2,6-difluoro-4-cyano, R3 is methoxy and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 119

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2,6-difluoro-4-methyl, R3 is methoxy and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 120

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2,6-difluoro-4-methoxycarbonyl, R3 is methoxy and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 121

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2-chloro,4-methoxy, R3 is methoxy and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 122

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2-chloro,4-methyl, R3 is methoxy and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 123

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, it, Iu, Iv, Iw and Ix in which Ln is 2-chloro,4-methoxycarbonyl, R3 is methoxy and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 124

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2-chloro,4-bromo, R3 is methoxy and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 125

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2-chloro,4-cyano, R3 is methoxy and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 126

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2,6-difluoro,4-methoxy, R3 is methoxy and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 127

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2-fluoro,3-methyl, R3 is methoxy and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 128

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, IU, Iv, Iw and Ix in which Ln is 2,5-dimethyl, R3 is methoxy and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 129

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2-methyl,4-cyano, R3 is methoxy and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 130

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2-methyl,4-bromo, R3 is methoxy and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 131

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2-methyl,5-fluoro, R3 is methoxy and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 132

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2-methyl,4-methoxy, R3 is methoxy and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 133

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2-methyl,4-methoxycarbonyl, R3 is methoxy and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 134

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2,5-dimethyl,4-bromo, R3 is methoxy and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 135

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2-fluoro,4-bromo, R3 is methoxy and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 136

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2-fluoro,4-methoxy, R3 is methoxy and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 137

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2-fluoro,5-methyl, R3 is methoxy and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 138

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is pentafluoro, R3 is methoxy and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 139

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2-fluoro,6-chloro, R3 is cyano and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 140

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2,6-difluoro, R3 is cyano and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 141

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2,6-dichloro, R3 is cyano and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 142

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2-fluoro,6-methyl, R3 is cyano and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 143

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2,4,6-trifluoro, R3 is cyano and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 144

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2-methyl,4-fluoro, R3 is cyano and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 145

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2-fluoro,4-methoxycarbonyl, R3 is cyano and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 146

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2-fluoro,4-CN, R3 is cyano and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 147

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2,4,5-trifluoro, R3 is cyano and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 148

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2,4-dichloro, R3 is cyano and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 149

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2-chloro, R3 is cyano and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 150

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2-fluoro, R3 is cyano and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 151

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2,4-difluoro, R3 is cyano and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 152

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2-fluoro-4-chloro, R3 is cyano and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 153

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2-chloro-4-fluoro, R3 is cyano and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 154

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2-chloro-5-fluoro, R3 is cyano and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 155

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2,3-difluoro, R3 is cyano and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 156

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2,5-difluoro, R3 is cyano and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 157

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2,3,4-trifluoro, R3 is cyano and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 158

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2-methyl, R3 is cyano and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 159

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2,4-dimethyl, R3 is cyano and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 160

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2-methyl-4-chloro, R3 is cyano and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 161

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2-fluoro-4-methyl, R3 is cyano and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 162

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2,6-dimethyl, R3 is cyano and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 163

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2,4,6-trimethyl, R3 is cyano and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 164

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2,6-difluoro-4-cyano, R3 is cyano and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 165

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2,6-difluoro-4-methyl, R3 is cyano and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 166

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2,6-difluoro-4-methoxycarbonyl, R3 is cyano and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 167

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2-chloro,4-methoxy, R3 is cyano and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 168

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2-chloro,4-methyl, R3 is cyano and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 169

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2-chloro,4-methoxycarbonyl, R3 is cyano and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 170

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2-chloro,4-bromo, R3 is cyano and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 171

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2-chloro,4-cyano, R3 is cyano and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 172

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2,6-difluoro,4-methoxy, R3 is cyano and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 173

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2-fluoro,3-methyl, R3 is cyano and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 174

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2,5-dimethyl, R3 is cyano and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 175

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2-methyl,4-cyano, R3 is cyano and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 176

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2-methyl,4-bromo, R3 is cyano and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 177

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2-methyl,5-fluoro, R3 is cyano and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 178

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2-methyl,4-methoxy, R3 is cyano and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 179

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2-methyl,4-methoxycarbonyl, R3 is cyano and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 180

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2,5-dimethyl,4-bromo, R3 is cyano and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 181

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2-fluoro,4-bromo, R3 is cyano and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 182

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2-fluoro,4-methoxy, R3 is cyano and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 183

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is 2-fluoro,5-methyl, R3 is cyano and R1 and R11 for a compound corresponds in each case to one row of Table A


Table 184

Compounds of the formulae Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, IL, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw and Ix in which Ln is pentafluoro, R3 is cyano and R1 and R11 for a compound corresponds in each case to one row of Table A











TABLE A





No.
R1
R11







A-1
CH2CH3
CH3


A-2
CH2CH2CH3
CH3


A-3
CH2CH2F
CH3


A-4
CH3
CH3


A-5
H
CH3


A-6
CH(CH3)2
CH3


A-7
CH2C(CH3)3
CH3


A-8
CH2CH(CH3)2
CH3


A-9
(±)CH(CH2CH3)CH3
CH3


A-10
(R)CH(CH2CH3)CH3
CH3


A-11
(S)CH(CH2CH3)CH3
CH3


A-12
(±)CH(CH3)—CH(CH3)2
CH3


A-13
(R)CH(CH3)—CH(CH3)2
CH3


A-14
(S)CH(CH3)—CH(CH3)2
CH3


A-15
(±)CH(CH3)—C(CH3)3
CH3


A-16
(R)CH(CH3)—C(CH3)3
CH3


A-17
(S)CH(CH3)—C(CH3)3
CH3


A-18
(±)CH(CH3)—CF3
CH3


A-19
(R)CH(CH3)—CF3
CH3


A-20
(S)CH(CH3)—CF3
CH3


A-21
(±)CH(CH3)—CCl3
CH3


A-22
(R)CH(CH3)—CCl3
CH3


A-23
(S)CH(CH3)—CCl3
CH3


A-24
CH2C(CH3)═CH2
CH3


A-25
cyclopentyl
CH3


A-26
cyclohexyl
CH3


A-27
(CH2)3CH3
CH3


A-28
C(CH3)3
CH3


A-29
(CH2)4CH3
CH3


A-30
CH(CH2CH3)2
CH3


A-31
CH2CH2CH(CH3)2
CH3


A-32
(±)CH(CH3)(CH2)2CH3
CH3


A-33
(R)CH(CH3)(CH2)2CH3
CH3


A-34
(S)CH(CH3)(CH2)2CH3
CH3


A-35
(±)CH2CH(CH3)CH2CH3
CH3


A-36
(R)CH2CH(CH3)CH2CH3
CH3


A-37
(S)CH2CH(CH3)CH2CH3
CH3


A-38
(±)CH(CH3)CH(CH3)2
CH3


A-39
(R)CH(CH3)CH(CH3)2
CH3


A-40
(S)CH(CH3)CH(CH3)2
CH3


A-41
(CH2)5CH3
CH3


A-42
(±,±)CH(CH3)CH(CH3)CH2CH3
CH3


A-43
(±,R)CH(CH3)CH(CH3)CH2CH3
CH3


A-44
(±,S)CH(CH3)CH(CH3)CH2CH3
CH3


A-45
(±)CH2CH(CH3)CF3
CH3


A-46
(R)CH2CH(CH3)CF3
CH3


A-47
(S)CH2CH(CH3)CF3
CH3


A-48
(±)CH2CH(CF3)CH2CH3
CH3


A-49
(R)CH2CH(CF3)CH2CH3
CH3


A-50
(S)CH2CH(CF3)CH2CH3
CH3


A-51
(±,±)CH(CH3)CH(CH3)CF3
CH3


A-52
(±,R)CH(CH3)CH(CH3)CF3
CH3


A-53
(±,S)CH(CH3)CH(CH3)CF3
CH3


A-54
(±,±)CH(CH3)CH(CF3)CH2CH3
CH3


A-55
(±,R)CH(CH3)CH(CF3)CH2CH3
CH3


A-56
(±,S)CH(CH3)CH(CF3)CH2CH3
CH3


A-57
CF3
CH3


A-58
CF2CF3
CH3


A-59
CF2CF2CF3
CH3


A-60
cyclo-C3H5
CH3


A-61
(1-CH3)-cyclo-C3H4
CH3


A-62
cyclo-C5H9
CH3


A-63
cyclo-C6H11
CH3


A-64
(4-CH3)-cyclo-C6H10
CH3


A-65
CH2C(CH3)═CH2
CH3


A-66
CH2CH2C(CH3)═CH2
CH3


A-67
CH2—C(CH3)3
CH3


A-68
CH2—Si(CH3)3
CH3


A-69
n-C6H13
CH3


A-70
(CH2)3—CH(CH3)2
CH3


A-71
(CH2)2—CH(CH3)—C2H5
CH3


A-72
CH2—CH(CH3)-n-C3H7
CH3


A-73
CH(CH3)-n-C4H9
CH3


A-74
CH2—CH(C2H5)2
CH3


A-75
CH(C2H5)-n-C3H7
CH3


A-76
CH2-cyclo-C5H9
CH3


A-77
CH2—CH(CH3)—CH(CH3)2
CH3


A-78
CH(CH3)—CH2CH(CH3)2
CH3


A-79
CH(CH3)—CH(CH3)—C2H5
CH3


A-80
CH(CH3)—C(CH3)3
CH3


A-81
(CH2)2—C(CH3)3
CH3


A-82
CH2—C(CH3)2—C2H5
CH3


A-83
2-CH3-cyclo-C5H8
CH3


A-84
3-CH3-cyclo-C5H8
CH3


A-85
C(CH3)2-n-C3H7
CH3


A-86
(CH2)6—CH3
CH3


A-87
(CH2)4—CH(CH3)2
CH3


A-88
(CH2)3—CH(CH3)—C2H5
CH3


A-89
(CH2)2—CH(CH3)-n-C3H7
CH3


A-90
CH2—CH(CH3)-n-C4H9
CH3


A-91
CH(CH3)-n-C5H11
CH3


A-92
(CH2)3C(CH3)3
CH3


A-93
(CH2)2CH(CH3)—CH(CH3)2
CH3


A-94
(CH2)CH(CH3)—CH2CH(CH3)2
CH3


A-95
CH(CH3)(CH2)2—CH(CH3)2
CH3


A-96
(CH2)2C(CH3)2C2H5
CH3


A-97
CH2CH(CH3)CH(CH3)C2H5
CH3


A-98
CH(CH3)CH2CH(CH3)C2H5
CH3


A-99
CH2C(CH3)2-n-C3H7
CH3


A-100
CH(CH3)CH(CH3)-n-C3H7
CH3


A-101
C(CH3)2-n-C4H9
CH3


A-102
(CH2)2CH(C2H5)2
CH3


A-103
CH2CH(C2H5)-n-C3H7
CH3


A-104
CH(C2H5)-n-C4H9
CH3


A-105
CH2CH(CH3)C(CH3)3
CH3


A-106
CH(CH3)CH2C(CH3)3
CH3


A-107
CH2C(CH3)2CH(CH3)2
CH3


A-108
CH2CH(C2H5)CH(CH3)2
CH3


A-109
CH(CH3)CH(CH3)CH(CH3)2
CH3


A-110
C(CH3)2CH2CH(CH3)2
CH3


A-111
CH(C2H5)CH2CH(CH3)2
CH3


A-112
CH(CH3)C(CH3)2C2H5
CH3


A-113
CH(CH3)CH(C2H5)2
CH3


A-114
C(CH3)2CH(CH3)C2H5
CH3


A-115
CH(C2H5)CH(CH3)C2H5
CH3


A-116
C(CH3)(C2H5)-n-C3H7
CH3


A-117
CH(n-C3H7)2
CH3


A-118
CH(n-C3H7)CH(CH3)2
CH3


A-119
C(CH3)2C(CH3)3
CH3


A-120
C(CH3)(C2H5)—CH(CH3)2
CH3


A-121
C(C2H5)3
CH3


A-122
(3-CH3)-cyclo-C6H10
CH3


A-123
(2-CH3)-cyclo-C6H10
CH3


A-124
n-C8H17
CH3


A-125
CH2C(═NO—CH3)CH3
CH3


A-126
CH2C(═NO—C2H5)CH3
CH3


A-127
CH2C(═NO-n-C3H7)CH3
CH3


A-128
CH2C(═NO-i-C3H7)CH3
CH3


A-129
CH(CH3)C(═NOCH3)CH3
CH3


A-130
CH(CH3)C(═NOC2H5)CH3
CH3


A-131
CH(CH3)C(═NO-n-C3H7)CH3
CH3


A-132
CH(CH3)C(═NO-i-C3H7)CH3
CH3


A-133
CH2C(═NO—CH3)C2H5
CH3


A-134
CH2C(═NO—C2H5)C2H5
CH3


A-135
CH2C(50 NO-n-C3H7)C2H5
CH3


A-136
CH2C(═NO-i-C3H7)C2H5
CH3


A-137
CH(CH3)C(═NOCH3)C2H5
CH3


A-138
CH(CH3)C(═NOC2H5)C2H5
CH3


A-139
CH(CH3)C(═NO-n-C3H7)C2H5
CH3


A-140
CH(CH3)C(═NO-n-C3H7)C2H5
CH3


A-141
CH═CH—CH2CH3
CH3


A-142
CH2—CH═CH—CH3
CH3


A-143
CH2—CH2—CH═CH2
CH3


A-144
C(CH3)2CH2CH3
CH3


A-145
CH═C(CH3)2
CH3


A-146
C(═CH2)—CH2CH3
CH3


A-147
C(CH3)═CH—CH3
CH3


A-148
CH(CH3)CH═CH2
CH3


A-149
CH═CH-n-C3H7
CH3


A-150
CH2—CH═CH—C2H5
CH3


A-151
(CH2)2—CH═CH—CH3
CH3


A-152
(CH2)3—CH═CH2
CH3


A-153
CH═CH—CH(CH3)2
CH3


A-154
CH2—CH═C(CH3)2
CH3


A-155
(CH2)2—C(CH3)═CH2
CH3


A-156
CH═C(CH3)—C2H5
CH3


A-157
CH2—C(═CH2)—C2H5
CH3


A-158
CH2—C(CH3)═CH—CH3
CH3


A-159
CH2—CH(CH3)—CH═CH2
CH3


A-160
C(═CH2)—CH2—CH2—CH3
CH3


A-161
C(CH3)═CH—CH2—CH3
CH3


A-162
CH(CH3)—CH═CH—CH3
CH3


A-163
CH(CH3)—CH2—CH═CH2
CH3


A-164
C(═CH2)CH(CH3)2
CH3


A-165
C(CH3)═C(CH3)2
CH3


A-166
CH(CH3)—C(═CH2)—CH3
CH3


A-167
C(CH3)2—CH═CH2
CH3


A-168
C(C2H5)═CH—CH3
CH3


A-169
CH(C2H5)—CH═CH2
CH3


A-170
CH═CH—CH2—CH2—CH2—CH3
CH3


A-171
CH2—CH═CH—CH2—CH2—CH3
CH3


A-172
CH2—CH2—CH═CH—CH2—CH3
CH3


A-173
CH2—CH2—CH2—CH═CH—CH3
CH3


A-174
CH2—CH2—CH2—CH2—CH═CH2
CH3


A-175
CH═CH—CH2—CH(CH3)CH3
CH3


A-176
CH2—CH═CH—CH(CH3)CH3
CH3


A-177
CH2—CH2—CH═C(CH3)CH3
CH3


A-178
CH2—CH2—CH2—C(CH3)═CH2
CH3


A-179
CH═CH—CH(CH3)—CH2—CH3
CH3


A-180
CH2—CH═C(CH3)—CH2—CH3
CH3


A-181
CH2—CH2—C(═CH2)—CH2—CH3
CH3


A-182
CH2—CH2—C(CH3)═CH—CH3
CH3


A-183
CH2—CH2—CH(CH3)—CH═CH2
CH3


A-184
CH═C(CH3)—CH2—CH2—CH3
CH3


A-185
CH2—C(═CH2)—CH2—CH2—CH3
CH3


A-186
CH2—C(CH3)═CH—CH2—CH3
CH3


A-187
CH2—CH(CH3)—CH═CH—CH3
CH3


A-188
CH2—CH(CH3)—CH2—CH═CH2
CH3


A-189
C(═CH2)—CH2—CH2—CH2—CH3
CH3


A-190
C(CH3)═CH—CH2—CH2—CH3
CH3


A-191
CH(CH3)—CH═CH—CH2—CH3
CH3


A-192
CH(CH3)—CH2—CH═CH—CH3
CH3


A-193
CH(CH3)—CH2—CH2—CH═CH2
CH3


A-194
CH═CH—C(CH3)3
CH3


A-195
CH═C(CH3)—CH(CH3)—CH3
CH3


A-196
CH2—C(═CH2)—CH(CH3)—CH3
CH3


A-197
CH2—C(CH3)═C(CH3)—CH3
CH3


A-198
CH2—CH(CH3)—C(═CH2)—CH3
CH3


A-199
C(═CH2)—CH2—CH(CH3)—CH3
CH3


A-200
C(CH3)═CH—CH(CH3)—CH3
CH3


A-201
CH(CH3)—CH═(CH3)—CH3
CH3


A-202
CH(CH3)—CH2—C(═CH2)—CH3
CH3


A-203
CH═C(CH2—CH3)—CH2—CH3
CH3


A-204
CH2—C(═CH—CH3)—CH2—CH3
CH3


A-205
CH2—CH(CH═CH2)—CH2—CH3
CH3


A-206
C(═CH—CH3)—CH2—CH2—CH3
CH3


A-207
CH(CH═CH2)—CH2—CH2—CH3
CH3


A-208
C(CH2—CH3)═CH—CH2—CH3
CH3


A-209
CH(CH2—CH3)—CH═CH—CH3
CH3


A-210
CH(CH2—CH3)—CH2—CH═CH2
CH3


A-211
CH2—C(CH3)2—CH═CH2
CH3


A-212
C(═CH2)—CH(CH3)—CH2—CH3
CH3


A-213
C(CH3)═C(CH3)—CH2—CH3
CH3


A-214
CH(CH3)—C(═CH2)—CH2—CH3
CH3


A-215
CH(CH3)—C(CH3)═CH—CH3
CH3


A-216
CH(CH3)—CH(CH3)—CH═CH2
CH3


A-217
C(CH3)2—CH═CH—CH3
CH3


A-218
C(CH3)2—CH2—CH═CH2
CH3


A-219
C(═CH2)—C(CH3)3
CH3


A-220
C(═CH—CH3)—CH(CH3)—CH3
CH3


A-221
CH(CH═CH2)—CH(CH3)—CH3
CH3


A-222
C(CH2—CH3)═C(CH3)—CH3
CH3


A-223
CH(CH2—CH3)—C(═CH2)—CH3
CH3


A-224
C(CH3)2—C(═CH2)—CH3
CH3


A-225
C(CH3)(CH═CH2)—CH2—CH3
CH3


A-226
C(CH3)(CH2CH3)—CH2—CH2—CH3
CH3


A-227
CH(CH2CH3)—CH(CH3)—CH2—CH3
CH3


A-228
CH(CH2CH3)—CH2—CH(CH3)—CH3
CH3


A-229
C(CH3)2—C(CH3)3
CH3


A-230
C(CH2—CH3)—C(CH3)3
CH3


A-231
C(CH3)(CH2—CH3)—CH(CH3)2
CH3


A-232
CH(CH(CH3)2)—CH(CH3)2
CH3


A-233
CH═CH—CH2—CH2—CH2—CH2—CH3
CH3


A-234
CH2—CH═CH—CH2—CH2—CH2—CH3
CH3


A-235
CH2—CH2—CH═CH—CH2—CH2—CH3
CH3


A-236
CH2—CH2—CH2—CH═CH—CH2—CH3
CH3


A-237
CH2—CH2—CH2—CH2—CH═CH—CH3
CH3


A-238
CH2—CH2—CH2—CH2—CH2—CH═CH2
CH3


A-239
CH═CH—CH2—CH2—CH(CH3)—CH3
CH3


A-240
CH2—CH═CH—CH2—CH(CH3)—CH3
CH3


A-241
CH2—CH2—CH═CH—CH(CH3)—CH3
CH3


A-242
CH2—CH2—CH2—CH═C(CH3)—CH3
CH3


A-243
CH2—CH2—CH2—CH2—C(═CH2)—CH3
CH3


A-244
CH═CH—CH2—CH(CH3)—CH2—CH3
CH3


A-245
CH2—CH═CH—CH(CH3)—CH2—CH3
CH3


A-246
CH2—CH2—CH═C(CH3)—CH2—CH3
CH3


A-247
CH2—CH2—CH2—C(═CH2)—CH2—CH3
CH3


A-248
CH2—CH2—CH2—C(CH3)═CH—CH3
CH3


A-249
CH2—CH2—CH2—CH(CH3)—CH═CH2
CH3


A-250
CH═CH—CH(CH3)—CH2—CH2—CH3
CH3


A-251
CH2—CH═C(CH3)—CH2—CH2—CH3
CH3


A-252
CH2—CH2—C(═CH2)—CH2—CH2—CH3
CH3


A-253
CH2—CH2—C(CH3)═CH—CH2—CH3
CH3


A-254
CH2—CH2—CH(CH3)—CH═CH—CH3
CH3


A-255
CH2—CH2—CH(CH3)—CH2—CH═CH2
CH3


A-256
CH═C(CH3)—CH2—CH2—CH2—CH3
CH3


A-257
CH2—C(═CH2)—CH2—CH2—CH2—CH3
CH3


A-258
CH2—C(CH3)═CH—CH2—CH2—CH3
CH3


A-259
CH2—CH(CH3)—CH═CH—CH2—CH3
CH3


A-260
CH2—CH(CH3)—CH2—CH═CH—CH3
CH3


A-261
CH2—CH(CH3)—CH2—CH2—CH═CH2
CH3


A-262
C(═CH2)—CH2—CH2—CH2—CH2—CH3
CH3


A-263
C(CH3)═CH—CH2—CH2—CH2—CH3
CH3


A-264
CH(CH3)—CH═CH—CH2—CH2—CH3
CH3


A-265
CH(CH3)—CH2—CH═CH—CH2—CH3
CH3


A-266
CH(CH3)—CH2—CH2—CH═CH—CH3
CH3


A-267
CH(CH3)—CH2—CH2—CH2—CH═CH2
CH3


A-268
CH═CH—CH2—C(CH3)3
CH3


A-269
CH2—CH═CH—C(CH3)3
CH3


A-270
CH═CH—CH(CH3)—CH(CH3)2
CH3


A-271
CH2—CH═C(CH3)—CH(CH3)2
CH3


A-272
CH2—CH2—C(═CH2)—CH(CH3)2
CH3


A-273
CH2—CH2—C(CH3)═C(CH3)2
CH3


A-274
CH2—CH2—CH(CH3)—C(═CH2)—CH3
CH3


A-275
CH═C(CH3)—CH2—CH(CH3)2
CH3


A-276
CH2—C(═CH2)—CH2—CH(CH3)2
CH3


A-277
CH2—C(CH3)═CH—CH(CH3)2
CH3


A-278
CH2—CH(CH3)—CH═C(CH3)2
CH3


A-279
CH2—CH(CH3)—CH2—C(═CH2)—CH3
CH3


A-280
C(═CH2)—CH2—CH2—CH(CH3)2
CH3


A-281
C(CH3)═CH—CH2—CH(CH3)2
CH3


A-282
CH(CH3)—CH═CH—CH(CH3)2
CH3


A-283
CH(CH3)—CH2—CH═(CH3)2
CH3


A-284
CH(CH3)—CH2—CH2—C(═CH2)—CH3
CH3


A-285
CH═CH—C(CH3)2—CH2—CH3
CH3


A-286
CH2—CH2—C(CH3)2—CH═CH2
CH3


A-287
CH═C(CH3)—CH(CH3)—CH2—CH3
CH3


A-288
CH2—C(═CH2)—CH(CH3)—CH2—CH3
CH3


A-289
CH2—C(CH3)═C(CH3)—CH2—CH3
CH3


A-290
CH2—CH(CH3)—C(═CH2)—CH2—CH3
CH3


A-291
CH2—CH(CH3)—C(CH3)═CH—CH3
CH3


A-292
CH2—CH(CH3)—CH(CH3)—CH═CH2
CH3


A-293
C(═CH2)—CH2—CH(CH3)—CH2—CH3
CH3


A-294
C(CH3)═CH—CH(CH3)—CH2—CH3
CH3


A-295
CH(CH3)—CH═(CH3)—CH2—CH3
CH3


A-296
CH(CH3)—CH2—C(═CH2)—CH2—CH3
CH3


A-297
CH(CH3)—CH2—C(CH3)═CH—CH3
CH3


A-298
CH(CH3)—CH2—CH(CH3)—CH═CH2
CH3


A-299
CH2—C(CH3)2—CH═CH—CH3
CH3


A-300
CH2—C(CH3)2—CH2—CH═CH2
CH3


A-301
C(═CH2)—CH(CH3)—CH2—CH2—CH3
CH3


A-302
C(CH3)═C(CH3)—CH2—CH2—CH3
CH3


A-303
CH(CH3)—C(═CH2)—CH2—CH2—CH3
CH3


A-304
CH(CH3)—C(CH3)═CH—CH2—CH3
CH3


A-305
CH(CH3)—CH(CH3)—CH═CH—CH3
CH3


A-306
CH(CH3)—CH(CH3)—CH2—CH═CH2
CH3


A-307
C(CH3)2—CH═CH—CH2—CH3
CH3


A-308
C(CH3)2—CH2—CH═CH—CH3
CH3


A-309
C(CH3)2—CH2—CH2—CH═CH2
CH3


A-310
CH═CH—CH(CH2—CH3)—CH2—CH3
CH3


A-311
CH2—CH═C(CH2—CH3)—CH2—CH3
CH3


A-312
CH2—CH2—C(═CH—CH3)—CH2—CH3
CH3


A-313
CH2—CH2—CH(CH═CH2)—CH2—CH3
CH3


A-314
CH═C(CH2—CH3)—CH2—CH2—CH3
CH3


A-315
CH2—C(═CH—CH3)—CH2—CH2—CH3
CH3


A-316
CH2—CH(CH═CH2)—CH2—CH2—CH3
CH3


A-317
CH2—C(CH2—CH3)═CH—CH2—CH3
CH3


A-318
CH2—CH(CH2—CH3)—CH═CH—CH3
CH3


A-319
CH2—CH(CH2—CH3)—CH—CH═CH2
CH3


A-320
C(═CH—CH3)—CH2—CH2—CH2—CH3
CH3


A-321
CH(CH═CH2)—CH2—CH2—CH2—CH3
CH3


A-322
C(CH2—CH3)═CH—CH2—CH2—CH3
CH3


A-323
CH(CH2—CH3)—CH═CH—CH2—CH3
CH3


A-324
CH(CH2—CH3)—CH2—CH═CH—CH3
CH3


A-325
CH(CH2—CH3)—CH2—CH2—CH═CH2
CH3


A-326
C(═CH—CH2—CH3)—CH2—CH2—CH3
CH3


A-327
C(CH═CH—CH3)—CH2—CH2—CH3
CH3


A-328
C(CH2—CH═CH2)—CH2—CH2—CH3
CH3


A-329
CH═C(CH3)—C(CH3)3
CH3


A-330
CH2—C(═CH2)—C(CH3)3
CH3


A-331
CH2—C(CH3)2—CH(═CH2)—CH3
CH3


A-332
C(═CH2)—CH(CH3)—CH(CH3)—CH3
CH3


A-333
C(CH3)═C(CH3)—CH(CH3)—CH3
CH3


A-334
CH(CH3)—C(═CH2)—CH(CH3)—CH3
CH3


A-335
CH(CH3)—C(CH3)═C(CH3)—CH3
CH3


A-336
CH(CH3)—CH(CH3)—C(═CH2)—CH3
CH3


A-337
C(CH3)2—CH═C(CH3)—CH3
CH3


A-338
C(CH3)2—CH2—C(═CH2)—CH3
CH3


A-339
C(CH3)2—C(═CH2)—CH2—CH3
CH3


A-340
C(CH3)2—C(CH3)═CH—CH3
CH3


A-341
C(CH3)2—CH(CH3)CH═CH2
CH3


A-342
CH(CH2—CH3)—CH2—CH(CH3)—CH3
CH3


A-343
CH(CH2—CH3)—CH(CH3)—CH2—CH3
CH3


A-344
C(CH3)(CH2—CH3)—CH2—CH2—CH3
CH3


A-345
CH(i-C3H7)—CH2—CH2—CH3
CH3


A-346
CH═C(CH2—CH3)—CH(CH3)—CH3
CH3


A-347
CH2—C(═CH—CH3)—CH(CH3)—CH3
CH3


A-348
CH2—CH(CH═CH2)—CH(CH3)—CH3
CH3


A-349
CH2—C(CH2—CH3)═C(CH3)—CH3
CH3


A-350
CH2—CH(CH2—CH3)—C(═CH2)—CH3
CH3


A-351
CH2—C(CH3)(CH═CH2)—CH2—CH3
CH3


A-352
C(═CH2)—CH(CH2—CH3)—CH2—CH3
CH3


A-353
C(CH3)═C(CH2—CH3)—CH2—CH3
CH3


A-354
CH(CH3)—C(═CH—CH3)—CH2—CH3
CH3


A-355
CH(CH3)—CH(CH═CH2)—CH2—CH3
CH3


A-356
CH═C(CH2—CH3)—CH(CH3)—CH3
CH3


A-357
CH2—C(═CH—CH3)—CH(CH3)—CH3
CH3


A-358
CH2—CH(CH═CH2)—CH(CH3)—CH3
CH3


A-359
CH2—C(CH2—CH3)═C(CH3)—CH3
CH3


A-360
CH2—CH(CH2—CH3)—C(═CH2)—CH3
CH3


A-361
C(═CH—CH3)—CH2—CH(CH3)—CH3
CH3


A-362
CH(CH═CH2)—CH2—CH(CH3)—CH3
CH3


A-363
C(CH2—CH3)═CH—CH(CH3)—CH3
CH3


A-364
CH(CH2—CH3)CH═C(CH3)—CH3
CH3


A-365
CH(CH2—CH3)CH2—C(═CH2)—CH3
CH3


A-366
C(═CH—CH3)CH(CH3)—CH2—CH3
CH3


A-367
CH(CH═CH2)CH(CH3)—CH2—CH3
CH3


A-368
C(CH2—CH3)═C(CH3)—CH2—CH3
CH3


A-369
CH(CH2—CH3)—C(═CH2)—CH2—CH3
CH3


A-370
CH(CH2—CH3)—C(CH3)═CH—CH3
CH3


A-371
CH(CH2—CH3)—CH(CH3)—CH═CH2
CH3


A-372
C(CH3)(CH═CH2)—CH2—CH2—CH3
CH3


A-373
C(CH3)(CH2—CH3)—CH═CH—CH3
CH3


A-374
C(CH3)(CH2—CH3)—CH2—CH═CH2
CH3


A-375
C[═C(CH3)—CH3]—CH2—CH2—CH3
CH3


A-376
CH[C(═CH2)—CH3]—CH2—CH2—CH3
CH3


A-377
C(i-C3H7)═CH—CH2—CH3
CH3


A-378
CH(i-C3H7)—CH═CH—CH3
CH3


A-379
CH(i-C3H7)—CH2—CH═CH2
CH3


A-380
C(═CH—CH3)—C(CH3)3
CH3


A-381
CH(CH═CH2)—C(CH3)3
CH3


A-382
C(CH3)(CH═CH2)CH(CH3)—CH3
CH3


A-383
C(CH3)(CH2—CH3)C(═CH2)—CH3
CH3


A-384
2-CH3-cyclohex-1-enyl
CH3


A-385
[2-(═CH2)]-cyclo-C6H9
CH3


A-386
2-CH3-cyclohex-2-enyl
CH3


A-387
2-CH3-cyclohex-3-enyl
CH3


A-388
2-CH3-cyclohex-4-enyl
CH3


A-389
2-CH3-cyclohex-5-enyl
CH3


A-390
2-CH3-cyclohex-6-enyl
CH3


A-391
3-CH3-cyclohex-1-enyl
CH3


A-392
3-CH3-cyclohex-2-enyl
CH3


A-393
[3-(═CH2)]-cyclo-C6H9
CH3


A-394
3-CH3-cyclohex-3-enyl
CH3


A-395
3-CH3-cyclohex-4-enyl
CH3


A-396
3-CH3-cyclohex-5-enyl
CH3


A-397
3-CH3-cyclohex-6-enyl
CH3


A-398
4-CH3-cyclohex-1-enyl
CH3


A-399
4-CH3-cyclohex-2-enyl
CH3


A-400
4-CH3-cyclohex-3-enyl
CH3


A-401
[4-(═CH2)]-cyclo-C6H9
CH3


A-402
CH2CF3
CH3


A-403
CH2CCl3
CH3


A-404
CH2(cyclo-C3H5)
CH3


A-405
CH(CH3)2
CH2CH3


A-406
CH(CH3)2
CH2CH2CH3


A-407
CH(CH3)2
CH2CH2F


A-408
CH(CH3)2
H


A-409
CH(CH3)2
CH(CH3)2


A-410
CH(CH3)2
CH2C(CH3)3


A-411
CH(CH3)2
CH2CH(CH3)2


A-412
CH(CH3)2
(±)CH(CH2CH3)CH3


A-413
CH(CH3)2
(R)CH(CH2CH3)CH3


A-414
CH(CH3)2
(S)CH(CH2CH3)CH3


A-415
CH(CH3)2
(±)CH(CH3)—CH(CH3)2


A-416
CH(CH3)2
(R)CH(CH3)—CH(CH3)2


A-417
CH(CH3)2
(S)CH(CH3)—CH(CH3)2


A-418
CH(CH3)2
(±)CH(CH3)—C(CH3)3


A-419
CH(CH3)2
(R)CH(CH3)—C(CH3)3


A-420
CH(CH3)2
(S)CH(CH3)—C(CH3)3


A-421
CH(CH3)2
(±)CH(CH3)—CF3


A-422
CH(CH3)2
(R)CH(CH3)—CF3


A-423
CH(CH3)2
(S)CH(CH3)—CF3


A-424
CH(CH3)2
(±)CH(CH3)—CCl3


A-425
CH(CH3)2
(R)CH(CH3)—CCl3


A-426
CH(CH3)2
(S)CH(CH3)—CCl3


A-427
CH(CH3)2
CH2C(CH3)═CH2


A-428
CH(CH3)2
cyclopentyl


A-429
CH(CH3)2
cyclohexyl


A-430
CH(CH3)2
(CH2)3CH3


A-431
CH(CH3)2
C(CH3)3


A-432
CH(CH3)2
(CH2)4CH3


A-433
CH(CH3)2
CH(CH2CH3)2


A-434
CH(CH3)2
CH2CH2CH(CH3)2


A-435
CH(CH3)2
(±)CH(CH3)(CH2)2CH3


A-436
CH(CH3)2
(R)CH(CH3)(CH2)2CH3


A-437
CH(CH3)2
(S)CH(CH3)(CH2)2CH3


A-438
CH(CH3)2
(±)CH2CH(CH3)CH2CH3


A-439
CH(CH3)2
(R)CH2CH(CH3)CH2CH3


A-440
CH(CH3)2
(S)CH2CH(CH3)CH2CH3


A-441
CH(CH3)2
(±)CH(CH3)CH(CH3)2


A-442
CH(CH3)2
(R)CH(CH3)CH(CH3)2


A-443
CH(CH3)2
(S)CH(CH3)CH(CH3)2


A-444
CH(CH3)2
(CH2)5CH3


A-445
CH(CH3)2
(±,±)CH(CH3)CH(CH3)CH2CH3


A-446
CH(CH3)2
(±,R)CH(CH3)CH(CH3)CH2CH3


A-447
CH(CH3)2
(±,S)CH(CH3)CH(CH3)CH2CH3


A-448
CH(CH3)2
(±)CH2CH(CH3)CF3


A-449
CH(CH3)2
(R)CH2CH(CH3)CF3


A-450
CH(CH3)2
(S)CH2CH(CH3)CF3


A-451
CH(CH3)2
(±)CH2CH(CF3)CH2CH3


A-452
CH(CH3)2
(R)CH2CH(CF3)CH2CH3


A-453
CH(CH3)2
(S)CH2CH(CF3)CH2CH3


A-454
CH(CH3)2
(±,±)CH(CH3)CH(CH3)CF3


A-455
CH(CH3)2
(±,R)CH(CH3)CH(CH3)CF3


A-456
CH(CH3)2
(±,S)CH(CH3)CH(CH3)CF3


A-457
CH(CH3)2
(±,±)CH(CH3)CH(CF3)CH2CH3


A-458
CH(CH3)2
(±,R)CH(CH3)CH(CF3)CH2CH3


A-459
CH(CH3)2
(±,S)CH(CH3)CH(CF3)CH2CH3


A-460
CH(CH3)2
CF3


A-461
CH(CH3)2
CF2CF3


A-462
CH(CH3)2
CF2CF2CF3


A-463
CH(CH3)2
cyclo-C3H5


A-464
CH(CH3)2
(1-CH3)-cyclo-C3H4


A-465
CH(CH3)2
cyclo-C5H9


A-466
CH(CH3)2
cyclo-C6H11


A-467
CH(CH3)2
(4-CH3)-cyclo-C6H10


A-468
CH(CH3)2
CH2C(CH3)═CH2


A-469
CH(CH3)2
CH2CH2C(CH3)═CH2


A-470
CH(CH3)2
CH2—C(CH3)3


A-471
CH(CH3)2
CH2—Si(CH3)3


A-472
CH(CH3)2
n-C6H13


A-473
CH(CH3)2
(CH2)3—CH(CH3)2


A-474
CH(CH3)2
(CH2)2—CH(CH3)—C2H5


A-475
CH(CH3)2
CH2—CH(CH3)-n-C3H7


A-476
CH(CH3)2
CH(CH3)-n-C4H9


A-477
CH(CH3)2
CH2—CH(C2H5)2


A-478
CH(CH3)2
CH(C2H5)-n-C3H7


A-479
CH(CH3)2
CH2-cyclo-C5H9


A-480
CH(CH3)2
CH2—CH(CH3)—CH(CH3)2


A-481
CH(CH3)2
CH(CH3)—CH2CH(CH3)2


A-482
CH(CH3)2
CH(CH3)—CH(CH3)—C2H5


A-483
CH(CH3)2
CH(CH3)—C(CH3)3


A-484
CH(CH3)2
(CH2)2—C(CH3)3


A-485
CH(CH3)2
CH2—C(CH3)2—C2H5


A-486
CH(CH3)2
2-CH3-cyclo-C5H8


A-487
CH(CH3)2
3-CH3-cyclo-C5H8


A-488
CH(CH3)2
C(CH3)2-n-C3H7


A-489
CH(CH3)2
(CH2)6—CH3


A-490
CH(CH3)2
(CH2)4—CH(CH3)2


A-491
CH(CH3)2
(CH2)3—CH(CH3)—C2H5


A-492
CH(CH3)2
(CH2)2—CH(CH3)-n-C3H7


A-493
CH(CH3)2
CH2—CH(CH3)-n-C4H9


A-494
CH(CH3)2
CH(CH3)-n-C5H11


A-495
CH(CH3)2
(CH2)3C(CH3)3


A-496
CH(CH3)2
(CH2)2CH(CH3)—CH(CH3)2


A-497
CH(CH3)2
(CH2)CH(CH3)—CH2CH(CH3)2


A-498
CH(CH3)2
CH(CH3)(CH2)2—CH(CH3)2


A-499
CH(CH3)2
(CH2)2C(CH3)2C2H5


A-500
CH(CH3)2
CH2CH(CH3)CH(CH3)C2H5


A-501
CH(CH3)2
CH(CH3)CH2CH(CH3)C2H5


A-502
CH(CH3)2
CH2C(CH3)2-n-C3H7


A-503
CH(CH3)2
CH(CH3)CH(CH3)-n-C3H7


A-504
CH(CH3)2
C(CH3)2-n-C4H9


A-505
CH(CH3)2
(CH2)2CH(C2H5)2


A-506
CH(CH3)2
CH2CH(C2H5)-n-C3H7


A-507
CH(CH3)2
CH(C2H5)-n-C4H9


A-508
CH(CH3)2
CH2CH(CH3)C(CH3)3


A-509
CH(CH3)2
CH(CH3)CH2C(CH3)3


A-510
CH(CH3)2
CH2C(CH3)2CH(CH3)2


A-511
CH(CH3)2
CH2CH(C2H5)CH(CH3)2


A-512
CH(CH3)2
CH(CH3)CH(CH3)CH(CH3)2


A-513
CH(CH3)2
C(CH3)2CH2CH(CH3)2


A-514
CH(CH3)2
CH(C2H5)CH2CH(CH3)2


A-515
CH(CH3)2
CH(CH3)C(CH3)2C2H5


A-516
CH(CH3)2
CH(CH3)CH(C2H5)2


A-517
CH(CH3)2
C(CH3)2CH(CH3)C2H5


A-518
CH(CH3)2
CH(C2H5)CH(CH3)C2H5


A-519
CH(CH3)2
C(CH3)(C2H5)-n-C3H7


A-520
CH(CH3)2
CH(n-C3H7)2


A-521
CH(CH3)2
CH(n-C3H7)CH(CH3)2


A-522
CH(CH3)2
C(CH3)2C(CH3)3


A-523
CH(CH3)2
C(CH3)(C2H5)—CH(CH3)2


A-524
CH(CH3)2
C(C2H5)3


A-525
CH(CH3)2
(3-CH3)-cyclo-C6H10


A-526
CH(CH3)2
(2-CH3)-cyclo-C6H10


A-527
CH(CH3)2
n-C8H17


A-528
CH(CH3)2
CH2C(═NO—CH3)CH3


A-529
CH(CH3)2
CH2C(═NO—C2H5)CH3


A-530
CH(CH3)2
CH2C(═NO-n-C3H7)CH3


A-531
CH(CH3)2
CH2C(═NO-i-C3H7)CH3


A-532
CH(CH3)2
CH(CH3)C(═NOCH3)CH3


A-533
CH(CH3)2
CH(CH3)C(═NOC2H5)CH3


A-534
CH(CH3)2
CH(CH3)C(═NO-n-C3H7)CH3


A-535
CH(CH3)2
CH(CH3)C(═NO-i-C3H7)CH3


A-536
CH(CH3)2
CH2C(═NO—CH3)C2H5


A-537
CH(CH3)2
CH2C(═NO—C2H5)C2H5


A-538
CH(CH3)2
CH2C(═NO-n-C3H7)C2H5


A-539
CH(CH3)2
CH2C(═NO-i-C3H7)C2H5


A-540
CH(CH3)2
CH(CH3)C(═NOCH3)C2H5


A-541
CH(CH3)2
CH(CH3)C(═NOC2H5)C2H5


A-542
CH(CH3)2
CH(CH3)C(═NO-n-C3H7)C2H5


A-543
CH(CH3)2
CH(CH3)C(═NO-n-C3H7)C2H5


A-544
CH(CH3)2
CH═CH—CH2CH3


A-545
CH(CH3)2
CH2—CH═CH—CH3


A-546
CH(CH3)2
CH2—CH2—CH═CH2


A-547
CH(CH3)2
C(CH3)2CH2CH3


A-548
CH(CH3)2
CH═C(CH3)2


A-549
CH(CH3)2
C(═CH2)—CH2CH3


A-550
CH(CH3)2
C(CH3)═CH—CH3


A-551
CH(CH3)2
CH(CH3)CH═CH2


A-552
CH(CH3)2
CH═CH-n-C3H7


A-553
CH(CH3)2
CH2—CH═CH—C2H5


A-554
CH(CH3)2
(CH2)2—CH═CH—CH3


A-555
CH(CH3)2
(CH2)3—CH═CH2


A-556
CH(CH3)2
CH═CH—CH(CH3)2


A-557
CH(CH3)2
CH2—CH═C(CH3)2


A-558
CH(CH3)2
(CH2)2—C(CH3)═CH2


A-559
CH(CH3)2
CH═C(CH3)—C2H5


A-560
CH(CH3)2
CH2—C(═CH2)—C2H5


A-561
CH(CH3)2
CH2—C(CH3)═CH—CH3


A-562
CH(CH3)2
CH2—CH(CH3)—CH═CH2


A-563
CH(CH3)2
C(═CH2)—CH2—CH2—CH3


A-564
CH(CH3)2
C(CH3)═CH—CH2—CH3


A-565
CH(CH3)2
CH(CH3)—CH═CH—CH3


A-566
CH(CH3)2
CH(CH3)—CH2—CH═CH2


A-567
CH(CH3)2
C(═CH2)CH(CH3)2


A-568
CH(CH3)2
C(CH3)═C(CH3)2


A-569
CH(CH3)2
CH(CH3)—C(═CH2)—CH3


A-570
CH(CH3)2
C(CH3)2—CH═CH2


A-571
CH(CH3)2
C(C2H5)═CH—CH3


A-572
CH(CH3)2
CH(C2H5)—CH═CH2


A-573
CH(CH3)2
CH═CH—CH2—CH2—CH2—CH3


A-574
CH(CH3)2
CH2—CH═CH—CH2—CH2—CH3


A-575
CH(CH3)2
CH2—CH2—CH═CH—CH2—CH3


A-576
CH(CH3)2
CH2—CH2—CH2—CH═CH—CH3


A-577
CH(CH3)2
CH2—CH2—CH2—CH2—CH═CH2


A-578
CH(CH3)2
CH═CH—CH2—CH(CH3)CH3


A-579
CH(CH3)2
CH2—CH═CH—CH(CH3)CH3


A-580
CH(CH3)2
CH2—CH2—CH═C(CH3)CH3


A-581
CH(CH3)2
CH2—CH2—CH2—C(CH3)═CH2


A-582
CH(CH3)2
CH═CH—CH(CH3)—CH2—CH3


A-583
CH(CH3)2
CH2—CH═C(CH3)—CH2—CH3


A-584
CH(CH3)2
CH2—CH2—C(═CH2)—CH2—CH3


A-585
CH(CH3)2
CH2—CH2—C(CH3)═CH—CH3


A-586
CH(CH3)2
CH2—CH2—CH(CH3)—CH═CH2


A-587
CH(CH3)2
CH═C(CH3)—CH2—CH2—CH3


A-588
CH(CH3)2
CH2—C(═CH2)—CH2—CH2—CH3


A-589
CH(CH3)2
CH2—C(CH3)═CH—CH2—CH3


A-590
CH(CH3)2
CH2—CH(CH3)—CH═CH—CH3


A-591
CH(CH3)2
CH2—CH(CH3)—CH2—CH═CH2


A-592
CH(CH3)2
C(═CH2)—CH2—CH2—CH2—CH3


A-593
CH(CH3)2
C(CH3)═CH—CH2—CH2—CH3


A-594
CH(CH3)2
CH(CH3)—CH═CH—CH2—CH3


A-595
CH(CH3)2
CH(CH3)—CH2—CH═CH—CH3


A-596
CH(CH3)2
CH(CH3)—CH2—CH2—CH═CH2


A-597
CH(CH3)2
CH═CH—C(CH3)3


A-598
CH(CH3)2
CH═C(CH3)—CH(CH3)—CH3


A-599
CH(CH3)2
CH2—C(═CH2)—CH(CH3)—CH3


A-600
CH(CH3)2
CH2—C(CH3)═C(CH3)—CH3


A-601
CH(CH3)2
CH2—CH(CH3)—C(═CH2)—CH3


A-602
CH(CH3)2
C(═CH2)—CH2—CH(CH3)—CH3


A-603
CH(CH3)2
C(CH3)═CH—CH(CH3)—CH3


A-604
CH(CH3)2
CH(CH3)—CH═C(CH3)—CH3


A-605
CH(CH3)2
CH(CH3)—CH2—C(═CH2)—CH3


A-606
CH(CH3)2
CH═C(CH2—CH3)—CH2—CH3


A-607
CH(CH3)2
CH2—C(═CH—CH3)—CH2—CH3


A-608
CH(CH3)2
CH2—CH(CH═CH2)—CH2—CH3


A-609
CH(CH3)2
C(═CH—CH3)—CH2—CH2—CH3


A-610
CH(CH3)2
CH(CH═CH2)—CH2—CH2—CH3


A-611
CH(CH3)2
C(CH2—CH3)═CH—CH2—CH3


A-612
CH(CH3)2
CH(CH2—CH3)—CH═CH—CH3


A-613
CH(CH3)2
CH(CH2—CH3)—CH2—CH═CH2


A-614
CH(CH3)2
CH2—C(CH3)2—CH═CH2


A-615
CH(CH3)2
C(═CH2)—CH(CH3)—CH2—CH3


A-616
CH(CH3)2
C(CH3)═C(CH3)—CH2—CH3


A-617
CH(CH3)2
CH(CH3)—C(═CH2)—CH2—CH3


A-618
CH(CH3)2
CH(CH3)—C(CH3)═CH—CH3


A-619
CH(CH3)2
CH(CH3)—CH(CH3)—CH═CH2


A-620
CH(CH3)2
C(CH3)2—CH═CH—CH3


A-621
CH(CH3)2
C(CH3)2—CH2—CH═CH2


A-622
CH(CH3)2
C(═CH2)—C(CH3)3


A-623
CH(CH3)2
C(═CH—CH3)—CH(CH3)—CH3


A-624
CH(CH3)2
CH(CH═CH2)—CH(CH3)—CH3


A-625
CH(CH3)2
C(CH2—CH3)═C(CH3)—CH3


A-626
CH(CH3)2
CH(CH2—CH3)—C(═CH2)—CH3


A-627
CH(CH3)2
C(CH3)2—C(═CH2)—CH3


A-628
CH(CH3)2
C(CH3)(CH═CH2)—CH2—CH3


A-629
CH(CH3)2
C(CH3)(CH2CH3)—CH2—CH2—CH3


A-630
CH(CH3)2
CH(CH2CH3)—CH(CH3)—CH2—CH3


A-631
CH(CH3)2
CH(CH2CH3)—CH2—CH(CH3)—CH3


A-632
CH(CH3)2
C(CH3)2—C(CH3)3


A-633
CH(CH3)2
C(CH2—CH3)—C(CH3)3


A-634
CH(CH3)2
C(CH3)(CH2—CH3)—CH(CH3)2


A-635
CH(CH3)2
CH(CH(CH3)2)—CH(CH3)2


A-636
CH(CH3)2
CH═CH—CH2—CH2—CH2—CH2—CH3


A-637
CH(CH3)2
CH2—CH═CH—CH2—CH2—CH2—CH3


A-638
CH(CH3)2
CH2—CH2—CH═CH—CH2—CH2—CH3


A-639
CH(CH3)2
CH2—CH2—CH2—CH═CH—CH2—CH3


A-640
CH(CH3)2
CH2—CH2—CH2—CH2—CH═CH—CH3


A-641
CH(CH3)2
CH2—CH2—CH2—CH2—CH2—CH═CH2


A-642
CH(CH3)2
CH═CH—CH2—CH2—CH(CH3)—CH3


A-643
CH(CH3)2
CH2—CH═CH—CH2—CH(CH3)—CH3


A-644
CH(CH3)2
CH2—CH2—CH═CH—CH(CH3)—CH3


A-645
CH(CH3)2
CH2—CH2—CH2—CH═C(CH3)—CH3


A-646
CH(CH3)2
CH2—CH2—CH2—CH2—C(═CH2)—CH3


A-647
CH(CH3)2
CH═CH—CH2—CH(CH3)—CH2—CH3


A-648
CH(CH3)2
CH2—CH═CH—CH(CH3)—CH2—CH3


A-649
CH(CH3)2
CH2—CH2—CH═C(CH3)—CH2—CH3


A-650
CH(CH3)2
CH2—CH2—CH2—C(═CH2)—CH2—CH3


A-651
CH(CH3)2
CH2—CH2—CH2—C(CH3)═CH—CH3


A-652
CH(CH3)2
CH2—CH2—CH2—CH(CH3)—CH═CH2


A-653
CH(CH3)2
CH═CH—CH(CH3)—CH2—CH2—CH3


A-654
CH(CH3)2
CH2—CH═C(CH3)—CH2—CH2—CH3


A-655
CH(CH3)2
CH2—CH2—C(═CH2)—CH2—CH2—CH3


A-656
CH(CH3)2
CH2—CH2—C(CH3)═CH—CH2—CH3


A-657
CH(CH3)2
CH2—CH2—CH(CH3)—CH═CH—CH3


A-658
CH(CH3)2
CH2—CH2—CH(CH3)—CH2—CH═CH2


A-659
CH(CH3)2
CH═C(CH3)—CH2—CH2—CH2—CH3


A-660
CH(CH3)2
CH2—C(═CH2)—CH2—CH2—CH2—CH3


A-661
CH(CH3)2
CH2—C(CH3)═CH—CH2—CH2—CH3


A-662
CH(CH3)2
CH2—CH(CH3)—CH═CH—CH2—CH3


A-663
CH(CH3)2
CH2—CH(CH3)—CH2—CH═CH—CH3


A-664
CH(CH3)2
CH2—CH(CH3)—CH2—CH2—CH═CH2


A-665
CH(CH3)2
C(═CH2)—CH2—CH2—CH2—CH2—CH3


A-666
CH(CH3)2
C(CH3)═CH—CH2—CH2—CH2—CH3


A-667
CH(CH3)2
CH(CH3)—CH═CH—CH2—CH2—CH3


A-668
CH(CH3)2
CH(CH3)—CH2—CH═CH—CH2—CH3


A-669
CH(CH3)2
CH(CH3)—CH2—CH2—CH═CH—CH3


A-670
CH(CH3)2
CH(CH3)—CH2—CH2—CH2—CH═CH2


A-671
CH(CH3)2
CH═CH—CH2—C(CH3)3


A-672
CH(CH3)2
CH2—CH═CH—C(CH3)3


A-673
CH(CH3)2
CH═CH—CH(CH3)—CH(CH3)2


A-674
CH(CH3)2
CH2—CH═C(CH3)—CH(CH3)2


A-675
CH(CH3)2
CH2—CH2—C(═CH2)—CH(CH3)2


A-676
CH(CH3)2
CH2—CH2—C(CH3)═C(CH3)2


A-677
CH(CH3)2
CH2—CH2—CH(CH3)—C(═CH2)—CH3


A-678
CH(CH3)2
CH═C(CH3)—CH2—CH(CH3)2


A-679
CH(CH3)2
CH2—C(═CH2)—CH2—CH(CH3)2


A-680
CH(CH3)2
CH2—C(CH3)═CH—CH(CH3)2


A-681
CH(CH3)2
CH2—CH(CH3)—CH═C(CH3)2


A-682
CH(CH3)2
CH2—CH(CH3)—CH2—C(═CH2)—CH3


A-683
CH(CH3)2
C(═CH2)—CH2—CH2—CH(CH3)2


A-684
CH(CH3)2
C(CH3)═CH—CH2—CH(CH3)2


A-685
CH(CH3)2
CH(CH3)—CH═CH—CH(CH3)2


A-686
CH(CH3)2
CH(CH3)—CH2—CH═C(CH3)2


A-687
CH(CH3)2
CH(CH3)—CH2—CH2—C(═CH2)—CH3


A-688
CH(CH3)2
CH═CH—C(CH3)2—CH2—CH3


A-689
CH(CH3)2
CH2—CH2—C(CH3)2—CH═CH2


A-690
CH(CH3)2
CH═C(CH3)—CH(CH3)—CH2—CH3


A-691
CH(CH3)2
CH2—C(═CH2)—CH(CH3)—CH2—CH3


A-692
CH(CH3)2
CH2—C(CH3)═C(CH3)—CH2—CH3


A-693
CH(CH3)2
CH2—CH(CH3)—C(═CH2)—CH2—CH3


A-694
CH(CH3)2
CH2—CH(CH3)—C(CH3)═CH—CH3


A-695
CH(CH3)2
CH2—CH(CH3)—CH(CH3)—CH═CH2


A-696
CH(CH3)2
C(═CH2)—CH2—CH(CH3)—CH2—CH3


A-697
CH(CH3)2
C(CH3)═CH—CH(CH3)—CH2—CH3


A-698
CH(CH3)2
CH(CH3)—CH═C(CH3)—CH2—CH3


A-699
CH(CH3)2
CH(CH3)—CH2—C(═CH2)—CH2—CH3


A-700
CH(CH3)2
CH(CH3)—CH2—C(CH3)═CH—CH3


A-701
CH(CH3)2
CH(CH3)—CH2—CH(CH3)—CH═CH2


A-702
CH(CH3)2
CH2—C(CH3)2—CH═CH—CH3


A-703
CH(CH3)2
CH2—C(CH3)2—CH2—CH═CH2


A-704
CH(CH3)2
C(═CH2)—CH(CH3)—CH2—CH2—CH3


A-705
CH(CH3)2
C(CH3)═C(CH3)—CH2—CH2—CH3


A-706
CH(CH3)2
CH(CH3)—C(═CH2)—CH2—CH2—CH3


A-707
CH(CH3)2
CH(CH3)—C(CH3)═CH—CH2—CH3


A-708
CH(CH3)2
CH(CH3)—CH(CH3)—CH═CH—CH3


A-709
CH(CH3)2
CH(CH3)—CH(CH3)—CH2—CH═CH2


A-710
CH(CH3)2
C(CH3)2—CH═CH—CH2—CH3


A-711
CH(CH3)2
C(CH3)2—CH2—CH═CH—CH3


A-712
CH(CH3)2
C(CH3)2—CH2—CH2—CH═CH2


A-713
CH(CH3)2
CH═CH—CH(CH2—CH3)—CH2—CH3


A-714
CH(CH3)2
CH2—CH═C(CH2—CH3)—CH2—CH3


A-715
CH(CH3)2
CH2—CH2—C(═CH—CH3)—CH2—CH3


A-716
CH(CH3)2
CH2—CH2—CH(CH═CH2)—CH2—CH3


A-717
CH(CH3)2
CH═C(CH2—CH3)—CH2—CH2—CH3


A-718
CH(CH3)2
CH2—C(═CH—CH3)—CH2—CH2—CH3


A-719
CH(CH3)2
CH2—CH(CH═CH2)—CH2—CH2—CH3


A-720
CH(CH3)2
CH2—C(CH2—CH3)═CH—CH2—CH3


A-721
CH(CH3)2
CH2—CH(CH2—CH3)—CH═CH—CH3


A-722
CH(CH3)2
CH2—CH(CH2—CH3)—CH—CH═CH2


A-723
CH(CH3)2
C(═CH—CH3)—CH2—CH2—CH2—CH3


A-724
CH(CH3)2
CH(CH═CH2)—CH2—CH2—CH2—CH3


A-725
CH(CH3)2
C(CH2—CH3)═CH—CH2—CH2—CH3


A-726
CH(CH3)2
CH(CH2—CH3)—CH═CH—CH2—CH3


A-727
CH(CH3)2
CH(CH2—CH3)—CH2—CH═CH—CH3


A-728
CH(CH3)2
CH(CH2—CH3)—CH2—CH2—CH═CH2


A-729
CH(CH3)2
C(═CH—CH2—CH3)—CH2—CH2—CH3


A-730
CH(CH3)2
C(CH═CH—CH3)—CH2—CH2—CH3


A-731
CH(CH3)2
C(CH2—CH═CH2)—CH2—CH2—CH3


A-732
CH(CH3)2
CH═C(CH3)—C(CH3)3


A-733
CH(CH3)2
CH2—C(═CH2)—C(CH3)3


A-734
CH(CH3)2
CH2—C(CH3)2—CH(═CH2)—CH3


A-735
CH(CH3)2
C(═CH2)—CH(CH3)—CH(CH3)—CH3


A-736
CH(CH3)2
C(CH3)═C(CH3)—CH(CH3)—CH3


A-737
CH(CH3)2
CH(CH3)—C(═CH2)—CH(CH3)—CH3


A-738
CH(CH3)2
CH(CH3)—C(CH3)═C(CH3)—CH3


A-739
CH(CH3)2
CH(CH3)—CH(CH3)—C(═CH2)—CH3


A-740
CH(CH3)2
C(CH3)2—CH═C(CH3)—CH3


A-741
CH(CH3)2
C(CH3)2—CH2—C(═CH2)—CH3


A-742
CH(CH3)2
C(CH3)2—C(═CH2)—CH2—CH3


A-743
CH(CH3)2
C(CH3)2—C(CH3)═CH—CH3


A-744
CH(CH3)2
C(CH3)2—CH(CH3)CH═CH2


A-745
CH(CH3)2
CH(CH2—CH3)—CH2—CH(CH3)—CH3


A-746
CH(CH3)2
CH(CH2—CH3)—CH(CH3)—CH2—CH3


A-747
CH(CH3)2
C(CH3)(CH2—CH3)—CH2—CH2—CH3


A-748
CH(CH3)2
CH(i-C3H7)—CH2—CH2—CH3


A-749
CH(CH3)2
CH═C(CH2—CH3)—CH(CH3)—CH3


A-750
CH(CH3)2
CH2—C(═CH—CH3)—CH(CH3)—CH3


A-751
CH(CH3)2
CH2—CH(CH═CH2)—CH(CH3)—CH3


A-752
CH(CH3)2
CH2—C(CH2—CH3)═C(CH3)—CH3


A-753
CH(CH3)2
CH2—CH(CH2—CH3)—C(═CH2)—CH3


A-754
CH(CH3)2
CH2—C(CH3)(CH═CH2)—CH2—CH3


A-755
CH(CH3)2
C(═CH2)—CH(CH2—CH3)—CH2—CH3


A-756
CH(CH3)2
C(CH3)═C(CH2—CH3)—CH2—CH3


A-757
CH(CH3)2
CH(CH3)—C(═CH—CH3)—CH2—CH3


A-758
CH(CH3)2
CH(CH3)—CH(CH═CH2)—CH2—CH3


A-759
CH(CH3)2
CH═C(CH2—CH3)—CH(CH3)—CH3


A-760
CH(CH3)2
CH2—C(═CH—CH3)—CH(CH3)—CH3


A-761
CH(CH3)2
CH2—CH(CH═CH2)—CH(CH3)—CH3


A-762
CH(CH3)2
CH2—C(CH2—CH3)═C(CH3)—CH3


A-763
CH(CH3)2
CH2—CH(CH2—CH3)—C(═CH2)—CH3


A-764
CH(CH3)2
C(═CH—CH3)—CH2—CH(CH3)—CH3


A-765
CH(CH3)2
CH(CH═CH2)—CH2—CH(CH3)—CH3


A-766
CH(CH3)2
C(CH2—CH3)═CH—CH(CH3)—CH3


A-767
CH(CH3)2
CH(CH2—CH3)CH═C(CH3)—CH3


A-768
CH(CH3)2
CH(CH2—CH3)CH2—C(═CH2)—CH3


A-769
CH(CH3)2
C(═CH—CH3)CH(CH3)—CH2—CH3


A-770
CH(CH3)2
CH(CH═CH2)CH(CH3)—CH2—CH3


A-771
CH(CH3)2
C(CH2—CH3)═C(CH3)—CH2—CH3


A-772
CH(CH3)2
CH(CH2—CH3)—C(═CH2)—CH2—CH3


A-773
CH(CH3)2
CH(CH2—CH3)—C(CH3)═CH—CH3


A-774
CH(CH3)2
CH(CH2—CH3)—CH(CH3)—CH═CH2


A-775
CH(CH3)2
C(CH3)(CH═CH2)—CH2—CH2—CH3


A-776
CH(CH3)2
C(CH3)(CH2—CH3)—CH═CH—CH3


A-777
CH(CH3)2
C(CH3)(CH2—CH3)—CH2—CH═CH2


A-778
CH(CH3)2
C[═C(CH3)—CH3]—CH2—CH2—CH3


A-779
CH(CH3)2
CH[C(═CH2)—CH3]—CH2—CH2—CH3


A-780
CH(CH3)2
C(i-C3H7)═CH—CH2—CH3


A-781
CH(CH3)2
CH(i-C3H7)—CH═CH—CH3


A-782
CH(CH3)2
CH(i-C3H7)—CH2—CH═CH2


A-783
CH(CH3)2
C(═CH—CH3)—C(CH3)3


A-784
CH(CH3)2
CH(CH═CH2)—C(CH3)3


A-785
CH(CH3)2
C(CH3)(CH═CH2)CH(CH3)—CH3


A-786
CH(CH3)2
C(CH3)(CH2—CH3)C(═CH2)—CH3


A-787
CH(CH3)2
2-CH3-cyclohex-1-enyl


A-788
CH(CH3)2
[2-(═CH2)]-cyclo-C6H9


A-789
CH(CH3)2
2-CH3-cyclohex-2-enyl


A-790
CH(CH3)2
2-CH3-cyclohex-3-enyl


A-791
CH(CH3)2
2-CH3-cyclohex-4-enyl


A-792
CH(CH3)2
2-CH3-cyclohex-5-enyl


A-793
CH(CH3)2
2-CH3-cyclohex-6-enyl


A-794
CH(CH3)2
3-CH3-cyclohex-1-enyl


A-795
CH(CH3)2
3-CH3-cyclohex-2-enyl


A-796
CH(CH3)2
[3-(═CH2)]-cyclo-C6H9


A-797
CH(CH3)2
3-CH3-cyclohex-3-enyl


A-798
CH(CH3)2
3-CH3-cyclohex-4-enyl


A-799
CH(CH3)2
3-CH3-cyclohex-5-enyl


A-800
CH(CH3)2
3-CH3-cyclohex-6-enyl


A-801
CH(CH3)2
4-CH3-cyclohex-1-enyl


A-802
CH(CH3)2
4-CH3-cyclohex-2-enyl


A-803
CH(CH3)2
4-CH3-cyclohex-3-enyl


A-804
CH(CH3)2
[4-(═CH2)]-cyclo-C6H9


A-805
CH(CH3)2
CH2CF3


A-806
CH(CH3)2
CH2CCl3


A-807
CH(CH3)2
CH2(cyclo-C3H5)


A-808
CH2(cyclo-C3H5)
CH2CH3


A-809
CH2(cyclo-C3H5)
CH2CH2CH3


A-810
CH2(cyclo-C3H5)
CH2CH2F


A-811
CH2(cyclo-C3H5)
H


A-812
CH2(cyclo-C3H5)
CH(CH3)2


A-813
CH2(cyclo-C3H5)
CH2C(CH3)3


A-814
CH2(cyclo-C3H5)
CH2CH(CH3)2


A-815
CH2(cyclo-C3H5)
(±)CH(CH2CH3)CH3


A-816
CH2(cyclo-C3H5)
(R)CH(CH2CH3)CH3


A-817
CH2(cyclo-C3H5)
(S)CH(CH2CH3)CH3


A-818
CH2(cyclo-C3H5)
(±)CH(CH3)—CH(CH3)2


A-819
CH2(cyclo-C3H5)
(R)CH(CH3)—CH(CH3)2


A-820
CH2(cyclo-C3H5)
(S)CH(CH3)—CH(CH3)2


A-821
CH2(cyclo-C3H5)
(±)CH(CH3)—C(CH3)3


A-822
CH2(cyclo-C3H5)
(R)CH(CH3)—C(CH3)3


A-823
CH2(cyclo-C3H5)
(S)CH(CH3)—C(CH3)3


A-824
CH2(cyclo-C3H5)
(±)CH(CH3)—CF3


A-825
CH2(cyclo-C3H5)
(R)CH(CH3)—CF3


A-826
CH2(cyclo-C3H5)
(S)CH(CH3)—CF3


A-827
CH2(cyclo-C3H5)
(±)CH(CH3)—CCl3


A-828
CH2(cyclo-C3H5)
(R)CH(CH3)—CCl3


A-829
CH2(cyclo-C3H5)
(S)CH(CH3)—CCl3


A-830
CH2(cyclo-C3H5)
CH2C(CH3)═CH2


A-831
CH2(cyclo-C3H5)
cyclopentyl


A-832
CH2(cyclo-C3H5)
cyclohexyl


A-833
CH2(cyclo-C3H5)
(CH2)3CH3


A-834
CH2(cyclo-C3H5)
C(CH3)3


A-835
CH2(cyclo-C3H5)
(CH2)4CH3


A-836
CH2(cyclo-C3H5)
CH(CH2CH3)2


A-837
CH2(cyclo-C3H5)
CH2CH2CH(CH3)2


A-838
CH2(cyclo-C3H5)
(±)CH(CH3)(CH2)2CH3


A-839
CH2(cyclo-C3H5)
(R)CH(CH3)(CH2)2CH3


A-840
CH2(cyclo-C3H5)
(S)CH(CH3)(CH2)2CH3


A-841
CH2(cyclo-C3H5)
(±)CH2CH(CH3)CH2CH3


A-842
CH2(cyclo-C3H5)
(R)CH2CH(CH3)CH2CH3


A-843
CH2(cyclo-C3H5)
(S)CH2CH(CH3)CH2CH3


A-844
CH2(cyclo-C3H5)
(±)CH(CH3)CH(CH3)2


A-845
CH2(cyclo-C3H5)
(R)CH(CH3)CH(CH3)2


A-846
CH2(cyclo-C3H5)
(S)CH(CH3)CH(CH3)2


A-847
CH2(cyclo-C3H5)
(CH2)5CH3


A-848
CH2(cyclo-C3H5)
(±,±)CH(CH3)CH(CH3)CH2CH3


A-849
CH2(cyclo-C3H5)
(±,R)CH(CH3)CH(CH3)CH2CH3


A-850
CH2(cyclo-C3H5)
(±,S)CH(CH3)CH(CH3)CH2CH3


A-851
CH2(cyclo-C3H5)
(±)CH2CH(CH3)CF3


A-852
CH2(cyclo-C3H5)
(R)CH2CH(CH3)CF3


A-853
CH2(cyclo-C3H5)
(S)CH2CH(CH3)CF3


A-854
CH2(cyclo-C3H5)
(±)CH2CH(CF3)CH2CH3


A-855
CH2(cyclo-C3H5)
(R)CH2CH(CF3)CH2CH3


A-856
CH2(cyclo-C3H5)
(S)CH2CH(CF3)CH2CH3


A-857
CH2(cyclo-C3H5)
(±,±)CH(CH3)CH(CH3)CF3


A-858
CH2(cyclo-C3H5)
(±,R)CH(CH3)CH(CH3)CF3


A-859
CH2(cyclo-C3H5)
(±,S)CH(CH3)CH(CH3)CF3


A-860
CH2(cyclo-C3H5)
(±,±)CH(CH3)CH(CF3)CH2CH3


A-861
CH2(cyclo-C3H5)
(±,R)CH(CH3)CH(CF3)CH2CH3


A-862
CH2(cyclo-C3H5)
(±,S)CH(CH3)CH(CF3)CH2CH3


A-863
CH2(cyclo-C3H5)
CF3


A-864
CH2(cyclo-C3H5)
CF2CF3


A-865
CH2(cyclo-C3H5)
CF2CF2CF3


A-866
CH2(cyclo-C3H5)
cyclo-C3H5


A-867
CH2(cyclo-C3H5)
(1-CH3)-cyclo-C3H4


A-868
CH2(cyclo-C3H5)
cyclo-C5H9


A-869
CH2(cyclo-C3H5)
cyclo-C6H11


A-870
CH2(cyclo-C3H5)
(4-CH3)-cyclo-C6H10


A-871
CH2(cyclo-C3H5)
CH2C(CH3)═CH2


A-872
CH2(cyclo-C3H5)
CH2CH2C(CH3)═CH2


A-873
CH2(cyclo-C3H5)
CH2—C(CH3)3


A-874
CH2(cyclo-C3H5)
CH2—Si(CH3)3


A-875
CH2(cyclo-C3H5)
n-C6H13


A-876
CH2(cyclo-C3H5)
(CH2)3—CH(CH3)2


A-877
CH2(cyclo-C3H5)
(CH2)2—CH(CH3)—C2H5


A-878
CH2(cyclo-C3H5)
CH2—CH(CH3)-n-C3H7


A-879
CH2(cyclo-C3H5)
CH(CH3)-n-C4H9


A-880
CH2(cyclo-C3H5)
CH2—CH(C2H5)2


A-881
CH2(cyclo-C3H5)
CH(C2H5)-n-C3H7


A-882
CH2(cyclo-C3H5)
CH2-cyclo-C5H9


A-883
CH2(cyclo-C3H5)
CH2—CH(CH3)—CH(CH3)2


A-884
CH2(cyclo-C3H5)
CH(CH3)—CH2CH(CH3)2


A-885
CH2(cyclo-C3H5)
CH(CH3)—CH(CH3)—C2H5


A-886
CH2(cyclo-C3H5)
CH(CH3)—C(CH3)3


A-887
CH2(cyclo-C3H5)
(CH2)2—C(CH3)3


A-888
CH2(cyclo-C3H5)
CH2—C(CH3)2—C2H5


A-889
CH2(cyclo-C3H5)
2-CH3-cyclo-C5H8


A-890
CH2(cyclo-C3H5)
3-CH3-cyclo-C5H8


A-891
CH2(cyclo-C3H5)
C(CH3)2-n-C3H7


A-892
CH2(cyclo-C3H5)
(CH2)6—CH3


A-893
CH2(cyclo-C3H5)
(CH2)4—CH(CH3)2


A-894
CH2(cyclo-C3H5)
(CH2)3—CH(CH3)—C2H5


A-895
CH2(cyclo-C3H5)
(CH2)2—CH(CH3)-n-C3H7


A-896
CH2(cyclo-C3H5)
CH2—CH(CH3)-n-C4H9


A-897
CH2(cyclo-C3H5)
CH(CH3)-n-C5H11


A-898
CH2(cyclo-C3H5)
(CH2)3C(CH3)3


A-899
CH2(cyclo-C3H5)
(CH2)2CH(CH3)—CH(CH3)2


A-900
CH2(cyclo-C3H5)
(CH2)CH(CH3)—CH2CH(CH3)2


A-901
CH2(cyclo-C3H5)
CH(CH3)(CH2)2—CH(CH3)2


A-902
CH2(cyclo-C3H5)
(CH2)2C(CH3)2C2H5


A-903
CH2(cyclo-C3H5)
CH2CH(CH3)CH(CH3)C2H5


A-904
CH2(cyclo-C3H5)
CH(CH3)CH2CH(CH3)C2H5


A-905
CH2(cyclo-C3H5)
CH2C(CH3)2-n-C3H7


A-906
CH2(cyclo-C3H5)
CH(CH3)CH(CH3)-n-C3H7


A-907
CH2(cyclo-C3H5)
C(CH3)2-n-C4H9


A-908
CH2(cyclo-C3H5)
(CH2)2CH(C2H5)2


A-909
CH2(cyclo-C3H5)
CH2CH(C2H5)-n-C3H7


A-910
CH2(cyclo-C3H5)
CH(C2H5)-n-C4H9


A-911
CH2(cyclo-C3H5)
CH2CH(CH3)C(CH3)3


A-912
CH2(cyclo-C3H5)
CH(CH3)CH2C(CH3)3


A-913
CH2(cyclo-C3H5)
CH2C(CH3)2CH(CH3)2


A-914
CH2(cyclo-C3H5)
CH2CH(C2H5)CH(CH3)2


A-915
CH2(cyclo-C3H5)
CH(CH3)CH(CH3)CH(CH3)2


A-916
CH2(cyclo-C3H5)
C(CH3)2CH2CH(CH3)2


A-917
CH2(cyclo-C3H5)
CH(C2H5)CH2CH(CH3)2


A-918
CH2(cyclo-C3H5)
CH(CH3)C(CH3)2C2H5


A-919
CH2(cyclo-C3H5)
CH(CH3)CH(C2H5)2


A-920
CH2(cyclo-C3H5)
C(CH3)2CH(CH3)C2H5


A-921
CH2(cyclo-C3H5)
CH(C2H5)CH(CH3)C2H5


A-922
CH2(cyclo-C3H5)
C(CH3)(C2H5)-n-C3H7


A-923
CH2(cyclo-C3H5)
CH(n-C3H7)2


A-924
CH2(cyclo-C3H5)
CH(n-C3H7)CH(CH3)2


A-925
CH2(cyclo-C3H5)
C(CH3)2C(CH3)3


A-926
CH2(cyclo-C3H5)
C(CH3)(C2H5)—CH(CH3)2


A-927
CH2(cyclo-C3H5)
C(C2H5)3


A-928
CH2(cyclo-C3H5)
(3-CH3)-cyclo-C6H10


A-929
CH2(cyclo-C3H5)
(2-CH3)-cyclo-C6H10


A-930
CH2(cyclo-C3H5)
n-C8H17


A-931
CH2(cyclo-C3H5)
CH2C(═NO—CH3)CH3


A-932
CH2(cyclo-C3H5)
CH2C(═NO—C2H5)CH3


A-933
CH2(cyclo-C3H5)
CH2C(═NO-n-C3H7)CH3


A-934
CH2(cyclo-C3H5)
CH2C(═NO-i-C3H7)CH3


A-935
CH2(cyclo-C3H5)
CH(CH3)C(═NOCH3)CH3


A-936
CH2(cyclo-C3H5)
CH(CH3)C(═NOC2H5)CH3


A-937
CH2(cyclo-C3H5)
CH(CH3)C(═NO-n-C3H7)CH3


A-938
CH2(cyclo-C3H5)
CH(CH3)C(═NO-i-C3H7)CH3


A-939
CH2(cyclo-C3H5)
CH2C(═NO—CH3)C2H5


A-940
CH2(cyclo-C3H5)
CH2C(═NO—C2H5)C2H5


A-941
CH2(cyclo-C3H5)
CH2C(═NO-n-C3H7)C2H5


A-942
CH2(cyclo-C3H5)
CH2C(═NO-i-C3H7)C2H5


A-943
CH2(cyclo-C3H5)
CH(CH3)C(═NOCH3)C2H5


A-944
CH2(cyclo-C3H5)
CH(CH3)C(═NOC2H5)C2H5


A-945
CH2(cyclo-C3H5)
CH(CH3)C(═NO-n-C3H7)C2H5


A-946
CH2(cyclo-C3H5)
CH(CH3)C(═NO-n-C3H7)C2H5


A-947
CH2(cyclo-C3H5)
CH═CH—CH2CH3


A-948
CH2(cyclo-C3H5)
CH2—CH═CH—CH3


A-949
CH2(cyclo-C3H5)
CH2—CH2—CH═CH2


A-950
CH2(cyclo-C3H5)
C(CH3)2CH2CH3


A-951
CH2(cyclo-C3H5)
CH═C(CH3)2


A-952
CH2(cyclo-C3H5)
C(═CH2)—CH2CH3


A-953
CH2(cyclo-C3H5)
C(CH3)═CH—CH3


A-954
CH2(cyclo-C3H5)
CH(CH3)CH═CH2


A-955
CH2(cyclo-C3H5)
CH═CH-n-C3H7


A-956
CH2(cyclo-C3H5)
CH2—CH═CH—C2H5


A-957
CH2(cyclo-C3H5)
(CH2)2—CH═CH—CH3


A-958
CH2(cyclo-C3H5)
(CH2)3—CH═CH2


A-959
CH2(cyclo-C3H5)
CH═CH—CH(CH3)2


A-960
CH2(cyclo-C3H5)
CH2—CH═C(CH3)2


A-961
CH2(cyclo-C3H5)
(CH2)2—C(CH3)═CH2


A-962
CH2(cyclo-C3H5)
CH═C(CH3)—C2H5


A-963
CH2(cyclo-C3H5)
CH2—C(═CH2)—C2H5


A-964
CH2(cyclo-C3H5)
CH2—C(CH3)═CH—CH3


A-965
CH2(cyclo-C3H5)
CH2—CH(CH3)—CH═CH2


A-966
CH2(cyclo-C3H5)
C(═CH2)—CH2—CH2—CH3


A-967
CH2(cyclo-C3H5)
C(CH3)═CH—CH2—CH3


A-968
CH2(cyclo-C3H5)
CH(CH3)—CH═CH—CH3


A-969
CH2(cyclo-C3H5)
CH(CH3)—CH2—CH═CH2


A-970
CH2(cyclo-C3H5)
C(═CH2)CH(CH3)2


A-971
CH2(cyclo-C3H5)
C(CH3)═C(CH3)2


A-972
CH2(cyclo-C3H5)
CH(CH3)—C(═CH2)—CH3


A-973
CH2(cyclo-C3H5)
C(CH3)2—CH═CH2


A-974
CH2(cyclo-C3H5)
C(C2H5)═CH—CH3


A-975
CH2(cyclo-C3H5)
CH(C2H5)—CH═CH2


A-976
CH2(cyclo-C3H5)
CH═CH—CH2—CH2—CH2—CH3


A-977
CH2(cyclo-C3H5)
CH2—CH═CH—CH2—CH2—CH3


A-978
CH2(cyclo-C3H5)
CH2—CH2—CH═CH—CH2—CH3


A-979
CH2(cyclo-C3H5)
CH2—CH2—CH2—CH═CH—CH3


A-980
CH2(cyclo-C3H5)
CH2—CH2—CH2—CH2—CH═CH2


A-981
CH2(cyclo-C3H5)
CH═CH—CH2—CH(CH3)CH3


A-982
CH2(cyclo-C3H5)
CH2—CH═CH—CH(CH3)CH3


A-983
CH2(cyclo-C3H5)
CH2—CH2—CH═C(CH3)CH3


A-984
CH2(cyclo-C3H5)
CH2—CH2—CH2—C(CH3)═CH2


A-985
CH2(cyclo-C3H5)
CH═CH—CH(CH3)—CH2—CH3


A-986
CH2(cyclo-C3H5)
CH2—CH═C(CH3)—CH2—CH3


A-987
CH2(cyclo-C3H5)
CH2—CH2—C(═CH2)—CH2—CH3


A-988
CH2(cyclo-C3H5)
CH2—CH2—C(CH3)═CH—CH3


A-989
CH2(cyclo-C3H5)
CH2—CH2—CH(CH3)—CH═CH2


A-990
CH2(cyclo-C3H5)
CH═C(CH3)—CH2—CH2—CH3


A-991
CH2(cyclo-C3H5)
CH2—C(═CH2)—CH2—CH2—CH3


A-992
CH2(cyclo-C3H5)
CH2—C(CH3)═CH—CH2—CH3


A-993
CH2(cyclo-C3H5)
CH2—CH(CH3)—CH═CH—CH3


A-994
CH2(cyclo-C3H5)
CH2—CH(CH3)—CH2—CH═CH2


A-995
CH2(cyclo-C3H5)
C(═CH2)—CH2—CH2—CH2—CH3


A-996
CH2(cyclo-C3H5)
C(CH3)═CH—CH2—CH2—CH3


A-997
CH2(cyclo-C3H5)
CH(CH3)—CH═CH—CH2—CH3


A-998
CH2(cyclo-C3H5)
CH(CH3)—CH2—CH═CH—CH3


A-999
CH2(cyclo-C3H5)
CH(CH3)—CH2—CH2—CH═CH2


A-1000
CH2(cyclo-C3H5)
CH═CH—C(CH3)3


A-1001
CH2(cyclo-C3H5)
CH═C(CH3)—CH(CH3)—CH3


A-1002
CH2(cyclo-C3H5)
CH2—C(═CH2)—CH(CH3)—CH3


A-1003
CH2(cyclo-C3H5)
CH2—C(CH3)═C(CH3)—CH3


A-1004
CH2(cyclo-C3H5)
CH2—CH(CH3)—C(═CH2)—CH3


A-1005
CH2(cyclo-C3H5)
C(═CH2)—CH2—CH(CH3)—CH3


A-1006
CH2(cyclo-C3H5)
C(CH3)═CH—CH(CH3)—CH3


A-1007
CH2(cyclo-C3H5)
CH(CH3)—CH═C(CH3)—CH3


A-1008
CH2(cyclo-C3H5)
CH(CH3)—CH2—C(═CH2)—CH3


A-1009
CH2(cyclo-C3H5)
CH═C(CH2—CH3)—CH2—CH3


A-1010
CH2(cyclo-C3H5)
CH2—C(═CH—CH3)—CH2—CH3


A-1011
CH2(cyclo-C3H5)
CH2—CH(CH═CH2)—CH2—CH3


A-1012
CH2(cyclo-C3H5)
C(═CH—CH3)—CH2—CH2—CH3


A-1013
CH2(cyclo-C3H5)
CH(CH═CH2)—CH2—CH2—CH3


A-1014
CH2(cyclo-C3H5)
C(CH2—CH3)═CH—CH2—CH3


A-1015
CH2(cyclo-C3H5)
CH(CH2—CH3)—CH═CH—CH3


A-1016
CH2(cyclo-C3H5)
CH(CH2—CH3)—CH2—CH═CH2


A-1017
CH2(cyclo-C3H5)
CH2—C(CH3)2—CH═CH2


A-1018
CH2(cyclo-C3H5)
C(═CH2)—CH(CH3)—CH2—CH3


A-1019
CH2(cyclo-C3H5)
C(CH3)═C(CH3)—CH2—CH3


A-1020
CH2(cyclo-C3H5)
CH(CH3)—C(═CH2)—CH2—CH3


A-1021
CH2(cyclo-C3H5)
CH(CH3)—C(CH3)═CH—CH3


A-1022
CH2(cyclo-C3H5)
CH(CH3)—CH(CH3)—CH═CH2


A-1023
CH2(cyclo-C3H5)
C(CH3)2—CH═CH—CH3


A-1024
CH2(cyclo-C3H5)
C(CH3)2—CH2—CH═CH2


A-1025
CH2(cyclo-C3H5)
C(═CH2)—C(CH3)3


A-1026
CH2(cyclo-C3H5)
C(═CH—CH3)—CH(CH3)—CH3


A-1027
CH2(cyclo-C3H5)
CH(CH═CH2)—CH(CH3)—CH3


A-1028
CH2(cyclo-C3H5)
C(CH2—CH3)═C(CH3)—CH3


A-1029
CH2(cyclo-C3H5)
CH(CH2—CH3)—C(═CH2)—CH3


A-1030
CH2(cyclo-C3H5)
C(CH3)2—C(═CH2)—CH3


A-1031
CH2(cyclo-C3H5)
C(CH3)(CH═CH2)—CH2—CH3


A-1032
CH2(cyclo-C3H5)
C(CH3)(CH2CH3)—CH2—CH2—CH3


A-1033
CH2(cyclo-C3H5)
CH(CH2CH3)—CH(CH3)—CH2—CH3


A-1034
CH2(cyclo-C3H5)
CH(CH2CH3)—CH2—CH(CH3)—CH3


A-1035
CH2(cyclo-C3H5)
C(CH3)2—C(CH3)3


A-1036
CH2(cyclo-C3H5)
C(CH2—CH3)—C(CH3)3


A-1037
CH2(cyclo-C3H5)
C(CH3)(CH2—CH3)—CH(CH3)2


A-1038
CH2(cyclo-C3H5)
CH(CH(CH3)2)—CH(CH3)2


A-1039
CH2(cyclo-C3H5)
CH═CH—CH2—CH2—CH2—CH2—CH3


A-1040
CH2(cyclo-C3H5)
CH2—CH═CH—CH2—CH2—CH2—CH3


A-1041
CH2(cyclo-C3H5)
CH2—CH2—CH═CH—CH2—CH2—CH3


A-1042
CH2(cyclo-C3H5)
CH2—CH2—CH2—CH═CH—CH2—CH3


A-1043
CH2(cyclo-C3H5)
CH2—CH2—CH2—CH2—CH═CH—CH3


A-1044
CH2(cyclo-C3H5)
CH2—CH2—CH2—CH2—CH2—CH═CH2


A-1045
CH2(cyclo-C3H5)
CH═CH—CH2—CH2—CH(CH3)—CH3


A-1046
CH2(cyclo-C3H5)
CH2—CH═CH—CH2—CH(CH3)—CH3


A-1047
CH2(cyclo-C3H5)
CH2—CH2—CH═CH—CH(CH3)—CH3


A-1048
CH2(cyclo-C3H5)
CH2—CH2—CH2—CH═C(CH3)—CH3


A-1049
CH2(cyclo-C3H5)
CH2—CH2—CH2—CH2—C(═CH2)—CH3


A-1050
CH2(cyclo-C3H5)
CH═CH—CH2—CH(CH3)—CH2—CH3


A-1051
CH2(cyclo-C3H5)
CH2—CH═CH—CH(CH3)—CH2—CH3


A-1052
CH2(cyclo-C3H5)
CH2—CH2—CH═C(CH3)—CH2—CH3


A-1053
CH2(cyclo-C3H5)
CH2—CH2—CH2—C(═CH2)—CH2—CH3


A-1054
CH2(cyclo-C3H5)
CH2—CH2—CH2—C(CH3)═CH—CH3


A-1055
CH2(cyclo-C3H5)
CH2—CH2—CH2—CH(CH3)—CH═CH2


A-1056
CH2(cyclo-C3H5)
CH═CH—CH(CH3)—CH2—CH2—CH3


A-1057
CH2(cyclo-C3H5)
CH2—CH═C(CH3)—CH2—CH2—CH3


A-1058
CH2(cyclo-C3H5)
CH2—CH2—C(═CH2)—CH2—CH2—CH3


A-1059
CH2(cyclo-C3H5)
CH2—CH2—C(CH3)═CH—CH2—CH3


A-1060
CH2(cyclo-C3H5)
CH2—CH2—CH(CH3)—CH═CH—CH3


A-1061
CH2(cyclo-C3H5)
CH2—CH2—CH(CH3)—CH2—CH═CH2


A-1062
CH2(cyclo-C3H5)
CH═C(CH3)—CH2—CH2—CH2—CH3


A-1063
CH2(cyclo-C3H5)
CH2—C(═CH2)—CH2—CH2—CH2—CH3


A-1064
CH2(cyclo-C3H5)
CH2—C(CH3)═CH—CH2—CH2—CH3


A-1065
CH2(cyclo-C3H5)
CH2—CH(CH3)—CH═CH—CH2—CH3


A-1066
CH2(cyclo-C3H5)
CH2—CH(CH3)—CH2—CH═CH—CH3


A-1067
CH2(cyclo-C3H5)
CH2—CH(CH3)—CH2—CH2—CH═CH2


A-1068
CH2(cyclo-C3H5)
C(═CH2)—CH2—CH2—CH2—CH2—CH3


A-1069
CH2(cyclo-C3H5)
C(CH3)═CH—CH2—CH2—CH2—CH3


A-1070
CH2(cyclo-C3H5)
CH(CH3)—CH═CH—CH2—CH2—CH3


A-1071
CH2(cyclo-C3H5)
CH(CH3)—CH2—CH═CH—CH2—CH3


A-1072
CH2(cyclo-C3H5)
CH(CH3)—CH2—CH2—CH═CH—CH3


A-1073
CH2(cyclo-C3H5)
CH(CH3)—CH2—CH2—CH2—CH═CH2


A-1074
CH2(cyclo-C3H5)
CH═CH—CH2—C(CH3)3


A-1075
CH2(cyclo-C3H5)
CH2—CH═CH—C(CH3)3


A-1076
CH2(cyclo-C3H5)
CH═CH—CH(CH3)—CH(CH3)2


A-1077
CH2(cyclo-C3H5)
CH2—CH═C(CH3)—CH(CH3)2


A-1078
CH2(cyclo-C3H5)
CH2—CH2—C(═CH2)—CH(CH3)2


A-1079
CH2(cyclo-C3H5)
CH2—CH2—C(CH3)═C(CH3)2


A-1080
CH2(cyclo-C3H5)
CH2—CH2—CH(CH3)—C(═CH2)—CH3


A-1081
CH2(cyclo-C3H5)
CH═C(CH3)—CH2—CH(CH3)2


A-1082
CH2(cyclo-C3H5)
CH2—C(═CH2)—CH2—CH(CH3)2


A-1083
CH2(cyclo-C3H5)
CH2—C(CH3)═CH—CH(CH3)2


A-1084
CH2(cyclo-C3H5)
CH2—CH(CH3)—CH═C(CH3)2


A-1085
CH2(cyclo-C3H5)
CH2—CH(CH3)—CH2—C(═CH2)—CH3


A-1086
CH2(cyclo-C3H5)
C(═CH2)—CH2—CH2—CH(CH3)2


A-1087
CH2(cyclo-C3H5)
C(CH3)═CH—CH2—CH(CH3)2


A-1088
CH2(cyclo-C3H5)
CH(CH3)—CH═CH—CH(CH3)2


A-1089
CH2(cyclo-C3H5)
CH(CH3)—CH2—CH═C(CH3)2


A-1090
CH2(cyclo-C3H5)
CH(CH3)—CH2—CH2—C(═CH2)—CH3


A-1091
CH2(cyclo-C3H5)
CH═CH—C(CH3)2—CH2—CH3


A-1092
CH2(cyclo-C3H5)
CH2—CH2—C(CH3)2—CH═CH2


A-1093
CH2(cyclo-C3H5)
CH═C(CH3)—CH(CH3)—CH2—CH3


A-1094
CH2(cyclo-C3H5)
CH2—C(═CH2)—CH(CH3)—CH2—CH3


A-1095
CH2(cyclo-C3H5)
CH2—C(CH3)═C(CH3)—CH2—CH3


A-1096
CH2(cyclo-C3H5)
CH2—CH(CH3)—C(═CH2)—CH2—CH3


A-1097
CH2(cyclo-C3H5)
CH2—CH(CH3)—C(CH3)═CH—CH3


A-1098
CH2(cyclo-C3H5)
CH2—CH(CH3)—CH(CH3)—CH═CH2


A-1099
CH2(cyclo-C3H5)
C(═CH2)—CH2—CH(CH3)—CH2—CH3


A-1100
CH2(cyclo-C3H5)
C(CH3)═CH—CH(CH3)—CH2—CH3


A-1101
CH2(cyclo-C3H5)
CH(CH3)—CH═C(CH3)—CH2—CH3


A-1102
CH2(cyclo-C3H5)
CH(CH3)—CH2—C(═CH2)—CH2—CH3


A-1103
CH2(cyclo-C3H5)
CH(CH3)—CH2—C(CH3)═CH—CH3


A-1104
CH2(cyclo-C3H5)
CH(CH3)—CH2—CH(CH3)—CH═CH2


A-1105
CH2(cyclo-C3H5)
CH2—C(CH3)2—CH═CH—CH3


A-1106
CH2(cyclo-C3H5)
CH2—C(CH3)2—CH2—CH═CH2


A-1107
CH2(cyclo-C3H5)
C(═CH2)—CH(CH3)—CH2—CH2—CH3


A-1108
CH2(cyclo-C3H5)
C(CH3)═C(CH3)—CH2—CH2—CH3


A-1109
CH2(cyclo-C3H5)
CH(CH3)—C(═CH2)—CH2—CH2—CH3


A-1110
CH2(cyclo-C3H5)
CH(CH3)—C(CH3)═CH—CH2—CH3


A-1111
CH2(cyclo-C3H5)
CH(CH3)—CH(CH3)—CH═CH—CH3


A-1112
CH2(cyclo-C3H5)
CH(CH3)—CH(CH3)—CH2—CH═CH2


A-1113
CH2(cyclo-C3H5)
C(CH3)2—CH═CH—CH2—CH3


A-1114
CH2(cyclo-C3H5)
C(CH3)2—CH2—CH═CH—CH3


A-1115
CH2(cyclo-C3H5)
C(CH3)2—CH2—CH2—CH═CH2


A-1116
CH2(cyclo-C3H5)
CH═CH—CH(CH2—CH3)—CH2—CH3


A-1117
CH2(cyclo-C3H5)
CH2—CH═C(CH2—CH3)—CH2—CH3


A-1118
CH2(cyclo-C3H5)
CH2—CH2—C(═CH—CH3)—CH2—CH3


A-1119
CH2(cyclo-C3H5)
CH2—CH2—CH(CH═CH2)—CH2—CH3


A-1120
CH2(cyclo-C3H5)
CH═C(CH2—CH3)—CH2—CH2—CH3


A-1121
CH2(cyclo-C3H5)
CH2—C(═CH—CH3)—CH2—CH2—CH3


A-1122
CH2(cyclo-C3H5)
CH2—CH(CH═CH2)—CH2—CH2—CH3


A-1123
CH2(cyclo-C3H5)
CH2—C(CH2—CH3)═CH—CH2—CH3


A-1124
CH2(cyclo-C3H5)
CH2—CH(CH2—CH3)—CH═CH—CH3


A-1125
CH2(cyclo-C3H5)
CH2—CH(CH2—CH3)—CH—CH═CH2


A-1126
CH2(cyclo-C3H5)
C(═CH—CH3)—CH2—CH2—CH2—CH3


A-1127
CH2(cyclo-C3H5)
CH(CH═CH2)—CH2—CH2—CH2—CH3


A-1128
CH2(cyclo-C3H5)
C(CH2—CH3)═CH—CH2—CH2—CH3


A-1129
CH2(cyclo-C3H5)
CH(CH2—CH3)—CH═CH—CH2—CH3


A-1130
CH2(cyclo-C3H5)
CH(CH2—CH3)—CH2—CH═CH—CH3


A-1131
CH2(cyclo-C3H5)
CH(CH2—CH3)—CH2—CH2—CH═CH2


A-1132
CH2(cyclo-C3H5)
C(═CH—CH2—CH3)—CH2—CH2—CH3


A-1133
CH2(cyclo-C3H5)
C(CH═CH—CH3)—CH2—CH2—CH3


A-1134
CH2(cyclo-C3H5)
C(CH2—CH═CH2)—CH2—CH2—CH3


A-1135
CH2(cyclo-C3H5)
CH═C(CH3)—C(CH3)3


A-1136
CH2(cyclo-C3H5)
CH2—C(═CH2)—C(CH3)3


A-1137
CH2(cyclo-C3H5)
CH2—C(CH3)2—CH(═CH2)—CH3


A-1138
CH2(cyclo-C3H5)
C(═CH2)—CH(CH3)—CH(CH3)—CH3


A-1139
CH2(cyclo-C3H5)
C(CH3)═C(CH3)—CH(CH3)—CH3


A-1140
CH2(cyclo-C3H5)
CH(CH3)—C(═CH2)—CH(CH3)—CH3


A-1141
CH2(cyclo-C3H5)
CH(CH3)—C(CH3)═C(CH3)—CH3


A-1142
CH2(cyclo-C3H5)
CH(CH3)—CH(CH3)—C(═CH2)—CH3


A-1143
CH2(cyclo-C3H5)
C(CH3)2—CH═C(CH3)—CH3


A-1144
CH2(cyclo-C3H5)
C(CH3)2—CH2—C(═CH2)—CH3


A-1145
CH2(cyclo-C3H5)
C(CH3)2—C(═CH2)—CH2—CH3


A-1146
CH2(cyclo-C3H5)
C(CH3)2—C(CH3)═CH—CH3


A-1147
CH2(cyclo-C3H5)
C(CH3)2—CH(CH3)CH═CH2


A-1148
CH2(cyclo-C3H5)
CH(CH2—CH3)—CH2—CH(CH3)—CH3


A-1149
CH2(cyclo-C3H5)
CH(CH2—CH3)—CH(CH3)—CH2—CH3


A-1150
CH2(cyclo-C3H5)
C(CH3)(CH2—CH3)—CH2—CH2—CH3


A-1151
CH2(cyclo-C3H5)
CH(i-C3H7)—CH2—CH2—CH3


A-1152
CH2(cyclo-C3H5)
CH═C(CH2—CH3)—CH(CH3)—CH3


A-1153
CH2(cyclo-C3H5)
CH2—C(═CH—CH3)—CH(CH3)—CH3


A-1154
CH2(cyclo-C3H5)
CH2—CH(CH═CH2)—CH(CH3)—CH3


A-1155
CH2(cyclo-C3H5)
CH2—C(CH2—CH3)═C(CH3)—CH3


A-1156
CH2(cyclo-C3H5)
CH2—CH(CH2—CH3)—(═CH2)—CH3


A-1157
CH2(cyclo-C3H5)
CH2—C(CH3)(CH═CH2)—CH2—CH3


A-1158
CH2(cyclo-C3H5)
C(═CH2)—CH(CH2—CH3)—CH2—CH3


A-1159
CH2(cyclo-C3H5)
C(CH3)═C(CH2—CH3)—CH2—CH3


A-1160
CH2(cyclo-C3H5)
CH(CH3)—C(═CH—CH3)—CH2—CH3


A-1161
CH2(cyclo-C3H5)
CH(CH3)—CH(CH═CH2)—CH2—CH3


A-1162
CH2(cyclo-C3H5)
CH═C(CH2—CH3)—CH(CH3)—CH3


A-1163
CH2(cyclo-C3H5)
CH2—C(═CH—CH3)—CH(CH3)—CH3


A-1164
CH2(cyclo-C3H5)
CH2—CH(CH═CH2)—CH(CH3)—CH3


A-1165
CH2(cyclo-C3H5)
CH2—C(CH2—CH3)═C(CH3)—CH3


A-1166
CH2(cyclo-C3H5)
CH2—CH(CH2—CH3)—C(═CH2)—CH3


A-1167
CH2(cyclo-C3H5)
C(═CH—CH3)—CH2—CH(CH3)—CH3


A-1168
CH2(cyclo-C3H5)
CH(CH═CH2)—CH2—CH(CH3)—CH3


A-1169
CH2(cyclo-C3H5)
C(CH2—CH3)═CH—CH(CH3)—CH3


A-1170
CH2(cyclo-C3H5)
CH(CH2—CH3)CH═C(CH3)—CH3


A-1171
CH2(cyclo-C3H5)
CH(CH2—CH3)CH2—C(═CH2)—CH3


A-1172
CH2(cyclo-C3H5)
C(═CH—CH3)CH(CH3)—CH2—CH3


A-1173
CH2(cyclo-C3H5)
CH(CH═CH2)CH(CH3)—CH2—CH3


A-1174
CH2(cyclo-C3H5)
C(CH2—CH3)═C(CH3)—CH2—CH3


A-1175
CH2(cyclo-C3H5)
CH(CH2—CH3)—C(═CH2)—CH2—CH3


A-1176
CH2(cyclo-C3H5)
CH(CH2—CH3)—C(CH3)═CH—CH3


A-1177
CH2(cyclo-C3H5)
CH(CH2—CH3)—CH(CH3)—CH═CH2


A-1178
CH2(cyclo-C3H5)
C(CH3)(CH═CH2)—CH2—CH2—CH3


A-1179
CH2(cyclo-C3H5)
C(CH3)(CH2—CH3)—CH═CH—CH3


A-1180
CH2(cyclo-C3H5)
C(CH3)(CH2—CH3)—CH2—CH═CH2


A-1181
CH2(cyclo-C3H5)
C[═C(CH3)—CH3]—CH2—CH2—CH3


A-1182
CH2(cyclo-C3H5)
CH[C(═CH2)—CH3]—CH2—CH2—CH3


A-1183
CH2(cyclo-C3H5)
C(i-C3H7)═CH—CH2—CH3


A-1184
CH2(cyclo-C3H5)
CH(i-C3H7)—CH═CH—CH3


A-1185
CH2(cyclo-C3H5)
CH(i-C3H7)—CH2—CH═CH2


A-1186
CH2(cyclo-C3H5)
C(═CH—CH3)—C(CH3)3


A-1187
CH2(cyclo-C3H5)
CH(CH═CH2)—C(CH3)3


A-1188
CH2(cyclo-C3H5)
C(CH3)(CH═CH2)CH(CH3)—CH3


A-1189
CH2(cyclo-C3H5)
C(CH3)(CH2—CH3)C(═CH2)—CH3


A-1190
CH2(cyclo-C3H5)
2-CH3-cyclohex-1-enyl


A-1191
CH2(cyclo-C3H5)
[2-(═CH2)]-cyclo-C6H9


A-1192
CH2(cyclo-C3H5)
2-CH3-cyclohex-2-enyl


A-1193
CH2(cyclo-C3H5)
2-CH3-cyclohex-3-enyl


A-1194
CH2(cyclo-C3H5)
2-CH3-cyclohex-4-enyl


A-1195
CH2(cyclo-C3H5)
2-CH3-cyclohex-5-enyl


A-1196
CH2(cyclo-C3H5)
2-CH3-cyclohex-6-enyl


A-1197
CH2(cyclo-C3H5)
3-CH3-cyclohex-1-enyl


A-1198
CH2(cyclo-C3H5)
3-CH3-cyclohex-2-enyl


A-1199
CH2(cyclo-C3H5)
[3-(═CH2)]-cyclo-C6H9


A-1200
CH2(cyclo-C3H5)
3-CH3-cyclohex-3-enyl


A-1201
CH2(cyclo-C3H5)
3-CH3-cyclohex-4-enyl


A-1202
CH2(cyclo-C3H5)
3-CH3-cyclohex-5-enyl


A-1203
CH2(cyclo-C3H5)
3-CH3-cyclohex-6-enyl


A-1204
CH2(cyclo-C3H5)
4-CH3-cyclohex-1-enyl


A-1205
CH2(cyclo-C3H5)
4-CH3-cyclohex-2-enyl


A-1206
CH2(cyclo-C3H5)
4-CH3-cyclohex-3-enyl


A-1207
CH2(cyclo-C3H5)
[4-(═CH2)]-cyclo-C6H9


A-1208
CH2(cyclo-C3H5)
CH2CF3


A-1209
CH2(cyclo-C3H5)
CH2CCl3


A-1210
CH2(cyclo-C3H5)
CH2(cyclo-C3H5)








A-1211
—CH2—CH2—CH2—CH2—


A-1212
—CH2—CH2—CH2—


A-1213
—CH2—CH2—CH(CH3)—


A-1214
—CH(CH3)—CH2—CH2—


A-1215
—CH2—C(CH3)2—CH2—


A-1216
—CH(CH3)—CH2—CH2—CH2—


A-1217
—CH2—CH2—CH2—CH(CH3)—


A-1218
—CH2—CH2—CH(CH3)—CH2—


A-1219
—CH2—CH(CH3)—CH2—CH2—


A-1220
—C(CH3)2—CH2—CH2—CH2—


A-1221
—C(CH3)2—CH2—CH2—CH2—


A-1222
—CH2—CH2—CH2—C(CH3)2—


A-1223
—CH2—C(CH3)2—CH2—CH2—


A-1224
—CH2—CH2—C(CH3)2—CH2—


A-1225
(RR)—CH(CH3)—CH(CH3)—


A-1226
(SS)—CH(CH3)—CH(CH3)—


A-1227
(RS)—CH(CH3)—CH(CH3)—


A-1228
(SR)—CH(CH3)—CH(CH3)—


A-1229
—C(CH3)2—CH2—CH2—


A-1230
—CH(C2H5)—CH2—CH2—CH2—


A-1231
—CH2—CH2—CH2—CH(C2H5)—


A-1232
—CH2—CH2—CH(C2H5)—CH2—


A-1233
—CH2—CH(C2H5)—CH2—CH2—


A-1234
—CH2—CH2—C(CH3)2—









The compounds according to the invention and/or their agriculturally acceptable salts are suitable as fungicides. They are distinguished by excellent activity against a broad spectrum of phytopathogenic fungi from the class of the Ascomycetes, Deuteromycetes, Basidiomycetes and Peronosporomycetes (syn. Oomycetes). Some of them are systemically active and can be used in crop protection as foliar fungicides, as fungicides for seed dressing and as soil fungicides.


They are particularly important in the control of a large number of fungi on various crop plants, such as wheat, rye, barley, oats, rice, corn, grass, bananas, cotton, soybeans, coffee, sugar cane, grapevines, fruit and ornamental plants and vegetables, such as cucumbers, beans, tomatoes, potatoes and cucurbits, and also on the seeds of these plants.


The compounds I are suitable for controlling Alternaria species on vegetables, rapeseed, sugarbeet and fruit and rice, such as, for example, A. solani or A. alternata on potatoes and tomatoes.


The compounds I are suitable for controlling Aphanomyces species on sugarbeet and vegetables.


The compounds I are suitable for controlling Ascochyta species on cereals and vegetables.


The compounds I are suitable for controlling Bipolaris and Drechslera species on corn, cereals, rice and lawns, such as, for example, D. maydis on corn.


The compounds I are suitable for controlling Blumeria graminis (powdery mildew) on cereals.


The compounds I are suitable for controlling Botrytis cinerea (gray mold) on strawberries, vegetables, flowers and grapevines.


The compounds I are suitable for controlling Bremia lactucae on lettuce.


The compounds I are suitable for controlling Cercospora species on corn, soybeans, rice and sugarbeet.


The compounds I are suitable for controlling Cochliobolus species on corn, cereals, rice, such as, for example, Cochliobolus sativus on cereals, Cochliobolus miyabeanus on rice.


The compounds I are suitable for controlling Colletotricum species on soybeans and cotton.


The compounds I are suitable for controlling Drechslera species, Pyrenophora species on corn, cereals, rice and lawns, such as, for example, D. teres on barley or D. tritici-repentis on wheat.


The compounds I are suitable for controlling Esca on grapevines, caused by Phaeoacremonium chlamydosporium, Ph. Aleophilum, and Formitipora punctata (syn. Phellinus punctatus).


The compounds I are suitable for controlling Elisinoe ampelina on grapevines.


The compounds I are suitable for controlling Exserohilum species on corn.


The compounds I are suitable for controlling Erysiphe cichoracearum and Sphaerotheca fuliginea on cucumbers.


The compounds I are suitable for controlling Fusarium and Verticillium species on various plants, such as, for example, F. graminearum or F. culmorum on cereals or F. oxysporum on a large number of plants, such as, for example, tomatoes.


The compounds I are suitable for controlling Gaeumanomyces graminis on cereals.


The compounds I are suitable for controlling Gibberella species on cereals and rice (for example Gibberella fujikuroi on rice).


The compounds I are suitable for controlling Glomerella cingulata on grapevines and other plants.


The compounds I are suitable for controlling Grainstaining complex on rice.


The compounds I are suitable for controlling Guignardia budwelli on grapevines.


The compounds I are suitable for controlling Helminthosporium species on corn and rice.


The compounds I are suitable for controlling Isariopsis clavispora on grapevines.


The compounds I are suitable for controlling Michrodochium nivale on cereals.


The compounds I are suitable for controlling Mycosphaerella species on cereals, bananas and peanuts, such as, for example, M. graminicola on wheat or M. fijiensis on bananas.


The compounds I are suitable for controlling Peronospora species on cabbage and bulbous plants, such as, for example, P. brassicae on cabbage or P. destructor on onions.


The compounds I are suitable for controlling Phakopsara pachyrhizi and Phakopsara meibomiae on soybeans.


The compounds I are suitable for controlling Phomopsis species on soybeans and sunflowers.


The compounds I are suitable for controlling Phytophthora infestans on potatoes and tomatoes.


The compounds I are suitable for controlling Phytophthora species on various plants, such as, for example, P. capsici on bell peppers.


The compounds I are suitable for controlling Plasmopara viticola on grapevines.


The compounds I are suitable for controlling Podosphaera leucotricha on apples.


The compounds I are suitable for controlling Pseudocercosporella herpotrichoides on cereals.


The compounds I are suitable for controlling Pseudoperonospora on various plants, such as, for example, P. cubensis on cucumbers or P. humili on hops.


The compounds I are suitable for controlling Pseudopezicula tracheiphilai on grapevines.


The compounds I are suitable for controlling Puccinia species on various plants, such as, for example, P. triticina, P. striformins, P. hordei or P. graminis on cereals, or P. asparagi on asparagus.


The compounds I are suitable for controlling Pyricularia oryzae, Corticium sasakii, Sarocladium oryzae, S. attenuatum, Entyloma oryzae on rice.


The compounds I are suitable for controlling Pyricularia grisea on lawns and cereals. The compounds I are suitable for controlling Pythium spp. on lawns, rice, corn, cotton, rapeseed, sunflowers, sugarbeet, vegetables and other plants, such as, for example, P. ultiumum on various plants, P. aphanidermatum on lawns.


The compounds I are suitable for controlling Rhizoctonia species on cotton, rice, potatoes, lawns, corn, rapeseed, potatoes, sugarbeet, vegetables and on various plants, such as, for example, R. solani on beet and various plants.


The compounds I are suitable for controlling Rhynchosporium secalis on barley, rye and triticale.


The compounds I are suitable for controlling Sclerotinia species on rapeseed and sunflowers.


The compounds I are suitable for controlling Septoria tritici and Stagonospora nodorum on wheat.


The compounds I are suitable for controlling Erysiphe (syn. Uncinula) necator on grapevines.


The compounds I are suitable for controlling Setospaeria species on corn and lawns.


The compounds I are suitable for controlling Sphacelotheca reilinia on corn.


The compounds I are suitable for controlling Thievaliopsis species on soybeans and cotton.


The compounds I are suitable for controlling Tilletia species on cereals.


The compounds I are suitable for controlling Ustilago species on cereals, corn and sugarcane, such as, for example, U. maydis on corn.


The compounds I are suitable for controlling Venturia species (scab) on apples and pears, such as, for example, V. inaequalis on apples.


The compounds I are furthermore suitable for controlling harmful fungi in the protection of materials (for example wood, paper, paint dispersions, fibers or fabrics) and in the protection of stored products. In the protection of wood, particular attention is paid to the following harmful fungi: Ascomycetes, such as Ophiostoma spp., Ceratocystis spp., Aureobasidium pullulans, Sclerophoma spp., Chaetomium spp., Humicola spp., Petriella spp., Trichurus spp.; Basidiomycetes, such as Coniophora spp., Coriolus spp., Gloeophyllum spp., Lentinus spp., Pleurotus spp., Poria spp., Serpula spp. and Tyromyces spp., Deuteromycetes, such as Aspergillus spp., Cladosporium spp., Penicillium spp., Trichoderma spp., Alternaria spp., Paecilomyces spp. and Zygomycetes, such as Mucor spp., additionally in the protection of materials the following yeasts: Candida spp. and Saccharomyces cerevisae.


Accordingly, the present invention furthermore provides the use of the compounds according to the invention and/or their agriculturally acceptable salts for controlling phytopathogenic fungi.


In addition, the compounds according to the invention can also be used in crops which, owing to breeding including genetical engineering, are tolerant to attack by insects or fungi.


The compounds according to the invention and/or their agriculturally acceptable salts are employed by treating the fungi active or the plants, seeds, materials or soil to be protected from fungal attack with a fungicidally effective amount of these compounds. The application can be carried out both before and after the infection of the materials, plants or seeds by the fungi.


Accordingly, the present invention furthermore provides a method for controlling phytopathogenic fungi, which method comprises treating the fungi or the materials, plants, the soil or seed to be protected against fungal attack with an effective amount of at least one compound according to the invention and/or an agriculturally acceptable salt thereof.


The present invention furthermore provides a composition for controlling phytopathogenic fungi, which composition comprises at least one compound according to the invention and/or an agriculturally acceptable salt thereof and at least one solid or liquid carrier.


The fungicidal compositions generally comprise between 0.1 and 95%, preferably between 0.5 and 90%, by weight of active compound.


When employed in plant protection, the amounts applied are, depending on the kind of effect desired, between 0.01 and 2.0 kg of active compound per ha.


In the treatment of seed, the amounts of active compound employed are generally from 1 to 1000 g/100 kg, preferably from 1 to 200 g/100 kg, in particular from 5 to 100 g/100 kg of seed.


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


The compounds according to the invention and/or their agriculturally acceptable salts can be converted into the customary formulations, for example solutions, emulsions, suspensions, dusts, powders, pastes and granules. The use form depends on the particular intended purpose; in each case, it should ensure a fine and even distribution of the compound according to the invention.


The formulations are prepared in a known manner, for example by extending the active compound with solvents and/or carriers, if desired using emulsifiers and dispersants. Solvents/auxiliaries which are suitable are essentially:

    • water, aromatic solvents (for example Solvesso products, xylene), paraffins (for example mineral oil fractions), alcohols (for example methanol, butanol, pentanol, benzyl alcohol), ketones (for example cyclohexanone, gamma-butyrolactone), pyrrolidones (NMP, NOP), acetates (glycol diacetate), glycols, fatty acid dimethylamides, fatty acids and fatty acid esters. In principle, solvent mixtures may also be used,
    • carriers such as ground natural minerals (for example kaolins, clays, talc, chalk) and ground synthetic minerals (for example finely divided silica, silicates); emulsifiers such as nonionic and anionic emulsifiers (for example polyoxyethylene fatty alcohol ethers, alkylsulfonates and arylsulfonates) and dispersants such as lignosulfite waste liquors and methylcellulose.


Suitable surfactants are alkali metal, alkaline earth metal and ammonium salts of lignosulfonic acid, naphthalenesulfonic acid, phenolsulfonic acid, dibutylnaphthalenesulfonic acid, alkylarylsulfonates, alkyl sulfates, alkylsulfonates, fatty alcohol sulfates, fatty acids and sulfated fatty alcohol glycol ethers, furthermore condensates of sulfonated naphthalene and naphthalene derivatives with formaldehyde, condensates of naphthalene or of naphthalenesulfonic acid with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctylphenol, octylphenol, nonylphenol, alkylphenol polyglycol ethers, tributylphenyl polyglycol ether, tristearylphenyl polyglycol ether, alkylaryl polyether alcohols, alcohol and fatty alcohol/ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers, ethoxylated polyoxypropylene, lauryl alcohol polyglycol ether acetal, sorbitol esters, lignosulfite waste liquors and methylcellulose.


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


Powders, materials for spreading and dustable products can be prepared by mixing or concomitantly grinding the active substances with a solid carrier.


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


In general, the formulations comprise from 0.01 to 95% by weight, preferably from 0.1 to 90% by weight, of the active compound. The active compounds are employed in a purity of from 90% to 100%, preferably 95% to 100% (according to NMR spectrum).


The following are examples of formulations: 1. Products for dilution with water


A Water-Soluble Concentrates (SL, LS)

10 parts by weight of the active compounds are dissolved 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 formulation having an active compound content of 10% by weight.


B Dispersible Concentrates (DC)

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


C Emulsifiable Concentrates (EC)

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


D Emulsions (EW, EO, ES)

25 parts by weight of the active compounds are dissolved in 35 parts by weight of xylene with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight). This mixture is 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 formulation has an active compound content of 25% by weight.


E Suspensions (SC, OD, FS)

In an agitated ball mill, 20 parts by weight of the active compounds are comminuted with addition of 10 parts by weight of dispersants and wetters and 70 parts by weight of water or an organic solvent to give a fine active compound suspension. Dilution with water gives a stable suspension of the active compound. The active compound content in the formulation is 20% by weight.


F Water-Dispersible Granules and Water-Soluble Granules (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 formulation has an active compound content of 50% by weight.


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

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


H Gel Formulations (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. Products to be Applied Undiluted

I Dustable powders (DP, DS)


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


J Granules (GR, FG, GG, MG)

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


K ULV solutions (UL)


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


Seed treatment typically utilizes water-soluble concentrates (LS), suspensions (FS), dusts (DS), water-dispersible and water-soluble powders (WS, SS), emulsions (ES), emulsifiable concentrates (EC) and gel formulations (GF). These formulations can be applied neat or preferably diluted to the seed. The application can take place prior to sowing.


The active compounds can be used as such, in the form of their formulations or the use forms prepared therefrom, for example in the form of directly sprayable solutions, powders, suspensions or dispersions, emulsions, oil dispersions, pastes, dustable products, materials for spreading, or granules, by means of spraying, atomizing, dusting, spreading or pouring. The use forms 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 wetting agent, 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 formulations comprising over 95% by weight of active compound, or even to apply the active compound without additives.


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


Suitable adjuvants in this sense are in particular: 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 compounds according to the invention can, in the application form as fungicides, also be present together with other active compounds, for example with herbicides, insecticides, growth regulators, fungicides or also with fertilizers. When mixing the compounds according to the invention or the compositions comprising them with one or more further active compounds, in particular fungicides, it is in many cases possible for example to broaden the activity spectrum or to prevent the development of resistance. In many cases, synergistic effects are obtained.


The invention furthermore provides therefore a composition of at least one compound according to the invention and/or an agriculturally acceptable salt thereof and at least one further fungicidally, insecticidally, herbicidally and/or growth-regulating active compound.


The present invention also provides a pesticidal composition comprising at least one compound I, in particular a compound I described in the present description as being preferred and/or an agriculturally acceptable salt thereof, and at least one solid or liquid carrier. Such a pesticidal composition may comprise at least one further fungicidally, insecticidally and/or herbicidally active compound.


The following list L of fungicides, together with which the compounds according to the invention may be used, is meant to illustrate the combination possibilities, but not to limit them:


List L:
Strobilurins





    • azoxystrobin, dimoxystrobin, enestroburin, fluoxastrobin, kresoxim-methyl, metominostrobin, picoxystrobin, pyraclostrobin, trifloxystrobin, orysastrobin, methyl (2-chloro-5-[1-(3-methylbenzyloxyimino)ethyl]benzyl)carbamate, methyl (2-chloro-5-[1-(6-methylpyridin-2-ylmethoxyimino)ethyl]benzyl)carbamate, methyl 2-(ortho-((2,5-dimethylphenyloxymethylene)phenyl)-3-methoxyacrylate;





Carboxamides





    • carboxanilides: benalaxyl, benodanil, boscalid, carboxin, mepronil, fenfuram, fenhexamid, flutolanil, furametpyr, metalaxyl, ofurace, oxadixyl, oxycarboxin, penthiopyrad, thifluzamide, tiadinil, N-(4′-bromobiphenyl-2-yl)-4-difluoromethyl-2-methylthiazole-5-carboxamide, N-(4′-trifluoromethylbiphenyl-2-yl)-4-difluoromethyl-2-methylthiazole-5-carboxamide, N-(4′-chloro-3′-fluorobiphenyl-2-yl)-4-difluoromethyl-2-methylthiazole-5-carboxamide, N-(3′,4′-dichloro-4-fluoro-biphenyl-2-yl)-3-difluoromethyl-1-methylpyrazole-4-carboxamide, N-(3′,4′-dichloro-5-fluoro-biphenyl-2-yl)-3-difluoromethyl-1-methylpyrazole-4-carboxamide, N-(2-cyanophenyl)-3,4-dichloroisothiazole-5-carboxamide;

    • carboxylic acid morpholides: dimethomorph, flumorph;

    • benzamides: flumetover, fluopicolide (picobenzamid), zoxamide;

    • other carboxamides: carpropamid, diclocymet, mandipropamid, N-(2-(4-[3-(4-chlorophenyl)prop-2-ynyloxy]-3-methoxyphenyl)ethyl)-2-methanesulfonylamino-3-methylbutyramide, N-(2-(4-[3-(4-chlorophenyl)prop-2-ynyloxy]-3-methoxyphenyl)ethyl)-2-ethanesulfonylamino-3-methylbutyramide;





Azoles





    • triazoles: bitertanol, bromuconazole, cyproconazole, difenoconazole, diniconazole, enilconazole, epoxiconazole, fenbuconazole, flusilazole, fluquinconazole, flutriafol, hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil, penconazole, propiconazole, prothioconazole, simeconazole, tebuconazole, tetraconazole, triadimenol, triadimefon, triticonazole;

    • imidazoles: cyazofamid, imazalil, pefurazoate, prochloraz, triflumizole;

    • benzimidazoles: benomyl, carbendazim, fuberidazole, thiabendazole;

    • others: ethaboxam, etridiazole, hymexazole;





Nitrogenous Heterocyclyl Compounds:





    • pyridines: fluazinam, pyrifenox, 3-[5-(4-chlorophenyl)-2,3-dimethylisoxazolidin-3-yl]pyridine;

    • pyrimidines: bupirimate, cyprodinil, ferimzone, fenarimol, mepanipyrim, nuarimol,

    • pyrimethanil;

    • piperazines: triforine;

    • pyrroles: fludioxonil, fenpiclonil;

    • morpholines: aldimorph, dodemorph, fenpropimorph, tridemorph;

    • dicarboximides: iprodione, procymidone, vinclozolin;

    • others: acibenzolar-S-methyl, anilazine, captan, captafol, dazomet, diclomezine, fenoxanil, folpet, fenpropidin, famoxadone, fenamidone, octhilinone, probenazole, proquinazid, pyroquilon, quinoxyfen, tricyclazole, 5-chloro-7-(4-methylpiperidin-1-yl)-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine, 2-butoxy-6-iodo-3-propylchromen-4-one, N,N-dimethyl-3-(3-bromo-6-fluoro-2-methylindole-1-sulfonyl)-[1,2,4]triazole-1-sulfonamide;





Carbamates and Dithiocarbamates





    • dithiocarbamates: ferbam, mancozeb, maneb, metiram, metam, propineb, thiram, zineb, ziram;

    • carbamates: diethofencarb, flubenthiavalicarb, iprovalicarb, propamocarb, methyl 3-(4-chlorophenyl)-3-(2-isopropoxycarbonylamino-3-methylbutyrylamino)propionate, 4-fluorophenyl N-(1-(1-(4-cyanophenyl)ethanesulfonyl)but-2-yl)carbamate;





Other Fungicides





    • guanidines: dodine, iminoctadine, guazatine;

    • antibiotics: kasugamycin, polyoxins, streptomycin, validamycin A;

    • organometal compounds: fentin salts;

    • sulfur-containing heterocyclyl compounds: isoprothiolane, dithianon;

    • organophosphorous compounds: edifenphos, fosetyl, fosetyl-aluminum, iprobenfos, pyrazophos, tolclofos-methyl, phosphorous acid and its salts;

    • organochlorine compounds: thiophanate methyl, chlorothalonil, dichlofluanid, tolylfluanid, flusulfamide, phthalide, hexachlorobenzene, pencycuron, quintozene;

    • nitrophenyl derivatives: binapacryl, dinocap, dinobuton;

    • inorganic active compounds: Bordeaux mixture, copper acetate, copper hydroxide, copper oxychloride, basic copper sulfate, sulfur;

    • others: spiroxamine, cyflufenamid, cymoxanil, metrafenone.





Accordingly, the present invention furthermore relates to the compositions listed in Table B, where a row of Table B corresponds in each case to a fungicidal composition comprising a compound of the formula I (component 1), which is preferably one of the compounds described herein as being preferred, and the respective further active compound (component 2) stated in the row in question. According to one embodiment of the invention, component 1 in each row of Table B is in each case one of the compounds of the formula I specifically individualized in Tables 1 to 184.











TABLE B





No.
Component 1
Component 2







B-1
a compound of the formula I
azoxystrobin


B-2
a compound of the formula I
dimoxystrobin


B-3
a compound of the formula I
enestroburin


B-4
a compound of the formula I
fluoxastrobin


B-5
a compound of the formula I
kresoxim-methyl


B-6
a compound of the formula I
metominostrobin


B-7
a compound of the formula I
picoxystrobin


B-8
a compound of the formula I
pyraclostrobin


B-9
a compound of the formula I
trifloxystrobin


B-10
a compound of the formula I
orysastrobin


B-11
a compound of the formula I
methyl (2-chloro-5-[1-(3-methylbenzyloxyimino)




ethyl]benzyl)carbamate


B-12
a compound of the formula I
methyl (2-chloro-5-[1-(6-methylpyridin-2-yl-




methoxyimino)ethyl]benzyl)carbamate


B-13
a compound of the formula I
methyl 2-(ortho-(2,5-dimethylphenyloxy-




methylene)phenyl)-3-methoxyacrylate


B-14
a compound of the formula I
benalaxyl


B-15
a compound of the formula I
benodanil


B-16
a compound of the formula I
boscalid


B-17
a compound of the formula I
carboxin


B-18
a compound of the formula I
mepronil


B-19
a compound of the formula I
fenfuram


B-20
a compound of the formula I
fenhexamid


B-21
a compound of the formula I
flutolanil


B-22
a compound of the formula I
furametpyr


B-23
a compound of the formula I
metalaxyl


B-24
a compound of the formula I
ofurace


B-25
a compound of the formula I
oxadixyl


B-26
a compound of the formula I
oxycarboxin


B-27
a compound of the formula I
penthiopyrad


B-28
a compound of the formula I
thifluzamide


B-29
a compound of the formula I
tiadinil


B-30
a compound of the formula I
N-(4′-bromobiphenyl-2-yl)-4-difluoromethyl-2-




methylthiazole-5-carboxamide


B-31
a compound of the formula I
N-(4′-trifluoromethylbiphenyl-2-yl)-4-di-




fluoromethyl-2-methylthiazole-5-carboxamide


B-32
a compound of the formula I
N-(4′-chloro-3′-fluorobiphenyl-2-yl)-4-di-




fluoromethyl-2-methylthiazole-5-carboxamide


B-33
a compound of the formula I
N-(3′,4′-dichloro-4-fluorobiphenyl-2-yl)-3-di-




fluoromethyl-1-methylpyrazole-4-carboxamide


B-34
a compound of the formula I
N-(3′,4′-dichloro-5-fluorobiphenyl-2-yl)-3-di-




fluoromethyl-1-methylpyrazole-4-carboxamide


B-35
a compound of the formula I
N-(2-cyanophenyl)-3,4-dichloroisothiazole-5-




carboxamide


B-36
a compound of the formula I
dimethomorph


B-37
a compound of the formula I
flumorph


B-38
a compound of the formula I
flumetover


B-39
a compound of the formula I
fluopicolide (picobenzamid)


B-40
a compound of the formula I
zoxamide


B-41
a compound of the formula I
carpropamid


B-42
a compound of the formula I
diclocymet


B-43
a compound of the formula I
mandipropamid


B-44
a compound of the formula I
N-(2-(4-[3-(4-chlorophenyl)prop-2-ynyloxy]-3-




methoxyphenyl)ethyl)-2-methanesulfonyl-




amino-3-methylbutyramide


B-45
a compound of the formula I
N-(2-(4-[3-(4-chlorophenyl)prop-2-ynyloxy]-3-




methoxyphenyl)ethyl)-2-ethanesulfonylamino-




3-methylbutyramide


B-46
a compound of the formula I
bitertanol


B-47
a compound of the formula I
bromuconazole


B-48
a compound of the formula I
cyproconazole


B-49
a compound of the formula I
difenoconazole


B-50
a compound of the formula I
diniconazole


B-51
a compound of the formula I
enilconazole


B-52
a compound of the formula I
epoxiconazole


B-53
a compound of the formula I
fenbuconazole


B-54
a compound of the formula I
flusilazole


B-55
a compound of the formula I
fluquinconazole


B-56
a compound of the formula I
flutriafol


B-57
a compound of the formula I
hexaconazol


B-58
a compound of the formula I
imibenconazole


B-59
a compound of the formula I
ipconazole


B-60
a compound of the formula I
metconazol


B-61
a compound of the formula I
myclobutanil


B-62
a compound of the formula I
penconazole


B-63
a compound of the formula I
propiconazole


B-64
a compound of the formula I
prothioconazole


B-65
a compound of the formula I
simeconazole


B-66
a compound of the formula I
tebuconazole


B-67
a compound of the formula I
tetraconazole


B-68
a compound of the formula I
triadimenol


B-69
a compound of the formula I
triadimefon


B-70
a compound of the formula I
triticonazole


B-71
a compound of the formula I
cyazofamid


B-72
a compound of the formula I
imazalil


B-73
a compound of the formula I
pefurazoate


B-74
a compound of the formula I
prochloraz


B-75
a compound of the formula I
triflumizole


B-76
a compound of the formula I
benomyl


B-77
a compound of the formula I
carbendazim


B-78
a compound of the formula I
fuberidazole


B-79
a compound of the formula I
thiabendazole


B-80
a compound of the formula I
ethaboxam


B-81
a compound of the formula I
etridiazole


B-82
a compound of the formula I
hymexazole


B-83
a compound of the formula I
fluazinam


B-84
a compound of the formula I
pyrifenox


B-85
a compound of the formula I
3-[5-(4-chlorophenyl)-2,3-dimethylisoxazolidin-




3-yl]pyridine


B-86
a compound of the formula I
bupirimate


B-87
a compound of the formula I
cyprodinil


B-88
a compound of the formula I
ferimzone


B-89
a compound of the formula I
fenarimol


B-90
a compound of the formula I
mepanipyrim


B-91
a compound of the formula I
nuarimol


B-92
a compound of the formula I
pyrimethanil


B-93
a compound of the formula I
triforine


B-94
a compound of the formula I
fludioxonil


B-95
a compound of the formula I
fenpiclonil


B-96
a compound of the formula I
aldimorph


B-97
a compound of the formula I
dodemorph


B-98
a compound of the formula I
fenpropimorph


B-99
a compound of the formula I
tridemorph


B-100
a compound of the formula I
iprodione


B-101
a compound of the formula I
procymidone


B-102
a compound of the formula I
vinclozolin


B-103
a compound of the formula I
acibenzolar-S-methyl


B-104
a compound of the formula I
anilazin


B-105
a compound of the formula I
captan


B-106
a compound of the formula I
captafol


B-107
a compound of the formula I
dazomet


B-108
a compound of the formula I
diclomezine


B-109
a compound of the formula I
fenoxanil


B-110
a compound of the formula I
folpet


B-111
a compound of the formula I
fenpropidin


B-112
a compound of the formula I
famoxadone


B-113
a compound of the formula I
fenamidone


B-114
a compound of the formula I
octhilinone


B-115
a compound of the formula I
probenazole


B-116
a compound of the formula I
proquinazid


B-117
a compound of the formula I
pyroquilon


B-118
a compound of the formula I
quinoxyfen


B-119
a compound of the formula I
tricyclazole


B-120
a compound of the formula I
5-chloro-7-(4-methylpiperidin-1-yl)-6-(2,4,6-




trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine


B-121
a compound of the formula I
2-butoxy-6-iodo-3-propylchromene-4-one


B-122
a compound of the formula I
N,N-dimethyl-3-(3-bromo-6-fluoro-2-methyl-




indole-1-sulfonyl)-[1,2,4]triazole-1-sulfonamide


B-123
a compound of the formula I
ferbam


B-124
a compound of the formula I
mancozeb


B-125
a compound of the formula I
maneb


B-126
a compound of the formula I
metiram


B-127
a compound of the formula I
metam


B-128
a compound of the formula I
propineb


B-129
a compound of the formula I
thiram


B-130
a compound of the formula I
zineb


B-131
a compound of the formula I
ziram


B-132
a compound of the formula I
diethofencarb


B-133
a compound of the formula I
flubenthiavalicarb


B-134
a compound of the formula I
iprovalicarb


B-135
a compound of the formula I
propamocarb


B-136
a compound of the formula I
methyl 3-(4-chlorophenyl)-3-(2-isopropoxy-




carbonylamino-3-methylbutyrylamino)-




propionate


B-137
a compound of the formula I
4-fluorophenyl N-(1-(1-(4-cyanophenyl)-




ethanesulfonyl)but-2-yl)carbamate


B-138
a compound of the formula I
dodine


B-139
a compound of the formula I
iminoctadine


B-140
a compound of the formula I
guazatine


B-141
a compound of the formula I
kasugamycin


B-142
a compound of the formula I
polyoxine


B-143
a compound of the formula I
streptomycin


B-144
a compound of the formula I
validamycin A


B-145
a compound of the formula I
fentin salts


B-146
a compound of the formula I
isoprothiolane


B-147
a compound of the formula I
dithianon


B-148
a compound of the formula I
edifenphos


B-149
a compound of the formula I
fosetyl


B-150
a compound of the formula I
fosetyl-aluminum


B-151
a compound of the formula I
iprobenfos


B-152
a compound of the formula I
pyrazophos


B-153
a compound of the formula I
tolclofos-methyl


B-154
a compound of the formula I
phosphorous acid and its salts


B-155
a compound of the formula I
thiophanate methyl


B-156
a compound of the formula I
chlorothalonil


B-157
a compound of the formula I
dichlofluanid


B-158
a compound of the formula I
tolylfluanid


B-159
a compound of the formula I
flusulfamide


B-160
a compound of the formula I
phthalide


B-161
a compound of the formula I
hexachlorobenzene


B-162
a compound of the formula I
pencycuron


B-163
a compound of the formula I
quintozene


B-164
a compound of the formula I
binapacryl


B-165
a compound of the formula I
dinocap


B-166
a compound of the formula I
dinobuton


B-167
a compound of the formula I
Bordeaux mixture


B-168
a compound of the formula I
copper acetate


B-169
a compound of the formula I
copper hydroxide


B-170
a compound of the formula I
copper oxychloride


B-171
a compound of the formula I
basic copper sulfate


B-172
a compound of the formula I
sulfur


B-173
a compound of the formula I
spiroxamine


B-174
a compound of the formula I
cyflufenamid


B-175
a compound of the formula I
cymoxanil


B-176
a compound of the formula I
metrafenone









The active compounds II, mentioned above as component 2, their preparation and their action against harmful fungi are generally known (cf.: http://www.hclrss.demon.co.uk/index.html); they are commercially available. The compounds named according to IUPAC, their preparation and their fungicidal action are likewise known [cf. in EP-A 226 917; EP-A 10 28 125; EP-A 10 35 122; EP-A 12 01 648; WO 98/46608; WO 99/24413; WO 03/14103; WO 03/053145; WO 03/066609 and WO 04/049804].


The present invention furthermore relates to the pharmaceutical use of the compounds according to the invention, in particular the compounds according to the invention described as preferred, and/or the pharmaceutically acceptable salts thereof, in particular their use for controlling tumors in mammals such as, for example, humans.


The compounds according to the invention and/or their agriculturally acceptable salts can be present in various crystal modifications which may differ in their biological activity. They are also provided by the present invention.







SYNTHESIS EXAMPLES

With appropriate modification of the starting materials, the procedures given in the synthesis examples below were used to obtain further compounds according to the invention:


Example A
4-Chloro-6-(6-methyltetrahydro-2H-(1,2)-oxazin-2-yl)-2-(1,2,4-triazol-1-yl)-5-(2,4,6-trifluorophenyl)pyrimidine (Table C, No. 21)
Aa) 2-Ethoxycarbonyl-6-methyltetrahydro-2H-(1,2)-oxazine

12.23 g (185.3 mmol) of potassium hydroxide were dissolved in 100 ml of ethanol, and, at room temperature, 19.47 g (185.3 mmol) of O-ethyl N-hydroxyurethane and then 21.29 g (92.6 mmol) of 1,4-dibromopentane were added a little at a time with stirring. The mixture was boiled under reflux for 6 h and concentrated under reduced pressure, and the residue was suspended in 300 ml of methyl tert-butyl ether and filtered. The filtrate was again concentrated under reduced pressure. The residue (13.27 g) was then directly reacted further.


Ab) 6-Methyltetrahydro-2H-(1,2)-oxazine

The product from the preceding experiment was boiled in 300 g of 10% strength hydrochloric acid for 2 h. The solution was washed three times with in each case 100 ml of methyl tert-butyl ether and concentrated under reduced pressure. The residue was dissolved in warm diisopropyl ether, filtered and again concentrated under reduced pressure. 10 ml of 50% strength aqueous sodium hydroxide solution were added to the residue (8.1 g) and the mixture was subjected to fractional distillation at atmospheric pressure. The product was collected at a transition temperature of 85-95° C. The product (4.96 g) was directly used further.


Ac) 4-Chloro-6-(6-methyltetrahydro-2H-(1,2)-oxazin-2-yl)-2-methylthio-5-(2,4,6-trifluorophenyl)pyrimidine

At room temperature, 2.5 g of 6-methyltetrahydro-2H-(1,2)-oxazine from the preceding experiment, 4.2 g (12.9 mmol) of 4,6-dichloro-2-methylthio-5-(2,4,6-trifluorophenyl)pyrimidine and 2.2 g (21.5 mmol) of triethylamine were dissolved in 20 ml of dimethyl sulfoxide and then stirred at 100° C. for 5 h. The mixture was then added to 200 ml of water and 100 ml of methyl tert-butyl ether, the pH was adjusted to 8 using sodium bicarbonate and the organic phase was separated off. The aqueous phase was extracted twice with in each case 100 ml of methyl tert-butyl ether and the combined organic phases were dried over sodium sulfate and concentrated under reduced pressure. The crude product (5.1 g) was purified by chromatography on silica gel using cyclohexane/methyl tert-butyl ether. Yield 4.47 g, m.p. 110-111° C.


Ad) 4-Chloro-2-methylsulfonyl-6-(6-methyltetrahydro-2H-(1,2)-oxazin-2-yl)-5-(2,4,6-trifluorophenyl)pyrimidine

4.40 g (11.3 mmol) of 4-chloro-6-(6-methyltetrahydro-2H-(1,2)-oxazin-2-yl)-2-methylthio-5-(2,4,6-trifluorophenyl)pyrimidine were dissolved in 50 ml of methylene chloride, and, at 0-5° C., 5.56 g of 3-chloroperbenzoic acid were added a little at a time with stirring. At 5° C., the mixture was stirred for 7 h, another 0.5 g of 3-chloroperbenzoic acid was added, the mixture was stirred at 0° C. for 5 h and concentrated under reduced pressure and the residue was dissolved in 30 ml of ethyl acetate, washed three times with in each case 15 ml of saturated sodium bicarbonate solution, dried over sodium sulfate, concentrated under reduced pressure, triturated with diisopropyl ether and dried under reduced pressure. Yield 2.9 g, m.p. 160-162° C.


Ae) 4-Chloro-6-(6-methyltetrahydro-2H-(1,2)-oxazin-2-yl)-2-(1,2,4-triazol-1-yl)-5-(2,4,6-trifluorophenyl)pyrimidine

At room temperature, 26 mg (1.04 mmol) of 95% pure sodium hydride were initially charged in 4.0 ml of tetrahydrofuran, 69 mg (1.00 mmol) of (1,2,4)-triazole were then added and the mixture was stirred for 3 h. 0.40 g (0.95 mmol) of 4-chloro-2-methylsulfonyl-6-(6-methyltetrahydro-2H-(1,2)-oxazin-2-yl)-5-(2,4,6-trifluorophenyl)pyrimidine was then added and the mixture was stirred at room temperature overnight. After addition of 20 ml of methyl tert-butyl ether, the mixture was washed three times with in each case 3 ml of water, dried over sodium sulfate, concentrated under reduced pressure and purified by chromatography on silica gel using cyclohexane/ethyl acetate. Yield 140 mg, m.p. 141-143° C. 1H-NMR (CDCl3) δ=1.37 (d); 1.45-2.10 (m); 3.50 (m); 5.13 (m); 6.75 (m); 8.15 (s); 9.15 (s).


Example B
N-Methoxy-4-chloro-6-(isoxazolidin-2-yl)-5-(2,4,6-trifluorophenyl)-2-pyrimidinecarboximidamide (Table C, No. 17)
Ba) 4-Chloro-6 (isoxazolidin-2-yl)-2-methylthio-5-(2,4,6-trifluorophenyl)pyrimidine

At room temperature, 2.02 g (18.5 mmol) of isoxazolidine hydrochloride, 5.00 g (15.4 mmol) of 4,6-dichloro-2-methylthio-5-(2,4,6-trifluorophenyl)pyrimidine and 3.42 g (33.8 mmol) of triethylamine were dissolved in 20 ml of dimethyl sulfoxide and then stirred at 10° C. for 5 h. The mixture was added to 200 ml of water and 100 ml of methyl tert-butyl ether, the pH was adjusted to 8 using sodium bicarbonate and the organic phase was separated off. The aqueous phase was extracted twice with in each case 100 ml of methyl tert-butyl ether and the combined organic phases were dried over sodium sulfate and concentrated under reduced pressure. The crude product was purified by chromatography on silica gel using cyclohexane/methyl tert-butyl ether. Yield 2.6 g, m.p. 106-109° C.


Bb) 4-Chloro-6-(isoxazolidin-2-yl)-2-methylsulfonyl-5-(2,4,6-trifluorophenyl)pyrimidine

2.60 g (7.19 mmol) of 4-chloro-6-(isoxazolidin-2-yl)-2-methylthio-5-(2,4,6-trifluorophenyl)pyrimidine were dissolved in 30 ml of methylene chloride, and at 0° C. 3.54 g of 3-chloroperbenzoic acid were added a little at a time, with stirring. The mixture was stirred at 0° C. for 6 h and then at room temperature for 3 d. After the addition of 300 ml of ethyl acetate, the mixture was washed three times with in each case 100 ml of saturated sodium bicarbonate solution, dried over sodium sulfate and concentrated under reduced pressure. The crude product (3.6 g) was purified by chromatography on silica gel using cyclohexane/methyl tert-butyl ether/ethyl acetate. Yield 2.0 g, m.p. 210-219° C.


Bc) 4-Chloro-2-cyano-6-(isoxazolidin-2-yl)-5-(2,4,6-trifluorophenyl)pyrimidine

At room temperature, 1.50 g (3.81 mmol) of 4-chloro-6-(isoxazolidin-2-yl)-2-methylsulfonyl-5-(2,4,6-trifluorophenyl)pyrimidine, 397 mg (6.09 mmol) of potassium cyanide and 13 mg of crown ether (18-crown-6) were added to 15 ml of acetonitrile. The mixture was stirred for 1 d and concentrated under reduced pressure, 50 ml of ethyl acetate were added and the mixture was washed three times with in each case 20 ml of water, dried over sodium sulfate and concentrated under reduced pressure. The crude product (1.7 g) was purified by chromatography on silica gel using cyclohexane/methyl tert-butyl ether. Yield 0.68 g, m.p. 107-113° C.


Bd) N-Methoxy-4-chloro-6-(isoxazolidin-2-yl)-5-(2,4,6-trifluorophenyl)-2-pyrimidine-carboximidamide

At 0° C., 400 mg (1.17 mmol) of 4-chloro-2-cyano-6-(isoxazolidin-2-yl)-5-(2,4,6-trifluorophenyl)pyrimidine and 127 mg (1.17 mmol) of 50% strength sodium methoxide solution in methanol were stirred in 5 ml of methanol for 1 d. 118 mg (1.41 mmol) of methoxyamine hydrochloride were then added, the mixture was stirred at room temperature for 6 h and concentrated under reduced pressure, 12 ml of ethyl acetate and 12 ml of saturated sodium bicarbonate solution were added, the aqueous phase was separated off and extracted with 12 ml of ethyl acetate and the combined organic phases were dried over sodium sulfate and concentrated under reduced pressure. Recrystallisation from acetonitrile gave 180 mg, m.p. 192-193° C. 1H-NMR (CDCl3) δ=2.25 (m); 3.73 (m); 4.00 (m); 4.05 (s); 5.41 (br); 6.74 (m).


Example C
4-Chloro-6-(isoxazolidin-2-yl)-5-(2,4,6-trifluorophenyl)-2-pyrimidinecarboxmide (Table C, No. 19)

22 mg (0.16 mmol) of potassium carbonate and 94 mg (0.83 mmol) of 30% strength hydrogen peroxide were added to 270 mg (0.79 mmol) of 4-chloro-2-cyano-6-(isoxazolidin-2-yl)-5-(2,4,6-trifluorophenyl)pyrimidine in 1 ml of dimethyl sulfoxide, and the mixture was stirred at room temperature for 16 h. The mixture was added to 15 ml of water and extracted three times with in each case 10 ml of ethyl acetate and the combined extracts were dried over sodium sulfate and concentrated under reduced pressure. The crude product was purified by chromatography on reverse-phase material (Chromolith 100×5) using acetonitrile/water. Yield 60 mg. 1H-NMR (CDCl3) δ=2.28 (m); 3.76 (m); 4.04 (m); 5.90 (br); 6.75 (m).


Example D
N-Methoxy-4-chloro-6-(N-cyclopropylmethyl-N-methoxyamino)-5-(2,4,6-trifluorophenyl)-2-pyrimidinecarboximidamide (Table C, No. 27)
Da) 4-Chloro-6-(methoxyamino)-2-methylthio-5-(2,4,6-trifluorphenyl)-pyrimidine

At room temperature, 1.41 g (16.9 mmol) of methoxyamine hydrochloride and 3.74 g (36.9 mmol) of triethylamine were added with stirring to 5.00 g (15.4 mmol) of 4,6-dichloro-2-methylthio-5-(2,4,6-trifluorophenyl)pyrimidine in 20 ml of dimethyl sulfoxide, and the mixture was then stirred at 95° C. for 7 h. The mixture was added to 250 ml of water and extracted three times with in each case 100 ml of methyl tert-butyl ether, and the combined organic phases were dried over sodium sulfate and concentrated under reduced pressure. The crude product was purified by chromatography on silica gel using cyclohexane/methyl tert-butyl ether. Yield 4.2 g.


Db) 4-Chloro-6-(N-cyclopropylmethyl-N-methoxyamino)-2-methylthio-5-(2,4,6-trifluorphenyl)-pyrimidine

1.13 g (8.34 mmol) of cyclopropylmethyl bromide were added to 1.40 g (4.17 mmol) of 4-chloro-6-(methoxyamino)-2-methylthio-5-(2,4,6-trifluorophenyl)pyrimidine in 7 ml of dimethylacetamide, and at 0-5° C. 116 mg (4.59 mmol) of 95% pure sodium hydride was then added a little at a time, with stirring. The mixture was stirred at 0° C. for 2 h and at room temperature for 3 d, poured into 70 ml of water and extracted three times with in each case 20 ml of methyl tert-butyl ether, and the combined organic phases were dried over sodium sulfate and concentrated under reduced pressure. Yield 1.68 g.


Dc) 4-Chloro-6-(N-cyclopropylmethyl-N-methoxyamino)-2-methylsulfonyl-5-(2,4,6-trifluorophenyl)pyrimidine

1.68 g (4.31 mmol) of 4-chloro-6-(N-cyclopropylmethyl-N-methoxyamino)-2-methylthio-5-(2,4,6-trifluorophenyl)pyrimidine were dissolved in 20 ml of methylene chloride, and at 0-5° C. 2.13 g of 3-chloroperbenzoic acid were added a little at a time with stirring. The mixture was stirred at 5° C. for 7 h and then at room temperature for 16 h and concentrated under reduced pressure, and the residue was suspended in 30 ml of ethyl acetate, washed three times with in each case 15 ml of saturated sodium bicarbonate solution, dried over sodium sulfate and concentrated under reduced pressure. The crude product was purified by chromatography on silica gel using cyclohexane/methyl tert-butyl ether. Yield 1.3 g.


Dd) 4-Chloro-2-cyano-6-(N-cyclopropylmethyl-N-methoxyamino)-5-(2,4,6-trifluorophenyl)pyrimidine (Table B, No. 25)

At room temperature, 1.30 g (3.08 mmol) of 4-chloro-6-(N-cyclopropylmethyl-N-methoxyamino)-2-methylsulfonyl-5-(2,4,6-trifluorophenyl)pyrimidine were added to 10 ml of acetonitrile, 351 mg (5.39 mmol) of potassium cyanide and 13 mg of crown ether (18-crown-6) were added and the mixture was stirred for 16 h. The mixture was concentrated under reduced pressure, 25 ml of ethyl acetate were added, and the mixture was washed three times with in each case 10 ml of water, dried over sodium sulfate and concentrated under reduced pressure. The crude product (1.0 g) was purified by chromatography on silica gel using cyclohexane/methyl tert-butyl ether. Yield 0.90 g. 1H-NMR (CDCl3) δ=0.34 (m); 0.56 (m); 1.20 (m); 3.18 (s); 3.75 (d); 6.78 (m).


De) N-Methoxy-4-chloro-6-(N-cyclopropylmethyl-N-methoxyamino)-5-(2,4,6-trifluorophenyl)-2-pyrimidinecarboximidamide

At −10° C., 5 mg (0.22 mmol) of lithium hydroxide were added with stirring to 800 mg (2.17 mmol) of 4-chloro-2-cyano-6-(N-cyclopropylmethyl-N-methoxyamino)-5-(2,4,6-trifluorophenyl)pyrimidine in 5 ml of methanol, and the mixture was stirred at −10° C. for 15 h and at room temperature for 2 d. 217 mg (2.60 mmol) of methoxyamine hydrochloride were then added, the mixture was stirred at room temperature for 18 h and concentrated under reduced pressure, 20 ml of methyl tert-butyl ether and 12 ml of saturated sodium bicarbonate solution were added, the aqueous phase was separated off and extracted with 20 ml of methyl tert-butyl ether and the combined organic phases were dried over sodium sulfate and concentrated under reduced pressure. The crude product was purified by chromatography on silica gel using cyclohexane/methyl tert-butyl ether. Yield 380 mg. 1H-NMR (CDCl3) δ=0.30 (m); 0.53 (m); 1.17 (m); 3.15 (s); 3.75 (d); 4.05 (s); 5.38 (br); 6.75 (m).


All experiments were carried out under protective gas (nitrogen).









TABLE C







Active compounds























No.
R11
R1





R3
R4
Physical data
















1
CH2-cyclo(C3H5)
H
2,4,6-trifluorophenyl
Cl
N
m.p. 98° C.


2
CH2-cyclo(C3H5)
H
2,4,6-trifluorophenyl
Cl
C(NH2)═NOH
m.p. 148-151° C.


3
CH3
CH3
2,4,6-trifluorophenyl
Cl
C(NH2)═NOH
m.p. 190° C.


4
CH2-cyclo(C3H5)
H
2,4,6-trifluorophenyl
Cl
C(NH2)═N—OCH3

1H-NMR (CDCl3) δ = 0.45








(m); 0.85(m); 3.17(d);








4.03(s); 5.40(br.); 6.78








(m).


5
CH3
CH3
2,4,6-trifluorophenyl
Cl
C(NH2)═NOCH3

1H-NMR (CDCl3) δ = 3.10








(s); 3.40(s); 4.02(s); 5.40








(br.); 6.77(t).


6
CH3
CH3
2-chloro-4-fluorophenyl
Cl
CN
m.p. 83-84° C.


7
CH3
CH3
2-chloro-4-fluorophenyl
Cl
1,2,4-triazol-1-yl
m.p. 144-146° C.


8
CH3
CH3
2-chloro-4-fluorophenyl
Cl
C(NH2)═N—OCH3

1H-NMR (CDCl3) δ = 3.00








(s); 3.35(s); 4.02(s); 5.40








(br.); 7.05(m); 7.23(m).


9
CH(CH3)2
CH3
2-chloro-4-fluorophenyl
Cl
N
m.p. 85-90° C.


10
CH(CH3)2
CH3
2-chloro-4-fluorophenyl
Cl
C(NH2)═N—OCH3
m.p. 164-165° C.


11
CH3
CH3
2-chloro-4-fluorophenyl
Cl
C(═O)NH2
m.p. 178-180° C.


12
CH(CH3)2
CH3
2-chloro-4-fluorophenyl
Cl
1,2,4-triazol-1-yl
m.p. 109-110° C.


13
CH3
CH3
2-chloro-4-methoxyphenyl
Cl
C(NH2)═N—OCH3

1H-NMR (CDCl3) δ = 2.99








(s); 3.35(s); 3.87(s); 4.05








(s); 5.40(br.); 6.87(m);








7.04(m); 7.15(m).


14
CH(CH3)2
CH3
2-chloro-4-fluorophenyl
Cl
C(═O)NH2
m.p. 172-174° C.


15
CH2-cyclo(C3H5)
CH3
2-chloro-4-fluorophenyl
Cl
1,2,4-triazol-1-yl
m.p. 137-139° C.


16
CH2-cyclo(C3H5)
CH3
2-chloro-4-fluorophenyl
Cl
CN
m.p. 103-104° C.












17
—CH2—CH2—CH2—
2,4,6-trifluorophenyl
Cl
C(NH2)═N—OCH3
m.p. 192-193° C.


18
—CH2—CH2—CH2—
2,4,6-trifluorophenyl
Cl
1,2,4-triazol-1-yl

1H-NMR (CDCl3) δ = 2.33







(m); 3.83(m); 4.07(m);







6.75(m); 8.15(s); 9.18







(s).


19
—CH2—CH2—CH2—
2,4,6-trifluorophenyl
Cl
C(═O)NH2

1H-NMR (CDCl3) δ = 2.28







(m); 3.76(m); 4.04(m);







5.90(br.); 6.75(m).


20
—CH2—CH2—CH2—CH2—
2,4,6-trifluorophenyl
Cl
1,2,4-triazol-1-yl
m.p. 133-134° C.


21
—CH(CH3)—CH2—CH2—CH2—
2,4,6-trifluorophenyl
Cl
1,2,4-triazol-1-yl
m.p. 141-143° C.


22
—CH2—CH2—CH2—CH2—
2,4,6-trifluorophenyl
Cl
C(NH2)═N—OCH3
m.p. 176-177° C.


23
—CH(CH3)—CH2—CH2—CH2—
2,4,6-trifluorophenyl
Cl
C(NH2)═N—OCH3
m.p. 126-128° C.













24
CH3
CH(CH3)2
2,4,6-trifluorophenyl
Cl
CN
m.p. 90-91° C.


25
CH3
CH2-cyclo(C3H5)
2,4,6-trifluorophenyl
Cl
CN

1H-NMR (CDCl3) δ = 0.34








(m); 0.56(m); 1.20(m);








3.18(s); 3.75(d); 6.78








(m).


26
CH3
CH(CH3)2
2,4,6-trifluorophenyl
Cl
C(NH2)═N—OCH3
m.p. 159-161° C.


27
CH3
CH2-cyclo(C3H5)
2,4,6-trifluorophenyl
Cl
C(NH2)═N—OCH3

1H-NMR (CDCl3) δ = 0.30








(m); 0.53(m); 1.17(m);








3.15(s); 3.75(d); 4.05(s);








5.38(br.); 6.75(m).


28
CH3
CH2—CH2—OCH3
2,4,6-trifluorophenyl
Cl
CN

1H-NMR (CDCl3) δ = 3.17








(s); 3.33(s); 3.62(t); 4.05








(t); 6.76(m).


29
CH3
CH2—CH2—OCH3
2,4,6-trifluorophenyl
Cl
C(NH2)═N—OCH3

1H-NMR (CDCl3) δ = 3.15








(s); 3.35(s); 3.62(t); 4.05








(s); 4.07(t); 5.35(br.);








6.74(m).












30
—CH2—CH2—CH2—CH2—
2,4,6-trifluorophenyl
Cl
C(═O)NH2
m.p. 195-198° C.













31
CH3
CH2-cyclo(C3H5)
2-chloro-6-fluorophenyl
Cl
CN
84-85° C.


32
CH3
CH(CH3)2
2-chloro-6-fluorophenyl
Cl
CN

1H NMR (400 MHz) in








CDCl3 [ppm]; 1.3(m, 6 H);








3.1(s, 3 H); 5.0(s, 1 H);








7.1(t, 1 H); 7.2-7.4(m,








2 H)


33
CH3
CH2-cyclo(C3H5)
2-chloro-6-fluorophenyl
Cl
C(NH2)═N—OCH3
116-118° C.


34
CH3
CH(CH3)2
2-chloro-6-fluorophenyl
Cl
C(NH2)═N—OCH3
152-154° C.


35
CH3
CH2-cyclo(C3H5)
2,6-difluorophenyl
Cl
CN
116-118° C.












36
—CH(CH3)—CH2—CH2—CH2—
2-chloro-6-fluorophenyl
Cl
C(NH2)═N—OCH3
129-131° C.













37
CH3
CH(CH3)2
2,6-difluorophenyl
Cl
CN
76-78° C.


38
CH3
CH2-cyclo(C3H5)
2,6-difluorophenyl
Cl
C(NH2)═N—OCH3
132-134° C.


39
CH3
CH(CH3)2
2,6-difluorophenyl
Cl
C(NH2)═N—OCH3
158-160° C.


40
CH3
CH2-cyclo(C3H5)
2,4,6-trifluorophenyl
Cl
OCH3

1H NMR (400 MHz) in








CDCl3 [ppm]: 0.3(m, 2 H);








0.5(m, 2 H); 1.2(m ,1 H);








3.1(s, 3 H); 3.7(d, 2 H); 4.0








(s, 3 H); 6.7(m, 2 H)


41
CH3
CH2—CH═CH2
2,4,6-trifluorophenyl
Cl
C(NH2)═N—OCH3

1H NMR (400 MHz) in








CDCl3 [ppm]: 3.1(s, 3 H);








4.0(s, 3 H); 4.5(m, 2 H);








5.2(m, 4 H); 5.9(m, 1 H);








6.8(m, 2 H)


42
CH3
CH2—CH3
2,4,6-trifluorophenyl
Cl
C(NH2)═N—OCH3

1H NMR (400 MHz) in








CDCl3 [ppm]: 1.7(m, 3 H);








3.1(s, 3 H); 3.9(m, 2 H);








4.1(s, 3 H); 5.5(s, 2 H);








6.7(m, 2 H)


43
CH3
CH2—C6C5
2,4,6-trifluorophenyl
Cl
C(NH2)═N—OCH3

1H NMR (400 MHz) in








CDCl3 [ppm]: 3.2(s, 3 H);








4.0(s, 3 H); 5.1(s, 2 H);








5.5(s, 2 H); 6.7(m, 2 H);








7.3(m, 5 H)


44
CH3
CH2CH2CH3
2,4,6-trifluorophenyl
Cl
C(NH2)═N—OCH3

1H NMR (400 MHz) in








CDCl3 [ppm]: 0.9(t, 3 H);








1.7(m, 2 H); 3.1(s, 3 H);








3.8(t, 2 H); 4.0(s, 3 H); 5.4








(s, 2 H); 6.7(m, 2 H)


45
CH3
CH(CH3)C2H5
2-chloro-6-fluorophenyl
Cl
C(NH2)═N—OCH3

1H NMR (400 MHz) in








CDCl3 [ppm]: 1.9(m, 3 H);








1.2(m, 3 H); 1.5(m ,1 H);








1.8(m ,1 H); 3.2(s, 3 H);








4.0(s, 3 H); 4.6(m, 1 H);








5.3(s, 2 H); 7.1(m, 1 H);








7.3(m, 2 H)


46
CH3
CH2CH(CH3)2
2-chloro-6-fluorophenyl
Cl
C(NH2)═N—OCH3


47
CH3
cyclo-(C5H9)
2-chloro-6-fluorophenyl
Cl
C(NH2)═N—OCH3


48
CH3
CH2OCH3
2-chloro-6-fluorophenyl
Cl
C(NH2)═N—OCH3












49
—CH2—CH2—CH(CH3)—CH2—
2,4,6-trifluorophenyl
Cl
C(NH2)═N—OCH3
119-120° C.









Examples of the Action Against Harmful Fungi
A Greenhouse Experiments

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 having emulsifying and dispersing action based on ethoxylated alkylphenols) in a volume ratio solvent/emulsifier of 99 to 1. The solution was then made up to 100 ml with water. This stock solution was diluted to the active compound concentration stated below using the solvent/emulsifier/water mixture described.


Use Example 1
Activity Against Early Blight on Tomatoes Caused by Alternaria solani

Leaves of potted plants of the cultivar “Goldene Königin” were sprayed to runoff point with an aqueous suspension having the concentration of active compound stated below. The next day, the leaves were infected with an aqueous spore suspension of Alternaria solani in a 2% biomalt solution having a density of 0.17×106 spores/ml. The plants were then placed in a water vapor-saturated chamber at temperatures between 20 and 22° C. After 5 days, the disease on the untreated, but infected control plants had developed to such an extent that the infection could be determined visually in %.


The plants which had been treated with an application rate of in each case 250 ppm of the compounds 3 to 5, 7, 8, 10 to 13, 15, 17, 18, 20 to 27, 30, 36, 41, 42, 43 or 46 to 49 of Table C showed an infection of at most 20%, whereas the untreated control plants were 90% infected.


The plants treated with the compounds 33 and 34, respectively, of Table C at an application rate of in each case 63 ppm showed an infection of at most 7%, whereas the untreated control plants were 90% infected.


Use Example 2
Curative Activity Against Brown Rust of Wheat Caused by Puccinia recondita

Leaves of potted wheat seedlings of the cultivar “Kanzler” were inoculated with a spore suspension of brown rust (Puccinia recondita). The pots were then placed into a chamber with high atmospheric humidity (90-95%) at 20-22° C. for 24 hours. During this time, the spores germinated and the germ tubes penetrated into the leaf tissue. The next day, the infected plants were sprayed to runoff point with the active compound solution described above having the concentration of active compound stated below. After the spray coating had dried on, the test plants were cultivated in a greenhouse at temperatures between 20 and 22° C. and at 65 to 70% relative atmospheric humidity for 7 days. The extent of the rust fungus development on the leaves was then determined.


The plants which had been treated with an application rate of 250 ppm of the compound 9 showed an infection of 10%, whereas the untreated control plants were 80% infected.


The plants which had been treated with an application rate of in each case 250 ppm of the compounds 37 to 39, 44 and 45, respectively, showed an infection of at most 10%, whereas the untreated control plants were 90% infected.


The plants which had been treated with an application rate of 63 ppm of the compound 33 showed an infection of 0%, whereas the untreated control plants were 90% infected.


Use Example 3
Activity Against Late Blight on Tomatoes Caused by Phytophthora infestans, Protective Treatment

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


The plants which had been treated with an application rate of in each case 250 ppm of the compounds 24, 25, 28, 29 or 31 showed an infection of at most 20%, whereas the untreated control plants were 90% infected.


Use Example 4
Activity Against Net Blotch of Barley Caused by Pyrenophora teres, 1 Day Protective Application

Leaves of potted barley seedlings were sprayed to runoff point with an aqueous suspension having the concentration of active compound stated below. 24 hours after the spray coating had dried on, the test plants were inoculated with an aqueous spore suspension of Pyrenophora [syn. Drechslera] teres, the net blotch pathogen. The test plants were then placed into a greenhouse at temperatures between 20 and 24° C. and 95 to 100% relative atmospheric humidity. After 6 days, the extent of the development of the disease was determined visually in % infection of the total leaf area.


The plants which had been treated with an application rate of in each case 250 ppm of the compounds 3 to 5, 7, 8, 11 to 15, 18 to 22, 26 and 27 showed an infection of at most 20%, whereas the untreated control plants were 90% infected.


Use Example 5
Protective Activity Against Puccinia recondita on Wheat (Brown Rust of Wheat)

Leaves of potted wheat seedlings of the cultivar “Kanzler” were sprayed to runoff point with an aqueous suspension having the concentration of active compound stated below. The next day, the treated plants were inoculated with a spore suspension of brown rust of wheat (Puccinia recondita). The plants were then placed in a chamber with high atmospheric humidity (90 to 95%) at 20 to 22° C. for 24 hours. During this time, the spores germinated and the germ tubes penetrated into the leaf tissue. The next day, the test plants were returned to the greenhouse and cultivated at temperatures between 20 and 22° C. and at 65 to 70% relative atmospheric humidity for a further 7 days. The extent of the rust fungus development on the leaves was then determined visually.


The plants which had been treated with an application rate of in each case 250 ppm of the compounds 9, 17, 23, 19, 28, 36 to 39, 41, 42 or 44 to 49 showed an infection of at most 15%, whereas the untreated control plants were 90% infected.


Use Example 6
Activity Against Mildew of Wheat Caused by Erysiphe [syn. Blumeria] graminis Forma Specialis, tritici

Leaves of potted wheat seedlings were sprayed to runoff point with an aqueous suspension having the concentration of active compound stated below. The suspension or emulsion had been prepared as described above. 24 hours after the spray coating had dried on, dusted with spores of mildew of wheat (Erysiphe [syn. Blumeria] graminis forma specialis. tritici). The test plants were then placed in a greenhouse at temperatures between 20 and 24° C. and 60 to 90% relative atmospheric humidity. After 7 days, the extent of the mildew development was determined visually in % infection of the total leaf area.


The plants which had been treated with an application rate of 250 ppm of the compound 35 showed an infection of 5%, whereas the control plants were 90% infected.


B Microtest

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


Microtest No. 1—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 an aqueous malt-based fungus nutrient medium to the stated active compound concentration. An aqueous spore suspension of Septoria tritici was then added. The plates were placed in a water vapor-saturated chamber at temperatures of 18° C. On day 7 after the inoculation, the MTPs were measured in an absorption photometer at 405 nm. 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 a concentration of in each case 125 ppm, the compounds 32 and 40, respectively, caused a relative growth of 0%.


Microtest No. 2—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 an aqueous malt-based fungus nutrient medium to the stated active compound concentration. An aqueous spore suspension of Pyricularia oryzae was then added. The plates were placed in a water vapor-saturated chamber at temperatures of 18° C. On day 7 after the inoculation, the MTPs were measured in an absorption photometer at 405 nm. 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 a concentration of in each case 125 ppm, the compounds 32 and 40, respectively, caused a relative growth of 0%.

Claims
  • 1-21. (canceled)
  • 22. A compound of formula I,
  • 23. The compound of claim 22, having the formula I′
  • 24. The compound of claim 23, wherein: R1 and R11 independently of one another are C1-C6-alkyl, C3-C6-cycloalkyl, C1-C4-alkyl-C3-C6-cycloalkyl, C3-C6-cycloalkyl-C1-C6-alkyl, di-C1-C4-alkyl-C3-C6-cycloalkyl, C1-C4-alkoxy-C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl or C2-C6-haloalkynyl, wherein R1 and R11 together may also form a five-, six- or seven-membered saturated or unsaturated heterocycle; whereinR1 and/or R11 or a heterocycle formed by R1 and R11 may carry one, two, three or four identical or different substituents R2, wherein R2 is:R2 is halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C4-C6-cycloalkenyl, hydroxyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C8-alkenyloxy, C3-C6-cycloalkyloxy, —C(═O)-A, —C(═O)—O-A, —C(═O)—N(A′)A, C(A′)(═N—OA), N(A′)A, N(A′)-C(═O)-A, N(A″)—C(═O)—N(A′)A, or phenyl, wherein the phenyl moiety may carry one, two or three radicals independently of one another selected from the group consisting of: halogen, C1-C6-alkyl, C2-C6-alkenyl, C3-C6-cycloalkyl, C1-C6-haloalkyl, C1-C6-alkoxy, cyano, nitro, —C(═O)-A, —C(═O)—O-A, —C(═O)—N(A′)A, C(A′)(═N—OA), N(A′)A; wherein,A, A′, A″ independently of one another hydrogen or C1-C6-alkyl which may be partially or fully halogenated and/or may be substituted by C1-C4-alkoxy;R3 is halogen, cyano, C1-C4-alkyl, C1-C4-alkoxy, halogenmethoxy or C1-C4-haloalkyl;R4 is pyrazolyl, 1,2,3-triazolyl or 1,2,4-triazolyl, wherein R4 is attached to the pyrimidine ring via N and is unsubstituted or substituted by one or two substituents Ru:Ru is halogen, cyano, C1-C4-alkyl, C1-C4-alkoxy, —C(═O)—O-A, —C(═O)—N(A′)A, C(A′)(═N—OA), N(A′)A, N(A′)-C(═O)-A; wherein A,A′ are as defined above; R4 may furthermore be: C(═O)NRzRb, C(═O)ORa, C(═NORa)NH2, C(═NORb)Ra or NRa(C(═O)ORb); wherein:Ra, Rb and Rc independently of one another are hydrogen, C1-C6-alkyl, or C3-C6-cycloalkyl;Rz has the same meanings as Ra and may additionally be —CO—Rd or —COO—Rd;L is halogen, cyano, methyl, methoxy, —C(═O)—O-A, —C(═O)—N(A′)A, —C(═S)—N(A′)A, C(A′)(—N—OA), N(A′)A, N(A′)-C(═O)-A; wherein A and A′ are as defined above; andn is 1, 2 or 3, wherein at least one substituent L on the phenyl ring is located in the ortho-position to the point of attachment to the pyrimidine.
  • 25. The compound of claim 22, wherein: R4 is 1-pyrazolyl or 1-[1,2,4]triazolyl.
  • 26. The compound of claim 22, wherein: R4 is 2-pyridinyl, 3-pyridazinyl, 1-pyridin(1,2-dihydro)-2-onyl or 1-pyrrolidonyl.
  • 27. The compound of claim 22, wherein: R4 is 2-pyrimidinyl.
  • 28. The compound of claim 22, wherein: R4 is C(=Z)ORa, C(=Z)NRzRb or C(=Z)Ra andZ is O, NRd or NORd.
  • 29. The compound of claim 22, wherein: R1 and R11 independently of one another are C1-C6-alkyl, C3-C6-cycloalkyl, C1-C4-alkyl-C3-C6-cycloalkyl, C3-C6-cycloalkyl-C1-C6-alkyl, di-C1-C4-alkyl-C3-C6-cycloalkyl, C1-C4-alkoxy-C1-C6-alkyl, C2-C6-alkenyl, C1-C6-haloalkyl or C2-C6-haloalkenyl.
  • 30. The compound of claim 22, wherein: R1 and R11 together form a five-, six- or seven-membered saturated or unsaturated heterocycle which may carry one, two, three or four identical or different substituents R2, wherein:R2 is halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C4-C6-cycloalkenyl, hydroxyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C8-alkenyloxy, C3-C6-cycloalkyloxy, —C(═O)-A, —C(═O)—O-A, —C(═O)—N(A′)A, C(A′)(═N—OA), N(A′)A, N(A′)-C(═O)-A, N(A″)—C(═O)—N(A′)A, or phenyl, wherein the phenyl moiety may carry one, two or three radicals independently of one another selected from the group consisting of: halogen, C1-C6-alkyl, C2-C6-alkenyl, C3-C6-cycloalkyl, C1-C6-haloalkyl, C1-C6-alkoxy, cyano, nitro, —C(═O)-A, —C(═O)—O-A, —C(═O)—N(A′)A, C(A′)(═N—OA), N(A′)A; wherein,A, A′, A″ independently of one another hydrogen, C1-C6-alkyl, C2-C6-alkenyl, phenyl, wherein the organic radicals may be partially or fully halogenated and/or may be substituted by C1-C4-alkoxy; A and A′ together with the atoms to which they are attached may also be a five- or six-membered saturated heterocycle which contains one or two heteroatoms from the group consisting of O, N and S.
  • 31. The compound of claim 30, wherein: R1 and R11 together form a saturated five- or six-membered ring which may carry one, two, three or four identical or different substituents R2.
  • 32. The compound of claim 31, wherein R2 is C1-C6-alkyl or C1-C6-haloalkyl.
  • 33. The compound of claim 32, wherein: B is substituted by Ln is of the formula:
  • 34. The compound of claim 22, having the formula Ia
  • 35. A pesticidal composition comprising at least one compound of formula I
  • 36. The pesticidal composition of 35, further comprising at least one fungicidally, insecticidally and/or herbicidally active compound.
  • 37. A composition of at least one compound of formula I
  • 38. The composition of claim 37, comprising a compound of formula Ia
  • 39. The composition of claim 37, comprising a compound formula I, wherein R11 is CH3, R1 is CH3,
  • 40. A method for controlling phytopathogenic fungi comprising, treating the fungi and/or the materials, plants, the soil or seed to be protected against fungal attack with an effective amount of at least one compound of formula I
  • 41. A method for controlling animal pests in agriculture comprising, treating the pests and/or the materials, plants, the soil or seed to be protected against fungal attack with an effective amount of at least one compound of formula I
  • 42. A seed comprising in an amount of from 1 to 1000 g per 100 kg a compound of formula I
Priority Claims (1)
Number Date Country Kind
102005046592.7 Sep 2005 DE national
PCT Information
Filing Document Filing Date Country Kind 371c Date
PCT/EP2006/066572 9/21/2006 WO 00 3/24/2008